(2R)-2-amino-N-[(4R,7S,10S,13S,16S,19R)-10-(3-aminopropyl)-4-{[(1R)-1-carbamoyl-2-(naphthalen-2-yl)ethyl]carbamoyl}-16-[(4-hydroxyphenyl)methyl]-13-(1H-indol-3-ylmethyl)-6,9,12,15,18-pentaoxo-7-(propan-2-yl)-1,2-dithia-5,8,11,14,17-pentaazacycloicosan-19-yl]-3-(naphthalen-2-yl)propanamide

• ChemBase ID: 153609
• Molecular Formular: C62H71N11O9S2
• Molecular Mass: 1178.42544
• Monoisotopic Mass: 1177.48776491
• SMILES: CC(C)[C@@H]1C(=O)N[C@@H](CSSC[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@@H](C(=O)N1)CCCN)Cc1c[nH]c2c1cccc2)Cc1ccc(cc1)O)NC(=O)[C@@H](Cc1ccc2ccccc2c1)N)C(=O)N[C@H](Cc1ccc2ccccc2c1)C(=O)N
• Canonical SMILES: NCCC[C@H]1NC(=O)[C@@H](NC(=O)[C@H](Cc2ccc(cc2)O)NC(=O)[C@@H](CSSC[C@H](NC(=O)[C@H](NC1=O)C(C)C)C(=O)N[C@@H](C(=O)N)Cc1ccc2c(c1)cccc2)NC(=O)[C@@H](Cc1ccc2c(c1)cccc2)N)Cc1c[nH]c2c1cccc2
• InChI: InChI=1S/C62H71N11O9S2/c1-35(2)54-62(82)72-53(60(80)68-49(55(65)75)30-38-18-22-40-11-4-6-13-42(40)27-38)34-84-83-33-52(71-56(76)46(64)28-37-17-21-39-10-3-5-12-41(39)26-37)61(81)69-50(29-36-19-23-44(74)24-20-36)58(78)70-51(31-43-32-66-47-15-8-7-14-45(43)47)59(79)67-48(16-9-25-63)57(77)73-54/h3-8,10-15,17-24,26-27,32,35,46,48-54,66,74H,9,16,25,28-31,33-34,63-64H2,1-2H3,(H2,65,75)(H,67,79)(H,68,80)(H,69,81)(H,70,78)(H,71,76)(H,72,82)(H,73,77)/t46-,48+,49-,50+,51+,52+,53+,54+/m1/s1
• InChIKey: GLVLDCUADDSQSK-CCNIVULGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-2-amino-N-[(4R,7S,10S,13S,16S,19R)-10-(3-aminopropyl)-4-{[(1R)-1-carbamoyl-2-(naphthalen-2-yl)ethyl]carbamoyl}-16-[(4-hydroxyphenyl)methyl]-13-(1H-indol-3-ylmethyl)-6,9,12,15,18-pentaoxo-7-(propan-2-yl)-1,2-dithia-5,8,11,14,17-pentaazacycloicosan-19-yl]-3-(naphthalen-2-yl)propanamide
• IUPAC Traditional name: (2R)-2-amino-N-[(4R,7S,10S,13S,16S,19R)-10-(3-aminopropyl)-4-{[(1R)-1-carbamoyl-2-(naphthalen-2-yl)ethyl]carbamoyl}-16-[(4-hydroxyphenyl)methyl]-13-(1H-indol-3-ylmethyl)-7-isopropyl-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentaazacycloicosan-19-yl]-3-(naphthalen-2-yl)propanamide
• Synonyms: BIM-23127; β-(2-Naphthyl)-D-Ala-Cys-Tyr-D-Trp-Orn-Val-Cys-β-(2-Naphthyl)-D-Ala-NH2 [disulfide bridge: 2-7]

Database IDs

• CAS Number: 179188-73-9
• MDL Number: MFCD03452984
• PubChem SID: 162247748
• PubChem CID: 71311699

CALCULATED PROPERTIES

• Acid pKa: 9.256049
• H Acceptors: 11
• H Donor: 12
• LogD (pH = 5.5): -1.7803572
• LogD (pH = 7.4): 0.77965665
• Log P: 2.640247
• Molar Refractivity: 323.4291 cm^3
• Polarizability: 129.63985 Å^3
• Polar Surface Area: 334.85 Å^2
• Rotatable Bonds: 17
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Apperance: solid

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: >97% (HPLC)
• Empirical Formula (Hill Notation): C62H71N11O9S2

DETAILS

Sigma Aldrich - N3280

Amino Acid Sequence
D-2-Nal-Cys-Tyr-D-Trp-Orn-Val-Cys-2-Nal-NH2 [Disulfide Bridge: 2-7]
Biochem/physiol Actions
Selective neuromedin B receptor antagonist.