NPASS Compound

Natural Product: NPC151428

Natural Product ID	NPC151428
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	FZBIESPTFIVNEJ-UHFFFAOYSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	14833269
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0000324] Fatty acid esters [CHEMONTID:0001421] Glycidol 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 40 40 0 0 0 0 0 0 0 0999 V2000 -6.2435 1.0742 0.2361 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0155 1.6662 -0.4203 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8911 0.6468 -0.5374 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5453 0.1986 0.8364 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4437 -0.8176 0.9031 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1478 -0.3563 0.3382 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1462 -1.4877 0.4794 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2043 -1.1394 -0.0587 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8063 0.0524 0.6507 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1590 0.3714 0.0855 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7692 1.3320 0.5781 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6339 -0.4022 -0.9237 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8715 -0.2189 -1.5256 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0243 -0.4512 -0.6043 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0746 0.5072 -0.5454 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0927 0.4085 0.5427 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.2335 -0.0284 0.2250 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3458 1.4023 1.2942 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1767 1.4046 -0.2795 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2500 2.1323 -1.3954 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6206 2.4539 0.2850 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2933 -0.1728 -1.1746 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0580 1.1716 -1.0499 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4643 -0.1772 1.3293 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2342 1.0945 1.4213 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8031 -1.7333 0.3649 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2863 -1.1144 1.9598 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2055 -0.0211 -0.7041 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8265 0.5491 0.9309 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5778 -2.3613 -0.0151 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0280 -1.7325 1.5689 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8753 -1.9990 0.1447 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1980 -0.9334 -1.1414 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8529 -0.1112 1.7485 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1281 0.9364 0.5053 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9448 -0.9530 -2.3874 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9450 0.8080 -2.0105 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1976 -1.5266 -0.3794 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0864 0.2836 -0.1813 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9728 1.4777 -1.0943 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 1 0 6 7 1 0 7 8 1 0 8 9 1 0 9 10 1 0 10 11 2 0 10 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 14 1 0 1 17 1 0 1 18 1 0 1 19 1 0 2 20 1 0 2 21 1 0 3 22 1 0 3 23 1 0 4 24 1 0 4 25 1 0 5 26 1 0 5 27 1 0 6 28 1 0 6 29 1 0 7 30 1 0 7 31 1 0 8 32 1 0 8 33 1 0 9 34 1 0 9 35 1 0 13 36 1 0 13 37 1 0 14 38 1 0 15 39 1 0 15 40 1 0 M END

Standard InCHIKey	FZBIESPTFIVNEJ-UHFFFAOYSA-N
Standard InCHI	InChI=1S/C13H24O3/c1-2-3-4-5-6-7-8-9-13(14)16-11-12-10-15-12/h12H,2-11H2,1H3
SMILES	CCCCCCCCCC(=O)OCC1CO1

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
NPO21355	Elsholtzia ciliata	Species	Lamiaceae	Eukaryota	Aerial Parts	n.a.	n.a.	PMID[32991171]
NPO21355	Elsholtzia ciliata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18046	Mosla chinensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21355	Elsholtzia ciliata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18046	Mosla chinensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18046	Mosla chinensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21355	Elsholtzia ciliata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18046	Mosla chinensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21355	Elsholtzia ciliata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18046	Mosla chinensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO21355	Elsholtzia ciliata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO18046	Mosla chinensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21355	Elsholtzia ciliata	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	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 NPC151428 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	24783
0.1-0.2	23025
0.2-0.3	1761
0.3-0.4	169
0.4-0.5	74
0.5-0.6	26
0.6-0.7	17
0.7-0.8	0
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
0.8214	Intermediate Similarity	NPC55678
0.6923	Remote Similarity	NPC250028
0.6923	Remote Similarity	NPC236579
0.6923	Remote Similarity	NPC80234
0.6923	Remote Similarity	NPC203531
0.6923	Remote Similarity	NPC256163
0.6923	Remote Similarity	NPC40597
0.6286	Remote Similarity	NPC602940
0.6216	Remote Similarity	NPC54925
0.6207	Remote Similarity	NPC603612
0.6154	Remote Similarity	NPC53541
0.6129	Remote Similarity	NPC488257
0.6129	Remote Similarity	NPC469937
0.6129	Remote Similarity	NPC94699
0.6129	Remote Similarity	NPC320588
0.6129	Remote Similarity	NPC53463
0.6	Remote Similarity	NPC149299
0.6	Remote Similarity	NPC310746
0.5806	Remote Similarity	NPC26253
0.5714	Remote Similarity	NPC47363
0.5714	Remote Similarity	NPC287231
0.5667	Remote Similarity	NPC80396
0.5667	Remote Similarity	NPC154642
0.5667	Remote Similarity	NPC600941
0.5625	Remote Similarity	NPC128061
0.5556	Remote Similarity	NPC201622
0.5556	Remote Similarity	NPC305660
0.5556	Remote Similarity	NPC12156
0.5556	Remote Similarity	NPC161097
0.5556	Remote Similarity	NPC28598
0.5556	Remote Similarity	NPC22903
0.5556	Remote Similarity	NPC54980
0.5349	Remote Similarity	NPC224700
0.5349	Remote Similarity	NPC320663
0.5333	Remote Similarity	NPC603863
0.525	Remote Similarity	NPC48218
0.525	Remote Similarity	NPC141481
0.525	Remote Similarity	NPC464342
0.5172	Remote Similarity	NPC81263
0.5172	Remote Similarity	NPC317128
0.5161	Remote Similarity	NPC80641
0.5143	Remote Similarity	NPC223677
0.5143	Remote Similarity	NPC28779
0.5135	Remote Similarity	NPC104537

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC151428 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6631
0.1-0.2	2346
0.2-0.3	143
0.3-0.4	19
0.4-0.5	5
0.5-0.6	3
0.6-0.7	1
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8214	Intermediate Similarity	NPD6125	Phase 4
0.6176	Remote Similarity	NPD3730	Pre-clinical
0.5714	Remote Similarity	NPD2699	Pre-clinical
0.5385	Remote Similarity	NPD3728	Approved
0.5349	Remote Similarity	NPD8278	Phase 4

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