NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	173.0
Volume:	152.672
LogP:	0.615
LogD:	1.416
LogS:	-2.632
# Rotatable Bonds:	2
TPSA:	26.94
# H-Bond Aceptor:	2
# H-Bond Donor:	0
# Rings:	1
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.387
Synthetic Accessibility Score:	3.432
Fsp3:	0.167
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.45
MDCK Permeability:	3.910272062057629e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.019

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.731
Plasma Protein Binding (PPB):	28.667770385742188%
Volume Distribution (VD):	0.621
Pgp-substrate:	74.80530548095703%

ADMET: Metabolism

CYP1A2-inhibitor:	0.246
CYP1A2-substrate:	0.844
CYP2C19-inhibitor:	0.391
CYP2C19-substrate:	0.55
CYP2C9-inhibitor:	0.048
CYP2C9-substrate:	0.129
CYP2D6-inhibitor:	0.017
CYP2D6-substrate:	0.098
CYP3A4-inhibitor:	0.004
CYP3A4-substrate:	0.231

ADMET: Excretion

Clearance (CL):	11.752
Half-life (T1/2):	0.677

ADMET: Toxicity

hERG Blockers:	0.235
Human Hepatotoxicity (H-HT):	0.286
Drug-inuced Liver Injury (DILI):	0.464
AMES Toxicity:	0.739
Rat Oral Acute Toxicity:	0.798
Maximum Recommended Daily Dose:	0.031
Skin Sensitization:	0.923
Carcinogencity:	0.55
Eye Corrosion:	0.976
Eye Irritation:	0.99
Respiratory Toxicity:	0.984

Download Data

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

Natural Product: NPC11863

Natural Product ID:	NPC11863
*Common Name:**	2-(Methyldithio)Pyridine-N-Oxide
IUPAC Name:	2-(methyldisulfanyl)-1-oxidopyridin-1-ium
Synonyms:	2-(Methyldisulfanyl)Pyridine 1-Oxide
Standard InCHIKey:	XKLCDAACRKRTLY-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C6H7NOS2/c1-9-10-6-4-2-3-5-7(6)8/h2-5H,1H3
SMILES:	CSSc1ccccn1=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL538132
PubChem CID:	13386157
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000089] Pyridines and derivatives [CHEMONTID:0001764] Pyridinium 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
NPO13010	Allium stipitatum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19093848]
NPO13010	Allium stipitatum	Species	Amaryllidaceae	Eukaryota	n.a.	bulb	n.a.	PMID[19093848]
NPO13010	Allium stipitatum	Species	Amaryllidaceae	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
IC50	5
MIC	9
Others	6

Activity Type	# Activity
Cell Line	4
Organism	15
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	350.0	nM	PMID[569849]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	220.0	nM	PMID[569849]
NPT139	Cell Line	HT-29	Homo sapiens	IC50	=	1840.0	nM	PMID[569849]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	2300.0	nM	PMID[569849]
NPT1176	Organism	Mycobacterium fortuitum	Mycobacterium fortuitum	MIC	=	8.0	ug.mL-1	PMID[569849]
NPT602	Organism	Mycobacterium smegmatis	Mycobacterium smegmatis	MIC	=	8.0	ug.mL-1	PMID[569849]
NPT1177	Organism	Mycobacterium phlei	Mycobacterium phlei	MIC	=	2.0	ug.mL-1	PMID[569849]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	2.0	ug.mL-1	PMID[569849]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	1.0	ug.mL-1	PMID[569849]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	0.5	ug.mL-1	PMID[569849]
NPT32	Organism	Mus musculus	Mus musculus	MTD	=	30.0	mg kg-1	PMID[569849]
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	log10cfu	=	8.17	n.a.	PMID[569849]
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	log10cfu	=	6.17	n.a.	PMID[569849]
NPT1108	Organism	Mycobacterium bovis BCG	Mycobacterium bovis BCG	MIC	=	0.1	ug.mL-1	PMID[569849]
NPT27	Others	Unspecified		IC50	=	800.0	nM	PMID[569849]
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	Activity	=	99.0	%	PMID[569849]
NPT790	Organism	Mycobacterium tuberculosis H37Rv	Mycobacterium tuberculosis H37Rv	MIC	=	1.25	ug.mL-1	PMID[569850]

