NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	157.0
Volume:	143.881
LogP:	2.175
LogD:	2.756
LogS:	-2.451
# Rotatable Bonds:	2
TPSA:	12.89
# H-Bond Aceptor:	1
# H-Bond Donor:	0
# Rings:	1
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.612
Synthetic Accessibility Score:	2.654
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:	-4.215
MDCK Permeability:	2.805993972287979e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.042
30% Bioavailability (F30%):	0.71

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.866
Plasma Protein Binding (PPB):	36.2867317199707%
Volume Distribution (VD):	1.807
Pgp-substrate:	60.37778091430664%

ADMET: Metabolism

CYP1A2-inhibitor:	0.946
CYP1A2-substrate:	0.74
CYP2C19-inhibitor:	0.891
CYP2C19-substrate:	0.714
CYP2C9-inhibitor:	0.586
CYP2C9-substrate:	0.656
CYP2D6-inhibitor:	0.011
CYP2D6-substrate:	0.46
CYP3A4-inhibitor:	0.013
CYP3A4-substrate:	0.318

ADMET: Excretion

Clearance (CL):	12.148
Half-life (T1/2):	0.446

ADMET: Toxicity

hERG Blockers:	0.169
Human Hepatotoxicity (H-HT):	0.178
Drug-inuced Liver Injury (DILI):	0.741
AMES Toxicity:	0.624
Rat Oral Acute Toxicity:	0.607
Maximum Recommended Daily Dose:	0.035
Skin Sensitization:	0.946
Carcinogencity:	0.267
Eye Corrosion:	0.966
Eye Irritation:	0.996
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: NPC473901

Natural Product ID:	NPC473901
*Common Name:**	2-(Methyldithio)Pyridine
IUPAC Name:	2-(methyldisulfanyl)pyridine
Synonyms:	2-(2-Methyldisulfanyl)Pyridine; 2-(Methyldithio)Pyridine
Standard InCHIKey:	BHANCCMWYDZQOR-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C6H7NS2/c1-8-9-6-4-2-3-5-7-6/h2-5H,1H3
SMILES:	CSSc1ccccn1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL454604
PubChem CID:	173923
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
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
MIC	6
Others	17

Activity Type	# Activity
Organism	23

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IZ	=	23.0	mm	PMID[528903]
NPT1176	Organism	Mycobacterium fortuitum	Mycobacterium fortuitum	MIC	=	8.0	ug.mL-1	PMID[528904]
NPT602	Organism	Mycobacterium smegmatis	Mycobacterium smegmatis	MIC	=	8.0	ug.mL-1	PMID[528904]
NPT1177	Organism	Mycobacterium phlei	Mycobacterium phlei	MIC	=	16.0	ug.mL-1	PMID[528904]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	2.0	ug.mL-1	PMID[528904]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	4.0	ug.mL-1	PMID[528904]
NPT173	Organism	Klebsiella pneumoniae	Klebsiella pneumoniae	IZ	=	0.0	mm	PMID[528905]
NPT1033	Organism	Enterobacter cloacae	Enterobacter cloacae	IZ	=	10.0	mm	PMID[528905]
NPT19	Organism	Escherichia coli	Escherichia coli	IZ	=	12.0	mm	PMID[528905]
NPT747	Organism	Acinetobacter baumannii	Acinetobacter baumannii	IZ	=	15.0	mm	PMID[528905]
NPT1550	Organism	Bacillus anthracis	Bacillus anthracis	IZ	=	48.0	mm	PMID[528905]
NPT1531	Organism	Enterococcus faecium	Enterococcus faecium	IZ	=	0.0	mm	PMID[528905]
NPT175	Organism	Enterococcus faecalis	Enterococcus faecalis	IZ	=	23.0	mm	PMID[528905]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IZ	=	20.0	mm	PMID[528905]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IZ	=	21.0	mm	PMID[528905]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IZ	=	25.0	mm	PMID[528905]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IZ	=	12.0	mm	PMID[528905]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IZ	=	13.0	mm	PMID[528905]
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	IZ	=	21.0	mm	PMID[528905]
NPT747	Organism	Acinetobacter baumannii	Acinetobacter baumannii	IZ	=	21.0	mm	PMID[528905]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	IZ	=	0.0	mm	PMID[528905]

