NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	111.03
Volume:	107.148
LogP:	-0.273
LogD:	-0.031
LogS:	0.251
# Rotatable Bonds:	0
TPSA:	53.09
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	1
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.498
Synthetic Accessibility Score:	2.482
Fsp3:	0.0
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.572
MDCK Permeability:	1.1917789379367605e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.005
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	0.192

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.407
Plasma Protein Binding (PPB):	19.42930793762207%
Volume Distribution (VD):	0.526
Pgp-substrate:	76.6543197631836%

ADMET: Metabolism

CYP1A2-inhibitor:	0.05
CYP1A2-substrate:	0.267
CYP2C19-inhibitor:	0.061
CYP2C19-substrate:	0.062
CYP2C9-inhibitor:	0.013
CYP2C9-substrate:	0.836
CYP2D6-inhibitor:	0.012
CYP2D6-substrate:	0.257
CYP3A4-inhibitor:	0.009
CYP3A4-substrate:	0.082

ADMET: Excretion

Clearance (CL):	12.426
Half-life (T1/2):	0.924

ADMET: Toxicity

hERG Blockers:	0.019
Human Hepatotoxicity (H-HT):	0.141
Drug-inuced Liver Injury (DILI):	0.805
AMES Toxicity:	0.289
Rat Oral Acute Toxicity:	0.94
Maximum Recommended Daily Dose:	0.008
Skin Sensitization:	0.258
Carcinogencity:	0.36
Eye Corrosion:	0.72
Eye Irritation:	0.988
Respiratory Toxicity:	0.84

Download Data

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

Natural Product: NPC318935

Natural Product ID:	NPC318935
*Common Name:**	Pyridine-2,3-Diol
IUPAC Name:	3-hydroxy-1H-pyridin-2-one
Synonyms:	Pyridine-2,3-Diol
Standard InCHIKey:	GGOZGYRTNQBSSA-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C5H5NO2/c7-4-2-1-3-6-5(4)8/h1-3,7H,(H,6,8)
SMILES:	C1=CNC(=O)C(=C1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL287899
PubChem CID:	28115
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000089] Pyridines and derivatives [CHEMONTID:0002224] Hydropyridines [CHEMONTID:0001160] Pyridinones

*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
NPO4011	Chlamydomonas reinhardtii	Species	Chlamydomonadaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20581114]
NPO4011	Chlamydomonas reinhardtii	Species	Chlamydomonadaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25515814]
NPO4011	Chlamydomonas reinhardtii	Species	Chlamydomonadaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]
NPO4011	Chlamydomonas reinhardtii	Species	Chlamydomonadaceae	Eukaryota	n.a.	n.a.	n.a.	Database[MetaboLights]
NPO4011	Chlamydomonas reinhardtii	Species	Chlamydomonadaceae	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	6
Others	12

