NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	392.96
Volume:	290.237
LogP:	-1.047
LogD:	0.04
LogS:	0.363
# Rotatable Bonds:	6
TPSA:	49.36
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	1
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.691
Synthetic Accessibility Score:	3.483
Fsp3:	0.462
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:	-5.326
MDCK Permeability:	3.452829332672991e-05
Pgp-inhibitor:	0.007
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.645
20% Bioavailability (F20%):	0.937
30% Bioavailability (F30%):	0.99

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.129
Plasma Protein Binding (PPB):	81.90971374511719%
Volume Distribution (VD):	0.692
Pgp-substrate:	35.819091796875%

ADMET: Metabolism

CYP1A2-inhibitor:	0.203
CYP1A2-substrate:	0.792
CYP2C19-inhibitor:	0.039
CYP2C19-substrate:	0.057
CYP2C9-inhibitor:	0.008
CYP2C9-substrate:	0.502
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.787
CYP3A4-inhibitor:	0.005
CYP3A4-substrate:	0.067

ADMET: Excretion

Clearance (CL):	1.801
Half-life (T1/2):	0.903

ADMET: Toxicity

hERG Blockers:	0.01
Human Hepatotoxicity (H-HT):	0.695
Drug-inuced Liver Injury (DILI):	0.02
AMES Toxicity:	0.001
Rat Oral Acute Toxicity:	0.181
Maximum Recommended Daily Dose:	0.505
Skin Sensitization:	0.029
Carcinogencity:	0.141
Eye Corrosion:	0.01
Eye Irritation:	0.075
Respiratory Toxicity:	0.022

Download Data

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

Natural Product: NPC195902

Natural Product ID:	NPC195902
*Common Name:**	Purpuroine B
IUPAC Name:	(2R)-4-(2,4-dibromophenoxy)-2-(trimethylazaniumyl)butanoate
Synonyms:	Purpuroine B
Standard InCHIKey:	WSYAJSUDDFHTBT-LLVKDONJSA-N
Standard InCHI:	InChI=1S/C13H17Br2NO3/c1-16(2,3)11(13(17)18)6-7-19-12-5-4-9(14)8-10(12)15/h4-5,8,11H,6-7H2,1-3H3/t11-/m1/s1
SMILES:	C[N+](C)(C)[C@H](CCOc1ccc(cc1Br)Br)C(=O)[O-]
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2204066
PubChem CID:	71454033
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0000013] Amino acids, peptides, and analogues [CHEMONTID:0000347] Amino acids and derivatives [CHEMONTID:0000060] Alpha amino acids and derivatives [CHEMONTID:0002404] Alpha amino acids [CHEMONTID:0004145] D-alpha-amino acids

*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
NPO9305	Iotrochota purpurea	Species	Iotrochotidae	Eukaryota	n.a.	n.a.	n.a.	PMID[10924179]
NPO9305	Iotrochota purpurea	Species	Iotrochotidae	Eukaryota	n.a.	n.a.	n.a.	PMID[23131412]
NPO9305	Iotrochota purpurea	Species	Iotrochotidae	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	3

Activity Type	# Activity
Individual Protein	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1371	Individual Protein	Cyclin-dependent kinase 2	Homo sapiens	IC50	>	50.0	ug.mL-1	PMID[568187]
NPT13	Individual Protein	Tyrosine-protein kinase LCK	Homo sapiens	IC50	=	12.76	ug.mL-1	PMID[568187]
NPT831	Individual Protein	Serine/threonine-protein kinase PLK1	Homo sapiens	IC50	>	50.0	ug.mL-1	PMID[568187]

