Natural Product: NPC44193
Natural Product ID:   | NPC44193 |
Common Name*:   | Isobungeanool |
IUPAC Name:   | (2E,4E,8Z,11E)-N-(2-hydroxy-2-methylpropyl)tetradeca-2,4,8,11-tetraenamide |
Synonyms:   | |
Standard InCHIKey:   | HSFPMLIZJAVYHM-NPNWTSAVSA-N |
Standard InCHI:   | InChI=1S/C18H29NO2/c1-4-5-6-7-8-9-10-11-12-13-14-15-17(20)19-16-18(2,3)21/h5-6,8-9,12-15,21H,4,7,10-11,16H2,1-3H3,(H,19,20)/b6-5+,9-8-,13-12+,15-14+ |
SMILES:   | CC/C=C/C/C=CCC/C=C/C=C/C(=NCC(C)(C)O)O
|
Synthetic Gene Cluster:   |
n.a. |
ChEMBL Identifier:   |
CHEMBL505802 |
PubChem CID:   |
14135320 |
Chemical Classification**:   |
-
CHEMONTID:0000000 [Organic compounds]
-
[CHEMONTID:0000012] Lipids and lipid-like molecules
-
[CHEMONTID:0003909] Fatty Acyls
[CHEMONTID:0000331] Fatty amides[CHEMONTID:0001096] N-acyl amines
|
*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.
  Species Source
Organism ID |
Organism Name |
Taxonomy Level |
Family |
SuperKingdom |
Isolation Part |
Collection Location |
Collection Time |
Reference |
NPO5852 |
Litsea glutinosa |
Species |
Lauraceae |
Eukaryota |
n.a. |
stem |
n.a. |
DOI[10.1016/S0031-9422(00)88469-1] |
NPO5852 |
Litsea glutinosa |
Species |
Lauraceae |
Eukaryota |
n.a. |
leaf |
n.a. |
DOI[10.1016/S0031-9422(00)88469-1] |
NPO21390 |
Zanthoxylum integrifoliolum |
Species |
Rutaceae |
Eukaryota |
fruit |
Lanyu Island, Taitung County, Taiwan |
n.a. |
PMID[10395498] |
NPO21390 |
Zanthoxylum integrifoliolum |
Species |
Rutaceae |
Eukaryota |
n.a. |
n.a. |
n.a. |
PMID[17822293] |
NPO5315 |
Zanthoxylum bungeanum |
Species |
Rutaceae |
Eukaryota |
n.a. |
n.a. |
n.a. |
PMID[24175626] |
NPO12970 |
Aspergillus fischeri |
Species |
Aspergillaceae |
Eukaryota |
n.a. |
n.a. |
n.a. |
PMID[31920082] |
NPO10128 |
Aplysia punctata |
Species |
Aplysiidae |
Eukaryota |
n.a. |
n.a. |
n.a. |
PMID[9213585] |
NPO5315 |
Zanthoxylum bungeanum |
Species |
Rutaceae |
Eukaryota |
n.a. |
n.a. |
n.a. |
Database[HerDing] |
NPO4340 |
Peucedanum praeruptorum |
Species |
Apiaceae |
Eukaryota |
n.a. |
n.a. |
n.a. |
Database[HerDing] |
NPO1070 |
Matricaria suffruticosa |
Species |
Asteraceae |
Eukaryota |
n.a. |
n.a. |
n.a. |
Database[HerDing] |
NPO2892 |
Wikstroemia chamaedaphne |
Species |
Thymelaeaceae |
Eukaryota |
n.a. |
n.a. |
n.a. |
Database[HerDing] |
NPO8471 |
Angelica taiwaniana |
Species |
Apiaceae |
Eukaryota |
n.a. |
n.a. |
n.a. |
Database[HerDing] |
NPO8642 |
Lithospermum officinale |
Species |
Boraginaceae |
Eukaryota |
n.a. |
n.a. |
n.a. |
Database[HerDing] |
NPO4120 |
Ulmus americana |
