NPASS Compound

Natural Product: NPC141791

Natural Product ID	NPC141791
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	2-Phenylethyl (Z)-3-(3,4-Dihydroxyphenyl)Prop-2-Enoate
IUPAC Name	2-phenylethyl (Z)-3-(3,4-dihydroxyphenyl)prop-2-enoate
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL1397711
PubChem CID	6603789
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000476] Cinnamic acids and derivatives [CHEMONTID:0001391] Hydroxycinnamic acids and derivatives [CHEMONTID:0000059] Coumaric acids and derivatives

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 37 38 0 0 0 0 0 0 0 0999 V2000 -0.3734 -0.0013 -0.5357 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5487 -1.0187 -1.2037 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.7327 -1.5674 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9367 -1.3828 -1.2817 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3659 -0.2217 -0.5724 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8570 1.0188 -0.4857 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3888 1.9617 0.3796 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4587 1.6983 1.1929 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0083 0.4429 1.1297 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4846 -0.4852 0.2802 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1047 0.1445 1.9482 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9760 2.6660 2.0565 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6678 -1.5848 -1.7077 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9058 -0.9729 -1.4150 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2426 -0.9412 0.0458 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5525 -0.2885 0.3024 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6710 1.0705 0.5379 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9401 1.5917 0.7661 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0691 0.8171 0.7667 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9486 -0.5387 0.5316 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6843 -1.0730 0.3018 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5996 -2.7027 -2.1646 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7407 -2.1043 -1.6626 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0869 1.3380 -1.1333 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9539 2.9465 0.4258 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9558 -1.4658 0.2666 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8175 -0.4645 1.5291 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9129 3.0083 1.8975 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6549 -1.4587 -2.0332 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7935 0.0895 -1.7622 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4606 -0.5519 0.7009 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3582 -2.0267 0.3476 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7854 1.7046 0.5416 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0410 2.6623 0.9524 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0679 1.2032 0.9424 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8162 -1.2044 0.5207 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6428 -2.1432 0.1223 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 2 3 1 0 3 4 2 0 4 5 1 0 5 6 2 0 6 7 1 0 7 8 2 0 8 9 1 0 9 10 2 0 9 11 1 0 8 12 1 0 2 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 2 0 17 18 1 0 18 19 2 0 19 20 1 0 20 21 2 0 10 5 1 0 21 16 1 0 3 22 1 0 4 23 1 0 6 24 1 0 7 25 1 0 10 26 1 0 11 27 1 0 12 28 1 0 14 29 1 0 14 30 1 0 15 31 1 0 15 32 1 0 17 33 1 0 18 34 1 0 19 35 1 0 20 36 1 0 21 37 1 0 M END

Standard InCHIKey	SWUARLUWKZWEBQ-CLFYSBASSA-N
Standard InCHI	InChI=1S/C17H16O4/c18-15-8-6-14(12-16(15)19)7-9-17(20)21-11-10-13-4-2-1-3-5-13/h1-9,12,18-19H,10-11H2/b9-7-
SMILES	O=C(/C=Cc1ccc(c(c1)O)O)OCCc1ccccc1

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
NPO18176	Ephedra sinica	Species	Ephedraceae	Eukaryota	n.a.	root	n.a.	PMID[18975262]
NPO18176	Ephedra sinica	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24333010]
NPO15961	Sida cordifolia	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO30607	Coprinus atramentarius	Species	Agaricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26396	Coprinopsis atramentaria	Species	Psathyrellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8300	Apis mellifera ligustica	Species	Apidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18176	Ephedra sinica	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7804	Desmodium gangeticum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7804	Desmodium gangeticum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15961	Sida cordifolia	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO30607	Coprinus atramentarius	Species	Agaricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18176	Ephedra sinica	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15961	Sida cordifolia	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26396	Coprinopsis atramentaria	Species	Psathyrellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7804	Desmodium gangeticum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18176	Ephedra sinica	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8300	Apis mellifera ligustica	Species	Apidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO30607	Coprinus atramentarius	Species	Agaricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18176	Ephedra sinica	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7804	Desmodium gangeticum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18176	Ephedra sinica	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO26396	Coprinopsis atramentaria	Species	Psathyrellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18176	Ephedra sinica	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15961	Sida cordifolia	Species	Malvaceae	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