☑ 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 NPC195902 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	197
0.1-0.2	3874
0.2-0.3	13319
0.3-0.4	7358
0.4-0.5	15493
0.5-0.6	2276
0.6-0.7	168
0.7-0.8	8
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9836	High Similarity	NPC280736
0.96	High Similarity	NPC70485
0.8156	Intermediate Similarity	NPC142803
0.7692	Intermediate Similarity	NPC470709
0.75	Intermediate Similarity	NPC40321
0.7391	Intermediate Similarity	NPC110131
0.7317	Intermediate Similarity	NPC313918
0.7231	Intermediate Similarity	NPC95977
0.7222	Intermediate Similarity	NPC319933
0.7123	Intermediate Similarity	NPC470249
0.709	Intermediate Similarity	NPC162294
0.7039	Intermediate Similarity	NPC296085
0.7015	Intermediate Similarity	NPC221301
0.7	Intermediate Similarity	NPC308571
0.6968	Remote Similarity	NPC47672
0.6943	Remote Similarity	NPC233926
0.6928	Remote Similarity	NPC71629
0.6912	Remote Similarity	NPC264379
0.6892	Remote Similarity	NPC470248
0.6842	Remote Similarity	NPC135349
0.6831	Remote Similarity	NPC272463
0.6812	Remote Similarity	NPC71186
0.68	Remote Similarity	NPC470250
0.68	Remote Similarity	NPC128877
0.6795	Remote Similarity	NPC258222
0.6783	Remote Similarity	NPC124776
0.669	Remote Similarity	NPC116562
0.6667	Remote Similarity	NPC170824
0.6624	Remote Similarity	NPC76412
0.6623	Remote Similarity	NPC78530
0.6622	Remote Similarity	NPC470392
0.6582	Remote Similarity	NPC109968
0.6577	Remote Similarity	NPC243404
0.6527	Remote Similarity	NPC477255
0.6525	Remote Similarity	NPC44270
0.6525	Remote Similarity	NPC86007
0.6522	Remote Similarity	NPC156311
0.6513	Remote Similarity	NPC474673
0.6503	Remote Similarity	NPC173511
0.6503	Remote Similarity	NPC235166
0.6503	Remote Similarity	NPC88733
0.649	Remote Similarity	NPC235633
0.649	Remote Similarity	NPC470471
0.6486	Remote Similarity	NPC135173
0.6466	Remote Similarity	NPC17537
0.6466	Remote Similarity	NPC473855
0.6462	Remote Similarity	NPC307039
0.6462	Remote Similarity	NPC132725
0.6454	Remote Similarity	NPC104124
0.6443	Remote Similarity	NPC11449
0.6438	Remote Similarity	NPC469711
0.6438	Remote Similarity	NPC136112
0.6438	Remote Similarity	NPC141739
0.6438	Remote Similarity	NPC320242
0.6434	Remote Similarity	NPC153580
0.6434	Remote Similarity	NPC226737
0.6434	Remote Similarity	NPC47769
0.6434	Remote Similarity	NPC299939
0.6434	Remote Similarity	NPC196371
0.6418	Remote Similarity	NPC176971
0.6414	Remote Similarity	NPC68350
0.6414	Remote Similarity	NPC81149
0.6414	Remote Similarity	NPC197576
0.6414	Remote Similarity	NPC230013
0.6414	Remote Similarity	NPC131940
0.6405	Remote Similarity	NPC470470
0.6391	Remote Similarity	NPC283546
0.637	Remote Similarity	NPC157473
0.637	Remote Similarity	NPC1744
0.637	Remote Similarity	NPC151530
0.637	Remote Similarity	NPC163019
0.6364	Remote Similarity	NPC63317
0.6364	Remote Similarity	NPC41232
0.6345	Remote Similarity	NPC175520
0.6345	Remote Similarity	NPC295879
0.6345	Remote Similarity	NPC159866
0.6345	Remote Similarity	NPC25134
0.6345	Remote Similarity	NPC97157
0.6345	Remote Similarity	NPC64130
0.6343	Remote Similarity	NPC128730
0.6338	Remote Similarity	NPC191194
0.6299	Remote Similarity	NPC213471
0.6296	Remote Similarity	NPC41594
0.6288	Remote Similarity	NPC107101
0.6286	Remote Similarity	NPC477254
0.6276	Remote Similarity	NPC474375
0.6276	Remote Similarity	NPC137922
0.6276	Remote Similarity	NPC40302
0.6271	Remote Similarity	NPC80337
0.6257	Remote Similarity	NPC248822
0.625	Remote Similarity	NPC180207
0.6242	Remote Similarity	NPC122359
0.6242	Remote Similarity	NPC78061
0.6242	Remote Similarity	NPC159987
0.6242	Remote Similarity	NPC470247
