2-[3-{4-[Bis-(2-chloro-ethyl)-amino]-phenyl}-2-(2-{2-[2-diallylamino-3-(4-hydroxy-phenyl)-propionylamino]-2-methyl-propionylamino}-2-methyl-propionylamino)-propionylamino]-4-methyl-pentanoic acid

ID: ALA3144363

PubChem CID: 13893385

Max Phase: Preclinical

Molecular Formula: C42H60Cl2N6O7

Molecular Weight: 831.88

Molecule Type: Protein

Names and Identifiers

Canonical SMILES:  C=CCN(CC=C)[C@@H](Cc1ccc(O)cc1)C(=O)NC(C)(C)C(=O)NC(C)(C)C(=O)N[C@@H](Cc1ccc(N(CCCl)CCCl)cc1)C(=O)N[C@@H](CC(C)C)C(=O)O

Standard InChI:  InChI=1S/C42H60Cl2N6O7/c1-9-21-50(22-10-2)35(27-30-13-17-32(51)18-14-30)37(53)47-42(7,8)40(57)48-41(5,6)39(56)46-33(36(52)45-34(38(54)55)25-28(3)4)26-29-11-15-31(16-12-29)49(23-19-43)24-20-44/h9-18,28,33-35,51H,1-2,19-27H2,3-8H3,(H,45,52)(H,46,56)(H,47,53)(H,48,57)(H,54,55)/t33-,34-,35-/m0/s1

Standard InChI Key:  RPJYDHKYCWHHOP-IMKBVMFZSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA3144363

   (2S)-2-[[(2S)-3-[4-[bis(2-chloroethyl)amino]phenyl]-2-[[2-[[2-[[(2S)-2-[bis(prop-2-enyl)amino]-3-(4-hydroxyphenyl)propanoyl]amino]-2-methylpropanoyl]amino]-2-methylpropanoyl]amino]propanoyl]amino]-4-methylpentanoic acid

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Protein

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 831.88

Molecular Weight (Monoisotopic): 830.3901

AlogP: 4.39

#Rotatable Bonds: 25

Polar Surface Area: 180.41

Molecular Species: ACID

HBA: 8

HBD: 6

#RO5 Violations: 2

HBA (Lipinski): 13

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 4.10

CX Basic pKa: 6.57

CX LogP: 3.64

CX LogD: 2.97

Aromatic Rings: 2

Heavy Atoms: 57

QED Weighted: 0.06

Np Likeness Score: -0.24

References

1. Lovett JA, Portoghese PS..  (1987)  Synthesis and evaluation of melphalan-containing N,N-dialkylenkephalin analogues as irreversible antagonists of the delta opioid receptor.,  30  (9): [PMID:3041000] [10.1021/jm00392a025]

Source

Source(1):

• Scientific Literature