NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	275.12
Volume:	281.222
LogP:	2.142
LogD:	1.336
LogS:	-3.2
# Rotatable Bonds:	3
TPSA:	83.47
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.648
Synthetic Accessibility Score:	2.554
Fsp3:	0.4
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.674
MDCK Permeability:	2.736718306550756e-05
Pgp-inhibitor:	0.03
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	0.01

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.45
Plasma Protein Binding (PPB):	74.87113189697266%
Volume Distribution (VD):	0.348
Pgp-substrate:	37.77352523803711%

ADMET: Metabolism

CYP1A2-inhibitor:	0.152
CYP1A2-substrate:	0.315
CYP2C19-inhibitor:	0.282
CYP2C19-substrate:	0.218
CYP2C9-inhibitor:	0.196
CYP2C9-substrate:	0.588
CYP2D6-inhibitor:	0.046
CYP2D6-substrate:	0.184
CYP3A4-inhibitor:	0.116
CYP3A4-substrate:	0.283

ADMET: Excretion

Clearance (CL):	8.75
Half-life (T1/2):	0.822

ADMET: Toxicity

hERG Blockers:	0.014
Human Hepatotoxicity (H-HT):	0.44
Drug-inuced Liver Injury (DILI):	0.056
AMES Toxicity:	0.045
Rat Oral Acute Toxicity:	0.115
Maximum Recommended Daily Dose:	0.113
Skin Sensitization:	0.212
Carcinogencity:	0.052
Eye Corrosion:	0.003
Eye Irritation:	0.047
Respiratory Toxicity:	0.03

Download Data

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

Natural Product: NPC236795

Natural Product ID:	NPC236795
*Common Name:**	4-[2-(2-Hydroxy-3,5-Dimethylphenyl)-2-Oxoethyl]Piperidine-2,6-Dione
IUPAC Name:	4-[2-(2-hydroxy-3,5-dimethylphenyl)-2-oxoethyl]piperidine-2,6-dione
Synonyms:
Standard InCHIKey:	YTLMIHBTPWTPEV-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C15H17NO4/c1-8-3-9(2)15(20)11(4-8)12(17)5-10-6-13(18)16-14(19)7-10/h3-4,10,20H,5-7H2,1-2H3,(H,16,18,19)
SMILES:	Cc1cc(C)c(c(c1)C(=O)CC1CC(=NC(=O)C1)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3186963
PubChem CID:	245940
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0001831] Carbonyl compounds [CHEMONTID:0000118] Ketones [CHEMONTID:0003670] Aryl ketones [CHEMONTID:0004296] Phenylketones [CHEMONTID:0004298] Alkyl-phenylketones

*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
NPO3333	Aglaia gigantea	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17880174]
NPO1526	Ratibida latipalearis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1800631]
NPO24652	Toxicodendron succedaneum	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8416	Picrorhiza kurrooa	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24652	Toxicodendron succedaneum	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9603	Croton sparsiflorus	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8416	Picrorhiza kurrooa	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24652	Toxicodendron succedaneum	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9603	Croton sparsiflorus	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8416	Picrorhiza kurrooa	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO1937	Andropogon nardus	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2805	Distolasterias nipon	Species	Asteriidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3333	Aglaia gigantea	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO729	Espeletia marcana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9320	Weddellina squamulosa	Species	Podostemaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5219	Dendrobium rotundatum	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18350	Culcitium canescens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6787	Neoalsomitra integrifolia	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9937	Piptolepis leptospermoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24652	Toxicodendron succedaneum	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1526	Ratibida latipalearis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8416	Picrorhiza kurrooa	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9603	Croton sparsiflorus	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10867	Graphis elongata	Species	Aclididae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11355	Homarus americanus	Species	Nephropidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9020	Eriostemon fitzgeraldii	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12481	Croton californicus	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8547	Petasites niveus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12309	Malva crispa	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7365	Clibadium pentaneuron	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12535	Solanum toxicarium	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3900	Phellinus xeranticus	Species	Hymenochaetaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3202	0lina erumpens	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7883	Albugo candida	Species	Albuginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9227	Xylaria berteri	Species	Xylariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24849	Rhinella paracnemis	Species	Bufonidae	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	2

