NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	255.13
Volume:	278.301
LogP:	2.741
LogD:	2.945
LogS:	-3.394
# Rotatable Bonds:	6
TPSA:	38.33
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.892
Synthetic Accessibility Score:	1.334
Fsp3:	0.188
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:	-4.631
MDCK Permeability:	1.6095063983811997e-05
Pgp-inhibitor:	0.18
Pgp-substrate:	0.034
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.302
30% Bioavailability (F30%):	0.972

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.401
Plasma Protein Binding (PPB):	95.65613555908203%
Volume Distribution (VD):	0.975
Pgp-substrate:	2.966442346572876%

ADMET: Metabolism

CYP1A2-inhibitor:	0.952
CYP1A2-substrate:	0.889
CYP2C19-inhibitor:	0.963
CYP2C19-substrate:	0.357
CYP2C9-inhibitor:	0.896
CYP2C9-substrate:	0.898
CYP2D6-inhibitor:	0.927
CYP2D6-substrate:	0.884
CYP3A4-inhibitor:	0.699
CYP3A4-substrate:	0.433

ADMET: Excretion

Clearance (CL):	8.44
Half-life (T1/2):	0.622

ADMET: Toxicity

hERG Blockers:	0.592
Human Hepatotoxicity (H-HT):	0.515
Drug-inuced Liver Injury (DILI):	0.371
AMES Toxicity:	0.337
Rat Oral Acute Toxicity:	0.028
Maximum Recommended Daily Dose:	0.214
Skin Sensitization:	0.55
Carcinogencity:	0.214
Eye Corrosion:	0.003
Eye Irritation:	0.191
Respiratory Toxicity:	0.037

Download Data

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

Natural Product: NPC43275

Natural Product ID:	NPC43275
*Common Name:**	N-[2-(4-Methoxyphenyl)Ethyl]Benzamide
IUPAC Name:	N-[2-(4-methoxyphenyl)ethyl]benzamide
Synonyms:
Standard InCHIKey:	RAOWOXJDGFFKKD-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C16H17NO2/c1-19-15-9-7-13(8-10-15)11-12-17-16(18)14-5-3-2-4-6-14/h2-10H,11-12H2,1H3,(H,17,18)
SMILES:	COc1ccc(cc1)CCN=C(c1ccccc1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1497400
PubChem CID:	3083797
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000176] Benzoic acids and derivatives [CHEMONTID:0000178] Benzamides

*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
NPO7317	Citrus aurantium	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10606602]
NPO587	Saussurea stella	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17844995]
NPO7317	Citrus aurantium	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2017	Poa sphondylodes	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2017	Poa sphondylodes	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7317	Citrus aurantium	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7317	Citrus aurantium	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2017	Poa sphondylodes	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7317	Citrus aurantium	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO11564	Ruditapes philippinarum	Species	Veneridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO587	Saussurea stella	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9119	Pterocladiella capillacea	Species	Gelidiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7317	Citrus aurantium	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2017	Poa sphondylodes	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9593	Anoectochilus koshunensis	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21916.1	Herbertus juniperoideus subsp. acanthelius	Subspecies	Herbertaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO371	Courbonia virgata	n.a.	n.a.	n.a.	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
Potency	7

Activity Type	# Activity
Individual Protein	3
Organism	1
Others	1
Uncleic Acid	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT64	Individual Protein	ATPase family AAA domain-containing protein 5	Homo sapiens	Potency	n.a.	35481.3	nM	PMID[552574]
NPT484	Individual Protein	Luciferin 4-monooxygenase	Photinus pyralis	Potency	n.a.	26854.5	nM	PMID[552574]
NPT536	Uncleic Acid	microRNA 21	Homo sapiens	Potency	=	13091.8	nM	PMID[552574]
NPT2	Others	Unspecified		Potency	n.a.	11220.2	nM	PMID[552574]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	6573.3	nM	PMID[552574]
NPT8	Individual Protein	DNA polymerase iota	Homo sapiens	Potency	n.a.	89125.1	nM	PMID[552574]

