NP-MRD: Showing NP-Card for (1s,2r,6s,7s,9r,11s,12s,15r,16s)-6-[(1r)-2,2-dimethyl-3-oxocyclopropoxy]-15-[(1s)-1-[(2r)-5-(hydroxymethyl)-4-methyl-6-oxo-2,3-dihydropyran-2-yl]ethyl]-2,16-dimethyl-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadecan-3-one (NP0326603)

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Record Information

Version

2.0

Created at

2022-09-12 08:18:47 UTC

Updated at

2022-09-12 08:18:47 UTC

NP-MRD ID

NP0326603

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,2r,6s,7s,9r,11s,12s,15r,16s)-6-[(1r)-2,2-dimethyl-3-oxocyclopropoxy]-15-[(1s)-1-[(2r)-5-(hydroxymethyl)-4-methyl-6-oxo-2,3-dihydropyran-2-yl]ethyl]-2,16-dimethyl-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadecan-3-one

Description

(1S,2R,6S,7S,9R,11S,12S,15R,16S)-6-[(1R)-2,2-dimethyl-3-oxocyclopropoxy]-15-[(1S)-1-[(2R)-5-(hydroxymethyl)-4-methyl-6-oxo-3,6-dihydro-2H-pyran-2-yl]ethyl]-2,16-dimethyl-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]Octadecan-3-one belongs to the class of organic compounds known as withanolides and derivatives. These are c28 steroids structurally characterized by an ergostane skeleton usually functionalized at carbons 1, 22 and 26 to form a lactone ring. (1s,2r,6s,7s,9r,11s,12s,15r,16s)-6-[(1r)-2,2-dimethyl-3-oxocyclopropoxy]-15-[(1s)-1-[(2r)-5-(hydroxymethyl)-4-methyl-6-oxo-2,3-dihydropyran-2-yl]ethyl]-2,16-dimethyl-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadecan-3-one is found in Withania somnifera. Based on a literature review very few articles have been published on (1S,2R,6S,7S,9R,11S,12S,15R,16S)-6-[(1R)-2,2-dimethyl-3-oxocyclopropoxy]-15-[(1S)-1-[(2R)-5-(hydroxymethyl)-4-methyl-6-oxo-3,6-dihydro-2H-pyran-2-yl]ethyl]-2,16-dimethyl-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]Octadecan-3-one.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309122210182D          

 40 46  0  0  1  0            999 V2000
    8.6555    3.9323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1492    3.2810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4601    2.5168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2773    2.4040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7837    3.0553    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9537    1.8655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2646    1.1013    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1365    1.9784    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8256    2.7425    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.0083    2.8554    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.6974    3.6196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5020    2.2041    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7313    1.4116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0484    0.9486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3971    1.4549    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5850    1.3097    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3047    0.5338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4926    0.3886    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6805    0.2434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9608    1.0193    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1486    0.8741    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8683    0.0982    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0562   -0.0471    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5745   -0.5789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8548   -1.3548    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7197    0.2332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5171    0.4448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7936    1.0549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6168    1.5048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8971    2.2807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7092    2.4259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9895    3.2018    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2411    1.7952    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5214    2.5711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0532    1.9404    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3335    2.7164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1456    2.8616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6774    2.2309    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0373    2.9732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3319    3.3939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  3  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  1  0  0  0
 10 11  1  6  0  0  0
 12 10  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 15 14  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  1  6  0  0  0
 17 18  1  0  0  0  0
 18 19  1  1  0  0  0
 20 19  1  1  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  1  0  0  0
 23 22  1  1  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 23 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 21 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 31 33  1  0  0  0  0
 20 33  1  0  0  0  0
 33 34  1  1  0  0  0
 33 35  1  0  0  0  0
 16 35  1  0  0  0  0
 35 36  1  1  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 15 38  1  0  0  0  0
 12 38  1  0  0  0  0
 38 39  1  1  0  0  0
  9 40  1  0  0  0  0
  2 40  1  0  0  0  0
M  END


