NP-MRD: Showing NP-Card for 4',5'-dihydro-11,5'-dihydroxy-4'-methoxytephrosin (NP0043810)

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Record Information

Version

1.0

Created at

2021-06-22 17:18:45 UTC

Updated at

2021-06-22 17:18:45 UTC

NP-MRD ID

NP0043810

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4',5'-dihydro-11,5'-dihydroxy-4'-methoxytephrosin

Description

4',5'-Dihydro-11,5'-dihydroxy-4'-methoxytephrosin, also known as DDMT CPD, 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. 4',5'-Dihydro-11,5'-dihydroxy-4'-methoxytephrosin is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. 4',5'-dihydro-11,5'-dihydroxy-4'-methoxytephrosin is found in Tephrosia toxicaria. It was first documented in 2002 (PMID: 29437326). Based on a literature review a significant number of articles have been published on 4',5'-dihydro-11,5'-dihydroxy-4'-methoxytephrosin (PMID: 14510590) (PMID: 27466641) (PMID: 27253005) (PMID: 26389468).

Structure

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


  Mrv1652306222119182D          

 35 39  0  0  1  0            999 V2000
    3.1895    0.4125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020    1.1270    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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M  END

NP0043810
     RDKit          3D

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M  END


  Mrv1652306222119182D          

 35 39  0  0  1  0            999 V2000
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M  END
> <DATABASE_ID>
NP0043810

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]12COC3=C(C=C(OC)C(OC)=C3)[C@]1(O)C(=O)C1=C(O2)C2=C(OC(C)(C)C(O)C2OC)C=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C24H26O10/c1-23(2)22(27)20(31-5)18-15(34-23)7-11(25)17-19(18)33-16-9-32-12-8-14(30-4)13(29-3)6-10(12)24(16,28)21(17)26/h6-8,16,20,22,25,27-28H,9H2,1-5H3/t16-,20?,22?,24-/m1/s1

> <INCHI_KEY>
RTUABMSWXKMPKI-JIEJDMOWSA-N

> <FORMULA>
C24H26O10

> <MOLECULAR_WEIGHT>
474.462

> <EXACT_MASS>
474.152597037

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
60

> <JCHEM_AVERAGE_POLARIZABILITY>
47.63473306392899

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,14R)-6,11,14-trihydroxy-5,17,18-trimethoxy-7,7-dimethyl-2,8,21-trioxapentacyclo[12.8.0.0^{3,12}.0^{4,9}.0^{15,20}]docosa-3(12),4(9),10,15(20),16,18-hexaen-13-one

> <ALOGPS_LOGP>
1.43

> <JCHEM_LOGP>
1.8316637723333338

> <ALOGPS_LOGS>
-3.04

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.095202243651126

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.455888151736056

> <JCHEM_PKA_STRONGEST_BASIC>
-3.7314319972310157

> <JCHEM_POLAR_SURFACE_AREA>
133.14000000000001

> <JCHEM_REFRACTIVITY>
116.80250000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.30e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,14R)-6,11,14-trihydroxy-5,17,18-trimethoxy-7,7-dimethyl-2,8,21-trioxapentacyclo[12.8.0.0^{3,12}.0^{4,9}.0^{15,20}]docosa-3(12),4(9),10,15(20),16,18-hexaen-13-one

