Natural Product: NPC163099

Natural Product ID:  NPC163099
Common Name:   Agmatine
IUPAC Name:   2-(4-aminobutyl)guanidine
Synonyms:   Agmatine
Molecular Formula:   C5H14N4
Standard InCHIKey:  QYPPJABKJHAVHS-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C5H14N4/c6-3-1-2-4-9-5(7)8/h1-4,6H2,(H4,7,8,9)
Canonical SMILES:  NCCCCNC(=N)N
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
NPO32747 verbesina caracasana Species Asteraceae Eukaryota PMID[10576697]
NPO19602 Nephelium maingayi Species Sapindaceae Eukaryota UNPD*
NPO10029 Prunus dulcis Species Rosaceae Eukaryota UNPD*
NPO8884 Cuscuta reflexa Species Convolvulaceae Eukaryota UNPD*
NPO19542 Grindelia havardii Species Asteraceae Eukaryota UNPD*
NPO19474 Clavaria pyxidata Species Clavariaceae Eukaryota UNPD*
NPO19343 Centaurea glastifolia Species Asteraceae Eukaryota UNPD*
NPO19673 Galanthus nivalis Species Amaryllidaceae Eukaryota UNPD*
NPO17305 Oenanthe phellandrium Species Muscicapidae Eukaryota UNPD*
NPO15688 Astragalus oxyphysus Species Fabaceae Eukaryota UNPD*
NPO22602 Pityrogramma tartarea Species Pteridaceae Eukaryota UNPD*
NPO19214 Polyscias scutellaria Species Araliaceae Eukaryota UNPD*
NPO8918 Plantago depressa Species Plantaginaceae Eukaryota UNPD*
NPO19801 Euphorbia armena Species Euphorbiaceae Eukaryota UNPD*
NPO20977 Capparis masaikai Species Capparaceae Eukaryota UNPD*
NPO18559 Cucumaria okhotensis Species Cucumariidae Eukaryota UNPD*
NPO17557 Hydrodictyon reticulatum Species Hydrodictyaceae Eukaryota UNPD*
NPO21260 Nectandra pichurim Species Lauraceae Eukaryota UNPD*
NPO1797 Homo sapiens Species Hominidae Eukaryota saliva DOI[10.1007/s11306-012-0464-y]
NPO1797 Homo sapiens Species Hominidae Eukaryota urine PMID[16820162]
NPO1797 Homo sapiens Species Hominidae Eukaryota cerebrospinal fluid PMID[19296353]
NPO20338 Mus musculus Species Muridae Eukaryota PMID[19425150]
NPO24009 Claviceps purpurea Species Clavicipitaceae Eukaryota TCM_Taiwan*
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria PMID[21988831]
NPO14500 Pyrus pyraster Species Rosaceae Eukaryota UNPD*
NPO18991 Senecio candollei Species Asteraceae Eukaryota UNPD*

