(E)-4-[(1R,2R,13R,15S)-6,8-dihydroxy-5-[(2R)-2-hydroxy-3-methylbut-3-enyl]-17,17-dimethyl-7-(3-methylbut-2-enyl)-10,14-dioxo-3,16-dioxapentacyclo[11.4.1.02,11.02,15.04,9]octadeca-4,6,8,11-tetraen-15-yl]-2-methylbut-2-enal

Details

• Internal ID: 5f3029e8-c92e-4bd7-9369-2bda98723086
• Taxonomy: Organoheterocyclic compounds > Benzopyrans > 1-benzopyrans > Xanthones
• IUPAC Name: (E)-4-[(1R,2R,13R,15S)-6,8-dihydroxy-5-[(2R)-2-hydroxy-3-methylbut-3-enyl]-17,17-dimethyl-7-(3-methylbut-2-enyl)-10,14-dioxo-3,16-dioxapentacyclo[11.4.1.02,11.02,15.04,9]octadeca-4,6,8,11-tetraen-15-yl]-2-methylbut-2-enal
• SMILES (Canonical): CC(=CCC1=C(C(=C2C(=C1O)C(=O)C3=CC4CC5C3(O2)C(C4=O)(OC5(C)C)CC=C(C)C=O)CC(C(=C)C)O)O)C
• SMILES (Isomeric): CC(=CCC1=C(C(=C2C(=C1O)C(=O)C3=C[C@H]4C[C@H]5[C@]3(O2)[C@@](C4=O)(OC5(C)C)C/C=C(\C)/C=O)C[C@H](C(=C)C)O)O)C
• InChI: InChI=1S/C33H38O8/c1-16(2)8-9-20-26(36)21(14-23(35)17(3)4)29-25(27(20)37)28(38)22-12-19-13-24-31(6,7)41-32(30(19)39,33(22,24)40-29)11-10-18(5)15-34/h8,10,12,15,19,23-24,35-37H,3,9,11,13-14H2,1-2,4-7H3/b18-10+/t19-,23+,24+,32+,33-/m0/s1
• InChI Key: YJAOBKYEAUHQLQ-VWVIGZQTSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₃H₃₈O₈
• Molecular Weight: 562.60 g/mol
• Exact Mass: 562.25666817 g/mol
• Topological Polar Surface Area (TPSA): 130.00 Ų
• XlogP: 4.90
• Atomic LogP (AlogP): 4.63
• H-Bond Acceptor: 8
• H-Bond Donor: 3
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9897	98.97%
Caco-2	-	0.7850	78.50%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.6362	63.62%
OATP2B1 inhibitior	-	0.7086	70.86%
OATP1B1 inhibitior	+	0.7364	73.64%
OATP1B3 inhibitior	+	0.8864	88.64%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.9784	97.84%
P-glycoprotein inhibitior	+	0.7388	73.88%
P-glycoprotein substrate	+	0.6728	67.28%
CYP3A4 substrate	+	0.7015	70.15%
CYP2C9 substrate	-	0.7987	79.87%
CYP2D6 substrate	-	0.8339	83.39%
CYP3A4 inhibition	-	0.7161	71.61%
CYP2C9 inhibition	-	0.5257	52.57%
CYP2C19 inhibition	-	0.6616	66.16%
CYP2D6 inhibition	-	0.8751	87.51%
CYP1A2 inhibition	-	0.6346	63.46%
CYP2C8 inhibition	+	0.7121	71.21%
CYP inhibitory promiscuity	-	0.6682	66.82%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9200	92.00%
Carcinogenicity (trinary)	Non-required	0.5739	57.39%
Eye corrosion	-	0.9868	98.68%
Eye irritation	-	0.8805	88.05%
Skin irritation	-	0.6622	66.22%
Skin corrosion	-	0.9002	90.02%
Ames mutagenesis	+	0.5200	52.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4806	48.06%
Micronuclear	-	0.6300	63.00%
Hepatotoxicity	-	0.6500	65.00%
skin sensitisation	-	0.7158	71.58%
Respiratory toxicity	+	0.6667	66.67%
Reproductive toxicity	+	0.9333	93.33%
Mitochondrial toxicity	+	0.8500	85.00%
Nephrotoxicity	-	0.7323	73.23%
Acute Oral Toxicity (c)	III	0.3656	36.56%
Estrogen receptor binding	+	0.7762	77.62%
Androgen receptor binding	+	0.7361	73.61%
Thyroid receptor binding	+	0.6110	61.10%
Glucocorticoid receptor binding	+	0.8320	83.20%
Aromatase binding	+	0.7606	76.06%
PPAR gamma	+	0.7240	72.40%
Honey bee toxicity	-	0.6260	62.60%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	-	0.7100	71.00%
Fish aquatic toxicity	+	0.9912	99.12%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.41%	91.11%
CHEMBL2581	P07339	Cathepsin D	98.12%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.85%	94.45%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	93.83%	85.14%
CHEMBL1806	P11388	DNA topoisomerase II alpha	93.63%	89.00%
CHEMBL3401	O75469	Pregnane X receptor	90.44%	94.73%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.94%	96.09%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	87.74%	96.90%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.18%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.44%	95.56%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.06%	100.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.86%	95.89%
CHEMBL284	P27487	Dipeptidyl peptidase IV	82.55%	95.69%
CHEMBL3492	P49721	Proteasome Macropain subunit	81.91%	90.24%
CHEMBL215	P09917	Arachidonate 5-lipoxygenase	81.16%	92.68%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	80.88%	95.50%
CHEMBL3038469	P24941	CDK2/Cyclin A	80.85%	91.38%

Plants that contains it

• Garcinia gaudichaudii

Cross-Links

• PubChem: 163190718
• LOTUS: LTS0262486
• wikiData: Q105349148