(4S)-4-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-6-amino-2-[(2S)-2-amino-3-phenylpropanamido]hexanamido]-3-methylbutanamido]-3-carboxypropanamido]-4-carboxybutanamido]-4-{[(1S)-1-{[(1S)-1-({2-[(2S)-2-{[(1S,2S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-4-carbamimidamido-1-{[(1S)-4-carbamimidamido-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(2S)-5-carbamimidamido-1-[(2S)-2-{[(1S)-4-carbamimidamido-1-{[(1S)-1,2-dicarbamoylethyl]carbamoyl}butyl]carbamoyl}pyrrolidin-1-yl]-1-oxopentan-2-yl]carbamoyl}-2-phenylethyl]carbamoyl}-3-methylbutyl]carbamoyl}-2-phenylethyl]carbamoyl}-2-(4-hydroxyphenyl)ethyl]carbamoyl}butyl]carbamoyl}butyl]carbamoyl}-2-carbamoylethyl]carbamoyl}-3-carbamoylpropyl]carbamoyl}-2-hydroxyethyl]carbamoyl}-2-methylpropyl]carbamoyl}-2-methylbutyl]carbamoyl}pyrrolidin-1-yl]-2-oxoethyl}carbamoyl)-3-carbamoylpropyl]carbamoyl}-2-phenylethyl]carbamoyl}butanoic acid

