4-[(1S,2S,5S,7R,10R,11S,14R,15S,16R)-5-{[(2R,4S,5S,6R)-5-{[(2S,4S,5S,6R)-5-{[(2S,4S,5S,6R)-4,5-dihydroxy-6-methyloxan-2-yl]oxy}-4-hydroxy-6-methyloxan-2-yl]oxy}-4-hydroxy-6-methyloxan-2-yl]oxy}-11,16-dihydroxy-2,15-dimethyltetracyclo[8.7.0.02,7.011,15]heptadecan-14-yl]-2,5-dihydrofuran-2-one

• ChemBase ID: 104918
• Molecular Formular: C41H64O14
• Molecular Mass: 780.93846
• Monoisotopic Mass: 780.42960673
• SMILES: O=C1OCC(=C1)[C@H]1CC[C@@]2(O)[C@]1(C)[C@H](O)C[C@H]1[C@H]2CC[C@H]2[C@]1(C)CC[C@H](O[C@@H]1O[C@H](C)[C@@H](O[C@@H]3O[C@@H]([C@@H](O[C@@H]4O[C@@H]([C@@H](O)[C@@H](O)C4)C)[C@@H](O)C3)C)[C@@H](O)C1)C2
• Canonical SMILES: O=C1OCC(=C1)[C@H]1CC[C@]2([C@]1(C)[C@H](O)C[C@H]1[C@H]2CC[C@H]2[C@]1(C)CC[C@@H](C2)O[C@H]1C[C@H](O)[C@@H]([C@H](O1)C)O[C@H]1C[C@H](O)[C@@H]([C@H](O1)C)O[C@H]1C[C@H](O)[C@@H]([C@H](O1)C)O)O
• InChI: InChI=1S/C41H64O14/c1-19-36(47)28(42)15-34(50-19)54-38-21(3)52-35(17-30(38)44)55-37-20(2)51-33(16-29(37)43)53-24-8-10-39(4)23(13-24)6-7-26-27(39)14-31(45)40(5)25(9-11-41(26,40)48)22-12-32(46)49-18-22/h12,19-21,23-31,33-38,42-45,47-48H,6-11,13-18H2,1-5H3/t19-,20-,21-,23-,24+,25-,26-,27+,28+,29+,30+,31-,33+,34+,35+,36-,37-,38-,39+,40+,41+/m1/s1
• InChIKey: LTMHDMANZUZIPE-PUGKRICDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-[(1S,2S,5S,7R,10R,11S,14R,15S,16R)-5-{[(2R,4S,5S,6R)-5-{[(2S,4S,5S,6R)-5-{[(2S,4S,5S,6R)-4,5-dihydroxy-6-methyloxan-2-yl]oxy}-4-hydroxy-6-methyloxan-2-yl]oxy}-4-hydroxy-6-methyloxan-2-yl]oxy}-11,16-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan-14-yl]-2,5-dihydrofuran-2-one; 4-[(1S,2S,5S,7R,10R,11S,14R,15S,16R)-5-{[(2R,4S,5S,6R)-5-{[(2S,4S,5S,6R)-5-{[(2S,4S,5S,6R)-4,5-dihydroxy-6-methyloxan-2-yl]oxy}-4-hydroxy-6-methyloxan-2-yl]oxy}-4-hydroxy-6-methyloxan-2-yl]oxy}-11,16-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0?,?.0??,??]heptadecan-14-yl]-2,5-dihydrofuran-2-one
• IUPAC Traditional name: digoxin
• Synonyms: 12β-Hydroxydigitoxin; Digoxin; 12β-Hydroxydigitoxin; DIGOXIN; 异羟基洋地黄毒苷; 地高辛

Database IDs

• CAS Number: 20830-75-5
• EC Number: 244-068-1
• MDL Number: MFCD00003674
• Beilstein Number: 77011
• Merck Index: 143167
• PubChem SID: 24893992; 162092035; 24863090; 24894045
• PubChem CID: 2724385

CALCULATED PROPERTIES

• Acid pKa: 7.151116
• H Acceptors: 13
• H Donor: 6
• LogD (pH = 5.5): 2.3571007
• LogD (pH = 7.4): 1.9245013
• Log P: 2.3666806
• Molar Refractivity: 193.2328 cm^3
• Polarizability: 79.00782 Å^3
• Polar Surface Area: 203.06 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Melting Point: ca 250°C dec.
• Optical Rotation: [α]20/D +11.5±1.5°, c = 10% in pyridine

Safety Information

• RTECS: IH6125000
• European Hazard Symbols: Toxic (T)
• UN Number: 3462; UN2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 2; II
• Risk Statements: 23/25; 25
• Safety Statements: 20-36-45-60; 22-36/37/39-45
• TSCA Listed: 是
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H300; H300 + H330
• GHS Precautionary statements: P260-P264-P284-P301 + P310-P310; P264-P270-P301+P310-P321-P405-P501A
• Personal Protective Equipment: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
• RID/ADR: UN 3462 6.1/PG 2

Pharmacology Properties

• Gene Information: human ... ABCB1(5243), CYP3A4(1576)mouse ... Abcb1a(18671), Abcb1b(18669)rat ... Atp1a1(24211)

Product Information

• Purity: ≥95.0% (HPLC); 96%
• Grade: analytical standard
• Packaging: vial of 250 mg
• Suitability: suitable for 1694 per US EPA
• Ignition Residue: ≤0.1%
• Loss on Drying: ≤1% loss on drying, 110 °C
• Empirical Formula (Hill Notation): C41H64O14
• Classification: Genuine Natural Compounds

DETAILS

MP Biomedicals - 05201683

MP Biomedicals Rare Chemical collection

MP Biomedicals - 02157722

(12β-Hydroxydigitoxin)
Crystalline

Sigma Aldrich - D6770

包装
Supplied in amber screw-cap vials
Biochem/physiol Actions
一种强心苷，P-糖蛋白的底物，上调 Pgp 表达和下调 SXR（固醇类异生物受体）。

Sigma Aldrich - 37100

Biochem/physiol Actions
A cardiac glycoside, substrate for Pgp, upregulates Pgp expression and down regulates SXR (Steroid Xenobiotic Receptor).

Sigma Aldrich - D6003

包装
1, 5 g in glass bottle
100 mg in glass bottle
Biochem/physiol Actions
一种强心苷，P-糖蛋白的底物，上调 Pgp 表达和下调 SXR（固醇类异生物受体）。