Ingredient Details :(3beta,6alpha,19alpha)-3,6,19-Trihydroxy-12-ursen-28-oic acid


TCMI-ID: TCMI15849


Physicochemical Property
Ingredient Name (3beta,6alpha,19alpha)-3,6,19-Trihydroxy-12-ursen-28-oic acid
Pubchem CID 14355557
Iupac name 1,8,10-trihydroxy-1,2,6a,6b,9,9,12a-heptamethyl-2,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid
Molecular Formula C30H48O5
Molecular Weight 488.7
Isomeric smiles CC1CCC2(CCC3(C(=CCC4C3(CC(C5C4(CCC(C5(C)C)O)C)O)C)C2C1(C)O)C)C(=O)O
InChI InChI=1S/C30H48O5/c1-17-10-13-30(24(33)34)15-14-27(5)18(22(30)29(17,7)35)8-9-20-26(4)12-11-21(32)25(2,3)23(26)19(31)16-28(20,27)6/h8,17,19-23,31-32,35H,9-16H2,1-7H3,(H,33,34)
InChIKey JPGOJQJBPLCRQP-UHFFFAOYSA-N
External Database Links TCMSID: 12282  
Structural Information
nHA(Number of hydrogen bond acceptors) 5
nHD(Number of hydrogen bond donors) 4
nRot(Number of rotatable bonds) 1
nRing(Number of rings) 5
MaxRing(Number of atoms in the biggest ring) 22
nHet(Number of heteroatoms) 5

Stability
nRig(Number of rigid bonds) 27
Flexibility 0.037
Stereo Centers(Number of stereocenters) 11

Solubility
TPSA(Topological polar surface area) 97.99
logS(The logarithm of aqueous solubility value) -3.781
logP(The logarithm of the n-octanol/water distribution coefficient) 4.269
logD7.4(The logarithm of the n-octanol/water distribution coefficients at pH=7.4) 4.05

Pharmacokinetic Property
Quantitative Estimate of Drug-likeness 0.382
Synthetic accessibility score 5.089
Natural Product-likeness score 3.45
Lipinski Rule Accepted
GSK Rule Rejected
Golden Triangle Accepted

Absorption
Caco-2 Permeability -5.384
MDCK Permeability 2.19E-05
Pgp-substrate 0.002
HIA(human intestinal absorption) 0.115
F20%(20% Oral Bioavailability) 0.006
F30%(30% Oral Bioavailability) 0.106

Distribution
PPB(Plasma protein binding) 92.83%
VD(Volume Distribution) 0.726
BBB Penetration(Blood brain barrier penetration) 0.872
B3 Penetration(Blood brain barrier penetration) Non-Permeable
Fu(The fraction unbound in plasms) 5.46%

Metabolism
CYP1A2 inhibitor 0.002
CYP1A2 substrate 0.43
CYP2C19 inhibitor 0.006
CYP2C19 substrate 0.901
CYP2C9 inhibitor 0.067
CYP2C9 substrate 0.544
CYP2D6 inhibitor 0.003
CYP2D6 substrate 0.167
CYP3A4 inhibitor 0.111
CYP3A4 substrate 0.186

Excretion
CL(The clearance of a drug) 3.347
T1/2 0.032

Toxicology
NonBiodegradable Rule 0
Pfizer Rule Accepted
SR-MMP 0.959

Toxic Dose
FDAMDD(FDA Maximum (Recommended) Daily Dose) 0.466
IGC50 4.877
LC50FM 6.013
LC50DM 5.772

Reproductive Effects
NR-AR(Androgen receptor) 0.004
NR-AR-LBD(Androgen receptor) 0.01
NR-Aromatase 0.885
NR-ER(Estrogen receptor) 0.085
NR-ER-LBD(Estrogen receptor) 0.184

Allergy
Skin Sensitization Rule 0
Skin Sensitization 0.01

Acute Toxicity
Acute Toxicity Rule 1
Rat Oral Acute Toxicity 0.29

Organ Toxicity
hERG Blockers 0
H-HT(The human hepatotoxicity) 0.193
DILI(Drug-induced liver injury) 0.012

Primary Irritation
Eye Corrosion 0.003
Eye Irritation 0.06
Respiratory Toxicity 0.982

Mutagenic Effects
AMES Toxicity 0.032

Tumorigenic Effects
Carcinogencity 0.025
SR-ARE(Antioxidant Response Element) 0.493
SR-ATAD5(ATPase family AAA domain-containing protein 5) 0.013
SR-p53 0.593

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