(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; acetic acid

• ChemBase ID: 133294
• Molecular Formular: C77H112N20O15
• Molecular Mass: 1557.83818
• Monoisotopic Mass: 1556.86160298
• 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.CC(=O)O
• Canonical SMILES: CC(=O)O.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.C2H4O2/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;1-2(3)4/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);1H3,(H,3,4)/t49-,52+,53+,54+,55+,56+,57+,58-,59-,60+,61+;/m1./s1
• InChIKey: RXTRFXUUDKVCOG-BHCZHNAISA-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; acetic acid
• 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; acetic acid
• Synonyms: Spantide I; [D-Arg1, D-Trp7,9, Leu11]-Substance P acetate salt

Database IDs

• CAS Number: 91224-37-2
• PubChem SID: 162227571
• PubChem CID: 71308650

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 ... TACR1(6869)mouse ... TACR1(21336)rat ... TACR1(24807)

Product Information

• Purity: ≥97% (HPLC)

DETAILS

Sigma Aldrich - S0274

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