Grindelic acid

Details

• Internal ID: b881f1a1-5d5d-4f10-9e22-61d264cd1b68
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids
• IUPAC Name: 2-[(2'R,8R,8aS)-2',4,4,7,8a-pentamethylspiro[2,3,4a,5-tetrahydro-1H-naphthalene-8,5'-oxolane]-2'-yl]acetic acid
• SMILES (Canonical): CC1=CCC2C(CCCC2(C13CCC(O3)(C)CC(=O)O)C)(C)C
• SMILES (Isomeric): CC1=CCC2[C@@]([C@@]13CC[C@](O3)(C)CC(=O)O)(CCCC2(C)C)C
• InChI: InChI=1S/C20H32O3/c1-14-7-8-15-17(2,3)9-6-10-19(15,5)20(14)12-11-18(4,23-20)13-16(21)22/h7,15H,6,8-13H2,1-5H3,(H,21,22)/t15?,18-,19+,20-/m1/s1
• InChI Key: XLWWERNKTLITEF-FOUFQHLJSA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₃₂O₃
• Molecular Weight: 320.50 g/mol
• Exact Mass: 320.23514488 g/mol
• Topological Polar Surface Area (TPSA): 46.50 Ų
• XlogP: 4.10
• Atomic LogP (AlogP): 4.95
• H-Bond Acceptor: 2
• H-Bond Donor: 1
• Rotatable Bonds: 2

Synonyms

• DTXSID10878535
• 2-[(2'R,8R,8As)-2',4,4,7,8a-pentamethylspiro[2,3,4a,5-tetrahydro-1H-naphthalene-8,5'-oxolane]-2'-yl]acetic acid
• 1438-57-9
• MEGxp0_000954
• SCHEMBL5085539
• ACon1_001186
• CHEBI:182124
• AKOS040735821
• NCGC00169595-01
• NCGC00169595-03
• BRD-A71384443-001-01-2

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9942	99.42%
Caco-2	+	0.7555	75.55%
Blood Brain Barrier	+	0.7500	75.00%
Human oral bioavailability	+	0.6143	61.43%
Subcellular localzation	Mitochondria	0.4976	49.76%
OATP2B1 inhibitior	-	0.8590	85.90%
OATP1B1 inhibitior	+	0.8261	82.61%
OATP1B3 inhibitior	+	0.9203	92.03%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.5750	57.50%
BSEP inhibitior	-	0.5000	50.00%
P-glycoprotein inhibitior	-	0.8322	83.22%
P-glycoprotein substrate	-	0.9158	91.58%
CYP3A4 substrate	+	0.5536	55.36%
CYP2C9 substrate	-	0.6031	60.31%
CYP2D6 substrate	-	0.8568	85.68%
CYP3A4 inhibition	-	0.7702	77.02%
CYP2C9 inhibition	-	0.7012	70.12%
CYP2C19 inhibition	-	0.6323	63.23%
CYP2D6 inhibition	-	0.9312	93.12%
CYP1A2 inhibition	-	0.7687	76.87%
CYP2C8 inhibition	-	0.6229	62.29%
CYP inhibitory promiscuity	-	0.7537	75.37%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8700	87.00%
Carcinogenicity (trinary)	Non-required	0.5819	58.19%
Eye corrosion	-	0.9851	98.51%
Eye irritation	-	0.7581	75.81%
Skin irritation	-	0.5302	53.02%
Skin corrosion	-	0.9386	93.86%
Ames mutagenesis	-	0.6754	67.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.3761	37.61%
Micronuclear	-	0.8500	85.00%
Hepatotoxicity	-	0.6250	62.50%
skin sensitisation	-	0.5729	57.29%
Respiratory toxicity	+	0.5111	51.11%
Reproductive toxicity	+	0.6889	68.89%
Mitochondrial toxicity	+	0.8250	82.50%
Nephrotoxicity	-	0.8357	83.57%
Acute Oral Toxicity (c)	III	0.5702	57.02%
Estrogen receptor binding	+	0.7554	75.54%
Androgen receptor binding	+	0.5973	59.73%
Thyroid receptor binding	+	0.7188	71.88%
Glucocorticoid receptor binding	-	0.4949	49.49%
Aromatase binding	+	0.7504	75.04%
PPAR gamma	+	0.6071	60.71%
Honey bee toxicity	-	0.9655	96.55%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.7500	75.00%
Fish aquatic toxicity	+	0.9843	98.43%

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	92.08%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	90.96%	91.11%
CHEMBL2581	P07339	Cathepsin D	88.02%	98.95%
CHEMBL221	P23219	Cyclooxygenase-1	85.97%	90.17%
CHEMBL3401	O75469	Pregnane X receptor	83.59%	94.73%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.03%	95.56%
CHEMBL253	P34972	Cannabinoid CB2 receptor	81.59%	97.25%

Plants that contains it

• Grindelia hirsutula
• Grindelia squarrosa
• Isocoma coronopifolia
• Isocoma tenuisecta
• Xanthocephalum gymnospermoides

Cross-Links

• PubChem: 20054931
• LOTUS: LTS0210969
• wikiData: Q104253413