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ACETOXYGLYCYRRHIZIN, 22beta-

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 099694eb-25ed-4fbf-9da5-2b8ee2d2a3f9
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Triterpene glycosides > Triterpene saponins
IUPAC Name (2S,3S,4S,5R,6R)-6-[(2R,3R,4S,5S,6S)-2-[[(3S,4aR,6aR,6bS,8aR,9R,11R,12aS,14aR,14bS)-9-acetyloxy-11-carboxy-4,4,6a,6b,8a,11,14b-heptamethyl-14-oxo-2,3,4a,5,6,7,8,9,10,12,12a,14a-dodecahydro-1H-picen-3-yl]oxy]-6-carboxy-4,5-dihydroxyoxan-3-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid
SMILES (Canonical) CC(=O)OC1CC(CC2C1(CCC3(C2=CC(=O)C4C3(CCC5C4(CCC(C5(C)C)OC6C(C(C(C(O6)C(=O)O)O)O)OC7C(C(C(C(O7)C(=O)O)O)O)O)C)C)C)C)(C)C(=O)O
SMILES (Isomeric) CC(=O)O[C@@H]1C[C@](C[C@@H]2[C@]1(CC[C@@]3(C2=CC(=O)[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)C(=O)O)O)O)O[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)C(=O)O)O)O)O)C)C)C)C)(C)C(=O)O
InChI InChI=1S/C44H64O18/c1-18(45)58-24-17-40(4,38(56)57)16-20-19-15-21(46)33-42(6)11-10-23(39(2,3)22(42)9-12-44(33,8)43(19,7)14-13-41(20,24)5)59-37-32(28(50)27(49)31(61-37)35(54)55)62-36-29(51)25(47)26(48)30(60-36)34(52)53/h15,20,22-33,36-37,47-51H,9-14,16-17H2,1-8H3,(H,52,53)(H,54,55)(H,56,57)/t20-,22-,23-,24+,25-,26-,27-,28-,29+,30-,31-,32+,33+,36-,37+,40+,41+,42-,43+,44+/m0/s1
InChI Key OBFDSOYVKVRFGY-AZFCQWTHSA-N
Popularity 2 references in papers

Physical and Chemical Properties

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Molecular Formula C44H64O18
Molecular Weight 881.00 g/mol
Exact Mass 880.40926519 g/mol
Topological Polar Surface Area (TPSA) 293.00 Ų
XlogP 3.00
Atomic LogP (AlogP) 1.79
H-Bond Acceptor 15
H-Bond Donor 8
Rotatable Bonds 8

Synonyms

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22-beta-Acetoxyglycyrrhizin
VFH398C4TK
22beta-Acetoxyglycyrrhizin
Acetoxyglycyrrhizin, 22beta-
938042-17-2
UNII-VFH398C4TK
beta-D-Glucopyranosiduronic acid, (3beta,22beta,20beta)-22-(acetyloxy)-20-carboxy-11-oxo-30-norolean-12-en-3-yl 2-o-beta-D-glucopyranuronosyl-
(2S,3S,4S,5R,6R)-6-(((3S,4AR,6AR,6BS,8AR,9R,11R,12AS,14AR,14BS)-9-(ACETYLOXY)-11-CARBOXY-4,4,6A,6B,8A,11,14B-HEPTAMETHYL-14-OXO-1,2,3,4,4A,5,6,6A,6B,7,8,8A,9,10,11,12,12A,14,14A,14B-ICOSAHYDROPICEN-3-YL)OXY)-5-(((2R,3R,4S,5S,6S)-6-CARBOXY-3,4,5-TRIHYDROXYOXAN-2-YL)OXY)-3,4-DIHYDROXYOXANE-2-CARBOXYLIC ACID
22.BETA.-ACETOXYGLYCYRRHIZIN
HY-N11026
There are more than 10 synonyms. If you wish to see them all click here.

