NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	95.04
Volume:	98.358
LogP:	0.357
LogD:	0.605
LogS:	0.228
# Rotatable Bonds:	0
TPSA:	33.12
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.516
Synthetic Accessibility Score:	1.924
Fsp3:	0.0
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:	-4.273
MDCK Permeability:	2.8521950298454612e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.55
30% Bioavailability (F30%):	0.199

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.19
Plasma Protein Binding (PPB):	22.150249481201172%
Volume Distribution (VD):	1.626
Pgp-substrate:	75.74090576171875%

ADMET: Metabolism

CYP1A2-inhibitor:	0.25
CYP1A2-substrate:	0.686
CYP2C19-inhibitor:	0.095
CYP2C19-substrate:	0.326
CYP2C9-inhibitor:	0.02
CYP2C9-substrate:	0.747
CYP2D6-inhibitor:	0.045
CYP2D6-substrate:	0.596
CYP3A4-inhibitor:	0.059
CYP3A4-substrate:	0.223

ADMET: Excretion

Clearance (CL):	15.355
Half-life (T1/2):	0.807

ADMET: Toxicity

hERG Blockers:	0.027
Human Hepatotoxicity (H-HT):	0.05
Drug-inuced Liver Injury (DILI):	0.451
AMES Toxicity:	0.013
Rat Oral Acute Toxicity:	0.902
Maximum Recommended Daily Dose:	0.018
Skin Sensitization:	0.931
Carcinogencity:	0.422
Eye Corrosion:	0.97
Eye Irritation:	0.994
Respiratory Toxicity:	0.5

Download Data

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

Natural Product: NPC174421

Natural Product ID:	NPC174421
*Common Name:**	Pyridin-3-Ol
IUPAC Name:	pyridin-3-ol
Synonyms:	SR-1C8
Standard InCHIKey:	GRFNBEZIAWKNCO-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C5H5NO/c7-5-2-1-3-6-4-5/h1-4,7H
SMILES:	Oc1cccnc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL237847
PubChem CID:	7971
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000089] Pyridines and derivatives [CHEMONTID:0004151] Hydroxypyridines

*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
NPO16501	Capsicum annuum	Species	Solanaceae	Eukaryota	n.a.	fruit	n.a.	PMID[12932131]
NPO16501	Capsicum annuum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20460582]
NPO16501	Capsicum annuum	Species	Solanaceae	Eukaryota	n.a.	fruit	n.a.	PMID[25172746]
NPO16501	Capsicum annuum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8910532]
NPO16501	Capsicum annuum	Species	Solanaceae	Eukaryota	Tissue Culture	n.a.	n.a.	Database[FooDB]
NPO16501	Capsicum annuum	Species	Solanaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO16501	Capsicum annuum	Species	Solanaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO16501	Capsicum annuum	Species	Solanaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO16501	Capsicum annuum	Species	Solanaceae	Eukaryota	Pericarp	n.a.	n.a.	Database[FooDB]
NPO16501	Capsicum annuum	Species	Solanaceae	Eukaryota	Resin, Exudate, Sap	n.a.	n.a.	Database[FooDB]
NPO16501	Capsicum annuum	Species	Solanaceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO16501	Capsicum annuum	Species	Solanaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO16501	Capsicum annuum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16501	Capsicum annuum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16501	Capsicum annuum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO16501	Capsicum annuum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO16501	Capsicum annuum	Species	Solanaceae	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	7
MIC	2
Others	3

