(2S)-N-[(2S)-5-carbamimidamido-1-[(2S)-2-[(carbamoylmethyl)carbamoyl]pyrrolidin-1-yl]-1-oxopentan-2-yl]-2-[(2R)-2-[(2S)-2-[(2S)-3-hydroxy-2-[(2R)-3-(1H-indol-3-yl)-2-[(2R)-2-{[(2R)-5-oxopyrrolidin-2-yl]formamido}-3-phenylpropanamido]propanamido]propanamido]-3-(4-hydroxyphenyl)propanamido]-3-(1H-indol-3-yl)propanamido]-4-methylpentanamide

• ChemBase ID: 132243
• Molecular Formular: C67H84N16O13
• Molecular Mass: 1321.48326
• Monoisotopic Mass: 1320.64037683
• SMILES: CC(C)C[C@@H](C(=O)N[C@@H](CCCNC(=N)N)C(=O)N1CCC[C@H]1C(=O)NCC(=O)N)NC(=O)[C@@H](Cc1c[nH]c2c1cccc2)NC(=O)[C@H](Cc1ccc(cc1)O)NC(=O)[C@H](CO)NC(=O)[C@@H](Cc1c[nH]c2c1cccc2)NC(=O)[C@@H](Cc1ccccc1)NC(=O)[C@H]1CCC(=O)N1
• Canonical SMILES: OC[C@@H](C(=O)N[C@H](C(=O)N[C@@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N1CCC[C@H]1C(=O)NCC(=O)N)CCCNC(=N)N)CC(C)C)Cc1c[nH]c2c1cccc2)Cc1ccc(cc1)O)NC(=O)[C@@H](Cc1c[nH]c2c1cccc2)NC(=O)[C@H](NC(=O)[C@H]1CCC(=O)N1)Cc1ccccc1
• InChI: InChI=1S/C67H84N16O13/c1-37(2)28-49(59(89)76-48(18-10-26-71-67(69)70)66(96)83-27-11-19-55(83)65(95)74-35-56(68)86)77-62(92)52(31-40-33-72-45-16-8-6-14-43(40)45)80-61(91)51(30-39-20-22-42(85)23-21-39)79-64(94)54(36-84)82-63(93)53(32-41-34-73-46-17-9-7-15-44(41)46)81-60(90)50(29-38-12-4-3-5-13-38)78-58(88)47-24-25-57(87)75-47/h3-9,12-17,20-23,33-34,37,47-55,72-73,84-85H,10-11,18-19,24-32,35-36H2,1-2H3,(H2,68,86)(H,74,95)(H,75,87)(H,76,89)(H,77,92)(H,78,88)(H,79,94)(H,80,91)(H,81,90)(H,82,93)(H4,69,70,71)/t47-,48+,49+,50-,51+,52-,53-,54+,55+/m1/s1
• InChIKey: NYWIVATZZKIKCF-FKDXDCHSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-N-[(2S)-5-carbamimidamido-1-[(2S)-2-[(carbamoylmethyl)carbamoyl]pyrrolidin-1-yl]-1-oxopentan-2-yl]-2-[(2R)-2-[(2S)-2-[(2S)-3-hydroxy-2-[(2R)-3-(1H-indol-3-yl)-2-[(2R)-2-{[(2R)-5-oxopyrrolidin-2-yl]formamido}-3-phenylpropanamido]propanamido]propanamido]-3-(4-hydroxyphenyl)propanamido]-3-(1H-indol-3-yl)propanamido]-4-methylpentanamide
• IUPAC Traditional name: (2S)-N-[(2S)-5-carbamimidamido-1-[(2S)-2-(carbamoylmethylcarbamoyl)pyrrolidin-1-yl]-1-oxopentan-2-yl]-2-[(2R)-2-[(2S)-2-[(2S)-3-hydroxy-2-[(2R)-3-(1H-indol-3-yl)-2-[(2R)-2-{[(2R)-5-oxopyrrolidin-2-yl]formamido}-3-phenylpropanamido]propanamido]propanamido]-3-(4-hydroxyphenyl)propanamido]-3-(1H-indol-3-yl)propanamido]-4-methylpentanamide
• Synonyms: [D-pGlu1, D-Phe2, D-Trp3,6]-LH-RH

Database IDs

• CAS Number: 68059-94-9
• MDL Number: MFCD00076582
• PubChem SID: 162226520
• PubChem CID: 25078138

CALCULATED PROPERTIES

• Acid pKa: 9.492937
• H Acceptors: 16
• H Donor: 17
• LogD (pH = 5.5): -3.4155343
• LogD (pH = 7.4): -3.1355903
• Log P: -1.4907758
• Molar Refractivity: 360.0548 cm^3
• Polarizability: 137.49776 Å^3
• Polar Surface Area: 459.24 Å^2
• Rotatable Bonds: 33
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• European Hazard Symbols: Toxic (T)
• German water hazard class: 3
• Risk Statements: 60
• Safety Statements: 53-22-36/37/39-45
• GHS Pictograms: GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H360
• GHS Precautionary statements: P201-P308 + P313
• Personal Protective Equipment: Eyeshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• Storage Temperature: -20°C

Product Information

• Purity: ≥97% (HPLC)

DETAILS

Sigma Aldrich - L2636

Amino Acid Sequence
D-pGlu-D-Phe-D-Trp-Ser-Tyr-D-Trp-Leu-Arg-Pro-Gly-NH2
Biochem/physiol Actions
Substance P antagonist; inhibits spinal cord vasomotor responses

Sigma Aldrich - L6524

Amino Acid Sequence
D-pGlu-D-Phe-D-Trp-Ser-Tyr-D-Trp-Leu-Arg-Pro-Gly-NH2
Biochem/physiol Actions
Substance P antagonist; inhibits spinal cord vasomotor responses
Linkage
Similar to L 2636, but produced by Sigma.