NP-MRD: Showing NP-Card for usararotenoid C (NP0030906)

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Record Information

Version

2.0

Created at

2021-06-19 22:08:14 UTC

Updated at

2021-06-29 23:59:10 UTC

NP-MRD ID

NP0030906

Secondary Accession Numbers

None

Natural Product Identification

Common Name

usararotenoid C

Provided By

JEOL Database JEOL Logo

Description

Usararotenoid C 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. usararotenoid C is found in Millettia usaramensis and Millettia usaramensis subsp. usaramensis . usararotenoid C was first documented in 2003 (Yenesew, A., et al.). Based on a literature review very few articles have been published on Usararotenoid C.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202100083D          

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     RDKit          3D

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  Mrv1652306202100083D          

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    0.8447    3.3896    0.6343 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7321    3.0614   -3.2202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0211    1.5571   -3.0292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2236    2.8234   -0.7832 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2781    1.9485   -7.0331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2331    3.6364   -6.7800 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  4  2  0  0  0  0
 23 22  2  0  0  0  0
 22 21  1  0  0  0  0
  7 14  1  0  0  0  0
 20 19  1  0  0  0  0
 19 18  2  0  0  0  0
 20 21  2  0  0  0  0
  6 26  1  0  0  0  0
 26 24  1  0  0  0  0
 15 14  1  0  0  0  0
 15 24  1  0  0  0  0
  7  8  2  0  0  0  0
 21 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 20  1  0  0  0  0
  8  3  1  0  0  0  0
  8  9  1  0  0  0  0
  7  6  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  3  0  0  0
 15 16  1  0  0  0  0
 11 12  1  0  0  0  0
 24 23  1  0  0  0  0
 11 13  1  0  0  0  0
 18 17  1  0  0  0  0
  3  2  1  0  0  0  0
 17 16  1  0  0  0  0
  2  1  1  0  0  0  0
  4  5  1  0  0  0  0
 26 27  2  0  0  0  0
  5  6  2  0  0  0  0
 15 45  1  6  0  0  0
 18 23  1  0  0  0  0
 24 25  1  1  0  0  0
  4 34  1  0  0  0  0
  5 35  1  0  0  0  0
 16 46  1  0  0  0  0
 16 47  1  0  0  0  0
 22 49  1  0  0  0  0
 19 48  1  0  0  0  0
 29 51  1  0  0  0  0
 29 52  1  0  0  0  0
  9 36  1  0  0  0  0
  9 37  1  0  0  0  0
 10 38  1  0  0  0  0
 12 39  1  0  0  0  0
 12 40  1  0  0  0  0
 12 41  1  0  0  0  0
 13 42  1  0  0  0  0
 13 43  1  0  0  0  0
 13 44  1  0  0  0  0
  1 31  1  0  0  0  0
  1 32  1  0  0  0  0
  1 33  1  0  0  0  0
 25 50  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0030906

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@]12C(=O)C3=C([H])C([H])=C(OC([H])([H])[H])C(=C3O[C@]1([H])C([H])([H])OC1=C([H])C3=C(OC([H])([H])O3)C([H])=C21)C([H])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C23H22O7/c1-12(2)4-5-13-16(26-3)7-6-14-21(13)30-20-10-27-17-9-19-18(28-11-29-19)8-15(17)23(20,25)22(14)24/h4,6-9,20,25H,5,10-11H2,1-3H3/t20-,23+/m1/s1

> <INCHI_KEY>
ZFSLOJRJABHMTL-OFNKIYASSA-N

> <FORMULA>
C23H22O7

> <MOLECULAR_WEIGHT>
410.422

> <EXACT_MASS>
410.136553048

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
43.457516802117524

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,13R)-1-hydroxy-17-methoxy-16-(3-methylbut-2-en-1-yl)-5,7,11,14-tetraoxapentacyclo[11.8.0.0^{2,10}.0^{4,8}.0^{15,20}]henicosa-2,4(8),9,15,17,19-hexaen-21-one

