gamma-Mangostin

Details

• Internal ID: 658d96b9-2f21-4b48-84d6-2c5b2f37f146
• Taxonomy: Organoheterocyclic compounds > Benzopyrans > 1-benzopyrans > Xanthones > 8-prenylated xanthones
• IUPAC Name: 1,3,6,7-tetrahydroxy-2,8-bis(3-methylbut-2-enyl)xanthen-9-one
• SMILES (Canonical): CC(=CCC1=C(C2=C(C=C1O)OC3=C(C2=O)C(=C(C(=C3)O)O)CC=C(C)C)O)C
• SMILES (Isomeric): CC(=CCC1=C(C2=C(C=C1O)OC3=C(C2=O)C(=C(C(=C3)O)O)CC=C(C)C)O)C
• InChI: InChI=1S/C23H24O6/c1-11(2)5-7-13-15(24)9-18-20(22(13)27)23(28)19-14(8-6-12(3)4)21(26)16(25)10-17(19)29-18/h5-6,9-10,24-27H,7-8H2,1-4H3
• InChI Key: VEZXFTKZUMARDU-UHFFFAOYSA-N
• Popularity: 472 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₃H₂₄O₆
• Molecular Weight: 396.40 g/mol
• Exact Mass: 396.15728848 g/mol
• Topological Polar Surface Area (TPSA): 107.00 Ų
• XlogP: 5.90
• Atomic LogP (AlogP): 4.79
• H-Bond Acceptor: 6
• H-Bond Donor: 4
• Rotatable Bonds: 4

Synonyms

• 31271-07-5
• Normangostin
• 1,3,6,7-tetrahydroxy-2,8-bis(3-methylbut-2-en-1-yl)-9H-xanthen-9-one
• G7HS6P8ZEC
• 1,3,6,7-tetrahydroxy-2,8-bis(3-methylbut-2-enyl)xanthen-9-one
• CHEBI:67548
• UNII-G7HS6P8ZEC
• CHEMBL260553
• DTXSID50185194
• 1,3,6,7-Tetrahydroxy-2,5-bis(3-methyl-2-butenyl)-9H-xanthen-9-one
• 2,8-Bis(3-methyl-2-butenyl)-1,3,6,7-tetrahydroxy-9H-xanthen-9-one
• 9H-Xanthen-9-one, 1,3,6,7-tetrahydroxy-2,8-bis(3-methyl-2-butenyl)-
• 1,7-BIS(3-METHYLBUT-2-ENYL)-2,3,6,8-TETRAKIS(OXIDANYL)XANTHEN-9-ONE
• 9H-XANTHEN-9-ONE, 1,3,6,7-TETRAHYDROXY-2,8-BIS(3-METHYL-2-BUTEN-1-YL)
• g-Mangostin
• gamma- Mangostin
• | pound- MANGOSTIN
• SCHEMBL3753526
• DTXCID60107685
• VEZXFTKZUMARDU-UHFFFAOYSA-N
• 7-O-DEMETHYL-alpha-MANGOSTIN
• HY-N1957
• gamma-Mangostin, >=98% (HPLC)
• BDBM50241453
• MFCD00951752
• PDSP1_000060
• PDSP2_000060
• AKOS022190352
• 7-O-DEMETHYL-.ALPHA.-MANGOSTIN
• AC-35173
• MS-26679
• CS-0018275
• FT-0686617
• Q-100393
• Q27136016
• 1,3,6,7-Tetrahydroxy-2,8-bis(3-methyl-2-butenyl)-9H-xanthen-9-one, 9CI
• 1,3,6,7-tetrahydroxy-2,8-bis(3-methylbut-2-enyl)-9H-xanthen-9-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9465	94.65%
Caco-2	-	0.5247	52.47%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	+	0.6714	67.14%
Subcellular localzation	Mitochondria	0.5218	52.18%
OATP2B1 inhibitior	+	0.5811	58.11%
OATP1B1 inhibitior	+	0.9240	92.40%
OATP1B3 inhibitior	+	0.9804	98.04%
MATE1 inhibitior	-	0.7000	70.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.5228	52.28%
P-glycoprotein inhibitior	-	0.5403	54.03%
P-glycoprotein substrate	-	0.8656	86.56%
CYP3A4 substrate	-	0.5627	56.27%
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	-	0.7596	75.96%
CYP inhibitory promiscuity	+	0.7829	78.29%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.7043	70.43%
Eye corrosion	-	0.9905	99.05%
Eye irritation	-	0.5246	52.46%
Skin irritation	-	0.7006	70.06%
Skin corrosion	-	0.9132	91.32%
Ames mutagenesis	+	0.6000	60.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4143	41.43%
Micronuclear	-	0.5100	51.00%
Hepatotoxicity	-	0.6000	60.00%
skin sensitisation	-	0.7155	71.55%
Respiratory toxicity	+	0.6778	67.78%
Reproductive toxicity	+	0.8444	84.44%
Mitochondrial toxicity	+	0.7500	75.00%
Nephrotoxicity	-	0.8053	80.53%
Acute Oral Toxicity (c)	III	0.5700	57.00%
Estrogen receptor binding	+	0.9023	90.23%
Androgen receptor binding	+	0.7395	73.95%
Thyroid receptor binding	-	0.5124	51.24%
Glucocorticoid receptor binding	+	0.7852	78.52%
Aromatase binding	+	0.6634	66.34%
PPAR gamma	+	0.9227	92.27%
Honey bee toxicity	-	0.8941	89.41%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.5200	52.00%
Fish aquatic toxicity	+	0.9924	99.24%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL221	P23219	Cyclooxygenase-1	800 nM	IC50	PMID: 16038536
CHEMBL230	P35354	Cyclooxygenase-2	2000 nM	IC50	PMID: 16038536
CHEMBL1978	P11511	Cytochrome P450 19A1	6900 nM; 4970 nM	IC50; IC50	PMID: 18558747; PMID: 18558747
CHEMBL4158	P49327	Fatty acid synthase	1240 nM	IC50	PMID: 20817450
CHEMBL2007625	O75874	Isocitrate dehydrogenase [NADP] cytoplasmic	3170 nM	Ki	PMID: 26508549

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.19%	91.11%
CHEMBL3401	O75469	Pregnane X receptor	95.18%	94.73%
CHEMBL2581	P07339	Cathepsin D	93.54%	98.95%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	93.03%	89.34%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.93%	89.00%
CHEMBL3038469	P24941	CDK2/Cyclin A	87.96%	91.38%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.52%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.88%	86.33%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	84.75%	94.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.53%	95.56%
CHEMBL3194	P02766	Transthyretin	82.08%	90.71%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.43%	99.17%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	80.24%	90.71%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	80.02%	85.14%

Plants that contains it

• Aster bellidiastrum
• Caragana halodendron
• Cratoxylum cochinchinense
• Davallia divaricata
• Dolomiaea souliei
• Eucalyptus camaldulensis
• Garcinia costata
• Garcinia esculenta
• Garcinia mangostana
• Garcinia xipshuanbannaensis
• Hypericum androsaemum
• Hypericum patulum
• Hypericum perforatum
• Ligularia vellerea
• Lonicera hypoleuca
• Nicotiana sylvestris
• Serpocaulon triseriale

Cross-Links

• PubChem: 5464078
• NPASS: NPC142339
• ChEMBL: CHEMBL260553
• LOTUS: LTS0090390
• wikiData: Q27136016