NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	470.87
Volume:	309.52
LogP:	-0.179
LogD:	0.211
LogS:	0.19
# Rotatable Bonds:	6
TPSA:	49.36
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	1
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.597
Synthetic Accessibility Score:	3.691
Fsp3:	0.462
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.295
MDCK Permeability:	2.0214194591972046e-05
Pgp-inhibitor:	0.009
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.701
20% Bioavailability (F20%):	0.945
30% Bioavailability (F30%):	0.989

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.108
Plasma Protein Binding (PPB):	93.1603012084961%
Volume Distribution (VD):	0.697
Pgp-substrate:	18.249197006225586%

ADMET: Metabolism

CYP1A2-inhibitor:	0.349
CYP1A2-substrate:	0.789
CYP2C19-inhibitor:	0.03
CYP2C19-substrate:	0.057
CYP2C9-inhibitor:	0.01
CYP2C9-substrate:	0.384
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.573
CYP3A4-inhibitor:	0.007
CYP3A4-substrate:	0.053

ADMET: Excretion

Clearance (CL):	1.707
Half-life (T1/2):	0.908

ADMET: Toxicity

hERG Blockers:	0.008
Human Hepatotoxicity (H-HT):	0.743
Drug-inuced Liver Injury (DILI):	0.02
AMES Toxicity:	0.001
Rat Oral Acute Toxicity:	0.341
Maximum Recommended Daily Dose:	0.656
Skin Sensitization:	0.027
Carcinogencity:	0.275
Eye Corrosion:	0.004
Eye Irritation:	0.047
Respiratory Toxicity:	0.026

Download Data

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

Natural Product: NPC280736

Natural Product ID:	NPC280736
*Common Name:**	Purpuroine A
IUPAC Name:	(2R)-4-(2,4,6-tribromophenoxy)-2-(trimethylazaniumyl)butanoate
Synonyms:	Purpuroine A
Standard InCHIKey:	PKQKGGKFHVXXND-LLVKDONJSA-N
Standard InCHI:	InChI=1S/C13H16Br3NO3/c1-17(2,3)11(13(18)19)4-5-20-12-9(15)6-8(14)7-10(12)16/h6-7,11H,4-5H2,1-3H3/t11-/m1/s1
SMILES:	C[N+](C)(C)[C@H](CCOc1c(cc(cc1Br)Br)Br)C(=O)[O-]
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2204065
PubChem CID:	71450398
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	4

Activity Type	# Activity
Individual Protein	3
Organism	1

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[486395]
NPT13	Individual Protein	Tyrosine-protein kinase LCK	Homo sapiens	IC50	=	2.35	ug.mL-1	PMID[486395]
NPT831	Individual Protein	Serine/threonine-protein kinase PLK1	Homo sapiens	IC50	>	50.0	ug.mL-1	PMID[486395]
NPT87	Organism	Aspergillus fumigatus	Aspergillus fumigatus	IC50	=	28.58	ug.mL-1	PMID[486395]