• ChemBase ID: 155494
• Molecular Formular: C144H217N43O37
• Molecular Mass: 3142.52968
• Monoisotopic Mass: 3140.6420551
• SMILES: CC[C@H](C)[C@@H](C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCC(=O)N)C(=O)N[C@@H](CC(=O)N)C(=O)N[C@@H](CCCNC(=N)N)C(=O)N[C@@H](CCCNC(=N)N)C(=O)N[C@@H](Cc1ccc(cc1)O)C(=O)N[C@@H](Cc1ccccc1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](Cc1ccccc1)C(=O)N[C@@H](CCCNC(=N)N)C(=O)N1CCC[C@H]1C(=O)N[C@@H](CCCNC(=N)N)C(=O)N[C@@H](CC(=O)N)C(=O)N)NC(=O)[C@@H]1CCCN1C(=O)CNC(=O)[C@H](CCC(=O)N)NC(=O)[C@H](Cc1ccccc1)NC(=O)[C@H](CCC(=O)O)NC(=O)[C@H](CCC(=O)O)NC(=O)[C@H](CC(=O)O)NC(=O)[C@H](C(C)C)NC(=O)[C@H](CCCCN)NC(=O)[C@H](Cc1ccccc1)N
• Canonical SMILES: NCCCC[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)NCC(=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[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)N[C@H](C(=O)N[C@H](C(=O)N)CC(=O)N)CCCNC(=N)N)CCCNC(=N)N)Cc1ccccc1)CC(C)C)Cc1ccccc1)Cc1ccc(cc1)O)CCCNC(=N)N)CCCNC(=N)N)CC(=O)N)CCC(=O)N)CO)C(C)C)[C@H](CC)C)CCC(=O)N)Cc1ccccc1)CCC(=O)O)CCC(=O)O)CC(=O)O)C(C)C)NC(=O)[C@H](Cc1ccccc1)N
• InChI: InChI=1S/C144H217N43O37/c1-9-78(8)116(185-136(220)104-43-28-62-186(104)110(194)73-164-119(203)90(49-53-106(147)190)168-128(212)97(66-80-32-16-11-17-33-80)177-125(209)93(52-56-112(197)198)169-123(207)92(51-55-111(195)196)170-133(217)102(72-113(199)200)181-137(221)114(76(4)5)183-126(210)86(38-22-23-57-145)165-118(202)85(146)65-79-30-14-10-15-31-79)139(223)184-115(77(6)7)138(222)182-103(74-188)134(218)171-91(50-54-107(148)191)124(208)180-101(71-109(150)193)132(216)167-87(39-24-58-160-141(152)153)120(204)166-88(40-25-59-161-142(154)155)122(206)176-100(69-83-45-47-84(189)48-46-83)131(215)179-99(68-82-36-20-13-21-37-82)130(214)175-96(64-75(2)3)127(211)178-98(67-81-34-18-12-19-35-81)129(213)173-94(42-27-61-163-144(158)159)140(224)187-63-29-44-105(187)135(219)172-89(41-26-60-162-143(156)157)121(205)174-95(117(151)201)70-108(149)192/h10-21,30-37,45-48,75-78,85-105,114-116,188-189H,9,22-29,38-44,49-74,145-146H2,1-8H3,(H2,147,190)(H2,148,191)(H2,149,192)(H2,150,193)(H2,151,201)(H,164,203)(H,165,202)(H,166,204)(H,167,216)(H,168,212)(H,169,207)(H,170,217)(H,171,218)(H,172,219)(H,173,213)(H,174,205)(H,175,214)(H,176,206)(H,177,209)(H,178,211)(H,179,215)(H,180,208)(H,181,221)(H,182,222)(H,183,210)(H,184,223)(H,185,220)(H,195,196)(H,197,198)(H,199,200)(H4,152,153,160)(H4,154,155,161)(H4,156,157,162)(H4,158,159,163)/t78-,85-,86-,87-,88-,89-,90-,91-,92-,93-,94-,95-,96-,97-,98-,99-,100-,101-,102-,103-,104-,105-,114-,115-,116-/m0/s1
• InChIKey: YTYIPBDDJNZTTI-DXVWOPCVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4S)-4-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-6-amino-2-[(2S)-2-amino-3-phenylpropanamido]hexanamido]-3-methylbutanamido]-3-carboxypropanamido]-4-carboxybutanamido]-4-{[(1S)-1-{[(1S)-1-({2-[(2S)-2-{[(1S,2S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-4-carbamimidamido-1-{[(1S)-4-carbamimidamido-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(2S)-5-carbamimidamido-1-[(2S)-2-{[(1S)-4-carbamimidamido-1-{[(1S)-1,2-dicarbamoylethyl]carbamoyl}butyl]carbamoyl}pyrrolidin-1-yl]-1-oxopentan-2-yl]carbamoyl}-2-phenylethyl]carbamoyl}-3-methylbutyl]carbamoyl}-2-phenylethyl]carbamoyl}-2-(4-hydroxyphenyl)ethyl]carbamoyl}butyl]carbamoyl}butyl]carbamoyl}-2-carbamoylethyl]carbamoyl}-3-carbamoylpropyl]carbamoyl}-2-hydroxyethyl]carbamoyl}-2-methylpropyl]carbamoyl}-2-methylbutyl]carbamoyl}pyrrolidin-1-yl]-2-oxoethyl}carbamoyl)-3-carbamoylpropyl]carbamoyl}-2-phenylethyl]carbamoyl}butanoic acid
• IUPAC Traditional name: (4S)-4-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-6-amino-2-[(2S)-2-amino-3-phenylpropanamido]hexanamido]-3-methylbutanamido]-3-carboxypropanamido]-4-carboxybutanamido]-4-{[(1S)-1-{[(1S)-1-({2-[(2S)-2-{[(1S,2S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-4-carbamimidamido-1-{[(1S)-4-carbamimidamido-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(2S)-5-carbamimidamido-1-[(2S)-2-{[(1S)-4-carbamimidamido-1-{[(1S)-1,2-dicarbamoylethyl]carbamoyl}butyl]carbamoyl}pyrrolidin-1-yl]-1-oxopentan-2-yl]carbamoyl}-2-phenylethyl]carbamoyl}-3-methylbutyl]carbamoyl}-2-phenylethyl]carbamoyl}-2-(4-hydroxyphenyl)ethyl]carbamoyl}butyl]carbamoyl}butyl]carbamoyl}-2-carbamoylethyl]carbamoyl}-3-carbamoylpropyl]carbamoyl}-2-hydroxyethyl]carbamoyl}-2-methylpropyl]carbamoyl}-2-methylbutyl]carbamoyl}pyrrolidin-1-yl]-2-oxoethyl}carbamoyl)-3-carbamoylpropyl]carbamoyl}-2-phenylethyl]carbamoyl}butanoic acid
• Synonyms: NMU-25; Neuromedin U-25 porcine

Database IDs

• CAS Number: 98395-76-7
• MDL Number: MFCD00076671
• PubChem SID: 162249632
• PubChem CID: 16136617

CALCULATED PROPERTIES

• Acid pKa: 3.0432992
• H Acceptors: 51
• H Donor: 46
• LogD (pH = 5.5): -23.71886
• LogD (pH = 7.4): -23.272282
• Log P: -18.825533
• Molar Refractivity: 839.7944 cm^3
• Polarizability: 311.038 Å^3
• Polar Surface Area: 1348.27 Å^2
• Rotatable Bonds: 102
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Apperance: solid

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ≥97% (HPLC)
• Empirical Formula (Hill Notation): C144H217N43O37

DETAILS

Sigma Aldrich - N8138

Amino Acid Sequence
Phe-Lys-Val-Asp-Glu-Glu-Phe-Gin-Gly-Pro-Ile-Val-Ser-Gin-Asn-Arg-Arg-Tyr-Phe-Leu-Phe-Arg-Pro-Arg-Asn-NH2
Biochem/physiol Actions
Potent stimulator of rat uterus smooth muscle.