Activity Type	# Activity
Cell Line	2
Individual Protein	13
Organism	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	ID50	=	300.0	uM	PMID[475667]
NPT280	Individual Protein	Matrix metalloproteinase 9	Homo sapiens	Inhibition	=	21.0	%	PMID[475669]
NPT568	Individual Protein	Matrix metalloproteinase-2	Homo sapiens	Inhibition	=	-18.0	%	PMID[475669]
NPT569	Individual Protein	Matrix metalloproteinase 8	Homo sapiens	Inhibition	=	7.0	%	PMID[475669]
NPT150	Individual Protein	Anthrax lethal factor	Bacillus anthracis	Inhibition	=	-19.0	%	PMID[475669]
NPT270	Individual Protein	Nitric oxide synthase, inducible	Mus musculus	Inhibition	=	0.0	%	PMID[475669]
NPT567	Individual Protein	Matrix metalloproteinase 3	Homo sapiens	Inhibition	=	-7.0	%	PMID[475669]
NPT43	Individual Protein	Tyrosinase	Agaricus bisporus	Inhibition	=	-9.0	%	PMID[475669]
NPT570	Individual Protein	Arachidonate 5-lipoxygenase	Homo sapiens	Inhibition	=	90.0	%	PMID[475669]
NPT645	Individual Protein	D-amino-acid oxidase	Homo sapiens	IC50	=	1150.0	nM	PMID[475671]
NPT1970	Cell Line	THP-1	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[475672]
NPT69	Individual Protein	Matrix metalloproteinase-1	Homo sapiens	Inhibition	=	8.0	%	PMID[475669]
NPT687	Individual Protein	Histone deacetylase 8	Homo sapiens	Inhibition	<	20.0	%	PMID[475670]
NPT692	Individual Protein	Histone deacetylase 6	Homo sapiens	Inhibition	<	20.0	%	PMID[475670]
NPT684	Individual Protein	Histone deacetylase 1	Homo sapiens	IC50	<	20.0	nM	PMID[475670]
NPT633	Organism	Leishmania donovani	Leishmania donovani	IC50	>	40.0	ug.mL-1	PMID[475672]
NPT633	Organism	Leishmania donovani	Leishmania donovani	IC50	>	10.0	ug.mL-1	PMID[475672]

