NP-MRD: Showing NP-Card for Withastramonolide E (NP0332985)

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Record Information

Version

2.0

Created at

2024-05-03 03:54:07 UTC

Updated at

2025-02-11 15:43:48 UTC

NP-MRD ID

NP0332985

Natural Product DOI

https://doi.org/10.57994/2266

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Withastramonolide E

Description

Withastramonolide E 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. Withastramonolide E was first documented in 2024 (PMID: 38084071). Based on a literature review very few articles have been published on Withastramonolide E.

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 01152306302D          

 51 56  0  0  1  0            999 V2000
   -3.8244   -0.8429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0071   -0.7301    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5008   -1.3814    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3110   -1.5369    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7301   -2.1739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0473   -2.6369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3959   -2.1305    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8641   -1.4998    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5838   -2.2757    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1156   -2.9064    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3035   -3.0516    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8353   -3.6824    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5550   -4.4583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0868   -5.0890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5086   -3.1969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0404   -2.5662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7601   -1.7902    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4798   -1.0143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0520   -1.6450    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2283   -2.4209    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3323   -0.8691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1444   -0.7239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6762   -1.3546    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0361   -0.6122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8526   -2.7114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3844   -2.0807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1041   -1.3047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2920   -1.1595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0117   -0.3836    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6962    0.0341    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5135   -0.0787    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2026    0.6855    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8917    1.4496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0745    1.5625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7636    2.3267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9463    2.4395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6354    3.2037    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1418    3.8550    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9590    3.7422    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1818    3.3165    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4927    4.0807    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3099    4.1936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6208    4.9578    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0137    4.7321    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2972    5.4962    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8309    4.6192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3373    5.2705    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5681    0.9112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7509    1.0240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8790    0.1470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3981    2.1010    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  3  2  1  6  0  0  0
  3  4  1  1  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  7  6  1  0  0  0  0
  7  8  1  1  0  0  0
  9  7  1  0  0  0  0
  9 10  1  6  0  0  0
  9 11  1  0  0  0  0
 11 12  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 11 15  1  0  0  0  0
 15 16  2  0  0  0  0
 17 16  1  0  0  0  0
 17 18  1  6  0  0  0
 19 17  1  0  0  0  0
  9 19  1  0  0  0  0
 19 20  1  1  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 23 22  1  0  0  0  0
  7 23  1  0  0  0  0
 23  3  1  0  0  0  0
 23 24  1  6  0  0  0
 16 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 17 28  1  0  0  0  0
 28 29  2  0  0  0  0
  2 30  1  0  0  0  0
 30 31  1  1  0  0  0
 30 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 37 36  1  1  0  0  0
 37 38  1  0  0  0  0
 38 39  1  6  0  0  0
 37 40  1  0  0  0  0
 41 40  1  0  0  0  0
 41 42  1  1  0  0  0
 42 43  1  0  0  0  0
 41 44  1  0  0  0  0
 44 45  1  6  0  0  0
 44 46  1  0  0  0  0
 38 46  1  0  0  0  0
 46 47  1  0  0  0  0
 34 48  2  0  0  0  0
 48 49  1  0  0  0  0
 48 50  1  0  0  0  0
 30 50  1  0  0  0  0
 33 51  2  0  0  0  0
M  END


