[(2R)-1-[(5R,6R)-5-ethenyl-5-methyl-6-(3-oxoprop-1-en-2-yl)cyclohexen-1-yl]propan-2-yl] 6-nitronaphtho[2,1-g][1,3]benzodioxole-5-carboxylate

Details

• Internal ID: 0d862f30-ae40-48a7-87f3-01a924e61be8
• Taxonomy: Benzenoids > Phenanthrenes and derivatives > Aristolochic acids and derivatives
• IUPAC Name: [(2R)-1-[(5R,6R)-5-ethenyl-5-methyl-6-(3-oxoprop-1-en-2-yl)cyclohexen-1-yl]propan-2-yl] 6-nitronaphtho[2,1-g][1,3]benzodioxole-5-carboxylate
• SMILES (Canonical): CC(CC1=CCCC(C1C(=C)C=O)(C)C=C)OC(=O)C2=CC3=C(C4=C2C(=CC5=CC=CC=C54)[N+](=O)[O-])OCO3
• SMILES (Isomeric): C[C@H](CC1=CCC[C@]([C@@H]1C(=C)C=O)(C)C=C)OC(=O)C2=CC3=C(C4=C2C(=CC5=CC=CC=C54)[N+](=O)[O-])OCO3
• InChI: InChI=1S/C31H29NO7/c1-5-31(4)12-8-10-21(28(31)18(2)16-33)13-19(3)39-30(34)23-15-25-29(38-17-37-25)27-22-11-7-6-9-20(22)14-24(26(23)27)32(35)36/h5-7,9-11,14-16,19,28H,1-2,8,12-13,17H2,3-4H3/t19-,28-,31+/m1/s1
• InChI Key: IIBMSRRBRIHDMP-CBZABXCBSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₁H₂₉NO₇
• Molecular Weight: 527.60 g/mol
• Exact Mass: 527.19440226 g/mol
• Topological Polar Surface Area (TPSA): 108.00 Ų
• XlogP: 7.20
• Atomic LogP (AlogP): 6.85
• H-Bond Acceptor: 7
• H-Bond Donor: 0
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9610	96.10%
Caco-2	-	0.8456	84.56%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Mitochondria	0.5616	56.16%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8604	86.04%
OATP1B3 inhibitior	+	0.9275	92.75%
MATE1 inhibitior	-	0.8000	80.00%
OCT2 inhibitior	-	0.7250	72.50%
BSEP inhibitior	+	0.9773	97.73%
P-glycoprotein inhibitior	+	0.8665	86.65%
P-glycoprotein substrate	+	0.5270	52.70%
CYP3A4 substrate	+	0.7151	71.51%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8710	87.10%
CYP3A4 inhibition	+	0.6950	69.50%
CYP2C9 inhibition	-	0.5652	56.52%
CYP2C19 inhibition	+	0.5337	53.37%
CYP2D6 inhibition	-	0.8052	80.52%
CYP1A2 inhibition	+	0.5372	53.72%
CYP2C8 inhibition	+	0.8117	81.17%
CYP inhibitory promiscuity	+	0.8896	88.96%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.5700	57.00%
Carcinogenicity (trinary)	Non-required	0.4975	49.75%
Eye corrosion	-	0.9784	97.84%
Eye irritation	-	0.9283	92.83%
Skin irritation	-	0.7752	77.52%
Skin corrosion	-	0.9249	92.49%
Ames mutagenesis	+	0.6600	66.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4595	45.95%
Micronuclear	+	0.9100	91.00%
Hepatotoxicity	+	0.6399	63.99%
skin sensitisation	-	0.8242	82.42%
Respiratory toxicity	+	0.6556	65.56%
Reproductive toxicity	+	0.6556	65.56%
Mitochondrial toxicity	+	0.5750	57.50%
Nephrotoxicity	+	0.5278	52.78%
Acute Oral Toxicity (c)	III	0.5614	56.14%
Estrogen receptor binding	+	0.7822	78.22%
Androgen receptor binding	+	0.7684	76.84%
Thyroid receptor binding	+	0.6502	65.02%
Glucocorticoid receptor binding	+	0.8361	83.61%
Aromatase binding	+	0.5849	58.49%
PPAR gamma	+	0.6858	68.58%
Honey bee toxicity	-	0.6983	69.83%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	+	0.5245	52.45%
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
CHEMBL240	Q12809	HERG	99.95%	89.76%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.97%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	97.91%	94.45%
CHEMBL2581	P07339	Cathepsin D	97.15%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.88%	96.09%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	95.29%	96.77%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	95.16%	92.62%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.61%	86.33%
CHEMBL3902	P09211	Glutathione S-transferase Pi	92.16%	93.81%
CHEMBL3401	O75469	Pregnane X receptor	92.13%	94.73%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.50%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.30%	89.00%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	89.21%	95.71%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	86.83%	95.50%
CHEMBL221	P23219	Cyclooxygenase-1	86.73%	90.17%
CHEMBL5028	O14672	ADAM10	86.68%	97.50%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.65%	99.23%
CHEMBL4208	P20618	Proteasome component C5	83.50%	90.00%
CHEMBL4225	P49760	Dual specificity protein kinase CLK2	83.40%	80.96%
CHEMBL4072	P07858	Cathepsin B	82.95%	93.67%
CHEMBL2716	Q8WUI4	Histone deacetylase 7	81.30%	89.44%
CHEMBL4224	P49759	Dual specificty protein kinase CLK1	80.98%	85.30%
CHEMBL2378	P30307	Dual specificity phosphatase Cdc25C	80.89%	96.67%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	80.73%	94.80%
CHEMBL340	P08684	Cytochrome P450 3A4	80.02%	91.19%

Plants that contains it

• Aristolochia kaempferi

Cross-Links

• PubChem: 100956032
• LOTUS: LTS0275916
• wikiData: Q105113372