Retinal

Details

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Internal ID a1204620-23d9-405d-b30c-cbbdb3badcaf
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Retinoids
IUPAC Name (2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenal
SMILES (Canonical) CC1=C(C(CCC1)(C)C)C=CC(=CC=CC(=CC=O)C)C
SMILES (Isomeric) CC1=C(C(CCC1)(C)C)/C=C/C(=C/C=C/C(=C/C=O)/C)/C
InChI InChI=1S/C20H28O/c1-16(8-6-9-17(2)13-15-21)11-12-19-18(3)10-7-14-20(19,4)5/h6,8-9,11-13,15H,7,10,14H2,1-5H3/b9-6+,12-11+,16-8+,17-13+
InChI Key NCYCYZXNIZJOKI-OVSJKPMPSA-N
Popularity 4,801 references in papers

Physical and Chemical Properties

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Molecular Formula C20H28O
Molecular Weight 284.40 g/mol
Exact Mass 284.214015512 g/mol
Topological Polar Surface Area (TPSA) 17.10 Ų
XlogP 6.20
Atomic LogP (AlogP) 5.72
H-Bond Acceptor 1
H-Bond Donor 0
Rotatable Bonds 5

Synonyms

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retinal
retinaldehyde
116-31-4
vitamin A aldehyde
trans-Retinal
retinene
axerophthal
all-E-Retinal
all trans-Retinal
E-Retinal
There are more than 10 synonyms. If you wish to see them all click here.

2D Structure

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2D Structure of Retinal

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9951 99.51%
Caco-2 + 0.9262 92.62%
Blood Brain Barrier + 0.9500 95.00%
Human oral bioavailability - 0.6714 67.14%
Subcellular localzation Lysosomes 0.5203 52.03%
OATP2B1 inhibitior - 0.8599 85.99%
OATP1B1 inhibitior - 0.6996 69.96%
OATP1B3 inhibitior - 0.4214 42.14%
MATE1 inhibitior - 0.9800 98.00%
OCT2 inhibitior - 0.6500 65.00%
BSEP inhibitior + 0.9446 94.46%
P-glycoprotein inhibitior - 0.8094 80.94%
P-glycoprotein substrate - 0.9300 93.00%
CYP3A4 substrate + 0.6155 61.55%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8715 87.15%
CYP3A4 inhibition - 0.9546 95.46%
CYP2C9 inhibition - 0.8872 88.72%
CYP2C19 inhibition - 0.8739 87.39%
CYP2D6 inhibition - 0.9536 95.36%
CYP1A2 inhibition - 0.8525 85.25%
CYP2C8 inhibition - 0.8316 83.16%
CYP inhibitory promiscuity - 0.7610 76.10%
UGT catelyzed - 0.0000 0.00%
Carcinogenicity (binary) - 0.6700 67.00%
Carcinogenicity (trinary) Non-required 0.5578 55.78%
Eye corrosion - 0.8835 88.35%
Eye irritation - 0.8634 86.34%
Skin irritation + 0.8196 81.96%
Skin corrosion - 0.9610 96.10%
Ames mutagenesis + 0.7390 73.90%
Human Ether-a-go-go-Related Gene inhibition + 0.8034 80.34%
Micronuclear - 0.9900 99.00%
Hepatotoxicity + 0.6798 67.98%
skin sensitisation + 0.9313 93.13%
Respiratory toxicity + 0.6889 68.89%
Reproductive toxicity + 0.9111 91.11%
Mitochondrial toxicity - 0.8125 81.25%
Nephrotoxicity + 0.7929 79.29%
Acute Oral Toxicity (c) III 0.8115 81.15%
Estrogen receptor binding + 0.6787 67.87%
Androgen receptor binding - 0.4853 48.53%
Thyroid receptor binding + 0.6898 68.98%
Glucocorticoid receptor binding - 0.6343 63.43%
Aromatase binding + 0.8685 86.85%
PPAR gamma + 0.8707 87.07%
Honey bee toxicity - 0.9011 90.11%
Biodegradation - 0.8000 80.00%
Crustacea aquatic toxicity - 0.6100 61.00%
Fish aquatic toxicity + 0.9898 98.98%

Targets

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Proven Targets:

CHEMBL ID UniProt ID Name Min activity Assay type Source
CHEMBL3577 P00352 Aldehyde dehydrogenase 1A1 22387.2 nM
Potency
via CMAUP
CHEMBL2903 P16050 Arachidonate 15-lipoxygenase 15848.9 nM
Potency
via CMAUP
CHEMBL4096 P04637 Cellular tumor antigen p53 12.6 nM
12.6 nM
Potency
Potency
via CMAUP
via Super-PRED
CHEMBL340 P08684 Cytochrome P450 3A4 12589.3 nM
12589.3 nM
Potency
Potency
via CMAUP
via CMAUP
CHEMBL1075138 Q9NUW8 Tyrosyl-DNA phosphodiesterase 1 10000 nM
Potency
via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID UniProt ID Name Probability Model accuracy
CHEMBL2061 P19793 Retinoid X receptor alpha 94.82% 91.67%
CHEMBL1870 P28702 Retinoid X receptor beta 94.14% 95.00%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 94.05% 91.11%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 94.03% 95.56%
CHEMBL2004 P48443 Retinoid X receptor gamma 93.40% 100.00%
CHEMBL3091268 Q92753 Nuclear receptor ROR-beta 91.06% 95.50%
CHEMBL230 P35354 Cyclooxygenase-2 89.43% 89.63%
CHEMBL1293249 Q13887 Kruppel-like factor 5 87.59% 86.33%
CHEMBL1937 Q92769 Histone deacetylase 2 87.48% 94.75%
CHEMBL2288 Q13526 Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1 87.44% 91.71%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 86.20% 96.09%
CHEMBL325 Q13547 Histone deacetylase 1 84.90% 95.92%
CHEMBL1994 P08235 Mineralocorticoid receptor 81.29% 100.00%

Plants that contains it

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Below are displayed all the plants proven (via scientific papers) to contain this compound!
To see more specific details click the taxa you are interested in.
Panax ginseng

Cross-Links

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PubChem 638015
NPASS NPC281986
ChEMBL CHEMBL81379
LOTUS LTS0275050
wikiData Q28529715