  Mrv1652309122210182D          

 40 46  0  0  1  0            999 V2000
    8.6555    3.9323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1492    3.2810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4601    2.5168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2773    2.4040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7837    3.0553    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9537    1.8655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2646    1.1013    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1365    1.9784    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8256    2.7425    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.0083    2.8554    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.6974    3.6196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5020    2.2041    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7313    1.4116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0484    0.9486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3971    1.4549    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5850    1.3097    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3047    0.5338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4926    0.3886    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6805    0.2434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9608    1.0193    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1486    0.8741    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8683    0.0982    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0562   -0.0471    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5745   -0.5789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8548   -1.3548    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7197    0.2332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5171    0.4448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7936    1.0549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6168    1.5048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8971    2.2807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7092    2.4259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9895    3.2018    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2411    1.7952    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5214    2.5711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0532    1.9404    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3335    2.7164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1456    2.8616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6774    2.2309    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0373    2.9732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3319    3.3939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  3  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  1  0  0  0
 10 11  1  6  0  0  0
 12 10  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 15 14  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  1  6  0  0  0
 17 18  1  0  0  0  0
 18 19  1  1  0  0  0
 20 19  1  1  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  1  0  0  0
 23 22  1  1  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 23 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 21 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 31 33  1  0  0  0  0
 20 33  1  0  0  0  0
 33 34  1  1  0  0  0
 33 35  1  0  0  0  0
 16 35  1  0  0  0  0
 35 36  1  1  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 15 38  1  0  0  0  0
 12 38  1  0  0  0  0
 38 39  1  1  0  0  0
  9 40  1  0  0  0  0
  2 40  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0326603

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]([C@H]1CC[C@H]2[C@@H]3C[C@H]4O[C@]44[C@H](CCC(=O)[C@]4(C)[C@H]3CC[C@]12C)O[C@H]1C(=O)C1(C)C)[C@H]1CC(C)=C(CO)C(=O)O1

> <INCHI_IDENTIFIER>
InChI=1S/C33H46O7/c1-16-13-23(38-29(37)19(16)15-34)17(2)20-7-8-21-18-14-26-33(40-26)25(39-28-27(36)30(28,3)4)10-9-24(35)32(33,6)22(18)11-12-31(20,21)5/h17-18,20-23,25-26,28,34H,7-15H2,1-6H3/t17-,18-,20+,21-,22-,23+,25-,26+,28-,31+,32-,33+/m0/s1

> <INCHI_KEY>
ULRJIYSLHJKKKN-KFALQCPXSA-N

> <FORMULA>
C33H46O7

> <MOLECULAR_WEIGHT>
554.724

> <EXACT_MASS>
554.324353821

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
86

> <JCHEM_AVERAGE_POLARIZABILITY>
62.97390711398805

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2R,6S,7S,9R,11S,12S,15R,16S)-6-[(1R)-2,2-dimethyl-3-oxocyclopropoxy]-15-[(1S)-1-[(2R)-5-(hydroxymethyl)-4-methyl-6-oxo-3,6-dihydro-2H-pyran-2-yl]ethyl]-2,16-dimethyl-8-oxapentacyclo[9.7.0.0^{2,7}.0^{7,9}.0^{12,16}]octadecan-3-one

