NP-MRD: Showing NP-Card for 11,22-dihydroxy-17,18-dimethoxy-7,7-dimethyl-2,8,21-trioxapentacyclo[12.8.0.0³,¹².0⁴,⁹.0¹⁵,²⁰]docosa-1(14),3,5,9,11,15(20),16,18-octaen-13-one (NP0311179)

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Record Information

Version

2.0

Created at

2022-09-11 07:00:34 UTC

Updated at

2022-09-11 07:00:34 UTC

NP-MRD ID

NP0311179

Secondary Accession Numbers

None

Natural Product Identification

Common Name

11,22-dihydroxy-17,18-dimethoxy-7,7-dimethyl-2,8,21-trioxapentacyclo[12.8.0.0³,¹².0⁴,⁹.0¹⁵,²⁰]docosa-1(14),3,5,9,11,15(20),16,18-octaen-13-one

Description

6-Hydroxy-6a,12a-dehydro-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, 6-hydroxy-6a,12a-dehydro-alpha-toxicarol is considered to be a flavonoid lipid molecule. 11,22-dihydroxy-17,18-dimethoxy-7,7-dimethyl-2,8,21-trioxapentacyclo[12.8.0.0³,¹².0⁴,⁹.0¹⁵,²⁰]docosa-1(14),3,5,9,11,15(20),16,18-octaen-13-one is found in Millettia brandisiana. 6-Hydroxy-6a,12a-dehydro-alpha-toxicarol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004231523102D          

 31 35  0  0  0  0            999 V2000
    2.9388   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3513   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1763   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5888   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4138   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8263   -3.4914    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6513   -3.4914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0638   -4.2059    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0638   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6513   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0638   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6513   -0.6336    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8888   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3013   -0.6336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8888    0.0809    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1263   -0.6336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5388   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3638   -1.3480    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7763   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4083   -1.5322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4083   -2.5928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3638   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5388   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1263   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3013   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8888   -2.7770    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8263   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4138   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5888   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1763   -0.6336    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3513   -0.6336    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
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
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 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 14 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
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 19 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 17 24  1  0  0  0  0
 24 25  2  0  0  0  0
 13 25  1  0  0  0  0
 25 26  1  0  0  0  0
  9 26  1  0  0  0  0
 10 27  1  0  0  0  0
  5 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
  3 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
M  END

     RDKit          3D

 51 55  0  0  0  0  0  0  0  0999 V2000
   -7.1428   -1.3736    2.0161 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7004   -0.6482    0.8904 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3429   -0.4918    0.6938 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4743   -1.0480    1.6012 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0859   -0.9320    1.4693 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6052   -0.2238    0.3716 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4270    0.3413   -0.5484 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8127    0.1953   -0.3689 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6964    0.7470   -1.2699 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2923    1.4696   -2.3932 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1498   -0.1095    0.2445 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3332   -0.6959    1.1976 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9863   -0.5887    1.0767 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5048    0.0526    0.0854 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8939    0.1424   -0.0057 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5291    0.8049   -1.0261 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7321    1.4058   -2.0015 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3554    1.3407   -1.9488 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5443    1.9280   -2.9032 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7817    0.6596   -0.8969 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6181    0.5768   -0.8171 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2768    1.1341   -1.7188 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9153    0.8738   -1.0845 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7492    0.2775   -0.1152 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6165    1.3446    0.5183 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6089   -0.7602   -0.8392 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0282   -0.4167    0.9522 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7113   -0.4896    1.0193 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8663   -1.4549    2.3738 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3092   -2.7314    2.4341 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2539   -1.5115    2.4122 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.7830   -0.8788    2.9605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6536   -2.3903    2.0435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8195   -1.6108    2.4752 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.2056    1.5853   -3.0470 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.9192    2.4920   -2.1012 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2299    1.9332   -2.8142 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9746    2.4312   -3.6802 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7721    2.2184   -0.1566 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5872    0.9491    0.8560 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0918    1.7419    1.4348 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0685   -1.7163   -0.9467 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8462   -0.4128   -1.8764 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5289   -0.9815   -0.2587 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6158   -0.8981    1.7316 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1998   -1.0163    1.8303 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5435   -0.8391    3.2660 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2828   -2.7637    3.2259 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
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  6 11  1  0
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 13 14  1  0
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 23 16  1  0
 16 17  2  0
 17 18  1  0
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 18 20  2  0
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 21 22  2  0
 12 29  1  0
 29 30  1  0
 29 31  1  0
  8  3  1  0
 21 11  1  0
 31  5  1  0
 20 14  1  0
 16 15  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  4 35  1  0
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 10 37  1  0
 10 38  1  0
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 28 49  1  0
 27 48  1  0
 25 42  1  0
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 26 45  1  0
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 26 47  1  0
 17 40  1  0
 19 41  1  0
 29 50  1  1
 30 51  1  0
M  END