> <JCHEM_VEBER_RULE>
0

$$$$

NP0043810
     RDKit          3D

 60 64  0  0  0  0  0  0  0  0999 V2000
    6.6059   -2.5907   -2.3064 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5503   -1.3780   -1.6017 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3615   -0.7761   -1.2115 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1807   -1.4091   -1.5371 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9883   -0.8085   -1.1474 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0168    0.3820   -0.4585 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2125    1.0102   -0.1362 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4045    0.4143   -0.5232 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6086    1.0367   -0.2047 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6403    2.2491    0.4965 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7087    0.9748   -0.0678 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9277    2.3259    0.1603 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3068    0.3233    1.1999 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1327    0.0127    2.0807 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0906    0.0335    1.4332 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5339   -0.6552    2.5592 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4358   -1.0580    3.4624 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8815   -0.9217    2.7613 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8206   -0.5075    1.8441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3713    0.1710    0.7370 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0444    0.4500    0.5090 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6017    1.1453   -0.6292 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6879    0.8184   -1.1529 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6015   -0.5798   -1.7012 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7452   -1.3521   -1.4192 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3633    0.6319   -0.2742 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9872    1.7545    0.2665 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8320    2.8741   -0.5466 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3961   -0.4467   -0.4140 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3799   -0.0346   -1.3089 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9802   -0.9200    0.8677 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2471   -0.0885    1.1181 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4849   -2.3669    0.7620 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1744   -0.7506    2.0034 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6405   -2.7430   -2.6590 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3188   -3.4587   -1.6760 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9453   -2.5625   -3.2045 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1385   -2.3414   -2.0759 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1798    1.9484    0.4088 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0635    2.1494    1.4398 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6908    2.4936    0.7722 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1754    3.0891   -0.0695 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3070    2.4213    1.0679 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1215   -1.5680    4.2992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1626   -1.4591    3.6529 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8997    1.5752   -1.9364 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4523   -0.5353   -2.8065 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2788   -1.1140   -1.2890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8976    0.9137   -1.2231 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3389    3.7461   -0.0884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7392    3.1283   -0.5666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2496    2.7391   -1.5530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8892   -1.3217   -0.9027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7030    0.8709   -1.1626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1023   -0.5370    0.5509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1190    0.9561    0.8356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5179   -0.2215    2.2029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4700   -2.3407    0.2465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5791   -2.8314    1.7492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8124   -2.9606    0.0786 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 12  1  1
 11 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 20 26  1  0
 26 27  1  0
 27 28  1  0
 26 29  1  0
 29 30  1  0
 29 31  1  0
 31 32  1  0
 31 33  1  0
 31 34  1  0
  8  3  1  0
 23 11  1  0
 25  5  1  0
 21 15  1  0
 34 19  1  0
  1 35  1  0
  1 36  1  0
  1 37  1  0
  4 38  1  0
  7 39  1  0
 10 40  1  0
 10 41  1  0
 10 42  1  0
 12 43  1  0
 17 44  1  0
 18 45  1  0
 23 46  1  6
 24 47  1  0
 24 48  1  0
 26 49  1  0
 28 50  1  0
 28 51  1  0
 28 52  1  0
 29 53  1  0
 30 54  1  0
 32 55  1  0
 32 56  1  0
 32 57  1  0
 33 58  1  0
 33 59  1  0
 33 60  1  0
M  END

HEADER    PROTEIN                                 22-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-JUN-21         0                                  
HETATM    1  H   UNK     0       5.954   0.770   0.000  0.00  0.00           H+0
HETATM    2  C   UNK     0       6.724   2.104   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.494   3.437   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       9.034   3.437   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       9.804   2.104   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.034   0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.804  -0.564   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      11.344  -0.564   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      12.114  -1.897   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      13.654  -1.897   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      12.114   0.770   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      13.654   0.770   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      14.424   2.104   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      11.344   2.104   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.494   0.770   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       8.264  -0.564   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       6.724  -0.564   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       7.494  -1.897   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       5.184  -0.564   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.414   0.770   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       5.184   2.104   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       2.874   0.770   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.104  -0.564   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       0.564  -0.564   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -0.206   0.770   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -1.386  -0.220   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -1.386   1.760   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       0.564   2.104   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -0.206   3.437   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       2.104   2.104   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       2.874   3.437   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       4.414   3.437   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       2.874  -1.897   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       4.414  -1.897   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       5.184  -3.231   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   15   21                                             
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   14                                                  
CONECT    6    5    7   15                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   11                                                  
CONECT    9    8   10                                                       
CONECT   10    9                                                            
CONECT   11    8   12   14                                                  
CONECT   12   11   13                                                       
CONECT   13   12                                                            
CONECT   14   11    5                                                       
CONECT   15    6    2   16   17                                             
CONECT   16   15                                                            
CONECT   17   15   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   34                                                  
CONECT   20   19   21   22                                                  
CONECT   21   20    2                                                       
CONECT   22   20   23   30                                                  
CONECT   23   22   24   33                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   27   28                                             
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   25   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   22   31                                                  
CONECT   31   30   32                                                       
CONECT   32   31                                                            
CONECT   33   23   34                                                       
CONECT   34   33   19   35                                                  
CONECT   35   34                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   78    0
END