> <JCHEM_LOGP>
5.128277126333332

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
17.934105718556644

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.873765773112364

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8538493304385115

> <JCHEM_POLAR_SURFACE_AREA>
102.43

> <JCHEM_REFRACTIVITY>
147.60339999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,6S,7S,9R,11S,12S,15R,16S)-6-[(1R)-2,2-dimethyl-3-oxocyclopropoxy]-15-[(1S)-1-[(2R)-5-(hydroxymethyl)-4-methyl-6-oxo-2,3-dihydropyran-2-yl]ethyl]-2,16-dimethyl-8-oxapentacyclo[9.7.0.0^{2,7}.0^{7,9}.0^{12,16}]octadecan-3-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0      16.157   7.340   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      15.212   6.125   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      15.792   4.698   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      17.318   4.487   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      18.263   5.703   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      14.847   3.482   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      15.427   2.056   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      13.321   3.693   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      12.741   5.119   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      11.216   5.330   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.635   6.757   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.270   4.114   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.698   2.635   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.424   1.771   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.208   2.716   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.692   2.445   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.169   0.996   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.653   0.725   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       3.137   0.454   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       3.660   1.903   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.144   1.632   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       1.621   0.183   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       0.105  -0.088   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -1.072  -1.081   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -1.596  -2.529   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      -1.343   0.435   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -2.832   0.830   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -1.481   1.969   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       1.151   2.809   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       1.675   4.257   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       3.191   4.528   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       3.714   5.977   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       4.183   3.351   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       4.707   4.799   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       5.699   3.622   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       6.222   5.071   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       7.738   5.342   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       8.731   4.164   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       9.403   5.550   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      13.686   6.335   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   40                                                  
CONECT    3    2    4    6                                                  
CONECT    4    3    5                                                       
CONECT    5    4                                                            
CONECT    6    3    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10   40                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   38                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   38                                                  
CONECT   16   15   17   35                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18   20                                                       
CONECT   20   19   18   21   33                                             
CONECT   21   20   22   29                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   26                                                  
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   23   27   28                                             
CONECT   27   26                                                            
CONECT   28   26                                                            
CONECT   29   21   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   20   34   35                                             
CONECT   34   33                                                            
CONECT   35   33   16   36                                                  
CONECT   36   35   37                                                       
CONECT   37   36   38                                                       
CONECT   38   37   15   12   39                                             
CONECT   39   38                                                            
CONECT   40    9    2                                                       
MASTER        0    0    0    0    0    0    0    0   40    0   92    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₃H₄₆O₇

Average Mass

554.7240 Da

Monoisotopic Mass

554.32435 Da

IUPAC Name

Traditional Name

(1S,2R,6S,7S,9R,11S,12S,15R,16S)-6-[(1R)-2,2-dimethyl-3-oxocyclopropoxy]-15-[(1S)-1-[(2R)-5-(hydroxymethyl)-4-methyl-6-oxo-2,3-dihydropyran-2-yl]ethyl]-2,16-dimethyl-8-oxapentacyclo[9.7.0.0^{2,7}.0^{7,9}.0^{12,16}]octadecan-3-one

CAS Registry Number

Not Available

SMILES

C[C@@H]([C@H]1CC[C@H]2[C@@H]3C[C@H]4O[C@]44[C@H](CCC(=O)[C@]4(C)[C@H]3CC[C@]12C)O[C@H]1C(=O)C1(C)C)[C@H]1CC(C)=C(CO)C(=O)O1

InChI Identifier

InChI=1S/C33H46O7/c1-16-13-23(38-29(37)19(16)15-34)17(2)20-7-8-21-18-14-26-33(40-26)25(39-28-27(36)30(28,3)4)10-9-24(35)32(33,6)22(18)11-12-31(20,21)5/h17-18,20-23,25-26,28,34H,7-15H2,1-6H3/t17-,18-,20+,21-,22-,23+,25-,26+,28-,31+,32-,33+/m0/s1

InChI Key

ULRJIYSLHJKKKN-KFALQCPXSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Withania somnifera	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as withanolides and derivatives. These are c28 steroids structurally characterized by an ergostane skeleton usually functionalized at carbons 1, 22 and 26 to form a lactone ring.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroid lactones

Direct Parent

Withanolides and derivatives

Alternative Parents

Substituents

Withanolide-skeleton
5,6-epoxysteroid
Dihydropyranone
Oxepane
Pyran
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Cyclic ketone
Ketone
Lactone
Oxacycle
Carboxylic acid derivative
Organoheterocyclic compound
Dialkyl ether
Oxirane
Ether
Monocarboxylic acid or derivatives
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
Organooxygen compound
Primary alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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	5.13	ChemAxon
pKa (Strongest Acidic)	14.87	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	102.43 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	147.6 m³·mol⁻¹	ChemAxon
Polarizability	62.97 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

162893298

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,2r,6s,7s,9r,11s,12s,15r,16s)-6-[(1r)-2,2-dimethyl-3-oxocyclopropoxy]-15-[(1s)-1-[(2r)-5-(hydroxymethyl)-4-methyl-6-oxo-2,3-dihydropyran-2-yl]ethyl]-2,16-dimethyl-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadecan-3-one (NP0326603)

