NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	93.06
Volume:	106.863
LogP:	0.965
LogD:	0.867
LogS:	0.823
# Rotatable Bonds:	0
TPSA:	12.89
# H-Bond Aceptor:	1
# H-Bond Donor:	0
# Rings:	1
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.472
Synthetic Accessibility Score:	1.556
Fsp3:	0.167
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:	-4.163
MDCK Permeability:	3.8426216633524746e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.038
30% Bioavailability (F30%):	0.002

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.826
Plasma Protein Binding (PPB):	31.38161277770996%
Volume Distribution (VD):	2.078
Pgp-substrate:	62.06041717529297%

ADMET: Metabolism

CYP1A2-inhibitor:	0.469
CYP1A2-substrate:	0.53
CYP2C19-inhibitor:	0.079
CYP2C19-substrate:	0.733
CYP2C9-inhibitor:	0.01
CYP2C9-substrate:	0.245
CYP2D6-inhibitor:	0.024
CYP2D6-substrate:	0.645
CYP3A4-inhibitor:	0.012
CYP3A4-substrate:	0.294

ADMET: Excretion

Clearance (CL):	5.861
Half-life (T1/2):	0.541

ADMET: Toxicity

hERG Blockers:	0.022
Human Hepatotoxicity (H-HT):	0.548
Drug-inuced Liver Injury (DILI):	0.206
AMES Toxicity:	0.105
Rat Oral Acute Toxicity:	0.656
Maximum Recommended Daily Dose:	0.021
Skin Sensitization:	0.71
Carcinogencity:	0.479
Eye Corrosion:	0.977
Eye Irritation:	0.996
Respiratory Toxicity:	0.952

Download Data

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

Natural Product: NPC231655

Natural Product ID:	NPC231655
*Common Name:**	2-Methylpyridine
IUPAC Name:	2-methylpyridine
Synonyms:	2-Methyl-Pyridine
Standard InCHIKey:	BSKHPKMHTQYZBB-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C6H7N/c1-6-4-2-3-5-7-6/h2-5H,1H3
SMILES:	Cc1ccccn1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL15732
PubChem CID:	7975
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000089] Pyridines and derivatives [CHEMONTID:0004152] Methylpyridines

*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

☑ 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
IC50	2
Kd	3
Others	6
Potency	8

Activity Type	# Activity
Individual Protein	1
ORGANISM	2
Others	10
Protein Complex	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT300	Individual Protein	Thromboxane-A synthase	Homo sapiens	Inhibition	=	14.7	%	PMID[516872]
NPT413	Protein Complex	Neuronal acetylcholine receptor	Rattus norvegicus	Kd	=	50.0	nM	PMID[516873]
NPT413	Protein Complex	Neuronal acetylcholine receptor	Rattus norvegicus	Kd	=	890000.0	nM	PMID[516873]
NPT413	Protein Complex	Neuronal acetylcholine receptor	Rattus norvegicus	Kd	=	64000000.0	nM	PMID[516873]
NPT413	Protein Complex	Neuronal acetylcholine receptor	Rattus norvegicus	Enhancement	=	38.0	%	PMID[516873]
NPT413	Protein Complex	Neuronal acetylcholine receptor	Rattus norvegicus	Inhibition	=	166.0	%	PMID[516873]
NPT413	Protein Complex	Neuronal acetylcholine receptor	Rattus norvegicus	Mean enhancement of binding	=	20.7	n.a.	PMID[516873]
NPT35	Others	n.a.		pKa	=	6.0	n.a.	PMID[516874]
NPT35	Others	n.a.		pKa	=	5.94	n.a.	PMID[516875]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	IC50	>	20000.0	nM	PMID[516876]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	IC50	>	19952.62	nM	PMID[516876]
NPT2	Others	Unspecified		Potency	n.a.	10671.7	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	74072.2	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	12589.3	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	59359.2	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	23423.7	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	33491.5	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	52439.1	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	471.5	nM	PubChem BioAssay data set

☑ 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 NPC231655 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	3934
0.1-0.2	17810
0.2-0.3	13743
0.3-0.4	3241
0.4-0.5	2214
0.5-0.6	1186
0.6-0.7	418
0.7-0.8	129
0.8-0.85	15
0.85-0.9	4
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.94	High Similarity	NPC83987
0.9048	High Similarity	NPC76540
0.8972	High Similarity	NPC27802
0.8824	High Similarity	NPC213774
0.8559	High Similarity	NPC473901
0.8468	Intermediate Similarity	NPC235843
0.8462	Intermediate Similarity	NPC46358
0.8291	Intermediate Similarity	NPC182570
0.8291	Intermediate Similarity	NPC265605
0.8291	Intermediate Similarity	NPC48564
0.8261	Intermediate Similarity	NPC297486
0.8261	Intermediate Similarity	NPC240136
0.8261	Intermediate Similarity	NPC471402
0.8246	Intermediate Similarity	NPC84268
0.819	Intermediate Similarity	NPC91958
0.819	Intermediate Similarity	NPC143603
0.812	Intermediate Similarity	NPC11863
0.8115	Intermediate Similarity	NPC313823
0.8	Intermediate Similarity	NPC290094
0.7934	Intermediate Similarity	NPC27740
0.792	Intermediate Similarity	NPC256893
0.7917	Intermediate Similarity	NPC56856
0.7869	Intermediate Similarity	NPC245244
0.7869	Intermediate Similarity	NPC146373
0.7869	Intermediate Similarity	NPC166424
0.7805	Intermediate Similarity	NPC169625
0.7805	Intermediate Similarity	NPC202957
0.7787	Intermediate Similarity	NPC476322
0.7752	Intermediate Similarity	NPC314102
0.7752	Intermediate Similarity	NPC251722
0.7742	Intermediate Similarity	NPC471311
0.7742	Intermediate Similarity	NPC471313
0.7698	Intermediate Similarity	NPC282398
0.768	Intermediate Similarity	NPC89490
0.7674	Intermediate Similarity	NPC328029
0.7638	Intermediate Similarity	NPC82295
0.7634	Intermediate Similarity	NPC315348
0.7634	Intermediate Similarity	NPC316811
0.7634	Intermediate Similarity	NPC32002
0.7619	Intermediate Similarity	NPC329896
0.7619	Intermediate Similarity	NPC475105
0.7619	Intermediate Similarity	NPC475090
0.76	Intermediate Similarity	NPC212125
0.7581	Intermediate Similarity	NPC151489
0.7563	Intermediate Similarity	NPC148140
0.7557	Intermediate Similarity	NPC169433
0.7542	Intermediate Similarity	NPC143156
0.7538	Intermediate Similarity	NPC29886
0.7538	Intermediate Similarity	NPC261195
0.752	Intermediate Similarity	NPC135488
0.75	Intermediate Similarity	NPC324611
0.75	Intermediate Similarity	NPC471322
0.75	Intermediate Similarity	NPC81561
0.7481	Intermediate Similarity	NPC150259
0.7481	Intermediate Similarity	NPC84911
0.748	Intermediate Similarity	NPC71236
0.748	Intermediate Similarity	NPC329825
0.748	Intermediate Similarity	NPC476131
0.746	Intermediate Similarity	NPC165370
0.746	Intermediate Similarity	NPC306397
0.7422	Intermediate Similarity	NPC315320
0.7422	Intermediate Similarity	NPC69914
0.7417	Intermediate Similarity	NPC476566
0.7405	Intermediate Similarity	NPC96102
0.7402	Intermediate Similarity	NPC471589
0.7368	Intermediate Similarity	NPC73767
0.7368	Intermediate Similarity	NPC110126
0.7364	Intermediate Similarity	NPC101165
0.7348	Intermediate Similarity	NPC105127
0.7348	Intermediate Similarity	NPC65408
0.7333	Intermediate Similarity	NPC14223
0.7328	Intermediate Similarity	NPC291517
0.7317	Intermediate Similarity	NPC215519
0.7313	Intermediate Similarity	NPC469784
0.7313	Intermediate Similarity	NPC469780
0.7313	Intermediate Similarity	NPC469761
0.7313	Intermediate Similarity	NPC469767
0.7313	Intermediate Similarity	NPC469768
0.7313	Intermediate Similarity	NPC469779
0.7313	Intermediate Similarity	NPC469783
0.7308	Intermediate Similarity	NPC322488
0.7295	Intermediate Similarity	NPC162689
0.7295	Intermediate Similarity	NPC54102
0.7259	Intermediate Similarity	NPC469766
0.7246	Intermediate Similarity	NPC470111
0.7246	Intermediate Similarity	NPC201380
0.7246	Intermediate Similarity	NPC179787
0.7231	Intermediate Similarity	NPC174421
0.7226	Intermediate Similarity	NPC86288
0.7218	Intermediate Similarity	NPC471312
0.7206	Intermediate Similarity	NPC190296
0.7194	Intermediate Similarity	NPC321911
0.7185	Intermediate Similarity	NPC230002
0.7185	Intermediate Similarity	NPC279081
0.7176	Intermediate Similarity	NPC330326
0.7174	Intermediate Similarity	NPC302159
0.7174	Intermediate Similarity	NPC63545
0.7174	Intermediate Similarity	NPC220523
0.7164	Intermediate Similarity	NPC104049
0.7143	Intermediate Similarity	NPC40070
0.7122	Intermediate Similarity	NPC469811
0.7101	Intermediate Similarity	NPC285731
0.7101	Intermediate Similarity	NPC467188
0.7101	Intermediate Similarity	NPC314372
0.7092	Intermediate Similarity	NPC470233
0.709	Intermediate Similarity	NPC472288
0.7087	Intermediate Similarity	NPC122718
0.7068	Intermediate Similarity	NPC23215
0.7015	Intermediate Similarity	NPC29702
0.7007	Intermediate Similarity	NPC476454
0.7	Intermediate Similarity	NPC287895
0.7	Intermediate Similarity	NPC471957
0.6978	Remote Similarity	NPC159856
0.6977	Remote Similarity	NPC476140
0.6972	Remote Similarity	NPC70406
0.6963	Remote Similarity	NPC114310
0.6944	Remote Similarity	NPC476464
0.694	Remote Similarity	NPC198988
0.6929	Remote Similarity	NPC143872
0.6929	Remote Similarity	NPC316069
0.6929	Remote Similarity	NPC288838
0.6929	Remote Similarity	NPC41174
0.6923	Remote Similarity	NPC325903
0.6923	Remote Similarity	NPC278451
0.6923	Remote Similarity	NPC138842
0.6906	Remote Similarity	NPC471323
0.6901	Remote Similarity	NPC313889
0.6901	Remote Similarity	NPC105818
0.6901	Remote Similarity	NPC53947
0.6901	Remote Similarity	NPC24678
0.6897	Remote Similarity	NPC236711
0.6897	Remote Similarity	NPC129721
0.6889	Remote Similarity	NPC325252
0.6879	Remote Similarity	NPC105811
0.6861	Remote Similarity	NPC104483
0.6853	Remote Similarity	NPC470823
0.6853	Remote Similarity	NPC472260
0.6849	Remote Similarity	NPC477591
0.6849	Remote Similarity	NPC56765
0.6849	Remote Similarity	NPC80681
0.6847	Remote Similarity	NPC196580
0.6835	Remote Similarity	NPC20144
0.6812	Remote Similarity	NPC318935
0.6806	Remote Similarity	NPC469763
0.6806	Remote Similarity	NPC469786
0.6806	Remote Similarity	NPC73952
0.6806	Remote Similarity	NPC251391
0.6806	Remote Similarity	NPC469765
0.6806	Remote Similarity	NPC141926
0.6806	Remote Similarity	NPC25008
0.6806	Remote Similarity	NPC259644
0.6806	Remote Similarity	NPC469760
0.6806	Remote Similarity	NPC200214
0.6803	Remote Similarity	NPC25899
0.6803	Remote Similarity	NPC215584
0.6803	Remote Similarity	NPC44773
0.6786	Remote Similarity	NPC230085
0.6786	Remote Similarity	NPC159630
0.6767	Remote Similarity	NPC22079
0.6761	Remote Similarity	NPC477974
0.6759	Remote Similarity	NPC262236
0.6759	Remote Similarity	NPC212376
0.6759	Remote Similarity	NPC211572
0.6759	Remote Similarity	NPC34844
0.6759	Remote Similarity	NPC277608
0.6759	Remote Similarity	NPC70922
0.6759	Remote Similarity	NPC209362
0.6759	Remote Similarity	NPC75540
0.6759	Remote Similarity	NPC80597
0.6736	Remote Similarity	NPC216713
0.6735	Remote Similarity	NPC293487
0.6729	Remote Similarity	NPC76536
0.6712	Remote Similarity	NPC51054
0.6711	Remote Similarity	NPC478182
0.6711	Remote Similarity	NPC265100
0.6711	Remote Similarity	NPC90723
0.6691	Remote Similarity	NPC59084
0.6691	Remote Similarity	NPC2949
0.6689	Remote Similarity	NPC470204
0.6689	Remote Similarity	NPC122141
0.6667	Remote Similarity	NPC286427
0.6644	Remote Similarity	NPC478185
0.6644	Remote Similarity	NPC225018
0.6644	Remote Similarity	NPC48192
0.6644	Remote Similarity	NPC229055
0.6644	Remote Similarity	NPC470203
0.6643	Remote Similarity	NPC473868
0.6643	Remote Similarity	NPC112741
0.6643	Remote Similarity	NPC63157
0.6641	Remote Similarity	NPC273714
0.6623	Remote Similarity	NPC41717
0.6622	Remote Similarity	NPC318065
0.6622	Remote Similarity	NPC41257
0.6622	Remote Similarity	NPC206819
0.662	Remote Similarity	NPC167400
0.6619	Remote Similarity	NPC88097
0.66	Remote Similarity	NPC317105
0.66	Remote Similarity	NPC478184
0.6599	Remote Similarity	NPC469785
0.6599	Remote Similarity	NPC74357

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 NPC231655 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	602
0.1-0.2	1134
0.2-0.3	1415
0.3-0.4	2456
0.4-0.5	2094
0.5-0.6	1064
0.6-0.7	301
0.7-0.8	61
0.8-0.85	14
0.85-0.9	6
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Drug ID	Developmental Stage
1.0	High Similarity	NPD9099	Clinical (unspecified phase)
1.0	High Similarity	NPD9098	Phase 3
0.9091	High Similarity	NPD9396	Approved
0.9091	High Similarity	NPD9392	Approved
0.8807	High Similarity	NPD4823	Approved
0.8807	High Similarity	NPD4824	Approved
0.8547	High Similarity	NPD9357	Approved
0.8407	Intermediate Similarity	NPD269	Clinical (unspecified phase)
0.8403	Intermediate Similarity	NPD9583	Approved
0.8333	Intermediate Similarity	NPD2119	Approved
0.8333	Intermediate Similarity	NPD2118	Approved
0.8291	Intermediate Similarity	NPD271	Approved
0.8291	Intermediate Similarity	NPD268	Approved
0.8291	Intermediate Similarity	NPD270	Clinical (unspecified phase)
0.8246	Intermediate Similarity	NPD60	Approved
0.8182	Intermediate Similarity	NPD991	Phase 2
0.8182	Intermediate Similarity	NPD992	Clinical (unspecified phase)
0.8136	Intermediate Similarity	NPD9598	Discontinued
0.813	Intermediate Similarity	NPD715	Phase 3
0.813	Intermediate Similarity	NPD3476	Approved
0.813	Intermediate Similarity	NPD3475	Approved
0.8103	Intermediate Similarity	NPD8840	Approved
0.8049	Intermediate Similarity	NPD9305	Clinical (unspecified phase)
0.7937	Intermediate Similarity	NPD4029	Approved
0.7937	Intermediate Similarity	NPD4028	Approved
0.7937	Intermediate Similarity	NPD3942	Approved
0.7937	Intermediate Similarity	NPD3944	Approved
0.7937	Intermediate Similarity	NPD4030	Approved
0.7823	Intermediate Similarity	NPD1095	Clinical (unspecified phase)
0.7638	Intermediate Similarity	NPD803	Phase 1
0.7638	Intermediate Similarity	NPD809	Discontinued
0.7634	Intermediate Similarity	NPD2070	Approved
0.7634	Intermediate Similarity	NPD2072	Approved
0.7634	Intermediate Similarity	NPD2071	Approved
0.7634	Intermediate Similarity	NPD2068	Approved
0.7634	Intermediate Similarity	NPD2069	Approved
0.7634	Intermediate Similarity	NPD2074	Approved
0.7634	Intermediate Similarity	NPD174	Discontinued
0.7634	Intermediate Similarity	NPD2075	Approved
0.7634	Intermediate Similarity	NPD2073	Approved
0.7623	Intermediate Similarity	NPD5787	Discontinued
0.7623	Intermediate Similarity	NPD748	Clinical (unspecified phase)
0.7603	Intermediate Similarity	NPD4811	Discontinued
0.76	Intermediate Similarity	NPD1598	Discontinued
0.76	Intermediate Similarity	NPD9284	Approved
0.7557	Intermediate Similarity	NPD9076	Clinical (unspecified phase)
0.754	Intermediate Similarity	NPD1031	Discontinued
0.7463	Intermediate Similarity	NPD3717	Discontinued
0.7463	Intermediate Similarity	NPD2006	Phase 2
0.746	Intermediate Similarity	NPD9080	Approved
0.7442	Intermediate Similarity	NPD1627	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD1995	Approved
0.7442	Intermediate Similarity	NPD1993	Approved
0.7442	Intermediate Similarity	NPD1994	Approved
0.7422	Intermediate Similarity	NPD9207	Approved
0.7422	Intermediate Similarity	NPD9206	Approved
0.7407	Intermediate Similarity	NPD1918	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD198	Clinical (unspecified phase)
0.7388	Intermediate Similarity	NPD1722	Approved
0.7368	Intermediate Similarity	NPD786	Approved
0.7348	Intermediate Similarity	NPD201	Phase 2
0.7348	Intermediate Similarity	NPD200	Phase 2
0.7333	Intermediate Similarity	NPD2007	Clinical (unspecified phase)
0.7328	Intermediate Similarity	NPD2140	Approved
0.7328	Intermediate Similarity	NPD2141	Approved
0.7328	Intermediate Similarity	NPD2142	Approved
0.7299	Intermediate Similarity	NPD7469	Discontinued
0.7279	Intermediate Similarity	NPD649	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD792	Discontinued
0.7246	Intermediate Similarity	NPD4702	Approved
0.7246	Intermediate Similarity	NPD4703	Approved
0.7246	Intermediate Similarity	NPD4547	Phase 3
0.7239	Intermediate Similarity	NPD945	Clinical (unspecified phase)
0.7231	Intermediate Similarity	NPD9726	Discontinued
0.7197	Intermediate Similarity	NPD272	Approved
0.7194	Intermediate Similarity	NPD2430	Phase 2
0.7176	Intermediate Similarity	NPD9100	Approved
0.7143	Intermediate Similarity	NPD7913	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD206	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD461	Approved
0.7122	Intermediate Similarity	NPD1661	Suspended
0.7121	Intermediate Similarity	NPD3385	Approved
0.7111	Intermediate Similarity	NPD4804	Approved
0.7111	Intermediate Similarity	NPD768	Clinical (unspecified phase)
0.7077	Intermediate Similarity	NPD3654	Approved
0.7071	Intermediate Similarity	NPD1183	Approved
0.7063	Intermediate Similarity	NPD1561	Phase 2
0.7059	Intermediate Similarity	NPD2222	Discontinued
0.7059	Intermediate Similarity	NPD1649	Discontinued
0.7059	Intermediate Similarity	NPD9599	Approved
0.7042	Intermediate Similarity	NPD2012	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD180	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD2896	Discontinued
0.7029	Intermediate Similarity	NPD1352	Discontinued
0.7021	Intermediate Similarity	NPD971	Clinical (unspecified phase)
0.7015	Intermediate Similarity	NPD490	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD4805	Approved
0.6993	Remote Similarity	NPD4436	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD2165	Phase 1
0.6972	Remote Similarity	NPD9343	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD9506	Approved
0.6957	Remote Similarity	NPD4510	Discontinued
0.695	Remote Similarity	NPD2102	Approved
0.695	Remote Similarity	NPD3100	Discontinued
0.695	Remote Similarity	NPD2104	Approved
0.6944	Remote Similarity	NPD3114	Approved
0.6944	Remote Similarity	NPD3113	Approved
0.6944	Remote Similarity	NPD3115	Approved
0.6944	Remote Similarity	NPD3112	Approved
0.6934	Remote Similarity	NPD1395	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD2837	Discontinued
0.6923	Remote Similarity	NPD3339	Approved
0.6912	Remote Similarity	NPD1380	Discovery
0.6912	Remote Similarity	NPD203	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD751	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD3813	Approved
0.6901	Remote Similarity	NPD2172	Phase 1
0.6897	Remote Similarity	NPD2582	Approved
0.6897	Remote Similarity	NPD2865	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD6497	Approved
0.6897	Remote Similarity	NPD2581	Approved
0.6889	Remote Similarity	NPD1255	Approved
0.6889	Remote Similarity	NPD1253	Approved
0.6889	Remote Similarity	NPD1256	Approved
0.6889	Remote Similarity	NPD1254	Approved
0.6875	Remote Similarity	NPD975	Approved
0.6875	Remote Similarity	NPD977	Approved
0.6875	Remote Similarity	NPD976	Approved
0.687	Remote Similarity	NPD5352	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD175	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD2103	Approved
0.6849	Remote Similarity	NPD604	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD5255	Approved
0.6838	Remote Similarity	NPD6554	Approved
0.6838	Remote Similarity	NPD45	Approved
0.6831	Remote Similarity	NPD4374	Clinical (unspecified phase)
0.6812	Remote Similarity	NPD107	Approved
0.6812	Remote Similarity	NPD165	Phase 2
0.6809	Remote Similarity	NPD6148	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD491	Approved
0.6783	Remote Similarity	NPD2465	Approved
0.6783	Remote Similarity	NPD2462	Phase 3
0.6783	Remote Similarity	NPD2466	Phase 3
0.6781	Remote Similarity	NPD1192	Clinical (unspecified phase)
0.6781	Remote Similarity	NPD1869	Phase 2
0.6763	Remote Similarity	NPD1382	Phase 2
0.6763	Remote Similarity	NPD1383	Phase 3
0.6761	Remote Similarity	NPD2110	Approved
0.6761	Remote Similarity	NPD1270	Approved
0.6757	Remote Similarity	NPD2385	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD1015	Phase 2
0.6757	Remote Similarity	NPD1016	Phase 2
0.6757	Remote Similarity	NPD5315	Discontinued
0.6757	Remote Similarity	NPD4384	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD6771	Discontinued
0.6738	Remote Similarity	NPD1366	Approved
0.6738	Remote Similarity	NPD1364	Approved
0.6738	Remote Similarity	NPD1365	Approved
0.6735	Remote Similarity	NPD3433	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD5418	Discontinued
0.6714	Remote Similarity	NPD1427	Clinical (unspecified phase)
0.6714	Remote Similarity	NPD4637	Clinical (unspecified phase)
0.6712	Remote Similarity	NPD473	Clinical (unspecified phase)
0.6712	Remote Similarity	NPD2580	Discontinued
0.6711	Remote Similarity	NPD3323	Discontinued
0.6692	Remote Similarity	NPD947	Approved
0.6691	Remote Similarity	NPD7135	Phase 2
0.669	Remote Similarity	NPD1917	Discontinued
0.6689	Remote Similarity	NPD112	Approved
0.6689	Remote Similarity	NPD9705	Discontinued
0.6667	Remote Similarity	NPD925	Approved
0.6667	Remote Similarity	NPD2059	Approved
0.6667	Remote Similarity	NPD1333	Phase 3
0.6667	Remote Similarity	NPD2057	Approved
0.6667	Remote Similarity	NPD926	Approved
0.6667	Remote Similarity	NPD2058	Phase 2
0.6667	Remote Similarity	NPD2323	Clinical (unspecified phase)
0.6644	Remote Similarity	NPD1853	Clinical (unspecified phase)
0.6644	Remote Similarity	NPD5358	Clinical (unspecified phase)
0.6644	Remote Similarity	NPD2809	Approved
0.6644	Remote Similarity	NPD5400	Approved
0.6643	Remote Similarity	NPD5020	Approved
0.6643	Remote Similarity	NPD9271	Approved
0.6623	Remote Similarity	NPD3929	Clinical (unspecified phase)
0.6622	Remote Similarity	NPD704	Clinical (unspecified phase)
0.6621	Remote Similarity	NPD4641	Discontinued
0.662	Remote Similarity	NPD9074	Approved
0.662	Remote Similarity	NPD9075	Approved
0.6599	Remote Similarity	NPD2748	Clinical (unspecified phase)
0.6597	Remote Similarity	NPD162	Approved
0.6597	Remote Similarity	NPD426	Approved
0.6597	Remote Similarity	NPD428	Approved
0.6597	Remote Similarity	NPD427	Approved
0.6593	Remote Similarity	NPD1251	Discontinued
0.6579	Remote Similarity	NPD2640	Approved
0.6579	Remote Similarity	NPD4779	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD7287	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD1343	Approved
0.6579	Remote Similarity	NPD2390	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD2641	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