Structure

Physi-Chem Properties

Molecular Weight:  291.26
Volume:  340.501
LogP:  5.504
LogD:  4.179
LogS:  -4.706
# Rotatable Bonds:  11
TPSA:  20.31
# H-Bond Aceptor:  2
# H-Bond Donor:  0
# Rings:  1
# Heavy Atoms:  2

MedChem Properties

QED Drug-Likeness Score:  0.397
Synthetic Accessibility Score:  2.41
Fsp3:  0.737
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.716
MDCK Permeability:  1.4630779332946986e-05
Pgp-inhibitor:  0.475
Pgp-substrate:  0.003
Human Intestinal Absorption (HIA):  0.005
20% Bioavailability (F20%):  0.977
30% Bioavailability (F30%):  0.941

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.822
Plasma Protein Binding (PPB):  96.22505950927734%
Volume Distribution (VD):  0.92
Pgp-substrate:  3.215123414993286%

ADMET: Metabolism

CYP1A2-inhibitor:  0.541
CYP1A2-substrate:  0.639
CYP2C19-inhibitor:  0.522
CYP2C19-substrate:  0.547
CYP2C9-inhibitor:  0.355
CYP2C9-substrate:  0.735
CYP2D6-inhibitor:  0.275
CYP2D6-substrate:  0.374
CYP3A4-inhibitor:  0.881
CYP3A4-substrate:  0.191

ADMET: Excretion

Clearance (CL):  4.229
Half-life (T1/2):  0.232

ADMET: Toxicity

hERG Blockers:  0.322
Human Hepatotoxicity (H-HT):  0.634
Drug-inuced Liver Injury (DILI):  0.022
AMES Toxicity:  0.007
Rat Oral Acute Toxicity:  0.272
Maximum Recommended Daily Dose:  0.655
Skin Sensitization:  0.985
Carcinogencity:  0.179
Eye Corrosion:  0.429
Eye Irritation:  0.667
Respiratory Toxicity:  0.963

Download Data

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

  Natural Product: NPC206660

Natural Product ID:  NPC206660
Common Name*:   1-[(2E,4E)-Tetradecadienoyl]Piperidine
IUPAC Name:   (2E,4E)-1-piperidin-1-yltetradeca-2,4-dien-1-one
Synonyms:  
Standard InCHIKey:  ARLNCELWGQDJPO-QDTXCPDVSA-N
Standard InCHI:  InChI=1S/C19H33NO/c1-2-3-4-5-6-7-8-9-10-11-13-16-19(21)20-17-14-12-15-18-20/h10-11,13,16H,2-9,12,14-15,17-18H2,1H3/b11-10+,16-13+
SMILES:  CCCCCCCCC/C=C/C=C/C(=O)N1CCCCC1
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL2442642
PubChem CID:   11130083
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0000195] Piperidines
        • [CHEMONTID:0000335] N-acylpiperidines

*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
NPO14864 Clerodendrum cyrtophyllum Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[11473423]
NPO10210 Artabotrys uncinatus Species Annonaceae Eukaryota n.a. n.a. n.a. PMID[11575948]
NPO12347 Pseudomonas syringae Species Pseudomonadaceae Bacteria n.a. n.a. n.a. PMID[14714872]
NPO15548 Sinularia leptoclados Species Alcyoniidae Eukaryota n.a. n.a. n.a. PMID[16724859]
NPO12993 Polypodium vulgare Species Polypodiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO10210 Artabotrys uncinatus Species Annonaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO15166 Cephalotaxus hainanensis Species Taxaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO15166 Cephalotaxus hainanensis Species Taxaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7042 Myrica arborea Species Myricaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO8392 Iryanthera polyneura Species Myristicaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO10210 Artabotrys uncinatus Species Annonaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO12993 Polypodium vulgare Species Polypodiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO9734 Vincetoxicum hirundinaria Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15166 Cephalotaxus hainanensis Species Taxaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO12993 Polypodium vulgare Species Polypodiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO5469 Pseudoxandra sclerocarpa Species Annonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22084 Stypandra imbricata Species Asphodelaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7042 Myrica arborea Species Myricaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4518.1 Saccharothrix mutabilis subsp. capreolus Subspecies Pseudonocardiaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO12993 Polypodium vulgare Species Polypodiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6367 Cortinarius viola Species Cortinariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15166 Cephalotaxus hainanensis Species Taxaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13549 Otanthus maritimus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26712 Cladrastis kentukea Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12121 Streptomyces naraensis Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO3974 Ferula gummosa Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14989 Acanthothamnus aphyllus Species Celastraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13320 Glycosmis puberula Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11505 Nigella aristata Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9338 Polygala aureocauda Species Polygalaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14191 Berkheya rhapontica Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15066 Iridaea membranacea Species Gigartinaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15548 Sinularia leptoclados Species Alcyoniidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1027 Scrophularia leucoclada Species Scrophulariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4699 Dracaena ombet Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12347 Pseudomonas syringae Species Pseudomonadaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO8392 Iryanthera polyneura Species Myristicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11151 Arnebia decumbens Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19872 Achillea magnifica Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10210 Artabotrys uncinatus Species Annonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9734 Vincetoxicum hirundinaria Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4503 Bryonopsis laciniosa n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO14864 Clerodendrum cyrtophyllum Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20070 Crinum stuhlmannii Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12539 Lissoclinum japonicum Species Didemnidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11683 Crotalaria mitchellii Species Fabaceae 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
NPT1167 Individual Protein Delta opioid receptor Mus musculus Ki = 6500.0 nM PMID[522438]
NPT1168 Individual Protein Mu opioid receptor Mus musculus Ki = 5750.0 nM PMID[522438]
NPT1169 Individual Protein Cannabinoid CB2 receptor Mus musculus Ki = 24000.0 nM PMID[522438]
NPT1170 Individual Protein Cannabinoid CB1 receptor Mus musculus Ki = 6700.0 nM PMID[522438]
NPT2 Others Unspecified Ratio Ki = 1.13 n.a. PMID[522438]
NPT2 Others Unspecified Ratio Ki = 0.28 n.a. PMID[522438]

