6-amino-N-{1-[(5-carbamimidamido-1-{2-[(carbamoylmethyl)carbamoyl]pyrrolidin-1-yl}-1-oxopentan-2-yl)carbamoyl]-3-methylbutyl}-2-[2-(3-hydroxy-2-{2-[3-(1H-imidazol-5-yl)-2-[(5-oxopyrrolidin-2-yl)formamido]propanamido]-3-(1H-indol-3-yl)propanamido}propanamido)-3-(4-hydroxyphenyl)propanamido]hexanamide

• ChemBase ID: 131188
• Molecular Formular: C59H84N18O13
• Molecular Mass: 1253.41106
• Monoisotopic Mass: 1252.64652484
• SMILES: CC(C)CC(C(=O)NC(CCCNC(=N)N)C(=O)N1CCCC1C(=O)NCC(=O)N)NC(=O)C(CCCCN)NC(=O)C(Cc1ccc(cc1)O)NC(=O)C(CO)NC(=O)C(Cc1c[nH]c2c1cccc2)NC(=O)C(Cc1cnc[nH]1)NC(=O)C1CCC(=O)N1
• Canonical SMILES: NCCCCC(C(=O)NC(C(=O)NC(C(=O)N1CCCC1C(=O)NCC(=O)N)CCCNC(=N)N)CC(C)C)NC(=O)C(NC(=O)C(NC(=O)C(Cc1c[nH]c2c1cccc2)NC(=O)C(NC(=O)C1CCC(=O)N1)Cc1[nH]cnc1)CO)Cc1ccc(cc1)O
• InChI: InChI=1S/C59H84N18O13/c1-32(2)23-42(52(84)71-41(12-7-21-65-59(62)63)58(90)77-22-8-13-47(77)57(89)67-29-48(61)80)72-50(82)39(11-5-6-20-60)70-53(85)43(24-33-14-16-36(79)17-15-33)73-56(88)46(30-78)76-54(86)44(25-34-27-66-38-10-4-3-9-37(34)38)74-55(87)45(26-35-28-64-31-68-35)75-51(83)40-18-19-49(81)69-40/h3-4,9-10,14-17,27-28,31-32,39-47,66,78-79H,5-8,11-13,18-26,29-30,60H2,1-2H3,(H2,61,80)(H,64,68)(H,67,89)(H,69,81)(H,70,85)(H,71,84)(H,72,82)(H,73,88)(H,74,87)(H,75,83)(H,76,86)(H4,62,63,65)
• InChIKey: HOWBSMILMYIFKQ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 6-amino-N-{1-[(5-carbamimidamido-1-{2-[(carbamoylmethyl)carbamoyl]pyrrolidin-1-yl}-1-oxopentan-2-yl)carbamoyl]-3-methylbutyl}-2-[2-(3-hydroxy-2-{2-[3-(1H-imidazol-5-yl)-2-[(5-oxopyrrolidin-2-yl)formamido]propanamido]-3-(1H-indol-3-yl)propanamido}propanamido)-3-(4-hydroxyphenyl)propanamido]hexanamide
• IUPAC Traditional name: 6-amino-N-[1-({5-carbamimidamido-1-[2-(carbamoylmethylcarbamoyl)pyrrolidin-1-yl]-1-oxopentan-2-yl}carbamoyl)-3-methylbutyl]-2-[2-(3-hydroxy-2-{2-[3-(3H-imidazol-4-yl)-2-[(5-oxopyrrolidin-2-yl)formamido]propanamido]-3-(1H-indol-3-yl)propanamido}propanamido)-3-(4-hydroxyphenyl)propanamido]hexanamide
• Synonyms: [D-Lys6]-LH-RH

Database IDs

• CAS Number: 52671-12-2
• MDL Number: MFCD00133504
• PubChem SID: 162225466; 24896386
• PubChem CID: 5176735

CALCULATED PROPERTIES

• Acid pKa: 9.414195
• H Acceptors: 18
• H Donor: 18
• LogD (pH = 5.5): -11.280696
• LogD (pH = 7.4): -10.113745
• Log P: -6.0431447
• Molar Refractivity: 334.6042 cm^3
• Polarizability: 126.71122 Å^3
• Polar Surface Area: 498.15 Å^2
• Rotatable Bonds: 35
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Apperance: powder

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

Pharmacology Properties

• Gene Information: human ... GNRH1(2796)

Product Information

• Purity: ≥95% (HPLC)

DETAILS

Sigma Aldrich - L5022

Amino Acid Sequence
pGlu-His-Trp-Ser-Tyr-D-Lys-Leu-Arg-Pro-Gly-NH2
Biochem/physiol Actions
LH-RH agonist. It has been conjugated to cytotoxic compounds such as methotrexate (MTX), doxorubicin (DOX), and glutaryl-2-(hydroxymethyl)anthraquinone (G-HMAQ), and together with other conjugated LH-RH analogs comprise a class of targeted chemotherapeutic agents for cancers expressing receptors for LH-RH.