norquadrangularic acid A

Details

• Internal ID: 5fb56bf0-7069-421d-83a7-22d3031770d4
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
• IUPAC Name: (1S,3S,4S,6S,7S,8R,11S,12S,15R,16R)-15-[(2R)-4-carboxybutan-2-yl]-4,6-dihydroxy-7,12,16-trimethylpentacyclo[9.7.0.01,3.03,8.012,16]octadecane-7-carboxylic acid
• SMILES (Canonical): CC(CCC(=O)O)C1CCC2(C1(CCC34C2CCC5C3(C4)C(CC(C5(C)C(=O)O)O)O)C)C
• SMILES (Isomeric): C[C@H](CCC(=O)O)[C@H]1CC[C@@]2([C@@]1(CC[C@]34[C@H]2CC[C@@H]5[C@]3(C4)[C@H](C[C@@H]([C@@]5(C)C(=O)O)O)O)C)C
• InChI: InChI=1S/C27H42O6/c1-15(5-8-21(30)31)16-9-10-24(3)17-6-7-18-25(4,22(32)33)19(28)13-20(29)27(18)14-26(17,27)12-11-23(16,24)2/h15-20,28-29H,5-14H2,1-4H3,(H,30,31)(H,32,33)/t15-,16-,17+,18+,19+,20+,23-,24+,25+,26+,27-/m1/s1
• InChI Key: PLBUBUFCNAFBIN-IQPYMKAHSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₄₂O₆
• Molecular Weight: 462.60 g/mol
• Exact Mass: 462.29813906 g/mol
• Topological Polar Surface Area (TPSA): 115.00 Ų
• XlogP: 5.20
• Atomic LogP (AlogP): 4.32
• H-Bond Acceptor: 4
• H-Bond Donor: 4
• Rotatable Bonds: 5

Synonyms

• CHEMBL479490
• PLBUBUFCNAFBIN-IQPYMKAHSA-
• InChI=1/C27H42O6/c1-15(5-8-21(30)31)16-9-10-24(3)17-6-7-18-25(4,22(32)33)19(28)13-20(29)27(18)14-26(17,27)12-11-23(16,24)2/h15-20,28-29H,5-14H2,1-4H3,(H,30,31)(H,32,33)/t15-,16-,17+,18+,19+,20+,23-,24+,25+,26+,27-/m1/s1

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9518	95.18%
Caco-2	-	0.6697	66.97%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Mitochondria	0.6715	67.15%
OATP2B1 inhibitior	-	0.5682	56.82%
OATP1B1 inhibitior	+	0.8527	85.27%
OATP1B3 inhibitior	+	0.9319	93.19%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.5159	51.59%
P-glycoprotein inhibitior	-	0.6557	65.57%
P-glycoprotein substrate	-	0.5745	57.45%
CYP3A4 substrate	+	0.6660	66.60%
CYP2C9 substrate	-	0.6762	67.62%
CYP2D6 substrate	-	0.8321	83.21%
CYP3A4 inhibition	-	0.7770	77.70%
CYP2C9 inhibition	-	0.7978	79.78%
CYP2C19 inhibition	-	0.8919	89.19%
CYP2D6 inhibition	-	0.9662	96.62%
CYP1A2 inhibition	-	0.8428	84.28%
CYP2C8 inhibition	-	0.7178	71.78%
CYP inhibitory promiscuity	-	0.9610	96.10%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.7337	73.37%
Eye corrosion	-	0.9933	99.33%
Eye irritation	-	0.9362	93.62%
Skin irritation	+	0.6019	60.19%
Skin corrosion	-	0.9115	91.15%
Ames mutagenesis	-	0.7419	74.19%
Human Ether-a-go-go-Related Gene inhibition	-	0.3993	39.93%
Micronuclear	-	0.8000	80.00%
Hepatotoxicity	-	0.5868	58.68%
skin sensitisation	-	0.8672	86.72%
Respiratory toxicity	+	0.6556	65.56%
Reproductive toxicity	+	0.9889	98.89%
Mitochondrial toxicity	+	0.9500	95.00%
Nephrotoxicity	-	0.8817	88.17%
Acute Oral Toxicity (c)	I	0.3268	32.68%
Estrogen receptor binding	+	0.6994	69.94%
Androgen receptor binding	+	0.7444	74.44%
Thyroid receptor binding	+	0.6069	60.69%
Glucocorticoid receptor binding	+	0.7517	75.17%
Aromatase binding	+	0.7790	77.90%
PPAR gamma	+	0.5661	56.61%
Honey bee toxicity	-	0.8340	83.40%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.7800	78.00%
Fish aquatic toxicity	+	0.9865	98.65%

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	97.02%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	96.90%	97.25%
CHEMBL221	P23219	Cyclooxygenase-1	93.98%	90.17%
CHEMBL2179	P04062	Beta-glucocerebrosidase	92.47%	85.31%
CHEMBL218	P21554	Cannabinoid CB1 receptor	90.35%	96.61%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	90.28%	96.38%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	90.23%	96.95%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	90.12%	95.17%
CHEMBL340	P08684	Cytochrome P450 3A4	89.27%	91.19%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	89.22%	93.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.13%	94.45%
CHEMBL2581	P07339	Cathepsin D	87.83%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.75%	97.09%
CHEMBL4040	P28482	MAP kinase ERK2	86.58%	83.82%
CHEMBL4227	P25090	Lipoxin A4 receptor	86.19%	100.00%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	85.70%	91.11%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	84.98%	96.47%
CHEMBL236	P41143	Delta opioid receptor	84.78%	99.35%
CHEMBL4618	P09960	Leukotriene A4 hydrolase	84.28%	97.86%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	84.10%	90.71%
CHEMBL3359	P21462	Formyl peptide receptor 1	83.61%	93.56%
CHEMBL2514	O95665	Neurotensin receptor 2	83.09%	100.00%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	82.60%	93.04%
CHEMBL2815	P04629	Nerve growth factor receptor Trk-A	82.02%	87.16%
CHEMBL274	P51681	C-C chemokine receptor type 5	81.39%	98.77%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	81.26%	82.69%
CHEMBL4330	Q9NS75	Cysteinyl leukotriene receptor 2	80.79%	98.00%

Plants that contains it

• Clerodendrum calamitosum
• Combretum quadrangulare
• Isatis tinctoria
• Saussurea medusa

Cross-Links

• PubChem: 10790237
• NPASS: NPC302111
• LOTUS: LTS0264868
• wikiData: Q105185003