COMPND    NP0043810
HETATM    1  C1  UNL     1       6.606  -2.591  -2.306  1.00  0.00           C  
HETATM    2  O1  UNL     1       6.550  -1.378  -1.602  1.00  0.00           O  
HETATM    3  C2  UNL     1       5.361  -0.776  -1.211  1.00  0.00           C  
HETATM    4  C3  UNL     1       4.181  -1.409  -1.537  1.00  0.00           C  
HETATM    5  C4  UNL     1       2.988  -0.809  -1.147  1.00  0.00           C  
HETATM    6  C5  UNL     1       3.017   0.382  -0.459  1.00  0.00           C  
HETATM    7  C6  UNL     1       4.213   1.010  -0.136  1.00  0.00           C  
HETATM    8  C7  UNL     1       5.405   0.414  -0.523  1.00  0.00           C  
HETATM    9  O2  UNL     1       6.609   1.037  -0.205  1.00  0.00           O  
HETATM   10  C8  UNL     1       6.640   2.249   0.497  1.00  0.00           C  
HETATM   11  C9  UNL     1       1.709   0.975  -0.068  1.00  0.00           C  
HETATM   12  O3  UNL     1       1.928   2.326   0.160  1.00  0.00           O  
HETATM   13  C10 UNL     1       1.307   0.323   1.200  1.00  0.00           C  
HETATM   14  O4  UNL     1       2.133   0.013   2.081  1.00  0.00           O  
HETATM   15  C11 UNL     1      -0.091   0.033   1.433  1.00  0.00           C  
HETATM   16  C12 UNL     1      -0.534  -0.655   2.559  1.00  0.00           C  
HETATM   17  O5  UNL     1       0.436  -1.058   3.462  1.00  0.00           O  
HETATM   18  C13 UNL     1      -1.882  -0.922   2.761  1.00  0.00           C  
HETATM   19  C14 UNL     1      -2.821  -0.508   1.844  1.00  0.00           C  
HETATM   20  C15 UNL     1      -2.371   0.171   0.737  1.00  0.00           C  
HETATM   21  C16 UNL     1      -1.044   0.450   0.509  1.00  0.00           C  
HETATM   22  O6  UNL     1      -0.602   1.145  -0.629  1.00  0.00           O  
HETATM   23  C17 UNL     1       0.688   0.818  -1.153  1.00  0.00           C  
HETATM   24  C18 UNL     1       0.602  -0.580  -1.701  1.00  0.00           C  
HETATM   25  O7  UNL     1       1.745  -1.352  -1.419  1.00  0.00           O  
HETATM   26  C19 UNL     1      -3.363   0.632  -0.274  1.00  0.00           C  
HETATM   27  O8  UNL     1      -3.987   1.755   0.266  1.00  0.00           O  
HETATM   28  C20 UNL     1      -3.832   2.874  -0.547  1.00  0.00           C  
HETATM   29  C21 UNL     1      -4.396  -0.447  -0.414  1.00  0.00           C  
HETATM   30  O9  UNL     1      -5.380  -0.035  -1.309  1.00  0.00           O  
HETATM   31  C22 UNL     1      -4.980  -0.920   0.868  1.00  0.00           C  
HETATM   32  C23 UNL     1      -6.247  -0.088   1.118  1.00  0.00           C  
HETATM   33  C24 UNL     1      -5.485  -2.367   0.762  1.00  0.00           C  
HETATM   34  O10 UNL     1      -4.174  -0.751   2.003  1.00  0.00           O  