Activity Type	# Activity
Individual Protein	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1797	Individual Protein	Alpha trans-inducing protein (VP16)	Herpes simplex virus (type 1 / strain 17)	IC50	>	85413.0	nM	PMID[533022]
NPT3133	Individual Protein	COUP transcription factor 2	Homo sapiens	IC50	=	9879.0	nM	PMID[533022]

☑ 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 NPC236795 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	240
0.1-0.2	1288
0.2-0.3	4650
0.3-0.4	12250
0.4-0.5	7228
0.5-0.6	11319
0.6-0.7	5353
0.7-0.8	368
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.7899	Intermediate Similarity	NPC473751
0.7786	Intermediate Similarity	NPC242136
0.7785	Intermediate Similarity	NPC314693
0.7722	Intermediate Similarity	NPC101207
0.7698	Intermediate Similarity	NPC475733
0.7681	Intermediate Similarity	NPC472029
0.7681	Intermediate Similarity	NPC65761
0.7664	Intermediate Similarity	NPC215392
0.7664	Intermediate Similarity	NPC226275
0.7664	Intermediate Similarity	NPC303737
0.766	Intermediate Similarity	NPC473017
0.7609	Intermediate Similarity	NPC282577
0.7609	Intermediate Similarity	NPC91105
0.7609	Intermediate Similarity	NPC309765
0.7606	Intermediate Similarity	NPC474998
0.7591	Intermediate Similarity	NPC146642
0.7589	Intermediate Similarity	NPC72158
0.7589	Intermediate Similarity	NPC98254
0.7589	Intermediate Similarity	NPC190043
0.7589	Intermediate Similarity	NPC266689
0.7589	Intermediate Similarity	NPC103356
0.7589	Intermediate Similarity	NPC23126
0.7589	Intermediate Similarity	NPC105157
0.7589	Intermediate Similarity	NPC169250
0.7589	Intermediate Similarity	NPC100067
0.7589	Intermediate Similarity	NPC30501
0.7589	Intermediate Similarity	NPC162612
0.7578	Intermediate Similarity	NPC12890
0.7574	Intermediate Similarity	NPC473767
0.7546	Intermediate Similarity	NPC315406
0.7538	Intermediate Similarity	NPC224584
0.7535	Intermediate Similarity	NPC221777
0.7535	Intermediate Similarity	NPC21305
0.7518	Intermediate Similarity	NPC294037
0.7518	Intermediate Similarity	NPC267846
0.7518	Intermediate Similarity	NPC62952
0.75	Intermediate Similarity	NPC184527
0.75	Intermediate Similarity	NPC275504
0.7481	Intermediate Similarity	NPC83718
0.7481	Intermediate Similarity	NPC95172
0.7465	Intermediate Similarity	NPC116513
0.7464	Intermediate Similarity	NPC149246
0.7447	Intermediate Similarity	NPC123506
0.7429	Intermediate Similarity	NPC306288
0.7426	Intermediate Similarity	NPC174087
0.7413	Intermediate Similarity	NPC95537
0.7407	Intermediate Similarity	NPC161304
0.7407	Intermediate Similarity	NPC322197
0.7397	Intermediate Similarity	NPC53896
0.7397	Intermediate Similarity	NPC115458
0.7397	Intermediate Similarity	NPC213485
0.7397	Intermediate Similarity	NPC40524
0.7397	Intermediate Similarity	NPC139074
0.7394	Intermediate Similarity	NPC305717
0.7388	Intermediate Similarity	NPC211421
0.7383	Intermediate Similarity	NPC33011
0.7379	Intermediate Similarity	NPC475042
0.7379	Intermediate Similarity	NPC17083
0.7379	Intermediate Similarity	NPC328070
0.7376	Intermediate Similarity	NPC199273
0.7372	Intermediate Similarity	NPC40649
0.7372	Intermediate Similarity	NPC209486
0.7372	Intermediate Similarity	NPC273282
0.7372	Intermediate Similarity	NPC474890
0.7372	Intermediate Similarity	NPC161943
0.7365	Intermediate Similarity	NPC86524
0.7362	Intermediate Similarity	NPC54661
0.7362	Intermediate Similarity	NPC163924
0.7361	Intermediate Similarity	NPC476119
0.7361	Intermediate Similarity	NPC99731
0.7357	Intermediate Similarity	NPC232708
0.7357	Intermediate Similarity	NPC307174
0.7357	Intermediate Similarity	NPC133909
0.7357	Intermediate Similarity	NPC32032
0.7357	Intermediate Similarity	NPC475192
0.7357	Intermediate Similarity	NPC218333
0.7353	Intermediate Similarity	NPC477453
0.7351	Intermediate Similarity	NPC297322
0.7349	Intermediate Similarity	NPC313708
0.7347	Intermediate Similarity	NPC475088
0.7347	Intermediate Similarity	NPC166480
0.7347	Intermediate Similarity	NPC282780
0.7343	Intermediate Similarity	NPC72667
0.7343	Intermediate Similarity	NPC78364
0.7343	Intermediate Similarity	NPC84672
0.7343	Intermediate Similarity	NPC176130
0.7343	Intermediate Similarity	NPC69424
0.7333	Intermediate Similarity	NPC162939
0.7333	Intermediate Similarity	NPC13696
0.7329	Intermediate Similarity	NPC175738
0.7328	Intermediate Similarity	NPC226699
0.7328	Intermediate Similarity	NPC228737
0.7324	Intermediate Similarity	NPC10926
0.732	Intermediate Similarity	NPC476444
0.7319	Intermediate Similarity	NPC161617
0.7315	Intermediate Similarity	NPC471452
0.7315	Intermediate Similarity	NPC238108
0.7305	Intermediate Similarity	NPC477153
0.7303	Intermediate Similarity	NPC193555
0.7299	Intermediate Similarity	NPC269414
0.7297	Intermediate Similarity	NPC61153
0.7297	Intermediate Similarity	NPC80035
0.7297	Intermediate Similarity	NPC70859
0.7297	Intermediate Similarity	NPC130899
0.7297	Intermediate Similarity	NPC283590
0.7292	Intermediate Similarity	NPC48248
0.7292	Intermediate Similarity	NPC96024
0.7292	Intermediate Similarity	NPC470981
0.7286	Intermediate Similarity	NPC115159
0.7286	Intermediate Similarity	NPC267552
0.7286	Intermediate Similarity	NPC196976
0.7286	Intermediate Similarity	NPC73532
0.7286	Intermediate Similarity	NPC156139
0.7286	Intermediate Similarity	NPC45438
0.7286	Intermediate Similarity	NPC242895
0.7286	Intermediate Similarity	NPC224273
0.7286	Intermediate Similarity	NPC19174
0.7286	Intermediate Similarity	NPC143427
0.7279	Intermediate Similarity	NPC240163
0.7279	Intermediate Similarity	NPC470988
0.7279	Intermediate Similarity	NPC254603
0.7279	Intermediate Similarity	NPC477139
0.7279	Intermediate Similarity	NPC48036
0.7279	Intermediate Similarity	NPC285054
0.7273	Intermediate Similarity	NPC306765
0.7273	Intermediate Similarity	NPC231774
0.7273	Intermediate Similarity	NPC8745
0.7273	Intermediate Similarity	NPC254492
0.7273	Intermediate Similarity	NPC3224
0.7273	Intermediate Similarity	NPC328983
0.7267	Intermediate Similarity	NPC13715
0.7267	Intermediate Similarity	NPC4214
0.7266	Intermediate Similarity	NPC285829
0.7266	Intermediate Similarity	NPC206778
0.726	Intermediate Similarity	NPC244699
0.726	Intermediate Similarity	NPC41847
0.7254	Intermediate Similarity	NPC310540
0.7254	Intermediate Similarity	NPC13238
0.7254	Intermediate Similarity	NPC142956
0.7252	Intermediate Similarity	NPC6984
0.7248	Intermediate Similarity	NPC474311
0.7248	Intermediate Similarity	NPC194764
0.7248	Intermediate Similarity	NPC272268
0.7248	Intermediate Similarity	NPC65005
0.7248	Intermediate Similarity	NPC472308
0.7248	Intermediate Similarity	NPC264112
0.7246	Intermediate Similarity	NPC41567
0.7246	Intermediate Similarity	NPC249435
0.7241	Intermediate Similarity	NPC171460
0.7241	Intermediate Similarity	NPC109123
0.7241	Intermediate Similarity	NPC25736
0.7239	Intermediate Similarity	NPC114682
0.7234	Intermediate Similarity	NPC68167
0.723	Intermediate Similarity	NPC470984
0.723	Intermediate Similarity	NPC50924
0.723	Intermediate Similarity	NPC474519
0.7222	Intermediate Similarity	NPC329205
0.7222	Intermediate Similarity	NPC316625
0.7219	Intermediate Similarity	NPC473988
0.7214	Intermediate Similarity	NPC297186
0.7214	Intermediate Similarity	NPC190971
0.7214	Intermediate Similarity	NPC216216
0.7214	Intermediate Similarity	NPC229649
0.7211	Intermediate Similarity	NPC58685
0.7211	Intermediate Similarity	NPC27490
0.7211	Intermediate Similarity	NPC185624
0.7203	Intermediate Similarity	NPC477454
0.72	Intermediate Similarity	NPC475957
0.7197	Intermediate Similarity	NPC141523
0.7192	Intermediate Similarity	NPC117609
0.7192	Intermediate Similarity	NPC198305
0.7192	Intermediate Similarity	NPC470987
0.7192	Intermediate Similarity	NPC108129
0.7192	Intermediate Similarity	NPC21378
0.7183	Intermediate Similarity	NPC174991
0.7183	Intermediate Similarity	NPC375356
0.7183	Intermediate Similarity	NPC273683
0.7181	Intermediate Similarity	NPC470210
0.7181	Intermediate Similarity	NPC473055
0.7181	Intermediate Similarity	NPC290803
0.7181	Intermediate Similarity	NPC258502
0.7181	Intermediate Similarity	NPC473052
0.7181	Intermediate Similarity	NPC283088
0.7174	Intermediate Similarity	NPC121259
0.7172	Intermediate Similarity	NPC229894
0.7172	Intermediate Similarity	NPC282923
0.7172	Intermediate Similarity	NPC478147
0.7172	Intermediate Similarity	NPC41263
0.7172	Intermediate Similarity	NPC3009
0.7171	Intermediate Similarity	NPC169452
0.7171	Intermediate Similarity	NPC470986
0.7171	Intermediate Similarity	NPC477956
0.7171	Intermediate Similarity	NPC283429
0.7171	Intermediate Similarity	NPC181560
0.7164	Intermediate Similarity	NPC116842
0.7163	Intermediate Similarity	NPC295034
0.7162	Intermediate Similarity	NPC52407
0.7162	Intermediate Similarity	NPC267205
0.7153	Intermediate Similarity	NPC160499
0.7153	Intermediate Similarity	NPC23402