☑ 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 NPC43275 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	142
0.1-0.2	1713
0.2-0.3	8324
0.3-0.4	9388
0.4-0.5	6349
0.5-0.6	11239
0.6-0.7	4735
0.7-0.8	715
0.8-0.85	66
0.85-0.9	20
0.9-0.95	5
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9407	High Similarity	NPC29477
0.9224	High Similarity	NPC263835
0.916	High Similarity	NPC95733
0.916	High Similarity	NPC62101
0.9076	High Similarity	NPC211218
0.8957	High Similarity	NPC303370
0.8938	High Similarity	NPC166837
0.8852	High Similarity	NPC301713
0.8839	High Similarity	NPC153690
0.8833	High Similarity	NPC471314
0.8833	High Similarity	NPC471315
0.878	High Similarity	NPC251571
0.872	High Similarity	NPC114102
0.871	High Similarity	NPC155838
0.8673	High Similarity	NPC24101
0.8673	High Similarity	NPC96224
0.8667	High Similarity	NPC83279
0.8655	High Similarity	NPC256369
0.8651	High Similarity	NPC214869
0.864	High Similarity	NPC195749
0.864	High Similarity	NPC52029
0.864	High Similarity	NPC35961
0.8583	High Similarity	NPC471308
0.8583	High Similarity	NPC289330
0.8583	High Similarity	NPC53596
0.8583	High Similarity	NPC160120
0.8583	High Similarity	NPC321133
0.8583	High Similarity	NPC17388
0.8496	Intermediate Similarity	NPC231705
0.8496	Intermediate Similarity	NPC113457
0.848	Intermediate Similarity	NPC153990
0.8435	Intermediate Similarity	NPC258056
0.8421	Intermediate Similarity	NPC142297
0.8362	Intermediate Similarity	NPC474149
0.8348	Intermediate Similarity	NPC309982
0.8333	Intermediate Similarity	NPC186898
0.8321	Intermediate Similarity	NPC204848
0.8321	Intermediate Similarity	NPC14600
0.8321	Intermediate Similarity	NPC312770
0.8321	Intermediate Similarity	NPC254610
0.8321	Intermediate Similarity	NPC160607
0.8321	Intermediate Similarity	NPC41473
0.8279	Intermediate Similarity	NPC41801
0.8258	Intermediate Similarity	NPC299583
0.8254	Intermediate Similarity	NPC218323
0.825	Intermediate Similarity	NPC258992
0.825	Intermediate Similarity	NPC82963
0.823	Intermediate Similarity	NPC178902
0.8217	Intermediate Similarity	NPC130595
0.8217	Intermediate Similarity	NPC471953
0.8217	Intermediate Similarity	NPC93882
0.819	Intermediate Similarity	NPC201959
0.819	Intermediate Similarity	NPC75440
0.819	Intermediate Similarity	NPC146530
0.8182	Intermediate Similarity	NPC311737
0.8182	Intermediate Similarity	NPC38458
0.8182	Intermediate Similarity	NPC323948
0.8167	Intermediate Similarity	NPC37302
0.8162	Intermediate Similarity	NPC313414
0.8154	Intermediate Similarity	NPC6854
0.8154	Intermediate Similarity	NPC313737
0.8154	Intermediate Similarity	NPC285078
0.8134	Intermediate Similarity	NPC474128
0.812	Intermediate Similarity	NPC474272
0.812	Intermediate Similarity	NPC296898
