Basic information
- CAS
630-60-4- Standard SMILES
CC1OC(OC2CC(O)C3(CO)C4C(O)CC5(C)C(C6=CC(=O)OC6)CCC5(O)C4CCC3(O)C2)C(O)C(O)C1O- InChIKey
LPMXVESGRSUGHW-UHFFFAOYSA-N- Molecular formula
- C29H44O12
- Average molar mass
- 584.7 g/mol
- Monoisotopic mass
- 584.28327683
Overview
3-[1,5,11,14-tetrahydroxy-10-(hydroxymethyl)-13-methyl-3-[(3,4,5-trihydroxy-6-methyl-2-oxanyl)oxy]-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2H-furan-5-one is a cardenolide glycoside.
Names & identifiers
- Preferred name
- 3-((6-Deoxyhexopyranosyl)oxy)-1,5,11,14,19-pentahydroxycard-20(22)-enolide
- IUPAC
- 3-[1,5,11,14-tetrahydroxy-10-(hydroxymethyl)-13-methyl-3-(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2H-furan-5-one
- English name
- G-STROPHANTHIN
- Molecular formula
- C29H44O12
- Molecular weight
- 584.66
Names & synonyms
DTXSID008595153-[(6-Deoxyhexopyranosyl)oxy]-1,5,11,14,19-pentahydroxycard-20(22)-enolide3-((6-deoxyhexopyranosyl)oxy)-1,5,11,14,19-pentahydroxycard-20(22)-enolideRefChem:1066315DTXCID70196883StrodivalMLS002702983NSC25485KombetinCHEMBL1720907CHEBI:91723HMS3267G08
Show more names
OUABAINoubainQUABAINuabainauabaninouabaineNSC 25485ASTROBAINGRATIBAIN
3beta-[(6-Deoxy-alpha-L-talopyranosyl)oxy]-1beta,5,11alpha,14,19-pentahydroxy-5beta-card-20(22)-enolideNCI60_002047SMR001551689Card-20(22)-enolide, 3-[(6-deoxy-.alpha.-L-mannopyranosyl)oxy]-1,5,11,14,19-pentahydroxy-, octahydrate, (1.beta.,3.beta.,5.beta.,11.alpha.)-BRD-A46747628-001-01-9Q27163538Card-20(22)-enolide,5,11,14,19-pentahydroxy-, (1.beta.,3.beta.,5.beta.,11.alpha.)-WLN: L E5 B666TJ A1Q CQ E1 IQ MQ QQ F- DT5OV EHJ& OO- BT6OTJ CQ DQ EQ F1
Database identifiers
Properties
Computed structural properties
- XLogP
- -1.7
- Topological polar surface area
- 207 Ų
- Hydrogen bond donors
- 8
- Hydrogen bond acceptors
- 12
- Rotatable bonds
- 4
- Heavy atoms
- 41
- Formal charge
- 0
- Complexity
- 1,080
Experimental & physicochemical properties
DrugsPharmaceuticals
Physicochemical properties
- Melting point
- 200 °C · 200°C
- Boiling point
- 561.69 °C · 561.69°C (rough estimate)
- Density
- 1.1941 · 1.1941 (rough estimate)
- refractive index
- -32 ° · -32 ° (C=1, H2O)
- storage temp.
- -20 °C · Desiccate at -20°C
- solubility
- 2 O: · H2O: 10 mg/mL cold
- form
- powder
- pka
- 13.04 · 13.04±0.70(Predicted)
- color
- white
- Water Solubility
- 13 g/L · 13g/L(25 ºC)
- Merck
- 6901 · 6901
- Stability
- Hygroscopic
- Major Application
- food and beverages
- InChIKey
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- F
- 8
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- RN3850000
- ridadr
- UN 1544 6.1/PG 1
- Toxicity
- LD50 oral in guinea pig: 8280ug/kg
- risk_code
- 23/25-33
- Signal word
- Danger
- Symbol(GHS)
- GHS06,GHS08
- hazard_code
- T
- safety_code
- 45
- Storage Class
- 6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials
- Hazard statements
- H301-H331-H373
- Hazard Classifications
- Acute Tox. 1 OralAcute Tox. 3 InhalationSTOT RE 2
- Precautionary statements
- P264-P270-P261-P271-P260-P301+P310-P330-P304+P340-P311-P314-P405-P403+P233-P501
- Hazardous Substances Data
- 630-60-4(Hazardous Substances Data)
Chemistry & industry
Applications
DescriptionOne of several cardiac glycosides that have been used clinically as cardiotonic agents and diuretics. Ouabain is obtained from the seeds of Strophanthus gratus, Acokanthera ouabaio, and related species. It was formerly prescribed under the name strophanthuis as the purified seed extract.
UsesOuabain is a Na+/K+-ATPase inhibitor hormone, which negatively modulates allergic airway inflammation induced by ovalbumin (OVA).
General DescriptionOdorless, white crystals or crystalline powder as an octahydrate. Used to produce rapid digitalization in acute congestive heart failure. Also recommended in treatment of atrial or nodal paroxysmal tachycardia and atrial flutter.
Upstream & downstream products
Downstream products
Suppliers31 total
北京华美互利生物化工010-56205725 · [email protected]
南京世洲生物科技有限公司025-85560043 15850508050 · [email protected]
河南闰霖化工有限公司+86-18738066252; +86-18738066252 · [email protected]
LGM Pharma1-(800)-881-8210 · [email protected]
武汉易泰科技有限公司上海分公司18930552037 · [email protected]
上海晶抗生物工程有限公司021-54721350 13524668266 · [email protected]
InvivoChem中国13549236410 · [email protected]
Related reactions
0 records
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Compound notes
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