☑ 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 NPC11863 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	4783
0.1-0.2	20338
0.2-0.3	11419
0.3-0.4	3138
0.4-0.5	2098
0.5-0.6	727
0.6-0.7	156
0.7-0.8	30
0.8-0.85	3
0.85-0.9	1
0.9-0.95	1
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9739	High Similarity	NPC56856
0.9464	High Similarity	NPC473901
0.9091	High Similarity	NPC135488
0.8393	Intermediate Similarity	NPC83987
0.812	Intermediate Similarity	NPC231655
0.812	Intermediate Similarity	NPC76540
0.7917	Intermediate Similarity	NPC27802
0.7642	Intermediate Similarity	NPC235843
0.7538	Intermediate Similarity	NPC290094
0.746	Intermediate Similarity	NPC84268
0.7368	Intermediate Similarity	NPC169625
0.7368	Intermediate Similarity	NPC202957
0.7344	Intermediate Similarity	NPC471402
0.7344	Intermediate Similarity	NPC240136
0.7344	Intermediate Similarity	NPC297486
0.7287	Intermediate Similarity	NPC143603
0.7287	Intermediate Similarity	NPC91958
0.7259	Intermediate Similarity	NPC89490
0.7252	Intermediate Similarity	NPC265605
0.7252	Intermediate Similarity	NPC182570
0.7252	Intermediate Similarity	NPC48564
0.7206	Intermediate Similarity	NPC475090
0.7206	Intermediate Similarity	NPC475105
0.7206	Intermediate Similarity	NPC329896
0.7143	Intermediate Similarity	NPC213774
0.7111	Intermediate Similarity	NPC476140
0.7059	Intermediate Similarity	NPC212125
0.7059	Intermediate Similarity	NPC471311
0.7059	Intermediate Similarity	NPC471313
0.7037	Intermediate Similarity	NPC151489
0.7015	Intermediate Similarity	NPC46358
0.6963	Remote Similarity	NPC476322
0.6963	Remote Similarity	NPC27740
0.6934	Remote Similarity	NPC165370
0.6934	Remote Similarity	NPC306397
0.6912	Remote Similarity	NPC146373
0.6912	Remote Similarity	NPC245244
0.6912	Remote Similarity	NPC166424
0.6884	Remote Similarity	NPC471589
0.6884	Remote Similarity	NPC313823
0.6884	Remote Similarity	NPC287895
0.6871	Remote Similarity	NPC285731
0.6857	Remote Similarity	NPC471322
0.6786	Remote Similarity	NPC315320
0.6738	Remote Similarity	NPC256893
0.6738	Remote Similarity	NPC324611
0.6738	Remote Similarity	NPC174421
0.6714	Remote Similarity	NPC476131
0.6691	Remote Similarity	NPC329825
0.669	Remote Similarity	NPC322488
0.669	Remote Similarity	NPC330326
0.6667	Remote Similarity	NPC69914
0.6667	Remote Similarity	NPC282398
0.6621	Remote Similarity	NPC471312
0.6621	Remote Similarity	NPC65408
0.662	Remote Similarity	NPC101165
0.6581	Remote Similarity	NPC469897
0.6581	Remote Similarity	NPC14223
0.6552	Remote Similarity	NPC328029
0.6552	Remote Similarity	NPC29702
0.6507	Remote Similarity	NPC314102
0.6507	Remote Similarity	NPC114310
0.6507	Remote Similarity	NPC251722
0.6494	Remote Similarity	NPC138842
0.6479	Remote Similarity	NPC71236
0.6474	Remote Similarity	NPC236711
0.6447	Remote Similarity	NPC470111
0.6447	Remote Similarity	NPC471957
0.6429	Remote Similarity	NPC470823
0.6429	Remote Similarity	NPC273714
0.6419	Remote Similarity	NPC315348
0.6419	Remote Similarity	NPC316811
0.6419	Remote Similarity	NPC32002
0.64	Remote Similarity	NPC477977
0.6389	Remote Similarity	NPC82295
0.6376	Remote Similarity	NPC318935
0.6358	Remote Similarity	NPC230085
0.6358	Remote Similarity	NPC471323
0.6358	Remote Similarity	NPC159630
0.6351	Remote Similarity	NPC169433
0.6327	Remote Similarity	NPC29886
0.6327	Remote Similarity	NPC261195
0.6323	Remote Similarity	NPC216713
0.6312	Remote Similarity	NPC69277
0.6284	Remote Similarity	NPC150259
0.6284	Remote Similarity	NPC84911
0.6268	Remote Similarity	NPC151779
0.6259	Remote Similarity	NPC291517
0.625	Remote Similarity	NPC148140
0.6234	Remote Similarity	NPC112741
0.6234	Remote Similarity	NPC477974
0.6225	Remote Similarity	NPC476454
0.6222	Remote Similarity	NPC143156
