(1R,4S,7S,13S,16S,19R,22S,25S,31S,34S,37S,40S,46S,49R,52S,55S,58S,64S,67S,70S,73S,76S,79R,82R,87R,90S)-87-[(2S)-2-aminopropanamido]-76-benzyl-7,22,52-tris[(2S)-butan-2-yl]-4,34,37,64-tetrakis(3-carbamimidamidopropyl)-58-(2-carbamoylethyl)-31-(2-carboxyethyl)-46-[(1R)-1-hydroxyethyl]-40,55,90-tris[(4-hydroxyphenyl)methyl]-70-(1H-indol-3-ylmethyl)-16,25,73-trimethyl-67-(2-methylpropyl)-2,5,8,14,17,20,23,26,29,32,35,38,41,44,47,50,53,56,59,62,65,68,71,74,77,80,88,91-octacosaoxo-84,85,94,95,98,99-hexathia-3,6,9,15,18,21,24,27,30,33,36,39,42,45,48,51,54,57,60,63,66,69,72,75,78,81,89,92-octacosaazatetracyclo[47.43.4.419,79.09,13]100ne-82-carboxylic acid

• ChemBase ID: 134063
• Molecular Formular: C150H222N44O38S6
• Molecular Mass: 3442.02968
• Monoisotopic Mass: 3439.51159488
• SMILES: CC[C@H](C)[C@H]1C(=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)NCC(=O)N[C@H](C(=O)N[C@H]2CSSC[C@H]3C(=O)N[C@H](C(=O)N[C@H](C(=O)N4CCC[C@H]4C(=O)N[C@H](C(=O)N[C@@H](CSSC[C@@H](C(=O)N[C@@H](CSSC[C@@H](C(=O)N[C@H](C(=O)N3)Cc3ccc(cc3)O)NC(=O)[C@H](C)N)C(=O)O)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)CNC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC2=O)[C@@H](C)CC)Cc2ccc(cc2)O)CCC(=O)N)CCCNC(=N)N)CC(C)C)Cc2c[nH]c3c2cccc3)C)Cc2ccccc2)C(=O)N1)C)[C@@H](C)CC)CCCNC(=N)N)[C@@H](C)O)Cc1ccc(cc1)O)CCCNC(=N)N)CCCNC(=N)N)CCC(=O)O)C
• Canonical SMILES: CC[C@@H]([C@@H]1NC(=O)[C@@H]2CSSC[C@@H]3NC(=O)[C@H](Cc4ccc(cc4)O)NC(=O)[C@H](CSSC[C@H](NC(=O)[C@H](CSSC[C@H](NC(=O)[C@@H](NC(=O)[C@H]4N(C(=O)[C@@H](NC(=O)[C@@H](NC3=O)CCCNC(=N)N)[C@H](CC)C)CCC4)C)C(=O)N[C@@H]([C@H](CC)C)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)NCC(=O)N[C@H](C(=O)N2)[C@H](O)C)Cc2ccc(cc2)O)CCCNC(=N)N)CCCNC(=N)N)CCC(=O)O)C)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)CNC(=O)[C@@H](NC(=O)[C@@H](NC1=O)Cc1ccc(cc1)O)CCC(=O)N)CCCNC(=N)N)CC(C)C)Cc1c[nH]c2c1cccc2)C)Cc1ccccc1)C(=O)O)NC(=O)[C@@H](N)C)C
• InChI: InChI=1S/C150H222N44O38S6/c1-14-74(6)116-142(227)171-78(10)121(206)166-64-112(200)173-97(49-51-115(203)204)129(214)175-93(32-23-53-162-148(155)156)127(212)174-94(33-24-54-163-149(157)158)128(213)180-99(59-83-36-42-87(196)43-37-83)125(210)168-66-114(202)190-119(81(13)195)144(229)188-108-71-236-233-68-105-136(221)176-95(34-25-55-164-150(159)160)130(215)193-118(76(8)16-3)145(230)194-56-26-35-110(194)141(226)170-80(12)123(208)185-107(139(224)191-116)70-235-234-69-106(138(223)189-109(146(231)232)72-238-237-67-104(184-120(205)77(9)151)137(222)181-101(135(220)186-105)60-84-38-44-88(197)45-39-84)187-134(219)100(58-82-27-18-17-19-28-82)178-122(207)79(11)169-131(216)103(62-86-63-165-91-30-21-20-29-90(86)91)182-132(217)98(57-73(4)5)179-126(211)92(31-22-52-161-147(153)154)172-113(201)65-167-124(209)96(48-50-111(152)199)177-133(218)102(61-85-40-46-89(198)47-41-85)183-143(228)117(75(7)15-2)192-140(108)225/h17-21,27-30,36-47,63,73-81,92-110,116-119,165,195-198H,14-16,22-26,31-35,48-62,64-72,151H2,1-13H3,(H2,152,199)(H,166,206)(H,167,209)(H,168,210)(H,169,216)(H,170,226)(H,171,227)(H,172,201)(H,173,200)(H,174,212)(H,175,214)(H,176,221)(H,177,218)(H,178,207)(H,179,211)(H,180,213)(H,181,222)(H,182,217)(H,183,228)(H,184,205)(H,185,208)(H,186,220)(H,187,219)(H,188,229)(H,189,223)(H,190,202)(H,191,224)(H,192,225)(H,193,215)(H,203,204)(H,231,232)(H4,153,154,161)(H4,155,156,162)(H4,157,158,163)(H4,159,160,164)/t74-,75-,76-,77-,78-,79-,80-,81+,92-,93-,94-,95-,96-,97-,98-,99-,100-,101-,102-,103-,104-,105-,106-,107-,108-,109-,110-,116-,117-,118-,119-/m0/s1
• InChIKey: KRJOFJHOZZPBKI-KSWODRSDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,4S,7S,13S,16S,19R,22S,25S,31S,34S,37S,40S,46S,49R,52S,55S,58S,64S,67S,70S,73S,76S,79R,82R,87R,90S)-87-[(2S)-2-aminopropanamido]-76-benzyl-7,22,52-tris[(2S)-butan-2-yl]-4,34,37,64-tetrakis(3-carbamimidamidopropyl)-58-(2-carbamoylethyl)-31-(2-carboxyethyl)-46-[(1R)-1-hydroxyethyl]-40,55,90-tris[(4-hydroxyphenyl)methyl]-70-(1H-indol-3-ylmethyl)-16,25,73-trimethyl-67-(2-methylpropyl)-2,5,8,14,17,20,23,26,29,32,35,38,41,44,47,50,53,56,59,62,65,68,71,74,77,80,88,91-octacosaoxo-84,85,94,95,98,99-hexathia-3,6,9,15,18,21,24,27,30,33,36,39,42,45,48,51,54,57,60,63,66,69,72,75,78,81,89,92-octacosaazatetracyclo[47.43.4.4^1^9,^7^9.0^9,^1^3]100ne-82-carboxylic acid
• IUPAC Traditional name: (1R,4S,7S,13S,16S,19R,22S,25S,31S,34S,37S,40S,46S,49R,52S,55S,58S,64S,67S,70S,73S,76S,79R,82R,87R,90S)-87-[(2S)-2-aminopropanamido]-76-benzyl-7,22,52-tris[(2S)-butan-2-yl]-4,34,37,64-tetrakis(3-carbamimidamidopropyl)-58-(2-carbamoylethyl)-31-(2-carboxyethyl)-46-[(1R)-1-hydroxyethyl]-40,55,90-tris[(4-hydroxyphenyl)methyl]-70-(1H-indol-3-ylmethyl)-16,25,73-trimethyl-67-(2-methylpropyl)-2,5,8,14,17,20,23,26,29,32,35,38,41,44,47,50,53,56,59,62,65,68,71,74,77,80,88,91-octacosaoxo-84,85,94,95,98,99-hexathia-3,6,9,15,18,21,24,27,30,33,36,39,42,45,48,51,54,57,60,63,66,69,72,75,78,81,89,92-octacosaazatetracyclo[47.43.4.4^1^9,^7^9.0^9,^1^3]100ne-82-carboxylic acid
• Synonyms: Neutrophil Peptide-1; Defensin HNP-1 human