Species |
Ulmaceae |
Eukaryota |
n.a. |
n.a. |
n.a. |
Database[HerDing] |
NPO5852 |
Litsea glutinosa |
Species |
Lauraceae |
Eukaryota |
n.a. |
n.a. |
n.a. |
Database[HerDing] |
NPO9087 |
Sarcococca vagans |
Species |
Buxaceae |
Eukaryota |
n.a. |
n.a. |
n.a. |
Database[HerDing] |
NPO6320 |
Echinosophora koreensis |
Species |
Fabaceae |
Eukaryota |
n.a. |
n.a. |
n.a. |
Database[HerDing] |
NPO2892 |
Wikstroemia chamaedaphne |
Species |
Thymelaeaceae |
Eukaryota |
n.a. |
n.a. |
n.a. |
Database[TCMID] |
NPO21390 |
Zanthoxylum integrifoliolum |
Species |
Rutaceae |
Eukaryota |
n.a. |
n.a. |
n.a. |
Database[TCMID] |
NPO4120 |
Ulmus americana |
Species |
Ulmaceae |
Eukaryota |
n.a. |
n.a. |
n.a. |
Database[TCMID] |
NPO4340 |
Peucedanum praeruptorum |
Species |
Apiaceae |
Eukaryota |
n.a. |
n.a. |
n.a. |
Database[TCMID] |
NPO9087 |
Sarcococca vagans |
Species |
Buxaceae |
Eukaryota |
n.a. |
n.a. |
n.a. |
Database[TCMID] |
NPO8471 |
Angelica taiwaniana |
Species |
Apiaceae |
Eukaryota |
n.a. |
n.a. |
n.a. |
Database[TCMID] |
NPO6320 |
Echinosophora koreensis |
Species |
Fabaceae |
Eukaryota |
n.a. |
n.a. |
n.a. |
Database[TCMID] |
NPO1070 |
Matricaria suffruticosa |
Species |
Asteraceae |
Eukaryota |
n.a. |
n.a. |
n.a. |
Database[TCMID] |
NPO8642 |
Lithospermum officinale |
Species |
Boraginaceae |
Eukaryota |
n.a. |
n.a. |
n.a. |
Database[TCMID] |
NPO5852 |
Litsea glutinosa |
Species |
Lauraceae |
Eukaryota |
n.a. |
n.a. |
n.a. |
Database[TCMID] |
NPO5315 |
Zanthoxylum bungeanum |
Species |
Rutaceae |
Eukaryota |
n.a. |
n.a. |
n.a. |
Database[TCMID] |
NPO26898 |
Jacobaea vulgaris |
Species |
Asteraceae |
Eukaryota |
n.a. |
n.a. |
n.a. |
Database[TCMID] |
NPO5315 |
Zanthoxylum bungeanum |
Species |
Rutaceae |
Eukaryota |
n.a. |
n.a. |
n.a. |
Database[TCM_Taiwan] |
NPO4340 |
Peucedanum praeruptorum |
Species |
Apiaceae |
Eukaryota |
n.a. |
n.a. |
n.a. |
Database[TCM_Taiwan] |
NPO9087 |
Sarcococca vagans |
Species |
Buxaceae |
Eukaryota |
n.a. |
n.a. |
n.a. |
Database[TCM_Taiwan] |
NPO8642 |
Lithospermum officinale |
Species |
Boraginaceae |
Eukaryota |
n.a. |
n.a. |
n.a. |
Database[TCM_Taiwan] |
NPO4340 |
Peucedanum praeruptorum |
Species |
Apiaceae |
Eukaryota |
n.a. |
n.a. |
n.a. |
Database[TM-MC] |
NPO5315 |
Zanthoxylum bungeanum |
Species |
Rutaceae |
Eukaryota |
n.a. |
n.a. |
n.a. |
Database[TM-MC] |
NPO1070 |
Matricaria suffruticosa |
Species |
Asteraceae |
Eukaryota |
n.a. |
n.a. |
n.a. |
Database[UNPD] |
NPO8253 |
Alexandrium hiranoi |
Species |
Gonyaulacaceae |
Eukaryota |