Activity Type	# Activity
Cell Line	6
Individual Protein	3
Organism	2
Protein Complex	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT783	Cell Line	MIA PaCa-2	Homo sapiens	IC50	=	56480.0	nM	PMID[518062]
NPT783	Cell Line	MIA PaCa-2	Homo sapiens	IC50	=	73100.0	nM	PMID[518062]
NPT109	Individual Protein	Cytochrome P450 3A4	Homo sapiens	IC50	=	767361.49	nM	PMID[518063]
NPT2794	Individual Protein	Quinolone resistance protein norA	Staphylococcus aureus	Activity	>	128.0	ug ml-1	PMID[518064]
NPT1444	Individual Protein	PI3-kinase p110-alpha subunit	Homo sapiens	Inhibition	<	25.0	%	PMID[518065]
NPT171	Cell Line	MRC5	Homo sapiens	IC50	>	500000.0	nM	PMID[518066]
NPT1125	Cell Line	T98G	Homo sapiens	IC50	>	500000.0	nM	PMID[518066]
NPT2363	Cell Line	U-118-MG	Homo sapiens	IC50	>	500000.0	nM	PMID[518066]
NPT1535	Cell Line	U-87 MG	Homo sapiens	IC50	>	500000.0	nM	PMID[518066]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	128.0	ug.mL-1	PMID[518064]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>=	64.0	ug.mL-1	PMID[518064]
NPT6559	Protein Complex	PI3-kinase p110-alpha/p85-alpha	Homo sapiens	Inhibition	<	25.0	%	PMID[518065]

