NP-MRD: Showing NP-Card for (-)-alpha-Toxicarol (NP0070857)

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Record Information

Version

2.0

Created at

2022-04-28 16:16:29 UTC

Updated at

2022-04-28 16:16:29 UTC

NP-MRD ID

NP0070857

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-alpha-Toxicarol

Description

Toxicarol, also known as alpha-toxicarol, 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. Thus, toxicarol is considered to be a flavonoid. (-)-alpha-Toxicarol is found in Derris elliptica , Derris malaccensis, Derris trifoliata , Lonchocarpus utilis, Millettia brandisiana, Millettia pachycarpa, Millettia taiwaniana, Tephrosia candida, Tephrosia pentaphylla, Tephrosia purpurea and Tephrosia toxicaria. (-)-alpha-Toxicarol was first documented in 2009 (PMID: 19851932). Based on a literature review a small amount of articles have been published on Toxicarol (PMID: 22970736) (PMID: 22483325) (PMID: 32750400) (PMID: 19303755).

Structure

MOL 3D MOL SDF PDB SMILES InChI

  Mrv1652304282218162D          

 30 34  0  0  1  0            999 V2000
    4.8395   -1.0164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2520   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8395    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145    0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6020   -0.3020    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0145   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -0.3020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020    1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8390    0.0252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8390    0.7998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770    2.5559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2520    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0770    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4895    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0770   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3145    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7270    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4895    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3145    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  4  3  1  1  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  4 10  1  0  0  0  0
 10 11  2  0  0  0  0
  9 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
  8 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 14 19  1  0  0  0  0
 18 20  1  0  0  0  0
 18 21  1  0  0  0  0
 12 22  1  0  0  0  0
  3 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
  2 26  1  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 24 29  1  0  0  0  0
 29 30  1  0  0  0  0
M  END

     RDKit          3D

 52 56  0  0  0  0  0  0  0  0999 V2000
    6.6767   -0.1731   -2.6383 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4748    0.0860   -1.2618 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1720    0.1562   -0.8098 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0883   -0.0157   -1.6452 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8175    0.0595   -1.1690 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5941    0.3111    0.1691 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6592    0.4912    1.0492 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9418    0.4094    0.5373 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0290    0.5794    1.3626 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8519    0.8395    2.7425 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1862    0.3785    0.6146 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5791   -0.9867    0.3981 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2490   -2.0109    0.1828 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8811   -1.0902    0.4466 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5331   -2.2756    0.6862 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8737   -3.4599    0.9032 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9324   -2.2598    0.7090 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6534   -1.1122    0.5025 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9648    0.0469    0.2680 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5789    0.0968    0.2327 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9125    1.2900   -0.0079 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4422    1.2698   -0.3860 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5152    0.6780   -1.7766 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6752   -0.1065   -1.9703 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6654    1.3126    0.0392 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9819    1.2746    0.0713 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7787    0.0532    0.3198 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.7654   -0.1429   -0.8282 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5961    0.2593    1.6162 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0270   -1.0866    0.5228 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1570   -1.1268   -2.8601 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7354   -0.1912   -2.9226 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1030    0.6221   -3.1866 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2615   -0.2127   -2.6931 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4472    0.6867    2.0915 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7966    1.3169    3.1238 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6942   -0.0601    3.3374 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0628    1.6265    2.9098 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0400    0.7467    1.6242 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0736   -3.6393    0.9327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4704   -3.1952    0.8981 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8914    2.2708   -0.3411 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3519    0.0281   -1.9635 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5344    1.5267   -2.4912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1072    2.2196   -0.1448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5115    2.2340   -0.1022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1082   -1.1826   -0.7793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5500    0.6078   -0.6975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2072    0.0563   -1.7597 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9926    1.2903    1.6551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9201    0.0190    2.4569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3858   -0.5158    1.5850 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  2  0
  8  9  1  0
  9 10  1  0
  6 11  1  0
 11 22  1  0
 22 23  1  0
 23 24  1  0
 22 21  1  0
 21 20  1  0
 20 14  2  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 17 18  1  0
 18 19  2  0
 19 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  1  6
 27 29  1  0
 27 30  1  0
 14 12  1  0
 12 13  2  0
  8  3  1  0
 12 11  1  0
 24  5  1  0
 19 20  1  0
 30 18  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  4 34  1  0
  7 35  1  0
 10 36  1  0
 10 37  1  0
 10 38  1  0
 11 39  1  1
 22 42  1  6
 23 43  1  0
 23 44  1  0
 16 40  1  0
 17 41  1  0
 25 45  1  0
 26 46  1  0
 28 47  1  0
 28 48  1  0
 28 49  1  0
 29 50  1  0
 29 51  1  0
 29 52  1  0
M  END

