10-Acetyl-3'-(2-methylpropyl) docetaxel

ID: ALA126932

PubChem CID: 44350757

Max Phase: Preclinical

Molecular Formula: C43H59NO15

Molecular Weight: 829.94

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](CC(C)C)NC(=O)OC(C)(C)C)C(C)=C1C3(C)C)[C@]1(OC(C)=O)CO[C@@H]1C[C@@H]2O

Standard InChI:  InChI=1S/C43H59NO15/c1-21(2)17-26(44-38(52)59-39(6,7)8)31(48)37(51)56-27-19-43(53)35(57-36(50)25-15-13-12-14-16-25)33-41(11,28(47)18-29-42(33,20-54-29)58-24(5)46)34(49)32(55-23(4)45)30(22(27)3)40(43,9)10/h12-16,21,26-29,31-33,35,47-48,53H,17-20H2,1-11H3,(H,44,52)/t26-,27-,28-,29+,31+,32+,33-,35-,41+,42-,43+/m0/s1

Standard InChI Key:  FZKDZYMJFJHGJQ-LYEXFJIESA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA126932

   [(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-diacetyloxy-1,9-dihydroxy-15-[(2R,3S)-2-hydroxy-5-methyl-3-[(2-methylpropan-2-yl)oxycarbonylamino]hexanoyl]oxy-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: 829.94

Molecular Weight (Monoisotopic): 829.3885

AlogP: 3.50

#Rotatable Bonds: 10

Polar Surface Area: 230.52

Molecular Species: NEUTRAL

HBA: 15

HBD: 4

#RO5 Violations: 2

HBA (Lipinski): 16

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 12.01

CX Basic pKa: ┄

CX LogP: 3.24

CX LogD: 3.24

Aromatic Rings: 1

Heavy Atoms: 59

QED Weighted: 0.15

Np Likeness Score: 2.03

References

1. Ojima I, Slater JC, Michaud E, Kuduk SD, Bounaud PY, Vrignaud P, Bissery MC, Veith JM, Pera P, Bernacki RJ..  (1996)  Syntheses and structure-activity relationships of the second-generation antitumor taxoids: exceptional activity against drug-resistant cancer cells.,  39  (20): [PMID:8831755] [10.1021/jm9604080]

2. Matesanz R, Trigili C, Rodríguez-Salarichs J, Zanardi I, Pera B, Nogales A, Fang WS, Jímenez-Barbero J, Canales A, Barasoain I, Ojima I, Díaz JF..  (2014)  Taxanes with high potency inducing tubulin assembly overcome tumoural cell resistances.,  22  (18): [PMID:25047938] [10.1016/j.bmc.2014.05.048]

Source

Source(1):

• Scientific Literature