☑ 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 NPC206660 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
0.9492 High Similarity NPC42477
0.871 High Similarity NPC252684
0.8387 Intermediate Similarity NPC133923
0.8286 Intermediate Similarity NPC34672
0.8226 Intermediate Similarity NPC385
0.7733 Intermediate Similarity NPC209232
0.72 Intermediate Similarity NPC214125
0.72 Intermediate Similarity NPC320667
0.7067 Intermediate Similarity NPC63284
0.6944 Remote Similarity NPC96272
0.6923 Remote Similarity NPC120699
0.6923 Remote Similarity NPC127430
0.6914 Remote Similarity NPC61321
0.6914 Remote Similarity NPC78058
0.6914 Remote Similarity NPC234822
0.6914 Remote Similarity NPC135639
0.6914 Remote Similarity NPC143344
0.6812 Remote Similarity NPC477461
0.6812 Remote Similarity NPC477459
0.6667 Remote Similarity NPC86452
0.6667 Remote Similarity NPC470738
0.6667 Remote Similarity NPC244256
0.6533 Remote Similarity NPC97614
0.6506 Remote Similarity NPC207048
0.65 Remote Similarity NPC267203
0.65 Remote Similarity NPC77890
0.65 Remote Similarity NPC132858
0.6494 Remote Similarity NPC470994
0.6486 Remote Similarity NPC23721
0.6471 Remote Similarity NPC17497
0.6471 Remote Similarity NPC305602
0.6456 Remote Similarity NPC308050
0.6389 Remote Similarity NPC476559
0.6351 Remote Similarity NPC477460
0.6351 Remote Similarity NPC76869
0.6341 Remote Similarity NPC277341
0.6341 Remote Similarity NPC226982
0.631 Remote Similarity NPC475975
0.6203 Remote Similarity NPC281154
0.6163 Remote Similarity NPC157479
0.6143 Remote Similarity NPC231129
0.6098 Remote Similarity NPC471768
0.6076 Remote Similarity NPC470993
0.6076 Remote Similarity NPC470992
0.6056 Remote Similarity NPC82919
0.6047 Remote Similarity NPC147513
0.6 Remote Similarity NPC145707
0.5976 Remote Similarity NPC28529
0.5949 Remote Similarity NPC26932
0.5934 Remote Similarity NPC473661
0.5889 Remote Similarity NPC17143
0.5889 Remote Similarity NPC47230
0.5882 Remote Similarity NPC215474
0.5875 Remote Similarity NPC78562
0.5875 Remote Similarity NPC473588
0.5854 Remote Similarity NPC46268
0.5854 Remote Similarity NPC25513
0.5833 Remote Similarity NPC477523
0.5833 Remote Similarity NPC476560
0.5783 Remote Similarity NPC475363
0.5783 Remote Similarity NPC473972
0.5783 Remote Similarity NPC473971
0.5783 Remote Similarity NPC473695
0.5783 Remote Similarity NPC473446
0.5778 Remote Similarity NPC81195
0.5765 Remote Similarity NPC477524
0.5747 Remote Similarity NPC116881
0.5747 Remote Similarity NPC57163
0.5714 Remote Similarity NPC53240
0.5699 Remote Similarity NPC474974
0.5684 Remote Similarity NPC91036
0.5684 Remote Similarity NPC52820
0.5682 Remote Similarity NPC76283
0.5638 Remote Similarity NPC256452
0.5634 Remote Similarity NPC104138
0.5634 Remote Similarity NPC24216
0.5634 Remote Similarity NPC306420
0.5634 Remote Similarity NPC261158
0.5631 Remote Similarity NPC143173
0.5625 Remote Similarity NPC145755
0.5625 Remote Similarity NPC267514
0.5625 Remote Similarity NPC120203

  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 NPC206660 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
0.65 Remote Similarity NPD529 Approved
0.6026 Remote Similarity NPD815 Approved
0.6026 Remote Similarity NPD816 Approved
0.5714 Remote Similarity NPD3709 Clinical (unspecified phase)
0.5612 Remote Similarity NPD4803 Discontinued

  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