NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	285.1
Volume:	287.325
LogP:	1.894
LogD:	1.78
LogS:	-3.384
# Rotatable Bonds:	2
TPSA:	78.79
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.776
Synthetic Accessibility Score:	3.079
Fsp3:	0.188
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.983
MDCK Permeability:	1.0205849321209826e-05
Pgp-inhibitor:	0.004
Pgp-substrate:	0.549
Human Intestinal Absorption (HIA):	0.031
20% Bioavailability (F20%):	0.244
30% Bioavailability (F30%):	0.888

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.985
Plasma Protein Binding (PPB):	79.45328521728516%
Volume Distribution (VD):	0.71
Pgp-substrate:	18.506267547607422%

ADMET: Metabolism

CYP1A2-inhibitor:	0.075
CYP1A2-substrate:	0.429
CYP2C19-inhibitor:	0.311
CYP2C19-substrate:	0.853
CYP2C9-inhibitor:	0.117
CYP2C9-substrate:	0.73
CYP2D6-inhibitor:	0.06
CYP2D6-substrate:	0.707
CYP3A4-inhibitor:	0.109
CYP3A4-substrate:	0.755

ADMET: Excretion

Clearance (CL):	1.244
Half-life (T1/2):	0.395

ADMET: Toxicity

hERG Blockers:	0.042
Human Hepatotoxicity (H-HT):	0.391
Drug-inuced Liver Injury (DILI):	0.723
AMES Toxicity:	0.652
Rat Oral Acute Toxicity:	0.114
Maximum Recommended Daily Dose:	0.111
Skin Sensitization:	0.367
Carcinogencity:	0.078
Eye Corrosion:	0.003
Eye Irritation:	0.029
Respiratory Toxicity:	0.264

Download Data

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

Natural Product: NPC107287

Natural Product ID:	NPC107287
*Common Name:**	Ethyl Nicotinate
IUPAC Name:	ethyl pyridine-3-carboxylate
Synonyms:
Standard InCHIKey:	XBLVHTDFJBKJLG-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C8H9NO2/c1-2-11-8(10)7-4-3-5-9-6-7/h3-6H,2H2,1H3
SMILES:	CCOC(=O)c1cccnc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2251611
PubChem CID:	69188
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000089] Pyridines and derivatives [CHEMONTID:0001322] Pyridinecarboxylic acids and derivatives [CHEMONTID:0002414] Pyridinecarboxylic acids

*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
NPO3912	Areca catechu	Species	Arecaceae	Eukaryota	n.a.	fruit	n.a.	Database[Article]
NPO3912	Areca catechu	Species	Arecaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3912	Areca catechu	Species	Arecaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3912	Areca catechu	Species	Arecaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO3912	Areca catechu	Species	Arecaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO3912	Areca catechu	Species	Arecaceae	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

Activity Type	# Activity
Others	4
Potency	2

Activity Type	# Activity
Organism	4
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		Potency	n.a.	33491.5	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	298.5	nM	PubChem BioAssay data set
NPT1281	Organism	Thrips obscuratus	Thrips obscuratus	MAD	=	1.0	10'-6microL	PMID[528539]
NPT1280	Organism	Thrips tabaci	Thrips tabaci	Ratio	=	3.1	n.a.	PMID[528540]
NPT1281	Organism	Thrips obscuratus	Thrips obscuratus	Ratio	=	84.8	n.a.	PMID[528540]
NPT1281	Organism	Thrips obscuratus	Thrips obscuratus	Ratio	=	157.6	n.a.	PMID[528540]

