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Showing NP-Card for 5-hydroxy-3-(2-hydroxy-3-methylbut-3-en-1-yl)-2,8-dimethoxynaphthalene-1,4-dione (NP0283413)

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Record Information
Version2.0
Created at2022-09-09 10:39:55 UTC
Updated at2022-09-09 10:39:56 UTC
NP-MRD IDNP0283413
Secondary Accession NumbersNone
Natural Product Identification
Common Name5-hydroxy-3-(2-hydroxy-3-methylbut-3-en-1-yl)-2,8-dimethoxynaphthalene-1,4-dione
Description5-Hydroxy-3-(2-hydroxy-3-methylbut-3-en-1-yl)-2,8-dimethoxy-1,4-dihydronaphthalene-1,4-dione belongs to the class of organic compounds known as vitamin k compounds. These are quinone lipids containing a methylated naphthoquinone ring structure, and vary in the aliphatic side chain attached at the 3-position. 5-hydroxy-3-(2-hydroxy-3-methylbut-3-en-1-yl)-2,8-dimethoxynaphthalene-1,4-dione is found in Lantana involucrata. 5-Hydroxy-3-(2-hydroxy-3-methylbut-3-en-1-yl)-2,8-dimethoxy-1,4-dihydronaphthalene-1,4-dione is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0283413 (5-hydroxy-3-(2-hydroxy-3-methylbut-3-en-1-yl)-2,8-dimethoxynaphthalene-1,4-dione)


  Mrv1533004151519402D          

 23 24  0  0  0  0            999 V2000
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 O   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   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    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    0.0000    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
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    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
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    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
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
  4 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 18 21  2  0  0  0  0
 13 21  1  0  0  0  0
 21 22  1  0  0  0  0
  3 22  1  0  0  0  0
 22 23  2  0  0  0  0
M  END
Download

3D MOL for NP0283413 (5-hydroxy-3-(2-hydroxy-3-methylbut-3-en-1-yl)-2,8-dimethoxynaphthalene-1,4-dione)

Download
3D SDF for NP0283413 (5-hydroxy-3-(2-hydroxy-3-methylbut-3-en-1-yl)-2,8-dimethoxynaphthalene-1,4-dione)

  Mrv1533004151519402D          

 23 24  0  0  0  0            999 V2000
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 O   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   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    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    0.0000    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
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    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
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    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
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
  4 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 18 21  2  0  0  0  0
 13 21  1  0  0  0  0
 21 22  1  0  0  0  0
  3 22  1  0  0  0  0
 22 23  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0283413

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C2C(=O)C(OC)=C(CC(O)C(C)=C)C(=O)C2=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C17H18O6/c1-8(2)11(19)7-9-15(20)13-10(18)5-6-12(22-3)14(13)16(21)17(9)23-4/h5-6,11,18-19H,1,7H2,2-4H3

> <INCHI_KEY>
IGQHQXQDGDLBTH-UHFFFAOYSA-N

> <FORMULA>
C17H18O6

> <MOLECULAR_WEIGHT>
318.325

> <EXACT_MASS>
318.1103383

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
41

> <JCHEM_AVERAGE_POLARIZABILITY>
32.351139419112386

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-hydroxy-3-(2-hydroxy-3-methylbut-3-en-1-yl)-2,8-dimethoxy-1,4-dihydronaphthalene-1,4-dione

> <ALOGPS_LOGP>
1.70

> <JCHEM_LOGP>
1.7150697739999994

> <ALOGPS_LOGS>
-2.74

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.549147893585136

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.67174142131482

> <JCHEM_PKA_STRONGEST_BASIC>
-2.996004246279882

> <JCHEM_POLAR_SURFACE_AREA>
93.06

> <JCHEM_REFRACTIVITY>
85.3476

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.78e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-hydroxy-3-(2-hydroxy-3-methylbut-3-en-1-yl)-2,8-dimethoxynaphthalene-1,4-dione

