NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	279.09
Volume:	266.038
LogP:	1.474
LogD:	1.643
LogS:	-2.496
# Rotatable Bonds:	7
TPSA:	128.09
# H-Bond Aceptor:	8
# H-Bond Donor:	4
# Rings:	1
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.44
Synthetic Accessibility Score:	2.364
Fsp3:	0.167
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.289
MDCK Permeability:	2.8084289169783005e-06
Pgp-inhibitor:	0.0
Pgp-substrate:	0.009
Human Intestinal Absorption (HIA):	0.028
20% Bioavailability (F20%):	0.02
30% Bioavailability (F30%):	0.14

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.09
Plasma Protein Binding (PPB):	89.64546966552734%
Volume Distribution (VD):	0.188
Pgp-substrate:	8.193610191345215%

ADMET: Metabolism

CYP1A2-inhibitor:	0.029
CYP1A2-substrate:	0.029
CYP2C19-inhibitor:	0.098
CYP2C19-substrate:	0.041
CYP2C9-inhibitor:	0.129
CYP2C9-substrate:	0.649
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.105
CYP3A4-inhibitor:	0.05
CYP3A4-substrate:	0.016

ADMET: Excretion

Clearance (CL):	1.924
Half-life (T1/2):	0.956

ADMET: Toxicity

hERG Blockers:	0.112
Human Hepatotoxicity (H-HT):	0.122
Drug-inuced Liver Injury (DILI):	0.898
AMES Toxicity:	0.025
Rat Oral Acute Toxicity:	0.038
Maximum Recommended Daily Dose:	0.004
Skin Sensitization:	0.514
Carcinogencity:	0.025
Eye Corrosion:	0.004
Eye Irritation:	0.323
Respiratory Toxicity:	0.628

Download Data

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

Natural Product: NPC259678

Natural Product ID:	NPC259678
*Common Name:**	Farylhydrazone A
IUPAC Name:	2-[(2E)-2-[1-(carboxymethylamino)-1-oxopropan-2-ylidene]hydrazinyl]benzoic acid
Synonyms:	Farylhydrazone A
Standard InCHIKey:	XWKNZWMZVKJEKJ-VGOFMYFVSA-N
Standard InCHI:	InChI=1S/C12H13N3O5/c1-7(11(18)13-6-10(16)17)14-15-9-5-3-2-4-8(9)12(19)20/h2-5,15H,6H2,1H3,(H,13,18)(H,16,17)(H,19,20)/b14-7+
SMILES:	OC(=O)CN=C(/C(=N/Nc1ccccc1C(=O)O)/C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1669193
PubChem CID:	50994062
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:0001189] N-acyl-alpha amino acids and derivatives [CHEMONTID:0002402] N-acyl-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
NPO10809	Isaria farinosa	Species	Cordycipitaceae	Eukaryota	Cordyceps-colonizing isolate of Isaria farinosa	n.a.	n.a.	PMID[19572613]
NPO10809	Isaria farinosa	Species	Cordycipitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21158423]
NPO10809	Isaria farinosa	Species	Cordycipitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21495659]
NPO10809	Isaria farinosa	Species	Cordycipitaceae	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
Cell Line	2
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	>	150000.0	nM	PMID[463309]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	120000.0	nM	PMID[463309]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IC50	>	150000.0	nM	PMID[463309]
NPT1118	Organism	Streptococcus pneumoniae	Streptococcus pneumoniae	IC50	>	150000.0	nM	PMID[463309]

