Cantharidin

Details

• Internal ID: c63a3666-ceb2-4547-b7ea-4e8657babfc6
• Taxonomy: Organoheterocyclic compounds > Furofurans
• IUPAC Name: (1S,2R,6S,7R)-2,6-dimethyl-4,10-dioxatricyclo[5.2.1.02,6]decane-3,5-dione
• InChI: InChI=1S/C10H12O4/c1-9-5-3-4-6(13-5)10(9,2)8(12)14-7(9)11/h5-6H,3-4H2,1-2H3/t5-,6+,9+,10-
• InChI Key: DHZBEENLJMYSHQ-XCVPVQRUSA-N
• Popularity: 2,503 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₀H₁₂O₄
• Molecular Weight: 196.20 g/mol
• Exact Mass: 196.07355886 g/mol
• Topological Polar Surface Area (TPSA): 52.60 Ų
• XlogP: 0.60
• Atomic LogP (AlogP): 0.64
• H-Bond Acceptor: 4
• H-Bond Donor: 0
• Rotatable Bonds: 0

Synonyms

• Cantharone
• 56-25-7
• CANTHARIDINE
• Cantharides camphor
• Kantaridin
• Kantharidin
• Cantaridina
• Cantharidinum
• (3ar,4s,7r,7as)-3a,7a-dimethylhexahydro-4,7-epoxy-2-benzofuran-1,3-dione
• 1,2-Dimethyl-3,6-epoxyperhydrophthalic anhydride
• exo-1,2-cis-Dimethyl-3,6-epoxyhexahydrophthalic anhydride
• IGL471WQ8P
• NSC-61805
• YCANTH
• 2,3-Dimethyl-7-oxabicyclo(2.2.1)heptane-2,3-dicarboxylic anhydride
• CHEBI:64213
• 7-Oxabicyclo(2.2.1)heptane-2,3-dicarboxylic anhydride, 2,3-dimethyl-
• Hexahydro-3aalpha,7aalpha-dimethyl-4beta,7beta-epoxyisobenzofuran-1,3-dione
• (1S,2R,6S,7R)-2,6-dimethyl-4,10-dioxatricyclo(5.2.1.02,6)decane-3,5-dione
• (1S,2R,6S,7R)-2,6-dimethyl-4,10-dioxatricyclo[5.2.1.02,6]decane-3,5-dione
• RefChem:123249
• CANTHARIDIN 0.7%
• DTXCID601764425
• 200-263-3
• 4,7-Epoxyisobenzofuran-1,3-dione, hexahydro-3a,7a-dimethyl-, (3aalpha,4beta,7beta,7aalpha)-
• DTXSID7041752
• Cantharidin [USAN]
• NSC61805
• MFCD00134968
• CHEMBL48449
• 4,7-Epoxyisobenzofuran-1,3-dione, hexahydro-3a,7a-dimethyl-, (3aR,4S,7R,7aS)-rel-
• CAN [Alkaloid]
• NSC 61805
• Kantharidin [German]
• Caswell No. 157
• CCRIS 635
• HSDB 2181
• AI3-04021
• EINECS 200-263-3
• UNII-IGL471WQ8P
• EPA Pesticide Chemical Code 013101
• BRN 0085302
• CAS-56-25-7
• NCGC00016247-01
• Ycanth (TN)
• CANTHARIDIN [MI]
• Prestwick3_000885
• CANTHARIDIN [INN]
• Cantharidin (JAN/USAN)
• CANTHARIDIN [IARC]
• (1R,2S,3R,6S)-1,2-Dimethyl-3,6-epoxycyclohexane-1,2-dicarboxylic anhydride
• 2,3-dicarboxylic anhydride
• CANTHARIDIN [VANDF]
• CANTHARIDINE [HSDB]
• NCIMech_000301
• CANTHARIDIN [MART.]
• CANTHARIDINUM [HPUS]
• BSPBio_000670
• CANTHARIDIN [WHO-DD]
• 4,7-Epoxyisobenzofuran-1,3-dione, hexahydro-3a,7a-dimethyl-, (3a-alpha,4-beta,7-beta,7a-alpha)
• 5-19-05-00051 (Beilstein Handbook Reference)
• orb421994
• SCHEMBL152262
• BPBio1_000738
• orb2893612
• SCHEMBL31628232
• cid_6708701
• GTPL13081
• HMS2097B12
• HMS3412J13
• HMS3676J13
• 1,6-epoxyperhydrophthalic anhydride
• 4,7-Epoxyisobenzofuran-1,3-dione, hexahydro-3a,7a-dimethyl-, (3a.alpha.,4.beta.,7.beta.,7a.alpha.)-
• HY-N0209
• MSK40063
• BDBM50090505
• CCG-35382
• CCG-36082
• EBC-26179
• WHO 11470
• AKOS015895930
• AC-7967
• CS-4979
• DB12328
• FC29633
• (1R,2S,6R,7S)-2,6-dimethyl-4,10-dioxatricyclo[5.2.1.02,6]decane-3,5-dione
• 4,3-dione, hexahydro-3a,7a-dimethyl-
• exo-1,6-epoxyhexahydrophthalic anhydride
• NCGC00025212-02
• NCGC00025212-03
• NCGC00025212-04
• NCGC00025212-05
• NCGC00025212-31
• AS-18735
• NCI60_005413
• VP-102 drug/device delivering cantharidin
• WLN: T C555 A AO DVOVTJ C1 G1
• AB00513946
• Hexahydro-3a,7-epoxyisobenzofuran-1,3-dione
• D11745
• 7-Oxabicyclo[2.2.1]heptane-2, 2,3-dimethyl-
• 134C968
• EN300-24727854
• Q410884
• SR-01000597585
• SR-01000597585-1
• BRD-K80684056-001-01-0
• BRD-K80684056-001-04-4
• BRD-K80684056-001-05-1
• BRD-K80684056-001-06-9
• Ycanth (0.7% solution, single-use topical applicator)
• Hexahydro-3a,7a-dimethyl-4,7-epoxyisobenzo-furan-1,3-dione
• (3aR,4S,7R,7aS)-3a,7a-dimethylhexahydro-4,7-epoxyisobenzofuran-1,3-dione
• (1R,2S,6R,7S)-2,6-Dimethyl-4,10-dioxa-tricyclo[5.2.1.0*2,6*]decane-3,5-dione
• (1R,2S,6R,7S)-2,6-dimethyl-4,10-dioxatricyclo[5.2.1.0,2,6]decane-3,5-dione
• (1R,5S,6R,9S)-rel-1,5-Dimethyl-3,10-dioxatricyclo[3.2.1.01,5]decane-2,4-dione
• (1R,7S)-2,6-Dimethyl-4,10-dioxa-tricyclo[5.2.1.0*2,6*]decane-3,5-dione
• (1S,2R,6S,7R)-2,6-Dimethyl-4,10-dioxa-tricyclo[5.2.1.0*2,6*]decane-3,5-dione
• (1S,3S,4R,7R)-2,6-dimethyl-4,10-dioxa-tricyclo[5.2.1.0-2,6]decane-3,5-dione
• 4,3-dione, hexahydro-3a,7a-dimethyl-, (3a.alpha.,4.beta.,7.beta.,7a.alpha.)-
• HEXAHYDRO-3A.ALPHA.,7A.ALPHA.-DIMETHYL-4.BETA.,7.BETA.-EPOXYISOBENZOFURAN-1,3-DIONE
• Cantharidine; 3a,7a-Dimethylhexahydro-4,7-epoxyisobenzofuran-1,3-dione; 7a-Dimethylhexahydro-3a,4,7-epoxyisobenzofuran