0.8092	Intermediate Similarity	NPC218530
0.8087	Intermediate Similarity	NPC42383
0.8083	Intermediate Similarity	NPC118202
0.8074	Intermediate Similarity	NPC100478
0.8074	Intermediate Similarity	NPC222039
0.806	Intermediate Similarity	NPC83289
0.806	Intermediate Similarity	NPC189724
0.806	Intermediate Similarity	NPC212850
0.8049	Intermediate Similarity	NPC268572
0.8034	Intermediate Similarity	NPC97811
0.8033	Intermediate Similarity	NPC283468
0.8029	Intermediate Similarity	NPC5462
0.8017	Intermediate Similarity	NPC317254
0.8015	Intermediate Similarity	NPC63628
0.8015	Intermediate Similarity	NPC178466
0.8	Intermediate Similarity	NPC308885
0.8	Intermediate Similarity	NPC12987
0.8	Intermediate Similarity	NPC474603
0.8	Intermediate Similarity	NPC35344
0.8	Intermediate Similarity	NPC141003
0.8	Intermediate Similarity	NPC255550
0.7971	Intermediate Similarity	NPC132771
0.7967	Intermediate Similarity	NPC122009
0.7965	Intermediate Similarity	NPC100870
0.7939	Intermediate Similarity	NPC470392
0.7931	Intermediate Similarity	NPC470393
0.7931	Intermediate Similarity	NPC211551
0.7926	Intermediate Similarity	NPC477838
0.7926	Intermediate Similarity	NPC477837
0.7923	Intermediate Similarity	NPC470706
0.792	Intermediate Similarity	NPC284078
0.792	Intermediate Similarity	NPC318357
0.791	Intermediate Similarity	NPC471316
0.7907	Intermediate Similarity	NPC191302
0.7907	Intermediate Similarity	NPC157740
0.7907	Intermediate Similarity	NPC99798
0.7879	Intermediate Similarity	NPC169766
0.7869	Intermediate Similarity	NPC464
0.7869	Intermediate Similarity	NPC185541
0.7863	Intermediate Similarity	NPC45191
0.7851	Intermediate Similarity	NPC26524
0.7846	Intermediate Similarity	NPC147247
0.7846	Intermediate Similarity	NPC246974
0.7845	Intermediate Similarity	NPC38079
0.7845	Intermediate Similarity	NPC108875
0.7842	Intermediate Similarity	NPC245974
0.7829	Intermediate Similarity	NPC156944
0.7829	Intermediate Similarity	NPC251466
0.7826	Intermediate Similarity	NPC300166
0.7826	Intermediate Similarity	NPC247298
0.782	Intermediate Similarity	NPC303993
0.7805	Intermediate Similarity	NPC229147
0.7805	Intermediate Similarity	NPC54507
0.7805	Intermediate Similarity	NPC19290
0.7805	Intermediate Similarity	NPC85292
0.7797	Intermediate Similarity	NPC186469
0.7788	Intermediate Similarity	NPC33168
0.7778	Intermediate Similarity	NPC193528
0.7778	Intermediate Similarity	NPC154899
0.7778	Intermediate Similarity	NPC233396
0.7778	Intermediate Similarity	NPC183262
0.7769	Intermediate Similarity	NPC291449
0.7769	Intermediate Similarity	NPC41331
0.7762	Intermediate Similarity	NPC18614
0.7761	Intermediate Similarity	NPC237227
0.776	Intermediate Similarity	NPC283760
0.7759	Intermediate Similarity	NPC305205
0.7759	Intermediate Similarity	NPC192596
