Deamino[carba-1]-oxytocin

ID: ALA3276119

Chembl Id: CHEMBL3276119

PubChem CID: 90679377

Max Phase: Preclinical

Molecular Formula: C44H67N11O12S

Molecular Weight: 974.15

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC[C@H](C)[C@@H]1NC(=O)[C@H](Cc2ccc(O)cc2)NC(=O)CCCSC[C@@H](C(=O)N2CCC[C@H]2C(=O)N[C@@H](CC(C)C)C(=O)NCC(N)=O)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CCC(N)=O)NC1=O

Standard InChI:  InChI=1S/C44H67N11O12S/c1-5-24(4)37-43(66)50-27(14-15-33(45)57)39(62)51-30(20-34(46)58)40(63)53-31(22-68-17-7-9-36(60)49-29(41(64)54-37)19-25-10-12-26(56)13-11-25)44(67)55-16-6-8-32(55)42(65)52-28(18-23(2)3)38(61)48-21-35(47)59/h10-13,23-24,27-32,37,56H,5-9,14-22H2,1-4H3,(H2,45,57)(H2,46,58)(H2,47,59)(H,48,61)(H,49,60)(H,50,66)(H,51,62)(H,52,65)(H,53,63)(H,54,64)/t24-,27-,28-,29-,30-,31-,32-,37-/m0/s1

Standard InChI Key:  UBZUWPDBCILNBN-VNHOCEMUSA-N

Alternative Forms

1. Parent:

   

   ALA3276119

   (2S)-N-[(2S)-1-[(2-amino-2-oxoethyl)amino]-4-methyl-1-oxopentan-2-yl]-1-[(3R,6S,9S,12S,15S)-6-(2-amino-2-oxoethyl)-9-(3-amino-3-oxopropyl)-12-[(2S)-butan-2-yl]-15-[(4-hydroxyphenyl)methyl]-5,8,11,14,17-pentaoxo-1-thia-4,7,10,13,16-pentazacycloicosane-3-ca

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

Calculated Properties

Molecular Weight: 974.15

Molecular Weight (Monoisotopic): 973.4691

AlogP: -2.80

#Rotatable Bonds: 17

Polar Surface Area: 373.51

Molecular Species: NEUTRAL

HBA: 13

HBD: 11

#RO5 Violations: 3

HBA (Lipinski): 23

HBD (Lipinski): 14

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 9.50

CX Basic pKa: ┄

CX LogP: -3.73

CX LogD: -3.73

Aromatic Rings: 1

Heavy Atoms: 68

QED Weighted: 0.08

Np Likeness Score: 0.28

References

1. Manning M, Lowbridge J, Sawyer WH, Haldar J..  (1976)  Synthesis and some pharmacological properties of [1-(L-2-hydroxy-3-mercaptopropanoic acid), 4-threonine]oxytocin (hydroxy [4-thr]oxytocin), a peptide with strikingly high oxytocic potency and of [1-(L-2-hydroxy-3-mercaptopropanoic acid)]oxytocin (hydroxy-oxytocin).,  19  (3): [PMID:943546] [10.1021/jm00225a007]

2. Adachi Y, Sakimura K, Shimizu Y, Nakayama M, Terao Y, Yano T, Asami T..  (2017)  Potent and selective oxytocin receptor agonists without disulfide bridges.,  27  (11): [PMID:28438540] [10.1016/j.bmcl.2017.04.030]

Source

Source(1):

• Scientific Literature