NPASS Compound

Natural Product: NPC565629

Natural Product ID	NPC565629
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	ethyl nonadeca-5,8,11,14-tetraenoate
IUPAC Name	ethyl nonadeca-5,8,11,14-tetraenoate
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0000324] Fatty acid esters

The Chemical Classification was calculated by Classyfire, a software for chemical taxonomy calculation. Reference: DOI:10.1186/s13321-016-0174-y.

Chemical Representations

RDKit 3D 57 56 0 0 0 0 0 0 0 0999 V2000 -8.4049 -1.5048 0.6276 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1038 -1.0837 1.2198 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9077 -1.5797 0.4498 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8943 -1.0752 -0.9862 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8590 0.3990 -1.0411 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9257 1.1067 -1.5987 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7547 0.5500 -2.2655 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4694 0.9800 -1.6367 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3954 1.7697 -0.6007 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0436 2.1462 -0.0384 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0310 1.6697 1.3511 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2057 0.8118 1.8614 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8804 0.1607 1.1061 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1966 0.5194 1.7565 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1332 1.1629 1.0768 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4168 1.5128 1.7106 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5515 0.8726 0.9761 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4522 -0.6243 0.9578 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6018 -1.1967 0.2176 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6839 -2.4548 0.1000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.5518 -0.3761 -0.3253 O 0 0 0 0 0 0 0 0 0 0 0 0 8.6418 -0.9204 -1.0273 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1076 -1.7098 -2.2012 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.0945 -0.6265 0.4564 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3035 -2.0981 -0.3050 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.9473 -2.1528 1.3439 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0148 -1.4992 2.2431 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1093 0.0169 1.3312 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9929 -1.2108 0.9532 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8784 -2.6857 0.4733 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8286 -1.3806 -1.5171 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0658 -1.5797 -1.4749 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6959 0.9722 -0.5693 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0523 2.2229 -1.5508 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7557 1.0032 -3.3125 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8108 -0.5268 -2.3705 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5691 0.5977 -2.0895 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2404 2.1912 -0.0938 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9221 3.2572 -0.1028 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2790 1.6860 -0.6361 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8125 2.0873 2.0453 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3142 0.5379 2.9478 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8982 0.3843 0.0389 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7780 -0.9754 1.1644 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3107 0.2194 2.7869 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9529 1.4369 0.0369 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4210 1.2712 2.7801 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5559 2.6221 1.6310 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5282 1.2540 -0.0720 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5339 1.1625 1.3973 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4760 -0.9272 0.4783 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4794 -1.0412 1.9746 H 0 0 0 0 0 0 0 0 0 0 0 0 9.1871 -1.5915 -0.3093 H 0 0 0 0 0 0 0 0 0 0 0 0 9.3303 -0.1148 -1.3827 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2493 -1.1473 -2.6458 H 0 0 0 0 0 0 0 0 0 0 0 0 8.9249 -1.7646 -2.9644 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8392 -2.7367 -1.9293 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 1 0 4 5 1 0 5 6 2 3 6 7 1 0 7 8 1 0 8 9 2 3 9 10 1 0 10 11 1 0 11 12 2 3 12 13 1 0 13 14 1 0 14 15 2 3 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 2 0 19 21 1 0 21 22 1 0 22 23 1 0 1 24 1 0 1 25 1 0 1 26 1 0 2 27 1 0 2 28 1 0 3 29 1 0 3 30 1 0 4 31 1 0 4 32 1 0 5 33 1 0 6 34 1 0 7 35 1 0 7 36 1 0 8 37 1 0 9 38 1 0 10 39 1 0 10 40 1 0 11 41 1 0 12 42 1 0 13 43 1 0 13 44 1 0 14 45 1 0 15 46 1 0 16 47 1 0 16 48 1 0 17 49 1 0 17 50 1 0 18 51 1 0 18 52 1 0 22 53 1 0 22 54 1 0 23 55 1 0 23 56 1 0 23 57 1 0 M END

Standard InCHIKey	SDAXNCQMFACLJX-UHFFFAOYSA-N
Standard InCHI	InChI=1S/C21H34O2/c1-3-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21(22)23-4-2/h7-8,10-11,13-14,16-17H,3-6,9,12,15,18-20H2,1-2H3
SMILES	CCCCC=CCC=CCC=CCC=CCCCC(=O)OCC

