8alpha,15(S)-dihydroxy-23,6alpha-epoxy-labd-13(14),17-dien-16(S),19-olide

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)CO[C@@H](C[C@@]1(C)O)[C@@H]32

Standard InChI: InChI=1S/C25H38O5/c1-15(11-17(26)21-16(2)12-20(27)30-21)7-8-19-24(4)10-6-9-23(3)14-29-18(22(23)24)13-25(19,5)28/h11-12,17-19,21-22,26,28H,6-10,13-14H2,1-5H3/b15-11+/t17-,18-,19+,21-,22-,23-,24+,25+/m0/s1

Standard InChI Key: GAOMOYCMAISIED-URISLNGFSA-N

Molfile:

     RDKit          2D

 34 37  0  0  0  0  0  0  0  0999 V2000
    3.2375   -2.7333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2375   -3.5583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9495   -3.9667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9495   -2.3167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6615   -2.7333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6580   -3.5583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3668   -3.9716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0836   -3.5644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3622   -4.7965    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5292   -4.6792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3542   -4.6792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6555   -4.5583    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3738   -2.3216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0895   -2.7403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8033    0.1670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0885   -0.2521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0973   -1.0849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3746   -1.4947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2415   -1.8245    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3707    0.1546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3640    0.9796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5556    2.2032    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7472    2.3633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3405    1.6478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8976    1.0437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4056    3.1207    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6542   -1.9083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7350    0.2349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8000   -3.1500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4958   -2.0208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0751    1.3978    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6462    1.3862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4811    1.9367    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2297   -4.4770    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  5 13  1  0
  6  7  1  0
  7  8  1  0
 13 18  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
  8 14  1  0
 13 19  1  6
  3  6  1  0
 16 20  2  0
  7  9  1  0
 21 20  1  0
  5  4  1  0
 32 21  1  0
 32 22  1  0
  3 10  1  1
  5  6  1  0
  3 11  1  0
  9 11  1  0
 22 23  1  0
 23 24  1  0
 24 25  2  0
 32 25  1  0
 23 26  2  0
  6 12  1  6
  5 27  1  1
 13 14  1  0
 25 28  1  0
  1  2  1  0
 14 29  1  6
  1  4  1  0
 14 30  1  0
  2  3  1  0
 21 31  1  1
 32 33  1  1
  7 34  1  1
M  END

Alternative Forms

Parent:

ALA496239
(2S)-2-[(E,1S)-1-hydroxy-5-[(1S,4R,8S,9R,10R,12R)-10-hydroxy-4,8,10-trimethyl-2-oxatricyclo[6.3.1.04,12]dodecan-9-yl]-3-methylpent-2-enyl]-3-methyl-2H-furan-5-one

Associated Targets(Human)

TTL Tchem Tubulin--tyrosine ligase (25 Activities)

Discover Target: TTL

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

MCF7 (126967 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

HEK293 (82097 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Associated Targets(non-human)

J774.A1 (2436 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ALB Serum albumin (1163 Activities)

Discover Target: ALB

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

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

Drug Indications

MESH ID	MESH Heading	EFO IDs	EFO Terms	Max Phase for Indication	References

Mechanisms of Action

Mechanism of Action	Action Type	target ID	Target Name	Target Type	Target Organism	Binding Site Name	References

Calculated Properties

Molecular Weight: 418.57	Molecular Weight (Monoisotopic): 418.2719	AlogP: 3.93	#Rotatable Bonds: 5
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: 9.43	CX Basic pKa: ┄	CX LogP: 3.42	CX LogD: 3.42
Aromatic Rings: ┄	Heavy Atoms: 30	QED Weighted: 0.52	Np Likeness Score: 2.82

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]

Source

Source(1):

Scientific Literature