NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	255.11
Volume:	246.034
LogP:	-0.715
LogD:	0.137
LogS:	-0.121
# Rotatable Bonds:	3
TPSA:	102.18
# H-Bond Aceptor:	6
# H-Bond Donor:	5
# Rings:	2
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.481
Synthetic Accessibility Score:	3.645
Fsp3:	0.5
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.354
MDCK Permeability:	0.00012239853094797581
Pgp-inhibitor:	0.0
Pgp-substrate:	0.431
Human Intestinal Absorption (HIA):	0.88
20% Bioavailability (F20%):	0.018
30% Bioavailability (F30%):	0.089

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.347
Plasma Protein Binding (PPB):	32.8955078125%
Volume Distribution (VD):	1.242
Pgp-substrate:	60.528926849365234%

ADMET: Metabolism

CYP1A2-inhibitor:	0.037
CYP1A2-substrate:	0.207
CYP2C19-inhibitor:	0.023
CYP2C19-substrate:	0.329
CYP2C9-inhibitor:	0.008
CYP2C9-substrate:	0.364
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.34
CYP3A4-inhibitor:	0.016
CYP3A4-substrate:	0.103

ADMET: Excretion

Clearance (CL):	11.549
Half-life (T1/2):	0.684

ADMET: Toxicity

hERG Blockers:	0.04
Human Hepatotoxicity (H-HT):	0.8
Drug-inuced Liver Injury (DILI):	0.195
AMES Toxicity:	0.352
Rat Oral Acute Toxicity:	0.012
Maximum Recommended Daily Dose:	0.036
Skin Sensitization:	0.297
Carcinogencity:	0.464
Eye Corrosion:	0.032
Eye Irritation:	0.073
Respiratory Toxicity:	0.838

Download Data

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

Natural Product: NPC160931

Natural Product ID:	NPC160931
*Common Name:**	L-Radicamine A
IUPAC Name:	(2S,3S,4S,5S)-2-(3-hydroxy-4-methoxyphenyl)-5-(hydroxymethyl)pyrrolidine-3,4-diol
Synonyms:
Standard InCHIKey:	NEAQPVOYHYPSER-BVALORAHSA-N
Standard InCHI:	InChI=1S/C12H17NO5/c1-18-9-3-2-6(4-8(9)15)10-12(17)11(16)7(5-14)13-10/h2-4,7,10-17H,5H2,1H3/t7-,10-,11-,12-/m0/s1
SMILES:	OC[C@@H]1N[C@H]([C@@H]([C@H]1O)O)c1ccc(c(c1)O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL454551
PubChem CID:	10083681
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000218] Pyrrolidines [CHEMONTID:0002336] Phenylpyrrolidines

*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
NPO14650	Lobelia chinensis	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22540	Aquilegia vulgaris	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14650	Lobelia chinensis	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6890	Euphorbia jolkinii	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14650	Lobelia chinensis	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14650	Lobelia chinensis	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO14650	Lobelia chinensis	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15952	Adansonia digitata	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6890	Euphorbia jolkinii	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2723	Artemisia carvifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18018	Aster multiradiatus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22540	Aquilegia vulgaris	Species	Ranunculaceae	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	8

Activity Type	# Activity
Individual Protein	2
Others	5
SINGLE PROTEIN	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT497	Individual Protein	Maltase-glucoamylase	Homo sapiens	IC50	=	6700.0	nM	PMID[533851]
NPT496	Individual Protein	Alpha-L-fucosidase 1	Bos taurus	IC50	=	41000.0	nM	PMID[533851]
NPT2	Others	Unspecified		IC50	>	200000.0	nM	PMID[533850]
NPT2	Others	Unspecified		IC50	=	113000.0	nM	PMID[533850]
NPT2	Others	Unspecified		IC50	=	25210.0	nM	PMID[533851]
NPT24816	SINGLE PROTEIN	Alpha-mannosidase	Canavalia ensiformis	IC50	=	28000.0	nM	PMID[533851]