2D Structure

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2D Structure of ACETOXYGLYCYRRHIZIN, 22beta-

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9175 91.75%
Caco-2 - 0.8757 87.57%
Blood Brain Barrier - 0.6750 67.50%
Human oral bioavailability - 0.6714 67.14%
Subcellular localzation Mitochondria 0.8274 82.74%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior - 0.4084 40.84%
OATP1B3 inhibitior - 0.3487 34.87%
MATE1 inhibitior - 0.9400 94.00%
OCT2 inhibitior + 0.6250 62.50%
BSEP inhibitior + 0.6398 63.98%
P-glycoprotein inhibitior + 0.7581 75.81%
P-glycoprotein substrate - 0.6571 65.71%
CYP3A4 substrate + 0.7329 73.29%
CYP2C9 substrate - 0.7915 79.15%
CYP2D6 substrate - 0.8989 89.89%
CYP3A4 inhibition - 0.8221 82.21%
CYP2C9 inhibition - 0.8659 86.59%
CYP2C19 inhibition - 0.9292 92.92%
CYP2D6 inhibition - 0.9493 94.93%
CYP1A2 inhibition - 0.8720 87.20%
CYP2C8 inhibition + 0.6989 69.89%
CYP inhibitory promiscuity - 0.9677 96.77%
UGT catelyzed + 0.7000 70.00%
Carcinogenicity (binary) - 0.9600 96.00%
Carcinogenicity (trinary) Non-required 0.6115 61.15%
Eye corrosion - 0.9901 99.01%
Eye irritation - 0.9043 90.43%
Skin irritation - 0.5622 56.22%
Skin corrosion - 0.9226 92.26%
Ames mutagenesis - 0.8200 82.00%
Human Ether-a-go-go-Related Gene inhibition - 0.4641 46.41%
Micronuclear - 0.7000 70.00%
Hepatotoxicity + 0.5783 57.83%
skin sensitisation - 0.7947 79.47%
Respiratory toxicity + 0.6111 61.11%
Reproductive toxicity + 0.8667 86.67%
Mitochondrial toxicity + 0.6000 60.00%
Nephrotoxicity - 0.6164 61.64%
Acute Oral Toxicity (c) IV 0.6236 62.36%
Estrogen receptor binding + 0.7768 77.68%
Androgen receptor binding + 0.7416 74.16%
Thyroid receptor binding - 0.6719 67.19%
Glucocorticoid receptor binding + 0.7556 75.56%
Aromatase binding + 0.6453 64.53%
PPAR gamma + 0.8058 80.58%
Honey bee toxicity - 0.6870 68.70%
Biodegradation - 0.7250 72.50%
Crustacea aquatic toxicity - 0.5400 54.00%
Fish aquatic toxicity + 0.9872 98.72%

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 97.59% 91.11%
CHEMBL3746 P80365 11-beta-hydroxysteroid dehydrogenase 2 97.19% 94.78%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 93.08% 95.56%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 92.50% 96.09%
CHEMBL1951 P21397 Monoamine oxidase A 91.85% 91.49%
CHEMBL1806 P11388 DNA topoisomerase II alpha 91.01% 89.00%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 90.21% 94.45%
CHEMBL5608 Q16288 NT-3 growth factor receptor 88.69% 95.89%
CHEMBL2581 P07339 Cathepsin D 88.32% 98.95%
CHEMBL340 P08684 Cytochrome P450 3A4 86.55% 91.19%
CHEMBL3714130 P46095 G-protein coupled receptor 6 86.31% 97.36%
CHEMBL3807 P17706 T-cell protein-tyrosine phosphatase 85.37% 93.00%
CHEMBL221 P23219 Cyclooxygenase-1 84.56% 90.17%
CHEMBL1293249 Q13887 Kruppel-like factor 5 84.38% 86.33%
CHEMBL1994 P08235 Mineralocorticoid receptor 83.70% 100.00%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 82.79% 99.23%
CHEMBL5255 O00206 Toll-like receptor 4 82.53% 92.50%
CHEMBL4685 P14902 Indoleamine 2,3-dioxygenase 81.75% 96.38%

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.
Glycyrrhiza uralensis
Mitracarpus hirtus

Cross-Links

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PubChem 102051862
NPASS NPC182342