HETATM   35  H1  UNL     1       7.641  -2.743  -2.659  1.00  0.00           H  
HETATM   36  H2  UNL     1       6.319  -3.459  -1.676  1.00  0.00           H  
HETATM   37  H3  UNL     1       5.945  -2.563  -3.204  1.00  0.00           H  
HETATM   38  H4  UNL     1       4.139  -2.341  -2.076  1.00  0.00           H  
HETATM   39  H5  UNL     1       4.180   1.948   0.409  1.00  0.00           H  
HETATM   40  H6  UNL     1       6.064   2.149   1.440  1.00  0.00           H  
HETATM   41  H7  UNL     1       7.691   2.494   0.772  1.00  0.00           H  
HETATM   42  H8  UNL     1       6.175   3.089  -0.070  1.00  0.00           H  
HETATM   43  H9  UNL     1       2.307   2.421   1.068  1.00  0.00           H  
HETATM   44  H10 UNL     1       0.122  -1.568   4.299  1.00  0.00           H  
HETATM   45  H11 UNL     1      -2.163  -1.459   3.653  1.00  0.00           H  
HETATM   46  H12 UNL     1       0.900   1.575  -1.936  1.00  0.00           H  
HETATM   47  H13 UNL     1       0.452  -0.535  -2.807  1.00  0.00           H  
HETATM   48  H14 UNL     1      -0.279  -1.114  -1.289  1.00  0.00           H  
HETATM   49  H15 UNL     1      -2.898   0.914  -1.223  1.00  0.00           H  
HETATM   50  H16 UNL     1      -4.339   3.746  -0.088  1.00  0.00           H  
HETATM   51  H17 UNL     1      -2.739   3.128  -0.567  1.00  0.00           H  
HETATM   52  H18 UNL     1      -4.250   2.739  -1.553  1.00  0.00           H  
HETATM   53  H19 UNL     1      -3.889  -1.322  -0.903  1.00  0.00           H  
HETATM   54  H20 UNL     1      -5.703   0.871  -1.163  1.00  0.00           H  
HETATM   55  H21 UNL     1      -7.102  -0.537   0.551  1.00  0.00           H  
HETATM   56  H22 UNL     1      -6.119   0.956   0.836  1.00  0.00           H  
HETATM   57  H23 UNL     1      -6.518  -0.221   2.203  1.00  0.00           H  
HETATM   58  H24 UNL     1      -6.470  -2.341   0.246  1.00  0.00           H  
HETATM   59  H25 UNL     1      -5.579  -2.831   1.749  1.00  0.00           H  
HETATM   60  H26 UNL     1      -4.812  -2.961   0.079  1.00  0.00           H  
CONECT    1    2   35   36   37
CONECT    2    3
CONECT    3    4    4    8
CONECT    4    5   38
CONECT    5    6    6   25
CONECT    6    7   11
CONECT    7    8    8   39
CONECT    8    9
CONECT    9   10
CONECT   10   40   41   42
CONECT   11   12   13   23
CONECT   12   43
CONECT   13   14   14   15
CONECT   15   16   16   21
CONECT   16   17   18
CONECT   17   44
CONECT   18   19   19   45
CONECT   19   20   34
CONECT   20   21   21   26
CONECT   21   22
CONECT   22   23
CONECT   23   24   46
CONECT   24   25   47   48
CONECT   26   27   29   49
CONECT   27   28
CONECT   28   50   51   52
CONECT   29   30   31   53
CONECT   30   54
CONECT   31   32   33   34
CONECT   32   55   56   57
CONECT   33   58   59   60
END

