(2Z,4E)-3-hydroxy-5-(4-hydroxy-3-methoxyphenyl)-1-[(2R,3R,8R)-3-(4-hydroxy-3-methoxyphenyl)-6-methyl-8-(6-methylhept-5-en-2-yl)-2-bicyclo[2.2.2]oct-5-enyl]penta-2,4-dien-1-one

Details

• Internal ID: b03a7cfe-fcf8-4817-b805-23e37969da31
• Taxonomy: Phenylpropanoids and polyketides > Diarylheptanoids > Linear diarylheptanoids
• IUPAC Name: (2Z,4E)-3-hydroxy-5-(4-hydroxy-3-methoxyphenyl)-1-[(2R,3R,8R)-3-(4-hydroxy-3-methoxyphenyl)-6-methyl-8-(6-methylhept-5-en-2-yl)-2-bicyclo[2.2.2]oct-5-enyl]penta-2,4-dien-1-one
• SMILES (Canonical): CC1=CC2C(CC1C(C2C3=CC(=C(C=C3)O)OC)C(=O)C=C(C=CC4=CC(=C(C=C4)O)OC)O)C(C)CCC=C(C)C
• SMILES (Isomeric): CC1=CC2[C@H](CC1[C@H]([C@@H]2C3=CC(=C(C=C3)O)OC)C(=O)/C=C(/C=C/C4=CC(=C(C=C4)O)OC)\O)C(C)CCC=C(C)C
• InChI: InChI=1S/C36H44O6/c1-21(2)8-7-9-22(3)27-20-28-23(4)16-29(27)35(25-12-15-31(39)34(18-25)42-6)36(28)32(40)19-26(37)13-10-24-11-14-30(38)33(17-24)41-5/h8,10-19,22,27-29,35-39H,7,9,20H2,1-6H3/b13-10+,26-19-/t22?,27-,28?,29?,35-,36+/m1/s1
• InChI Key: VYQSPYUOLZWETA-YCIFWMGRSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₆H₄₄O₆
• Molecular Weight: 572.70 g/mol
• Exact Mass: 572.31378912 g/mol
• Topological Polar Surface Area (TPSA): 96.20 Ų
• XlogP: 8.10
• Atomic LogP (AlogP): 8.13
• H-Bond Acceptor: 6
• H-Bond Donor: 3
• Rotatable Bonds: 11

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9946	99.46%
Caco-2	-	0.7825	78.25%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.6286	62.86%
Subcellular localzation	Mitochondria	0.8650	86.50%
OATP2B1 inhibitior	-	0.7188	71.88%
OATP1B1 inhibitior	+	0.8713	87.13%
OATP1B3 inhibitior	+	0.8702	87.02%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8564	85.64%
BSEP inhibitior	+	0.9884	98.84%
P-glycoprotein inhibitior	+	0.8871	88.71%
P-glycoprotein substrate	+	0.6094	60.94%
CYP3A4 substrate	+	0.6493	64.93%
CYP2C9 substrate	-	0.7985	79.85%
CYP2D6 substrate	-	0.8451	84.51%
CYP3A4 inhibition	-	0.7246	72.46%
CYP2C9 inhibition	+	0.5885	58.85%
CYP2C19 inhibition	+	0.6842	68.42%
CYP2D6 inhibition	-	0.8470	84.70%
CYP1A2 inhibition	+	0.7098	70.98%
CYP2C8 inhibition	+	0.6464	64.64%
CYP inhibitory promiscuity	+	0.5821	58.21%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.8186	81.86%
Carcinogenicity (trinary)	Non-required	0.6887	68.87%
Eye corrosion	-	0.9919	99.19%
Eye irritation	-	0.9199	91.99%
Skin irritation	-	0.8031	80.31%
Skin corrosion	-	0.9558	95.58%
Ames mutagenesis	-	0.7800	78.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7893	78.93%
Micronuclear	-	0.7600	76.00%
Hepatotoxicity	-	0.5768	57.68%
skin sensitisation	-	0.7754	77.54%
Respiratory toxicity	+	0.7444	74.44%
Reproductive toxicity	+	0.7000	70.00%
Mitochondrial toxicity	-	0.5250	52.50%
Nephrotoxicity	-	0.8595	85.95%
Acute Oral Toxicity (c)	III	0.5246	52.46%
Estrogen receptor binding	+	0.8455	84.55%
Androgen receptor binding	+	0.7858	78.58%
Thyroid receptor binding	+	0.6892	68.92%
Glucocorticoid receptor binding	+	0.8774	87.74%
Aromatase binding	-	0.5000	50.00%
PPAR gamma	+	0.7203	72.03%
Honey bee toxicity	-	0.7443	74.43%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.6900	69.00%
Fish aquatic toxicity	+	1.0000	100.00%

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	98.96%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.92%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	97.43%	94.45%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	96.37%	96.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.66%	97.09%
CHEMBL2581	P07339	Cathepsin D	94.43%	98.95%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	93.84%	89.62%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	92.60%	90.71%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	92.21%	85.14%
CHEMBL2413	P32246	C-C chemokine receptor type 1	91.61%	89.50%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.31%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.28%	89.00%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	90.74%	95.50%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	90.58%	96.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.45%	95.56%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	87.71%	99.15%
CHEMBL3359	P21462	Formyl peptide receptor 1	86.63%	93.56%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	85.97%	97.21%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.91%	99.17%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.25%	95.89%
CHEMBL3194	P02766	Transthyretin	83.00%	90.71%
CHEMBL340	P08684	Cytochrome P450 3A4	82.84%	91.19%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.40%	92.62%

Plants that contains it

• Curcuma longa

Cross-Links

• PubChem: 102230690
• NPASS: NPC183754