Paclitaxel derivative

ID: ALA384552

Chembl Id: CHEMBL384552

PubChem CID: 44346114

Max Phase: Preclinical

Molecular Formula: C56H57NO15

Molecular Weight: 984.06

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)O[C@H]1C(=O)[C@@]2(C)C([C@H](OC(=O)c3ccccc3)C3C[C@H](OC(=O)[C@H](OC(=O)c4ccc(C(C)=O)cc4)[C@@H](NC(=O)c4ccccc4)c4ccccc4)C(C)=C1C3(C)C)[C@]1(OC(C)=O)COC1C[C@@H]2O

Standard InChI:  InChI=1S/C56H57NO15/c1-30-40(69-53(66)47(71-52(65)38-25-23-34(24-26-38)31(2)58)44(35-17-11-8-12-18-35)57-50(63)36-19-13-9-14-20-36)27-39-45(70-51(64)37-21-15-10-16-22-37)48-55(7,41(61)28-42-56(48,29-67-42)72-33(4)60)49(62)46(68-32(3)59)43(30)54(39,5)6/h8-26,39-42,44-48,61H,27-29H2,1-7H3,(H,57,63)/t39?,40-,41-,42?,44-,45+,46+,47+,48?,55+,56-/m0/s1

Standard InChI Key:  ZDKKTFKDAIEIPS-IWFXOQQCSA-N

Alternative Forms

1. Parent:

   

   ALA384552

   [(1S,2R)-1-benzamido-3-[[(2R,4S,9S,10S,12R,15S)-4,12-diacetyloxy-2-benzoyloxy-9-hydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-15-yl]oxy]-3-oxo-1-phenylpropan-2-yl] 4-acetylbenzoate

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: 984.06

Molecular Weight (Monoisotopic): 983.3728

AlogP: 6.69

#Rotatable Bonds: 13

Polar Surface Area: 224.20

Molecular Species: NEUTRAL

HBA: 15

HBD: 2

#RO5 Violations: 3

HBA (Lipinski): 16

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 12.59

CX Basic pKa:

CX LogP: 6.59

CX LogD: 6.59

Aromatic Rings: 4

Heavy Atoms: 72

QED Weighted: 0.06

Np Likeness Score: 1.46

References

1. Rodrigues P, Scheuermann K, Stockmar C, Maier G, Fiebig H, Unger C, Mulhaupt R, Kratz F..  (2003)  Synthesis and in vitro efficacy of acid-sensitive poly(ethylene glycol) paclitaxel conjugates.,  13  (3): [PMID:12882225] [10.1016/s0960-894x(02)01002-8]

Source

Source(1):

• Scientific Literature