☑ 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 NPC160931 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	267
0.1-0.2	1370
0.2-0.3	6832
0.3-0.4	11038
0.4-0.5	7319
0.5-0.6	11566
0.6-0.7	3449
0.7-0.8	742
0.8-0.85	101
0.85-0.9	10
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC37205
0.8553	High Similarity	NPC205167
0.8493	Intermediate Similarity	NPC208757
0.8487	Intermediate Similarity	NPC294249
0.8481	Intermediate Similarity	NPC147091
0.8462	Intermediate Similarity	NPC76213
0.8462	Intermediate Similarity	NPC277669
0.8438	Intermediate Similarity	NPC249274
0.8425	Intermediate Similarity	NPC329595
0.8425	Intermediate Similarity	NPC326599
0.8375	Intermediate Similarity	NPC59028
0.8375	Intermediate Similarity	NPC92191
0.8354	Intermediate Similarity	NPC2295
0.8354	Intermediate Similarity	NPC477564
0.8333	Intermediate Similarity	NPC207824
0.8333	Intermediate Similarity	NPC60538
0.8253	Intermediate Similarity	NPC477640
0.8253	Intermediate Similarity	NPC225597
0.8253	Intermediate Similarity	NPC470739
0.8221	Intermediate Similarity	NPC293871
0.8221	Intermediate Similarity	NPC124433
0.8193	Intermediate Similarity	NPC474475
0.8182	Intermediate Similarity	NPC210140
0.8176	Intermediate Similarity	NPC133011
0.8176	Intermediate Similarity	NPC82285
0.817	Intermediate Similarity	NPC204546
0.8153	Intermediate Similarity	NPC147390
0.8153	Intermediate Similarity	NPC246587
0.8153	Intermediate Similarity	NPC24233
0.8153	Intermediate Similarity	NPC135538
0.8153	Intermediate Similarity	NPC428
0.8153	Intermediate Similarity	NPC476571
0.8151	Intermediate Similarity	NPC323775
0.8151	Intermediate Similarity	NPC236347
0.8133	Intermediate Similarity	NPC58766
0.8133	Intermediate Similarity	NPC475686
0.8133	Intermediate Similarity	NPC266176
0.8133	Intermediate Similarity	NPC290759
0.8133	Intermediate Similarity	NPC82533
0.8133	Intermediate Similarity	NPC158148
0.8098	Intermediate Similarity	NPC18402
0.8095	Intermediate Similarity	NPC66341
0.8095	Intermediate Similarity	NPC477020
0.8095	Intermediate Similarity	NPC2314
0.8095	Intermediate Similarity	NPC192135
0.8092	Intermediate Similarity	NPC253429
0.8089	Intermediate Similarity	NPC321505
0.8089	Intermediate Similarity	NPC179825
0.8089	Intermediate Similarity	NPC191376
0.8084	Intermediate Similarity	NPC109925
0.8072	Intermediate Similarity	NPC150879
0.8072	Intermediate Similarity	NPC100566
0.8061	Intermediate Similarity	NPC134858
0.805	Intermediate Similarity	NPC274026
0.8047	Intermediate Similarity	NPC329969
0.8012	Intermediate Similarity	NPC476002
0.8	Intermediate Similarity	NPC233650
0.7987	Intermediate Similarity	NPC103379
0.7987	Intermediate Similarity	NPC477565
0.7977	Intermediate Similarity	NPC135772
0.7976	Intermediate Similarity	NPC69712
0.7976	Intermediate Similarity	NPC477562
0.7976	Intermediate Similarity	NPC26240
0.7964	Intermediate Similarity	NPC190332
0.7964	Intermediate Similarity	NPC181653
0.7963	Intermediate Similarity	NPC5238
0.7963	Intermediate Similarity	NPC469817
0.7963	Intermediate Similarity	NPC39701
0.7963	Intermediate Similarity	NPC172765
0.7963	Intermediate Similarity	NPC295691
0.7963	Intermediate Similarity	NPC184026
0.7963	Intermediate Similarity	NPC110416
0.7963	Intermediate Similarity	NPC278799
0.7963	Intermediate Similarity	NPC193949
0.7963	Intermediate Similarity	NPC2413
0.7963	Intermediate Similarity	NPC127674
0.7963	Intermediate Similarity	NPC276588
0.7963	Intermediate Similarity	NPC207757
0.7963	Intermediate Similarity	NPC54379
0.7963	Intermediate Similarity	NPC204828
0.7963	Intermediate Similarity	NPC249797
0.7963	Intermediate Similarity	NPC189266
0.7962	Intermediate Similarity	NPC185838
0.7952	Intermediate Similarity	NPC4138
0.7952	Intermediate Similarity	NPC284183
0.7952	Intermediate Similarity	NPC121275
0.7945	Intermediate Similarity	NPC13020
0.7945	Intermediate Similarity	NPC140359
0.7937	Intermediate Similarity	NPC151895
0.7937	Intermediate Similarity	NPC192768
0.7937	Intermediate Similarity	NPC97221
0.7937	Intermediate Similarity	NPC88249
0.7937	Intermediate Similarity	NPC220858
0.7917	Intermediate Similarity	NPC164429
0.7908	Intermediate Similarity	NPC131204
0.7908	Intermediate Similarity	NPC301050
0.7907	Intermediate Similarity	NPC474507
