NPASS Compound

Structure

NPC471314 OpenBabel07101718282D 24 25 0 0 0 0 0 0 0 0999 V2000 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3923 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5263 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3923 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5263 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 24 1 0 0 0 0 2 3 1 0 0 0 0 2 5 1 0 0 0 0 3 8 1 0 0 0 0 4 6 2 0 0 0 0 4 7 1 0 0 0 0 5 10 1 0 0 0 0 6 11 1 0 0 0 0 7 12 2 0 0 0 0 8 15 1 0 0 0 0 9 13 2 0 0 0 0 9 14 1 0 0 0 0 10 18 1 0 0 0 0 11 18 2 0 0 0 0 12 18 1 0 0 0 0 13 19 1 0 0 0 0 14 20 2 0 0 0 0 15 21 1 0 0 0 0 16 19 2 0 0 0 0 16 20 1 0 0 0 0 17 19 1 0 0 0 0 17 22 1 0 0 0 0 20 24 1 0 0 0 0 21 22 2 3 0 0 0 21 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	325.2
Volume:	364.781
LogP:	4.559
LogD:	3.906
LogS:	-4.495
# Rotatable Bonds:	11
TPSA:	38.33
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.653
Synthetic Accessibility Score:	1.637
Fsp3:	0.381
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.665
MDCK Permeability:	1.7136495443992317e-05
Pgp-inhibitor:	0.986
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.95
30% Bioavailability (F30%):	0.979

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.401
Plasma Protein Binding (PPB):	97.91626739501953%
Volume Distribution (VD):	0.971
Pgp-substrate:	0.8818238973617554%

ADMET: Metabolism

CYP1A2-inhibitor:	0.91
CYP1A2-substrate:	0.923
CYP2C19-inhibitor:	0.954
CYP2C19-substrate:	0.228
CYP2C9-inhibitor:	0.86
CYP2C9-substrate:	0.775
CYP2D6-inhibitor:	0.939
CYP2D6-substrate:	0.878
CYP3A4-inhibitor:	0.938
CYP3A4-substrate:	0.266

ADMET: Excretion

Clearance (CL):	8.913
Half-life (T1/2):	0.696

ADMET: Toxicity

hERG Blockers:	0.857
Human Hepatotoxicity (H-HT):	0.283
Drug-inuced Liver Injury (DILI):	0.039
AMES Toxicity:	0.025
Rat Oral Acute Toxicity:	0.016
Maximum Recommended Daily Dose:	0.101
Skin Sensitization:	0.913
Carcinogencity:	0.03
Eye Corrosion:	0.004
Eye Irritation:	0.075
Respiratory Toxicity:	0.044

Download Data

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

Natural Product: NPC471314

Natural Product ID:	NPC471314
*Common Name:**	N-(3-Methoxybenzyl)-7-Phenylheptanamide
IUPAC Name:	N-[(3-methoxyphenyl)methyl]-7-phenylheptanamide
Synonyms:
Standard InCHIKey:	UUSWZGGSKXQTSW-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C21H27NO2/c1-24-20-14-9-13-19(16-20)17-22-21(23)15-8-3-2-5-10-18-11-6-4-7-12-18/h4,6-7,9,11-14,16H,2-3,5,8,10,15,17H2,1H3,(H,22,23)
SMILES:	COc1cccc(c1)CN=C(CCCCCCc1ccccc1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2413172
PubChem CID:	71770425
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002341] Phenol ethers [CHEMONTID:0000138] Anisoles

*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
NPO18988	Lepidium meyenii	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12932133]
NPO18988	Lepidium meyenii	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23891163]
NPO18988	Lepidium meyenii	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24972328]
NPO18988	Lepidium meyenii	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[33320645]
NPO18988	Lepidium meyenii	Species	Brassicaceae	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	1
Others	2

Activity Type	# Activity
Individual Protein	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1418	Individual Protein	Anandamide amidohydrolase	Homo sapiens	IC50	>	500000.0	nM	PMID[474652]
NPT1418	Individual Protein	Anandamide amidohydrolase	Homo sapiens	Inhibition	<	10.0	%	PMID[474652]
NPT1418	Individual Protein	Anandamide amidohydrolase	Homo sapiens	Inhibition	=	16.1	%	PMID[474652]