☑ 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 NPC259678 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	203
0.1-0.2	2332
0.2-0.3	10156
0.3-0.4	11832
0.4-0.5	14269
0.5-0.6	3490
0.6-0.7	375
0.7-0.8	33
0.8-0.85	5
0.85-0.9	0
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9485	High Similarity	NPC181527
0.8235	Intermediate Similarity	NPC130931
0.8163	Intermediate Similarity	NPC43477
0.8125	Intermediate Similarity	NPC253476
0.8038	Intermediate Similarity	NPC189116
0.7872	Intermediate Similarity	NPC226794
0.7817	Intermediate Similarity	NPC205946
0.7708	Intermediate Similarity	NPC58827
0.7708	Intermediate Similarity	NPC72473
0.7708	Intermediate Similarity	NPC307437
0.7682	Intermediate Similarity	NPC316202
0.7655	Intermediate Similarity	NPC122235
0.76	Intermediate Similarity	NPC159722
0.7584	Intermediate Similarity	NPC173295
0.7571	Intermediate Similarity	NPC229353
0.7468	Intermediate Similarity	NPC314287
0.7465	Intermediate Similarity	NPC150323
0.7405	Intermediate Similarity	NPC241392
0.7362	Intermediate Similarity	NPC27904
0.7233	Intermediate Similarity	NPC300596
0.7233	Intermediate Similarity	NPC237649
0.72	Intermediate Similarity	NPC314098
0.7171	Intermediate Similarity	NPC91615
0.7143	Intermediate Similarity	NPC287358
0.7143	Intermediate Similarity	NPC43218
0.7135	Intermediate Similarity	NPC8467
0.7133	Intermediate Similarity	NPC477432
0.7097	Intermediate Similarity	NPC469828
0.7097	Intermediate Similarity	NPC319645
0.7089	Intermediate Similarity	NPC323798
0.7078	Intermediate Similarity	NPC122542
0.7063	Intermediate Similarity	NPC315829
0.7029	Intermediate Similarity	NPC37584
0.7024	Intermediate Similarity	NPC471130
0.702	Intermediate Similarity	NPC194562
0.7006	Intermediate Similarity	NPC88970
0.6982	Remote Similarity	NPC182131
0.6974	Remote Similarity	NPC316746
0.6962	Remote Similarity	NPC472241
0.6946	Remote Similarity	NPC322644
0.6943	Remote Similarity	NPC242933
0.6943	Remote Similarity	NPC472243
0.6937	Remote Similarity	NPC472242
0.6933	Remote Similarity	NPC314278
0.6923	Remote Similarity	NPC122553
0.6914	Remote Similarity	NPC475685
0.6906	Remote Similarity	NPC172170
0.6894	Remote Similarity	NPC478039
0.6893	Remote Similarity	NPC471742
0.6857	Remote Similarity	NPC256268
0.6831	Remote Similarity	NPC329011
0.68	Remote Similarity	NPC219848
0.68	Remote Similarity	NPC317758
0.6784	Remote Similarity	NPC41717
0.6778	Remote Similarity	NPC278434
0.6759	Remote Similarity	NPC197470
0.6748	Remote Similarity	NPC254798
0.6742	Remote Similarity	NPC243058
0.673	Remote Similarity	NPC314252
0.673	Remote Similarity	NPC181526
0.6711	Remote Similarity	NPC322433
0.6709	Remote Similarity	NPC316574
0.6705	Remote Similarity	NPC9475
0.6704	Remote Similarity	NPC203635
0.6686	Remote Similarity	NPC154478
0.6686	Remote Similarity	NPC475594
0.6685	Remote Similarity	NPC473815
0.6667	Remote Similarity	NPC314186
0.6667	Remote Similarity	NPC474584
0.6667	Remote Similarity	NPC27581
0.6648	Remote Similarity	NPC471743
0.6648	Remote Similarity	NPC475607
0.6648	Remote Similarity	NPC470317
0.6646	Remote Similarity	NPC301702
0.6645	Remote Similarity	NPC474926
0.663	Remote Similarity	NPC90415
0.6619	Remote Similarity	NPC164859
0.6614	Remote Similarity	NPC471944
0.6612	Remote Similarity	NPC471195
0.6612	Remote Similarity	NPC471196
0.661	Remote Similarity	NPC474081
0.661	Remote Similarity	NPC315631
0.6608	Remote Similarity	NPC475983
0.6603	Remote Similarity	NPC476685
0.6603	Remote Similarity	NPC476687
0.6603	Remote Similarity	NPC476689
0.6596	Remote Similarity	NPC327481
0.659	Remote Similarity	NPC278887
0.6585	Remote Similarity	NPC324445
0.6584	Remote Similarity	NPC85443
0.6581	Remote Similarity	NPC325651
0.6581	Remote Similarity	NPC472245
0.6577	Remote Similarity	NPC319950
