2-[3-(4-Amino-butylamino)-propylamino]-N-[(5S,5aS,8aR,9R)-9-(4-hydroxy-3,5-dimethoxy-phenyl)-8-oxo-5,5a,6,8,8a,9-hexahydro-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-5-yl]-acetamide

ID: ALA4249615

PubChem CID: 25229662

Max Phase: Preclinical

Molecular Formula: C30H40N4O8

Molecular Weight: 584.67

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc([C@@H]2c3cc4c(cc3[C@@H](NC(=O)CNCCCNCCCCN)[C@H]3COC(=O)[C@H]23)OCO4)cc(OC)c1O

Standard InChI:  InChI=1S/C30H40N4O8/c1-38-23-10-17(11-24(39-2)29(23)36)26-18-12-21-22(42-16-41-21)13-19(18)28(20-15-40-30(37)27(20)26)34-25(35)14-33-9-5-8-32-7-4-3-6-31/h10-13,20,26-28,32-33,36H,3-9,14-16,31H2,1-2H3,(H,34,35)/t20-,26+,27-,28+/m0/s1

Standard InChI Key:  UYIWMKHWVVWVNH-PCULNXKLSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA4249615

   N-[(5S,5aS,8aR,9R)-9-(4-hydroxy-3,5-dimethoxyphenyl)-8-oxo-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[5,6-f][1,3]benzodioxol-5-yl]-2-[3-(4-aminobutylamino)propylamino]acetamide

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: 584.67

Molecular Weight (Monoisotopic): 584.2846

AlogP: 1.54

#Rotatable Bonds: 14

Polar Surface Area: 162.63

Molecular Species: BASE

HBA: 11

HBD: 5

#RO5 Violations: 2

HBA (Lipinski): 12

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 9.24

CX Basic pKa: 10.62

CX LogP: -1.06

CX LogD: -5.09

Aromatic Rings: 2

Heavy Atoms: 42

QED Weighted: 0.16

Np Likeness Score: 0.88

References

1. Oviatt AA, Kuriappan JA, Minniti E, Vann KR, Onuorah P, Minarini A, De Vivo M, Osheroff N..  (2018)  Polyamine-containing etoposide derivatives as poisons of human type II topoisomerases: Differential effects on topoisomerase IIα and IIβ.,  28  (17): [PMID:30006062] [10.1016/j.bmcl.2018.07.010]

Source

Source(1):

• Scientific Literature