8alpha,15(S)-dihydroxylabd-13(14),17-dien-23,6alpha-16(S),19-diolide

ID: ALA496637

Chembl Id: CHEMBL496637

PubChem CID: 44157602

Max Phase: Preclinical

Molecular Formula: C25H36O6

Molecular Weight: 432.56

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1=CC(=O)O[C@@H]1[C@@H](O)/C=C(\C)CC[C@@H]1[C@@]2(C)CCC[C@@]3(C)C(=O)O[C@@H](C[C@@]1(C)O)[C@H]23

Standard InChI:  InChI=1S/C25H36O6/c1-14(11-16(26)20-15(2)12-19(27)31-20)7-8-18-23(3)9-6-10-24(4)21(23)17(30-22(24)28)13-25(18,5)29/h11-12,16-18,20-21,26,29H,6-10,13H2,1-5H3/b14-11+/t16-,17-,18+,20-,21+,23+,24+,25+/m0/s1

Standard InChI Key:  NFNKLYVALXQMTH-SUXGLGSNSA-N

Alternative Forms

1. Parent:

   

   ALA496637

   (1S,4R,8S,9R,10R,12R)-10-hydroxy-9-[(E,5S)-5-hydroxy-3-methyl-5-[(2S)-3-methyl-5-oxo-2H-furan-2-yl]pent-3-enyl]-4,8,10-trimethyl-2-oxatricyclo[6.3.1.04,12]dodecan-3-one

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: 432.56

Molecular Weight (Monoisotopic): 432.2512

AlogP: 3.45

#Rotatable Bonds: 5

Polar Surface Area: 93.06

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: 0

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 9.43

CX Basic pKa:

CX LogP: 3.39

CX LogD: 3.39

Aromatic Rings: 0

Heavy Atoms: 31

QED Weighted: 0.51

Np Likeness Score: 2.94

References

1. Dal Piaz F, Vassallo A, Lepore L, Tosco A, Bader A, De Tommasi N..  (2009)  Sesterterpenes as tubulin tyrosine ligase inhibitors. First insight of structure-activity relationships and discovery of new lead.,  52  (12): [PMID:19459643] [10.1021/jm801637f]

2. Bisio A, Schito AM, Pedrelli F, Danton O, Reinhardt JK, Poli G, Tuccinardi T, Bürgi T, De Riccardis F, Giacomini M, Calzia D, Panfoli I, Schito GC, Hamburger M, De Tommasi N..  (2020)  Antibacterial and ATP Synthesis Modulating Compounds from Salvia tingitana.,  83  (4): [PMID:32182064] [10.1021/acs.jnatprod.9b01024]

Source

Source(1):

• Scientific Literature