docetaxel analogue

ID: ALA355364

PubChem CID: 44379390

Max Phase: Preclinical

Molecular Formula: C46H57NO14

Molecular Weight: 847.96

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=C(C)c1ccc([C@H](NC(=O)OC(C)(C)C)[C@@H](O)C(=O)O[C@H]2C[C@@]3(O)[C@@H](OC(=O)c4ccccc4)[C@@H]4[C@]5(OC(C)=O)CO[C@@H]5C[C@H](O)[C@@]4(C)C(=O)[C@H](O)C(=C2C)C3(C)C)cc1

Standard InChI:  InChI=1S/C46H57NO14/c1-23(2)26-16-18-27(19-17-26)33(47-41(55)61-42(5,6)7)35(51)40(54)58-29-21-46(56)38(59-39(53)28-14-12-11-13-15-28)36-44(10,37(52)34(50)32(24(29)3)43(46,8)9)30(49)20-31-45(36,22-57-31)60-25(4)48/h11-19,29-31,33-36,38,49-51,56H,1,20-22H2,2-10H3,(H,47,55)/t29-,30-,31+,33-,34+,35+,36-,38-,44+,45-,46+/m0/s1

Standard InChI Key:  QUNXKUVMZDHZML-FTCBEXCOSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA355364

   [(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4-acetyloxy-1,9,12-trihydroxy-15-[(2R,3S)-2-hydroxy-3-[(2-methylpropan-2-yl)oxycarbonylamino]-3-(4-prop-1-en-2-ylphenyl)propanoyl]oxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] be

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: 847.96

Molecular Weight (Monoisotopic): 847.3779

AlogP: 4.29

#Rotatable Bonds: 9

Polar Surface Area: 224.45

Molecular Species: NEUTRAL

HBA: 14

HBD: 5

#RO5 Violations: 2

HBA (Lipinski): 15

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 11.90

CX Basic pKa: ┄

CX LogP: 3.95

CX LogD: 3.95

Aromatic Rings: 2

Heavy Atoms: 61

QED Weighted: 0.13

Np Likeness Score: 1.86

References

1. Bourzat J, Lavelle F, Commercon A.  (1995)  Synthesis and biological activity of Para-substituted 3-phenyl docetaxel analogs,  5  (8): [10.1016/0960-894X(95)00118-D]

Source

Source(1):

• Scientific Literature