NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	162.08
Volume:	167.345
LogP:	-0.094
LogD:	0.427
LogS:	-0.816
# Rotatable Bonds:	1
TPSA:	41.99
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.67
Synthetic Accessibility Score:	2.811
Fsp3:	0.333
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:	-4.345
MDCK Permeability:	2.3153257643571123e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.016
20% Bioavailability (F20%):	0.028
30% Bioavailability (F30%):	0.02

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.867
Plasma Protein Binding (PPB):	13.744160652160645%
Volume Distribution (VD):	1.278
Pgp-substrate:	78.19329833984375%

ADMET: Metabolism

CYP1A2-inhibitor:	0.067
CYP1A2-substrate:	0.66
CYP2C19-inhibitor:	0.085
CYP2C19-substrate:	0.478
CYP2C9-inhibitor:	0.027
CYP2C9-substrate:	0.586
CYP2D6-inhibitor:	0.009
CYP2D6-substrate:	0.377
CYP3A4-inhibitor:	0.109
CYP3A4-substrate:	0.316

ADMET: Excretion

Clearance (CL):	3.659
Half-life (T1/2):	0.653

ADMET: Toxicity

hERG Blockers:	0.046
Human Hepatotoxicity (H-HT):	0.191
Drug-inuced Liver Injury (DILI):	0.374
AMES Toxicity:	0.038
Rat Oral Acute Toxicity:	0.277
Maximum Recommended Daily Dose:	0.779
Skin Sensitization:	0.483
Carcinogencity:	0.157
Eye Corrosion:	0.003
Eye Irritation:	0.036
Respiratory Toxicity:	0.05

Download Data

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

Natural Product: NPC324611

Natural Product ID:	NPC324611
*Common Name:**	5-Pyridin-3-Ylpyrrolidin-2-One
IUPAC Name:	5-pyridin-3-ylpyrrolidin-2-one
Synonyms:
Standard InCHIKey:	FXFANIORDKRCCA-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C9H10N2O/c12-9-4-3-8(11-9)7-2-1-5-10-6-7/h1-2,5-6,8H,3-4H2,(H,11,12)
SMILES:	OC1=NC(CC1)c1cccnc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3126030
PubChem CID:	413
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

☑ 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
Others	10

Activity Type	# Activity
NON-MOLECULAR	10

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	75.5	%	PMID[490591]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	74.5	%	PMID[490591]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	82.0	%	PMID[490591]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	78.6	%	PMID[490591]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	66.9	%	PMID[490591]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	68.0	%	PMID[490591]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	68.3	%	PMID[490591]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	86.8	%	PMID[490591]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	93.6	%	PMID[490591]