n.a. |
n.a. |
n.a. |
Database[UNPD] |
NPO16266 |
Didymium bahiense |
Species |
Didymiaceae |
Eukaryota |
n.a. |
n.a. |
n.a. |
Database[UNPD] |
NPO9476 |
Metapenaeus bennettae |
Species |
Penaeidae |
Eukaryota |
n.a. |
n.a. |
n.a. |
Database[UNPD] |
NPO777 |
Kielmeyera coriacea |
Species |
Calophyllaceae |
Eukaryota |
n.a. |
n.a. |
n.a. |
Database[UNPD] |
NPO20059.1 |
Lactobacillus delbrueckii subsp. bulgaricus |
Subspecies |
Lactobacillaceae |
Bacteria |
n.a. |
n.a. |
n.a. |
Database[UNPD] |
NPO14793 |
Erica glauca |
Species |
Ericaceae |
Eukaryota |
n.a. |
n.a. |
n.a. |
Database[UNPD] |
NPO21390 |
Zanthoxylum integrifoliolum |
Species |
Rutaceae |
Eukaryota |
n.a. |
n.a. |
n.a. |
Database[UNPD] |
NPO2199 |
Tecoma pentaphylla |
Species |
Bignoniaceae |
Eukaryota |
n.a. |
n.a. |
n.a. |
Database[UNPD] |
NPO10128 |
Aplysia punctata |
Species |
Aplysiidae |
Eukaryota |
n.a. |
n.a. |
n.a. |
Database[UNPD] |
NPO9590 |
Xanthoria aureola |
Species |
Teloschistaceae |
Eukaryota |
n.a. |
n.a. |
n.a. |
Database[UNPD] |
NPO7028 |
Sida veronicaefolia |
Species |
Malvaceae |
Eukaryota |
n.a. |
n.a. |
n.a. |
Database[UNPD] |
NPO9995 |
Cynara humilis |
Species |
Asteraceae |
Eukaryota |
n.a. |
n.a. |
n.a. |
Database[UNPD] |
NPO3341 |
Leishmania major |
Species |
Trypanosomatidae |
Eukaryota |
n.a. |
n.a. |
n.a. |
Database[UNPD] |
NPO10264 |
Platonia insignis |
Species |
Clusiaceae |
Eukaryota |
n.a. |
n.a. |
n.a. |
Database[UNPD] |
NPO1682 |
Rhytidoponera metallica |
Species |
Formicidae |
Eukaryota |
n.a. |
n.a. |
n.a. |
Database[UNPD] |
NPO5604 |
Chelonia japonica |
Species |
Cheloniidae |
Eukaryota |
n.a. |
n.a. |
n.a. |
Database[UNPD] |
NPO6320 |
Echinosophora koreensis |
Species |
Fabaceae |
Eukaryota |
n.a. |
n.a. |
n.a. |
Database[UNPD] |
NPO13438 |
Centaurea calcitrapa |
Species |
Asteraceae |
Eukaryota |
n.a. |
n.a. |
n.a. |
Database[UNPD] |
NPO7650 |
Salvia munzii |
Species |
Lamiaceae |
Eukaryota |
n.a. |
n.a. |
n.a. |
Database[UNPD] |
NPO6801 |
Bellium bellidioides |
Species |
Asteraceae |
Eukaryota |
n.a. |
n.a. |
n.a. |
Database[UNPD] |
NPO2015 |
Udotea petiolata |
Species |
Udoteaceae |
Eukaryota |
n.a. |
n.a. |
n.a. |
Database[UNPD] |
NPO8642 |
Lithospermum officinale |
Species |
Boraginaceae |
Eukaryota |
n.a. |
n.a. |
n.a. |
Database[UNPD] |
NPO12970 |
Aspergillus fischeri |
Species |
Aspergillaceae |
Eukaryota |
n.a. |
n.a. |
n.a. |
Database[UNPD] |
NPO4523 |
Reaumuria hirtella |
Species |
Tamaricaceae |
Eukaryota |
n.a. |
n.a. |
n.a. |
Database[UNPD] |
NPO2999 |
Coprinellus flocculosus |
