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Showing NP-Card for 4-Amino-2-methyl-1-naphthol (NP0337491)

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Record Information
Version2.0
Created at2024-09-11 11:05:38 UTC
Updated at2024-09-11 11:05:38 UTC
NP-MRD IDNP0337491
Secondary Accession NumbersNone
Natural Product Identification
Common Name4-Amino-2-methyl-1-naphthol
Description4-Amino-2-methyl-1-naphthol, also known as vitamin K5 or 2-methyl-4-amino-1-naphthol, 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. Oral lethal dose for the HCl salt in rats is 0.7 G/kg.4-Amino-2-methyl-1-naphthol HCl salt is a vitamin K and prevents bleeding caused by vitamin K deficiency when given via intravenous or intramuscular injections at doses of about 1–3 mg. 4-Amino-2-methyl-1-naphthol is a very strong basic compound (based on its pKa). Vitamin K function of the compound was first noted in 1940. Its hydrochloride (HCl) salt is often called vitamin K5. Latter is formed via oxidation and deamination of 4-amino-2-methyl-1-naphthol.4-Amino-2-methyl-1-naphthol can be made from 2-methylnaphthalene or menadione.4-Amino-2-methyl-1-naphthol HCl salt prevents the growth of different molds and bacteria. It darkens at 262 °C and decays without melting at 280–282 °C.HCl salt breaks down in aqueous solutions via oxidation which is quite fast at neutral pH. First a pink and later a purple precipitant forms. The colored precipitant is (4-oxy-2-methylnaphtylimine)-2-methyl-1,4-naphthoquinone, which is a condensation reaction product of 4-amino-2-methyl-1-naphthol and menadione. 4-Amino-2-methyl-1-naphthol is a menadione analog. HCl salt is water-soluble and its parenteral administration requires no emulsifiers unlike fat-soluble phylloquinone for example, which is often in formulations with lecithin or glycocholic acid. HCl salt has been studied as a potential treatment for cancer as it prevents glycolysis in cancer cells, which provides them energy for growth. Thus it has been studied as potential food preservative. Parenterally given 1 mg/ml aqueous solutions and orally taken 4 mg tablets of the HCl salt have been available commercially.4-Amino-2-methyl-1-naphthol HCl salt has a mass of 209.57 G/mol. The HCl salt has been used as a medicine for vitamin K deficiency under tradenames such as Synkamin, which was sold by Parke-Davis, but has since been discontinued.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0337491 (4-Amino-2-methyl-1-naphthol)


  Mrv0541 05061306462D          

 13 14  0  0  0  0            999 V2000
    4.2868    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  7  1  1  0  0  0  0
  7  6  1  0  0  0  0
  8  4  2  0  0  0  0
  9  5  2  0  0  0  0
  9  8  1  0  0  0  0
 10  6  2  0  0  0  0
 10  8  1  0  0  0  0
 11  7  2  0  0  0  0
 11  9  1  0  0  0  0
 12 10  1  0  0  0  0
 13 11  1  0  0  0  0
M  END
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3D MOL for NP0337491 (4-Amino-2-methyl-1-naphthol)

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3D SDF for NP0337491 (4-Amino-2-methyl-1-naphthol)

  Mrv0541 05061306462D          

 13 14  0  0  0  0            999 V2000
    4.2868    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  7  1  1  0  0  0  0
  7  6  1  0  0  0  0
  8  4  2  0  0  0  0
  9  5  2  0  0  0  0
  9  8  1  0  0  0  0
 10  6  2  0  0  0  0
 10  8  1  0  0  0  0
 11  7  2  0  0  0  0
 11  9  1  0  0  0  0
 12 10  1  0  0  0  0
 13 11  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0337491

> <DATABASE_NAME>
NP-MRD

> <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

> <FORMULA>
C11H11NO

> <MOLECULAR_WEIGHT>
173.2111

> <EXACT_MASS>
173.084063979

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
18.99037274379453

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-amino-2-methylnaphthalen-1-ol

> <ALOGPS_LOGP>
2.03

> <JCHEM_LOGP>
2.343652686333333

> <ALOGPS_LOGS>
-2.49

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.380314691626822

> <JCHEM_PKA_STRONGEST_BASIC>
5.340598806699455

> <JCHEM_POLAR_SURFACE_AREA>
46.25

> <JCHEM_REFRACTIVITY>
54.23070000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.56e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-amino-2-methylnaphthalen-1-ol

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0337491 (4-Amino-2-methyl-1-naphthol)
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PDB for NP0337491 (4-Amino-2-methyl-1-naphthol)
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

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3D PDB for NP0337491 (4-Amino-2-methyl-1-naphthol)
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SMILES for NP0337491 (4-Amino-2-methyl-1-naphthol)
CC1=C(O)C2=CC=CC=C2C(N)=C1
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INCHI for NP0337491 (4-Amino-2-methyl-1-naphthol)
InChI=1S/C11H11NO/c1-7-6-10(12)8-4-2-3-5-9(8)11(7)13/h2-6,13H,12H2,1H3
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Synonyms
ValueSource
1-Naphthalenol, 4-amino-2-methyl-, hydrochlorideHMDB
1-Naphthol, 4-amino-2-methyl-, hydrochloride (8ci)HMDB
2-Methyl-4-amino-1-naphtholHMDB
2-Methyl-4-amino-1-naphthol hydrochlorideHMDB
4-Amino-2-methyl-1-naphthalenol, 9ciHMDB
4-Amino-2-methyl-1-naphthol hciHMDB
4-Amino-2-methylnaphthol hydrochlorideHMDB
4-Hydroxy-3-methyl-1-naphthylammonium chlorideHMDB
Synkamin hydrochlorideHMDB
Vitamin K5HMDB
Vitamin K5 hydrochlorideHMDB
4-Amino-2-methyl-1-naphthalenol, hydrochlorideMeSH
4-Amino-2-methyl-1-naphtholMeSH
Vitamin K5, hydrochlorideMeSH
Chemical FormulaC11H11NO
Average Mass173.2111 Da
Monoisotopic Mass173.08406 Da
IUPAC Name4-amino-2-methylnaphthalen-1-ol
Traditional Name4-amino-2-methylnaphthalen-1-ol
CAS Registry NumberNot Available
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 KeyUGQFCTZXVAPVCS-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
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.
KingdomOrganic compounds  
Super ClassBenzenoids  
ClassNaphthalenes  
Sub ClassNaphthols and derivatives  
Direct ParentNaphthols 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 FrameworkAromatic homopolycyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP2.03ALOGPS
logP2.34ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)10.38ChemAxon
pKa (Strongest Basic)5.34ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area46.25 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity54.23 m³·mol⁻¹ChemAxon
Polarizability18.99 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0032887  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB010869  
KNApSAcK IDNot Available
Chemspider ID6497  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link4-Amino-2-methyl-1-naphthol  
METLIN IDNot Available
PubChem Compound6754  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available