☑ 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 NPC471314 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	149
0.1-0.2	1348
0.2-0.3	7130
0.3-0.4	10470
0.4-0.5	6252
0.5-0.6	12221
0.6-0.7	4484
0.7-0.8	596
0.8-0.85	26
0.85-0.9	11
0.9-0.95	2
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC471315
0.9569	High Similarity	NPC17388
0.9569	High Similarity	NPC471308
0.9569	High Similarity	NPC160120
0.9569	High Similarity	NPC53596
0.9569	High Similarity	NPC289330
0.8915	High Similarity	NPC471316
0.8833	High Similarity	NPC43275
0.8682	High Similarity	NPC218530
0.8672	High Similarity	NPC130595
0.8672	High Similarity	NPC93882
0.8605	High Similarity	NPC285078
0.8605	High Similarity	NPC6854
0.8605	High Similarity	NPC313737
0.8594	High Similarity	NPC114102
0.8571	High Similarity	NPC301713
0.8504	High Similarity	NPC251571
0.8455	Intermediate Similarity	NPC263835
0.845	Intermediate Similarity	NPC308885
0.845	Intermediate Similarity	NPC255550
0.8438	Intermediate Similarity	NPC155838
0.8413	Intermediate Similarity	NPC62101
0.8413	Intermediate Similarity	NPC95733
0.8385	Intermediate Similarity	NPC214869
0.8372	Intermediate Similarity	NPC35961
0.8372	Intermediate Similarity	NPC52029
0.8372	Intermediate Similarity	NPC195749
0.8346	Intermediate Similarity	NPC29477
0.8333	Intermediate Similarity	NPC211218
0.8306	Intermediate Similarity	NPC321133
0.8217	Intermediate Similarity	NPC153990
0.8197	Intermediate Similarity	NPC303370
0.8167	Intermediate Similarity	NPC166837
0.8154	Intermediate Similarity	NPC471321
0.8154	Intermediate Similarity	NPC471306
0.8077	Intermediate Similarity	NPC172403
0.8077	Intermediate Similarity	NPC186898
0.8074	Intermediate Similarity	NPC14600
0.8074	Intermediate Similarity	NPC204848
0.8074	Intermediate Similarity	NPC41473
0.8074	Intermediate Similarity	NPC160607
0.8074	Intermediate Similarity	NPC312770
0.8067	Intermediate Similarity	NPC75440
0.8042	Intermediate Similarity	NPC275027
0.8015	Intermediate Similarity	NPC299583
0.7972	Intermediate Similarity	NPC52475
0.7939	Intermediate Similarity	NPC191302
0.7937	Intermediate Similarity	NPC256369
0.7937	Intermediate Similarity	NPC268572
0.7934	Intermediate Similarity	NPC474149
0.7917	Intermediate Similarity	NPC18614
0.7917	Intermediate Similarity	NPC96224
0.7917	Intermediate Similarity	NPC24101
0.7899	Intermediate Similarity	NPC231705
0.7899	Intermediate Similarity	NPC113457
0.7883	Intermediate Similarity	NPC296898
0.7851	Intermediate Similarity	NPC258056
0.7812	Intermediate Similarity	NPC83279
0.781	Intermediate Similarity	NPC254610
0.781	Intermediate Similarity	NPC193528
0.7801	Intermediate Similarity	NPC5462
0.7801	Intermediate Similarity	NPC185838
0.7778	Intermediate Similarity	NPC283468
0.7778	Intermediate Similarity	NPC323948
0.7769	Intermediate Similarity	NPC201959
0.7769	Intermediate Similarity	NPC153690
0.776	Intermediate Similarity	NPC53906
0.7759	Intermediate Similarity	NPC470161
0.7744	Intermediate Similarity	NPC147247
0.7744	Intermediate Similarity	NPC246974
0.7734	Intermediate Similarity	NPC41801
0.7731	Intermediate Similarity	NPC474603
0.7731	Intermediate Similarity	NPC12987
0.7727	Intermediate Similarity	NPC218323
0.7724	Intermediate Similarity	NPC21890
0.7717	Intermediate Similarity	NPC122009
0.7714	Intermediate Similarity	NPC100478
0.7714	Intermediate Similarity	NPC222039
0.7705	Intermediate Similarity	NPC474272
0.7704	Intermediate Similarity	NPC118419
0.7698	Intermediate Similarity	NPC189724
0.7698	Intermediate Similarity	NPC477838
0.7698	Intermediate Similarity	NPC212850
0.7698	Intermediate Similarity	NPC83289
0.7698	Intermediate Similarity	NPC314682
0.7698	Intermediate Similarity	NPC477837
0.7698	Intermediate Similarity	NPC82963
0.7692	Intermediate Similarity	NPC321505
0.7692	Intermediate Similarity	NPC476151
0.7692	Intermediate Similarity	NPC191376
0.7692	Intermediate Similarity	NPC179825
0.7687	Intermediate Similarity	NPC470706
0.7686	Intermediate Similarity	NPC186469
0.7686	Intermediate Similarity	NPC142297
0.768	Intermediate Similarity	NPC276737
0.768	Intermediate Similarity	NPC22610
0.7669	Intermediate Similarity	NPC99798
0.7669	Intermediate Similarity	NPC157740
0.7651	Intermediate Similarity	NPC329837
0.7647	Intermediate Similarity	NPC178902
0.7643	Intermediate Similarity	NPC188163
0.7643	Intermediate Similarity	NPC474915
0.7643	Intermediate Similarity	NPC328750
0.7643	Intermediate Similarity	NPC474128
0.7643	Intermediate Similarity	NPC213206
0.7642	Intermediate Similarity	NPC475852
0.7642	Intermediate Similarity	NPC2682
0.7639	Intermediate Similarity	NPC135538
0.7639	Intermediate Similarity	NPC24233
0.7639	Intermediate Similarity	NPC147390
0.7639	Intermediate Similarity	NPC476571
0.7639	Intermediate Similarity	NPC428
0.7639	Intermediate Similarity	NPC246587
0.7638	Intermediate Similarity	NPC69261
0.7638	Intermediate Similarity	NPC474933
0.7638	Intermediate Similarity	NPC33270
0.7638	Intermediate Similarity	NPC470759
0.7638	Intermediate Similarity	NPC311737
0.7638	Intermediate Similarity	NPC38458
0.7638	Intermediate Similarity	NPC15860
0.7638	Intermediate Similarity	NPC127894
0.7638	Intermediate Similarity	NPC219070
0.7634	Intermediate Similarity	NPC217277
0.7623	Intermediate Similarity	NPC146530
0.7619	Intermediate Similarity	NPC808
0.76	Intermediate Similarity	NPC35344
0.76	Intermediate Similarity	NPC141003
0.7594	Intermediate Similarity	NPC156944
0.7594	Intermediate Similarity	NPC251466
0.7586	Intermediate Similarity	NPC207824
0.7586	Intermediate Similarity	NPC103379
0.7586	Intermediate Similarity	NPC477565
0.7586	Intermediate Similarity	NPC60538
0.7578	Intermediate Similarity	NPC474040
0.7578	Intermediate Similarity	NPC190514
0.7578	Intermediate Similarity	NPC474214
0.7578	Intermediate Similarity	NPC470626
0.7574	Intermediate Similarity	NPC470392
0.7574	Intermediate Similarity	NPC471953
0.7569	Intermediate Similarity	NPC115144
0.7569	Intermediate Similarity	NPC277857
0.7563	Intermediate Similarity	NPC300166
0.7559	Intermediate Similarity	NPC141090
0.7559	Intermediate Similarity	NPC150624
0.7559	Intermediate Similarity	NPC114064
0.7556	Intermediate Similarity	NPC160193
0.7552	Intermediate Similarity	NPC313414
0.7541	Intermediate Similarity	NPC233320
0.754	Intermediate Similarity	NPC118202
0.754	Intermediate Similarity	NPC142599
0.7537	Intermediate Similarity	NPC291449
0.7537	Intermediate Similarity	NPC41331
0.7536	Intermediate Similarity	NPC11147
0.7521	Intermediate Similarity	NPC42383
0.7519	Intermediate Similarity	NPC184302
0.7519	Intermediate Similarity	NPC474320
0.7519	Intermediate Similarity	NPC152186
0.7519	Intermediate Similarity	NPC182147
0.7519	Intermediate Similarity	NPC246133
0.7519	Intermediate Similarity	NPC207541
0.7519	Intermediate Similarity	NPC281298
0.7519	Intermediate Similarity	NPC170583
0.7519	Intermediate Similarity	NPC310338
0.7519	Intermediate Similarity	NPC71105
0.7518	Intermediate Similarity	NPC275150
0.7517	Intermediate Similarity	NPC471032
0.7517	Intermediate Similarity	NPC470935
0.75	Intermediate Similarity	NPC120075
0.75	Intermediate Similarity	NPC293619
0.75	Intermediate Similarity	NPC140359
0.75	Intermediate Similarity	NPC13020
0.7483	Intermediate Similarity	NPC76213
0.7483	Intermediate Similarity	NPC476568
0.7483	Intermediate Similarity	NPC277669
0.7483	Intermediate Similarity	NPC127402
0.7483	Intermediate Similarity	NPC247298
0.7482	Intermediate Similarity	NPC131204
0.7482	Intermediate Similarity	NPC301050
0.7481	Intermediate Similarity	NPC211992
0.748	Intermediate Similarity	NPC97811
0.748	Intermediate Similarity	NPC167934
0.748	Intermediate Similarity	NPC317254
0.748	Intermediate Similarity	NPC309982
0.7462	Intermediate Similarity	NPC227217
0.7462	Intermediate Similarity	NPC165133
0.7462	Intermediate Similarity	NPC232316
0.7462	Intermediate Similarity	NPC56214
0.7462	Intermediate Similarity	NPC242885
0.7462	Intermediate Similarity	NPC95614
0.7462	Intermediate Similarity	NPC103916
0.7462	Intermediate Similarity	NPC117780
0.746	Intermediate Similarity	NPC165106
0.7444	Intermediate Similarity	NPC300955
0.744	Intermediate Similarity	NPC275627
0.7438	Intermediate Similarity	NPC241224
0.7424	Intermediate Similarity	NPC298486
0.7422	Intermediate Similarity	NPC258992
0.7415	Intermediate Similarity	NPC220858
0.7415	Intermediate Similarity	NPC478189
0.7415	Intermediate Similarity	NPC88249

