(2S,3S,4S)-2-((S)-2-amino-1-((2S,3S,4R,5R)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-4-hydroxy-3-methoxytetrahydrofuran-2-yl)-2-oxoethoxy)-3,4-dihydroxy-N-((S)-2-oxoazepan-3-yl)-3,4-dihydro-2H-pyran-6-carboxamide

ID: ALA5220005

Chembl Id: CHEMBL5220005

PubChem CID: 128200

Max Phase: Preclinical

Molecular Formula: C23H31N5O12

Molecular Weight: 569.52

Names and Identifiers

Canonical SMILES:  CO[C@H]1[C@@H](O)[C@H](n2ccc(=O)[nH]c2=O)O[C@@H]1[C@H](O[C@H]1OC(C(=O)N[C@H]2CCCCNC2=O)=C[C@H](O)[C@@H]1O)C(N)=O

Standard InChI:  InChI=1S/C23H31N5O12/c1-37-15-14(32)21(28-7-5-12(30)27-23(28)36)39-16(15)17(18(24)33)40-22-13(31)10(29)8-11(38-22)20(35)26-9-4-2-3-6-25-19(9)34/h5,7-10,13-17,21-22,29,31-32H,2-4,6H2,1H3,(H2,24,33)(H,25,34)(H,26,35)(H,27,30,36)/t9-,10-,13-,14+,15-,16-,17-,21+,22+/m0/s1

Standard InChI Key:  BISOEENGZHMDEO-MSHAWMIOSA-N

Alternative Forms

1. Parent:

   

   ALA5220005

   (2S,3S,4S)-2-[(1S)-2-amino-1-[(2S,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-4-hydroxy-3-methoxyoxolan-2-yl]-2-oxoethoxy]-3,4-dihydroxy-N-[(3S)-2-oxoazepan-3-yl]-3,4-dihydro-2H-pyran-6-carboxamide

Molecule Features

Natural Product: Yes

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 569.52

Molecular Weight (Monoisotopic): 569.1969

AlogP: -4.57

#Rotatable Bonds: 8

Polar Surface Area: 253.76

Molecular Species: NEUTRAL

HBA: 13

HBD: 7

#RO5 Violations: 3

HBA (Lipinski): 17

HBD (Lipinski): 8

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 9.70

CX Basic pKa:

CX LogP: -4.23

CX LogD: -4.23

Aromatic Rings: 1

Heavy Atoms: 40

QED Weighted: 0.16

Np Likeness Score: 0.83

References

1. Kusaka S, Yamamoto K, Shinohara M, Minato Y, Ichikawa S..  (2022)  Synthesis of capuramycin and its analogues via a Ferrier-type I reaction and their biological evaluation.,  73  [PMID:36191548] [10.1016/j.bmc.2022.117011]

Source

Source(1):

• Scientific Literature