☑ 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 NPC318935 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	1744
0.1-0.2	14230
0.2-0.3	6424
0.3-0.4	13956
0.4-0.5	4290
0.5-0.6	1696
0.6-0.7	303
0.7-0.8	49
0.8-0.85	0
0.85-0.9	3
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9394	High Similarity	NPC174421
0.8939	High Similarity	NPC151489
0.8811	High Similarity	NPC220523
0.7875	Intermediate Similarity	NPC253810
0.7746	Intermediate Similarity	NPC212125
0.7746	Intermediate Similarity	NPC165370
0.7746	Intermediate Similarity	NPC306397
0.7742	Intermediate Similarity	NPC63562
0.7733	Intermediate Similarity	NPC470403
0.7733	Intermediate Similarity	NPC470404
0.7733	Intermediate Similarity	NPC470394
0.7702	Intermediate Similarity	NPC473764
0.7702	Intermediate Similarity	NPC314940
0.7687	Intermediate Similarity	NPC328029
0.7643	Intermediate Similarity	NPC269919
0.7643	Intermediate Similarity	NPC132680
0.7632	Intermediate Similarity	NPC470395
0.7568	Intermediate Similarity	NPC29702
0.7562	Intermediate Similarity	NPC473057
0.7547	Intermediate Similarity	NPC25899
0.7547	Intermediate Similarity	NPC324203
0.7547	Intermediate Similarity	NPC63338
0.7547	Intermediate Similarity	NPC322976
0.7546	Intermediate Similarity	NPC252590
0.7532	Intermediate Similarity	NPC257142
0.75	Intermediate Similarity	NPC48192
0.7484	Intermediate Similarity	NPC113812
0.7453	Intermediate Similarity	NPC211187
0.7453	Intermediate Similarity	NPC263439
0.7407	Intermediate Similarity	NPC471178
0.7389	Intermediate Similarity	NPC284348
0.7362	Intermediate Similarity	NPC108469
0.7312	Intermediate Similarity	NPC138018
0.7312	Intermediate Similarity	NPC116573
0.7285	Intermediate Similarity	NPC114310
0.7284	Intermediate Similarity	NPC124542
0.7284	Intermediate Similarity	NPC59779
0.7284	Intermediate Similarity	NPC471177
0.7273	Intermediate Similarity	NPC256828
0.7244	Intermediate Similarity	NPC302159
0.7135	Intermediate Similarity	NPC219963
0.7135	Intermediate Similarity	NPC161887
0.7135	Intermediate Similarity	NPC266551
0.7134	Intermediate Similarity	NPC97367
0.7121	Intermediate Similarity	NPC83987
0.7119	Intermediate Similarity	NPC226202
0.7114	Intermediate Similarity	NPC315320
0.711	Intermediate Similarity	NPC20249
0.7073	Intermediate Similarity	NPC79911
0.707	Intermediate Similarity	NPC167400
0.7063	Intermediate Similarity	NPC153769
0.702	Intermediate Similarity	NPC322488
0.7012	Intermediate Similarity	NPC120798
0.7006	Intermediate Similarity	NPC319456
0.6977	Remote Similarity	NPC325705
0.6977	Remote Similarity	NPC52831
0.6949	Remote Similarity	NPC3715
0.6918	Remote Similarity	NPC161292
0.6899	Remote Similarity	NPC471323
0.6898	Remote Similarity	NPC18348
0.6879	Remote Similarity	NPC60553
0.6868	Remote Similarity	NPC192315
0.686	Remote Similarity	NPC184964
0.6857	Remote Similarity	NPC156059
0.6831	Remote Similarity	NPC476167
0.6824	Remote Similarity	NPC121658
0.6824	Remote Similarity	NPC14651
0.6821	Remote Similarity	NPC42979
0.6821	Remote Similarity	NPC149402
0.6812	Remote Similarity	NPC231655
0.6812	Remote Similarity	NPC76540
0.681	Remote Similarity	NPC312860
0.6805	Remote Similarity	NPC44161
0.6802	Remote Similarity	NPC224764
0.68	Remote Similarity	NPC471313
0.68	Remote Similarity	NPC471311
0.6796	Remote Similarity	NPC326634
0.6768	Remote Similarity	NPC263455
0.6765	Remote Similarity	NPC476518
0.6763	Remote Similarity	NPC96890
0.6747	Remote Similarity	NPC84508
0.6744	Remote Similarity	NPC95898
0.6742	Remote Similarity	NPC36498
0.6732	Remote Similarity	NPC324611
0.6723	Remote Similarity	NPC314002
0.672	Remote Similarity	NPC477111
0.6707	Remote Similarity	NPC36168
0.6705	Remote Similarity	NPC220765
0.6703	Remote Similarity	NPC146724
0.6702	Remote Similarity	NPC477113
0.6687	Remote Similarity	NPC159630
0.6687	Remote Similarity	NPC230085
