5-(2-{1-[5-Hydroxy-1-(4-hydroxy-4-methyl-pentyl)-5-methyl-hexyl]-7a-methyl-octahydro-inden-4-ylidene}-ethylidene)-4-methylene-cyclohexane-1,3-diol

ID: ALA94219

Chembl Id: CHEMBL94219

PubChem CID: 10436120

Max Phase: Preclinical

Molecular Formula: C32H54O4

Molecular Weight: 502.78

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=C1/C(=C\C=C2/CCC[C@]3(C)[C@@H](C(CCCC(C)(C)O)CCCC(C)(C)O)CC[C@@H]23)C[C@@H](O)C[C@@H]1O

Standard InChI:  InChI=1S/C32H54O4/c1-22-25(20-26(33)21-29(22)34)14-13-24-12-9-19-32(6)27(15-16-28(24)32)23(10-7-17-30(2,3)35)11-8-18-31(4,5)36/h13-14,23,26-29,33-36H,1,7-12,15-21H2,2-6H3/b24-13+,25-14-/t26-,27-,28+,29+,32-/m1/s1

Standard InChI Key:  WTQXZYVWLNPNEX-LKUPKUSPSA-N

Alternative Forms

1. Parent:

   

   ALA94219

   1alpha,25-Dihydroxy-21-(3-hydroxy-3-methylbutyl)vitamin D(3)

2. Alternative Forms:

   

   ALA94219

   (1R,3S,5Z)-5-[(2E)-2-[(1R,3aS,7aR)-7a-methyl-1-[(6S)-1,1,1-trideuterio-2,10-dihydroxy-10-methyl-2-(trideuteriomethyl)undecan-6-yl]-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-4-methylidenecyclohexane-1,3-diol
3. 

   ALA94219

   (1R,3S,5Z)-5-[(2E)-2-[(1R,3aS,7aR)-7a-methyl-1-[(6R)-1,1,1-trideuterio-2,10-dihydroxy-10-methyl-2-(trideuteriomethyl)undecan-6-yl]-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-4-methylidenecyclohexane-1,3-diol

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 502.78

Molecular Weight (Monoisotopic): 502.4022

AlogP: 6.63

#Rotatable Bonds: 10

Polar Surface Area: 80.92

Molecular Species: NEUTRAL

HBA: 4

HBD: 4

#RO5 Violations: 2

HBA (Lipinski): 4

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 2

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.94

CX LogD: 4.94

Aromatic Rings: ┄

Heavy Atoms: 36

QED Weighted: 0.27

Np Likeness Score: 2.20

References

1. Norman AW, Manchand PS, Uskokovic MR, Okamura WH, Takeuchi JA, Bishop JE, Hisatake JI, Koeffler HP, Peleg S..  (2000)  Characterization of a novel analogue of 1alpha,25(OH)(2)-vitamin D(3) with two side chains: interaction with its nuclear receptor and cellular actions.,  43  (14): [PMID:10893309] [10.1021/jm0000160]

2. Maehr H, Uskokovic MR, Adorini L, Reddy GS..  (2004)  Calcitriol derivatives with two different side chains at C-20. II. Diastereoselective syntheses of the metabolically produced 24(R)-hydroxygemini.,  47  (26): [PMID:15588082] [10.1021/jm049340b]

Source

Source(1):

• Scientific Literature