6-Deoxyjacareubin

Details

• Internal ID: 9d6cf343-f1e5-4f78-afe9-39f90c4dee1b
• Taxonomy: Organoheterocyclic compounds > Benzopyrans > 1-benzopyrans > Xanthones > Pyranoxanthones
• IUPAC Name: 5,10-dihydroxy-2,2-dimethylpyrano[3,2-b]xanthen-6-one
• SMILES (Canonical): CC1(C=CC2=C(O1)C=C3C(=C2O)C(=O)C4=C(O3)C(=CC=C4)O)C
• SMILES (Isomeric): CC1(C=CC2=C(O1)C=C3C(=C2O)C(=O)C4=C(O3)C(=CC=C4)O)C
• InChI: InChI=1S/C18H14O5/c1-18(2)7-6-9-12(23-18)8-13-14(15(9)20)16(21)10-4-3-5-11(19)17(10)22-13/h3-8,19-20H,1-2H3
• InChI Key: NHNIESSJWQBRJW-UHFFFAOYSA-N
• Popularity: 16 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₁₄O₅
• Molecular Weight: 310.30 g/mol
• Exact Mass: 310.08412354 g/mol
• Topological Polar Surface Area (TPSA): 76.00 Ų
• XlogP: 3.70
• Atomic LogP (AlogP): 3.54
• H-Bond Acceptor: 5
• H-Bond Donor: 2
• Rotatable Bonds: 0

Synonyms

• 16265-56-8
• 6-Dehydroxyjacareubin
• 6-Desoxyjacareubin
• Jacareubin, 6-deoxy-
• 5,10-dihydroxy-2,2-dimethylpyrano[3,2-b]xanthen-6-one
• CHEBI:2183
• 2H,6H-Pyrano[3,2-b]xanthen-6-one, 5,10-dihydroxy-2,2-dimethyl-
• 5,10-dihydroxy-2,2-dimethyl-pyrano[3,2-b]xanthen-6-one
• 5,10-Dihydroxy-2,2-dimethyl-2H,6H-pyrano[3,2-b]xanthen-6-one
• AC1NQYRP
• CHEMBL457949
• DTXSID00167420
• HY-N2707
• AKOS032948332
• CS-0023173
• C10059
• Q27105575
• 1,5-dihydroxy-2^,^,2^,^-dimethylpyrano-5^,^,6^,^:2,3-xanthone

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9844	98.44%
Caco-2	+	0.5196	51.96%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	+	0.6286	62.86%
Subcellular localzation	Mitochondria	0.7893	78.93%
OATP2B1 inhibitior	-	0.5687	56.87%
OATP1B1 inhibitior	+	0.9316	93.16%
OATP1B3 inhibitior	+	0.9791	97.91%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	+	0.6705	67.05%
P-glycoprotein inhibitior	-	0.4491	44.91%
P-glycoprotein substrate	-	0.6670	66.70%
CYP3A4 substrate	+	0.6184	61.84%
CYP2C9 substrate	-	0.6166	61.66%
CYP2D6 substrate	-	0.8394	83.94%
CYP3A4 inhibition	-	0.5844	58.44%
CYP2C9 inhibition	+	0.5890	58.90%
CYP2C19 inhibition	-	0.5000	50.00%
CYP2D6 inhibition	-	0.7327	73.27%
CYP1A2 inhibition	+	0.5570	55.70%
CYP2C8 inhibition	+	0.4532	45.32%
CYP inhibitory promiscuity	+	0.5416	54.16%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5703	57.03%
Eye corrosion	-	0.9875	98.75%
Eye irritation	+	0.7969	79.69%
Skin irritation	-	0.6672	66.72%
Skin corrosion	-	0.9381	93.81%
Ames mutagenesis	+	0.7300	73.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7726	77.26%
Micronuclear	+	0.7200	72.00%
Hepatotoxicity	+	0.5051	50.51%
skin sensitisation	-	0.6617	66.17%
Respiratory toxicity	+	0.6667	66.67%
Reproductive toxicity	+	0.6333	63.33%
Mitochondrial toxicity	+	0.5125	51.25%
Nephrotoxicity	-	0.8586	85.86%
Acute Oral Toxicity (c)	III	0.7361	73.61%
Estrogen receptor binding	+	0.9222	92.22%
Androgen receptor binding	+	0.7553	75.53%
Thyroid receptor binding	+	0.7752	77.52%
Glucocorticoid receptor binding	+	0.9428	94.28%
Aromatase binding	+	0.8229	82.29%
PPAR gamma	+	0.8944	89.44%
Honey bee toxicity	-	0.8867	88.67%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.5100	51.00%
Fish aquatic toxicity	+	0.9498	94.98%

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	99.32%	91.11%
CHEMBL2581	P07339	Cathepsin D	96.84%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	96.46%	89.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.68%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.19%	95.56%
CHEMBL3192	Q9BY41	Histone deacetylase 8	93.25%	93.99%
CHEMBL3401	O75469	Pregnane X receptor	93.23%	94.73%
CHEMBL1951	P21397	Monoamine oxidase A	93.15%	91.49%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	92.98%	99.23%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	89.01%	94.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	86.83%	99.15%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	86.78%	85.14%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.74%	86.33%
CHEMBL1937	Q92769	Histone deacetylase 2	85.83%	94.75%
CHEMBL2535	P11166	Glucose transporter	83.17%	98.75%
CHEMBL1907	P15144	Aminopeptidase N	82.61%	93.31%
CHEMBL3830	Q2M2I8	Adaptor-associated kinase	82.49%	83.10%
CHEMBL5409	Q8TDU6	G-protein coupled bile acid receptor 1	81.01%	93.65%

Plants that contains it

• Calophyllum apetalum
• Calophyllum austroindicum
• Calophyllum brasiliense
• Calophyllum calaba
• Calophyllum hosei
• Calophyllum inophyllum
• Calophyllum soulattri
• Calophyllum tomentosum
• Cratoxylum formosum
• Crocus sieberi
• Eugenia myrcianthes
• Euphorbia micractina
• Garcinia lancilimba
• Garcinia merguensis
• Garcinia nigrolineata
• Garcinia xanthochymus
• Gynochthodes officinalis
• Hypericum brasiliense
• Jacobaea persoonii
• Kielmeyera pumila
• Kielmeyera speciosa
• Maclura cochinchinensis
• Maclura pomifera
• Montanoa karwinskii
• Mourera fluviatilis
• Rosa roxburghii
• Salix babylonica
• Strychnos decussata
• Verbena bonariensis

Cross-Links

• PubChem: 5281629
• NPASS: NPC6633
• LOTUS: LTS0032665
• wikiData: Q27105575