(2S)-2-{[(2S)-1-[(2S)-6-amino-2-{[(2S)-1-[(2R)-2-amino-5-carbamimidamidopentanoyl]pyrrolidin-2-yl]formamido}hexanoyl]pyrrolidin-2-yl]formamido}-N-[(1S)-3-carbamoyl-1-{[(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]carbamoyl}propyl]pentanediamide

• ChemBase ID: 131218
• Molecular Formular: C75H108N20O13
• Molecular Mass: 1497.78622
• Monoisotopic Mass: 1496.84047362
• 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](CCC(=O)N)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)CCC(=O)N)NC(=O)[C@@H]1CCCN1C(=O)[C@@H](CCCNC(=N)N)N
• InChI: InChI=1S/C75H108N20O13/c1-42(2)35-55(64(80)98)89-67(101)56(36-43(3)4)90-69(103)59(39-46-41-85-51-23-11-9-20-48(46)51)93-68(102)57(37-44-17-6-5-7-18-44)91-70(104)58(38-45-40-84-50-22-10-8-19-47(45)50)92-66(100)52(27-29-62(78)96)86-65(99)53(28-30-63(79)97)87-71(105)61-26-16-34-95(61)74(108)54(24-12-13-31-76)88-72(106)60-25-15-33-94(60)73(107)49(77)21-14-32-83-75(81)82/h5-11,17-20,22-23,40-43,49,52-61,84-85H,12-16,21,24-39,76-77H2,1-4H3,(H2,78,96)(H2,79,97)(H2,80,98)(H,86,99)(H,87,105)(H,88,106)(H,89,101)(H,90,103)(H,91,104)(H,92,100)(H,93,102)(H4,81,82,83)/t49-,52+,53+,54+,55+,56+,57+,58-,59-,60+,61+/m1/s1
• InChIKey: SAPCBHPQLCZCDV-CHPWDEGWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-{[(2S)-1-[(2S)-6-amino-2-{[(2S)-1-[(2R)-2-amino-5-carbamimidamidopentanoyl]pyrrolidin-2-yl]formamido}hexanoyl]pyrrolidin-2-yl]formamido}-N-[(1S)-3-carbamoyl-1-{[(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]carbamoyl}propyl]pentanediamide
• IUPAC Traditional name: (2S)-2-{[(2S)-1-[(2S)-6-amino-2-{[(2S)-1-[(2R)-2-amino-5-carbamimidamidopentanoyl]pyrrolidin-2-yl]formamido}hexanoyl]pyrrolidin-2-yl]formamido}-N-[(1S)-3-carbamoyl-1-{[(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]carbamoyl}propyl]pentanediamide
• Synonyms: Spantide I; [D-Arg1, D-Trp7,9, Leu11]-Substance P

Database IDs

• CAS Number: 91224-37-2
• MDL Number: MFCD00076805
• PubChem SID: 162225496
• PubChem CID: 25079075

CALCULATED PROPERTIES

• Acid pKa: 11.534295
• H Acceptors: 18
• H Donor: 18
• LogD (pH = 5.5): -9.530102
• LogD (pH = 7.4): -7.4255753
• Log P: -2.532007
• Molar Refractivity: 410.0121 cm^3
• Polarizability: 157.92847 Å^3
• Polar Surface Area: 548.21 Å^2
• Rotatable Bonds: 43
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• German water hazard class: 3
• 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: ≥97% (HPLC)

DETAILS

Sigma Aldrich - S3641

Amino Acid Sequence
D-Arg-Pro-Lys-Pro-Gln-Gln-D-Trp-Phe-D-Trp-Leu-Leu-NH2
Biochem/physiol Actions
Potent substance P antagonist with weak histamine-releasing action