Cinobufotalin
Basic information
- CAS
1108-68-5- Standard SMILES
CC(=O)O[C@H]1[C@H]2O[C@]23[C@@H]2CC[C@]4(O)C[C@@H](O)CC[C@]4(C)[C@H]2CC[C@]3(C)[C@H]1c1ccc(=O)oc1- InChIKey
KBKUJJFDSHBPPA-ZNCGZLKOSA-N- Molecular formula
- C26H34O7
- Average molar mass
- 458.5 g/mol
- Monoisotopic mass
- 458.23045342
Overview
KBKUJJFDSHBPPA-ZNCGZLKOSA-N has been reported in Bufo bufo and Bufo with data available.
Names & identifiers
- Preferred name
- Cinobufotalin
- IUPAC
- [(1R,2S,4R,5R,6R,7R,10S,11R,14S,16S)-14,16-dihydroxy-7,11-dimethyl-6-(6-oxopyran-3-yl)-3-oxapentacyclo[8.8.0.02,4.02,7.011,16]octadecan-5-yl] acetate
- English name
- Cinobufotalin
- Molecular formula
- C26H34O7
- Molecular weight
- 458.54
Names & synonyms
Cinobufotalin1108-68-5CINOBUFOTLINCinobufagin metabolite m-2NSC-90326L0QBZ37386DTXSID1010265815-beta-Bufa-20,22-dienolide, 14,15-beta-epoxy-3-beta,5,16-beta-trihydroxy-, 16-acetateBufa-20,22-dienolide, 16-(acetyloxy)-14,15-epoxy-3,5-dihydroxy-, (3beta,5beta,15beta,16beta)-3beta,5beta-dihydroxy-16beta-acetoxy-14beta,15beta-epoxy-bufa-20,22-dienolide[(1R,2S,4R,5R,6R,7R,10S,11R,14S,16S)-14,16-dihydroxy-7,11-dimethyl-6-(6-oxopyran-3-yl)-3-oxapentacyclo[8.8.0.02,4.02,7.011,16]octadecan-5-yl] acetate((1R,2S,4R,5R,6R,7R,10S,11R,14S,16S)-14,16-dihydroxy-7,11-dimethyl-6-(6-oxopyran-3-yl)-3-oxapentacyclo(8.8.0.02,4.02,7.011,16)octadecan-5-yl) acetate
Show more names
Nsc90326ChinbufotalinCINOBUFOTALIN(RG)Cinobufotalin std.Cinobufotalin StandardCinobufotalin USP/EP/BPcinobufotalin venom toad5beta-Hydroxycinobufagin
RefChem:12628814,15b-Epoxy-3b,5a,16b-trihydroxy-5b,20(22)-bufadienolide 16-acetateDTXCID3015107385b,20(22)-Bufadienolide-14,15b-epoxy-3b,5a,16b-triol 16-Acetate634-568-1NSC 90326Cinobufotalin?UNII-L0QBZ37386
Properties
Computed structural properties
- XLogP
- 2.1
- Topological polar surface area
- 106 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 7
- Rotatable bonds
- 3
- Heavy atoms
- 33
- Formal charge
- 0
- Complexity
- 972
Experimental & physicochemical properties
LipidsLipids -> Sterol Lipids [ST] -> Sterols [ST01] -> Bufanolides and derivatives [ST0113]
Physicochemical properties
- Melting point
- 259 · 259-262°
- alpha
- 20 · D20 +11°
- Boiling point
- 627.3 · 627.3±55.0 °C(Predicted)
- Density
- 1.34 · 1.34±0.1 g/cm3(Predicted)
- storage temp.
- 2 · 2-8°C
- solubility
- 10 mg/ml; · DMF: 10 mg/ml; DMF:PBS (pH 7.2) (1:1): 0.5 mg/ml; DMSO: 5 mg/ml; Ethanol: 5 mg/ml
- pka
- 14.67 · 14.67±0.70(Predicted)
- form
- White to off-white solid.
- color
- White to off-white
- InChIKey
- KBKUJJFDSHBPPA-XYCOMLSLNA-N
- SMILES
- [C@]123O[C@@H]1[C@@H]([C@H](C1=COC(=O)C=C1)[C@@]2(C)CC[C@]1([H])[C@@]2(C)CC[C@H](O)C[C@@]2(O)CC[C@@]31[H])OC(=O)C |&1:0,2,3,4,12,16,18,22,25,29,r|
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Danger
H300 (100%): Fatal if swallowed [Danger Acute toxicity, oral]
P260, P262, P264, P270, P271, P280, P284, P301+P316, P302+P352, P304+P340, P316, P320, P321, P330, P361+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 39 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Hazard Classes and CategoriesAcute Tox. 2 (100%)
Safety data
- wgk
- 3
- rtecs
- EI2991000
- ridadr
- UN 2811 6.1/PG 1
- Toxicity
- cat,LD50,intravenous,200ug/kg (0.2mg/kg),"Die Herzwirksamen Glykoside," Baumgarten, G., and W. Forster, Leipzig, Ger. Dem. Rep., VEB Georg Thieme, 1963Vol. -, Pg. 189, 1963.
- risk_code
- 26/27/28
- Signal word
- Danger
- Symbol(GHS)
- GHS06
- hazard_code
- T+
- safety_code
- 22-36/37/39-45
- hazard_class
- 6.1(a)
- packing_group
- II
- Hazard statements
- H300+H310+H330
- Precautionary statements
- P260-P262-P264-P280-P302+P352+P310-P304+P340+P310
Chemistry & industry
Applications
DescriptionCinobufacin is an indole-type total alkaloid extracted from the dried toad skin of Chinese toad, which has the functions of clearing away heat and detoxifying, reducing swelling and pain, promoting blood circulation and removing blood stasis, softening and dispelling knots.
UsesCinobufotalin is a cardiotonic steroids or bufadienolides, is extracted from the skin secretions of the giant toads. Cinobufotalin has been used as a cardiotonic, diuretic and a hemostatic agent, Cinobufotalin is also a potential anti-lung cancer agent[1].
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Compound notes
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