NP-MRD: Showing NP-Card for rubescin A (NP0042817)

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Record Information

Version

1.0

Created at

2021-06-21 00:23:23 UTC

Updated at

2021-06-30 00:18:08 UTC

NP-MRD ID

NP0042817

Secondary Accession Numbers

None

Natural Product Identification

Common Name

rubescin A

Provided By

JEOL Database JEOL Logo

Description

(1R,2R,5S,6R,10R,15R)-6-(furan-3-yl)-1,5,10,15-tetramethyl-13-oxapentacyclo[10.6.1.0²,¹⁰.0⁵,⁹.0¹⁵,¹⁹]Nonadeca-8,12(19),16-triene-11,18-dione belongs to the class of organic compounds known as 17-furanylsteroids and derivatives. These are steroidal compounds having a furanyl group linked to the steroid backbone at the C17 position. rubescin A is found in Trichilia rubescens (Meliaceae). It was first documented in 2013 (Tontsa, A. T., et al.). Based on a literature review very few articles have been published on (1R,2R,5S,6R,10R,15R)-6-(furan-3-yl)-1,5,10,15-tetramethyl-13-oxapentacyclo[10.6.1.0²,¹⁰.0⁵,⁹.0¹⁵,¹⁹]Nonadeca-8,12(19),16-triene-11,18-dione.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306212102233D          

 58 63  0  0  0  0            999 V2000
   -1.1356   -0.5856    3.3150 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0516   -0.0003    2.2197 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5452    1.3552    1.7157 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2781    1.2873    0.8497 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0675   -0.1042    0.2498 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2229   -0.9166   -0.1440 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9643   -0.3044   -1.3514 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7934   -2.3483   -0.5630 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4508   -3.3657   -0.3524 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4649   -2.4514   -1.3473 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2935   -1.4224   -1.5153 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4687   -1.8902   -2.3195 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3908   -1.4786   -3.7964 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7561   -1.4249   -1.6960 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8202   -0.5327   -0.6972 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5981    0.1118   -0.1281 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7531    0.8350    0.8552 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2232   -0.0758   -0.8383 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1100    1.0791   -1.8468 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2635   -3.4185   -2.1927 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8638   -3.6487   -1.9300 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1983   -0.9466    1.0359 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3345   -1.6593    1.1473 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1228   -1.2960    2.3642 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5409    0.0867    2.6975 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.7705    0.5603    4.1017 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9054    1.9170    4.5226 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1021    1.8922    5.8823 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1013    0.6146    6.3351 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9024   -0.1855    5.2578 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0517    0.1005    4.1652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1159   -0.7712    2.9747 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5171   -1.5413    3.6924 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.3261    1.8354    1.1092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4033    2.0327    0.0583 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5611    1.6365    1.4602 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.3997   -0.4115   -2.2822 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9203   -0.8111   -1.5337 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1813    0.7585   -1.2043 H   0  0  0  0  0  0  0  0  0  0  0  0
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 12 20  1  0  0  0  0
  5 38  1  1  0  0  0
 12 13  1  6  0  0  0
 18 19  1  6  0  0  0
  6  7  1  6  0  0  0
  2 22  1  0  0  0  0
  5  6  1  0  0  0  0
  5  4  1  0  0  0  0
  6 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
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 25  2  1  0  0  0  0
  3  2  1  0  0  0  0
  3  4  1  0  0  0  0
 18 11  1  0  0  0  0
 18  5  1  0  0  0  0
 16 17  2  0  0  0  0
 11 10  2  0  0  0  0
  8  9  2  0  0  0  0
 10  8  1  0  0  0  0
 10 21  1  0  0  0  0
 20 21  1  0  0  0  0
  8  6  1  0  0  0  0
 25 26  1  0  0  0  0
 26 30  2  0  0  0  0
 15 14  2  0  0  0  0
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 14 12  1  0  0  0  0
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 30 29  1  0  0  0  0
 29 28  1  0  0  0  0
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  1 33  1  0  0  0  0
M  END

     RDKit          3D

 58 63  0  0  0  0  0  0  0  0999 V2000
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   -2.0516   -0.0003    2.2197 C   0  0  1  0  0  0  0  0  0  0  0  0
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    0.0675   -0.1042    0.2498 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2229   -0.9166   -0.1440 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -0.7934   -2.3483   -0.5630 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.3908   -1.4786   -3.7964 C   0  0  0  0  0  0  0  0  0  0  0  0
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  1 31  1  0
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M  END


