(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-amino-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: 134374
• Molecular Formular: C147H217N43O37S6
• Molecular Mass: 3370.95178
• Monoisotopic Mass: 3368.4744811
• 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)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](N)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)C
• InChI: InChI=1S/C147H217N43O37S6/c1-13-73(6)114-139(222)168-76(9)118(201)163-63-110(196)170-96(48-50-113(199)200)127(210)172-92(31-22-52-159-145(152)153)125(208)171-93(32-23-53-160-146(154)155)126(209)178-98(58-81-35-41-85(192)42-36-81)123(206)165-65-112(198)186-117(79(12)191)141(224)184-106-70-232-229-67-103-134(217)173-94(33-24-54-161-147(156)157)128(211)189-116(75(8)15-3)142(225)190-55-25-34-108(190)138(221)167-78(11)120(203)181-105(136(219)187-114)69-231-230-68-104(135(218)185-107(143(226)227)71-233-228-66-89(148)121(204)176-100(133(216)182-103)59-82-37-43-86(193)44-38-82)183-132(215)99(57-80-26-17-16-18-27-80)175-119(202)77(10)166-129(212)102(61-84-62-162-90-29-20-19-28-88(84)90)179-130(213)97(56-72(4)5)177-124(207)91(30-21-51-158-144(150)151)169-111(197)64-164-122(205)95(47-49-109(149)195)174-131(214)101(60-83-39-45-87(194)46-40-83)180-140(223)115(74(7)14-2)188-137(106)220/h16-20,26-29,35-46,62,72-79,89,91-108,114-117,162,191-194H,13-15,21-25,30-34,47-61,63-71,148H2,1-12H3,(H2,149,195)(H,163,201)(H,164,205)(H,165,206)(H,166,212)(H,167,221)(H,168,222)(H,169,197)(H,170,196)(H,171,208)(H,172,210)(H,173,217)(H,174,214)(H,175,202)(H,176,204)(H,177,207)(H,178,209)(H,179,213)(H,180,223)(H,181,203)(H,182,216)(H,183,215)(H,184,224)(H,185,218)(H,186,198)(H,187,219)(H,188,220)(H,189,211)(H,199,200)(H,226,227)(H4,150,151,158)(H4,152,153,159)(H4,154,155,160)(H4,156,157,161)/t73-,74-,75-,76-,77-,78-,79+,89-,91-,92-,93-,94-,95-,96-,97-,98-,99-,100-,101-,102-,103-,104-,105-,106-,107-,108-,114-,115-,116-,117-/m0/s1
• InChIKey: GRZXCHIIZXMEPJ-HTLKCAKFSA-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-amino-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-amino-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-2; Defensin HNP-2 human

Database IDs

• CAS Number: 99287-07-7
• MDL Number: MFCD00076222
• PubChem SID: 162228650
• PubChem CID: 16130867

CALCULATED PROPERTIES

• Acid pKa: 2.961086
• H Acceptors: 50
• H Donor: 48
• LogD (pH = 5.5): -20.980534
• LogD (pH = 7.4): -19.305285
• Log P: -16.677586
• Molar Refractivity: 898.3198 cm^3
• Polarizability: 334.2478 Å^3
• Polar Surface Area: 1294.03 Å^2
• Rotatable Bonds: 42
• 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: ≥95% (HPLC)

DETAILS

Sigma Aldrich - D6790

Amino Acid Sequence
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: 1-29, 3-18, 8-28]
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 famuly are variably arginine-rich and all share 6 conserved cysteine residues that participate in intramolecular disulfide bonds.