Taxol analogue

ID: ALA67756

PubChem CID: 44310800

Max Phase: Preclinical

Molecular Formula: C45H55NO14

Molecular Weight: 833.93

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)O[C@H]1C(=O)[C@@]2(C)[C@H]([C@H](OC(=O)c3ccccc3)[C@]3(O)C[C@H](OC(=O)[C@H](O)[C@@H](NC(=O)C(C)(C)C)c4ccccc4)C(C)=C1C3(C)C)[C@]1(OC(C)=O)CO[C@@H]1C[C@@H]2O

Standard InChI:  InChI=1S/C45H55NO14/c1-23-28(58-39(53)33(50)32(26-16-12-10-13-17-26)46-40(54)41(4,5)6)21-45(55)37(59-38(52)27-18-14-11-15-19-27)35-43(9,29(49)20-30-44(35,22-56-30)60-25(3)48)36(51)34(57-24(2)47)31(23)42(45,7)8/h10-19,28-30,32-35,37,49-50,55H,20-22H2,1-9H3,(H,46,54)/t28-,29-,30+,32-,33+,34+,35-,37-,43+,44-,45+/m0/s1

Standard InChI Key:  KNOHTDDBTZZQSM-OAGWZNDDSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA67756

   [(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-diacetyloxy-15-[(2R,3S)-3-(2,2-dimethylpropanoylamino)-2-hydroxy-3-phenylpropanoyl]oxy-1,9-dihydroxy-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: 833.93

Molecular Weight (Monoisotopic): 833.3623

AlogP: 3.47

#Rotatable Bonds: 9

Polar Surface Area: 221.29

Molecular Species: NEUTRAL

HBA: 14

HBD: 4

#RO5 Violations: 2

HBA (Lipinski): 15

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 11.85

CX Basic pKa: ┄

CX LogP: 3.48

CX LogD: 3.48

Aromatic Rings: 2

Heavy Atoms: 60

QED Weighted: 0.16

Np Likeness Score: 1.96

References

1. Czaplinski KA, Grunewald GL.  (1994)  A comparative molecular field analysis derived model of the binding of taxol analogues to microtubules,  4  (18): [10.1016/S0960-894X(00)80073-6]

2. Georg GI, Boge TC, Cheruvallath ZS, Harriman GC, Hepperle M, Park H, Himes RH.  (1994)  Schotten-Baumann acylation of N-debenzoyltaxol; an efficient route to N-acyl taxol analogues and their biological evaluation,  4  (2): [10.1016/S0960-894X(01)80139-6]

3. PubChem BioAssay data set, 

Source

Source(2):

• Scientific Literature
• PubChem BioAssays