NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	247.12
Volume:	257.772
LogP:	2.923
LogD:	3.507
LogS:	-4.305
# Rotatable Bonds:	5
TPSA:	47.56
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.83
Synthetic Accessibility Score:	2.101
Fsp3:	0.357
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:	-4.642
MDCK Permeability:	1.9534380044206046e-05
Pgp-inhibitor:	0.975
Pgp-substrate:	0.865
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.001
30% Bioavailability (F30%):	0.005

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.698
Plasma Protein Binding (PPB):	94.49829864501953%
Volume Distribution (VD):	1.267
Pgp-substrate:	7.042483806610107%

ADMET: Metabolism

CYP1A2-inhibitor:	0.971
CYP1A2-substrate:	0.154
CYP2C19-inhibitor:	0.853
CYP2C19-substrate:	0.449
CYP2C9-inhibitor:	0.504
CYP2C9-substrate:	0.952
CYP2D6-inhibitor:	0.786
CYP2D6-substrate:	0.824
CYP3A4-inhibitor:	0.878
CYP3A4-substrate:	0.222

ADMET: Excretion

Clearance (CL):	14.59
Half-life (T1/2):	0.547

ADMET: Toxicity

hERG Blockers:	0.104
Human Hepatotoxicity (H-HT):	0.206
Drug-inuced Liver Injury (DILI):	0.512
AMES Toxicity:	0.038
Rat Oral Acute Toxicity:	0.012
Maximum Recommended Daily Dose:	0.018
Skin Sensitization:	0.665
Carcinogencity:	0.893
Eye Corrosion:	0.041
Eye Irritation:	0.664
Respiratory Toxicity:	0.231

Download Data

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

Natural Product: NPC300955

Natural Product ID:	NPC300955
*Common Name:**	Fogaramide
IUPAC Name:	(E)-3-(1,3-benzodioxol-5-yl)-N-(2-methylpropyl)prop-2-enamide
Synonyms:	Fogaramide; Trans-Fagaramide
Standard InCHIKey:	WKWYNAMJWDRHBP-GQCTYLIASA-N
Standard InCHI:	InChI=1S/C14H17NO3/c1-10(2)8-15-14(16)6-4-11-3-5-12-13(7-11)18-9-17-12/h3-7,10H,8-9H2,1-2H3,(H,15,16)/b6-4+
SMILES:	CC(CN=C(/C=C/c1ccc2c(c1)OCO2)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL252709
PubChem CID:	5281772
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000296] Benzodioxoles

*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
NPO4756	Mesua elegans	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20943395]
NPO5710	Michelia rajaniana	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[3236012]
NPO32775	dinosperma erythrococca	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9599259]
NPO6280	Fagara xanthoxyloides	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[HerDing]
NPO27774	Asarum sagittarioides	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6280	Fagara xanthoxyloides	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]
NPO27774	Asarum sagittarioides	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29440	Sarcomyxa serotina	Species	Tricholomataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4442	Artemisia austriaca	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO81	Erythrina orientalis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3215	Phora atra	Species	Phoridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4756	Mesua elegans	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5710	Michelia rajaniana	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28383	Vernonia tufnellae	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11244	Chrysolaena propinqua	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9318	Stevia serrata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12990	Umbelopsis vinacea	Species	Umbelopsidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO924	Russula subnigricans	Species	Russulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8378	Fagara heitzii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO6557	Lotus villosus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5060	Onychopetalum amazonicum	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9469	Digitalis obscura	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25530	Daphne blagayana	Species	Thymelaeaceae	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
Others	2

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	13.2	%	PMID[482568]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	89.24	n.a.	PMID[482568]

☑ 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 NPC300955 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	165
0.1-0.2	1524
0.2-0.3	7701
0.3-0.4	11503
0.4-0.5	5934
0.5-0.6	10749
0.6-0.7	4273
0.7-0.8	778
0.8-0.85	43
0.85-0.9	6
0.9-0.95	6
0.95-1	15