0.7754	Intermediate Similarity	NPC78530
0.7752	Intermediate Similarity	NPC246133
0.7752	Intermediate Similarity	NPC207541
0.7752	Intermediate Similarity	NPC71105
0.7752	Intermediate Similarity	NPC170583
0.7752	Intermediate Similarity	NPC182147
0.7752	Intermediate Similarity	NPC152186
0.7748	Intermediate Similarity	NPC321956
0.7742	Intermediate Similarity	NPC474933
0.7739	Intermediate Similarity	NPC155847
0.7739	Intermediate Similarity	NPC289381
0.7734	Intermediate Similarity	NPC140359
0.7734	Intermediate Similarity	NPC328267
0.7734	Intermediate Similarity	NPC13020
0.773	Intermediate Similarity	NPC470935
0.773	Intermediate Similarity	NPC471032
0.7727	Intermediate Similarity	NPC476570
0.7724	Intermediate Similarity	NPC296526
0.7717	Intermediate Similarity	NPC474862
0.7712	Intermediate Similarity	NPC92623
0.7712	Intermediate Similarity	NPC135464
0.7699	Intermediate Similarity	NPC26244
0.7692	Intermediate Similarity	NPC52475
0.7692	Intermediate Similarity	NPC127402
0.768	Intermediate Similarity	NPC470626
0.768	Intermediate Similarity	NPC131118
0.7674	Intermediate Similarity	NPC300955
0.7672	Intermediate Similarity	NPC51633
0.7664	Intermediate Similarity	NPC77572
0.7661	Intermediate Similarity	NPC141090
0.766	Intermediate Similarity	NPC277857
0.766	Intermediate Similarity	NPC115144
0.7658	Intermediate Similarity	NPC71853
0.7647	Intermediate Similarity	NPC213471
0.7647	Intermediate Similarity	NPC251306
0.7643	Intermediate Similarity	NPC9373
0.7642	Intermediate Similarity	NPC228287
0.7642	Intermediate Similarity	NPC180508
0.7642	Intermediate Similarity	NPC142599
0.7634	Intermediate Similarity	NPC172403
0.7632	Intermediate Similarity	NPC473388
0.7626	Intermediate Similarity	NPC135349
0.7619	Intermediate Similarity	NPC310338
0.7619	Intermediate Similarity	NPC281298
0.7611	Intermediate Similarity	NPC151715
0.7611	Intermediate Similarity	NPC471581
0.7606	Intermediate Similarity	NPC153644
0.7603	Intermediate Similarity	NPC475852
0.76	Intermediate Similarity	NPC293619
0.76	Intermediate Similarity	NPC120075
0.7589	Intermediate Similarity	NPC290404
0.7586	Intermediate Similarity	NPC207675
0.7586	Intermediate Similarity	NPC212699
0.7581	Intermediate Similarity	NPC53906
0.7576	Intermediate Similarity	NPC469977
0.7568	Intermediate Similarity	NPC177844
0.7568	Intermediate Similarity	NPC8002
0.7568	Intermediate Similarity	NPC99886
0.7568	Intermediate Similarity	NPC259134
0.7565	Intermediate Similarity	NPC107619
0.7559	Intermediate Similarity	NPC242885
0.7559	Intermediate Similarity	NPC95614
0.7559	Intermediate Similarity	NPC56214
0.7559	Intermediate Similarity	NPC227217
0.7559	Intermediate Similarity	NPC117780
0.7559	Intermediate Similarity	NPC103916
0.7559	Intermediate Similarity	NPC165133

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 NPC43275 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	119
0.1-0.2	758
0.2-0.3	1036
0.3-0.4	1648
0.4-0.5	2619
0.5-0.6	1881
0.6-0.7	855
0.7-0.8	225
0.8-0.85	8
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8607	High Similarity	NPD1669	Approved
0.8607	High Similarity	NPD3676	Clinical (unspecified phase)
0.8583	High Similarity	NPD2668	Approved
0.8583	High Similarity	NPD2667	Approved
0.822	Intermediate Similarity	NPD821	Approved
0.8217	Intermediate Similarity	NPD2674	Phase 3
0.8217	Intermediate Similarity	NPD7477	Discontinued
0.816	Intermediate Similarity	NPD6583	Phase 3
0.816	Intermediate Similarity	NPD6582	Phase 2
0.808	Intermediate Similarity	NPD2232	Approved
0.808	Intermediate Similarity	NPD2230	Approved
0.808	Intermediate Similarity	NPD2233	Approved
0.8047	Intermediate Similarity	NPD4993	Discontinued
0.8	Intermediate Similarity	NPD3144	Approved
0.8	Intermediate Similarity	NPD3145	Approved
0.7969	Intermediate Similarity	NPD6584	Phase 3
0.7953	Intermediate Similarity	NPD2922	Phase 1
0.7951	Intermediate Similarity	NPD3596	Phase 2
0.7929	Intermediate Similarity	NPD7131	Phase 3
0.7914	Intermediate Similarity	NPD4123	Phase 3
0.7895	Intermediate Similarity	NPD1772	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD3052	Approved
0.7895	Intermediate Similarity	NPD3054	Approved
0.7883	Intermediate Similarity	NPD6331	Phase 2
0.7879	Intermediate Similarity	NPD5837	Clinical (unspecified phase)
0.7874	Intermediate Similarity	NPD3685	Discontinued
0.7874	Intermediate Similarity	NPD4129	Approved
0.7868	Intermediate Similarity	NPD7596	Clinical (unspecified phase)
0.7863	Intermediate Similarity	NPD3056	Clinical (unspecified phase)
0.7851	Intermediate Similarity	NPD2234	Approved
0.7851	Intermediate Similarity	NPD2228	Approved
0.7851	Intermediate Similarity	NPD2229	Approved
0.7823	Intermediate Similarity	NPD2486	Discontinued
0.7823	Intermediate Similarity	NPD6580	Approved
0.7823	Intermediate Similarity	NPD6581	Approved
0.7812	Intermediate Similarity	NPD7258	Clinical (unspecified phase)
0.7795	Intermediate Similarity	NPD2235	Phase 2
0.7795	Intermediate Similarity	NPD2231	Phase 2
0.7786	Intermediate Similarity	NPD1024	Discontinued
0.7778	Intermediate Similarity	NPD3847	Discontinued
0.7778	Intermediate Similarity	NPD3421	Phase 3
0.7769	Intermediate Similarity	NPD1712	Approved
0.7768	Intermediate Similarity	NPD2933	Approved
0.7768	Intermediate Similarity	NPD2934	Approved
0.7762	Intermediate Similarity	NPD6502	Phase 2
0.7761	Intermediate Similarity	NPD2157	Approved
0.776	Intermediate Similarity	NPD6830	Clinical (unspecified phase)
0.7754	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.7752	Intermediate Similarity	NPD3567	Approved
0.7752	Intermediate Similarity	NPD3568	Approved
0.7734	Intermediate Similarity	NPD2428	Approved
0.7734	Intermediate Similarity	NPD2429	Approved
0.7724	Intermediate Similarity	NPD709	Approved
0.7724	Intermediate Similarity	NPD2557	Approved
0.7721	Intermediate Similarity	NPD2161	Phase 2
0.771	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7708	Intermediate Similarity	NPD3796	Clinical (unspecified phase)
0.7699	Intermediate Similarity	NPD2859	Approved
0.7699	Intermediate Similarity	NPD2860	Approved
0.7698	Intermediate Similarity	NPD2556	Approved
0.7698	Intermediate Similarity	NPD2554	Approved
0.7698	Intermediate Similarity	NPD3692	Discontinued
0.7692	Intermediate Similarity	NPD7451	Discontinued
0.7681	Intermediate Similarity	NPD2460	Phase 3
