6alpha,8alpha,15(S)-trihydroxy-23-carbossimethyllabd-13(14),17-dien-16(S),19-olide

ID: ALA497636

Chembl Id: CHEMBL497636

PubChem CID: 44157608

Max Phase: Preclinical

Molecular Formula: C26H40O7

Molecular Weight: 464.60

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)[C@]1(C)CCC[C@@]2(C)[C@H]1[C@@H](O)C[C@@](C)(O)[C@@H]2CC/C(C)=C/[C@H](O)[C@H]1OC(=O)C=C1C

Standard InChI:  InChI=1S/C26H40O7/c1-15(12-17(27)21-16(2)13-20(29)33-21)8-9-19-24(3)10-7-11-25(4,23(30)32-6)22(24)18(28)14-26(19,5)31/h12-13,17-19,21-22,27-28,31H,7-11,14H2,1-6H3/b15-12+/t17-,18-,19+,21-,22+,24+,25+,26+/m0/s1

Standard InChI Key:  XTBDCOLQKPTUSD-LJEPAFQVSA-N

Alternative Forms

1. Parent:

   

   ALA497636

   methyl (1R,4aS,5R,6R,8S,8aR)-6,8-dihydroxy-5-[(E,5S)-5-hydroxy-3-methyl-5-[(2S)-3-methyl-5-oxo-2H-furan-2-yl]pent-3-enyl]-1,4a,6-trimethyl-3,4,5,7,8,8a-hexahydro-2H-naphthalene-1-carboxylate

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: 464.60

Molecular Weight (Monoisotopic): 464.2774

AlogP: 3.06

#Rotatable Bonds: 6

Polar Surface Area: 113.29

Molecular Species: NEUTRAL

HBA: 7

HBD: 3

#RO5 Violations: 0

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 9.43

CX Basic pKa:

CX LogP: 2.88

CX LogD: 2.87

Aromatic Rings: 0

Heavy Atoms: 33

QED Weighted: 0.41

Np Likeness Score: 2.75

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