MOL for NP0326603 ((1s,2r,6s,7s,9r,11s,12s,15r,16s)-6-[(1r)-2,2-dimethyl-3-oxocyclopropoxy]-15-[(1s)-1-[(2r)-5-(hydroxymethyl)-4-methyl-6-oxo-2,3-dihydropyran-2-yl]ethyl]-2,16-dimethyl-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadecan-3-one)

3D MOL for NP0326603 ((1s,2r,6s,7s,9r,11s,12s,15r,16s)-6-[(1r)-2,2-dimethyl-3-oxocyclopropoxy]-15-[(1s)-1-[(2r)-5-(hydroxymethyl)-4-methyl-6-oxo-2,3-dihydropyran-2-yl]ethyl]-2,16-dimethyl-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadecan-3-one)

3D SDF for NP0326603 ((1s,2r,6s,7s,9r,11s,12s,15r,16s)-6-[(1r)-2,2-dimethyl-3-oxocyclopropoxy]-15-[(1s)-1-[(2r)-5-(hydroxymethyl)-4-methyl-6-oxo-2,3-dihydropyran-2-yl]ethyl]-2,16-dimethyl-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadecan-3-one)

3D-SDF for NP0326603 ((1s,2r,6s,7s,9r,11s,12s,15r,16s)-6-[(1r)-2,2-dimethyl-3-oxocyclopropoxy]-15-[(1s)-1-[(2r)-5-(hydroxymethyl)-4-methyl-6-oxo-2,3-dihydropyran-2-yl]ethyl]-2,16-dimethyl-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadecan-3-one)

PDB for NP0326603 ((1s,2r,6s,7s,9r,11s,12s,15r,16s)-6-[(1r)-2,2-dimethyl-3-oxocyclopropoxy]-15-[(1s)-1-[(2r)-5-(hydroxymethyl)-4-methyl-6-oxo-2,3-dihydropyran-2-yl]ethyl]-2,16-dimethyl-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadecan-3-one)

3D PDB for NP0326603 ((1s,2r,6s,7s,9r,11s,12s,15r,16s)-6-[(1r)-2,2-dimethyl-3-oxocyclopropoxy]-15-[(1s)-1-[(2r)-5-(hydroxymethyl)-4-methyl-6-oxo-2,3-dihydropyran-2-yl]ethyl]-2,16-dimethyl-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadecan-3-one)

SMILES for NP0326603 ((1s,2r,6s,7s,9r,11s,12s,15r,16s)-6-[(1r)-2,2-dimethyl-3-oxocyclopropoxy]-15-[(1s)-1-[(2r)-5-(hydroxymethyl)-4-methyl-6-oxo-2,3-dihydropyran-2-yl]ethyl]-2,16-dimethyl-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadecan-3-one)

INCHI for NP0326603 ((1s,2r,6s,7s,9r,11s,12s,15r,16s)-6-[(1r)-2,2-dimethyl-3-oxocyclopropoxy]-15-[(1s)-1-[(2r)-5-(hydroxymethyl)-4-methyl-6-oxo-2,3-dihydropyran-2-yl]ethyl]-2,16-dimethyl-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadecan-3-one)

Structure for NP0326603 ((1s,2r,6s,7s,9r,11s,12s,15r,16s)-6-[(1r)-2,2-dimethyl-3-oxocyclopropoxy]-15-[(1s)-1-[(2r)-5-(hydroxymethyl)-4-methyl-6-oxo-2,3-dihydropyran-2-yl]ethyl]-2,16-dimethyl-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadecan-3-one)

3D Structure for NP0326603 ((1s,2r,6s,7s,9r,11s,12s,15r,16s)-6-[(1r)-2,2-dimethyl-3-oxocyclopropoxy]-15-[(1s)-1-[(2r)-5-(hydroxymethyl)-4-methyl-6-oxo-2,3-dihydropyran-2-yl]ethyl]-2,16-dimethyl-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadecan-3-one)