0.6686	Remote Similarity	NPC317010
0.6667	Remote Similarity	NPC27802
0.6667	Remote Similarity	NPC316403
0.6667	Remote Similarity	NPC204717
0.6667	Remote Similarity	NPC33229
0.6649	Remote Similarity	NPC472259
0.6648	Remote Similarity	NPC46580
0.6647	Remote Similarity	NPC41717
0.6646	Remote Similarity	NPC280853
0.6628	Remote Similarity	NPC273532
0.6623	Remote Similarity	NPC256893
0.6604	Remote Similarity	NPC245657
0.6604	Remote Similarity	NPC285016
0.6592	Remote Similarity	NPC171171
0.6591	Remote Similarity	NPC478032
0.659	Remote Similarity	NPC111624
0.6582	Remote Similarity	NPC173080
0.6582	Remote Similarity	NPC471596
0.6573	Remote Similarity	NPC235843
0.6564	Remote Similarity	NPC112741
0.6557	Remote Similarity	NPC329541
0.6557	Remote Similarity	NPC289786
0.6536	Remote Similarity	NPC295158
0.6534	Remote Similarity	NPC164340
0.6528	Remote Similarity	NPC473901
0.6514	Remote Similarity	NPC194724
0.6503	Remote Similarity	NPC99666
0.6497	Remote Similarity	NPC314270
0.6488	Remote Similarity	NPC212742
0.6481	Remote Similarity	NPC471598
0.648	Remote Similarity	NPC477110
0.648	Remote Similarity	NPC55038
0.6471	Remote Similarity	NPC71079
0.6452	Remote Similarity	NPC90229
0.6452	Remote Similarity	NPC267928
0.6444	Remote Similarity	NPC42591
0.6438	Remote Similarity	NPC84268
0.6438	Remote Similarity	NPC85443
0.6433	Remote Similarity	NPC474217
0.6429	Remote Similarity	NPC472289
0.6429	Remote Similarity	NPC32771
0.642	Remote Similarity	NPC203754
0.642	Remote Similarity	NPC150048
0.6415	Remote Similarity	NPC471312
0.6413	Remote Similarity	NPC324149
0.6413	Remote Similarity	NPC195268
0.6413	Remote Similarity	NPC133140
0.641	Remote Similarity	NPC202605
0.641	Remote Similarity	NPC112206
0.6409	Remote Similarity	NPC314573
0.6407	Remote Similarity	NPC107287
0.6404	Remote Similarity	NPC478023
0.6395	Remote Similarity	NPC85918
0.6392	Remote Similarity	NPC5145
0.6389	Remote Similarity	NPC207851
0.6387	Remote Similarity	NPC470500
0.6376	Remote Similarity	NPC11863
0.6374	Remote Similarity	NPC74382
0.6374	Remote Similarity	NPC206251
0.6374	Remote Similarity	NPC177404
0.6368	Remote Similarity	NPC211813
0.6368	Remote Similarity	NPC470678
0.6364	Remote Similarity	NPC77555
0.6364	Remote Similarity	NPC156704
0.6358	Remote Similarity	NPC278366
0.6358	Remote Similarity	NPC98187
0.6358	Remote Similarity	NPC127730
0.6354	Remote Similarity	NPC241025
0.6351	Remote Similarity	NPC471402
0.6351	Remote Similarity	NPC297486
0.6351	Remote Similarity	NPC240136
0.6349	Remote Similarity	NPC315491
0.6349	Remote Similarity	NPC45459
0.6339	Remote Similarity	NPC110741
0.6337	Remote Similarity	NPC162268
0.6335	Remote Similarity	NPC475774
0.6335	Remote Similarity	NPC200836
0.6324	Remote Similarity	NPC244536
0.6324	Remote Similarity	NPC56170
0.6316	Remote Similarity	NPC290094
0.6316	Remote Similarity	NPC131718
0.6313	Remote Similarity	NPC8022
0.6313	Remote Similarity	NPC271792
0.6313	Remote Similarity	NPC470799
0.631	Remote Similarity	NPC242209
0.631	Remote Similarity	NPC222018
0.6309	Remote Similarity	NPC91958
0.6309	Remote Similarity	NPC143603
0.6307	Remote Similarity	NPC471294
0.6302	Remote Similarity	NPC210256
0.6302	Remote Similarity	NPC329708
0.6302	Remote Similarity	NPC264166
0.6302	Remote Similarity	NPC274291
0.6302	Remote Similarity	NPC165349
0.6302	Remote Similarity	NPC118832
0.6302	Remote Similarity	NPC47059
0.63	Remote Similarity	NPC315804
0.63	Remote Similarity	NPC313804
0.6298	Remote Similarity	NPC284559
0.6294	Remote Similarity	NPC255721
0.6286	Remote Similarity	NPC126481
0.6286	Remote Similarity	NPC164664
0.6279	Remote Similarity	NPC47298
0.6279	Remote Similarity	NPC315214
0.6277	Remote Similarity	NPC224928
0.6273	Remote Similarity	NPC471594
0.6263	Remote Similarity	NPC213308
0.6263	Remote Similarity	NPC19872

