(2R,7S,8S,9R)-2,7,8-trihydroxy-9-propyl-5-nonen-9-olide

ID: ALA446877

Chembl Id: CHEMBL446877

PubChem CID: 9992042

Max Phase: Preclinical

Molecular Formula: C12H20O5

Molecular Weight: 244.29

Molecule Type: Small molecule

Names and Identifiers

Synonyms: herbarumin II | KQJGPGHQDDZVHJ-ZFOCBLLKSA-|herbarumin II|CHEMBL446877|(2R,3S,4S,5E,9R)-3,4,9-trihydroxy-2-propyl-2,3,4,7,8,9-hexahydrooxecin-10-one|InChI=1/C12H20O5/c1-2-5-10-11(15)8(13)6-3-4-7-9(14)12(16)17-10/h3,6,8-11,13-15H,2,4-5,7H2,1H3/b6-3+/t8-,9+,10+,11-/m0/s1

Canonical SMILES:  CCC[C@H]1OC(=O)[C@H](O)CC/C=C/[C@H](O)[C@@H]1O

Standard InChI:  InChI=1S/C12H20O5/c1-2-5-10-11(15)8(13)6-3-4-7-9(14)12(16)17-10/h3,6,8-11,13-15H,2,4-5,7H2,1H3/b6-3+/t8-,9+,10+,11-/m0/s1

Standard InChI Key:  KQJGPGHQDDZVHJ-ZFOCBLLKSA-N

Alternative Forms

1. Parent:

   

   ALA446877

   HERBARUMIN II

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: 244.29

Molecular Weight (Monoisotopic): 244.1311

AlogP: 0.13

#Rotatable Bonds: 2

Polar Surface Area: 86.99

Molecular Species: NEUTRAL

HBA: 5

HBD: 3

#RO5 Violations: 0

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 12.54

CX Basic pKa:

CX LogP: 0.53

CX LogD: 0.53

Aromatic Rings: 0

Heavy Atoms: 17

QED Weighted: 0.47

Np Likeness Score: 2.45

References

1. Rivero-Cruz JF, Macías M, Cerda-García-Rojas CM, Mata R..  (2003)  A new phytotoxic nonenolide from Phoma herbarum.,  66  (4): [PMID:12713403] [10.1021/np020501t]

2. Cimmino A, Andolfi A, Fondevilla S, Abouzeid MA, Rubiales D, Evidente A..  (2012)  Pinolide, a new nonenolide produced by Didymella pinodes , the causal agent of ascochyta blight on Pisum sativum.,  60  (21): [PMID:22568524] [10.1021/jf300824d]

Source

Source(1):

• Scientific Literature