NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	107.07
Volume:	124.159
LogP:	1.662
LogD:	1.449
LogS:	0.125
# Rotatable Bonds:	1
TPSA:	12.89
# H-Bond Aceptor:	1
# H-Bond Donor:	0
# Rings:	1
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.531
Synthetic Accessibility Score:	1.589
Fsp3:	0.286
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.074
MDCK Permeability:	3.853704038192518e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.141
30% Bioavailability (F30%):	0.034

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.858
Plasma Protein Binding (PPB):	40.2008171081543%
Volume Distribution (VD):	1.708
Pgp-substrate:	47.69662094116211%

ADMET: Metabolism

CYP1A2-inhibitor:	0.931
CYP1A2-substrate:	0.605
CYP2C19-inhibitor:	0.624
CYP2C19-substrate:	0.794
CYP2C9-inhibitor:	0.145
CYP2C9-substrate:	0.326
CYP2D6-inhibitor:	0.28
CYP2D6-substrate:	0.304
CYP3A4-inhibitor:	0.25
CYP3A4-substrate:	0.369

ADMET: Excretion

Clearance (CL):	12.669
Half-life (T1/2):	0.805

ADMET: Toxicity

hERG Blockers:	0.048
Human Hepatotoxicity (H-HT):	0.048
Drug-inuced Liver Injury (DILI):	0.376
AMES Toxicity:	0.009
Rat Oral Acute Toxicity:	0.716
Maximum Recommended Daily Dose:	0.051
Skin Sensitization:	0.922
Carcinogencity:	0.338
Eye Corrosion:	0.957
Eye Irritation:	0.99
Respiratory Toxicity:	0.645

Download Data

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

Natural Product: NPC27802

Natural Product ID:	NPC27802
*Common Name:**	3-Ethylpyridine
IUPAC Name:	3-ethylpyridine
Synonyms:	3-Ethyl-Pyridine
Standard InCHIKey:	MFEIKQPHQINPRI-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C7H9N/c1-2-7-4-3-5-8-6-7/h3-6H,2H2,1H3
SMILES:	CCc1cccnc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL23025
PubChem CID:	10823
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000089] Pyridines and derivatives

*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
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	Flowers	n.a.	n.a.	DOI[10.1002/elan.200403102]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	Flowers	n.a.	n.a.	DOI[10.1016/j.foodchem.2012.02.124]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	Flowers	n.a.	n.a.	PMID[11077184]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	Flowers	n.a.	n.a.	PMID[17328234]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	Flower buds	n.a.	n.a.	PMID[18321056]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	flower	n.a.	PMID[21804227]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	flower bud	n.a.	PMID[21942812]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	flower buds	Henan province, China	2005-MAY	PMID[21942812]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	leaf	n.a.	PMID[23265495]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	Flower buds	n.a.	n.a.	PMID[24279769]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	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
Kd	2
Others	3

Activity Type	# Activity
Protein Complex	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT413	Protein Complex	Neuronal acetylcholine receptor	Rattus norvegicus	Kd	=	9500.0	nM	PMID[473044]
NPT413	Protein Complex	Neuronal acetylcholine receptor	Rattus norvegicus	Kd	=	2800000.0	nM	PMID[473044]
NPT413	Protein Complex	Neuronal acetylcholine receptor	Rattus norvegicus	Enhancement	=	20.0	%	PMID[473044]
NPT413	Protein Complex	Neuronal acetylcholine receptor	Rattus norvegicus	Inhibition	=	109.0	%	PMID[473044]
NPT413	Protein Complex	Neuronal acetylcholine receptor	Rattus norvegicus	Mean enhancement of binding	=	5.4	n.a.	PMID[473044]

☑ 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 NPC27802 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	2435
0.1-0.2	13954
0.2-0.3	16597
0.3-0.4	4993
0.4-0.5	2584
0.5-0.6	1458
0.6-0.7	484
0.7-0.8	145
0.8-0.85	26
0.85-0.9	13
0.9-0.95	6
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9709	High Similarity	NPC76540
0.9189	High Similarity	NPC471402
0.9189	High Similarity	NPC297486
0.9189	High Similarity	NPC240136
0.9126	High Similarity	NPC83987
0.9107	High Similarity	NPC91958
0.9083	High Similarity	NPC235843
0.9035	High Similarity	NPC265605
0.9035	High Similarity	NPC182570
0.9035	High Similarity	NPC48564
0.8972	High Similarity	NPC231655
0.8938	High Similarity	NPC143603
0.8879	High Similarity	NPC290094
0.8655	High Similarity	NPC169625
0.8655	High Similarity	NPC202957
0.8644	High Similarity	NPC27740
0.8644	High Similarity	NPC476322
0.8571	High Similarity	NPC146373
0.8571	High Similarity	NPC166424
0.8571	High Similarity	NPC245244
0.8559	High Similarity	NPC46358
0.8512	High Similarity	NPC89490
0.8443	Intermediate Similarity	NPC475105
0.8443	Intermediate Similarity	NPC475090
0.8443	Intermediate Similarity	NPC329896
0.843	Intermediate Similarity	NPC471311
0.843	Intermediate Similarity	NPC471313
0.8333	Intermediate Similarity	NPC473901
0.8319	Intermediate Similarity	NPC329825
0.8293	Intermediate Similarity	NPC476131
0.8279	Intermediate Similarity	NPC212125
0.8226	Intermediate Similarity	NPC69914
0.8226	Intermediate Similarity	NPC282398
0.8226	Intermediate Similarity	NPC315320
0.816	Intermediate Similarity	NPC471322
0.816	Intermediate Similarity	NPC256893
0.816	Intermediate Similarity	NPC324611
0.816	Intermediate Similarity	NPC101165
0.8056	Intermediate Similarity	NPC213774
0.8034	Intermediate Similarity	NPC84268
0.7984	Intermediate Similarity	NPC314102
0.7984	Intermediate Similarity	NPC251722
0.7984	Intermediate Similarity	NPC65408
0.7984	Intermediate Similarity	NPC165370
0.7984	Intermediate Similarity	NPC306397
0.7953	Intermediate Similarity	NPC322488
0.792	Intermediate Similarity	NPC471589
0.7917	Intermediate Similarity	NPC11863
0.7869	Intermediate Similarity	NPC56856
0.7863	Intermediate Similarity	NPC32002
0.7863	Intermediate Similarity	NPC316811
0.7863	Intermediate Similarity	NPC315348
0.7846	Intermediate Similarity	NPC471312
0.7815	Intermediate Similarity	NPC148140
0.7786	Intermediate Similarity	NPC169433
0.7769	Intermediate Similarity	NPC29886
0.7769	Intermediate Similarity	NPC261195
0.775	Intermediate Similarity	NPC81561
0.7734	Intermediate Similarity	NPC82295
0.771	Intermediate Similarity	NPC150259
0.771	Intermediate Similarity	NPC84911
0.7674	Intermediate Similarity	NPC330326
0.7667	Intermediate Similarity	NPC476566
0.7634	Intermediate Similarity	NPC29702
0.7634	Intermediate Similarity	NPC96102
0.7612	Intermediate Similarity	NPC476454
0.7594	Intermediate Similarity	NPC110126
0.7594	Intermediate Similarity	NPC73767
0.7576	Intermediate Similarity	NPC105127
0.7561	Intermediate Similarity	NPC215519
0.7541	Intermediate Similarity	NPC162689
0.7541	Intermediate Similarity	NPC54102
0.7537	Intermediate Similarity	NPC469783
0.7537	Intermediate Similarity	NPC469779
0.7537	Intermediate Similarity	NPC469780
0.7537	Intermediate Similarity	NPC469767
0.7537	Intermediate Similarity	NPC469784
0.7537	Intermediate Similarity	NPC469761
0.7537	Intermediate Similarity	NPC469768
0.75	Intermediate Similarity	NPC471323
0.7481	Intermediate Similarity	NPC469766
0.748	Intermediate Similarity	NPC135488
0.7464	Intermediate Similarity	NPC477974
0.7464	Intermediate Similarity	NPC201380
0.7464	Intermediate Similarity	NPC470111
0.7464	Intermediate Similarity	NPC179787
0.7445	Intermediate Similarity	NPC467188
0.7445	Intermediate Similarity	NPC86288
0.7444	Intermediate Similarity	NPC114310
0.7426	Intermediate Similarity	NPC190296
0.741	Intermediate Similarity	NPC321911
0.7407	Intermediate Similarity	NPC279081
0.7402	Intermediate Similarity	NPC151489
0.7391	Intermediate Similarity	NPC63545
0.7364	Intermediate Similarity	NPC313823
0.7357	Intermediate Similarity	NPC40070
0.7338	Intermediate Similarity	NPC469811
0.7338	Intermediate Similarity	NPC105811
0.7323	Intermediate Similarity	NPC122718
0.7319	Intermediate Similarity	NPC314372
0.7319	Intermediate Similarity	NPC285731
0.7305	Intermediate Similarity	NPC470233
0.7279	Intermediate Similarity	NPC230002
0.7246	Intermediate Similarity	NPC230085
0.7246	Intermediate Similarity	NPC159630
0.7214	Intermediate Similarity	NPC471957
0.7209	Intermediate Similarity	NPC476140
0.7194	Intermediate Similarity	NPC159856
0.7183	Intermediate Similarity	NPC70406
0.7174	Intermediate Similarity	NPC477977
0.7165	Intermediate Similarity	NPC41174
0.7164	Intermediate Similarity	NPC198988
0.7154	Intermediate Similarity	NPC278451
0.7153	Intermediate Similarity	NPC476464
0.7143	Intermediate Similarity	NPC288838
0.7143	Intermediate Similarity	NPC143872
0.7133	Intermediate Similarity	NPC138842
0.7133	Intermediate Similarity	NPC325903
0.713	Intermediate Similarity	NPC14223
0.7113	Intermediate Similarity	NPC24678
0.7113	Intermediate Similarity	NPC53947
0.7113	Intermediate Similarity	NPC105818
0.7111	Intermediate Similarity	NPC328029
0.7111	Intermediate Similarity	NPC325252
0.7103	Intermediate Similarity	NPC236711
0.7103	Intermediate Similarity	NPC469897
0.7103	Intermediate Similarity	NPC129721
0.7092	Intermediate Similarity	NPC112741
0.7083	Intermediate Similarity	NPC209362
0.708	Intermediate Similarity	NPC104483
0.7071	Intermediate Similarity	NPC167400
0.7068	Intermediate Similarity	NPC174421
0.7063	Intermediate Similarity	NPC470823
0.7055	Intermediate Similarity	NPC80681
0.7055	Intermediate Similarity	NPC477591
0.7055	Intermediate Similarity	NPC56765
0.705	Intermediate Similarity	NPC20144
0.7021	Intermediate Similarity	NPC316069
0.7014	Intermediate Similarity	NPC469763
0.7014	Intermediate Similarity	NPC469765
0.7014	Intermediate Similarity	NPC73952
0.7014	Intermediate Similarity	NPC141926
0.7014	Intermediate Similarity	NPC25008
0.7014	Intermediate Similarity	NPC251391
0.7014	Intermediate Similarity	NPC200214
0.7014	Intermediate Similarity	NPC469760
0.7014	Intermediate Similarity	NPC259644
0.7014	Intermediate Similarity	NPC107287
0.7014	Intermediate Similarity	NPC469786
0.7007	Intermediate Similarity	NPC215584
0.7007	Intermediate Similarity	NPC44773
0.6993	Remote Similarity	NPC313889
0.6992	Remote Similarity	NPC22079
0.6966	Remote Similarity	NPC80597
0.6966	Remote Similarity	NPC212376
0.6966	Remote Similarity	NPC70922
0.6966	Remote Similarity	NPC211572
0.6966	Remote Similarity	NPC34844
0.6966	Remote Similarity	NPC75540
0.6966	Remote Similarity	NPC229055
0.6959	Remote Similarity	NPC71079
0.6944	Remote Similarity	NPC472260
0.6944	Remote Similarity	NPC216713
0.6939	Remote Similarity	NPC293487
0.6935	Remote Similarity	NPC143156
0.6918	Remote Similarity	NPC51054
0.6918	Remote Similarity	NPC74357
0.6913	Remote Similarity	NPC265100
0.6913	Remote Similarity	NPC474217
0.6913	Remote Similarity	NPC90723
0.6913	Remote Similarity	NPC473057
0.6913	Remote Similarity	NPC478182
0.6906	Remote Similarity	NPC2949
0.6906	Remote Similarity	NPC59084
0.6892	Remote Similarity	NPC470204
0.6892	Remote Similarity	NPC122141
0.6884	Remote Similarity	NPC104049
0.6871	Remote Similarity	NPC286427
0.6871	Remote Similarity	NPC213914
0.6867	Remote Similarity	NPC477975
0.6867	Remote Similarity	NPC85918
0.6857	Remote Similarity	NPC63157
0.6857	Remote Similarity	NPC473868
0.6849	Remote Similarity	NPC263455
0.6846	Remote Similarity	NPC124542
0.6846	Remote Similarity	NPC225018
0.6846	Remote Similarity	NPC59779
0.6846	Remote Similarity	NPC470203
0.6846	Remote Similarity	NPC471177
0.6835	Remote Similarity	NPC88097
0.6824	Remote Similarity	NPC318065
0.6824	Remote Similarity	NPC206819
0.6824	Remote Similarity	NPC41257
0.6821	Remote Similarity	NPC98187
0.6821	Remote Similarity	NPC127730
0.6821	Remote Similarity	NPC41717
0.6821	Remote Similarity	NPC278366
0.6818	Remote Similarity	NPC250361
0.6812	Remote Similarity	NPC125746
0.6806	Remote Similarity	NPC123906

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 NPC27802 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	540
0.1-0.2	998
0.2-0.3	1017
0.3-0.4	2310
0.4-0.5	2502
0.5-0.6	1304
0.6-0.7	351
0.7-0.8	96
0.8-0.85	21
0.85-0.9	10
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9182	High Similarity	NPD269	Clinical (unspecified phase)
0.9035	High Similarity	NPD268	Approved
0.9035	High Similarity	NPD271	Approved
0.9035	High Similarity	NPD270	Clinical (unspecified phase)
0.8972	High Similarity	NPD9099	Clinical (unspecified phase)
0.8972	High Similarity	NPD9098	Phase 3
0.8803	High Similarity	NPD9357	Approved
0.8739	High Similarity	NPD4824	Approved
0.8739	High Similarity	NPD4823	Approved
0.8655	High Similarity	NPD9583	Approved
0.8583	High Similarity	NPD2119	Approved
0.8583	High Similarity	NPD2118	Approved
0.843	Intermediate Similarity	NPD1598	Discontinued
0.843	Intermediate Similarity	NPD992	Clinical (unspecified phase)
0.843	Intermediate Similarity	NPD991	Phase 2
0.8374	Intermediate Similarity	NPD3475	Approved
0.8374	Intermediate Similarity	NPD3476	Approved
0.8362	Intermediate Similarity	NPD9392	Approved
0.8362	Intermediate Similarity	NPD9396	Approved
0.8319	Intermediate Similarity	NPD748	Clinical (unspecified phase)
0.8279	Intermediate Similarity	NPD9284	Approved
0.824	Intermediate Similarity	NPD1627	Clinical (unspecified phase)
0.824	Intermediate Similarity	NPD1994	Approved
0.824	Intermediate Similarity	NPD1993	Approved
0.824	Intermediate Similarity	NPD1995	Approved
0.8226	Intermediate Similarity	NPD9207	Approved
0.8226	Intermediate Similarity	NPD9206	Approved
0.8226	Intermediate Similarity	NPD715	Phase 3
0.8175	Intermediate Similarity	NPD3944	Approved
0.8175	Intermediate Similarity	NPD4029	Approved
0.8175	Intermediate Similarity	NPD4030	Approved
0.8175	Intermediate Similarity	NPD4028	Approved
0.8175	Intermediate Similarity	NPD3942	Approved
0.811	Intermediate Similarity	NPD2142	Approved
0.811	Intermediate Similarity	NPD2140	Approved
0.811	Intermediate Similarity	NPD2141	Approved
0.8047	Intermediate Similarity	NPD792	Discontinued
0.8034	Intermediate Similarity	NPD60	Approved
0.7984	Intermediate Similarity	NPD201	Phase 2
0.7984	Intermediate Similarity	NPD200	Phase 2
0.7984	Intermediate Similarity	NPD9080	Approved
0.7899	Intermediate Similarity	NPD8840	Approved
0.7874	Intermediate Similarity	NPD803	Phase 1
0.7874	Intermediate Similarity	NPD9726	Discontinued
0.7863	Intermediate Similarity	NPD2070	Approved
0.7863	Intermediate Similarity	NPD2069	Approved
0.7863	Intermediate Similarity	NPD2068	Approved
0.7863	Intermediate Similarity	NPD2075	Approved
0.7863	Intermediate Similarity	NPD2074	Approved
0.7863	Intermediate Similarity	NPD2071	Approved
0.7863	Intermediate Similarity	NPD2073	Approved
0.7863	Intermediate Similarity	NPD2072	Approved
0.7829	Intermediate Similarity	NPD272	Approved
0.7787	Intermediate Similarity	NPD9598	Discontinued
0.7786	Intermediate Similarity	NPD2896	Discontinued
0.7769	Intermediate Similarity	NPD206	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD768	Clinical (unspecified phase)
0.7687	Intermediate Similarity	NPD4510	Discontinued
0.7687	Intermediate Similarity	NPD2006	Phase 2
0.7674	Intermediate Similarity	NPD9100	Approved
0.7634	Intermediate Similarity	NPD198	Clinical (unspecified phase)
0.763	Intermediate Similarity	NPD1918	Clinical (unspecified phase)
0.763	Intermediate Similarity	NPD751	Clinical (unspecified phase)
0.7612	Intermediate Similarity	NPD1722	Approved
0.7597	Intermediate Similarity	NPD809	Discontinued
0.7594	Intermediate Similarity	NPD945	Clinical (unspecified phase)
0.7594	Intermediate Similarity	NPD786	Approved
0.7576	Intermediate Similarity	NPD9506	Approved
0.7556	Intermediate Similarity	NPD2007	Clinical (unspecified phase)
0.7537	Intermediate Similarity	NPD1649	Discontinued
0.7537	Intermediate Similarity	NPD9599	Approved
0.7519	Intermediate Similarity	NPD203	Clinical (unspecified phase)
0.7519	Intermediate Similarity	NPD1380	Discovery
0.7518	Intermediate Similarity	NPD6148	Clinical (unspecified phase)
0.7518	Intermediate Similarity	NPD7469	Discontinued
0.75	Intermediate Similarity	NPD3813	Approved
0.75	Intermediate Similarity	NPD1095	Clinical (unspecified phase)
0.7464	Intermediate Similarity	NPD2110	Approved
0.7464	Intermediate Similarity	NPD1270	Approved
0.7464	Intermediate Similarity	NPD4702	Approved
0.7464	Intermediate Similarity	NPD4547	Phase 3
0.7464	Intermediate Similarity	NPD4703	Approved
0.7442	Intermediate Similarity	NPD9305	Clinical (unspecified phase)
0.7426	Intermediate Similarity	NPD3717	Discontinued
0.741	Intermediate Similarity	NPD2430	Phase 2
0.7407	Intermediate Similarity	NPD1395	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD649	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD1352	Discontinued
0.7368	Intermediate Similarity	NPD490	Clinical (unspecified phase)
0.7357	Intermediate Similarity	NPD2462	Phase 3
0.7357	Intermediate Similarity	NPD2466	Phase 3
0.7357	Intermediate Similarity	NPD2465	Approved
0.7353	Intermediate Similarity	NPD1383	Phase 3
0.7353	Intermediate Similarity	NPD1382	Phase 2
0.7348	Intermediate Similarity	NPD3385	Approved
0.7338	Intermediate Similarity	NPD1661	Suspended
0.7319	Intermediate Similarity	NPD175	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD3654	Approved
0.7305	Intermediate Similarity	NPD4641	Discontinued
0.7302	Intermediate Similarity	NPD1561	Phase 2
0.7299	Intermediate Similarity	NPD1427	Clinical (unspecified phase)
0.7286	Intermediate Similarity	NPD1183	Approved
0.7279	Intermediate Similarity	NPD107	Approved
0.7254	Intermediate Similarity	NPD2012	Clinical (unspecified phase)
0.7214	Intermediate Similarity	NPD2089	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD2165	Phase 1
0.7183	Intermediate Similarity	NPD5965	Clinical (unspecified phase)
0.7183	Intermediate Similarity	NPD3262	Approved
0.7163	Intermediate Similarity	NPD3100	Discontinued
0.7153	Intermediate Similarity	NPD3113	Approved
0.7153	Intermediate Similarity	NPD3112	Approved
0.7153	Intermediate Similarity	NPD3114	Approved
0.7153	Intermediate Similarity	NPD3115	Approved
0.7153	Intermediate Similarity	NPD6026	Approved
0.7133	Intermediate Similarity	NPD3339	Approved
0.7133	Intermediate Similarity	NPD1917	Discontinued
0.7133	Intermediate Similarity	NPD2837	Discontinued
0.7113	Intermediate Similarity	NPD2172	Phase 1
0.7111	Intermediate Similarity	NPD1256	Approved
0.7111	Intermediate Similarity	NPD1255	Approved
0.7111	Intermediate Similarity	NPD1254	Approved
0.7111	Intermediate Similarity	NPD1253	Approved
0.7103	Intermediate Similarity	NPD6497	Approved
0.7103	Intermediate Similarity	NPD2581	Approved
0.7103	Intermediate Similarity	NPD2582	Approved
0.7103	Intermediate Similarity	NPD2865	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD9271	Approved
0.7083	Intermediate Similarity	NPD975	Approved
0.7083	Intermediate Similarity	NPD2061	Approved
0.7083	Intermediate Similarity	NPD2809	Approved
0.7083	Intermediate Similarity	NPD1328	Approved
