Gibberellin A20

Details

• Internal ID: 8b19db37-35e0-4479-a758-91765edb99ff
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids > C19-gibberellins > C19-gibberellin 6-carboxylic acids
• IUPAC Name: (1R,2R,5S,8S,9S,10R,11R)-5-hydroxy-11-methyl-6-methylidene-16-oxo-15-oxapentacyclo[9.3.2.15,8.01,10.02,8]heptadecane-9-carboxylic acid
• SMILES (Canonical): CC12CCCC3(C1C(C45C3CCC(C4)(C(=C)C5)O)C(=O)O)OC2=O
• SMILES (Isomeric): C[C@@]12CCC[C@@]3([C@@H]1[C@@H]([C@]45[C@H]3CC[C@](C4)(C(=C)C5)O)C(=O)O)OC2=O
• InChI: InChI=1S/C19H24O5/c1-10-8-17-9-18(10,23)7-4-11(17)19-6-3-5-16(2,15(22)24-19)13(19)12(17)14(20)21/h11-13,23H,1,3-9H2,2H3,(H,20,21)/t11-,12-,13-,16-,17+,18+,19-/m1/s1
• InChI Key: OXFPYCSNYOFUCH-KQBHUUJHSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₂₄O₅
• Molecular Weight: 332.40 g/mol
• Exact Mass: 332.16237386 g/mol
• Topological Polar Surface Area (TPSA): 83.80 Ų
• XlogP: 1.20
• Atomic LogP (AlogP): 2.28
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 1

Synonyms

• 19143-87-4
• Gibbane-1,10-dicarboxylic acid, 4a,7-dihydroxy-1-methyl-8-methylene-, 1,4a-lactone, (1alpha,4aalpha,4bbeta,10beta)-
• Gibberellin 20
• (1R,2R,5S,8S,9S,10R,11R)-5-Hydroxy-11-methyl-6-methylidene-16-oxo-15-oxapentacyclo[9.3.2.15,8.01,10.02,8]heptadecane-9-carboxylic acid
• GA20
• CHEBI:27742
• Q27103295
• (1R,2R,5S,8S,9S,10R,11R)-5-hydroxy-11-methyl-6-methylidene-16-oxo-15-oxapentacyclo[9.3.2.1(5,8).0(1,10).0(2,8)]heptadecane-9-carboxylic acid
• 7alpha-hydroxy-1beta-methyl-8-methylidene-13-oxo-4a,1alpha-epoxymethano-4aalpha,4bbeta-gibbane-10beta-carboxylic acid

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9867	98.67%
Caco-2	+	0.5836	58.36%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	+	0.5857	58.57%
Subcellular localzation	Mitochondria	0.7659	76.59%
OATP2B1 inhibitior	-	0.8569	85.69%
OATP1B1 inhibitior	+	0.9203	92.03%
OATP1B3 inhibitior	+	0.8961	89.61%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.5374	53.74%
BSEP inhibitior	-	0.9224	92.24%
P-glycoprotein inhibitior	-	0.8807	88.07%
P-glycoprotein substrate	-	0.8221	82.21%
CYP3A4 substrate	+	0.6024	60.24%
CYP2C9 substrate	-	0.7958	79.58%
CYP2D6 substrate	-	0.8664	86.64%
CYP3A4 inhibition	-	0.6859	68.59%
CYP2C9 inhibition	-	0.9088	90.88%
CYP2C19 inhibition	-	0.8714	87.14%
CYP2D6 inhibition	-	0.9419	94.19%
CYP1A2 inhibition	-	0.7171	71.71%
CYP2C8 inhibition	-	0.6638	66.38%
CYP inhibitory promiscuity	-	0.9455	94.55%
UGT catelyzed	-	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5156	51.56%
Eye corrosion	-	0.9909	99.09%
Eye irritation	-	0.8982	89.82%
Skin irritation	+	0.5539	55.39%
Skin corrosion	-	0.8940	89.40%
Ames mutagenesis	-	0.7700	77.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6657	66.57%
Micronuclear	-	0.7400	74.00%
Hepatotoxicity	+	0.5033	50.33%
skin sensitisation	-	0.7641	76.41%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	+	0.8778	87.78%
Mitochondrial toxicity	+	0.9625	96.25%
Nephrotoxicity	+	0.6943	69.43%
Acute Oral Toxicity (c)	III	0.4284	42.84%
Estrogen receptor binding	+	0.8529	85.29%
Androgen receptor binding	+	0.5570	55.70%
Thyroid receptor binding	+	0.5346	53.46%
Glucocorticoid receptor binding	+	0.7226	72.26%
Aromatase binding	+	0.6155	61.55%
PPAR gamma	-	0.5951	59.51%
Honey bee toxicity	-	0.9564	95.64%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.6700	67.00%
Fish aquatic toxicity	+	0.9968	99.68%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.74%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	93.14%	97.25%
CHEMBL2581	P07339	Cathepsin D	92.18%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.77%	95.56%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	87.43%	96.38%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.54%	94.45%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.22%	99.23%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	86.20%	93.04%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.76%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.17%	89.00%
CHEMBL340	P08684	Cytochrome P450 3A4	83.13%	91.19%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	82.13%	95.50%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.75%	100.00%

Plants that contains it

• Abelmoschus esculentus
• Agrostemma githago
• Arabidopsis thaliana
• Aralia cordata
• Cenchrus americanus
• Cibotium glaucum
• Cucumis melo
• Cucumis sativus
• Dioscorea japonica
• Dioscorea oppositifolia
• Dioscorea polystachya
• Eucalyptus globulus
• Eustoma grandiflorum
• Gentiana triflora
• Helianthus annuus
• Ipomoea batatas
• Ipomoea nil
• Ipomoea purpurea
• Juglans regia
• Kalanchoe daigremontiana
• Leucaena leucocephala
• Lolium perenne
• Lolium temulentum
• Lygodium circinatum
• Matthiola incana
• Ornithogalum thyrsoides
• Phaseolus vulgaris
• Picea abies
• Pinus sylvestris
• Prunus cerasus
• Silene armeria
• Thlaspi arvense
• Vicia faba

Cross-Links

• PubChem: 5280481
• NPASS: NPC169119
• LOTUS: LTS0041124
• wikiData: Q27103295