Nicansteroidin D; 15alpha-acetoxy-16beta,17beta-epoxy-6beta,14beta-dihydroxy-1-oxo-2alpha,5alpha-dioxy-witha-3,24-dien-26,22-olide

ID: ALA4857443

PubChem CID: 164614692

Max Phase: Preclinical

Molecular Formula: C30H38O10

Molecular Weight: 558.62

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC(=O)O[C@H]1[C@@H]2O[C@]2([C@H](C)[C@H]2CC(C)=C(C)C(=O)O2)[C@@]2(C)CC[C@H]3[C@@H](C[C@@H](O)[C@]45C=C[C@H](OO4)C(=O)[C@]35C)[C@@]12O

Standard InChI:  InChI=1S/C30H38O10/c1-13-11-20(37-25(34)14(13)2)15(3)30-24(38-30)23(36-16(4)31)29(35)18-12-21(32)28-10-8-19(39-40-28)22(33)27(28,6)17(18)7-9-26(29,30)5/h8,10,15,17-21,23-24,32,35H,7,9,11-12H2,1-6H3/t15-,17+,18-,19+,20-,21-,23+,24+,26+,27+,28+,29-,30+/m1/s1

Standard InChI Key:  UMKFPSOCMNHMRG-JLMBNDLYSA-N

Molfile:  

 
     RDKit          2D

 45 51  0  0  0  0  0  0  0  0999 V2000
    7.5635   -7.8512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1158   -8.4669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8538   -9.2521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0498   -9.4184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5007   -8.7955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6963   -8.9655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4361   -9.7480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9211  -10.4222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4331  -11.0912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6445  -10.8289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9336  -11.2405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9322  -12.0645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2151  -12.4771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4984  -12.0697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7922  -12.4758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0829  -12.0671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0829  -11.2421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7922  -10.8258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5057  -11.2421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2163  -10.8272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2110  -10.0003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9317   -9.5884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6490  -10.0017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6413   -9.1759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2094  -11.6508    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4994  -10.4172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7922  -10.0009    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9253  -10.4154    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6395  -11.6526    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6849  -11.8765    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4914  -12.0510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7391  -12.8322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0421  -11.4403    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2934   -9.6859    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1126   -8.3817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7556   -8.0171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3986   -9.8677    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9210   -8.3013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0809   -8.0801    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2172  -13.3001    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9328  -11.2432    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5587  -11.8043    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8213   -7.0696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3658  -10.8275    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5007  -11.0021    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  1  0
  4  3  1  0
  5  4  1  0
  6  5  1  0
  7  6  1  0
  8  7  1  0
  9  8  1  0
 10  9  1  0
 11 10  1  0
 12 11  1  0
 13 12  1  0
 14 13  1  0
 15 14  1  0
 16 15  2  0
 17 16  1  0
 17 18  1  0
 19 18  1  0
 19 20  1  0
 20 11  1  0
 20 21  1  0
 22 21  1  0
 23 22  1  0
 23 10  1  0
  7 23  1  0
 23 24  1  1
 20 25  1  6
 19 26  1  1
 19 14  1  0
 18 27  2  0
 11 28  1  1
 10 29  1  1
  9 30  1  6
 30 31  1  0
 31 32  1  0
 31 33  2  0
  7 34  1  1
  6 35  1  6
  5 36  1  0
  1 36  1  0
  3 37  2  0
  2 38  1  0
  5 39  1  6
 13 40  1  1
  8 34  1  0
 17 41  1  0
 41 42  1  0
 14 42  1  6
  1 43  1  0
 17 44  1  6
  8 45  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA4857443

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 558.62

Molecular Weight (Monoisotopic): 558.2465

AlogP: 2.10

#Rotatable Bonds: 3

Polar Surface Area: 141.12

Molecular Species: NEUTRAL

HBA: 10

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 10

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 13.02

CX Basic pKa: ┄

CX LogP: 2.61

CX LogD: 2.61

Aromatic Rings: ┄

Heavy Atoms: 40

QED Weighted: 0.23

Np Likeness Score: 2.88

References

1. Taddeo VA, Núñez MJ, Beltrán M, Castillo UG, Menjívar J, Jiménez IA, Alcamí J, Bedoya LM, Bazzocchi IL..  (2021)  Withanolide-Type Steroids from Physalis nicandroides Inhibit HIV Transcription.,  84  (10.0): [PMID:34549952] [10.1021/acs.jnatprod.1c00637]

Source

Source(1):

• Scientific Literature