0.6216	Remote Similarity	NPC96102
0.6209	Remote Similarity	NPC467188
0.6209	Remote Similarity	NPC167400
0.6204	Remote Similarity	NPC81561
0.62	Remote Similarity	NPC73767
0.62	Remote Similarity	NPC110126
0.6184	Remote Similarity	NPC190296
0.6179	Remote Similarity	NPC196580
0.6178	Remote Similarity	NPC200214
0.6174	Remote Similarity	NPC105127
0.6174	Remote Similarity	NPC472288
0.6169	Remote Similarity	NPC220523
0.6169	Remote Similarity	NPC302159
0.6159	Remote Similarity	NPC469784
0.6159	Remote Similarity	NPC469767
0.6159	Remote Similarity	NPC469779
0.6159	Remote Similarity	NPC469761
0.6159	Remote Similarity	NPC469768
0.6159	Remote Similarity	NPC469783
0.6159	Remote Similarity	NPC469780
0.6149	Remote Similarity	NPC23215
0.6133	Remote Similarity	NPC104049
0.6131	Remote Similarity	NPC476566
0.6129	Remote Similarity	NPC179787
0.6129	Remote Similarity	NPC201380
0.6129	Remote Similarity	NPC105811
0.6118	Remote Similarity	NPC469766
0.6118	Remote Similarity	NPC88121
0.6104	Remote Similarity	NPC314372
0.6104	Remote Similarity	NPC86288
0.609	Remote Similarity	NPC321911
0.6078	Remote Similarity	NPC320863
0.6076	Remote Similarity	NPC107287
0.6071	Remote Similarity	NPC215519
0.6065	Remote Similarity	NPC63545
0.6061	Remote Similarity	NPC32534
0.6061	Remote Similarity	NPC91895
0.6053	Remote Similarity	NPC230002
0.6053	Remote Similarity	NPC279081
0.6051	Remote Similarity	NPC40070
0.6049	Remote Similarity	NPC71079
0.6043	Remote Similarity	NPC162689
0.6043	Remote Similarity	NPC54102
0.6026	Remote Similarity	NPC469811
0.6013	Remote Similarity	NPC70406
0.6013	Remote Similarity	NPC472260
0.6013	Remote Similarity	NPC470233
0.6012	Remote Similarity	NPC474217
0.6	Remote Similarity	NPC159856
0.6	Remote Similarity	NPC469525
0.6	Remote Similarity	NPC51054
0.5977	Remote Similarity	NPC74382
0.5977	Remote Similarity	NPC206251
0.5976	Remote Similarity	NPC85918
0.5975	Remote Similarity	NPC312860
0.5963	Remote Similarity	NPC129721
0.5951	Remote Similarity	NPC48192
0.5951	Remote Similarity	NPC225018
0.5949	Remote Similarity	NPC148592
0.5949	Remote Similarity	NPC24678
0.5949	Remote Similarity	NPC105818
0.5949	Remote Similarity	NPC313889
0.5939	Remote Similarity	NPC127730
0.5939	Remote Similarity	NPC278366
0.5938	Remote Similarity	NPC263455
0.5938	Remote Similarity	NPC229055
0.5938	Remote Similarity	NPC209362
0.5926	Remote Similarity	NPC80681
0.5906	Remote Similarity	NPC164228
0.5903	Remote Similarity	NPC122718
0.5901	Remote Similarity	NPC476464
0.5901	Remote Similarity	NPC74357
0.589	Remote Similarity	NPC278451
0.589	Remote Similarity	NPC25899
0.5882	Remote Similarity	NPC104483
0.5875	Remote Similarity	NPC469786
0.5875	Remote Similarity	NPC73952
0.5875	Remote Similarity	NPC25008
0.5875	Remote Similarity	NPC469765
0.5875	Remote Similarity	NPC469763
0.5875	Remote Similarity	NPC251391
0.5875	Remote Similarity	NPC325903
0.5875	Remote Similarity	NPC259644
0.5875	Remote Similarity	NPC469760
0.5868	Remote Similarity	NPC476518
0.5864	Remote Similarity	NPC138018
0.586	Remote Similarity	NPC288838
0.586	Remote Similarity	NPC143872
0.586	Remote Similarity	NPC316069
0.5854	Remote Similarity	NPC242116
0.5849	Remote Similarity	NPC53947
0.5839	Remote Similarity	NPC70922
0.5839	Remote Similarity	NPC75540
0.5839	Remote Similarity	NPC80597
0.5839	Remote Similarity	NPC212376
0.5839	Remote Similarity	NPC211572
0.5833	Remote Similarity	NPC14651
0.5833	Remote Similarity	NPC121658
0.5828	Remote Similarity	NPC113812
0.5828	Remote Similarity	NPC56765
0.5828	Remote Similarity	NPC198988
0.5828	Remote Similarity	NPC293487
0.5828	Remote Similarity	NPC477591
0.5818	Remote Similarity	NPC478182
0.5818	Remote Similarity	NPC265100
0.5818	Remote Similarity	NPC473057
0.5802	Remote Similarity	NPC115049