☑ 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 NPC473901 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	5730
0.1-0.2	20084
0.2-0.3	10779
0.3-0.4	3064
0.4-0.5	2106
0.5-0.6	721
0.6-0.7	167
0.7-0.8	37
0.8-0.85	2
0.85-0.9	4
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9464	High Similarity	NPC11863
0.9217	High Similarity	NPC56856
0.8868	High Similarity	NPC83987
0.8595	High Similarity	NPC135488
0.8559	High Similarity	NPC231655
0.8559	High Similarity	NPC76540
0.8333	Intermediate Similarity	NPC27802
0.8034	Intermediate Similarity	NPC235843
0.7833	Intermediate Similarity	NPC84268
0.7705	Intermediate Similarity	NPC240136
0.7705	Intermediate Similarity	NPC471402
0.7705	Intermediate Similarity	NPC297486
0.7642	Intermediate Similarity	NPC91958
0.7642	Intermediate Similarity	NPC143603
0.76	Intermediate Similarity	NPC265605
0.76	Intermediate Similarity	NPC48564
0.76	Intermediate Similarity	NPC182570
0.7522	Intermediate Similarity	NPC213774
0.748	Intermediate Similarity	NPC290094
0.7442	Intermediate Similarity	NPC476140
0.7344	Intermediate Similarity	NPC46358
0.7308	Intermediate Similarity	NPC202957
0.7308	Intermediate Similarity	NPC169625
0.7287	Intermediate Similarity	NPC476322
0.7287	Intermediate Similarity	NPC27740
0.7252	Intermediate Similarity	NPC471311
0.7252	Intermediate Similarity	NPC212125
0.7252	Intermediate Similarity	NPC471313
0.7231	Intermediate Similarity	NPC151489
0.7231	Intermediate Similarity	NPC245244
0.7231	Intermediate Similarity	NPC146373
0.7231	Intermediate Similarity	NPC166424
0.7197	Intermediate Similarity	NPC287895
0.7197	Intermediate Similarity	NPC89490
0.7143	Intermediate Similarity	NPC475105
0.7143	Intermediate Similarity	NPC475090
0.7143	Intermediate Similarity	NPC329896
0.7121	Intermediate Similarity	NPC165370
0.7121	Intermediate Similarity	NPC306397
0.7068	Intermediate Similarity	NPC471589
0.7068	Intermediate Similarity	NPC313823
0.7037	Intermediate Similarity	NPC471322
0.7015	Intermediate Similarity	NPC476131
0.7	Intermediate Similarity	NPC329825
0.6963	Remote Similarity	NPC315320
0.6963	Remote Similarity	NPC282398
0.6963	Remote Similarity	NPC69914
0.6937	Remote Similarity	NPC14223
0.6912	Remote Similarity	NPC101165
0.6912	Remote Similarity	NPC174421
0.6912	Remote Similarity	NPC324611
0.6912	Remote Similarity	NPC256893
0.6861	Remote Similarity	NPC322488
0.6861	Remote Similarity	NPC330326
0.6806	Remote Similarity	NPC285731
0.6786	Remote Similarity	NPC251722
0.6786	Remote Similarity	NPC65408
0.6786	Remote Similarity	NPC314102
0.6786	Remote Similarity	NPC471312
0.6733	Remote Similarity	NPC469897
0.6716	Remote Similarity	NPC273714
0.6714	Remote Similarity	NPC328029
0.6714	Remote Similarity	NPC29702
0.669	Remote Similarity	NPC316811
0.669	Remote Similarity	NPC315348
0.669	Remote Similarity	NPC32002
0.6689	Remote Similarity	NPC470823
0.6667	Remote Similarity	NPC82295
0.6667	Remote Similarity	NPC114310
0.6642	Remote Similarity	NPC71236
0.662	Remote Similarity	NPC169433
0.6599	Remote Similarity	NPC471957
0.6596	Remote Similarity	NPC29886
0.6596	Remote Similarity	NPC261195
0.6593	Remote Similarity	NPC69277
0.6552	Remote Similarity	NPC477977
0.6549	Remote Similarity	NPC84911
0.6549	Remote Similarity	NPC150259
0.6538	Remote Similarity	NPC148140
0.6528	Remote Similarity	NPC318935
0.6512	Remote Similarity	NPC143156
0.6507	Remote Similarity	NPC471323
0.6507	Remote Similarity	NPC230085
0.6507	Remote Similarity	NPC159630
0.6496	Remote Similarity	NPC196580
0.6489	Remote Similarity	NPC81561
0.6483	Remote Similarity	NPC476454
0.6479	Remote Similarity	NPC96102
0.6467	Remote Similarity	NPC216713
0.6458	Remote Similarity	NPC73767
0.6458	Remote Similarity	NPC110126
0.6434	Remote Similarity	NPC105127
