Limonol

ID: ALA2269932

Chembl Id: CHEMBL2269932

PubChem CID: 76312411

Max Phase: Preclinical

Molecular Formula: C26H32O8

Molecular Weight: 472.53

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1(C)O[C@H]2CC(=O)OC[C@]23[C@H]2CC[C@@]4(C)[C@@H](c5ccoc5)OC(=O)[C@H]5O[C@]54[C@]2(C)[C@H](O)C[C@@H]13

Standard InChI:  InChI=1S/C26H32O8/c1-22(2)15-9-16(27)24(4)14(25(15)12-31-18(28)10-17(25)33-22)5-7-23(3)19(13-6-8-30-11-13)32-21(29)20-26(23,24)34-20/h6,8,11,14-17,19-20,27H,5,7,9-10,12H2,1-4H3/t14-,15-,16+,17-,19+,20+,23-,24-,25+,26+/m0/s1

Standard InChI Key:  ZFIURKZEANVFML-RVWQQJOKSA-N

Alternative Forms

1. Parent:

   

   ALA2269932

   LIMONOL

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: 472.53

Molecular Weight (Monoisotopic): 472.2097

AlogP: 2.93

#Rotatable Bonds: 1

Polar Surface Area: 107.73

Molecular Species: NEUTRAL

HBA: 8

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 1.89

CX LogD: 1.89

Aromatic Rings: 1

Heavy Atoms: 34

QED Weighted: 0.49

Np Likeness Score: 3.63

References

1. Govindachari T, Suresh G, Gopalakrishnan G, Masilamani S, Banumathi B.  (2000)  Antifungal activity of some tetranortriterpenoids,  71  (4): [10.1016/S0367-326X(99)00155-0]

2. Ruberto G, Renda A, Tringali C, Napoli EM, Simmonds MS..  (2002)  Citrus limonoids and their semisynthetic derivatives as antifeedant agents against Spodoptera frugiperda larvae. A structure-activity relationship study.,  50  (23): [PMID:12405773] [10.1021/jf020607u]

Source

Source(1):

• Scientific Literature