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158053-05-5 molecular structure
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(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 and InChIs

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

Cite this record

CBID:133521 http://www.chembase.cn/molecule-133521.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
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
CAS Number
158053-05-5
MDL Number
MFCD00236927
PubChem SID
162227798
PubChem CID
71308683

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID Price
Sigma Aldrich
F0166 external link Add to cart Please log in.
Data Source Data ID
PubChem 71308683 external link

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
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 cm3 Polarizability 316.24 Å3
Polar Surface Area 1430.85 Å2 Rotatable Bonds 105 
Lipinski's Rule of Five false 

PROPERTIES

PROPERTIES

Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
German water hazard class
3 expand Show data source
Personal Protective Equipment
Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter expand Show data source
Storage Temperature
-20°C expand Show data source
Gene Information
human ... F13A1(2162) expand Show data source
Purity
≥90% (HPLC) expand Show data source

DETAILS

DETAILS

Sigma Aldrich Sigma Aldrich
Sigma Aldrich - F0166 external link
Biochem/physiol Actions
Inhibits the transglutaminase activity of Factor XIIIa, thus blocking the cross-linking of fibrin, fibronectin, and N,N′-dimethylcasein.

REFERENCES

REFERENCES

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PATENTS

PATENTS

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