☑ 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 NPC280736 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	194
0.1-0.2	3756
0.2-0.3	13555
0.3-0.4	7926
0.4-0.5	15449
0.5-0.6	1669
0.6-0.7	138
0.7-0.8	6
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	NPC195902
0.9756	High Similarity	NPC70485
0.8273	Intermediate Similarity	NPC142803
0.7676	Intermediate Similarity	NPC470709
0.7606	Intermediate Similarity	NPC40321
0.75	Intermediate Similarity	NPC110131
0.7154	Intermediate Similarity	NPC313918
0.7095	Intermediate Similarity	NPC308571
0.7077	Intermediate Similarity	NPC95977
0.7063	Intermediate Similarity	NPC319933
0.6992	Remote Similarity	NPC221301
0.6986	Remote Similarity	NPC470248
0.6986	Remote Similarity	NPC470249
0.694	Remote Similarity	NPC162294
0.6929	Remote Similarity	NPC272463
0.6908	Remote Similarity	NPC296085
0.6908	Remote Similarity	NPC71629
0.6892	Remote Similarity	NPC470250
0.6892	Remote Similarity	NPC128877
0.6889	Remote Similarity	NPC264379
0.6879	Remote Similarity	NPC124776
0.6839	Remote Similarity	NPC47672
0.6821	Remote Similarity	NPC135349
0.6815	Remote Similarity	NPC233926
0.6788	Remote Similarity	NPC71186
0.6786	Remote Similarity	NPC116562
0.6667	Remote Similarity	NPC258222
0.6667	Remote Similarity	NPC243404
0.6643	Remote Similarity	NPC170824
0.6606	Remote Similarity	NPC477255
0.6603	Remote Similarity	NPC76412
0.66	Remote Similarity	NPC474673
0.6577	Remote Similarity	NPC235633
0.6575	Remote Similarity	NPC135173
0.6519	Remote Similarity	NPC469711
0.6494	Remote Similarity	NPC78530
0.6486	Remote Similarity	NPC470392
0.6479	Remote Similarity	NPC88733
0.6479	Remote Similarity	NPC235166
0.6479	Remote Similarity	NPC173511
0.6467	Remote Similarity	NPC470471
0.6456	Remote Similarity	NPC109968
0.6429	Remote Similarity	NPC104124
0.6398	Remote Similarity	NPC156311
0.6389	Remote Similarity	NPC230013
0.6389	Remote Similarity	NPC197576
0.6389	Remote Similarity	NPC68350
0.6389	Remote Similarity	NPC131940
0.6389	Remote Similarity	NPC81149
0.6383	Remote Similarity	NPC86007
0.6383	Remote Similarity	NPC44270
0.6382	Remote Similarity	NPC470470
0.6358	Remote Similarity	NPC477254
0.6345	Remote Similarity	NPC163019
0.6345	Remote Similarity	NPC1744
0.6338	Remote Similarity	NPC41232
0.6338	Remote Similarity	NPC63317
0.6338	Remote Similarity	NPC180207
0.6323	Remote Similarity	NPC470247
0.6316	Remote Similarity	NPC17537
0.6316	Remote Similarity	NPC473855
0.6309	Remote Similarity	NPC11449
0.6308	Remote Similarity	NPC307039
0.6308	Remote Similarity	NPC132725
0.6301	Remote Similarity	NPC320242
0.6301	Remote Similarity	NPC136112
0.6301	Remote Similarity	NPC141739
0.6294	Remote Similarity	NPC299939
0.6294	Remote Similarity	NPC196371
0.6294	Remote Similarity	NPC153580
0.6294	Remote Similarity	NPC226737
0.6294	Remote Similarity	NPC47769
0.6269	Remote Similarity	NPC176971
0.625	Remote Similarity	NPC40302
0.625	Remote Similarity	NPC80337
0.625	Remote Similarity	NPC137922
0.6241	Remote Similarity	NPC283546
0.6222	Remote Similarity	NPC157473
0.6222	Remote Similarity	NPC151530
0.6207	Remote Similarity	NPC64130
0.6207	Remote Similarity	NPC295879
0.6207	Remote Similarity	NPC175520
0.6207	Remote Similarity	NPC159866
0.6207	Remote Similarity	NPC97157
0.6207	Remote Similarity	NPC25134
0.6197	Remote Similarity	NPC191194
0.6194	Remote Similarity	NPC128730
0.6193	Remote Similarity	NPC121571
0.6193	Remote Similarity	NPC8093
0.618	Remote Similarity	NPC230539
0.6178	Remote Similarity	NPC470472
0.6169	Remote Similarity	NPC213471
0.6148	Remote Similarity	NPC41594
0.6145	Remote Similarity	NPC248822
0.6138	Remote Similarity	NPC474375
0.6136	Remote Similarity	NPC107101
