NP-MRD: Showing NP-Card for Ophiopogonanone A (NP0075631)

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Record Information

Version

2.0

Created at

2022-04-28 20:53:27 UTC

Updated at

2022-04-28 20:53:27 UTC

NP-MRD ID

NP0075631

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Ophiopogonanone A

Description

ZINC13481909 belongs to the class of organic compounds known as homoisoflavanones. These are homoisoflavonoids with a structure based on the chromanone system. Chromanone is a bicyclic compound consisting of a 3,4-dihydro-1-benzopyran, which bears a ketone group at the 4-position. Ophiopogonanone A is found in Ophiopogon japonicus and Ophiopogon japonicus Ker-Gawler . Based on a literature review very few articles have been published on ZINC13481909.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 40 43  0  0  0  0  0  0  0  0999 V2000
    5.9793   -0.7112    0.0221 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6641   -0.0799   -0.1814 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5200    0.8743   -1.1550 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5760    1.2769   -1.9691 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2975    1.4798   -1.3643 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2255    1.1138   -0.5832 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3571    0.1426    0.4139 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5772   -0.4593    0.6192 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7484   -1.4236    1.5923 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1931   -0.1853    1.2113 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3470   -0.4773    2.4039 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1527   -0.1506    0.5342 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2565    0.0188    1.5154 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5642   -0.1972    0.8722 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9987   -1.5140    0.7584 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2066   -1.7847    0.1521 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9792   -0.7741   -0.3369 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5496    0.5306   -0.2243 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3268    0.8352    0.3872 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5123    1.3614   -0.7971 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6945    0.5898   -0.9282 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2192   -0.7510   -0.9853 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1666    0.7644   -0.6295 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9547    1.6500   -0.7007 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8751   -1.6513    0.5974 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4276   -0.9549   -0.9672 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6167    0.0361    0.5565 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5001    0.9096   -1.9081 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1626    2.2447   -2.1371 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0718   -1.7862    2.2028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2543   -1.2103    0.1339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1220   -0.6602    2.3992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1971    1.0569    1.9609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4218   -2.3519    1.1307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5840   -2.8012    0.0424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0417    1.8607    0.4621 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3114    0.6800   -0.0060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2488    0.8800   -1.8356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2350    0.1865   -1.5907 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0509    1.4320   -0.6554 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  8  2  0
  8  9  1  0
  8  7  1  0
  7  6  2  0
  6 24  1  0
 24 23  1  0
 23 12  1  0
 12 13  1  0
 13 14  1  0
 14 19  2  0
 19 18  1  0
 18 17  2  0
 17 22  1  0
 22 21  1  0
 21 20  1  0
 17 16  1  0
 16 15  2  0
 12 10  1  0
 10 11  2  0
  6  5  1  0
  5  3  2  0
  3  4  1  0
  3  2  1  0
 10  7  1  0
 15 14  1  0
 20 18  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  9 30  1  0
 23 39  1  0
 23 40  1  0
 12 31  1  6
 13 32  1  0
 13 33  1  0
 19 36  1  0
 21 37  1  0
 21 38  1  0
 16 35  1  0
 15 34  1  0
  5 29  1  0
  4 28  1  0
M  END


  Mrv1652304282222532D          

 24 27  0  0  1  0            999 V2000
    4.7079   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4223   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1368   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1368   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4223   -4.9500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7079   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4223   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4943   -2.6326    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0094   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4943   -3.9674    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4223   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079   -8.6625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  6  7  2  0  0  0  0
  5  8  1  1  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
  9 14  1  0  0  0  0
 12 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 11 17  1  0  0  0  0
  2 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
  1 21  1  0  0  0  0
 21 22  1  0  0  0  0
 20 23  1  0  0  0  0
 19 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0075631

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=C(O)C2=C(OC[C@H](CC3=CC4=C(OCO4)C=C3)C2=O)C=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C18H16O6/c1-9-12(19)6-15-16(17(9)20)18(21)11(7-22-15)4-10-2-3-13-14(5-10)24-8-23-13/h2-3,5-6,11,19-20H,4,7-8H2,1H3/t11-/m0/s1

> <INCHI_KEY>
QBRLTNYECODTFP-NSHDSACASA-N

> <FORMULA>
C18H16O6

> <MOLECULAR_WEIGHT>
328.32

> <EXACT_MASS>
328.094688235

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
33.58619998780952

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3S)-3-[(2H-1,3-benzodioxol-5-yl)methyl]-5,7-dihydroxy-6-methyl-3,4-dihydro-2H-1-benzopyran-4-one

