Ingredient Details :Coclaurine


TCMI-ID: TCMI04666


Physicochemical Property
Ingredient Name Coclaurine
Pubchem CID 160487
Iupac name (1S)-1-[(4-hydroxyphenyl)methyl]-6-methoxy-1,2,3,4-tetrahydroisoquinolin-7-ol
Molecular Formula C17H19NO3
Molecular Weight 285.34
Isomeric smiles COC1=C(C=C2[C@@H](NCCC2=C1)CC3=CC=C(C=C3)O)O
InChI InChI=1S/C17H19NO3/c1-21-17-9-12-6-7-18-15(14(12)10-16(17)20)8-11-2-4-13(19)5-3-11/h2-5,9-10,15,18-20H,6-8H2,1H3/t15-/m0/s1
InChIKey LVVKXRQZSRUVPY-HNNXBMFYSA-N
External Database Links HERB2.0: HBIN043428   SymMap: SMIT03925   TCMSID: 1481   TCMSP: 1522   ChEMBL: CHEMBL446211  
Structural Information
nHA(Number of hydrogen bond acceptors) 4
nHD(Number of hydrogen bond donors) 3
nRot(Number of rotatable bonds) 3
nRing(Number of rings) 3
MaxRing(Number of atoms in the biggest ring) 10
nHet(Number of heteroatoms) 4

Stability
nRig(Number of rigid bonds) 17
Flexibility 0.176
Stereo Centers(Number of stereocenters) 1

Solubility
TPSA(Topological polar surface area) 61.72
logS(The logarithm of aqueous solubility value) -1.996
logP(The logarithm of the n-octanol/water distribution coefficient) 1.128
logD7.4(The logarithm of the n-octanol/water distribution coefficients at pH=7.4) 2.428

Pharmacokinetic Property
Quantitative Estimate of Drug-likeness 0.811
Synthetic accessibility score 2.732
Natural Product-likeness score 1.365
Lipinski Rule Accepted
GSK Rule Accepted
Golden Triangle Accepted

Absorption
Caco-2 Permeability -5.042
MDCK Permeability 1.46E-05
Pgp-substrate 0.948
HIA(human intestinal absorption) 0.017
F20%(20% Oral Bioavailability) 0.993
F30%(30% Oral Bioavailability) 0.98

Distribution
PPB(Plasma protein binding) 50.67%
VD(Volume Distribution) 2.492
BBB Penetration(Blood brain barrier penetration) 0.092
B3 Penetration(Blood brain barrier penetration) Non-Permeable
Fu(The fraction unbound in plasms) 34.77%

Metabolism
CYP1A2 inhibitor 0.299
CYP1A2 substrate 0.937
CYP2C19 inhibitor 0.355
CYP2C19 substrate 0.45
CYP2C9 inhibitor 0.037
CYP2C9 substrate 0.754
CYP2D6 inhibitor 0.692
CYP2D6 substrate 0.927
CYP3A4 inhibitor 0.04
CYP3A4 substrate 0.68

Excretion
CL(The clearance of a drug) 14.283
T1/2 0.867

Toxicology
NonBiodegradable Rule 0
Pfizer Rule Accepted
SR-MMP 0.724

Toxic Dose
FDAMDD(FDA Maximum (Recommended) Daily Dose) 0.973
IGC50 4.835
LC50FM 5.161
LC50DM 5.965

Reproductive Effects
NR-AR(Androgen receptor) 0.026
NR-AR-LBD(Androgen receptor) 0.051
NR-Aromatase 0.241
NR-ER(Estrogen receptor) 0.666
NR-ER-LBD(Estrogen receptor) 0.587

Allergy
Skin Sensitization Rule 4
Skin Sensitization 0.93

Acute Toxicity
Acute Toxicity Rule 0
Rat Oral Acute Toxicity 0.796

Organ Toxicity
hERG Blockers 0.368
H-HT(The human hepatotoxicity) 0.398
DILI(Drug-induced liver injury) 0.091

Primary Irritation
Eye Corrosion 0.004
Eye Irritation 0.014
Respiratory Toxicity 0.897

Mutagenic Effects
AMES Toxicity 0.205

Tumorigenic Effects
Carcinogencity 0.108
SR-ARE(Antioxidant Response Element) 0.612
SR-ATAD5(ATPase family AAA domain-containing protein 5) 0.737
SR-p53 0.62

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