nomilin

ID: ALA500167

Chembl Id: CHEMBL500167

PubChem CID: 12313416

Max Phase: Preclinical

Molecular Formula: C28H34O9

Molecular Weight: 514.57

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Nomilin | Nomilin|CHEMBL500167|BDBM50480319|[(1R,2R,4S,7R,8S,11R,12R,13S,18R)-7-(Furan-3-yl)-1,8,12,17,17-pentamethyl-5,15,20-trioxo-3,6,16-trioxapentacyclo[9.9.0.02,4.02,8.012,18]icosan-13-yl] acetate

Canonical SMILES:  CC(=O)O[C@H]1CC(=O)OC(C)(C)[C@@H]2CC(=O)[C@]3(C)[C@H](CC[C@@]4(C)[C@@H](c5ccoc5)OC(=O)[C@H]5O[C@]543)[C@@]12C

Standard InChI:  InChI=1S/C28H34O9/c1-14(29)34-19-12-20(31)36-24(2,3)17-11-18(30)27(6)16(26(17,19)5)7-9-25(4)21(15-8-10-33-13-15)35-23(32)22-28(25,27)37-22/h8,10,13,16-17,19,21-22H,7,9,11-12H2,1-6H3/t16-,17+,19+,21-,22-,25+,26-,27+,28-/m1/s1

Standard InChI Key:  KPDOJFFZKAUIOE-MFPNAYRGSA-N

Alternative Forms

1. Parent:

   

   ALA500167

   NOMILIN

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: 514.57

Molecular Weight (Monoisotopic): 514.2203

AlogP: 3.69

#Rotatable Bonds: 2

Polar Surface Area: 121.64

Molecular Species: NEUTRAL

HBA: 9

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 9

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.02

CX LogD: 3.02

Aromatic Rings: 1

Heavy Atoms: 37

QED Weighted: 0.33

Np Likeness Score: 3.10

References

1. Tan GT, Pezzuto JM, Kinghorn AD, Hughes SH..  (1991)  Evaluation of natural products as inhibitors of human immunodeficiency virus type 1 (HIV-1) reverse transcriptase.,  54  (1): [PMID:1710653] [10.1021/np50073a012]

2. Balestrieri E, Pizzimenti F, Ferlazzo A, Giofrè SV, Iannazzo D, Piperno A, Romeo R, Chiacchio MA, Mastino A, Macchi B..  (2011)  Antiviral activity of seed extract from Citrus bergamia towards human retroviruses.,  19  (6): [PMID:21334901] [10.1016/j.bmc.2011.01.024]

3. 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