☑ 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 NPC324611 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	357
0.1-0.2	4108
0.2-0.3	19131
0.3-0.4	11860
0.4-0.5	3668
0.5-0.6	2378
0.6-0.7	965
0.7-0.8	212
0.8-0.85	15
0.85-0.9	0
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9062	High Similarity	NPC471313
0.9062	High Similarity	NPC471311
0.8594	High Similarity	NPC182570
0.8594	High Similarity	NPC265605
0.8594	High Similarity	NPC48564
0.8467	Intermediate Similarity	NPC471312
0.8397	Intermediate Similarity	NPC27740
0.8296	Intermediate Similarity	NPC315320
0.8195	Intermediate Similarity	NPC146373
0.8195	Intermediate Similarity	NPC166424
0.8195	Intermediate Similarity	NPC245244
0.8182	Intermediate Similarity	NPC290094
0.816	Intermediate Similarity	NPC27802
0.814	Intermediate Similarity	NPC297486
0.814	Intermediate Similarity	NPC471402
0.814	Intermediate Similarity	NPC240136
0.8102	Intermediate Similarity	NPC256893
0.8077	Intermediate Similarity	NPC91958
0.8074	Intermediate Similarity	NPC212125
0.8071	Intermediate Similarity	NPC65408
0.8043	Intermediate Similarity	NPC322488
0.8	Intermediate Similarity	NPC169625
0.8	Intermediate Similarity	NPC202957
0.7971	Intermediate Similarity	NPC471322
0.7941	Intermediate Similarity	NPC306397
0.7941	Intermediate Similarity	NPC278451
0.7939	Intermediate Similarity	NPC143603
0.792	Intermediate Similarity	NPC76540
0.7883	Intermediate Similarity	NPC89490
0.7852	Intermediate Similarity	NPC476322
0.7826	Intermediate Similarity	NPC329896
0.7826	Intermediate Similarity	NPC475090
0.7826	Intermediate Similarity	NPC475105
0.7815	Intermediate Similarity	NPC129721
0.781	Intermediate Similarity	NPC165370
0.7778	Intermediate Similarity	NPC59779
0.7778	Intermediate Similarity	NPC46358
0.7778	Intermediate Similarity	NPC471177
0.7778	Intermediate Similarity	NPC124542
0.7752	Intermediate Similarity	NPC235843
0.7746	Intermediate Similarity	NPC29702
0.7733	Intermediate Similarity	NPC259644
0.7733	Intermediate Similarity	NPC469760
0.7733	Intermediate Similarity	NPC469765
0.7733	Intermediate Similarity	NPC469763
0.7733	Intermediate Similarity	NPC469786
0.7733	Intermediate Similarity	NPC25008
0.7733	Intermediate Similarity	NPC73952
0.7712	Intermediate Similarity	NPC279918
0.7682	Intermediate Similarity	NPC211572
0.7682	Intermediate Similarity	NPC80597
0.7682	Intermediate Similarity	NPC75540
0.7682	Intermediate Similarity	NPC212376
0.7682	Intermediate Similarity	NPC70922
0.7662	Intermediate Similarity	NPC282231
0.7643	Intermediate Similarity	NPC282398
0.7632	Intermediate Similarity	NPC469785
0.7619	Intermediate Similarity	NPC471323
0.7613	Intermediate Similarity	NPC97367
0.7597	Intermediate Similarity	NPC131718
0.7589	Intermediate Similarity	NPC101165
0.7582	Intermediate Similarity	NPC469762
0.7581	Intermediate Similarity	NPC83987
0.7574	Intermediate Similarity	NPC329825
0.7571	Intermediate Similarity	NPC476131
0.7568	Intermediate Similarity	NPC314372
0.7564	Intermediate Similarity	NPC471178
0.7551	Intermediate Similarity	NPC190296
0.7532	Intermediate Similarity	NPC230869
0.7518	Intermediate Similarity	NPC69914
0.7516	Intermediate Similarity	NPC474561
0.7516	Intermediate Similarity	NPC54988
0.7516	Intermediate Similarity	NPC160105
0.7516	Intermediate Similarity	NPC49954
0.75	Intermediate Similarity	NPC78375
0.75	Intermediate Similarity	NPC476446
0.75	Intermediate Similarity	NPC328029
0.75	Intermediate Similarity	NPC469813
0.75	Intermediate Similarity	NPC231655
0.7468	Intermediate Similarity	NPC63751
0.7453	Intermediate Similarity	NPC203754
0.7453	Intermediate Similarity	NPC150048
0.745	Intermediate Similarity	NPC159856
0.7436	Intermediate Similarity	NPC71079
0.7405	Intermediate Similarity	NPC98187
0.7405	Intermediate Similarity	NPC41717
0.7389	Intermediate Similarity	NPC311276
0.7389	Intermediate Similarity	NPC474217
0.7389	Intermediate Similarity	NPC194640
0.7389	Intermediate Similarity	NPC102423
0.7365	Intermediate Similarity	NPC476454
0.7342	Intermediate Similarity	NPC85918
0.7329	Intermediate Similarity	NPC314102
0.7329	Intermediate Similarity	NPC105127
0.7329	Intermediate Similarity	NPC314603
0.7329	Intermediate Similarity	NPC251722
0.7329	Intermediate Similarity	NPC114310
0.7296	Intermediate Similarity	NPC127730
0.7296	Intermediate Similarity	NPC278366
0.7286	Intermediate Similarity	NPC151489
0.7284	Intermediate Similarity	NPC149155
0.7284	Intermediate Similarity	NPC203468
0.7284	Intermediate Similarity	NPC110500
0.7278	Intermediate Similarity	NPC473057
0.726	Intermediate Similarity	NPC96102
0.7255	Intermediate Similarity	NPC24678
0.7255	Intermediate Similarity	NPC105818
0.725	Intermediate Similarity	NPC78020
0.725	Intermediate Similarity	NPC201700
0.7239	Intermediate Similarity	NPC267885
0.7237	Intermediate Similarity	NPC471957
0.7237	Intermediate Similarity	NPC470111
0.7233	Intermediate Similarity	NPC477975
0.723	Intermediate Similarity	NPC110126
0.723	Intermediate Similarity	NPC316811
0.723	Intermediate Similarity	NPC32002
0.723	Intermediate Similarity	NPC315348
0.7222	Intermediate Similarity	NPC82295
0.7219	Intermediate Similarity	NPC285731
0.7219	Intermediate Similarity	NPC86288
0.7211	Intermediate Similarity	NPC84911
0.7211	Intermediate Similarity	NPC150259
0.7205	Intermediate Similarity	NPC314940
0.7205	Intermediate Similarity	NPC473764
0.7195	Intermediate Similarity	NPC59269
0.7188	Intermediate Similarity	NPC108469
0.7178	Intermediate Similarity	NPC469938
0.717	Intermediate Similarity	NPC40779
0.7169	Intermediate Similarity	NPC233936
0.7162	Intermediate Similarity	NPC169433
0.7152	Intermediate Similarity	NPC248041
0.7152	Intermediate Similarity	NPC283219
0.7152	Intermediate Similarity	NPC248462
0.7152	Intermediate Similarity	NPC126709
0.7143	Intermediate Similarity	NPC188387
0.7143	Intermediate Similarity	NPC261195
0.7143	Intermediate Similarity	NPC29886
0.7143	Intermediate Similarity	NPC40070
0.7143	Intermediate Similarity	NPC163421
0.7134	Intermediate Similarity	NPC212742
0.7134	Intermediate Similarity	NPC138018
0.7133	Intermediate Similarity	NPC471589
0.7126	Intermediate Similarity	NPC48938
0.7117	Intermediate Similarity	NPC313791
0.7114	Intermediate Similarity	NPC73767
0.7097	Intermediate Similarity	NPC216713
0.7091	Intermediate Similarity	NPC248454
0.7067	Intermediate Similarity	NPC469783
0.7067	Intermediate Similarity	NPC469761
0.7067	Intermediate Similarity	NPC279081
0.7067	Intermediate Similarity	NPC469768
0.7067	Intermediate Similarity	NPC469767
0.7067	Intermediate Similarity	NPC469779
0.7067	Intermediate Similarity	NPC469780
0.7067	Intermediate Similarity	NPC469784
0.7059	Intermediate Similarity	NPC63545
0.7055	Intermediate Similarity	NPC330326
0.7051	Intermediate Similarity	NPC138842
0.7044	Intermediate Similarity	NPC25899
0.7041	Intermediate Similarity	NPC15102
0.7024	Intermediate Similarity	NPC220765
0.702	Intermediate Similarity	NPC469766
0.7013	Intermediate Similarity	NPC469811
0.7013	Intermediate Similarity	NPC201380
0.7013	Intermediate Similarity	NPC477974
0.7013	Intermediate Similarity	NPC179787
0.7012	Intermediate Similarity	NPC477976
0.7007	Intermediate Similarity	NPC148140
0.7007	Intermediate Similarity	NPC476566
0.7	Intermediate Similarity	NPC48192
0.7	Intermediate Similarity	NPC474707
0.7	Intermediate Similarity	NPC62749
0.6993	Remote Similarity	NPC167400
0.6993	Remote Similarity	NPC467188
0.6988	Remote Similarity	NPC151939
0.6988	Remote Similarity	NPC111275
0.6988	Remote Similarity	NPC184964
0.6988	Remote Similarity	NPC64436
0.6986	Remote Similarity	NPC174421
0.6982	Remote Similarity	NPC204717
0.6981	Remote Similarity	NPC135141
0.6981	Remote Similarity	NPC293487
0.6981	Remote Similarity	NPC92796
0.6977	Remote Similarity	NPC95783
0.6975	Remote Similarity	NPC49217
0.6968	Remote Similarity	NPC321911
0.6962	Remote Similarity	NPC285469
0.6959	Remote Similarity	NPC317030
0.6959	Remote Similarity	NPC204565
0.6957	Remote Similarity	NPC478184
0.6957	Remote Similarity	NPC81561
0.6957	Remote Similarity	NPC162268
0.6954	Remote Similarity	NPC230002
0.6954	Remote Similarity	NPC329541
0.6951	Remote Similarity	NPC252590
0.6946	Remote Similarity	NPC213468
0.6946	Remote Similarity	NPC55772
0.6941	Remote Similarity	NPC314002
0.6941	Remote Similarity	NPC62510
0.6937	Remote Similarity	NPC81229

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 NPC324611 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	205
0.1-0.2	617
0.2-0.3	1086
0.3-0.4	1462
0.4-0.5	3037
0.5-0.6	1960
0.6-0.7	640
0.7-0.8	133
0.8-0.85	10
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8594	High Similarity	NPD268	Approved
0.8594	High Similarity	NPD270	Clinical (unspecified phase)
0.8594	High Similarity	NPD271	Approved
0.8322	Intermediate Similarity	NPD4703	Approved
0.8322	Intermediate Similarity	NPD4702	Approved
0.8298	Intermediate Similarity	NPD3717	Discontinued
0.8296	Intermediate Similarity	NPD9207	Approved
0.8296	Intermediate Similarity	NPD9206	Approved
0.8284	Intermediate Similarity	NPD1095	Clinical (unspecified phase)
0.8252	Intermediate Similarity	NPD6148	Clinical (unspecified phase)
0.8143	Intermediate Similarity	NPD2896	Discontinued
0.8112	Intermediate Similarity	NPD3813	Approved
0.8112	Intermediate Similarity	NPD751	Clinical (unspecified phase)
0.8074	Intermediate Similarity	NPD991	Phase 2
0.8074	Intermediate Similarity	NPD992	Clinical (unspecified phase)
0.8074	Intermediate Similarity	NPD9284	Approved
0.8071	Intermediate Similarity	NPD201	Phase 2
0.8071	Intermediate Similarity	NPD200	Phase 2
0.797	Intermediate Similarity	NPD748	Clinical (unspecified phase)
0.7941	Intermediate Similarity	NPD9080	Approved
0.7881	Intermediate Similarity	NPD5255	Approved
0.7868	Intermediate Similarity	NPD9583	Approved
0.7852	Intermediate Similarity	NPD9357	Approved
0.7846	Intermediate Similarity	NPD269	Clinical (unspecified phase)
0.7823	Intermediate Similarity	NPD1661	Suspended
0.781	Intermediate Similarity	NPD2119	Approved
0.781	Intermediate Similarity	NPD2118	Approved
0.781	Intermediate Similarity	NPD1598	Discontinued
0.7785	Intermediate Similarity	NPD3262	Approved
0.7778	Intermediate Similarity	NPD1649	Discontinued
0.777	Intermediate Similarity	NPD3475	Approved
0.777	Intermediate Similarity	NPD3476	Approved
0.7762	Intermediate Similarity	NPD203	Clinical (unspecified phase)
0.7748	Intermediate Similarity	NPD6026	Approved
0.7697	Intermediate Similarity	NPD5541	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD9506	Approved
0.7667	Intermediate Similarity	NPD510	Phase 1
0.7662	Intermediate Similarity	NPD8026	Phase 1
0.766	Intermediate Similarity	NPD1627	Clinical (unspecified phase)
0.7635	Intermediate Similarity	NPD7469	Discontinued
0.7619	Intermediate Similarity	NPD1352	Discontinued
0.7616	Intermediate Similarity	NPD2012	Clinical (unspecified phase)
0.7615	Intermediate Similarity	NPD4824	Approved
0.7615	Intermediate Similarity	NPD4823	Approved
0.7606	Intermediate Similarity	NPD4029	Approved
0.7606	Intermediate Similarity	NPD4028	Approved
0.7606	Intermediate Similarity	NPD4030	Approved
0.7595	Intermediate Similarity	NPD5934	Clinical (unspecified phase)
0.7594	Intermediate Similarity	NPD9396	Approved
0.7594	Intermediate Similarity	NPD9392	Approved
0.7566	Intermediate Similarity	NPD2809	Approved
0.7518	Intermediate Similarity	NPD715	Phase 3
0.75	Intermediate Similarity	NPD9098	Phase 3
0.75	Intermediate Similarity	NPD5065	Approved
0.75	Intermediate Similarity	NPD9099	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD2511	Approved
0.7483	Intermediate Similarity	NPD3942	Approved
0.7483	Intermediate Similarity	NPD3944	Approved
0.7466	Intermediate Similarity	NPD768	Clinical (unspecified phase)
0.7465	Intermediate Similarity	NPD9726	Discontinued
0.7453	Intermediate Similarity	NPD6375	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD926	Approved