> <ALOGPS_LOGP>
2.00

> <JCHEM_LOGP>
3.3215364783333325

> <ALOGPS_LOGS>
-4.11

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.05788550392876

> <JCHEM_PKA_STRONGEST_BASIC>
-4.2514874312451

> <JCHEM_POLAR_SURFACE_AREA>
83.45000000000002

> <JCHEM_REFRACTIVITY>
107.61709999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.17e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,13R)-1-hydroxy-17-methoxy-16-(3-methylbut-2-en-1-yl)-5,7,11,14-tetraoxapentacyclo[11.8.0.0^{2,10}.0^{4,8}.0^{15,20}]henicosa-2,4(8),9,15,17,19-hexaen-21-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 52 56  0  0  0  0  0  0  0  0999 V2000
   -3.0980   -3.1138    4.9158 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1930   -2.0393    4.6965 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1048   -1.5262    3.4278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8420   -1.9991    2.3363 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6878   -1.4224    1.0747 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7885   -0.3703    0.8944 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0308    0.1005    1.9716 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1957   -0.4579    3.2547 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3666    0.0489    4.4213 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9217   -0.7179    4.5779 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1876   -0.2682    4.4679 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5859    1.1436    4.1404 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3507   -1.2034    4.6760 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1226    1.1227    1.8381 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3531    1.2610    0.4945 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3243    2.4262    0.4187 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9687    2.4806   -0.8557 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1303    2.3640   -1.9353 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7036    2.7243   -3.1600 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9148    2.6547   -4.2844 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3932    2.2457   -4.2191 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9819    1.8716   -3.0281 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2074    1.9019   -1.8512 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7864    1.5254   -0.4972 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5957    2.6301   -0.0641 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6547    0.2665   -0.4397 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2839   -0.1967   -1.3880 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0032    2.2618   -5.4342 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0781    2.7147   -6.2751 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2971    2.9756   -5.5488 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1293   -2.8098    4.7091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8168   -3.9929    4.3270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0385   -3.3894    5.9731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5504   -2.8157    2.4329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2775   -1.7942    0.2389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9392   -0.0420    5.3531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2064    1.1263    4.3202 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7689   -1.7684    4.8280 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7392    1.8086    3.9619 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1692    1.5692    4.9637 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2055    1.1577    3.2375 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9642   -1.2523    3.7704 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0287   -2.2227    4.9141 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9767   -0.8514    5.5026 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9028    0.3461    0.2201 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1072    2.3067    1.1759 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8447    3.3896    0.6343 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7321    3.0614   -3.2202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0211    1.5571   -3.0292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2236    2.8234   -0.7832 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2781    1.9485   -7.0331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2331    3.6364   -6.7800 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  4  2  0
 23 22  2  0
 22 21  1  0
  7 14  1  0
 20 19  1  0
 19 18  2  0
 20 21  2  0
  6 26  1  0
 26 24  1  0
 15 14  1  0
 15 24  1  0
  7  8  2  0
 21 28  1  0
 28 29  1  0
 29 30  1  0
 30 20  1  0
  8  3  1  0
  8  9  1  0
  7  6  1  0
  9 10  1  0
 10 11  2  3
 15 16  1  0
 11 12  1  0
 24 23  1  0
 11 13  1  0
 18 17  1  0
  3  2  1  0
 17 16  1  0
  2  1  1  0
  4  5  1  0
 26 27  2  0
  5  6  2  0
 15 45  1  6
 18 23  1  0
 24 25  1  1
  4 34  1  0
  5 35  1  0
 16 46  1  0
 16 47  1  0
 22 49  1  0
 19 48  1  0
 29 51  1  0
 29 52  1  0
  9 36  1  0
  9 37  1  0
 10 38  1  0
 12 39  1  0
 12 40  1  0
 12 41  1  0
 13 42  1  0
 13 43  1  0
 13 44  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
 25 50  1  0
M  END

