(1S,2S,13S,15R)-6,8-dihydroxy-17,17-dimethyl-5,15-bis(3-methylbut-2-enyl)-3,16-dioxapentacyclo[11.4.1.02,11.02,15.04,9]octadeca-4,6,8,11-tetraene-10,14-dione

Details

• Internal ID: 77d3ed08-1add-48c6-b3dc-823bec3ec861
• Taxonomy: Organoheterocyclic compounds > Benzopyrans > 1-benzopyrans > Xanthones
• IUPAC Name: (1S,2S,13S,15R)-6,8-dihydroxy-17,17-dimethyl-5,15-bis(3-methylbut-2-enyl)-3,16-dioxapentacyclo[11.4.1.02,11.02,15.04,9]octadeca-4,6,8,11-tetraene-10,14-dione
• SMILES (Canonical): CC(=CCC1=C2C(=C(C=C1O)O)C(=O)C3=CC4CC5C3(O2)C(C4=O)(OC5(C)C)CC=C(C)C)C
• SMILES (Isomeric): CC(=CCC1=C2C(=C(C=C1O)O)C(=O)C3=C[C@@H]4C[C@@H]5[C@@]3(O2)[C@](C4=O)(OC5(C)C)CC=C(C)C)C
• InChI: InChI=1S/C28H32O6/c1-14(2)7-8-17-19(29)13-20(30)22-23(31)18-11-16-12-21-26(5,6)34-27(25(16)32,10-9-15(3)4)28(18,21)33-24(17)22/h7,9,11,13,16,21,29-30H,8,10,12H2,1-6H3/t16-,21+,27+,28-/m1/s1
• InChI Key: LWIGRTRTVVPXOZ-DLPQTZSGSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₃₂O₆
• Molecular Weight: 464.50 g/mol
• Exact Mass: 464.21988874 g/mol
• Topological Polar Surface Area (TPSA): 93.10 Ų
• XlogP: 5.40
• Atomic LogP (AlogP): 4.97
• H-Bond Acceptor: 6
• H-Bond Donor: 2
• Rotatable Bonds: 4

Synonyms

• BDBM50366228

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9895	98.95%
Caco-2	-	0.5431	54.31%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Mitochondria	0.7131	71.31%
OATP2B1 inhibitior	-	0.8584	85.84%
OATP1B1 inhibitior	+	0.8017	80.17%
OATP1B3 inhibitior	+	0.8588	85.88%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	+	0.9751	97.51%
P-glycoprotein inhibitior	+	0.6938	69.38%
P-glycoprotein substrate	-	0.5763	57.63%
CYP3A4 substrate	+	0.6490	64.90%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8338	83.38%
CYP3A4 inhibition	-	0.8232	82.32%
CYP2C9 inhibition	+	0.5921	59.21%
CYP2C19 inhibition	-	0.6074	60.74%
CYP2D6 inhibition	-	0.8783	87.83%
CYP1A2 inhibition	-	0.5671	56.71%
CYP2C8 inhibition	+	0.6016	60.16%
CYP inhibitory promiscuity	+	0.5000	50.00%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.5623	56.23%
Eye corrosion	-	0.9881	98.81%
Eye irritation	-	0.7806	78.06%
Skin irritation	-	0.6777	67.77%
Skin corrosion	-	0.9058	90.58%
Ames mutagenesis	+	0.5100	51.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6424	64.24%
Micronuclear	-	0.6200	62.00%
Hepatotoxicity	-	0.6031	60.31%
skin sensitisation	-	0.7293	72.93%
Respiratory toxicity	+	0.6333	63.33%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	+	0.7875	78.75%
Nephrotoxicity	-	0.6083	60.83%
Acute Oral Toxicity (c)	III	0.3899	38.99%
Estrogen receptor binding	+	0.8681	86.81%
Androgen receptor binding	+	0.7690	76.90%
Thyroid receptor binding	+	0.6223	62.23%
Glucocorticoid receptor binding	+	0.8068	80.68%
Aromatase binding	+	0.7538	75.38%
PPAR gamma	+	0.7991	79.91%
Honey bee toxicity	-	0.6868	68.68%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.6500	65.00%
Fish aquatic toxicity	+	0.9880	98.80%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1991	O14920	Inhibitor of nuclear factor kappa B kinase beta subunit	6600 nM	IC50	PMID: 22472167

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.53%	91.11%
CHEMBL2581	P07339	Cathepsin D	95.11%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.63%	89.00%
CHEMBL3401	O75469	Pregnane X receptor	93.76%	94.73%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.71%	94.45%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	91.56%	85.14%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	90.99%	93.40%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.87%	97.09%
CHEMBL3038469	P24941	CDK2/Cyclin A	89.40%	91.38%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	86.25%	96.95%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.04%	100.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	86.01%	96.09%
CHEMBL226	P30542	Adenosine A1 receptor	85.70%	95.93%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.87%	95.56%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	83.55%	96.90%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.46%	99.23%
CHEMBL241	Q14432	Phosphodiesterase 3A	83.34%	92.94%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.22%	86.33%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	81.74%	86.92%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	80.55%	97.21%
CHEMBL284	P27487	Dipeptidyl peptidase IV	80.36%	95.69%

Plants that contains it

• Callitriche stagnalis
• Croton discolor
• Eclipta prostrata
• Fragaria chiloensis
• Garcinia hanburyi
• Hemionitis glauca
• Millettia extensa
• Rhizomnium pseudopunctatum
• Ruscus hypoglossum
• Salix babylonica
• Scrophularia glabrata
• Toxicodendron radicans
• Vernonanthura discolor
• Wrightia coccinea

Cross-Links

• PubChem: 57393978
• NPASS: NPC94796
• ChEMBL: CHEMBL1958314
• LOTUS: LTS0231663
• wikiData: Q105158316