  Mrv1652304282218162D          

 30 34  0  0  1  0            999 V2000
    4.8395   -1.0164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2520   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8395    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145    0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6020   -0.3020    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0145   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -0.3020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020    1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8390    0.0252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8390    0.7998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770    2.5559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2520    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0770    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4895    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0770   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3145    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7270    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4895    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3145    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  4  3  1  1  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  4 10  1  0  0  0  0
 10 11  2  0  0  0  0
  9 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
  8 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 14 19  1  0  0  0  0
 18 20  1  0  0  0  0
 18 21  1  0  0  0  0
 12 22  1  0  0  0  0
  3 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
  2 26  1  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 24 29  1  0  0  0  0
 29 30  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0070857

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC2=C(C=C1OC)[C@H]1[C@@H](CO2)OC2=C(C(O)=CC3=C2C=CC(C)(C)O3)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C23H22O7/c1-23(2)6-5-11-15(30-23)8-13(24)20-21(25)19-12-7-16(26-3)17(27-4)9-14(12)28-10-18(19)29-22(11)20/h5-9,18-19,24H,10H2,1-4H3/t18-,19+/m1/s1

> <INCHI_KEY>
JLTNCZQNGBLBGO-MOPGFXCFSA-N

> <FORMULA>
C23H22O7

> <MOLECULAR_WEIGHT>
410.422

> <EXACT_MASS>
410.136553048

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
43.03677657994693

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,14S)-11-hydroxy-17,18-dimethoxy-7,7-dimethyl-2,8,21-trioxapentacyclo[12.8.0.0^{3,12}.0^{4,9}.0^{15,20}]docosa-3(12),4(9),5,10,15(20),16,18-heptaen-13-one

> <ALOGPS_LOGP>
3.91

> <JCHEM_LOGP>
3.650640489000001

> <ALOGPS_LOGS>
-4.33

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.134410323404952

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.8686195857597

> <JCHEM_PKA_STRONGEST_BASIC>
-4.2088790266741025

> <JCHEM_POLAR_SURFACE_AREA>
83.45000000000002

> <JCHEM_REFRACTIVITY>
109.19890000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.94e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,14S)-11-hydroxy-17,18-dimethoxy-7,7-dimethyl-2,8,21-trioxapentacyclo[12.8.0.0^{3,12}.0^{4,9}.0^{15,20}]docosa-3(12),4(9),5,10,15(20),16,18-heptaen-13-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  O   UNK     0       9.034  -1.897   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       9.804  -0.564   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.034   0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.494   0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.724  -0.564   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.494  -1.897   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       5.184  -0.564   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       4.414   0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.184   2.104   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.724   2.104   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       7.494   3.437   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       4.414   3.437   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.874   3.437   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.104   2.104   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.874   0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.104  -0.564   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.564  -0.564   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.206   0.770   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       0.564   2.104   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -1.566   0.047   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.566   1.493   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       5.184   4.771   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       9.804   2.104   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      11.344   2.104   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      12.114   0.770   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      11.344  -0.564   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      13.654   0.770   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      14.424   2.104   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      12.114   3.437   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      13.654   3.437   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3   26                                                  
CONECT    3    2    4   23                                                  
CONECT    4    3    5   10                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8                                                       
CONECT    8    7    9   15                                                  
CONECT    9    8   10   12                                                  
CONECT   10    9    4   11                                                  
CONECT   11   10                                                            
CONECT   12    9   13   22                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   19                                                  
CONECT   15   14    8   16                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20   21                                             
CONECT   19   18   14                                                       
CONECT   20   18                                                            
CONECT   21   18                                                            
CONECT   22   12                                                            
CONECT   23    3   24                                                       
CONECT   24   23   25   29                                                  
CONECT   25   24   26   27                                                  
CONECT   26   25    2                                                       
CONECT   27   25   28                                                       
CONECT   28   27                                                            
CONECT   29   24   30                                                       
CONECT   30   29                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   68    0
END

