(2S)-2-[(2S)-2-{2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S,3R)-2-[(2S)-2-[(2S)-2-[(2S)-2-{2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-amino-3-carboxypropanamido]propanamido]propanamido]-5-carbamimidamidopentanamido]-4-carboxybutanamido]acetamido}-3-phenylpropanamido]-4-methylpentanamido]propanamido]-3-hydroxybutanamido]-4-methylpentanamido]-3-methylbutanamido]-3-methylbutanamido]-4-methylpentanamido]-3-(1H-imidazol-4-yl)propanamido]-5-carbamimidamidopentanamido]propanamido]acetamido}propanamido]-5-carbamimidamidopentanoic acid

• ChemBase ID: 132288
• Molecular Formular: C93H155N31O26
• Molecular Mass: 2123.4179
• Monoisotopic Mass: 2122.17595424
• SMILES: C[C@H]([C@@H](C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](Cc1c[nH]cn1)C(=O)N[C@@H](CCCNC(=N)N)C(=O)N[C@@H](C)C(=O)NCC(=O)N[C@@H](C)C(=O)N[C@@H](CCCNC(=N)N)C(=O)O)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](Cc1ccccc1)NC(=O)CNC(=O)[C@H](CCC(=O)O)NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CC(=O)O)N)O
• Canonical SMILES: NC(=N)NCCC[C@@H](C(=O)N[C@H](C(=O)NCC(=O)N[C@H](C(=O)N[C@H](C(=O)O)CCCNC(=N)N)C)C)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H](C(C)C)NC(=O)[C@H](C(C)C)NC(=O)[C@@H](NC(=O)[C@H]([C@H](O)C)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H](Cc1ccccc1)NC(=O)CNC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H](CC(=O)O)N)C)C)CCCNC(=N)N)CCC(=O)O)CC(C)C)C)CC(C)C)CC(C)C)Cc1nc[nH]c1
• InChI: InChI=1S/C93H155N31O26/c1-43(2)33-61(118-84(143)64(36-54-23-18-17-19-24-54)113-67(127)41-106-79(138)59(28-29-68(128)129)116-81(140)58(26-21-31-103-92(97)98)114-76(135)51(14)109-74(133)50(13)110-78(137)56(94)38-69(130)131)82(141)112-52(15)77(136)124-72(53(16)125)89(148)121-63(35-45(5)6)86(145)122-71(47(9)10)88(147)123-70(46(7)8)87(146)120-62(34-44(3)4)83(142)119-65(37-55-39-101-42-107-55)85(144)115-57(25-20-30-102-91(95)96)80(139)111-48(11)73(132)105-40-66(126)108-49(12)75(134)117-60(90(149)150)27-22-32-104-93(99)100/h17-19,23-24,39,42-53,56-65,70-72,125H,20-22,25-38,40-41,94H2,1-16H3,(H,101,107)(H,105,132)(H,106,138)(H,108,126)(H,109,133)(H,110,137)(H,111,139)(H,112,141)(H,113,127)(H,114,135)(H,115,144)(H,116,140)(H,117,134)(H,118,143)(H,119,142)(H,120,146)(H,121,148)(H,122,145)(H,123,147)(H,124,136)(H,128,129)(H,130,131)(H,149,150)(H4,95,96,102)(H4,97,98,103)(H4,99,100,104)/t48-,49-,50-,51-,52-,53+,56-,57-,58-,59-,60-,61-,62-,63-,64-,65-,70-,71-,72-/m0/s1
• InChIKey: SRSWQMWUNOIPDH-QCDQIEFZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-[(2S)-2-{2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S,3R)-2-[(2S)-2-[(2S)-2-[(2S)-2-{2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-amino-3-carboxypropanamido]propanamido]propanamido]-5-carbamimidamidopentanamido]-4-carboxybutanamido]acetamido}-3-phenylpropanamido]-4-methylpentanamido]propanamido]-3-hydroxybutanamido]-4-methylpentanamido]-3-methylbutanamido]-3-methylbutanamido]-4-methylpentanamido]-3-(1H-imidazol-4-yl)propanamido]-5-carbamimidamidopentanamido]propanamido]acetamido}propanamido]-5-carbamimidamidopentanoic acid
• IUPAC Traditional name: (2S)-2-[(2S)-2-{2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S,3R)-2-[(2S)-2-[(2S)-2-[(2S)-2-{2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-amino-3-carboxypropanamido]propanamido]propanamido]-5-carbamimidamidopentanamido]-4-carboxybutanamido]acetamido}-3-phenylpropanamido]-4-methylpentanamido]propanamido]-3-hydroxybutanamido]-4-methylpentanamido]-3-methylbutanamido]-3-methylbutanamido]-4-methylpentanamido]-3-(1H-imidazol-4-yl)propanamido]-5-carbamimidamidopentanamido]propanamido]acetamido}propanamido]-5-carbamimidamidopentanoic acid
• Synonyms: [Ala92]-p16 fragment 84-103; [Ala92]-Peptide 6

Database IDs

• CAS Number: 189064-08-2
• MDL Number: MFCD00798769
• PubChem SID: 162226565
• PubChem CID: 71308539

CALCULATED PROPERTIES

• Acid pKa: 2.9858184
• H Acceptors: 37
• H Donor: 34
• LogD (pH = 5.5): -17.780066
• LogD (pH = 7.4): -15.372388
• Log P: -14.460567
• Molar Refractivity: 563.8528 cm^3
• Polarizability: 207.9222 Å^3
• Polar Surface Area: 925.43 Å^2
• Rotatable Bonds: 69
• 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 ... CDKN2A(1029)

DETAILS

Sigma Aldrich - P7967

Amino Acid Sequence
Asp-Ala-Ala-Arg-Glu-Gly-Phe-Leu-Ala-Thr-Leu-Val-Val-Leu-His-Arg-Ala-Gly-Ala-Arg
Biochem/physiol Actions
Modified fragment from the third ankyrin-like repeat of p16 that binds to cdk4 and cdk6 and inhibits phosphorylation of the retinoblastoma gene product pRb mediated by cdk4-cyclin D.