(4S)-4-{[(1S)-5-amino-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-4-carbamimidamido-1-[({[(1S)-1-carboxy-2-(4-hydroxyphenyl)ethyl]carbamoyl}methyl)carbamoyl]butyl]carbamoyl}-2-(1H-imidazol-4-yl)ethyl]carbamoyl}-2-hydroxyethyl]carbamoyl}-2-(1H-imidazol-4-yl)ethyl]carbamoyl}-2-(1H-imidazol-4-yl)ethyl]carbamoyl}pentyl]carbamoyl}-4-[(2S)-2-[(2S)-2-[(2S)-6-amino-2-[(2S)-2-[(2S)-6-amino-2-[(2S)-2-{2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-6-amino-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-amino-3-carboxypropanamido]-3-hydroxypropanamido]-3-(1H-imidazol-4-yl)propanamido]propanamido]hexanamido]-5-carbamimidamidopentanamido]-3-(1H-imidazol-4-yl)propanamido]-3-(1H-imidazol-4-yl)propanamido]acetamido}-3-(4-hydroxyphenyl)propanamido]hexanamido]-5-carbamimidamidopentanamido]hexanamido]-3-phenylpropanamido]-3-(1H-imidazol-4-yl)propanamido]butanoic acid

• ChemBase ID: 133089
• Molecular Formular: C133H195N51O33
• Molecular Mass: 3036.2933
• Monoisotopic Mass: 3034.51483796
• SMILES: C[C@@H](C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCNC(=N)N)C(=O)N[C@@H](Cc1c[nH]cn1)C(=O)N[C@@H](Cc1c[nH]cn1)C(=O)NCC(=O)N[C@@H](Cc1ccc(cc1)O)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCNC(=N)N)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](Cc1ccccc1)C(=O)N[C@@H](Cc1c[nH]cn1)C(=O)N[C@@H](CCC(=O)O)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](Cc1c[nH]cn1)C(=O)N[C@@H](Cc1c[nH]cn1)C(=O)N[C@@H](CO)C(=O)N[C@@H](Cc1c[nH]cn1)C(=O)N[C@@H](CCCNC(=N)N)C(=O)NCC(=O)N[C@@H](Cc1ccc(cc1)O)C(=O)O)NC(=O)[C@H](Cc1c[nH]cn1)NC(=O)[C@H](CO)NC(=O)[C@H](CC(=O)O)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)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)O)Cc1ccc(cc1)O)CCCNC(=N)N)Cc1c[nH]cn1)CO)Cc1c[nH]cn1)Cc1c[nH]cn1)CCCCN)CCC(=O)O)Cc1c[nH]cn1)Cc1ccccc1)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H](Cc1ccc(cc1)O)NC(=O)CNC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H](CC(=O)O)N)CO)Cc1c[nH]cn1)C)CCCCN)CCCNC(=N)N)Cc1c[nH]cn1)Cc1c[nH]cn1)CCCCN)CCCNC(=N)N
• InChI: InChI=1S/C133H195N51O33/c1-71(164-120(206)96(46-76-54-146-65-158-76)181-128(214)103(62-185)183-110(196)84(138)52-108(193)194)109(195)167-86(18-5-9-35-134)113(199)172-91(24-15-41-154-133(143)144)118(204)178-99(49-79-57-149-68-161-79)125(211)176-95(45-75-53-145-64-157-75)112(198)156-60-105(189)165-93(43-73-25-29-82(187)30-26-73)121(207)173-87(19-6-10-36-135)114(200)171-90(23-14-40-153-132(141)142)115(201)169-88(20-7-11-37-136)116(202)175-94(42-72-16-3-2-4-17-72)122(208)179-97(47-77-55-147-66-159-77)124(210)174-92(33-34-107(191)192)119(205)170-89(21-8-12-38-137)117(203)177-100(50-80-58-150-69-162-80)126(212)180-101(51-81-59-151-70-163-81)127(213)184-104(63-186)129(215)182-98(48-78-56-148-67-160-78)123(209)168-85(22-13-39-152-131(139)140)111(197)155-61-106(190)166-102(130(216)217)44-74-27-31-83(188)32-28-74/h2-4,16-17,25-32,53-59,64-71,84-104,185-188H,5-15,18-24,33-52,60-63,134-138H2,1H3,(H,145,157)(H,146,158)(H,147,159)(H,148,160)(H,149,161)(H,150,162)(H,151,163)(H,155,197)(H,156,198)(H,164,206)(H,165,189)(H,166,190)(H,167,195)(H,168,209)(H,169,201)(H,170,205)(H,171,200)(H,172,199)(H,173,207)(H,174,210)(H,175,202)(H,176,211)(H,177,203)(H,178,204)(H,179,208)(H,180,212)(H,181,214)(H,182,215)(H,183,196)(H,184,213)(H,191,192)(H,193,194)(H,216,217)(H4,139,140,152)(H4,141,142,153)(H4,143,144,154)/t71-,84-,85-,86-,87-,88-,89-,90-,91-,92-,93-,94-,95-,96-,97-,98-,99-,100-,101-,102-,103-,104-/m0/s1
• InChIKey: KSXBMTJGDUPBBN-VPKNIDFUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4S)-4-{[(1S)-5-amino-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-4-carbamimidamido-1-[({[(1S)-1-carboxy-2-(4-hydroxyphenyl)ethyl]carbamoyl}methyl)carbamoyl]butyl]carbamoyl}-2-(1H-imidazol-4-yl)ethyl]carbamoyl}-2-hydroxyethyl]carbamoyl}-2-(1H-imidazol-4-yl)ethyl]carbamoyl}-2-(1H-imidazol-4-yl)ethyl]carbamoyl}pentyl]carbamoyl}-4-[(2S)-2-[(2S)-2-[(2S)-6-amino-2-[(2S)-2-[(2S)-6-amino-2-[(2S)-2-{2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-6-amino-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-amino-3-carboxypropanamido]-3-hydroxypropanamido]-3-(1H-imidazol-4-yl)propanamido]propanamido]hexanamido]-5-carbamimidamidopentanamido]-3-(1H-imidazol-4-yl)propanamido]-3-(1H-imidazol-4-yl)propanamido]acetamido}-3-(4-hydroxyphenyl)propanamido]hexanamido]-5-carbamimidamidopentanamido]hexanamido]-3-phenylpropanamido]-3-(1H-imidazol-4-yl)propanamido]butanoic acid
• IUPAC Traditional name: (4S)-4-{[(1S)-5-amino-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-4-carbamimidamido-1-[({[(1S)-1-carboxy-2-(4-hydroxyphenyl)ethyl]carbamoyl}methyl)carbamoyl]butyl]carbamoyl}-2-(1H-imidazol-4-yl)ethyl]carbamoyl}-2-hydroxyethyl]carbamoyl}-2-(1H-imidazol-4-yl)ethyl]carbamoyl}-2-(1H-imidazol-4-yl)ethyl]carbamoyl}pentyl]carbamoyl}-4-[(2S)-2-[(2S)-2-[(2S)-6-amino-2-[(2S)-2-[(2S)-6-amino-2-[(2S)-2-{2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-6-amino-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-amino-3-carboxypropanamido]-3-hydroxypropanamido]-3-(1H-imidazol-4-yl)propanamido]propanamido]hexanamido]-5-carbamimidamidopentanamido]-3-(1H-imidazol-4-yl)propanamido]-3-(1H-imidazol-4-yl)propanamido]acetamido}-3-(4-hydroxyphenyl)propanamido]hexanamido]-5-carbamimidamidopentanamido]hexanamido]-3-phenylpropanamido]-3-(1H-imidazol-4-yl)propanamido]butanoic acid
• Synonyms: Histatin 5

