(3S,6R,9S,12S,15S,18S,21S)-9,18-bis(3-amino-3-oxopropyl)-21-(3-guanidinopropyl)-15-(4-hydroxybenzyl)-3-(hydroxymethyl)-12-isobutyl-6-(mercaptomethyl)-1,4,7,10,13,16,19-heptaoxo-1-((S)-pyrrolidin-2-yl)-2,5,8,11,14,17,20-heptaazadocosan-22-oic acid

ID: ALA4246576

PubChem CID: 145983341

Max Phase: Preclinical

Molecular Formula: C42H67N13O13S

Molecular Weight: 994.14

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)C[C@H](NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CS)NC(=O)[C@H](CO)NC(=O)[C@@H]1CCCN1)C(=O)N[C@@H](Cc1ccc(O)cc1)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCCNC(=N)N)C(=O)O

Standard InChI:  InChI=1S/C42H67N13O13S/c1-21(2)17-28(52-36(62)26(12-14-33(44)59)50-40(66)31(20-69)55-39(65)30(19-56)54-34(60)24-5-3-15-47-24)37(63)53-29(18-22-7-9-23(57)10-8-22)38(64)49-25(11-13-32(43)58)35(61)51-27(41(67)68)6-4-16-48-42(45)46/h7-10,21,24-31,47,56-57,69H,3-6,11-20H2,1-2H3,(H2,43,58)(H2,44,59)(H,49,64)(H,50,66)(H,51,61)(H,52,62)(H,53,63)(H,54,60)(H,55,65)(H,67,68)(H4,45,46,48)/t24-,25-,26-,27-,28-,29-,30-,31-/m0/s1

Standard InChI Key:  AAGFVZROTPWZAC-NLXVKQHPSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA4246576

   ---

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: 994.14

Molecular Weight (Monoisotopic): 993.4702

AlogP: -5.07

#Rotatable Bonds: 31

Polar Surface Area: 441.57

Molecular Species: ZWITTERION

HBA: 15

HBD: 17

#RO5 Violations: 3

HBA (Lipinski): 26

HBD (Lipinski): 19

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 3.90

CX Basic pKa: 11.79

CX LogP: -7.90

CX LogD: -9.20

Aromatic Rings: 1

Heavy Atoms: 69

QED Weighted: 0.01

Np Likeness Score: 0.26

References

1. Saxena P, Severi L, Santucci M, Taddia L, Ferrari S, Luciani R, Marverti G, Marraccini C, Tondi D, Mor M, Scalvini L, Vitiello S, Losi L, Fonda S, Pacifico S, Guerrini R, D'Arca D, Ponterini G, Costi MP..  (2018)  Conformational Propensity and Biological Studies of Proline Mutated LR Peptides Inhibiting Human Thymidylate Synthase and Ovarian Cancer Cell Growth.,  61  (16): [PMID:30035541] [10.1021/acs.jmedchem.7b01699]

Source

Source(1):

• Scientific Literature