rel-(2S,5R,6R,8S,9S,10R,18S,19R)-18,19-diacetoxy-18,19-epoxy-6-methoxy-2-(2-methylbutanoyloxy)cleroda-3,13(16),14-triene

ID: ALA456511

Chembl Id: CHEMBL456511

PubChem CID: 44593673

Max Phase: Preclinical

Molecular Formula: C30H44O8

Molecular Weight: 532.67

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](OC)C[C@@H]1C

Standard InChI:  InChI=1S/C30H44O8/c1-10-17(3)12-13-29(8)19(5)14-25(34-9)30-23(27(35-20(6)31)38-28(30)36-21(7)32)15-22(16-24(29)30)37-26(33)18(4)11-2/h10,15,18-19,22,24-25,27-28H,1,3,11-14,16H2,2,4-9H3/t18?,19-,22+,24+,25+,27+,28-,29-,30-/m0/s1

Standard InChI Key:  PRXYABXGJNKXKE-JQOSQATJSA-N

Alternative Forms

1. Parent:

   

   ALA456511

   [(1R,3S,5S,6aR,7S,8S,10R,10aR)-1,3-diacetyloxy-10-methoxy-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: 532.67

Molecular Weight (Monoisotopic): 532.3036

AlogP: 5.27

#Rotatable Bonds: 10

Polar Surface Area: 97.36

Molecular Species: NEUTRAL

HBA: 8

HBD: ┄

#RO5 Violations: 2

HBA (Lipinski): 8

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 2

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 5.20

CX LogD: 5.20

Aromatic Rings: ┄

Heavy Atoms: 38

QED Weighted: 0.16

Np Likeness Score: 3.40

References

1. 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]

2. 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]

Source

Source(1):

• Scientific Literature