0.6241	Remote Similarity	NPC307425
0.6225	Remote Similarity	NPC178301
0.6222	Remote Similarity	NPC473393
0.6222	Remote Similarity	NPC238115
0.6214	Remote Similarity	NPC26524
0.6211	Remote Similarity	NPC214239
0.621	Remote Similarity	NPC23837
0.6204	Remote Similarity	NPC291837
0.6203	Remote Similarity	NPC470472
0.6201	Remote Similarity	NPC230539
0.6194	Remote Similarity	NPC179686
0.6184	Remote Similarity	NPC274732
0.6184	Remote Similarity	NPC307123
0.6184	Remote Similarity	NPC97870
0.6184	Remote Similarity	NPC247018
0.6184	Remote Similarity	NPC474753
0.6181	Remote Similarity	NPC234956
0.6178	Remote Similarity	NPC204546
0.6176	Remote Similarity	NPC326447
0.6172	Remote Similarity	NPC318429
0.6159	Remote Similarity	NPC259554
0.6133	Remote Similarity	NPC64066
0.6124	Remote Similarity	NPC121571
0.6124	Remote Similarity	NPC8093
0.6115	Remote Similarity	NPC25067
0.6115	Remote Similarity	NPC88868
0.6115	Remote Similarity	NPC231251
0.6111	Remote Similarity	NPC159916
0.6111	Remote Similarity	NPC293424
0.6104	Remote Similarity	NPC303993
0.6098	Remote Similarity	NPC73132
0.6098	Remote Similarity	NPC235033
0.6098	Remote Similarity	NPC471235
0.6093	Remote Similarity	NPC283079
0.6081	Remote Similarity	NPC255253
0.608	Remote Similarity	NPC125306
0.6076	Remote Similarity	NPC474128
0.6069	Remote Similarity	NPC98748
0.6067	Remote Similarity	NPC45728
0.6066	Remote Similarity	NPC475843
0.6066	Remote Similarity	NPC124576
0.6058	Remote Similarity	NPC1065
0.6044	Remote Similarity	NPC102245
0.6043	Remote Similarity	NPC149545
0.604	Remote Similarity	NPC213414
0.604	Remote Similarity	NPC236265
0.6034	Remote Similarity	NPC259071
0.6034	Remote Similarity	NPC77435
0.6029	Remote Similarity	NPC109637
0.6027	Remote Similarity	NPC31314
0.6027	Remote Similarity	NPC193193
0.6026	Remote Similarity	NPC307682
0.6025	Remote Similarity	NPC189908
0.6011	Remote Similarity	NPC474678
0.6011	Remote Similarity	NPC471338
0.6	Remote Similarity	NPC51633
0.5989	Remote Similarity	NPC473450
0.5987	Remote Similarity	NPC318591
0.5987	Remote Similarity	NPC231163
0.5986	Remote Similarity	NPC322569
0.5984	Remote Similarity	NPC252149
0.5974	Remote Similarity	NPC259017
0.5973	Remote Similarity	NPC328267
0.5973	Remote Similarity	NPC320287
0.5972	Remote Similarity	NPC33717
0.597	Remote Similarity	NPC471576
0.5967	Remote Similarity	NPC147847
0.5962	Remote Similarity	NPC196708
0.5959	Remote Similarity	NPC256369
0.5957	Remote Similarity	NPC245552
0.5957	Remote Similarity	NPC233238
0.5956	Remote Similarity	NPC192596
0.5949	Remote Similarity	NPC317741
0.5949	Remote Similarity	NPC241086
0.5949	Remote Similarity	NPC318984
0.5949	Remote Similarity	NPC282087
0.5949	Remote Similarity	NPC318028
0.5949	Remote Similarity	NPC259800
0.5949	Remote Similarity	NPC328137
0.5948	Remote Similarity	NPC206183
0.5948	Remote Similarity	NPC222684
0.5944	Remote Similarity	NPC87563
0.5944	Remote Similarity	NPC235250
0.5941	Remote Similarity	NPC472923
0.5938	Remote Similarity	NPC206876
0.593	Remote Similarity	NPC186617
0.5929	Remote Similarity	NPC234639
0.5918	Remote Similarity	NPC321133
0.5918	Remote Similarity	NPC263835
0.5915	Remote Similarity	NPC280760
0.5912	Remote Similarity	NPC108875
0.5912	Remote Similarity	NPC2518
0.5912	Remote Similarity	NPC83289
0.5912	Remote Similarity	NPC189724
0.5912	Remote Similarity	NPC212850
0.5912	Remote Similarity	NPC38079
0.5912	Remote Similarity	NPC174607
0.5909	Remote Similarity	NPC143450
0.5906	Remote Similarity	NPC296202
0.5904	Remote Similarity	NPC470710
0.5903	Remote Similarity	NPC51345
0.5896	Remote Similarity	NPC473693
0.5896	Remote Similarity	NPC471568
0.5894	Remote Similarity	NPC170749
0.5891	Remote Similarity	NPC157213

