Madolin A

Details

• Internal ID: d0523c70-24fa-48ed-9700-df63fe6cb41a
• Taxonomy: Organoheterocyclic compounds > Epoxides
• IUPAC Name: (1R,4R,6R,9E,11S)-4,12,12-trimethyl-5-oxatricyclo[9.1.0.04,6]dodec-9-ene-9-carbaldehyde
• SMILES (Canonical): CC1(C2C1C=C(CCC3C(O3)(CC2)C)C=O)C
• SMILES (Isomeric): C[C@@]12CC[C@@H]3[C@@H](C3(C)C)/C=C(\CC[C@H]1O2)/C=O
• InChI: InChI=1S/C15H22O2/c1-14(2)11-6-7-15(3)13(17-15)5-4-10(9-16)8-12(11)14/h8-9,11-13H,4-7H2,1-3H3/b10-8+/t11-,12+,13-,15-/m1/s1
• InChI Key: ZWFIFCRKFITASO-IVYHSSSVSA-N
• Popularity: 10 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₂O₂
• Molecular Weight: 234.33 g/mol
• Exact Mass: 234.161979940 g/mol
• Topological Polar Surface Area (TPSA): 29.60 Ų
• XlogP: 2.60
• Atomic LogP (AlogP): 3.12
• H-Bond Acceptor: 2
• H-Bond Donor: 0
• Rotatable Bonds: 1

Synonyms

• (+)-Madolin A
• WE7GW30253
• 205371-29-5
• 5-Oxatricyclo(9.1.0.04,6)dodec-9-ene-9-carboxaldehyde, 4,12,12-trimethyl-, (1R,4R,6R,9E,11S)-
• UNII-WE7GW30253
• CHEMBL1224785
• Q27292587

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9952	99.52%
Caco-2	+	0.8892	88.92%
Blood Brain Barrier	+	0.8750	87.50%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Mitochondria	0.3734	37.34%
OATP2B1 inhibitior	-	0.8540	85.40%
OATP1B1 inhibitior	+	0.9100	91.00%
OATP1B3 inhibitior	+	0.9690	96.90%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.6250	62.50%
BSEP inhibitior	-	0.6937	69.37%
P-glycoprotein inhibitior	-	0.8503	85.03%
P-glycoprotein substrate	-	0.9237	92.37%
CYP3A4 substrate	+	0.6043	60.43%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8444	84.44%
CYP3A4 inhibition	-	0.8224	82.24%
CYP2C9 inhibition	+	0.6131	61.31%
CYP2C19 inhibition	+	0.7422	74.22%
CYP2D6 inhibition	-	0.9304	93.04%
CYP1A2 inhibition	+	0.7664	76.64%
CYP2C8 inhibition	-	0.8371	83.71%
CYP inhibitory promiscuity	-	0.8649	86.49%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.7400	74.00%
Carcinogenicity (trinary)	Non-required	0.5790	57.90%
Eye corrosion	-	0.9181	91.81%
Eye irritation	-	0.9531	95.31%
Skin irritation	+	0.5590	55.90%
Skin corrosion	-	0.9630	96.30%
Ames mutagenesis	-	0.6800	68.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4550	45.50%
Micronuclear	-	0.7300	73.00%
Hepatotoxicity	+	0.6178	61.78%
skin sensitisation	+	0.7854	78.54%
Respiratory toxicity	+	0.6889	68.89%
Reproductive toxicity	-	0.7333	73.33%
Mitochondrial toxicity	-	0.6250	62.50%
Nephrotoxicity	+	0.4704	47.04%
Acute Oral Toxicity (c)	III	0.7545	75.45%
Estrogen receptor binding	+	0.6536	65.36%
Androgen receptor binding	-	0.5234	52.34%
Thyroid receptor binding	+	0.5227	52.27%
Glucocorticoid receptor binding	+	0.6545	65.45%
Aromatase binding	-	0.6601	66.01%
PPAR gamma	-	0.7252	72.52%
Honey bee toxicity	-	0.8653	86.53%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	+	0.6400	64.00%
Fish aquatic toxicity	+	0.9041	90.41%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.69%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.51%	95.56%
CHEMBL1994	P08235	Mineralocorticoid receptor	90.40%	100.00%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	90.37%	93.40%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.22%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.97%	86.33%
CHEMBL253	P34972	Cannabinoid CB2 receptor	83.51%	97.25%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.71%	95.89%
CHEMBL4208	P20618	Proteasome component C5	81.58%	90.00%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	81.56%	91.11%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	80.91%	97.14%
CHEMBL2781	P19634	Sodium/hydrogen exchanger 1	80.28%	90.24%

Plants that contains it

• Aristolochia cucurbitifolia
• Aristolochia kaempferi
• Aristolochia mollissima

Cross-Links

• PubChem: 10561685
• LOTUS: LTS0092838
• wikiData: Q27292587