12-(4-benzoylphenethylcarbonyloxy)-2-benzyloxy-1,15-dihydroxy-10,14,17,17-tetramethyl-4-methylcarbonyloxy-11-oxo-(1S,2S,3R,4S,7R,9S,10S,12R,15S)-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-9-yl 3-(2-naphthyl)-(E)-2

ID: ALA383907

PubChem CID: 44401334

Max Phase: Preclinical

Molecular Formula: C58H58O12

Molecular Weight: 947.09

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)O[C@@]12CO[C@@H]1C[C@H](OC(=O)/C=C/c1ccc3ccccc3c1)[C@@]1(C)C(=O)[C@H](OC(=O)CCc3ccc(C(=O)c4ccccc4)cc3)C3=C(C)[C@@H](O)C[C@@](O)([C@@H](OCc4ccccc4)[C@H]21)C3(C)C

Standard InChI:  InChI=1S/C58H58O12/c1-35-44(60)32-58(65)54(66-33-39-14-8-6-9-15-39)52-56(5,45(31-46-57(52,34-67-46)70-36(2)59)68-47(61)29-24-38-22-25-40-16-12-13-19-43(40)30-38)53(64)51(49(35)55(58,3)4)69-48(62)28-23-37-20-26-42(27-21-37)50(63)41-17-10-7-11-18-41/h6-22,24-27,29-30,44-46,51-52,54,60,65H,23,28,31-34H2,1-5H3/b29-24+/t44-,45-,46+,51+,52-,54-,56+,57-,58+/m0/s1

Standard InChI Key:  ZAAVDKNOJOHYDH-OEGQEXDLSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA383907

   [(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4-acetyloxy-1,15-dihydroxy-10,14,17,17-tetramethyl-9-[(E)-3-naphthalen-2-ylprop-2-enoyl]oxy-11-oxo-2-phenylmethoxy-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-12-yl] 3-(4-benzoylphenyl)propanoate

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: 947.09

Molecular Weight (Monoisotopic): 946.3928

AlogP: 8.27

#Rotatable Bonds: 13

Polar Surface Area: 171.96

Molecular Species: NEUTRAL

HBA: 12

HBD: 2

#RO5 Violations: 3

HBA (Lipinski): 12

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 12.27

CX Basic pKa: ┄

CX LogP: 8.68

CX LogD: 8.68

Aromatic Rings: 5

Heavy Atoms: 70

QED Weighted: 0.04

Np Likeness Score: 1.62

References

1. Ojima I, Borella CP, Wu X, Bounaud PY, Oderda CF, Sturm M, Miller ML, Chakravarty S, Chen J, Huang Q, Pera P, Brooks TA, Baer MR, Bernacki RJ..  (2005)  Design, synthesis and structure-activity relationships of novel taxane-based multidrug resistance reversal agents.,  48  (6): [PMID:15771464] [10.1021/jm049483y]

Source

Source(1):

• Scientific Literature