(2S,3aS,7aS)-1-[(3R)-2-[(2S)-2-[(2S)-2-(2-{[(2S,4R)-1-[(2S)-1-[(2S)-2-[(2R)-2-amino-5-carbamimidamidopentanamido]-5-carbamimidamidopentanoyl]pyrrolidine-2-carbonyl]-4-hydroxypyrrolidin-2-yl]formamido}acetamido)-3-(thiophen-2-yl)propanamido]-3-hydroxypropanoyl]-1,2,3,4-tetrahydroisoquinoline-3-carbonyl]-octahydro-1H-indole-2-carboxylic acid

• ChemBase ID: 134099
• Molecular Formular: C53H77N15O12S
• Molecular Mass: 1148.33678
• Monoisotopic Mass: 1147.55968398
• SMILES: c1ccc2c(c1)C[C@@H](N(C2)C(=O)[C@H](CO)NC(=O)[C@H](Cc1cccs1)NC(=O)CNC(=O)[C@@H]1C[C@H](CN1C(=O)[C@@H]1CCCN1C(=O)[C@H](CCCNC(=N)N)NC(=O)[C@@H](CCCNC(=N)N)N)O)C(=O)N1[C@H]2CCCC[C@H]2C[C@H]1C(=O)O
• Canonical SMILES: OC[C@@H](C(=O)N1Cc2ccccc2C[C@@H]1C(=O)N1[C@H]2CCCC[C@H]2C[C@H]1C(=O)O)NC(=O)[C@H](Cc1cccs1)NC(=O)CNC(=O)[C@@H]1C[C@H](CN1C(=O)[C@@H]1CCCN1C(=O)[C@@H](NC(=O)[C@@H](CCCNC(=N)N)N)CCCNC(=N)N)O
• InChI: InChI=1S/C53H77N15O12S/c54-34(13-5-17-59-52(55)56)44(72)63-35(14-6-18-60-53(57)58)47(75)65-19-7-16-39(65)49(77)67-27-32(70)23-40(67)46(74)61-25-43(71)62-36(24-33-12-8-20-81-33)45(73)64-37(28-69)48(76)66-26-31-11-2-1-9-29(31)21-41(66)50(78)68-38-15-4-3-10-30(38)22-42(68)51(79)80/h1-2,8-9,11-12,20,30,32,34-42,69-70H,3-7,10,13-19,21-28,54H2,(H,61,74)(H,62,71)(H,63,72)(H,64,73)(H,79,80)(H4,55,56,59)(H4,57,58,60)/t30-,32+,34+,35-,36-,37-,38-,39-,40-,41+,42-/m0/s1
• InChIKey: TZWJLAAYNDPYBS-ZYEJRSMVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3aS,7aS)-1-[(3R)-2-[(2S)-2-[(2S)-2-(2-{[(2S,4R)-1-[(2S)-1-[(2S)-2-[(2R)-2-amino-5-carbamimidamidopentanamido]-5-carbamimidamidopentanoyl]pyrrolidine-2-carbonyl]-4-hydroxypyrrolidin-2-yl]formamido}acetamido)-3-(thiophen-2-yl)propanamido]-3-hydroxypropanoyl]-1,2,3,4-tetrahydroisoquinoline-3-carbonyl]-octahydro-1H-indole-2-carboxylic acid
• IUPAC Traditional name: (2S,3aS,7aS)-1-[(3R)-2-[(2S)-2-[(2S)-2-(2-{[(2S,4R)-1-[(2S)-1-[(2S)-2-[(2R)-2-amino-5-carbamimidamidopentanamido]-5-carbamimidamidopentanoyl]pyrrolidine-2-carbonyl]-4-hydroxypyrrolidin-2-yl]formamido}acetamido)-3-(thiophen-2-yl)propanamido]-3-hydroxypropanoyl]-3,4-dihydro-1H-isoquinoline-3-carbonyl]-octahydroindole-2-carboxylic acid
• Synonyms: D-Arg-L-Arg-L-prolyl-L-Hyp-Gly-L-(2-thienyl)Ala-L-Ser-D-1,2,3,4-tetrahydro-3-isoquinolinecarbonyl-L-(2α,3β,7aβ)-octahydro-1H-indole-2-carboxylic acid; [des-Arg10]-HOE 140

Database IDs

• PubChem SID: 162228376
• PubChem CID: 5311112

CALCULATED PROPERTIES

• Acid pKa: -1.199221
• H Acceptors: 19
• H Donor: 14
• LogD (pH = 5.5): -10.3933325
• LogD (pH = 7.4): -8.709356
• Log P: -6.6318536
• Molar Refractivity: 313.0659 cm^3
• Polarizability: 113.41619 Å^3
• Polar Surface Area: 425.22 Å^2
• Rotatable Bonds: 24
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Apperance: white powder

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: >98%
• Biological Source: synthetic

DETAILS

Sigma Aldrich - H158

Amino Acid Sequence
D-Arg-Arg-Pro-Hyp-Gly-Thi-Ser-D-Tic-Oic
Biochem/physiol Actions
Potent B1 bradykinin receptor antagonist.