Gibberellic acid

Details

Top
Internal ID ac38359e-3aed-4819-a44d-01af9c49f3c3
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Diterpenoids > C19-gibberellins > C19-gibberellin 6-carboxylic acids
IUPAC Name (1R,2R,5S,8S,9S,10R,11S,12S)-5,12-dihydroxy-11-methyl-6-methylidene-16-oxo-15-oxapentacyclo[9.3.2.15,8.01,10.02,8]heptadec-13-ene-9-carboxylic acid
SMILES (Canonical) CC12C(C=CC3(C1C(C45C3CCC(C4)(C(=C)C5)O)C(=O)O)OC2=O)O
SMILES (Isomeric) C[C@@]12[C@H](C=C[C@@]3([C@@H]1[C@@H]([C@]45[C@H]3CC[C@](C4)(C(=C)C5)O)C(=O)O)OC2=O)O
InChI InChI=1S/C19H22O6/c1-9-7-17-8-18(9,24)5-3-10(17)19-6-4-11(20)16(2,15(23)25-19)13(19)12(17)14(21)22/h4,6,10-13,20,24H,1,3,5,7-8H2,2H3,(H,21,22)/t10-,11+,12-,13-,16-,17+,18+,19-/m1/s1
InChI Key IXORZMNAPKEEDV-OBDJNFEBSA-N
Popularity 12,504 references in papers

Physical and Chemical Properties

Top
Molecular Formula C19H22O6
Molecular Weight 346.40 g/mol
Exact Mass 346.14163842 g/mol
Topological Polar Surface Area (TPSA) 104.00 Ų
XlogP 0.20
Atomic LogP (AlogP) 1.03
H-Bond Acceptor 5
H-Bond Donor 3
Rotatable Bonds 1

Synonyms

Top
Gibberellin A3
77-06-5
Gibberellin
Berelex
Brellin
Gibberellin X
Gib-Tabs
Gib-Sol
Gibberellic acid GA3
Cekugib
There are more than 10 synonyms. If you wish to see them all click here.

2D Structure

Top
2D Structure of Gibberellic acid

3D Structure

Top

ADMET Properties (via admetSAR 2)

Top
Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9775 97.75%
Caco-2 - 0.5742 57.42%
Blood Brain Barrier + 0.5500 55.00%
Human oral bioavailability + 0.6571 65.71%
Subcellular localzation Mitochondria 0.7926 79.26%
OATP2B1 inhibitior - 0.8611 86.11%
OATP1B1 inhibitior + 0.9413 94.13%
OATP1B3 inhibitior + 0.9479 94.79%
MATE1 inhibitior - 0.9800 98.00%
OCT2 inhibitior - 0.6592 65.92%
BSEP inhibitior - 0.9743 97.43%
P-glycoprotein inhibitior - 0.9085 90.85%
P-glycoprotein substrate - 0.7393 73.93%
CYP3A4 substrate + 0.6207 62.07%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8586 85.86%
CYP3A4 inhibition - 0.8404 84.04%
CYP2C9 inhibition - 0.9071 90.71%
CYP2C19 inhibition - 0.9026 90.26%
CYP2D6 inhibition - 0.9417 94.17%
CYP1A2 inhibition - 0.9045 90.45%
CYP2C8 inhibition - 0.6811 68.11%
CYP inhibitory promiscuity - 0.9518 95.18%
UGT catelyzed - 0.9000 90.00%
Carcinogenicity (binary) - 0.9900 99.00%
Carcinogenicity (trinary) Non-required 0.4590 45.90%
Eye corrosion - 0.9789 97.89%
Eye irritation - 0.9633 96.33%
Skin irritation - 0.5905 59.05%
Skin corrosion - 0.8988 89.88%
Ames mutagenesis - 0.9300 93.00%
Human Ether-a-go-go-Related Gene inhibition - 0.7593 75.93%
Micronuclear - 0.7300 73.00%
Hepatotoxicity + 0.5408 54.08%
skin sensitisation - 0.7729 77.29%
Respiratory toxicity + 0.7667 76.67%
Reproductive toxicity + 0.8556 85.56%
Mitochondrial toxicity + 0.8875 88.75%
Nephrotoxicity + 0.6575 65.75%
Acute Oral Toxicity (c) IV 0.6316 63.16%
Estrogen receptor binding + 0.7572 75.72%
Androgen receptor binding - 0.8513 85.13%
Thyroid receptor binding + 0.6115 61.15%
Glucocorticoid receptor binding + 0.6849 68.49%
Aromatase binding + 0.6063 60.63%
PPAR gamma - 0.6263 62.63%
Honey bee toxicity - 0.9679 96.79%
Biodegradation - 0.8000 80.00%
Crustacea aquatic toxicity - 0.7800 78.00%
Fish aquatic toxicity + 0.9826 98.26%

Targets

Top

Proven Targets:

CHEMBL ID UniProt ID Name Min activity Assay type Source
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 96.18% 91.11%
CHEMBL2581 P07339 Cathepsin D 95.39% 98.95%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 93.71% 94.45%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 91.90% 95.56%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 90.20% 96.09%
CHEMBL221 P23219 Cyclooxygenase-1 89.15% 90.17%
CHEMBL3137262 O60341 LSD1/CoREST complex 86.49% 97.09%
CHEMBL1806 P11388 DNA topoisomerase II alpha 86.28% 89.00%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 85.93% 99.23%
CHEMBL4685 P14902 Indoleamine 2,3-dioxygenase 81.96% 96.38%
CHEMBL4227 P25090 Lipoxin A4 receptor 81.16% 100.00%
CHEMBL253 P34972 Cannabinoid CB2 receptor 80.72% 97.25%
CHEMBL1994 P08235 Mineralocorticoid receptor 80.49% 100.00%

Cross-Links

Top
PubChem 6466
NPASS NPC9848
ChEMBL CHEMBL1232952
LOTUS LTS0185015
wikiData Q411138