5beta,6beta-Dihydroxyboschnaloside

Details

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Internal ID 760b75c6-1737-4a3a-b657-23c68b6556b5
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
IUPAC Name (1S,4aR,5R,7R,7aR)-4a,5-dihydroxy-7-methyl-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-5,6,7,7a-tetrahydro-1H-cyclopenta[c]pyran-4-carbaldehyde
SMILES (Canonical) CC1CC(C2(C1C(OC=C2C=O)OC3C(C(C(C(O3)CO)O)O)O)O)O
SMILES (Isomeric) C[C@@H]1C[C@H]([C@]2([C@@H]1[C@@H](OC=C2C=O)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)O)O
InChI InChI=1S/C16H24O10/c1-6-2-9(19)16(23)7(3-17)5-24-14(10(6)16)26-15-13(22)12(21)11(20)8(4-18)25-15/h3,5-6,8-15,18-23H,2,4H2,1H3/t6-,8-,9-,10+,11-,12+,13-,14+,15+,16-/m1/s1
InChI Key LANDSIPVLIDHEU-NKFHIRRBSA-N
Popularity 1 reference in papers

Physical and Chemical Properties

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Molecular Formula C16H24O10
Molecular Weight 376.36 g/mol
Exact Mass 376.13694696 g/mol
Topological Polar Surface Area (TPSA) 166.00 Ų
XlogP -2.30
Atomic LogP (AlogP) -3.01
H-Bond Acceptor 10
H-Bond Donor 6
Rotatable Bonds 4

Synonyms

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(1S,4aR,5R,7R,7aR)-4a,5-dihydroxy-7-methyl-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-5,6,7,7a-tetrahydro-1H-cyclopenta[c]pyran-4-carbaldehyde

2D Structure

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2D Structure of 5beta,6beta-Dihydroxyboschnaloside

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.7115 71.15%
Caco-2 - 0.8608 86.08%
Blood Brain Barrier - 0.5250 52.50%
Human oral bioavailability - 0.8714 87.14%
Subcellular localzation Mitochondria 0.6595 65.95%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.7786 77.86%
OATP1B3 inhibitior + 0.9476 94.76%
MATE1 inhibitior - 0.9600 96.00%
OCT2 inhibitior - 0.9250 92.50%
BSEP inhibitior - 0.8659 86.59%
P-glycoprotein inhibitior - 0.8612 86.12%
P-glycoprotein substrate - 0.8508 85.08%
CYP3A4 substrate + 0.5996 59.96%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8528 85.28%
CYP3A4 inhibition - 0.9377 93.77%
CYP2C9 inhibition - 0.9055 90.55%
CYP2C19 inhibition - 0.8851 88.51%
CYP2D6 inhibition - 0.9118 91.18%
CYP1A2 inhibition - 0.8960 89.60%
CYP2C8 inhibition - 0.7348 73.48%
CYP inhibitory promiscuity - 0.8494 84.94%
UGT catelyzed + 0.7000 70.00%
Carcinogenicity (binary) - 1.0000 100.00%
Carcinogenicity (trinary) Non-required 0.6294 62.94%
Eye corrosion - 0.9903 99.03%
Eye irritation - 0.9792 97.92%
Skin irritation - 0.7163 71.63%
Skin corrosion - 0.9443 94.43%
Ames mutagenesis - 0.5254 52.54%
Human Ether-a-go-go-Related Gene inhibition - 0.5232 52.32%
Micronuclear - 0.7200 72.00%
Hepatotoxicity - 0.7552 75.52%
skin sensitisation - 0.8626 86.26%
Respiratory toxicity - 0.5111 51.11%
Reproductive toxicity + 0.8222 82.22%
Mitochondrial toxicity + 0.6000 60.00%
Nephrotoxicity + 0.5190 51.90%
Acute Oral Toxicity (c) III 0.4392 43.92%
Estrogen receptor binding - 0.5632 56.32%
Androgen receptor binding + 0.5391 53.91%
Thyroid receptor binding + 0.5452 54.52%
Glucocorticoid receptor binding - 0.6330 63.30%
Aromatase binding + 0.5951 59.51%
PPAR gamma + 0.5624 56.24%
Honey bee toxicity - 0.8291 82.91%
Biodegradation - 0.7500 75.00%
Crustacea aquatic toxicity - 0.6255 62.55%
Fish aquatic toxicity + 0.6574 65.74%

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
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 95.95% 96.09%
CHEMBL218 P21554 Cannabinoid CB1 receptor 92.49% 96.61%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 91.46% 95.56%
CHEMBL3137262 O60341 LSD1/CoREST complex 90.81% 97.09%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 88.81% 91.11%
CHEMBL2581 P07339 Cathepsin D 86.83% 98.95%
CHEMBL1806 P11388 DNA topoisomerase II alpha 86.56% 89.00%
CHEMBL1293249 Q13887 Kruppel-like factor 5 86.34% 86.33%
CHEMBL4208 P20618 Proteasome component C5 85.51% 90.00%
CHEMBL1994 P08235 Mineralocorticoid receptor 83.59% 100.00%
CHEMBL253 P34972 Cannabinoid CB2 receptor 82.27% 97.25%
CHEMBL3401 O75469 Pregnane X receptor 81.68% 94.73%

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.
Euphrasia nemorosa
Titanotrichum oldhamii

Cross-Links

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PubChem 21609758
NPASS NPC210633
LOTUS LTS0057805
wikiData Q105148747