  Mrv2104 01152306302D          

 51 56  0  0  1  0            999 V2000
   -3.8244   -0.8429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0071   -0.7301    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5008   -1.3814    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3110   -1.5369    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7301   -2.1739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0473   -2.6369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3959   -2.1305    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8641   -1.4998    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5838   -2.2757    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1156   -2.9064    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3035   -3.0516    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8353   -3.6824    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5550   -4.4583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0868   -5.0890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5086   -3.1969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0404   -2.5662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7601   -1.7902    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4798   -1.0143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0520   -1.6450    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2283   -2.4209    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3323   -0.8691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1444   -0.7239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6762   -1.3546    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0361   -0.6122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8526   -2.7114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3844   -2.0807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1041   -1.3047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2920   -1.1595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0117   -0.3836    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6962    0.0341    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5135   -0.0787    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2026    0.6855    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8917    1.4496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0745    1.5625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7636    2.3267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9463    2.4395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6354    3.2037    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1418    3.8550    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9590    3.7422    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1818    3.3165    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4927    4.0807    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3099    4.1936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6208    4.9578    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0137    4.7321    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2972    5.4962    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8309    4.6192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3373    5.2705    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5681    0.9112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7509    1.0240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8790    0.1470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3981    2.1010    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  3  2  1  6  0  0  0
  3  4  1  1  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  7  6  1  0  0  0  0
  7  8  1  1  0  0  0
  9  7  1  0  0  0  0
  9 10  1  6  0  0  0
  9 11  1  0  0  0  0
 11 12  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 11 15  1  0  0  0  0
 15 16  2  0  0  0  0
 17 16  1  0  0  0  0
 17 18  1  6  0  0  0
 19 17  1  0  0  0  0
  9 19  1  0  0  0  0
 19 20  1  1  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 23 22  1  0  0  0  0
  7 23  1  0  0  0  0
 23  3  1  0  0  0  0
 23 24  1  6  0  0  0
 16 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 17 28  1  0  0  0  0
 28 29  2  0  0  0  0
  2 30  1  0  0  0  0
 30 31  1  1  0  0  0
 30 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 37 36  1  1  0  0  0
 37 38  1  0  0  0  0
 38 39  1  6  0  0  0
 37 40  1  0  0  0  0
 41 40  1  0  0  0  0
 41 42  1  1  0  0  0
 42 43  1  0  0  0  0
 41 44  1  0  0  0  0
 44 45  1  6  0  0  0
 44 46  1  0  0  0  0
 38 46  1  0  0  0  0
 46 47  1  0  0  0  0
 34 48  2  0  0  0  0
 48 49  1  0  0  0  0
 48 50  1  0  0  0  0
 30 50  1  0  0  0  0
 33 51  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0332985

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@H](OCC)C=C4CC=CC(=O)[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)[C@@]1([H])CC(C)=C(CO[C@@H]2O[C@H](CO)[C@@H](O)C(O)[C@H]2O)C(=O)O1

> <INCHI_IDENTIFIER>
InChI=1S/C36H52O10/c1-6-43-26-15-20-8-7-9-28(38)36(20,5)24-12-13-35(4)22(10-11-23(35)29(24)26)19(3)25-14-18(2)21(33(42)45-25)17-44-34-32(41)31(40)30(39)27(16-37)46-34/h7,9,15,19,22-27,29-32,34,37,39-41H,6,8,10-14,16-17H2,1-5H3/t19-,22+,23-,24-,25+,26+,27+,29-,30+,31?,32+,34+,35+,36-/m0/s1

> <INCHI_KEY>
VQOOXUHQGODEKM-ICQVLRJQSA-N

> <FORMULA>
C36H52O10

> <MOLECULAR_WEIGHT>
644.802

> <EXACT_MASS>
644.356047874

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
98

> <JCHEM_AVERAGE_POLARIZABILITY>
72.3012276820367

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(6R)-6-[(1S)-1-[(1R,3aS,3bS,4S,9aR,9bS,11aR)-4-ethoxy-9a,11a-dimethyl-9-oxo-1H,2H,3H,3aH,3bH,4H,6H,9H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthren-1-yl]ethyl]-4-methyl-3-({[(2R,3R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-5,6-dihydro-2H-pyran-2-one

