(2S)-2-{[(3R)-5-chloro-8-hydroxy-3-methyl-1-oxo-3,4-dihydro-1H-2-benzopyran-7-yl]formamido}-3-phenylpropanoic acid

• ChemBase ID: 128689
• Molecular Formular: C20H18ClNO6
• Molecular Mass: 403.81302
• Monoisotopic Mass: 403.08226498
• SMILES: O=C(O)[C@@H](NC(=O)c1c(O)c2c(c(Cl)c1)C[C@H](OC2=O)C)Cc1ccccc1
• Canonical SMILES: C[C@H]1OC(=O)c2c(C1)c(Cl)cc(c2O)C(=O)N[C@H](C(=O)O)Cc1ccccc1
• InChI: InChI=1S/C20H18ClNO6/c1-10-7-12-14(21)9-13(17(23)16(12)20(27)28-10)18(24)22-15(19(25)26)8-11-5-3-2-4-6-11/h2-6,9-10,15,23H,7-8H2,1H3,(H,22,24)(H,25,26)/t10-,15+/m1/s1
• InChIKey: RWQKHEORZBHNRI-BMIGLBTASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-{[(3R)-5-chloro-8-hydroxy-3-methyl-1-oxo-3,4-dihydro-1H-2-benzopyran-7-yl]formamido}-3-phenylpropanoic acid
• IUPAC Traditional name: ochratoxin A
• Synonyms: Ochratoxin A solution; N-[(3R)-(5-Chloro-8-hydroxy-3-methyl-1-oxo-7-isochromanyl)carbonyl]-L-phenylalanine; Ochratoxin A; (R)-N- [(5-Chloro- 3,4-dihydro- 8-hydroxy- 3-methyl- 1-oxo- 1H-2-benzopyran-7-yl) -carbonyl]- L- phenylalanine; (-)-N- [(5-Chloro- 8-hydroxy- 3-methyl- 1-oxo- 7-isochromanyl) carbonyl]- 3-phenylalanine; Ochratoxin A; Ochratoxin A-BSA conjugate from Aspergillus ochraceus; 赭曲霉素 A 溶液; N-[(3R)-(5-氯-8-羟基-3-甲基-1-氧代-7-苯并二氢异吡喃基)羰基]-L-苯丙氨酸; 赭曲霉素 A

Database IDs

• CAS Number: 303-47-9
• EC Number: 206-143-7; 200-835-2
• MDL Number: MFCD00078079
• Beilstein Number: 8169012; 1301486
• PubChem SID: 24897954; 24860804; 24897972; 162222995; 24870560
• PubChem CID: 442530
• CHEBI ID: 7719
• CHEMBL: 589366
• Chemspider ID: 390954
• KEGG ID: C09955
• Wikipedia Title: Ochratoxin_A

CALCULATED PROPERTIES

• Acid pKa: 3.1733449
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): 2.307228
• LogD (pH = 7.4): 1.0533841
• Log P: 4.611056
• Molar Refractivity: 101.77 cm^3
• Polarizability: 38.76207 Å^3
• Polar Surface Area: 112.93 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: ethanol: soluble
• Apperance: powder
• Melting Point: 169°C
• Flash Point: -11 °C; 12.2 °F; 2 °C; 35.6 °F

Safety Information

• RTECS: AY4375000
• European Hazard Symbols: Flammable (F); Toxic (T); Highly toxic (T+); Harmful (Xn)
• UN Number: 1114; 1648; 2811; 3462
• German water hazard class: 2; 3
• Hazard Class: 3; 6.1
• Packing Group: 2
• Risk Statements: 11-20/21/22-36; 28-40; 45-46-11-36/38-48/23/24/25-65; 45-46-61-26/27/28
• Safety Statements: 16-36/37; 28-36/37-45; 53-16-26-45-62; 53-22-36/37/39-45
• GHS Pictograms: GHS02; GHS06; GHS07; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H225-H302-H312-H319-H332; H225-H304-H315-H319-H341-H350-H372; H300-H310-H330-H350-H360; H300-H351-H413
• GHS Precautionary statements: P201-P210-P281-P301 + P310-P305 + P351 + P338-P308 + P313; P201-P260-P264-P280-P284-P302 + P350; P210-P280-P305 + P351 + P338; P264-P281-P301 + 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; Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter; Faceshields, full-face respirator (US), Gloves, Goggles, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 1114 3/PG 2; UN 1648 3/PG 2; UN 2811 6.1/PG 2; UN 3462 6.1/PG 2
• Storage Temperature: -20°C; 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Concentration: 10 μg/mL in acetonitrile; 50 μg/mL in benzene: acetic acid (99:1)
• Grade: analytical standard; analytical standard, for environmental analysis
• Packaging: ampule of 1 mL
• Impurities: Benzene, free
• Biological Source: from Aspergillus ochraceus; from Petromyces albertensis
• Extent of Labeling: 3-6 mol ochratoxin A per mol BSA
• Quality Level: PREMIUM
• Empirical Formula (Hill Notation): C20H18ClNO6

DETAILS

Sigma Aldrich - O1877

Biochem/physiol Actions
Ochratoxin A is a mycotoxin found in food that is nephrotoxic and carcinogenic in the kidney and induces differentiation in cloned renal cell lines. Increases endoplasmic reticulum ATP-dependent Ca2+ pump activity.

Sigma Aldrich - 34037

General description
Certan Vial