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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:52:29 UTC

Update Date

2023-02-21 17:22:43 UTC

HMDB ID

HMDB0032887

Secondary Accession Numbers

HMDB32887

Metabolite Identification

Common Name

4-Amino-2-methyl-1-naphthol

Description

4-Amino-2-methyl-1-naphthol, also known as vitamin K5, hydrochloride, belongs to the class of organic compounds known as naphthols and derivatives. These are naphthalene derivatives carrying one or more hydroxyl (-OH) groups at any ring position. Based on a literature review very few articles have been published on 4-Amino-2-methyl-1-naphthol.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0       5.335   0.000   0.000  0.00  0.00           N+0
HETATM   13  O   UNK     0       5.335   6.160   0.000  0.00  0.00           O+0
CONECT    1    7                                                            
CONECT    2    3    4                                                       
CONECT    3    2    5                                                       
CONECT    4    2    8                                                       
CONECT    5    3    9                                                       
CONECT    6    7   10                                                       
CONECT    7    1    6   11                                                  
CONECT    8    4    9   10                                                  
CONECT    9    5    8   11                                                  
CONECT   10    6    8   12                                                  
CONECT   11    7    9   13                                                  
CONECT   12   10                                                            
CONECT   13   11                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   28    0
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
4-Amino-2-methyl-1-naphthalenol, hydrochloride	MeSH
Vitamin K5, hydrochloride	MeSH
1-Naphthalenol, 4-amino-2-methyl-, hydrochloride	HMDB
1-Naphthol, 4-amino-2-methyl-, hydrochloride (8ci)	HMDB
2-Methyl-4-amino-1-naphthol	HMDB
2-Methyl-4-amino-1-naphthol hydrochloride	HMDB
4-amino-2-Methyl-1-naphthalenol, 9ci	HMDB
4-amino-2-METHYL-1-naphthol hci	HMDB
4-amino-2-Methylnaphthol hydrochloride	HMDB
4-Hydroxy-3-methyl-1-naphthylammonium chloride	HMDB
Synkamin hydrochloride	HMDB
Vitamin K5	HMDB
Vitamin K5 hydrochloride	HMDB
4-Amino-2-methyl-1-naphthol	MeSH

Chemical Formula

C₁₁H₁₁NO

Average Molecular Weight

173.2111

Monoisotopic Molecular Weight

173.084063979

IUPAC Name

4-amino-2-methylnaphthalen-1-ol

Traditional Name

4-amino-2-methylnaphthalen-1-ol

CAS Registry Number

83-70-5

SMILES

CC1=C(O)C2=CC=CC=C2C(N)=C1

InChI Identifier

InChI=1S/C11H11NO/c1-7-6-10(12)8-4-2-3-5-9(8)11(7)13/h2-6,13H,12H2,1H3

InChI Key

UGQFCTZXVAPVCS-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthols and derivatives. These are naphthalene derivatives carrying one or more hydroxyl (-OH) groups at any ring position.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Naphthalenes

Sub Class

Naphthols and derivatives

Direct Parent

Naphthols and derivatives

Alternative Parents

Substituents

1-naphthol
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Hydrocarbon derivative
Primary amine
Organooxygen compound
Organonitrogen compound
Amine
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0032887)
Cytoplasm (HMDB: HMDB0032887)