  Mrv1652306212102233D          

 58 63  0  0  0  0            999 V2000
   -1.1356   -0.5856    3.3150 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0516   -0.0003    2.2197 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5452    1.3552    1.7157 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2781    1.2873    0.8497 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0675   -0.1042    0.2498 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2229   -0.9166   -0.1440 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9643   -0.3044   -1.3514 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7934   -2.3483   -0.5630 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4508   -3.3657   -0.3524 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4649   -2.4514   -1.3473 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2935   -1.4224   -1.5153 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4687   -1.8902   -2.3195 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3908   -1.4786   -3.7964 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7561   -1.4249   -1.6960 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8202   -0.5327   -0.6972 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5981    0.1118   -0.1281 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7531    0.8350    0.8552 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.8638   -3.6487   -1.9300 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1983   -0.9466    1.0359 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3345   -1.6593    1.1473 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.5409    0.0867    2.6975 C   0  0  1  0  0  0  0  0  0  0  0  0
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    0.5162   -0.6752    1.0746 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.9445    1.0856   -2.5542 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.5417   -3.9635   -3.1016 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.0715    0.8033    2.0475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8624    2.8038    3.9056 H   0  0  0  0  0  0  0  0  0  0  0  0
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 12 20  1  0  0  0  0
  5 38  1  1  0  0  0
 12 13  1  6  0  0  0
 18 19  1  6  0  0  0
  6  7  1  6  0  0  0
  2 22  1  0  0  0  0
  5  6  1  0  0  0  0
  5  4  1  0  0  0  0
  6 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25  2  1  0  0  0  0
  3  2  1  0  0  0  0
  3  4  1  0  0  0  0
 18 11  1  0  0  0  0
 18  5  1  0  0  0  0
 16 17  2  0  0  0  0
 11 10  2  0  0  0  0
  8  9  2  0  0  0  0
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 10 21  1  0  0  0  0
 20 21  1  0  0  0  0
  8  6  1  0  0  0  0
 25 26  1  0  0  0  0
 26 30  2  0  0  0  0
 15 14  2  0  0  0  0
 15 16  1  0  0  0  0
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 30 29  1  0  0  0  0
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 28 27  2  0  0  0  0
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  2  1  1  1  0  0  0
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  7 39  1  0  0  0  0
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 23 52  1  0  0  0  0
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  3 34  1  0  0  0  0
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  1 31  1  0  0  0  0
  1 32  1  0  0  0  0
  1 33  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0042817

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]C1=C([H])C(=C([H])O1)[C@]1([H])C([H])([H])C([H])=C2[C@@]1(C([H])([H])[H])C([H])([H])C([H])([H])[C@@]1([H])[C@]2(C(=O)C2=C3[C@](C([H])=C([H])C(=O)[C@]13C([H])([H])[H])(C([H])([H])[H])C([H])([H])O2)C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C26H28O4/c1-23-10-8-19(27)26(4)18-7-11-24(2)16(15-9-12-29-13-15)5-6-17(24)25(18,3)22(28)20(21(23)26)30-14-23/h6,8-10,12-13,16,18H,5,7,11,14H2,1-4H3/t16-,18-,23-,24-,25-,26-/m0/s1

> <INCHI_KEY>
MHHWKYUSJKVZMV-RUEDEKCXSA-N

> <FORMULA>
C26H28O4

> <MOLECULAR_WEIGHT>
404.506

> <EXACT_MASS>
404.198759382

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
58

> <JCHEM_AVERAGE_POLARIZABILITY>
44.6547009726273

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,2R,5S,6R,10R,15R)-6-(furan-3-yl)-1,5,10,15-tetramethyl-13-oxapentacyclo[10.6.1.0^{2,10}.0^{5,9}.0^{15,19}]nonadeca-8,12(19),16-triene-11,18-dione

> <ALOGPS_LOGP>
4.95

> <JCHEM_LOGP>
4.313286921333332

> <ALOGPS_LOGS>
-4.48

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8005265716072762

> <JCHEM_POLAR_SURFACE_AREA>
56.510000000000005

> <JCHEM_REFRACTIVITY>
116.4904

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.33e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,5S,6R,10R,15R)-6-(furan-3-yl)-1,5,10,15-tetramethyl-13-oxapentacyclo[10.6.1.0^{2,10}.0^{5,9}.0^{15,19}]nonadeca-8,12(19),16-triene-11,18-dione

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

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  1 32  1  0
  1 33  1  0
M  END

