Structure

Physi-Chem Properties

Molecular Weight:  303.26
Volume:  361.081
LogP:  3.767
LogD:  3.681
LogS:  -3.479
# Rotatable Bonds:  13
TPSA:  29.1
# H-Bond Aceptor:  2
# H-Bond Donor:  1
# Rings:  0
# Heavy Atoms:  2

MedChem Properties

QED Drug-Likeness Score:  0.294
Synthetic Accessibility Score:  2.983
Fsp3:  0.55
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.563
MDCK Permeability:  0.00010206689330516383
Pgp-inhibitor:  0.0
Pgp-substrate:  0.0
Human Intestinal Absorption (HIA):  0.013
20% Bioavailability (F20%):  0.712
30% Bioavailability (F30%):  0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.51
Plasma Protein Binding (PPB):  97.48503112792969%
Volume Distribution (VD):  0.838
Pgp-substrate:  2.6569881439208984%

ADMET: Metabolism

CYP1A2-inhibitor:  0.802
CYP1A2-substrate:  0.424
CYP2C19-inhibitor:  0.862
CYP2C19-substrate:  0.72
CYP2C9-inhibitor:  0.681
CYP2C9-substrate:  0.928
CYP2D6-inhibitor:  0.598
CYP2D6-substrate:  0.856
CYP3A4-inhibitor:  0.882
CYP3A4-substrate:  0.185

ADMET: Excretion

Clearance (CL):  8.539
Half-life (T1/2):  0.913

ADMET: Toxicity

hERG Blockers:  0.059
Human Hepatotoxicity (H-HT):  0.17
Drug-inuced Liver Injury (DILI):  0.027
AMES Toxicity:  0.117
Rat Oral Acute Toxicity:  0.023
Maximum Recommended Daily Dose:  0.334
Skin Sensitization:  0.958
Carcinogencity:  0.541
Eye Corrosion:  0.016
Eye Irritation:  0.308
Respiratory Toxicity:  0.933

Download Data

Data Type Select
General Info & Identifiers & Properties  
Structure MOL file  
Source Organisms  
Biological Activities  
Similar NPs/Drugs  

  Natural Product: NPC297020

Natural Product ID:  NPC297020
Common Name*:   Hexadeca-2E,9Z,12Z,14E-Tetraenoic Acid Isobutylamide
IUPAC Name:   (2E,9Z,12Z,14E)-N-(2-methylpropyl)hexadeca-2,9,12,14-tetraenamide
Synonyms:  
Standard InCHIKey:  TUOUAZDJHYHIRF-XJOGYUGASA-N
Standard InCHI:  InChI=1S/C20H33NO/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-20(22)21-18-19(2)3/h4-7,9-10,16-17,19H,8,11-15,18H2,1-3H3,(H,21,22)/b5-4+,7-6-,10-9-,17-16+
SMILES:  C/C=C/C=CC/C=CCCCCC/C=C/C(=NCC(C)C)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL572337
PubChem CID:   44140283
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
NPO14484 Echinacea purpurea Species Asteraceae Eukaryota root n.a. n.a. PMID[15921428]
NPO14484 Echinacea purpurea Species Asteraceae Eukaryota flowers n.a. n.a. PMID[19374389]
NPO14484 Echinacea purpurea Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO14484 Echinacea purpurea Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14484 Echinacea purpurea Species Asteraceae 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

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT99 Individual Protein Peroxisome proliferator-activated receptor gamma Homo sapiens FC = 10.0 n.a. PMID[544018]