☑ 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 NPC107287 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	359
0.1-0.2	5196
0.2-0.3	12000
0.3-0.4	15875
0.4-0.5	5782
0.5-0.6	2501
0.6-0.7	813
0.7-0.8	152
0.8-0.85	10
0.85-0.9	2
0.9-0.95	5
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9718	High Similarity	NPC112741
0.9236	High Similarity	NPC159630
0.9236	High Similarity	NPC230085
0.9128	High Similarity	NPC263455
0.9041	High Similarity	NPC167400
0.8974	High Similarity	NPC249614
0.8808	High Similarity	NPC312860
0.8462	Intermediate Similarity	NPC113812
0.8415	Intermediate Similarity	NPC317010
0.8264	Intermediate Similarity	NPC471589
0.8188	Intermediate Similarity	NPC114310
0.8121	Intermediate Similarity	NPC29702
0.8121	Intermediate Similarity	NPC476419
0.8105	Intermediate Similarity	NPC471323
0.8049	Intermediate Similarity	NPC273532
0.8046	Intermediate Similarity	NPC135950
0.7966	Intermediate Similarity	NPC103361
0.7965	Intermediate Similarity	NPC44354
0.7895	Intermediate Similarity	NPC282103
0.7845	Intermediate Similarity	NPC289086
0.7823	Intermediate Similarity	NPC165370
0.7823	Intermediate Similarity	NPC212125
0.7797	Intermediate Similarity	NPC109922
0.7758	Intermediate Similarity	NPC41717
0.7717	Intermediate Similarity	NPC63041
0.7717	Intermediate Similarity	NPC470190
0.7709	Intermediate Similarity	NPC320748
0.7709	Intermediate Similarity	NPC324245
0.7705	Intermediate Similarity	NPC309498
0.7682	Intermediate Similarity	NPC322488
0.7676	Intermediate Similarity	NPC472550
0.7676	Intermediate Similarity	NPC304179
0.7676	Intermediate Similarity	NPC48042
0.7676	Intermediate Similarity	NPC472752
0.767	Intermediate Similarity	NPC138370
0.763	Intermediate Similarity	NPC207851
0.7624	Intermediate Similarity	NPC79223
0.7614	Intermediate Similarity	NPC469489
0.7602	Intermediate Similarity	NPC164340
0.7594	Intermediate Similarity	NPC470189
0.7594	Intermediate Similarity	NPC40919
0.7584	Intermediate Similarity	NPC306397
0.7582	Intermediate Similarity	NPC32451
0.7582	Intermediate Similarity	NPC328559
0.7574	Intermediate Similarity	NPC191310
0.7569	Intermediate Similarity	NPC123395
0.7556	Intermediate Similarity	NPC329024
0.7553	Intermediate Similarity	NPC476467
0.7553	Intermediate Similarity	NPC472553
0.7553	Intermediate Similarity	NPC280473
0.7553	Intermediate Similarity	NPC323551
0.7547	Intermediate Similarity	NPC302159
0.7513	Intermediate Similarity	NPC41724
0.7513	Intermediate Similarity	NPC51008
0.7513	Intermediate Similarity	NPC165837
0.75	Intermediate Similarity	NPC105811
0.7485	Intermediate Similarity	NPC209362
0.7484	Intermediate Similarity	NPC467188
0.7474	Intermediate Similarity	NPC228331
0.7474	Intermediate Similarity	NPC4421
0.7474	Intermediate Similarity	NPC319128
0.7474	Intermediate Similarity	NPC264674
0.7435	Intermediate Similarity	NPC477910
0.7435	Intermediate Similarity	NPC42678
0.7435	Intermediate Similarity	NPC193361
0.7435	Intermediate Similarity	NPC62844
0.7435	Intermediate Similarity	NPC477907
0.7435	Intermediate Similarity	NPC207531
0.7435	Intermediate Similarity	NPC470306
0.7435	Intermediate Similarity	NPC477909
0.7418	Intermediate Similarity	NPC59033
0.7418	Intermediate Similarity	NPC317672
0.7396	Intermediate Similarity	NPC477908
0.7396	Intermediate Similarity	NPC206343
0.7396	Intermediate Similarity	NPC6981
0.7396	Intermediate Similarity	NPC470894
0.7396	Intermediate Similarity	NPC475408
0.7396	Intermediate Similarity	NPC471016
0.7396	Intermediate Similarity	NPC471014
0.738	Intermediate Similarity	NPC156044
0.7362	Intermediate Similarity	NPC70406
0.7358	Intermediate Similarity	NPC294579
0.7358	Intermediate Similarity	NPC75600
0.7358	Intermediate Similarity	NPC212768
0.7358	Intermediate Similarity	NPC144779
0.7358	Intermediate Similarity	NPC6576
0.7358	Intermediate Similarity	NPC473115
0.7358	Intermediate Similarity	NPC319556
0.7358	Intermediate Similarity	NPC158020
0.7358	Intermediate Similarity	NPC62367
0.7358	Intermediate Similarity	NPC187494
0.7358	Intermediate Similarity	NPC473089
0.7337	Intermediate Similarity	NPC470279
0.732	Intermediate Similarity	NPC216428
0.732	Intermediate Similarity	NPC84815
