(2S)-2-[(2S)-2-[(2S)-2-{[(2S)-1-[(2S)-2-[(2S)-2-{[(2S)-1-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S,3S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-{2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S,3S)-2-[(2S)-2-[(2S)-6-amino-2-[(2S)-2-amino-3-carbamoylpropanamido]hexanamido]-4-methylpentanamido]-3-methylpentanamido]-3-methylbutanamido]-5-carbamimidamidopentanamido]-5-carbamimidamidopentanamido]acetamido}-4-carbamoylbutanamido]-3-hydroxypropanamido]-3-phenylpropanamido]-3-(4-hydroxyphenyl)propanamido]-3-methylbutanamido]-4-carbamoylbutanamido]-3-methylpentanamido]-3-carboxypropanamido]-3-phenylpropanamido]-3-hydroxypropanamido]-5-carbamimidamidopentanoyl]pyrrolidin-2-yl]formamido}-3-(4-hydroxyphenyl)propanamido]-3-carboxypropanoyl]pyrrolidin-2-yl]formamido}-5-carbamimidamidopentanamido]-5-carbamimidamidopentanamido]butanedioic acid

• ChemBase ID: 133521
• Molecular Formular: C144H225N45O40
• Molecular Mass: 3226.6048
• Monoisotopic Mass: 3224.69554723
• SMILES: CC[C@H](C)[C@@H](C(=O)N[C@@H](CC(=O)O)C(=O)N[C@@H](Cc1ccccc1)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCCNC(=N)N)C(=O)N1CCC[C@H]1C(=O)N[C@@H](Cc1ccc(cc1)O)C(=O)N[C@@H](CC(=O)O)C(=O)N1CCC[C@H]1C(=O)N[C@@H](CCCNC(=N)N)C(=O)N[C@@H](CCCNC(=N)N)C(=O)N[C@@H](CC(=O)O)C(=O)O)NC(=O)[C@H](CCC(=O)N)NC(=O)[C@H](C(C)C)NC(=O)[C@H](Cc1ccc(cc1)O)NC(=O)[C@H](Cc1ccccc1)NC(=O)[C@H](CO)NC(=O)[C@H](CCC(=O)N)NC(=O)CNC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H](C(C)C)NC(=O)[C@H]([C@@H](C)CC)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CC(=O)N)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)NCC(=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)N1CCC[C@H]1C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)O)CC(=O)O)CCCNC(=N)N)CCCNC(=N)N)CC(=O)O)Cc1ccc(cc1)O)CCCNC(=N)N)CO)Cc1ccccc1)CC(=O)O)[C@H](CC)C)CCC(=O)N)C(C)C)Cc1ccc(cc1)O)Cc1ccccc1)CO)CCC(=O)N)CCCNC(=N)N)CCCNC(=N)N)C(C)C)[C@H](CC)C)CC(C)C)NC(=O)[C@H](CC(=O)N)N
• InChI: InChI=1S/C144H225N45O40/c1-11-75(9)113(135(224)179-97(66-108(198)199)126(215)175-94(62-78-30-17-14-18-31-78)125(214)183-100(70-190)129(218)173-91(37-25-57-164-144(158)159)137(226)188-58-26-39-103(188)132(221)178-95(63-79-40-44-81(192)45-41-79)124(213)180-98(67-109(200)201)138(227)189-59-27-38-102(189)131(220)170-87(35-23-55-162-142(154)155)117(206)169-86(34-22-54-161-141(152)153)120(209)181-99(139(228)229)68-110(202)203)186-122(211)90(49-51-105(148)195)172-133(222)111(73(5)6)184-128(217)96(64-80-42-46-82(193)47-43-80)176-123(212)93(61-77-28-15-13-16-29-77)177-130(219)101(71-191)182-121(210)89(48-50-104(147)194)166-107(197)69-165-116(205)84(33-21-53-160-140(150)151)168-118(207)88(36-24-56-163-143(156)157)171-134(223)112(74(7)8)185-136(225)114(76(10)12-2)187-127(216)92(60-72(3)4)174-119(208)85(32-19-20-52-145)167-115(204)83(146)65-106(149)196/h13-18,28-31,40-47,72-76,83-103,111-114,190-193H,11-12,19-27,32-39,48-71,145-146H2,1-10H3,(H2,147,194)(H2,148,195)(H2,149,196)(H,165,205)(H,166,197)(H,167,204)(H,168,207)(H,169,206)(H,170,220)(H,171,223)(H,172,222)(H,173,218)(H,174,208)(H,175,215)(H,176,212)(H,177,219)(H,178,221)(H,179,224)(H,180,213)(H,181,209)(H,182,210)(H,183,214)(H,184,217)(H,185,225)(H,186,211)(H,187,216)(H,198,199)(H,200,201)(H,202,203)(H,228,229)(H4,150,151,160)(H4,152,153,161)(H4,154,155,162)(H4,156,157,163)(H4,158,159,164)/t75-,76-,83-,84-,85-,86-,87-,88-,89-,90-,91-,92-,93-,94-,95-,96-,97-,98-,99-,100-,101-,102-,103-,111-,112-,113-,114-/m0/s1