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT1879 Individual Protein Deoxyhypusine synthase Rattus norvegicus IC50 = 156000 nM 7636868
NPT613 Individual Protein Solute carrier family 22 member 1 Homo sapiens Inhibition = 2.1 % 18788725
NPT4887 Individual Protein Nischarin Rattus norvegicus IC50 = 36532 nM 19101144
NPT2 Others Unspecified Ki = 416700 nM 19101144
NPT2 Others Unspecified Ki = 31700 nM 19101144
NPT4888 Individual Protein Polyamine oxidase Zea mays Ki = 3000 nM 19591488
NPT163 Individual Protein Nuclear factor NF-kappa-B p105 subunit Homo sapiens Potency = 354.8 nM PubChem BioAssay data set
NPT791 Individual Protein Cruzipain Trypanosoma cruzi Potency = 39810.7 nM PubChem BioAssay data set
NPT792 Individual Protein Arachidonate 15-lipoxygenase Homo sapiens Potency = 12589.3 nM PubChem BioAssay data set
NPT150 Individual Protein Anthrax lethal factor Bacillus anthracis Potency = 2511.9 nM PubChem BioAssay data set
NPT4887 Individual Protein Nischarin Rattus norvegicus IC50 = 36532 nM 21159515
NPT2 Others Unspecified Ki = 416700 nM 21159515
NPT2 Others Unspecified Ki = 31700 nM 21159515
NPT5 Individual Protein Histone-lysine N-methyltransferase, H3 lysine-9 specific 3 Homo sapiens Potency 5623.4 nM PubChem BioAssay data set
NPT208 Individual Protein Cytochrome P450 1A2 Homo sapiens AC50 = 31622.78 nM PubChem BioAssay data set
NPT7 Individual Protein Thioredoxin reductase 1, cytoplasmic Rattus norvegicus Potency 562.3 nM PubChem BioAssay data set
NPT613 Individual Protein Solute carrier family 22 member 1 Homo sapiens Ki = 24000000 nM 12538837
NPT435 Individual Protein Solute carrier family 22 member 1 Rattus norvegicus Ki = 8600000 nM 12538837
NPT2 Others Unspecified Potency 6683.8 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency 8414.4 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency 14125.4 nM PubChem BioAssay data set
NPT582 Individual Protein Monoamine oxidase B Homo sapiens IC50 = 100000 nM Patent: CN102159208 B
NPT261 Individual Protein Monoamine oxidase A Homo sapiens IC50 = 100000 nM Patent: CN102159208 B

  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 NPC163099 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
0.9143 High Similarity NPC270319
0.8889 High Similarity NPC240230
0.7111 Intermediate Similarity NPC32934
0.6905 Remote Similarity NPC97568
0.6905 Remote Similarity NPC253366
0.6667 Remote Similarity NPC95589
0.6571 Remote Similarity NPC193536
0.6571 Remote Similarity NPC152949
0.6444 Remote Similarity NPC188989
0.6327 Remote Similarity NPC245768
0.6286 Remote Similarity NPC27675
0.6111 Remote Similarity NPC270175
0.6111 Remote Similarity NPC232311
0.6053 Remote Similarity NPC320889
0.6 Remote Similarity NPC230775
0.5938 Remote Similarity NPC309330
0.5938 Remote Similarity NPC28081
0.5918 Remote Similarity NPC230087
0.5882 Remote Similarity NPC39250
0.5854 Remote Similarity NPC74599
0.5814 Remote Similarity NPC323113
0.58 Remote Similarity NPC153280
0.58 Remote Similarity NPC202525
0.5789 Remote Similarity NPC21157
0.5652 Remote Similarity NPC223653
0.5625 Remote Similarity NPC314598
0.5625 Remote Similarity NPC182969
0.561 Remote Similarity NPC14922
0.56 Remote Similarity NPC110136

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC163099 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
0.9412 High Similarity NPD9059 Approved
0.8205 Intermediate Similarity NPD9458 Approved
0.725 Intermediate Similarity NPD9015 Phase 2
0.7111 Intermediate Similarity NPD395 Approved
0.7111 Intermediate Similarity NPD396 Approved
0.6667 Remote Similarity NPD401 Approved
0.6087 Remote Similarity NPD8793 Approved
0.6087 Remote Similarity NPD8792 Approved
0.6053 Remote Similarity NPD1156 Clinical (unspecified phase)
0.6 Remote Similarity NPD8555 Approved
0.6 Remote Similarity NPD8554 Approved
0.5938 Remote Similarity NPD8560 Clinical (unspecified phase)
0.5897 Remote Similarity NPD2276 Clinical (unspecified phase)
0.5833 Remote Similarity NPD9063 Approved
0.5833 Remote Similarity NPD9064 Approved
0.5818 Remote Similarity NPD1155 Discontinued
0.58 Remote Similarity NPD8815 Suspended
0.5676 Remote Similarity NPD9465 Approved

Structure

External Identifiers

PubChem CID   199
ChEMBL   CHEMBL58343
ZINC  

Physicochemical Properties

Molecular Weight:  130.12
ALogP:  -1.7722
MLogP:  1.57
XLogP:  -0.243
# Rotatable Bonds:  7
Polar Surface Area:  87.92
# H-Bond Aceptor:  4
# H-Bond Donor:  4
# Rings:  0
# Heavy Atoms:  9

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