NP-MRD: Showing NP-Card for Obovatin (NP0043936)

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Record Information

Version

1.0

Created at

2021-06-22 17:41:42 UTC

Updated at

2021-06-22 17:41:42 UTC

NP-MRD ID

NP0043936

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Obovatin

Description

Obovatin belongs to the class of organic compounds known as pyranoflavonoids. Pyranoflavonoids are compounds containing a pyran ring fused to a 2-phenyl-1,4-benzopyran skeleton. Obovatin is found in Dalea boliviana, Ficus formosana, Tephrosia abbottiae, Tephrosia leiocarpa, Tephrosia obovata, Tephrosia pentaphylla , Tephrosia pumila and Tephrosia toxicaria. It was first documented in 2011 (PMID: 21226489). Based on a literature review a significant number of articles have been published on Obovatin (PMID: 31842487) (PMID: 26969405) (PMID: 22970736) (PMID: 22483325).

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

NP0043936
     RDKit          3D

 42 45  0  0  0  0  0  0  0  0999 V2000
    4.9224    0.6568   -1.3504 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0098    0.9367   -0.1521 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7484    1.8099    0.8617 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8235    1.6321   -0.6546 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5827    1.1940   -0.5770 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4288   -0.1187    0.0841 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5107   -0.8155    0.5748 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3310   -2.0534    1.1939 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0293   -2.5640    1.3020 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8398   -3.7698    1.9003 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0217   -1.8369    0.8002 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1417   -0.5937    0.1758 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9859    0.0463   -0.2912 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1293   -0.6193   -0.7934 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3168    0.2818   -0.6571 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2330    0.4555   -1.6741 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3331    1.2947   -1.5381 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5311    1.9802   -0.3637 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6282    1.8269    0.6768 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5432    0.9876    0.5178 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3801   -1.9578   -0.1434 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3985   -2.2937    0.8858 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7455   -2.9888    1.8645 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7886   -0.2967    0.4599 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4575   -0.1658   -1.9050 H   0  0  0  0  0  0  0  0  0  0  0  0
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    5.8830    0.2716   -0.9220 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3395    2.5884    0.3769 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9495    2.2447    1.5190 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3799    1.1659    1.4951 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9778    2.5893   -1.1317 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7296    1.7211   -0.9524 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1663   -2.5993    1.5768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0013   -4.2504    2.0279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9414   -0.8108   -1.8705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0634   -0.0922   -2.5950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0500    1.4292   -2.3368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3886    2.6435   -0.2382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8126    2.3802    1.5875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8363    0.8699    1.3378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4014   -2.7941   -0.9003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3859   -1.9287    0.3176 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 14 21  1  0
 21 22  1  0
 22 23  2  0
  7 24  1  0
 24  2  1  0
 12  6  1  0
 20 15  1  0
 22 11  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  3 28  1  0
  3 29  1  0
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  4 31  1  0
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  8 33  1  0
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 16 36  1  0
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 18 38  1  0
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 21 42  1  0
M  END


  Mrv1652306222119412D          

 24 27  0  0  1  0            999 V2000
    1.4009   -0.2947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0329   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4009   -1.3553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4454   -0.1105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    3.6829    0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.9204    1.3184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9204   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7454   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1579    0.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1579   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7454   -1.5395    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9204   -1.5395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5079   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6829   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2704   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4454   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1579   -2.2539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9829   -2.2539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3954   -2.9684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9829   -3.6829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1579   -3.6829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7454   -2.9684    0.0000 C   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
  2  4  1  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
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 17 18  2  0  0  0  0
  2 18  1  0  0  0  0
 13 19  1  1  0  0  0
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 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 19 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0043936

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)OC2=CC(O)=C3C(=O)C[C@H](OC3=C2C=C1)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C20H18O4/c1-20(2)9-8-13-17(24-20)11-15(22)18-14(21)10-16(23-19(13)18)12-6-4-3-5-7-12/h3-9,11,16,22H,10H2,1-2H3/t16-/m0/s1

