Icacenone

Details

• Internal ID: 546f7bc4-5d81-42ad-98fe-3923a3abda55
• Taxonomy: Organoheterocyclic compounds > Naphthopyrans
• IUPAC Name: 16,20-dihydroxy-8,13,17-trioxahexacyclo[14.2.2.11,12.02,10.05,9.015,21]henicosa-5(9),6-diene-4,14-dione
• InChI: InChI=1S/C18H18O7/c19-10-4-9-8(15-7(10)1-2-23-15)3-11-13-14(16(21)25-11)18(22)12(20)5-17(9,13)6-24-18/h1-2,8-9,11-14,20,22H,3-6H2
• InChI Key: HRFDAMLQNPGNEH-UHFFFAOYSA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₁₈O₇
• Molecular Weight: 346.30 g/mol
• Exact Mass: 346.10525291 g/mol
• Topological Polar Surface Area (TPSA): 106.00 Ų
• XlogP: -0.50
• Atomic LogP (AlogP): 0.60
• H-Bond Acceptor: 7
• H-Bond Donor: 2
• Rotatable Bonds: 0

Synonyms

• NSC383339
• NSC-383339
• 6H-5b,8-Ethano-4H,9H-benzofuro[7,6-h]furo[4,3,2-de][2]benzopyran-4,9-dione, 5,5a,8,8a,10a,10b,11,11a-octahydro-8,12-dihydroxy-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8489	84.89%
Caco-2	-	0.6526	65.26%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Mitochondria	0.8148	81.48%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8872	88.72%
OATP1B3 inhibitior	+	0.9536	95.36%
MATE1 inhibitior	-	0.8000	80.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.7445	74.45%
P-glycoprotein inhibitior	-	0.8685	86.85%
P-glycoprotein substrate	+	0.5229	52.29%
CYP3A4 substrate	+	0.6521	65.21%
CYP2C9 substrate	-	0.5998	59.98%
CYP2D6 substrate	-	0.8515	85.15%
CYP3A4 inhibition	-	0.9124	91.24%
CYP2C9 inhibition	-	0.8897	88.97%
CYP2C19 inhibition	-	0.8076	80.76%
CYP2D6 inhibition	-	0.9170	91.70%
CYP1A2 inhibition	-	0.8585	85.85%
CYP2C8 inhibition	+	0.4445	44.45%
CYP inhibitory promiscuity	-	0.9890	98.90%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.5882	58.82%
Eye corrosion	-	0.9891	98.91%
Eye irritation	-	0.9401	94.01%
Skin irritation	-	0.7746	77.46%
Skin corrosion	-	0.9381	93.81%
Ames mutagenesis	+	0.5130	51.30%
Human Ether-a-go-go-Related Gene inhibition	-	0.5820	58.20%
Micronuclear	+	0.5800	58.00%
Hepatotoxicity	+	0.6375	63.75%
skin sensitisation	-	0.8536	85.36%
Respiratory toxicity	+	0.8111	81.11%
Reproductive toxicity	+	0.8333	83.33%
Mitochondrial toxicity	+	0.7000	70.00%
Nephrotoxicity	+	0.5690	56.90%
Acute Oral Toxicity (c)	III	0.4253	42.53%
Estrogen receptor binding	+	0.8547	85.47%
Androgen receptor binding	+	0.6488	64.88%
Thyroid receptor binding	-	0.5620	56.20%
Glucocorticoid receptor binding	+	0.7072	70.72%
Aromatase binding	+	0.6546	65.46%
PPAR gamma	+	0.7163	71.63%
Honey bee toxicity	-	0.6480	64.80%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	+	0.5900	59.00%
Fish aquatic toxicity	+	0.9159	91.59%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.05%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.61%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	92.06%	89.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.58%	97.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	89.89%	100.00%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	88.96%	96.38%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.84%	95.56%
CHEMBL1951	P21397	Monoamine oxidase A	86.68%	91.49%
CHEMBL253	P34972	Cannabinoid CB2 receptor	83.28%	97.25%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	82.92%	93.04%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.40%	99.23%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	82.21%	85.14%
CHEMBL2581	P07339	Cathepsin D	81.24%	98.95%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.66%	95.89%

Plants that contains it

• Icacina mannii
• Icacina oliviformis

Cross-Links

• PubChem: 436138
• LOTUS: LTS0174190
• wikiData: Q105032637