Citrusal

Details

• Internal ID: e558205b-842a-4ae4-851a-5fe77eb471d1
• Taxonomy: Phenylpropanoids and polyketides > Coumarins and derivatives
• IUPAC Name: 3-(7-methoxy-2-oxochromen-8-yl)-2,2-dimethylpropanal
• SMILES (Canonical): CC(C)(CC1=C(C=CC2=C1OC(=O)C=C2)OC)C=O
• SMILES (Isomeric): CC(C)(CC1=C(C=CC2=C1OC(=O)C=C2)OC)C=O
• InChI: InChI=1S/C15H16O4/c1-15(2,9-16)8-11-12(18-3)6-4-10-5-7-13(17)19-14(10)11/h4-7,9H,8H2,1-3H3
• InChI Key: VCYVDHAWDPDCKW-UHFFFAOYSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₆O₄
• Molecular Weight: 260.28 g/mol
• Exact Mass: 260.10485899 g/mol
• Topological Polar Surface Area (TPSA): 52.60 Ų
• XlogP: 2.50
• Atomic LogP (AlogP): 2.57
• H-Bond Acceptor: 4
• H-Bond Donor: 0
• Rotatable Bonds: 4

Synonyms

• Morphine sulphate (anhydrous)
• 3-(7-methoxy-2-oxochromen-8-yl)-2,2-dimethylpropanal
• CHEBI:174411
• 7-Methoxy-8-(2-formyl-2-methylpropyl)coumarin
• 7-Methoxy-8-(2'-formyl-2'-methylpropyl) coumarin
• 3-(7-methoxy-2-oxo-2H-chromen-8-yl)-2,2-dimethylpropanal
• 7-Methoxy-8-(2-formyl-2-methylpropyl)-2H-1-benzopyran-2-one
• 8-(2,2-Dimethyl-3-oxopropyl)-7-methoxy-2H-1-benzopyran-2-one, 9CI

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9740	97.40%
Caco-2	+	0.7621	76.21%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	+	0.5714	57.14%
Subcellular localzation	Mitochondria	0.6288	62.88%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8938	89.38%
OATP1B3 inhibitior	+	0.9712	97.12%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.4712	47.12%
P-glycoprotein inhibitior	-	0.9198	91.98%
P-glycoprotein substrate	-	0.8470	84.70%
CYP3A4 substrate	-	0.5718	57.18%
CYP2C9 substrate	-	0.6506	65.06%
CYP2D6 substrate	-	0.8167	81.67%
CYP3A4 inhibition	-	0.7038	70.38%
CYP2C9 inhibition	+	0.5727	57.27%
CYP2C19 inhibition	-	0.6471	64.71%
CYP2D6 inhibition	-	0.9295	92.95%
CYP1A2 inhibition	+	0.7597	75.97%
CYP2C8 inhibition	-	0.6974	69.74%
CYP inhibitory promiscuity	-	0.5980	59.80%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9513	95.13%
Carcinogenicity (trinary)	Non-required	0.6015	60.15%
Eye corrosion	-	0.9774	97.74%
Eye irritation	-	0.8569	85.69%
Skin irritation	-	0.8639	86.39%
Skin corrosion	-	0.9688	96.88%
Ames mutagenesis	-	0.6100	61.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4441	44.41%
Micronuclear	-	0.5500	55.00%
Hepatotoxicity	+	0.7000	70.00%
skin sensitisation	-	0.8921	89.21%
Respiratory toxicity	-	0.6667	66.67%
Reproductive toxicity	+	0.6889	68.89%
Mitochondrial toxicity	+	0.5250	52.50%
Nephrotoxicity	-	0.5934	59.34%
Acute Oral Toxicity (c)	III	0.5636	56.36%
Estrogen receptor binding	+	0.7167	71.67%
Androgen receptor binding	+	0.6329	63.29%
Thyroid receptor binding	-	0.7144	71.44%
Glucocorticoid receptor binding	+	0.5489	54.89%
Aromatase binding	+	0.8513	85.13%
PPAR gamma	+	0.6843	68.43%
Honey bee toxicity	-	0.8920	89.20%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5500	55.00%
Fish aquatic toxicity	+	0.9900	99.00%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.22%	95.56%
CHEMBL2581	P07339	Cathepsin D	90.78%	98.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	90.00%	94.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.73%	86.33%
CHEMBL3401	O75469	Pregnane X receptor	85.81%	94.73%
CHEMBL1255126	O15151	Protein Mdm4	84.85%	90.20%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	82.84%	80.78%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	81.18%	89.34%
CHEMBL4306	P22460	Voltage-gated potassium channel subunit Kv1.5	80.08%	94.03%

Plants that contains it

• Dracaena cochinchinensis
• Murraya paniculata

Cross-Links

• PubChem: 5319433
• NPASS: NPC175076
• LOTUS: LTS0124546
• wikiData: Q105284034