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 NPC11863 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	625
0.1-0.2	1166
0.2-0.3	1723
0.3-0.4	2846
0.4-0.5	1999
0.5-0.6	627
0.6-0.7	138
0.7-0.8	23
0.8-0.85	1
0.85-0.9	0
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9643	High Similarity	NPD60	Approved
0.9474	High Similarity	NPD8840	Approved
0.812	Intermediate Similarity	NPD9099	Clinical (unspecified phase)
0.812	Intermediate Similarity	NPD9098	Phase 3
0.7787	Intermediate Similarity	NPD4824	Approved
0.7787	Intermediate Similarity	NPD4823	Approved
0.76	Intermediate Similarity	NPD269	Clinical (unspecified phase)
0.7481	Intermediate Similarity	NPD9357	Approved
0.748	Intermediate Similarity	NPD9396	Approved
0.748	Intermediate Similarity	NPD9392	Approved
0.7391	Intermediate Similarity	NPD792	Discontinued
0.7368	Intermediate Similarity	NPD9583	Approved
0.7324	Intermediate Similarity	NPD4510	Discontinued
0.7252	Intermediate Similarity	NPD270	Clinical (unspecified phase)
0.7252	Intermediate Similarity	NPD268	Approved
0.7252	Intermediate Similarity	NPD271	Approved
0.7153	Intermediate Similarity	NPD649	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD206	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD1095	Clinical (unspecified phase)
0.7121	Intermediate Similarity	NPD9598	Discontinued
0.7059	Intermediate Similarity	NPD9284	Approved
0.7014	Intermediate Similarity	NPD461	Approved
0.6986	Remote Similarity	NPD1366	Approved
0.6986	Remote Similarity	NPD1364	Approved
0.6986	Remote Similarity	NPD1365	Approved
0.698	Remote Similarity	NPD4641	Discontinued
0.6978	Remote Similarity	NPD9726	Discontinued
0.6957	Remote Similarity	NPD9305	Clinical (unspecified phase)
0.6934	Remote Similarity	NPD2118	Approved
0.6934	Remote Similarity	NPD9080	Approved
0.6934	Remote Similarity	NPD2119	Approved
0.6906	Remote Similarity	NPD235	Discontinued
0.6897	Remote Similarity	NPD1382	Phase 2
0.6897	Remote Similarity	NPD1383	Phase 3
0.6892	Remote Similarity	NPD2089	Clinical (unspecified phase)
0.6812	Remote Similarity	NPD992	Clinical (unspecified phase)
0.6812	Remote Similarity	NPD1598	Discontinued
0.6812	Remote Similarity	NPD991	Phase 2
0.6809	Remote Similarity	NPD1627	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD1352	Discontinued
0.6786	Remote Similarity	NPD3475	Approved
0.6786	Remote Similarity	NPD715	Phase 3
0.6786	Remote Similarity	NPD9206	Approved
0.6786	Remote Similarity	NPD9207	Approved
0.6786	Remote Similarity	NPD3476	Approved
0.6776	Remote Similarity	NPD4436	Clinical (unspecified phase)
0.6738	Remote Similarity	NPD809	Discontinued
0.6736	Remote Similarity	NPD9506	Approved
0.6733	Remote Similarity	NPD2104	Approved
0.6733	Remote Similarity	NPD2102	Approved
0.6713	Remote Similarity	NPD272	Approved
0.6691	Remote Similarity	NPD748	Clinical (unspecified phase)
0.669	Remote Similarity	NPD9100	Approved
0.669	Remote Similarity	NPD1995	Approved
0.669	Remote Similarity	NPD1994	Approved
0.669	Remote Similarity	NPD1380	Discovery
0.669	Remote Similarity	NPD1993	Approved
0.6645	Remote Similarity	NPD2103	Approved
0.6643	Remote Similarity	NPD3944	Approved
0.6643	Remote Similarity	NPD4029	Approved
0.6643	Remote Similarity	NPD4030	Approved
0.6643	Remote Similarity	NPD4028	Approved
0.6643	Remote Similarity	NPD3942	Approved
