rel-(2S,5R,6R,8S,9S,10R,18S,19R)-2-(2-methylbutyryloxy)-6-hydroxy-18,19-di-O-acetyl-18,19-epoxycleroda-3,13(16),14-triene

ID: ALA518074

Chembl Id: CHEMBL518074

PubChem CID: 44593487

Max Phase: Preclinical

Molecular Formula: C29H42O8

Molecular Weight: 518.65

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=CC(=C)CC[C@]1(C)[C@H]2C[C@H](OC(=O)C(C)CC)C=C3[C@H](OC(C)=O)O[C@H](OC(C)=O)[C@@]32[C@H](O)C[C@@H]1C

Standard InChI:  InChI=1S/C29H42O8/c1-9-16(3)11-12-28(8)18(5)13-24(32)29-22(26(34-19(6)30)37-27(29)35-20(7)31)14-21(15-23(28)29)36-25(33)17(4)10-2/h9,14,17-18,21,23-24,26-27,32H,1,3,10-13,15H2,2,4-8H3/t17?,18-,21+,23+,24+,26+,27-,28-,29-/m0/s1

Standard InChI Key:  UCTQGEZEUWGOLP-RVMSXZCWSA-N

Alternative Forms

1. Parent:

   

   ALA518074

   [(1R,3S,5S,6aR,7S,8S,10R,10aR)-1,3-diacetyloxy-10-hydroxy-7,8-dimethyl-7-(3-methylidenepent-4-enyl)-1,3,5,6,6a,8,9,10-octahydrobenzo[d][2]benzofuran-5-yl] 2-methylbutanoate

Molecule Features

Natural Product: Yes

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: 518.65

Molecular Weight (Monoisotopic): 518.2880

AlogP: 4.62

#Rotatable Bonds: 9

Polar Surface Area: 108.36

Molecular Species: NEUTRAL

HBA: 8

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 8

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.56

CX LogD: 4.56

Aromatic Rings: ┄

Heavy Atoms: 37

QED Weighted: 0.20

Np Likeness Score: 3.47

References

1. Shen YC, Cheng YB, Ahmed AF, Lee CL, Chen SY, Chien CT, Kuo YH, Tzeng GL..  (2005)  Cytotoxic clerodane diterpenoids from Casearia membranacea.,  68  (11): [PMID:16309320] [10.1021/np058063o]

2. Shen YC, Wang CH, Cheng YB, Wang LT, Guh JH, Chien CT, Khalil AT..  (2004)  New cytotoxic clerodane diterpenoids from the leaves and twigs of Casearia membranacea.,  67  (3): [PMID:15043402] [10.1021/np0303658]

3. Kanokmedhakul S, Kanokmedhakul K, Kanarsa T, Buayairaksa M..  (2005)  New bioactive clerodane diterpenoids from the bark of Casearia grewiifolia.,  68  (2): [PMID:15730240] [10.1021/np049757k]

4. Sai Prakash CV, Hoch JM, Kingston DG..  (2002)  Structure and stereochemistry of new cytotoxic clerodane diterpenoids from the bark of Casearia lucida from the Madagascar rainforest.,  65  (2): [PMID:11858738] [10.1021/np010405c]

5. Wang B, Wang XL, Wang SQ, Shen T, Liu YQ, Yuan H, Lou HX, Wang XN..  (2013)  Cytotoxic clerodane diterpenoids from the leaves and twigs of Casearia balansae.,  76  (9): [PMID:24033131] [10.1021/np400212d]

Source

Source(1):

• Scientific Literature