Source

Exogenous

Food

Food (HMDB: HMDB0032887)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0032887)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.56 g/L	ALOGPS
logP	2.03	ALOGPS
logP	2.34	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	10.38	ChemAxon
pKa (Strongest Basic)	5.34	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	54.23 m³·mol⁻¹	ChemAxon
Polarizability	18.99 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	138.399	31661259
DarkChem	[M-H]-	136.272	31661259
DeepCCS	[M+H]+	136.166	30932474
DeepCCS	[M-H]-	133.728	30932474
DeepCCS	[M-2H]-	169.305	30932474
DeepCCS	[M+Na]+	143.764	30932474
AllCCS	[M+H]+	136.1	32859911
AllCCS	[M+H-H2O]+	131.5	32859911
AllCCS	[M+NH4]+	140.3	32859911
AllCCS	[M+Na]+	141.5	32859911
AllCCS	[M-H]-	136.9	32859911
AllCCS	[M+Na-2H]-	137.2	32859911
AllCCS	[M+HCOO]-	137.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4-Amino-2-methyl-1-naphthol	CC1=C(O)C2=CC=CC=C2C(N)=C1	2832.8	Standard polar	33892256
4-Amino-2-methyl-1-naphthol	CC1=C(O)C2=CC=CC=C2C(N)=C1	1852.4	Standard non polar	33892256
4-Amino-2-methyl-1-naphthol	CC1=C(O)C2=CC=CC=C2C(N)=C1	1942.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
4-Amino-2-methyl-1-naphthol,1TMS,isomer #1	CC1=CC(N)=C2C=CC=CC2=C1O[Si](C)(C)C	1980.9	Semi standard non polar	33892256
4-Amino-2-methyl-1-naphthol,1TMS,isomer #2	CC1=CC(N[Si](C)(C)C)=C2C=CC=CC2=C1O	2027.2	Semi standard non polar	33892256
4-Amino-2-methyl-1-naphthol,2TMS,isomer #1	CC1=CC(N[Si](C)(C)C)=C2C=CC=CC2=C1O[Si](C)(C)C	2070.7	Semi standard non polar	33892256
4-Amino-2-methyl-1-naphthol,2TMS,isomer #1	CC1=CC(N[Si](C)(C)C)=C2C=CC=CC2=C1O[Si](C)(C)C	1923.7	Standard non polar	33892256
4-Amino-2-methyl-1-naphthol,2TMS,isomer #2	CC1=CC(N([Si](C)(C)C)[Si](C)(C)C)=C2C=CC=CC2=C1O	2075.2	Semi standard non polar	33892256
4-Amino-2-methyl-1-naphthol,2TMS,isomer #2	CC1=CC(N([Si](C)(C)C)[Si](C)(C)C)=C2C=CC=CC2=C1O	2030.8	Standard non polar	33892256
4-Amino-2-methyl-1-naphthol,3TMS,isomer #1	CC1=CC(N([Si](C)(C)C)[Si](C)(C)C)=C2C=CC=CC2=C1O[Si](C)(C)C	2043.3	Semi standard non polar	33892256
4-Amino-2-methyl-1-naphthol,3TMS,isomer #1	CC1=CC(N([Si](C)(C)C)[Si](C)(C)C)=C2C=CC=CC2=C1O[Si](C)(C)C	1984.8	Standard non polar	33892256
4-Amino-2-methyl-1-naphthol,1TBDMS,isomer #1	CC1=CC(N)=C2C=CC=CC2=C1O[Si](C)(C)C(C)(C)C	2247.4	Semi standard non polar	33892256
4-Amino-2-methyl-1-naphthol,1TBDMS,isomer #2	CC1=CC(N[Si](C)(C)C(C)(C)C)=C2C=CC=CC2=C1O	2275.4	Semi standard non polar	33892256
4-Amino-2-methyl-1-naphthol,2TBDMS,isomer #1	CC1=CC(N[Si](C)(C)C(C)(C)C)=C2C=CC=CC2=C1O[Si](C)(C)C(C)(C)C	2506.4	Semi standard non polar	33892256
4-Amino-2-methyl-1-naphthol,2TBDMS,isomer #1	CC1=CC(N[Si](C)(C)C(C)(C)C)=C2C=CC=CC2=C1O[Si](C)(C)C(C)(C)C	2343.4	Standard non polar	33892256
4-Amino-2-methyl-1-naphthol,2TBDMS,isomer #2	CC1=CC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C2C=CC=CC2=C1O	2535.5	Semi standard non polar	33892256
4-Amino-2-methyl-1-naphthol,2TBDMS,isomer #2	CC1=CC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C2C=CC=CC2=C1O	2423.8	Standard non polar	33892256
4-Amino-2-methyl-1-naphthol,3TBDMS,isomer #1	CC1=CC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C2C=CC=CC2=C1O[Si](C)(C)C(C)(C)C	2734.9	Semi standard non polar	33892256