0.6423	Remote Similarity	NPC151779
0.6414	Remote Similarity	NPC469761
0.6414	Remote Similarity	NPC469767
0.6414	Remote Similarity	NPC469784
0.6414	Remote Similarity	NPC469768
0.6414	Remote Similarity	NPC469780
0.6414	Remote Similarity	NPC469783
0.6414	Remote Similarity	NPC469779
0.6412	Remote Similarity	NPC476566
0.6408	Remote Similarity	NPC291517
0.6376	Remote Similarity	NPC179787
0.6376	Remote Similarity	NPC112741
0.6376	Remote Similarity	NPC470111
0.6376	Remote Similarity	NPC477974
0.6376	Remote Similarity	NPC201380
0.637	Remote Similarity	NPC469766
0.6351	Remote Similarity	NPC86288
0.6351	Remote Similarity	NPC467188
0.6351	Remote Similarity	NPC167400
0.6343	Remote Similarity	NPC215519
0.6333	Remote Similarity	NPC321911
0.6327	Remote Similarity	NPC320863
0.6327	Remote Similarity	NPC190296
0.6319	Remote Similarity	NPC472288
0.6316	Remote Similarity	NPC54102
0.6316	Remote Similarity	NPC200214
0.6316	Remote Similarity	NPC162689
0.6309	Remote Similarity	NPC220523
0.6309	Remote Similarity	NPC63545
0.6309	Remote Similarity	NPC302159
0.6301	Remote Similarity	NPC279081
0.6301	Remote Similarity	NPC230002
0.6294	Remote Similarity	NPC23215
0.6291	Remote Similarity	NPC40070
0.6276	Remote Similarity	NPC104049
0.6267	Remote Similarity	NPC469811
0.6267	Remote Similarity	NPC105811
0.6259	Remote Similarity	NPC88121
0.625	Remote Similarity	NPC470233
0.6242	Remote Similarity	NPC314372
0.6209	Remote Similarity	NPC107287
0.6188	Remote Similarity	NPC91895
0.6184	Remote Similarity	NPC148592
0.6159	Remote Similarity	NPC122718
0.6144	Remote Similarity	NPC70406
0.6144	Remote Similarity	NPC472260
0.6133	Remote Similarity	NPC159856
0.6129	Remote Similarity	NPC476464
0.6121	Remote Similarity	NPC164228
0.6104	Remote Similarity	NPC325903
0.6104	Remote Similarity	NPC312860
0.6104	Remote Similarity	NPC138842
0.6093	Remote Similarity	NPC143872
0.6093	Remote Similarity	NPC316069
0.6093	Remote Similarity	NPC288838
0.609	Remote Similarity	NPC236711
0.609	Remote Similarity	NPC129721
0.6078	Remote Similarity	NPC53947
0.6078	Remote Similarity	NPC313889
0.6078	Remote Similarity	NPC24678
0.6078	Remote Similarity	NPC105818
0.6069	Remote Similarity	NPC198988
0.6065	Remote Similarity	NPC263455
0.6065	Remote Similarity	NPC209362
0.6065	Remote Similarity	NPC229055
0.6051	Remote Similarity	NPC56765
0.6051	Remote Similarity	NPC477591
0.6051	Remote Similarity	NPC80681
0.6028	Remote Similarity	NPC278451
0.6027	Remote Similarity	NPC325252
0.6026	Remote Similarity	NPC74357
0.6014	Remote Similarity	NPC104483
0.6014	Remote Similarity	NPC41174
0.6013	Remote Similarity	NPC44773
0.6013	Remote Similarity	NPC25899
0.6013	Remote Similarity	NPC215584
0.6	Remote Similarity	NPC20144
0.6	Remote Similarity	NPC469765
0.6	Remote Similarity	NPC469786
0.6	Remote Similarity	NPC469760
0.6	Remote Similarity	NPC251391
0.6	Remote Similarity	NPC469763
0.6	Remote Similarity	NPC25008
0.6	Remote Similarity	NPC259644
0.6	Remote Similarity	NPC141926
0.6	Remote Similarity	NPC73952
0.5987	Remote Similarity	NPC138018
0.5975	Remote Similarity	NPC71079
0.5962	Remote Similarity	NPC34844
0.5962	Remote Similarity	NPC211572
0.5962	Remote Similarity	NPC212376
0.5962	Remote Similarity	NPC70922
0.5962	Remote Similarity	NPC80597
0.5962	Remote Similarity	NPC75540
0.5957	Remote Similarity	NPC75999
0.5949	Remote Similarity	NPC113812
0.5949	Remote Similarity	NPC293487
0.5938	Remote Similarity	NPC473057
0.5938	Remote Similarity	NPC90723
0.5938	Remote Similarity	NPC474217
0.5938	Remote Similarity	NPC265100
0.5938	Remote Similarity	NPC478182
0.5924	Remote Similarity	NPC51054
0.5912	Remote Similarity	NPC470204
0.5912	Remote Similarity	NPC122141
0.5906	Remote Similarity	NPC206251
0.5906	Remote Similarity	NPC74382
0.5904	Remote Similarity	NPC248454

