Garcinone A

Details

• Internal ID: 99393907-bff1-49ea-a4cb-d681d6bd6f48
• Taxonomy: Organoheterocyclic compounds > Benzopyrans > 1-benzopyrans > Xanthones > 4-prenylated xanthones
• IUPAC Name: 1,3,6-trihydroxy-2,4-bis(3-methylbut-2-enyl)xanthen-9-one
• SMILES (Canonical): CC(=CCC1=C(C(=C2C(=C1O)C(=O)C3=C(O2)C=C(C=C3)O)CC=C(C)C)O)C
• SMILES (Isomeric): CC(=CCC1=C(C(=C2C(=C1O)C(=O)C3=C(O2)C=C(C=C3)O)CC=C(C)C)O)C
• InChI: InChI=1S/C23H24O5/c1-12(2)5-8-16-20(25)17(9-6-13(3)4)23-19(22(16)27)21(26)15-10-7-14(24)11-18(15)28-23/h5-7,10-11,24-25,27H,8-9H2,1-4H3
• InChI Key: HHHZYUKPVCUMDR-UHFFFAOYSA-N
• Popularity: 4 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₃H₂₄O₅
• Molecular Weight: 380.40 g/mol
• Exact Mass: 380.16237386 g/mol
• Topological Polar Surface Area (TPSA): 87.00 Ų
• XlogP: 6.30
• Atomic LogP (AlogP): 5.08
• H-Bond Acceptor: 5
• H-Bond Donor: 3
• Rotatable Bonds: 4

Synonyms

• CHEMBL2029703
• CHEBI:175006
• 1,3,6-trihydroxy-2,4-bis(3-methylbut-2-enyl)xanthen-9-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9901	99.01%
Caco-2	+	0.5000	50.00%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	+	0.5286	52.86%
Subcellular localzation	Mitochondria	0.7091	70.91%
OATP2B1 inhibitior	+	0.5780	57.80%
OATP1B1 inhibitior	+	0.8124	81.24%
OATP1B3 inhibitior	+	0.9450	94.50%
MATE1 inhibitior	-	0.7400	74.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.7307	73.07%
P-glycoprotein inhibitior	+	0.5970	59.70%
P-glycoprotein substrate	-	0.5751	57.51%
CYP3A4 substrate	+	0.5264	52.64%
CYP2C9 substrate	-	0.5755	57.55%
CYP2D6 substrate	-	0.8328	83.28%
CYP3A4 inhibition	-	0.6682	66.82%
CYP2C9 inhibition	+	0.8254	82.54%
CYP2C19 inhibition	+	0.8703	87.03%
CYP2D6 inhibition	-	0.6789	67.89%
CYP1A2 inhibition	+	0.9044	90.44%
CYP2C8 inhibition	-	0.5974	59.74%
CYP inhibitory promiscuity	+	0.8828	88.28%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.7426	74.26%
Eye corrosion	-	0.9897	98.97%
Eye irritation	+	0.6928	69.28%
Skin irritation	-	0.7196	71.96%
Skin corrosion	-	0.9401	94.01%
Ames mutagenesis	-	0.5000	50.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5971	59.71%
Micronuclear	-	0.5200	52.00%
Hepatotoxicity	+	0.6000	60.00%
skin sensitisation	-	0.6866	68.66%
Respiratory toxicity	+	0.6556	65.56%
Reproductive toxicity	+	0.7889	78.89%
Mitochondrial toxicity	+	0.7250	72.50%
Nephrotoxicity	-	0.7095	70.95%
Acute Oral Toxicity (c)	III	0.6365	63.65%
Estrogen receptor binding	+	0.9122	91.22%
Androgen receptor binding	+	0.8617	86.17%
Thyroid receptor binding	+	0.5653	56.53%
Glucocorticoid receptor binding	+	0.8583	85.83%
Aromatase binding	+	0.6721	67.21%
PPAR gamma	+	0.9477	94.77%
Honey bee toxicity	-	0.8582	85.82%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.6200	62.00%
Fish aquatic toxicity	+	0.9962	99.62%

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	99.21%	91.11%
CHEMBL2581	P07339	Cathepsin D	96.87%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.13%	94.45%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.40%	89.00%
CHEMBL3401	O75469	Pregnane X receptor	93.95%	94.73%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.51%	95.56%
CHEMBL1951	P21397	Monoamine oxidase A	89.88%	91.49%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.88%	86.33%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	86.40%	89.34%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	83.17%	94.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	82.60%	99.17%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.02%	99.23%

Plants that contains it

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

Cross-Links

• PubChem: 70689919
• NPASS: NPC69769
• LOTUS: LTS0183316
• wikiData: Q105028299