Structure

Physi-Chem Properties

Molecular Weight:  247.19
Volume:  291.897
LogP:  3.107
LogD:  3.073
LogS:  -2.876
# Rotatable Bonds:  9
TPSA:  29.1
# H-Bond Aceptor:  2
# H-Bond Donor:  1
# Rings:  0
# Heavy Atoms:  2

MedChem Properties

QED Drug-Likeness Score:  0.65
Synthetic Accessibility Score:  3.13
Fsp3:  0.438
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:  -4.164
MDCK Permeability:  4.9139158363686875e-05
Pgp-inhibitor:  0.001
Pgp-substrate:  0.001
Human Intestinal Absorption (HIA):  0.004
20% Bioavailability (F20%):  0.003
30% Bioavailability (F30%):  0.641

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.431
Plasma Protein Binding (PPB):  95.80390167236328%
Volume Distribution (VD):  1.108
Pgp-substrate:  2.6754040718078613%

ADMET: Metabolism

CYP1A2-inhibitor:  0.78
CYP1A2-substrate:  0.11
CYP2C19-inhibitor:  0.59
CYP2C19-substrate:  0.586
CYP2C9-inhibitor:  0.386
CYP2C9-substrate:  0.051
CYP2D6-inhibitor:  0.067
CYP2D6-substrate:  0.075
CYP3A4-inhibitor:  0.572
CYP3A4-substrate:  0.274

ADMET: Excretion

Clearance (CL):  12.693
Half-life (T1/2):  0.874

ADMET: Toxicity

hERG Blockers:  0.698
Human Hepatotoxicity (H-HT):  0.864
Drug-inuced Liver Injury (DILI):  0.031
AMES Toxicity:  0.259
Rat Oral Acute Toxicity:  0.91
Maximum Recommended Daily Dose:  0.928
Skin Sensitization:  0.97
Carcinogencity:  0.282
Eye Corrosion:  0.025
Eye Irritation:  0.422
Respiratory Toxicity:  0.964

Download Data

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

  Natural Product: NPC145032

Natural Product ID:  NPC145032
Common Name*:   Dodeca-2E,4E,8Z,10Z-Tetraenoic Acid Isobutylamide
IUPAC Name:   (2E,4E,8Z,10Z)-N-(2-methylpropyl)dodeca-2,4,8,10-tetraenamide
Synonyms:   Dodeca-2E,4E,8Z,10Z-Tetraenoic Acid Isobutylamide
Standard InCHIKey:  VLGRWXYRKYWRPX-VSRLVKTQSA-N
Standard InCHI:  InChI=1S/C16H25NO/c1-4-5-6-7-8-9-10-11-12-13-16(18)17-14-15(2)3/h4-7,10-13,15H,8-9,14H2,1-3H3,(H,17,18)/b5-4-,7-6-,11-10+,13-12+
SMILES:  C/C=CC=C/CC/C=C/C=C/C(=NCC(C)C)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL463546
PubChem CID:   11413953
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]
NPO726 Echinacea angustifolia 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]
NPO726 Echinacea angustifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
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
NPT113 Cell Line RAW264.7 Mus musculus TD50 = 50.0 ug ml-1 PMID[462933]
NPT113 Cell Line RAW264.7 Mus musculus ID50 = 6.0 ug ml-1 PMID[462933]
NPT232 Individual Protein Cannabinoid CB1 receptor Homo sapiens Ki = 6210.0 nM PMID[462935]
NPT1287 Individual Protein Cannabinoid CB2 receptor Homo sapiens Ki = 57.0 nM PMID[462935]
NPT99 Individual Protein Peroxisome proliferator-activated receptor gamma Homo sapiens FC = 2.0 n.a. PMID[462934]

