Gibberellin A1

Details

• Internal ID: cf8fa547-50e5-47ed-8512-ebedb8d2a12a
• 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]heptadecane-9-carboxylic acid
• SMILES (Canonical): CC12C(CCC3(C1C(C45C3CCC(C4)(C(=C)C5)O)C(=O)O)OC2=O)O
• SMILES (Isomeric): C[C@@]12[C@H](CC[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/C19H24O6/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/h10-13,20,24H,1,3-8H2,2H3,(H,21,22)/t10-,11+,12-,13-,16-,17+,18+,19-/m1/s1
• InChI Key: JLJLRLWOEMWYQK-OBDJNFEBSA-N
• Popularity: 15 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₂₄O₆
• Molecular Weight: 348.40 g/mol
• Exact Mass: 348.15728848 g/mol
• Topological Polar Surface Area (TPSA): 104.00 Ų
• XlogP: 0.20
• Atomic LogP (AlogP): 1.25
• H-Bond Acceptor: 5
• H-Bond Donor: 3
• Rotatable Bonds: 1

Synonyms

• 545-97-1
• Gibberellin 1
• (1S,2S,4aR,4bR,7S,9aS,10S,10aR)-2,7-Dihydroxy-1-methyl-8-methylene-13-oxododecahydro-4a,1-(epoxymethano)-7,9a-methanobenzo[a]azulene-10-carboxylic acid
• SCHEMBL676051
• CHEBI:27717
• DTXSID60969689
• EX-A7055
• HY-N7443
• AKOS026751552
• MS-25364
• CS-0129118
• GA1
• Gibberellin A1 100 microg/mL in Acetonitrile
• Q20972182
• (1alpha,2beta,4aalpha,4bbeta,10beta)-2,4a,7-Trihydroxy-1-methyl-8-methylenegibbane-1,10-dicarboxylic acid 1,4a-lactone
• (1R,2R,5S,8S,9S,10R,11S,12S)-5,12-dihydroxy-11-methyl-6-methylidene-16-oxo-15-oxapentacyclo[9.3.2.1(5,8).0(1,10).0(2,8)]heptadecane-9-carboxylic acid
• 2beta,7alpha-dihydroxy-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	+	0.9834	98.34%
Caco-2	+	0.5000	50.00%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Mitochondria	0.7547	75.47%
OATP2B1 inhibitior	-	0.8602	86.02%
OATP1B1 inhibitior	+	0.9282	92.82%
OATP1B3 inhibitior	+	0.9237	92.37%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.6592	65.92%
BSEP inhibitior	-	0.9411	94.11%
P-glycoprotein inhibitior	-	0.8947	89.47%
P-glycoprotein substrate	-	0.7805	78.05%
CYP3A4 substrate	+	0.6353	63.53%
CYP2C9 substrate	-	0.8108	81.08%
CYP2D6 substrate	-	0.8571	85.71%
CYP3A4 inhibition	-	0.7960	79.60%
CYP2C9 inhibition	-	0.8987	89.87%
CYP2C19 inhibition	-	0.8833	88.33%
CYP2D6 inhibition	-	0.9492	94.92%
CYP1A2 inhibition	-	0.7942	79.42%
CYP2C8 inhibition	-	0.7467	74.67%
CYP inhibitory promiscuity	-	0.9583	95.83%
UGT catelyzed	-	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.4814	48.14%
Eye corrosion	-	0.9867	98.67%
Eye irritation	-	0.9318	93.18%
Skin irritation	+	0.5170	51.70%
Skin corrosion	-	0.8746	87.46%
Ames mutagenesis	-	0.8100	81.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6931	69.31%
Micronuclear	-	0.7300	73.00%
Hepatotoxicity	-	0.5217	52.17%
skin sensitisation	-	0.7817	78.17%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	+	0.9750	97.50%
Nephrotoxicity	+	0.6641	66.41%
Acute Oral Toxicity (c)	IV	0.4947	49.47%
Estrogen receptor binding	+	0.8648	86.48%
Androgen receptor binding	-	0.5397	53.97%
Thyroid receptor binding	+	0.6029	60.29%
Glucocorticoid receptor binding	+	0.7313	73.13%
Aromatase binding	+	0.6180	61.80%
PPAR gamma	-	0.6152	61.52%
Honey bee toxicity	-	0.9563	95.63%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.6200	62.00%
Fish aquatic toxicity	+	0.9922	99.22%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	94.19%	96.38%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.27%	95.56%
CHEMBL2581	P07339	Cathepsin D	89.84%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.82%	94.45%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	88.43%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.91%	97.09%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.79%	99.23%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	87.42%	93.04%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.31%	89.00%
CHEMBL340	P08684	Cytochrome P450 3A4	83.79%	91.19%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.63%	100.00%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	82.97%	93.03%
CHEMBL5028	O14672	ADAM10	82.26%	97.50%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	81.96%	93.00%

Plants that contains it

• Agrostemma githago
• Alcea rosea
• Arabidopsis thaliana
• Aralia cordata
• Campanula isophylla
• Carica papaya
• Cenchrus americanus
• Cibotium glaucum
• Cucumis melo
• Cucurbita maxima
• Eucalyptus globulus
• Eustoma grandiflorum
• Fragaria × ananassa
• Gentiana triflora
• Helianthus annuus
• Ipomoea batatas
• Ipomoea nil
• Juglans regia
• Laburnum anagyroidis
• Leucaena leucocephala
• Lolium perenne
• Lolium temulentum
• Lupinus albus
• Marah macrocarpa
• Matthiola incana
• Picea sitchensis
• Populus balsamifera
• Prunus armeniaca
• Prunus avium
• Prunus mandshurica
• Prunus persica
• Prunus sibirica
• Pseudotsuga menziesii
• Sicyos edulis
• Silene armeria
• Solanum tuberosum
• Thlaspi arvense

Cross-Links

• PubChem: 5280379
• NPASS: NPC58792
• LOTUS: LTS0013777
• wikiData: Q20972182