NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	225.1
Volume:	219.948
LogP:	-1.27
LogD:	-0.204
LogS:	-0.322
# Rotatable Bonds:	2
TPSA:	92.95
# H-Bond Aceptor:	5
# H-Bond Donor:	5
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.451
Synthetic Accessibility Score:	3.596
Fsp3:	0.455
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:	-5.412
MDCK Permeability:	7.97919256001478e-06
Pgp-inhibitor:	0.0
Pgp-substrate:	0.275
Human Intestinal Absorption (HIA):	0.831
20% Bioavailability (F20%):	0.996
30% Bioavailability (F30%):	0.994

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.133
Plasma Protein Binding (PPB):	28.129600524902344%
Volume Distribution (VD):	1.192
Pgp-substrate:	75.57917022705078%

ADMET: Metabolism

CYP1A2-inhibitor:	0.041
CYP1A2-substrate:	0.051
CYP2C19-inhibitor:	0.025
CYP2C19-substrate:	0.52
CYP2C9-inhibitor:	0.004
CYP2C9-substrate:	0.652
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.269
CYP3A4-inhibitor:	0.018
CYP3A4-substrate:	0.068

ADMET: Excretion

Clearance (CL):	6.143
Half-life (T1/2):	0.752

ADMET: Toxicity

hERG Blockers:	0.059
Human Hepatotoxicity (H-HT):	0.9
Drug-inuced Liver Injury (DILI):	0.26
AMES Toxicity:	0.067
Rat Oral Acute Toxicity:	0.011
Maximum Recommended Daily Dose:	0.035
Skin Sensitization:	0.208
Carcinogencity:	0.02
Eye Corrosion:	0.005
Eye Irritation:	0.033
Respiratory Toxicity:	0.415

Download Data

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

Natural Product: NPC208757

Natural Product ID:	NPC208757
*Common Name:**	Radicamine B
IUPAC Name:	(2R,3R,4R,5R)-2-(hydroxymethyl)-5-(4-hydroxyphenyl)pyrrolidine-3,4-diol
Synonyms:
Standard InCHIKey:	BRPXIQPSCKPBLH-GWOFURMSSA-N
Standard InCHI:	InChI=1S/C11H15NO4/c13-5-8-10(15)11(16)9(12-8)6-1-3-7(14)4-2-6/h1-4,8-16H,5H2/t8-,9-,10-,11-/m1/s1
SMILES:	OC[C@H]1N[C@@H]([C@H]([C@@H]1O)O)c1ccc(cc1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL466791
PubChem CID:	15953621
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]
NPO14650	Lobelia chinensis	Species	Campanulaceae	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]

☑ 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	4

Activity Type	# Activity
Others	4

Target ID	Target Type	Target Name	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified	IC50	>	200000.0	nM	PMID[464309]
NPT2	Others	Unspecified	IC50	=	24000.0	nM	PMID[464309]
NPT2	Others	Unspecified	IC50	=	10000.0	nM	PMID[464309]

