6,7'-dihydroxy-2,5,5,8a-tetramethyl-3,4,4a,5,6,7,8,8a-octahydro-2H-3',11'-dioxaspiro[naphthalene-1,4'-tricyclo[7.3.0.0^{2,6}]dodecane]-1',6',8'-trien-10'-one

ID: ALA1170697

Chembl Id: CHEMBL1170697

Cas Number: 149691-31-6

PubChem CID: 11383606

Max Phase: Preclinical

Molecular Formula: C23H30O5

Molecular Weight: 386.49

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@@H]1CC[C@H]2C(C)(C)[C@H](O)CC[C@]2(C)[C@@]12Cc1c(O)cc3c(c1O2)COC3=O

Standard InChI:  InChI=1S/C23H30O5/c1-12-5-6-17-21(2,3)18(25)7-8-22(17,4)23(12)10-14-16(24)9-13-15(19(14)28-23)11-27-20(13)26/h9,12,17-18,24-25H,5-8,10-11H2,1-4H3/t12-,17+,18-,22+,23-/m1/s1

Standard InChI Key:  HKNSYAPUOMHZDE-RCJATNNHSA-N

Alternative Forms

1. Parent:

   

   ALA1170697

   Stachybotrolide

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: 386.49

Molecular Weight (Monoisotopic): 386.2093

AlogP: 3.97

#Rotatable Bonds: ┄

Polar Surface Area: 75.99

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.76

CX Basic pKa: ┄

CX LogP: 4.01

CX LogD: 3.99

Aromatic Rings: 1

Heavy Atoms: 28

QED Weighted: 0.66

Np Likeness Score: 3.08

References

1. Kaur K, Jain M, Kaur T, Jain R..  (2009)  Antimalarials from nature.,  17  (9): [PMID:19299148] [10.1016/j.bmc.2009.02.050]

2. Tedaldi L, Wagner GK.  (2014)  Beyond substrate analogues: new inhibitor chemotypes for glycosyltransferases,  5  (8): [10.1039/C4MD00086B]

3. Yang J, Wang Y, Guan W, Su W, Li G, Zhang S, Yao H..  (2022)  Spiral molecules with antimalarial activities: A review.,  237  [PMID:35461019] [10.1016/j.ejmech.2022.114361]

Source

Source(1):

• Scientific Literature