Database IDs

• CAS Number: 104339-66-4
• MDL Number: MFCD00210682
• PubChem SID: 162227366
• PubChem CID: 71308633

CALCULATED PROPERTIES

• Acid pKa: 2.899968
• H Acceptors: 54
• H Donor: 51
• LogD (pH = 5.5): -30.059708
• LogD (pH = 7.4): -29.204706
• Log P: -24.267977
• Molar Refractivity: 795.5799 cm^3
• Polarizability: 296.97293 Å^3
• Polar Surface Area: 1378.68 Å^2
• Rotatable Bonds: 102
• 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 ... HTN3(3347)

Product Information

• Purity: ≥97% (HPLC)

DETAILS

Sigma Aldrich - H6027

Amino Acid Sequence
Asp-Ser-His-Ala-Lys-Arg-His-His-Gly-Tyr-Lys-Arg-Lys-Phe-His-Glu-Lys-His-His-Ser-His-Arg-Gly-Tyr
Biochem/physiol Actions
A human salivary peptide that inhibits the protease of Bacteroides gingivalis, as well as clostripain.
The antifungal (Candida, Leishmania) activity of histatin 5 involves penetration of the microbial cell, localization in the mitochondria, and inhibition of F1-F0 ATPase, with rapid depletion of ATP.1