(2S)-2-[(2R)-2-{[(2S)-1-[(2S)-6-amino-2-{[(2S)-1-[(2R)-2-amino-5-carbamimidamidopentanoyl]pyrrolidin-2-yl]formamido}hexanoyl]pyrrolidin-2-yl]formamido}-3-phenylpropanamido]-N-[(1R)-1-{[(1S)-1-{[(1R)-1-{[(1S)-1-{[(1S)-1-carbamoyl-3-methylbutyl]carbamoyl}-3-methylbutyl]carbamoyl}-2-(1H-indol-3-yl)ethyl]carbamoyl}-2-phenylethyl]carbamoyl}-2-(1H-indol-3-yl)ethyl]pentanediamide

• ChemBase ID: 134373
• Molecular Formular: C79H109N19O12
• Molecular Mass: 1516.83086
• Monoisotopic Mass: 1515.85031002
• SMILES: CC(C)C[C@@H](C(=O)N)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](Cc1c[nH]c2c1cccc2)NC(=O)[C@H](Cc1ccccc1)NC(=O)[C@@H](Cc1c[nH]c2c1cccc2)NC(=O)[C@H](CCC(=O)N)NC(=O)[C@@H](Cc1ccccc1)NC(=O)[C@@H]1CCCN1C(=O)[C@H](CCCCN)NC(=O)[C@@H]1CCCN1C(=O)[C@@H](CCCNC(=N)N)N
• Canonical SMILES: NCCCC[C@@H](C(=O)N1CCC[C@H]1C(=O)N[C@@H](C(=O)N[C@H](C(=O)N[C@@H](C(=O)N[C@H](C(=O)N[C@@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N)CC(C)C)CC(C)C)Cc1c[nH]c2c1cccc2)Cc1ccccc1)Cc1c[nH]c2c1cccc2)CCC(=O)N)Cc1ccccc1)NC(=O)[C@@H]1CCCN1C(=O)[C@@H](CCCNC(=N)N)N
• InChI: InChI=1S/C79H109N19O12/c1-46(2)38-59(68(83)100)91-70(102)60(39-47(3)4)92-73(105)64(43-51-45-88-56-28-14-12-25-53(51)56)95-72(104)61(40-48-20-7-5-8-21-48)93-74(106)63(42-50-44-87-55-27-13-11-24-52(50)55)94-69(101)57(32-33-67(82)99)89-71(103)62(41-49-22-9-6-10-23-49)96-76(108)66-31-19-37-98(66)78(110)58(29-15-16-34-80)90-75(107)65-30-18-36-97(65)77(109)54(81)26-17-35-86-79(84)85/h5-14,20-25,27-28,44-47,54,57-66,87-88H,15-19,26,29-43,80-81H2,1-4H3,(H2,82,99)(H2,83,100)(H,89,103)(H,90,107)(H,91,102)(H,92,105)(H,93,106)(H,94,101)(H,95,104)(H,96,108)(H4,84,85,86)/t54-,57+,58+,59+,60+,61+,62-,63-,64-,65+,66+/m1/s1
• InChIKey: XVOCEQLNJQGCQG-ACRSGXKRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-[(2R)-2-{[(2S)-1-[(2S)-6-amino-2-{[(2S)-1-[(2R)-2-amino-5-carbamimidamidopentanoyl]pyrrolidin-2-yl]formamido}hexanoyl]pyrrolidin-2-yl]formamido}-3-phenylpropanamido]-N-[(1R)-1-{[(1S)-1-{[(1R)-1-{[(1S)-1-{[(1S)-1-carbamoyl-3-methylbutyl]carbamoyl}-3-methylbutyl]carbamoyl}-2-(1H-indol-3-yl)ethyl]carbamoyl}-2-phenylethyl]carbamoyl}-2-(1H-indol-3-yl)ethyl]pentanediamide
• IUPAC Traditional name: (2S)-2-[(2R)-2-{[(2S)-1-[(2S)-6-amino-2-{[(2S)-1-[(2R)-2-amino-5-carbamimidamidopentanoyl]pyrrolidin-2-yl]formamido}hexanoyl]pyrrolidin-2-yl]formamido}-3-phenylpropanamido]-N-[(1R)-1-{[(1S)-1-{[(1R)-1-{[(1S)-1-{[(1S)-1-carbamoyl-3-methylbutyl]carbamoyl}-3-methylbutyl]carbamoyl}-2-(1H-indol-3-yl)ethyl]carbamoyl}-2-phenylethyl]carbamoyl}-2-(1H-indol-3-yl)ethyl]pentanediamide
• Synonyms: D-Arg-Pro-Lys-Pro-D-Phe-Gln-D-Trp-Phe-D-Trp-Leu-Leu-NH2; Antagonist D; [D-Arg1, D-Phe5, D-Trp7,9, Leu11]-Substance P

Database IDs

• CAS Number: 96736-12-8
• MDL Number: MFCD00076802
• PubChem SID: 162228649
• PubChem CID: 25091011

CALCULATED PROPERTIES

• Acid pKa: 11.556986
• H Acceptors: 17
• H Donor: 17
• LogD (pH = 5.5): -6.713686
• LogD (pH = 7.4): -4.6094017
• Log P: 0.33591542
• Molar Refractivity: 422.0185 cm^3
• Polarizability: 162.57762 Å^3
• Polar Surface Area: 505.12 Å^2
• Rotatable Bonds: 42
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

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

Pharmacology Properties

• Gene Information: human ... TAC1(6863), TACR1(6869)mouse ... TAC1(21333), TACR1(21336)rat ... TAC1(24806), TACR1(24807)

Product Information

• Purity: ≥95% (HPLC)

DETAILS

Sigma Aldrich - S3144

Amino Acid Sequence
Arg-Pro-Lys-Pro-Phe-Gln-Trp-Phe-Trp-Leu-Leu-NH2
Biochem/physiol Actions
NK-1 tachykinin receptor antagonist