T3DB: 3-Aminophenol

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Gene Regulation Targets (15)XML

Targets (15)

Record Information

Version

2.0

Creation Date

2009-11-11 22:22:53 UTC

Update Date

2014-12-24 20:26:12 UTC

Accession Number

T3D3601

Identification

Common Name

3-Aminophenol

Class

Small Molecule

Description

3-Aminophenol is an amphoteric molecule and a reducing agent. Aminophenols are intermediates in the synthesis of dyes and can thus be found in numerous cosmetics products, particularly hair dyes. (6)

Compound Type

Amine
Aromatic Hydrocarbon
Cosmetic Toxin
Household Toxin
Natural Compound
Organic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym
-hydroxybenzenamine
1-Amino-3-hydroxybenzene
3-Amino-1-hydroxybenzene
3-Hydroxyaniline
3-Hydroxyanilinel AC
3-Hydroxybenzenamine
Basf ursol eg
Fouramine eg
Fourrine 65
Fourrine eg
Furro eg
Futramine eg
M-aminofenol
M-aminophenol
M-hydroxyaminobenzene
M-hydroxyaniline
M-hydroxyphenylamine
Nako teg
Pelagol eg
Renal eg
Rodinal
Tertral eg
Ursol eg

Chemical Formula

C₆H₇NO

Average Molecular Mass

109.126 g/mol

Monoisotopic Mass

109.053 g/mol

CAS Registry Number

591-27-5

IUPAC Name

3-aminophenol

Traditional Name

m-aminophenol

SMILES

NC1=CC=CC(O)=C1

InChI Identifier

InChI=1S/C6H7NO/c7-5-2-1-3-6(8)4-5/h1-4,8H,7H2

InChI Key

InChIKey=CWLKGDAVCFYWJK-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as aniline and substituted anilines. These are organic compounds containing an aminobenzene moiety.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Aniline and substituted anilines

Direct Parent

Aniline and substituted anilines

Alternative Parents

Substituents

M-aminophenol
Aniline or substituted anilines
Aminophenol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Hydrocarbon derivative
Primary amine
Organooxygen compound
Organonitrogen compound
Amine
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

aminophenol (CHEBI:28924 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Extracellular

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	123°C
Boiling Point	Not Available
Solubility	27 mg/mL at 20°C
LogP	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	98.3 g/L	ALOGPS
logP	0.43	ALOGPS
logP	0.84	ChemAxon
logS	-0.05	ALOGPS
pKa (Strongest Acidic)	9.82	ChemAxon
pKa (Strongest Basic)	4.02	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	46.25 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	32.74 m³·mol⁻¹	ChemAxon
Polarizability	11.22 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	Not Available	2020-06-30	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	Not Available	2020-06-30	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	Not Available	2020-06-30	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	Not Available	2020-06-30	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive	Not Available	2020-06-30	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-4900000000-a4a9fe19d8204063a0a1	2021-09-23	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-03	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 3V, negative	splash10-0a4i-1900000000-721604165cf24d59220a	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - n/a 7V, negative	splash10-014i-9000000000-bab101816aea97360a06	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 3V, positive	splash10-03di-1900000000-05190e4b13fe2b48bc64	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 4V, positive	splash10-03di-1900000000-f6c081468897bdc743a1	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 5V, positive	splash10-03di-1900000000-d84028ec5ae86688def4	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 7V, positive	splash10-03di-2900000000-8ddd827b9a2bd3240f6a	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 10V, positive	splash10-03di-5900000000-8a3580af40459f7d97e9	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 15V, positive	splash10-03xu-9400000000-75cbe10fa8b47df0df6b	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 17V, positive	splash10-02tc-9200000000-648483fd6f1d73f805f9	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 20V, positive	splash10-014l-9100000000-b0b9496fd6b6fbc18600	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 23V, positive	splash10-014i-9000000000-685317cd4c77e7cb6fa5	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 25V, positive	splash10-014i-9000000000-16522bd5184444337e26	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 27V, positive	splash10-014i-9000000000-c6fbe0407dca71b1bbb8	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 30V, positive	splash10-014i-9000000000-7f1ace16286d7d01ebde	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 33V, positive	splash10-014r-9000000000-786f2d238803501a32b4	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 35V, positive	splash10-014r-9000000000-8dd83d0e1c328e3936f3	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 40V, positive	splash10-00kr-9000000000-606b4ab540d5f21542e9	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 45V, positive	splash10-000i-9000000000-34721f503ff167afb907	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 2V, positive	splash10-03di-2900000000-9b1eee9f0d9a44187ca4	2020-07-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0900000000-e51735a6e5d4a3e5eead	2016-06-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-1900000000-09d13b69959de03f7d24	2016-06-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0gb9-9100000000-6803b31dff294a8f675c	2016-06-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0900000000-81db2f962b909ae3bce5	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-0900000000-440dd43ef196996903c0	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9500000000-f0a2d17e6f8da98a7b0a	2016-08-03	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0a4i-7900000000-6422996aedcba7475ca2	2014-09-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, DMSO-d6, experimental)	Not Available	2014-09-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 22.53 MHz, DMSO-d6, experimental)	Not Available	2014-09-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	2021-10-13	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	2021-10-13	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	2021-10-13	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	2021-10-13	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	2021-10-13	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	2021-10-13	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	2021-10-13	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	2021-10-13	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	2021-10-13	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	2021-10-13	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	2021-10-13	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	2021-10-13	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	2021-10-13	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	2021-10-13	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	2021-10-13	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	2021-10-13	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	2021-10-13	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	2021-10-13	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	2021-10-13	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	2021-10-13	View Spectrum

