NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	148.1
Volume:	161.192
LogP:	-0.043
LogD:	0.693
LogS:	0.48
# Rotatable Bonds:	1
TPSA:	24.92
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.653
Synthetic Accessibility Score:	2.698
Fsp3:	0.444
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:	-4.531
MDCK Permeability:	1.9450013496680185e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.169
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.473
30% Bioavailability (F30%):	0.478

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.802
Plasma Protein Binding (PPB):	19.300945281982422%
Volume Distribution (VD):	2.597
Pgp-substrate:	83.6375961303711%

ADMET: Metabolism

CYP1A2-inhibitor:	0.092
CYP1A2-substrate:	0.672
CYP2C19-inhibitor:	0.126
CYP2C19-substrate:	0.826
CYP2C9-inhibitor:	0.012
CYP2C9-substrate:	0.365
CYP2D6-inhibitor:	0.062
CYP2D6-substrate:	0.884
CYP3A4-inhibitor:	0.176
CYP3A4-substrate:	0.413

ADMET: Excretion

Clearance (CL):	8.064
Half-life (T1/2):	0.589

ADMET: Toxicity

hERG Blockers:	0.049
Human Hepatotoxicity (H-HT):	0.539
Drug-inuced Liver Injury (DILI):	0.075
AMES Toxicity:	0.014
Rat Oral Acute Toxicity:	0.728
Maximum Recommended Daily Dose:	0.915
Skin Sensitization:	0.926
Carcinogencity:	0.042
Eye Corrosion:	0.077
Eye Irritation:	0.102
Respiratory Toxicity:	0.875

Download Data

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

Natural Product: NPC27740

Natural Product ID:	NPC27740
*Common Name:**	(R)-3-Pyrrolidin-2-Yl-Pyridine
IUPAC Name:	3-[(2R)-pyrrolidin-2-yl]pyridine
Synonyms:
Standard InCHIKey:	MYKUKUCHPMASKF-SECBINFHSA-N
Standard InCHI:	InChI=1S/C9H12N2/c1-3-8(7-10-5-1)9-4-2-6-11-9/h1,3,5,7,9,11H,2,4,6H2/t9-/m1/s1
SMILES:	C1CN[C@H](C1)c1cccnc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL264213
PubChem CID:	93047
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000089] Pyridines and derivatives [CHEMONTID:0001975] Pyrrolidinylpyridines

*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
Ki	6
Others	1

Activity Type	# Activity
Others	5
Protein Complex	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT413	Protein Complex	Neuronal acetylcholine receptor	Rattus norvegicus	Ki	=	17.0	nM	PMID[479346]
NPT413	Protein Complex	Neuronal acetylcholine receptor	Rattus norvegicus	Dopamine release	=	93.0	%	PMID[479346]
NPT2	Others	Unspecified		Ki	=	17.0	nM	PMID[479347]
NPT2	Others	Unspecified		Ki	=	41.0	nM	PMID[479347]
NPT2	Others	Unspecified		Ki	>	20000.0	nM	PMID[479347]
NPT2	Others	Unspecified		Ki	=	300.0	nM	PMID[479347]