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 NPC236795 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	178
0.1-0.2	723
0.2-0.3	1116
0.3-0.4	2401
0.4-0.5	2771
0.5-0.6	1666
0.6-0.7	288
0.7-0.8	7
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7445	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD1164	Approved
0.7178	Intermediate Similarity	NPD3286	Discontinued
0.7143	Intermediate Similarity	NPD3300	Phase 2
0.7133	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7122	Intermediate Similarity	NPD1759	Phase 1
0.7101	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD1470	Approved
0.705	Intermediate Similarity	NPD1758	Phase 1
0.7042	Intermediate Similarity	NPD1201	Approved
0.702	Intermediate Similarity	NPD2799	Discontinued
0.6993	Remote Similarity	NPD3655	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD4208	Discontinued
0.698	Remote Similarity	NPD943	Approved
0.6974	Remote Similarity	NPD2935	Discontinued
0.6918	Remote Similarity	NPD2798	Approved
0.6917	Remote Similarity	NPD1018	Approved
0.6908	Remote Similarity	NPD1510	Phase 2
0.6901	Remote Similarity	NPD5637	Discontinued
0.6889	Remote Similarity	NPD74	Approved
0.6889	Remote Similarity	NPD9266	Approved
0.6867	Remote Similarity	NPD1240	Approved
0.6863	Remote Similarity	NPD5404	Approved
0.6863	Remote Similarity	NPD5406	Approved
0.6863	Remote Similarity	NPD5408	Approved
0.6863	Remote Similarity	NPD5405	Approved
0.6857	Remote Similarity	NPD9493	Approved
0.6846	Remote Similarity	NPD2313	Discontinued
0.6835	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD1755	Approved
0.6824	Remote Similarity	NPD6020	Phase 2
0.6824	Remote Similarity	NPD4207	Discontinued
0.6815	Remote Similarity	NPD9264	Approved
0.6815	Remote Similarity	NPD9263	Approved
0.6815	Remote Similarity	NPD9267	Approved
0.6795	Remote Similarity	NPD3400	Discontinued
0.6776	Remote Similarity	NPD1607	Approved
0.6772	Remote Similarity	NPD7390	Discontinued
0.6753	Remote Similarity	NPD7450	Phase 2
0.6731	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6728	Remote Similarity	NPD6585	Discontinued
0.671	Remote Similarity	NPD2344	Approved
0.6691	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD520	Approved
0.6688	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD5889	Approved
0.6687	Remote Similarity	NPD5890	Approved
0.6667	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD256	Approved
0.6667	Remote Similarity	NPD3136	Phase 2
0.6667	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6651	Approved
0.6667	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD255	Approved
0.6648	Remote Similarity	NPD5968	Phase 3
0.6647	Remote Similarity	NPD3823	Discontinued
0.6643	Remote Similarity	NPD5303	Approved
0.6643	Remote Similarity	NPD5304	Approved
0.6626	Remote Similarity	NPD4380	Phase 2
0.6625	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6621	Remote Similarity	NPD3143	Discontinued
0.662	Remote Similarity	NPD7325	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD5027	Approved
0.6609	Remote Similarity	NPD5029	Approved
0.6609	Remote Similarity	NPD5031	Approved
0.6596	Remote Similarity	NPD9281	Approved
0.6585	Remote Similarity	NPD7411	Suspended
0.6581	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD7318	Phase 3
0.6565	Remote Similarity	NPD1809	Phase 2
0.6561	Remote Similarity	NPD1549	Phase 2
0.6556	Remote Similarity	NPD5937	Approved
0.6552	Remote Similarity	NPD1252	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD3019	Approved
0.6552	Remote Similarity	NPD2932	Approved
0.6541	Remote Similarity	NPD2309	Approved
0.6538	Remote Similarity	NPD845	Approved
0.6533	Remote Similarity	NPD4212	Discontinued
0.6531	Remote Similarity	NPD9717	Approved
0.6528	Remote Similarity	NPD9545	Approved
0.6525	Remote Similarity	NPD2234	Approved
0.6525	Remote Similarity	NPD2228	Approved
0.6525	Remote Similarity	NPD2229	Approved
0.6524	Remote Similarity	NPD6502	Phase 2
0.6522	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6519	Remote Similarity	NPD2654	Approved
0.6519	Remote Similarity	NPD2800	Approved
0.6519	Remote Similarity	NPD9261	Approved
0.6513	Remote Similarity	NPD3268	Approved
0.651	Remote Similarity	NPD1203	Approved
0.65	Remote Similarity	NPD6884	Clinical (unspecified phase)
0.6497	Remote Similarity	NPD2346	Discontinued
0.6497	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6497	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6477	Remote Similarity	NPD5032	Approved
0.6477	Remote Similarity	NPD4954	Approved
0.6477	Remote Similarity	NPD4955	Approved
0.6477	Remote Similarity	NPD5028	Approved
0.6477	Remote Similarity	NPD36	Approved
0.6477	Remote Similarity	NPD5026	Approved
