NP-MRD: Showing NP-Card for (1s,14r)-11,14-dihydroxy-17,18-dimethoxy-7,7-dimethyl-2,8,21-trioxapentacyclo[12.8.0.0³,¹².0⁴,⁹.0¹⁵,²⁰]docosa-3,5,9,11,15(20),16,18-heptaen-13-one (NP0224546)

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Record Information

Version

2.0

Created at

2022-09-06 02:55:57 UTC

Updated at

2022-09-06 02:55:58 UTC

NP-MRD ID

NP0224546

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,14r)-11,14-dihydroxy-17,18-dimethoxy-7,7-dimethyl-2,8,21-trioxapentacyclo[12.8.0.0³,¹².0⁴,⁹.0¹⁵,²⁰]docosa-3,5,9,11,15(20),16,18-heptaen-13-one

Description

ZINC14721538 belongs to the class of organic compounds known as rotenones. These are rotenoids with a structure based on a 6a,12a-dihydrochromeno[3,4-b]chromen-12(6H)-one skeleton. (1s,14r)-11,14-dihydroxy-17,18-dimethoxy-7,7-dimethyl-2,8,21-trioxapentacyclo[12.8.0.0³,¹².0⁴,⁹.0¹⁵,²⁰]docosa-3,5,9,11,15(20),16,18-heptaen-13-one is found in Amorpha fruticosa, Tephrosia candida and Tephrosia villosa. Based on a literature review very few articles have been published on ZINC14721538.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309062204562D          

 31 35  0  0  1  0            999 V2000
   -5.6349   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2224   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3974   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9849   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1599   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7474   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1599   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9849   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3974   -3.4914    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2224   -3.4914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9224   -2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3349   -2.7770    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5099   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9224   -3.4914    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6849   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2724   -3.4914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6849   -4.2059    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5526   -3.4914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9651   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5526   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2724   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6849   -1.3480    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5099   -1.3480    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9224   -0.6336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7474   -0.6336    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9651   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7901   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2026   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8346   -1.5322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8346   -2.5928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7901   -2.7770    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
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  9 10  1  0  0  0  0
  6 11  1  0  0  0  0
 11 12  1  6  0  0  0
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 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
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 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 15 21  1  0  0  0  0
 21 22  1  0  0  0  0
 23 22  1  6  0  0  0
 11 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
  5 25  1  0  0  0  0
 20 26  1  0  0  0  0
 26 27  2  0  0  0  0
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 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 28 31  1  0  0  0  0
 19 31  1  0  0  0  0
M  END

     RDKit          3D

 53 57  0  0  0  0  0  0  0  0999 V2000
    7.4049    0.7111    1.6145 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5855   -0.4017    1.3176 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2118   -0.3057    1.1599 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5468    0.8968    1.2840 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1801    1.0060    1.1295 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4890   -0.1528    0.8408 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1539   -1.3554    0.7166 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5212   -1.4644    0.8713 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1860   -2.6827    0.7444 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4444   -3.8453    0.4486 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0368   -0.1208    0.6617 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4542   -0.6682    1.8111 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5690   -0.8413   -0.5542 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2772   -1.5599   -1.2722 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8592   -0.6512   -0.8871 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5047   -1.4842   -1.7700 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8101   -2.5100   -2.3521 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8381   -1.2811   -2.0602 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5548   -0.2443   -1.4768 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8802    0.5734   -0.5962 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5432    0.3877   -0.2909 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8929    1.2378    0.6072 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5110    1.3084    0.5159 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1236    2.2218    1.5235 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5358    2.2374    1.2613 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5862    1.6642    0.0338 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8537    1.8606   -0.2393 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.1982    1.9526   -2.2271 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.6256   -2.2944    0.4870 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.8170    1.6548   -0.5033 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6958    3.2187    1.4086 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9363    1.7791    2.5364 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.3733    2.6808    0.2383 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.4003   -0.4770    0.2185 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
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 13 11  1  0
 25  5  1  0
 15 21  1  0
 19 20  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  4 35  1  0
  7 36  1  0
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 30 52  1  0
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 18 42  1  0
 17 41  1  0
M  END


  Mrv1652309062204562D          

 31 35  0  0  1  0            999 V2000
   -5.6349   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2224   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3974   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9849   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1599   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7474   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1599   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9849   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3974   -3.4914    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2224   -3.4914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9224   -2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3349   -2.7770    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5099   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9224   -3.4914    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6849   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2724   -3.4914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6849   -4.2059    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5526   -3.4914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9651   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5526   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2724   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6849   -1.3480    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5099   -1.3480    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9224   -0.6336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7474   -0.6336    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.2026   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.8346   -2.5928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7901   -2.7770    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  2  0  0  0  0
  3  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  6 11  1  0  0  0  0
 11 12  1  6  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 16 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
 15 21  1  0  0  0  0
 21 22  1  0  0  0  0
 23 22  1  6  0  0  0
 11 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
  5 25  1  0  0  0  0
 20 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 28 31  1  0  0  0  0
 19 31  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0224546

