(4S,5S,6S)-6-{(R)-Carbamoyl-[(2S,3S,4R,5R)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-hydroxy-3-methoxy-tetrahydro-furan-2-yl]-methoxy}-4,5-dihydroxy-5,6-dihydro-4H-pyran-2-carboxylic acid ((S)-2-oxo-azepan-3-yl)-amide

ID: ALA96695

Chembl Id: CHEMBL96695

Cas Number: 102770-00-3

PubChem CID: 5487121

Max Phase: Preclinical

Molecular Formula: C23H31N5O12

Molecular Weight: 569.52

Molecule Type: Small molecule

Associated Items:

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-RLXIHFJVSA-N

Alternative Forms

  1. Parent:

    ALA96695

    CAPURAMYCIN

Associated Targets(Human)

DPAGT1 Tchem UDP-N-acetylglucosamine--dolichyl-phosphate N-acetylglucosaminephosphotransferase (17 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
KB (17409 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SiHa (2051 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HCT-116 (91556 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
DLD-1 (17511 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CAPAN-1 (772 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PANC-1 (6144 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ASPC1 (1310 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

mraY Phospho-N-acetylmuramoyl-pentapeptide-transferase (152 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Mycolicibacterium smegmatis (8003 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Mycobacterium avium (4587 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Mycobacterium intracellulare (1532 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Mycobacterium kansasii (6484 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Vero (26788 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
mraY Phospho-N-acetylmuramoyl-pentapeptide-transferase (78 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Mycobacterium tuberculosis (203094 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Enterococcus faecium (13803 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Staphylococcus aureus (210822 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Klebsiella pneumoniae (43867 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Acinetobacter baumannii (41033 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Pseudomonas aeruginosa (123386 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Enterobacter sp. (336 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

Natural Product: YesOral: NoChemical Probe: NoParenteral: No
Molecule Type: Small moleculeTopical: NoFirst In Class: NoBlack Box: No
Chirality: NoAvailability: NoProdrug: No

Drug Indications

MESH IDMESH Heading EFO IDsEFO TermsMax Phase for IndicationReferences

Mechanisms of Action

Mechanism of ActionAction Typetarget IDTarget NameTarget TypeTarget OrganismBinding Site NameReferences

Calculated Properties

Molecular Weight: 569.52Molecular Weight (Monoisotopic): 569.1969AlogP: -4.57#Rotatable Bonds: 8
Polar Surface Area: 253.76Molecular Species: NEUTRALHBA: 13HBD: 7
#RO5 Violations: 3HBA (Lipinski): 17HBD (Lipinski): 8#RO5 Violations (Lipinski): 3
CX Acidic pKa: 9.70CX Basic pKa: CX LogP: -4.23CX LogD: -4.23
Aromatic Rings: 1Heavy Atoms: 40QED Weighted: 0.16Np Likeness Score: 0.83

References

1. Hotoda H, Furukawa M, Daigo M, Murayama K, Kaneko M, Muramatsu Y, Ishii MM, Miyakoshi S, Takatsu T, Inukai M, Kakuta M, Abe T, Harasaki T, Fukuoka T, Utsui Y, Ohya S..  (2003)  Synthesis and antimycobacterial activity of capuramycin analogues. Part 1: substitution of the azepan-2-one moiety of capuramycin.,  13  (17): [PMID:14611838] [10.1016/s0960-894x(03)00596-1]
2. Hotoda H, Daigo M, Furukawa M, Murayama K, Hasegawa CA, Kaneko M, Muramatsu Y, Ishii MM, Miyakoshi S, Takatsu T, Inukai M, Kakuta M, Abe T, Fukuoka T, Utsui Y, Ohya S..  (2003)  Synthesis and antimycobacterial activity of capuramycin analogues. Part 2: acylated derivatives of capuramycin-related compounds.,  13  (17): [PMID:14611839] [10.1016/s0960-894x(03)00597-3]
3. 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]
4. 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