  Mrv1533004231523102D          

 31 35  0  0  0  0            999 V2000
    2.9388   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3513   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1763   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5888   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4138   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8263   -3.4914    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6513   -3.4914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0638   -4.2059    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0638   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6513   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0638   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6513   -0.6336    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8888   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3013   -0.6336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8888    0.0809    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1263   -0.6336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5388   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3638   -1.3480    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7763   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4083   -1.5322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4083   -2.5928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3638   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5388   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1263   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3013   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8888   -2.7770    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8263   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4138   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5888   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1763   -0.6336    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3513   -0.6336    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
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  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
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
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 19 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 17 24  1  0  0  0  0
 24 25  2  0  0  0  0
 13 25  1  0  0  0  0
 25 26  1  0  0  0  0
  9 26  1  0  0  0  0
 10 27  1  0  0  0  0
  5 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
  3 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0311179

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC2=C(C=C1OC)C1=C(OC3=C4C=CC(C)(C)OC4=CC(O)=C3C1=O)C(O)O2

> <INCHI_IDENTIFIER>
InChI=1S/C23H20O8/c1-23(2)6-5-10-14(31-23)8-12(24)18-19(25)17-11-7-15(27-3)16(28-4)9-13(11)29-22(26)21(17)30-20(10)18/h5-9,22,24,26H,1-4H3

> <INCHI_KEY>
NVIZHSSHHRHDLE-UHFFFAOYSA-N

> <FORMULA>
C23H20O8

> <MOLECULAR_WEIGHT>
424.405

> <EXACT_MASS>
424.115817604

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
43.777565008191175

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
11,22-dihydroxy-17,18-dimethoxy-7,7-dimethyl-2,8,21-trioxapentacyclo[12.8.0.0³,¹².0⁴,⁹.0¹⁵,²⁰]docosa-1(14),3,5,9,11,15(20),16,18-octaen-13-one

> <ALOGPS_LOGP>
2.81

> <JCHEM_LOGP>
3.421128508333333

> <ALOGPS_LOGS>
-3.95

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.871781097772168

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.525471733582051

> <JCHEM_PKA_STRONGEST_BASIC>
-4.30763539557576

> <JCHEM_POLAR_SURFACE_AREA>
103.68

> <JCHEM_REFRACTIVITY>
111.63550000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.75e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
11,22-dihydroxy-17,18-dimethoxy-7,7-dimethyl-2,8,21-trioxapentacyclo[12.8.0.0³,¹².0⁴,⁹.0¹⁵,²⁰]docosa-1(14),3,5,9,11,15(20),16,18-octaen-13-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-APR-15         0                                  
HETATM    1  C   UNK     0       5.486  -2.516   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       6.256  -3.850   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       7.796  -3.850   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.566  -5.184   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.106  -5.184   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      10.876  -6.517   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      12.416  -6.517   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      13.186  -7.851   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      13.186  -5.184   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      12.416  -3.850   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      13.186  -2.516   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      12.416  -1.183   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      14.726  -2.516   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      15.496  -1.183   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      14.726   0.151   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      17.036  -1.183   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      17.806  -2.516   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      19.346  -2.516   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      20.116  -3.850   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      21.295  -2.860   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      21.295  -4.840   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      19.346  -5.184   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      17.806  -5.184   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      17.036  -3.850   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      15.496  -3.850   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      14.726  -5.184   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      10.876  -3.850   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      10.106  -2.516   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       8.566  -2.516   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       7.796  -1.183   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       6.256  -1.183   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   29                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   27                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   26                                                  
CONECT   10    9   11   27                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   25                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18   24                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   21   22                                             
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22   19   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   17   25                                                  
CONECT   25   24   13   26                                                  
CONECT   26   25    9                                                       
CONECT   27   10    5   28                                                  
CONECT   28   27   29                                                       
CONECT   29   28    3   30                                                  
CONECT   30   29   31                                                       
CONECT   31   30                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   70    0
END

View in JSmol

Synonyms

Value	Source
6-Hydroxy-6a,12a-dehydro-a-toxicarol	Generator
6-Hydroxy-6a,12a-dehydro-α-toxicarol	Generator

Chemical Formula

C₂₃H₂₀O₈

Average Mass

424.4050 Da

Monoisotopic Mass

424.11582 Da

IUPAC Name

11,22-dihydroxy-17,18-dimethoxy-7,7-dimethyl-2,8,21-trioxapentacyclo[12.8.0.0³,¹².0⁴,⁹.0¹⁵,²⁰]docosa-1(14),3,5,9,11,15(20),16,18-octaen-13-one

Traditional Name

11,22-dihydroxy-17,18-dimethoxy-7,7-dimethyl-2,8,21-trioxapentacyclo[12.8.0.0³,¹².0⁴,⁹.0¹⁵,²⁰]docosa-1(14),3,5,9,11,15(20),16,18-octaen-13-one