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC2=C(C=C1OC)[C@@]1(O)[C@H](CO2)OC2=C3C=CC(C)(C)OC3=CC(O)=C2C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C23H22O8/c1-22(2)6-5-11-14(31-22)8-13(24)19-20(11)30-18-10-29-15-9-17(28-4)16(27-3)7-12(15)23(18,26)21(19)25/h5-9,18,24,26H,10H2,1-4H3/t18-,23+/m0/s1

> <INCHI_KEY>
OFLCPNIRDVOOEZ-FDDCHVKYSA-N

> <FORMULA>
C23H22O8

> <MOLECULAR_WEIGHT>
426.421

> <EXACT_MASS>
426.131467668

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
53

> <JCHEM_AVERAGE_POLARIZABILITY>
44.17649620530049

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,14R)-11,14-dihydroxy-17,18-dimethoxy-7,7-dimethyl-2,8,21-trioxapentacyclo[12.8.0.0^{3,12}.0^{4,9}.0^{15,20}]docosa-3,5,9,11,15(20),16,18-heptaen-13-one

> <JCHEM_LOGP>
3.059122826000001

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.105574933498291

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.744726171060034

> <JCHEM_PKA_STRONGEST_BASIC>
-4.21518976627349

> <JCHEM_POLAR_SURFACE_AREA>
103.68

> <JCHEM_REFRACTIVITY>
110.44489999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,14R)-11,14-dihydroxy-17,18-dimethoxy-7,7-dimethyl-2,8,21-trioxapentacyclo[12.8.0.0^{3,12}.0^{4,9}.0^{15,20}]docosa-3,5,9,11,15(20),16,18-heptaen-13-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     -10.518  -5.184   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -9.748  -3.850   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -8.208  -3.850   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -7.438  -2.516   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -5.898  -2.516   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -5.128  -3.850   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -5.898  -5.184   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -7.438  -5.184   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -8.208  -6.517   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -9.748  -6.517   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.588  -3.850   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -4.358  -5.184   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -2.818  -5.184   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -3.588  -6.517   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -1.278  -5.184   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.508  -6.517   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -1.278  -7.851   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       1.032  -6.517   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.802  -5.184   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.032  -3.850   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.508  -3.850   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -1.278  -2.516   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -2.818  -2.516   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -3.588  -1.183   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -5.128  -1.183   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       1.802  -2.516   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       3.342  -2.516   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.112  -3.850   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       5.291  -2.860   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       5.291  -4.840   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       3.342  -5.184   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   25                                                  
CONECT    6    5    7   11                                                  
CONECT    7    6    8                                                       
CONECT    8    7    3    9                                                  
CONECT    9    8   10                                                       
CONECT   10    9                                                            
CONECT   11    6   12   13   23                                             
CONECT   12   11                                                            
CONECT   13   11   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   21                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20   31                                                  
CONECT   20   19   21   26                                                  
CONECT   21   20   15   22                                                  
CONECT   22   21   23                                                       
CONECT   23   22   11   24                                                  
CONECT   24   23   25                                                       
CONECT   25   24    5                                                       
CONECT   26   20   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   30   31                                             
CONECT   29   28                                                            
CONECT   30   28                                                            
CONECT   31   28   19                                                       
MASTER        0    0    0    0    0    0    0    0   31    0   70    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₃H₂₂O₈

Average Mass

426.4210 Da

Monoisotopic Mass

426.13147 Da

IUPAC Name

(1S,14R)-11,14-dihydroxy-17,18-dimethoxy-7,7-dimethyl-2,8,21-trioxapentacyclo[12.8.0.0^{3,12}.0^{4,9}.0^{15,20}]docosa-3,5,9,11,15(20),16,18-heptaen-13-one

Traditional Name

(1S,14R)-11,14-dihydroxy-17,18-dimethoxy-7,7-dimethyl-2,8,21-trioxapentacyclo[12.8.0.0^{3,12}.0^{4,9}.0^{15,20}]docosa-3,5,9,11,15(20),16,18-heptaen-13-one

CAS Registry Number

Not Available

SMILES

COC1=CC2=C(C=C1OC)[C@@]1(O)[C@H](CO2)OC2=C3C=CC(C)(C)OC3=CC(O)=C2C1=O

InChI Identifier

InChI=1S/C23H22O8/c1-22(2)6-5-11-14(31-22)8-13(24)19-20(11)30-18-10-29-15-9-17(28-4)16(27-3)7-12(15)23(18,26)21(19)25/h5-9,18,24,26H,10H2,1-4H3/t18-,23+/m0/s1

