(4S)-5-[(2S)-2-{[(1S)-1-{[(1S,2S)-1-[({[(1S)-1-{[(1S)-5-amino-1-{[(1S)-5-amino-1-{[(1S,2R)-1-carboxy-2-hydroxypropyl]carbamoyl}pentyl]carbamoyl}pentyl]carbamoyl}-4-carbamimidamidobutyl]carbamoyl}methyl)carbamoyl]-2-methylbutyl]carbamoyl}-3-methylbutyl]carbamoyl}pyrrolidin-1-yl]-4-[(2S)-2-[(2S)-6-amino-2-[(2S)-4-carbamoyl-2-[(2S)-3-carbamoyl-2-[(2S)-3-carbamoyl-2-[(2S)-2,6-diaminohexanamido]propanamido]propanamido]butanamido]hexanamido]-3-hydroxypropanamido]-5-oxopentanoic acid

• ChemBase ID: 133717
• Molecular Formular: C74H133N25O23
• Molecular Mass: 1741.00152
• Monoisotopic Mass: 1740.00061564
• SMILES: CC[C@H](C)[C@@H](C(=O)NCC(=O)N[C@@H](CCCNC(=N)N)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H]([C@@H](C)O)C(=O)O)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H]1CCCN1C(=O)[C@H](CCC(=O)O)NC(=O)[C@H](CO)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CCC(=O)N)NC(=O)[C@H](CC(=O)N)NC(=O)[C@H](CC(=O)N)NC(=O)[C@H](CCCCN)N
• Canonical SMILES: NCCCC[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)NCC(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)O)[C@H](O)C)CCCCN)CCCCN)CCCNC(=N)N)[C@H](CC)C)CC(C)C)CCC(=O)O)CO)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H](CCCCN)N)CC(=O)N)CC(=O)N)CCC(=O)N
• InChI: InChI=1S/C74H133N25O23/c1-6-39(4)58(71(119)86-36-56(105)87-42(21-15-31-85-74(83)84)61(109)88-43(18-8-12-28-76)62(110)90-45(20-10-14-30-78)65(113)98-59(40(5)101)73(121)122)97-68(116)48(33-38(2)3)95-70(118)52-22-16-32-99(52)72(120)47(24-26-57(106)107)92-69(117)51(37-100)96-63(111)44(19-9-13-29-77)89-64(112)46(23-25-53(80)102)91-66(114)50(35-55(82)104)94-67(115)49(34-54(81)103)93-60(108)41(79)17-7-11-27-75/h38-52,58-59,100-101H,6-37,75-79H2,1-5H3,(H2,80,102)(H2,81,103)(H2,82,104)(H,86,119)(H,87,105)(H,88,109)(H,89,112)(H,90,110)(H,91,114)(H,92,117)(H,93,108)(H,94,115)(H,95,118)(H,96,111)(H,97,116)(H,98,113)(H,106,107)(H,121,122)(H4,83,84,85)/t39-,40+,41-,42-,43-,44-,45-,46-,47-,48-,49-,50-,51-,52-,58-,59-/m0/s1
• InChIKey: ZOAMLYRGMMOBAS-GDMZPDKKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4S)-5-[(2S)-2-{[(1S)-1-{[(1S,2S)-1-[({[(1S)-1-{[(1S)-5-amino-1-{[(1S)-5-amino-1-{[(1S,2R)-1-carboxy-2-hydroxypropyl]carbamoyl}pentyl]carbamoyl}pentyl]carbamoyl}-4-carbamimidamidobutyl]carbamoyl}methyl)carbamoyl]-2-methylbutyl]carbamoyl}-3-methylbutyl]carbamoyl}pyrrolidin-1-yl]-4-[(2S)-2-[(2S)-6-amino-2-[(2S)-4-carbamoyl-2-[(2S)-3-carbamoyl-2-[(2S)-3-carbamoyl-2-[(2S)-2,6-diaminohexanamido]propanamido]propanamido]butanamido]hexanamido]-3-hydroxypropanamido]-5-oxopentanoic acid
• IUPAC Traditional name: (4S)-5-[(2S)-2-{[(1S)-1-{[(1S,2S)-1-[({[(1S)-1-{[(1S)-5-amino-1-{[(1S)-5-amino-1-{[(1S,2R)-1-carboxy-2-hydroxypropyl]carbamoyl}pentyl]carbamoyl}pentyl]carbamoyl}-4-carbamimidamidobutyl]carbamoyl}methyl)carbamoyl]-2-methylbutyl]carbamoyl}-3-methylbutyl]carbamoyl}pyrrolidin-1-yl]-4-[(2S)-2-[(2S)-6-amino-2-[(2S)-4-carbamoyl-2-[(2S)-3-carbamoyl-2-[(2S)-3-carbamoyl-2-[(2S)-2,6-diaminohexanamido]propanamido]propanamido]butanamido]hexanamido]-3-hydroxypropanamido]-5-oxopentanoic acid
• Synonyms: Fibronectin Fragment 1977-1991

Database IDs

• MDL Number: MFCD00672458
• PubChem SID: 162227994
• PubChem CID: 25074476

CALCULATED PROPERTIES

• Acid pKa: 3.1528397
• H Acceptors: 31
• H Donor: 28
• LogD (pH = 5.5): -28.795809
• LogD (pH = 7.4): -25.497908
• Log P: -17.692505
• Molar Refractivity: 442.4253 cm^3
• Polarizability: 170.46016 Å^3
• Polar Surface Area: 834.94 Å^2
• Rotatable Bonds: 64
• 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 ... FN1(2335)

Product Information

• Purity: ≥97% (HPLC)

DETAILS

Sigma Aldrich - F7049

Amino Acid Sequence
Lys-Asn-Asn-Gln-Lys-Ser-Glu-Pro-Leu-Ile-Gly-Arg-Lys-Lys-Thr
Biochem/physiol Actions
Mediates cell adhesion; promotes neuronal adhesion and neurite outgrowth. Binds to the cell surface heparan sulfate proteoglycan (HSPG).
Other Notes
Peptide derived from the C-terminal heparin-binding domain of fibronectin.