(1S,2R,5S,6S,8R,9S,10R,12S,15R,16S,25R,27S,28R)-21-chloro-15,16,33,33-tetramethyl-24-methylidene-10-(prop-1-en-2-yl)-7,11,32-trioxa-18-azadecacyclo[25.4.2.02,16.05,15.06,8.06,12.017,31.019,30.022,29.025,28]tritriaconta-17(31),19(30),20,22(29)-tetraene-5,9,28-triol

• ChemBase ID: 105755
• Molecular Formular: C37H44ClNO6
• Molecular Mass: 634.20136
• Monoisotopic Mass: 633.28571581
• SMILES: C=C(C)[C@@H]1[C@@H]([C@@H]2[C@]3([C@H](CC[C@]4(C)[C@]5(C)[C@@H](CC[C@@]34O)[C@H]3c4c6c(cc(c7CC(=C)[C@H]8C[C@H](C(C)(C)O3)[C@]8(c67)O)Cl)[nH]c54)O1)O2)O
• Canonical SMILES: CC(=C)[C@H]1O[C@H]2CC[C@]3([C@@]([C@]42[C@@H]([C@H]1O)O4)(O)CC[C@@H]1[C@]3(C)c2[nH]c3c4c2[C@H]1OC(C)(C)[C@@H]1[C@]2(c4c(c(c3)Cl)CC(=C)[C@H]2C1)O)C
• InChI: InChI=1S/C37H44ClNO6/c1-15(2)28-27(40)31-37(45-31)23(43-28)9-10-33(6)34(7)18(8-11-35(33,37)41)29-25-24-21(39-30(25)34)14-20(38)17-12-16(3)19-13-22(32(4,5)44-29)36(19,42)26(17)24/h14,18-19,22-23,27-29,31,39-42H,1,3,8-13H2,2,4-7H3/t18-,19+,22+,23-,27-,28+,29-,31+,33+,34+,35-,36+,37-/m0/s1
• InChIKey: JDUWHZOLEDOQSR-JKPSMKLGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,5S,6S,8R,9S,10R,12S,15R,16S,25R,27S,28R)-21-chloro-15,16,33,33-tetramethyl-24-methylidene-10-(prop-1-en-2-yl)-7,11,32-trioxa-18-azadecacyclo[25.4.2.0^2,^1^6.0^5,^1^5.0^6,^8.0^6,^1^2.0^1^7,^3^1.0^1^9,^3^0.0^2^2,^2^9.0^2^5,^2^8]tritriaconta-17(31),19(30),20,22(29)-tetraene-5,9,28-triol; (1S,2R,5S,6S,8R,9S,10R,12S,15R,16S,25R,27S,28R)-21-chloro-15,16,33,33-tetramethyl-24-methylidene-10-(prop-1-en-2-yl)-7,11,32-trioxa-18-azadecacyclo[25.4.2.0?,??.0?,??.0?,?.0?,??.0??,??.0??,??.0??,??.0??,??]tritriaconta-17(31),19,21,29-tetraene-5,9,28-triol
• IUPAC Traditional name: (1S,2R,5S,6S,8R,9S,10R,12S,15R,16S,25R,27S,28R)-21-chloro-15,16,33,33-tetramethyl-24-methylidene-10-(prop-1-en-2-yl)-7,11,32-trioxa-18-azadecacyclo[25.4.2.0^2,^1^6.0^5,^1^5.0^6,^8.0^6,^1^2.0^1^7,^3^1.0^1^9,^3^0.0^2^2,^2^9.0^2^5,^2^8]tritriaconta-17(31),19(30),20,22(29)-tetraene-5,9,28-triol; (1S,2R,5S,6S,8R,9S,10R,12S,15R,16S,25R,27S,28R)-21-chloro-15,16,33,33-tetramethyl-24-methylidene-10-(prop-1-en-2-yl)-7,11,32-trioxa-18-azadecacyclo[25.4.2.0?,??.0?,??.0?,?.0?,??.0??,??.0??,??.0??,??.0??,??]tritriaconta-17(31),19,21,29-tetraene-5,9,28-triol
• Synonyms: Penitrem A; Tremortin A; PENITREM A

Database IDs

• CAS Number: 12627-35-9
• MDL Number: MFCD00083465
• PubChem SID: 24898385; 162093116
• PubChem CID: 6610243

CALCULATED PROPERTIES

• Acid pKa: 12.726915
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): 4.3208504
• LogD (pH = 7.4): 4.3208485
• Log P: 4.3208504
• Molar Refractivity: 168.9462 cm^3
• Polarizability: 68.34126 Å^3
• Polar Surface Area: 107.47 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• Storage Condition: -20°C
• RTECS: RY7535000
• European Hazard Symbols: Highly toxic (T+)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 2
• Risk Statements: 26/27/28
• Safety Statements: 36/37/39-45
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H300-H310-H330
• GHS Precautionary statements: P260-P264-P280-P284-P302 + P350-P310
• Personal Protective Equipment: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• RID/ADR: UN 2811 6.1/PG 2
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥95% (HPLC and TLC)

DETAILS

MP Biomedicals - 02193945

From Penicillium palitans
A tremorgenic fungal mycotoxin which increases GABA release and aspartate from cerebrocortical synaptosomes and acetylcholine in rat neuromuscular junction.

Sigma Aldrich - P3053

Biochem/physiol Actions
Tremorgenic fungal toxin; blocks high-conductance Ca2+-activated K+ channels.
Other Notes
Originally isolated from Penicillium palitans

REFERENCES

• Wilson, et al., Brain Res. , 40 : 540 (1972).