Garcinone E

Details

• Internal ID: 66672dc9-251f-4f92-93e3-a0ae5d3d6086
• Taxonomy: Organoheterocyclic compounds > Benzopyrans > 1-benzopyrans > Xanthones > 8-prenylated xanthones
• IUPAC Name: 2,3,6,8-tetrahydroxy-1,4,7-tris(3-methylbut-2-enyl)xanthen-9-one
• SMILES (Canonical): CC(=CCC1=C(C2=C(C=C1O)OC3=C(C(=C(C(=C3C2=O)CC=C(C)C)O)O)CC=C(C)C)O)C
• SMILES (Isomeric): CC(=CCC1=C(C2=C(C=C1O)OC3=C(C(=C(C(=C3C2=O)CC=C(C)C)O)O)CC=C(C)C)O)C
• InChI: InChI=1S/C28H32O6/c1-14(2)7-10-17-20(29)13-21-23(24(17)30)27(33)22-18(11-8-15(3)4)25(31)26(32)19(28(22)34-21)12-9-16(5)6/h7-9,13,29-32H,10-12H2,1-6H3
• InChI Key: WVJYEKGQSBGNRP-UHFFFAOYSA-N
• Popularity: 17 references 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): 107.00 Ų
• XlogP: 7.90
• Atomic LogP (AlogP): 6.29
• H-Bond Acceptor: 6
• H-Bond Donor: 4
• Rotatable Bonds: 6

Synonyms

• 112649-21-5
• 83JJA5L4ZG
• UNII-83JJA5L4ZG
• 2,3,6,8-tetrahydroxy-1,4,7-tris(3-methylbut-2-enyl)xanthen-9-one
• CHEMBL454580
• 7-O-Demethyl-5-prenyl-alpha-mangostin
• 1,4,7-Tris(3-methylbut-2-enyl)-2,3,6,8-tetrakis(oxidanyl)xanthen-9-one
• 9H-Xanthen-9-one, 2,3,6,8-tetrahydroxy-1,4,7-tris(3-methyl-2-buten-1-yl)-
• 2,3,6,8-TETRAHYDROXY-1,4,7-TRIS(3-METHYLBUT-2-EN-1-YL)-9H-XANTHEN-9-ONE
• MLS000863599
• MEGxp0_001391
• SCHEMBL4755998
• ACon0_000339
• ACon1_001486
• CHEBI:185712
• cid_10298511
• DTXSID001318292
• HMS2269C06
• REGID_for_CID_10298511
• BDBM50242205
• AKOS040761773
• NCGC00180455-01
• SMR000440775
• HY-123901
• CS-0086788
• 7-O-DEMETHYL-5-PRENYL-.ALPHA.-MANGOSTIN
• BRD-K71193328-001-01-5

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9465	94.65%
Caco-2	-	0.7296	72.96%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	+	0.5571	55.71%
Subcellular localzation	Mitochondria	0.5218	52.18%
OATP2B1 inhibitior	+	0.5790	57.90%
OATP1B1 inhibitior	+	0.9049	90.49%
OATP1B3 inhibitior	+	0.9804	98.04%
MATE1 inhibitior	-	0.7000	70.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.7154	71.54%
P-glycoprotein inhibitior	+	0.6396	63.96%
P-glycoprotein substrate	-	0.8394	83.94%
CYP3A4 substrate	-	0.5276	52.76%
CYP2C9 substrate	-	0.6039	60.39%
CYP2D6 substrate	-	0.8389	83.89%
CYP3A4 inhibition	-	0.7973	79.73%
CYP2C9 inhibition	+	0.7988	79.88%
CYP2C19 inhibition	+	0.7334	73.34%
CYP2D6 inhibition	+	0.5063	50.63%
CYP1A2 inhibition	+	0.8535	85.35%
CYP2C8 inhibition	-	0.7043	70.43%
CYP inhibitory promiscuity	+	0.7829	78.29%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.7043	70.43%
Eye corrosion	-	0.9905	99.05%
Eye irritation	-	0.7783	77.83%
Skin irritation	-	0.7006	70.06%
Skin corrosion	-	0.9132	91.32%
Ames mutagenesis	+	0.6200	62.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3799	37.99%
Micronuclear	-	0.5100	51.00%
Hepatotoxicity	-	0.6947	69.47%
skin sensitisation	-	0.7155	71.55%
Respiratory toxicity	+	0.6444	64.44%
Reproductive toxicity	+	0.8444	84.44%
Mitochondrial toxicity	+	0.7500	75.00%
Nephrotoxicity	-	0.7758	77.58%
Acute Oral Toxicity (c)	III	0.5700	57.00%
Estrogen receptor binding	+	0.9011	90.11%
Androgen receptor binding	+	0.6939	69.39%
Thyroid receptor binding	+	0.5708	57.08%
Glucocorticoid receptor binding	+	0.8108	81.08%
Aromatase binding	+	0.7491	74.91%
PPAR gamma	+	0.8846	88.46%
Honey bee toxicity	-	0.8730	87.30%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5800	58.00%
Fish aquatic toxicity	+	0.9924	99.24%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293237	P54132	Bloom syndrome protein	28183.8 nM	Potency	via CMAUP
CHEMBL1978	P11511	Cytochrome P450 19A1	25100 nM	IC50	PMID: 18558747
CHEMBL2392	P06746	DNA polymerase beta	44668.4 nM	Potency	via CMAUP
CHEMBL4158	P49327	Fatty acid synthase	3300 nM	IC50	PMID: 20817450
CHEMBL1293226	B2RXH2	Lysine-specific demethylase 4D-like	28183.8 nM	Potency	via CMAUP
CHEMBL4040	P28482	MAP kinase ERK2	14125.4 nM	Potency	via CMAUP
CHEMBL1293224	P10636	Microtubule-associated protein tau	22387.2 nM; 14125.4 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1741176	P17861	X-box-binding protein 1	5240 nM	IC50	via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.44%	91.11%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	98.18%	89.34%
CHEMBL2581	P07339	Cathepsin D	94.13%	98.95%
CHEMBL3401	O75469	Pregnane X receptor	93.94%	94.73%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.15%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.65%	86.33%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	87.60%	96.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.94%	95.56%
CHEMBL3060	Q9Y345	Glycine transporter 2	82.49%	99.17%
CHEMBL3194	P02766	Transthyretin	82.17%	90.71%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	81.56%	94.00%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	81.40%	97.21%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	80.94%	90.71%

Plants that contains it

• Aster bellidiastrum
• Caragana halodendron
• Cistanche salsa
• Davallia divaricata
• Dolomiaea souliei
• Eucalyptus camaldulensis
• Garcinia costata
• Garcinia mangostana
• Garcinia morella
• Garcinia oblongifolia
• Garcinia xipshuanbannaensis
• Hypericum perforatum
• Ligularia vellerea
• Lonicera hypoleuca
• Nicotiana sylvestris
• Pentadesma butyracea
• Piper wightii
• Serpocaulon triseriale
• Trifolium resupinatum

Cross-Links

• PubChem: 10298511
• NPASS: NPC119224
• ChEMBL: CHEMBL454580
• LOTUS: LTS0075006
• wikiData: Q104399550