Jolkinolide B

Details

• Internal ID: 6d6d7880-0e7d-49e5-b245-8a71229562c3
• Taxonomy: Organoheterocyclic compounds > Naphthofurans
• IUPAC Name: (1S,3R,8R,10R,11R,12R,17R)-5,12,16,16-tetramethyl-2,7,9-trioxahexacyclo[9.8.0.01,3.04,8.08,10.012,17]nonadec-4-en-6-one
• SMILES (Canonical): CC1=C2C3C4(O3)CCC5C(CCCC5(C4C6C2(O6)OC1=O)C)(C)C
• SMILES (Isomeric): CC1=C2[C@@H]3[C@]4(O3)CC[C@H]5[C@]([C@@H]4[C@@H]6[C@]2(O6)OC1=O)(CCCC5(C)C)C
• InChI: InChI=1S/C20H26O4/c1-10-12-14-19(22-14)9-6-11-17(2,3)7-5-8-18(11,4)13(19)15-20(12,23-15)24-16(10)21/h11,13-15H,5-9H2,1-4H3/t11-,13+,14-,15-,18-,19+,20-/m1/s1
• InChI Key: SOVOCMGDFRGRKF-MCDHERAVSA-N
• Popularity: 42 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₆O₄
• Molecular Weight: 330.40 g/mol
• Exact Mass: 330.18310931 g/mol
• Topological Polar Surface Area (TPSA): 51.40 Ų
• XlogP: 3.20
• Atomic LogP (AlogP): 3.35
• H-Bond Acceptor: 4
• H-Bond Donor: 0
• Rotatable Bonds: 0

Synonyms

• 37905-08-1
• CHEBI:69827
• (1S,3R,8R,10R,11R,12R,17R)-5,12,16,16-tetramethyl-2,7,9-trioxahexacyclo[9.8.0.01,3.04,8.08,10.012,17]nonadec-4-en-6-one
• CHEMBL404387
• DTXSID70958923
• HY-N0732
• NSC700087
• AKOS032946071
• NSC-700087
• MS-24967
• NCI60_035896
• A7147
• CS-0009745
• Q27138168
• (1S,3R,8R,10R,11R,12R,17R)-5,12,16,16-tetramethyl-2,7,9-trioxahexacyclo[9.8.0.0,.0,.0,.0,nonadec-4-en-6-one
• (4aR,6aS,7aR,10aR,11aR,11bR,11cR)-4,4,8,11c-tetramethyl-1,2,3,4,4a,5,6,11a,11b,11c-decahydrobis(oxireno)[2',3':1,10a;2'',3'':3,4]phenanthro[3,2-b]furan-9(7aH)-one
• 4,4,8,11b-tetramethyl-2,3,4,4a,5,6,6a,7,10a,11,11a,11b-dodecahydro- 1H,9H-6a:7,10a:11-diepoxyphenanthro[3,2-b]furan-9-one
• 4,4,8,11c-Tetramethyl-1,2,3,4,4a,5,6,11a,11b,11c-decahydrobisoxireno[3,4:1,10a]phenanthro[3,2-b]furan-9(7aH)-one
• Bisoxireno(1,10a:3,4)phenanthro(3,2-b)furan-9(7aH)-one, 1,2,3,4,4a,5,6,11a,11b,11c-decahydro-4,4,8,11c-tetramethyl-, (4aR-(4aalpha,6aS*,7abeta,10aR*,11abeta,11balpha,11cbeta))-
• Bisoxireno[1,10a:3,4]phenanthro[3,2-b]furan-9(7aH)-one, 1,2,3,4,4a,5,6,11a,11b,11c-decahydro-4,4,8,11c-tetramethyl-, [4aR-(4a.alpha.,6aS*,7a.beta.,10aR*,11a.beta.,11b.alpha.,11c.beta.)]-
• Bisoxireno[1,4]phenanthro[3,2-b]furan-9(7aH)-one, 1,2, 3,4,4a,5,6,11a,11b,11c-decahydro-4,4,8,11c-tetramethyl-, [4aR-(4a.alpha.,6aS*,7a.beta.,10aR*,11a.beta.,11b.alpha.,11c.beta,)]-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9929	99.29%
Caco-2	+	0.7831	78.31%
Blood Brain Barrier	+	0.8000	80.00%
Human oral bioavailability	+	0.7000	70.00%
Subcellular localzation	Mitochondria	0.7040	70.40%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8949	89.49%
OATP1B3 inhibitior	+	0.9768	97.68%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.5000	50.00%
BSEP inhibitior	-	0.5661	56.61%
P-glycoprotein inhibitior	-	0.4860	48.60%
P-glycoprotein substrate	-	0.8664	86.64%
CYP3A4 substrate	+	0.6482	64.82%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8696	86.96%
CYP3A4 inhibition	-	0.8098	80.98%
CYP2C9 inhibition	-	0.8264	82.64%
CYP2C19 inhibition	-	0.8275	82.75%
CYP2D6 inhibition	-	0.9355	93.55%
CYP1A2 inhibition	-	0.5000	50.00%
CYP2C8 inhibition	-	0.6327	63.27%
CYP inhibitory promiscuity	-	0.8889	88.89%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.4752	47.52%
Eye corrosion	-	0.9882	98.82%
Eye irritation	-	0.8844	88.44%
Skin irritation	-	0.5417	54.17%
Skin corrosion	-	0.9009	90.09%
Ames mutagenesis	-	0.7600	76.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3744	37.44%
Micronuclear	-	0.6000	60.00%
Hepatotoxicity	-	0.6250	62.50%
skin sensitisation	-	0.7340	73.40%
Respiratory toxicity	-	0.5556	55.56%
Reproductive toxicity	+	0.8444	84.44%
Mitochondrial toxicity	+	0.8125	81.25%
Nephrotoxicity	+	0.7803	78.03%
Acute Oral Toxicity (c)	III	0.5119	51.19%
Estrogen receptor binding	+	0.8157	81.57%
Androgen receptor binding	+	0.6705	67.05%
Thyroid receptor binding	+	0.8398	83.98%
Glucocorticoid receptor binding	+	0.8512	85.12%
Aromatase binding	+	0.6840	68.40%
PPAR gamma	+	0.7904	79.04%
Honey bee toxicity	-	0.7790	77.90%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	+	0.6400	64.00%
Fish aquatic toxicity	+	0.9943	99.43%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.50%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.33%	91.11%
CHEMBL3524	P56524	Histone deacetylase 4	88.93%	92.97%
CHEMBL253	P34972	Cannabinoid CB2 receptor	87.00%	97.25%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.56%	97.09%
CHEMBL2581	P07339	Cathepsin D	86.51%	98.95%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	85.10%	97.14%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	85.09%	93.04%
CHEMBL4302	P08183	P-glycoprotein 1	84.40%	92.98%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.18%	99.23%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	83.76%	96.38%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.10%	100.00%
CHEMBL1871	P10275	Androgen Receptor	81.97%	96.43%
CHEMBL5805	Q9NR97	Toll-like receptor 8	81.84%	96.25%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	81.67%	82.69%

Plants that contains it

• Euphorbia ebracteolata
• Euphorbia fischeriana
• Euphorbia portulacoides
• Euphorbia seguieriana
• Euphorbia sessiliflora
• Suregada glomerulata
• Suregada multiflora

Cross-Links

• PubChem: 161954
• NPASS: NPC165608
• ChEMBL: CHEMBL404387
• LOTUS: LTS0243479
• wikiData: Q27138168