Calculated Properties

Physi-Chem Properties

MedChem Properties

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

ADMET: Distribution

ADMET: Metabolism

ADMET: Excretion

ADMET: Toxicity

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO47570	Nephthea hainansis	Genus	Nephtheidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]

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	Organism Name	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

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

In vivo activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

Experimental ADME

Experiment Model	Experiment Tissue	ADME Type	ADME Relation	ADME Value	ADME Unit	Reference

Experimental Toxicity

Quantitative toxicity

Experiment Model	Experiment Organism	Toxicity Type	Toxicity Relation	Toxicity Value	Toxicity Unit	Reference

Common Abbreviations:
LC: Lethal Concentration; LD: Lethal Dose; LT:Lethal Time; NOAEL: No-observed-adverse-effect Level; BMDL: Benchmark Dose Lower Confidence Limit; BMD: Benchmark Dose; BMC:Benchmark Concentration; LOAEL: Lowest Observed Adverse Effect Level; RfD:Reference Dose; RfC:Reference Concentration; MRL: Minimal Risk Level; MEG: Maximum Exposure Guideline; PAC: Protective Action Criteria

Categorical toxicity labels

Hepatotoxicity	Carcinogenicity	Mutagenicity	Cardiotoxicity	Respiratory Toxicity	Eye Irritation	Endocrine Disruption

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 toxicity records from domain-specific databases. These databases include:
☉ ToxValDB: a curated database that compiles quantitative toxicity values for chemicals from diverse public sources to support toxicological research and risk assessment.
☉ TOXRIC: a comprehensive, free-to-access, online database providing toxicological/feature data. The toxicity labels are retrieved from this database. [PMID: 36400569]

Chemically structural similarity

Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes approximately 50,000 NPs with experimentally-derived bioactivity available in NPASS)

Similarity is measured using the Tanimoto coefficient (Tc) , which compares the binary fingerprints of two molecules. Tc is calculated as the intersection divided by the union of '1' bits in the fingerprints, ranging from 0 to 1, with 1 indicating highest similarity.

● The left chart: Distribution of similarity level between NPC565629 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	25159
0.1-0.2	22836
0.2-0.3	1576
0.3-0.4	204
0.4-0.5	47
0.5-0.6	22
0.6-0.7	7
0.7-0.8	1
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8333	Intermediate Similarity	NPC28779
0.7742	Intermediate Similarity	NPC10316
0.7742	Intermediate Similarity	NPC200845
0.7333	Intermediate Similarity	NPC128061
0.6667	Remote Similarity	NPC321919
0.6216	Remote Similarity	NPC475443
0.6216	Remote Similarity	NPC473829
0.6061	Remote Similarity	NPC39633
0.6053	Remote Similarity	NPC330426
0.6053	Remote Similarity	NPC127091
0.6053	Remote Similarity	NPC22101
0.5897	Remote Similarity	NPC54925
0.5862	Remote Similarity	NPC250028
0.5862	Remote Similarity	NPC236579
0.5862	Remote Similarity	NPC80234
0.5862	Remote Similarity	NPC203531
0.5862	Remote Similarity	NPC256163
0.5862	Remote Similarity	NPC40597
0.5714	Remote Similarity	NPC53541
0.5714	Remote Similarity	NPC223677
0.5641	Remote Similarity	NPC271921
0.5588	Remote Similarity	NPC139545
0.5556	Remote Similarity	NPC143211
0.5526	Remote Similarity	NPC81896
0.5405	Remote Similarity	NPC277597
0.5385	Remote Similarity	NPC143857
0.5385	Remote Similarity	NPC229252
0.5349	Remote Similarity	NPC473559
0.5349	Remote Similarity	NPC324981
0.5263	Remote Similarity	NPC104537
0.5238	Remote Similarity	NPC473772
0.5152	Remote Similarity	NPC309606
0.5143	Remote Similarity	NPC71761

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC565629 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6903
0.1-0.2	2099
0.2-0.3	125
0.3-0.4	19
0.4-0.5	1
0.5-0.6	0
0.6-0.7	0
0.7-0.8	1
0.8-0.85	1
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8929	High Similarity	NPD5343	Phase 4
0.8333	Intermediate Similarity	NPD6096	Phase 4
0.7	Intermediate Similarity	NPD6097	Approved

Bioactivity similarity

Similar Natural Products in NPASS

Similarity level is defined by 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