HEADER    PROTEIN                                 20-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-21         0                                  
HETATM    1  C   UNK     0      -3.098  -3.114   4.916  0.00  0.00           C+0
HETATM    2  O   UNK     0      -2.193  -2.039   4.697  0.00  0.00           O+0
HETATM    3  C   UNK     0      -2.105  -1.526   3.428  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.842  -1.999   2.336  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.688  -1.422   1.075  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.789  -0.370   0.894  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.031   0.101   1.972  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.196  -0.458   3.255  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.367   0.049   4.421  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.922  -0.718   4.578  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.188  -0.268   4.468  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.586   1.144   4.140  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.351  -1.203   4.676  0.00  0.00           C+0
HETATM   14  O   UNK     0      -0.123   1.123   1.838  0.00  0.00           O+0
HETATM   15  C   UNK     0       0.353   1.261   0.495  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.324   2.426   0.419  0.00  0.00           C+0
HETATM   17  O   UNK     0       1.969   2.481  -0.856  0.00  0.00           O+0
HETATM   18  C   UNK     0       1.130   2.364  -1.935  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.704   2.724  -3.160  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.915   2.655  -4.284  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.393   2.246  -4.219  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.982   1.872  -3.028  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.207   1.902  -1.851  0.00  0.00           C+0
HETATM   24  C   UNK     0      -0.786   1.525  -0.497  0.00  0.00           C+0
HETATM   25  O   UNK     0      -1.596   2.630  -0.064  0.00  0.00           O+0
HETATM   26  C   UNK     0      -1.655   0.267  -0.440  0.00  0.00           C+0
HETATM   27  O   UNK     0      -2.284  -0.197  -1.388  0.00  0.00           O+0
HETATM   28  O   UNK     0      -1.003   2.262  -5.434  0.00  0.00           O+0
HETATM   29  C   UNK     0       0.078   2.715  -6.275  0.00  0.00           C+0
HETATM   30  O   UNK     0       1.297   2.976  -5.549  0.00  0.00           O+0
HETATM   31  H   UNK     0      -4.129  -2.810   4.709  0.00  0.00           H+0
HETATM   32  H   UNK     0      -2.817  -3.993   4.327  0.00  0.00           H+0
HETATM   33  H   UNK     0      -3.038  -3.389   5.973  0.00  0.00           H+0
HETATM   34  H   UNK     0      -3.550  -2.816   2.433  0.00  0.00           H+0
HETATM   35  H   UNK     0      -3.277  -1.794   0.239  0.00  0.00           H+0
HETATM   36  H   UNK     0      -0.939  -0.042   5.353  0.00  0.00           H+0
HETATM   37  H   UNK     0      -0.206   1.126   4.320  0.00  0.00           H+0
HETATM   38  H   UNK     0       0.769  -1.768   4.828  0.00  0.00           H+0
HETATM   39  H   UNK     0       1.739   1.809   3.962  0.00  0.00           H+0
HETATM   40  H   UNK     0       3.169   1.569   4.964  0.00  0.00           H+0
HETATM   41  H   UNK     0       3.205   1.158   3.237  0.00  0.00           H+0
HETATM   42  H   UNK     0       3.964  -1.252   3.770  0.00  0.00           H+0
HETATM   43  H   UNK     0       3.029  -2.223   4.914  0.00  0.00           H+0
HETATM   44  H   UNK     0       3.977  -0.851   5.503  0.00  0.00           H+0
HETATM   45  H   UNK     0       0.903   0.346   0.220  0.00  0.00           H+0
HETATM   46  H   UNK     0       2.107   2.307   1.176  0.00  0.00           H+0
HETATM   47  H   UNK     0       0.845   3.390   0.634  0.00  0.00           H+0
HETATM   48  H   UNK     0       2.732   3.061  -3.220  0.00  0.00           H+0
HETATM   49  H   UNK     0      -2.021   1.557  -3.029  0.00  0.00           H+0
HETATM   50  H   UNK     0      -2.224   2.823  -0.783  0.00  0.00           H+0
HETATM   51  H   UNK     0       0.278   1.948  -7.033  0.00  0.00           H+0
HETATM   52  H   UNK     0      -0.233   3.636  -6.780  0.00  0.00           H+0
CONECT    1    2   31   32   33                                             
CONECT    2    3    1                                                       
CONECT    3    4    8    2                                                  
CONECT    4    3    5   34                                                  
CONECT    5    4    6   35                                                  
CONECT    6   26    7    5                                                  
CONECT    7   14    8    6                                                  
CONECT    8    7    3    9                                                  
CONECT    9    8   10   36   37                                             
CONECT   10    9   11   38                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11   39   40   41                                             
CONECT   13   11   42   43   44                                             
CONECT   14    7   15                                                       
CONECT   15   14   24   16   45                                             
CONECT   16   15   17   46   47                                             
CONECT   17   18   16                                                       
CONECT   18   19   17   23                                                  
CONECT   19   20   18   48                                                  
CONECT   20   19   21   30                                                  
CONECT   21   22   20   28                                                  
CONECT   22   23   21   49                                                  
CONECT   23   22   24   18                                                  
CONECT   24   26   15   23   25                                             
CONECT   25   24   50                                                       
CONECT   26    6   24   27                                                  
CONECT   27   26                                                            
CONECT   28   21   29                                                       
CONECT   29   28   30   51   52                                             
CONECT   30   29   20                                                       
CONECT   31    1                                                            
CONECT   32    1                                                            
CONECT   33    1                                                            
CONECT   34    4                                                            
CONECT   35    5                                                            
CONECT   36    9                                                            
CONECT   37    9                                                            
CONECT   38   10                                                            
CONECT   39   12                                                            
CONECT   40   12                                                            
CONECT   41   12                                                            
CONECT   42   13                                                            
CONECT   43   13                                                            
CONECT   44   13                                                            
CONECT   45   15                                                            
CONECT   46   16                                                            
CONECT   47   16                                                            
CONECT   48   19                                                            
CONECT   49   22                                                            
CONECT   50   25                                                            
CONECT   51   29                                                            
CONECT   52   29                                                            
MASTER        0    0    0    0    0    0    0    0   52    0  112    0
END

