CID 12313004

Details

• Internal ID: d6011451-6e3c-4d00-9c04-5704c73a91bc
• Taxonomy: Organoheterocyclic compounds > Benzopyrans > 1-benzopyrans > Xanthones > Pyranoxanthones
• IUPAC Name: (E)-4-[(1S,2S,17S,19R)-12-hydroxy-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),5,9,11,15-pentaen-19-yl]-2-methylbut-2-enal
• SMILES (Canonical): CC(=CCC1=C2C(=C(C3=C1OC45C6CC(C=C4C3=O)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=C4C3=O)C(=O)[C@@]5(OC6(C)C)C/C=C(\C)/C=O)O)C=CC(O2)(C)C)C
• InChI: InChI=1S/C33H36O7/c1-17(2)8-9-21-27-20(11-12-30(4,5)38-27)25(35)24-26(36)22-14-19-15-23-31(6,7)40-32(29(19)37,13-10-18(3)16-34)33(22,23)39-28(21)24/h8,10-12,14,16,19,23,35H,9,13,15H2,1-7H3/b18-10+/t19-,23+,32+,33-/m1/s1
• InChI Key: COQAPWLZSHQTKA-PVKLYBQVSA-N
• Popularity: 4 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₃H₃₆O₇
• Molecular Weight: 544.60 g/mol
• Exact Mass: 544.24610348 g/mol
• Topological Polar Surface Area (TPSA): 99.10 Ų
• XlogP: 5.30
• Atomic LogP (AlogP): 5.63
• H-Bond Acceptor: 7
• H-Bond Donor: 1
• Rotatable Bonds: 5

Synonyms

• 1064-71-7
• 1,5-Methano-11H-furo[3,2-g]pyrano[3,2-b]xanthene-3a(4H)-crotonaldehyde, 1,2,5,7-tetrahydro-8-hydroxy-.alpha.,2,2,11,11-pentamethyl-13-(3-methyl-2-butenyl)-4,7-dioxo-, cis-
• 2-Butenal, 2-methyl-4-[3a,4,5,7-tetrahydro-8-hydroxy-3,3,11,11-tetramethyl-13-(3-methyl-2-butenyl)-7,15-dioxo-1,5-methano-1H,3H,11H-furo[3,4-g]pyrano[3,2-b]xanthen-1-yl]-, [1R-[1.alpha.,1(E),3a.beta.,5.alpha.,14aS*]]-
• (E)-2-Methyl-4-[(1R,14aS)-3abeta,4,5,7-tetrahydro-8-hydroxy-3,3,11,11-tetramethyl-13-(3-methyl-2-buteny
• (E)-4-[(1S,2S,17S,19R)-12-hydroxy-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),5,9,11,15-pentaen-19-yl]-2-methylbut-2-enal

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9946	99.46%
Caco-2	-	0.7305	73.05%
Blood Brain Barrier	+	0.7500	75.00%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.8144	81.44%
OATP2B1 inhibitior	-	0.8591	85.91%
OATP1B1 inhibitior	-	0.3205	32.05%
OATP1B3 inhibitior	+	0.9195	91.95%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.9974	99.74%
P-glycoprotein inhibitior	+	0.8529	85.29%
P-glycoprotein substrate	+	0.6521	65.21%
CYP3A4 substrate	+	0.6939	69.39%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8434	84.34%
CYP3A4 inhibition	-	0.7398	73.98%
CYP2C9 inhibition	+	0.5201	52.01%
CYP2C19 inhibition	-	0.5353	53.53%
CYP2D6 inhibition	-	0.8844	88.44%
CYP1A2 inhibition	-	0.6042	60.42%
CYP2C8 inhibition	+	0.6929	69.29%
CYP inhibitory promiscuity	-	0.5776	57.76%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.5203	52.03%
Eye corrosion	-	0.9890	98.90%
Eye irritation	-	0.8609	86.09%
Skin irritation	-	0.6549	65.49%
Skin corrosion	-	0.9058	90.58%
Ames mutagenesis	+	0.5700	57.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3876	38.76%
Micronuclear	-	0.6600	66.00%
Hepatotoxicity	-	0.6750	67.50%
skin sensitisation	-	0.6872	68.72%
Respiratory toxicity	+	0.6778	67.78%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.7000	70.00%
Nephrotoxicity	-	0.7782	77.82%
Acute Oral Toxicity (c)	III	0.4134	41.34%
Estrogen receptor binding	+	0.8412	84.12%
Androgen receptor binding	+	0.7478	74.78%
Thyroid receptor binding	+	0.6553	65.53%
Glucocorticoid receptor binding	+	0.8736	87.36%
Aromatase binding	+	0.7388	73.88%
PPAR gamma	+	0.7617	76.17%
Honey bee toxicity	-	0.6610	66.10%
Biodegradation	-	0.9500	95.00%
Crustacea aquatic toxicity	-	0.6400	64.00%
Fish aquatic toxicity	+	0.9889	98.89%

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	99.44%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.90%	94.45%
CHEMBL2581	P07339	Cathepsin D	95.69%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.89%	89.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	90.93%	85.14%
CHEMBL3401	O75469	Pregnane X receptor	90.16%	94.73%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.05%	96.09%
CHEMBL3038469	P24941	CDK2/Cyclin A	86.90%	91.38%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.71%	97.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.48%	95.89%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.74%	100.00%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	85.40%	96.90%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.05%	95.56%
CHEMBL1951	P21397	Monoamine oxidase A	84.33%	91.49%
CHEMBL284	P27487	Dipeptidyl peptidase IV	83.85%	95.69%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	81.41%	95.71%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	81.38%	89.34%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	81.18%	86.92%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.68%	99.23%
CHEMBL3830	Q2M2I8	Adaptor-associated kinase	80.25%	83.10%
CHEMBL2964	P36507	Dual specificity mitogen-activated protein kinase kinase 2	80.05%	80.00%

Plants that contains it

• Callitriche stagnalis
• Catalpa ovata
• 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: 12313004
• NPASS: NPC285154
• LOTUS: LTS0202286
• wikiData: Q105135766