Methanone, (2,6-dihydroxy-4-methoxyphenyl)[(1R,5S,6R)-4-methyl-5-(3-methyl-2-butenyl)-6-phenyl-3-cyclohexen-1-yl]-, rel-

Details

• Internal ID: 1a974720-8f33-409d-9e1e-ec82ea4ced04
• Taxonomy: Phenylpropanoids and polyketides > Diarylheptanoids > Linear diarylheptanoids
• IUPAC Name: (2,6-dihydroxy-4-methoxyphenyl)-[4-methyl-5-(3-methylbut-2-enyl)-6-phenylcyclohex-3-en-1-yl]methanone
• SMILES (Canonical): CC1=CCC(C(C1CC=C(C)C)C2=CC=CC=C2)C(=O)C3=C(C=C(C=C3O)OC)O
• SMILES (Isomeric): CC1=CCC(C(C1CC=C(C)C)C2=CC=CC=C2)C(=O)C3=C(C=C(C=C3O)OC)O
• InChI: InChI=1S/C26H30O4/c1-16(2)10-12-20-17(3)11-13-21(24(20)18-8-6-5-7-9-18)26(29)25-22(27)14-19(30-4)15-23(25)28/h5-11,14-15,20-21,24,27-28H,12-13H2,1-4H3
• InChI Key: CIQQYRZTKOGULG-UHFFFAOYSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₆H₃₀O₄
• Molecular Weight: 406.50 g/mol
• Exact Mass: 406.21440943 g/mol
• Topological Polar Surface Area (TPSA): 66.80 Ų
• XlogP: 6.00
• Atomic LogP (AlogP): 6.01
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 6

Synonyms

• Nicolaioidesin B
• (.+/-.)-Nicolaioidesin B
• CIQQYRZTKOGULG-UHFFFAOYSA-N
• (2,6-Dihydroxy-4-methoxyphenyl)((1R,2R,6S)-5-methyl-6-(3-methylbut-2-en-1-yl)-1,2,3,6-tetrahydro-[1,1'-biphenyl]-2-yl)methanone
• (2,6-dihydroxy-4-methoxyphenyl)-[4-methyl-5-(3-methylbut-2-enyl)-6-phenylcyclohex-3-en-1-yl]methanone
• Methanone, (2,6-dihydroxy-4-methoxyphenyl)[(1R,5S,6R)-4-methyl-5-(3-methyl-2-buten-1-yl)-6-phenyl-3-cyclohexen-1-yl]-, rel-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9948	99.48%
Caco-2	+	0.6305	63.05%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Mitochondria	0.8798	87.98%
OATP2B1 inhibitior	-	0.8616	86.16%
OATP1B1 inhibitior	+	0.9198	91.98%
OATP1B3 inhibitior	+	0.8448	84.48%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.9378	93.78%
P-glycoprotein inhibitior	+	0.8818	88.18%
P-glycoprotein substrate	-	0.7720	77.20%
CYP3A4 substrate	+	0.5565	55.65%
CYP2C9 substrate	-	0.7904	79.04%
CYP2D6 substrate	-	0.8029	80.29%
CYP3A4 inhibition	-	0.6279	62.79%
CYP2C9 inhibition	+	0.8401	84.01%
CYP2C19 inhibition	+	0.9529	95.29%
CYP2D6 inhibition	-	0.7652	76.52%
CYP1A2 inhibition	+	0.8348	83.48%
CYP2C8 inhibition	+	0.6720	67.20%
CYP inhibitory promiscuity	+	0.9354	93.54%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.7627	76.27%
Carcinogenicity (trinary)	Non-required	0.7440	74.40%
Eye corrosion	-	0.9904	99.04%
Eye irritation	-	0.8896	88.96%
Skin irritation	-	0.8239	82.39%
Skin corrosion	-	0.9558	95.58%
Ames mutagenesis	-	0.5700	57.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7895	78.95%
Micronuclear	+	0.5100	51.00%
Hepatotoxicity	+	0.6250	62.50%
skin sensitisation	-	0.7651	76.51%
Respiratory toxicity	+	0.6333	63.33%
Reproductive toxicity	+	0.7000	70.00%
Mitochondrial toxicity	-	0.6000	60.00%
Nephrotoxicity	+	0.5000	50.00%
Acute Oral Toxicity (c)	III	0.6726	67.26%
Estrogen receptor binding	+	0.6877	68.77%
Androgen receptor binding	+	0.8168	81.68%
Thyroid receptor binding	+	0.6771	67.71%
Glucocorticoid receptor binding	+	0.8164	81.64%
Aromatase binding	-	0.5376	53.76%
PPAR gamma	+	0.8061	80.61%
Honey bee toxicity	-	0.8668	86.68%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.6700	67.00%
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	98.27%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.05%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.85%	95.56%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	91.90%	96.95%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	91.10%	99.15%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.57%	86.33%
CHEMBL2581	P07339	Cathepsin D	90.33%	98.95%
CHEMBL3401	O75469	Pregnane X receptor	90.02%	94.73%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	88.97%	95.50%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.60%	99.17%
CHEMBL4208	P20618	Proteasome component C5	86.48%	90.00%
CHEMBL221	P23219	Cyclooxygenase-1	86.42%	90.17%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	84.38%	94.08%
CHEMBL240	Q12809	HERG	83.32%	89.76%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	83.01%	95.89%
CHEMBL2535	P11166	Glucose transporter	82.35%	98.75%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.14%	97.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	80.13%	85.14%

Plants that contains it

• Boesenbergia rotunda
• Renealmia nicolaioides

Cross-Links

• PubChem: 22297525
• LOTUS: LTS0065167
• wikiData: Q104960150