☑ 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 NPC145032 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
1.0 High Similarity NPC243539
1.0 High Similarity NPC267340
1.0 High Similarity NPC54542
1.0 High Similarity NPC304223
0.9787 High Similarity NPC267692
0.9787 High Similarity NPC307435
0.9592 High Similarity NPC119655
0.9592 High Similarity NPC303672
0.94 High Similarity NPC56028
0.94 High Similarity NPC167759
0.94 High Similarity NPC305288
0.94 High Similarity NPC163912
0.9388 High Similarity NPC195986
0.9216 High Similarity NPC273023
0.9216 High Similarity NPC471991
0.9216 High Similarity NPC297020
0.9216 High Similarity NPC471992
0.9038 High Similarity NPC261158
0.9038 High Similarity NPC24216
0.9038 High Similarity NPC104138
0.9038 High Similarity NPC306420
0.9038 High Similarity NPC477049
0.902 High Similarity NPC44193
0.902 High Similarity NPC246519
0.902 High Similarity NPC14234
0.902 High Similarity NPC132669
0.902 High Similarity NPC184014
0.902 High Similarity NPC123669
0.902 High Similarity NPC269800
0.8393 Intermediate Similarity NPC6795
0.8302 Intermediate Similarity NPC13011
0.8302 Intermediate Similarity NPC124382
0.8214 Intermediate Similarity NPC312826
0.82 Intermediate Similarity NPC91044
0.8182 Intermediate Similarity NPC245650
0.7797 Intermediate Similarity NPC471023
0.7705 Intermediate Similarity NPC187315
0.7667 Intermediate Similarity NPC253468
0.7667 Intermediate Similarity NPC235311
0.7586 Intermediate Similarity NPC74617
0.7586 Intermediate Similarity NPC150505
0.7541 Intermediate Similarity NPC477525
0.75 Intermediate Similarity NPC77891
0.7419 Intermediate Similarity NPC315141
0.7419 Intermediate Similarity NPC129995
0.74 Intermediate Similarity NPC86121
0.74 Intermediate Similarity NPC470439
0.7368 Intermediate Similarity NPC4881
0.7333 Intermediate Similarity NPC324077
0.7167 Intermediate Similarity NPC309877
0.7167 Intermediate Similarity NPC130807
0.7077 Intermediate Similarity NPC471022
0.7049 Intermediate Similarity NPC273614
0.6833 Remote Similarity NPC210999
0.6792 Remote Similarity NPC299114
0.6774 Remote Similarity NPC29468
0.6765 Remote Similarity NPC314678
0.6667 Remote Similarity NPC182758
0.661 Remote Similarity NPC242930
0.6604 Remote Similarity NPC138935
0.6418 Remote Similarity NPC249713
0.629 Remote Similarity NPC325734
0.629 Remote Similarity NPC321030
0.6226 Remote Similarity NPC206906
0.619 Remote Similarity NPC329003
0.619 Remote Similarity NPC326524
0.619 Remote Similarity NPC325550
0.6184 Remote Similarity NPC14326
0.6102 Remote Similarity NPC208638
0.6087 Remote Similarity NPC103712
0.6087 Remote Similarity NPC45060
0.6087 Remote Similarity NPC280065
0.6087 Remote Similarity NPC291196
0.6071 Remote Similarity NPC180575
0.6038 Remote Similarity NPC269823
0.6 Remote Similarity NPC313911
0.6 Remote Similarity NPC314854
0.5962 Remote Similarity NPC15934
0.5962 Remote Similarity NPC182840
0.5962 Remote Similarity NPC29091
0.5962 Remote Similarity NPC103213
0.5962 Remote Similarity NPC255042
0.5932 Remote Similarity NPC261571
0.5926 Remote Similarity NPC213538
0.5926 Remote Similarity NPC256766
0.5909 Remote Similarity NPC477106
0.5909 Remote Similarity NPC316674
0.5849 Remote Similarity NPC56917
0.5849 Remote Similarity NPC145077
0.5833 Remote Similarity NPC188341
0.5833 Remote Similarity NPC49494
0.5818 Remote Similarity NPC116934
0.58 Remote Similarity NPC58957
0.5763 Remote Similarity NPC291437
0.5763 Remote Similarity NPC328784
0.5753 Remote Similarity NPC288086
0.575 Remote Similarity NPC3210
0.5676 Remote Similarity NPC476923
0.5667 Remote Similarity NPC71053
0.5667 Remote Similarity NPC59408
0.5667 Remote Similarity NPC43053
0.5636 Remote Similarity NPC68889
0.5636 Remote Similarity NPC51758
0.5636 Remote Similarity NPC209279
0.5636 Remote Similarity NPC304151
0.5636 Remote Similarity NPC88079
0.5636 Remote Similarity NPC108494
0.5636 Remote Similarity NPC180871
0.5636 Remote Similarity NPC67761
0.5636 Remote Similarity NPC194586
0.5614 Remote Similarity NPC160628
0.5614 Remote Similarity NPC269074
0.5614 Remote Similarity NPC140501
0.561 Remote Similarity NPC473031
0.56 Remote Similarity NPC250734
0.56 Remote Similarity NPC263266

  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 NPC145032 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
0.6481 Remote Similarity NPD860 Phase 2
0.614 Remote Similarity NPD4220 Pre-registration
0.5645 Remote Similarity NPD9652 Approved
0.5614 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