8-Desoxygartanin

Details

• Internal ID: a071f485-db46-4056-b23c-5e443ca07853
• Taxonomy: Organoheterocyclic compounds > Benzopyrans > 1-benzopyrans > Xanthones > 4-prenylated xanthones
• IUPAC Name: 1,3,5-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(=CC=C3)O)CC=C(C)C)O)C
• SMILES (Isomeric): CC(=CCC1=C(C(=C2C(=C1O)C(=O)C3=C(O2)C(=CC=C3)O)CC=C(C)C)O)C
• InChI: InChI=1S/C23H24O5/c1-12(2)8-10-14-19(25)16(11-9-13(3)4)23-18(20(14)26)21(27)15-6-5-7-17(24)22(15)28-23/h5-9,24-26H,10-11H2,1-4H3
• InChI Key: GVQOVMKBYJKZSY-UHFFFAOYSA-N
• Popularity: 14 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

• 8-DEOXYGARTANIN
• 33390-41-9
• 1,3,5-trihydroxy-2,4-bis(3-methylbut-2-enyl)xanthen-9-one
• CHEMBL488606
• 1,3,5-trihydroxy-2,4-bis(3-methylbut-2-en-1-yl)-9h-xanthen-9-one
• 9H-Xanthen-9-one, 1,3,5-trihydroxy-2,4-bis(3-methyl-2-butenyl)-
• Deoxygartinin
• NSC692944
• D01FEA
• SCHEMBL17056909
• CHEBI:175007
• DTXSID101316906
• HY-N6009
• BDBM50311742
• MFCD09264646
• AKOS028108663
• NSC-692944
• MS-26222
• PD125187
• CS-0032146
• FT-0686569
• 1,3,5-Trihydroxy-2,4-bis(3-methyl-2-butenyl)-9H-xanthen-9-one
• 1,3,5-Trihydroxy-2-(3-methyl-but-2-enyl)-4-((Z)-3-methyl-but-2-enyl)-xanthen-9-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9855	98.55%
Caco-2	+	0.4877	48.77%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	+	0.5571	55.71%
Subcellular localzation	Mitochondria	0.5811	58.11%
OATP2B1 inhibitior	+	0.5781	57.81%
OATP1B1 inhibitior	+	0.8955	89.55%
OATP1B3 inhibitior	+	0.9456	94.56%
MATE1 inhibitior	-	0.7400	74.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.7736	77.36%
P-glycoprotein inhibitior	-	0.4290	42.90%
P-glycoprotein substrate	-	0.7596	75.96%
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	-	0.7439	74.39%
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	+	0.7331	73.31%
Skin irritation	-	0.7124	71.24%
Skin corrosion	-	0.9331	93.31%
Ames mutagenesis	+	0.6600	66.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5187	51.87%
Micronuclear	-	0.5200	52.00%
Hepatotoxicity	+	0.5500	55.00%
skin sensitisation	-	0.6833	68.33%
Respiratory toxicity	+	0.7667	76.67%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.7125	71.25%
Nephrotoxicity	-	0.7013	70.13%
Acute Oral Toxicity (c)	III	0.6305	63.05%
Estrogen receptor binding	+	0.8842	88.42%
Androgen receptor binding	+	0.6545	65.45%
Thyroid receptor binding	+	0.5683	56.83%
Glucocorticoid receptor binding	+	0.8578	85.78%
Aromatase binding	+	0.5977	59.77%
PPAR gamma	+	0.9550	95.50%
Honey bee toxicity	-	0.8673	86.73%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	-	0.5400	54.00%
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	11300 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	98.24%	91.11%
CHEMBL2581	P07339	Cathepsin D	96.99%	98.95%
CHEMBL3401	O75469	Pregnane X receptor	95.89%	94.73%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.11%	95.56%
CHEMBL1951	P21397	Monoamine oxidase A	92.91%	91.49%
CHEMBL1806	P11388	DNA topoisomerase II alpha	92.64%	89.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.59%	94.45%
CHEMBL3192	Q9BY41	Histone deacetylase 8	90.49%	93.99%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	88.80%	99.23%
CHEMBL1937	Q92769	Histone deacetylase 2	87.39%	94.75%
CHEMBL3830	Q2M2I8	Adaptor-associated kinase	85.52%	83.10%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	85.46%	89.34%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	84.94%	94.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.62%	86.33%
CHEMBL3959	P16083	Quinone reductase 2	82.42%	89.49%
CHEMBL5103	Q969S8	Histone deacetylase 10	81.06%	90.08%

Plants that contains it

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

Cross-Links

• PubChem: 392450
• NPASS: NPC33051
• ChEMBL: CHEMBL488606