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9802	98.02%
Caco-2	+	0.7334	73.34%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	+	0.7143	71.43%
Subcellular localzation	Mitochondria	0.6456	64.56%
OATP2B1 inhibitior	-	0.8530	85.30%
OATP1B1 inhibitior	+	0.9604	96.04%
OATP1B3 inhibitior	+	0.9676	96.76%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.9753	97.53%
P-glycoprotein inhibitior	-	0.9387	93.87%
P-glycoprotein substrate	-	0.9860	98.60%
CYP3A4 substrate	-	0.5732	57.32%
CYP2C9 substrate	-	0.7982	79.82%
CYP2D6 substrate	-	0.8010	80.10%
CYP3A4 inhibition	-	0.8309	83.09%
CYP2C9 inhibition	-	0.9606	96.06%
CYP2C19 inhibition	-	0.9592	95.92%
CYP2D6 inhibition	-	0.9660	96.60%
CYP1A2 inhibition	-	0.9046	90.46%
CYP2C8 inhibition	-	0.9922	99.22%
CYP inhibitory promiscuity	-	0.9805	98.05%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.5921	59.21%
Eye corrosion	-	0.9371	93.71%
Eye irritation	-	0.5489	54.89%
Skin irritation	+	0.5000	50.00%
Skin corrosion	+	0.9671	96.71%
Ames mutagenesis	-	0.6900	69.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7233	72.33%
Micronuclear	-	0.7900	79.00%
Hepatotoxicity	+	0.8607	86.07%
skin sensitisation	-	0.8100	81.00%
Respiratory toxicity	+	0.5333	53.33%
Reproductive toxicity	+	0.5111	51.11%
Mitochondrial toxicity	+	0.6875	68.75%
Nephrotoxicity	+	0.8445	84.45%
Acute Oral Toxicity (c)	III	0.6701	67.01%
Estrogen receptor binding	+	0.8636	86.36%
Androgen receptor binding	-	0.6094	60.94%
Thyroid receptor binding	-	0.6866	68.66%
Glucocorticoid receptor binding	-	0.8429	84.29%
Aromatase binding	-	0.7369	73.69%
PPAR gamma	-	0.5987	59.87%
Honey bee toxicity	-	0.9387	93.87%
Biodegradation	-	0.6000	60.00%
Crustacea aquatic toxicity	+	0.5300	53.00%
Fish aquatic toxicity	+	0.7183	71.83%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293237	P54132	Bloom syndrome protein	44.7 nM	Potency	via Super-PRED
CHEMBL1293277	O15118	Niemann-Pick C1 protein	316.2 nM	Potency	via Super-PRED
CHEMBL1293294	P51151	Ras-related protein Rab-9A	562.3 nM	Potency	via Super-PRED
CHEMBL2164	P62136	Serine/threonine protein phosphatase PP1-alpha catalytic subunit	271.6 nM	IC50	via Super-PRED
CHEMBL1293265	Q9BPW0	Serine/threonine-protein phosphatase	239.16 nM	IC50	via Super-PRED
CHEMBL1293232	Q16637	Survival motor neuron protein	707.9 nM	Potency	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	89.44%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.82%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.36%	97.09%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	82.46%	96.09%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.85%	99.23%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.23%	100.00%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 5944
• LOTUS: LTS0020911
• wikiData: Q410884