> <ALOGPS_LOGP>
2.61

> <JCHEM_LOGP>
3.6124469576666662

> <ALOGPS_LOGS>
-3.56

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.78458740581805

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.237615727892827

> <JCHEM_PKA_STRONGEST_BASIC>
-4.513679346252788

> <JCHEM_POLAR_SURFACE_AREA>
85.22000000000001

> <JCHEM_REFRACTIVITY>
85.1047

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.00e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3S)-3-(2H-1,3-benzodioxol-5-ylmethyl)-5,7-dihydroxy-6-methyl-2,3-dihydro-1-benzopyran-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       8.788 -11.550   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.122 -12.320   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      11.455 -11.550   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      11.455 -10.010   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.122  -9.240   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.788 -10.010   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       7.454  -9.240   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      10.122  -7.700   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.788  -6.930   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.454  -7.700   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.121  -6.930   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.121  -5.390   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.454  -4.620   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.788  -5.390   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       4.656  -4.914   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       3.751  -6.160   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       4.656  -7.406   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      10.122 -13.860   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.788 -14.630   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.454 -13.860   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.454 -12.320   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       6.121 -11.550   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       6.121 -14.630   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       8.788 -16.170   0.000  0.00  0.00           O+0
CONECT    1    2    6   21                                                  
CONECT    2    1    3   18                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    8                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6                                                            
CONECT    8    5    9                                                       
CONECT    9    8   10   14                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   17                                                  
CONECT   12   11   13   15                                                  
CONECT   13   12   14                                                       
CONECT   14   13    9                                                       
CONECT   15   12   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   11                                                       
CONECT   18    2   19                                                       
CONECT   19   18   20   24                                                  
CONECT   20   19   21   23                                                  
CONECT   21   20    1   22                                                  
CONECT   22   21                                                            
CONECT   23   20                                                            
CONECT   24   19                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   54    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₈H₁₆O₆

Average Mass

328.3200 Da

Monoisotopic Mass

328.09469 Da

IUPAC Name

(3S)-3-[(2H-1,3-benzodioxol-5-yl)methyl]-5,7-dihydroxy-6-methyl-3,4-dihydro-2H-1-benzopyran-4-one

Traditional Name

(3S)-3-(2H-1,3-benzodioxol-5-ylmethyl)-5,7-dihydroxy-6-methyl-2,3-dihydro-1-benzopyran-4-one

CAS Registry Number

Not Available

SMILES

CC1=C(O)C2=C(OC[C@H](CC3=CC4=C(OCO4)C=C3)C2=O)C=C1O

InChI Identifier

InChI=1S/C18H16O6/c1-9-12(19)6-15-16(17(9)20)18(21)11(7-22-15)4-10-2-3-13-14(5-10)24-8-23-13/h2-3,5-6,11,19-20H,4,7-8H2,1H3/t11-/m0/s1

InChI Key

QBRLTNYECODTFP-NSHDSACASA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Ophiopogon japonicus	LOTUS Database	35616633
Ophiopogon japonicus Ker-Gawler	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as homoisoflavanones. These are homoisoflavonoids with a structure based on the chromanone system. Chromanone is a bicyclic compound consisting of a 3,4-dihydro-1-benzopyran, which bears a ketone group at the 4-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Homoisoflavonoids

Sub Class

Homoisoflavans

Direct Parent

Homoisoflavanones

Alternative Parents

Substituents

Homoisoflavanone
Chromone
Chromane
Benzopyran
1-benzopyran
Benzodioxole
Aryl ketone
Aryl alkyl ketone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Benzenoid
Vinylogous acid
Ketone
Ether
Acetal
Oxacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Organic oxygen compound
Aldehyde
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	2.61	ALOGPS
logP	3.61	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	8.24	ChemAxon
pKa (Strongest Basic)	-4.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	85.22 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	85.1 m³·mol⁻¹	ChemAxon
Polarizability	33.59 Å³	ChemAxon
Number of Rings	4	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

92449513

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Ophiopogonanone A (NP0075631)

MOL for NP0075631 (Ophiopogonanone A)

3D MOL for NP0075631 (Ophiopogonanone A)

3D SDF for NP0075631 (Ophiopogonanone A)

3D-SDF for NP0075631 (Ophiopogonanone A)

PDB for NP0075631 (Ophiopogonanone A)

3D PDB for NP0075631 (Ophiopogonanone A)

SMILES for NP0075631 (Ophiopogonanone A)

INCHI for NP0075631 (Ophiopogonanone A)

Structure for NP0075631 (Ophiopogonanone A)

3D Structure for NP0075631 (Ophiopogonanone A)