NP-MRD: Showing NP-Card for (2r)-7-hydroxy-8-(3-hydroxy-3-methylbut-1-en-1-yl)-2-(4-hydroxyphenyl)-5-methoxy-2,3-dihydro-1-benzopyran-4-one (NP0224843)

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Record Information

Version

2.0

Created at

2022-09-06 03:23:29 UTC

Updated at

2022-09-06 03:23:30 UTC

NP-MRD ID

NP0224843

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2r)-7-hydroxy-8-(3-hydroxy-3-methylbut-1-en-1-yl)-2-(4-hydroxyphenyl)-5-methoxy-2,3-dihydro-1-benzopyran-4-one

Description

(2R)-7-hydroxy-8-(3-hydroxy-3-methylbut-1-en-1-yl)-2-(4-hydroxyphenyl)-5-methoxy-3,4-dihydro-2H-1-benzopyran-4-one belongs to the class of organic compounds known as 5-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C5 atom of the flavonoid backbone. (2r)-7-hydroxy-8-(3-hydroxy-3-methylbut-1-en-1-yl)-2-(4-hydroxyphenyl)-5-methoxy-2,3-dihydro-1-benzopyran-4-one is found in Tephrosia candida. Based on a literature review very few articles have been published on (2R)-7-hydroxy-8-(3-hydroxy-3-methylbut-1-en-1-yl)-2-(4-hydroxyphenyl)-5-methoxy-3,4-dihydro-2H-1-benzopyran-4-one.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309062205232D          

 27 29  0  0  1  0            999 V2000
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 O   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 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1105   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5395   -3.7125    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
    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
    2.1434   -1.2375    0.0000 C   0  0  2  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
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    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
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    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
  5  7  2  0  0  0  0
  8  7  1  4  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 10 13  1  0  0  0  0
  7 14  1  0  0  0  0
 14 15  2  0  0  0  0
  3 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  6  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  2  0  0  0  0
 20 26  1  0  0  0  0
 19 27  1  0  0  0  0
 14 27  1  0  0  0  0
M  END


  Mrv1652309062205232D          

 27 29  0  0  1  0            999 V2000
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 O   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 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1105   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5395   -3.7125    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
    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
    2.1434   -1.2375    0.0000 C   0  0  2  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
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    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
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    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
  5  7  2  0  0  0  0
  8  7  1  4  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 10 13  1  0  0  0  0
  7 14  1  0  0  0  0
 14 15  2  0  0  0  0
  3 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  6  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  2  0  0  0  0
 20 26  1  0  0  0  0
 19 27  1  0  0  0  0
 14 27  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0224843

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(O)=C(C=CC(C)(C)O)C2=C1C(=O)C[C@@H](O2)C1=CC=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C21H22O6/c1-21(2,25)9-8-14-15(23)10-18(26-3)19-16(24)11-17(27-20(14)19)12-4-6-13(22)7-5-12/h4-10,17,22-23,25H,11H2,1-3H3/t17-/m1/s1

> <INCHI_KEY>
UQJDHMKAJSKDGS-QGZVFWFLSA-N

> <FORMULA>
C21H22O6

> <MOLECULAR_WEIGHT>
370.401

> <EXACT_MASS>
370.141638428

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
49

> <JCHEM_AVERAGE_POLARIZABILITY>
38.89914696453972

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R)-7-hydroxy-8-(3-hydroxy-3-methylbut-1-en-1-yl)-2-(4-hydroxyphenyl)-5-methoxy-3,4-dihydro-2H-1-benzopyran-4-one

> <JCHEM_LOGP>
2.870719705333333

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.480059217373213

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.753756406119146

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7954040128049886

> <JCHEM_POLAR_SURFACE_AREA>
96.22

> <JCHEM_REFRACTIVITY>
101.96360000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2R)-7-hydroxy-8-(3-hydroxy-3-methylbut-1-en-1-yl)-2-(4-hydroxyphenyl)-5-methoxy-2,3-dihydro-1-benzopyran-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       0.000  -0.000   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      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -2.667  -3.080   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.334  -8.470   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.206  -6.930   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -2.874  -6.930   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       9.336  -5.390   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   15                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   14                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12   13                                             
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13   10                                                            
CONECT   14    7   15   27                                                  
CONECT   15   14    3   16                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20   27                                                  
CONECT   20   19   21   26                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   20                                                       
CONECT   27   19   14                                                       
MASTER        0    0    0    0    0    0    0    0   27    0   58    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₁H₂₂O₆

