(1R,4R,5R,6R,16R)-5,6-dihydroxy-4,5,6-trimethyl-2,8-dioxa-13-azatricyclo[8.5.1.013,16]hexadec-10-ene-3,7-dione

• ChemBase ID: 133056
• Molecular Formular: C16H23NO6
• Molecular Mass: 325.35692
• Monoisotopic Mass: 325.15253746
• SMILES: C[C@H]1C(=O)O[C@@H]2CCN3[C@@H]2C(=CC3)COC(=O)[C@]([C@]1(C)O)(C)O
• Canonical SMILES: O=C1O[C@@H]2CCN3[C@@H]2C(=CC3)COC(=O)[C@]([C@]([C@H]1C)(C)O)(C)O
• InChI: InChI=1S/C16H23NO6/c1-9-13(18)23-11-5-7-17-6-4-10(12(11)17)8-22-14(19)16(3,21)15(9,2)20/h4,9,11-12,20-21H,5-8H2,1-3H3/t9-,11+,12+,15+,16-/m0/s1
• InChIKey: QVCMHGGNRFRMAD-XFGHUUIASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,4R,5R,6R,16R)-5,6-dihydroxy-4,5,6-trimethyl-2,8-dioxa-13-azatricyclo[8.5.1.0^1^3,^1^6]hexadec-10-ene-3,7-dione
• IUPAC Traditional name: (1R,4R,5R,6R,16R)-5,6-dihydroxy-4,5,6-trimethyl-2,8-dioxa-13-azatricyclo[8.5.1.0^1^3,^1^6]hexadec-10-ene-3,7-dione; monocrotaline
• Synonyms: (3R,4R,5R,13aR,13bR)-4,5,8,10,12,13,13a,13b-Octahydro-4,5-dihydroxy-3,4,5-trimethyl-2H-[1,6]dioxacycloundecino[2,3,4-gh]pyrrolizine-2,6(3H)-dione; (13α,14α)-14,19-dihydro-12,13-dihydroxy-20-Norcrotalanan-11,15-dione; (-)-Monocrotaline; Monocrotalin; NSC 28693; Monocrotaline; Monocrotaline; Crotaline; 野百合碱; 单响尾蛇毒蛋白

Database IDs

• CAS Number: 315-22-0
• MDL Number: MFCD00084656
• Beilstein Number: 48732
• PubChem SID: 24892326; 162227333
• PubChem CID: 9415

CALCULATED PROPERTIES

• Acid pKa: 11.494293
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): -2.866132
• LogD (pH = 7.4): -1.0958016
• Log P: -0.33238804
• Molar Refractivity: 80.7028 cm^3
• Polarizability: 32.17088 Å^3
• Polar Surface Area: 96.3 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform
• Apperance: White Solid
• Melting Point: >140°C (dec.); 204 °C (dec.)(lit.)

Safety Information

• Storage Condition: -20°C Freezer
• RTECS: QB3140000
• European Hazard Symbols: Toxic (T)
• UN Number: 1544
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3
• Risk Statements: 25-40
• Safety Statements: 36/37/39-45
• GHS Pictograms: GHS06; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H301-H351
• GHS Precautionary statements: 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
• RID/ADR: UN 1544 6.1/PG 3
• Storage Temperature: 2-8°C

Pharmacology Properties

• Mechanism of Action: Causes denudation of the hepatic sinusoidal endothelium and increased serum hyaluronic acid levels, along with superior transplanted cell engraftment

Product Information

• Biological Source: Alkaloid from Crotalaria retusa, Crotalaria spectabilis, Crotalaria aegyptiaca, Crotalaria burhia and Lindelofia spectabilis (Leguminosae, Boraginaceae)
• Application(s): Antineoplastic activity esp. vs. adenocarcinoma; Hepatotoxin; Male insect sterilant

DETAILS

Sigma Aldrich - C2401

包装
1 g in glass bottle
500 mg in glass bottle

Toronto Research Chemicals - M526000

A toxic pyrrolizidine alkaloid isolated from Crotalaria spp. It is used for inducing pulmonary diseases in rats.

REFERENCES

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