> <INCHI_KEY>
VYVZELWVPQMZDE-INIZCTEOSA-N

> <FORMULA>
C20H18O4

> <MOLECULAR_WEIGHT>
322.36

> <EXACT_MASS>
322.12050906

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
42

> <JCHEM_AVERAGE_POLARIZABILITY>
34.942595652761895

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S)-5-hydroxy-8,8-dimethyl-2-phenyl-2H,3H,4H,8H-pyrano[2,3-f]chromen-4-one

> <ALOGPS_LOGP>
4.22

> <JCHEM_LOGP>
4.342862095666666

> <ALOGPS_LOGS>
-4.39

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.885148979596266

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.901070590928741

> <JCHEM_PKA_STRONGEST_BASIC>
-4.649300328959044

> <JCHEM_POLAR_SURFACE_AREA>
55.760000000000005

> <JCHEM_REFRACTIVITY>
91.72140000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.30e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-5-hydroxy-8,8-dimethyl-2-phenyl-2H,3H-pyrano[2,3-f]chromen-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

NP0043936
     RDKit          3D

 42 45  0  0  0  0  0  0  0  0999 V2000
    4.9224    0.6568   -1.3504 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0098    0.9367   -0.1521 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7484    1.8099    0.8617 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8235    1.6321   -0.6546 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5827    1.1940   -0.5770 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4288   -0.1187    0.0841 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5107   -0.8155    0.5748 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3310   -2.0534    1.1939 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0293   -2.5640    1.3020 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8398   -3.7698    1.9003 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0217   -1.8369    0.8002 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1417   -0.5937    0.1758 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9859    0.0463   -0.2912 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1293   -0.6193   -0.7934 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3168    0.2818   -0.6571 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2330    0.4555   -1.6741 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3331    1.2947   -1.5381 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5311    1.9802   -0.3637 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6282    1.8269    0.6768 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5432    0.9876    0.5178 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3801   -1.9578   -0.1434 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3985   -2.2937    0.8858 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7455   -2.9888    1.8645 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7886   -0.2967    0.4599 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4575   -0.1658   -1.9050 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0875    1.5433   -1.9600 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8830    0.2716   -0.9220 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3395    2.5884    0.3769 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9495    2.2447    1.5190 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3799    1.1659    1.4951 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9778    2.5893   -1.1317 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7296    1.7211   -0.9524 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1663   -2.5993    1.5768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0013   -4.2504    2.0279 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.0634   -0.0922   -2.5950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0500    1.4292   -2.3368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3886    2.6435   -0.2382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8126    2.3802    1.5875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8363    0.8699    1.3378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4014   -2.7941   -0.9003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3859   -1.9287    0.3176 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 14 21  1  0
 21 22  1  0
 22 23  2  0
  7 24  1  0
 24  2  1  0
 12  6  1  0
 20 15  1  0
 22 11  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  3 28  1  0
  3 29  1  0
  3 30  1  0
  4 31  1  0
  5 32  1  0
  8 33  1  0
 10 34  1  0
 14 35  1  6
 16 36  1  0
 17 37  1  0
 18 38  1  0
 19 39  1  0
 20 40  1  0
 21 41  1  0
 21 42  1  0
M  END

HEADER    PROTEIN                                 22-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-JUN-21         0                                  
HETATM    1  C   UNK     0       2.615  -0.550   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.795  -1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.615  -2.530   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       4.565  -0.206   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       6.105  -0.206   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.875   1.127   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.415   1.127   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       9.185   2.461   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       9.185  -0.206   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.725  -0.206   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      11.495   1.127   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      11.495  -1.540   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.725  -2.874   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       9.185  -2.874   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       8.415  -1.540   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.875  -1.540   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.105  -2.874   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.565  -2.874   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      11.495  -4.207   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      13.035  -4.207   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      13.805  -5.541   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      13.035  -6.875   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      11.495  -6.875   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      10.725  -5.541   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4   18                                             
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   16                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   15                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14   19                                                  
CONECT   14   13   15                                                       
CONECT   15   14    9   16                                                  
CONECT   16   15    5   17                                                  
CONECT   17   16   18                                                       
CONECT   18   17    2                                                       
CONECT   19   13   20   24                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   19                                                       
MASTER        0    0    0    0    0    0    0    0   24    0   54    0
END

