Calabaxanthone

Details

• Internal ID: 03ac54cc-7b9a-4675-bf8d-002e7fdeeb86
• Taxonomy: Organoheterocyclic compounds > Benzopyrans > 1-benzopyrans > Xanthones > 8-prenylated xanthones
• IUPAC Name: 5-hydroxy-8-methoxy-2,2-dimethyl-7-(3-methylbut-2-enyl)pyrano[3,2-b]xanthen-6-one
• SMILES (Canonical): CC(=CCC1=C(C=CC2=C1C(=O)C3=C(C4=C(C=C3O2)OC(C=C4)(C)C)O)OC)C
• SMILES (Isomeric): CC(=CCC1=C(C=CC2=C1C(=O)C3=C(C4=C(C=C3O2)OC(C=C4)(C)C)O)OC)C
• InChI: InChI=1S/C24H24O5/c1-13(2)6-7-14-16(27-5)8-9-17-20(14)23(26)21-19(28-17)12-18-15(22(21)25)10-11-24(3,4)29-18/h6,8-12,25H,7H2,1-5H3
• InChI Key: PLKQPRRVFTZBAE-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₄H₂₄O₅
• Molecular Weight: 392.40 g/mol
• Exact Mass: 392.16237386 g/mol
• Topological Polar Surface Area (TPSA): 65.00 Ų
• XlogP: 6.00
• Atomic LogP (AlogP): 5.35
• H-Bond Acceptor: 5
• H-Bond Donor: 1
• Rotatable Bonds: 3

Synonyms

• 39011-96-6
• 5-hydroxy-8-methoxy-2,2-dimethyl-7-(3-methylbut-2-enyl)pyrano[3,2-b]xanthen-6-one
• NSC 372808
• NSC-372808
• NSC372808
• Y7Z3U6WUB8
• DTXSID40321281
• CHEBI:172627
• 2H,6H-Pyrano[3,2-b]xanthen-6-one, 5-hydroxy-8-methoxy-2,2-dimethyl-7-(3-methyl-2-buten-1-yl)-
• 2H,6H-Pyrano[3,2-b]xanthen-6-one, 5-hydroxy-8-methoxy-2,2-dimethyl-7-(3-methyl-2-butenyl)-
• 5-Hydroxy-8-methoxy-2,2-dimethyl-7-(3-methyl-2-buten-1-yl)-2H,6H-pyrano[3,2-b]xanthen-6-one
• 5-Hydroxy-8-methoxy-2,2-dimethyl-7-(3-methyl-2-butenyl)-2H,6H-pyrano[3,2-b]xanthen-6-one, 9CI
• 5-hydroxy-8-methoxy-2,2-dimethyl-7-(3-methylbut-2-en-1-yl)-2,6-dihydro-1,11-dioxatetracen-6-one
• 8-METHOXY-2,2-DIMETHYL-7-(3-METHYLBUT-2-ENYL)-5-OXIDANYL-PYRANO(3,2-B)XANTHEN-6-ONE

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9922	99.22%
Caco-2	+	0.8279	82.79%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	+	0.6000	60.00%
Subcellular localzation	Mitochondria	0.7240	72.40%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8977	89.77%
OATP1B3 inhibitior	+	0.8888	88.88%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.9288	92.88%
P-glycoprotein inhibitior	+	0.8828	88.28%
P-glycoprotein substrate	-	0.5337	53.37%
CYP3A4 substrate	+	0.6252	62.52%
CYP2C9 substrate	-	0.5948	59.48%
CYP2D6 substrate	-	0.8144	81.44%
CYP3A4 inhibition	-	0.6310	63.10%
CYP2C9 inhibition	+	0.5752	57.52%
CYP2C19 inhibition	+	0.8560	85.60%
CYP2D6 inhibition	-	0.7753	77.53%
CYP1A2 inhibition	+	0.6619	66.19%
CYP2C8 inhibition	+	0.6229	62.29%
CYP inhibitory promiscuity	+	0.7660	76.60%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9513	95.13%
Carcinogenicity (trinary)	Non-required	0.6283	62.83%
Eye corrosion	-	0.9896	98.96%
Eye irritation	-	0.4832	48.32%
Skin irritation	-	0.7397	73.97%
Skin corrosion	-	0.9626	96.26%
Ames mutagenesis	+	0.6300	63.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7349	73.49%
Micronuclear	-	0.6300	63.00%
Hepatotoxicity	-	0.6272	62.72%
skin sensitisation	-	0.7453	74.53%
Respiratory toxicity	+	0.6444	64.44%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	+	0.5750	57.50%
Nephrotoxicity	-	0.8534	85.34%
Acute Oral Toxicity (c)	III	0.7174	71.74%
Estrogen receptor binding	+	0.9081	90.81%
Androgen receptor binding	+	0.7516	75.16%
Thyroid receptor binding	+	0.6412	64.12%
Glucocorticoid receptor binding	+	0.9116	91.16%
Aromatase binding	+	0.7402	74.02%
PPAR gamma	+	0.8873	88.73%
Honey bee toxicity	-	0.7493	74.93%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.6100	61.00%
Fish aquatic toxicity	+	0.9863	98.63%

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	99.11%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	98.77%	94.45%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	95.71%	85.14%
CHEMBL2581	P07339	Cathepsin D	95.18%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.79%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.13%	89.00%
CHEMBL3401	O75469	Pregnane X receptor	91.04%	94.73%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	89.97%	94.00%
CHEMBL1255126	O15151	Protein Mdm4	89.54%	90.20%
CHEMBL1951	P21397	Monoamine oxidase A	87.25%	91.49%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.65%	95.56%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.78%	99.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	83.15%	96.09%
CHEMBL2413	P32246	C-C chemokine receptor type 1	82.63%	89.50%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.23%	95.89%
CHEMBL4208	P20618	Proteasome component C5	82.16%	90.00%
CHEMBL2535	P11166	Glucose transporter	82.03%	98.75%
CHEMBL3192	Q9BY41	Histone deacetylase 8	82.01%	93.99%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	81.06%	96.00%
CHEMBL3492	P49721	Proteasome Macropain subunit	80.19%	90.24%

Plants that contains it

• Calophyllum calaba
• Calophyllum tomentosum
• Crocus sieberi
• Eugenia myrcianthes
• Garcinia mangostana
• Gynochthodes officinalis
• Jacobaea persoonii
• Montanoa karwinskii
• Salix babylonica
• Strychnos decussata
• Verbena bonariensis

Cross-Links

• PubChem: 341188
• NPASS: NPC158259
• LOTUS: LTS0005339
• wikiData: Q82079085