0.7681	Intermediate Similarity	NPD2459	Approved
0.7681	Intermediate Similarity	NPD2458	Approved
0.7669	Intermediate Similarity	NPD840	Approved
0.7669	Intermediate Similarity	NPD839	Approved
0.7669	Intermediate Similarity	NPD3058	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD5451	Approved
0.7652	Intermediate Similarity	NPD5163	Phase 2
0.7647	Intermediate Similarity	NPD4108	Discontinued
0.7642	Intermediate Similarity	NPD593	Approved
0.7642	Intermediate Similarity	NPD595	Approved
0.7639	Intermediate Similarity	NPD4675	Approved
0.7639	Intermediate Similarity	NPD4678	Approved
0.7638	Intermediate Similarity	NPD3294	Phase 2
0.763	Intermediate Similarity	NPD4097	Suspended
0.7619	Intermediate Similarity	NPD6382	Discontinued
0.7619	Intermediate Similarity	NPD2595	Approved
0.7619	Intermediate Similarity	NPD2594	Approved
0.7619	Intermediate Similarity	NPD3049	Approved
0.7612	Intermediate Similarity	NPD2238	Phase 2
0.7609	Intermediate Similarity	NPD4149	Clinical (unspecified phase)
0.7609	Intermediate Similarity	NPD7153	Discontinued
0.7594	Intermediate Similarity	NPD1048	Approved
0.7594	Intermediate Similarity	NPD5718	Phase 2
0.7583	Intermediate Similarity	NPD2684	Approved
0.7569	Intermediate Similarity	NPD6523	Clinical (unspecified phase)
0.7569	Intermediate Similarity	NPD4005	Discontinued
0.7563	Intermediate Similarity	NPD968	Approved
0.7559	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.7557	Intermediate Similarity	NPD7905	Discontinued
0.7554	Intermediate Similarity	NPD3060	Approved
0.7542	Intermediate Similarity	NPD9608	Approved
0.7542	Intermediate Similarity	NPD9610	Approved
0.7519	Intermediate Similarity	NPD2562	Approved
0.7519	Intermediate Similarity	NPD2561	Approved
0.7519	Intermediate Similarity	NPD2337	Clinical (unspecified phase)
0.7518	Intermediate Similarity	NPD6380	Phase 1
0.75	Intermediate Similarity	NPD4579	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3020	Approved
0.7483	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7482	Intermediate Similarity	NPD3655	Clinical (unspecified phase)
0.7481	Intermediate Similarity	NPD1232	Clinical (unspecified phase)
0.7481	Intermediate Similarity	NPD4098	Discontinued
0.7481	Intermediate Similarity	NPD1558	Phase 1
0.748	Intermediate Similarity	NPD4093	Discontinued
0.748	Intermediate Similarity	NPD3444	Approved
0.748	Intermediate Similarity	NPD3443	Approved
0.748	Intermediate Similarity	NPD3445	Approved
0.7463	Intermediate Similarity	NPD3374	Clinical (unspecified phase)
0.7463	Intermediate Similarity	NPD5109	Approved
0.7463	Intermediate Similarity	NPD5110	Phase 2
0.7463	Intermediate Similarity	NPD1039	Discontinued
0.7463	Intermediate Similarity	NPD5111	Phase 2
0.7462	Intermediate Similarity	NPD6542	Approved
0.7462	Intermediate Similarity	NPD6543	Approved
0.7462	Intermediate Similarity	NPD6540	Phase 3
0.7462	Intermediate Similarity	NPD6539	Approved
0.7462	Intermediate Similarity	NPD4659	Approved
0.746	Intermediate Similarity	NPD1758	Phase 1
0.7447	Intermediate Similarity	NPD5241	Discontinued
0.7445	Intermediate Similarity	NPD3555	Approved
0.7445	Intermediate Similarity	NPD3553	Approved
0.7445	Intermediate Similarity	NPD3552	Approved
0.7445	Intermediate Similarity	NPD3554	Approved
0.7444	Intermediate Similarity	NPD2614	Approved
0.7429	Intermediate Similarity	NPD2976	Clinical (unspecified phase)
0.7424	Intermediate Similarity	NPD7018	Phase 2
0.7419	Intermediate Similarity	NPD5283	Phase 1
0.7413	Intermediate Similarity	NPD2874	Phase 2