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 NPC473901 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	694
0.1-0.2	1119
0.2-0.3	1737
0.3-0.4	2802
0.4-0.5	1969
0.5-0.6	647
0.6-0.7	147
0.7-0.8	30
0.8-0.85	2
0.85-0.9	2
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9107	High Similarity	NPD60	Approved
0.8947	High Similarity	NPD8840	Approved
0.8559	High Similarity	NPD9098	Phase 3
0.8559	High Similarity	NPD9099	Clinical (unspecified phase)
0.819	Intermediate Similarity	NPD4824	Approved
0.819	Intermediate Similarity	NPD4823	Approved
0.7983	Intermediate Similarity	NPD269	Clinical (unspecified phase)
0.7851	Intermediate Similarity	NPD9396	Approved
0.7851	Intermediate Similarity	NPD9392	Approved
0.784	Intermediate Similarity	NPD9357	Approved
0.7717	Intermediate Similarity	NPD9583	Approved
0.7647	Intermediate Similarity	NPD4510	Discontinued
0.76	Intermediate Similarity	NPD270	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD268	Approved
0.76	Intermediate Similarity	NPD271	Approved
0.7594	Intermediate Similarity	NPD792	Discontinued
0.7464	Intermediate Similarity	NPD649	Clinical (unspecified phase)
0.746	Intermediate Similarity	NPD9598	Discontinued
0.7333	Intermediate Similarity	NPD206	Clinical (unspecified phase)
0.7286	Intermediate Similarity	NPD1366	Approved
0.7286	Intermediate Similarity	NPD1365	Approved
0.7286	Intermediate Similarity	NPD1364	Approved
0.7273	Intermediate Similarity	NPD9305	Clinical (unspecified phase)
0.7252	Intermediate Similarity	NPD2119	Approved
0.7252	Intermediate Similarity	NPD9284	Approved
0.7252	Intermediate Similarity	NPD2118	Approved
0.7218	Intermediate Similarity	NPD235	Discontinued
0.7194	Intermediate Similarity	NPD461	Approved
0.7153	Intermediate Similarity	NPD4641	Discontinued
0.7121	Intermediate Similarity	NPD991	Phase 2
0.7121	Intermediate Similarity	NPD992	Clinical (unspecified phase)
0.7121	Intermediate Similarity	NPD9080	Approved
0.7121	Intermediate Similarity	NPD1598	Discontinued
0.709	Intermediate Similarity	NPD3475	Approved
0.709	Intermediate Similarity	NPD3476	Approved
0.709	Intermediate Similarity	NPD715	Phase 3
0.7068	Intermediate Similarity	NPD1095	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD809	Discontinued
0.7014	Intermediate Similarity	NPD2104	Approved
0.7014	Intermediate Similarity	NPD2102	Approved
0.7	Intermediate Similarity	NPD748	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD1627	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD1995	Approved
0.6985	Remote Similarity	NPD1993	Approved
0.6985	Remote Similarity	NPD1994	Approved
0.6963	Remote Similarity	NPD9207	Approved
0.6963	Remote Similarity	NPD9206	Approved
0.6939	Remote Similarity	NPD4436	Clinical (unspecified phase)
0.6934	Remote Similarity	NPD4030	Approved
0.6934	Remote Similarity	NPD4028	Approved
0.6934	Remote Similarity	NPD4029	Approved
0.6934	Remote Similarity	NPD3944	Approved
0.6934	Remote Similarity	NPD3942	Approved
0.6918	Remote Similarity	NPD2103	Approved
0.6912	Remote Similarity	NPD803	Phase 1
0.6912	Remote Similarity	NPD9726	Discontinued
0.6884	Remote Similarity	NPD272	Approved
0.6884	Remote Similarity	NPD2140	Approved
0.6884	Remote Similarity	NPD2142	Approved
0.6884	Remote Similarity	NPD2141	Approved
0.6861	Remote Similarity	NPD9100	Approved