☑ 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

●  The left chart: Distribution of similarity level between NPC297020 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
0.9808 High Similarity NPC306420
0.9808 High Similarity NPC104138
0.9808 High Similarity NPC261158
0.9808 High Similarity NPC24216
0.9615 High Similarity NPC273023
0.9608 High Similarity NPC303672
0.9412 High Similarity NPC195986
0.9245 High Similarity NPC471992
0.9216 High Similarity NPC267340
0.9216 High Similarity NPC304223
0.9216 High Similarity NPC54542
0.9216 High Similarity NPC145032
0.9216 High Similarity NPC243539
0.902 High Similarity NPC267692
0.902 High Similarity NPC307435
0.8929 High Similarity NPC312826
0.8889 High Similarity NPC471991
0.8868 High Similarity NPC119655
0.8704 High Similarity NPC305288
0.8704 High Similarity NPC163912
0.8704 High Similarity NPC167759
0.8704 High Similarity NPC56028
0.8448 Intermediate Similarity NPC6795
0.8393 Intermediate Similarity NPC477049
0.8364 Intermediate Similarity NPC132669
0.8364 Intermediate Similarity NPC13011
0.8364 Intermediate Similarity NPC184014
0.8364 Intermediate Similarity NPC124382
0.8364 Intermediate Similarity NPC246519
0.8364 Intermediate Similarity NPC14234
0.8364 Intermediate Similarity NPC44193
0.8364 Intermediate Similarity NPC123669
0.8364 Intermediate Similarity NPC269800
0.8197 Intermediate Similarity NPC477525
0.8065 Intermediate Similarity NPC187315
0.7833 Intermediate Similarity NPC130807
0.7759 Intermediate Similarity NPC4881
0.7627 Intermediate Similarity NPC245650
0.7593 Intermediate Similarity NPC91044
0.7581 Intermediate Similarity NPC471023
0.7541 Intermediate Similarity NPC309877
0.75 Intermediate Similarity NPC315141
0.75 Intermediate Similarity NPC129995
0.7419 Intermediate Similarity NPC29468
0.7419 Intermediate Similarity NPC324077
0.7188 Intermediate Similarity NPC253468
0.7188 Intermediate Similarity NPC235311
0.7101 Intermediate Similarity NPC314678
0.7097 Intermediate Similarity NPC74617
0.7097 Intermediate Similarity NPC150505
0.7031 Intermediate Similarity NPC77891
0.7031 Intermediate Similarity NPC182758
0.7015 Intermediate Similarity NPC249713
0.7 Intermediate Similarity NPC242930
0.6935 Remote Similarity NPC210999
0.6935 Remote Similarity NPC321030
0.6912 Remote Similarity NPC471022
0.6852 Remote Similarity NPC470439
0.6852 Remote Similarity NPC86121
0.6825 Remote Similarity NPC325550
0.6825 Remote Similarity NPC329003
0.6825 Remote Similarity NPC326524
0.678 Remote Similarity NPC208638
0.6727 Remote Similarity NPC138935
0.6667 Remote Similarity NPC280065
0.6667 Remote Similarity NPC45060
0.6667 Remote Similarity NPC325734
0.6667 Remote Similarity NPC291196
0.6667 Remote Similarity NPC103712
0.6615 Remote Similarity NPC273614
0.661 Remote Similarity NPC261571
0.6515 Remote Similarity NPC316674
0.65 Remote Similarity NPC188341
0.65 Remote Similarity NPC49494
0.6494 Remote Similarity NPC14326
0.6491 Remote Similarity NPC180575
0.6316 Remote Similarity NPC299114
0.6301 Remote Similarity NPC288086
0.619 Remote Similarity NPC329686
0.6182 Remote Similarity NPC269823
0.6167 Remote Similarity NPC182102
0.6167 Remote Similarity NPC26960
0.6111 Remote Similarity NPC15934
0.6076 Remote Similarity NPC39966
0.6076 Remote Similarity NPC224072
0.6071 Remote Similarity NPC206906
0.6071 Remote Similarity NPC256766
0.6071 Remote Similarity NPC213538
0.6066 Remote Similarity NPC59408
0.6066 Remote Similarity NPC71053
0.6049 Remote Similarity NPC3210
0.6034 Remote Similarity NPC269074
0.6029 Remote Similarity NPC55068
0.6029 Remote Similarity NPC477106
0.6024 Remote Similarity NPC316186
0.6 Remote Similarity NPC476923
0.597 Remote Similarity NPC176621
0.5965 Remote Similarity NPC116934
0.5938 Remote Similarity NPC474644
0.5904 Remote Similarity NPC473031
0.5902 Remote Similarity NPC474642
0.5902 Remote Similarity NPC473913
0.5902 Remote Similarity NPC249670
0.5897 Remote Similarity NPC314854
0.5897 Remote Similarity NPC313911
0.5873 Remote Similarity NPC61177
0.5846 Remote Similarity NPC474643
0.5846 Remote Similarity NPC249645
0.5846 Remote Similarity NPC55412
0.5846 Remote Similarity NPC473865
0.5818 Remote Similarity NPC29091
0.5818 Remote Similarity NPC103213
0.5818 Remote Similarity NPC182840
0.5818 Remote Similarity NPC255042
0.5806 Remote Similarity NPC474495
0.5806 Remote Similarity NPC473672
0.5789 Remote Similarity NPC476924
0.5789 Remote Similarity NPC304151
0.5783 Remote Similarity NPC203076
0.5781 Remote Similarity NPC110732
0.5769 Remote Similarity NPC473695
0.5769 Remote Similarity NPC473446
0.5763 Remote Similarity NPC276825
0.5763 Remote Similarity NPC160628
0.5763 Remote Similarity NPC140501
0.575 Remote Similarity NPC82799
0.5738 Remote Similarity NPC248884
0.5738 Remote Similarity NPC153538
0.5738 Remote Similarity NPC31194
0.5738 Remote Similarity NPC85079
0.5714 Remote Similarity NPC68014
0.5696 Remote Similarity NPC471597
0.5672 Remote Similarity NPC181872
0.5667 Remote Similarity NPC19834
0.5667 Remote Similarity NPC308331
0.5667 Remote Similarity NPC55063
0.5667 Remote Similarity NPC124183
0.5667 Remote Similarity NPC35141
0.5663 Remote Similarity NPC152684
0.5652 Remote Similarity NPC469728
0.5645 Remote Similarity NPC199286
0.5645 Remote Similarity NPC328784
0.5645 Remote Similarity NPC471281
0.5645 Remote Similarity NPC291437
0.5645 Remote Similarity NPC474460
0.5645 Remote Similarity NPC477727
0.5645 Remote Similarity NPC72699
0.5636 Remote Similarity NPC266298
0.5634 Remote Similarity NPC308844
0.5625 Remote Similarity NPC476560
0.5625 Remote Similarity NPC34577
0.5625 Remote Similarity NPC311369
0.5625 Remote Similarity NPC474496
0.5618 Remote Similarity NPC233273
0.5618 Remote Similarity NPC50902
0.5618 Remote Similarity NPC205546
0.561 Remote Similarity NPC228638

  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 NPC297020 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
0.6034 Remote Similarity NPD860 Phase 2
0.6029 Remote Similarity NPD3210 Clinical (unspecified phase)
0.6 Remote Similarity NPD4220 Pre-registration
0.5846 Remote Similarity NPD4219 Approved
0.5763 Remote Similarity NPD4265 Approved

  Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity
B: biological targets similarity
C: networks similarity
D: cell-based bioactivity similarity
E: similarity based on clinical data