3'-Dephenyl-3'-(2-methylpropyl)-10-n-propanoyldocetaxel

ID: ALA420349

PubChem CID: 10843217

Max Phase: Preclinical

Molecular Formula: C44H61NO15

Molecular Weight: 843.96

Molecule Type: Small molecule

Names and Identifiers

Synonyms: SB-T-1103 | CHEMBL420349|SB-T-1103

Canonical SMILES:  CCC(=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/C44H61NO15/c1-12-30(48)57-33-31-23(4)27(56-38(52)32(49)26(18-22(2)3)45-39(53)60-40(6,7)8)20-44(54,41(31,9)10)36(58-37(51)25-16-14-13-15-17-25)34-42(11,35(33)50)28(47)19-29-43(34,21-55-29)59-24(5)46/h13-17,22,26-29,32-34,36,47,49,54H,12,18-21H2,1-11H3,(H,45,53)/t26-,27-,28-,29+,32+,33+,34-,36-,42+,43-,44+/m0/s1

Standard InChI Key:  JTFSQGOZNMBTHL-YIFABKNJSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA420349

   [(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4-acetyloxy-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-12-propanoyloxy-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: 843.96

Molecular Weight (Monoisotopic): 843.4041

AlogP: 3.89

#Rotatable Bonds: 11

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: 11.84

CX Basic pKa: ┄

CX LogP: 3.94

CX LogD: 3.94

Aromatic Rings: 1

Heavy Atoms: 60

QED Weighted: 0.14

Np Likeness Score: 1.98

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. Kuznetsova L, Chen J, Sun L, Wu X, Pepe A, Veith JM, Pera P, Bernacki RJ, Ojima I..  (2006)  Syntheses and evaluation of novel fatty acid-second-generation taxoid conjugates as promising anticancer agents.,  16  (4): [PMID:16298526] [10.1016/j.bmcl.2005.10.089]

3. Ojima I, Chen J, Sun L, Borella CP, Wang T, Miller ML, Lin S, Geng X, Kuznetsova L, Qu C, Gallager D, Zhao X, Zanardi I, Xia S, Horwitz SB, Mallen-St Clair J, Guerriero JL, Bar-Sagi D, Veith JM, Pera P, Bernacki RJ..  (2008)  Design, synthesis, and biological evaluation of new-generation taxoids.,  51  (11): [PMID:18465846] [10.1021/jm800086e]

4. Ojima I, Das M..  (2009)  Recent advances in the chemistry and biology of new generation taxoids.,  72  (3): [PMID:19239240] [10.1021/np8006556]

Source

Source(1):

• Scientific Literature