0.6828	Remote Similarity	NPD2089	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD201	Phase 2
0.6786	Remote Similarity	NPD200	Phase 2
0.6712	Remote Similarity	NPD1661	Suspended
0.6711	Remote Similarity	NPD1328	Approved
0.6691	Remote Similarity	NPD1031	Discontinued
0.669	Remote Similarity	NPD4804	Approved
0.669	Remote Similarity	NPD2075	Approved
0.669	Remote Similarity	NPD2069	Approved
0.669	Remote Similarity	NPD2071	Approved
0.669	Remote Similarity	NPD174	Discontinued
0.669	Remote Similarity	NPD2072	Approved
0.669	Remote Similarity	NPD2074	Approved
0.669	Remote Similarity	NPD2068	Approved
0.669	Remote Similarity	NPD2070	Approved
0.669	Remote Similarity	NPD2073	Approved
0.6667	Remote Similarity	NPD9506	Approved
0.6667	Remote Similarity	NPD427	Approved
0.6667	Remote Similarity	NPD426	Approved
0.6667	Remote Similarity	NPD162	Approved
0.6667	Remote Similarity	NPD754	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD428	Approved
0.6644	Remote Similarity	NPD491	Approved
0.6643	Remote Similarity	NPD2222	Discontinued
0.6643	Remote Similarity	NPD1649	Discontinued
0.6643	Remote Similarity	NPD9599	Approved
0.6621	Remote Similarity	NPD3401	Clinical (unspecified phase)
0.662	Remote Similarity	NPD2896	Discontinued
0.662	Remote Similarity	NPD9076	Clinical (unspecified phase)
0.662	Remote Similarity	NPD203	Clinical (unspecified phase)
0.662	Remote Similarity	NPD1380	Discovery
0.6617	Remote Similarity	NPD5787	Discontinued
0.6601	Remote Similarity	NPD2385	Clinical (unspecified phase)
0.6597	Remote Similarity	NPD4805	Approved
0.6591	Remote Similarity	NPD4811	Discontinued
0.6573	Remote Similarity	NPD945	Clinical (unspecified phase)
0.6573	Remote Similarity	NPD768	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD3717	Discontinued
0.6552	Remote Similarity	NPD2006	Phase 2
0.6528	Remote Similarity	NPD107	Approved
0.6528	Remote Similarity	NPD1395	Clinical (unspecified phase)
0.6528	Remote Similarity	NPD7135	Phase 2
0.651	Remote Similarity	NPD971	Clinical (unspecified phase)
0.6507	Remote Similarity	NPD5503	Approved
0.6507	Remote Similarity	NPD1918	Clinical (unspecified phase)
0.6507	Remote Similarity	NPD5502	Approved
0.6507	Remote Similarity	NPD1352	Discontinued
0.6507	Remote Similarity	NPD4509	Discontinued
0.6507	Remote Similarity	NPD751	Clinical (unspecified phase)
0.6503	Remote Similarity	NPD2059	Approved
0.6503	Remote Similarity	NPD2058	Phase 2
0.6503	Remote Similarity	NPD2057	Approved
0.6483	Remote Similarity	NPD1722	Approved
0.6483	Remote Similarity	NPD1382	Phase 2
0.6483	Remote Similarity	NPD1383	Phase 3
0.6479	Remote Similarity	NPD198	Clinical (unspecified phase)
0.6479	Remote Similarity	NPD490	Clinical (unspecified phase)
0.6463	Remote Similarity	NPD175	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD786	Approved
0.6438	Remote Similarity	NPD2007	Clinical (unspecified phase)
0.6438	Remote Similarity	NPD1427	Clinical (unspecified phase)
0.6419	Remote Similarity	NPD7469	Discontinued
0.6419	Remote Similarity	NPD6148	Clinical (unspecified phase)
0.6405	Remote Similarity	NPD2145	Clinical (unspecified phase)
0.6395	Remote Similarity	NPD3813	Approved
0.6387	Remote Similarity	NPD5315	Discontinued
0.6376	Remote Similarity	NPD4547	Phase 3
0.6376	Remote Similarity	NPD9271	Approved