0.6133	Remote Similarity	NPC475843
0.6111	Remote Similarity	NPC64066
0.6107	Remote Similarity	NPC122359
0.6107	Remote Similarity	NPC159987
0.6107	Remote Similarity	NPC78061
0.6102	Remote Similarity	NPC259071
0.6102	Remote Similarity	NPC77435
0.6093	Remote Similarity	NPC178301
0.609	Remote Similarity	NPC307425
0.6087	Remote Similarity	NPC214239
0.6077	Remote Similarity	NPC471338
0.6077	Remote Similarity	NPC474678
0.6074	Remote Similarity	NPC473393
0.6074	Remote Similarity	NPC238115
0.6071	Remote Similarity	NPC26524
0.6058	Remote Similarity	NPC291837
0.6053	Remote Similarity	NPC274732
0.6053	Remote Similarity	NPC474753
0.6053	Remote Similarity	NPC247018
0.6053	Remote Similarity	NPC307123
0.6053	Remote Similarity	NPC259017
0.6053	Remote Similarity	NPC97870
0.6051	Remote Similarity	NPC204546
0.6048	Remote Similarity	NPC23837
0.6045	Remote Similarity	NPC179686
0.6042	Remote Similarity	NPC234956
0.604	Remote Similarity	NPC45728
0.6029	Remote Similarity	NPC326447
0.6022	Remote Similarity	NPC102245
0.6016	Remote Similarity	NPC318429
0.6014	Remote Similarity	NPC236265
0.6014	Remote Similarity	NPC259554
0.5976	Remote Similarity	NPC235033
0.5976	Remote Similarity	NPC471235
0.5976	Remote Similarity	NPC73132
0.5974	Remote Similarity	NPC303993
0.5972	Remote Similarity	NPC159916
0.5972	Remote Similarity	NPC293424
0.5971	Remote Similarity	NPC88868
0.5971	Remote Similarity	NPC25067
0.5971	Remote Similarity	NPC231251
0.596	Remote Similarity	NPC283079
0.5959	Remote Similarity	NPC56634
0.5952	Remote Similarity	NPC252149
0.5949	Remote Similarity	NPC474128
0.5946	Remote Similarity	NPC105999
0.5946	Remote Similarity	NPC255253
0.5944	Remote Similarity	NPC147847
0.5931	Remote Similarity	NPC98748
0.5921	Remote Similarity	NPC206183
0.5921	Remote Similarity	NPC222684
0.592	Remote Similarity	NPC125306
0.5912	Remote Similarity	NPC1065
0.5906	Remote Similarity	NPC213414
0.5902	Remote Similarity	NPC124576
0.5902	Remote Similarity	NPC227953
0.5901	Remote Similarity	NPC189908
0.5899	Remote Similarity	NPC149545
0.5897	Remote Similarity	NPC307682
0.5896	Remote Similarity	NPC90245
0.589	Remote Similarity	NPC31314
0.589	Remote Similarity	NPC193193
0.5889	Remote Similarity	NPC174607
0.5886	Remote Similarity	NPC143450
0.5886	Remote Similarity	NPC475976
0.5882	Remote Similarity	NPC109637
0.5882	Remote Similarity	NPC471337
0.5882	Remote Similarity	NPC473450
0.587	Remote Similarity	NPC202866
0.586	Remote Similarity	NPC231163
0.586	Remote Similarity	NPC318591
0.5852	Remote Similarity	NPC51633
0.585	Remote Similarity	NPC322569
0.5839	Remote Similarity	NPC328267
0.5839	Remote Similarity	NPC320287
0.5833	Remote Similarity	NPC196708
0.5833	Remote Similarity	NPC33717
0.5824	Remote Similarity	NPC472923
0.5823	Remote Similarity	NPC318984
0.5823	Remote Similarity	NPC326860
0.5823	Remote Similarity	NPC259800
0.5823	Remote Similarity	NPC197239
0.5823	Remote Similarity	NPC328137
0.5823	Remote Similarity	NPC317741
0.5823	Remote Similarity	NPC241086
0.5823	Remote Similarity	NPC282087
0.5823	Remote Similarity	NPC318028
0.5822	Remote Similarity	NPC256369
0.5821	Remote Similarity	NPC471576
0.5819	Remote Similarity	NPC475120
0.5816	Remote Similarity	NPC245552
0.5816	Remote Similarity	NPC233238
0.5814	Remote Similarity	NPC186617
0.5811	Remote Similarity	NPC26285
0.5809	Remote Similarity	NPC192596
0.5804	Remote Similarity	NPC235250
0.5804	Remote Similarity	NPC87563
0.5798	Remote Similarity	NPC123140
0.5786	Remote Similarity	NPC212850
0.5786	Remote Similarity	NPC234639
0.5786	Remote Similarity	NPC81137
0.5786	Remote Similarity	NPC83289
0.5786	Remote Similarity	NPC189724
0.5783	Remote Similarity	NPC470710