Toxicity Profile

Route of Exposure

Oral (4) ; inhalation (4)

Mechanism of Toxicity

3-Aminophenol interacts with both adult and fetal hemoglobin, forming methemoglobin. In comparison to its isomers, 2-aminophenol and 4-aminophenol, 3-aminophenol is the least effective in forming methemoglobin. Since methemoglobin cannot bind oxygen like hemoglobin can, elevated levels of methemoglobin cause a condition called methemoglobinemia, which can result in tissue hypoxia. (5, 1)

Metabolism

Not Available

Toxicity Values

LD50: 150 mg/kg (Intraperitoneal, Mouse) (2) LD50: 750 mg/kg (Oral, Quail) (2)

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

Aminophenols are also intermediates in the synthesis of dyes and can thus be found in numerous cosmetics products, particularly hair dyes. (6)

Minimum Risk Level

Not Available

Health Effects

3-Aminophenol may act as a skin sensitizer and cause contact dermatitis. In addition, inhalation of large amounts can cause methemoglobinemia and bronchial asthma. (3)

Symptoms

3-Aminophenol may cause contact dermatitis. Signs and symptoms of methemoglobinemia may include shortness of breath, cyanosis, mental status changes, headache, fatigue, exercise intolerance, dizziness and loss of consciousness. Severe methemoglobinemia can result in dysrhythmias, seizures, coma, and death. (3, 5)

Treatment

Methemoglobinemia can be treated with supplemental oxygen and methylene blue 1% solution administered intravenously slowly over five minutes followed by IV flush with normal saline. Methylene blue restores the iron in hemoglobin to its normal (reduced) oxygen-carrying state. (5)

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

Not Available

PubChem Compound ID

ChEMBL ID

ChemSpider ID

KEGG ID

UniProt ID

Not Available

OMIM ID

ChEBI ID

BioCyc ID

CTD ID

Stitch ID

PDB ID

Not Available

ACToR ID

219691

Wikipedia Link

3-Aminophenol

References

Synthesis Reference

Not Available

MSDS

T3D3601.pdf

General References

Wind M, Stern A: Comparison of human adult and fetal hemoglobin: aminophenol-induced methemoglobin formation. Experientia. 1977 Nov 15;33(11):1500-1. [923727 ]
Lewis RJ (1996). Sax's Dangerous Properties of Industrial Materials. 9th ed. Volumes 1-3. New York, NY: Van Nostrand Reinhold.
Clayton GD and Clayton FE (eds) (1993-1994). Patty's Industrial Hygiene and Toxicology. Volumes 2A, 2B, 2C, 2D, 2E, 2F: Toxicology. 4th ed. New York, NY: John Wiley & Sons Inc.
HSDB: Hazardous Substances Data Bank. National Library of Medicine (2001). [Link]
Wikipedia. Methemoglobinemia. Last Updated 22 July 2009. [Link]
Wikipedia. 2-Aminophenol. Last Updated 12 June 2009. [Link]

Gene Regulation

Up-Regulated Genes

Gene	Gene Symbol	Gene ID	Interaction	Chromosome	Details

Down-Regulated Genes

Not Available

Targets

Target Details

1. Hemoglobin subunit alpha

General Function:: Oxygen transporter activity
Specific Function:: Involved in oxygen transport from the lung to the various peripheral tissues.
Gene Name:: HBA1
Uniprot ID:: P69905
Molecular Weight:: 15257.405 Da

References

Target Details

2. Hemoglobin subunit beta

General Function:: Oxygen transporter activity
Specific Function:: Involved in oxygen transport from the lung to the various peripheral tissues.LVV-hemorphin-7 potentiates the activity of bradykinin, causing a decrease in blood pressure.Spinorphin: functions as an endogenous inhibitor of enkephalin-degrading enzymes such as DPP3, and as a selective antagonist of the P2RX3 receptor which is involved in pain signaling, these properties implicate it as a regulator of pain and inflammation.
Gene Name:: HBB
Uniprot ID:: P68871
Molecular Weight:: 15998.34 Da

References

Target Details

3. Hemoglobin subunit delta

General Function:: Oxygen transporter activity
Specific Function:: Involved in oxygen transport from the lung to the various peripheral tissues.
Gene Name:: HBD
Uniprot ID:: P02042
Molecular Weight:: 16055.41 Da