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 NPC471314 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	126
0.1-0.2	694
0.2-0.3	959
0.3-0.4	1526
0.4-0.5	2568
0.5-0.6	2107
0.6-0.7	969
0.7-0.8	187
0.8-0.85	11
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.878	High Similarity	NPD1669	Approved
0.8672	High Similarity	NPD7477	Discontinued
0.8672	High Similarity	NPD2674	Phase 3
0.845	Intermediate Similarity	NPD3145	Approved
0.845	Intermediate Similarity	NPD3144	Approved
0.8333	Intermediate Similarity	NPD3676	Clinical (unspecified phase)
0.8306	Intermediate Similarity	NPD2667	Approved
0.8306	Intermediate Similarity	NPD2668	Approved
0.8254	Intermediate Similarity	NPD2232	Approved
0.8254	Intermediate Similarity	NPD2230	Approved
0.8254	Intermediate Similarity	NPD2233	Approved
0.8231	Intermediate Similarity	NPD1024	Discontinued
0.8217	Intermediate Similarity	NPD1712	Approved
0.8162	Intermediate Similarity	NPD7153	Discontinued
0.8043	Intermediate Similarity	NPD6331	Phase 2
0.8015	Intermediate Similarity	NPD2161	Phase 2
0.797	Intermediate Similarity	NPD839	Approved
0.797	Intermediate Similarity	NPD840	Approved
0.7941	Intermediate Similarity	NPD4108	Discontinued
0.7926	Intermediate Similarity	NPD2157	Approved
0.7903	Intermediate Similarity	NPD709	Approved
0.7899	Intermediate Similarity	NPD3655	Clinical (unspecified phase)
0.7863	Intermediate Similarity	NPD7905	Discontinued
0.7863	Intermediate Similarity	NPD6584	Phase 3
0.7846	Intermediate Similarity	NPD2922	Phase 1
0.7829	Intermediate Similarity	NPD2231	Phase 2
0.7829	Intermediate Similarity	NPD2235	Phase 2
0.7826	Intermediate Similarity	NPD3656	Approved
0.7817	Intermediate Similarity	NPD4123	Phase 3
0.781	Intermediate Similarity	NPD3693	Clinical (unspecified phase)
0.7805	Intermediate Similarity	NPD821	Approved
0.7795	Intermediate Similarity	NPD2595	Approved
0.7795	Intermediate Similarity	NPD2594	Approved
0.777	Intermediate Similarity	NPD7596	Clinical (unspecified phase)
0.7769	Intermediate Similarity	NPD1421	Approved
0.7769	Intermediate Similarity	NPD1420	Approved
0.7717	Intermediate Similarity	NPD2486	Discontinued
0.7714	Intermediate Similarity	NPD2460	Phase 3
0.7714	Intermediate Similarity	NPD2459	Approved
0.7714	Intermediate Similarity	NPD2458	Approved
0.7704	Intermediate Similarity	NPD4474	Approved
0.7704	Intermediate Similarity	NPD4475	Approved
0.7674	Intermediate Similarity	NPD3294	Phase 2
0.7664	Intermediate Similarity	NPD2986	Phase 2
0.7664	Intermediate Similarity	NPD2989	Phase 2
0.766	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.7656	Intermediate Similarity	NPD3049	Approved
0.7647	Intermediate Similarity	NPD5837	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD2238	Phase 2
0.7643	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.7639	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7634	Intermediate Similarity	NPD6583	Phase 3
0.7634	Intermediate Similarity	NPD6582	Phase 2
0.763	Intermediate Similarity	NPD1039	Discontinued
0.7626	Intermediate Similarity	NPD3156	Discontinued
0.7619	Intermediate Similarity	NPD2557	Approved
0.7616	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.7612	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7606	Intermediate Similarity	NPD3692	Discontinued
0.7597	Intermediate Similarity	NPD2423	Clinical (unspecified phase)
0.7589	Intermediate Similarity	NPD5177	Phase 3
0.7576	Intermediate Similarity	NPD7258	Clinical (unspecified phase)
0.7569	Intermediate Similarity	NPD2874	Phase 2
