cis-dihydronarciclasine

ID: ALA463048

Chembl Id: CHEMBL463048

PubChem CID: 3000372

Max Phase: Preclinical

Molecular Formula: C14H15NO7

Molecular Weight: 309.27

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Cis-Dihydronarciclasine | cis-Dihydronarciclasine|CHEMBL463048|SCHEMBL14732744

Canonical SMILES:  O=C1N[C@H]2[C@H](O)[C@H](O)[C@@H](O)C[C@H]2c2cc3c(c(O)c21)OCO3

Standard InChI:  InChI=1S/C14H15NO7/c16-6-1-5-4-2-7-13(22-3-21-7)11(18)8(4)14(20)15-9(5)12(19)10(6)17/h2,5-6,9-10,12,16-19H,1,3H2,(H,15,20)/t5-,6-,9+,10+,12-/m0/s1

Standard InChI Key:  SBTGHBALOCEVOR-GUHAZCHASA-N

Alternative Forms

1. Parent:

   

   ALA463048

   (2S,3R,4S,4aR,11bS)-2,3,4,7-tetrahydroxy-2,3,4,4a,5,11b-hexahydro-1H-[1,3]dioxolo[4,5-j]phenanthridin-6-one

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: -1.20

#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: 8.48

CX Basic pKa: ┄

CX LogP: -0.88

CX LogD: -0.92

Aromatic Rings: 1

Heavy Atoms: 22

QED Weighted: 0.41

Np Likeness Score: 2.26

References

1. Pettit GR, Cragg GM, Singh SB, Duke JA, Doubek DL..  (1990)  Antineoplastic agents, 162. Zephyranthes candida.,  53  (1): [PMID:2348199] [10.1021/np50067a026]

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