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Showing NP-Card for Sativol (NP0047716)

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Record Information
Version2.0
Created at2022-03-17 20:44:46 UTC
Updated at2022-03-17 20:44:46 UTC
NP-MRD IDNP0047716
Secondary Accession NumbersNone
Natural Product Identification
Common NameSativol
Description6Alpha-Hydroxymaackiain, also known as 6a-hydroxyinermin, belongs to the class of organic compounds known as pterocarpans. These are benzo-pyrano-furano-benzene compounds, containing the 6H-[1]benzofuro[3,2-c]chromene skeleton. They are derivatives of isoflavonoids. Thus, 6alpha-hydroxymaackiain is considered to be a flavonoid lipid molecule. 6Alpha-Hydroxymaackiain is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, 6alpha-Hydroxymaackiain has been detected, but not quantified in, several different foods, such as common pea, herbs and spices, pulses, and tea. This could make 6alpha-hydroxymaackiain a potential biomarker for the consumption of these foods.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0047716 (Sativol)


  Mrv0541 05061307192D          

 22 25  0  0  0  0            999 V2000
   -2.7328    1.2437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6087    0.8585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8754    1.2366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3435   -0.3244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1671   -0.2772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9538   -0.4116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6479    0.0344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1813    0.7906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1092    0.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5381    0.4596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2205   -0.0335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3855    1.0079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0855    1.1494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9328    0.3182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2618    1.1022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0145    1.7448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3811   -0.3437    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4565    1.8863    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4671    2.4345    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3618    0.5068    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4489   -0.3254    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1908    1.7920    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0  0  0  0
  5  4  2  0  0  0  0
  7  2  1  0  0  0  0
  7  6  2  0  0  0  0
  8  3  1  0  0  0  0
  9  4  1  0  0  0  0
 10  5  1  0  0  0  0
 11  6  1  0  0  0  0
 11  8  2  0  0  0  0
 12  8  1  0  0  0  0
 13 10  2  0  0  0  0
 14  9  1  0  0  0  0
 14 12  2  0  0  0  0
 15  9  2  0  0  0  0
 15 13  1  0  0  0  0
 16 12  1  0  0  0  0
 17  7  1  0  0  0  0
 18 13  1  0  0  0  0
 19 16  2  0  0  0  0
 20  1  1  0  0  0  0
 20 10  1  0  0  0  0
 21 11  1  0  0  0  0
 21 14  1  0  0  0  0
 22 15  1  0  0  0  0
 22 16  1  0  0  0  0
M  END
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3D MOL for NP0047716 (Sativol)

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3D SDF for NP0047716 (Sativol)

  Mrv0541 05061307192D          

 22 25  0  0  0  0            999 V2000
   -2.7328    1.2437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6087    0.8585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8754    1.2366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3435   -0.3244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1671   -0.2772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9538   -0.4116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6479    0.0344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1813    0.7906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1092    0.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5381    0.4596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2205   -0.0335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3855    1.0079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0855    1.1494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9328    0.3182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2618    1.1022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0145    1.7448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3811   -0.3437    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4565    1.8863    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4671    2.4345    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3618    0.5068    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4489   -0.3254    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1908    1.7920    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0  0  0  0
  5  4  2  0  0  0  0
  7  2  1  0  0  0  0
  7  6  2  0  0  0  0
  8  3  1  0  0  0  0
  9  4  1  0  0  0  0
 10  5  1  0  0  0  0
 11  6  1  0  0  0  0
 11  8  2  0  0  0  0
 12  8  1  0  0  0  0
 13 10  2  0  0  0  0
 14  9  1  0  0  0  0
 14 12  2  0  0  0  0
 15  9  2  0  0  0  0
 15 13  1  0  0  0  0
 16 12  1  0  0  0  0
 17  7  1  0  0  0  0
 18 13  1  0  0  0  0
 19 16  2  0  0  0  0
 20  1  1  0  0  0  0
 20 10  1  0  0  0  0
 21 11  1  0  0  0  0
 21 14  1  0  0  0  0
 22 15  1  0  0  0  0
 22 16  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0047716

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(O)C2=C(C=C1)C1=C(C3=C(O1)C=C(O)C=C3)C(=O)O2

> <INCHI_IDENTIFIER>
InChI=1S/C16H10O6/c1-20-10-5-4-9-14-12(16(19)22-15(9)13(10)18)8-3-2-7(17)6-11(8)21-14/h2-6,17-18H,1H3

> <INCHI_KEY>
YLRNDYZYIUVEDH-UHFFFAOYSA-N

> <FORMULA>
C16H10O6

> <MOLECULAR_WEIGHT>
298.247

> <EXACT_MASS>
298.047738052

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
29.444644119224495

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6,14-dihydroxy-5-methoxy-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(10),2(7),3,5,11(16),12,14-heptaen-9-one

> <ALOGPS_LOGP>
2.48

> <JCHEM_LOGP>
2.889650056666666

> <ALOGPS_LOGS>
-2.98

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.412767405241457

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.084498110042784

> <JCHEM_PKA_STRONGEST_BASIC>
-3.5074163181426234

> <JCHEM_POLAR_SURFACE_AREA>
89.13000000000001

> <JCHEM_REFRACTIVITY>
76.0827

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.10e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6,14-dihydroxy-5-methoxy-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(10),2(7),3,5,11(16),12,14-heptaen-9-one