Species |
Psathyrellaceae |
Eukaryota |
n.a. |
n.a. |
n.a. |
Database[UNPD] |
NPO7841 |
Solanum transcaucasicum |
Species |
Solanaceae |
Eukaryota |
n.a. |
n.a. |
n.a. |
Database[UNPD] |
NPO9733 |
Spongia bilamellata |
Species |
Spongiidae |
Eukaryota |
n.a. |
n.a. |
n.a. |
Database[UNPD] |
NPO8022 |
Consolida hohenackeri |
Species |
Ranunculaceae |
Eukaryota |
n.a. |
n.a. |
n.a. |
Database[UNPD] |
NPO24083.1 |
Melanelixia fuliginosa subsp. glabratula |
Subspecies |
Parmeliaceae |
Eukaryota |
n.a. |
n.a. |
n.a. |
Database[UNPD] |
NPO8471 |
Angelica taiwaniana |
Species |
Apiaceae |
Eukaryota |
n.a. |
n.a. |
n.a. |
Database[UNPD] |
NPO4340 |
Peucedanum praeruptorum |
Species |
Apiaceae |
Eukaryota |
n.a. |
n.a. |
n.a. |
Database[UNPD] |
NPO15558 |
Leucas neufliseana |
Species |
Lamiaceae |
Eukaryota |
n.a. |
n.a. |
n.a. |
Database[UNPD] |
NPO26898 |
Jacobaea vulgaris |
Species |
Asteraceae |
Eukaryota |
n.a. |
n.a. |
n.a. |
Database[UNPD] |
NPO6556 |
Garcinia intermedia |
Species |
Clusiaceae |
Eukaryota |
n.a. |
n.a. |
n.a. |
Database[UNPD] |
NPO6894 |
Elegia deusta |
Species |
Restionaceae |
Eukaryota |
n.a. |
n.a. |
n.a. |
Database[UNPD] |
NPO5852 |
Litsea glutinosa |
Species |
Lauraceae |
Eukaryota |
n.a. |
n.a. |
n.a. |
Database[UNPD] |
NPO1467 |
Wedelia prostrata |
Species |
Asteraceae |
Eukaryota |
n.a. |
n.a. |
n.a. |
Database[UNPD] |
NPO7847 |
Senecio densiflorus |
Species |
Asteraceae |
Eukaryota |
n.a. |
n.a. |
n.a. |
Database[UNPD] |
NPO4120 |
Ulmus americana |
Species |
Ulmaceae |
Eukaryota |
n.a. |
n.a. |
n.a. |
Database[UNPD] |
NPO5315 |
Zanthoxylum bungeanum |
Species |
Rutaceae |
Eukaryota |
n.a. |
n.a. |
n.a. |
Database[UNPD] |
NPO9087 |
Sarcococca vagans |
Species |
Buxaceae |
Eukaryota |
n.a. |
n.a. |
n.a. |
Database[UNPD] |
NPO2892 |
Wikstroemia chamaedaphne |
Species |
Thymelaeaceae |
Eukaryota |
n.a. |
n.a. |
n.a. |
Database[UNPD] |
NPO9221 |
Trachelospermum lucidum |
Species |
Apocynaceae |
Eukaryota |
n.a. |
n.a. |
n.a. |
Database[UNPD] |
NPO6378 |
Wilcoxia viperina |
n.a. |
n.a. |
n.a. |
n.a. |
n.a. |
n.a. |
Database[UNPD] |
NPO4895 |
Coleus esquirolii |
Species |
Lamiaceae |
Eukaryota |
n.a. |
n.a. |
n.a. |
Database[UNPD] |
☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].
  NP Quantity Composition/Concentration
Organism ID |
NP ID |
Organism Material Preparation |
Organism Part |
NP Quantity (Standard) |
NP Quantity (Minimum) |
NP Quantity (Maximum) |
Quantity Unit |
Reference |
☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].