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 NPC195902 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	144
0.1-0.2	854
0.2-0.3	2244
0.3-0.4	2891
0.4-0.5	2138
0.5-0.6	780
0.6-0.7	98
0.7-0.8	1
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7231	Intermediate Similarity	NPD2673	Approved
0.7231	Intermediate Similarity	NPD2671	Approved
0.7143	Intermediate Similarity	NPD1318	Phase 2
0.7063	Intermediate Similarity	NPD5746	Approved
0.7	Intermediate Similarity	NPD5373	Approved
0.7	Intermediate Similarity	NPD5374	Approved
0.6966	Remote Similarity	NPD5745	Approved
0.6897	Remote Similarity	NPD3374	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD5689	Approved
0.6892	Remote Similarity	NPD5688	Approved
0.68	Remote Similarity	NPD6032	Approved
0.6763	Remote Similarity	NPD1797	Approved
0.6763	Remote Similarity	NPD1798	Approved
0.6757	Remote Similarity	NPD4622	Approved
0.6757	Remote Similarity	NPD4618	Approved
0.6689	Remote Similarity	NPD2240	Approved
0.6689	Remote Similarity	NPD2239	Approved
0.6619	Remote Similarity	NPD1102	Approved
0.6619	Remote Similarity	NPD1103	Approved
0.6575	Remote Similarity	NPD2237	Approved
0.6558	Remote Similarity	NPD4487	Clinical (unspecified phase)
0.6536	Remote Similarity	NPD5865	Clinical (unspecified phase)
0.6513	Remote Similarity	NPD2164	Clinical (unspecified phase)
0.65	Remote Similarity	NPD1408	Clinical (unspecified phase)
0.6493	Remote Similarity	NPD9624	Approved
0.6486	Remote Similarity	NPD5163	Phase 2
0.6478	Remote Similarity	NPD5586	Clinical (unspecified phase)
0.6475	Remote Similarity	NPD2557	Approved
0.6467	Remote Similarity	NPD1393	Approved
0.6454	Remote Similarity	NPD7534	Approved
0.6454	Remote Similarity	NPD7533	Approved
0.6438	Remote Similarity	NPD1817	Approved
0.6438	Remote Similarity	NPD1820	Approved
0.6438	Remote Similarity	NPD1818	Approved
0.6438	Remote Similarity	NPD1819	Approved
0.6438	Remote Similarity	NPD1794	Approved
0.6434	Remote Similarity	NPD3447	Discontinued
0.6429	Remote Similarity	NPD3596	Phase 2
0.6408	Remote Similarity	NPD2595	Approved
0.6408	Remote Similarity	NPD2594	Approved
0.64	Remote Similarity	NPD4870	Approved
0.6398	Remote Similarity	NPD2052	Approved
0.6358	Remote Similarity	NPD2053	Approved
0.6358	Remote Similarity	NPD22	Approved
0.6338	Remote Similarity	NPD6580	Approved
0.6338	Remote Similarity	NPD6581	Approved
0.6319	Remote Similarity	NPD2513	Approved
0.6312	Remote Similarity	NPD4186	Clinical (unspecified phase)
0.6294	Remote Similarity	NPD6830	Clinical (unspecified phase)
0.6294	Remote Similarity	NPD6382	Discontinued
0.6284	Remote Similarity	NPD2987	Approved
0.6284	Remote Similarity	NPD2990	Approved
0.6282	Remote Similarity	NPD2897	Discontinued
0.628	Remote Similarity	NPD2515	Approved
0.628	Remote Similarity	NPD3007	Approved
0.6267	Remote Similarity	NPD9718	Approved
0.6267	Remote Similarity	NPD3179	Approved
0.6267	Remote Similarity	NPD3180	Approved
0.6267	Remote Similarity	NPD3166	Approved
0.6267	Remote Similarity	NPD3164	Approved
0.6267	Remote Similarity	NPD3165	Approved
0.6267	Remote Similarity	NPD3167	Approved
0.6258	Remote Similarity	NPD4477	Approved
