1,9,12-trihydroxy-10,14,17,17-tetramethyl-4-methylcarbonyloxy-11-oxo-2-phenylcarbonyloxy-(1S,2S,3R,4S,7R,9S,10S,12R,15S)-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-15-yl 3-(4-benzoylphenyl)-(E)-2-propenoate

ID: ALA299041

PubChem CID: 11158560

Max Phase: Preclinical

Molecular Formula: C45H46O12

Molecular Weight: 778.85

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)O[C@@]12CO[C@@H]1C[C@H](O)[C@@]1(C)C(=O)[C@H](O)C3=C(C)[C@@H](OC(=O)/C=C/c4ccc(C(=O)c5ccccc5)cc4)C[C@@](O)([C@@H](OC(=O)c4ccccc4)[C@H]21)C3(C)C

Standard InChI:  InChI=1S/C45H46O12/c1-25-31(55-34(48)21-18-27-16-19-29(20-17-27)36(49)28-12-8-6-9-13-28)23-45(53)40(56-41(52)30-14-10-7-11-15-30)38-43(5,39(51)37(50)35(25)42(45,3)4)32(47)22-33-44(38,24-54-33)57-26(2)46/h6-21,31-33,37-38,40,47,50,53H,22-24H2,1-5H3/b21-18+/t31-,32-,33+,37+,38-,40-,43+,44-,45+/m0/s1

Standard InChI Key:  VAOIACFXRUOHSN-WOHIVVFVSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA299041

   [(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4-acetyloxy-15-[(E)-3-(4-benzoylphenyl)prop-2-enoyl]oxy-1,9,12-trihydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] benzoate

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: 778.85

Molecular Weight (Monoisotopic): 778.2989

AlogP: 4.58

#Rotatable Bonds: 8

Polar Surface Area: 182.96

Molecular Species: NEUTRAL

HBA: 12

HBD: 3

#RO5 Violations: 2

HBA (Lipinski): 12

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 12.64

CX Basic pKa: ┄

CX LogP: 5.09

CX LogD: 5.09

Aromatic Rings: 3

Heavy Atoms: 57

QED Weighted: 0.10

Np Likeness Score: 2.07

References

1. Ojima I, Bounaud PY, Takeuchi C, Pera P, Bernacki RJ..  (1998)  New taxanes as highly efficient reversal agents for multidrug resistance in cancer cells.,  8  (2): [PMID:9871652] [10.1016/s0960-894x(97)10218-9]

2. Huang Q, Kirikae F, Kirikae T, Pepe A, Amin A, Respicio L, Slayden RA, Tonge PJ, Ojima I..  (2006)  Targeting FtsZ for antituberculosis drug discovery: noncytotoxic taxanes as novel antituberculosis agents.,  49  (2): [PMID:16420032] [10.1021/jm050920y]

Source

Source(1):

• Scientific Literature