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 NPC318935 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	345
0.1-0.2	1150
0.2-0.3	657
0.3-0.4	2634
0.4-0.5	3092
0.5-0.6	1060
0.6-0.7	176
0.7-0.8	34
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.817	Intermediate Similarity	NPD604	Clinical (unspecified phase)
0.8079	Intermediate Similarity	NPD9706	Clinical (unspecified phase)
0.7919	Intermediate Similarity	NPD8823	Approved
0.7746	Intermediate Similarity	NPD9080	Approved
0.7746	Intermediate Similarity	NPD9284	Approved
0.7727	Intermediate Similarity	NPD9596	Approved
0.7727	Intermediate Similarity	NPD9595	Approved
0.7669	Intermediate Similarity	NPD158	Discontinued
0.7643	Intermediate Similarity	NPD9383	Approved
0.7643	Intermediate Similarity	NPD9382	Approved
0.7547	Intermediate Similarity	NPD9398	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD9506	Approved
0.7467	Intermediate Similarity	NPD9076	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD203	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD852	Discontinued
0.7455	Intermediate Similarity	NPD9690	Approved
0.7421	Intermediate Similarity	NPD9574	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD424	Approved
0.7362	Intermediate Similarity	NPD425	Approved
0.7346	Intermediate Similarity	NPD863	Approved
0.7346	Intermediate Similarity	NPD861	Approved
0.7346	Intermediate Similarity	NPD862	Approved
0.7329	Intermediate Similarity	NPD112	Approved
0.7329	Intermediate Similarity	NPD9705	Discontinued
0.7273	Intermediate Similarity	NPD565	Phase 2
0.7255	Intermediate Similarity	NPD1649	Discontinued
0.7169	Intermediate Similarity	NPD5320	Approved
0.7169	Intermediate Similarity	NPD5319	Approved
0.7126	Intermediate Similarity	NPD2123	Phase 3
0.7119	Intermediate Similarity	NPD9695	Approved
0.7115	Intermediate Similarity	NPD1352	Discontinued
0.7114	Intermediate Similarity	NPD9206	Approved
0.7114	Intermediate Similarity	NPD9207	Approved
0.7091	Intermediate Similarity	NPD925	Approved
0.7091	Intermediate Similarity	NPD926	Approved
0.707	Intermediate Similarity	NPD9075	Approved
0.707	Intermediate Similarity	NPD9074	Approved
0.7024	Intermediate Similarity	NPD9548	Phase 2
0.7012	Intermediate Similarity	NPD1418	Phase 2
0.7006	Intermediate Similarity	NPD3813	Approved
0.7006	Intermediate Similarity	NPD6872	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD9510	Approved
0.6959	Remote Similarity	NPD5751	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD5255	Approved
0.6949	Remote Similarity	NPD1213	Phase 3
0.6872	Remote Similarity	NPD9689	Approved
0.6867	Remote Similarity	NPD1095	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD1620	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD107	Approved
0.6812	Remote Similarity	NPD9098	Phase 3
0.6812	Remote Similarity	NPD9099	Clinical (unspecified phase)
0.6805	Remote Similarity	NPD2781	Approved
0.6786	Remote Similarity	NPD2780	Approved
0.6786	Remote Similarity	NPD2782	Approved
0.6763	Remote Similarity	NPD6159	Phase 2
0.6744	Remote Similarity	NPD1923	Clinical (unspecified phase)
0.6743	Remote Similarity	NPD7414	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD1034	Phase 3
0.6742	Remote Similarity	NPD1033	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD9364	Phase 2