Database IDs

• CAS Number: 99287-08-8
• MDL Number: MFCD00214572
• PubChem SID: 162228340
• PubChem CID: 16130476

CALCULATED PROPERTIES

• Acid pKa: 2.8741152
• H Acceptors: 51
• H Donor: 49
• LogD (pH = 5.5): -21.8638
• LogD (pH = 7.4): -20.158974
• Log P: -17.21443
• Molar Refractivity: 915.6172 cm^3
• Polarizability: 341.01828 Å^3
• Polar Surface Area: 1323.13 Å^2
• Rotatable Bonds: 44
• 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 ... DEFA1(1667)

Product Information

• Purity: ≥80% (HPLC)
• Compostion: Peptide content, ~70%

DETAILS

Sigma Aldrich - D2043

Amino Acid Sequence
Ala-Cys-Tyr-Cys-Arg-Ile-Pro-Ala-Cys-Ile-Ala-Gly-Glu-Arg-Arg-Tyr-Gly-Thr-Cys-Ile-Tyr-Gln-Gly-Arg-Leu-Trp-Ala-Phe-Cys-Cys [Disulfide bridges: 2-30; 4-19; 9-29]
Biochem/physiol Actions
This is an endogenous antibiotic peptide and monocyte chemotactic peptide produced by human neutrophils. Defensins are a family of 3-4 kDa (29-34 amino acids) peptides found in the granules of mammalian phagocytes. The members of this family are variably arginine-rich and share six conserved cysteine residues that participate in intramolecular disulfide bonds.