2-[(9R,10R)-10-hydroxy-3,7,9,11-tetramethyltrideca-2,5,7,11-tetraen-1-yl]-5,6-dimethoxy-3-methylpyridin-4-ol

• ChemBase ID: 156069
• Molecular Formular: C25H37NO4
• Molecular Mass: 415.56558
• Monoisotopic Mass: 415.27225867
• SMILES: C/C=C(\C)/[C@@H]([C@H](C)/C=C(\C)/C=C/C/C(=C/Cc1c(c(c(c(n1)OC)OC)O)C)/C)O
• Canonical SMILES: C/C=C(/[C@@H]([C@@H](/C=C(/C=C/C/C(=C/Cc1nc(OC)c(c(c1C)O)OC)/C)\C)C)O)\C
• InChI: InChI=1S/C25H37NO4/c1-9-18(4)22(27)19(5)15-17(3)12-10-11-16(2)13-14-21-20(6)23(28)24(29-7)25(26-21)30-8/h9-10,12-13,15,19,22,27H,11,14H2,1-8H3,(H,26,28)/t19-,22+/m1/s1
• InChIKey: BBLGCDSLCDDALX-KNQAVFIVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(9R,10R)-10-hydroxy-3,7,9,11-tetramethyltrideca-2,5,7,11-tetraen-1-yl]-5,6-dimethoxy-3-methylpyridin-4-ol
• IUPAC Traditional name: 2-[(9R,10R)-10-hydroxy-3,7,9,11-tetramethyltrideca-2,5,7,11-tetraen-1-yl]-5,6-dimethoxy-3-methylpyridin-4-ol
• Synonyms: 2,6,9,11-Tridecatetraen-4-ol,13-(4-hydrox-5,6-dimethoxy-3-methyl-2-pyridyl)-3,5,7,11-tetramethyl-(all-E)-(4R,5R); 4-Pyridinol,2-(10-hydroxy-3,7,9,11-tetramethyl-2,5,7,11-tridecatetraenyl)-5,6-dimethoxy- [R-[R*,R*-(all-E)]]-3-methyl-; Piericidin A1; SN 198E; Shaoguamycin B; Piericidin A from microbial source; Shaoguanmycin B; Piericidin A from Streptomyces mobaraensis

Database IDs

• CAS Number: 2738-64-9
• MDL Number: MFCD01677956
• PubChem SID: 162250207; 24898532
• PubChem CID: 6437838

CALCULATED PROPERTIES

• Acid pKa: 10.905995
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 5.383146
• LogD (pH = 7.4): 5.38313
• Log P: 5.3832645
• Molar Refractivity: 127.292 cm^3
• Polarizability: 47.806007 Å^3
• Polar Surface Area: 71.81 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Apperance: DMSO solution; green-yellow liquid
• Flash Point: 185 °F; 85 °C

Safety Information

• RTECS: YD4588000
• European Hazard Symbols: Highly toxic (T+); Harmful (Xn)
• UN Number: 3382
• German water hazard class: 1; 3
• Hazard Class: 6.1
• Packing Group: 1
• Risk Statements: 20/21/22; 26/27/28
• Safety Statements: 28-36/37-45; 36/37
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H300-H310-H330
• GHS Precautionary statements: P260-P264-P280-P284-P301 + P310-P302 + P350
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 3382 6.1/PG 1
• Storage Temperature: 2-8°C

Product Information

• Purity: >95% (HPLC); ≥90.0% (HPLC)
• Loss on Drying: <10% loss on drying
• Shipped in: wet ice
• Empirical Formula (Hill Notation): C25H37NO4

DETAILS

Sigma Aldrich - P4368

Biochem/physiol Actions
Piericidin A is a potent inhibitor of the mitochondrial and bacterial type I NADH-ubiquinone oxireductase (Complex I). It is considered to bind to the ubiquinone binding sites of the enzyme. Peiricidin A inactivation of complex I completely prevents NADH-induced proton translocation in the NADH-endogenous ubiquinone reductase reaction.

Sigma Aldrich - 96861

Other Notes
Neurotoxin for the respiratory chain1