Gartanin

Details

• Internal ID: 7fbbed7b-2add-41aa-a5ba-471847cfe6c5
• Taxonomy: Organoheterocyclic compounds > Benzopyrans > 1-benzopyrans > Xanthones > 4-prenylated xanthones
• IUPAC Name: 1,3,5,8-tetrahydroxy-2,4-bis(3-methylbut-2-enyl)xanthen-9-one
• SMILES (Canonical): CC(=CCC1=C(C(=C2C(=C1O)C(=O)C3=C(C=CC(=C3O2)O)O)CC=C(C)C)O)C
• SMILES (Isomeric): CC(=CCC1=C(C(=C2C(=C1O)C(=O)C3=C(C=CC(=C3O2)O)O)CC=C(C)C)O)C
• InChI: InChI=1S/C23H24O6/c1-11(2)5-7-13-19(26)14(8-6-12(3)4)22-18(20(13)27)21(28)17-15(24)9-10-16(25)23(17)29-22/h5-6,9-10,24-27H,7-8H2,1-4H3
• InChI Key: OJXQLGQIDIPMTE-UHFFFAOYSA-N
• Popularity: 20 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

• 33390-42-0
• 1,3,5,8-Tetrahydroxy-2,4-bis(3-methylbut-2-en-1-yl)-9H-xanthen-9-one
• Gartinin
• 9H-Xanthen-9-one, 1,3,5,8-tetrahydroxy-2,4-bis(3-methyl-2-butenyl)-
• 1,3,5,8-tetrahydroxy-2,4-bis(3-methylbut-2-enyl)xanthen-9-one
• CHEBI:5279
• CHEMBL487992
• 1,3,5,8-Tetrahydroxy-2,4-diprenylxanthone
• MK212HYDROCHLORIDE
• D0O8EB
• 1,3,5,8-TETRAHYDROXY-2,4-BIS(3-METHYL-2-BUTENYL)-9H-XANTHEN-9-ONE
• SCHEMBL1516414
• DTXSID20187024
• HY-N6038
• BDBM50311743
• NSC692946
• AKOS016009589
• NSC-692946
• MS-26677
• CS-0032218
• FT-0686620
• Q-100408
• Q27106703
• 1,3,5,8-Tetrahydroxy-2,4-bis(3-methyl-2-butenyl)-9H-xanthen-9-one, 9CI

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9855	98.55%
Caco-2	-	0.6397	63.97%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.5811	58.11%
OATP2B1 inhibitior	+	0.5837	58.37%
OATP1B1 inhibitior	+	0.8960	89.60%
OATP1B3 inhibitior	+	0.9456	94.56%
MATE1 inhibitior	-	0.7400	74.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.6301	63.01%
P-glycoprotein inhibitior	-	0.5295	52.95%
P-glycoprotein substrate	-	0.8780	87.80%
CYP3A4 substrate	-	0.5489	54.89%
CYP2C9 substrate	-	0.5755	57.55%
CYP2D6 substrate	-	0.8328	83.28%
CYP3A4 inhibition	-	0.7858	78.58%
CYP2C9 inhibition	+	0.8121	81.21%
CYP2C19 inhibition	+	0.8262	82.62%
CYP2D6 inhibition	-	0.6117	61.17%
CYP1A2 inhibition	+	0.8597	85.97%
CYP2C8 inhibition	-	0.8264	82.64%
CYP inhibitory promiscuity	+	0.8399	83.99%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.7457	74.57%
Eye corrosion	-	0.9893	98.93%
Eye irritation	+	0.7302	73.02%
Skin irritation	-	0.7124	71.24%
Skin corrosion	-	0.9331	93.31%
Ames mutagenesis	+	0.7236	72.36%
Human Ether-a-go-go-Related Gene inhibition	-	0.5276	52.76%
Micronuclear	-	0.5200	52.00%
Hepatotoxicity	+	0.5625	56.25%
skin sensitisation	-	0.6833	68.33%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.7125	71.25%
Nephrotoxicity	+	0.5165	51.65%
Acute Oral Toxicity (c)	III	0.6305	63.05%
Estrogen receptor binding	+	0.8938	89.38%
Androgen receptor binding	+	0.7212	72.12%
Thyroid receptor binding	+	0.5390	53.90%
Glucocorticoid receptor binding	+	0.8643	86.43%
Aromatase binding	+	0.6054	60.54%
PPAR gamma	+	0.9486	94.86%
Honey bee toxicity	-	0.8998	89.98%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.6200	62.00%
Fish aquatic toxicity	+	0.9947	99.47%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL5533	Q04206	Nuclear factor NF-kappa-B p65 subunit	19000 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	98.88%	91.11%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	95.99%	89.34%
CHEMBL2581	P07339	Cathepsin D	93.89%	98.95%
CHEMBL3401	O75469	Pregnane X receptor	93.06%	94.73%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.68%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.16%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.32%	89.00%
CHEMBL1163101	O75460	Serine/threonine-protein kinase/endoribonuclease IRE1	85.68%	98.11%
CHEMBL1951	P21397	Monoamine oxidase A	83.87%	91.49%
CHEMBL4224	P49759	Dual specificty protein kinase CLK1	83.48%	85.30%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.24%	86.33%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	80.39%	94.00%

Plants that contains it

• Aster bellidiastrum
• Caragana halodendron
• Davallia divaricata
• Dolomiaea souliei
• Eucalyptus camaldulensis
• Garcinia dulcis
• Garcinia mangostana
• Garcinia morella
• Garcinia staudtii
• Ligularia vellerea
• Lonicera hypoleuca
• Maclura tinctoria
• Morus insignis
• Nicotiana sylvestris
• Pentadesma butyracea
• Serpocaulon triseriale

Cross-Links

• PubChem: 5281633
• NPASS: NPC191146
• ChEMBL: CHEMBL487992
• LOTUS: LTS0169459
• wikiData: Q27106703