COMPND    NP0043936
HETATM    1  C1  UNL     1       4.922   0.657  -1.350  1.00  0.00           C  
HETATM    2  C2  UNL     1       4.010   0.937  -0.152  1.00  0.00           C  
HETATM    3  C3  UNL     1       4.748   1.810   0.862  1.00  0.00           C  
HETATM    4  C4  UNL     1       2.823   1.632  -0.655  1.00  0.00           C  
HETATM    5  C5  UNL     1       1.583   1.194  -0.577  1.00  0.00           C  
HETATM    6  C6  UNL     1       1.429  -0.119   0.084  1.00  0.00           C  
HETATM    7  C7  UNL     1       2.511  -0.816   0.575  1.00  0.00           C  
HETATM    8  C8  UNL     1       2.331  -2.053   1.194  1.00  0.00           C  
HETATM    9  C9  UNL     1       1.029  -2.564   1.302  1.00  0.00           C  
HETATM   10  O1  UNL     1       0.840  -3.770   1.900  1.00  0.00           O  
HETATM   11  C10 UNL     1      -0.022  -1.837   0.800  1.00  0.00           C  
HETATM   12  C11 UNL     1       0.142  -0.594   0.176  1.00  0.00           C  
HETATM   13  O2  UNL     1      -0.986   0.046  -0.291  1.00  0.00           O  
HETATM   14  C12 UNL     1      -2.129  -0.619  -0.793  1.00  0.00           C  
HETATM   15  C13 UNL     1      -3.317   0.282  -0.657  1.00  0.00           C  
HETATM   16  C14 UNL     1      -4.233   0.455  -1.674  1.00  0.00           C  
HETATM   17  C15 UNL     1      -5.333   1.295  -1.538  1.00  0.00           C  
HETATM   18  C16 UNL     1      -5.531   1.980  -0.364  1.00  0.00           C  
HETATM   19  C17 UNL     1      -4.628   1.827   0.677  1.00  0.00           C  
HETATM   20  C18 UNL     1      -3.543   0.988   0.518  1.00  0.00           C  
HETATM   21  C19 UNL     1      -2.380  -1.958  -0.143  1.00  0.00           C  
HETATM   22  C20 UNL     1      -1.398  -2.294   0.886  1.00  0.00           C  
HETATM   23  O3  UNL     1      -1.745  -2.989   1.864  1.00  0.00           O  
HETATM   24  O4  UNL     1       3.789  -0.297   0.460  1.00  0.00           O  
HETATM   25  H1  UNL     1       4.458  -0.166  -1.905  1.00  0.00           H  
HETATM   26  H2  UNL     1       5.087   1.543  -1.960  1.00  0.00           H  
HETATM   27  H3  UNL     1       5.883   0.272  -0.922  1.00  0.00           H  
HETATM   28  H4  UNL     1       5.340   2.588   0.377  1.00  0.00           H  
HETATM   29  H5  UNL     1       3.950   2.245   1.519  1.00  0.00           H  
HETATM   30  H6  UNL     1       5.380   1.166   1.495  1.00  0.00           H  
HETATM   31  H7  UNL     1       2.978   2.589  -1.132  1.00  0.00           H  
HETATM   32  H8  UNL     1       0.730   1.721  -0.952  1.00  0.00           H  
HETATM   33  H9  UNL     1       3.166  -2.599   1.577  1.00  0.00           H  
HETATM   34  H10 UNL     1      -0.001  -4.250   2.028  1.00  0.00           H  
HETATM   35  H11 UNL     1      -1.941  -0.811  -1.871  1.00  0.00           H  
HETATM   36  H12 UNL     1      -4.063  -0.092  -2.595  1.00  0.00           H  
HETATM   37  H13 UNL     1      -6.050   1.429  -2.337  1.00  0.00           H  
HETATM   38  H14 UNL     1      -6.389   2.643  -0.238  1.00  0.00           H  
HETATM   39  H15 UNL     1      -4.813   2.380   1.588  1.00  0.00           H  
HETATM   40  H16 UNL     1      -2.836   0.870   1.338  1.00  0.00           H  
HETATM   41  H17 UNL     1      -2.401  -2.794  -0.900  1.00  0.00           H  
HETATM   42  H18 UNL     1      -3.386  -1.929   0.318  1.00  0.00           H  
CONECT    1    2   25   26   27
CONECT    2    3    4   24
CONECT    3   28   29   30
CONECT    4    5    5   31
CONECT    5    6   32
CONECT    6    7    7   12
CONECT    7    8   24
CONECT    8    9    9   33
CONECT    9   10   11
CONECT   10   34
CONECT   11   12   12   22
CONECT   12   13
CONECT   13   14
CONECT   14   15   21   35
CONECT   15   16   16   20
CONECT   16   17   36
CONECT   17   18   18   37
CONECT   18   19   38
CONECT   19   20   20   39
CONECT   20   40
CONECT   21   22   41   42
CONECT   22   23   23
END

