Ingredient Details :2-[(4E,12E)-1,7-dihydroxytetradeca-4,12-dien-8,10-diyn-6-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol


TCMI-ID: TCMI11549


Physicochemical Property
Ingredient Name 2-[(4E,12E)-1,7-dihydroxytetradeca-4,12-dien-8,10-diyn-6-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
Pubchem CID 6369123
Iupac name 2-[(4E,12E)-1,7-dihydroxytetradeca-4,12-dien-8,10-diyn-6-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
Molecular Formula C20H28O8
Molecular Weight 396.4
Isomeric smiles C/C=C/C#CC#CC(C(/C=C/CCCO)OC1C(C(C(C(O1)CO)O)O)O)O
InChI InChI=1S/C20H28O8/c1-2-3-4-5-7-10-14(23)15(11-8-6-9-12-21)27-20-19(26)18(25)17(24)16(13-22)28-20/h2-3,8,11,14-26H,6,9,12-13H2,1H3/b3-2+,11-8+
InChIKey MMMUDYVKKPDZHS-FWTOVJONSA-N
External Database Links TCMSID: 5885  
Structural Information
nHA(Number of hydrogen bond acceptors) 8
nHD(Number of hydrogen bond donors) 6
nRot(Number of rotatable bonds) 8
nRing(Number of rings) 1
MaxRing(Number of atoms in the biggest ring) 6
nHet(Number of heteroatoms) 8

Stability
nRig(Number of rigid bonds) 10
Flexibility 0.8
Stereo Centers(Number of stereocenters) 7

Solubility
TPSA(Topological polar surface area) 139.84
logS(The logarithm of aqueous solubility value) -1.777
logP(The logarithm of the n-octanol/water distribution coefficient) -0.319
logD7.4(The logarithm of the n-octanol/water distribution coefficients at pH=7.4) 0.834

Pharmacokinetic Property
Quantitative Estimate of Drug-likeness 0.165
Synthetic accessibility score 5.061
Natural Product-likeness score 2.914
Lipinski Rule Accepted
GSK Rule Accepted
Golden Triangle Accepted

Absorption
Caco-2 Permeability -5.365
MDCK Permeability 0.000770314
Pgp-substrate 0.148
HIA(human intestinal absorption) 0.988
F20%(20% Oral Bioavailability) 0.403
F30%(30% Oral Bioavailability) 1

Distribution
PPB(Plasma protein binding) 99.89%
VD(Volume Distribution) 0.558
BBB Penetration(Blood brain barrier penetration) 0.048
B3 Penetration(Blood brain barrier penetration) Non-Permeable
Fu(The fraction unbound in plasms) 2.82%

Metabolism
CYP1A2 inhibitor 0.024
CYP1A2 substrate 0.025
CYP2C19 inhibitor 0.287
CYP2C19 substrate 0.572
CYP2C9 inhibitor 0.193
CYP2C9 substrate 0.982
CYP2D6 inhibitor 0.005
CYP2D6 substrate 0.273
CYP3A4 inhibitor 0.113
CYP3A4 substrate 0.025

Excretion
CL(The clearance of a drug) 1.25
T1/2 0.474

Toxicology
NonBiodegradable Rule 1
Pfizer Rule Accepted
SR-MMP 0.034

Toxic Dose
FDAMDD(FDA Maximum (Recommended) Daily Dose) 0.021
IGC50 4.599
LC50FM 6.802
LC50DM 6.511

Reproductive Effects
NR-AR(Androgen receptor) 0.001
NR-AR-LBD(Androgen receptor) 0.055
NR-Aromatase 0.918
NR-ER(Estrogen receptor) 0.08
NR-ER-LBD(Estrogen receptor) 0.126

Allergy
Skin Sensitization Rule 1
Skin Sensitization 0.764

Acute Toxicity
Acute Toxicity Rule 2
Rat Oral Acute Toxicity 0.277

Organ Toxicity
hERG Blockers 0.001
H-HT(The human hepatotoxicity) 0.341
DILI(Drug-induced liver injury) 0.978

Primary Irritation
Eye Corrosion 0.003
Eye Irritation 0.009
Respiratory Toxicity 0.849

Mutagenic Effects
AMES Toxicity 0.768

Tumorigenic Effects
Carcinogencity 0.46
SR-ARE(Antioxidant Response Element) 0.924
SR-ATAD5(ATPase family AAA domain-containing protein 5) 0.909
SR-p53 0.885

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