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 NPC280736 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	142
0.1-0.2	838
0.2-0.3	2329
0.3-0.4	2975
0.4-0.5	2109
0.5-0.6	693
0.6-0.7	64
0.7-0.8	0
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
0.7077	Intermediate Similarity	NPD2671	Approved
0.7077	Intermediate Similarity	NPD2673	Approved
0.7	Intermediate Similarity	NPD1318	Phase 2
0.6923	Remote Similarity	NPD5746	Approved
0.6846	Remote Similarity	NPD5373	Approved
0.6846	Remote Similarity	NPD5374	Approved
0.6828	Remote Similarity	NPD5745	Approved
0.6759	Remote Similarity	NPD3374	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD5688	Approved
0.6757	Remote Similarity	NPD5689	Approved
0.6667	Remote Similarity	NPD6032	Approved
0.6622	Remote Similarity	NPD4622	Approved
0.6622	Remote Similarity	NPD4618	Approved
0.6619	Remote Similarity	NPD1798	Approved
0.6619	Remote Similarity	NPD1797	Approved
0.6556	Remote Similarity	NPD2240	Approved
0.6556	Remote Similarity	NPD2239	Approved
0.6552	Remote Similarity	NPD2237	Approved
0.6475	Remote Similarity	NPD1103	Approved
0.6475	Remote Similarity	NPD1102	Approved
0.6429	Remote Similarity	NPD4487	Clinical (unspecified phase)
0.6405	Remote Similarity	NPD5865	Clinical (unspecified phase)
0.6382	Remote Similarity	NPD2164	Clinical (unspecified phase)
0.6357	Remote Similarity	NPD1408	Clinical (unspecified phase)
0.6352	Remote Similarity	NPD5586	Clinical (unspecified phase)
0.6351	Remote Similarity	NPD5163	Phase 2
0.6351	Remote Similarity	NPD9718	Approved
0.6343	Remote Similarity	NPD9624	Approved
0.6333	Remote Similarity	NPD1393	Approved
0.6331	Remote Similarity	NPD2557	Approved
0.6312	Remote Similarity	NPD7534	Approved
0.6312	Remote Similarity	NPD7533	Approved
0.6301	Remote Similarity	NPD1818	Approved
0.6301	Remote Similarity	NPD1817	Approved
0.6301	Remote Similarity	NPD1820	Approved
0.6301	Remote Similarity	NPD1794	Approved
0.6301	Remote Similarity	NPD1819	Approved
0.6294	Remote Similarity	NPD3447	Discontinued
0.6286	Remote Similarity	NPD3596	Phase 2
0.6273	Remote Similarity	NPD2052	Approved
0.6268	Remote Similarity	NPD2594	Approved
0.6268	Remote Similarity	NPD2595	Approved
0.6267	Remote Similarity	NPD4870	Approved
0.6235	Remote Similarity	NPD22	Approved
0.6235	Remote Similarity	NPD2053	Approved
0.6197	Remote Similarity	NPD6580	Approved
0.6197	Remote Similarity	NPD6581	Approved
0.6196	Remote Similarity	NPD2513	Approved
0.6188	Remote Similarity	NPD4186	Clinical (unspecified phase)
0.6187	Remote Similarity	NPD592	Approved
0.6187	Remote Similarity	NPD594	Approved
0.6159	Remote Similarity	NPD3007	Approved
0.6159	Remote Similarity	NPD2515	Approved
0.6154	Remote Similarity	NPD6382	Discontinued
0.6154	Remote Similarity	NPD6830	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD2897	Discontinued
0.6149	Remote Similarity	NPD2990	Approved
0.6149	Remote Similarity	NPD2987	Approved
0.6133	Remote Similarity	NPD3166	Approved
0.6133	Remote Similarity	NPD3167	Approved
0.6133	Remote Similarity	NPD3165	Approved
0.6133	Remote Similarity	NPD3180	Approved
0.6133	Remote Similarity	NPD3179	Approved