References

Target Details

4. Hemoglobin subunit epsilon

General Function:: Oxygen transporter activity
Specific Function:: The epsilon chain is a beta-type chain of early mammalian embryonic hemoglobin.
Gene Name:: HBE1
Uniprot ID:: P02100
Molecular Weight:: 16202.71 Da

References

Target Details

5. Hemoglobin subunit gamma-1

General Function:: Oxygen transporter activity
Specific Function:: Gamma chains make up the fetal hemoglobin F, in combination with alpha chains.
Gene Name:: HBG1
Uniprot ID:: P69891
Molecular Weight:: 16140.37 Da

References

Target Details

6. Hemoglobin subunit gamma-2

General Function:: Gamma chains make up the fetal hemoglobin F, in combination with alpha chains.
Specific Function:: Heme binding
Gene Name:: HBG2
Uniprot ID:: P69892
Molecular Weight:: 16126.35 Da

References

Target Details

7. Hemoglobin subunit mu

General Function:: Oxygen transporter activity
Specific Function:: Not Available
Gene Name:: HBM
Uniprot ID:: Q6B0K9
Molecular Weight:: 15617.97 Da

References

Target Details

8. Hemoglobin subunit theta-1

General Function:: Oxygen transporter activity
Specific Function:: Not Available
Gene Name:: HBQ1
Uniprot ID:: P09105
Molecular Weight:: 15507.575 Da

References

Target Details

9. Hemoglobin subunit zeta

General Function:: Oxygen transporter activity
Specific Function:: The zeta chain is an alpha-type chain of mammalian embryonic hemoglobin.
Gene Name:: HBZ
Uniprot ID:: P02008
Molecular Weight:: 15636.845 Da

References

Target Details

10. Carbonic anhydrase 1

General Function:: Zinc ion binding
Specific Function:: Reversible hydration of carbon dioxide. Can hydrates cyanamide to urea.
Gene Name:: CA1
Uniprot ID:: P00915
Molecular Weight:: 28870.0 Da

Binding/Activity Constants

Type	Value	Assay Type	Assay Source
Inhibitory	4.9 uM	Not Available	BindingDB 50428384

References

Target Details

11. Carbonic anhydrase 12

General Function:: Zinc ion binding
Specific Function:: Reversible hydration of carbon dioxide.
Gene Name:: CA12
Uniprot ID:: O43570
Molecular Weight:: 39450.615 Da

Binding/Activity Constants

Type	Value	Assay Type	Assay Source
Inhibitory	7.7 uM	Not Available	BindingDB 50428384

References

Target Details

12. Carbonic anhydrase 14

General Function:: Metal ion binding
Specific Function:: Reversible hydration of carbon dioxide.
Gene Name:: CA14
Uniprot ID:: Q9ULX7
Molecular Weight:: 37667.37 Da

Binding/Activity Constants

Type	Value	Assay Type	Assay Source
Inhibitory	7.2 uM	Not Available	BindingDB 50428384

References

Target Details

13. Carbonic anhydrase 2

General Function:: Zinc ion binding
Specific Function:: Essential for bone resorption and osteoclast differentiation (By similarity). Reversible hydration of carbon dioxide. Can hydrate cyanamide to urea. Involved in the regulation of fluid secretion into the anterior chamber of the eye. Contributes to intracellular pH regulation in the duodenal upper villous epithelium during proton-coupled peptide absorption. Stimulates the chloride-bicarbonate exchange activity of SLC26A6.
Gene Name:: CA2
Uniprot ID:: P00918
Molecular Weight:: 29245.895 Da

Binding/Activity Constants

Type	Value	Assay Type	Assay Source
Inhibitory	4.7 uM	Not Available	BindingDB 50428384

References

Target Details

14. Carbonic anhydrase 7

General Function:: Zinc ion binding
Specific Function:: Reversible hydration of carbon dioxide.
Gene Name:: CA7
Uniprot ID:: P43166
Molecular Weight:: 29658.235 Da

Binding/Activity Constants

Type	Value	Assay Type	Assay Source
Inhibitory	5.9 uM	Not Available	BindingDB 50428384

References

Target Details

15. Carbonic anhydrase 9

General Function:: Zinc ion binding
Specific Function:: Reversible hydration of carbon dioxide. Participates in pH regulation. May be involved in the control of cell proliferation and transformation. Appears to be a novel specific biomarker for a cervical neoplasia.
Gene Name:: CA9
Uniprot ID:: Q16790
Molecular Weight:: 49697.36 Da

Binding/Activity Constants

Type	Value	Assay Type	Assay Source
Inhibitory	4.9 uM	Not Available	BindingDB 50428384

References

3-Aminophenol (T3D3601)

Structure for T3D3601: 3-Aminophenol

Targets

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Binding/Activity Constants

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