☑ 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 NPC208757 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	212
0.1-0.2	1140
0.2-0.3	7372
0.3-0.4	10437
0.4-0.5	13528
0.5-0.6	8318
0.6-0.7	1545
0.7-0.8	136
0.8-0.85	5
0.85-0.9	2
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.8493	Intermediate Similarity	NPC160931
0.8493	Intermediate Similarity	NPC37205
0.8203	Intermediate Similarity	NPC137096
0.8189	Intermediate Similarity	NPC213
0.8189	Intermediate Similarity	NPC10286
0.8134	Intermediate Similarity	NPC323775
0.8134	Intermediate Similarity	NPC236347
0.7907	Intermediate Similarity	NPC101139
0.7902	Intermediate Similarity	NPC204546
0.7868	Intermediate Similarity	NPC322366
0.7857	Intermediate Similarity	NPC290566
0.7857	Intermediate Similarity	NPC145638
0.7842	Intermediate Similarity	NPC302171
0.7842	Intermediate Similarity	NPC33338
0.7842	Intermediate Similarity	NPC300020
0.7832	Intermediate Similarity	NPC323123
0.7794	Intermediate Similarity	NPC318965
0.7762	Intermediate Similarity	NPC211468
0.7762	Intermediate Similarity	NPC170170
0.7762	Intermediate Similarity	NPC219233
0.7744	Intermediate Similarity	NPC118522
0.7744	Intermediate Similarity	NPC169207
0.7744	Intermediate Similarity	NPC115627
0.7727	Intermediate Similarity	NPC85276
0.76	Intermediate Similarity	NPC147000
0.76	Intermediate Similarity	NPC226778
0.76	Intermediate Similarity	NPC304761
0.76	Intermediate Similarity	NPC150254
0.7586	Intermediate Similarity	NPC251439
0.7552	Intermediate Similarity	NPC64205
0.7536	Intermediate Similarity	NPC320242
0.7518	Intermediate Similarity	NPC307020
0.75	Intermediate Similarity	NPC29601
0.7464	Intermediate Similarity	NPC171372
0.7448	Intermediate Similarity	NPC214988
0.744	Intermediate Similarity	NPC327226
0.7419	Intermediate Similarity	NPC125732
0.7405	Intermediate Similarity	NPC146422
0.7386	Intermediate Similarity	NPC476268
0.7383	Intermediate Similarity	NPC294249
0.7347	Intermediate Similarity	NPC168861
0.7343	Intermediate Similarity	NPC247018
0.7343	Intermediate Similarity	NPC307123
0.7343	Intermediate Similarity	NPC97870
0.7308	Intermediate Similarity	NPC147091
0.7286	Intermediate Similarity	NPC136112
0.7286	Intermediate Similarity	NPC141739
0.7279	Intermediate Similarity	NPC283760
0.7273	Intermediate Similarity	NPC277669
0.7273	Intermediate Similarity	NPC76213
0.7255	Intermediate Similarity	NPC207824
0.7255	Intermediate Similarity	NPC60538
0.7244	Intermediate Similarity	NPC68055
0.7222	Intermediate Similarity	NPC289381
0.7222	Intermediate Similarity	NPC155847
0.7205	Intermediate Similarity	NPC195392
0.72	Intermediate Similarity	NPC303611
0.72	Intermediate Similarity	NPC226096
0.72	Intermediate Similarity	NPC290515
0.72	Intermediate Similarity	NPC164514
0.72	Intermediate Similarity	NPC108606
0.7185	Intermediate Similarity	NPC188867
0.7185	Intermediate Similarity	NPC281686
0.7185	Intermediate Similarity	NPC106551
0.7183	Intermediate Similarity	NPC145888
0.7183	Intermediate Similarity	NPC16031
0.7183	Intermediate Similarity	NPC161593
0.7179	Intermediate Similarity	NPC477564
0.7179	Intermediate Similarity	NPC2295
0.7172	Intermediate Similarity	NPC267237
0.717	Intermediate Similarity	NPC205167
0.7153	Intermediate Similarity	NPC329595
0.7153	Intermediate Similarity	NPC326599
0.7152	Intermediate Similarity	NPC125852
0.7107	Intermediate Similarity	NPC92191
0.7107	Intermediate Similarity	NPC59028
0.7103	Intermediate Similarity	NPC88667
0.7097	Intermediate Similarity	NPC20142
0.7097	Intermediate Similarity	NPC476742
0.7097	Intermediate Similarity	NPC215351
0.7095	Intermediate Similarity	NPC238412
0.7087	Intermediate Similarity	NPC214200
0.7087	Intermediate Similarity	NPC228400
0.7075	Intermediate Similarity	NPC109580
0.7073	Intermediate Similarity	NPC474475
0.7067	Intermediate Similarity	NPC326241
0.7063	Intermediate Similarity	NPC249274
0.7055	Intermediate Similarity	NPC210140
0.7055	Intermediate Similarity	NPC328494
0.7051	Intermediate Similarity	NPC476741
