Glycyrrhizic acid
General Information
| Chemical name | Glycyrrhizic acid |
| CAS number | 1405-86-3 |
| COE number | 2221 |
| Flavouring type | substances |
| FL No. | 16.012 |
| Mixture | No |
| Purity of the named substance at least 95% unless otherwise specified | |
| Reference body | EFSA |
From webgate.ec.europa.eu
Computed Descriptors
Download SDF| 2D Structure | |
| CID | 14982 |
| IUPAC Name | (2S,3S,4S,5R,6R)-6-[(2S,3R,4S,5S,6S)-2-[[(3S,4aR,6aR,6bS,8aS,11S,12aR,14aR,14bS)-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 |
| InChI | InChI=1S/C42H62O16/c1-37(2)21-8-11-42(7)31(20(43)16-18-19-17-39(4,36(53)54)13-12-38(19,3)14-15-41(18,42)6)40(21,5)10-9-22(37)55-35-30(26(47)25(46)29(57-35)33(51)52)58-34-27(48)23(44)24(45)28(56-34)32(49)50/h16,19,21-31,34-35,44-48H,8-15,17H2,1-7H3,(H,49,50)(H,51,52)(H,53,54)/t19-,21-,22-,23-,24-,25-,26-,27+,28-,29-,30+,31+,34-,35-,38+,39-,40-,41+,42+/m0/s1 |
| InChI Key | LPLVUJXQOOQHMX-QWBHMCJMSA-N |
| Canonical SMILES | CC1(C2CCC3(C(C2(CCC1OC4C(C(C(C(O4)C(=O)O)O)O)OC5C(C(C(C(O5)C(=O)O)O)O)O)C)C(=O)C=C6C3(CCC7(C6CC(CC7)(C)C(=O)O)C)C)C)C |
| Molecular Formula | C42H62O16 |
| Wikipedia | glycyrrhizin |
From Pubchem
Computed Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 822.942 |
| Hydrogen Bond Donor Count | 8 |
| Hydrogen Bond Acceptor Count | 16 |
| Rotatable Bond Count | 7 |
| Complexity | 1730.0 |
| CACTVS Substructure Key Fingerprint | A A A D c f B 8 P g A A A A A A A A A A A A A A A A A A A A A A A A A 0 a M G C A A A A A A D A A A A A G g A A C A A A D x S w g A M C C A A A B g C I A q D S C A I A A A A g A A A A C A F A A E g R E B Y A A Q Q i Q A A F o A A P A Q P K 7 P z P g A A A A A A A A A D A A A Y A A D A A A A A A A A A A A A = = |
| Topological Polar Surface Area | 267.0 |
| Monoisotopic Mass | 822.404 |
| Exact Mass | 822.404 |
| XLogP3 | None |
| XLogP3-AA | 3.7 |
| Compound Is Canonicalized | True |
| Formal Charge | 0 |
| Heavy Atom Count | 58 |
| Defined Atom Stereocenter Count | 19 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Isotope Atom Count | 0 |
| Covalently-Bonded Unit Count | 1 |
From Pubchem
Food Additives Biosynthesis/Degradation
ADMET Predicted Profile --- Classification
| Model | Result | Probability |
|---|---|---|
| Absorption | ||
| Blood-Brain Barrier | BBB- | 0.5591 |
| Human Intestinal Absorption | HIA+ | 0.5824 |
| Caco-2 Permeability | Caco2- | 0.8298 |
| P-glycoprotein Substrate | Substrate | 0.8729 |
| P-glycoprotein Inhibitor | Inhibitor | 0.5000 |
| Non-inhibitor | 0.5523 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.8730 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.8383 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.8668 |
| CYP450 2D6 Substrate | Non-substrate | 0.8973 |
| CYP450 3A4 Substrate | Substrate | 0.7351 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.8358 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.8692 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9423 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.9112 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.8309 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.9568 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9677 |
| Non-inhibitor | 0.6995 | |
| AMES Toxicity | Non AMES toxic | 0.9133 |
| Carcinogens | Non-carcinogens | 0.9655 |
| Fish Toxicity | High FHMT | 0.9865 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.9938 |
| Honey Bee Toxicity | High HBT | 0.8222 |
| Biodegradation | Not ready biodegradable | 0.9621 |
| Acute Oral Toxicity | IV | 0.6130 |
| Carcinogenicity (Three-class) | Non-required | 0.6106 |
From admetSAR
ADMET Predicted Profile --- Regression
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -4.5128 | LogS |
| Caco-2 Permeability | 0.1226 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 1.9551 | LD50, mol/kg |
| Fish Toxicity | 0.9106 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 1.0272 | pIGC50, ug/L |
From admetSAR
Taxonomic Classification
| Kingdom | Organic compounds |
|---|---|
| Superclass | Lipids and lipid-like molecules |
| Class | Prenol lipids |
| Subclass | Terpene glycosides |
| Intermediate Tree Nodes | Triterpene glycosides |
| Direct Parent | Triterpene saponins |
| Alternative Parents | |
| Molecular Framework | Aliphatic heteropolycyclic compounds |
| Substituents | Triterpene saponin - Triterpenoid - 1-o-glucuronide - O-glucuronide - Glucuronic acid or derivatives - Disaccharide - Glycosyl compound - O-glycosyl compound - Tricarboxylic acid or derivatives - Beta-hydroxy acid - Cyclohexenone - Pyran - Oxane - Hydroxy acid - Secondary alcohol - Ketone - Organoheterocyclic compound - Oxacycle - Polyol - Carboxylic acid derivative - Carboxylic acid - Acetal - Carbonyl group - Hydrocarbon derivative - Organic oxygen compound - Alcohol - Organooxygen compound - Organic oxide - Aliphatic heteropolycyclic compound |
| Description | This compound belongs to the class of organic compounds known as triterpene saponins. These are glycosylated derivatives of triterpene sapogenins. The sapogenin moiety backbone is usually based on the oleanane, ursane, taraxastane, bauerane, lanostane, lupeol, lupane, dammarane, cycloartane, friedelane, hopane, 9b,19-cyclo-lanostane, cycloartane, or cycloartanol skeleton. |
From ClassyFire