> <JCHEM_LOGP>
3.2441320553333317

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.200058865062205

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.210491255587606

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981083553717509

> <JCHEM_POLAR_SURFACE_AREA>
151.98000000000002

> <JCHEM_REFRACTIVITY>
170.80930000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(6R)-6-[(1S)-1-[(1R,3aS,3bS,4S,9aR,9bS,11aR)-4-ethoxy-9a,11a-dimethyl-9-oxo-1H,2H,3H,3aH,3bH,4H,6H,9bH,10H,11H-cyclopenta[a]phenanthren-1-yl]ethyl]-4-methyl-3-({[(2R,3R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-5,6-dihydropyran-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 15-JAN-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   15-JAN-23         0                                  
HETATM    1  C   UNK     0      -7.139  -1.573   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.613  -1.363   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.668  -2.579   0.000  0.00  0.00           C+0
HETATM    4  H   UNK     0      -6.181  -2.869   0.000  0.00  0.00           H+0
HETATM    5  C   UNK     0      -5.096  -4.058   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.822  -4.922   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.606  -3.977   0.000  0.00  0.00           C+0
HETATM    8  H   UNK     0      -1.613  -2.800   0.000  0.00  0.00           H+0
HETATM    9  C   UNK     0      -1.090  -4.248   0.000  0.00  0.00           C+0
HETATM   10  H   UNK     0      -2.082  -5.425   0.000  0.00  0.00           H+0
HETATM   11  C   UNK     0      -0.567  -5.696   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -1.559  -6.874   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -1.036  -8.322   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.029  -9.499   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.949  -5.967   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.942  -4.790   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.419  -3.342   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.896  -1.893   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.097  -3.071   0.000  0.00  0.00           C+0
HETATM   20  H   UNK     0       0.426  -4.519   0.000  0.00  0.00           H+0
HETATM   21  C   UNK     0      -0.620  -1.622   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -2.136  -1.351   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -3.129  -2.529   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -3.801  -1.143   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.458  -5.061   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.451  -3.884   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       3.928  -2.436   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.412  -2.164   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       1.888  -0.716   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      -5.033   0.064   0.000  0.00  0.00           C+0
HETATM   31  H   UNK     0      -6.559  -0.147   0.000  0.00  0.00           H+0
HETATM   32  O   UNK     0      -5.978   1.280   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      -5.398   2.706   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -3.872   2.917   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -3.292   4.343   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      -1.766   4.554   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      -1.186   5.980   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -2.131   7.196   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      -3.657   6.985   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0       0.339   6.191   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0       0.920   7.617   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       2.445   7.828   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0       3.026   9.254   0.000  0.00  0.00           O+0
HETATM   44  C   UNK     0      -0.025   8.833   0.000  0.00  0.00           C+0
HETATM   45  O   UNK     0       0.555  10.260   0.000  0.00  0.00           O+0
HETATM   46  C   UNK     0      -1.551   8.623   0.000  0.00  0.00           C+0
HETATM   47  O   UNK     0      -2.496   9.838   0.000  0.00  0.00           O+0
HETATM   48  C   UNK     0      -2.927   1.701   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0      -1.402   1.911   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0      -3.507   0.274   0.000  0.00  0.00           C+0
HETATM   51  O   UNK     0      -6.343   3.922   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   30                                                  
CONECT    3    2    4    5   23                                             
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9   23                                             
CONECT    8    7                                                            
CONECT    9    7   10   11   19                                             
CONECT   10    9                                                            
CONECT   11    9   12   15                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13                                                            
CONECT   15   11   16                                                       
CONECT   16   15   17   25                                                  
CONECT   17   16   18   19   28                                             
CONECT   18   17                                                            
CONECT   19   17    9   20   21                                             
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22    7    3   24                                             
CONECT   24   23                                                            
CONECT   25   16   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   17   29                                                  
CONECT   29   28                                                            
CONECT   30    2   31   32   50                                             
CONECT   31   30                                                            
CONECT   32   30   33                                                       
CONECT   33   32   34   51                                                  
CONECT   34   33   35   48                                                  
CONECT   35   34   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36   38   40                                                  
CONECT   38   37   39   46                                                  
CONECT   39   38                                                            
CONECT   40   37   41                                                       
CONECT   41   40   42   44                                                  
CONECT   42   41   43                                                       
CONECT   43   42                                                            
CONECT   44   41   45   46                                                  
CONECT   45   44                                                            
CONECT   46   44   38   47                                                  
CONECT   47   46                                                            
CONECT   48   34   49   50                                                  
CONECT   49   48                                                            
CONECT   50   48   30                                                       
CONECT   51   33                                                            
MASTER        0    0    0    0    0    0    0    0   51    0  112    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₆H₅₂O₁₀

