Vulgarin

Details

• Internal ID: 0b33246b-8667-4cf6-8787-9063d4ec3b71
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Eudesmanolides, secoeudesmanolides, and derivatives
• IUPAC Name: (3S,3aS,5aR,9R,9aS,9bS)-9-hydroxy-3,5a,9-trimethyl-3,3a,4,5,9a,9b-hexahydrobenzo[g][1]benzofuran-2,6-dione
• SMILES (Canonical): CC1C2CCC3(C(C2OC1=O)C(C=CC3=O)(C)O)C
• SMILES (Isomeric): C[C@H]1[C@@H]2CC[C@@]3([C@@H]([C@H]2OC1=O)[C@](C=CC3=O)(C)O)C
• InChI: InChI=1S/C15H20O4/c1-8-9-4-6-14(2)10(16)5-7-15(3,18)12(14)11(9)19-13(8)17/h5,7-9,11-12,18H,4,6H2,1-3H3/t8-,9-,11-,12+,14-,15+/m0/s1
• InChI Key: NGPDZEACIWDCKX-WUDKWMPASA-N
• Popularity: 9 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₀O₄
• Molecular Weight: 264.32 g/mol
• Exact Mass: 264.13615911 g/mol
• Topological Polar Surface Area (TPSA): 63.60 Ų
• XlogP: 1.20
• Atomic LogP (AlogP): 1.47
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 0

Synonyms

• Barrelin
• 3162-56-9
• Tauremizin
• Tauremisin
• Judaicin (sesquiterpene)
• Judaicin (eudesmane naphthofuran)
• Judaicin
• TAUREMIZINE
• (3S,3aS,5aR,9R,9aS,9bS)-9-hydroxy-3,5a,9-trimethyl-3,3a,4,5,9a,9b-hexahydrobenzo[g][1]benzofuran-2,6-dione
• CHEBI:10024
• 3a,5,5a,9,9a,9b-Hexahydro-9-hydroxy-3,5a,9-trimethylnaphtho(1,2-b)furan-2,6(3H,4H)-dione
• Eudesm-2-en-12-oic acid, 4,6-alpha-dihydroxy-1-oxo-, gamma-lactone, (11S)-
• (3aS,5aR,9R,9aS,9bS)-9-hydroxy-3,5a,9-trimethyl-3a,5,5a,9,9a,9b-hexahydronaphtho[1,2-b]furan-2,6(3H,4H)-dione
• Naphtho(1,2-b)furan-2,6(3H,4H)-dione, 3a,5,5a,9,9a,9b-hexahydro-9-hydroxy-3,5a,9-trimethyl-, (3S,3aS,5aR,9R,9aS,9bS)-
• Naphtho(1,2-b)furan-2,6(3H,4H)-dione, 3a,5,5a,9,9a,9b-hexahydro-9-hydroxy-3,5a,9-trimethyl-, (3S-(3alpha,3aalpha,5abeta,9alpha,9aalpha,9bbeta))-
• SMR000445685
• MLS000728573
• MLS001185447
• CHEMBL1422618
• DTXSID30928884
• HMS2225C10
• BBL034028
• STK013739
• AKOS001483019
• Vulgarin, >=90% (LC/MS-ELSD)
• NCGC00247310-01
• NCGC00247310-02
• NCGC00247310-03
• LS-68583
• VS-12384
• C09600
• Q27108555
• Eudesm-2-en-12-oic acid, 4,6.alpha.-dihydroxy-1-oxo-, .gamma.-lactone, (11S)-
• (3S,3AS,5AR,9R,9AS,9BS)-9-HYDROXY-3,5A,9-TRIMETHYL-2H,3H,3AH,4H,5H,5AH,6H,9H,9AH,9BH-NAPHTHO[1,2-B]FURAN-2,6-DIONE
• Naphtho[1,2-b]furan-2,6(3H,4H)-dione, 3a,5,5a,9,9a,9b-hexahydro-9-hydroxy-3,5a,9-trimethyl-, [3S-(3.alpha.,3a.alpha.,5a.beta.,9.alpha.,9a.alpha.,9b.beta.)]-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9765	97.65%
Caco-2	+	0.5214	52.14%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.5571	55.71%
Subcellular localzation	Mitochondria	0.5857	58.57%
OATP2B1 inhibitior	-	0.8537	85.37%
OATP1B1 inhibitior	+	0.9219	92.19%
OATP1B3 inhibitior	+	0.9374	93.74%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.6750	67.50%
BSEP inhibitior	-	0.9277	92.77%
P-glycoprotein inhibitior	-	0.9085	90.85%
P-glycoprotein substrate	-	0.8343	83.43%
CYP3A4 substrate	+	0.5692	56.92%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9037	90.37%
CYP3A4 inhibition	-	0.7615	76.15%
CYP2C9 inhibition	-	0.8735	87.35%
CYP2C19 inhibition	-	0.9431	94.31%
CYP2D6 inhibition	-	0.9620	96.20%
CYP1A2 inhibition	-	0.5000	50.00%
CYP2C8 inhibition	-	0.9358	93.58%
CYP inhibitory promiscuity	-	0.9076	90.76%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.4284	42.84%
Eye corrosion	-	0.9829	98.29%
Eye irritation	-	0.9117	91.17%
Skin irritation	+	0.6224	62.24%
Skin corrosion	-	0.5867	58.67%
Ames mutagenesis	-	0.7540	75.40%
Human Ether-a-go-go-Related Gene inhibition	-	0.7089	70.89%
Micronuclear	-	0.7800	78.00%
Hepatotoxicity	+	0.6982	69.82%
skin sensitisation	-	0.7711	77.11%
Respiratory toxicity	+	0.6333	63.33%
Reproductive toxicity	+	0.6667	66.67%
Mitochondrial toxicity	+	0.8000	80.00%
Nephrotoxicity	-	0.6115	61.15%
Acute Oral Toxicity (c)	III	0.4216	42.16%
Estrogen receptor binding	+	0.6046	60.46%
Androgen receptor binding	+	0.6024	60.24%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	-	0.5192	51.92%
Aromatase binding	-	0.7941	79.41%
PPAR gamma	-	0.6639	66.39%
Honey bee toxicity	-	0.9096	90.96%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.5400	54.00%
Fish aquatic toxicity	+	0.9822	98.22%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293236	P46063	ATP-dependent DNA helicase Q1	177.8 nM; 177.8 nM	Potency; Potency	via CMAUP; via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.56%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	91.31%	97.25%
CHEMBL1994	P08235	Mineralocorticoid receptor	87.97%	100.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	87.49%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.46%	95.56%
CHEMBL4803	P29474	Nitric-oxide synthase, endothelial	87.32%	86.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	86.01%	85.14%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.36%	97.09%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	85.23%	94.80%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	83.48%	94.45%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.95%	99.23%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.59%	89.00%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	80.39%	93.04%

Plants that contains it

• Achillea fragrantissima
• Achillea millefolium
• Artemisia abyssinica
• Artemisia annua
• Artemisia cana
• Artemisia judaica
• Cicer bijugum
• Cicer judaicum
• Cornus officinalis
• Echinops ritro
• Eucommia ulmoides
• Gymnosporia cassinoides
• Hippophae rhamnoides
• Panax ginseng
• Seriphidium lessingianum
• Tanacetum achilleifolium
• Xanthium strumarium
• Ziziphus jujuba

Cross-Links

• PubChem: 94253
• NPASS: NPC252433
• ChEMBL: CHEMBL1422618
• LOTUS: LTS0062007
• wikiData: Q27108555