0.6571	Remote Similarity	NPC273532
0.6568	Remote Similarity	NPC84317
0.6566	Remote Similarity	NPC144691
0.6562	Remote Similarity	NPC315224
0.6559	Remote Similarity	NPC476256
0.6559	Remote Similarity	NPC259791
0.6559	Remote Similarity	NPC476212
0.6559	Remote Similarity	NPC476207
0.6559	Remote Similarity	NPC476205
0.6559	Remote Similarity	NPC476206
0.6559	Remote Similarity	NPC476257
0.6559	Remote Similarity	NPC476129
0.6556	Remote Similarity	NPC469831
0.6536	Remote Similarity	NPC4974
0.6529	Remote Similarity	NPC153694
0.6529	Remote Similarity	NPC211525
0.6528	Remote Similarity	NPC319579
0.6527	Remote Similarity	NPC314223
0.6524	Remote Similarity	NPC476218
0.6524	Remote Similarity	NPC108804
0.6522	Remote Similarity	NPC313293
0.6522	Remote Similarity	NPC12730
0.6519	Remote Similarity	NPC469829
0.6516	Remote Similarity	NPC150863
0.6503	Remote Similarity	NPC469830
0.6497	Remote Similarity	NPC40364
0.6494	Remote Similarity	NPC127362
0.6489	Remote Similarity	NPC141454
0.6486	Remote Similarity	NPC138370
0.648	Remote Similarity	NPC474041
0.648	Remote Similarity	NPC475761
0.6474	Remote Similarity	NPC314431
0.6467	Remote Similarity	NPC221873
0.6463	Remote Similarity	NPC470550
0.6463	Remote Similarity	NPC205652
0.6463	Remote Similarity	NPC130797
0.6443	Remote Similarity	NPC470786
0.6436	Remote Similarity	NPC108847
0.6429	Remote Similarity	NPC470343
0.6429	Remote Similarity	NPC207851
0.6429	Remote Similarity	NPC472244
0.6424	Remote Similarity	NPC179605
0.6424	Remote Similarity	NPC279385
0.642	Remote Similarity	NPC471778
0.6416	Remote Similarity	NPC476231
0.6405	Remote Similarity	NPC35996
0.64	Remote Similarity	NPC314992
0.6398	Remote Similarity	NPC92803
0.6395	Remote Similarity	NPC263709
0.6395	Remote Similarity	NPC310403
0.6395	Remote Similarity	NPC148468
0.6395	Remote Similarity	NPC243673
0.6395	Remote Similarity	NPC63210
0.6395	Remote Similarity	NPC97380
0.6393	Remote Similarity	NPC282103
0.6392	Remote Similarity	NPC207428
0.6392	Remote Similarity	NPC326966
0.6392	Remote Similarity	NPC225400
0.6383	Remote Similarity	NPC178681
0.6382	Remote Similarity	NPC103292
0.6379	Remote Similarity	NPC204867
0.6378	Remote Similarity	NPC18890
0.6376	Remote Similarity	NPC2265
0.6376	Remote Similarity	NPC147957
0.6373	Remote Similarity	NPC165599
0.6369	Remote Similarity	NPC280807
0.6369	Remote Similarity	NPC226662
0.6368	Remote Similarity	NPC474916
0.6364	Remote Similarity	NPC470894
0.6364	Remote Similarity	NPC136002
0.6359	Remote Similarity	NPC472538
0.6359	Remote Similarity	NPC471155
0.6354	Remote Similarity	NPC98864
0.6344	Remote Similarity	NPC83111
0.6344	Remote Similarity	NPC144381
0.6343	Remote Similarity	NPC52059
0.6343	Remote Similarity	NPC470069
0.6327	Remote Similarity	NPC270241
0.6322	Remote Similarity	NPC289776
0.6322	Remote Similarity	NPC199737
0.6322	Remote Similarity	NPC133470
0.6322	Remote Similarity	NPC191863
0.6319	Remote Similarity	NPC475962
0.6316	Remote Similarity	NPC114808
0.6313	Remote Similarity	NPC470548
0.6313	Remote Similarity	NPC303225
0.6313	Remote Similarity	NPC248862
0.6312	Remote Similarity	NPC184437
0.6306	Remote Similarity	NPC259098
0.6306	Remote Similarity	NPC209389
0.6306	Remote Similarity	NPC197680
0.6304	Remote Similarity	NPC3371
0.6304	Remote Similarity	NPC477391
0.6299	Remote Similarity	NPC254698
0.6296	Remote Similarity	NPC202812
0.6287	Remote Similarity	NPC470579
0.6283	Remote Similarity	NPC248782
0.628	Remote Similarity	NPC471574
0.628	Remote Similarity	NPC2823
0.6276	Remote Similarity	NPC244741
0.6273	Remote Similarity	NPC300299
0.6271	Remote Similarity	NPC470971
0.6267	Remote Similarity	NPC106551
0.6267	Remote Similarity	NPC281686
0.6267	Remote Similarity	NPC188867
0.6266	Remote Similarity	NPC478147
0.6263	Remote Similarity	NPC309845