0.7051	Intermediate Similarity	NPC244509
0.7048	Intermediate Similarity	NPC119652
0.7048	Intermediate Similarity	NPC97526
0.7044	Intermediate Similarity	NPC79328
0.7037	Intermediate Similarity	NPC280022
0.7037	Intermediate Similarity	NPC134858
0.703	Intermediate Similarity	NPC470739
0.703	Intermediate Similarity	NPC225597
0.703	Intermediate Similarity	NPC477640
0.7029	Intermediate Similarity	NPC239697
0.7013	Intermediate Similarity	NPC473491
0.7013	Intermediate Similarity	NPC476743
0.7012	Intermediate Similarity	NPC475686
0.7012	Intermediate Similarity	NPC58766
0.7006	Intermediate Similarity	NPC133011
0.7006	Intermediate Similarity	NPC82285
0.7	Intermediate Similarity	NPC474862
0.7	Intermediate Similarity	NPC27581
0.6987	Remote Similarity	NPC274026
0.6985	Remote Similarity	NPC317254
0.6981	Remote Similarity	NPC29647
0.698	Remote Similarity	NPC253429
0.698	Remote Similarity	NPC48202
0.698	Remote Similarity	NPC471201
0.6977	Remote Similarity	NPC178902
0.6975	Remote Similarity	NPC233650
0.6975	Remote Similarity	NPC293871
0.6975	Remote Similarity	NPC124433
0.697	Remote Similarity	NPC471165
0.6968	Remote Similarity	NPC147390
0.6968	Remote Similarity	NPC428
0.6968	Remote Similarity	NPC135538
0.6968	Remote Similarity	NPC24233
0.6968	Remote Similarity	NPC246587
0.6968	Remote Similarity	NPC476744
0.6968	Remote Similarity	NPC476571
0.6962	Remote Similarity	NPC323336
0.6962	Remote Similarity	NPC326349
0.6957	Remote Similarity	NPC97072
0.6957	Remote Similarity	NPC215829
0.6951	Remote Similarity	NPC89831
0.6933	Remote Similarity	NPC209377
0.6933	Remote Similarity	NPC476989
0.6923	Remote Similarity	NPC262166
0.6918	Remote Similarity	NPC244336
0.6913	Remote Similarity	NPC313694
0.6913	Remote Similarity	NPC242159
0.6912	Remote Similarity	NPC142599
0.6912	Remote Similarity	NPC118202
0.6909	Remote Similarity	NPC266176
0.6909	Remote Similarity	NPC158148
0.6909	Remote Similarity	NPC290759
0.6909	Remote Similarity	NPC82533
0.6903	Remote Similarity	NPC191376
0.6903	Remote Similarity	NPC179825
0.6903	Remote Similarity	NPC321505
0.6901	Remote Similarity	NPC140359
0.6901	Remote Similarity	NPC318777
0.6901	Remote Similarity	NPC13020
0.6899	Remote Similarity	NPC91461
0.6899	Remote Similarity	NPC7686
0.6899	Remote Similarity	NPC40258
0.6897	Remote Similarity	NPC271808
0.689	Remote Similarity	NPC193853
0.689	Remote Similarity	NPC223077
0.689	Remote Similarity	NPC56887
0.6886	Remote Similarity	NPC2314
0.6884	Remote Similarity	NPC311737
0.6884	Remote Similarity	NPC38458
0.6883	Remote Similarity	NPC185838
0.688	Remote Similarity	NPC138117
0.688	Remote Similarity	NPC325292
0.6875	Remote Similarity	NPC321561
0.6871	Remote Similarity	NPC149379
0.6867	Remote Similarity	NPC193528
0.6866	Remote Similarity	NPC474149
0.6855	Remote Similarity	NPC300017
0.6852	Remote Similarity	NPC63931
0.6848	Remote Similarity	NPC100566
0.6848	Remote Similarity	NPC150879
0.6848	Remote Similarity	NPC181653
0.6848	Remote Similarity	NPC190332
0.6842	Remote Similarity	NPC13696
0.6842	Remote Similarity	NPC476575
0.6842	Remote Similarity	NPC97811
0.6842	Remote Similarity	NPC153690
0.6835	Remote Similarity	NPC317784
0.6835	Remote Similarity	NPC142638
0.6831	Remote Similarity	NPC298486
0.6829	Remote Similarity	NPC121275
0.6829	Remote Similarity	NPC4138
0.6829	Remote Similarity	NPC284183
0.6824	Remote Similarity	NPC160692
0.6822	Remote Similarity	NPC213730
0.6821	Remote Similarity	NPC197921
0.6818	Remote Similarity	NPC231705
0.6815	Remote Similarity	NPC103379
0.6815	Remote Similarity	NPC56685
0.6815	Remote Similarity	NPC477565
0.6813	Remote Similarity	NPC172765
0.6813	Remote Similarity	NPC193949
0.6813	Remote Similarity	NPC110416
0.6813	Remote Similarity	NPC207757
0.6813	Remote Similarity	NPC469428
0.6813	Remote Similarity	NPC249797
0.6813	Remote Similarity	NPC184026
0.6813	Remote Similarity	NPC5238
0.6813	Remote Similarity	NPC39701
0.6813	Remote Similarity	NPC127674
0.6813	Remote Similarity	NPC204828