NP0043936
     RDKit          3D

42 45  0  0  0  0  0  0  0  0999 V2000
    4.9224    0.6568   -1.3504 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0098    0.9367   -0.1521 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7484    1.8099    0.8617 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8235    1.6321   -0.6546 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5827    1.1940   -0.5770 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4288   -0.1187    0.0841 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5107   -0.8155    0.5748 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3310   -2.0534    1.1939 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0293   -2.5640    1.3020 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8398   -3.7698    1.9003 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0217   -1.8369    0.8002 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1417   -0.5937    0.1758 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9859    0.0463   -0.2912 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1293   -0.6193   -0.7934 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3168    0.2818   -0.6571 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2330    0.4555   -1.6741 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3331    1.2947   -1.5381 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5311    1.9802   -0.3637 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6282    1.8269    0.6768 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5432    0.9876    0.5178 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3801   -1.9578   -0.1434 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3985   -2.2937    0.8858 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7455   -2.9888    1.8645 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7886   -0.2967    0.4599 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4575   -0.1658   -1.9050 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0875    1.5433   -1.9600 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8830    0.2716   -0.9220 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3395    2.5884    0.3769 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9495    2.2447    1.5190 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3799    1.1659    1.4951 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9778    2.5893   -1.1317 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7296    1.7211   -0.9524 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1663   -2.5993    1.5768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0013   -4.2504    2.0279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9414   -0.8108   -1.8705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0634   -0.0922   -2.5950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0500    1.4292   -2.3368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3886    2.6435   -0.2382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8126    2.3802    1.5875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8363    0.8699    1.3378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4014   -2.7941   -0.9003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3859   -1.9287    0.3176 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 14 21  1  0
 21 22  1  0
 22 23  2  0
  7 24  1  0
 24  2  1  0
 12  6  1  0
 20 15  1  0
 22 11  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  3 28  1  0
  3 29  1  0
  3 30  1  0
  4 31  1  0
  5 32  1  0
  8 33  1  0
 10 34  1  0
 14 35  1  6
 16 36  1  0
 17 37  1  0
 18 38  1  0
 19 39  1  0
 20 40  1  0
 21 41  1  0
 21 42  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₁₈O₄

Average Mass

322.3600 Da

Monoisotopic Mass

322.12051 Da

IUPAC Name

(2S)-5-hydroxy-8,8-dimethyl-2-phenyl-2H,3H,4H,8H-pyrano[2,3-f]chromen-4-one

Traditional Name

(2S)-5-hydroxy-8,8-dimethyl-2-phenyl-2H,3H-pyrano[2,3-f]chromen-4-one

CAS Registry Number

Not Available

SMILES

CC1(C)OC2=CC(O)=C3C(=O)C[C@H](OC3=C2C=C1)C1=CC=CC=C1

InChI Identifier

InChI=1S/C20H18O4/c1-20(2)9-8-13-17(24-20)11-15(22)18-14(21)10-16(23-19(13)18)12-6-4-3-5-7-12/h3-9,11,16,22H,10H2,1-2H3/t16-/m0/s1