☑ 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 NPC174421 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	2450
0.1-0.2	14128
0.2-0.3	8477
0.3-0.4	11835
0.4-0.5	3796
0.5-0.6	1646
0.6-0.7	303
0.7-0.8	56
0.8-0.85	1
0.85-0.9	0
0.9-0.95	4
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9394	High Similarity	NPC318935
0.9055	High Similarity	NPC151489
0.9051	High Similarity	NPC220523
0.8052	Intermediate Similarity	NPC253810
0.7987	Intermediate Similarity	NPC314940
0.7987	Intermediate Similarity	NPC473764
0.7941	Intermediate Similarity	NPC165370
0.7941	Intermediate Similarity	NPC212125
0.7941	Intermediate Similarity	NPC306397
0.7917	Intermediate Similarity	NPC470403
0.7917	Intermediate Similarity	NPC470404
0.7917	Intermediate Similarity	NPC470394
0.7872	Intermediate Similarity	NPC328029
0.7808	Intermediate Similarity	NPC470395
0.78	Intermediate Similarity	NPC63562
0.7712	Intermediate Similarity	NPC25899
0.7707	Intermediate Similarity	NPC252590
0.7703	Intermediate Similarity	NPC257142
0.7697	Intermediate Similarity	NPC132680
0.7697	Intermediate Similarity	NPC269919
0.7662	Intermediate Similarity	NPC48192
0.7622	Intermediate Similarity	NPC29702
0.7597	Intermediate Similarity	NPC63338
0.7597	Intermediate Similarity	NPC322976
0.7597	Intermediate Similarity	NPC324203
0.7581	Intermediate Similarity	NPC83987
0.7569	Intermediate Similarity	NPC114310
0.755	Intermediate Similarity	NPC284348
0.7548	Intermediate Similarity	NPC124542
0.7548	Intermediate Similarity	NPC471177
0.7548	Intermediate Similarity	NPC59779
0.75	Intermediate Similarity	NPC263439
0.75	Intermediate Similarity	NPC211187
0.75	Intermediate Similarity	NPC473057
0.7452	Intermediate Similarity	NPC471178
0.7419	Intermediate Similarity	NPC113812
0.74	Intermediate Similarity	NPC302159
0.7355	Intermediate Similarity	NPC116573
0.7312	Intermediate Similarity	NPC256828
0.7296	Intermediate Similarity	NPC108469
0.7273	Intermediate Similarity	NPC161887
0.7273	Intermediate Similarity	NPC219963
0.7273	Intermediate Similarity	NPC266551
0.7273	Intermediate Similarity	NPC315320
0.7231	Intermediate Similarity	NPC231655
0.7231	Intermediate Similarity	NPC76540
0.7172	Intermediate Similarity	NPC322488
0.717	Intermediate Similarity	NPC97367
0.7152	Intermediate Similarity	NPC120798
0.7134	Intermediate Similarity	NPC138018
0.7107	Intermediate Similarity	NPC79911
0.7105	Intermediate Similarity	NPC167400
0.7083	Intermediate Similarity	NPC156059
0.7076	Intermediate Similarity	NPC3715
0.7068	Intermediate Similarity	NPC27802
0.7063	Intermediate Similarity	NPC471311
0.7063	Intermediate Similarity	NPC471313
0.7052	Intermediate Similarity	NPC226202
0.7048	Intermediate Similarity	NPC149402
0.7041	Intermediate Similarity	NPC20249
0.7006	Intermediate Similarity	NPC52831
0.7006	Intermediate Similarity	NPC325705
0.6989	Remote Similarity	NPC192315
0.6988	Remote Similarity	NPC184964
0.6987	Remote Similarity	NPC153769
0.6986	Remote Similarity	NPC324611
0.6986	Remote Similarity	NPC256893
0.6963	Remote Similarity	NPC235843
0.6951	Remote Similarity	NPC14651
0.6951	Remote Similarity	NPC121658
0.6949	Remote Similarity	NPC476167
0.6946	Remote Similarity	NPC42979
0.6933	Remote Similarity	NPC44161
0.6928	Remote Similarity	NPC471323
0.6928	Remote Similarity	NPC224764
0.6912	Remote Similarity	NPC473901
0.6908	Remote Similarity	NPC60553
0.689	Remote Similarity	NPC476518
0.6886	Remote Similarity	NPC96890
0.6839	Remote Similarity	NPC161292
0.6835	Remote Similarity	NPC36168
0.6835	Remote Similarity	NPC312860
0.6829	Remote Similarity	NPC319456
0.6824	Remote Similarity	NPC220765
0.6813	Remote Similarity	NPC477113
0.6812	Remote Similarity	NPC84268
0.6807	Remote Similarity	NPC111624
0.6792	Remote Similarity	NPC263455
0.6784	Remote Similarity	NPC204717
0.6776	Remote Similarity	NPC316403
0.6768	Remote Similarity	NPC41717
