[(1S,4R,9R,10R,13R,14R)-14-(hydroxymethyl)-5,5,9-trimethyl-14-tetracyclo[11.2.1.01,10.04,9]hexadecanyl] 8-methoxy-6-nitronaphtho[1,2-e][1,3]benzodioxole-5-carboxylate

Details

• Internal ID: 8b5cf7f3-92f2-4da7-99a4-92f509745292
• Taxonomy: Benzenoids > Phenanthrenes and derivatives > Aristolochic acids and derivatives
• IUPAC Name: [(1S,4R,9R,10R,13R,14R)-14-(hydroxymethyl)-5,5,9-trimethyl-14-tetracyclo[11.2.1.01,10.04,9]hexadecanyl] 8-methoxy-6-nitronaphtho[1,2-e][1,3]benzodioxole-5-carboxylate
• SMILES (Canonical): CC1(CCCC2(C1CCC34C2CCC(C3)C(C4)(CO)OC(=O)C5=CC6=C(C7=C8C=CC=C(C8=CC(=C57)[N+](=O)[O-])OC)OCO6)C)C
• SMILES (Isomeric): C[C@@]12CCCC([C@H]1CC[C@]34[C@H]2CC[C@H](C3)[C@](C4)(CO)OC(=O)C5=CC6=C(C7=C8C=CC=C(C8=CC(=C57)[N+](=O)[O-])OC)OCO6)(C)C
• InChI: InChI=1S/C37H43NO8/c1-34(2)12-6-13-35(3)28(34)11-14-36-17-21(9-10-29(35)36)37(18-36,19-39)46-33(40)24-16-27-32(45-20-44-27)31-22-7-5-8-26(43-4)23(22)15-25(30(24)31)38(41)42/h5,7-8,15-16,21,28-29,39H,6,9-14,17-20H2,1-4H3/t21-,28-,29+,35-,36+,37+/m1/s1
• InChI Key: KFVNSGSGMMBVOZ-ITGUHTALSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₇H₄₃NO₈
• Molecular Weight: 629.70 g/mol
• Exact Mass: 629.29886733 g/mol
• Topological Polar Surface Area (TPSA): 120.00 Ų
• XlogP: 9.20
• Atomic LogP (AlogP): 7.96
• H-Bond Acceptor: 8
• H-Bond Donor: 1
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8920	89.20%
Caco-2	-	0.8201	82.01%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	+	0.5143	51.43%
Subcellular localzation	Mitochondria	0.5068	50.68%
OATP2B1 inhibitior	-	0.5781	57.81%
OATP1B1 inhibitior	+	0.8552	85.52%
OATP1B3 inhibitior	+	0.9273	92.73%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.5000	50.00%
BSEP inhibitior	+	0.9909	99.09%
P-glycoprotein inhibitior	+	0.7759	77.59%
P-glycoprotein substrate	+	0.6433	64.33%
CYP3A4 substrate	+	0.7448	74.48%
CYP2C9 substrate	+	0.5870	58.70%
CYP2D6 substrate	-	0.8464	84.64%
CYP3A4 inhibition	+	0.5468	54.68%
CYP2C9 inhibition	-	0.6712	67.12%
CYP2C19 inhibition	-	0.5806	58.06%
CYP2D6 inhibition	-	0.8321	83.21%
CYP1A2 inhibition	-	0.6209	62.09%
CYP2C8 inhibition	+	0.8312	83.12%
CYP inhibitory promiscuity	-	0.5722	57.22%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.7400	74.00%
Carcinogenicity (trinary)	Non-required	0.5132	51.32%
Eye corrosion	-	0.9794	97.94%
Eye irritation	-	0.9257	92.57%
Skin irritation	-	0.7780	77.80%
Skin corrosion	-	0.9254	92.54%
Ames mutagenesis	+	0.6500	65.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6999	69.99%
Micronuclear	+	0.8900	89.00%
Hepatotoxicity	-	0.5679	56.79%
skin sensitisation	-	0.8404	84.04%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.6889	68.89%
Mitochondrial toxicity	+	0.6000	60.00%
Nephrotoxicity	-	0.7223	72.23%
Acute Oral Toxicity (c)	III	0.5522	55.22%
Estrogen receptor binding	+	0.8235	82.35%
Androgen receptor binding	+	0.7486	74.86%
Thyroid receptor binding	+	0.5632	56.32%
Glucocorticoid receptor binding	+	0.8013	80.13%
Aromatase binding	+	0.7668	76.68%
PPAR gamma	+	0.6965	69.65%
Honey bee toxicity	-	0.7307	73.07%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.6233	62.33%
Fish aquatic toxicity	+	0.9932	99.32%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	98.31%	94.45%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.89%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.84%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	97.80%	86.33%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	97.26%	96.77%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	96.51%	92.62%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	95.83%	94.80%
CHEMBL2581	P07339	Cathepsin D	94.99%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.45%	95.56%
CHEMBL2535	P11166	Glucose transporter	91.61%	98.75%
CHEMBL5608	Q16288	NT-3 growth factor receptor	91.58%	95.89%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.12%	89.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.55%	97.09%
CHEMBL1741221	Q9Y4P1	Cysteine protease ATG4B	88.22%	87.50%
CHEMBL1255126	O15151	Protein Mdm4	87.49%	90.20%
CHEMBL240	Q12809	HERG	86.84%	89.76%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	86.60%	96.21%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	86.55%	95.83%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.21%	100.00%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	85.47%	95.50%
CHEMBL3192	Q9BY41	Histone deacetylase 8	85.12%	93.99%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	84.89%	97.14%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	83.34%	92.88%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.10%	99.17%
CHEMBL5028	O14672	ADAM10	82.75%	97.50%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	82.53%	94.00%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	82.20%	96.00%
CHEMBL340	P08684	Cytochrome P450 3A4	82.18%	91.19%
CHEMBL253	P34972	Cannabinoid CB2 receptor	80.90%	97.25%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	80.46%	95.71%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	80.30%	94.33%

Plants that contains it

• Aristolochia pubescens

Cross-Links

• PubChem: 21604196
• LOTUS: LTS0158567
• wikiData: Q105140575