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(1S,4aS,7S,7aS)-1-[(2S,3R,4S,5S,6R)-3-[(2R,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-7-hydroxy-7-methyl-4a,5,6,7a-tetrahydro-1H-cyclopenta[c]pyran-4-carboxylic acid

Table of Contents

Details
Physical and Chemical Properties
Synonyms
2D Structure
3D Structure
ADMET Properties
Targets (proven and/or predicted)
Plants that contains it
Cross-Links

Details

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Internal ID d578a463-66b4-4056-bc15-bff5da04ff18
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
IUPAC Name (1S,4aS,7S,7aS)-1-[(2S,3R,4S,5S,6R)-3-[(2R,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-7-hydroxy-7-methyl-4a,5,6,7a-tetrahydro-1H-cyclopenta[c]pyran-4-carboxylic acid
SMILES (Canonical) CC1(CCC2C1C(OC=C2C(=O)O)OC3C(C(C(C(O3)CO)O)O)OC4C(C(CO4)(CO)O)O)O
SMILES (Isomeric) C[C@@]1(CC[C@H]2[C@@H]1[C@@H](OC=C2C(=O)O)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O[C@@H]4[C@@H]([C@](CO4)(CO)O)O)O
InChI InChI=1S/C21H32O14/c1-20(29)3-2-8-9(16(27)28)5-31-17(11(8)20)35-18-14(13(25)12(24)10(4-22)33-18)34-19-15(26)21(30,6-23)7-32-19/h5,8,10-15,17-19,22-26,29-30H,2-4,6-7H2,1H3,(H,27,28)/t8-,10-,11-,12-,13+,14-,15+,17+,18+,19-,20+,21-/m1/s1
InChI Key AMVJBPWDFCUNOH-DSQLMUDDSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C21H32O14
Molecular Weight 508.50 g/mol
Exact Mass 508.17920569 g/mol
Topological Polar Surface Area (TPSA) 225.00 Ų
XlogP -3.20
Atomic LogP (AlogP) -3.63
H-Bond Acceptor 13
H-Bond Donor 8
Rotatable Bonds 7

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of (1S,4aS,7S,7aS)-1-[(2S,3R,4S,5S,6R)-3-[(2R,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-7-hydroxy-7-methyl-4a,5,6,7a-tetrahydro-1H-cyclopenta[c]pyran-4-carboxylic acid

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.7318 73.18%
Caco-2 - 0.8747 87.47%
Blood Brain Barrier - 0.5000 50.00%
Human oral bioavailability - 0.7286 72.86%
Subcellular localzation Mitochondria 0.7327 73.27%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.7502 75.02%
OATP1B3 inhibitior + 0.9380 93.80%
MATE1 inhibitior - 0.9800 98.00%
OCT2 inhibitior - 0.7500 75.00%
BSEP inhibitior - 0.6206 62.06%
P-glycoprotein inhibitior - 0.7070 70.70%
P-glycoprotein substrate - 0.7455 74.55%
CYP3A4 substrate + 0.6723 67.23%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8863 88.63%
CYP3A4 inhibition - 0.9394 93.94%
CYP2C9 inhibition - 0.8898 88.98%
CYP2C19 inhibition - 0.8892 88.92%
CYP2D6 inhibition - 0.9080 90.80%
CYP1A2 inhibition - 0.8671 86.71%
CYP2C8 inhibition + 0.5000 50.00%
CYP inhibitory promiscuity - 0.8768 87.68%
UGT catelyzed + 0.7000 70.00%
Carcinogenicity (binary) - 1.0000 100.00%
Carcinogenicity (trinary) Non-required 0.5648 56.48%
Eye corrosion - 0.9902 99.02%
Eye irritation - 0.9435 94.35%
Skin irritation - 0.6026 60.26%
Skin corrosion - 0.9265 92.65%
Ames mutagenesis - 0.5970 59.70%
Human Ether-a-go-go-Related Gene inhibition - 0.4463 44.63%
Micronuclear - 0.8700 87.00%
Hepatotoxicity - 0.6940 69.40%
skin sensitisation - 0.8910 89.10%
Respiratory toxicity + 0.5556 55.56%
Reproductive toxicity + 0.8222 82.22%
Mitochondrial toxicity + 0.5375 53.75%
Nephrotoxicity + 0.6213 62.13%
Acute Oral Toxicity (c) III 0.4111 41.11%
Estrogen receptor binding + 0.7993 79.93%
Androgen receptor binding + 0.6259 62.59%
Thyroid receptor binding + 0.5354 53.54%
Glucocorticoid receptor binding + 0.6489 64.89%
Aromatase binding + 0.7554 75.54%
PPAR gamma + 0.6761 67.61%
Honey bee toxicity - 0.8051 80.51%
Biodegradation - 0.8250 82.50%
Crustacea aquatic toxicity - 0.7150 71.50%
Fish aquatic toxicity + 0.7298 72.98%

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 94.99% 96.09%
CHEMBL226 P30542 Adenosine A1 receptor 94.51% 95.93%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 92.65% 91.11%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 91.98% 95.56%
CHEMBL3137262 O60341 LSD1/CoREST complex 91.19% 97.09%
CHEMBL4016 P42262 Glutamate receptor ionotropic, AMPA 2 87.24% 86.92%
CHEMBL1994 P08235 Mineralocorticoid receptor 87.07% 100.00%
CHEMBL5255 O00206 Toll-like receptor 4 86.97% 92.50%
CHEMBL1806 P11388 DNA topoisomerase II alpha 86.62% 89.00%
CHEMBL1293249 Q13887 Kruppel-like factor 5 85.88% 86.33%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 84.45% 99.23%
CHEMBL5608 Q16288 NT-3 growth factor receptor 83.99% 95.89%
CHEMBL1966 Q02127 Dihydroorotate dehydrogenase 83.77% 96.09%
CHEMBL2111367 P27986 PI3-kinase p110-alpha/p85-alpha 83.65% 94.33%
CHEMBL1907603 Q05586 Glutamate NMDA receptor; GRIN1/GRIN2B 83.64% 95.89%
CHEMBL4208 P20618 Proteasome component C5 82.58% 90.00%
CHEMBL2035 P08912 Muscarinic acetylcholine receptor M5 82.39% 94.62%
CHEMBL2581 P07339 Cathepsin D 81.59% 98.95%
CHEMBL221 P23219 Cyclooxygenase-1 80.43% 90.17%
CHEMBL216 P11229 Muscarinic acetylcholine receptor M1 80.38% 94.23%
CHEMBL4187 Q99250 Sodium channel protein type II alpha subunit 80.08% 95.50%

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.
Volkameria inermis

Cross-Links

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PubChem 163012989
LOTUS LTS0267087
wikiData Q104914963