(E)-4-[(1R,13R,15S)-6,8-dihydroxy-5-[(E)-2-hydroxypent-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: f88e6664-483d-4cd2-94c7-63640b07afb0
• Taxonomy: Organoheterocyclic compounds > Benzopyrans > 1-benzopyrans > Xanthones
• IUPAC Name: (E)-4-[(1R,13R,15S)-6,8-dihydroxy-5-[(E)-2-hydroxypent-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=CC(CC1=C2C(=C(C(=C1O)CC=C(C)C)O)C(=O)C3=CC4CC5C3(O2)C(C4=O)(OC5(C)C)CC=C(C)C=O)O
• SMILES (Isomeric): C/C=C/C(CC1=C2C(=C(C(=C1O)CC=C(C)C)O)C(=O)C3=C[C@H]4C[C@H]5C3(O2)[C@@](C4=O)(OC5(C)C)C/C=C(\C)/C=O)O
• InChI: InChI=1S/C33H38O8/c1-7-8-20(35)15-22-26(36)21(10-9-17(2)3)27(37)25-28(38)23-13-19-14-24-31(5,6)41-32(30(19)39,12-11-18(4)16-34)33(23,24)40-29(22)25/h7-9,11,13,16,19-20,24,35-37H,10,12,14-15H2,1-6H3/b8-7+,18-11+/t19-,20?,24+,32+,33?/m0/s1
• InChI Key: NEAHESPJKUPLDM-GHAMOEKNSA-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: 4.50
• 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	+	0.9917	99.17%
Caco-2	-	0.7874	78.74%
Blood Brain Barrier	+	0.5888	58.88%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.6494	64.94%
OATP2B1 inhibitior	-	0.7109	71.09%
OATP1B1 inhibitior	+	0.7168	71.68%
OATP1B3 inhibitior	+	0.9102	91.02%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.9926	99.26%
P-glycoprotein inhibitior	+	0.7982	79.82%
P-glycoprotein substrate	+	0.6795	67.95%
CYP3A4 substrate	+	0.7028	70.28%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8431	84.31%
CYP3A4 inhibition	-	0.7796	77.96%
CYP2C9 inhibition	-	0.5070	50.70%
CYP2C19 inhibition	-	0.6917	69.17%
CYP2D6 inhibition	-	0.8770	87.70%
CYP1A2 inhibition	-	0.6342	63.42%
CYP2C8 inhibition	+	0.7161	71.61%
CYP inhibitory promiscuity	-	0.6430	64.30%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.5320	53.20%
Eye corrosion	-	0.9883	98.83%
Eye irritation	-	0.9014	90.14%
Skin irritation	-	0.6637	66.37%
Skin corrosion	-	0.9084	90.84%
Ames mutagenesis	-	0.5000	50.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4112	41.12%
Micronuclear	-	0.6200	62.00%
Hepatotoxicity	-	0.6625	66.25%
skin sensitisation	-	0.7329	73.29%
Respiratory toxicity	+	0.6889	68.89%
Reproductive toxicity	+	0.9333	93.33%
Mitochondrial toxicity	+	0.8375	83.75%
Nephrotoxicity	-	0.7701	77.01%
Acute Oral Toxicity (c)	III	0.3448	34.48%
Estrogen receptor binding	+	0.8293	82.93%
Androgen receptor binding	+	0.7395	73.95%
Thyroid receptor binding	+	0.6237	62.37%
Glucocorticoid receptor binding	+	0.8485	84.85%
Aromatase binding	+	0.7191	71.91%
PPAR gamma	+	0.7234	72.34%
Honey bee toxicity	-	0.6206	62.06%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.7200	72.00%
Fish aquatic toxicity	+	0.9827	98.27%

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	99.32%	91.11%
CHEMBL2581	P07339	Cathepsin D	98.06%	98.95%
CHEMBL284	P27487	Dipeptidyl peptidase IV	95.64%	95.69%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.39%	94.45%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	94.97%	85.14%
CHEMBL1806	P11388	DNA topoisomerase II alpha	93.89%	89.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.47%	96.09%
CHEMBL3401	O75469	Pregnane X receptor	90.80%	94.73%
CHEMBL3492	P49721	Proteasome Macropain subunit	89.60%	90.24%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.65%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.44%	95.56%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.19%	100.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.45%	99.23%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	82.17%	96.90%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	81.38%	95.50%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	81.24%	97.14%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.02%	95.89%
CHEMBL3830	Q2M2I8	Adaptor-associated kinase	80.99%	83.10%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	80.69%	90.71%

Plants that contains it

• Garcinia gaudichaudii

Cross-Links

• PubChem: 101949809
• LOTUS: LTS0217188
• wikiData: Q105177806