NP-MRD: Showing NP-Card for 2-Methyl-1,4-naphthalenediol bis(dihydrogen phosphate) (NP0336623)

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Record Information

Version

2.0

Created at

2024-09-11 07:07:54 UTC

Updated at

2024-09-11 07:07:55 UTC

NP-MRD ID

NP0336623

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-Methyl-1,4-naphthalenediol bis(dihydrogen phosphate)

Description

2-Methyl-1,4-naphthalenediol bis(dihydrogen phosphate), also known as menadiol diphosphate or synkavite, belongs to the class of organic compounds known as naphthalenes. Naphthalenes are compounds containing a naphthalene moiety, which consists of two fused benzene rings. 2-Methyl-1,4-naphthalenediol bis(dihydrogen phosphate) is a drug. 2-Methyl-1,4-naphthalenediol bis(dihydrogen phosphate) is a moderately acidic compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061306392D          

 21 22  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
    1.4289   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5559   -1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7309    0.3020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5559    4.4270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7309    2.9980    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 O   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
    2.1434   -0.4125    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    3.7125    0.0000 P   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
 18 10  1  0  0  0  0
 19 11  1  0  0  0  0
 20 12  1  0  0  0  0
 20 13  1  0  0  0  0
 20 14  2  0  0  0  0
 20 18  1  0  0  0  0
 21 15  1  0  0  0  0
 21 16  1  0  0  0  0
 21 17  2  0  0  0  0
 21 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0336623

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=C(OP(O)(O)=O)C2=CC=CC=C2C(OP(O)(O)=O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C11H12O8P2/c1-7-6-10(18-20(12,13)14)8-4-2-3-5-9(8)11(7)19-21(15,16)17/h2-6H,1H3,(H2,12,13,14)(H2,15,16,17)

> <INCHI_KEY>
JTNHOVZOOVVGHI-UHFFFAOYSA-N

> <FORMULA>
C11H12O8P2

> <MOLECULAR_WEIGHT>
334.1557

> <EXACT_MASS>
334.000740384

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
27.428663525030892

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
{[2-methyl-4-(phosphonooxy)naphthalen-1-yl]oxy}phosphonic acid

> <ALOGPS_LOGP>
0.84

> <JCHEM_LOGP>
1.5612830273333334

> <ALOGPS_LOGS>
-2.59

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-4

> <JCHEM_PKA>
2.075618569922639

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.4713832235792101

> <JCHEM_POLAR_SURFACE_AREA>
133.52

> <JCHEM_REFRACTIVITY>
73.257

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.54e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[2-methyl-4-(phosphonooxy)naphthalen-1-yl]oxyphosphonic acid

> <JCHEM_VEBER_RULE>
0

$$$$

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  O   UNK     0       2.667  -1.540   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       4.771  -2.104   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       3.231   0.564   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       2.667   7.700   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       4.771   8.264   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       3.231   5.596   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       5.335   0.000   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       5.335   6.160   0.000  0.00  0.00           O+0
HETATM   20  P   UNK     0       4.001  -0.770   0.000  0.00  0.00           P+0
HETATM   21  P   UNK     0       4.001   6.930   0.000  0.00  0.00           P+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   18                                                  
CONECT   11    7    9   19                                                  
CONECT   12   20                                                            
CONECT   13   20                                                            
CONECT   14   20                                                            
CONECT   15   21                                                            
CONECT   16   21                                                            
CONECT   17   21                                                            
CONECT   18   10   20                                                       
CONECT   19   11   21                                                       
CONECT   20   12   13   14   18                                             
CONECT   21   15   16   17   19                                             
MASTER        0    0    0    0    0    0    0    0   21    0   44    0
END

View in JSmol

Synonyms

Value	Source
2-Methyl-1,4-naphthalenediol bis(dihydrogen phosphoric acid)	Generator
1,4-Naphthalenediol, 2-methyl-, bis(dihydrogen phosphate)	HMDB
131-13-5 (Tetra-hydrochloride salt)	HMDB
Menadiol diphosphate	HMDB
2-Methyl-1,4-naphthoquinol	HMDB
Synkavite	HMDB
Menadiol diphosphate ion	HMDB
Menadiol diphosphate, monosodium salt	HMDB
Menadiol, (-1)-ion	HMDB
2-Methyl-1,4-naphthohydroquinone	HMDB
Dihydrovitamin K3	HMDB
Menadiol diphosphate, tetrasodium salt	HMDB
Menadiol, monopotassium salt	HMDB
Naphtadon	HMDB
Synkavit	HMDB
Menadiol	HMDB
Reduced menadione	HMDB
{[3-methyl-4-(phosphonooxy)naphthalen-1-yl]oxy}phosphonate	Generator

Chemical Formula

C₁₁H₁₂O₈P₂

Average Mass

334.1557 Da

Monoisotopic Mass

334.00074 Da

IUPAC Name

{[2-methyl-4-(phosphonooxy)naphthalen-1-yl]oxy}phosphonic acid

Traditional Name

[2-methyl-4-(phosphonooxy)naphthalen-1-yl]oxyphosphonic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C11H12O8P2/c1-7-6-10(18-20(12,13)14)8-4-2-3-5-9(8)11(7)19-21(15,16)17/h2-6H,1H3,(H2,12,13,14)(H2,15,16,17)

InChI Key

JTNHOVZOOVVGHI-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthalenes. Naphthalenes are compounds containing a naphthalene moiety, which consists of two fused benzene rings.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Naphthalenes

Sub Class

Not Available

Direct Parent

Naphthalenes

Alternative Parents

Substituents

Aryl phosphate
Aryl phosphomonoester
Naphthalene
Phosphoric acid ester
Organic phosphoric acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental 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

Predicted Properties

Property	Value	Source
logP	0.84	ALOGPS
logP	1.56	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	1.47	ChemAxon
Physiological Charge	-4	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	133.52 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	73.26 m³·mol⁻¹	ChemAxon
Polarizability	27.43 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

External Links

HMDB ID

HMDB0032721

DrugBank ID

DBSALT000878

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB010682

KNApSAcK ID

Not Available

Chemspider ID

8238

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

8556

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 2-Methyl-1,4-naphthalenediol bis(dihydrogen phosphate) (NP0336623)

MOL for NP0336623 (2-Methyl-1,4-naphthalenediol bis(dihydrogen phosphate))

3D MOL for NP0336623 (2-Methyl-1,4-naphthalenediol bis(dihydrogen phosphate))

3D SDF for NP0336623 (2-Methyl-1,4-naphthalenediol bis(dihydrogen phosphate))

3D-SDF for NP0336623 (2-Methyl-1,4-naphthalenediol bis(dihydrogen phosphate))

PDB for NP0336623 (2-Methyl-1,4-naphthalenediol bis(dihydrogen phosphate))

3D PDB for NP0336623 (2-Methyl-1,4-naphthalenediol bis(dihydrogen phosphate))

SMILES for NP0336623 (2-Methyl-1,4-naphthalenediol bis(dihydrogen phosphate))

INCHI for NP0336623 (2-Methyl-1,4-naphthalenediol bis(dihydrogen phosphate))

Structure for NP0336623 (2-Methyl-1,4-naphthalenediol bis(dihydrogen phosphate))

3D Structure for NP0336623 (2-Methyl-1,4-naphthalenediol bis(dihydrogen phosphate))