Cycloaltilisin 6

Details

• Internal ID: 9585f132-2bc3-447b-904c-ddbfccd80d42
• Taxonomy: Phenylpropanoids and polyketides > Linear 1,3-diarylpropanoids > Chalcones and dihydrochalcones > 2-Hydroxy-dihydrochalcones
• IUPAC Name: 1-(2,4-dihydroxyphenyl)-3-[5-[2-[3-(2,4-dihydroxyphenyl)-3-oxopropyl]-3-[(2E)-3,7-dimethylocta-2,6-dienyl]-4,5-dihydroxyphenyl]-2-[(2E)-3,7-dimethylocta-2,6-dienyl]-3,4-dihydroxyphenyl]propan-1-one
• SMILES (Canonical): CC(=CCCC(=CCC1=C(C(=C(C=C1CCC(=O)C2=C(C=C(C=C2)O)O)C3=CC(=C(C(=C3CCC(=O)C4=C(C=C(C=C4)O)O)CC=C(C)CCC=C(C)C)O)O)O)O)C)C
• SMILES (Isomeric): CC(=CCC/C(=C/CC1=C(C(=C(C=C1CCC(=O)C2=C(C=C(C=C2)O)O)C3=CC(=C(C(=C3CCC(=O)C4=C(C=C(C=C4)O)O)C/C=C(\C)/CCC=C(C)C)O)O)O)O)/C)C
• InChI: InChI=1S/C50H58O10/c1-29(2)9-7-11-31(5)13-18-36-33(15-23-43(53)39-20-16-34(51)26-45(39)55)25-42(50(60)49(36)59)41-28-47(57)48(58)38(19-14-32(6)12-8-10-30(3)4)37(41)22-24-44(54)40-21-17-35(52)27-46(40)56/h9-10,13-14,16-17,20-21,25-28,51-52,55-60H,7-8,11-12,15,18-19,22-24H2,1-6H3/b31-13+,32-14+
• InChI Key: BHDBRCJCCXGBOF-GCFMLEDASA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₅₀H₅₈O₁₀
• Molecular Weight: 819.00 g/mol
• Exact Mass: 818.40299804 g/mol
• Topological Polar Surface Area (TPSA): 196.00 Ų
• XlogP: 12.50
• Atomic LogP (AlogP): 11.10
• H-Bond Acceptor: 10
• H-Bond Donor: 8
• Rotatable Bonds: 19

Synonyms

• CHEMBL508746
• BDBM50260286
• 1-(2,4-dihydroxyphenyl)-3-[5-[2-[3-(2,4-dihydroxyphenyl)-3-oxopropyl]-3-[(2E)-3,7-dimethylocta-2,6-dienyl]-4,5-dihydroxyphenyl]-2-[(2E)-3,7-dimethylocta-2,6-dienyl]-3,4-dihydroxyphenyl]propan-1-one
• 3,3'-[4,5,5',6'-Tetrahydroxy-3,4'-bis(3,7-dimethyl-2,6-octadienyl)-1,1'-biphenyl-2,3'-diyl]bis[1-(2,4-dihydroxyphenyl)-1-propanone]

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9686	96.86%
Caco-2	-	0.8539	85.39%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.8513	85.13%
OATP2B1 inhibitior	+	0.5772	57.72%
OATP1B1 inhibitior	+	0.7971	79.71%
OATP1B3 inhibitior	+	0.8650	86.50%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.7250	72.50%
BSEP inhibitior	+	0.9878	98.78%
P-glycoprotein inhibitior	+	0.7896	78.96%
P-glycoprotein substrate	-	0.5526	55.26%
CYP3A4 substrate	+	0.6182	61.82%
CYP2C9 substrate	-	0.7962	79.62%
CYP2D6 substrate	-	0.8274	82.74%
CYP3A4 inhibition	+	0.5103	51.03%
CYP2C9 inhibition	-	0.5479	54.79%
CYP2C19 inhibition	-	0.5072	50.72%
CYP2D6 inhibition	-	0.8305	83.05%
CYP1A2 inhibition	+	0.6596	65.96%
CYP2C8 inhibition	+	0.6846	68.46%
CYP inhibitory promiscuity	-	0.7069	70.69%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.8623	86.23%
Carcinogenicity (trinary)	Non-required	0.7319	73.19%
Eye corrosion	-	0.9914	99.14%
Eye irritation	-	0.8833	88.33%
Skin irritation	-	0.7592	75.92%
Skin corrosion	-	0.9217	92.17%
Ames mutagenesis	-	0.5554	55.54%
Human Ether-a-go-go-Related Gene inhibition	+	0.7558	75.58%
Micronuclear	-	0.7700	77.00%
Hepatotoxicity	-	0.6217	62.17%
skin sensitisation	-	0.7032	70.32%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.6778	67.78%
Mitochondrial toxicity	-	0.5000	50.00%
Nephrotoxicity	-	0.7587	75.87%
Acute Oral Toxicity (c)	III	0.5189	51.89%
Estrogen receptor binding	+	0.8362	83.62%
Androgen receptor binding	+	0.7997	79.97%
Thyroid receptor binding	+	0.5789	57.89%
Glucocorticoid receptor binding	+	0.7338	73.38%
Aromatase binding	+	0.5710	57.10%
PPAR gamma	+	0.7043	70.43%
Honey bee toxicity	-	0.8319	83.19%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.6300	63.00%
Fish aquatic toxicity	+	1.0000	100.00%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL268	P43235	Cathepsin K	98 nM	IC50	PMID: 19854643

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.35%	91.11%
CHEMBL2581	P07339	Cathepsin D	96.92%	98.95%
CHEMBL3401	O75469	Pregnane X receptor	95.08%	94.73%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.94%	96.09%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	89.86%	93.10%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.80%	86.33%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.45%	99.17%
CHEMBL4208	P20618	Proteasome component C5	89.18%	90.00%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	87.34%	95.17%
CHEMBL4769	O95749	Geranylgeranyl pyrophosphate synthetase	85.49%	92.08%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	83.44%	99.15%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	83.20%	95.50%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.02%	95.56%
CHEMBL1929	P47989	Xanthine dehydrogenase	82.90%	96.12%
CHEMBL2535	P11166	Glucose transporter	82.20%	98.75%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	81.85%	83.57%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	81.61%	96.95%
CHEMBL5852	Q96P65	Pyroglutamylated RFamide peptide receptor	81.35%	85.00%

Plants that contains it

• Artocarpus altilis

Cross-Links

• PubChem: 10190977
• NPASS: NPC35
• ChEMBL: CHEMBL508746
• LOTUS: LTS0248720
• wikiData: Q104935886