HEADER    PROTEIN                                 21-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-JUN-21         0                                  
HETATM    1  C   UNK     0      -1.136  -0.586   3.315  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.052  -0.000   2.220  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.545   1.355   1.716  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.278   1.287   0.850  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.068  -0.104   0.250  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.223  -0.917  -0.144  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.964  -0.304  -1.351  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.793  -2.348  -0.563  0.00  0.00           C+0
HETATM    9  O   UNK     0      -1.451  -3.366  -0.352  0.00  0.00           O+0
HETATM   10  C   UNK     0       0.465  -2.451  -1.347  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.294  -1.422  -1.515  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.469  -1.890  -2.320  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.391  -1.479  -3.796  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.756  -1.425  -1.696  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.820  -0.533  -0.697  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.598   0.112  -0.128  0.00  0.00           C+0
HETATM   17  O   UNK     0       2.753   0.835   0.855  0.00  0.00           O+0
HETATM   18  C   UNK     0       1.223  -0.076  -0.838  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.110   1.079  -1.847  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.264  -3.418  -2.193  0.00  0.00           C+0
HETATM   21  O   UNK     0       0.864  -3.649  -1.930  0.00  0.00           O+0
HETATM   22  C   UNK     0      -2.198  -0.947   1.036  0.00  0.00           C+0
HETATM   23  C   UNK     0      -3.334  -1.659   1.147  0.00  0.00           C+0
HETATM   24  C   UNK     0      -4.123  -1.296   2.364  0.00  0.00           C+0
HETATM   25  C   UNK     0      -3.541   0.087   2.697  0.00  0.00           C+0
HETATM   26  C   UNK     0      -3.771   0.560   4.102  0.00  0.00           C+0
HETATM   27  C   UNK     0      -3.905   1.917   4.523  0.00  0.00           C+0
HETATM   28  C   UNK     0      -4.102   1.892   5.882  0.00  0.00           C+0
HETATM   29  O   UNK     0      -4.101   0.615   6.335  0.00  0.00           O+0
HETATM   30  C   UNK     0      -3.902  -0.186   5.258  0.00  0.00           C+0
HETATM   31  H   UNK     0      -1.052   0.101   4.165  0.00  0.00           H+0
HETATM   32  H   UNK     0      -0.116  -0.771   2.975  0.00  0.00           H+0
HETATM   33  H   UNK     0      -1.517  -1.541   3.692  0.00  0.00           H+0
HETATM   34  H   UNK     0      -1.374   2.040   2.556  0.00  0.00           H+0
HETATM   35  H   UNK     0      -2.326   1.835   1.109  0.00  0.00           H+0
HETATM   36  H   UNK     0      -0.403   2.033   0.058  0.00  0.00           H+0
HETATM   37  H   UNK     0       0.561   1.637   1.460  0.00  0.00           H+0
HETATM   38  H   UNK     0       0.516  -0.675   1.075  0.00  0.00           H+0
HETATM   39  H   UNK     0      -1.400  -0.412  -2.282  0.00  0.00           H+0
HETATM   40  H   UNK     0      -2.920  -0.811  -1.534  0.00  0.00           H+0
HETATM   41  H   UNK     0      -2.181   0.759  -1.204  0.00  0.00           H+0
HETATM   42  H   UNK     0       2.578  -0.411  -3.943  0.00  0.00           H+0
HETATM   43  H   UNK     0       1.409  -1.705  -4.229  0.00  0.00           H+0
HETATM   44  H   UNK     0       3.142  -2.014  -4.390  0.00  0.00           H+0
HETATM   45  H   UNK     0       4.682  -1.850  -2.079  0.00  0.00           H+0
HETATM   46  H   UNK     0       4.763  -0.233  -0.251  0.00  0.00           H+0
HETATM   47  H   UNK     0       0.189   1.043  -2.431  0.00  0.00           H+0
HETATM   48  H   UNK     0       1.944   1.086  -2.554  0.00  0.00           H+0
HETATM   49  H   UNK     0       1.164   2.055  -1.353  0.00  0.00           H+0
HETATM   50  H   UNK     0       2.542  -3.963  -3.102  0.00  0.00           H+0
HETATM   51  H   UNK     0       2.834  -3.850  -1.359  0.00  0.00           H+0
HETATM   52  H   UNK     0      -3.681  -2.394   0.431  0.00  0.00           H+0
HETATM   53  H   UNK     0      -5.193  -1.226   2.144  0.00  0.00           H+0
HETATM   54  H   UNK     0      -3.973  -2.046   3.147  0.00  0.00           H+0
HETATM   55  H   UNK     0      -4.072   0.803   2.047  0.00  0.00           H+0
HETATM   56  H   UNK     0      -3.862   2.804   3.906  0.00  0.00           H+0
HETATM   57  H   UNK     0      -4.252   2.655   6.633  0.00  0.00           H+0
HETATM   58  H   UNK     0      -3.875  -1.245   5.472  0.00  0.00           H+0
CONECT    1    2   31   32   33                                             
CONECT    2   22   25    3    1                                             
CONECT    3    2    4   34   35                                             
CONECT    4    5    3   36   37                                             
CONECT    5   38    6    4   18                                             
CONECT    6    7    5   22    8                                             
CONECT    7    6   39   40   41                                             
CONECT    8    9   10    6                                                  
CONECT    9    8                                                            
CONECT   10   11    8   21                                                  
CONECT   11   18   10   12                                                  
CONECT   12   20   13   14   11                                             
CONECT   13   12   42   43   44                                             
CONECT   14   15   12   45                                                  
CONECT   15   14   16   46                                                  
CONECT   16   17   15   18                                                  
CONECT   17   16                                                            
CONECT   18   19   11    5   16                                             
CONECT   19   18   47   48   49                                             
CONECT   20   12   21   50   51                                             
CONECT   21   10   20                                                       
CONECT   22    2    6   23                                                  
CONECT   23   22   24   52                                                  
CONECT   24   23   25   53   54                                             
CONECT   25   24    2   26   55                                             
CONECT   26   25   30   27                                                  
CONECT   27   28   26   56                                                  
CONECT   28   29   27   57                                                  
CONECT   29   30   28                                                       
CONECT   30   26   29   58                                                  
CONECT   31    1                                                            
CONECT   32    1                                                            
CONECT   33    1                                                            
CONECT   34    3                                                            
CONECT   35    3                                                            
CONECT   36    4                                                            
CONECT   37    4                                                            
CONECT   38    5                                                            
CONECT   39    7                                                            
CONECT   40    7                                                            
CONECT   41    7                                                            
CONECT   42   13                                                            
CONECT   43   13                                                            
CONECT   44   13                                                            
CONECT   45   14                                                            
CONECT   46   15                                                            
CONECT   47   19                                                            
CONECT   48   19                                                            
CONECT   49   19                                                            
CONECT   50   20                                                            
CONECT   51   20                                                            
CONECT   52   23                                                            
CONECT   53   24                                                            
CONECT   54   24                                                            
CONECT   55   25                                                            
CONECT   56   27                                                            
CONECT   57   28                                                            
CONECT   58   30                                                            
MASTER        0    0    0    0    0    0    0    0   58    0  126    0
END

