(1S,4S,5S,6R,7R,8S,9R,10S)-1,6-Diacetoxy-9-benzoyloxy-8-cinnamoyloxy-4-hydroxydihydro-beta-agarofuran

ID: ALA499498

Chembl Id: CHEMBL499498

PubChem CID: 25016918

Max Phase: Preclinical

Molecular Formula: C35H40O10

Molecular Weight: 620.70

Molecule Type: Small molecule

Associated Items:

Names and Identifiers

Canonical SMILES:  CC(=O)O[C@H]1CC[C@](C)(O)[C@]23OC(C)(C)[C@H]([C@H](OC(=O)/C=C/c4ccccc4)[C@H](OC(=O)c4ccccc4)[C@]12C)[C@H]3OC(C)=O

Standard InChI:  InChI=1S/C35H40O10/c1-21(36)41-25-19-20-33(5,40)35-29(42-22(2)37)27(32(3,4)45-35)28(43-26(38)18-17-23-13-9-7-10-14-23)30(34(25,35)6)44-31(39)24-15-11-8-12-16-24/h7-18,25,27-30,40H,19-20H2,1-6H3/b18-17+/t25-,27+,28-,29+,30-,33-,34-,35-/m0/s1

Standard InChI Key:  OVQQPOHQLNLSCP-HHATXKITSA-N

Associated Targets(Human)

ABCB1 Tchem P-glycoprotein 1 (14716 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

Mycobacterium tuberculosis (203094 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

Natural Product: NoOral: NoChemical Probe: NoParenteral: No
Molecule Type: Small moleculeTopical: NoFirst In Class: NoBlack Box: No
Chirality: NoAvailability: NoProdrug: No

Drug Indications

MESH IDMESH Heading EFO IDsEFO TermsMax Phase for IndicationReferences

Mechanisms of Action

Mechanism of ActionAction Typetarget IDTarget NameTarget TypeTarget OrganismBinding Site NameReferences

Calculated Properties

Molecular Weight: 620.70Molecular Weight (Monoisotopic): 620.2621AlogP: 4.43#Rotatable Bonds: 7
Polar Surface Area: 134.66Molecular Species: NEUTRALHBA: 10HBD: 1
#RO5 Violations: 1HBA (Lipinski): 10HBD (Lipinski): 1#RO5 Violations (Lipinski): 1
CX Acidic pKa: 13.76CX Basic pKa: CX LogP: 4.90CX LogD: 4.90
Aromatic Rings: 2Heavy Atoms: 45QED Weighted: 0.27Np Likeness Score: 2.14

References

1. Torres-Romero D, King-Díaz B, Jiménez IA, Lotina-Hennsen B, Bazzocchi IL..  (2008)  Sesquiterpenes from Celastrus vulcanicola as photosynthetic inhibitors.,  71  (8): [PMID:18616221] [10.1021/np070647y]
2. Torres-Romero D, Jiménez IA, Rojas R, Gilman RH, López M, Bazzocchi IL..  (2011)  Dihydro-β-agarofuran sesquiterpenes isolated from Celastrus vulcanicola as potential anti-Mycobacterium tuberculosis multidrug-resistant agents.,  19  (7): [PMID:21419633] [10.1016/j.bmc.2011.02.034]
3. Callies O, Sánchez-Cañete MP, Gamarro F, Jiménez IA, Castanys S, Bazzocchi IL..  (2016)  Optimization by Molecular Fine Tuning of Dihydro-β-agarofuran Sesquiterpenoids as Reversers of P-Glycoprotein-Mediated Multidrug Resistance.,  59  (5): [PMID:26836364] [10.1021/acs.jmedchem.5b01429]

Source