rac-[3-[(2R)-2-amino-3-[[(1S)-1-(hydroxymethyl)-2-methoxy-2-oxo-ethyl]amino]-3-oxo-propyl]sulfanyl-2-hexadecanoyloxy-propyl]hexadecanoate hydrochloride

ID: ALA5172445

Chembl Id: CHEMBL5172445

PubChem CID: 168270237

Max Phase: Preclinical

Molecular Formula: C42H81ClN2O8S

Molecular Weight: 773.18

Names and Identifiers

Canonical SMILES:  CCCCCCCCCCCCCCCC(=O)OCC(CSC[C@H](N)C(=O)N[C@@H](CO)C(=O)OC)OC(=O)CCCCCCCCCCCCCCC.Cl

Standard InChI:  InChI=1S/C42H80N2O8S.ClH/c1-4-6-8-10-12-14-16-18-20-22-24-26-28-30-39(46)51-33-36(34-53-35-37(43)41(48)44-38(32-45)42(49)50-3)52-40(47)31-29-27-25-23-21-19-17-15-13-11-9-7-5-2;/h36-38,45H,4-35,43H2,1-3H3,(H,44,48);1H/t36?,37-,38-;/m0./s1

Standard InChI Key:  MGBVNDUTHSYBNT-VVDJBGIMSA-N

Molecule Features

Natural Product: No

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: 773.18

Molecular Weight (Monoisotopic): 772.5635

AlogP: 9.11

#Rotatable Bonds: 39

Polar Surface Area: 154.25

Molecular Species: NEUTRAL

HBA: 10

HBD: 3

#RO5 Violations: 2

HBA (Lipinski): 10

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 11.53

CX Basic pKa: 8.06

CX LogP: 10.68

CX LogD: 9.94

Aromatic Rings: ┄

Heavy Atoms: 53

QED Weighted: 0.03

Np Likeness Score: 0.38

References

1. Kaur A, Piplani S, Kaushik D, Fung J, Sakala IG, Honda-Okubo Y, Mehta SK, Petrovsky N, Salunke DB..  (2022)  Stereoisomeric Pam₂CS based TLR2 agonists: synthesis, structural modelling and activity as vaccine adjuvants.,  13  (5.0): [PMID:35694694] [10.1039/d1md00372k]

Source

Source(1):

• Scientific Literature