Taxane analogue

ID: ALA58623

PubChem CID: 11193429

Max Phase: Preclinical

Molecular Formula: C42H44O11

Molecular Weight: 724.80

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)O[C@@]12CO[C@@H]1C[C@H](O)[C@@]1(C)C(=O)[C@H](O)C3=C(C)[C@@H](OC(=O)/C=C/c4ccc5ccccc5c4)C[C@@](O)([C@@H](OC(=O)c4ccccc4)[C@H]21)C3(C)C

Standard InChI:  InChI=1S/C42H44O11/c1-23-29(51-32(45)18-16-25-15-17-26-11-9-10-14-28(26)19-25)21-42(49)37(52-38(48)27-12-7-6-8-13-27)35-40(5,36(47)34(46)33(23)39(42,3)4)30(44)20-31-41(35,22-50-31)53-24(2)43/h6-19,29-31,34-35,37,44,46,49H,20-22H2,1-5H3/b18-16+/t29-,30-,31+,34+,35-,37-,40+,41-,42+/m0/s1

Standard InChI Key:  MYSWFMUVRHEUJM-LUZZEONASA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA58623

   (2alpha,5beta,7beta,10beta,13alpha)-4-(Acetyloxy)-1,7,10-trihydroxy-13-{[3-(naphthalen-2-yl)prop-2-enoyl]oxy}-9-oxo-5,20-epoxytax-11-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: 724.80

Molecular Weight (Monoisotopic): 724.2884

AlogP: 4.50

#Rotatable Bonds: 6

Polar Surface Area: 165.89

Molecular Species: NEUTRAL

HBA: 11

HBD: 3

#RO5 Violations: 2

HBA (Lipinski): 11

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 12.64

CX Basic pKa: ┄

CX LogP: 4.62

CX LogD: 4.62

Aromatic Rings: 3

Heavy Atoms: 53

QED Weighted: 0.14

Np Likeness Score: 2.25

References

1. Ojima I, Bounaud PY, Takeuchi C, Pera P, Bernacki RJ..  (1998)  New taxanes as highly efficient reversal agents for multidrug resistance in cancer cells.,  8  (2): [PMID:9871652] [10.1016/s0960-894x(97)10218-9]

2. Huang Q, Kirikae F, Kirikae T, Pepe A, Amin A, Respicio L, Slayden RA, Tonge PJ, Ojima I..  (2006)  Targeting FtsZ for antituberculosis drug discovery: noncytotoxic taxanes as novel antituberculosis agents.,  49  (2): [PMID:16420032] [10.1021/jm050920y]

3. Hurley KA, Santos TM, Nepomuceno GM, Huynh V, Shaw JT, Weibel DB..  (2016)  Targeting the Bacterial Division Protein FtsZ.,  59  (15): [PMID:26756351] [10.1021/acs.jmedchem.5b01098]

Source

Source(1):

• Scientific Literature