4-Amino-2-methyl-1-naphthol,3TBDMS,isomer #1	CC1=CC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C2C=CC=CC2=C1O[Si](C)(C)C(C)(C)C	2615.9	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Amino-2-methyl-1-naphthol GC-MS (Non-derivatized) - 70eV, Positive	splash10-00di-0900000000-6677c2f4f2ad22c0082c	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Amino-2-methyl-1-naphthol GC-MS (1 TMS) - 70eV, Positive	splash10-00ec-7890000000-1b00de3c036af1a480dc	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Amino-2-methyl-1-naphthol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Amino-2-methyl-1-naphthol 10V, Positive-QTOF	splash10-05fr-0900000000-32a317e92f65cb346309	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Amino-2-methyl-1-naphthol 20V, Positive-QTOF	splash10-05fr-0900000000-0f9658734f5e9a49bf8a	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Amino-2-methyl-1-naphthol 40V, Positive-QTOF	splash10-0a4i-1900000000-99337b7ed86fcc70d9f2	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Amino-2-methyl-1-naphthol 10V, Negative-QTOF	splash10-00di-0900000000-f41821de00def2a3dd2f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Amino-2-methyl-1-naphthol 20V, Negative-QTOF	splash10-00di-0900000000-facff9937db0e20a348c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Amino-2-methyl-1-naphthol 40V, Negative-QTOF	splash10-0ab9-0900000000-e8d4f8a39e289fb6d764	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Amino-2-methyl-1-naphthol 10V, Negative-QTOF	splash10-00di-0900000000-4c1ad417189eea157a87	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Amino-2-methyl-1-naphthol 20V, Negative-QTOF	splash10-00di-0900000000-3153ae705b940a890d19	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Amino-2-methyl-1-naphthol 40V, Negative-QTOF	splash10-0200-9500000000-220ac355fe481206396c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Amino-2-methyl-1-naphthol 10V, Positive-QTOF	splash10-00di-0900000000-911e02e0c3fb31dd9b95	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Amino-2-methyl-1-naphthol 20V, Positive-QTOF	splash10-0ab9-0900000000-630b5a4805b79a21ac35	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Amino-2-methyl-1-naphthol 40V, Positive-QTOF	splash10-004i-5900000000-4ae6d66e97b26429e884	2021-09-23	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB010869

KNApSAcK ID

Not Available

Chemspider ID

6497

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

4-Amino-2-methyl-1-naphthol

METLIN ID

Not Available

PubChem Compound

6754

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for 4-Amino-2-methyl-1-naphthol (HMDB0032887)

MOL for HMDB0032887 (4-Amino-2-methyl-1-naphthol)

3D MOL for HMDB0032887 (4-Amino-2-methyl-1-naphthol)

3D SDF for HMDB0032887 (4-Amino-2-methyl-1-naphthol)

3D-SDF for HMDB0032887 (4-Amino-2-methyl-1-naphthol)

PDB for HMDB0032887 (4-Amino-2-methyl-1-naphthol)

3D PDB for HMDB0032887 (4-Amino-2-methyl-1-naphthol)

SMILES for HMDB0032887 (4-Amino-2-methyl-1-naphthol)

INCHI for HMDB0032887 (4-Amino-2-methyl-1-naphthol)

Structure for HMDB0032887 (4-Amino-2-methyl-1-naphthol)

3D Structure for HMDB0032887 (4-Amino-2-methyl-1-naphthol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra