NP-MRD: Showing NP-Card for 22-hydroxy-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 (NP0204655)

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Record Information

Version

2.0

Created at

2022-09-05 00:22:28 UTC

Updated at

2022-09-05 00:22:29 UTC

NP-MRD ID

NP0204655

Secondary Accession Numbers

None

Natural Product Identification

Common Name

22-hydroxy-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

22-Hydroxy-17,18-dimethoxy-7,7-dimethyl-2,8,21-trioxapentacyclo[12.8.0.0³,¹².0⁴,⁹.0¹⁵,²⁰]Docosa-1(14),3(12),4(9),5,10,15,17,19-octaen-13-one 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. 22-hydroxy-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 duchesnei. 22-Hydroxy-17,18-dimethoxy-7,7-dimethyl-2,8,21-trioxapentacyclo[12.8.0.0³,¹².0⁴,⁹.0¹⁵,²⁰]Docosa-1(14),3(12),4(9),5,10,15,17,19-octaen-13-one is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004241515232D          

 30 34  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
    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
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  4  5  1  0  0  0  0
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  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
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 16 17  1  0  0  0  0
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 16 23  1  0  0  0  0
 23 24  2  0  0  0  0
 13 24  1  0  0  0  0
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  9 25  1  0  0  0  0
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  5 26  2  0  0  0  0
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 27 28  2  0  0  0  0
  3 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
M  END

     RDKit          3D

 50 54  0  0  0  0  0  0  0  0999 V2000
   -7.4485   -1.4738    0.2401 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7587   -0.2386   -0.0008 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3509   -0.2113    0.0333 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6249   -1.3475    0.2932 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2266   -1.2679    0.3160 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6062   -0.0366    0.0741 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3404    1.0764   -0.1811 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7366    0.9857   -0.2015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5089    2.1310   -0.4646 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8496    3.3769   -0.7082 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1421    0.0245    0.1018 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4270   -1.1359    0.3657 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8845   -1.0813    0.3907 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5316    0.0200    0.1771 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9398   -0.0058    0.2216 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6989    1.1232    0.0053 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0440    2.3026   -0.2608 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6676    2.3308   -0.3050 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9021    1.2093   -0.0905 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4828    1.2119   -0.1296 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0370    2.2918   -0.3720 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0736    1.0210    0.0650 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7466   -0.1658    0.3330 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6923   -0.5450   -0.8210 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6171    0.1120    1.5712 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8987   -1.3432    0.5571 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5983   -1.2778    0.5073 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0919   -2.4457    0.6226 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6171   -3.4228   -0.2655 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4554   -2.3570    0.5673 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5290   -1.2660    0.1429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2789   -1.8271    1.2677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2040   -2.2294   -0.5364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1076   -2.2924    0.4786 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.2296    3.2415   -1.6177 H   0  0  0  0  0  0  0  0  0  0  0  0
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    3.6238    3.1925   -0.4318 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1545    3.2739   -0.5176 H   0  0  0  0  0  0  0  0  0  0  0  0
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    6.0693   -0.1088    2.5039 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9478    1.1633    1.5152 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.9540   -2.1449    0.6717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8038   -2.7072    1.6745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2491   -4.2084    0.2330 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
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  6 11  1  0
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 23 25  1  0
 23 22  1  0
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 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
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 28 29  1  0
 28 30  1  0
  8  3  1  0
 20 11  1  0
 30  5  1  0
 19 14  1  0
 16 15  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
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 25 44  1  0
 25 45  1  0
 25 46  1  0
 17 39  1  0
 18 40  1  0
 28 49  1  1
 29 50  1  0
M  END


  Mrv1533004241515232D          

 30 34  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
    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
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
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 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 16 23  1  0  0  0  0
 23 24  2  0  0  0  0
 13 24  1  0  0  0  0
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  9 25  1  0  0  0  0
 10 26  1  0  0  0  0
  5 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
  3 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0204655

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C23H20O7/c1-23(2)8-7-11-14(30-23)6-5-12-19(24)18-13-9-16(26-3)17(27-4)10-15(13)28-22(25)21(18)29-20(11)12/h5-10,22,25H,1-4H3

> <INCHI_KEY>
MOMKOGNUPUNXPC-UHFFFAOYSA-N

> <FORMULA>
C23H20O7

> <MOLECULAR_WEIGHT>
408.406

> <EXACT_MASS>
408.120902984

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
50

> <JCHEM_AVERAGE_POLARIZABILITY>
42.909212581422686

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
22-hydroxy-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>
2.85

> <JCHEM_LOGP>
3.07469383

> <ALOGPS_LOGS>
-4.54

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.871444577614575

> <JCHEM_PKA_STRONGEST_BASIC>
-4.304408303323683

> <JCHEM_POLAR_SURFACE_AREA>
83.45

> <JCHEM_REFRACTIVITY>
109.65460000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.18e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
22-hydroxy-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                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-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  C   UNK     0      17.036  -1.183   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      17.806  -2.516   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      19.346  -2.516   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      20.116  -3.850   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      21.295  -2.860   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      21.295  -4.840   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      19.346  -5.184   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      17.806  -5.184   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      17.036  -3.850   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      15.496  -3.850   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      14.726  -5.184   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      10.876  -3.850   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      10.106  -2.516   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       8.566  -2.516   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       7.796  -1.183   0.000  0.00  0.00           O+0
HETATM   30  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   28                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   26                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   25                                                  
CONECT   10    9   11   26                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   24                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   23                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   20   21                                             
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21   18   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   16   24                                                  
CONECT   24   23   13   25                                                  
CONECT   25   24    9                                                       
CONECT   26   10    5   27                                                  
CONECT   27   26   28                                                       
CONECT   28   27    3   29                                                  
CONECT   29   28   30                                                       
CONECT   30   29                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   68    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₃H₂₀O₇

Average Mass

408.4060 Da

Monoisotopic Mass

408.12090 Da

IUPAC Name

22-hydroxy-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

22-hydroxy-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=C3C1=O)C(O)O2

InChI Identifier

InChI=1S/C23H20O7/c1-23(2)8-7-11-14(30-23)6-5-12-19(24)18-13-9-16(26-3)17(27-4)10-15(13)28-22(25)21(18)29-20(11)12/h5-10,22,25H,1-4H3

InChI Key

MOMKOGNUPUNXPC-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 duchesnei	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
Alkyl aryl ether
Pyranone
Benzenoid
Pyran
Heteroaromatic compound
Hemiacetal
Oxacycle
Ether
Organoheterocyclic compound
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	2.85	ALOGPS
logP	3.07	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	10.87	ChemAxon
pKa (Strongest Basic)	-4.3	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	109.65 m³·mol⁻¹	ChemAxon
Polarizability	42.91 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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 22-hydroxy-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 (NP0204655)

MOL for NP0204655 (22-hydroxy-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 NP0204655 (22-hydroxy-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 NP0204655 (22-hydroxy-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 NP0204655 (22-hydroxy-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 NP0204655 (22-hydroxy-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 NP0204655 (22-hydroxy-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 NP0204655 (22-hydroxy-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 NP0204655 (22-hydroxy-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 NP0204655 (22-hydroxy-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 NP0204655 (22-hydroxy-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)