☑ 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 NPC27740 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	1076
0.1-0.2	13686
0.2-0.3	17986
0.3-0.4	4471
0.4-0.5	2720
0.5-0.6	1732
0.6-0.7	754
0.7-0.8	221
0.8-0.85	38
0.85-0.9	6
0.9-0.95	6
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9421	High Similarity	NPC166424
0.9421	High Similarity	NPC146373
0.9421	High Similarity	NPC245244
0.9412	High Similarity	NPC48564
0.9412	High Similarity	NPC182570
0.9412	High Similarity	NPC265605
0.8657	High Similarity	NPC476454
0.8644	High Similarity	NPC27802
0.8636	High Similarity	NPC105127
0.8607	High Similarity	NPC297486
0.8607	High Similarity	NPC240136
0.8607	High Similarity	NPC471402
0.8594	High Similarity	NPC89490
0.8561	High Similarity	NPC96102
0.8538	High Similarity	NPC101165
0.8538	High Similarity	NPC82295
0.8537	High Similarity	NPC91958
0.8527	High Similarity	NPC475105
0.8527	High Similarity	NPC475090
0.8527	High Similarity	NPC329896
0.8507	High Similarity	NPC110126
0.8496	Intermediate Similarity	NPC84911
0.8462	Intermediate Similarity	NPC282398
0.8421	Intermediate Similarity	NPC261195
0.8421	Intermediate Similarity	NPC29886
0.8397	Intermediate Similarity	NPC324611
0.8397	Intermediate Similarity	NPC471322
0.839	Intermediate Similarity	NPC76540
0.8387	Intermediate Similarity	NPC143603
0.837	Intermediate Similarity	NPC73767
0.8358	Intermediate Similarity	NPC65408
0.8346	Intermediate Similarity	NPC290094
0.8309	Intermediate Similarity	NPC469767
0.8309	Intermediate Similarity	NPC469783
0.8309	Intermediate Similarity	NPC469761
0.8309	Intermediate Similarity	NPC279081
0.8309	Intermediate Similarity	NPC469780
0.8309	Intermediate Similarity	NPC469768
0.8309	Intermediate Similarity	NPC469784
0.8309	Intermediate Similarity	NPC469779
0.8281	Intermediate Similarity	NPC476322
0.8248	Intermediate Similarity	NPC469766
0.8214	Intermediate Similarity	NPC469811
0.8203	Intermediate Similarity	NPC46358
0.8197	Intermediate Similarity	NPC235843
0.8188	Intermediate Similarity	NPC190296
0.8175	Intermediate Similarity	NPC230002
0.8156	Intermediate Similarity	NPC321911
0.8154	Intermediate Similarity	NPC169625
0.8154	Intermediate Similarity	NPC202957
0.8143	Intermediate Similarity	NPC63545
0.8092	Intermediate Similarity	NPC471313
0.8092	Intermediate Similarity	NPC471311
0.8085	Intermediate Similarity	NPC179787
0.8085	Intermediate Similarity	NPC201380
0.8071	Intermediate Similarity	NPC159856
0.8071	Intermediate Similarity	NPC314372
0.8034	Intermediate Similarity	NPC83987
0.8015	Intermediate Similarity	NPC325252
0.8014	Intermediate Similarity	NPC288838
0.8014	Intermediate Similarity	NPC143872
0.7986	Intermediate Similarity	NPC325903
0.7984	Intermediate Similarity	NPC329825
0.797	Intermediate Similarity	NPC476131
0.7958	Intermediate Similarity	NPC471957
0.7934	Intermediate Similarity	NPC231655
0.7917	Intermediate Similarity	NPC470233
0.791	Intermediate Similarity	NPC69914
0.7891	Intermediate Similarity	NPC56765
0.7852	Intermediate Similarity	NPC256893
0.7847	Intermediate Similarity	NPC105818
0.7847	Intermediate Similarity	NPC53947
0.7847	Intermediate Similarity	NPC24678
0.7826	Intermediate Similarity	NPC150259
0.781	Intermediate Similarity	NPC198988
0.7793	Intermediate Similarity	NPC216713
0.7793	Intermediate Similarity	NPC470823
0.7762	Intermediate Similarity	NPC316069
0.7755	Intermediate Similarity	NPC476464
0.7754	Intermediate Similarity	NPC218268
0.774	Intermediate Similarity	NPC469760
0.774	Intermediate Similarity	NPC469763
0.774	Intermediate Similarity	NPC259644
0.774	Intermediate Similarity	NPC141926
0.774	Intermediate Similarity	NPC469765
0.774	Intermediate Similarity	NPC469786
0.774	Intermediate Similarity	NPC25008
0.774	Intermediate Similarity	NPC73952
0.774	Intermediate Similarity	NPC200214
0.7733	Intermediate Similarity	NPC317105
0.773	Intermediate Similarity	NPC63157
0.773	Intermediate Similarity	NPC473868
0.7724	Intermediate Similarity	NPC40070
0.7718	Intermediate Similarity	NPC122141
0.7718	Intermediate Similarity	NPC470204
0.7717	Intermediate Similarity	NPC84268
0.7714	Intermediate Similarity	NPC88097
0.771	Intermediate Similarity	NPC41174