0.7452	Intermediate Similarity	NPD925	Approved
0.745	Intermediate Similarity	NPD175	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD2007	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD1183	Approved
0.7413	Intermediate Similarity	NPD1995	Approved
0.7413	Intermediate Similarity	NPD1994	Approved
0.7413	Intermediate Similarity	NPD1993	Approved
0.7405	Intermediate Similarity	NPD424	Approved
0.7405	Intermediate Similarity	NPD425	Approved
0.7379	Intermediate Similarity	NPD206	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD792	Discontinued
0.7372	Intermediate Similarity	NPD9598	Discontinued
0.7365	Intermediate Similarity	NPD1592	Phase 3
0.7365	Intermediate Similarity	NPD4805	Approved
0.7358	Intermediate Similarity	NPD6872	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD5862	Discovery
0.7355	Intermediate Similarity	NPD2581	Approved
0.7355	Intermediate Similarity	NPD2582	Approved
0.7347	Intermediate Similarity	NPD945	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD5100	Phase 3
0.7343	Intermediate Similarity	NPD803	Phase 1
0.7338	Intermediate Similarity	NPD5358	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD750	Phase 2
0.732	Intermediate Similarity	NPD6158	Phase 2
0.732	Intermediate Similarity	NPD9706	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD6476	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD2006	Phase 2
0.7312	Intermediate Similarity	NPD2619	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD2620	Phase 2
0.731	Intermediate Similarity	NPD272	Approved
0.7308	Intermediate Similarity	NPD704	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD604	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD3575	Approved
0.7303	Intermediate Similarity	NPD3576	Approved
0.7301	Intermediate Similarity	NPD8123	Approved
0.7301	Intermediate Similarity	NPD8122	Approved
0.7297	Intermediate Similarity	NPD1395	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD482	Approved
0.7284	Intermediate Similarity	NPD5322	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD1380	Discovery
0.7278	Intermediate Similarity	NPD8129	Discovery
0.7278	Intermediate Similarity	NPD5088	Discontinued
0.726	Intermediate Similarity	NPD198	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD1722	Approved
0.7246	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD2720	Phase 1
0.7233	Intermediate Similarity	NPD2719	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD786	Approved
0.723	Intermediate Similarity	NPD2070	Approved
0.723	Intermediate Similarity	NPD2071	Approved
0.723	Intermediate Similarity	NPD2074	Approved
0.723	Intermediate Similarity	NPD2069	Approved
0.723	Intermediate Similarity	NPD2068	Approved
0.723	Intermediate Similarity	NPD2075	Approved
0.723	Intermediate Similarity	NPD2073	Approved
0.723	Intermediate Similarity	NPD4804	Approved
0.723	Intermediate Similarity	NPD2072	Approved
0.7229	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD966	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD4239	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD1427	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD2144	Approved
0.7192	Intermediate Similarity	NPD2142	Approved
0.7192	Intermediate Similarity	NPD2140	Approved
0.7192	Intermediate Similarity	NPD2141	Approved
0.7188	Intermediate Similarity	NPD5611	Phase 2
0.7188	Intermediate Similarity	NPD4174	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD9599	Approved
