rel-(3R,4R)-9-(1,1-Dimethyl-2-propen-1-yl)-3,4-dihydro-3,4,8,11-tetrahydroxy-2,2-dimethylpyrano[3,2-c]xanthen-7(2H)-one

Details

• Internal ID: 3e1bf640-bcbf-4e0e-b154-7c8a8de18a0f
• Taxonomy: Organoheterocyclic compounds > Benzopyrans > 1-benzopyrans > Xanthones > Pyranoxanthones
• IUPAC Name: (3S,4S)-3,4,8,11-tetrahydroxy-2,2-dimethyl-9-(2-methylbut-3-en-2-yl)-3,4-dihydropyrano[3,2-c]xanthen-7-one
• SMILES (Canonical): CC1(C(C(C2=C(O1)C3=C(C=C2)C(=O)C4=C(C(=CC(=C4O3)O)C(C)(C)C=C)O)O)O)C
• SMILES (Isomeric): CC1([C@H]([C@H](C2=C(O1)C3=C(C=C2)C(=O)C4=C(C(=CC(=C4O3)O)C(C)(C)C=C)O)O)O)C
• InChI: InChI=1S/C23H24O7/c1-6-22(2,3)12-9-13(24)20-14(17(12)27)15(25)10-7-8-11-16(26)21(28)23(4,5)30-19(11)18(10)29-20/h6-9,16,21,24,26-28H,1H2,2-5H3/t16-,21-/m0/s1
• InChI Key: CKSZVVYEZUCUBU-KKSFZXQISA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₃H₂₄O₇
• Molecular Weight: 412.40 g/mol
• Exact Mass: 412.15220310 g/mol
• Topological Polar Surface Area (TPSA): 116.00 Ų
• XlogP: 3.60
• Atomic LogP (AlogP): 3.39
• H-Bond Acceptor: 7
• H-Bond Donor: 4
• Rotatable Bonds: 2

Synonyms

• 124676-45-5
• rel-(3R,4R)-9-(1,1-Dimethyl-2-propen-1-yl)-3,4-dihydro-3,4,8,11-tetrahydroxy-2,2-dimethylpyrano[3,2-c]xanthen-7(2H)-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9623	96.23%
Caco-2	-	0.6864	68.64%
Blood Brain Barrier	-	0.7250	72.50%
Human oral bioavailability	+	0.5429	54.29%
Subcellular localzation	Mitochondria	0.7249	72.49%
OATP2B1 inhibitior	-	0.5657	56.57%
OATP1B1 inhibitior	+	0.8735	87.35%
OATP1B3 inhibitior	+	0.9803	98.03%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	+	0.7819	78.19%
P-glycoprotein inhibitior	-	0.4472	44.72%
P-glycoprotein substrate	-	0.5373	53.73%
CYP3A4 substrate	+	0.6646	66.46%
CYP2C9 substrate	-	0.6318	63.18%
CYP2D6 substrate	-	0.8327	83.27%
CYP3A4 inhibition	-	0.5942	59.42%
CYP2C9 inhibition	-	0.7395	73.95%
CYP2C19 inhibition	-	0.6173	61.73%
CYP2D6 inhibition	-	0.8657	86.57%
CYP1A2 inhibition	+	0.6207	62.07%
CYP2C8 inhibition	+	0.6798	67.98%
CYP inhibitory promiscuity	-	0.6656	66.56%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5922	59.22%
Eye corrosion	-	0.9884	98.84%
Eye irritation	-	0.7267	72.67%
Skin irritation	-	0.6835	68.35%
Skin corrosion	-	0.8770	87.70%
Ames mutagenesis	+	0.6200	62.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6721	67.21%
Micronuclear	+	0.6700	67.00%
Hepatotoxicity	-	0.5250	52.50%
skin sensitisation	-	0.6622	66.22%
Respiratory toxicity	+	0.6556	65.56%
Reproductive toxicity	+	0.6333	63.33%
Mitochondrial toxicity	-	0.5000	50.00%
Nephrotoxicity	+	0.5062	50.62%
Acute Oral Toxicity (c)	III	0.6632	66.32%
Estrogen receptor binding	+	0.7754	77.54%
Androgen receptor binding	+	0.6730	67.30%
Thyroid receptor binding	+	0.6009	60.09%
Glucocorticoid receptor binding	+	0.7825	78.25%
Aromatase binding	+	0.8028	80.28%
PPAR gamma	+	0.7410	74.10%
Honey bee toxicity	-	0.7359	73.59%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	+	0.5800	58.00%
Fish aquatic toxicity	+	0.9887	98.87%

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	99.59%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	96.77%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.03%	95.56%
CHEMBL2581	P07339	Cathepsin D	94.93%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.41%	94.45%
CHEMBL3401	O75469	Pregnane X receptor	90.21%	94.73%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.03%	86.33%
CHEMBL1951	P21397	Monoamine oxidase A	87.74%	91.49%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.47%	95.89%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.09%	99.23%
CHEMBL3192	Q9BY41	Histone deacetylase 8	86.75%	93.99%
CHEMBL5966	P55899	IgG receptor FcRn large subunit p51	86.33%	90.93%
CHEMBL4530	P00488	Coagulation factor XIII	86.07%	96.00%
CHEMBL1937	Q92769	Histone deacetylase 2	85.70%	94.75%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	85.42%	97.33%
CHEMBL241	Q14432	Phosphodiesterase 3A	84.62%	92.94%
CHEMBL1902	P62942	FK506-binding protein 1A	83.98%	97.05%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	82.96%	100.00%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	81.33%	89.34%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	81.18%	94.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.26%	100.00%

Plants that contains it

• Garcinia gerrardii

Cross-Links

• PubChem: 163056261
• LOTUS: LTS0011417
• wikiData: Q104962754