Average Mass

370.4010 Da

Monoisotopic Mass

370.14164 Da

IUPAC Name

(2R)-7-hydroxy-8-(3-hydroxy-3-methylbut-1-en-1-yl)-2-(4-hydroxyphenyl)-5-methoxy-3,4-dihydro-2H-1-benzopyran-4-one

Traditional Name

(2R)-7-hydroxy-8-(3-hydroxy-3-methylbut-1-en-1-yl)-2-(4-hydroxyphenyl)-5-methoxy-2,3-dihydro-1-benzopyran-4-one

CAS Registry Number

Not Available

SMILES

COC1=CC(O)=C(C=CC(C)(C)O)C2=C1C(=O)C[C@@H](O2)C1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C21H22O6/c1-21(2,25)9-8-14-15(23)10-18(26-3)19-16(24)11-17(27-20(14)19)12-4-6-13(22)7-5-12/h4-10,17,22-23,25H,11H2,1-3H3/t17-/m1/s1

InChI Key

UQJDHMKAJSKDGS-QGZVFWFLSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Tephrosia candida	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 5-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C5 atom of the flavonoid backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

O-methylated flavonoids

Direct Parent

5-O-methylated flavonoids

Alternative Parents

Substituents

5-methoxyflavonoid-skeleton
Hydroxyflavonoid
Flavanone
7-hydroxyflavonoid
4'-hydroxyflavonoid
Flavan
Chromone
1-benzopyran
Benzopyran
Chromane
Aryl alkyl ketone
Aryl ketone
Styrene
Anisole
1-hydroxy-2-unsubstituted benzenoid
Phenol
Alkyl aryl ether
Benzenoid
Monocyclic benzene moiety
Tertiary alcohol
Ketone
Oxacycle
Organoheterocyclic compound
Ether
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic 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	2.87	ChemAxon
pKa (Strongest Acidic)	7.75	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	96.22 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	101.96 m³·mol⁻¹	ChemAxon
Polarizability	38.9 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

163019860

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2r)-7-hydroxy-8-(3-hydroxy-3-methylbut-1-en-1-yl)-2-(4-hydroxyphenyl)-5-methoxy-2,3-dihydro-1-benzopyran-4-one (NP0224843)

MOL for NP0224843 ((2r)-7-hydroxy-8-(3-hydroxy-3-methylbut-1-en-1-yl)-2-(4-hydroxyphenyl)-5-methoxy-2,3-dihydro-1-benzopyran-4-one)

3D MOL for NP0224843 ((2r)-7-hydroxy-8-(3-hydroxy-3-methylbut-1-en-1-yl)-2-(4-hydroxyphenyl)-5-methoxy-2,3-dihydro-1-benzopyran-4-one)

3D SDF for NP0224843 ((2r)-7-hydroxy-8-(3-hydroxy-3-methylbut-1-en-1-yl)-2-(4-hydroxyphenyl)-5-methoxy-2,3-dihydro-1-benzopyran-4-one)

3D-SDF for NP0224843 ((2r)-7-hydroxy-8-(3-hydroxy-3-methylbut-1-en-1-yl)-2-(4-hydroxyphenyl)-5-methoxy-2,3-dihydro-1-benzopyran-4-one)

PDB for NP0224843 ((2r)-7-hydroxy-8-(3-hydroxy-3-methylbut-1-en-1-yl)-2-(4-hydroxyphenyl)-5-methoxy-2,3-dihydro-1-benzopyran-4-one)

3D PDB for NP0224843 ((2r)-7-hydroxy-8-(3-hydroxy-3-methylbut-1-en-1-yl)-2-(4-hydroxyphenyl)-5-methoxy-2,3-dihydro-1-benzopyran-4-one)

SMILES for NP0224843 ((2r)-7-hydroxy-8-(3-hydroxy-3-methylbut-1-en-1-yl)-2-(4-hydroxyphenyl)-5-methoxy-2,3-dihydro-1-benzopyran-4-one)

INCHI for NP0224843 ((2r)-7-hydroxy-8-(3-hydroxy-3-methylbut-1-en-1-yl)-2-(4-hydroxyphenyl)-5-methoxy-2,3-dihydro-1-benzopyran-4-one)

Structure for NP0224843 ((2r)-7-hydroxy-8-(3-hydroxy-3-methylbut-1-en-1-yl)-2-(4-hydroxyphenyl)-5-methoxy-2,3-dihydro-1-benzopyran-4-one)

3D Structure for NP0224843 ((2r)-7-hydroxy-8-(3-hydroxy-3-methylbut-1-en-1-yl)-2-(4-hydroxyphenyl)-5-methoxy-2,3-dihydro-1-benzopyran-4-one)