Roccellaric acid

Details

• Internal ID: 40dae1c6-1907-4b4f-8f99-a26cd08384ad
• Taxonomy: Organoheterocyclic compounds > Lactones > Gamma butyrolactones
• IUPAC Name: (2R,3S,4S)-4-methyl-5-oxo-2-tridecyloxolane-3-carboxylic acid
• SMILES (Canonical): CCCCCCCCCCCCCC1C(C(C(=O)O1)C)C(=O)O
• SMILES (Isomeric): CCCCCCCCCCCCC[C@@H]1[C@H]([C@@H](C(=O)O1)C)C(=O)O
• InChI: InChI=1S/C19H34O4/c1-3-4-5-6-7-8-9-10-11-12-13-14-16-17(18(20)21)15(2)19(22)23-16/h15-17H,3-14H2,1-2H3,(H,20,21)/t15-,16+,17-/m0/s1
• InChI Key: WLGALFYTFVOQPY-BBWFWOEESA-N
• Popularity: 6 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₃₄O₄
• Molecular Weight: 326.50 g/mol
• Exact Mass: 326.24570956 g/mol
• Topological Polar Surface Area (TPSA): 63.60 Ų
• XlogP: 6.70
• Atomic LogP (AlogP): 4.95
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 13

Synonyms

• Rocellaric acid
• 19464-85-8
• Nephromopsinic acid (-)
• SCHEMBL16639648
• CHEBI:144295
• (2R,3S,4S)-4-methyl-5-oxo-2-tridecyloxolane-3-carboxylic acid

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9314	93.14%
Caco-2	+	0.5740	57.40%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	-	0.6286	62.86%
Subcellular localzation	Mitochondria	0.7486	74.86%
OATP2B1 inhibitior	-	0.8521	85.21%
OATP1B1 inhibitior	+	0.8879	88.79%
OATP1B3 inhibitior	+	0.9407	94.07%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.7250	72.50%
BSEP inhibitior	-	0.5654	56.54%
P-glycoprotein inhibitior	-	0.6888	68.88%
P-glycoprotein substrate	-	0.8519	85.19%
CYP3A4 substrate	-	0.5996	59.96%
CYP2C9 substrate	+	0.6248	62.48%
CYP2D6 substrate	-	0.8868	88.68%
CYP3A4 inhibition	-	0.6786	67.86%
CYP2C9 inhibition	-	0.8713	87.13%
CYP2C19 inhibition	-	0.8256	82.56%
CYP2D6 inhibition	-	0.9226	92.26%
CYP1A2 inhibition	-	0.8344	83.44%
CYP2C8 inhibition	-	0.9442	94.42%
CYP inhibitory promiscuity	-	0.9565	95.65%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.7428	74.28%
Eye corrosion	-	0.9570	95.70%
Eye irritation	+	0.5425	54.25%
Skin irritation	+	0.5460	54.60%
Skin corrosion	-	0.8177	81.77%
Ames mutagenesis	-	0.9200	92.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5189	51.89%
Micronuclear	-	0.9600	96.00%
Hepatotoxicity	+	0.6387	63.87%
skin sensitisation	-	0.9068	90.68%
Respiratory toxicity	-	0.7111	71.11%
Reproductive toxicity	-	0.7333	73.33%
Mitochondrial toxicity	-	0.5625	56.25%
Nephrotoxicity	+	0.6383	63.83%
Acute Oral Toxicity (c)	III	0.5673	56.73%
Estrogen receptor binding	-	0.5437	54.37%
Androgen receptor binding	-	0.4912	49.12%
Thyroid receptor binding	+	0.5917	59.17%
Glucocorticoid receptor binding	+	0.5520	55.20%
Aromatase binding	-	0.8129	81.29%
PPAR gamma	+	0.6193	61.93%
Honey bee toxicity	-	0.9883	98.83%
Biodegradation	+	0.6250	62.50%
Crustacea aquatic toxicity	+	0.7312	73.12%
Fish aquatic toxicity	+	0.9637	96.37%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4040	P28482	MAP kinase ERK2	96.59%	83.82%
CHEMBL2581	P07339	Cathepsin D	93.58%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.78%	96.09%
CHEMBL230	P35354	Cyclooxygenase-2	90.54%	89.63%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.73%	99.17%
CHEMBL4769	O95749	Geranylgeranyl pyrophosphate synthetase	86.49%	92.08%
CHEMBL253	P34972	Cannabinoid CB2 receptor	84.14%	97.25%
CHEMBL3892	Q99500	Sphingosine 1-phosphate receptor Edg-3	82.19%	97.29%

Plants that contains it

• Calypogeia integristipula
• Cirsium brevistylum
• Gentiana dahurica
• Gymnanthemum amygdalinum
• Hylodesmum podocarpum subsp. oxyphyllum
• Putterlickia verrucosa

Cross-Links

• PubChem: 10019295
• NPASS: NPC162202
• LOTUS: LTS0141865
• wikiData: Q105307941