  Biological Activity
Activity Type |
# Activity |
IC50 |
2 |
Others |
11 |
Activity Type |
# Activity |
Individual Protein |
4 |
NON-MOLECULAR |
8 |
Others |
1 |
Target ID |
Target Type |
Target Name |
Target Organism |
Activity Type |
Activity Relation |
Value |
Unit |
Reference |
NPT1287 |
Individual Protein |
Cannabinoid CB2 receptor |
Homo sapiens |
Inhibition |
= |
62.0 |
% |
PMID[464481] |
NPT1287 |
Individual Protein |
Cannabinoid CB2 receptor |
Homo sapiens |
IC50 |
= |
9100.0 |
nM |
PMID[464481] |
NPT232 |
Individual Protein |
Cannabinoid CB1 receptor |
Homo sapiens |
Inhibition |
= |
45.0 |
% |
PMID[464481] |
NPT232 |
Individual Protein |
Cannabinoid CB1 receptor |
Homo sapiens |
IC50 |
= |
2400.0 |
nM |
PMID[464481] |
NPT20529 |
NON-MOLECULAR |
NON-PROTEIN TARGET |
n.a. |
Activity |
= |
89.2 |
% |
PMID[464480] |
NPT20529 |
NON-MOLECULAR |
NON-PROTEIN TARGET |
n.a. |
Activity |
= |
0.0 |
% |
PMID[464480] |
NPT20529 |
NON-MOLECULAR |
NON-PROTEIN TARGET |
n.a. |
Activity |
= |
4.0 |
% |
PMID[464480] |
NPT20529 |
NON-MOLECULAR |
NON-PROTEIN TARGET |
n.a. |
Activity |
= |
27.8 |
% |
PMID[464480] |
NPT20529 |
NON-MOLECULAR |
NON-PROTEIN TARGET |
n.a. |
Activity |
= |
46.2 |
% |
PMID[464480] |
NPT20529 |
NON-MOLECULAR |
NON-PROTEIN TARGET |
n.a. |
Activity |
= |
38.4 |
% |
PMID[464480] |
NPT2 |
Others |
Unspecified |
|
Ratio IC50 |
= |
0.26 |
n.a. |
PMID[464481] |
☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.
  Chemically structural similarity: I. Similar Active Natural Products in NPASS
Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available 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 ![](images/questionmark.png)
●  The left chart: Distribution of similarity level between NPC44193 and all remaining natural products in the NPASS database.
●  The right table: Most similar natural products (Tc>=0.56 or Top200).
range |
Tanimoto Coefficient |
0-0.1 | 38 |
0.1-0.2 | 8855 |
0.2-0.3 | 26023 |
0.3-0.4 | 6370 |
0.4-0.5 | 1104 |
0.5-0.6 | 203 |
0.6-0.7 | 42 |
0.7-0.8 | 22 |
0.8-0.85 | 22 |
0.85-0.9 | 11 |
0.9-0.95 | 1 |
0.95-1 | 6 |
  Chemically structural similarity: II. Similar Clinical/Approved Drugs
Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.
●  The left chart: Distribution of similarity level between NPC44193 and all drugs/candidates.
●  The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).
range |
Tanimoto Coefficient |
0-0.1 | 54 |
0.1-0.2 | 1710 |
0.2-0.3 | 6035 |
0.3-0.4 | 1233 |
0.4-0.5 | 106 |
0.5-0.6 | 11 |
0.6-0.7 | 1 |
0.7-0.8 | 0 |
0.8-0.85 | 0 |
0.85-0.9 | 0 |
0.9-0.95 | 0 |
0.95-1 | 0 |
Similarity Score |
Similarity Level |
Drug ID |
Developmental Stage |
0.6727 |
Remote Similarity |
NPD860 |
Phase 2 |
0.6102 |
Remote Similarity |
NPD4220 |
Pre-registration |
0.5882 |
Remote Similarity |
NPD3210 |
Clinical (unspecified phase) |
0.5758
|
Remote Similarity |
NPD9368 |
Phase 2 |