22S,25-Epoxylanosta-7,9(11)-dien-3beta,24R-diol

ID: ALA5278696

Max Phase: Preclinical

Molecular Formula: C30H48O3

Molecular Weight: 456.71

Names and Identifiers

Canonical SMILES:  C[C@H]([C@@H]1C[C@@H](O)C(C)(C)O1)[C@H]1CC[C@@]2(C)C3=CC[C@H]4C(C)(C)[C@@H](O)CC[C@]4(C)C3=CC[C@]12C

Standard InChI:  InChI=1S/C30H48O3/c1-18(22-17-25(32)27(4,5)33-22)19-11-15-30(8)21-9-10-23-26(2,3)24(31)13-14-28(23,6)20(21)12-16-29(19,30)7/h9,12,18-19,22-25,31-32H,10-11,13-17H2,1-8H3/t18-,19+,22-,23-,24-,25+,28+,29+,30-/m0/s1

Standard InChI Key:  ZSJNLSFWYLWTHK-SNLWPZNCSA-N

Molfile:  

 
     RDKit          2D

 36 40  0  0  0  0  0  0  0  0999 V2000
   -3.3915   -1.0367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6771   -0.6241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9626   -1.0367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9626   -1.8617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6771   -2.2742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3915   -1.8617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2481   -0.6241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5336   -1.0367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5336   -1.8617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2481   -2.2742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2480    0.2008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5335    0.6133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1809    0.2008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1808   -0.6242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9654   -0.8791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9655    0.4556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4504   -0.2118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1791    1.2528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5955    1.8364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9762    1.4664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2718    2.2364    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0956    2.1933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3091    1.3965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6173    0.9473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1062   -2.2743    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9626   -0.2114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1809    1.0260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9626   -2.6869    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1808   -1.4494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1062    1.1829    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8942    2.4073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3101    2.9902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7769    0.6060    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0904   -2.9902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2652   -2.9902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3927    2.0499    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  3  2  1  0
  4  3  1  0
  5  4  1  0
  1  6  1  0
  6  5  1  0
  3  7  1  0
  8  7  1  0
  9  8  2  0
 10  9  1  0
  4 10  1  0
  7 11  2  0
 12 11  1  0
 13 12  1  0
 14 13  1  0
  8 14  1  0
 14 15  1  0
 13 16  1  0
 16 17  1  0
 17 15  1  0
 16 18  1  0
 18 19  1  6
 18 20  1  0
 21 20  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 20  1  0
  6 25  1  1
  3 26  1  1
 13 27  1  1
  4 28  1  6
 14 29  1  6
 23 30  1  6
 22 31  1  0
 22 32  1  0
 16 33  1  6
  5 34  1  0
  5 35  1  0
 20 36  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA5278696

   ---

Molecule Features

Natural Product: Yes

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 456.71

Molecular Weight (Monoisotopic): 456.3603

AlogP: 6.44

#Rotatable Bonds: 2

Polar Surface Area: 49.69

Molecular Species: NEUTRAL

HBA: 3

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 3

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 13.93

CX Basic pKa: ┄

CX LogP: 4.98

CX LogD: 4.98

Aromatic Rings: ┄

Heavy Atoms: 33

QED Weighted: 0.50

Np Likeness Score: 3.31

References

1. Han Y, Cheng Y, Tian LW..  (2023)  Semisynthesis of 22,25-Epoxylanostane Triterpenoids: Structure Revision and Protective Effects against Oxygen-Glucose Deprivation/Reoxygenation Injury in H9c2 Cells.,  86  (2.0): [PMID:36748235] [10.1021/acs.jnatprod.2c01029]

Source

Source(1):

• Scientific Literature