• InChIKey: COSNLKCXZQMASK-SUYFAVNQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-[(2S)-2-[(2S)-2-{[(2S)-1-[(2S)-2-[(2S)-2-{[(2S)-1-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S,3S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-{2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S,3S)-2-[(2S)-2-[(2S)-6-amino-2-[(2S)-2-amino-3-carbamoylpropanamido]hexanamido]-4-methylpentanamido]-3-methylpentanamido]-3-methylbutanamido]-5-carbamimidamidopentanamido]-5-carbamimidamidopentanamido]acetamido}-4-carbamoylbutanamido]-3-hydroxypropanamido]-3-phenylpropanamido]-3-(4-hydroxyphenyl)propanamido]-3-methylbutanamido]-4-carbamoylbutanamido]-3-methylpentanamido]-3-carboxypropanamido]-3-phenylpropanamido]-3-hydroxypropanamido]-5-carbamimidamidopentanoyl]pyrrolidin-2-yl]formamido}-3-(4-hydroxyphenyl)propanamido]-3-carboxypropanoyl]pyrrolidin-2-yl]formamido}-5-carbamimidamidopentanamido]-5-carbamimidamidopentanamido]butanedioic acid
• IUPAC Traditional name: (2S)-2-[(2S)-2-[(2S)-2-{[(2S)-1-[(2S)-2-[(2S)-2-{[(2S)-1-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S,3S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-{2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S,3S)-2-[(2S)-2-[(2S)-6-amino-2-[(2S)-2-amino-3-carbamoylpropanamido]hexanamido]-4-methylpentanamido]-3-methylpentanamido]-3-methylbutanamido]-5-carbamimidamidopentanamido]-5-carbamimidamidopentanamido]acetamido}-4-carbamoylbutanamido]-3-hydroxypropanamido]-3-phenylpropanamido]-3-(4-hydroxyphenyl)propanamido]-3-methylbutanamido]-4-carbamoylbutanamido]-3-methylpentanamido]-3-carboxypropanamido]-3-phenylpropanamido]-3-hydroxypropanamido]-5-carbamimidamidopentanoyl]pyrrolidin-2-yl]formamido}-3-(4-hydroxyphenyl)propanamido]-3-carboxypropanoyl]pyrrolidin-2-yl]formamido}-5-carbamimidamidopentanamido]-5-carbamimidamidopentanamido]butanedioic acid
• Synonyms: Asn-Lys-Leu-Ile-Val-Arg-Arg-Gly-Gln-Ser-Phe-Tyr-Val-Gln-Ile-Asp-Phe-Ser-Arg-Pro-Tyr-Asp-Pro-Arg-Arg-Asp; Factor XIIIa Fragment 72-97

Database IDs

• CAS Number: 158053-05-5
• MDL Number: MFCD00236927
• PubChem SID: 162227798
• PubChem CID: 71308683

CALCULATED PROPERTIES

• Acid pKa: 3.0306754
• H Acceptors: 57
• H Donor: 51
• LogD (pH = 5.5): -24.622623
• LogD (pH = 7.4): -24.524035
• Log P: -20.273031
• Molar Refractivity: 863.83 cm^3
• Polarizability: 316.24 Å^3
• Polar Surface Area: 1430.85 Å^2
• Rotatable Bonds: 105
• Lipinski's Rule of Five: false

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 ... F13A1(2162)

Product Information

• Purity: ≥90% (HPLC)

DETAILS

Sigma Aldrich - F0166

Biochem/physiol Actions
Inhibits the transglutaminase activity of Factor XIIIa, thus blocking the cross-linking of fibrin, fibronectin, and N,N′-dimethylcasein.