0.7703	Intermediate Similarity	NPC236711
0.7698	Intermediate Similarity	NPC125746
0.7698	Intermediate Similarity	NPC251722
0.7698	Intermediate Similarity	NPC314102
0.7687	Intermediate Similarity	NPC212376
0.7687	Intermediate Similarity	NPC34844
0.7687	Intermediate Similarity	NPC75540
0.7687	Intermediate Similarity	NPC211572
0.7687	Intermediate Similarity	NPC70922
0.7687	Intermediate Similarity	NPC80597
0.7667	Intermediate Similarity	NPC470203
0.766	Intermediate Similarity	NPC115611
0.766	Intermediate Similarity	NPC59084
0.7656	Intermediate Similarity	NPC476566
0.7651	Intermediate Similarity	NPC41257
0.7651	Intermediate Similarity	NPC206819
0.7651	Intermediate Similarity	NPC318065
0.7647	Intermediate Similarity	NPC22079
0.7635	Intermediate Similarity	NPC469785
0.7616	Intermediate Similarity	NPC90723
0.76	Intermediate Similarity	NPC279918
0.76	Intermediate Similarity	NPC44773
0.76	Intermediate Similarity	NPC215584
0.7589	Intermediate Similarity	NPC316811
0.7589	Intermediate Similarity	NPC32002
0.7589	Intermediate Similarity	NPC315348
0.7586	Intermediate Similarity	NPC470111
0.7584	Intermediate Similarity	NPC216643
0.7584	Intermediate Similarity	NPC286427
0.7584	Intermediate Similarity	NPC469897
0.7584	Intermediate Similarity	NPC469762
0.7571	Intermediate Similarity	NPC471312
0.7569	Intermediate Similarity	NPC285731
0.7569	Intermediate Similarity	NPC204141
0.7569	Intermediate Similarity	NPC86288
0.7556	Intermediate Similarity	NPC306397
0.755	Intermediate Similarity	NPC225018
0.755	Intermediate Similarity	NPC282231
0.7535	Intermediate Similarity	NPC2949
0.7533	Intermediate Similarity	NPC92796
0.7533	Intermediate Similarity	NPC135141
0.7518	Intermediate Similarity	NPC169433
0.7483	Intermediate Similarity	NPC131718
0.7481	Intermediate Similarity	NPC250361
0.7466	Intermediate Similarity	NPC21605
0.7452	Intermediate Similarity	NPC474958
0.7451	Intermediate Similarity	NPC274229
0.745	Intermediate Similarity	NPC477815
0.7448	Intermediate Similarity	NPC467188
0.7426	Intermediate Similarity	NPC212125
0.7417	Intermediate Similarity	NPC230869
0.7403	Intermediate Similarity	NPC160105
0.7403	Intermediate Similarity	NPC49954
0.7403	Intermediate Similarity	NPC54988
0.7403	Intermediate Similarity	NPC474561
0.7394	Intermediate Similarity	NPC104049
0.7391	Intermediate Similarity	NPC315320
0.7386	Intermediate Similarity	NPC469813
0.7386	Intermediate Similarity	NPC311276
0.7386	Intermediate Similarity	NPC78375
0.7386	Intermediate Similarity	NPC478184
0.7386	Intermediate Similarity	NPC476446
0.7385	Intermediate Similarity	NPC148140
0.7372	Intermediate Similarity	NPC82331
0.7372	Intermediate Similarity	NPC473762
0.7355	Intermediate Similarity	NPC63751
0.7351	Intermediate Similarity	NPC167635
0.7351	Intermediate Similarity	NPC193740
0.7347	Intermediate Similarity	NPC105811
0.7338	Intermediate Similarity	NPC17751
0.7338	Intermediate Similarity	NPC280864
0.7333	Intermediate Similarity	NPC476297
0.7333	Intermediate Similarity	NPC476219
0.7329	Intermediate Similarity	NPC470440
0.7328	Intermediate Similarity	NPC81561
0.7319	Intermediate Similarity	NPC473587
0.731	Intermediate Similarity	NPC20144
0.7308	Intermediate Similarity	NPC194411
0.7308	Intermediate Similarity	NPC97343
0.7292	Intermediate Similarity	NPC284635
0.729	Intermediate Similarity	NPC49217
0.7287	Intermediate Similarity	NPC473901
0.7286	Intermediate Similarity	NPC330326
0.7273	Intermediate Similarity	NPC54102
0.7273	Intermediate Similarity	NPC213774
0.7273	Intermediate Similarity	NPC162689
0.7273	Intermediate Similarity	NPC40779
0.7273	Intermediate Similarity	NPC102423
0.7273	Intermediate Similarity	NPC149265
0.7267	Intermediate Similarity	NPC138842
0.7266	Intermediate Similarity	NPC475428
0.7248	Intermediate Similarity	NPC33421
0.7248	Intermediate Similarity	NPC473878
0.7237	Intermediate Similarity	NPC129721
0.7233	Intermediate Similarity	NPC280852
0.7222	Intermediate Similarity	NPC104483
0.7215	Intermediate Similarity	NPC314603
0.7215	Intermediate Similarity	NPC477611
0.7214	Intermediate Similarity	NPC475450
0.7214	Intermediate Similarity	NPC179365
0.719	Intermediate Similarity	NPC477591
0.719	Intermediate Similarity	NPC474492

