(2S)-2-{2-[(1S,2S)-1-{[(1R)-1-{[(1S)-1-{[(4S,7S)-7-{2-[(2S)-2-amino-4-methylpentanamido]acetamido}-2,9-dimethyl-5,6-dioxodecan-4-yl]carbamoyl}-2-methylpropyl]carbamoyl}ethyl]carbamoyl}-2-methylbutyl]hydrazin-1-yl}-3-methylbutanoic acid; trifluoroacetic acid

• ChemBase ID: 154637
• Molecular Formular: C41H73F3N8O11
• Molecular Mass: 911.0605296
• Monoisotopic Mass: 910.53508986
• SMILES: CC[C@H](C)[C@@H](C(=O)N[C@H](C)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC(C)C)C(=O)C(=O)[C@H](CC(C)C)NC(=O)CNC(=O)[C@H](CC(C)C)N)NN[C@@H](C(C)C)C(=O)O.C(=O)(C(F)(F)F)O
• Canonical SMILES: OC(=O)C(F)(F)F.CC[C@@H]([C@@H](C(=O)N[C@@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)C(=O)[C@@H](NC(=O)CNC(=O)[C@H](CC(C)C)N)CC(C)C)CC(C)C)C(C)C)C)NN[C@H](C(=O)O)C(C)C)C
• InChI: InChI=1S/C39H72N8O9.C2HF3O2/c1-14-24(12)32(47-46-31(23(10)11)39(55)56)38(54)42-25(13)35(51)45-30(22(8)9)37(53)44-28(17-21(6)7)34(50)33(49)27(16-20(4)5)43-29(48)18-41-36(52)26(40)15-19(2)3;3-2(4,5)1(6)7/h19-28,30-32,46-47H,14-18,40H2,1-13H3,(H,41,52)(H,42,54)(H,43,48)(H,44,53)(H,45,51)(H,55,56);(H,6,7)/t24-,25+,26-,27-,28-,30-,31-,32-;/m0./s1
• InChIKey: YOPDKLRUJCDCMP-AFAMYAHFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-{2-[(1S,2S)-1-{[(1R)-1-{[(1S)-1-{[(4S,7S)-7-{2-[(2S)-2-amino-4-methylpentanamido]acetamido}-2,9-dimethyl-5,6-dioxodecan-4-yl]carbamoyl}-2-methylpropyl]carbamoyl}ethyl]carbamoyl}-2-methylbutyl]hydrazin-1-yl}-3-methylbutanoic acid; trifluoroacetic acid
• IUPAC Traditional name: (2S)-2-{2-[(1S,2S)-1-{[(1R)-1-{[(1S)-1-{[(4S,7S)-7-{2-[(2S)-2-amino-4-methylpentanamido]acetamido}-2,9-dimethyl-5,6-dioxodecan-4-yl]carbamoyl}-2-methylpropyl]carbamoyl}ethyl]carbamoyl}-2-methylbutyl]hydrazin-1-yl}-3-methylbutanoic acid; trifluoroacetic acid
• Synonyms: LGLLVAIV trifluoroacetate salt; Leu-Gly-Leu-Leu-Val-Ala-Ile-Val trifluoroacetate salt; γ6 TM1a trifluoroacetate salt

Database IDs

• CAS Number: 1163243-88-6
• MDL Number: MFCD17215947
• PubChem SID: 162248775
• PubChem CID: 71311921

CALCULATED PROPERTIES

• LogD (pH = 5.5): 0.90312046
• LogD (pH = 7.4): 0.9954763
• Log P: 1.0753012
• Molar Refractivity: 231.7326 cm^3
• Polarizability: 83.73928 Å^3
• Polar Surface Area: 267.02 Å^2
• Rotatable Bonds: 28
• Lipinski's Rule of Five: false
• Acid pKa: 5.393284
• H Acceptors: 12
• H Donor: 9

PROPERTIES

Physical Property

• Solubility: H2O: >1 mg/mL
• Apperance: lyophilized powder

Safety Information

• German water hazard class: 3
• Storage Temperature: -20°C

Product Information

• Purity: ≥95% (HPLC)
• Empirical Formula (Hill Notation): C39H72N8O9 · xC2HF3O2

DETAILS

Sigma Aldrich - T2955

Amino Acid Sequence
Leu-Gly-Leu-Leu-Val-Ala-Ile-Val
Biochem/physiol Actions
The calcium channel γ family is a subgroup of the tetraspanin proteins. There are the eight γ subunits that have been identified to date. Among these γ1 subunit acts as an endogenous antagonist of the skeletal HVA calcium current, and γ6 inhibits the low voltage-activated (LVA) Cav3.1 calcium current. A GxxxA motif in the first transmembrane domain (TM1) of γ6 was identified as critical for inhibiting the Cav3.1 current. γ6 TM1a is an octapeptide contains residues 41 through 48 of the native γ6 protein. The peptide inhibits the Cav3.1 calcium current in a dose-dependent manner. The reduction of channel current is mostly due to the inhibition of both resting and inactivated channels relatively independent of membrane potential. Thus γ6 TM1might function as a pore blocker. Also γ6 TM1a peptide inhibits Cav1.2 current with reduced efficacy. The γ6 TM1a peptide has the potential of being further developed as a novel therapeutic agent targeting Cav3.1 and possibly Cav1.2 calcium current.