5,6-Dihydroxy-4-methyl-13-methylidenetetracyclo[10.2.1.01,9.03,8]pentadecane-2,4,8-tricarboxylic acid

Details

• Internal ID: fabc74a9-2bd9-4ea8-bfa7-9b8463d443a3
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids > C20-gibberellins > C20-gibberellin 20-carboxylic acids
• IUPAC Name: 5,6-dihydroxy-4-methyl-13-methylidenetetracyclo[10.2.1.01,9.03,8]pentadecane-2,4,8-tricarboxylic acid
• SMILES (Canonical): CC1(C2C(C34CC(CCC3C2(CC(C1O)O)C(=O)O)C(=C)C4)C(=O)O)C(=O)O
• SMILES (Isomeric): CC1(C2C(C34CC(CCC3C2(CC(C1O)O)C(=O)O)C(=C)C4)C(=O)O)C(=O)O
• InChI: InChI=1S/C20H26O8/c1-8-5-19-6-9(8)3-4-11(19)20(17(27)28)7-10(21)14(22)18(2,16(25)26)13(20)12(19)15(23)24/h9-14,21-22H,1,3-7H2,2H3,(H,23,24)(H,25,26)(H,27,28)
• InChI Key: FQTLNSKVFLETSS-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₆O₈
• Molecular Weight: 394.40 g/mol
• Exact Mass: 394.16276778 g/mol
• Topological Polar Surface Area (TPSA): 152.00 Ų
• XlogP: 0.80
• Atomic LogP (AlogP): 0.97
• H-Bond Acceptor: 5
• H-Bond Donor: 5
• Rotatable Bonds: 3

Synonyms

• 5,6-dihydroxy-4-methyl-13-methylidenetetracyclo[10.2.1.01,9.03,8]pentadecane-2,4,8-tricarboxylic acid

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8926	89.26%
Caco-2	-	0.6920	69.20%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Mitochondria	0.7697	76.97%
OATP2B1 inhibitior	-	0.8584	85.84%
OATP1B1 inhibitior	+	0.8912	89.12%
OATP1B3 inhibitior	+	0.9149	91.49%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.7500	75.00%
BSEP inhibitior	-	0.9549	95.49%
P-glycoprotein inhibitior	-	0.8467	84.67%
P-glycoprotein substrate	-	0.6698	66.98%
CYP3A4 substrate	+	0.6083	60.83%
CYP2C9 substrate	-	0.6419	64.19%
CYP2D6 substrate	-	0.8453	84.53%
CYP3A4 inhibition	-	0.9260	92.60%
CYP2C9 inhibition	-	0.8721	87.21%
CYP2C19 inhibition	-	0.8516	85.16%
CYP2D6 inhibition	-	0.9397	93.97%
CYP1A2 inhibition	-	0.8700	87.00%
CYP2C8 inhibition	-	0.7362	73.62%
CYP inhibitory promiscuity	-	0.9821	98.21%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5852	58.52%
Eye corrosion	-	0.9888	98.88%
Eye irritation	-	0.8760	87.60%
Skin irritation	-	0.5347	53.47%
Skin corrosion	-	0.9100	91.00%
Ames mutagenesis	-	0.8000	80.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7363	73.63%
Micronuclear	-	0.7300	73.00%
Hepatotoxicity	+	0.5618	56.18%
skin sensitisation	-	0.7623	76.23%
Respiratory toxicity	-	0.6000	60.00%
Reproductive toxicity	+	0.9444	94.44%
Mitochondrial toxicity	+	0.9625	96.25%
Nephrotoxicity	+	0.6188	61.88%
Acute Oral Toxicity (c)	IV	0.3850	38.50%
Estrogen receptor binding	+	0.7130	71.30%
Androgen receptor binding	+	0.5971	59.71%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	+	0.6682	66.82%
Aromatase binding	+	0.6016	60.16%
PPAR gamma	-	0.5773	57.73%
Honey bee toxicity	-	0.9339	93.39%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.6400	64.00%
Fish aquatic toxicity	+	0.9856	98.56%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL221	P23219	Cyclooxygenase-1	93.32%	90.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.03%	96.09%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	92.94%	96.38%
CHEMBL253	P34972	Cannabinoid CB2 receptor	88.40%	97.25%
CHEMBL340	P08684	Cytochrome P450 3A4	87.77%	91.19%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	86.60%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.15%	94.45%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	83.89%	93.00%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	83.19%	95.50%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	80.23%	95.56%

Plants that contains it

• Marah macrocarpa

Cross-Links

• PubChem: 14833730
• LOTUS: LTS0270301
• wikiData: Q104999864