Gentiacaulein

Details

• Internal ID: dcc26eee-e485-473b-ba25-aa64c31217bb
• Taxonomy: Organoheterocyclic compounds > Benzopyrans > 1-benzopyrans > Xanthones
• IUPAC Name: 2,8-dihydroxy-1,6-dimethoxyxanthen-9-one
• SMILES (Canonical): COC1=CC(=C2C(=C1)OC3=C(C2=O)C(=C(C=C3)O)OC)O
• SMILES (Isomeric): COC1=CC(=C2C(=C1)OC3=C(C2=O)C(=C(C=C3)O)OC)O
• InChI: InChI=1S/C15H12O6/c1-19-7-5-9(17)12-11(6-7)21-10-4-3-8(16)15(20-2)13(10)14(12)18/h3-6,16-17H,1-2H3
• InChI Key: WYOSCUWDVFHQFY-UHFFFAOYSA-N
• Popularity: 24 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₂O₆
• Molecular Weight: 288.25 g/mol
• Exact Mass: 288.06338810 g/mol
• Topological Polar Surface Area (TPSA): 85.20 Ų
• XlogP: 2.70
• Atomic LogP (AlogP): 2.37
• H-Bond Acceptor: 6
• H-Bond Donor: 2
• Rotatable Bonds: 2

Synonyms

• 15402-27-4
• 2,6-dimethoxyxanthone
• 2,8-dihydroxy-1,6-dimethoxyxanthone
• Getiacaulein
• NSC661743
• 2,8-dihydroxy-1,6-dimethoxyxanthen-9-one
• MLS000563494
• CHEBI:5313
• 2,8-Dihydroxy-1,6-dimethoxy-9H-xanthen-9-one
• 2,8-dihydroxy-1,6-dimethoxy-xanthen-9-one
• AC1NQYS1
• CHEMBL467590
• DTXSID10415161
• BDBM174835
• HMS2227I16
• HMS3338N03
• 1,7-dihydroxy-3,8-dimethoxyxanthone
• NSC-661743
• SMR000232301
• US9114126, 2027BA1
• Q27106712

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9642	96.42%
Caco-2	+	0.7107	71.07%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Mitochondria	0.7364	73.64%
OATP2B1 inhibitior	-	0.7092	70.92%
OATP1B1 inhibitior	+	0.9272	92.72%
OATP1B3 inhibitior	+	0.9851	98.51%
MATE1 inhibitior	+	0.5400	54.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.8296	82.96%
P-glycoprotein inhibitior	-	0.5963	59.63%
P-glycoprotein substrate	-	0.9558	95.58%
CYP3A4 substrate	-	0.5318	53.18%
CYP2C9 substrate	-	0.6401	64.01%
CYP2D6 substrate	-	0.8296	82.96%
CYP3A4 inhibition	-	0.6420	64.20%
CYP2C9 inhibition	-	0.7071	70.71%
CYP2C19 inhibition	+	0.7531	75.31%
CYP2D6 inhibition	-	0.6235	62.35%
CYP1A2 inhibition	+	0.9606	96.06%
CYP2C8 inhibition	-	0.5654	56.54%
CYP inhibitory promiscuity	+	0.6446	64.46%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6331	63.31%
Eye corrosion	-	0.9655	96.55%
Eye irritation	+	0.7853	78.53%
Skin irritation	-	0.6099	60.99%
Skin corrosion	-	0.9698	96.98%
Ames mutagenesis	+	0.8000	80.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5759	57.59%
Micronuclear	+	0.9100	91.00%
Hepatotoxicity	+	0.5375	53.75%
skin sensitisation	-	0.9149	91.49%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.6125	61.25%
Nephrotoxicity	-	0.7263	72.63%
Acute Oral Toxicity (c)	III	0.5708	57.08%
Estrogen receptor binding	+	0.8644	86.44%
Androgen receptor binding	+	0.7837	78.37%
Thyroid receptor binding	+	0.5566	55.66%
Glucocorticoid receptor binding	+	0.8824	88.24%
Aromatase binding	+	0.9000	90.00%
PPAR gamma	+	0.7947	79.47%
Honey bee toxicity	-	0.9326	93.26%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5300	53.00%
Fish aquatic toxicity	+	0.8585	85.85%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	14125.4 nM	Potency	via CMAUP
CHEMBL3577	P00352	Aldehyde dehydrogenase 1A1	22387.2 nM	Potency	via CMAUP
CHEMBL1293226	B2RXH2	Lysine-specific demethylase 4D-like	28183.8 nM	Potency	via CMAUP
CHEMBL1293224	P10636	Microtubule-associated protein tau	12589.3 nM; 25118.9 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1293235	P02545	Prelamin-A/C	15848.9 nM	Potency	via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.26%	91.11%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	95.03%	99.15%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.31%	95.56%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	93.17%	94.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.55%	94.45%
CHEMBL3192	Q9BY41	Histone deacetylase 8	88.41%	93.99%
CHEMBL4208	P20618	Proteasome component C5	87.20%	90.00%
CHEMBL2581	P07339	Cathepsin D	87.10%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.06%	89.00%
CHEMBL2535	P11166	Glucose transporter	86.44%	98.75%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.19%	86.33%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.14%	99.17%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.22%	99.23%
CHEMBL3401	O75469	Pregnane X receptor	83.22%	94.73%
CHEMBL3194	P02766	Transthyretin	82.76%	90.71%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	81.23%	80.78%

Plants that contains it

• Artemisia capillaris
• Brocchia cinerea
• Daphne genkwa
• Gentiana acaulis
• Gentianopsis ciliata
• Gentianopsis paludosa
• Glycyrrhiza glabra
• Haploclathra leiantha
• Haploclathra paniculata
• Prunus pseudocerasus
• Rosmarinus officinalis
• Swertia punicea

Cross-Links

• PubChem: 5281634
• NPASS: NPC120537
• ChEMBL: CHEMBL467590
• LOTUS: LTS0127979
• wikiData: Q27106712