0.6621	Remote Similarity	NPD201	Phase 2
0.6621	Remote Similarity	NPD200	Phase 2
0.662	Remote Similarity	NPD803	Phase 1
0.6601	Remote Similarity	NPD2012	Clinical (unspecified phase)
0.6599	Remote Similarity	NPD1395	Clinical (unspecified phase)
0.6597	Remote Similarity	NPD2142	Approved
0.6597	Remote Similarity	NPD2141	Approved
0.6597	Remote Similarity	NPD2140	Approved
0.6558	Remote Similarity	NPD1328	Approved
0.6556	Remote Similarity	NPD1661	Suspended
0.6531	Remote Similarity	NPD4804	Approved
0.6525	Remote Similarity	NPD1031	Discontinued
0.6522	Remote Similarity	NPD754	Clinical (unspecified phase)
0.6513	Remote Similarity	NPD426	Approved
0.6513	Remote Similarity	NPD162	Approved
0.6513	Remote Similarity	NPD427	Approved
0.6513	Remote Similarity	NPD428	Approved
0.651	Remote Similarity	NPD1427	Clinical (unspecified phase)
0.6494	Remote Similarity	NPD491	Approved
0.6486	Remote Similarity	NPD2222	Discontinued
0.6486	Remote Similarity	NPD9599	Approved
0.6486	Remote Similarity	NPD1649	Discontinued
0.6463	Remote Similarity	NPD203	Clinical (unspecified phase)
0.6463	Remote Similarity	NPD9076	Clinical (unspecified phase)
0.6463	Remote Similarity	NPD2896	Discontinued
0.6456	Remote Similarity	NPD2385	Clinical (unspecified phase)
0.6443	Remote Similarity	NPD4805	Approved
0.6419	Remote Similarity	NPD2069	Approved
0.6419	Remote Similarity	NPD2070	Approved
0.6419	Remote Similarity	NPD174	Discontinued
0.6419	Remote Similarity	NPD2073	Approved
0.6419	Remote Similarity	NPD2068	Approved
0.6419	Remote Similarity	NPD2072	Approved
0.6419	Remote Similarity	NPD2075	Approved
0.6419	Remote Similarity	NPD2071	Approved
0.6419	Remote Similarity	NPD2074	Approved
0.64	Remote Similarity	NPD3717	Discontinued
0.6376	Remote Similarity	NPD107	Approved
0.6358	Remote Similarity	NPD3401	Clinical (unspecified phase)
0.6358	Remote Similarity	NPD751	Clinical (unspecified phase)
0.6331	Remote Similarity	NPD5787	Discontinued
0.6316	Remote Similarity	NPD175	Clinical (unspecified phase)
0.6309	Remote Similarity	NPD768	Clinical (unspecified phase)
0.6309	Remote Similarity	NPD945	Clinical (unspecified phase)
0.6304	Remote Similarity	NPD4811	Discontinued
0.6291	Remote Similarity	NPD2006	Phase 2
0.6275	Remote Similarity	NPD7469	Discontinued
0.6275	Remote Similarity	NPD6148	Clinical (unspecified phase)
0.6267	Remote Similarity	NPD7135	Phase 2
0.6266	Remote Similarity	NPD2145	Clinical (unspecified phase)
0.6258	Remote Similarity	NPD971	Clinical (unspecified phase)
0.625	Remote Similarity	NPD5503	Approved
0.625	Remote Similarity	NPD1918	Clinical (unspecified phase)
0.625	Remote Similarity	NPD3813	Approved
0.625	Remote Similarity	NPD5502	Approved
0.625	Remote Similarity	NPD4509	Discontinued
0.6242	Remote Similarity	NPD5358	Clinical (unspecified phase)
0.6242	Remote Similarity	NPD2059	Approved
0.6242	Remote Similarity	NPD2058	Phase 2
0.6242	Remote Similarity	NPD2057	Approved
0.6234	Remote Similarity	NPD9271	Approved
0.6234	Remote Similarity	NPD4702	Approved
0.6234	Remote Similarity	NPD1270	Approved
0.6234	Remote Similarity	NPD4703	Approved
0.6226	Remote Similarity	NPD1679	Approved
0.6226	Remote Similarity	NPD704	Clinical (unspecified phase)
0.6225	Remote Similarity	NPD1722	Approved
0.6216	Remote Similarity	NPD490	Clinical (unspecified phase)
