(R)-4-((3R,5R,8R,9S,10S,13R,14S,17R)-10,13-dimethyl-3-(methylsulfonyloxy)hexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoic acid

ID: ALA4540985

Chembl Id: CHEMBL4540985

PubChem CID: 21771350

Max Phase: Preclinical

Molecular Formula: C25H42O5S

Molecular Weight: 454.67

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](OS(C)(=O)=O)CC[C@]4(C)[C@H]3CC[C@]12C

Standard InChI:  InChI=1S/C25H42O5S/c1-16(5-10-23(26)27)20-8-9-21-19-7-6-17-15-18(30-31(4,28)29)11-13-24(17,2)22(19)12-14-25(20,21)3/h16-22H,5-15H2,1-4H3,(H,26,27)/t16-,17-,18-,19+,20-,21+,22+,24+,25-/m1/s1

Standard InChI Key:  QKDRPUDDQCLYDP-ULCLHEGSSA-N

Alternative Forms

1. Parent:

   

   ALA4540985

   (4~{R})-4-[(3~{R},5~{R},8~{R},9~{S},10~{S},13~{R},14~{S},17~{R})-10,13-dimethyl-3-methylsulfonyloxy-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1~{H}-cyclopenta[a]phenanthren-17-yl]pentanoic acid

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: 454.67

Molecular Weight (Monoisotopic): 454.2753

AlogP: 5.49

#Rotatable Bonds: 6

Polar Surface Area: 80.67

Molecular Species: ACID

HBA: 4

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 4.79

CX Basic pKa: ┄

CX LogP: 4.96

CX LogD: 2.40

Aromatic Rings: ┄

Heavy Atoms: 31

QED Weighted: 0.54

Np Likeness Score: 1.92

References

1. Masuno H, Kazui Y, Tanatani A, Fujii S, Kawachi E, Ikura T, Ito N, Yamamoto K, Kagechika H..  (2019)  Development of novel lithocholic acid derivatives as vitamin D receptor agonists.,  27  (16): [PMID:31300316] [10.1016/j.bmc.2019.07.003]

2. Sasaki H,Masuno H,Kawasaki H,Yoshihara A,Numoto N,Ito N,Ishida H,Yamamoto K,Hirata N,Kanda Y,Kawachi E,Kagechika H,Tanatani A.  (2021)  Lithocholic Acid Derivatives as Potent Vitamin D Receptor Agonists.,  64  (1.0): [PMID:33369416] [10.1021/acs.jmedchem.0c01420]

Source

Source(1):

• Scientific Literature