0.6742	Remote Similarity	NPD9363	Approved
0.6721	Remote Similarity	NPD1229	Phase 2
0.6688	Remote Similarity	NPD1380	Discovery
0.6685	Remote Similarity	NPD3039	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD9688	Approved
0.6649	Remote Similarity	NPD9687	Approved
0.6611	Remote Similarity	NPD4021	Phase 2
0.6593	Remote Similarity	NPD5317	Clinical (unspecified phase)
0.6592	Remote Similarity	NPD4375	Approved
0.6573	Remote Similarity	NPD4823	Approved
0.6573	Remote Similarity	NPD4824	Approved
0.6571	Remote Similarity	NPD1032	Phase 2
0.6564	Remote Similarity	NPD9271	Approved
0.6562	Remote Similarity	NPD1383	Phase 3
0.6562	Remote Similarity	NPD1382	Phase 2
0.6552	Remote Similarity	NPD60	Approved
0.6528	Remote Similarity	NPD3779	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD1427	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD3717	Discontinued
0.6503	Remote Similarity	NPD6569	Phase 2
0.6488	Remote Similarity	NPD2582	Approved
0.6488	Remote Similarity	NPD2581	Approved
0.6484	Remote Similarity	NPD4081	Clinical (unspecified phase)
0.6478	Remote Similarity	NPD2896	Discontinued
0.6477	Remote Similarity	NPD4071	Approved
0.6477	Remote Similarity	NPD4072	Approved
0.6471	Remote Similarity	NPD2175	Phase 3
0.6471	Remote Similarity	NPD2176	Approved
0.6471	Remote Similarity	NPD2177	Approved
0.6467	Remote Similarity	NPD6361	Phase 2
0.6467	Remote Similarity	NPD4551	Phase 2
0.6463	Remote Similarity	NPD8840	Approved
0.6461	Remote Similarity	NPD9362	Approved
0.646	Remote Similarity	NPD4805	Approved
0.6452	Remote Similarity	NPD2952	Discontinued
0.6452	Remote Similarity	NPD1622	Discontinued
0.645	Remote Similarity	NPD704	Clinical (unspecified phase)
0.6448	Remote Similarity	NPD4148	Approved
0.6438	Remote Similarity	NPD269	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD5352	Clinical (unspecified phase)
0.6413	Remote Similarity	NPD3923	Approved
0.6413	Remote Similarity	NPD3921	Approved
0.6413	Remote Similarity	NPD3924	Approved
0.6413	Remote Similarity	NPD3922	Approved
0.6404	Remote Similarity	NPD2599	Approved
0.6404	Remote Similarity	NPD2600	Approved
0.6404	Remote Similarity	NPD2601	Approved
0.6398	Remote Similarity	NPD3478	Clinical (unspecified phase)
0.6398	Remote Similarity	NPD3477	Phase 2
0.6393	Remote Similarity	NPD5316	Approved
0.6391	Remote Similarity	NPD820	Phase 3
0.6389	Remote Similarity	NPD3569	Discontinued
0.6383	Remote Similarity	NPD5999	Phase 2
0.638	Remote Similarity	NPD751	Clinical (unspecified phase)
0.6378	Remote Similarity	NPD5575	Clinical (unspecified phase)
0.6374	Remote Similarity	NPD6257	Clinical (unspecified phase)
0.6369	Remote Similarity	NPD1570	Approved
0.6369	Remote Similarity	NPD3386	Phase 2
0.6364	Remote Similarity	NPD2959	Phase 3
0.6364	Remote Similarity	NPD4702	Approved
0.6364	Remote Similarity	NPD4703	Approved
0.6364	Remote Similarity	NPD7948	Phase 1
0.6359	Remote Similarity	NPD4131	Phase 3
0.6351	Remote Similarity	NPD9396	Approved
0.6351	Remote Similarity	NPD9392	Approved
0.6349	Remote Similarity	NPD484	Approved
0.6347	Remote Similarity	NPD510	Phase 1
0.6344	Remote Similarity	NPD1602	Discontinued
0.6337	Remote Similarity	NPD5088	Discontinued
0.6335	Remote Similarity	NPD4804	Approved
0.6333	Remote Similarity	NPD952	Approved
0.6324	Remote Similarity	NPD4086	Phase 1
0.6324	Remote Similarity	NPD4372	Phase 1
