NPASS Compound

Natural Product: NPC68577

Natural Product ID	NPC68577
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Decyl 2-Methylprop-2-Enoate
IUPAC Name	decyl 2-methylprop-2-enoate
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL1578928
PubChem CID	18510
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0001722] Fatty alcohol 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 42 41 0 0 0 0 0 0 0 0999 V2000 -6.7549 -0.5778 -0.7919 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8224 -1.7706 -0.8078 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4816 -1.3645 -0.1964 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5227 -2.5169 -0.1906 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2167 -2.1191 0.4107 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5338 -0.9952 -0.3272 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2218 -0.6837 0.3702 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4594 0.4426 -0.3719 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7806 0.7742 0.3097 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4116 1.8888 -0.4594 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6463 2.3192 0.0402 O 0 0 0 0 0 0 0 0 0 0 0 0 4.7784 1.5304 0.1690 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6871 0.3301 -0.1933 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0366 2.0682 0.7059 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1031 3.3227 1.0758 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2469 1.2252 0.8435 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9732 -0.2069 -1.8083 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7186 -0.8233 -0.2795 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3245 0.2677 -0.1943 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2460 -2.5958 -0.2078 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6013 -2.1023 -1.8539 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6803 -1.0371 0.8258 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0353 -0.5470 -0.8157 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3215 -2.8770 -1.2312 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9948 -3.3724 0.3331 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3566 -1.7721 1.4572 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5650 -3.0131 0.4439 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3184 -1.3513 -1.3631 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1240 -0.0784 -0.3458 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4627 -1.5522 0.3844 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4661 -0.3253 1.3850 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6557 0.2124 -1.4205 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1897 1.3297 -0.2797 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5392 1.0446 1.3558 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4517 -0.0884 0.3351 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5060 1.5425 -1.5217 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7199 2.7686 -0.4050 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0144 3.7234 1.4678 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2385 3.9505 0.9846 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0445 1.5449 0.1179 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7098 1.3112 1.8491 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9767 0.1735 0.6883 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 1 0 11 12 1 0 12 13 2 0 12 14 1 0 14 15 2 0 14 16 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 10 36 1 0 10 37 1 0 15 38 1 0 15 39 1 0 16 40 1 0 16 41 1 0 16 42 1 0 M END

Standard InCHIKey	GTBGXKPAKVYEKJ-UHFFFAOYSA-N
Standard InCHI	InChI=1S/C14H26O2/c1-4-5-6-7-8-9-10-11-12-16-14(15)13(2)3/h2,4-12H2,1,3H3
SMILES	CCCCCCCCCCOC(=O)C(=C)C

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
NPO8108.1	Citrullus lanatus subsp. vulgaris	Subspecies	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8108.1	Citrullus lanatus subsp. vulgaris	Subspecies	Cucurbitaceae	Eukaryota	Fruits	n.a.		Database[Phenol-Explorer]
NPO8108.1	Citrullus lanatus subsp. vulgaris	Subspecies	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]

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

Activity Type	# Activity
Potency	20

Activity Type	# Activity
Individual protein	8
Cell line	1
Others	11

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT153	Individual protein	Androgen Receptor	Homo sapiens	Potency	n.a.	69078.2	nM	PubChem BioAssay data set
NPT106	Individual protein	Peroxisome proliferator-activated receptor delta	Homo sapiens	Potency	n.a.	55337.8	nM	PubChem BioAssay data set
NPT162	Individual protein	Heat shock protein beta-1	Homo sapiens	Potency	n.a.	55337.8	nM	PubChem BioAssay data set
NPT106	Individual protein	Peroxisome proliferator-activated receptor delta	Homo sapiens	Potency	n.a.	22030.4	nM	PubChem BioAssay data set
NPT210	Individual protein	Thyroid stimulating hormone receptor	Homo sapiens	Potency	=	1258.9	nM	PubChem BioAssay data set
NPT98	Individual protein	HERG	Homo sapiens	Potency	n.a.	3548.1	nM	PubChem BioAssay data set
NPT74	Individual protein	Proto-oncogene c-JUN	Homo sapiens	Potency	n.a.	62090.1	nM	PubChem BioAssay data set

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT347	Cell line	Lymphoblastoid cells	Homo sapiens	Potency	=	39810.7	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	55337.8	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	39176.2	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	49319.9	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	43956.4	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	877	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	62090.1	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	38845.5	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	24509.9	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	69078.2	nM	PubChem BioAssay data set

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
-	Homo sapiens	DNEL systemic	=	2.5	mg/m3	ToxVal

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 NPC68577 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	25237
0.1-0.2	22178
0.2-0.3	2170
0.3-0.4	204
0.4-0.5	42
0.5-0.6	9
0.6-0.7	13
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC223675
0.6923	Remote Similarity	NPC86545
0.6923	Remote Similarity	NPC286498
0.6923	Remote Similarity	NPC223374
0.6923	Remote Similarity	NPC196442
0.6923	Remote Similarity	NPC301398
0.6923	Remote Similarity	NPC608162
0.6923	Remote Similarity	NPC609004
0.6786	Remote Similarity	NPC80641
0.6667	Remote Similarity	NPC322892
0.6552	Remote Similarity	NPC149299
0.6538	Remote Similarity	NPC40965
0.6429	Remote Similarity	NPC154396
0.6207	Remote Similarity	NPC80396
0.5862	Remote Similarity	NPC155872
0.5667	Remote Similarity	NPC154642
0.5667	Remote Similarity	NPC603612
0.5556	Remote Similarity	NPC248233
0.5517	Remote Similarity	NPC223249
0.5517	Remote Similarity	NPC12904
0.5484	Remote Similarity	NPC14608
0.5333	Remote Similarity	NPC286695
0.5172	Remote Similarity	NPC147054

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC68577 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6819
0.1-0.2	2163
0.2-0.3	143
0.3-0.4	19
0.4-0.5	2
0.5-0.6	3
0.6-0.7	1
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.6471	Remote Similarity	NPD3205	Discontinued
0.5484	Remote Similarity	NPD9378	Phase 4
0.5278	Remote Similarity	NPD631	Phase 4
0.5135	Remote Similarity	NPD630	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