View in JSmol

Synonyms

Value	Source
alpha-Toxicarol	Kegg
a-Toxicarol	Generator
Α-toxicarol	Generator

Chemical Formula

C₂₃H₂₂O₇

Average Mass

410.4220 Da

Monoisotopic Mass

410.13655 Da

IUPAC Name

(1S,14S)-11-hydroxy-17,18-dimethoxy-7,7-dimethyl-2,8,21-trioxapentacyclo[12.8.0.0^{3,12}.0^{4,9}.0^{15,20}]docosa-3(12),4(9),5,10,15(20),16,18-heptaen-13-one

Traditional Name

(1S,14S)-11-hydroxy-17,18-dimethoxy-7,7-dimethyl-2,8,21-trioxapentacyclo[12.8.0.0^{3,12}.0^{4,9}.0^{15,20}]docosa-3(12),4(9),5,10,15(20),16,18-heptaen-13-one

CAS Registry Number

Not Available

SMILES

COC1=CC2=C(C=C1OC)[C@H]1[C@@H](CO2)OC2=C(C(O)=CC3=C2C=CC(C)(C)O3)C1=O

InChI Identifier

InChI=1S/C23H22O7/c1-23(2)6-5-11-15(30-23)8-13(24)20-21(25)19-12-7-16(26-3)17(27-4)9-14(12)28-10-18(19)29-22(11)20/h5-9,18-19,24H,10H2,1-4H3/t18-,19+/m1/s1

InChI Key

JLTNCZQNGBLBGO-MOPGFXCFSA-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
Derris elliptica	Plant	KNApSAcK
Derris malaccensis	Plant	KNApSAcK
Derris trifoliata	Plant	KNApSAcK
Lonchocarpus utilis	LOTUS Database	35616633
Millettia brandisiana	Plant	KNApSAcK
Millettia pachycarpa	LOTUS Database	35616633
Millettia taiwaniana	Plant	KNApSAcK
Tephrosia candida	LOTUS Database	35616633
Tephrosia pentaphylla	LOTUS Database	35616633
Tephrosia purpurea	Plant	KNApSAcK
Tephrosia toxicaria	Plant	KNApSAcK

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
Chromane
Benzopyran
1-benzopyran
Anisole
Aryl alkyl ketone
Aryl ketone
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Benzenoid
Vinylogous acid
Ketone
Ether
Organoheterocyclic compound
Oxacycle
Organooxygen compound
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

isoflavanones (CHEBI:9643 )
rotenones (C10537 )
Rotenoid flavonoids (C10537 )
Rotenoid flavonoids (LMPK12060027 )

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	3.91	ALOGPS
logP	3.65	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	8.87	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	83.45 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	109.2 m³·mol⁻¹	ChemAxon
Polarizability	43.04 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

C00002580

Chemspider ID

391144

KEGG Compound ID

C10537

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

442826

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

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 ]
Owor RO, Derese S, Bedane KG, Zuhlke S, Ndakala A, Spiteller M: Isoflavones from the seedpods of Tephrosia vogelii and pyrazoisopongaflavone with anti-inflammatory effects. Fitoterapia. 2020 Oct;146:104695. doi: 10.1016/j.fitote.2020.104695. Epub 2020 Aug 1. [PubMed:32750400 ]
Shankar T, Muthusubramanian S, Gandhidasan R: A chromanone alkaloid from Derris ovalifolia stem. Nat Prod Res. 2009;23(17):1652-6. doi: 10.1080/14786410903306126. [PubMed:19851932 ]
Tewtrakul S, Cheenpracha S, Karalai C: Nitric oxide inhibitory principles from Derris trifoliata stems. Phytomedicine. 2009 Jun;16(6-7):568-72. doi: 10.1016/j.phymed.2008.12.015. Epub 2009 Mar 20. [PubMed:19303755 ]

Showing NP-Card for (-)-alpha-Toxicarol (NP0070857)

MOL for NP0070857 ((-)-alpha-Toxicarol)

3D MOL for NP0070857 ((-)-alpha-Toxicarol)

3D SDF for NP0070857 ((-)-alpha-Toxicarol)

3D-SDF for NP0070857 ((-)-alpha-Toxicarol)

PDB for NP0070857 ((-)-alpha-Toxicarol)

3D PDB for NP0070857 ((-)-alpha-Toxicarol)

SMILES for NP0070857 ((-)-alpha-Toxicarol)

INCHI for NP0070857 ((-)-alpha-Toxicarol)

Structure for NP0070857 ((-)-alpha-Toxicarol)

3D Structure for NP0070857 ((-)-alpha-Toxicarol)