(1R,2S,3S,4S,4aR,11bR)-1,2,3,4-Tetrahydroxy-1,3,4,4a,5,11b-hexahydro-2H-[1,3]dioxolo[4,5-j]phenanthridin-6-one

ID: ALA98481

Chembl Id: CHEMBL98481

PubChem CID: 443741

Max Phase: Preclinical

Molecular Formula: C14H15NO7

Molecular Weight: 309.27

Molecule Type: Small molecule

Names and Identifiers

Synonyms: 7-Deoxypancratistatin | 7-Deoxypancratistatin|CHEBI:31142|CHEMBL98481|(1R,2S,3S,4S,4aR,11bR)-1,2,3,4-tetrahydroxy-2,3,4,4a,5,11b-hexahydro-1H-[1,3]dioxolo[4,5-j]phenanthridin-6-one|C12255|SCHEMBL21162145|Q27114174

Canonical SMILES:  O=C1N[C@H]2[C@H](O)[C@H](O)[C@@H](O)[C@H](O)[C@@H]2c2cc3c(cc21)OCO3

Standard InChI:  InChI=1S/C14H15NO7/c16-10-8-4-1-6-7(22-3-21-6)2-5(4)14(20)15-9(8)11(17)13(19)12(10)18/h1-2,8-13,16-19H,3H2,(H,15,20)/t8-,9-,10-,11+,12+,13+/m1/s1

Standard InChI Key:  GVGWJJOWWDRYOF-DZDPUUJWSA-N

Alternative Forms

1. Parent:

   

   ALA98481

   7-Deoxypancratistatin

Molecule Features

Natural Product: Yes

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: 309.27

Molecular Weight (Monoisotopic): 309.0849

AlogP: -1.93

#Rotatable Bonds: ┄

Polar Surface Area: 128.48

Molecular Species: NEUTRAL

HBA: 7

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.68

CX Basic pKa: ┄

CX LogP: -2.26

CX LogD: -2.26

Aromatic Rings: 1

Heavy Atoms: 22

QED Weighted: 0.38

Np Likeness Score: 1.68

References

1. Rinner U, Hillebrenner HL, Adams DR, Hudlicky T, Pettit GR..  (2004)  Synthesis and biological activity of some structural modifications of pancratistatin.,  14  (11): [PMID:15125958] [10.1016/j.bmcl.2004.03.032]

2. Gabrielsen B, Monath TP, Huggins JW, Kefauver DF, Pettit GR, Groszek G, Hollingshead M, Kirsi JJ, Shannon WM, Schubert EM..  (1992)  Antiviral (RNA) activity of selected Amaryllidaceae isoquinoline constituents and synthesis of related substances.,  55  (11): [PMID:1336040] [10.1021/np50089a003]

Source

Source(1):

• Scientific Literature