0.7083	Intermediate Similarity	NPD976	Approved
0.7083	Intermediate Similarity	NPD977	Approved
0.708	Intermediate Similarity	NPD4804	Approved
0.708	Intermediate Similarity	NPD174	Discontinued
0.7071	Intermediate Similarity	NPD9075	Approved
0.7071	Intermediate Similarity	NPD9074	Approved
0.7059	Intermediate Similarity	NPD6554	Approved
0.7059	Intermediate Similarity	NPD45	Approved
0.7055	Intermediate Similarity	NPD5255	Approved
0.7042	Intermediate Similarity	NPD4374	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD2748	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD5787	Discontinued
0.7008	Intermediate Similarity	NPD4811	Discontinued
0.7007	Intermediate Similarity	NPD2511	Approved
0.7	Intermediate Similarity	NPD1988	Phase 1
0.6986	Remote Similarity	NPD1192	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD5541	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD4805	Approved
0.697	Remote Similarity	NPD1031	Discontinued
0.6966	Remote Similarity	NPD5358	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD8026	Phase 1
0.6959	Remote Similarity	NPD6771	Discontinued
0.6959	Remote Similarity	NPD5315	Discontinued
0.6959	Remote Similarity	NPD2385	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD4384	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD5418	Discontinued
0.6929	Remote Similarity	NPD4637	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD473	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD2580	Discontinued
0.6917	Remote Similarity	NPD947	Approved
0.6913	Remote Similarity	NPD3583	Phase 2
0.6913	Remote Similarity	NPD5088	Discontinued
0.6913	Remote Similarity	NPD3323	Discontinued
0.6913	Remote Similarity	NPD6635	Approved
0.6906	Remote Similarity	NPD2222	Discontinued
0.6892	Remote Similarity	NPD6454	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD9076	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD2323	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD820	Phase 3
0.6867	Remote Similarity	NPD925	Approved
0.6867	Remote Similarity	NPD926	Approved
0.6857	Remote Similarity	NPD5020	Approved
0.6857	Remote Similarity	NPD461	Approved
0.6846	Remote Similarity	NPD5400	Approved
0.6846	Remote Similarity	NPD1853	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD704	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD4174	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD5611	Phase 2
0.6821	Remote Similarity	NPD3929	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD1251	Discontinued
0.6786	Remote Similarity	NPD165	Phase 2
0.6783	Remote Similarity	NPD1683	Approved
0.6779	Remote Similarity	NPD112	Approved
0.6779	Remote Similarity	NPD1403	Approved
0.6779	Remote Similarity	NPD9705	Discontinued
0.6779	Remote Similarity	NPD1404	Approved
0.6776	Remote Similarity	NPD7287	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD4779	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD6872	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD2640	Approved
0.6776	Remote Similarity	NPD2390	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD2641	Approved
0.6776	Remote Similarity	NPD1343	Approved
0.6761	Remote Similarity	NPD3401	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD2145	Clinical (unspecified phase)
0.6755	Remote Similarity	NPD2782	Approved
0.6755	Remote Similarity	NPD2720	Phase 1
0.6755	Remote Similarity	NPD2719	Clinical (unspecified phase)
0.6755	Remote Similarity	NPD2780	Approved

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