0.6258	Remote Similarity	NPD4476	Approved
0.6242	Remote Similarity	NPD5266	Clinical (unspecified phase)
0.6242	Remote Similarity	NPD2250	Discontinued
0.6216	Remote Similarity	NPD1770	Clinical (unspecified phase)
0.6216	Remote Similarity	NPD4098	Discontinued
0.6214	Remote Similarity	NPD592	Approved
0.6214	Remote Similarity	NPD594	Approved
0.6211	Remote Similarity	NPD2184	Approved
0.6211	Remote Similarity	NPD2183	Approved
0.6207	Remote Similarity	NPD155	Clinical (unspecified phase)
0.619	Remote Similarity	NPD6582	Phase 2
0.619	Remote Similarity	NPD6583	Phase 3
0.6184	Remote Similarity	NPD1423	Approved
0.6184	Remote Similarity	NPD2245	Discovery
0.6181	Remote Similarity	NPD3443	Approved
0.6181	Remote Similarity	NPD3444	Approved
0.6181	Remote Similarity	NPD3445	Approved
0.6181	Remote Similarity	NPD5585	Approved
0.6176	Remote Similarity	NPD3134	Approved
0.6173	Remote Similarity	NPD8330	Clinical (unspecified phase)
0.6172	Remote Similarity	NPD9365	Approved
0.6169	Remote Similarity	NPD4579	Clinical (unspecified phase)
0.6149	Remote Similarity	NPD196	Phase 1
0.6144	Remote Similarity	NPD3142	Approved
0.6144	Remote Similarity	NPD756	Suspended
0.6144	Remote Similarity	NPD3140	Approved
0.6143	Remote Similarity	NPD2496	Approved
0.6143	Remote Similarity	NPD769	Approved
0.6143	Remote Similarity	NPD2497	Approved
0.6139	Remote Similarity	NPD2976	Clinical (unspecified phase)
0.6138	Remote Similarity	NPD1010	Approved
0.6138	Remote Similarity	NPD2554	Approved
0.6138	Remote Similarity	NPD2556	Approved
0.6133	Remote Similarity	NPD4993	Discontinued
0.6131	Remote Similarity	NPD1358	Approved
0.6125	Remote Similarity	NPD6667	Approved
0.6125	Remote Similarity	NPD6666	Approved
0.6121	Remote Similarity	NPD6677	Suspended
0.6118	Remote Similarity	NPD1048	Approved
0.6118	Remote Similarity	NPD3056	Clinical (unspecified phase)
0.6115	Remote Similarity	NPD3656	Approved
0.6111	Remote Similarity	NPD2676	Approved
0.6111	Remote Similarity	NPD2675	Approved
0.6093	Remote Similarity	NPD3537	Clinical (unspecified phase)
0.6081	Remote Similarity	NPD1421	Approved
0.6081	Remote Similarity	NPD6540	Phase 3
0.6081	Remote Similarity	NPD1420	Approved
0.6081	Remote Similarity	NPD6539	Approved
0.6081	Remote Similarity	NPD6543	Approved
0.6081	Remote Similarity	NPD6542	Approved
0.6078	Remote Similarity	NPD3162	Approved
0.6078	Remote Similarity	NPD3163	Approved
0.6074	Remote Similarity	NPD7131	Phase 3
0.6069	Remote Similarity	NPD3049	Approved
0.6067	Remote Similarity	NPD7018	Phase 2
0.6067	Remote Similarity	NPD6584	Phase 3
0.6056	Remote Similarity	NPD593	Approved
0.6056	Remote Similarity	NPD595	Approved
0.6051	Remote Similarity	NPD1725	Approved
0.6049	Remote Similarity	NPD5348	Clinical (unspecified phase)
0.6049	Remote Similarity	NPD3536	Discontinued
0.6049	Remote Similarity	NPD3146	Approved
0.6049	Remote Similarity	NPD3688	Clinical (unspecified phase)
0.604	Remote Similarity	NPD6538	Approved
0.604	Remote Similarity	NPD6541	Approved
0.6039	Remote Similarity	NPD3597	Clinical (unspecified phase)
0.6039	Remote Similarity	NPD4101	Phase 1
0.6027	Remote Similarity	NPD2423	Clinical (unspecified phase)
