Garcinone C

Details

• Internal ID: 4bfadb10-d747-4323-b264-4512a9b60bcf
• Taxonomy: Organoheterocyclic compounds > Benzopyrans > 1-benzopyrans > Xanthones > 8-prenylated xanthones
• IUPAC Name: 1,3,6,7-tetrahydroxy-8-(3-hydroxy-3-methylbutyl)-2-(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)CCC(C)(C)O)O)C
• SMILES (Isomeric): CC(=CCC1=C(C2=C(C=C1O)OC3=C(C2=O)C(=C(C(=C3)O)O)CCC(C)(C)O)O)C
• InChI: InChI=1S/C23H26O7/c1-11(2)5-6-12-14(24)9-17-19(21(12)27)22(28)18-13(7-8-23(3,4)29)20(26)15(25)10-16(18)30-17/h5,9-10,24-27,29H,6-8H2,1-4H3
• InChI Key: HLOCLVMUASBDDP-UHFFFAOYSA-N
• Popularity: 13 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₃H₂₆O₇
• Molecular Weight: 414.40 g/mol
• Exact Mass: 414.16785316 g/mol
• Topological Polar Surface Area (TPSA): 127.00 Ų
• XlogP: 4.60
• Atomic LogP (AlogP): 3.98
• H-Bond Acceptor: 7
• H-Bond Donor: 5
• Rotatable Bonds: 5

Synonyms

• 76996-27-5
• 1,3,6,7-tetrahydroxy-8-(3-hydroxy-3-methylbutyl)-2-(3-methylbut-2-enyl)xanthen-9-one
• CHEMBL4440642
• 1,3,6,7-TETRAHYDROXY-8-(3-HYDROXY-3-METHYLBUTYL)-2-(3-METHYLBUT-2-EN-1-YL)-9H-XANTHEN-9-ONE
• GarcinoneC
• Garcinone-C
• DTXSID60657670
• CHEBI:175308
• HY-N6954
• BDBM50509699
• AKOS032948214
• MS-27173
• CS-0027744
• FT-0686618
• A14802
• F82148

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9600	96.00%
Caco-2	-	0.5514	55.14%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	+	0.5857	58.57%
Subcellular localzation	Mitochondria	0.5814	58.14%
OATP2B1 inhibitior	-	0.5532	55.32%
OATP1B1 inhibitior	+	0.8995	89.95%
OATP1B3 inhibitior	+	0.9589	95.89%
MATE1 inhibitior	-	0.6200	62.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	-	0.4778	47.78%
P-glycoprotein inhibitior	-	0.6212	62.12%
P-glycoprotein substrate	-	0.6852	68.52%
CYP3A4 substrate	+	0.5265	52.65%
CYP2C9 substrate	-	0.6000	60.00%
CYP2D6 substrate	-	0.8446	84.46%
CYP3A4 inhibition	-	0.6960	69.60%
CYP2C9 inhibition	-	0.6107	61.07%
CYP2C19 inhibition	-	0.5077	50.77%
CYP2D6 inhibition	-	0.7530	75.30%
CYP1A2 inhibition	+	0.5783	57.83%
CYP2C8 inhibition	-	0.5914	59.14%
CYP inhibitory promiscuity	-	0.6656	66.56%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.6813	68.13%
Eye corrosion	-	0.9917	99.17%
Eye irritation	-	0.6037	60.37%
Skin irritation	-	0.6814	68.14%
Skin corrosion	-	0.9011	90.11%
Ames mutagenesis	+	0.6100	61.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4494	44.94%
Micronuclear	-	0.7400	74.00%
Hepatotoxicity	-	0.5968	59.68%
skin sensitisation	-	0.7405	74.05%
Respiratory toxicity	+	0.6778	67.78%
Reproductive toxicity	+	0.9556	95.56%
Mitochondrial toxicity	+	0.8250	82.50%
Nephrotoxicity	-	0.8739	87.39%
Acute Oral Toxicity (c)	III	0.5283	52.83%
Estrogen receptor binding	+	0.9006	90.06%
Androgen receptor binding	+	0.7418	74.18%
Thyroid receptor binding	+	0.5508	55.08%
Glucocorticoid receptor binding	+	0.8494	84.94%
Aromatase binding	+	0.7490	74.90%
PPAR gamma	+	0.9094	90.94%
Honey bee toxicity	-	0.8345	83.45%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	+	0.5300	53.00%
Fish aquatic toxicity	+	0.9804	98.04%

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	99.49%	91.11%
CHEMBL3401	O75469	Pregnane X receptor	96.53%	94.73%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	95.68%	89.34%
CHEMBL2581	P07339	Cathepsin D	94.42%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.58%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.25%	89.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.37%	94.45%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	85.28%	94.00%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	85.23%	96.95%
CHEMBL3038469	P24941	CDK2/Cyclin A	83.23%	91.38%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.06%	95.56%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.51%	99.17%
CHEMBL3194	P02766	Transthyretin	80.41%	90.71%

Plants that contains it

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

Cross-Links

• PubChem: 44159808
• NPASS: NPC92032
• LOTUS: LTS0066957
• wikiData: Q72480074