NP0043810
     RDKit          3D

60 64  0  0  0  0  0  0  0  0999 V2000
    6.6059   -2.5907   -2.3064 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5503   -1.3780   -1.6017 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3615   -0.7761   -1.2115 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1807   -1.4091   -1.5371 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9883   -0.8085   -1.1474 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0168    0.3820   -0.4585 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2125    1.0102   -0.1362 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4045    0.4143   -0.5232 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6086    1.0367   -0.2047 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6403    2.2491    0.4965 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7087    0.9748   -0.0678 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9277    2.3259    0.1603 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3068    0.3233    1.1999 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1327    0.0127    2.0807 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0906    0.0335    1.4332 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5339   -0.6552    2.5592 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4358   -1.0580    3.4624 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8815   -0.9217    2.7613 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8206   -0.5075    1.8441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3713    0.1710    0.7370 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0444    0.4500    0.5090 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6017    1.1453   -0.6292 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6879    0.8184   -1.1529 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6015   -0.5798   -1.7012 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7452   -1.3521   -1.4192 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3633    0.6319   -0.2742 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9872    1.7545    0.2665 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8320    2.8741   -0.5466 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3961   -0.4467   -0.4140 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3799   -0.0346   -1.3089 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9802   -0.9200    0.8677 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2471   -0.0885    1.1181 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4849   -2.3669    0.7620 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1744   -0.7506    2.0034 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6405   -2.7430   -2.6590 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3188   -3.4587   -1.6760 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9453   -2.5625   -3.2045 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1385   -2.3414   -2.0759 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1798    1.9484    0.4088 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0635    2.1494    1.4398 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6908    2.4936    0.7722 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1754    3.0891   -0.0695 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3070    2.4213    1.0679 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1215   -1.5680    4.2992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1626   -1.4591    3.6529 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8997    1.5752   -1.9364 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4523   -0.5353   -2.8065 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2788   -1.1140   -1.2890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8976    0.9137   -1.2231 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3389    3.7461   -0.0884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7392    3.1283   -0.5666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2496    2.7391   -1.5530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8892   -1.3217   -0.9027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7030    0.8709   -1.1626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1023   -0.5370    0.5509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1190    0.9561    0.8356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5179   -0.2215    2.2029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4700   -2.3407    0.2465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5791   -2.8314    1.7492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8124   -2.9606    0.0786 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 12  1  1
 11 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 20 26  1  0
 26 27  1  0
 27 28  1  0
 26 29  1  0
 29 30  1  0
 29 31  1  0
 31 32  1  0
 31 33  1  0
 31 34  1  0
  8  3  1  0
 23 11  1  0
 25  5  1  0
 21 15  1  0
 34 19  1  0
  1 35  1  0
  1 36  1  0
  1 37  1  0
  4 38  1  0
  7 39  1  0
 10 40  1  0
 10 41  1  0
 10 42  1  0
 12 43  1  0
 17 44  1  0
 18 45  1  0
 23 46  1  6
 24 47  1  0
 24 48  1  0
 26 49  1  0
 28 50  1  0
 28 51  1  0
 28 52  1  0
 29 53  1  0
 30 54  1  0
 32 55  1  0
 32 56  1  0
 32 57  1  0
 33 58  1  0
 33 59  1  0
 33 60  1  0
M  END

View in JSmol

Synonyms

Value	Source
DDMT CPD	MeSH

Chemical Formula

C₂₄H₂₆O₁₀

Average Mass

474.4620 Da

Monoisotopic Mass

474.15260 Da

IUPAC Name

(1R,14R)-6,11,14-trihydroxy-5,17,18-trimethoxy-7,7-dimethyl-2,8,21-trioxapentacyclo[12.8.0.0^{3,12}.0^{4,9}.0^{15,20}]docosa-3(12),4(9),10,15(20),16,18-hexaen-13-one

Traditional Name

(1R,14R)-6,11,14-trihydroxy-5,17,18-trimethoxy-7,7-dimethyl-2,8,21-trioxapentacyclo[12.8.0.0^{3,12}.0^{4,9}.0^{15,20}]docosa-3(12),4(9),10,15(20),16,18-hexaen-13-one

CAS Registry Number

Not Available

SMILES

[H][C@@]12COC3=C(C=C(OC)C(OC)=C3)[C@]1(O)C(=O)C1=C(O2)C2=C(OC(C)(C)C(O)C2OC)C=C1O

InChI Identifier

InChI=1S/C24H26O10/c1-23(2)22(27)20(31-5)18-15(34-23)7-11(25)17-19(18)33-16-9-32-12-8-14(30-4)13(29-3)6-10(12)24(16,28)21(17)26/h6-8,16,20,22,25,27-28H,9H2,1-5H3/t16-,20?,22?,24-/m1/s1

