(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-amino-3-(4-hydroxyphenyl)propanamido]-3-carbamoylpropanamido]-3-(1H-indol-3-yl)propanamido]-N-[(1S)-1-{[(1S)-1-[({[(1S)-1-{[(1S)-4-carbamimidamido-1-{[(1S)-1-carbamoyl-2-phenylethyl]carbamoyl}butyl]carbamoyl}-3-methylbutyl]carbamoyl}methyl)carbamoyl]-2-phenylethyl]carbamoyl}-2-hydroxyethyl]butanediamide

• ChemBase ID: 153753
• Molecular Formular: C63H83N17O14
• Molecular Mass: 1302.43862
• Monoisotopic Mass: 1301.63054042
• SMILES: CC(C)C[C@@H](C(=O)N[C@@H](CCCNC(=N)N)C(=O)N[C@@H](Cc1ccccc1)C(=O)N)NC(=O)CNC(=O)[C@H](Cc1ccccc1)NC(=O)[C@H](CO)NC(=O)[C@H](CC(=O)N)NC(=O)[C@H](Cc1c[nH]c2c1cccc2)NC(=O)[C@H](CC(=O)N)NC(=O)[C@H](Cc1ccc(cc1)O)N
• Canonical SMILES: OC[C@@H](C(=O)N[C@H](C(=O)NCC(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N)Cc1ccccc1)CCCNC(=N)N)CC(C)C)Cc1ccccc1)NC(=O)[C@@H](NC(=O)[C@H](Cc1c[nH]c2c1cccc2)NC(=O)[C@@H](NC(=O)[C@H](Cc1ccc(cc1)O)N)CC(=O)N)CC(=O)N
• InChI: InChI=1S/C63H83N17O14/c1-34(2)24-45(58(90)74-43(18-11-23-70-63(68)69)57(89)75-44(54(67)86)26-35-12-5-3-6-13-35)73-53(85)32-72-56(88)46(27-36-14-7-4-8-15-36)77-62(94)50(33-81)80-61(93)49(30-52(66)84)79-59(91)47(28-38-31-71-42-17-10-9-16-40(38)42)78-60(92)48(29-51(65)83)76-55(87)41(64)25-37-19-21-39(82)22-20-37/h3-10,12-17,19-22,31,34,41,43-50,71,81-82H,11,18,23-30,32-33,64H2,1-2H3,(H2,65,83)(H2,66,84)(H2,67,86)(H,72,88)(H,73,85)(H,74,90)(H,75,89)(H,76,87)(H,77,94)(H,78,92)(H,79,91)(H,80,93)(H4,68,69,70)/t41-,43-,44-,45-,46-,47-,48-,49-,50-/m0/s1
• InChIKey: RITKWYDZSSQNJI-INXYWQKQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-amino-3-(4-hydroxyphenyl)propanamido]-3-carbamoylpropanamido]-3-(1H-indol-3-yl)propanamido]-N-[(1S)-1-{[(1S)-1-[({[(1S)-1-{[(1S)-4-carbamimidamido-1-{[(1S)-1-carbamoyl-2-phenylethyl]carbamoyl}butyl]carbamoyl}-3-methylbutyl]carbamoyl}methyl)carbamoyl]-2-phenylethyl]carbamoyl}-2-hydroxyethyl]butanediamide
• IUPAC Traditional name: (2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-amino-3-(4-hydroxyphenyl)propanamido]-3-carbamoylpropanamido]-3-(1H-indol-3-yl)propanamido]-N-[(1S)-1-{[(1S)-1-[({[(1S)-1-{[(1S)-4-carbamimidamido-1-{[(1S)-1-carbamoyl-2-phenylethyl]carbamoyl}butyl]carbamoyl}-3-methylbutyl]carbamoyl}methyl)carbamoyl]-2-phenylethyl]carbamoyl}-2-hydroxyethyl]butanediamide
• Synonyms: Gene product (112-121) amide, human; KiSS-1; Kisspeptin-10; Metastin (45-54) amide, human

Database IDs

• MDL Number: MFCD03452696
• PubChem SID: 162247892
• PubChem CID: 25240297

CALCULATED PROPERTIES

• Rotatable Bonds: 38
• Lipinski's Rule of Five: false
• Acid pKa: 9.504837
• H Acceptors: 18
• H Donor: 19
• LogD (pH = 5.5): -8.546473
• LogD (pH = 7.4): -6.5950665
• Log P: -4.445137
• Molar Refractivity: 349.4039 cm^3
• Polarizability: 132.89232 Å^3
• Polar Surface Area: 535.34 Å^2

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 ... KISS1(3814)

Product Information

• Purity: ≥95%
• Empirical Formula (Hill Notation): C63H83N17O14

DETAILS

Sigma Aldrich - M2816

Amino Acid Sequence
Tyr-Asn-Trp-Asn-Ser-Phe-Gly-Leu-Arg-Phe-NH2
Biochem/physiol Actions
Metastin is an endogenous ligand to G-protein-coupled orphan receptors such as OT7T175 (also known as AXOR12) and GPR54. Novel placenta-derived hormone. The amide form of metastin is found to be 3-10 times more active than the free acid form of metastin.