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

Details

• Internal ID: 1dc395e0-bcd9-45c8-8eb2-3fc1dfb7f987
• Taxonomy: Organoheterocyclic compounds > Benzopyrans > 1-benzopyrans > Xanthones > Pyranoxanthones
• IUPAC Name: (1S,2S,17R,19R)-12-hydroxy-19-[(E)-4-hydroxy-3-methylbut-2-enyl]-17-methoxy-8,8,21,21-tetramethyl-5-(3-methylbut-2-enyl)-3,7,20-trioxahexacyclo[15.4.1.02,15.02,19.04,13.06,11]docosa-4(13),5,9,11,15-pentaene-14,18-dione
• SMILES (Canonical): CC(=CCC1=C2C(=C(C3=C1OC45C6CC(C=C4C3=O)(C(=O)C5(OC6(C)C)CC=C(C)CO)OC)O)C=CC(O2)(C)C)C
• SMILES (Isomeric): CC(=CCC1=C2C(=C(C3=C1O[C@@]45[C@H]6C[C@@](C=C4C3=O)(C(=O)[C@@]5(OC6(C)C)C/C=C(\C)/CO)OC)O)C=CC(O2)(C)C)C
• InChI: InChI=1S/C34H40O8/c1-18(2)9-10-21-27-20(12-13-30(4,5)40-27)25(36)24-26(37)22-15-32(39-8)16-23-31(6,7)42-33(29(32)38,14-11-19(3)17-35)34(22,23)41-28(21)24/h9,11-13,15,23,35-36H,10,14,16-17H2,1-8H3/b19-11+/t23-,32-,33-,34+/m0/s1
• InChI Key: FJWBQUVKMGEVOU-YBWDRDJKSA-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): 112.00 Ų
• XlogP: 5.20
• Atomic LogP (AlogP): 5.19
• H-Bond Acceptor: 8
• H-Bond Donor: 2
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9833	98.33%
Caco-2	-	0.7227	72.27%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	-	0.6714	67.14%
Subcellular localzation	Mitochondria	0.8210	82.10%
OATP2B1 inhibitior	-	0.8582	85.82%
OATP1B1 inhibitior	+	0.7073	70.73%
OATP1B3 inhibitior	+	0.9338	93.38%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.7814	78.14%
BSEP inhibitior	+	0.9910	99.10%
P-glycoprotein inhibitior	+	0.8087	80.87%
P-glycoprotein substrate	+	0.6587	65.87%
CYP3A4 substrate	+	0.7034	70.34%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8334	83.34%
CYP3A4 inhibition	-	0.5163	51.63%
CYP2C9 inhibition	-	0.7112	71.12%
CYP2C19 inhibition	-	0.6656	66.56%
CYP2D6 inhibition	-	0.8941	89.41%
CYP1A2 inhibition	-	0.6417	64.17%
CYP2C8 inhibition	+	0.6953	69.53%
CYP inhibitory promiscuity	-	0.6128	61.28%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.5386	53.86%
Eye corrosion	-	0.9885	98.85%
Eye irritation	-	0.8697	86.97%
Skin irritation	-	0.7115	71.15%
Skin corrosion	-	0.9394	93.94%
Ames mutagenesis	+	0.5900	59.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5401	54.01%
Micronuclear	-	0.6400	64.00%
Hepatotoxicity	-	0.6323	63.23%
skin sensitisation	-	0.8290	82.90%
Respiratory toxicity	+	0.6667	66.67%
Reproductive toxicity	+	0.9667	96.67%
Mitochondrial toxicity	+	0.7125	71.25%
Nephrotoxicity	+	0.4663	46.63%
Acute Oral Toxicity (c)	I	0.4760	47.60%
Estrogen receptor binding	+	0.7995	79.95%
Androgen receptor binding	+	0.7741	77.41%
Thyroid receptor binding	+	0.6384	63.84%
Glucocorticoid receptor binding	+	0.8089	80.89%
Aromatase binding	+	0.8107	81.07%
PPAR gamma	+	0.7253	72.53%
Honey bee toxicity	-	0.6700	67.00%
Biodegradation	-	0.9500	95.00%
Crustacea aquatic toxicity	-	0.7000	70.00%
Fish aquatic toxicity	+	0.9920	99.20%

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	99.43%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	99.09%	94.45%
CHEMBL1951	P21397	Monoamine oxidase A	98.15%	91.49%
CHEMBL1937	Q92769	Histone deacetylase 2	96.31%	94.75%
CHEMBL2581	P07339	Cathepsin D	95.30%	98.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	94.90%	85.14%
CHEMBL1806	P11388	DNA topoisomerase II alpha	93.48%	89.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.07%	96.09%
CHEMBL3401	O75469	Pregnane X receptor	89.30%	94.73%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.62%	95.89%
CHEMBL1994	P08235	Mineralocorticoid receptor	87.27%	100.00%
CHEMBL3038469	P24941	CDK2/Cyclin A	86.75%	91.38%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.70%	97.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.26%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.57%	95.56%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	84.55%	86.92%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	83.95%	91.71%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.65%	99.23%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	80.75%	94.00%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	80.11%	97.14%

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: 25208912
• NPASS: NPC182107
• LOTUS: LTS0273782
• wikiData: Q104996367