5-(1-Hydroxy-2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl)-3-methylpenta-2,4-dienoic acid

Details

• Internal ID: de0524ec-b8e1-4101-a2a9-022fb660b7a0
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids > Abscisic acids and derivatives
• IUPAC Name: 5-(1-hydroxy-2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl)-3-methylpenta-2,4-dienoic acid
• SMILES (Canonical): CC1=CC(=O)CC(C1(C=CC(=CC(=O)O)C)O)(C)C
• SMILES (Isomeric): CC1=CC(=O)CC(C1(C=CC(=CC(=O)O)C)O)(C)C
• InChI: InChI=1S/C15H20O4/c1-10(7-13(17)18)5-6-15(19)11(2)8-12(16)9-14(15,3)4/h5-8,19H,9H2,1-4H3,(H,17,18)
• InChI Key: JLIDBLDQVAYHNE-UHFFFAOYSA-N
• Popularity: 10,056 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₀O₄
• Molecular Weight: 264.32 g/mol
• Exact Mass: 264.13615911 g/mol
• Topological Polar Surface Area (TPSA): 74.60 Ų
• XlogP: 1.60
• Atomic LogP (AlogP): 2.25
• H-Bond Acceptor: 3
• H-Bond Donor: 2
• Rotatable Bonds: 3

Synonyms

• 21293-29-8
• 5-(1-hydroxy-2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl)-3-methylpenta-2,4-dienoic acid
• Dormin
• (+/-)-2-cis-4-trans-Abscisic acid; (+/-)-ABA
• NSC148832
• Spectrum_001158
• SpecPlus_000450
• Spectrum2_001503
• Spectrum3_001528
• Spectrum4_001841
• Oprea1_187043
• KBioGR_002242
• KBioSS_001638
• DivK1c_006546
• SPBio_001545
• KBio1_001490
• KBio2_001638
• KBio2_004206
• KBio2_006774
• KBio3_002416
• DTXSID90860135
• 17alpha-HydroxyprogesteroneCaproate
• ABA
• BCP32061
• AKOS030241514
• NCI60_001025
• FT-0604385
• FT-0604467
• FT-0619562
• FT-0619875
• FT-0621710
• Q27165538
• (+)-Abscisic acid;Abscisinsaeure;( inverted exclamation markA)-cis,trans-Abscisic acid
• 5-(1-hydroxy-2,6,6-trimethyl-4-oxo-1-cyclohex-2-enyl)-3-methylpenta-2,4-dienoic acid
• 5-(1-hydroxy-2,6,6-trimethyl-4-oxo-2-cyclohexen-1-yl)-3-methyl-2,4-pentadienoic acid
• 5-(1-hydroxy-4-oxo-2,6,6-trimethylcyclohex-2-enyl)-3-methylpenta-2,4-dienoic acid
• (2Z,4E)-5-(1-Hydroxy-2,6,6-trimethyl-4-oxo-2-cyclohexen-1-yl)-3-methyl-2,4-pentadienoic acid

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9785	97.85%
Caco-2	+	0.6081	60.81%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	+	0.6286	62.86%
Subcellular localzation	Mitochondria	0.8663	86.63%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8958	89.58%
OATP1B3 inhibitior	+	0.9480	94.80%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.7162	71.62%
P-glycoprotein inhibitior	-	0.9617	96.17%
P-glycoprotein substrate	-	0.8854	88.54%
CYP3A4 substrate	+	0.5711	57.11%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9115	91.15%
CYP3A4 inhibition	-	0.9097	90.97%
CYP2C9 inhibition	-	0.9071	90.71%
CYP2C19 inhibition	-	0.9377	93.77%
CYP2D6 inhibition	-	0.9441	94.41%
CYP1A2 inhibition	-	0.9535	95.35%
CYP2C8 inhibition	-	0.9365	93.65%
CYP inhibitory promiscuity	-	0.9557	95.57%
UGT catelyzed	-	0.8000	80.00%
Carcinogenicity (binary)	-	0.7648	76.48%
Carcinogenicity (trinary)	Non-required	0.5812	58.12%
Eye corrosion	-	0.9726	97.26%
Eye irritation	-	0.6595	65.95%
Skin irritation	-	0.6095	60.95%
Skin corrosion	-	0.9492	94.92%
Ames mutagenesis	-	0.6854	68.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.8325	83.25%
Micronuclear	-	0.7000	70.00%
Hepatotoxicity	+	0.5552	55.52%
skin sensitisation	+	0.7695	76.95%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.6222	62.22%
Mitochondrial toxicity	-	0.6625	66.25%
Nephrotoxicity	-	0.6416	64.16%
Acute Oral Toxicity (c)	III	0.6395	63.95%
Estrogen receptor binding	+	0.6386	63.86%
Androgen receptor binding	-	0.5397	53.97%
Thyroid receptor binding	-	0.5322	53.22%
Glucocorticoid receptor binding	+	0.6523	65.23%
Aromatase binding	+	0.5784	57.84%
PPAR gamma	+	0.5820	58.20%
Honey bee toxicity	-	0.9350	93.50%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.7400	74.00%
Fish aquatic toxicity	+	0.9754	97.54%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1963	P16473	Thyroid stimulating hormone receptor	31.6 nM	Potency	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.54%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.47%	86.33%
CHEMBL1870	P28702	Retinoid X receptor beta	89.04%	95.00%
CHEMBL2004	P48443	Retinoid X receptor gamma	88.59%	100.00%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	88.48%	91.11%
CHEMBL4224	P49759	Dual specificty protein kinase CLK1	87.83%	85.30%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	85.89%	96.09%
CHEMBL2061	P19793	Retinoid X receptor alpha	85.12%	91.67%
CHEMBL4208	P20618	Proteasome component C5	84.86%	90.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.13%	89.00%
CHEMBL2581	P07339	Cathepsin D	83.32%	98.95%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	82.88%	95.50%
CHEMBL1937	Q92769	Histone deacetylase 2	81.87%	94.75%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.62%	99.23%
CHEMBL221	P23219	Cyclooxygenase-1	81.39%	90.17%
CHEMBL3492	P49721	Proteasome Macropain subunit	81.28%	90.24%

Plants that contains it

• Artemisia capillaris
• Cinnamomum subavenium
• Cuscuta pentagona
• Dioscorea japonica
• Hordeum vulgare
• Ipomoea nil
• Isatis tinctoria
• Lonicera japonica
• Lygodium japonicum
• Macaranga triloba
• Machilus zuihoensis
• Nicotiana tabacum
• Prunus davidiana
• Prunus domestica
• Prunus persica
• Robinia pseudoacacia
• Vicia faba
• Vigna unguiculata
• Xylocarpus granatum
• Zanthoxylum simulans
• Zea mays

Cross-Links

• PubChem: 287291
• NPASS: NPC184416
• LOTUS: LTS0021517
• wikiData: Q27165538