0.6216	Remote Similarity	NPD198	Clinical (unspecified phase)
0.6209	Remote Similarity	NPD9075	Approved
0.6209	Remote Similarity	NPD9074	Approved
0.6205	Remote Similarity	NPD2771	Approved
0.62	Remote Similarity	NPD786	Approved
0.6196	Remote Similarity	NPD7287	Clinical (unspecified phase)
0.6184	Remote Similarity	NPD2007	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD7913	Clinical (unspecified phase)
0.6149	Remote Similarity	NPD418	Approved
0.6149	Remote Similarity	NPD5315	Discontinued
0.6139	Remote Similarity	NPD2809	Approved
0.6129	Remote Similarity	NPD2110	Approved
0.6129	Remote Similarity	NPD4547	Phase 3
0.6118	Remote Similarity	NPD952	Approved
0.6115	Remote Similarity	NPD9596	Approved
0.6115	Remote Similarity	NPD9595	Approved
0.6111	Remote Similarity	NPD1545	Discontinued
0.6098	Remote Similarity	NPD2641	Approved
0.6098	Remote Similarity	NPD2640	Approved
0.609	Remote Similarity	NPD1183	Approved
0.609	Remote Similarity	NPD2430	Phase 2
0.6087	Remote Similarity	NPD1404	Approved
0.6087	Remote Similarity	NPD1403	Approved
0.6082	Remote Similarity	NPD2416	Approved
0.6082	Remote Similarity	NPD2417	Approved
0.6076	Remote Similarity	NPD180	Clinical (unspecified phase)
0.6053	Remote Similarity	NPD165	Phase 2
0.6051	Remote Similarity	NPD2466	Phase 3
0.6051	Remote Similarity	NPD2462	Phase 3
0.6051	Remote Similarity	NPD2465	Approved
0.6049	Remote Similarity	NPD4239	Clinical (unspecified phase)
0.6048	Remote Similarity	NPD3859	Clinical (unspecified phase)
0.6048	Remote Similarity	NPD158	Discontinued
0.6037	Remote Similarity	NPD5636	Discontinued
0.6036	Remote Similarity	NPD2084	Discontinued
0.6013	Remote Similarity	NPD3262	Approved
0.6013	Remote Similarity	NPD9343	Clinical (unspecified phase)
0.6013	Remote Similarity	NPD5965	Clinical (unspecified phase)
0.6013	Remote Similarity	NPD510	Phase 1
0.6012	Remote Similarity	NPD3238	Discontinued
0.6012	Remote Similarity	NPD3039	Clinical (unspecified phase)
0.6	Remote Similarity	NPD1928	Discontinued
0.6	Remote Similarity	NPD6026	Approved
0.5978	Remote Similarity	NPD4899	Clinical (unspecified phase)
0.5976	Remote Similarity	NPD2753	Discontinued
0.5976	Remote Similarity	NPD2719	Clinical (unspecified phase)
0.5976	Remote Similarity	NPD2720	Phase 1
0.5973	Remote Similarity	NPD3385	Approved
0.5965	Remote Similarity	NPD1570	Approved
0.5964	Remote Similarity	NPD2620	Phase 2
0.5964	Remote Similarity	NPD2619	Clinical (unspecified phase)
0.5963	Remote Similarity	NPD2582	Approved
0.5963	Remote Similarity	NPD2581	Approved
0.5963	Remote Similarity	NPD820	Phase 3
0.5939	Remote Similarity	NPD2639	Approved
0.5939	Remote Similarity	NPD2642	Approved
0.5938	Remote Similarity	NPD2165	Phase 1
0.5938	Remote Similarity	NPD2061	Approved
0.5935	Remote Similarity	NPD8823	Approved
0.5928	Remote Similarity	NPD3610	Approved
0.5928	Remote Similarity	NPD3609	Approved
0.5926	Remote Similarity	NPD5255	Approved
0.5926	Remote Similarity	NPD604	Clinical (unspecified phase)
0.5921	Remote Similarity	NPD852	Discontinued
0.5918	Remote Similarity	NPD3654	Approved
0.5917	Remote Similarity	NPD3348	Phase 2
0.5917	Remote Similarity	NPD6044	Discontinued
0.5915	Remote Similarity	NPD5925	Phase 1
0.5906	Remote Similarity	NPD4556	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