RDKit          3D

52 56  0  0  0  0  0  0  0  0999 V2000
   -3.0980   -3.1138    4.9158 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1930   -2.0393    4.6965 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1048   -1.5262    3.4278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8420   -1.9991    2.3363 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6878   -1.4224    1.0747 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7885   -0.3703    0.8944 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0308    0.1005    1.9716 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1957   -0.4579    3.2547 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3666    0.0489    4.4213 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9217   -0.7179    4.5779 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1876   -0.2682    4.4679 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5859    1.1436    4.1404 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3507   -1.2034    4.6760 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1226    1.1227    1.8381 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3531    1.2610    0.4945 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3243    2.4262    0.4187 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9687    2.4806   -0.8557 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1303    2.3640   -1.9353 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7036    2.7243   -3.1600 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9148    2.6547   -4.2844 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3932    2.2457   -4.2191 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9819    1.8716   -3.0281 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2074    1.9019   -1.8512 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7864    1.5254   -0.4972 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5957    2.6301   -0.0641 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6547    0.2665   -0.4397 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2839   -0.1967   -1.3880 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0032    2.2618   -5.4342 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0781    2.7147   -6.2751 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2971    2.9756   -5.5488 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1293   -2.8098    4.7091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8168   -3.9929    4.3270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0385   -3.3894    5.9731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5504   -2.8157    2.4329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2775   -1.7942    0.2389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9392   -0.0420    5.3531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2064    1.1263    4.3202 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7689   -1.7684    4.8280 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7392    1.8086    3.9619 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1692    1.5692    4.9637 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2055    1.1577    3.2375 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9642   -1.2523    3.7704 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0287   -2.2227    4.9141 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9767   -0.8514    5.5026 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9028    0.3461    0.2201 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1072    2.3067    1.1759 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8447    3.3896    0.6343 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7321    3.0614   -3.2202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0211    1.5571   -3.0292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2236    2.8234   -0.7832 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2781    1.9485   -7.0331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2331    3.6364   -6.7800 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  4  2  0
 23 22  2  0
 22 21  1  0
  7 14  1  0
 20 19  1  0
 19 18  2  0
 20 21  2  0
  6 26  1  0
 26 24  1  0
 15 14  1  0
 15 24  1  0
  7  8  2  0
 21 28  1  0
 28 29  1  0
 29 30  1  0
 30 20  1  0
  8  3  1  0
  8  9  1  0
  7  6  1  0
  9 10  1  0
 10 11  2  3
 15 16  1  0
 11 12  1  0
 24 23  1  0
 11 13  1  0
 18 17  1  0
  3  2  1  0
 17 16  1  0
  2  1  1  0
  4  5  1  0
 26 27  2  0
  5  6  2  0
 15 45  1  6
 18 23  1  0
 24 25  1  1
  4 34  1  0
  5 35  1  0
 16 46  1  0
 16 47  1  0
 22 49  1  0
 19 48  1  0
 29 51  1  0
 29 52  1  0
  9 36  1  0
  9 37  1  0
 10 38  1  0
 12 39  1  0
 12 40  1  0
 12 41  1  0
 13 42  1  0
 13 43  1  0
 13 44  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
 25 50  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₃H₂₂O₇

