(1R,3R,4R,4aS,5'S,8S,8aR)-5'-(furan-3-yl)-1,8-dihydroxy-8,8a-bis(hydroxymethyl)-3-methylspiro[2,3,4a,5,6,7-hexahydro-1H-naphthalene-4,3'-oxolane]-2'-one

Details

Top
Internal ID 6023ec79-8120-458b-aaa5-11aacefe9deb
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Diterpene lactones
IUPAC Name (1R,3R,4R,4aS,5'S,8S,8aR)-5'-(furan-3-yl)-1,8-dihydroxy-8,8a-bis(hydroxymethyl)-3-methylspiro[2,3,4a,5,6,7-hexahydro-1H-naphthalene-4,3'-oxolane]-2'-one
SMILES (Canonical) CC1CC(C2(C(C13CC(OC3=O)C4=COC=C4)CCCC2(CO)O)CO)O
SMILES (Isomeric) C[C@@H]1C[C@H]([C@@]2([C@@H]([C@@]13C[C@H](OC3=O)C4=COC=C4)CCC[C@]2(CO)O)CO)O
InChI InChI=1S/C20H28O7/c1-12-7-16(23)20(11-22)15(3-2-5-18(20,25)10-21)19(12)8-14(27-17(19)24)13-4-6-26-9-13/h4,6,9,12,14-16,21-23,25H,2-3,5,7-8,10-11H2,1H3/t12-,14+,15-,16-,18-,19-,20+/m1/s1
InChI Key HIYFFAFPIZXJIY-HPQWIRMFSA-N
Popularity 6 references in papers

Physical and Chemical Properties

Top
Molecular Formula C20H28O7
Molecular Weight 380.40 g/mol
Exact Mass 380.18350323 g/mol
Topological Polar Surface Area (TPSA) 120.00 Ų
XlogP 0.70
Atomic LogP (AlogP) 1.16
H-Bond Acceptor 7
H-Bond Donor 4
Rotatable Bonds 3

Synonyms

Top
There are no found synonyms.

2D Structure

Top
2D Structure of (1R,3R,4R,4aS,5'S,8S,8aR)-5'-(furan-3-yl)-1,8-dihydroxy-8,8a-bis(hydroxymethyl)-3-methylspiro[2,3,4a,5,6,7-hexahydro-1H-naphthalene-4,3'-oxolane]-2'-one

3D Structure

Top

ADMET Properties (via admetSAR 2)

Top
Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.8665 86.65%
Caco-2 - 0.6922 69.22%
Blood Brain Barrier - 0.5750 57.50%
Human oral bioavailability - 0.6857 68.57%
Subcellular localzation Mitochondria 0.7474 74.74%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8161 81.61%
OATP1B3 inhibitior + 0.9525 95.25%
MATE1 inhibitior - 0.9200 92.00%
OCT2 inhibitior - 0.7537 75.37%
BSEP inhibitior - 0.6889 68.89%
P-glycoprotein inhibitior - 0.8838 88.38%
P-glycoprotein substrate - 0.6779 67.79%
CYP3A4 substrate + 0.6443 64.43%
CYP2C9 substrate - 0.8038 80.38%
CYP2D6 substrate - 0.7958 79.58%
CYP3A4 inhibition - 0.8353 83.53%
CYP2C9 inhibition - 0.8916 89.16%
CYP2C19 inhibition - 0.8538 85.38%
CYP2D6 inhibition - 0.9465 94.65%
CYP1A2 inhibition - 0.9157 91.57%
CYP2C8 inhibition - 0.5823 58.23%
CYP inhibitory promiscuity - 0.9568 95.68%
UGT catelyzed - 0.5000 50.00%
Carcinogenicity (binary) - 0.9900 99.00%
Carcinogenicity (trinary) Non-required 0.5232 52.32%
Eye corrosion - 0.9939 99.39%
Eye irritation - 0.9776 97.76%
Skin irritation - 0.6793 67.93%
Skin corrosion - 0.9485 94.85%
Ames mutagenesis - 0.5895 58.95%
Human Ether-a-go-go-Related Gene inhibition + 0.6949 69.49%
Micronuclear - 0.8000 80.00%
Hepatotoxicity + 0.6225 62.25%
skin sensitisation - 0.9271 92.71%
Respiratory toxicity + 0.7333 73.33%
Reproductive toxicity + 0.8111 81.11%
Mitochondrial toxicity + 0.6500 65.00%
Nephrotoxicity - 0.5605 56.05%
Acute Oral Toxicity (c) I 0.3502 35.02%
Estrogen receptor binding + 0.9135 91.35%
Androgen receptor binding + 0.6511 65.11%
Thyroid receptor binding + 0.5788 57.88%
Glucocorticoid receptor binding + 0.8182 81.82%
Aromatase binding + 0.8245 82.45%
PPAR gamma - 0.6008 60.08%
Honey bee toxicity - 0.8819 88.19%
Biodegradation - 0.7250 72.50%
Crustacea aquatic toxicity - 0.5000 50.00%
Fish aquatic toxicity + 0.9516 95.16%

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
CHEMBL3137262 O60341 LSD1/CoREST complex 97.05% 97.09%
CHEMBL221 P23219 Cyclooxygenase-1 96.09% 90.17%
CHEMBL253 P34972 Cannabinoid CB2 receptor 92.93% 97.25%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 92.13% 91.11%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 91.59% 96.09%
CHEMBL1994 P08235 Mineralocorticoid receptor 89.95% 100.00%
CHEMBL1293249 Q13887 Kruppel-like factor 5 87.19% 86.33%
CHEMBL1806 P11388 DNA topoisomerase II alpha 86.54% 89.00%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 86.22% 95.56%
CHEMBL5608 Q16288 NT-3 growth factor receptor 83.95% 95.89%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 83.75% 94.00%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 82.64% 99.23%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 80.71% 85.14%
CHEMBL2581 P07339 Cathepsin D 80.27% 98.95%
CHEMBL1907600 Q00535 Cyclin-dependent kinase 5/CDK5 activator 1 80.17% 93.03%

Plants that contains it

Top
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.
Teucrium lamiifolium
Teucrium montanum
Teucrium polium
Teucrium scordium

Cross-Links

Top
PubChem 101198592
LOTUS LTS0095661
wikiData Q104401888