Norbadione A

Details

• Internal ID: 566e2322-7eed-438e-92b7-322f6b3be424
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Tetracarboxylic acids and derivatives
• IUPAC Name: (2E)-2-[4-[9-[(5E)-5-[carboxy-(4-hydroxyphenyl)methylidene]-4-hydroxy-2-oxofuran-3-yl]-11-hydroxy-3-oxo-2-oxatricyclo[6.3.1.04,12]dodeca-1(11),4,6,8(12),9-pentaen-6-yl]-3-hydroxy-5-oxofuran-2-ylidene]-2-(4-hydroxyphenyl)acetic acid
• SMILES (Canonical): C1=CC(=CC=C1C(=C2C(=C(C(=O)O2)C3=CC4=C5C(=C3)C(=O)OC5=C(C=C4C6=C(C(=C(C7=CC=C(C=C7)O)C(=O)O)OC6=O)O)O)O)C(=O)O)O
• SMILES (Isomeric): C1=CC(=CC=C1/C(=C\2/C(=C(C(=O)O2)C3=CC4=C5C(=C3)C(=O)OC5=C(C=C4C6=C(/C(=C(/C7=CC=C(C=C7)O)\C(=O)O)/OC6=O)O)O)O)/C(=O)O)O
• InChI: InChI=1S/C35H18O15/c36-15-5-1-12(2-6-15)22(31(41)42)29-26(39)21(34(46)49-29)14-9-17-18(11-20(38)28-24(17)19(10-14)33(45)48-28)25-27(40)30(50-35(25)47)23(32(43)44)13-3-7-16(37)8-4-13/h1-11,36-40H,(H,41,42)(H,43,44)/b29-22+,30-23+
• InChI Key: NEAFOYGNZAYARY-KBWMUOTDSA-N
• Popularity: 11 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₅H₁₈O₁₅
• Molecular Weight: 678.50 g/mol
• Exact Mass: 678.06456986 g/mol
• Topological Polar Surface Area (TPSA): 255.00 Ų
• XlogP: 3.10
• Atomic LogP (AlogP): 4.13
• H-Bond Acceptor: 13
• H-Bond Donor: 7
• Rotatable Bonds: 6

Synonyms

• 8DH6BNL8BA
• 90295-68-4
• UNII-8DH6BNL8BA
• NSC605656
• Norbadion A
• SCHEMBL12766867
• DTXSID301045531
• NSC-605656
• Q15425764
• Naphthalenoid pulvinic acid derv. from Pisolithus tinctorius fungus
• (.ALPHA.E,.ALPHA.E)-.ALPHA.,.ALPHA.-((8-HYDROXY-2-OXO-2H-NAPHTHO(1,8-BC)FURAN-4,6-DIYL)BIS(3-HYDROXY-5-OXO-4-FURANYL-2(5H)-YLIDENE))BIS(4-HYDROXYBENZENEACETIC ACID)
• BENZENEACETIC ACID, .ALPHA.,.ALPHA.-((8-HYDROXY-2-OXO-2H-NAPHTHO(1,8-BC)FURAN-4,6-DIYL)BIS(3-HYDROXY-5-OXO-4-FURANYL-2(5H)-YLIDENE))BIS(4-HYDROXY-, (.ALPHA.E,.ALPHA.E)-
• BENZENEACETIC ACID, .ALPHA.,.ALPHA.-((8-HYDROXY-2-OXO-2H-NAPHTHO(1,8-BC)FURAN-4,6-DIYL)BIS(3-HYDROXY-5-OXO-4-FURANYL-2(5H)-YLIDENE))BIS(4-HYDROXY-, (E,E)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9905	99.05%
Caco-2	-	0.8823	88.23%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	-	0.5571	55.71%
Subcellular localzation	Mitochondria	0.7590	75.90%
OATP2B1 inhibitior	+	0.5774	57.74%
OATP1B1 inhibitior	+	0.8559	85.59%
OATP1B3 inhibitior	+	0.8561	85.61%
MATE1 inhibitior	-	0.6000	60.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	+	0.7873	78.73%
P-glycoprotein inhibitior	+	0.7240	72.40%
P-glycoprotein substrate	-	0.6686	66.86%
CYP3A4 substrate	+	0.5685	56.85%
CYP2C9 substrate	-	0.8040	80.40%
CYP2D6 substrate	-	0.8898	88.98%
CYP3A4 inhibition	-	0.7575	75.75%
CYP2C9 inhibition	+	0.9261	92.61%
CYP2C19 inhibition	+	0.5771	57.71%
CYP2D6 inhibition	-	0.9201	92.01%
CYP1A2 inhibition	-	0.5509	55.09%
CYP2C8 inhibition	+	0.8715	87.15%
CYP inhibitory promiscuity	+	0.7236	72.36%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9643	96.43%
Carcinogenicity (trinary)	Danger	0.4239	42.39%
Eye corrosion	-	0.9885	98.85%
Eye irritation	-	0.7475	74.75%
Skin irritation	-	0.5463	54.63%
Skin corrosion	-	0.9527	95.27%
Ames mutagenesis	+	0.5800	58.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4079	40.79%
Micronuclear	+	0.9300	93.00%
Hepatotoxicity	-	0.5199	51.99%
skin sensitisation	-	0.7012	70.12%
Respiratory toxicity	+	0.6778	67.78%
Reproductive toxicity	+	0.6444	64.44%
Mitochondrial toxicity	+	0.6875	68.75%
Nephrotoxicity	-	0.6079	60.79%
Acute Oral Toxicity (c)	II	0.3705	37.05%
Estrogen receptor binding	+	0.7688	76.88%
Androgen receptor binding	+	0.8619	86.19%
Thyroid receptor binding	+	0.5363	53.63%
Glucocorticoid receptor binding	+	0.6441	64.41%
Aromatase binding	-	0.5669	56.69%
PPAR gamma	+	0.7106	71.06%
Honey bee toxicity	-	0.8592	85.92%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.6200	62.00%
Fish aquatic toxicity	+	0.9960	99.60%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1951	P21397	Monoamine oxidase A	99.07%	91.49%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.94%	91.11%
CHEMBL2581	P07339	Cathepsin D	94.54%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.84%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.86%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.09%	86.33%
CHEMBL242	Q92731	Estrogen receptor beta	90.71%	98.35%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	88.25%	99.23%
CHEMBL2535	P11166	Glucose transporter	87.34%	98.75%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.76%	99.17%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	84.11%	95.50%
CHEMBL3194	P02766	Transthyretin	82.07%	90.71%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	81.93%	94.00%
CHEMBL3401	O75469	Pregnane X receptor	81.72%	94.73%

Plants that contains it

• Humulus scandens

Cross-Links

• PubChem: 54679293
• NPASS: NPC88609
• LOTUS: LTS0125919
• wikiData: Q15425764