Average Mass

410.4220 Da

Monoisotopic Mass

410.13655 Da

IUPAC Name

(1S,13R)-1-hydroxy-17-methoxy-16-(3-methylbut-2-en-1-yl)-5,7,11,14-tetraoxapentacyclo[11.8.0.0^{2,10}.0^{4,8}.0^{15,20}]henicosa-2,4(8),9,15,17,19-hexaen-21-one

Traditional Name

(1S,13R)-1-hydroxy-17-methoxy-16-(3-methylbut-2-en-1-yl)-5,7,11,14-tetraoxapentacyclo[11.8.0.0^{2,10}.0^{4,8}.0^{15,20}]henicosa-2,4(8),9,15,17,19-hexaen-21-one

CAS Registry Number

Not Available

SMILES

[H]O[C@]12C(=O)C3=C([H])C([H])=C(OC([H])([H])[H])C(=C3O[C@]1([H])C([H])([H])OC1=C([H])C3=C(OC([H])([H])O3)C([H])=C21)C([H])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C23H22O7/c1-12(2)4-5-13-16(26-3)7-6-14-21(13)30-20-10-27-17-9-19-18(28-11-29-19)8-15(17)23(20,25)22(14)24/h4,6-9,20,25H,5,10-11H2,1-3H3/t20-,23+/m1/s1

InChI Key

ZFSLOJRJABHMTL-OFNKIYASSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CDCl₃, 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
Millettia usaramensis	JEOL database	Yenesew, A., et al, Phytochemistry 64, 773 (2003)
Millettia usaramensis subsp. usaramensis	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

Rotenone or derivatives
8-prenylated isoflavanone
Isoflavanone
Isoflavan
Chromone
Chromane
Benzopyran
1-benzopyran
Benzodioxole
Anisole
Aryl alkyl ketone
Aryl ketone
Alkyl aryl ether
Benzenoid
Tertiary alcohol
Ketone
Organoheterocyclic compound
Ether
Oxacycle
Acetal
Organooxygen compound
Alcohol
Hydrocarbon derivative
Organic oxide
Organic oxygen 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	ALOGPS
logP	3.32	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	11.06	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	3	ChemAxon
Refractivity	107.62 m³·mol⁻¹	ChemAxon
Polarizability	43.46 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

556990

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

641748

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Yenesew, A., et al. (2003). Yenesew, A., et al, Phytochemistry 64, 773 (2003). Phytochem..

Showing NP-Card for usararotenoid C (NP0030906)

MOL for NP0030906 (usararotenoid C)

3D MOL for NP0030906 (usararotenoid C)

3D SDF for NP0030906 (usararotenoid C)

3D-SDF for NP0030906 (usararotenoid C)

PDB for NP0030906 (usararotenoid C)

3D PDB for NP0030906 (usararotenoid C)

SMILES for NP0030906 (usararotenoid C)

INCHI for NP0030906 (usararotenoid C)

Structure for NP0030906 (usararotenoid C)

3D Structure for NP0030906 (usararotenoid C)