0.732	Intermediate Similarity	NPC472555
0.732	Intermediate Similarity	NPC301368
0.7293	Intermediate Similarity	NPC103230
0.7289	Intermediate Similarity	NPC213914
0.7282	Intermediate Similarity	NPC477901
0.7278	Intermediate Similarity	NPC114974
0.7273	Intermediate Similarity	NPC25442
0.7273	Intermediate Similarity	NPC12944
0.7263	Intermediate Similarity	NPC123839
0.7245	Intermediate Similarity	NPC477912
0.7245	Intermediate Similarity	NPC477903
0.7212	Intermediate Similarity	NPC251391
0.7208	Intermediate Similarity	NPC127720
0.7208	Intermediate Similarity	NPC477788
0.7208	Intermediate Similarity	NPC477911
0.7208	Intermediate Similarity	NPC127026
0.7208	Intermediate Similarity	NPC235364
0.7197	Intermediate Similarity	NPC328029
0.7195	Intermediate Similarity	NPC313889
0.719	Intermediate Similarity	NPC313823
0.7188	Intermediate Similarity	NPC118940
0.7186	Intermediate Similarity	NPC138018
0.7184	Intermediate Similarity	NPC84347
0.7172	Intermediate Similarity	NPC250807
0.7172	Intermediate Similarity	NPC76565
0.7172	Intermediate Similarity	NPC57797
0.7172	Intermediate Similarity	NPC471980
0.7169	Intermediate Similarity	NPC229055
0.7158	Intermediate Similarity	NPC266249
0.7143	Intermediate Similarity	NPC82053
0.7136	Intermediate Similarity	NPC473850
0.7136	Intermediate Similarity	NPC477899
0.7136	Intermediate Similarity	NPC477900
0.7136	Intermediate Similarity	NPC26881
0.7136	Intermediate Similarity	NPC328154
0.7136	Intermediate Similarity	NPC477902
0.7136	Intermediate Similarity	NPC475498
0.7136	Intermediate Similarity	NPC475137
0.7136	Intermediate Similarity	NPC233727
0.7126	Intermediate Similarity	NPC74357
0.7115	Intermediate Similarity	NPC330326
0.7111	Intermediate Similarity	NPC278434
0.71	Intermediate Similarity	NPC473506
0.71	Intermediate Similarity	NPC148860
0.7066	Intermediate Similarity	NPC33229
0.7065	Intermediate Similarity	NPC146824
0.7065	Intermediate Similarity	NPC87152
0.7065	Intermediate Similarity	NPC211920
0.7065	Intermediate Similarity	NPC328186
0.7065	Intermediate Similarity	NPC228377
0.7065	Intermediate Similarity	NPC475631
0.7065	Intermediate Similarity	NPC475600
0.7065	Intermediate Similarity	NPC476110
0.7065	Intermediate Similarity	NPC477787
0.7065	Intermediate Similarity	NPC14116
0.7065	Intermediate Similarity	NPC285411
0.7065	Intermediate Similarity	NPC124029
0.7065	Intermediate Similarity	NPC475601
0.7065	Intermediate Similarity	NPC122968
0.7059	Intermediate Similarity	NPC242116
0.7043	Intermediate Similarity	NPC474916
0.7042	Intermediate Similarity	NPC76540
0.703	Intermediate Similarity	NPC470486
0.703	Intermediate Similarity	NPC475362
0.703	Intermediate Similarity	NPC311196
0.703	Intermediate Similarity	NPC471190
0.703	Intermediate Similarity	NPC123906
0.703	Intermediate Similarity	NPC134384
0.703	Intermediate Similarity	NPC475644
0.703	Intermediate Similarity	NPC471977
0.7027	Intermediate Similarity	NPC77061
0.7018	Intermediate Similarity	NPC265100
0.7016	Intermediate Similarity	NPC475835
0.7014	Intermediate Similarity	NPC27802
0.7	Intermediate Similarity	NPC295158
0.6995	Remote Similarity	NPC91125
0.6994	Remote Similarity	NPC70949
0.6989	Remote Similarity	NPC90229
0.6983	Remote Similarity	NPC327373
0.6973	Remote Similarity	NPC146724
0.6966	Remote Similarity	NPC61011
0.6961	Remote Similarity	NPC150698
0.6961	Remote Similarity	NPC475596
0.6961	Remote Similarity	NPC96801
0.6961	Remote Similarity	NPC118084
0.6961	Remote Similarity	NPC473689
0.6961	Remote Similarity	NPC194040
0.6961	Remote Similarity	NPC316841
0.6961	Remote Similarity	NPC477906
0.6961	Remote Similarity	NPC475303
0.6961	Remote Similarity	NPC292416
0.6957	Remote Similarity	NPC471546
0.6946	Remote Similarity	NPC472260
0.694	Remote Similarity	NPC83111
0.6937	Remote Similarity	NPC472288
0.6936	Remote Similarity	NPC114637
0.6927	Remote Similarity	NPC244839
0.6927	Remote Similarity	NPC193238
0.6927	Remote Similarity	NPC320324
0.6927	Remote Similarity	NPC469748
0.6927	Remote Similarity	NPC30456
0.6927	Remote Similarity	NPC213143
0.6927	Remote Similarity	NPC319880
0.6923	Remote Similarity	NPC328798
0.6923	Remote Similarity	NPC111732