InChI Key

RTUABMSWXKMPKI-JIEJDMOWSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, Acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, Acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, Acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, Acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, Acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, Acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, Acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, Acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, Acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, Acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, Acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, Acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, Acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, Acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, Acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, Acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, Acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, Acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, Acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, Acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Tephrosia toxicaria	Linigton's dataset	14510590

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
8-prenylated isoflavanone
Isoflavanone
Isoflavan
Pyranochromene
2,2-dimethyl-1-benzopyran
Chromone
1-benzopyran
Chromane
Benzopyran
Anisole
Aryl ketone
Aryl alkyl ketone
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Vinylogous acid
Tertiary alcohol
Secondary alcohol
Ketone
Polyol
Ether
Dialkyl ether
Organoheterocyclic compound
Oxacycle
Alcohol
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

cyclic ketone (CHEBI:65772 )
tertiary alcohol (CHEBI:65772 )
aromatic ether (CHEBI:65772 )
secondary alcohol (CHEBI:65772 )
organic heteropentacyclic compound (CHEBI:65772 )
rotenones (CHEBI:65772 )

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	1.43	ALOGPS
logP	1.83	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	8.46	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	133.14 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	116.8 m³·mol⁻¹	ChemAxon
Polarizability	47.63 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

C00019219

Chemspider ID

9937202

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11762505

PDB ID

Not Available

ChEBI ID

65772

Good Scents ID

Not Available

References

General References

Jang DS, Park EJ, Kang YH, Hawthorne ME, Vigo JS, Graham JG, Cabieses F, Fong HH, Mehta RG, Pezzuto JM, Kinghorn AD: Potential cncer chemopreventive flavonoids from the stems of Tephrosia toxicaria. J Nat Prod. 2003 Sep;66(9):1166-70. doi: 10.1021/np0302100. [PubMed:14510590 ]
Authors unspecified: Childhood Cancer Genomics (PDQ(R)): Health Professional Version. 2002. [PubMed:27466641 ]
Authors unspecified: Thyroid Cancer Screening (PDQ(R)): Patient Version. 2002. [PubMed:29437326 ]
Authors unspecified: Childhood Vascular Tumors Treatment (PDQ(R)): Patient Version. 2002. [PubMed:27253005 ]
Authors unspecified: Stomach (Gastric) Cancer Prevention (PDQ(R)): Patient Version. 2002. [PubMed:26389468 ]

Showing NP-Card for 4',5'-dihydro-11,5'-dihydroxy-4'-methoxytephrosin (NP0043810)

MOL for NP0043810 (4',5'-dihydro-11,5'-dihydroxy-4'-methoxytephrosin)

3D MOL for NP0043810 (4',5'-dihydro-11,5'-dihydroxy-4'-methoxytephrosin)

3D SDF for NP0043810 (4',5'-dihydro-11,5'-dihydroxy-4'-methoxytephrosin)

3D-SDF for NP0043810 (4',5'-dihydro-11,5'-dihydroxy-4'-methoxytephrosin)

PDB for NP0043810 (4',5'-dihydro-11,5'-dihydroxy-4'-methoxytephrosin)

3D PDB for NP0043810 (4',5'-dihydro-11,5'-dihydroxy-4'-methoxytephrosin)

SMILES for NP0043810 (4',5'-dihydro-11,5'-dihydroxy-4'-methoxytephrosin)

INCHI for NP0043810 (4',5'-dihydro-11,5'-dihydroxy-4'-methoxytephrosin)

Structure for NP0043810 (4',5'-dihydro-11,5'-dihydroxy-4'-methoxytephrosin)

3D Structure for NP0043810 (4',5'-dihydro-11,5'-dihydroxy-4'-methoxytephrosin)