0.6766	Remote Similarity	NPC95898
0.6763	Remote Similarity	NPC36498
0.6744	Remote Similarity	NPC314002
0.6739	Remote Similarity	NPC477111
0.6738	Remote Similarity	NPC11863
0.6714	Remote Similarity	NPC297486
0.6714	Remote Similarity	NPC471402
0.6714	Remote Similarity	NPC240136
0.671	Remote Similarity	NPC230085
0.671	Remote Similarity	NPC159630
0.6705	Remote Similarity	NPC171171
0.6687	Remote Similarity	NPC33229
0.6686	Remote Similarity	NPC55038
0.6667	Remote Similarity	NPC329541
0.6667	Remote Similarity	NPC84508
0.6667	Remote Similarity	NPC290094
0.6667	Remote Similarity	NPC91958
0.6667	Remote Similarity	NPC46580
0.6667	Remote Similarity	NPC143603
0.6647	Remote Similarity	NPC273532
0.6647	Remote Similarity	NPC295158
0.6645	Remote Similarity	NPC471312
0.6629	Remote Similarity	NPC146724
0.6627	Remote Similarity	NPC203754
0.6627	Remote Similarity	NPC150048
0.661	Remote Similarity	NPC324149
0.6608	Remote Similarity	NPC478032
0.6597	Remote Similarity	NPC56856
0.6582	Remote Similarity	NPC112741
0.6576	Remote Similarity	NPC472259
0.6559	Remote Similarity	NPC18348
0.6558	Remote Similarity	NPC280853
0.6558	Remote Similarity	NPC85443
0.6556	Remote Similarity	NPC267928
0.6556	Remote Similarity	NPC90229
0.6554	Remote Similarity	NPC471589
0.6554	Remote Similarity	NPC313823
0.6533	Remote Similarity	NPC471322
0.6531	Remote Similarity	NPC202957
0.6531	Remote Similarity	NPC169625
0.6528	Remote Similarity	NPC265605
0.6528	Remote Similarity	NPC48564
0.6528	Remote Similarity	NPC182570
0.6524	Remote Similarity	NPC131718
0.6517	Remote Similarity	NPC99666
0.6516	Remote Similarity	NPC245657
0.6516	Remote Similarity	NPC285016
0.6512	Remote Similarity	NPC478023
0.6512	Remote Similarity	NPC317010
0.6503	Remote Similarity	NPC212742
0.6494	Remote Similarity	NPC471596
0.6492	Remote Similarity	NPC477110
0.6486	Remote Similarity	NPC470500
0.6485	Remote Similarity	NPC177404
0.648	Remote Similarity	NPC289786
0.6477	Remote Similarity	NPC74382
0.6477	Remote Similarity	NPC206251
0.6467	Remote Similarity	NPC98187
0.6453	Remote Similarity	NPC164340
0.6448	Remote Similarity	NPC19872
0.6446	Remote Similarity	NPC118511
0.6446	Remote Similarity	NPC102423
0.6444	Remote Similarity	NPC326634
0.6443	Remote Similarity	NPC89490
0.6441	Remote Similarity	NPC472289
0.6441	Remote Similarity	NPC32771
0.6438	Remote Similarity	NPC46358
0.6425	Remote Similarity	NPC314270
0.6423	Remote Similarity	NPC255721
0.642	Remote Similarity	NPC107287
0.642	Remote Similarity	NPC314573
0.6419	Remote Similarity	NPC135488
0.6416	Remote Similarity	NPC271792
0.6409	Remote Similarity	NPC222018
0.6409	Remote Similarity	NPC242209
0.6402	Remote Similarity	NPC5145
0.64	Remote Similarity	NPC207851
0.64	Remote Similarity	NPC475090
0.64	Remote Similarity	NPC329896
0.64	Remote Similarity	NPC475105
0.6398	Remote Similarity	NPC118832
0.6398	Remote Similarity	NPC165349
0.6398	Remote Similarity	NPC274291
0.6398	Remote Similarity	NPC264166
0.6398	Remote Similarity	NPC329708
0.6398	Remote Similarity	NPC47059
0.6395	Remote Similarity	NPC476322
0.6395	Remote Similarity	NPC27740
0.6392	Remote Similarity	NPC313804
0.6392	Remote Similarity	NPC315804
0.6392	Remote Similarity	NPC471598
0.6391	Remote Similarity	NPC164664
0.6389	Remote Similarity	NPC84853
0.6382	Remote Similarity	NPC330326
0.6378	Remote Similarity	NPC470678
0.6378	Remote Similarity	NPC211813
0.6374	Remote Similarity	NPC77555
0.6374	Remote Similarity	NPC156704
0.6364	Remote Similarity	NPC42591
0.6364	Remote Similarity	NPC241025
0.6364	Remote Similarity	NPC213774
0.6359	Remote Similarity	NPC45459
0.6359	Remote Similarity	NPC315491
0.6351	Remote Similarity	NPC146373
0.6351	Remote Similarity	NPC166424
0.6351	Remote Similarity	NPC245244
0.6348	Remote Similarity	NPC224327
0.6348	Remote Similarity	NPC110741
0.6347	Remote Similarity	NPC162268