0.7907	Intermediate Similarity	NPC244554
0.7904	Intermediate Similarity	NPC264850
0.7904	Intermediate Similarity	NPC81247
0.7904	Intermediate Similarity	NPC13916
0.7904	Intermediate Similarity	NPC35627
0.7904	Intermediate Similarity	NPC476573
0.7895	Intermediate Similarity	NPC474470
0.7879	Intermediate Similarity	NPC215829
0.7879	Intermediate Similarity	NPC97072
0.7879	Intermediate Similarity	NPC4304
0.7877	Intermediate Similarity	NPC298486
0.7866	Intermediate Similarity	NPC40389
0.7866	Intermediate Similarity	NPC148014
0.7866	Intermediate Similarity	NPC315707
0.7866	Intermediate Similarity	NPC78359
0.7866	Intermediate Similarity	NPC65490
0.7866	Intermediate Similarity	NPC475326
0.7862	Intermediate Similarity	NPC476151
0.7861	Intermediate Similarity	NPC476574
0.7861	Intermediate Similarity	NPC312918
0.7861	Intermediate Similarity	NPC155442
0.7861	Intermediate Similarity	NPC477561
0.7857	Intermediate Similarity	NPC252960
0.7857	Intermediate Similarity	NPC193528
0.7844	Intermediate Similarity	NPC276944
0.7844	Intermediate Similarity	NPC238530
0.7844	Intermediate Similarity	NPC232514
0.7844	Intermediate Similarity	NPC24465
0.7836	Intermediate Similarity	NPC187678
0.7829	Intermediate Similarity	NPC160692
0.7824	Intermediate Similarity	NPC108434
0.7824	Intermediate Similarity	NPC475215
0.7818	Intermediate Similarity	NPC111485
0.7816	Intermediate Similarity	NPC476575
0.7816	Intermediate Similarity	NPC275132
0.7811	Intermediate Similarity	NPC83198
0.7811	Intermediate Similarity	NPC160570
0.7811	Intermediate Similarity	NPC204908
0.7809	Intermediate Similarity	NPC117717
0.7798	Intermediate Similarity	NPC195392
0.7791	Intermediate Similarity	NPC237044
0.7791	Intermediate Similarity	NPC476577
0.7791	Intermediate Similarity	NPC148709
0.7791	Intermediate Similarity	NPC173416
0.7784	Intermediate Similarity	NPC320104
0.7784	Intermediate Similarity	NPC218614
0.7778	Intermediate Similarity	NPC190783
0.7778	Intermediate Similarity	NPC152680
0.7778	Intermediate Similarity	NPC232386
0.7778	Intermediate Similarity	NPC218530
0.7765	Intermediate Similarity	NPC311991
0.7763	Intermediate Similarity	NPC302171
0.7763	Intermediate Similarity	NPC33338
0.7763	Intermediate Similarity	NPC93882
0.7763	Intermediate Similarity	NPC300020
0.7763	Intermediate Similarity	NPC130595
0.7758	Intermediate Similarity	NPC129603
0.7756	Intermediate Similarity	NPC323123
0.7751	Intermediate Similarity	NPC81218
0.7751	Intermediate Similarity	NPC306555
0.7751	Intermediate Similarity	NPC158376
0.7751	Intermediate Similarity	NPC474931
0.7751	Intermediate Similarity	NPC12053
0.7751	Intermediate Similarity	NPC205421
0.7751	Intermediate Similarity	NPC145832
0.7751	Intermediate Similarity	NPC117188
0.7748	Intermediate Similarity	NPC262641
0.7746	Intermediate Similarity	NPC474325
0.7742	Intermediate Similarity	NPC14600
0.7742	Intermediate Similarity	NPC312770
0.7742	Intermediate Similarity	NPC41473
0.7742	Intermediate Similarity	NPC204848
0.7742	Intermediate Similarity	NPC160607
0.774	Intermediate Similarity	NPC186546
0.774	Intermediate Similarity	NPC476576
0.7738	Intermediate Similarity	NPC76116
0.7736	Intermediate Similarity	NPC130926
0.7733	Intermediate Similarity	NPC304675
0.7733	Intermediate Similarity	NPC49353
0.7727	Intermediate Similarity	NPC11147
0.7718	Intermediate Similarity	NPC320242
0.7718	Intermediate Similarity	NPC318965
0.7714	Intermediate Similarity	NPC248642
0.7712	Intermediate Similarity	NPC6854
0.7712	Intermediate Similarity	NPC313737
0.7712	Intermediate Similarity	NPC285078
0.7707	Intermediate Similarity	NPC328750
0.7707	Intermediate Similarity	NPC66518
0.7707	Intermediate Similarity	NPC213206
0.7707	Intermediate Similarity	NPC474915
0.7707	Intermediate Similarity	NPC188163
0.7701	Intermediate Similarity	NPC474745
0.7701	Intermediate Similarity	NPC99179
0.7697	Intermediate Similarity	NPC186063
0.7697	Intermediate Similarity	NPC175890
0.7697	Intermediate Similarity	NPC82457
0.7697	Intermediate Similarity	NPC48490
0.7697	Intermediate Similarity	NPC274661
0.7697	Intermediate Similarity	NPC11296
0.7692	Intermediate Similarity	NPC124657
0.7692	Intermediate Similarity	NPC219233
0.7692	Intermediate Similarity	NPC170170
0.7692	Intermediate Similarity	NPC211468