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 NPC259678 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	138
0.1-0.2	530
0.2-0.3	1111
0.3-0.4	1357
0.4-0.5	3625
0.5-0.6	2067
0.6-0.7	301
0.7-0.8	21
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
0.7582	Intermediate Similarity	NPD1625	Approved
0.7566	Intermediate Similarity	NPD9477	Approved
0.7516	Intermediate Similarity	NPD1189	Approved
0.7484	Intermediate Similarity	NPD2360	Approved
0.7465	Intermediate Similarity	NPD9272	Approved
0.7342	Intermediate Similarity	NPD4888	Discontinued
0.732	Intermediate Similarity	NPD1626	Approved
0.7292	Intermediate Similarity	NPD9693	Approved
0.7292	Intermediate Similarity	NPD9692	Approved
0.7279	Intermediate Similarity	NPD1593	Approved
0.7266	Intermediate Similarity	NPD181	Approved
0.725	Intermediate Similarity	NPD1230	Approved
0.7241	Intermediate Similarity	NPD6163	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD1514	Discontinued
0.7114	Intermediate Similarity	NPD698	Approved
0.7114	Intermediate Similarity	NPD701	Approved
0.7097	Intermediate Similarity	NPD1110	Approved
0.7097	Intermediate Similarity	NPD3170	Approved
0.7097	Intermediate Similarity	NPD1109	Approved
0.7095	Intermediate Similarity	NPD1574	Approved
0.7071	Intermediate Similarity	NPD9508	Approved
0.707	Intermediate Similarity	NPD168	Phase 1
0.707	Intermediate Similarity	NPD6414	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD167	Phase 2
0.7067	Intermediate Similarity	NPD663	Approved
0.7067	Intermediate Similarity	NPD662	Approved
0.7067	Intermediate Similarity	NPD658	Approved
0.7067	Intermediate Similarity	NPD656	Approved
0.7067	Intermediate Similarity	NPD659	Approved
0.7047	Intermediate Similarity	NPD553	Approved
0.7047	Intermediate Similarity	NPD9567	Approved
0.7047	Intermediate Similarity	NPD552	Approved
0.7027	Intermediate Similarity	NPD182	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD661	Approved
0.7027	Intermediate Similarity	NPD660	Approved
0.7027	Intermediate Similarity	NPD657	Approved
0.7027	Intermediate Similarity	NPD655	Approved
0.6975	Remote Similarity	NPD2737	Clinical (unspecified phase)
0.697	Remote Similarity	NPD2672	Discontinued
0.6946	Remote Similarity	NPD4311	Approved
0.6944	Remote Similarity	NPD5042	Phase 1
0.6941	Remote Similarity	NPD2821	Approved
0.6928	Remote Similarity	NPD212	Discontinued
0.6914	Remote Similarity	NPD1664	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD1210	Approved
0.6867	Remote Similarity	NPD2836	Approved
0.686	Remote Similarity	NPD1165	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD4077	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD6359	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD1874	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD1348	Approved
0.6758	Remote Similarity	NPD5077	Approved
0.6758	Remote Similarity	NPD5076	Approved
0.6757	Remote Similarity	NPD6161	Approved
0.6757	Remote Similarity	NPD6162	Approved
0.6748	Remote Similarity	NPD1802	Approved
0.6748	Remote Similarity	NPD1801	Approved
0.6728	Remote Similarity	NPD2887	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD1079	Discontinued
0.6711	Remote Similarity	NPD9540	Approved
0.6709	Remote Similarity	NPD9279	Approved
0.6708	Remote Similarity	NPD1195	Approved