Activity Type	# Activity
Potency	27
AC50	5

Activity Type	# Activity
Individual protein	31
Others	1

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT163	Individual protein	Nuclear factor NF-kappa-B p105 subunit	Homo sapiens	Potency	=	2238.7	nM	PubChem BioAssay data set
NPT149	Individual protein	Endoplasmic reticulum-associated amyloid beta-peptide-binding protein	Homo sapiens	Potency	=	19952.6	nM	PubChem BioAssay data set
NPT2741	Individual protein	Pyruvate kinase	Leishmania mexicana	Potency	=	19952.6	nM	PubChem BioAssay data set
NPT210	Individual protein	Thyroid stimulating hormone receptor	Homo sapiens	Potency	=	5011.9	nM	PubChem BioAssay data set
NPT213	Individual protein	Cytochrome P450 2C19	Homo sapiens	Potency	=	12589.3	nM	PubChem BioAssay data set
NPT211	Individual protein	Hypoxia-inducible factor 1 alpha	Homo sapiens	Potency	=	5011.9	nM	PubChem BioAssay data set
NPT1119	Individual protein	Arachidonate 12-lipoxygenase	Homo sapiens	Potency	=	14125.4	nM	PubChem BioAssay data set
NPT282	Individual protein	MAP kinase ERK2	Homo sapiens	Potency	=	25118.9	nM	PubChem BioAssay data set
NPT150	Individual protein	Anthrax lethal factor	Bacillus anthracis	Potency	=	15848.9	nM	PubChem BioAssay data set
NPT149	Individual protein	Endoplasmic reticulum-associated amyloid beta-peptide-binding protein	Homo sapiens	Potency	=	12589.3	nM	PubChem BioAssay data set
NPT109	Individual protein	Cytochrome P450 3A4	Homo sapiens	Potency	=	15848.9	nM	PubChem BioAssay data set
NPT110	Individual protein	Cytochrome P450 2D6	Homo sapiens	Potency	=	39810.7	nM	PubChem BioAssay data set
NPT212	Individual protein	Cytochrome P450 2C9	Homo sapiens	Potency	=	39810.7	nM	PubChem BioAssay data set
NPT1139	Individual protein	Arachidonate 15-lipoxygenase, type II	Homo sapiens	Potency	n.a.	12589.3	nM	PubChem BioAssay data set
NPT110	Individual protein	Cytochrome P450 2D6	Homo sapiens	AC50	=	39810.72	nM	PubChem BioAssay data set
NPT208	Individual protein	Cytochrome P450 1A2	Homo sapiens	AC50	=	1000.0	nM	PubChem BioAssay data set
NPT213	Individual protein	Cytochrome P450 2C19	Homo sapiens	AC50	=	12589.25	nM	PubChem BioAssay data set
NPT109	Individual protein	Cytochrome P450 3A4	Homo sapiens	AC50	=	15848.93	nM	PubChem BioAssay data set
NPT212	Individual protein	Cytochrome P450 2C9	Homo sapiens	AC50	=	39810.72	nM	PubChem BioAssay data set
NPT96	Individual protein	Thrombopoietin	Homo sapiens	Potency	=	251.2	nM	PubChem BioAssay data set
NPT792	Individual protein	Arachidonate 15-lipoxygenase	Homo sapiens	Potency	=	794.3	nM	PubChem BioAssay data set
NPT52	Individual protein	Pyruvate kinase isozymes M1/M2	Homo sapiens	Potency	=	25118.9	nM	PubChem BioAssay data set
NPT539	Individual protein	Cellular tumor antigen p53	Homo sapiens	Potency	=	12589.3	nM	PubChem BioAssay data set
NPT539	Individual protein	Cellular tumor antigen p53	Homo sapiens	Potency	=	31622.8	nM	PubChem BioAssay data set

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified	n.a.	Potency	n.a.	10000.0	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

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 NPC141791 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	18300
0.1-0.2	26696
0.2-0.3	4221
0.3-0.4	452
0.4-0.5	140
0.5-0.6	24
0.6-0.7	8
0.7-0.8	0
0.8-0.85	1
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	NPC263386
0.8182	Intermediate Similarity	NPC147654
0.7209	Intermediate Similarity	NPC213156
0.7209	Intermediate Similarity	NPC240108
0.6923	Remote Similarity	NPC120225
0.6818	Remote Similarity	NPC95381
0.6458	Remote Similarity	NPC261453
0.6383	Remote Similarity	NPC217472
0.6136	Remote Similarity	NPC226250
0.6122	Remote Similarity	NPC275519
0.6122	Remote Similarity	NPC474967
0.6122	Remote Similarity	NPC33749
0.5882	Remote Similarity	NPC328593
0.5714	Remote Similarity	NPC213552
0.566	Remote Similarity	NPC203124
0.566	Remote Similarity	NPC607366
0.5556	Remote Similarity	NPC65791
0.5536	Remote Similarity	NPC155209
0.549	Remote Similarity	NPC260952
0.5472	Remote Similarity	NPC283468
0.5455	Remote Similarity	NPC474895
0.541	Remote Similarity	NPC67349
0.54	Remote Similarity	NPC150610
0.5385	Remote Similarity	NPC287597
0.5345	Remote Similarity	NPC482045
0.5345	Remote Similarity	NPC475695
0.5273	Remote Similarity	NPC168799
0.5208	Remote Similarity	NPC304638
0.5192	Remote Similarity	NPC233669
0.5192	Remote Similarity	NPC217052
0.5192	Remote Similarity	NPC329344
0.5192	Remote Similarity	NPC237506
0.5192	Remote Similarity	NPC32626
0.5179	Remote Similarity	NPC470849
0.5106	Remote Similarity	NPC264558
0.5094	Remote Similarity	NPC281277

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC141791 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3489
0.1-0.2	5264
0.2-0.3	376
0.3-0.4	19
0.4-0.5	2
0.5-0.6	0
0.6-0.7	0
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
		NPD

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