(E)-4-[(1S,2S,15R,16S,17S,19R)-12-hydroxy-16-methoxy-8,8,21,21-tetramethyl-5-(3-methylbut-2-enyl)-14,18-dioxo-3,7,20-trioxahexacyclo[15.4.1.02,15.02,19.04,13.06,11]docosa-4(13),5,9,11-tetraen-19-yl]-2-methylbut-2-enal

Details

• Internal ID: 95e72b90-506b-4f03-bbd7-4f37aa0976d4
• Taxonomy: Organoheterocyclic compounds > Benzopyrans > 1-benzopyrans > Xanthones > Pyranoxanthones
• IUPAC Name: (E)-4-[(1S,2S,15R,16S,17S,19R)-12-hydroxy-16-methoxy-8,8,21,21-tetramethyl-5-(3-methylbut-2-enyl)-14,18-dioxo-3,7,20-trioxahexacyclo[15.4.1.02,15.02,19.04,13.06,11]docosa-4(13),5,9,11-tetraen-19-yl]-2-methylbut-2-enal
• SMILES (Canonical): CC(=CCC1=C2C(=C(C3=C1OC45C6CC(C(C4C3=O)OC)C(=O)C5(OC6(C)C)CC=C(C)C=O)O)C=CC(O2)(C)C)C
• SMILES (Isomeric): CC(=CCC1=C2C(=C(C3=C1O[C@@]45[C@H]6C[C@@H]([C@@H]([C@H]4C3=O)OC)C(=O)[C@@]5(OC6(C)C)C/C=C(\C)/C=O)O)C=CC(O2)(C)C)C
• InChI: InChI=1S/C34H40O8/c1-17(2)9-10-20-27-19(12-13-31(4,5)40-27)25(36)23-26(37)24-29(39-8)21-15-22-32(6,7)42-33(30(21)38,14-11-18(3)16-35)34(22,24)41-28(20)23/h9,11-13,16,21-22,24,29,36H,10,14-15H2,1-8H3/b18-11+/t21-,22-,24+,29-,33-,34-/m0/s1
• InChI Key: PSPHEZYRWQNMDW-JDRKPRMKSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₄H₄₀O₈
• Molecular Weight: 576.70 g/mol
• Exact Mass: 576.27231823 g/mol
• Topological Polar Surface Area (TPSA): 108.00 Ų
• XlogP: 4.90
• Atomic LogP (AlogP): 5.33
• H-Bond Acceptor: 8
• H-Bond Donor: 1
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9925	99.25%
Caco-2	-	0.7350	73.50%
Blood Brain Barrier	+	0.7000	70.00%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.7504	75.04%
OATP2B1 inhibitior	-	0.7120	71.20%
OATP1B1 inhibitior	+	0.7060	70.60%
OATP1B3 inhibitior	-	0.2246	22.46%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	+	0.9973	99.73%
P-glycoprotein inhibitior	+	0.8612	86.12%
P-glycoprotein substrate	+	0.6749	67.49%
CYP3A4 substrate	+	0.7055	70.55%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8434	84.34%
CYP3A4 inhibition	-	0.5982	59.82%
CYP2C9 inhibition	-	0.6536	65.36%
CYP2C19 inhibition	+	0.5682	56.82%
CYP2D6 inhibition	-	0.8545	85.45%
CYP1A2 inhibition	-	0.6370	63.70%
CYP2C8 inhibition	+	0.7142	71.42%
CYP inhibitory promiscuity	-	0.5257	52.57%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.5637	56.37%
Eye corrosion	-	0.9889	98.89%
Eye irritation	-	0.8818	88.18%
Skin irritation	-	0.7369	73.69%
Skin corrosion	-	0.9331	93.31%
Ames mutagenesis	-	0.5737	57.37%
Human Ether-a-go-go-Related Gene inhibition	-	0.4129	41.29%
Micronuclear	-	0.6100	61.00%
Hepatotoxicity	-	0.6250	62.50%
skin sensitisation	-	0.7224	72.24%
Respiratory toxicity	+	0.7444	74.44%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	+	0.6500	65.00%
Nephrotoxicity	-	0.6912	69.12%
Acute Oral Toxicity (c)	III	0.3587	35.87%
Estrogen receptor binding	+	0.8292	82.92%
Androgen receptor binding	+	0.7712	77.12%
Thyroid receptor binding	+	0.6797	67.97%
Glucocorticoid receptor binding	+	0.8790	87.90%
Aromatase binding	+	0.7487	74.87%
PPAR gamma	+	0.7504	75.04%
Honey bee toxicity	-	0.6543	65.43%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	-	0.5700	57.00%
Fish aquatic toxicity	+	0.9789	97.89%

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	99.65%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	98.18%	94.45%
CHEMBL1951	P21397	Monoamine oxidase A	95.24%	91.49%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.86%	97.09%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.73%	96.09%
CHEMBL2581	P07339	Cathepsin D	92.88%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	92.52%	89.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	91.26%	95.89%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	90.94%	95.50%
CHEMBL3922	P50579	Methionine aminopeptidase 2	90.36%	97.28%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	88.98%	85.14%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.39%	86.33%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	87.04%	89.34%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.39%	95.56%
CHEMBL3038469	P24941	CDK2/Cyclin A	86.21%	91.38%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	85.44%	95.71%
CHEMBL1929	P47989	Xanthine dehydrogenase	85.05%	96.12%
CHEMBL3830	Q2M2I8	Adaptor-associated kinase	83.72%	83.10%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.43%	99.17%
CHEMBL3401	O75469	Pregnane X receptor	82.86%	94.73%
CHEMBL340	P08684	Cytochrome P450 3A4	82.79%	91.19%
CHEMBL4224	P49759	Dual specificty protein kinase CLK1	82.31%	85.30%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	81.37%	94.00%

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: 11801290
• NPASS: NPC14148