RDKit          3D

58 63  0  0  0  0  0  0  0  0999 V2000
   -1.1356   -0.5856    3.3150 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0516   -0.0003    2.2197 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5452    1.3552    1.7157 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2781    1.2873    0.8497 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0675   -0.1042    0.2498 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2229   -0.9166   -0.1440 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9643   -0.3044   -1.3514 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7934   -2.3483   -0.5630 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4508   -3.3657   -0.3524 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4649   -2.4514   -1.3473 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2935   -1.4224   -1.5153 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4687   -1.8902   -2.3195 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3908   -1.4786   -3.7964 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7561   -1.4249   -1.6960 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8202   -0.5327   -0.6972 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5981    0.1118   -0.1281 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7531    0.8350    0.8552 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2232   -0.0758   -0.8383 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1100    1.0791   -1.8468 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2635   -3.4185   -2.1927 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8638   -3.6487   -1.9300 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1983   -0.9466    1.0359 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3345   -1.6593    1.1473 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1228   -1.2960    2.3642 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5409    0.0867    2.6975 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.7705    0.5603    4.1017 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9054    1.9170    4.5226 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1021    1.8922    5.8823 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1013    0.6146    6.3351 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9024   -0.1855    5.2578 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0517    0.1005    4.1652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1159   -0.7712    2.9747 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5171   -1.5413    3.6924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3737    2.0399    2.5559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3261    1.8354    1.1092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4033    2.0327    0.0583 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5611    1.6365    1.4602 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5162   -0.6752    1.0746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3997   -0.4115   -2.2822 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9203   -0.8111   -1.5337 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1813    0.7585   -1.2043 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5780   -0.4110   -3.9433 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4088   -1.7049   -4.2285 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1424   -2.0136   -4.3897 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6821   -1.8501   -2.0785 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7625   -0.2334   -0.2508 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1889    1.0434   -2.4312 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9445    1.0856   -2.5542 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1639    2.0549   -1.3526 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5417   -3.9635   -3.1016 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8342   -3.8498   -1.3588 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6808   -2.3944    0.4311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1928   -1.2256    2.1438 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9733   -2.0465    3.1467 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0715    0.8033    2.0475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8624    2.8038    3.9056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2516    2.6551    6.6333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8749   -1.2452    5.4723 H   0  0  0  0  0  0  0  0  0  0  0  0
 12 20  1  0
  5 38  1  1
 12 13  1  6
 18 19  1  6
  6  7  1  6
  2 22  1  0
  5  6  1  0
  5  4  1  0
  6 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  1  0
 25  2  1  0
  3  2  1  0
  3  4  1  0
 18 11  1  0
 18  5  1  0
 16 17  2  0
 11 10  2  0
  8  9  2  0
 10  8  1  0
 10 21  1  0
 20 21  1  0
  8  6  1  0
 25 26  1  0
 26 30  2  0
 15 14  2  0
 15 16  1  0
 14 12  1  0
 12 11  1  0
 30 29  1  0
 29 28  1  0
 28 27  2  0
 27 26  1  0
 18 16  1  0
  2  1  1  1
  4 36  1  0
  4 37  1  0
 15 46  1  0
 14 45  1  0
 20 50  1  0
 20 51  1  0
 13 42  1  0
 13 43  1  0
 13 44  1  0
 19 47  1  0
 19 48  1  0
 19 49  1  0
  7 39  1  0
  7 40  1  0
  7 41  1  0
 23 52  1  0
 24 53  1  0
 24 54  1  0
 25 55  1  6
  3 34  1  0
  3 35  1  0
 30 58  1  0
 28 57  1  0
 27 56  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₂₈O₄

