Beta-Mangostin

Details

• Internal ID: 617d8eb7-b482-438d-bf3e-9ba6624fc764
• Taxonomy: Organoheterocyclic compounds > Benzopyrans > 1-benzopyrans > Xanthones > 8-prenylated xanthones
• IUPAC Name: 1,6-dihydroxy-3,7-dimethoxy-2,8-bis(3-methylbut-2-enyl)xanthen-9-one
• SMILES (Canonical): CC(=CCC1=C(C=C2C(=C1O)C(=O)C3=C(O2)C=C(C(=C3CC=C(C)C)OC)O)OC)C
• SMILES (Isomeric): CC(=CCC1=C(C=C2C(=C1O)C(=O)C3=C(O2)C=C(C(=C3CC=C(C)C)OC)O)OC)C
• InChI: InChI=1S/C25H28O6/c1-13(2)7-9-15-18(29-5)12-20-22(23(15)27)24(28)21-16(10-8-14(3)4)25(30-6)17(26)11-19(21)31-20/h7-8,11-12,26-27H,9-10H2,1-6H3
• InChI Key: YRKKJHJIWCRNCW-UHFFFAOYSA-N
• Popularity: 44 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₅H₂₈O₆
• Molecular Weight: 424.50 g/mol
• Exact Mass: 424.18858861 g/mol
• Topological Polar Surface Area (TPSA): 85.20 Ų
• XlogP: 6.60
• Atomic LogP (AlogP): 5.39
• H-Bond Acceptor: 6
• H-Bond Donor: 2
• Rotatable Bonds: 6

Synonyms

• 20931-37-7
• b-Mangostin
• 1,6-dihydroxy-3,7-dimethoxy-2,8-bis(3-methylbut-2-enyl)xanthen-9-one
• CHEMBL261706
• 1,6-Dihydroxy-3,7-dimethoxy-2,8-diprenylxanthone
• 1,6-DIHYDROXY-3,7-DIMETHOXY-2,8-BIS(3-METHYLBUT-2-EN-1-YL)-9H-XANTHEN-9-ONE
• ??Mangostin
• SCHEMBL3742268
• DTXSID40420546
• CHEBI:175406
• YRKKJHJIWCRNCW-UHFFFAOYSA-N
• HY-N0941
• BDBM50241454
• 1,6-dihydroxy-3,7-dimethoxy-2,8-bis(3-methylbut-2-enyl)-9H-xanthen-9-one
• AKOS030526115
• CS-5295
• AC-34157
• MS-27465
• FT-0700515
• A14843
• Q-100264
• (2-methyl-1-propyl-1H-indol-3-yl)(naphthalen-1-yl)methanone
• 1,6-Dihydroxy-3,7-dimethoxy-2,8-bis(3-methyl-2-buten-1-yl)-9H-xanthen-9-one
• 1,6-Dihydroxy-3,7-dimethoxy-2,8-bis(3-methyl-2-butenyl)-9H-xanthen-9-one
• 9H-Xanthen-9-one, 1,6-dihydroxy-3,7-dimethoxy-2,8-bis(3-methyl-2-butenyl)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9785	97.85%
Caco-2	+	0.7443	74.43%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	+	0.6429	64.29%
Subcellular localzation	Mitochondria	0.5950	59.50%
OATP2B1 inhibitior	-	0.7128	71.28%
OATP1B1 inhibitior	+	0.9325	93.25%
OATP1B3 inhibitior	+	0.9421	94.21%
MATE1 inhibitior	-	0.8200	82.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.8635	86.35%
P-glycoprotein inhibitior	+	0.7942	79.42%
P-glycoprotein substrate	-	0.7269	72.69%
CYP3A4 substrate	+	0.5477	54.77%
CYP2C9 substrate	-	0.5929	59.29%
CYP2D6 substrate	-	0.8145	81.45%
CYP3A4 inhibition	-	0.8605	86.05%
CYP2C9 inhibition	+	0.8972	89.72%
CYP2C19 inhibition	+	0.9226	92.26%
CYP2D6 inhibition	+	0.8037	80.37%
CYP1A2 inhibition	+	0.9107	91.07%
CYP2C8 inhibition	+	0.5000	50.00%
CYP inhibitory promiscuity	+	0.8649	86.49%
UGT catelyzed	-	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6900	69.00%
Eye corrosion	-	0.9895	98.95%
Eye irritation	-	0.6434	64.34%
Skin irritation	-	0.7562	75.62%
Skin corrosion	-	0.9540	95.40%
Ames mutagenesis	-	0.5300	53.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4096	40.96%
Micronuclear	-	0.5400	54.00%
Hepatotoxicity	-	0.5500	55.00%
skin sensitisation	-	0.8057	80.57%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	+	0.8250	82.50%
Nephrotoxicity	-	0.8671	86.71%
Acute Oral Toxicity (c)	III	0.6502	65.02%
Estrogen receptor binding	+	0.8833	88.33%
Androgen receptor binding	+	0.6457	64.57%
Thyroid receptor binding	+	0.5421	54.21%
Glucocorticoid receptor binding	+	0.8545	85.45%
Aromatase binding	+	0.7139	71.39%
PPAR gamma	+	0.8633	86.33%
Honey bee toxicity	-	0.7212	72.12%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.5300	53.00%
Fish aquatic toxicity	+	0.9881	98.81%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL4158	P49327	Fatty acid synthase	24830 nM	IC50	PMID: 20817450
CHEMBL2007625	O75874	Isocitrate dehydrogenase [NADP] cytoplasmic	12000 nM	Ki	PMID: 26508549
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	7500 nM	IC50	PMID: 19839614
CHEMBL5533	Q04206	Nuclear factor NF-kappa-B p65 subunit	12100 nM	IC50	PMID: 19839614

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.09%	91.11%
CHEMBL2581	P07339	Cathepsin D	93.15%	98.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	91.97%	94.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.08%	94.45%
CHEMBL3060	Q9Y345	Glycine transporter 2	90.56%	99.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.38%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.07%	89.00%
CHEMBL3401	O75469	Pregnane X receptor	89.26%	94.73%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	87.79%	85.14%
CHEMBL1163101	O75460	Serine/threonine-protein kinase/endoribonuclease IRE1	87.16%	98.11%
CHEMBL1937	Q92769	Histone deacetylase 2	87.08%	94.75%
CHEMBL3194	P02766	Transthyretin	86.15%	90.71%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	86.10%	89.34%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	84.94%	96.00%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	84.48%	96.95%
CHEMBL3192	Q9BY41	Histone deacetylase 8	82.37%	93.99%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	80.45%	96.09%

Plants that contains it

• Allium cepa
• Aster bellidiastrum
• Caragana halodendron
• Cratoxylum cochinchinense
• Cratoxylum formosum
• Cratoxylum sumatranum
• Davallia divaricata
• Dolomiaea souliei
• Eucalyptus camaldulensis
• Garcinia cowa
• Garcinia dulcis
• Garcinia fusca
• Garcinia mangostana
• Garcinia oliveri
• Ligularia vellerea
• Lonicera hypoleuca
• Nicotiana sylvestris
• Serpocaulon triseriale

Cross-Links

• PubChem: 5495925
• NPASS: NPC14353
• ChEMBL: CHEMBL261706
• LOTUS: LTS0240441
• wikiData: Q105230137