0.6027	Remote Similarity	NPD1778	Approved
0.6026	Remote Similarity	NPD1536	Approved
0.6026	Remote Similarity	NPD2200	Suspended
0.6	Remote Similarity	NPD2486	Discontinued
0.6	Remote Similarity	NPD1562	Clinical (unspecified phase)
0.5988	Remote Similarity	NPD5356	Approved
0.5988	Remote Similarity	NPD5355	Approved
0.5987	Remote Similarity	NPD2156	Approved
0.5987	Remote Similarity	NPD2155	Approved
0.5987	Remote Similarity	NPD2154	Approved
0.5975	Remote Similarity	NPD7596	Clinical (unspecified phase)
0.5974	Remote Similarity	NPD3532	Approved
0.5974	Remote Similarity	NPD3531	Approved
0.5974	Remote Similarity	NPD4474	Approved
0.5974	Remote Similarity	NPD3530	Approved
0.5974	Remote Similarity	NPD4475	Approved
0.5973	Remote Similarity	NPD3685	Discontinued
0.5973	Remote Similarity	NPD4359	Approved
0.5973	Remote Similarity	NPD2428	Approved
0.5973	Remote Similarity	NPD2429	Approved
0.5972	Remote Similarity	NPD5291	Approved
0.5972	Remote Similarity	NPD5292	Approved
0.5962	Remote Similarity	NPD2653	Approved
0.5962	Remote Similarity	NPD3054	Approved
0.5962	Remote Similarity	NPD3052	Approved
0.5962	Remote Similarity	NPD2224	Approved
0.5962	Remote Similarity	NPD2223	Approved
0.5952	Remote Similarity	NPD7972	Discontinued
0.5949	Remote Similarity	NPD1538	Phase 1
0.5949	Remote Similarity	NPD1519	Approved
0.5949	Remote Similarity	NPD1422	Approved
0.5949	Remote Similarity	NPD3175	Clinical (unspecified phase)
0.5949	Remote Similarity	NPD1537	Approved
0.5946	Remote Similarity	NPD776	Approved
0.5939	Remote Similarity	NPD3686	Approved
0.5939	Remote Similarity	NPD3687	Approved
0.5935	Remote Similarity	NPD2203	Discontinued
0.5929	Remote Similarity	NPD556	Approved
0.5928	Remote Similarity	NPD6386	Approved
0.5928	Remote Similarity	NPD6385	Approved
0.5926	Remote Similarity	NPD5295	Discontinued
0.5924	Remote Similarity	NPD1520	Approved
0.5924	Remote Similarity	NPD1521	Approved
0.5921	Remote Similarity	NPD455	Discontinued
0.5918	Remote Similarity	NPD2667	Approved
0.5918	Remote Similarity	NPD2668	Approved
0.5915	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.5915	Remote Similarity	NPD5535	Approved
0.5915	Remote Similarity	NPD821	Approved
0.5909	Remote Similarity	NPD7294	Phase 1
0.5909	Remote Similarity	NPD1336	Approved
0.5906	Remote Similarity	NPD2233	Approved
0.5906	Remote Similarity	NPD2232	Approved
0.5906	Remote Similarity	NPD2230	Approved
0.5904	Remote Similarity	NPD2651	Approved
0.5904	Remote Similarity	NPD2649	Approved
0.5904	Remote Similarity	NPD8158	Clinical (unspecified phase)
0.5894	Remote Similarity	NPD6362	Approved
0.5891	Remote Similarity	NPD9295	Approved
0.5886	Remote Similarity	NPD3152	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD291	Approved
0.5882	Remote Similarity	NPD2614	Approved
0.5882	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.5878	Remote Similarity	NPD3847	Discontinued
0.5878	Remote Similarity	NPD3496	Discontinued
0.5878	Remote Similarity	NPD3294	Phase 2
0.5874	Remote Similarity	NPD1241	Discontinued
0.5874	Remote Similarity	NPD9069	Phase 1
0.5871	Remote Similarity	NPD7265	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