0.6133	Remote Similarity	NPD3164	Approved
0.6129	Remote Similarity	NPD4476	Approved
0.6129	Remote Similarity	NPD4477	Approved
0.6115	Remote Similarity	NPD2497	Approved
0.6115	Remote Similarity	NPD2496	Approved
0.6107	Remote Similarity	NPD5266	Clinical (unspecified phase)
0.6107	Remote Similarity	NPD2250	Discontinued
0.6087	Remote Similarity	NPD2675	Approved
0.6087	Remote Similarity	NPD2184	Approved
0.6087	Remote Similarity	NPD2183	Approved
0.6087	Remote Similarity	NPD2676	Approved
0.6081	Remote Similarity	NPD4098	Discontinued
0.6081	Remote Similarity	NPD1770	Clinical (unspecified phase)
0.6069	Remote Similarity	NPD155	Clinical (unspecified phase)
0.6054	Remote Similarity	NPD6583	Phase 3
0.6054	Remote Similarity	NPD6582	Phase 2
0.6053	Remote Similarity	NPD1423	Approved
0.6053	Remote Similarity	NPD2245	Discovery
0.6049	Remote Similarity	NPD8330	Clinical (unspecified phase)
0.6042	Remote Similarity	NPD3445	Approved
0.6042	Remote Similarity	NPD5585	Approved
0.6042	Remote Similarity	NPD3443	Approved
0.6042	Remote Similarity	NPD3444	Approved
0.6039	Remote Similarity	NPD4579	Clinical (unspecified phase)
0.6029	Remote Similarity	NPD3134	Approved
0.6016	Remote Similarity	NPD9365	Approved
0.6014	Remote Similarity	NPD196	Phase 1
0.6013	Remote Similarity	NPD756	Suspended
0.6013	Remote Similarity	NPD3142	Approved
0.6013	Remote Similarity	NPD2976	Clinical (unspecified phase)
0.6013	Remote Similarity	NPD3140	Approved
0.6	Remote Similarity	NPD2556	Approved
0.6	Remote Similarity	NPD769	Approved
0.6	Remote Similarity	NPD6677	Suspended
0.6	Remote Similarity	NPD6667	Approved
0.6	Remote Similarity	NPD6666	Approved
0.6	Remote Similarity	NPD1010	Approved
0.6	Remote Similarity	NPD2554	Approved
0.6	Remote Similarity	NPD4993	Discontinued
0.5987	Remote Similarity	NPD3056	Clinical (unspecified phase)
0.5987	Remote Similarity	NPD3656	Approved
0.5987	Remote Similarity	NPD1048	Approved
0.5985	Remote Similarity	NPD1358	Approved
0.596	Remote Similarity	NPD3537	Clinical (unspecified phase)
0.5951	Remote Similarity	NPD7131	Phase 3
0.5948	Remote Similarity	NPD3163	Approved
0.5948	Remote Similarity	NPD3162	Approved
0.5946	Remote Similarity	NPD6540	Phase 3
0.5946	Remote Similarity	NPD6539	Approved
0.5946	Remote Similarity	NPD1421	Approved
0.5946	Remote Similarity	NPD1420	Approved
0.5946	Remote Similarity	NPD6543	Approved
0.5946	Remote Similarity	NPD6542	Approved
0.5944	Remote Similarity	NPD5292	Approved
0.5944	Remote Similarity	NPD5291	Approved
0.5933	Remote Similarity	NPD7018	Phase 2
0.5933	Remote Similarity	NPD6584	Phase 3
0.5931	Remote Similarity	NPD3049	Approved
0.5926	Remote Similarity	NPD3536	Discontinued
0.5926	Remote Similarity	NPD3146	Approved
0.5926	Remote Similarity	NPD5348	Clinical (unspecified phase)
0.5926	Remote Similarity	NPD3688	Clinical (unspecified phase)
0.5924	Remote Similarity	NPD1725	Approved
0.5918	Remote Similarity	NPD776	Approved
0.5915	Remote Similarity	NPD593	Approved
0.5915	Remote Similarity	NPD595	Approved
0.5909	Remote Similarity	NPD2203	Discontinued
0.5909	Remote Similarity	NPD4101	Phase 1