0.6376	Remote Similarity	NPD4703	Approved
0.6376	Remote Similarity	NPD4702	Approved
0.6376	Remote Similarity	NPD2110	Approved
0.6376	Remote Similarity	NPD1270	Approved
0.6364	Remote Similarity	NPD1679	Approved
0.6364	Remote Similarity	NPD704	Clinical (unspecified phase)
0.6351	Remote Similarity	NPD9074	Approved
0.6351	Remote Similarity	NPD9075	Approved
0.6335	Remote Similarity	NPD2771	Approved
0.6333	Remote Similarity	NPD2430	Phase 2
0.6301	Remote Similarity	NPD165	Phase 2
0.6291	Remote Similarity	NPD7913	Clinical (unspecified phase)
0.6291	Remote Similarity	NPD2462	Phase 3
0.6291	Remote Similarity	NPD2466	Phase 3
0.6291	Remote Similarity	NPD2465	Approved
0.625	Remote Similarity	NPD9596	Approved
0.625	Remote Similarity	NPD9595	Approved
0.6242	Remote Similarity	NPD952	Approved
0.6242	Remote Similarity	NPD1545	Discontinued
0.6226	Remote Similarity	NPD2640	Approved
0.6226	Remote Similarity	NPD2641	Approved
0.6225	Remote Similarity	NPD1183	Approved
0.6224	Remote Similarity	NPD3385	Approved
0.622	Remote Similarity	NPD1928	Discontinued
0.6218	Remote Similarity	NPD1404	Approved
0.6218	Remote Similarity	NPD1403	Approved
0.6209	Remote Similarity	NPD2012	Clinical (unspecified phase)
0.6209	Remote Similarity	NPD180	Clinical (unspecified phase)
0.6205	Remote Similarity	NPD2417	Approved
0.6205	Remote Similarity	NPD2416	Approved
0.6173	Remote Similarity	NPD158	Discontinued
0.6173	Remote Similarity	NPD3859	Clinical (unspecified phase)
0.617	Remote Similarity	NPD3654	Approved
0.6169	Remote Similarity	NPD5358	Clinical (unspecified phase)
0.6169	Remote Similarity	NPD2165	Phase 1
0.6164	Remote Similarity	NPD5636	Discontinued
0.6159	Remote Similarity	NPD2084	Discontinued
0.6149	Remote Similarity	NPD3609	Approved
0.6149	Remote Similarity	NPD3610	Approved
0.6144	Remote Similarity	NPD3262	Approved
0.6144	Remote Similarity	NPD5965	Clinical (unspecified phase)
0.6144	Remote Similarity	NPD510	Phase 1
0.6144	Remote Similarity	NPD9343	Clinical (unspecified phase)
0.6131	Remote Similarity	NPD1561	Phase 2
0.6129	Remote Similarity	NPD6026	Approved
0.6129	Remote Similarity	NPD3113	Approved
0.6129	Remote Similarity	NPD3114	Approved
0.6129	Remote Similarity	NPD3112	Approved
0.6129	Remote Similarity	NPD3115	Approved
0.6127	Remote Similarity	NPD264	Clinical (unspecified phase)
0.6118	Remote Similarity	NPD3100	Discontinued
0.6104	Remote Similarity	NPD2837	Discontinued
0.6104	Remote Similarity	NPD1917	Discontinued
0.6104	Remote Similarity	NPD3339	Approved
0.6101	Remote Similarity	NPD2720	Phase 1
0.6101	Remote Similarity	NPD2719	Clinical (unspecified phase)
0.609	Remote Similarity	NPD820	Phase 3
0.609	Remote Similarity	NPD2581	Approved
0.609	Remote Similarity	NPD6497	Approved
0.609	Remote Similarity	NPD2582	Approved
0.609	Remote Similarity	NPD2865	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD2620	Phase 2
0.6087	Remote Similarity	NPD2619	Clinical (unspecified phase)
0.6084	Remote Similarity	NPD1570	Approved
0.6078	Remote Similarity	NPD2172	Phase 1
0.6067	Remote Similarity	NPD8823	Approved
0.6066	Remote Similarity	NPD9472	Phase 3
0.6065	Remote Similarity	NPD2061	Approved
0.6065	Remote Similarity	NPD976	Approved
0.6065	Remote Similarity	NPD2809	Approved
0.6065	Remote Similarity	NPD975	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