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 NPC160931 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	150
0.1-0.2	575
0.2-0.3	988
0.3-0.4	2236
0.4-0.5	2673
0.5-0.6	1740
0.6-0.7	580
0.7-0.8	197
0.8-0.85	8
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8839	High Similarity	NPD2977	Approved
0.8839	High Similarity	NPD2978	Approved
0.86	High Similarity	NPD3060	Approved
0.8493	Intermediate Similarity	NPD1132	Approved
0.8493	Intermediate Similarity	NPD1136	Approved
0.8493	Intermediate Similarity	NPD1130	Approved
0.8425	Intermediate Similarity	NPD597	Approved
0.8425	Intermediate Similarity	NPD598	Approved
0.8425	Intermediate Similarity	NPD601	Approved
0.8322	Intermediate Similarity	NPD823	Approved
0.8322	Intermediate Similarity	NPD817	Approved
0.8235	Intermediate Similarity	NPD4162	Approved
0.8151	Intermediate Similarity	NPD9621	Approved
0.8151	Intermediate Similarity	NPD9620	Approved
0.8151	Intermediate Similarity	NPD9619	Approved
0.8117	Intermediate Similarity	NPD4236	Phase 3
0.8117	Intermediate Similarity	NPD4237	Approved
0.8067	Intermediate Similarity	NPD3062	Approved
0.8067	Intermediate Similarity	NPD3059	Approved
0.8067	Intermediate Similarity	NPD3061	Approved
0.805	Intermediate Similarity	NPD3687	Approved
0.805	Intermediate Similarity	NPD3686	Approved
0.8025	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7961	Intermediate Similarity	NPD5314	Approved
0.7945	Intermediate Similarity	NPD9622	Approved
0.7914	Intermediate Similarity	NPD5772	Approved
0.7914	Intermediate Similarity	NPD5773	Approved
0.7881	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.7866	Intermediate Similarity	NPD2563	Approved
0.7866	Intermediate Similarity	NPD2560	Approved
0.7812	Intermediate Similarity	NPD52	Approved
0.7812	Intermediate Similarity	NPD7527	Clinical (unspecified phase)
0.7812	Intermediate Similarity	NPD7526	Approved
0.7799	Intermediate Similarity	NPD1774	Approved
0.7785	Intermediate Similarity	NPD5241	Discontinued
0.7763	Intermediate Similarity	NPD2674	Phase 3
0.775	Intermediate Similarity	NPD1424	Approved
0.775	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7748	Intermediate Similarity	NPD3180	Approved
0.7748	Intermediate Similarity	NPD3179	Approved
0.7727	Intermediate Similarity	NPD3052	Approved
0.7727	Intermediate Similarity	NPD2568	Approved
0.7727	Intermediate Similarity	NPD3054	Approved
0.7718	Intermediate Similarity	NPD1818	Approved
0.7718	Intermediate Similarity	NPD1820	Approved
0.7718	Intermediate Similarity	NPD1817	Approved
0.7718	Intermediate Similarity	NPD1819	Approved
0.7707	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.7683	Intermediate Similarity	NPD4773	Phase 2
0.7683	Intermediate Similarity	NPD4772	Phase 2
0.7682	Intermediate Similarity	NPD600	Approved
0.7682	Intermediate Similarity	NPD596	Approved
0.7673	Intermediate Similarity	NPD2677	Approved
0.7671	Intermediate Similarity	NPD9384	Approved
0.7671	Intermediate Similarity	NPD9381	Approved
0.7667	Intermediate Similarity	NPD602	Approved
0.7667	Intermediate Similarity	NPD599	Approved
0.7654	Intermediate Similarity	NPD6031	Approved
0.7654	Intermediate Similarity	NPD5976	Discontinued
0.7654	Intermediate Similarity	NPD6030	Approved
0.764	Intermediate Similarity	NPD2874	Phase 2
0.764	Intermediate Similarity	NPD3536	Discontinued
0.7605	Intermediate Similarity	NPD4581	Clinical (unspecified phase)
