(1S,2S,3S,4R,8S,9S,14S)-12,14-dihydroxy-4,8-dimethyl-13-methylidenetetracyclo[10.2.1.01,9.03,8]pentadecane-2,4-dicarboxylic acid

Details

• Internal ID: b8425913-d380-4d77-8472-aa113f0b11d7
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids > C20-gibberellins > C20-gibberellin 6-carboxylic acids
• IUPAC Name: (1S,2S,3S,4R,8S,9S,14S)-12,14-dihydroxy-4,8-dimethyl-13-methylidenetetracyclo[10.2.1.01,9.03,8]pentadecane-2,4-dicarboxylic acid
• SMILES (Canonical): CC12CCCC(C1C(C34C2CCC(C3)(C(=C)C4O)O)C(=O)O)(C)C(=O)O
• SMILES (Isomeric): C[C@@]12CCC[C@@]([C@H]1[C@@H]([C@@]34[C@H]2CCC(C3)(C(=C)[C@H]4O)O)C(=O)O)(C)C(=O)O
• InChI: InChI=1S/C20H28O6/c1-10-14(21)20-9-19(10,26)8-5-11(20)17(2)6-4-7-18(3,16(24)25)13(17)12(20)15(22)23/h11-14,21,26H,1,4-9H2,2-3H3,(H,22,23)(H,24,25)/t11-,12+,13-,14+,17-,18+,19?,20-/m0/s1
• InChI Key: GWJAUARFGPKLMT-OUUTUKGJSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₈O₆
• Molecular Weight: 364.40 g/mol
• Exact Mass: 364.18858861 g/mol
• Topological Polar Surface Area (TPSA): 115.00 Ų
• XlogP: 1.10
• Atomic LogP (AlogP): 2.05
• H-Bond Acceptor: 4
• H-Bond Donor: 4
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9754	97.54%
Caco-2	+	0.5000	50.00%
Blood Brain Barrier	+	0.6027	60.27%
Human oral bioavailability	+	0.5286	52.86%
Subcellular localzation	Mitochondria	0.7021	70.21%
OATP2B1 inhibitior	-	0.8607	86.07%
OATP1B1 inhibitior	+	0.8782	87.82%
OATP1B3 inhibitior	-	0.2325	23.25%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.6006	60.06%
BSEP inhibitior	-	0.9331	93.31%
P-glycoprotein inhibitior	-	0.8696	86.96%
P-glycoprotein substrate	-	0.7752	77.52%
CYP3A4 substrate	+	0.6187	61.87%
CYP2C9 substrate	-	0.8075	80.75%
CYP2D6 substrate	-	0.8553	85.53%
CYP3A4 inhibition	-	0.8667	86.67%
CYP2C9 inhibition	-	0.8498	84.98%
CYP2C19 inhibition	-	0.9223	92.23%
CYP2D6 inhibition	-	0.9505	95.05%
CYP1A2 inhibition	-	0.8619	86.19%
CYP2C8 inhibition	-	0.7566	75.66%
CYP inhibitory promiscuity	-	0.9581	95.81%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6197	61.97%
Eye corrosion	-	0.9930	99.30%
Eye irritation	-	0.8613	86.13%
Skin irritation	+	0.6033	60.33%
Skin corrosion	-	0.9177	91.77%
Ames mutagenesis	-	0.7500	75.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6388	63.88%
Micronuclear	-	0.7500	75.00%
Hepatotoxicity	-	0.7250	72.50%
skin sensitisation	-	0.7555	75.55%
Respiratory toxicity	+	0.5333	53.33%
Reproductive toxicity	+	0.9667	96.67%
Mitochondrial toxicity	+	0.9875	98.75%
Nephrotoxicity	+	0.6578	65.78%
Acute Oral Toxicity (c)	I	0.5149	51.49%
Estrogen receptor binding	+	0.7350	73.50%
Androgen receptor binding	+	0.6532	65.32%
Thyroid receptor binding	+	0.6316	63.16%
Glucocorticoid receptor binding	+	0.7651	76.51%
Aromatase binding	+	0.6311	63.11%
PPAR gamma	-	0.6198	61.98%
Honey bee toxicity	-	0.8893	88.93%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.6700	67.00%
Fish aquatic toxicity	+	1.0000	100.00%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL253	P34972	Cannabinoid CB2 receptor	91.19%	97.25%
CHEMBL221	P23219	Cyclooxygenase-1	90.58%	90.17%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	89.95%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.57%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.00%	95.56%
CHEMBL4227	P25090	Lipoxin A4 receptor	81.93%	100.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.93%	100.00%
CHEMBL2581	P07339	Cathepsin D	80.90%	98.95%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	80.13%	95.50%

Plants that contains it

• Helianthus annuus

Cross-Links

• PubChem: 163187856
• LOTUS: LTS0208593
• wikiData: Q105022434