Riccardiphenol A

Details

• Internal ID: 54f64fec-bd89-4d2d-b3eb-543de0c8cb5b
• Taxonomy: Organoheterocyclic compounds > Benzofurans
• IUPAC Name: (1'R,2R,3'S)-1',3'-dimethyl-1'-[(1E)-4-methylpenta-1,3-dienyl]spiro[3H-1-benzofuran-2,2'-cyclohexane]-5-ol
• SMILES (Canonical): CC1CCCC(C12CC3=C(O2)C=CC(=C3)O)(C)C=CC=C(C)C
• SMILES (Isomeric): C[C@H]1CCC[C@]([C@@]12CC3=C(O2)C=CC(=C3)O)(C)/C=C/C=C(C)C
• InChI: InChI=1S/C21H28O2/c1-15(2)7-5-11-20(4)12-6-8-16(3)21(20)14-17-13-18(22)9-10-19(17)23-21/h5,7,9-11,13,16,22H,6,8,12,14H2,1-4H3/b11-5+/t16-,20-,21+/m0/s1
• InChI Key: GYYIQXDKUXUMCC-JMNLPZGFSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₈O₂
• Molecular Weight: 312.40 g/mol
• Exact Mass: 312.208930132 g/mol
• Topological Polar Surface Area (TPSA): 29.50 Ų
• XlogP: 6.20
• Atomic LogP (AlogP): 5.41
• H-Bond Acceptor: 2
• H-Bond Donor: 1
• Rotatable Bonds: 2

Synonyms

• (1'R,2R,3'S)-1',3'-Dimethyl-1'-[(1E)-4-methylpenta-1,3-dienyl]spiro[3H-1-benzofuran-2,2'-cyclohexane]-5-ol

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	1.0000	100.00%
Caco-2	+	0.8371	83.71%
Blood Brain Barrier	+	0.7000	70.00%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.6290	62.90%
OATP2B1 inhibitior	-	0.8608	86.08%
OATP1B1 inhibitior	+	0.7841	78.41%
OATP1B3 inhibitior	+	0.9483	94.83%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.5250	52.50%
BSEP inhibitior	+	0.6493	64.93%
P-glycoprotein inhibitior	-	0.7453	74.53%
P-glycoprotein substrate	-	0.6992	69.92%
CYP3A4 substrate	+	0.6564	65.64%
CYP2C9 substrate	-	0.8111	81.11%
CYP2D6 substrate	+	0.3573	35.73%
CYP3A4 inhibition	-	0.6235	62.35%
CYP2C9 inhibition	-	0.7029	70.29%
CYP2C19 inhibition	+	0.7703	77.03%
CYP2D6 inhibition	-	0.8564	85.64%
CYP1A2 inhibition	+	0.7198	71.98%
CYP2C8 inhibition	+	0.6642	66.42%
CYP inhibitory promiscuity	+	0.6677	66.77%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.7800	78.00%
Carcinogenicity (trinary)	Non-required	0.5250	52.50%
Eye corrosion	-	0.9897	98.97%
Eye irritation	-	0.8989	89.89%
Skin irritation	-	0.6640	66.40%
Skin corrosion	-	0.9462	94.62%
Ames mutagenesis	-	0.7870	78.70%
Human Ether-a-go-go-Related Gene inhibition	+	0.7647	76.47%
Micronuclear	-	0.9200	92.00%
Hepatotoxicity	-	0.5783	57.83%
skin sensitisation	-	0.6556	65.56%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	+	0.8250	82.50%
Nephrotoxicity	-	0.6170	61.70%
Acute Oral Toxicity (c)	III	0.7536	75.36%
Estrogen receptor binding	+	0.8312	83.12%
Androgen receptor binding	+	0.6482	64.82%
Thyroid receptor binding	+	0.7231	72.31%
Glucocorticoid receptor binding	-	0.5383	53.83%
Aromatase binding	+	0.6768	67.68%
PPAR gamma	+	0.8073	80.73%
Honey bee toxicity	-	0.8717	87.17%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	+	0.7600	76.00%
Fish aquatic toxicity	+	0.9925	99.25%

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	99.38%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.34%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.02%	96.09%
CHEMBL242	Q92731	Estrogen receptor beta	92.21%	98.35%
CHEMBL241	Q14432	Phosphodiesterase 3A	90.73%	92.94%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.52%	86.33%
CHEMBL2581	P07339	Cathepsin D	90.44%	98.95%
CHEMBL1994	P08235	Mineralocorticoid receptor	89.08%	100.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.91%	95.89%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.90%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.31%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.16%	95.56%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	82.03%	89.05%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	81.32%	89.62%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	81.17%	95.89%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	81.13%	93.40%
CHEMBL3401	O75469	Pregnane X receptor	80.58%	94.73%

Plants that contains it

• Riccardia crassa

Cross-Links

• PubChem: 10859932
• LOTUS: LTS0164554
• wikiData: Q105024243