0.7602	Intermediate Similarity	NPD2489	Approved
0.7602	Intermediate Similarity	NPD27	Approved
0.76	Intermediate Similarity	NPD3055	Approved
0.76	Intermediate Similarity	NPD3053	Approved
0.7595	Intermediate Similarity	NPD7153	Discontinued
0.7595	Intermediate Similarity	NPD1372	Clinical (unspecified phase)
0.7588	Intermediate Similarity	NPD6071	Discontinued
0.7584	Intermediate Similarity	NPD7906	Approved
0.7582	Intermediate Similarity	NPD3145	Approved
0.7582	Intermediate Similarity	NPD3144	Approved
0.7562	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.755	Intermediate Similarity	NPD859	Approved
0.755	Intermediate Similarity	NPD858	Approved
0.7534	Intermediate Similarity	NPD316	Approved
0.7532	Intermediate Similarity	NPD1423	Approved
0.7531	Intermediate Similarity	NPD3157	Approved
0.7531	Intermediate Similarity	NPD4584	Approved
0.7531	Intermediate Similarity	NPD3158	Phase 1
0.7531	Intermediate Similarity	NPD1771	Clinical (unspecified phase)
0.753	Intermediate Similarity	NPD7298	Approved
0.7529	Intermediate Similarity	NPD6107	Approved
0.7528	Intermediate Similarity	NPD4663	Approved
0.7516	Intermediate Similarity	NPD3165	Approved
0.7516	Intermediate Similarity	NPD3167	Approved
0.7516	Intermediate Similarity	NPD3164	Approved
0.7516	Intermediate Similarity	NPD3166	Approved
0.75	Intermediate Similarity	NPD4210	Discontinued
0.7483	Intermediate Similarity	NPD1794	Approved
0.7471	Intermediate Similarity	NPD4666	Phase 3
0.7468	Intermediate Similarity	NPD1632	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD3056	Clinical (unspecified phase)
0.7466	Intermediate Similarity	NPD9613	Approved
0.7466	Intermediate Similarity	NPD318	Approved
0.7466	Intermediate Similarity	NPD16	Approved
0.7466	Intermediate Similarity	NPD9616	Approved
0.7466	Intermediate Similarity	NPD9615	Approved
0.7466	Intermediate Similarity	NPD317	Approved
0.7466	Intermediate Similarity	NPD856	Approved
0.7458	Intermediate Similarity	NPD4578	Approved
0.7458	Intermediate Similarity	NPD4577	Approved
0.7442	Intermediate Similarity	NPD2969	Approved
0.7442	Intermediate Similarity	NPD5137	Approved
0.7442	Intermediate Similarity	NPD4083	Discontinued
0.7442	Intermediate Similarity	NPD2970	Approved
0.7434	Intermediate Similarity	NPD558	Phase 2
0.743	Intermediate Similarity	NPD3857	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD4123	Phase 3
0.7416	Intermediate Similarity	NPD8053	Approved
0.7416	Intermediate Similarity	NPD8054	Approved
0.7412	Intermediate Similarity	NPD5709	Phase 3
0.7407	Intermediate Similarity	NPD3845	Phase 1
0.7403	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7401	Intermediate Similarity	NPD3936	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD2562	Approved
0.74	Intermediate Similarity	NPD2561	Approved
0.7399	Intermediate Similarity	NPD2898	Approved
0.7386	Intermediate Similarity	NPD6297	Approved
0.7384	Intermediate Similarity	NPD3051	Approved
0.7384	Intermediate Similarity	NPD4010	Discontinued
0.7372	Intermediate Similarity	NPD2238	Phase 2
0.7368	Intermediate Similarity	NPD1133	Approved
0.7368	Intermediate Similarity	NPD1131	Approved
0.7368	Intermediate Similarity	NPD1129	Approved
0.7368	Intermediate Similarity	NPD1135	Approved
0.7368	Intermediate Similarity	NPD1134	Approved
0.736	Intermediate Similarity	NPD7310	Approved
0.736	Intermediate Similarity	NPD7312	Approved
0.736	Intermediate Similarity	NPD7311	Approved