InChI Key

OFLCPNIRDVOOEZ-FDDCHVKYSA-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
Amorpha fruticosa	LOTUS Database	35616633
Tephrosia candida	LOTUS Database	35616633
Tephrosia villosa	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as rotenones. These are rotenoids with a structure based on a 6a,12a-dihydrochromeno[3,4-b]chromen-12(6H)-one skeleton.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

Rotenoids

Direct Parent

Rotenones

Alternative Parents

Substituents

8-prenylated isoflavanone
Rotenone or derivatives
Isoflavanone
Isoflavan
Pyranochromene
2,2-dimethyl-1-benzopyran
Chromone
1-benzopyran
Benzopyran
Chromane
Aryl alkyl ketone
Aryl ketone
Anisole
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Benzenoid
Vinylogous acid
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	3.06	ChemAxon
pKa (Strongest Acidic)	8.74	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	103.68 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	110.44 m³·mol⁻¹	ChemAxon
Polarizability	44.18 Å³	ChemAxon
Number of Rings	5	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

124355889

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,14r)-11,14-dihydroxy-17,18-dimethoxy-7,7-dimethyl-2,8,21-trioxapentacyclo[12.8.0.0³,¹².0⁴,⁹.0¹⁵,²⁰]docosa-3,5,9,11,15(20),16,18-heptaen-13-one (NP0224546)

MOL for NP0224546 ((1s,14r)-11,14-dihydroxy-17,18-dimethoxy-7,7-dimethyl-2,8,21-trioxapentacyclo[12.8.0.0³,¹².0⁴,⁹.0¹⁵,²⁰]docosa-3,5,9,11,15(20),16,18-heptaen-13-one)

3D MOL for NP0224546 ((1s,14r)-11,14-dihydroxy-17,18-dimethoxy-7,7-dimethyl-2,8,21-trioxapentacyclo[12.8.0.0³,¹².0⁴,⁹.0¹⁵,²⁰]docosa-3,5,9,11,15(20),16,18-heptaen-13-one)

3D SDF for NP0224546 ((1s,14r)-11,14-dihydroxy-17,18-dimethoxy-7,7-dimethyl-2,8,21-trioxapentacyclo[12.8.0.0³,¹².0⁴,⁹.0¹⁵,²⁰]docosa-3,5,9,11,15(20),16,18-heptaen-13-one)

3D-SDF for NP0224546 ((1s,14r)-11,14-dihydroxy-17,18-dimethoxy-7,7-dimethyl-2,8,21-trioxapentacyclo[12.8.0.0³,¹².0⁴,⁹.0¹⁵,²⁰]docosa-3,5,9,11,15(20),16,18-heptaen-13-one)

PDB for NP0224546 ((1s,14r)-11,14-dihydroxy-17,18-dimethoxy-7,7-dimethyl-2,8,21-trioxapentacyclo[12.8.0.0³,¹².0⁴,⁹.0¹⁵,²⁰]docosa-3,5,9,11,15(20),16,18-heptaen-13-one)

3D PDB for NP0224546 ((1s,14r)-11,14-dihydroxy-17,18-dimethoxy-7,7-dimethyl-2,8,21-trioxapentacyclo[12.8.0.0³,¹².0⁴,⁹.0¹⁵,²⁰]docosa-3,5,9,11,15(20),16,18-heptaen-13-one)

SMILES for NP0224546 ((1s,14r)-11,14-dihydroxy-17,18-dimethoxy-7,7-dimethyl-2,8,21-trioxapentacyclo[12.8.0.0³,¹².0⁴,⁹.0¹⁵,²⁰]docosa-3,5,9,11,15(20),16,18-heptaen-13-one)

INCHI for NP0224546 ((1s,14r)-11,14-dihydroxy-17,18-dimethoxy-7,7-dimethyl-2,8,21-trioxapentacyclo[12.8.0.0³,¹².0⁴,⁹.0¹⁵,²⁰]docosa-3,5,9,11,15(20),16,18-heptaen-13-one)

Structure for NP0224546 ((1s,14r)-11,14-dihydroxy-17,18-dimethoxy-7,7-dimethyl-2,8,21-trioxapentacyclo[12.8.0.0³,¹².0⁴,⁹.0¹⁵,²⁰]docosa-3,5,9,11,15(20),16,18-heptaen-13-one)

3D Structure for NP0224546 ((1s,14r)-11,14-dihydroxy-17,18-dimethoxy-7,7-dimethyl-2,8,21-trioxapentacyclo[12.8.0.0³,¹².0⁴,⁹.0¹⁵,²⁰]docosa-3,5,9,11,15(20),16,18-heptaen-13-one)