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0047716 (Sativol)
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PDB for NP0047716 (Sativol)
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      -5.101   2.322   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.736   1.603   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.367   2.308   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.641  -0.606   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.179  -0.517   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.514  -0.768   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.809   0.064   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.072   1.476   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.204   0.682   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.871   0.858   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.145  -0.063   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.586   1.881   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.026   2.146   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.741   0.594   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.489   2.057   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.894   3.257   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       8.178  -0.642   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -2.719   3.521   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       2.739   4.544   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -4.409   0.946   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       2.705  -0.607   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       0.356   3.345   0.000  0.00  0.00           O+0
CONECT    1   20                                                            
CONECT    2    3    7                                                       
CONECT    3    2    8                                                       
CONECT    4    5    9                                                       
CONECT    5    4   10                                                       
CONECT    6    7   11                                                       
CONECT    7    2    6   17                                                  
CONECT    8    3   11   12                                                  
CONECT    9    4   14   15                                                  
CONECT   10    5   13   20                                                  
CONECT   11    6    8   21                                                  
CONECT   12    8   14   16                                                  
CONECT   13   10   15   18                                                  
CONECT   14    9   12   21                                                  
CONECT   15    9   13   22                                                  
CONECT   16   12   19   22                                                  
CONECT   17    7                                                            
CONECT   18   13                                                            
CONECT   19   16                                                            
CONECT   20    1   10                                                       
CONECT   21   11   14                                                       
CONECT   22   15   16                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   50    0
END

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3D PDB for NP0047716 (Sativol)
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SMILES for NP0047716 (Sativol)
COC1=C(O)C2=C(C=C1)C1=C(C3=C(O1)C=C(O)C=C3)C(=O)O2
Download
INCHI for NP0047716 (Sativol)
InChI=1S/C16H10O6/c1-20-10-5-4-9-14-12(16(19)22-15(9)13(10)18)8-3-2-7(17)6-11(8)21-14/h2-6,17-18H,1H3
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View in JSmol
Synonyms
ValueSource
6a-HydroxymaackiainGenerator
6Α-hydroxymaackiainGenerator
3,6a-Dihydroxy-8,9-methylenedioxypterocarpanHMDB
6a-HydroxyinerminHMDB
4,9-Dihydroxy-3-methoxycoumestanHMDB
8,12-Dihydroxy-7-methoxycoumestanHMDB
Chemical FormulaC16H10O6
Average Mass298.2470 Da
Monoisotopic Mass298.04774 Da
IUPAC Name6,14-dihydroxy-5-methoxy-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(10),2(7),3,5,11(16),12,14-heptaen-9-one
Traditional Name6,14-dihydroxy-5-methoxy-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(10),2(7),3,5,11(16),12,14-heptaen-9-one
CAS Registry Number7331-58-0
SMILES
COC1=C(O)C2=C(C=C1)C1=C(C3=C(O1)C=C(O)C=C3)C(=O)O2
InChI Identifier
InChI=1S/C16H10O6/c1-20-10-5-4-9-14-12(16(19)22-15(9)13(10)18)8-3-2-7(17)6-11(8)21-14/h2-6,17-18H,1H3
InChI KeyYLRNDYZYIUVEDH-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Crocus sativusFooDB
Medicago sativaFooDB
Chemical Taxonomy
Description Belongs to the class of organic compounds known as pterocarpans. These are benzo-pyrano-furano-benzene compounds, containing the  6H-[1]benzofuro[3,2-c]chromene skeleton. They are derivatives of isoflavonoids.
KingdomOrganic compounds  
Super ClassPhenylpropanoids and polyketides  
ClassIsoflavonoids  
Sub ClassFuranoisoflavonoids  
Direct ParentPterocarpans  
Alternative Parents
Substituents
  • Pterocarpan
    • 

  • Isoflavanol
    • 

  • Isoflavan
    • 

  • Chromane
    • 

  • 1-benzopyran
    • 

  • Benzopyran
    • 

  • Coumaran
    • 

  • Benzodioxole
    • 

  • Benzofuran
    • 

  • 1-hydroxy-2-unsubstituted benzenoid
    • 

  • Alkyl aryl ether
    • 

  • Benzenoid
    • 

  • Tertiary alcohol
    • 

  • Acetal
    • 

  • Oxacycle
    • 

  • Organoheterocyclic compound
    • 

  • Ether
    • 

  • Hydrocarbon derivative
    • 

  • Alcohol
    • 

  • Organic oxygen compound
    • 

  • Organooxygen compound
    • 

  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
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
logP2.48ALOGPS
logP2.89ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)9.08ChemAxon
pKa (Strongest Basic)-3.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area89.13 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity76.08 m³·mol⁻¹ChemAxon
Polarizability29.44 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0033720  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB011839  
KNApSAcK IDC00009677  
Chemspider ID24785132  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound44257487  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available