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 NPC208757 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	133
0.1-0.2	465
0.2-0.3	931
0.3-0.4	1814
0.4-0.5	3237
0.5-0.6	1931
0.6-0.7	527
0.7-0.8	96
0.8-0.85	16
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.837	Intermediate Similarity	NPD1132	Approved
0.837	Intermediate Similarity	NPD1130	Approved
0.837	Intermediate Similarity	NPD1136	Approved
0.8346	Intermediate Similarity	NPD317	Approved
0.8346	Intermediate Similarity	NPD318	Approved
0.8321	Intermediate Similarity	NPD817	Approved
0.8321	Intermediate Similarity	NPD823	Approved
0.8296	Intermediate Similarity	NPD601	Approved
0.8296	Intermediate Similarity	NPD598	Approved
0.8296	Intermediate Similarity	NPD597	Approved
0.8281	Intermediate Similarity	NPD316	Approved
0.8203	Intermediate Similarity	NPD16	Approved
0.8203	Intermediate Similarity	NPD856	Approved
0.8203	Intermediate Similarity	NPD9613	Approved
0.8203	Intermediate Similarity	NPD9615	Approved
0.8203	Intermediate Similarity	NPD9616	Approved
0.8134	Intermediate Similarity	NPD9619	Approved
0.8134	Intermediate Similarity	NPD9621	Approved
0.8134	Intermediate Similarity	NPD9620	Approved
0.8106	Intermediate Similarity	NPD2561	Approved
0.8106	Intermediate Similarity	NPD2562	Approved
0.806	Intermediate Similarity	NPD1129	Approved
0.806	Intermediate Similarity	NPD1133	Approved
0.806	Intermediate Similarity	NPD1135	Approved
0.806	Intermediate Similarity	NPD1134	Approved
0.806	Intermediate Similarity	NPD1131	Approved
0.8058	Intermediate Similarity	NPD2568	Approved
0.8043	Intermediate Similarity	NPD3059	Approved
0.8043	Intermediate Similarity	NPD3061	Approved
0.8043	Intermediate Similarity	NPD3062	Approved
0.8	Intermediate Similarity	NPD602	Approved
0.8	Intermediate Similarity	NPD599	Approved
0.7969	Intermediate Similarity	NPD9614	Approved
0.7969	Intermediate Similarity	NPD9618	Approved
0.7929	Intermediate Similarity	NPD5314	Approved
0.791	Intermediate Similarity	NPD9622	Approved
0.7868	Intermediate Similarity	NPD859	Approved
0.7868	Intermediate Similarity	NPD858	Approved
0.7857	Intermediate Similarity	NPD9380	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD9381	Approved
0.7744	Intermediate Similarity	NPD9384	Approved
0.7714	Intermediate Similarity	NPD6407	Approved
0.7714	Intermediate Similarity	NPD6405	Approved
0.7703	Intermediate Similarity	NPD2874	Phase 2
0.7687	Intermediate Similarity	NPD2688	Clinical (unspecified phase)
0.7664	Intermediate Similarity	NPD3055	Approved
0.7664	Intermediate Similarity	NPD3053	Approved
0.7639	Intermediate Similarity	NPD1632	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD3555	Approved
0.7622	Intermediate Similarity	NPD3552	Approved
0.7622	Intermediate Similarity	NPD3553	Approved
0.7622	Intermediate Similarity	NPD3554	Approved
0.76	Intermediate Similarity	NPD9610	Approved
0.76	Intermediate Similarity	NPD310	Approved
0.76	Intermediate Similarity	NPD311	Approved
0.76	Intermediate Similarity	NPD314	Approved
0.76	Intermediate Similarity	NPD10	Approved
0.76	Intermediate Similarity	NPD9608	Approved
0.76	Intermediate Similarity	NPD309	Approved
0.76	Intermediate Similarity	NPD315	Approved
0.7536	Intermediate Similarity	NPD1820	Approved
0.7536	Intermediate Similarity	NPD4103	Phase 2
0.7536	Intermediate Similarity	NPD1817	Approved