0.736	Intermediate Similarity	NPD7313	Approved
0.7358	Intermediate Similarity	NPD9570	Approved
0.7358	Intermediate Similarity	NPD3175	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD5160	Discontinued
0.7345	Intermediate Similarity	NPD7038	Approved
0.7345	Intermediate Similarity	NPD7039	Approved
0.7337	Intermediate Similarity	NPD3558	Approved
0.7337	Intermediate Similarity	NPD3556	Approved
0.7337	Intermediate Similarity	NPD3559	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD3560	Approved
0.7337	Intermediate Similarity	NPD3557	Approved
0.7329	Intermediate Similarity	NPD5177	Phase 3
0.7329	Intermediate Similarity	NPD2460	Phase 3
0.7329	Intermediate Similarity	NPD2459	Approved
0.7329	Intermediate Similarity	NPD2458	Approved
0.7318	Intermediate Similarity	NPD6853	Approved
0.7318	Intermediate Similarity	NPD6851	Approved
0.7318	Intermediate Similarity	NPD7309	Approved
0.7312	Intermediate Similarity	NPD1375	Discontinued
0.7312	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD3163	Approved
0.7308	Intermediate Similarity	NPD839	Approved
0.7308	Intermediate Similarity	NPD840	Approved
0.7308	Intermediate Similarity	NPD3162	Approved
0.7305	Intermediate Similarity	NPD4678	Approved
0.7305	Intermediate Similarity	NPD4675	Approved
0.7303	Intermediate Similarity	NPD9634	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD5310	Approved
0.7303	Intermediate Similarity	NPD5311	Approved
0.7301	Intermediate Similarity	NPD2422	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD3122	Phase 3
0.7296	Intermediate Similarity	NPD2154	Approved
0.7296	Intermediate Similarity	NPD2155	Approved
0.7296	Intermediate Similarity	NPD2156	Approved
0.729	Intermediate Similarity	NPD3027	Phase 3
0.7283	Intermediate Similarity	NPD4166	Phase 2
0.7278	Intermediate Similarity	NPD2653	Approved
0.7273	Intermediate Similarity	NPD42	Phase 2
0.7273	Intermediate Similarity	NPD6042	Phase 2
0.7273	Intermediate Similarity	NPD4873	Discontinued
0.7267	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD9618	Approved
0.726	Intermediate Similarity	NPD9614	Approved
0.7251	Intermediate Similarity	NPD7831	Phase 2
0.7251	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7251	Intermediate Similarity	NPD7833	Phase 2
0.725	Intermediate Similarity	NPD2240	Approved
0.725	Intermediate Similarity	NPD2239	Approved
0.7248	Intermediate Similarity	NPD1798	Approved
0.7248	Intermediate Similarity	NPD1797	Approved
0.7246	Intermediate Similarity	NPD824	Approved
0.7239	Intermediate Similarity	NPD302	Approved
0.7226	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD4227	Discontinued
0.7212	Intermediate Similarity	NPD3645	Discontinued
0.7204	Intermediate Similarity	NPD4604	Approved
0.7204	Intermediate Similarity	NPD4605	Approved
0.7197	Intermediate Similarity	NPD3532	Approved
0.7197	Intermediate Similarity	NPD6405	Approved
0.7197	Intermediate Similarity	NPD3531	Approved
0.7197	Intermediate Similarity	NPD6407	Approved
0.7197	Intermediate Similarity	NPD3530	Approved
0.7195	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD6788	Approved
0.7176	Intermediate Similarity	NPD4585	Approved
0.7168	Intermediate Similarity	NPD2042	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD2041	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD5895	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD2845	Phase 2

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