Cocculin

Details

• Internal ID: 5dab4f85-166e-46a7-b3b3-e39c16203b0f
• Taxonomy: Organoheterocyclic compounds > Furopyrans
• IUPAC Name: (1R,3R,5S,8S,9R,12S,13R,14S)-1-hydroxy-14-(2-hydroxypropan-2-yl)-13-methyl-4,7,10-trioxapentacyclo[6.4.1.19,12.03,5.05,13]tetradecane-6,11-dione;(1R,3R,5S,8S,9R,12S,13R,14R)-1-hydroxy-13-methyl-14-prop-1-en-2-yl-4,7,10-trioxapentacyclo[6.4.1.19,12.03,5.05,13]tetradecane-6,11-dione
• SMILES (Canonical): CC(=C)C1C2C3C4(C(C1C(=O)O2)(CC5C4(O5)C(=O)O3)O)C.CC12C3C4C(C(C1(CC5C2(O5)C(=O)O3)O)C(=O)O4)C(C)(C)O
• SMILES (Isomeric): CC(=C)[C@@H]1[C@@H]2[C@@H]3[C@@]4([C@]([C@H]1C(=O)O2)(C[C@@H]5[C@]4(O5)C(=O)O3)O)C.C[C@@]12[C@H]3[C@H]4[C@H]([C@@H]([C@@]1(C[C@@H]5[C@]2(O5)C(=O)O3)O)C(=O)O4)C(C)(C)O
• InChI: InChI=1S/C15H18O7.C15H16O6/c1-12(2,18)6-7-10(16)20-8(6)9-13(3)14(7,19)4-5-15(13,22-5)11(17)21-9;1-5(2)7-8-11(16)19-9(7)10-13(3)14(8,18)4-6-15(13,21-6)12(17)20-10/h5-9,18-19H,4H2,1-3H3;6-10,18H,1,4H2,2-3H3/t5-,6+,7-,8-,9-,13-,14-,15+;6-,7+,8-,9-,10-,13-,14-,15+/m11/s1
• InChI Key: VJKUPQSHOVKBCO-AHMKVGDJSA-N
• Popularity: 4,151 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₀H₃₄O₁₃
• Molecular Weight: 602.60 g/mol
• Exact Mass: 602.19994113 g/mol
• Topological Polar Surface Area (TPSA): 191.00 Ų
• XlogP: 0.00
• Atomic LogP (AlogP): -0.93
• H-Bond Acceptor: 13
• H-Bond Donor: 3
• Rotatable Bonds: 2

Synonyms

• 124-87-8
• Picrotin - Picrotoxinin
• Cocculin
• Sesquiterpene
• NA1584
• UN1584
• C15H18O7.C15H16O6
• C15-H18-O7.C15-H16-O6
• P 1675
• Lopac0_000916
• SCHEMBL28587
• MLS001423995
• Picrotoxin (Compound of one mole Picrotoxinin and one mole Picrotin)
• CHEMBL506977
• DTXSID7045605
• HMS2051E09
• HMS2235M10
• HMS3262H14
• 3,6-Methano-8H-1,5,7-trioxacyclopenta(ij)cycloprop(a)azulene-4,8(3H)-dione, hexahydro-2a-hydroxy-9-(1-hydroxy-1-methylethyl)-8b-methyl-, (1aR-(1aalpha,2abeta,3beta,6beta,6abeta,8aS*,8bbeta,9S*))-, com
• Tox21_500916
• AKOS024456403
• CCG-100777
• LP00916
• NC00027
• SDCCGSBI-0050891.P002
• NCGC00261601-01
• Picrotoxin 100 microg/mL in Acetonitrile
• SMR000469289
• EU-0100916
• hydroxy-(1-hydroxy-1-methyl-ethyl)-methyl-[?]dione; hydroxy-isopropenyl-methyl-[?]dione
• 3,6-Methano-8H-1,5,7-trioxacyclopenta[ij]cycloprop[a]azulene-4,8(3H)-dione, hexahydro-2a-hydroxy-9-(1-hydroxy-1-methylethyl)-8b-methyl-, (1aR,2aR,3S,6R,6aS,8aS,8bR,9S)- & (1aR,2aR,3S,6R,6aS,8aS,8bR,9R)-hexahydro-2a-hydroxy-8b-methyl-9-(1-methylethenyl)-3,6-methano-8H-1,5,7-trioxacyclopenta[ij]cycloprop[a]azulene-4,8(3H)-dione (1:1)