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 NPC107287 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	199
0.1-0.2	758
0.2-0.3	867
0.3-0.4	1843
0.4-0.5	3222
0.5-0.6	1800
0.6-0.7	411
0.7-0.8	42
0.8-0.85	2
0.85-0.9	2
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9793	High Similarity	NPD820	Phase 3
0.9718	High Similarity	NPD9271	Approved
0.9296	High Similarity	NPD107	Approved
0.9041	High Similarity	NPD9074	Approved
0.9041	High Similarity	NPD9075	Approved
0.8931	High Similarity	NPD8304	Clinical (unspecified phase)
0.8272	Intermediate Similarity	NPD485	Clinical (unspecified phase)
0.8255	Intermediate Similarity	NPD203	Clinical (unspecified phase)
0.8054	Intermediate Similarity	NPD272	Approved
0.7845	Intermediate Similarity	NPD2831	Approved
0.7823	Intermediate Similarity	NPD9284	Approved
0.7747	Intermediate Similarity	NPD7396	Approved
0.7712	Intermediate Similarity	NPD9506	Approved
0.7663	Intermediate Similarity	NPD3371	Approved
0.7616	Intermediate Similarity	NPD1783	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD175	Clinical (unspecified phase)
0.7594	Intermediate Similarity	NPD4417	Approved
0.7584	Intermediate Similarity	NPD9080	Approved
0.7554	Intermediate Similarity	NPD3947	Discontinued
0.7542	Intermediate Similarity	NPD5975	Clinical (unspecified phase)
0.7528	Intermediate Similarity	NPD4376	Phase 3
0.75	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1270	Approved
0.7486	Intermediate Similarity	NPD1173	Approved
0.7452	Intermediate Similarity	NPD1649	Discontinued
0.7451	Intermediate Similarity	NPD1627	Clinical (unspecified phase)
0.7433	Intermediate Similarity	NPD2509	Approved
0.7433	Intermediate Similarity	NPD2510	Approved
0.7429	Intermediate Similarity	NPD1096	Discontinued
0.7425	Intermediate Similarity	NPD5088	Discontinued
0.7423	Intermediate Similarity	NPD180	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD1623	Approved
0.7337	Intermediate Similarity	NPD4491	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD2896	Discontinued
0.7312	Intermediate Similarity	NPD1352	Discontinued
0.7278	Intermediate Similarity	NPD4804	Approved
0.7235	Intermediate Similarity	NPD4174	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD7010	Phase 3
0.7228	Intermediate Similarity	NPD4987	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD5475	Discontinued
0.7205	Intermediate Similarity	NPD751	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD4805	Approved
0.7186	Intermediate Similarity	NPD2581	Approved
0.7186	Intermediate Similarity	NPD2582	Approved
0.7181	Intermediate Similarity	NPD944	Approved
0.7158	Intermediate Similarity	NPD1367	Phase 2
0.7157	Intermediate Similarity	NPD4301	Approved
0.7152	Intermediate Similarity	NPD5965	Clinical (unspecified phase)
0.715	Intermediate Similarity	NPD3794	Approved
0.715	Intermediate Similarity	NPD3795	Approved
0.7135	Intermediate Similarity	NPD3569	Discontinued
0.7125	Intermediate Similarity	NPD9599	Approved
0.7115	Intermediate Similarity	NPD9100	Approved
0.7099	Intermediate Similarity	NPD3813	Approved
0.7088	Intermediate Similarity	NPD2336	Approved
0.7077	Intermediate Similarity	NPD3389	Approved
0.7077	Intermediate Similarity	NPD3393	Approved
0.7077	Intermediate Similarity	NPD3394	Approved
0.7048	Intermediate Similarity	NPD510	Phase 1
0.7045	Intermediate Similarity	NPD5751	Clinical (unspecified phase)