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 NPC174421 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	428
0.1-0.2	1135
0.2-0.3	606
0.3-0.4	2654
0.4-0.5	3008
0.5-0.6	1058
0.6-0.7	216
0.7-0.8	42
0.8-0.85	2
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8493	Intermediate Similarity	NPD604	Clinical (unspecified phase)
0.8403	Intermediate Similarity	NPD9706	Clinical (unspecified phase)
0.8027	Intermediate Similarity	NPD9595	Approved
0.8027	Intermediate Similarity	NPD9596	Approved
0.7949	Intermediate Similarity	NPD158	Discontinued
0.7941	Intermediate Similarity	NPD9284	Approved
0.7941	Intermediate Similarity	NPD9080	Approved
0.7862	Intermediate Similarity	NPD8823	Approved
0.7815	Intermediate Similarity	NPD9574	Clinical (unspecified phase)
0.7762	Intermediate Similarity	NPD9076	Clinical (unspecified phase)
0.7722	Intermediate Similarity	NPD9690	Approved
0.7697	Intermediate Similarity	NPD9383	Approved
0.7697	Intermediate Similarity	NPD9382	Approved
0.7597	Intermediate Similarity	NPD9705	Discontinued
0.7597	Intermediate Similarity	NPD112	Approved
0.7597	Intermediate Similarity	NPD9398	Clinical (unspecified phase)
0.7569	Intermediate Similarity	NPD9506	Approved
0.7517	Intermediate Similarity	NPD852	Discontinued
0.7517	Intermediate Similarity	NPD203	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD862	Approved
0.75	Intermediate Similarity	NPD863	Approved
0.75	Intermediate Similarity	NPD861	Approved
0.7421	Intermediate Similarity	NPD5319	Approved
0.7421	Intermediate Similarity	NPD565	Phase 2
0.7421	Intermediate Similarity	NPD5320	Approved
0.7405	Intermediate Similarity	NPD424	Approved
0.7405	Intermediate Similarity	NPD425	Approved
0.7375	Intermediate Similarity	NPD9548	Phase 2
0.7372	Intermediate Similarity	NPD1418	Phase 2
0.7297	Intermediate Similarity	NPD1649	Discontinued
0.7273	Intermediate Similarity	NPD9206	Approved
0.7273	Intermediate Similarity	NPD9207	Approved
0.7267	Intermediate Similarity	NPD2123	Phase 3
0.7251	Intermediate Similarity	NPD9695	Approved
0.7231	Intermediate Similarity	NPD9099	Clinical (unspecified phase)
0.7231	Intermediate Similarity	NPD9098	Phase 3
0.7197	Intermediate Similarity	NPD5255	Approved
0.7152	Intermediate Similarity	NPD3813	Approved
0.7152	Intermediate Similarity	NPD1352	Discontinued
0.7143	Intermediate Similarity	NPD6872	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD926	Approved
0.7125	Intermediate Similarity	NPD925	Approved
0.7105	Intermediate Similarity	NPD9075	Approved
0.7105	Intermediate Similarity	NPD9074	Approved
0.7093	Intermediate Similarity	NPD9689	Approved
0.7076	Intermediate Similarity	NPD1213	Phase 3
0.7014	Intermediate Similarity	NPD1095	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD9510	Approved
0.6988	Remote Similarity	NPD5751	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD4824	Approved
0.6963	Remote Similarity	NPD4823	Approved
0.6946	Remote Similarity	NPD1620	Clinical (unspecified phase)
0.6934	Remote Similarity	NPD60	Approved
0.6933	Remote Similarity	NPD2781	Approved
0.6914	Remote Similarity	NPD2782	Approved
0.6914	Remote Similarity	NPD2780	Approved
0.6886	Remote Similarity	NPD6159	Phase 2
0.6864	Remote Similarity	NPD7414	Clinical (unspecified phase)
0.686	Remote Similarity	NPD1034	Phase 3
