Ingredient Details :18alpha-Glycyrrhetinic acid


TCMI-ID: TCMI03162


Physicochemical Property
Ingredient Name 18alpha-Glycyrrhetinic acid
Pubchem CID 73398
Iupac name (2S,4aS,6aR,6aS,6bR,8aR,10S,12aS,14bS)-10-hydroxy-2,4a,6a,6b,9,9,12a-heptamethyl-13-oxo-3,4,5,6,6a,7,8,8a,10,11,12,14b-dodecahydro-1H-picene-2-carboxylic acid
Molecular Formula C30H46O4
Molecular Weight 470.7
Isomeric smiles C[C@]12CC[C@](C[C@@H]1C3=CC(=O)[C@@H]4[C@]5(CC[C@@H](C([C@@H]5CC[C@]4([C@@]3(CC2)C)C)(C)C)O)C)(C)C(=O)O
InChI InChI=1S/C30H46O4/c1-25(2)21-8-11-30(7)23(28(21,5)10-9-22(25)32)20(31)16-18-19-17-27(4,24(33)34)13-12-26(19,3)14-15-29(18,30)6/h16,19,21-23,32H,8-15,17H2,1-7H3,(H,33,34)/t19-,21+,22+,23-,26-,27+,28+,29-,30-/m1/s1
InChIKey MPDGHEJMBKOTSU-PMTKVOBESA-N
External Database Links HERB2.0: HBIN018136   SymMap: SMIT18313   TCMSID: 4867   TCMSuite: 16672   ChEMBL: CHEMBL454067  
Structural Information
nHA(Number of hydrogen bond acceptors) 4
nHD(Number of hydrogen bond donors) 2
nRot(Number of rotatable bonds) 1
nRing(Number of rings) 5
MaxRing(Number of atoms in the biggest ring) 22
nHet(Number of heteroatoms) 4

Stability
nRig(Number of rigid bonds) 28
Flexibility 0.036
Stereo Centers(Number of stereocenters) 9

Solubility
TPSA(Topological polar surface area) 74.6
logS(The logarithm of aqueous solubility value) -4.461
logP(The logarithm of the n-octanol/water distribution coefficient) 5.849
logD7.4(The logarithm of the n-octanol/water distribution coefficients at pH=7.4) 4.343

Pharmacokinetic Property
Quantitative Estimate of Drug-likeness 0.464
Synthetic accessibility score 4.764
Natural Product-likeness score 3.183
Lipinski Rule Accepted
GSK Rule Rejected
Golden Triangle Accepted

Absorption
Caco-2 Permeability -5.504
MDCK Permeability 1.84E-05
Pgp-substrate 0.003
HIA(human intestinal absorption) 0.013
F20%(20% Oral Bioavailability) 0.014
F30%(30% Oral Bioavailability) 0.977

Distribution
PPB(Plasma protein binding) 88.83%
VD(Volume Distribution) 0.644
BBB Penetration(Blood brain barrier penetration) 0.275
B3 Penetration(Blood brain barrier penetration) Non-Permeable
Fu(The fraction unbound in plasms) 8.89%

Metabolism
CYP1A2 inhibitor 0.003
CYP1A2 substrate 0.816
CYP2C19 inhibitor 0.018
CYP2C19 substrate 0.842
CYP2C9 inhibitor 0.121
CYP2C9 substrate 0.065
CYP2D6 inhibitor 0.004
CYP2D6 substrate 0.029
CYP3A4 inhibitor 0.459
CYP3A4 substrate 0.501

Excretion
CL(The clearance of a drug) 2.65
T1/2 0.113

Toxicology
NonBiodegradable Rule 1
Pfizer Rule Rejected
SR-MMP 0.948

Toxic Dose
FDAMDD(FDA Maximum (Recommended) Daily Dose) 0.942
IGC50 4.876
LC50FM 5.782
LC50DM 6.493

Reproductive Effects
NR-AR(Androgen receptor) 0.846
NR-AR-LBD(Androgen receptor) 0.932
NR-Aromatase 0.766
NR-ER(Estrogen receptor) 0.28
NR-ER-LBD(Estrogen receptor) 0.468

Allergy
Skin Sensitization Rule 3
Skin Sensitization 0.221

Acute Toxicity
Acute Toxicity Rule 3
Rat Oral Acute Toxicity 0.577

Organ Toxicity
hERG Blockers 0.009
H-HT(The human hepatotoxicity) 0.353
DILI(Drug-induced liver injury) 0.006

Primary Irritation
Eye Corrosion 0.023
Eye Irritation 0.023
Respiratory Toxicity 0.983

Mutagenic Effects
AMES Toxicity 0.022

Tumorigenic Effects
Carcinogencity 0.212
SR-ARE(Antioxidant Response Element) 0.866
SR-ATAD5(ATPase family AAA domain-containing protein 5) 0.815
SR-p53 0.879

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