0.7561	Intermediate Similarity	NPD1792	Phase 2
0.7559	Intermediate Similarity	NPD3596	Phase 2
0.7557	Intermediate Similarity	NPD2337	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD4678	Approved
0.7551	Intermediate Similarity	NPD4675	Approved
0.754	Intermediate Similarity	NPD593	Approved
0.754	Intermediate Similarity	NPD595	Approved
0.7536	Intermediate Similarity	NPD4579	Clinical (unspecified phase)
0.7535	Intermediate Similarity	NPD3977	Clinical (unspecified phase)
0.7519	Intermediate Similarity	NPD3443	Approved
0.7519	Intermediate Similarity	NPD3445	Approved
0.7519	Intermediate Similarity	NPD3444	Approved
0.7517	Intermediate Similarity	NPD6090	Discontinued
0.75	Intermediate Similarity	NPD3685	Discontinued
0.75	Intermediate Similarity	NPD3796	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7438	Suspended
0.75	Intermediate Similarity	NPD5718	Phase 2
0.75	Intermediate Similarity	NPD3056	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4129	Approved
0.7483	Intermediate Similarity	NPD4055	Discovery
0.7482	Intermediate Similarity	NPD696	Discontinued
0.7481	Intermediate Similarity	NPD600	Approved
0.7481	Intermediate Similarity	NPD596	Approved
0.7464	Intermediate Similarity	NPD654	Phase 3
0.7462	Intermediate Similarity	NPD2554	Approved
0.7462	Intermediate Similarity	NPD2556	Approved
0.746	Intermediate Similarity	NPD2229	Approved
0.746	Intermediate Similarity	NPD2228	Approved
0.746	Intermediate Similarity	NPD2234	Approved
0.746	Intermediate Similarity	NPD5283	Phase 1
0.7459	Intermediate Similarity	NPD1445	Approved
0.7459	Intermediate Similarity	NPD1444	Approved
0.745	Intermediate Similarity	NPD3812	Clinical (unspecified phase)
0.7445	Intermediate Similarity	NPD3058	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD6580	Approved
0.7442	Intermediate Similarity	NPD6581	Approved
0.7432	Intermediate Similarity	NPD5617	Suspended
0.7432	Intermediate Similarity	NPD6502	Phase 2
0.7415	Intermediate Similarity	NPD950	Clinical (unspecified phase)
0.7415	Intermediate Similarity	NPD5267	Discontinued
0.741	Intermediate Similarity	NPD1772	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD2040	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD2407	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD3847	Discontinued
0.7405	Intermediate Similarity	NPD1980	Approved
0.7405	Intermediate Similarity	NPD1981	Approved
0.7405	Intermediate Similarity	NPD1983	Approved
0.74	Intermediate Similarity	NPD6060	Clinical (unspecified phase)
0.7388	Intermediate Similarity	NPD3568	Approved
0.7388	Intermediate Similarity	NPD4098	Discontinued
0.7388	Intermediate Similarity	NPD3567	Approved
0.7385	Intermediate Similarity	NPD4093	Discontinued
0.7385	Intermediate Similarity	NPD6382	Discontinued
0.7385	Intermediate Similarity	NPD6830	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD6087	Phase 1
0.7372	Intermediate Similarity	NPD5111	Phase 2
0.7372	Intermediate Similarity	NPD5110	Phase 2
0.7372	Intermediate Similarity	NPD6812	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD5109	Approved
0.7365	Intermediate Similarity	NPD4005	Discontinued
0.7365	Intermediate Similarity	NPD5811	Approved
0.7357	Intermediate Similarity	NPD6896	Approved
0.7357	Intermediate Similarity	NPD6895	Approved
0.7355	Intermediate Similarity	NPD4083	Discontinued
0.7344	Intermediate Similarity	NPD6671	Approved
0.7343	Intermediate Similarity	NPD3060	Approved
0.7333	Intermediate Similarity	NPD2990	Approved
0.7333	Intermediate Similarity	NPD2987	Approved
