(R)-6-(1,1-Dimethyl-allyl)-2-(1-hydroxy-1-methyl-ethyl)-2,3-dihydro-furo[3,2-g]chromen-7-one

ID: ALA1231470

Chembl Id: CHEMBL1231470

Cas Number: 14755-47-6

PubChem CID: 5287846

Max Phase: Preclinical

Molecular Formula: C19H22O4

Molecular Weight: 314.38

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Chalepin | Rutamarin alcohol|Chalepin, (+)-|(+)-rutamarin alcohol|Rutamarin alcohol, (+)-|V0632559OD|6-(1,1-DIMETHYLALLYL)-2-(1-HYDROXY-1-METHYLETHYL)-2,3-DIHYDRO-7H-FURO[3,2-G]CHROMEN-7-ONE|UNII-V0632559OD|14755-47-6|7H-Furo(3,2-g)(1)benzopyran-7-one, 6-(1,1-dimethyl-2-propen-1-yl)-2,3-dihydro-2-(1-hydroxy-1-methylethyl)-, (+)-|7H-Furo(3,2-g)(1)benzopyran-7-one, 6-(1,1-dimethyl-2-propenyl)-2,3-dihydro-2-(1-hydroxy-1-methylethyl)-, (+)-|(+)-Chalepin|MEGxp0_001084|CHEMBL1231470|ACon1_000926|DTXSIShow More⌵

Canonical SMILES:  C=CC(C)(C)c1cc2cc3c(cc2oc1=O)O[C@H](C(C)(C)O)C3

Standard InChI:  InChI=1S/C19H22O4/c1-6-18(2,3)13-8-11-7-12-9-16(19(4,5)21)22-14(12)10-15(11)23-17(13)20/h6-8,10,16,21H,1,9H2,2-5H3/t16-/m0/s1

Standard InChI Key:  JCDLLLXYAICSQV-INIZCTEOSA-N

Alternative Forms

1. Parent:

   

   ALA1231470

   CHALEPIN

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: 314.38

Molecular Weight (Monoisotopic): 314.1518

AlogP: 3.33

#Rotatable Bonds: 3

Polar Surface Area: 59.67

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.30

CX LogD: 3.30

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.70

Np Likeness Score: 2.23

References

1. Leitão A, Andricopulo AD, Oliva G, Pupo MT, de Marchi AA, Vieira PC, da Silva MF, Ferreira VF, de Souza MC, Sá MM, Moraes VR, Montanari CA..  (2004)  Structure-activity relationships of novel inhibitors of glyceraldehyde-3-phosphate dehydrogenase.,  14  (9): [PMID:15081008] [10.1016/j.bmcl.2004.02.025]

2. Freitas RF, Prokopczyk IM, Zottis A, Oliva G, Andricopulo AD, Trevisan MT, Vilegas W, Silva MG, Montanari CA..  (2009)  Discovery of novel Trypanosoma cruzi glyceraldehyde-3-phosphate dehydrogenase inhibitors.,  17  (6): [PMID:19254846] [10.1016/j.bmc.2009.01.079]

3. Prati F, Uliassi E, Bolognesi ML.  (2014)  Two diseases, one approach: multitarget drug discovery in Alzheimer's and neglected tropical diseases,  5  (7): [10.1039/C4MD00069B]

Source

Source(1):

• Scientific Literature