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

ID: ALA4746444

Chembl Id: CHEMBL4746444

PubChem CID: 10347650

Max Phase: Preclinical

Molecular Formula: C22H29N5O12

Molecular Weight: 555.50

Molecule Type: Unknown

Names and Identifiers

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

Standard InChI:  InChI=1S/C22H29N5O12/c23-17(33)16(15-13(31)14(32)20(38-15)27-6-4-11(29)26-22(27)36)39-21-12(30)9(28)7-10(37-21)19(35)25-8-3-1-2-5-24-18(8)34/h4,6-9,12-16,20-21,28,30-32H,1-3,5H2,(H2,23,33)(H,24,34)(H,25,35)(H,26,29,36)/t8-,9-,12-,13-,14+,15-,16+,20+,21+/m0/s1

Standard InChI Key:  ROPNVEBUXSKZCY-OXHOPNEESA-N

Alternative Forms

1. Parent:

   

   ALA4746444

   (2S,3S,4S)-2-[(1R)-2-amino-1-[(2S,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-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: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 555.50

Molecular Weight (Monoisotopic): 555.1813

AlogP: -5.23

#Rotatable Bonds: 7

Polar Surface Area: 264.76

Molecular Species: NEUTRAL

HBA: 13

HBD: 8

#RO5 Violations: 3

HBA (Lipinski): 17

HBD (Lipinski): 9

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 9.70

CX Basic pKa:

CX LogP: -4.87

CX LogD: -4.87

Aromatic Rings: 1

Heavy Atoms: 39

QED Weighted: 0.16

Np Likeness Score: 0.79

References

1. Mitachi K,Kansal RG,Hevener KE,Gillman CD,Hussain SM,Yun HG,Miranda-Carboni GA,Glazer ES,Clemons WM,Kurosu M.  (2020)  DPAGT1 Inhibitors of Capuramycin Analogues and Their Antimigratory Activities of Solid Tumors.,  63  (19): [PMID:32886511] [10.1021/acs.jmedchem.0c00545]

2. 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