0.7333	Intermediate Similarity	NPD558	Phase 2
0.7329	Intermediate Similarity	NPD4584	Approved
0.7329	Intermediate Similarity	NPD7019	Approved
0.7329	Intermediate Similarity	NPD7020	Approved
0.7329	Intermediate Similarity	NPD4739	Approved
0.7308	Intermediate Similarity	NPD2226	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD5163	Phase 2
0.7297	Intermediate Similarity	NPD4003	Phase 3
0.7286	Intermediate Similarity	NPD4097	Suspended
0.7286	Intermediate Similarity	NPD3054	Approved
0.7286	Intermediate Similarity	NPD3052	Approved
0.728	Intermediate Similarity	NPD5451	Approved
0.7279	Intermediate Similarity	NPD7527	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD52	Approved
0.7279	Intermediate Similarity	NPD4993	Discontinued
0.7279	Intermediate Similarity	NPD7526	Approved
0.7266	Intermediate Similarity	NPD3109	Approved
0.7266	Intermediate Similarity	NPD6346	Approved
0.7266	Intermediate Similarity	NPD3110	Approved
0.7255	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD6032	Approved
0.7248	Intermediate Similarity	NPD6523	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD5241	Discontinued
0.7241	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD2428	Approved
0.7239	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD2429	Approved
0.723	Intermediate Similarity	NPD1914	Approved
0.7222	Intermediate Similarity	NPD44	Approved
0.7222	Intermediate Similarity	NPD4162	Approved
0.7222	Intermediate Similarity	NPD6364	Approved
0.7218	Intermediate Similarity	NPD776	Approved
0.7218	Intermediate Similarity	NPD5350	Clinical (unspecified phase)
0.7218	Intermediate Similarity	NPD5351	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD7493	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD681	Clinical (unspecified phase)
0.7206	Intermediate Similarity	NPD7451	Discontinued
0.7203	Intermediate Similarity	NPD1375	Discontinued
0.7203	Intermediate Similarity	NPD7083	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD2684	Approved
0.72	Intermediate Similarity	NPD3679	Phase 2
0.7183	Intermediate Similarity	NPD3846	Clinical (unspecified phase)
0.7183	Intermediate Similarity	NPD6380	Phase 1
0.7183	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7183	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7183	Intermediate Similarity	NPD5788	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD2883	Discontinued
0.7177	Intermediate Similarity	NPD968	Approved
0.7171	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7165	Intermediate Similarity	NPD228	Approved
0.7153	Intermediate Similarity	NPD7037	Approved
0.7152	Intermediate Similarity	NPD5602	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD6072	Discontinued
0.7152	Intermediate Similarity	NPD980	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4357	Discontinued
0.7143	Intermediate Similarity	NPD2859	Approved
0.7143	Intermediate Similarity	NPD2860	Approved
0.7143	Intermediate Similarity	NPD5604	Discontinued
0.7143	Intermediate Similarity	NPD3453	Discontinued
0.7143	Intermediate Similarity	NPD7833	Phase 2
0.7143	Intermediate Similarity	NPD7831	Phase 2
0.7133	Intermediate Similarity	NPD4017	Approved
0.7132	Intermediate Similarity	NPD1793	Approved
0.7132	Intermediate Similarity	NPD1791	Approved
0.7114	Intermediate Similarity	NPD6031	Approved
0.7114	Intermediate Similarity	NPD5976	Discontinued
0.7114	Intermediate Similarity	NPD7131	Phase 3
0.7114	Intermediate Similarity	NPD6030	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