Natural Product: NPC2088

Natural Product ID:  NPC2088
Common Name:   Allicin
IUPAC Name:   3-prop-2-enylsulfinylsulfanylprop-1-ene
Synonyms:   Allicin; Diallyl Thiosulfinate
Molecular Formula:   C6H10OS2
Standard InCHIKey:  JDLKFOPOAOFWQN-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C6H10OS2/c1-3-5-8-9(7)6-4-2/h3-4H,1-2,5-6H2
Canonical SMILES:  C=CCSS(=O)CC=C
First Find Year:  
Max Developmental Stage:  
Synthetic Gene Cluster:   ;

  Species Source

Organism ID Organism Name Taxonomy Level Family SuperKingdom Isolation Part Collection Location Collection Time Reference
NPO28923 Allium fistulosum Species Amaryllidaceae Eukaryota TCM_Taiwan*
NPO28923 Allium fistulosum Species Amaryllidaceae Eukaryota HerDing*
NPO7103 Allium sativum Species Amaryllidaceae Eukaryota TCM_Taiwan*
NPO7103 Allium sativum Species Amaryllidaceae Eukaryota HerDing*
NPO8321 Allium chinense Species Amaryllidaceae Eukaryota TM-MC*
NPO4520 Allium macrostemon Species Amaryllidaceae Eukaryota TM-MC*
NPO7103 Allium sativum Species Amaryllidaceae Eukaryota TM-MC*
NPO667 Bulbus allii fistulosi NA NA NA TCMID*
NPO28923 Allium fistulosum Species Amaryllidaceae Eukaryota TCMID*
NPO7103 Allium sativum Species Amaryllidaceae Eukaryota TCMID*

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT463 Individual Protein HMG-CoA reductase Rattus norvegicus Ratio = 2.07 15454225
NPT464 Cell Line Daudi Homo sapiens IC50 = 35300 nM 18467007
NPT165 Cell Line HeLa Homo sapiens IC50 = 103500 nM 18467007
NPT465 Cell Line NCI-N87 Homo sapiens IC50 = 16800 nM 18467007
NPT116 Cell Line HL-60 Homo sapiens IC50 = 5500 nM 18467007
NPT466 Cell Line U-937 Homo sapiens IC50 = 19700 nM 18467007
NPT139 Cell Line HT-29 Homo sapiens IC50 = 83800 nM 18467007
NPT2 Others Unspecified IC50 = 20 nM 18467007
NPT29 Organism Rattus norvegicus Rattus norvegicus Activity = 2.15 mg/dl 18595719
NPT29 Organism Rattus norvegicus Rattus norvegicus Activity = 42.69 mg/dl 18595719
NPT29 Organism Rattus norvegicus Rattus norvegicus Activity = 20.34 mg/dl 18595719
NPT29 Organism Rattus norvegicus Rattus norvegicus Activity = 36.86 mg/dl 18595719
NPT467 Individual Protein Transient receptor potential cation channel subfamily A member 1 Mus musculus EC50 = 1320 nM 20356305
NPT346 Individual Protein Transient receptor potential cation channel subfamily A member 1 Homo sapiens EC50 = 1910 nM 20356305
NPT468 Individual Protein Vanilloid receptor Rattus norvegicus EC50 = 51220 nM 20356305
NPT214 Individual Protein Cathepsin B Homo sapiens Ki = 8600 nM 20692829
NPT469 Individual Protein Cathepsin L Homo sapiens Ki = 9300 nM 20692829
NPT2 Others Unspecified Ki = 1040 nM 20692829
NPT470 Individual Protein Rhodesain Trypanosoma brucei rhodesiense Ki = 5310 nM 20692829
NPT6 Organism Plasmodium falciparum Plasmodium falciparum IC50 = 5210 nM 20692829
NPT471 Organism Trypanosoma brucei brucei Trypanosoma brucei brucei IC50 = 13800 nM 20692829
NPT472 Individual Protein Vanilloid receptor Homo sapiens Activity = 0.099 nM 16408004
NPT346 Individual Protein Transient receptor potential cation channel subfamily A member 1 Homo sapiens Activity = 0.01 nM 16408004
NPT87 Organism Aspergillus fumigatus Aspergillus fumigatus MFC = 7.5 ug/ml 19949059
NPT87 Organism Aspergillus fumigatus Aspergillus fumigatus MFC = 15 ug/ml 19949059
NPT87 Organism Aspergillus fumigatus Aspergillus fumigatus MIC = 30 ug/ml 19949059
NPT473 Protein Complex Amiloride-sensitive sodium channel, ENaC Homo sapiens Inhibition = 77 % 22668601
NPT474 Organism Plasmodium berghei Plasmodium berghei IC50 = 6800 nM 22122518
NPT474 Organism Plasmodium berghei Plasmodium berghei IC50 = 39400 nM 22122518
NPT474 Organism Plasmodium berghei Plasmodium berghei Inhibition = 37 % 22122518
NPT475 Organism Plasmodium yoelii Plasmodium yoelii IC50 = 40000 nM 22122518
NPT450 Organism Meloidogyne incognita Meloidogyne incognita Activity = 50 % 12147760
NPT144 Individual Protein Telomerase reverse transcriptase Homo sapiens IC50 = 500 nM 10.1039/C0MD00241K

  Similar Natural Products in NPASS

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

●  The left chart: Distribution of similarity level between NPC2088 and all remaining natural products in the NPASS database.
●  The right table: Most similar natural products (Tc>=0.56 or Top200).

Similarity Score Similarity Level Natural Product ID
0.96 High Similarity NPC46648
0.8571 High Similarity NPC168614
0.8571 High Similarity NPC204251
0.8333 Intermediate Similarity NPC220140
0.8333 Intermediate Similarity NPC184203
0.8 Intermediate Similarity NPC142438
0.72 Intermediate Similarity NPC476548
0.72 Intermediate Similarity NPC326758
0.7037 Intermediate Similarity NPC156018
0.68 Remote Similarity NPC476549
0.6765 Remote Similarity NPC277288
0.6667 Remote Similarity NPC476550
0.6216 Remote Similarity NPC205586

  Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

●  The left chart: Distribution of similarity level between NPC2088 and all drugs/candidates.
●  The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

Similarity Score Similarity Level Drug ID Developmental Stage
0.5862 Remote Similarity NPD8550 Phase 3
0.5862 Remote Similarity NPD8552 Clinical (unspecified phase)
0.5714 Remote Similarity NPD8229 Phase 3
0.5667 Remote Similarity NPD8227 Approved
0.5667 Remote Similarity NPD8230 Phase 3

Structure

External Identifiers

PubChem CID   65036
ChEMBL   CHEMBL359965
ZINC  

Physicochemical Properties

Molecular Weight:  162.02
ALogP:  1.5076
MLogP:  1.79
XLogP:  0.237
# Rotatable Bonds:  5
Polar Surface Area:  61.58
# H-Bond Aceptor:  1
# H-Bond Donor:  0
# Rings:  0
# Heavy Atoms:  9

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