0.686	Remote Similarity	NPD1033	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD9688	Approved
0.6854	Remote Similarity	NPD9687	Approved
0.6842	Remote Similarity	NPD107	Approved
0.6835	Remote Similarity	NPD8840	Approved
0.6812	Remote Similarity	NPD269	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD3039	Clinical (unspecified phase)
0.677	Remote Similarity	NPD704	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD9364	Phase 2
0.6763	Remote Similarity	NPD9363	Approved
0.6753	Remote Similarity	NPD3717	Discontinued
0.6743	Remote Similarity	NPD4148	Approved
0.6742	Remote Similarity	NPD1229	Phase 2
0.6714	Remote Similarity	NPD9392	Approved
0.6714	Remote Similarity	NPD9396	Approved
0.6711	Remote Similarity	NPD1380	Discovery
0.6708	Remote Similarity	NPD2581	Approved
0.6708	Remote Similarity	NPD2582	Approved
0.6705	Remote Similarity	NPD4375	Approved
0.6686	Remote Similarity	NPD1032	Phase 2
0.6667	Remote Similarity	NPD1923	Clinical (unspecified phase)
0.6631	Remote Similarity	NPD3779	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD4021	Phase 2
0.661	Remote Similarity	NPD6569	Phase 2
0.661	Remote Similarity	NPD5317	Clinical (unspecified phase)
0.6601	Remote Similarity	NPD2896	Discontinued
0.6592	Remote Similarity	NPD3478	Clinical (unspecified phase)
0.6592	Remote Similarity	NPD3477	Phase 2
0.6591	Remote Similarity	NPD4081	Clinical (unspecified phase)
0.6582	Remote Similarity	NPD4702	Approved
0.6582	Remote Similarity	NPD9271	Approved
0.6582	Remote Similarity	NPD4703	Approved
0.6581	Remote Similarity	NPD1383	Phase 3
0.6581	Remote Similarity	NPD1382	Phase 2
0.6581	Remote Similarity	NPD4805	Approved
0.6573	Remote Similarity	NPD6361	Phase 2
0.6554	Remote Similarity	NPD5352	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD1427	Clinical (unspecified phase)
0.6533	Remote Similarity	NPD9726	Discontinued
0.6528	Remote Similarity	NPD270	Clinical (unspecified phase)
0.6528	Remote Similarity	NPD9598	Discontinued
0.6528	Remote Similarity	NPD268	Approved
0.6528	Remote Similarity	NPD271	Approved
0.6512	Remote Similarity	NPD2601	Approved
0.6512	Remote Similarity	NPD2600	Approved
0.6512	Remote Similarity	NPD2599	Approved
0.6496	Remote Similarity	NPD9376	Approved
0.649	Remote Similarity	NPD1627	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD5999	Phase 2
0.648	Remote Similarity	NPD5575	Clinical (unspecified phase)
0.648	Remote Similarity	NPD4551	Phase 2
0.6474	Remote Similarity	NPD1570	Approved
0.6474	Remote Similarity	NPD3386	Phase 2
0.6474	Remote Similarity	NPD9362	Approved
0.6464	Remote Similarity	NPD2952	Discontinued
0.6464	Remote Similarity	NPD2959	Phase 3
0.6464	Remote Similarity	NPD1622	Discontinued
0.6463	Remote Similarity	NPD3433	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD4804	Approved
0.6446	Remote Similarity	NPD5088	Discontinued
0.6437	Remote Similarity	NPD952	Approved
0.6425	Remote Similarity	NPD4372	Phase 1
0.6415	Remote Similarity	NPD7469	Discontinued
0.6415	Remote Similarity	NPD6148	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD5316	Approved
0.64	Remote Similarity	NPD3569	Discontinued
0.6398	Remote Similarity	NPD4033	Approved
0.6398	Remote Similarity	NPD4036	Approved
0.6398	Remote Similarity	NPD4038	Approved
0.6398	Remote Similarity	NPD4034	Approved
0.6398	Remote Similarity	NPD4037	Approved
0.6398	Remote Similarity	NPD4122	Approved