InChI Key

VYVZELWVPQMZDE-INIZCTEOSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Dalea boliviana	Linigton's dataset	21226489
Ficus formosana	Plant	KNApSAcK
Tephrosia abbottiae	Plant	KNApSAcK
Tephrosia leiocarpa	Plant	KNApSAcK
Tephrosia obovata	Plant	KNApSAcK
Tephrosia pentaphylla	Plant	KNApSAcK
Tephrosia pumila	Plant	KNApSAcK
Tephrosia toxicaria	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyranoflavonoids. Pyranoflavonoids are compounds containing a pyran ring fused to a 2-phenyl-1,4-benzopyran skeleton.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Pyranoflavonoids

Direct Parent

Pyranoflavonoids

Alternative Parents

Substituents

Pyranoflavonoid
5-hydroxyflavonoid
Flavanone
Hydroxyflavonoid
Flavan
Pyranochromene
2,2-dimethyl-1-benzopyran
Chromone
Chromane
Benzopyran
1-benzopyran
Aryl alkyl ketone
Aryl ketone
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Monocyclic benzene moiety
Benzenoid
Vinylogous acid
Ketone
Organoheterocyclic compound
Oxacycle
Ether
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

extended flavonoid (CHEBI:68376 )

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	4.22	ALOGPS
logP	4.34	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	8.9	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	55.76 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	91.72 m³·mol⁻¹	ChemAxon
Polarizability	34.94 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

C00008173

Chemspider ID

26393481

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

13940733

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Peralta MA, Ortega MG, Agnese AM, Cabrera JL: Prenylated flavanones with anti-tyrosinase activity from Dalea boliviana. J Nat Prod. 2011 Feb 25;74(2):158-62. doi: 10.1021/np1004664. Epub 2011 Jan 12. [PubMed:21226489 ]
Mkindi AG, Tembo Y, Mbega ER, Medvecky B, Kendal-Smith A, Farrell IW, Ndakidemi PA, Belmain SR, Stevenson PC: Phytochemical Analysis of Tephrosia vogelii across East Africa Reveals Three Chemotypes that Influence Its Use as a Pesticidal Plant. Plants (Basel). 2019 Dec 12;8(12). pii: plants8120597. doi: 10.3390/plants8120597. [PubMed:31842487 ]
Akter K, Barnes EC, Loa-Kum-Cheung WL, Yin P, Kichu M, Brophy JJ, Barrow RA, Imchen I, Vemulpad SR, Jamie JF: Antimicrobial and antioxidant activity and chemical characterisation of Erythrina stricta Roxb. (Fabaceae). J Ethnopharmacol. 2016 Jun 5;185:171-81. doi: 10.1016/j.jep.2016.03.011. Epub 2016 Mar 8. [PubMed:26969405 ]
Belmain SR, Amoah BA, Nyirenda SP, Kamanula JF, Stevenson PC: Highly variable insect control efficacy of Tephrosia vogelii chemotypes. J Agric Food Chem. 2012 Oct 10;60(40):10055-63. doi: 10.1021/jf3032217. Epub 2012 Sep 28. [PubMed:22970736 ]
Stevenson PC, Kite GC, Lewis GP, Forest F, Nyirenda SP, Belmain SR, Sileshi GW, Veitch NC: Distinct chemotypes of Tephrosia vogelii and implications for their use in pest control and soil enrichment. Phytochemistry. 2012 Jun;78:135-46. doi: 10.1016/j.phytochem.2012.02.025. Epub 2012 Apr 4. [PubMed:22483325 ]

Showing NP-Card for Obovatin (NP0043936)

MOL for NP0043936 (Obovatin)

3D MOL for NP0043936 (Obovatin)

3D SDF for NP0043936 (Obovatin)

3D-SDF for NP0043936 (Obovatin)

PDB for NP0043936 (Obovatin)

3D PDB for NP0043936 (Obovatin)

SMILES for NP0043936 (Obovatin)

INCHI for NP0043936 (Obovatin)

Structure for NP0043936 (Obovatin)

3D Structure for NP0043936 (Obovatin)