0.7536	Intermediate Similarity	NPD4104	Clinical (unspecified phase)
0.7536	Intermediate Similarity	NPD1818	Approved
0.7536	Intermediate Similarity	NPD1819	Approved
0.7532	Intermediate Similarity	NPD2977	Approved
0.7532	Intermediate Similarity	NPD2978	Approved
0.7518	Intermediate Similarity	NPD4659	Approved
0.7465	Intermediate Similarity	NPD829	Discontinued
0.7464	Intermediate Similarity	NPD9634	Clinical (unspecified phase)
0.7464	Intermediate Similarity	NPD5311	Approved
0.7464	Intermediate Similarity	NPD5310	Approved
0.745	Intermediate Similarity	NPD3845	Phase 1
0.745	Intermediate Similarity	NPD2422	Clinical (unspecified phase)
0.7431	Intermediate Similarity	NPD3054	Approved
0.7431	Intermediate Similarity	NPD3052	Approved
0.7405	Intermediate Similarity	NPD9379	Approved
0.7405	Intermediate Similarity	NPD9377	Approved
0.7397	Intermediate Similarity	NPD9570	Approved
0.7394	Intermediate Similarity	NPD3056	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD5137	Approved
0.7365	Intermediate Similarity	NPD3060	Approved
0.7365	Intermediate Similarity	NPD3638	Discontinued
0.7343	Intermediate Similarity	NPD1423	Approved
0.7324	Intermediate Similarity	NPD3179	Approved
0.7324	Intermediate Similarity	NPD3180	Approved
0.7324	Intermediate Similarity	NPD3167	Approved
0.7324	Intermediate Similarity	NPD3165	Approved
0.7324	Intermediate Similarity	NPD3164	Approved
0.7324	Intermediate Similarity	NPD3166	Approved
0.7286	Intermediate Similarity	NPD1794	Approved
0.7273	Intermediate Similarity	NPD2028	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD5160	Discontinued
0.7248	Intermediate Similarity	NPD2460	Phase 3
0.7248	Intermediate Similarity	NPD2458	Approved
0.7248	Intermediate Similarity	NPD4162	Approved
0.7248	Intermediate Similarity	NPD2459	Approved
0.7237	Intermediate Similarity	NPD3536	Discontinued
0.7237	Intermediate Similarity	NPD3645	Discontinued
0.723	Intermediate Similarity	NPD6809	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD3136	Phase 2
0.72	Intermediate Similarity	NPD9611	Approved
0.72	Intermediate Similarity	NPD9609	Approved
0.72	Intermediate Similarity	NPD9612	Approved
0.72	Intermediate Similarity	NPD7066	Clinical (unspecified phase)
0.7185	Intermediate Similarity	NPD9568	Approved
0.7183	Intermediate Similarity	NPD9569	Approved
0.7179	Intermediate Similarity	NPD7118	Clinical (unspecified phase)
0.7165	Intermediate Similarity	NPD854	Approved
0.7165	Intermediate Similarity	NPD855	Approved
0.7162	Intermediate Similarity	NPD3175	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD302	Approved
0.7133	Intermediate Similarity	NPD596	Approved
0.7133	Intermediate Similarity	NPD600	Approved
0.7123	Intermediate Similarity	NPD555	Phase 2
0.7114	Intermediate Similarity	NPD7978	Discontinued
0.7113	Intermediate Similarity	NPD558	Phase 2
0.7107	Intermediate Similarity	NPD4581	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD3162	Approved
0.7103	Intermediate Similarity	NPD3163	Approved
0.7103	Intermediate Similarity	NPD259	Phase 1
0.7095	Intermediate Similarity	NPD1753	Discontinued
0.709	Intermediate Similarity	NPD2234	Approved
0.709	Intermediate Similarity	NPD2228	Approved
0.709	Intermediate Similarity	NPD2229	Approved
0.708	Intermediate Similarity	NPD5303	Approved
0.708	Intermediate Similarity	NPD5304	Approved