0.631	Remote Similarity	NPD1704	Clinical (unspecified phase)
0.6306	Remote Similarity	NPD9726	Discontinued
0.6304	Remote Similarity	NPD2544	Clinical (unspecified phase)
0.6302	Remote Similarity	NPD31	Approved
0.6302	Remote Similarity	NPD4033	Approved
0.6302	Remote Similarity	NPD4036	Approved
0.6302	Remote Similarity	NPD4034	Approved
0.6302	Remote Similarity	NPD4038	Approved
0.6302	Remote Similarity	NPD4037	Approved
0.6302	Remote Similarity	NPD4035	Approved
0.6302	Remote Similarity	NPD32	Approved
0.6302	Remote Similarity	NPD4039	Approved
0.6302	Remote Similarity	NPD4122	Approved
0.6298	Remote Similarity	NPD1096	Discontinued
0.6284	Remote Similarity	NPD2383	Phase 1
0.6279	Remote Similarity	NPD1684	Approved
0.6279	Remote Similarity	NPD4239	Clinical (unspecified phase)
0.6279	Remote Similarity	NPD1685	Approved
0.6266	Remote Similarity	NPD1627	Clinical (unspecified phase)
0.6264	Remote Similarity	NPD3082	Discontinued
0.6264	Remote Similarity	NPD4889	Approved
0.6263	Remote Similarity	NPD4396	Clinical (unspecified phase)
0.6257	Remote Similarity	NPD3396	Approved
0.6257	Remote Similarity	NPD3395	Approved
0.625	Remote Similarity	NPD9376	Approved
0.625	Remote Similarity	NPD1078	Clinical (unspecified phase)
0.6237	Remote Similarity	NPD6290	Phase 2
0.6236	Remote Similarity	NPD5100	Phase 3
0.6215	Remote Similarity	NPD1599	Approved
0.6212	Remote Similarity	NPD2615	Phase 3
0.6212	Remote Similarity	NPD2616	Phase 3
0.6207	Remote Similarity	NPD8356	Approved
0.6205	Remote Similarity	NPD6148	Clinical (unspecified phase)
0.6203	Remote Similarity	NPD1038	Approved
0.6199	Remote Similarity	NPD4669	Clinical (unspecified phase)
0.6199	Remote Similarity	NPD4670	Clinical (unspecified phase)
0.6199	Remote Similarity	NPD4671	Clinical (unspecified phase)
0.6198	Remote Similarity	NPD3931	Approved
0.6198	Remote Similarity	NPD3928	Approved
0.6188	Remote Similarity	NPD1783	Clinical (unspecified phase)
0.6186	Remote Similarity	NPD6728	Phase 3
0.6184	Remote Similarity	NPD270	Clinical (unspecified phase)
0.6184	Remote Similarity	NPD9598	Discontinued
0.6184	Remote Similarity	NPD268	Approved
0.6184	Remote Similarity	NPD271	Approved
0.6183	Remote Similarity	NPD2334	Discontinued
0.6178	Remote Similarity	NPD6389	Clinical (unspecified phase)
0.6175	Remote Similarity	NPD2814	Clinical (unspecified phase)
0.6175	Remote Similarity	NPD6344	Clinical (unspecified phase)
0.6174	Remote Similarity	NPD313	Approved
0.6168	Remote Similarity	NPD1661	Suspended
0.6167	Remote Similarity	NPD443	Clinical (unspecified phase)
0.6166	Remote Similarity	NPD4044	Discontinued
0.6163	Remote Similarity	NPD3433	Clinical (unspecified phase)
0.6162	Remote Similarity	NPD9714	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD1392	Approved
0.6154	Remote Similarity	NPD796	Phase 2
0.6154	Remote Similarity	NPD9507	Approved
0.6154	Remote Similarity	NPD3262	Approved
0.615	Remote Similarity	NPD5612	Discontinued
0.6146	Remote Similarity	NPD1621	Discontinued
0.6141	Remote Similarity	NPD706	Phase 1
0.6129	Remote Similarity	NPD3321	Discontinued
0.6129	Remote Similarity	NPD8063	Discontinued
0.6127	Remote Similarity	NPD4945	Discontinued
0.6126	Remote Similarity	NPD2958	Clinical (unspecified phase)
0.6124	Remote Similarity	NPD2077	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