0.7178	Intermediate Similarity	NPD2928	Phase 2
0.717	Intermediate Similarity	NPD6635	Approved
0.717	Intermediate Similarity	NPD5925	Phase 1
0.7169	Intermediate Similarity	NPD8408	Discontinued
0.7162	Intermediate Similarity	NPD2323	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD8020	Approved
0.716	Intermediate Similarity	NPD8021	Approved
0.7152	Intermediate Similarity	NPD112	Approved
0.7152	Intermediate Similarity	NPD9705	Discontinued
0.7143	Intermediate Similarity	NPD5555	Phase 1
0.7143	Intermediate Similarity	NPD2781	Approved
0.7134	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD1382	Phase 2
0.7133	Intermediate Similarity	NPD1383	Phase 3
0.7126	Intermediate Similarity	NPD2092	Phase 2
0.7126	Intermediate Similarity	NPD2095	Phase 2
0.7126	Intermediate Similarity	NPD2094	Phase 2
0.7125	Intermediate Similarity	NPD2782	Approved
0.7125	Intermediate Similarity	NPD2780	Approved
0.7124	Intermediate Similarity	NPD1270	Approved
0.7124	Intermediate Similarity	NPD2089	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD4547	Phase 3
0.7115	Intermediate Similarity	NPD2061	Approved
0.711	Intermediate Similarity	NPD4427	Phase 2
0.7108	Intermediate Similarity	NPD6595	Phase 3
0.7097	Intermediate Similarity	NPD2882	Phase 1
0.7097	Intermediate Similarity	NPD5965	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD1272	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD2096	Phase 2
0.7083	Intermediate Similarity	NPD2091	Phase 2
0.7078	Intermediate Similarity	NPD2430	Phase 2
0.7073	Intermediate Similarity	NPD9690	Approved
0.707	Intermediate Similarity	NPD2748	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD3038	Discontinued
0.7055	Intermediate Similarity	NPD9100	Approved
0.7055	Intermediate Similarity	NPD1078	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD9076	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD687	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD1918	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD4640	Approved
0.7037	Intermediate Similarity	NPD4639	Approved
0.7037	Intermediate Similarity	NPD4638	Approved
0.7027	Intermediate Similarity	NPD490	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD2391	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD5020	Approved
0.7019	Intermediate Similarity	NPD1568	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD3385	Approved
0.7	Intermediate Similarity	NPD706	Phase 1
0.7	Intermediate Similarity	NPD6771	Discontinued
0.6993	Remote Similarity	NPD9075	Approved
0.6993	Remote Similarity	NPD9074	Approved
0.6988	Remote Similarity	NPD6203	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD1032	Phase 2
0.6981	Remote Similarity	NPD3433	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD4510	Discontinued
0.6971	Remote Similarity	NPD7818	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD3654	Approved
0.6964	Remote Similarity	NPD7414	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD3117	Approved
0.6951	Remote Similarity	NPD3116	Approved
0.6946	Remote Similarity	NPD8036	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD1620	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD8037	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD1917	Discontinued
0.6943	Remote Similarity	NPD2837	Discontinued
0.6941	Remote Similarity	NPD3082	Discontinued
0.6941	Remote Similarity	NPD6241	Phase 1
0.6937	Remote Similarity	NPD6454	Clinical (unspecified phase)
0.6934	Remote Similarity	NPD60	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