0.6477	Remote Similarity	NPD5034	Approved
0.6471	Remote Similarity	NPD5729	Clinical (unspecified phase)
0.6467	Remote Similarity	NPD2379	Clinical (unspecified phase)
0.6467	Remote Similarity	NPD257	Approved
0.6467	Remote Similarity	NPD258	Approved
0.6463	Remote Similarity	NPD3226	Approved
0.6446	Remote Similarity	NPD6844	Discontinued
0.6446	Remote Similarity	NPD7317	Phase 3
0.6444	Remote Similarity	NPD6836	Approved
0.6433	Remote Similarity	NPD2796	Approved
0.6429	Remote Similarity	NPD3142	Approved
0.6429	Remote Similarity	NPD3140	Approved
0.6425	Remote Similarity	NPD5038	Approved
0.6425	Remote Similarity	NPD5037	Approved
0.6423	Remote Similarity	NPD999	Phase 2
0.642	Remote Similarity	NPD5030	Phase 2
0.6418	Remote Similarity	NPD3020	Approved
0.6416	Remote Similarity	NPD3446	Phase 1
0.6415	Remote Similarity	NPD1243	Approved
0.6407	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.64	Remote Similarity	NPD1729	Discontinued
0.6397	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6397	Remote Similarity	NPD1930	Approved
0.6397	Remote Similarity	NPD1929	Approved
0.6391	Remote Similarity	NPD7075	Discontinued
0.6389	Remote Similarity	NPD9568	Approved
0.6379	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6377	Remote Similarity	NPD1444	Approved
0.6377	Remote Similarity	NPD1445	Approved
0.6376	Remote Similarity	NPD5159	Phase 2
0.6376	Remote Similarity	NPD5157	Phase 1
0.6376	Remote Similarity	NPD5158	Clinical (unspecified phase)
0.6375	Remote Similarity	NPD7003	Approved
0.6375	Remote Similarity	NPD1196	Approved
0.6375	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6369	Remote Similarity	NPD5036	Approved
0.6364	Remote Similarity	NPD7458	Discontinued
0.6358	Remote Similarity	NPD1511	Approved
0.6358	Remote Similarity	NPD1543	Discontinued
0.6358	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6358	Remote Similarity	NPD4980	Approved
0.6358	Remote Similarity	NPD6894	Phase 1
0.6357	Remote Similarity	NPD1792	Phase 2
0.6353	Remote Similarity	NPD3252	Approved
0.6351	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.635	Remote Similarity	NPD179	Clinical (unspecified phase)
0.635	Remote Similarity	NPD1237	Approved
0.6348	Remote Similarity	NPD5035	Approved
0.6335	Remote Similarity	NPD7910	Clinical (unspecified phase)
0.6335	Remote Similarity	NPD3295	Clinical (unspecified phase)
0.6328	Remote Similarity	NPD6104	Discontinued
0.6327	Remote Similarity	NPD1362	Clinical (unspecified phase)
0.6323	Remote Similarity	NPD826	Approved
0.6323	Remote Similarity	NPD6346	Approved
0.6323	Remote Similarity	NPD825	Approved
0.6319	Remote Similarity	NPD2533	Approved
0.6319	Remote Similarity	NPD2534	Approved
0.6319	Remote Similarity	NPD2532	Approved
0.6316	Remote Similarity	NPD2860	Approved
0.6316	Remote Similarity	NPD2859	Approved
0.6312	Remote Similarity	NPD1195	Approved
0.631	Remote Similarity	NPD7819	Suspended
0.631	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6309	Remote Similarity	NPD3972	Approved
0.6309	Remote Similarity	NPD3070	Discontinued
0.6304	Remote Similarity	NPD4363	Phase 3
0.6304	Remote Similarity	NPD4360	Phase 2
0.6301	Remote Similarity	NPD998	Approved
0.6299	Remote Similarity	NPD3764	Approved
0.6289	Remote Similarity	NPD7978	Discontinued
0.6289	Remote Similarity	NPD1471	Phase 3
0.6287	Remote Similarity	NPD2366	Approved
0.6287	Remote Similarity	NPD7118	Clinical (unspecified phase)
0.6284	Remote Similarity	NPD3819	Phase 2
0.6284	Remote Similarity	NPD2688	Clinical (unspecified phase)
0.628	Remote Similarity	NPD1512	Approved
0.6276	Remote Similarity	NPD3123	Discovery
0.6273	Remote Similarity	NPD3750	Approved
0.6272	Remote Similarity	NPD8438	Clinical (unspecified phase)
0.627	Remote Similarity	NPD4361	Phase 2
0.627	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.6267	Remote Similarity	NPD3676	Clinical (unspecified phase)
0.6267	Remote Similarity	NPD1669	Approved
0.6267	Remote Similarity	NPD182	Clinical (unspecified phase)
0.6266	Remote Similarity	NPD6866	Clinical (unspecified phase)
0.6266	Remote Similarity	NPD6867	Clinical (unspecified phase)
0.6265	Remote Similarity	NPD3455	Phase 2
0.6265	Remote Similarity	NPD824	Approved
0.6259	Remote Similarity	NPD4093	Discontinued
0.6258	Remote Similarity	NPD6682	Clinical (unspecified phase)
0.625	Remote Similarity	NPD7577	Discontinued
0.625	Remote Similarity	NPD9277	Approved
0.625	Remote Similarity	NPD7451	Discontinued
0.625	Remote Similarity	NPD475	Phase 2
0.625	Remote Similarity	NPD3589	Clinical (unspecified phase)
0.625	Remote Similarity	NPD7596	Clinical (unspecified phase)
0.625	Remote Similarity	NPD5951	Approved
0.625	Remote Similarity	NPD75	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