(R)-3-hydroxy-2-((5S,6S)-1,6,9,14-tetrahydroxy-5-((2S,3R,4S,5S,6R)-3-hydroxy-6-methyl-5-(methylamino)-4-((2S,3R,4S,5R)-3,4,5-trihydroxytetrahydro-2H-pyran-2-yloxy)tetrahydro-2H-pyran-2-yloxy)-11-methoxy-3-methyl-8,13-dioxo-5,6,8,13-tetrahydrobenzo[a]tetracene-2-carboxamido)propanoic acid

ID: ALA1945842

Chembl Id: CHEMBL1945842

PubChem CID: 57394362

Max Phase: Preclinical

Molecular Formula: C40H44N2O19

Molecular Weight: 856.79

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN[C@@H]1[C@H](O[C@@H]2OC[C@@H](O)[C@H](O)[C@H]2O)[C@@H](O)[C@H](O[C@H]2c3cc(C)c(C(=O)N[C@H](CO)C(=O)O)c(O)c3-c3c(cc4c(c3O)C(=O)c3cc(OC)cc(O)c3C4=O)[C@@H]2O)O[C@@H]1C

Standard InChI:  InChI=1S/C40H44N2O19/c1-11-5-17-24(31(50)21(11)37(54)42-18(9-43)38(55)56)23-15(8-16-25(32(23)51)28(47)14-6-13(57-4)7-19(44)22(14)27(16)46)29(48)35(17)60-40-34(53)36(26(41-3)12(2)59-40)61-39-33(52)30(49)20(45)10-58-39/h5-8,12,18,20,26,29-30,33-36,39-41,43-45,48-53H,9-10H2,1-4H3,(H,42,54)(H,55,56)/t12-,18-,20-,26+,29+,30+,33-,34-,35+,36+,39+,40+/m1/s1

Standard InChI Key:  SFXVRNRSRKABOY-FXQYFLPCSA-N

Alternative Forms

1. Parent:

   

   ALA1945842

   (2R)-3-hydroxy-2-[[(5S,6S)-1,6,9,14-tetrahydroxy-5-[(2S,3R,4S,5S,6R)-3-hydroxy-6-methyl-5-(methylamino)-4-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]oxy-11-methoxy-3-methyl-8,13-dioxo-5,6-dihydrobenzo[a]tetracene-2-carbonyl]amino]propanoic acid

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: 856.79

Molecular Weight (Monoisotopic): 856.2538

AlogP: -1.64

#Rotatable Bonds: 10

Polar Surface Area: 340.79

Molecular Species: ZWITTERION

HBA: 19

HBD: 12

#RO5 Violations: 3

HBA (Lipinski): 21

HBD (Lipinski): 12

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 2.95

CX Basic pKa: 8.97

CX LogP: -1.57

CX LogD: -2.15

Aromatic Rings: 3

Heavy Atoms: 61

QED Weighted: 0.09

Np Likeness Score: 1.61

References

1. Nakagawa Y, Doi T, Takegoshi K, Igarashi Y, Ito Y..  (2012)  Solid-state NMR analysis of calcium and d-mannose binding of BMY-28864, a water-soluble analogue of pradimicin A.,  22  (2): [PMID:22196119] [10.1016/j.bmcl.2011.11.106]

2. Liu W,Yuan L,Wang S.  (2020)  Recent Progress in the Discovery of Antifungal Agents Targeting the Cell Wall.,  63  (21.0): [PMID:32692166] [10.1021/acs.jmedchem.0c00748]

Source

Source(1):

• Scientific Literature