ID: ALA3414636

Max Phase: Preclinical

Molecular Formula: C42H58N8O12

Molecular Weight: 866.97

Molecule Type: Small molecule

Representations

Canonical SMILES:  COC(=O)[C@H](CCCNC(=N)N)NC(=O)COc1cc2oc3cc(OCC(=O)N[C@@H](CCCNC(=N)N)C(=O)OC)c(OC)c(CC=C(C)C)c3c(=O)c2c(O)c1CC=C(C)C

Standard InChI:  InChI=1S/C42H58N8O12/c1-22(2)12-14-24-28(60-20-32(51)49-26(39(55)58-6)10-8-16-47-41(43)44)18-30-35(36(24)53)37(54)34-25(15-13-23(3)4)38(57-5)31(19-29(34)62-30)61-21-33(52)50-27(40(56)59-7)11-9-17-48-42(45)46/h12-13,18-19,26-27,53H,8-11,14-17,20-21H2,1-7H3,(H,49,51)(H,50,52)(H4,43,44,47)(H4,45,46,48)/t26-,27-/m0/s1

Standard InChI Key:  IFZYKAZYHUCYHJ-SVBPBHIXSA-N

Molecule Features

Natural Product: No

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

Properties

Molecular Weight: 866.97

Molecular Weight (Monoisotopic): 866.4174

AlogP: 2.28

#Rotatable Bonds: 23

Polar Surface Area: 312.73

Molecular Species: BASE

HBA: 14

HBD: 9

#RO5 Violations: 3

HBA (Lipinski): 20

HBD (Lipinski): 11

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 8.13

CX Basic pKa: 12.46

CX LogP: 1.39

CX LogD: -0.75

Aromatic Rings: 3

Heavy Atoms: 62

QED Weighted: 0.02

Np Likeness Score: 0.76

References

1. Koh JJ, Lin S, Aung TT, Lim F, Zou H, Bai Y, Li J, Lin H, Pang LM, Koh WL, Salleh SM, Lakshminarayanan R, Zhou L, Qiu S, Pervushin K, Verma C, Tan DT, Cao D, Liu S, Beuerman RW..  (2015)  Amino acid modified xanthone derivatives: novel, highly promising membrane-active antimicrobials for multidrug-resistant Gram-positive bacterial infections.,  58  (2): [PMID:25474410] [10.1021/jm501285x]

2. Lin S, Sin WLW, Koh JJ, Lim F, Wang L, Cao D, Beuerman RW, Ren L, Liu S..  (2017)  Semisynthesis and Biological Evaluation of Xanthone Amphiphilics as Selective, Highly Potent Antifungal Agents to Combat Fungal Resistance.,  60  (24): [PMID:29155590] [10.1021/acs.jmedchem.7b01348]

3. Lin S, Koh JJ, Aung TT, Lim F, Li J, Zou H, Wang L, Lakshminarayanan R, Verma C, Wang Y, Tan DT, Cao D, Beuerman RW, Ren L, Liu S..  (2017)  Symmetrically Substituted Xanthone Amphiphiles Combat Gram-Positive Bacterial Resistance with Enhanced Membrane Selectivity.,  60  (4): [PMID:28122182] [10.1021/acs.jmedchem.6b01403]

Source

Source(1):

• Scientific Literature