NP-MRD: Showing NP-Card for 3',8-Dihydroxyvestitol (NP0138757)

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Record Information

Version

2.0

Created at

2022-06-29 18:34:51 UTC

Updated at

2022-06-29 18:34:51 UTC

NP-MRD ID

NP0138757

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3',8-Dihydroxyvestitol

Description

(3R)-3',8-dihydroxyvestitol belongs to the class of organic compounds known as 3'-hydroxy,4'-methoxyisoflavonoids. These are isoflavonoids carrying a methoxy group attached to the C4' atom, as well as a hydroxyl group at the C3'-position of the isoflavonoid backbone. 3',8-Dihydroxyvestitol is found in Dalbergia odorifera. Thus, (3R)-3',8-dihydroxyvestitol is considered to be a flavonoid lipid molecule (3r)-3',8-dihydroxyvestitol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 38 40  0  0  0  0  0  0  0  0999 V2000
    6.1467    0.8649   -0.0656 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1359    0.0144   -0.4533 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8103    0.0212   -0.1692 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2669    0.9822    0.6397 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9104    0.9575    0.9077 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1198   -0.0136    0.3728 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3281   -0.0464    0.5762 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8665    0.7178    1.7357 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3095    0.7829    1.6326 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9947    0.3333    0.5178 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3623    0.1934   -0.6984 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9942   -0.2472   -1.8390 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3381   -0.5715   -1.7781 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9994   -0.4419   -0.5719 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3392   -0.7626   -0.4988 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3374    0.0024    0.5560 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9753    0.1415    1.7874 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9220    0.5429   -0.7437 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6897   -0.9918   -0.4539 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8418   -1.9587   -0.9703 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0122   -0.9734   -0.7192 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6233   -1.9345   -1.5409 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1576    0.3870   -0.1361 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2427    1.8131   -0.6445 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9830    1.1928    0.9928 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8847    1.7703    1.0812 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4899    1.7230    1.5526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7117   -1.1004    0.6244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7032    0.0654    2.6467 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4261    1.6833    1.9490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5020   -0.3571   -2.7952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8492   -0.9281   -2.6865 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8757   -0.6929    0.3607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5202    0.4489    2.6149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8728    1.6559   -0.7047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3664    0.1100   -1.5714 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1497   -2.7042   -1.5591 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1293   -2.6798   -1.9725 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 18  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 16 17  1  0
  6 19  1  0
 19 20  1  0
 19 21  2  0
 21 22  1  0
 21  3  1  0
 18  7  1  0
 16 10  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  5 27  1  0
  7 28  1  1
  8 29  1  0
  8 30  1  0
 18 35  1  0
 18 36  1  0
 12 31  1  0
 13 32  1  0
 15 33  1  0
 17 34  1  0
 20 37  1  0
 22 38  1  0
M  END


  Mrv1533004171514562D          

 22 24  0  0  0  0            999 V2000
   -4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    1.2375    0.0000 O   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
   -2.1434    1.2375    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
   -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 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
    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
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 O   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
   -2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2375    0.0000 O   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
   -3.5724   -0.4125    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  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
  7 12  1  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
 15 16  1  0  0  0  0
 15 17  2  0  0  0  0
 10 17  1  0  0  0  0
 17 18  1  0  0  0  0
  6 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
  3 21  1  0  0  0  0
 21 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0138757

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C(C2COC3=C(C2)C=CC(O)=C3O)C(O)=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C16H16O6/c1-21-12-5-3-10(13(18)15(12)20)9-6-8-2-4-11(17)14(19)16(8)22-7-9/h2-5,9,17-20H,6-7H2,1H3

> <INCHI_KEY>
BPAJYCPZCVWTTL-UHFFFAOYSA-N

> <FORMULA>
C16H16O6

> <MOLECULAR_WEIGHT>
304.298

> <EXACT_MASS>
304.094688235

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
30.589691499240974

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-(2,3-dihydroxy-4-methoxyphenyl)-3,4-dihydro-2H-1-benzopyran-7,8-diol

> <ALOGPS_LOGP>
1.77

> <JCHEM_LOGP>
2.426875968333333

> <ALOGPS_LOGS>
-3.32

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.110501461471022

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.506041498023066

> <JCHEM_PKA_STRONGEST_BASIC>
-4.607588781766819

> <JCHEM_POLAR_SURFACE_AREA>
99.38000000000001

> <JCHEM_REFRACTIVITY>
79.3852

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.44e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3R)-3',8-dihydroxyvestitol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  C   UNK     0      -8.002   1.540   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -6.668   2.310   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -5.335   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -5.335   0.000   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -6.668  -0.770   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   21                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   19                                                  
CONECT    7    6    8   12                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   17                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11    7                                                       
CONECT   13   11   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   10   18                                                  
CONECT   18   17                                                            
CONECT   19    6   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19    3   22                                                  
CONECT   22   21                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₆H₁₆O₆

Average Mass

304.2980 Da

Monoisotopic Mass

304.09469 Da

IUPAC Name

3-(2,3-dihydroxy-4-methoxyphenyl)-3,4-dihydro-2H-1-benzopyran-7,8-diol

Traditional Name

(3R)-3',8-dihydroxyvestitol

CAS Registry Number

122587-87-5

SMILES

COC1=CC=C(C2COC3=C(C2)C=CC(O)=C3O)C(O)=C1O

InChI Identifier

InChI=1S/C16H16O6/c1-21-12-5-3-10(13(18)15(12)20)9-6-8-2-4-11(17)14(19)16(8)22-7-9/h2-5,9,17-20H,6-7H2,1H3

InChI Key

BPAJYCPZCVWTTL-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Dalbergia odorifera	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 3'-hydroxy,4'-methoxyisoflavonoids. These are isoflavonoids carrying a methoxy group attached to the C4' atom, as well as a hydroxyl group at the C3'-position of the isoflavonoid backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

O-methylated isoflavonoids

Direct Parent

3'-hydroxy,4'-methoxyisoflavonoids

Alternative Parents

Substituents

3'-hydroxy,4'-methoxyisoflavonoid
Hydroxyisoflavonoid
Isoflavanol
Isoflavan
Chromane
Benzopyran
Methoxyphenol
1-benzopyran
Phenoxy compound
Anisole
Catechol
Methoxybenzene
Phenol ether
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Benzenoid
Monocyclic benzene moiety
Oxacycle
Ether
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxygen compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Isoflavans (LMPK12080042 )

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	1.77	ALOGPS
logP	2.43	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	9.51	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	99.38 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	79.39 m³·mol⁻¹	ChemAxon
Polarizability	30.59 Å³	ChemAxon
Number of Rings	3	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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14353659

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 3',8-Dihydroxyvestitol (NP0138757)

MOL for NP0138757 (3',8-Dihydroxyvestitol)

3D MOL for NP0138757 (3',8-Dihydroxyvestitol)

3D SDF for NP0138757 (3',8-Dihydroxyvestitol)

3D-SDF for NP0138757 (3',8-Dihydroxyvestitol)

PDB for NP0138757 (3',8-Dihydroxyvestitol)

3D PDB for NP0138757 (3',8-Dihydroxyvestitol)

SMILES for NP0138757 (3',8-Dihydroxyvestitol)

INCHI for NP0138757 (3',8-Dihydroxyvestitol)

Structure for NP0138757 (3',8-Dihydroxyvestitol)

3D Structure for NP0138757 (3',8-Dihydroxyvestitol)