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(1S,4aS,7S,7aS)-1-[(2S,3R,4S,5S,6R)-3-[(2R,3R,4S)-3,4-dihydroxy-4-[(4-hydroxybenzoyl)oxymethyl]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 33178796-c912-4f0e-b9e0-b62fe57de6d4
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,4S)-3,4-dihydroxy-4-[(4-hydroxybenzoyl)oxymethyl]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)(COC(=O)C5=CC=C(C=C5)O)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)(COC(=O)C5=CC=C(C=C5)O)O)O)O
InChI InChI=1S/C28H36O16/c1-27(37)7-6-14-15(22(34)35)9-39-24(17(14)27)44-25-20(19(32)18(31)16(8-29)42-25)43-26-21(33)28(38,11-41-26)10-40-23(36)12-2-4-13(30)5-3-12/h2-5,9,14,16-21,24-26,29-33,37-38H,6-8,10-11H2,1H3,(H,34,35)/t14-,16-,17-,18-,19+,20-,21+,24+,25+,26-,27+,28-/m1/s1
InChI Key CFEHXHKHKXLAMI-RORGFKFASA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C28H36O16
Molecular Weight 628.60 g/mol
Exact Mass 628.20033506 g/mol
Topological Polar Surface Area (TPSA) 251.00 Ų
XlogP -1.90
Atomic LogP (AlogP) -2.06
H-Bond Acceptor 15
H-Bond Donor 8
Rotatable Bonds 9

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,4S)-3,4-dihydroxy-4-[(4-hydroxybenzoyl)oxymethyl]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 + 0.8133 81.33%
Caco-2 - 0.8970 89.70%
Blood Brain Barrier - 0.5000 50.00%
Human oral bioavailability - 0.8000 80.00%
Subcellular localzation Mitochondria 0.7533 75.33%
OATP2B1 inhibitior - 0.8627 86.27%
OATP1B1 inhibitior + 0.7509 75.09%
OATP1B3 inhibitior + 0.9332 93.32%
MATE1 inhibitior - 0.9800 98.00%
OCT2 inhibitior - 0.7271 72.71%
BSEP inhibitior - 0.7447 74.47%
P-glycoprotein inhibitior - 0.4862 48.62%
P-glycoprotein substrate - 0.5315 53.15%
CYP3A4 substrate + 0.7036 70.36%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8794 87.94%
CYP3A4 inhibition - 0.8361 83.61%
CYP2C9 inhibition - 0.8203 82.03%
CYP2C19 inhibition - 0.8236 82.36%
CYP2D6 inhibition - 0.8932 89.32%
CYP1A2 inhibition - 0.7906 79.06%
CYP2C8 inhibition + 0.8037 80.37%
CYP inhibitory promiscuity - 0.8268 82.68%
UGT catelyzed + 0.7000 70.00%
Carcinogenicity (binary) - 0.9800 98.00%
Carcinogenicity (trinary) Non-required 0.4922 49.22%
Eye corrosion - 0.9904 99.04%
Eye irritation - 0.9265 92.65%
Skin irritation - 0.6539 65.39%
Skin corrosion - 0.9257 92.57%
Ames mutagenesis - 0.6140 61.40%
Human Ether-a-go-go-Related Gene inhibition - 0.5000 50.00%
Micronuclear - 0.7400 74.00%
Hepatotoxicity - 0.6691 66.91%
skin sensitisation - 0.8679 86.79%
Respiratory toxicity + 0.6000 60.00%
Reproductive toxicity + 0.9111 91.11%
Mitochondrial toxicity + 0.7250 72.50%
Nephrotoxicity + 0.5083 50.83%
Acute Oral Toxicity (c) I 0.4359 43.59%
Estrogen receptor binding + 0.8155 81.55%
Androgen receptor binding + 0.7138 71.38%
Thyroid receptor binding - 0.5159 51.59%
Glucocorticoid receptor binding + 0.6593 65.93%
Aromatase binding + 0.6818 68.18%
PPAR gamma + 0.6985 69.85%
Honey bee toxicity - 0.7897 78.97%
Biodegradation - 0.7750 77.50%
Crustacea aquatic toxicity - 0.6550 65.50%
Fish aquatic toxicity + 0.9339 93.39%

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
CHEMBL226 P30542 Adenosine A1 receptor 94.88% 95.93%
CHEMBL1293249 Q13887 Kruppel-like factor 5 94.10% 86.33%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 93.44% 96.09%
CHEMBL3137262 O60341 LSD1/CoREST complex 93.37% 97.09%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 92.60% 91.11%
CHEMBL216 P11229 Muscarinic acetylcholine receptor M1 89.76% 94.23%
CHEMBL4208 P20618 Proteasome component C5 89.67% 90.00%
CHEMBL1806 P11388 DNA topoisomerase II alpha 88.46% 89.00%
CHEMBL2035 P08912 Muscarinic acetylcholine receptor M5 88.22% 94.62%
CHEMBL5255 O00206 Toll-like receptor 4 87.20% 92.50%
CHEMBL1994 P08235 Mineralocorticoid receptor 86.96% 100.00%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 86.17% 95.56%
CHEMBL5608 Q16288 NT-3 growth factor receptor 86.09% 95.89%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 85.68% 99.23%
CHEMBL2581 P07339 Cathepsin D 83.68% 98.95%
CHEMBL2996 Q05655 Protein kinase C delta 83.60% 97.79%
CHEMBL340 P08684 Cytochrome P450 3A4 83.02% 91.19%
CHEMBL1907603 Q05586 Glutamate NMDA receptor; GRIN1/GRIN2B 81.77% 95.89%
CHEMBL211 P08172 Muscarinic acetylcholine receptor M2 81.04% 94.97%
CHEMBL2111367 P27986 PI3-kinase p110-alpha/p85-alpha 80.64% 94.33%
CHEMBL3060 Q9Y345 Glycine transporter 2 80.58% 99.17%
CHEMBL4227 P25090 Lipoxin A4 receptor 80.57% 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.
Volkameria inermis

Cross-Links

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PubChem 162999511
LOTUS LTS0184463
wikiData Q104956430