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0283413 (5-hydroxy-3-(2-hydroxy-3-methylbut-3-en-1-yl)-2,8-dimethoxynaphthalene-1,4-dione)
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PDB for NP0283413 (5-hydroxy-3-(2-hydroxy-3-methylbut-3-en-1-yl)-2,8-dimethoxynaphthalene-1,4-dione)
HEADER    PROTEIN                                 15-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   15-APR-15         0                                  
HETATM    1  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -1.334  -2.310   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667   0.000   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  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   22                                                  
CONECT    4    3    5   11                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    4   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   21                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   21                                                  
CONECT   19   18   20                                                       
CONECT   20   19                                                            
CONECT   21   18   13   22                                                  
CONECT   22   21    3   23                                                  
CONECT   23   22                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   48    0
END

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3D PDB for NP0283413 (5-hydroxy-3-(2-hydroxy-3-methylbut-3-en-1-yl)-2,8-dimethoxynaphthalene-1,4-dione)
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SMILES for NP0283413 (5-hydroxy-3-(2-hydroxy-3-methylbut-3-en-1-yl)-2,8-dimethoxynaphthalene-1,4-dione)
COC1=C2C(=O)C(OC)=C(CC(O)C(C)=C)C(=O)C2=C(O)C=C1
Download
INCHI for NP0283413 (5-hydroxy-3-(2-hydroxy-3-methylbut-3-en-1-yl)-2,8-dimethoxynaphthalene-1,4-dione)
InChI=1S/C17H18O6/c1-8(2)11(19)7-9-15(20)13-10(18)5-6-12(22-3)14(13)16(21)17(9)23-4/h5-6,11,18-19H,1,7H2,2-4H3
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SynonymsNot Available
Chemical FormulaC17H18O6
Average Mass318.3250 Da
Monoisotopic Mass318.11034 Da
IUPAC Name5-hydroxy-3-(2-hydroxy-3-methylbut-3-en-1-yl)-2,8-dimethoxy-1,4-dihydronaphthalene-1,4-dione
Traditional Name5-hydroxy-3-(2-hydroxy-3-methylbut-3-en-1-yl)-2,8-dimethoxynaphthalene-1,4-dione
CAS Registry NumberNot Available
SMILES
COC1=C2C(=O)C(OC)=C(CC(O)C(C)=C)C(=O)C2=C(O)C=C1
InChI Identifier
InChI=1S/C17H18O6/c1-8(2)11(19)7-9-15(20)13-10(18)5-6-12(22-3)14(13)16(21)17(9)23-4/h5-6,11,18-19H,1,7H2,2-4H3
InChI KeyIGQHQXQDGDLBTH-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Lantana involucrataLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as vitamin k compounds. These are quinone lipids containing a methylated naphthoquinone ring structure, and vary in the aliphatic side chain attached at the 3-position.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassPrenol lipids  
Sub ClassQuinone and hydroquinone lipids  
Direct ParentVitamin K compounds  
Alternative Parents
Substituents
  • Naphthoquinone
    • 

  • Naphthalene
    • 

  • Anisole
    • 

  • Phenol ether
    • 

  • Aryl ketone
    • 

  • Quinone
    • 

  • 1-hydroxy-2-unsubstituted benzenoid
    • 

  • Alkyl aryl ether
    • 

  • Phenol
    • 

  • Benzenoid
    • 

  • Vinylogous ester
    • 

  • Vinylogous acid
    • 

  • Ketone
    • 

  • Secondary alcohol
    • 

  • Ether
    • 

  • Organooxygen compound
    • 

  • Alcohol
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxide
    • 

  • Organic oxygen compound
    • 

  • 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
logP1.7ALOGPS
logP1.72ChemAxon
logS-2.7ALOGPS
pKa (Strongest Acidic)8.67ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area93.06 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity85.35 m³·mol⁻¹ChemAxon
Polarizability32.35 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound11359041  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]