0.7022	Intermediate Similarity	NPD3178	Discontinued
0.7	Intermediate Similarity	NPD2511	Approved
0.7	Intermediate Similarity	NPD687	Clinical (unspecified phase)
0.697	Remote Similarity	NPD7404	Approved
0.6968	Remote Similarity	NPD5228	Phase 3
0.6964	Remote Similarity	NPD2809	Approved
0.6957	Remote Similarity	NPD981	Phase 2
0.6943	Remote Similarity	NPD6529	Discontinued
0.6941	Remote Similarity	NPD1630	Approved
0.6935	Remote Similarity	NPD2307	Discontinued
0.6935	Remote Similarity	NPD3280	Approved
0.6919	Remote Similarity	NPD4528	Approved
0.6919	Remote Similarity	NPD4526	Approved
0.6919	Remote Similarity	NPD4529	Approved
0.6892	Remote Similarity	NPD269	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD9207	Approved
0.6879	Remote Similarity	NPD9206	Approved
0.6878	Remote Similarity	NPD4396	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD9510	Approved
0.6864	Remote Similarity	NPD2061	Approved
0.6859	Remote Similarity	NPD5513	Phase 2
0.6856	Remote Similarity	NPD5583	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD4072	Approved
0.6854	Remote Similarity	NPD4071	Approved
0.6852	Remote Similarity	NPD569	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD9596	Approved
0.6845	Remote Similarity	NPD7061	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD9595	Approved
0.6837	Remote Similarity	NPD6657	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD9362	Approved
0.6832	Remote Similarity	NPD201	Phase 2
0.6832	Remote Similarity	NPD200	Phase 2
0.6827	Remote Similarity	NPD5891	Approved
0.6821	Remote Similarity	NPD1631	Approved
0.6821	Remote Similarity	NPD6635	Approved
0.6818	Remote Similarity	NPD5490	Discontinued
0.6813	Remote Similarity	NPD4889	Approved
0.6804	Remote Similarity	NPD7467	Discontinued
0.68	Remote Similarity	NPD6872	Clinical (unspecified phase)
0.678	Remote Similarity	NPD2076	Approved
0.678	Remote Similarity	NPD2077	Approved
0.677	Remote Similarity	NPD2670	Approved
0.6769	Remote Similarity	NPD4506	Discontinued
0.6766	Remote Similarity	NPD1996	Discontinued
0.6758	Remote Similarity	NPD721	Approved
0.6757	Remote Similarity	NPD4081	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD5322	Clinical (unspecified phase)
0.673	Remote Similarity	NPD9726	Discontinued
0.6716	Remote Similarity	NPD6770	Approved
0.6705	Remote Similarity	NPD1418	Phase 2
0.6705	Remote Similarity	NPD1343	Approved
0.6701	Remote Similarity	NPD4862	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD1643	Phase 3
0.6684	Remote Similarity	NPD6665	Discontinued
0.6667	Remote Similarity	NPD206	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD8063	Discontinued
0.6667	Remote Similarity	NPD1573	Approved
0.6667	Remote Similarity	NPD1575	Approved
0.6667	Remote Similarity	NPD6226	Phase 3
0.6649	Remote Similarity	NPD9363	Approved
0.6649	Remote Similarity	NPD7049	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD4948	Discontinued
0.6649	Remote Similarity	NPD9364	Phase 2
0.6648	Remote Similarity	NPD1923	Clinical (unspecified phase)
0.6631	Remote Similarity	NPD1977	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD1078	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD271	Approved
0.6623	Remote Similarity	NPD270	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD268	Approved
0.6617	Remote Similarity	NPD3326	Clinical (unspecified phase)