Average Mass

644.8020 Da

Monoisotopic Mass

644.35605 Da

IUPAC Name

(6R)-6-[(1S)-1-[(1R,3aS,3bS,4S,9aR,9bS,11aR)-4-ethoxy-9a,11a-dimethyl-9-oxo-1H,2H,3H,3aH,3bH,4H,6H,9H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthren-1-yl]ethyl]-4-methyl-3-({[(2R,3R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-5,6-dihydro-2H-pyran-2-one

Traditional Name

(6R)-6-[(1S)-1-[(1R,3aS,3bS,4S,9aR,9bS,11aR)-4-ethoxy-9a,11a-dimethyl-9-oxo-1H,2H,3H,3aH,3bH,4H,6H,9bH,10H,11H-cyclopenta[a]phenanthren-1-yl]ethyl]-4-methyl-3-({[(2R,3R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-5,6-dihydropyran-2-one

CAS Registry Number

Not Available

SMILES

[H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@H](OCC)C=C4CC=CC(=O)[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)[C@@]1([H])CC(C)=C(CO[C@@H]2O[C@H](CO)[C@@H](O)C(O)[C@H]2O)C(=O)O1

InChI Identifier

InChI=1S/C36H52O10/c1-6-43-26-15-20-8-7-9-28(38)36(20,5)24-12-13-35(4)22(10-11-23(35)29(24)26)19(3)25-14-18(2)21(33(42)45-25)17-44-34-32(41)31(40)30(39)27(16-37)46-34/h7,9,15,19,22-27,29-32,34,37,39-41H,6,8,10-14,16-17H2,1-5H3/t19-,22+,23-,24-,25+,26+,27+,29-,30+,31?,32+,34+,35+,36-/m0/s1

InChI Key

VQOOXUHQGODEKM-ICQVLRJQSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View

Predicted Spectra

Not Available

Chemical Shift Submissions

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 600, CD₃OD, simulated)	570075670@qq.com	黑龙江中医药大学	Pan juan	2024-05-03	View Spectrum

Species

Species of Origin

Species Name	Source	Reference
Datura stramonium		Not Available

Chemical Taxonomy

Description

This compound 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
Bile acid, alcohol, or derivatives
Steroid ester
Diterpenoid
Diterpene lactone
Oxosteroid
1-oxosteroid
Fatty acyl glycoside of mono- or disaccharide
Fatty acyl glycoside
Fatty alcohol ester
Alkyl glycoside
Fatty alcohol
Quinomethane
M-quinomethane
Cyclohexenone
Dihydropyranone
Fatty acyl
Pyran
Oxane
Monosaccharide
Alpha,beta-unsaturated ketone
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Enone
Acryloyl-group
Secondary alcohol
Lactone
Ketone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Ether
Dialkyl ether
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
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	3.24	ChemAxon
pKa (Strongest Acidic)	12.21	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	151.98 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	170.81 m³·mol⁻¹	ChemAxon
Polarizability	72.3 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

DOI: 10.1002/cbdv.202301655

Showing NP-Card for Withastramonolide E (NP0332985)

MOL for NP0332985 (Withastramonolide E)

3D MOL for NP0332985 (Withastramonolide E)

3D SDF for NP0332985 (Withastramonolide E)

3D-SDF for NP0332985 (Withastramonolide E)

PDB for NP0332985 (Withastramonolide E)

3D PDB for NP0332985 (Withastramonolide E)

SMILES for NP0332985 (Withastramonolide E)

INCHI for NP0332985 (Withastramonolide E)

Structure for NP0332985 (Withastramonolide E)

3D Structure for NP0332985 (Withastramonolide E)