0.5909	Remote Similarity	NPD3597	Clinical (unspecified phase)
0.5906	Remote Similarity	NPD6538	Approved
0.5906	Remote Similarity	NPD6541	Approved
0.5897	Remote Similarity	NPD2200	Suspended
0.5897	Remote Similarity	NPD1521	Approved
0.5897	Remote Similarity	NPD1520	Approved
0.5897	Remote Similarity	NPD1536	Approved
0.589	Remote Similarity	NPD2423	Clinical (unspecified phase)
0.589	Remote Similarity	NPD1778	Approved
0.5875	Remote Similarity	NPD1562	Clinical (unspecified phase)
0.5868	Remote Similarity	NPD5355	Approved
0.5868	Remote Similarity	NPD5356	Approved
0.5862	Remote Similarity	NPD2486	Discontinued
0.586	Remote Similarity	NPD2155	Approved
0.586	Remote Similarity	NPD2154	Approved
0.586	Remote Similarity	NPD2156	Approved
0.5849	Remote Similarity	NPD7596	Clinical (unspecified phase)
0.5844	Remote Similarity	NPD3531	Approved
0.5844	Remote Similarity	NPD3530	Approved
0.5844	Remote Similarity	NPD4475	Approved
0.5844	Remote Similarity	NPD3532	Approved
0.5844	Remote Similarity	NPD4474	Approved
0.5839	Remote Similarity	NPD2428	Approved
0.5839	Remote Similarity	NPD3685	Discontinued
0.5839	Remote Similarity	NPD2429	Approved
0.5839	Remote Similarity	NPD4359	Approved
0.5833	Remote Similarity	NPD3054	Approved
0.5833	Remote Similarity	NPD3052	Approved
0.5833	Remote Similarity	NPD7972	Discontinued
0.5833	Remote Similarity	NPD2653	Approved
0.5833	Remote Similarity	NPD2223	Approved
0.5833	Remote Similarity	NPD2224	Approved
0.5823	Remote Similarity	NPD1523	Approved
0.5823	Remote Similarity	NPD1519	Approved
0.5823	Remote Similarity	NPD3175	Clinical (unspecified phase)
0.5823	Remote Similarity	NPD1538	Phase 1
0.5823	Remote Similarity	NPD1522	Approved
0.5823	Remote Similarity	NPD1537	Approved
0.5823	Remote Similarity	NPD1422	Approved
0.5818	Remote Similarity	NPD3686	Approved
0.5818	Remote Similarity	NPD3687	Approved
0.5808	Remote Similarity	NPD6385	Approved
0.5808	Remote Similarity	NPD5889	Approved
0.5808	Remote Similarity	NPD6386	Approved
0.5808	Remote Similarity	NPD5890	Approved
0.5802	Remote Similarity	NPD5295	Discontinued
0.5799	Remote Similarity	NPD5353	Approved
0.5793	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.5789	Remote Similarity	NPD455	Discontinued
0.5787	Remote Similarity	NPD1298	Discontinued
0.5786	Remote Similarity	NPD5235	Approved
0.5786	Remote Similarity	NPD5237	Approved
0.5786	Remote Similarity	NPD5239	Approved
0.5786	Remote Similarity	NPD5240	Approved
0.5786	Remote Similarity	NPD5236	Approved
0.5786	Remote Similarity	NPD556	Approved
0.5783	Remote Similarity	NPD8158	Clinical (unspecified phase)
0.5783	Remote Similarity	NPD2649	Approved
0.5783	Remote Similarity	NPD2651	Approved
0.5782	Remote Similarity	NPD2667	Approved
0.5782	Remote Similarity	NPD2668	Approved
0.5779	Remote Similarity	NPD1336	Approved
0.5779	Remote Similarity	NPD7294	Phase 1
0.5775	Remote Similarity	NPD5535	Approved
0.5775	Remote Similarity	NPD821	Approved
0.5772	Remote Similarity	NPD2233	Approved
0.5772	Remote Similarity	NPD2230	Approved
0.5772	Remote Similarity	NPD2232	Approved
0.5762	Remote Similarity	NPD6362	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