CAS Registry Number

Not Available

SMILES

COC1=CC2=C(C=C1OC)C1=C(OC3=C4C=CC(C)(C)OC4=CC(O)=C3C1=O)C(O)O2

InChI Identifier

InChI=1S/C23H20O8/c1-23(2)6-5-10-14(31-23)8-12(24)18-19(25)17-11-7-15(27-3)16(28-4)9-13(11)29-22(26)21(17)30-20(10)18/h5-9,22,24,26H,1-4H3

InChI Key

NVIZHSSHHRHDLE-UHFFFAOYSA-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
Millettia brandisiana	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

Rotenone or derivatives
Isoflavone
Pyranochromene
2,2-dimethyl-1-benzopyran
Chromone
Benzopyran
1-benzopyran
Anisole
Phenol ether
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Pyranone
Benzenoid
Pyran
Heteroaromatic compound
Vinylogous acid
Hemiacetal
Organoheterocyclic compound
Ether
Oxacycle
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Rotenoid flavonoids (LMPK12060075 )

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	2.81	ALOGPS
logP	3.42	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	7.53	ChemAxon
pKa (Strongest Basic)	-4.3	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	111.64 m³·mol⁻¹	ChemAxon
Polarizability	43.78 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

44257423

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 11,22-dihydroxy-17,18-dimethoxy-7,7-dimethyl-2,8,21-trioxapentacyclo[12.8.0.0³,¹².0⁴,⁹.0¹⁵,²⁰]docosa-1(14),3,5,9,11,15(20),16,18-octaen-13-one (NP0311179)

MOL for NP0311179 (11,22-dihydroxy-17,18-dimethoxy-7,7-dimethyl-2,8,21-trioxapentacyclo[12.8.0.0³,¹².0⁴,⁹.0¹⁵,²⁰]docosa-1(14),3,5,9,11,15(20),16,18-octaen-13-one)

3D MOL for NP0311179 (11,22-dihydroxy-17,18-dimethoxy-7,7-dimethyl-2,8,21-trioxapentacyclo[12.8.0.0³,¹².0⁴,⁹.0¹⁵,²⁰]docosa-1(14),3,5,9,11,15(20),16,18-octaen-13-one)

3D SDF for NP0311179 (11,22-dihydroxy-17,18-dimethoxy-7,7-dimethyl-2,8,21-trioxapentacyclo[12.8.0.0³,¹².0⁴,⁹.0¹⁵,²⁰]docosa-1(14),3,5,9,11,15(20),16,18-octaen-13-one)

3D-SDF for NP0311179 (11,22-dihydroxy-17,18-dimethoxy-7,7-dimethyl-2,8,21-trioxapentacyclo[12.8.0.0³,¹².0⁴,⁹.0¹⁵,²⁰]docosa-1(14),3,5,9,11,15(20),16,18-octaen-13-one)

PDB for NP0311179 (11,22-dihydroxy-17,18-dimethoxy-7,7-dimethyl-2,8,21-trioxapentacyclo[12.8.0.0³,¹².0⁴,⁹.0¹⁵,²⁰]docosa-1(14),3,5,9,11,15(20),16,18-octaen-13-one)

3D PDB for NP0311179 (11,22-dihydroxy-17,18-dimethoxy-7,7-dimethyl-2,8,21-trioxapentacyclo[12.8.0.0³,¹².0⁴,⁹.0¹⁵,²⁰]docosa-1(14),3,5,9,11,15(20),16,18-octaen-13-one)

SMILES for NP0311179 (11,22-dihydroxy-17,18-dimethoxy-7,7-dimethyl-2,8,21-trioxapentacyclo[12.8.0.0³,¹².0⁴,⁹.0¹⁵,²⁰]docosa-1(14),3,5,9,11,15(20),16,18-octaen-13-one)

INCHI for NP0311179 (11,22-dihydroxy-17,18-dimethoxy-7,7-dimethyl-2,8,21-trioxapentacyclo[12.8.0.0³,¹².0⁴,⁹.0¹⁵,²⁰]docosa-1(14),3,5,9,11,15(20),16,18-octaen-13-one)

Structure for NP0311179 (11,22-dihydroxy-17,18-dimethoxy-7,7-dimethyl-2,8,21-trioxapentacyclo[12.8.0.0³,¹².0⁴,⁹.0¹⁵,²⁰]docosa-1(14),3,5,9,11,15(20),16,18-octaen-13-one)

3D Structure for NP0311179 (11,22-dihydroxy-17,18-dimethoxy-7,7-dimethyl-2,8,21-trioxapentacyclo[12.8.0.0³,¹².0⁴,⁹.0¹⁵,²⁰]docosa-1(14),3,5,9,11,15(20),16,18-octaen-13-one)