Anhydromarmeline

Details

• Internal ID: 413dd9c5-819d-4b2f-b7bb-8f5e4dfcffe6
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Cinnamic acid amides
• IUPAC Name: (E)-N-[(E)-2-[4-(3-methylbut-2-enoxy)phenyl]ethenyl]-3-phenylprop-2-enamide
• InChI: InChI=1S/C22H23NO2/c1-18(2)15-17-25-21-11-8-20(9-12-21)14-16-23-22(24)13-10-19-6-4-3-5-7-19/h3-16H,17H2,1-2H3,(H,23,24)/b13-10+,16-14+
• InChI Key: QBZNVFGBZZATNO-BMCDEEFISA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₂₃NO₂
• Molecular Weight: 333.40 g/mol
• Exact Mass: 333.172878976 g/mol
• Topological Polar Surface Area (TPSA): 38.30 Ų
• XlogP: 5.10
• Atomic LogP (AlogP): 4.83
• H-Bond Acceptor: 2
• H-Bond Donor: 1
• Rotatable Bonds: 7

Synonyms

• RefChem:112786
• (E)-N-((E)-2-(4-(3-methylbut-2-enoxy)phenyl)ethenyl)-3-phenylprop-2-enamide
• 1072443-48-1
• CHEMBL490179
• SCHEMBL30176874

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	1.0000	100.00%
Caco-2	+	0.7098	70.98%
Blood Brain Barrier	+	0.8000	80.00%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.8088	80.88%
OATP2B1 inhibitior	-	0.8599	85.99%
OATP1B1 inhibitior	+	0.9296	92.96%
OATP1B3 inhibitior	+	0.9424	94.24%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	+	0.9308	93.08%
P-glycoprotein inhibitior	+	0.6444	64.44%
P-glycoprotein substrate	-	0.8776	87.76%
CYP3A4 substrate	+	0.5252	52.52%
CYP2C9 substrate	-	0.7818	78.18%
CYP2D6 substrate	-	0.8437	84.37%
CYP3A4 inhibition	-	0.6201	62.01%
CYP2C9 inhibition	-	0.5961	59.61%
CYP2C19 inhibition	-	0.5240	52.40%
CYP2D6 inhibition	-	0.7975	79.75%
CYP1A2 inhibition	+	0.8610	86.10%
CYP2C8 inhibition	+	0.5990	59.90%
CYP inhibitory promiscuity	+	0.9121	91.21%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.7551	75.51%
Carcinogenicity (trinary)	Non-required	0.5376	53.76%
Eye corrosion	-	0.9912	99.12%
Eye irritation	-	0.7734	77.34%
Skin irritation	-	0.8311	83.11%
Skin corrosion	-	0.9716	97.16%
Ames mutagenesis	-	0.6800	68.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8122	81.22%
Micronuclear	+	0.6200	62.00%
Hepatotoxicity	-	0.6073	60.73%
skin sensitisation	-	0.8059	80.59%
Respiratory toxicity	-	0.5667	56.67%
Reproductive toxicity	+	0.7111	71.11%
Mitochondrial toxicity	+	0.5375	53.75%
Nephrotoxicity	+	0.5000	50.00%
Acute Oral Toxicity (c)	III	0.6776	67.76%
Estrogen receptor binding	+	0.8520	85.20%
Androgen receptor binding	+	0.8702	87.02%
Thyroid receptor binding	+	0.6511	65.11%
Glucocorticoid receptor binding	+	0.6633	66.33%
Aromatase binding	+	0.7568	75.68%
PPAR gamma	+	0.6433	64.33%
Honey bee toxicity	-	0.8845	88.45%
Biodegradation	-	0.9750	97.50%
Crustacea aquatic toxicity	-	0.6000	60.00%
Fish aquatic toxicity	+	0.9818	98.18%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL221	P23219	Cyclooxygenase-1	96.03%	90.17%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.97%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.22%	86.33%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	94.09%	96.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	92.86%	99.17%
CHEMBL4208	P20618	Proteasome component C5	91.57%	90.00%
CHEMBL3401	O75469	Pregnane X receptor	90.23%	94.73%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.87%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.40%	96.09%
CHEMBL2581	P07339	Cathepsin D	88.44%	98.95%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	87.03%	94.62%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	86.55%	95.50%
CHEMBL1293277	O15118	Niemann-Pick C1 protein	80.50%	81.11%

Plants that contains it

• Aegle marmelos

Cross-Links

• PubChem: 44579695
• NPASS: NPC256369
• LOTUS: LTS0177237
• wikiData: Q105218106