Average Mass

404.5060 Da

Monoisotopic Mass

404.19876 Da

IUPAC Name

(1R,2R,5S,6R,10R,15R)-6-(furan-3-yl)-1,5,10,15-tetramethyl-13-oxapentacyclo[10.6.1.0^{2,10}.0^{5,9}.0^{15,19}]nonadeca-8,12(19),16-triene-11,18-dione

Traditional Name

(1R,2R,5S,6R,10R,15R)-6-(furan-3-yl)-1,5,10,15-tetramethyl-13-oxapentacyclo[10.6.1.0^{2,10}.0^{5,9}.0^{15,19}]nonadeca-8,12(19),16-triene-11,18-dione

CAS Registry Number

Not Available

SMILES

[H]C1=C([H])C(=C([H])O1)[C@]1([H])C([H])([H])C([H])=C2[C@@]1(C([H])([H])[H])C([H])([H])C([H])([H])[C@@]1([H])[C@]2(C(=O)C2=C3[C@](C([H])=C([H])C(=O)[C@]13C([H])([H])[H])(C([H])([H])[H])C([H])([H])O2)C([H])([H])[H]

InChI Identifier

InChI=1S/C26H28O4/c1-23-10-8-19(27)26(4)18-7-11-24(2)16(15-9-12-29-13-15)5-6-17(24)25(18,3)22(28)20(21(23)26)30-14-23/h6,8-10,12-13,16,18H,5,7,11,14H2,1-4H3/t16-,18-,23-,24-,25-,26-/m0/s1

InChI Key

MHHWKYUSJKVZMV-RUEDEKCXSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
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, 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, 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, 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, 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
Trichilia rubescens	JEOL database	Tontsa, A. T., et al., Chem. Pharm. Bull. 61, 1178 (2013)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 17-furanylsteroids and derivatives. These are steroidal compounds having a furanyl group linked to the steroid backbone at the C17 position.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

17-furanylsteroids and derivatives

Direct Parent

17-furanylsteroids and derivatives

Alternative Parents

Substituents

17-furanylsteroid skeleton
Naphthofuran
Cyclohexenone
Heteroaromatic compound
Furan
Dihydrofuran
Ketone
Oxacycle
Organoheterocyclic compound
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
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	4.95	ALOGPS
logP	4.31	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	56.51 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	116.49 m³·mol⁻¹	ChemAxon
Polarizability	44.65 Å³	ChemAxon
Number of Rings	6	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

72712662

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Tontsa, A. T., et al. (2013). Tontsa, A. T., et al., Chem. Pharm. Bull. 61, 1178 (2013). Chem. Pharm. Bull..

Showing NP-Card for rubescin A (NP0042817)

MOL for NP0042817 (rubescin A)

3D MOL for NP0042817 (rubescin A)

3D SDF for NP0042817 (rubescin A)

3D-SDF for NP0042817 (rubescin A)

PDB for NP0042817 (rubescin A)

3D PDB for NP0042817 (rubescin A)

SMILES for NP0042817 (rubescin A)

INCHI for NP0042817 (rubescin A)

Structure for NP0042817 (rubescin A)

3D Structure for NP0042817 (rubescin A)