0.7413	Intermediate Similarity	NPD7020	Approved
0.7413	Intermediate Similarity	NPD7019	Approved
0.7407	Intermediate Similarity	NPD1423	Approved
0.7407	Intermediate Similarity	NPD5745	Approved
0.7405	Intermediate Similarity	NPD6538	Approved
0.7405	Intermediate Similarity	NPD6541	Approved
0.7405	Intermediate Similarity	NPD196	Phase 1
0.7402	Intermediate Similarity	NPD5304	Approved
0.7402	Intermediate Similarity	NPD1759	Phase 1
0.7402	Intermediate Similarity	NPD5303	Approved
0.7398	Intermediate Similarity	NPD228	Approved
0.7391	Intermediate Similarity	NPD3846	Clinical (unspecified phase)
0.7388	Intermediate Similarity	NPD6179	Discontinued
0.7377	Intermediate Similarity	NPD9380	Clinical (unspecified phase)
0.7377	Intermediate Similarity	NPD1792	Phase 2
0.7376	Intermediate Similarity	NPD5481	Discontinued
0.7348	Intermediate Similarity	NPD4104	Clinical (unspecified phase)
0.7348	Intermediate Similarity	NPD4103	Phase 2
0.7347	Intermediate Similarity	NPD7438	Suspended
0.7339	Intermediate Similarity	NPD5535	Approved
0.7339	Intermediate Similarity	NPD7843	Approved
0.7338	Intermediate Similarity	NPD1725	Approved
0.7333	Intermediate Similarity	NPD6812	Clinical (unspecified phase)
0.7328	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7323	Intermediate Similarity	NPD856	Approved
0.7323	Intermediate Similarity	NPD16	Approved
0.7319	Intermediate Similarity	NPD6895	Approved
0.7319	Intermediate Similarity	NPD6896	Approved
0.7315	Intermediate Similarity	NPD2379	Clinical (unspecified phase)
0.7313	Intermediate Similarity	NPD596	Approved
0.7313	Intermediate Similarity	NPD600	Approved
0.731	Intermediate Similarity	NPD2122	Discontinued
0.7305	Intermediate Similarity	NPD5177	Phase 3
0.7305	Intermediate Similarity	NPD44	Approved
0.7305	Intermediate Similarity	NPD6364	Approved
0.7305	Intermediate Similarity	NPD4162	Approved
0.7293	Intermediate Similarity	NPD3691	Phase 2
0.7293	Intermediate Similarity	NPD3690	Phase 2
0.7292	Intermediate Similarity	NPD4739	Approved
0.7292	Intermediate Similarity	NPD3536	Discontinued
0.7292	Intermediate Similarity	NPD3985	Discontinued
0.7292	Intermediate Similarity	NPD5348	Clinical (unspecified phase)
0.7287	Intermediate Similarity	NPD2423	Clinical (unspecified phase)
0.7286	Intermediate Similarity	NPD5865	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD5617	Suspended
0.7279	Intermediate Similarity	NPD7265	Discontinued
0.7273	Intermediate Similarity	NPD1445	Approved
0.7273	Intermediate Similarity	NPD1444	Approved
0.7273	Intermediate Similarity	NPD6667	Approved
0.7273	Intermediate Similarity	NPD6666	Approved
0.7267	Intermediate Similarity	NPD7773	Phase 2
0.7266	Intermediate Similarity	NPD1548	Phase 1
0.7259	Intermediate Similarity	NPD3136	Phase 2
0.7259	Intermediate Similarity	NPD5746	Approved
0.7254	Intermediate Similarity	NPD1662	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD179	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD6390	Discontinued
0.7241	Intermediate Similarity	NPD4186	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD7037	Approved
0.723	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD6072	Discontinued
0.7226	Intermediate Similarity	NPD3110	Approved
0.7226	Intermediate Similarity	NPD3109	Approved
0.7222	Intermediate Similarity	NPD7212	Phase 2
0.7222	Intermediate Similarity	NPD4357	Discontinued
0.7222	Intermediate Similarity	NPD7213	Phase 3
0.7219	Intermediate Similarity	NPD5604	Discontinued
0.7218	Intermediate Similarity	NPD3055	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