0.708	Intermediate Similarity	NPD2227	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD2239	Approved
0.7047	Intermediate Similarity	NPD2240	Approved
0.7039	Intermediate Similarity	NPD8131	Suspended
0.7034	Intermediate Similarity	NPD864	Approved
0.7034	Intermediate Similarity	NPD865	Approved
0.7029	Intermediate Similarity	NPD1710	Approved
0.7025	Intermediate Similarity	NPD4227	Discontinued
0.6986	Remote Similarity	NPD554	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD6283	Phase 2
0.6966	Remote Similarity	NPD9537	Phase 1
0.6966	Remote Similarity	NPD9536	Phase 1
0.6943	Remote Similarity	NPD6056	Approved
0.6943	Remote Similarity	NPD6057	Approved
0.6939	Remote Similarity	NPD3597	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD3557	Approved
0.6937	Remote Similarity	NPD3559	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD3556	Approved
0.6937	Remote Similarity	NPD3560	Approved
0.6937	Remote Similarity	NPD3558	Approved
0.6912	Remote Similarity	NPD1791	Approved
0.6912	Remote Similarity	NPD1793	Approved
0.6908	Remote Similarity	NPD5062	Approved
0.6908	Remote Similarity	NPD4236	Phase 3
0.6908	Remote Similarity	NPD4237	Approved
0.6908	Remote Similarity	NPD5061	Approved
0.6908	Remote Similarity	NPD2976	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD1922	Discontinued
0.6903	Remote Similarity	NPD3158	Phase 1
0.6903	Remote Similarity	NPD3157	Approved
0.689	Remote Similarity	NPD4652	Approved
0.6884	Remote Similarity	NPD828	Approved
0.6879	Remote Similarity	NPD3687	Approved
0.6879	Remote Similarity	NPD5351	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD5350	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD3686	Approved
0.6875	Remote Similarity	NPD257	Approved
0.6875	Remote Similarity	NPD258	Approved
0.6875	Remote Similarity	NPD6818	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD7451	Discontinued
0.6871	Remote Similarity	NPD2041	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD2042	Clinical (unspecified phase)
0.6861	Remote Similarity	NPD255	Approved
0.6861	Remote Similarity	NPD256	Approved
0.6859	Remote Similarity	NPD7527	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD52	Approved
0.6859	Remote Similarity	NPD7526	Approved
0.6839	Remote Similarity	NPD2421	Approved
0.6839	Remote Similarity	NPD2420	Approved
0.6824	Remote Similarity	NPD825	Approved
0.6824	Remote Similarity	NPD826	Approved
0.6818	Remote Similarity	NPD1444	Approved
0.6818	Remote Similarity	NPD2677	Approved
0.6818	Remote Similarity	NPD1445	Approved
0.6818	Remote Similarity	NPD5241	Discontinued
0.6795	Remote Similarity	NPD3985	Discontinued
0.6795	Remote Similarity	NPD6419	Discontinued
0.6791	Remote Similarity	NPD550	Approved
0.6791	Remote Similarity	NPD551	Approved
0.6788	Remote Similarity	NPD595	Approved
0.6788	Remote Similarity	NPD593	Approved
0.6784	Remote Similarity	NPD5895	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD3122	Phase 3
0.6772	Remote Similarity	NPD814	Clinical (unspecified phase)
0.677	Remote Similarity	NPD5772	Approved
0.677	Remote Similarity	NPD3465	Clinical (unspecified phase)
0.677	Remote Similarity	NPD5773	Approved
0.6768	Remote Similarity	NPD4666	Phase 3
0.6759	Remote Similarity	NPD2195	Approved
0.6759	Remote Similarity	NPD2194	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