0.6707	Remote Similarity	NPD4161	Discontinued
0.6687	Remote Similarity	NPD9274	Approved
0.6687	Remote Similarity	NPD9278	Suspended
0.6687	Remote Similarity	NPD9275	Approved
0.6687	Remote Similarity	NPD9276	Approved
0.6685	Remote Similarity	NPD4948	Discontinued
0.6667	Remote Similarity	NPD951	Approved
0.6667	Remote Similarity	NPD9509	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1211	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1196	Approved
0.6667	Remote Similarity	NPD1208	Approved
0.6646	Remote Similarity	NPD9277	Approved
0.6646	Remote Similarity	NPD75	Approved
0.6645	Remote Similarity	NPD1036	Approved
0.6629	Remote Similarity	NPD5445	Approved
0.6623	Remote Similarity	NPD1781	Discontinued
0.661	Remote Similarity	NPD3965	Phase 1
0.6609	Remote Similarity	NPD2369	Discontinued
0.6606	Remote Similarity	NPD7528	Approved
0.6604	Remote Similarity	NPD1532	Approved
0.6604	Remote Similarity	NPD4214	Discontinued
0.6596	Remote Similarity	NPD1499	Phase 3
0.6591	Remote Similarity	NPD2359	Approved
0.6579	Remote Similarity	NPD9539	Approved
0.6579	Remote Similarity	NPD9541	Approved
0.6562	Remote Similarity	NPD12	Approved
0.6562	Remote Similarity	NPD13	Approved
0.6562	Remote Similarity	NPD700	Approved
0.6562	Remote Similarity	NPD699	Approved
0.6562	Remote Similarity	NPD697	Approved
0.6561	Remote Similarity	NPD1527	Phase 2
0.6554	Remote Similarity	NPD2361	Approved
0.6548	Remote Similarity	NPD5086	Approved
0.6545	Remote Similarity	NPD1543	Discontinued
0.6541	Remote Similarity	NPD7569	Approved
0.6541	Remote Similarity	NPD7570	Approved
0.6533	Remote Similarity	NPD1362	Clinical (unspecified phase)
0.6525	Remote Similarity	NPD1040	Phase 2
0.6524	Remote Similarity	NPD6017	Discontinued
0.6519	Remote Similarity	NPD7546	Discontinued
0.6509	Remote Similarity	NPD3684	Discontinued
0.6509	Remote Similarity	NPD1092	Approved
0.6509	Remote Similarity	NPD1093	Approved
0.6507	Remote Similarity	NPD1681	Approved
0.6507	Remote Similarity	NPD1682	Approved
0.6507	Remote Similarity	NPD1680	Approved
0.6506	Remote Similarity	NPD979	Approved
0.65	Remote Similarity	NPD2670	Approved
0.6497	Remote Similarity	NPD9471	Clinical (unspecified phase)
0.6497	Remote Similarity	NPD3502	Discovery
0.6491	Remote Similarity	NPD4335	Clinical (unspecified phase)
0.649	Remote Similarity	NPD1236	Phase 3
0.6471	Remote Similarity	NPD2366	Approved
0.6471	Remote Similarity	NPD6913	Approved
0.6467	Remote Similarity	NPD5748	Phase 2
0.6467	Remote Similarity	NPD4504	Clinical (unspecified phase)
0.6463	Remote Similarity	NPD1968	Approved
0.6463	Remote Similarity	NPD1967	Approved
0.6461	Remote Similarity	NPD2083	Clinical (unspecified phase)
0.646	Remote Similarity	NPD4158	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD1107	Approved
0.6458	Remote Similarity	NPD1108	Approved
0.6455	Remote Similarity	NPD5856	Discontinued
0.6452	Remote Similarity	NPD5937	Approved
0.6433	Remote Similarity	NPD1070	Approved
0.6433	Remote Similarity	NPD486	Clinical (unspecified phase)
0.6433	Remote Similarity	NPD3136	Phase 2
0.6433	Remote Similarity	NPD1069	Approved
0.6415	Remote Similarity	NPD1531	Approved
0.6409	Remote Similarity	NPD3178	Discontinued
0.6408	Remote Similarity	NPD564	Approved
0.6408	Remote Similarity	NPD563	Approved
