16-Hydroxycarnosol

Details

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Internal ID 62cba262-f1d6-45c9-906e-6b759f9d3e34
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Diterpene lactones
IUPAC Name (1R,8S,10S)-3,4-dihydroxy-5-(1-hydroxypropan-2-yl)-11,11-dimethyl-16-oxatetracyclo[6.6.2.01,10.02,7]hexadeca-2,4,6-trien-15-one
SMILES (Canonical) CC(CO)C1=C(C(=C2C(=C1)C3CC4C2(CCCC4(C)C)C(=O)O3)O)O
SMILES (Isomeric) CC(CO)C1=C(C(=C2C(=C1)[C@@H]3C[C@@H]4[C@@]2(CCCC4(C)C)C(=O)O3)O)O
InChI InChI=1S/C20H26O5/c1-10(9-21)11-7-12-13-8-14-19(2,3)5-4-6-20(14,18(24)25-13)15(12)17(23)16(11)22/h7,10,13-14,21-23H,4-6,8-9H2,1-3H3/t10?,13-,14-,20+/m0/s1
InChI Key MWLHJCBZAWPKEY-NUDIBWDTSA-N
Popularity 5 references in papers

Physical and Chemical Properties

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Molecular Formula C20H26O5
Molecular Weight 346.40 g/mol
Exact Mass 346.17802393 g/mol
Topological Polar Surface Area (TPSA) 87.00 Ų
XlogP 3.20
Atomic LogP (AlogP) 3.26
H-Bond Acceptor 5
H-Bond Donor 3
Rotatable Bonds 2

Synonyms

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CHEMBL491307

2D Structure

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2D Structure of 16-Hydroxycarnosol

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.8888 88.88%
Caco-2 - 0.5183 51.83%
Blood Brain Barrier - 0.5500 55.00%
Human oral bioavailability - 0.7286 72.86%
Subcellular localzation Mitochondria 0.8774 87.74%
OATP2B1 inhibitior - 0.8595 85.95%
OATP1B1 inhibitior + 0.8265 82.65%
OATP1B3 inhibitior + 0.8858 88.58%
MATE1 inhibitior - 0.8800 88.00%
OCT2 inhibitior - 0.7000 70.00%
BSEP inhibitior - 0.7039 70.39%
P-glycoprotein inhibitior - 0.8300 83.00%
P-glycoprotein substrate - 0.7790 77.90%
CYP3A4 substrate + 0.6360 63.60%
CYP2C9 substrate - 0.7838 78.38%
CYP2D6 substrate - 0.7564 75.64%
CYP3A4 inhibition - 0.7714 77.14%
CYP2C9 inhibition - 0.8786 87.86%
CYP2C19 inhibition - 0.8426 84.26%
CYP2D6 inhibition - 0.9397 93.97%
CYP1A2 inhibition + 0.5324 53.24%
CYP2C8 inhibition - 0.7322 73.22%
CYP inhibitory promiscuity - 0.9159 91.59%
UGT catelyzed - 0.5000 50.00%
Carcinogenicity (binary) - 0.9300 93.00%
Carcinogenicity (trinary) Non-required 0.7318 73.18%
Eye corrosion - 0.9926 99.26%
Eye irritation - 0.9239 92.39%
Skin irritation - 0.7406 74.06%
Skin corrosion - 0.9566 95.66%
Ames mutagenesis - 0.6600 66.00%
Human Ether-a-go-go-Related Gene inhibition - 0.7932 79.32%
Micronuclear - 0.9300 93.00%
Hepatotoxicity - 0.6100 61.00%
skin sensitisation - 0.9002 90.02%
Respiratory toxicity + 0.5889 58.89%
Reproductive toxicity + 0.7444 74.44%
Mitochondrial toxicity + 0.5750 57.50%
Nephrotoxicity - 0.8248 82.48%
Acute Oral Toxicity (c) III 0.6567 65.67%
Estrogen receptor binding + 0.7652 76.52%
Androgen receptor binding + 0.6446 64.46%
Thyroid receptor binding + 0.6594 65.94%
Glucocorticoid receptor binding + 0.8981 89.81%
Aromatase binding + 0.5720 57.20%
PPAR gamma + 0.7997 79.97%
Honey bee toxicity - 0.8712 87.12%
Biodegradation - 0.8250 82.50%
Crustacea aquatic toxicity - 0.6200 62.00%
Fish aquatic toxicity + 0.9817 98.17%

Targets

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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 98.29% 91.11%
CHEMBL253 P34972 Cannabinoid CB2 receptor 96.46% 97.25%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 94.80% 94.45%
CHEMBL2581 P07339 Cathepsin D 93.38% 98.95%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 92.28% 96.09%
CHEMBL5845 P23415 Glycine receptor subunit alpha-1 90.75% 90.71%
CHEMBL3137262 O60341 LSD1/CoREST complex 90.32% 97.09%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 89.59% 95.56%
CHEMBL1806 P11388 DNA topoisomerase II alpha 88.45% 89.00%
CHEMBL1293249 Q13887 Kruppel-like factor 5 88.19% 86.33%
CHEMBL4685 P14902 Indoleamine 2,3-dioxygenase 86.92% 96.38%
CHEMBL3401 O75469 Pregnane X receptor 85.93% 94.73%
CHEMBL5608 Q16288 NT-3 growth factor receptor 85.88% 95.89%
CHEMBL1994 P08235 Mineralocorticoid receptor 84.48% 100.00%
CHEMBL1937 Q92769 Histone deacetylase 2 83.60% 94.75%
CHEMBL3359 P21462 Formyl peptide receptor 1 81.84% 93.56%
CHEMBL3351 Q13085 Acetyl-CoA carboxylase 1 81.57% 93.04%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 80.87% 92.62%

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.
Salvia apiana
Salvia clevelandii
Salvia mellifera
Salvia munzii
Salvia pachyphylla
Salvia rubescens

Cross-Links

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PubChem 44566424
NPASS NPC474991
ChEMBL CHEMBL491307
LOTUS LTS0192944
wikiData Q104402730