0.6615	Remote Similarity	NPD7289	Clinical (unspecified phase)
0.6613	Remote Similarity	NPD4021	Phase 2
0.6607	Remote Similarity	NPD1801	Approved
0.6607	Remote Similarity	NPD1802	Approved
0.6601	Remote Similarity	NPD8479	Phase 2
0.6596	Remote Similarity	NPD3406	Suspended
0.6593	Remote Similarity	NPD1291	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD1618	Phase 2
0.6593	Remote Similarity	NPD2601	Approved
0.6593	Remote Similarity	NPD2599	Approved
0.6593	Remote Similarity	NPD2600	Approved
0.6591	Remote Similarity	NPD1568	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD1380	Discovery
0.6584	Remote Similarity	NPD4429	Discontinued
0.6575	Remote Similarity	NPD1032	Phase 2
0.6568	Remote Similarity	NPD7528	Approved
0.6566	Remote Similarity	NPD5020	Approved
0.6564	Remote Similarity	NPD6987	Phase 1
0.6564	Remote Similarity	NPD5901	Discontinued
0.6556	Remote Similarity	NPD1586	Approved
0.6556	Remote Similarity	NPD4883	Approved
0.6554	Remote Similarity	NPD5611	Phase 2
0.6552	Remote Similarity	NPD6955	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD2952	Discontinued
0.6538	Remote Similarity	NPD1620	Clinical (unspecified phase)
0.6524	Remote Similarity	NPD3170	Approved
0.6519	Remote Similarity	NPD3238	Discontinued
0.6517	Remote Similarity	NPD5148	Clinical (unspecified phase)
0.6517	Remote Similarity	NPD1292	Clinical (unspecified phase)
0.6517	Remote Similarity	NPD5149	Phase 2
0.6512	Remote Similarity	NPD2512	Phase 3
0.6508	Remote Similarity	NPD4372	Phase 1
0.6503	Remote Similarity	NPD2479	Phase 3
0.6503	Remote Similarity	NPD2481	Approved
0.6502	Remote Similarity	NPD2011	Clinical (unspecified phase)
0.65	Remote Similarity	NPD7069	Discontinued
0.65	Remote Similarity	NPD750	Phase 2
0.6497	Remote Similarity	NPD9357	Approved
0.6494	Remote Similarity	NPD9574	Clinical (unspecified phase)
0.6494	Remote Similarity	NPD9383	Approved
0.6494	Remote Similarity	NPD9382	Approved
0.6486	Remote Similarity	NPD2417	Approved
0.6486	Remote Similarity	NPD2416	Approved
0.6485	Remote Similarity	NPD9076	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD2753	Discontinued
0.6484	Remote Similarity	NPD6642	Approved
0.6484	Remote Similarity	NPD6641	Approved
0.6482	Remote Similarity	NPD648	Clinical (unspecified phase)
0.648	Remote Similarity	NPD6323	Clinical (unspecified phase)
0.648	Remote Similarity	NPD565	Phase 2
0.6477	Remote Similarity	NPD6661	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD6257	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD4703	Approved
0.6471	Remote Similarity	NPD4702	Approved
0.6471	Remote Similarity	NPD4988	Discontinued
0.6467	Remote Similarity	NPD1383	Phase 3
0.6467	Remote Similarity	NPD4011	Clinical (unspecified phase)
0.6467	Remote Similarity	NPD1382	Phase 2
0.6467	Remote Similarity	NPD4824	Approved
0.6467	Remote Similarity	NPD3386	Phase 2
0.6467	Remote Similarity	NPD7414	Clinical (unspecified phase)
0.6467	Remote Similarity	NPD4823	Approved
0.6463	Remote Similarity	NPD9099	Clinical (unspecified phase)
0.6463	Remote Similarity	NPD9098	Phase 3
0.6461	Remote Similarity	NPD6446	Discontinued
0.6458	Remote Similarity	NPD1622	Discontinued
0.6457	Remote Similarity	NPD5255	Approved
0.6453	Remote Similarity	NPD1591	Approved
0.6452	Remote Similarity	NPD1308	Approved
0.6452	Remote Similarity	NPD7424	Clinical (unspecified phase)

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