0.6404	Remote Similarity	NPD5466	Approved
0.64	Remote Similarity	NPD2217	Approved
0.64	Remote Similarity	NPD2218	Phase 2
0.6395	Remote Similarity	NPD23	Approved
0.6387	Remote Similarity	NPD6302	Clinical (unspecified phase)
0.6387	Remote Similarity	NPD797	Clinical (unspecified phase)
0.6379	Remote Similarity	NPD1631	Approved
0.6378	Remote Similarity	NPD2792	Approved
0.6375	Remote Similarity	NPD2791	Discontinued
0.6374	Remote Similarity	NPD7105	Phase 1
0.6364	Remote Similarity	NPD8146	Phase 2
0.6364	Remote Similarity	NPD6657	Clinical (unspecified phase)
0.6359	Remote Similarity	NPD3154	Approved
0.6359	Remote Similarity	NPD6292	Clinical (unspecified phase)
0.6359	Remote Similarity	NPD3153	Approved
0.6348	Remote Similarity	NPD3952	Approved
0.6348	Remote Similarity	NPD3951	Phase 3
0.6348	Remote Similarity	NPD3953	Clinical (unspecified phase)
0.6341	Remote Similarity	NPD2365	Approved
0.634	Remote Similarity	NPD6323	Clinical (unspecified phase)
0.6339	Remote Similarity	NPD5923	Phase 1
0.6337	Remote Similarity	NPD3589	Clinical (unspecified phase)
0.6331	Remote Similarity	NPD5982	Phase 2
0.633	Remote Similarity	NPD7429	Clinical (unspecified phase)
0.6329	Remote Similarity	NPD1619	Phase 3
0.6329	Remote Similarity	NPD4738	Phase 2
0.6328	Remote Similarity	NPD7795	Phase 2
0.6322	Remote Similarity	NPD738	Approved
0.6319	Remote Similarity	NPD4707	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD4979	Clinical (unspecified phase)
0.6313	Remote Similarity	NPD6613	Clinical (unspecified phase)
0.631	Remote Similarity	NPD4432	Discontinued
0.6303	Remote Similarity	NPD2820	Phase 3
0.6303	Remote Similarity	NPD5024	Approved
0.6299	Remote Similarity	NPD5108	Clinical (unspecified phase)
0.6298	Remote Similarity	NPD5398	Clinical (unspecified phase)
0.629	Remote Similarity	NPD7855	Clinical (unspecified phase)
0.628	Remote Similarity	NPD3434	Clinical (unspecified phase)
0.6276	Remote Similarity	NPD476	Approved
0.6273	Remote Similarity	NPD1228	Phase 2
0.6273	Remote Similarity	NPD2470	Clinical (unspecified phase)
0.6271	Remote Similarity	NPD2037	Approved
0.6271	Remote Similarity	NPD2844	Phase 3
0.6269	Remote Similarity	NPD6733	Discontinued
0.6267	Remote Similarity	NPD733	Approved
0.6267	Remote Similarity	NPD732	Approved
0.6267	Remote Similarity	NPD9568	Approved
0.6259	Remote Similarity	NPD9566	Approved
0.6258	Remote Similarity	NPD6865	Phase 2
0.6258	Remote Similarity	NPD6864	Phase 2
0.625	Remote Similarity	NPD5430	Discontinued
0.625	Remote Similarity	NPD1541	Approved
0.625	Remote Similarity	NPD1340	Discontinued
0.625	Remote Similarity	NPD2212	Approved
0.625	Remote Similarity	NPD6682	Clinical (unspecified phase)
0.625	Remote Similarity	NPD2210	Approved
0.6243	Remote Similarity	NPD3812	Clinical (unspecified phase)
0.6243	Remote Similarity	NPD5498	Phase 2
0.6236	Remote Similarity	NPD1573	Approved
0.6236	Remote Similarity	NPD1575	Approved
0.6236	Remote Similarity	NPD1839	Phase 1
0.6235	Remote Similarity	NPD3528	Clinical (unspecified phase)
0.6235	Remote Similarity	NPD6817	Clinical (unspecified phase)
0.6231	Remote Similarity	NPD5416	Discontinued
0.6231	Remote Similarity	NPD683	Approved
0.6228	Remote Similarity	NPD1518	Clinical (unspecified phase)

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