(2S,3R,4S,4aR)-2,3,7-trihydroxy-4-((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yloxy)-3,4,4a,5-tetrahydro-[1,3]dioxolo[4,5-j]phenanthridin-6(2H)-one

ID: ALA4203404

PubChem CID: 101615679

Max Phase: Preclinical

Molecular Formula: C20H23NO12

Molecular Weight: 469.40

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C20H23NO12/c22-3-9-13(25)15(27)16(28)20(32-9)33-18-11-6(1-7(23)12(18)24)5-2-8-17(31-4-30-8)14(26)10(5)19(29)21-11/h1-2,7,9,11-13,15-16,18,20,22-28H,3-4H2,(H,21,29)/t7-,9+,11+,12+,13+,15-,16+,18-,20-/m0/s1

Standard InChI Key:  OHMFFIAKCHSDEB-QGPDEPKMSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA4203404

   (2S,3R,4S,4aR)-2,3,7-trihydroxy-4-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4,4a,5-tetrahydro-2H-[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: 469.40

Molecular Weight (Monoisotopic): 469.1220

AlogP: -3.46

#Rotatable Bonds: 3

Polar Surface Area: 207.63

Molecular Species: NEUTRAL

HBA: 12

HBD: 8

#RO5 Violations: 2

HBA (Lipinski): 13

HBD (Lipinski): 8

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 8.44

CX Basic pKa: ┄

CX LogP: -2.69

CX LogD: -2.72

Aromatic Rings: 1

Heavy Atoms: 33

QED Weighted: 0.22

Np Likeness Score: 2.36

References

1. Nair JJ, Wilhelm A, Bonnet SL, van Staden J..  (2017)  Antibacterial constituents of the plant family Amaryllidaceae.,  27  (22): [PMID:29033234] [10.1016/j.bmcl.2017.09.052]

Source

Source(1):

• Scientific Literature