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 NPC27740 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	392
0.1-0.2	852
0.2-0.3	1051
0.3-0.4	1881
0.4-0.5	2580
0.5-0.6	1668
0.6-0.7	560
0.7-0.8	139
0.8-0.85	17
0.85-0.9	8
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9412	High Similarity	NPD270	Clinical (unspecified phase)
0.9412	High Similarity	NPD268	Approved
0.9412	High Similarity	NPD271	Approved
0.9113	High Similarity	NPD991	Phase 2
0.9113	High Similarity	NPD992	Clinical (unspecified phase)
0.9068	High Similarity	NPD269	Clinical (unspecified phase)
0.8788	High Similarity	NPD768	Clinical (unspecified phase)
0.876	High Similarity	NPD9396	Approved
0.876	High Similarity	NPD9392	Approved
0.871	High Similarity	NPD748	Clinical (unspecified phase)
0.8682	High Similarity	NPD803	Phase 1
0.8661	High Similarity	NPD1598	Discontinued
0.8629	High Similarity	NPD9598	Discontinued
0.8583	High Similarity	NPD9583	Approved
0.8571	High Similarity	NPD9357	Approved
0.8561	High Similarity	NPD198	Clinical (unspecified phase)
0.8519	High Similarity	NPD1722	Approved
0.8507	High Similarity	NPD786	Approved
0.8462	Intermediate Similarity	NPD3476	Approved
0.8462	Intermediate Similarity	NPD3475	Approved
0.8358	Intermediate Similarity	NPD200	Phase 2
0.8358	Intermediate Similarity	NPD201	Phase 2
0.8284	Intermediate Similarity	NPD490	Clinical (unspecified phase)
0.8231	Intermediate Similarity	NPD2119	Approved
0.8231	Intermediate Similarity	NPD2118	Approved
0.8188	Intermediate Similarity	NPD2007	Clinical (unspecified phase)
0.8049	Intermediate Similarity	NPD4823	Approved
0.8049	Intermediate Similarity	NPD4824	Approved
0.8	Intermediate Similarity	NPD4028	Approved
0.8	Intermediate Similarity	NPD4030	Approved
0.8	Intermediate Similarity	NPD4029	Approved
0.7986	Intermediate Similarity	NPD2837	Discontinued
0.7934	Intermediate Similarity	NPD9098	Phase 3
0.7934	Intermediate Similarity	NPD9099	Clinical (unspecified phase)
0.7929	Intermediate Similarity	NPD2006	Phase 2
0.7929	Intermediate Similarity	NPD4637	Clinical (unspecified phase)
0.791	Intermediate Similarity	NPD715	Phase 3
0.7902	Intermediate Similarity	NPD4374	Clinical (unspecified phase)
0.7902	Intermediate Similarity	NPD3100	Discontinued
0.7868	Intermediate Similarity	NPD3942	Approved
0.7868	Intermediate Similarity	NPD3944	Approved
0.7852	Intermediate Similarity	NPD9726	Discontinued
0.7847	Intermediate Similarity	NPD2172	Phase 1
0.7794	Intermediate Similarity	NPD1995	Approved
0.7794	Intermediate Similarity	NPD1993	Approved
0.7794	Intermediate Similarity	NPD1994	Approved
0.7755	Intermediate Similarity	NPD3113	Approved
0.7755	Intermediate Similarity	NPD3114	Approved
0.7755	Intermediate Similarity	NPD3112	Approved
0.7755	Intermediate Similarity	NPD3115	Approved
0.7733	Intermediate Similarity	NPD3323	Discontinued
0.7708	Intermediate Similarity	NPD4547	Phase 3
0.7703	Intermediate Similarity	NPD1192	Clinical (unspecified phase)
0.7703	Intermediate Similarity	NPD2865	Clinical (unspecified phase)
0.7687	Intermediate Similarity	NPD975	Approved
0.7687	Intermediate Similarity	NPD976	Approved
0.7687	Intermediate Similarity	NPD2165	Phase 1
0.7687	Intermediate Similarity	NPD977	Approved
0.7667	Intermediate Similarity	NPD1853	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD2385	Clinical (unspecified phase)
0.7664	Intermediate Similarity	NPD1627	Clinical (unspecified phase)
0.766	Intermediate Similarity	NPD165	Phase 2
0.766	Intermediate Similarity	NPD9599	Approved
