Madolin B

Details

• Internal ID: ae947946-3e8d-42f6-834b-aac43855061f
• 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-carboxylic acid
• SMILES (Canonical): CC1(C2C1C=C(CCC3C(O3)(CC2)C)C(=O)O)C
• SMILES (Isomeric): C[C@@]12CC[C@@H]3[C@@H](C3(C)C)/C=C(\CC[C@H]1O2)/C(=O)O
• InChI: InChI=1S/C15H22O3/c1-14(2)10-6-7-15(3)12(18-15)5-4-9(13(16)17)8-11(10)14/h8,10-12H,4-7H2,1-3H3,(H,16,17)/b9-8+/t10-,11+,12-,15-/m1/s1
• InChI Key: FDRRKJHGACAWCZ-CBKTVSPZSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₂O₃
• Molecular Weight: 250.33 g/mol
• Exact Mass: 250.15689456 g/mol
• Topological Polar Surface Area (TPSA): 49.80 Ų
• XlogP: 2.70
• Atomic LogP (AlogP): 3.00
• H-Bond Acceptor: 2
• H-Bond Donor: 1
• Rotatable Bonds: 1

Synonyms

• (+)-Madolin B
• UNII-8L8514W2S1
• 8L8514W2S1
• 205239-54-9
• 5-Oxatricyclo(9.1.0.04,6)dodec-9-ene-9-carboxylic acid, 4,12,12-trimethyl-, (1R,4R,6R,9E,11S)-
• 5-Oxatricyclo(9.1.0.04,6)dodec-9-ene-9-carboxylic acid, 4,12,12-trimethyl-, (1R-(1R*,4R*,6R*,9E,11S*))-
• Q27270707

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9882	98.82%
Caco-2	+	0.8460	84.60%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	+	0.5429	54.29%
Subcellular localzation	Mitochondria	0.6112	61.12%
OATP2B1 inhibitior	-	0.8533	85.33%
OATP1B1 inhibitior	+	0.9360	93.60%
OATP1B3 inhibitior	+	0.9326	93.26%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.5000	50.00%
BSEP inhibitior	-	0.8565	85.65%
P-glycoprotein inhibitior	-	0.9103	91.03%
P-glycoprotein substrate	-	0.9460	94.60%
CYP3A4 substrate	+	0.5655	56.55%
CYP2C9 substrate	-	0.7980	79.80%
CYP2D6 substrate	-	0.9077	90.77%
CYP3A4 inhibition	-	0.7691	76.91%
CYP2C9 inhibition	+	0.5699	56.99%
CYP2C19 inhibition	+	0.5208	52.08%
CYP2D6 inhibition	-	0.9301	93.01%
CYP1A2 inhibition	+	0.6230	62.30%
CYP2C8 inhibition	-	0.8512	85.12%
CYP inhibitory promiscuity	-	0.9212	92.12%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8400	84.00%
Carcinogenicity (trinary)	Non-required	0.6191	61.91%
Eye corrosion	-	0.9552	95.52%
Eye irritation	-	0.8843	88.43%
Skin irritation	-	0.5228	52.28%
Skin corrosion	-	0.9506	95.06%
Ames mutagenesis	-	0.8300	83.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7430	74.30%
Micronuclear	-	0.7000	70.00%
Hepatotoxicity	+	0.7178	71.78%
skin sensitisation	+	0.6454	64.54%
Respiratory toxicity	+	0.7667	76.67%
Reproductive toxicity	+	0.5059	50.59%
Mitochondrial toxicity	+	0.5625	56.25%
Nephrotoxicity	-	0.7085	70.85%
Acute Oral Toxicity (c)	III	0.6270	62.70%
Estrogen receptor binding	+	0.6989	69.89%
Androgen receptor binding	+	0.5273	52.73%
Thyroid receptor binding	+	0.5934	59.34%
Glucocorticoid receptor binding	+	0.8441	84.41%
Aromatase binding	-	0.6951	69.51%
PPAR gamma	-	0.6414	64.14%
Honey bee toxicity	-	0.9205	92.05%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.6451	64.51%
Fish aquatic toxicity	+	0.9634	96.34%

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	97.13%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.02%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.23%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.14%	95.56%
CHEMBL253	P34972	Cannabinoid CB2 receptor	83.73%	97.25%
CHEMBL340	P08684	Cytochrome P450 3A4	82.44%	91.19%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.44%	100.00%
CHEMBL2581	P07339	Cathepsin D	81.09%	98.95%
CHEMBL5028	O14672	ADAM10	80.65%	97.50%

Plants that contains it

• Aristolochia cucurbitifolia
• Aristolochia kaempferi
• Aristolochia mollissima

Cross-Links

• PubChem: 10562641
• LOTUS: LTS0216092
• wikiData: Q27270707