(2S,3S)-2-[(2S)-2-{[(2S)-1-[(2S)-6-amino-2-{[(2S)-1-[(2S)-2-[(2S)-2-{[(2S)-1-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-{2-[(2S,3R)-2-amino-3-hydroxybutanamido]acetamido}-4-carbamoylbutanamido]-3-phenylpropanamido]-5-carbamimidamidopentanamido]-3-methylbutanamido]-3-(4-hydroxyphenyl)propanoyl]pyrrolidin-2-yl]formamido}-4-carboxybutanamido]-4-methylpentanoyl]pyrrolidin-2-yl]formamido}hexanoyl]pyrrolidin-2-yl]formamido}-3-hydroxypropanamido]-3-methylpentanoic acid

• ChemBase ID: 132167
• Molecular Formular: C81H126N20O22
• Molecular Mass: 1731.98794
• Monoisotopic Mass: 1730.93555577
• SMILES: CC[C@H](C)[C@@H](C(=O)O)NC(=O)[C@H](CO)NC(=O)[C@@H]1CCCN1C(=O)[C@H](CCCCN)NC(=O)[C@@H]1CCCN1C(=O)[C@H](CC(C)C)NC(=O)[C@H](CCC(=O)O)NC(=O)[C@@H]1CCCN1C(=O)[C@H](Cc1ccc(cc1)O)NC(=O)[C@H](C(C)C)NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H](Cc1ccccc1)NC(=O)[C@H](CCC(=O)N)NC(=O)CNC(=O)[C@H]([C@@H](C)O)N
• Canonical SMILES: NCCCC[C@@H](C(=O)N1CCC[C@H]1C(=O)N[C@H](C(=O)N[C@@H]([C@H](CC)C)C(=O)O)CO)NC(=O)[C@@H]1CCCN1C(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H]1CCCN1C(=O)[C@@H](NC(=O)[C@H](C(C)C)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)CNC(=O)[C@H]([C@H](O)C)N)CCC(=O)N)Cc1ccccc1)CCCNC(=N)N)Cc1ccc(cc1)O)CCC(=O)O)CC(C)C
• InChI: InChI=1S/C81H126N20O22/c1-8-45(6)66(80(122)123)98-71(113)57(42-102)96-74(116)60-24-15-35-99(60)77(119)53(20-12-13-33-82)92-73(115)59-23-17-36-100(59)78(120)55(38-43(2)3)94-68(110)52(30-32-63(107)108)91-72(114)58-22-16-37-101(58)79(121)56(40-48-25-27-49(104)28-26-48)95-76(118)65(44(4)5)97-69(111)50(21-14-34-87-81(85)86)90-70(112)54(39-47-18-10-9-11-19-47)93-67(109)51(29-31-61(83)105)89-62(106)41-88-75(117)64(84)46(7)103/h9-11,18-19,25-28,43-46,50-60,64-66,102-104H,8,12-17,20-24,29-42,82,84H2,1-7H3,(H2,83,105)(H,88,117)(H,89,106)(H,90,112)(H,91,114)(H,92,115)(H,93,109)(H,94,110)(H,95,118)(H,96,116)(H,97,111)(H,98,113)(H,107,108)(H,122,123)(H4,85,86,87)/t45-,46+,50-,51-,52-,53-,54-,55-,56-,57-,58-,59-,60-,64-,65-,66-/m0/s1
• InChIKey: LMDZISZNTCXHDM-KEDROYBBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S)-2-[(2S)-2-{[(2S)-1-[(2S)-6-amino-2-{[(2S)-1-[(2S)-2-[(2S)-2-{[(2S)-1-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-{2-[(2S,3R)-2-amino-3-hydroxybutanamido]acetamido}-4-carbamoylbutanamido]-3-phenylpropanamido]-5-carbamimidamidopentanamido]-3-methylbutanamido]-3-(4-hydroxyphenyl)propanoyl]pyrrolidin-2-yl]formamido}-4-carboxybutanamido]-4-methylpentanoyl]pyrrolidin-2-yl]formamido}hexanoyl]pyrrolidin-2-yl]formamido}-3-hydroxypropanamido]-3-methylpentanoic acid
• IUPAC Traditional name: (2S,3S)-2-[(2S)-2-{[(2S)-1-[(2S)-6-amino-2-{[(2S)-1-[(2S)-2-[(2S)-2-{[(2S)-1-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-{2-[(2S,3R)-2-amino-3-hydroxybutanamido]acetamido}-4-carbamoylbutanamido]-3-phenylpropanamido]-5-carbamimidamidopentanamido]-3-methylbutanamido]-3-(4-hydroxyphenyl)propanoyl]pyrrolidin-2-yl]formamido}-4-carboxybutanamido]-4-methylpentanoyl]pyrrolidin-2-yl]formamido}hexanoyl]pyrrolidin-2-yl]formamido}-3-hydroxypropanamido]-3-methylpentanoic acid
• Synonyms: Carcinoembryonic Antigen Fragment 101-115

Database IDs

• CAS Number: 145204-53-1
• MDL Number: MFCD00236907
• PubChem SID: 162226444
• PubChem CID: 71308528

CALCULATED PROPERTIES

• Acid pKa: 3.1082501
• H Acceptors: 27
• H Donor: 22
• LogD (pH = 5.5): -11.577851
• LogD (pH = 7.4): -9.926208
• Log P: -9.6645775
• Molar Refractivity: 450.3662 cm^3
• Polarizability: 172.3789 Å^3
• Polar Surface Area: 673.35 Å^2
• Rotatable Bonds: 51
• 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 ... CEACAM3(1084), CEACAM5(1048)

Product Information

• Purity: ≥95% (HPLC)

DETAILS

Sigma Aldrich - C3330

Amino Acid Sequence
Thr-Gly-Gln-Phe-Arg-Val-Tyr-Pro-Glu-Leu-Pro-Lys-Pro-Ser-Ile
Biochem/physiol Actions
Peptide with strong affinity for the 80 kDa surface protein on Kupffer cells, possibly involved in hepatic metastasis.