0.7655	Intermediate Similarity	NPD2430	Phase 2
0.7639	Intermediate Similarity	NPD1683	Approved
0.7635	Intermediate Similarity	NPD2580	Discontinued
0.7635	Intermediate Similarity	NPD473	Clinical (unspecified phase)
0.7626	Intermediate Similarity	NPD792	Discontinued
0.7626	Intermediate Similarity	NPD206	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD1917	Discontinued
0.7619	Intermediate Similarity	NPD3339	Approved
0.7609	Intermediate Similarity	NPD3385	Approved
0.7591	Intermediate Similarity	NPD809	Discontinued
0.7589	Intermediate Similarity	NPD2071	Approved
0.7589	Intermediate Similarity	NPD2068	Approved
0.7589	Intermediate Similarity	NPD2072	Approved
0.7589	Intermediate Similarity	NPD2073	Approved
0.7589	Intermediate Similarity	NPD2070	Approved
0.7589	Intermediate Similarity	NPD2074	Approved
0.7589	Intermediate Similarity	NPD2069	Approved
0.7589	Intermediate Similarity	NPD2075	Approved
0.7586	Intermediate Similarity	NPD4702	Approved
0.7586	Intermediate Similarity	NPD4703	Approved
0.7576	Intermediate Similarity	NPD5787	Discontinued
0.7574	Intermediate Similarity	NPD3654	Approved
0.7568	Intermediate Similarity	NPD1328	Approved
0.7557	Intermediate Similarity	NPD4811	Discontinued
0.7556	Intermediate Similarity	NPD9080	Approved
0.7554	Intermediate Similarity	NPD2142	Approved
0.7554	Intermediate Similarity	NPD2140	Approved
0.7554	Intermediate Similarity	NPD2141	Approved
0.7552	Intermediate Similarity	NPD3717	Discontinued
0.7535	Intermediate Similarity	NPD1395	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD5436	Phase 1
0.75	Intermediate Similarity	NPD3813	Approved
0.75	Intermediate Similarity	NPD5065	Approved
0.7484	Intermediate Similarity	NPD3609	Approved
0.7484	Intermediate Similarity	NPD3610	Approved
0.7483	Intermediate Similarity	NPD1404	Approved
0.7483	Intermediate Similarity	NPD1403	Approved
0.7468	Intermediate Similarity	NPD4779	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD2641	Approved
0.7468	Intermediate Similarity	NPD2640	Approved
0.7465	Intermediate Similarity	NPD945	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD6044	Discontinued
0.7434	Intermediate Similarity	NPD8026	Phase 1
0.7434	Intermediate Similarity	NPD6771	Discontinued
0.7432	Intermediate Similarity	NPD4641	Discontinued
0.7426	Intermediate Similarity	NPD9284	Approved
0.74	Intermediate Similarity	NPD2748	Clinical (unspecified phase)
0.7397	Intermediate Similarity	NPD7469	Discontinued
0.7394	Intermediate Similarity	NPD2896	Discontinued
0.7391	Intermediate Similarity	NPD9207	Approved
0.7391	Intermediate Similarity	NPD9206	Approved
0.7386	Intermediate Similarity	NPD3583	Phase 2
0.7379	Intermediate Similarity	NPD1918	Clinical (unspecified phase)
0.7376	Intermediate Similarity	NPD1254	Approved
0.7376	Intermediate Similarity	NPD1255	Approved
0.7376	Intermediate Similarity	NPD1253	Approved
0.7376	Intermediate Similarity	NPD1256	Approved
0.7372	Intermediate Similarity	NPD1095	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD3341	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD2185	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD2145	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD5300	Clinical (unspecified phase)
0.7319	Intermediate Similarity	NPD9305	Clinical (unspecified phase)
0.7319	Intermediate Similarity	NPD947	Approved
0.731	Intermediate Similarity	NPD4510	Discontinued
0.7308	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD272	Approved
0.7303	Intermediate Similarity	NPD1679	Approved