0.6398	Remote Similarity	NPD4039	Approved
0.6398	Remote Similarity	NPD31	Approved
0.6398	Remote Similarity	NPD4035	Approved
0.6398	Remote Similarity	NPD32	Approved
0.6395	Remote Similarity	NPD4071	Approved
0.6395	Remote Similarity	NPD9357	Approved
0.6395	Remote Similarity	NPD4072	Approved
0.6393	Remote Similarity	NPD2175	Phase 3
0.6393	Remote Similarity	NPD2176	Approved
0.6393	Remote Similarity	NPD2177	Approved
0.6392	Remote Similarity	NPD751	Clinical (unspecified phase)
0.6387	Remote Similarity	NPD2616	Phase 3
0.6387	Remote Similarity	NPD2615	Phase 3
0.6382	Remote Similarity	NPD9100	Approved
0.6378	Remote Similarity	NPD3931	Approved
0.6378	Remote Similarity	NPD3928	Approved
0.6375	Remote Similarity	NPD1661	Suspended
0.6374	Remote Similarity	NPD7948	Phase 1
0.6364	Remote Similarity	NPD4889	Approved
0.6359	Remote Similarity	NPD484	Approved
0.6358	Remote Similarity	NPD510	Phase 1
0.6358	Remote Similarity	NPD3262	Approved
0.6354	Remote Similarity	NPD3395	Approved
0.6354	Remote Similarity	NPD3396	Approved
0.6353	Remote Similarity	NPD1078	Clinical (unspecified phase)
0.6329	Remote Similarity	NPD3525	Discontinued
0.6319	Remote Similarity	NPD1704	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD2076	Approved
0.6316	Remote Similarity	NPD1599	Approved
0.6316	Remote Similarity	NPD2077	Approved
0.6309	Remote Similarity	NPD9583	Approved
0.6307	Remote Similarity	NPD1096	Discontinued
0.6303	Remote Similarity	NPD4671	Clinical (unspecified phase)
0.6303	Remote Similarity	NPD4669	Clinical (unspecified phase)
0.6303	Remote Similarity	NPD4670	Clinical (unspecified phase)
0.6303	Remote Similarity	NPD820	Phase 3
0.6299	Remote Similarity	NPD272	Approved
0.6294	Remote Similarity	NPD8356	Approved
0.6294	Remote Similarity	NPD313	Approved
0.6292	Remote Similarity	NPD6257	Clinical (unspecified phase)
0.6287	Remote Similarity	NPD1684	Approved
0.6287	Remote Similarity	NPD1685	Approved
0.6279	Remote Similarity	NPD5065	Approved
0.6278	Remote Similarity	NPD2334	Discontinued
0.6277	Remote Similarity	NPD9507	Approved
0.6271	Remote Similarity	NPD3082	Discontinued
0.627	Remote Similarity	NPD4396	Clinical (unspecified phase)
0.627	Remote Similarity	NPD6389	Clinical (unspecified phase)
0.6267	Remote Similarity	NPD1598	Discontinued
0.6267	Remote Similarity	NPD2119	Approved
0.6267	Remote Similarity	NPD992	Clinical (unspecified phase)
0.6267	Remote Similarity	NPD2118	Approved
0.6267	Remote Similarity	NPD991	Phase 2
0.6258	Remote Similarity	NPD5965	Clinical (unspecified phase)
0.6258	Remote Similarity	NPD206	Clinical (unspecified phase)
0.6257	Remote Similarity	NPD4044	Discontinued
0.6257	Remote Similarity	NPD408	Approved
0.625	Remote Similarity	NPD712	Clinical (unspecified phase)
0.625	Remote Similarity	NPD5522	Clinical (unspecified phase)
0.6243	Remote Similarity	NPD3921	Approved
0.6243	Remote Similarity	NPD5100	Phase 3
0.6243	Remote Similarity	NPD3923	Approved
0.6243	Remote Similarity	NPD3922	Approved
0.6243	Remote Similarity	NPD3924	Approved
0.6242	Remote Similarity	NPD6026	Approved
0.6237	Remote Similarity	NPD1621	Discontinued
0.6236	Remote Similarity	NPD4921	Phase 3
0.6236	Remote Similarity	NPD706	Phase 1
0.6236	Remote Similarity	NPD4920	Clinical (unspecified phase)

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data