Aristolochic acid II

Details

• Internal ID: 0e1a997e-903d-4487-8ede-abad73e209ce
• Taxonomy: Benzenoids > Phenanthrenes and derivatives > Aristolochic acids and derivatives
• IUPAC Name: 6-nitronaphtho[2,1-g][1,3]benzodioxole-5-carboxylic acid
• SMILES (Canonical): C1OC2=C(O1)C3=C(C(=C2)C(=O)O)C(=CC4=CC=CC=C43)[N+](=O)[O-]
• SMILES (Isomeric): C1OC2=C(O1)C3=C(C(=C2)C(=O)O)C(=CC4=CC=CC=C43)[N+](=O)[O-]
• InChI: InChI=1S/C16H9NO6/c18-16(19)10-6-12-15(23-7-22-12)14-9-4-2-1-3-8(9)5-11(13(10)14)17(20)21/h1-6H,7H2,(H,18,19)
• InChI Key: MEEXETVZNQYRSP-UHFFFAOYSA-N
• Popularity: 15 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₉NO₆
• Molecular Weight: 311.24 g/mol
• Exact Mass: 311.04298701 g/mol
• Topological Polar Surface Area (TPSA): 102.00 Ų
• XlogP: 3.60
• Atomic LogP (AlogP): 3.33
• H-Bond Acceptor: 5
• H-Bond Donor: 1
• Rotatable Bonds: 2

Synonyms

• Aristolochic acid II
• 475-80-9
• CCRIS 6497
• UNII-BB72D5PU2Y
• EINECS 207-499-6
• BB72D5PU2Y
• BRN 0329754
• CHEMBL602280
• Phenanthro(3,4-d)-1,3-dioxole-5-carboxylic acid, 6-nitro-
• DTXSID00197166
• 5-19-07-00425 (Beilstein Handbook Reference)
• 6-nitronaphtho[2,1-g][1,3]benzodioxole-5-carboxylic acid
• 6-nitrophenanthro[3,4-d][1,3]dioxole-5-carboxylic acid
• 3,4-(Methylenedioxy)-10-nitrophenanthrene-1-carboxylic Acid
• 6-nitronaphtho[1,2-e][1,3]benzodioxole-5-carboxylic acid
• 6-Nitrophenanthro(3,4-d)-1,3-dioxole-5-carboxylic acid
• 6-nitrophenanthro[3,4-d]-1,3-dioxole-5-carboxylic acid
• C16H9NO6
• AristolochicacidB
• SCHEMBL571697
• 6-nitrophenanthro(3,4-d)-3-dioxole-5-carboxylic acid
• DTXCID10119657
• CHEBI:194149
• C16-H9-N-O6
• HY-N0511
• Aristolochic acid II , HPLC Grade
• BDBM50306854
• MFCD01708574
• AKOS015889601
• Aristolochic acid B, >=97% (HPLC)
• AC-34517
• AS-78438
• LS-102940
• CS-0009051
• FT-0622473
• A904448
• Q-100503
• Q2548975
• 6-nitro-phenanthro-[3,4-d]-1,3-dioxole-5-carboxylic acid
• B2703-350870
• 10-Nitro-3,4-(epoxymethanoxy)phenanthrene-1-carboxylic acid
• 6-nitro-2H-phenanthro[3,4-d][1,3]dioxole-5-carboxylic acid
• GOR

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9541	95.41%
Caco-2	-	0.5437	54.37%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	+	0.8571	85.71%
Subcellular localzation	Mitochondria	0.6660	66.60%
OATP2B1 inhibitior	-	0.8613	86.13%
OATP1B1 inhibitior	+	0.9265	92.65%
OATP1B3 inhibitior	+	0.9381	93.81%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	+	0.6032	60.32%
P-glycoprotein inhibitior	-	0.8498	84.98%
P-glycoprotein substrate	-	0.9381	93.81%
CYP3A4 substrate	-	0.5375	53.75%
CYP2C9 substrate	-	0.7773	77.73%
CYP2D6 substrate	-	0.8908	89.08%
CYP3A4 inhibition	-	0.9347	93.47%
CYP2C9 inhibition	-	0.9137	91.37%
CYP2C19 inhibition	-	0.9367	93.67%
CYP2D6 inhibition	-	0.9264	92.64%
CYP1A2 inhibition	+	0.9009	90.09%
CYP2C8 inhibition	-	0.6018	60.18%
CYP inhibitory promiscuity	-	0.7142	71.42%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.5863	58.63%
Carcinogenicity (trinary)	Non-required	0.4262	42.62%
Eye corrosion	-	0.9707	97.07%
Eye irritation	+	0.7946	79.46%
Skin irritation	-	0.6468	64.68%
Skin corrosion	-	0.9383	93.83%
Ames mutagenesis	+	0.9100	91.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.9213	92.13%
Micronuclear	+	0.9700	97.00%
Hepatotoxicity	+	0.6875	68.75%
skin sensitisation	-	0.8055	80.55%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.6000	60.00%
Mitochondrial toxicity	-	0.5445	54.45%
Nephrotoxicity	+	0.5389	53.89%
Acute Oral Toxicity (c)	II	0.4824	48.24%
Estrogen receptor binding	+	0.8616	86.16%
Androgen receptor binding	+	0.6898	68.98%
Thyroid receptor binding	+	0.6489	64.89%
Glucocorticoid receptor binding	+	0.8957	89.57%
Aromatase binding	+	0.6348	63.48%
PPAR gamma	+	0.8347	83.47%
Honey bee toxicity	-	0.9315	93.15%
Biodegradation	-	0.9500	95.00%
Crustacea aquatic toxicity	-	0.7200	72.00%
Fish aquatic toxicity	+	0.9771	97.71%

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	92.81%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.40%	86.33%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.19%	91.11%
CHEMBL3902	P09211	Glutathione S-transferase Pi	91.30%	93.81%
CHEMBL2581	P07339	Cathepsin D	88.14%	98.95%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.49%	99.23%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	86.21%	94.80%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	84.37%	92.62%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.04%	89.00%
CHEMBL3401	O75469	Pregnane X receptor	82.69%	94.73%
CHEMBL1741221	Q9Y4P1	Cysteine protease ATG4B	81.36%	87.50%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	81.14%	96.77%

Plants that contains it

• Akebia quinata
• Akebia trifoliata
• Aristolochia argentina
• Aristolochia auricularia
• Aristolochia baetica
• Aristolochia clematitis
• Aristolochia contorta
• Aristolochia cucurbitifolia
• Aristolochia debilis
• Aristolochia fangchi
• Aristolochia kaempferi
• Aristolochia manshuriensis
• Aristolochia mollissima
• Aristolochia pontica
• Aristolochia pubescens
• Aristolochia rotunda
• Aristolochia tuberosa
• Aristolochia zollingeriana
• Asarum heterotropoides
• Asarum sieboldii
• Cocculus orbiculatus
• Sinomenium acutum
• Stephania tetrandra

Cross-Links

• PubChem: 108168
• NPASS: NPC46679
• LOTUS: LTS0226198
• wikiData: Q103818705