0.7296	Intermediate Similarity	NPD4181	Approved
0.7292	Intermediate Similarity	NPD3943	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD2642	Approved
0.729	Intermediate Similarity	NPD1248	Discontinued
0.729	Intermediate Similarity	NPD2639	Approved
0.7286	Intermediate Similarity	NPD9100	Approved
0.7285	Intermediate Similarity	NPD2150	Discontinued
0.7279	Intermediate Similarity	NPD6148	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD3117	Approved
0.7261	Intermediate Similarity	NPD3116	Approved
0.726	Intermediate Similarity	NPD649	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD1988	Phase 1
0.7248	Intermediate Similarity	NPD2462	Phase 3
0.7248	Intermediate Similarity	NPD2465	Approved
0.7248	Intermediate Similarity	NPD2466	Phase 3
0.7244	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD4075	Phase 2
0.723	Intermediate Similarity	NPD1661	Suspended
0.7219	Intermediate Similarity	NPD2061	Approved
0.7211	Intermediate Similarity	NPD175	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD5315	Discontinued
0.7205	Intermediate Similarity	NPD1291	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD6554	Approved
0.7203	Intermediate Similarity	NPD45	Approved
0.7197	Intermediate Similarity	NPD2875	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD1427	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD704	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.7185	Intermediate Similarity	NPD1561	Phase 2
0.7181	Intermediate Similarity	NPD1183	Approved
0.7181	Intermediate Similarity	NPD4371	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD60	Approved
0.7172	Intermediate Similarity	NPD1649	Discontinued
0.717	Intermediate Similarity	NPD482	Approved
0.717	Intermediate Similarity	NPD4128	Approved
0.717	Intermediate Similarity	NPD2928	Phase 2
0.716	Intermediate Similarity	NPD4649	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD1567	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD2012	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD751	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5254	Discontinued
0.7143	Intermediate Similarity	NPD6454	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD1270	Approved
0.7114	Intermediate Similarity	NPD2089	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD750	Phase 2
0.7099	Intermediate Similarity	NPD6277	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD1015	Phase 2
0.7097	Intermediate Similarity	NPD1016	Phase 2
0.7092	Intermediate Similarity	NPD1251	Discontinued
0.7086	Intermediate Similarity	NPD510	Phase 1
0.7083	Intermediate Similarity	NPD9506	Approved
0.7083	Intermediate Similarity	NPD1262	Discovery
0.7081	Intermediate Similarity	NPD3506	Approved
0.7081	Intermediate Similarity	NPD3505	Approved
0.7081	Intermediate Similarity	NPD2144	Approved
0.707	Intermediate Similarity	NPD5611	Phase 2
0.7068	Intermediate Similarity	NPD8840	Approved
0.7063	Intermediate Similarity	NPD5322	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD5806	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD3486	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD5934	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD4079	Approved
0.7037	Intermediate Similarity	NPD4076	Approved
0.7037	Intermediate Similarity	NPD2930	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD203	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD1380	Discovery
0.7027	Intermediate Similarity	NPD1352	Discontinued

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