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9742	97.42%
Caco-2	-	0.6869	68.69%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	+	0.5857	58.57%
Subcellular localzation	Mitochondria	0.6086	60.86%
OATP2B1 inhibitior	-	0.8552	85.52%
OATP1B1 inhibitior	+	0.9253	92.53%
OATP1B3 inhibitior	+	0.9554	95.54%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.9122	91.22%
P-glycoprotein inhibitior	-	0.5793	57.93%
P-glycoprotein substrate	+	0.5906	59.06%
CYP3A4 substrate	+	0.6601	66.01%
CYP2C9 substrate	-	0.8024	80.24%
CYP2D6 substrate	-	0.8631	86.31%
CYP3A4 inhibition	-	0.5167	51.67%
CYP2C9 inhibition	-	0.9071	90.71%
CYP2C19 inhibition	-	0.8809	88.09%
CYP2D6 inhibition	-	0.9307	93.07%
CYP1A2 inhibition	-	0.8981	89.81%
CYP2C8 inhibition	-	0.7024	70.24%
CYP inhibitory promiscuity	-	0.9290	92.90%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.4402	44.02%
Eye corrosion	-	0.9834	98.34%
Eye irritation	-	0.8416	84.16%
Skin irritation	-	0.5997	59.97%
Skin corrosion	-	0.8675	86.75%
Ames mutagenesis	+	0.5300	53.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5849	58.49%
Micronuclear	-	0.5500	55.00%
Hepatotoxicity	+	0.6125	61.25%
skin sensitisation	-	0.6951	69.51%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.8333	83.33%
Mitochondrial toxicity	+	0.8375	83.75%
Nephrotoxicity	+	0.8342	83.42%
Acute Oral Toxicity (c)	III	0.3686	36.86%
Estrogen receptor binding	+	0.7687	76.87%
Androgen receptor binding	+	0.7598	75.98%
Thyroid receptor binding	+	0.6241	62.41%
Glucocorticoid receptor binding	-	0.7021	70.21%
Aromatase binding	-	0.5420	54.20%
PPAR gamma	+	0.6305	63.05%
Honey bee toxicity	-	0.7555	75.55%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	+	0.5300	53.00%
Fish aquatic toxicity	+	0.9564	95.64%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293237	P54132	Bloom syndrome protein	177.8 nM	Potency	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL253	P34972	Cannabinoid CB2 receptor	97.36%	97.25%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	94.35%	85.14%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.20%	91.11%
CHEMBL218	P21554	Cannabinoid CB1 receptor	89.50%	96.61%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	88.67%	97.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.07%	95.56%
CHEMBL4040	P28482	MAP kinase ERK2	87.14%	83.82%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	87.00%	96.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.89%	89.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.32%	99.23%
CHEMBL2039	P27338	Monoamine oxidase B	84.00%	92.51%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.13%	100.00%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	81.87%	95.71%

Plants that contains it

• Aquilaria malaccensis
• Aquilaria sinensis
• Eleutherococcus senticosus
• Magnolia biondii
• Magnolia denudata
• Magnolia kobus
• Magnolia salicifolia
• Magnolia sprengeri
• Murraya exotica
• Murraya paniculata

Cross-Links

• PubChem: 6473767
• NPASS: NPC266061
• LOTUS: LTS0194535
• wikiData: Q105287333