(3S)-3-amino-3-{[(1S)-4-carbamimidamido-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-[({[(1S)-1-carbamoyl-3-methylbutyl]carbamoyl}methyl)carbamoyl]-2-phenylethyl]carbamoyl}-2-hydroxyethyl]carbamoyl}-2-(4-hydroxyphenyl)ethyl]carbamoyl}-3-methylbutyl]carbamoyl}butyl]carbamoyl}propanoic acid

• ChemBase ID: 155528
• Molecular Formular: C45H68N12O12
• Molecular Mass: 969.09462
• Monoisotopic Mass: 968.50796568
• SMILES: CC(C)C[C@@H](C(=O)N)NC(=O)CNC(=O)[C@H](Cc1ccccc1)NC(=O)[C@H](CO)NC(=O)[C@H](Cc1ccc(cc1)O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H](CC(=O)O)N
• Canonical SMILES: OC[C@@H](C(=O)N[C@H](C(=O)NCC(=O)N[C@H](C(=O)N)CC(C)C)Cc1ccccc1)NC(=O)[C@H](Cc1ccc(cc1)O)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H](CC(=O)O)N)CCCNC(=N)N)CC(C)C
• InChI: InChI=1S/C45H68N12O12/c1-24(2)17-31(38(47)63)52-36(60)22-51-40(65)33(19-26-9-6-5-7-10-26)55-44(69)35(23-58)57-43(68)34(20-27-12-14-28(59)15-13-27)56-42(67)32(18-25(3)4)54-41(66)30(11-8-16-50-45(48)49)53-39(64)29(46)21-37(61)62/h5-7,9-10,12-15,24-25,29-35,58-59H,8,11,16-23,46H2,1-4H3,(H2,47,63)(H,51,65)(H,52,60)(H,53,64)(H,54,66)(H,55,69)(H,56,67)(H,57,68)(H,61,62)(H4,48,49,50)/t29-,30-,31-,32-,33-,34-,35-/m0/s1
• InChIKey: BYSKWCFHMJZUBY-POFDKVPJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S)-3-amino-3-{[(1S)-4-carbamimidamido-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-[({[(1S)-1-carbamoyl-3-methylbutyl]carbamoyl}methyl)carbamoyl]-2-phenylethyl]carbamoyl}-2-hydroxyethyl]carbamoyl}-2-(4-hydroxyphenyl)ethyl]carbamoyl}-3-methylbutyl]carbamoyl}butyl]carbamoyl}propanoic acid
• IUPAC Traditional name: (3S)-3-amino-3-{[(1S)-4-carbamimidamido-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-[({[(1S)-1-carbamoyl-3-methylbutyl]carbamoyl}methyl)carbamoyl]-2-phenylethyl]carbamoyl}-2-hydroxyethyl]carbamoyl}-2-(4-hydroxyphenyl)ethyl]carbamoyl}-3-methylbutyl]carbamoyl}butyl]carbamoyl}propanoic acid
• Synonyms: Asp-Arg-Leu-Tyr-Ser-Phe-Gly-Leu-NH2; Allatostatin IV

Database IDs

• CAS Number: 123338-13-6
• MDL Number: MFCD00080034
• PubChem SID: 162249666
• PubChem CID: 11853851

CALCULATED PROPERTIES

• Acid pKa: -1.010628
• H Acceptors: 16
• H Donor: 15
• LogD (pH = 5.5): -6.973575
• LogD (pH = 7.4): -5.3001385
• Log P: -4.6191897
• Molar Refractivity: 258.4784 cm^3
• Polarizability: 96.880035 Å^3
• Polar Surface Area: 412.47 Å^2
• Rotatable Bonds: 30
• 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

Product Information

• Purity: ≥97% (HPLC)
• Empirical Formula (Hill Notation): C45H68N12O12

DETAILS

Sigma Aldrich - A9554

Amino Acid Sequence
Asp-Arg-Leu-Tyr-Ser-Phe-Gly-Leu-NH2
Biochem/physiol Actions
Inhibitor of juvenile hormone synthesis in insects.
Allatostatin IV, an octapeptide amine, is a member of the allatoregulatory peptide family found in insects which either inhibit (allatostatins) or stimulate (allatotropins) juvenile hormone (JH) synthesis.
Other Notes
Sequence highly conserved within the six C-terminal amino acids.