Similarity Score	Similarity Level	Natural Product ID
0.9915	High Similarity	NPC170583
0.9915	High Similarity	NPC182147
0.9915	High Similarity	NPC246133
0.9915	High Similarity	NPC207541
0.9915	High Similarity	NPC152186
0.9915	High Similarity	NPC71105
0.9832	High Similarity	NPC156944
0.9832	High Similarity	NPC251466
0.975	High Similarity	NPC99798
0.975	High Similarity	NPC41331
0.975	High Similarity	NPC291449
0.975	High Similarity	NPC157740
0.9669	High Similarity	NPC246974
0.9669	High Similarity	NPC147247
0.9426	High Similarity	NPC191302
0.935	High Similarity	NPC469977
0.9274	High Similarity	NPC470706
0.9134	High Similarity	NPC282477
0.9134	High Similarity	NPC473463
0.9134	High Similarity	NPC284855
0.8632	High Similarity	NPC127326
0.8583	High Similarity	NPC301713
0.8582	High Similarity	NPC275150
0.8516	High Similarity	NPC186898
0.8516	High Similarity	NPC153990
0.8496	Intermediate Similarity	NPC254610
0.8487	Intermediate Similarity	NPC166837
0.845	Intermediate Similarity	NPC155838
0.8403	Intermediate Similarity	NPC31279
0.8385	Intermediate Similarity	NPC52029
0.8385	Intermediate Similarity	NPC195749
0.8385	Intermediate Similarity	NPC35961
0.8346	Intermediate Similarity	NPC249788
0.8333	Intermediate Similarity	NPC327623
0.8321	Intermediate Similarity	NPC308885
0.8321	Intermediate Similarity	NPC255550
0.8258	Intermediate Similarity	NPC214869
0.824	Intermediate Similarity	NPC57501
0.8239	Intermediate Similarity	NPC474560
0.8235	Intermediate Similarity	NPC77572
0.8231	Intermediate Similarity	NPC251571
0.8182	Intermediate Similarity	NPC114102
0.8175	Intermediate Similarity	NPC344161
0.8154	Intermediate Similarity	NPC274356
0.8151	Intermediate Similarity	NPC227894
0.8134	Intermediate Similarity	NPC218530
0.812	Intermediate Similarity	NPC130595
0.812	Intermediate Similarity	NPC93882
0.811	Intermediate Similarity	NPC183262
0.8095	Intermediate Similarity	NPC69670
0.808	Intermediate Similarity	NPC212643
0.808	Intermediate Similarity	NPC199209
0.808	Intermediate Similarity	NPC33271
0.8065	Intermediate Similarity	NPC303370
0.806	Intermediate Similarity	NPC285078
0.806	Intermediate Similarity	NPC313737
0.806	Intermediate Similarity	NPC6854
0.8047	Intermediate Similarity	NPC301641
0.8047	Intermediate Similarity	NPC80241
0.8047	Intermediate Similarity	NPC114845
0.8034	Intermediate Similarity	NPC310905
0.8034	Intermediate Similarity	NPC12714
0.8033	Intermediate Similarity	NPC55300
0.8017	Intermediate Similarity	NPC36108
0.8017	Intermediate Similarity	NPC246358
0.8017	Intermediate Similarity	NPC7097
0.8017	Intermediate Similarity	NPC233731
0.8	Intermediate Similarity	NPC111225
0.7985	Intermediate Similarity	NPC318862
0.7967	Intermediate Similarity	NPC165646
0.7956	Intermediate Similarity	NPC312770
0.7956	Intermediate Similarity	NPC41473
0.7956	Intermediate Similarity	NPC14600
0.7956	Intermediate Similarity	NPC470707
0.7956	Intermediate Similarity	NPC204848
0.7956	Intermediate Similarity	NPC160607
0.7953	Intermediate Similarity	NPC119949
0.7951	Intermediate Similarity	NPC137685
0.791	Intermediate Similarity	NPC275950
0.7899	Intermediate Similarity	NPC299583
0.7899	Intermediate Similarity	NPC292792
0.7899	Intermediate Similarity	NPC296898
0.7886	Intermediate Similarity	NPC78918
0.7886	Intermediate Similarity	NPC257124
0.7886	Intermediate Similarity	NPC156840
0.7886	Intermediate Similarity	NPC139617
0.7886	Intermediate Similarity	NPC8547
0.7886	Intermediate Similarity	NPC173746
0.7879	Intermediate Similarity	NPC213711
0.7879	Intermediate Similarity	NPC40352
0.7868	Intermediate Similarity	NPC94280
0.7868	Intermediate Similarity	NPC103947
0.7868	Intermediate Similarity	NPC159150
0.7868	Intermediate Similarity	NPC328419
0.7868	Intermediate Similarity	NPC193673
0.7868	Intermediate Similarity	NPC45783
0.7868	Intermediate Similarity	NPC167096
0.7852	Intermediate Similarity	NPC217574
0.7852	Intermediate Similarity	NPC476345
0.7851	Intermediate Similarity	NPC258171
0.7846	Intermediate Similarity	NPC256167
0.784	Intermediate Similarity	NPC294941
0.7836	Intermediate Similarity	NPC470633
0.7836	Intermediate Similarity	NPC228769
0.7829	Intermediate Similarity	NPC83279
0.7812	Intermediate Similarity	NPC256369
0.781	Intermediate Similarity	NPC196609
0.781	Intermediate Similarity	NPC136330
0.781	Intermediate Similarity	NPC277042
0.781	Intermediate Similarity	NPC230698
0.781	Intermediate Similarity	NPC73883
0.781	Intermediate Similarity	NPC251454
0.781	Intermediate Similarity	NPC205178
0.781	Intermediate Similarity	NPC96406
0.781	Intermediate Similarity	NPC180647
0.781	Intermediate Similarity	NPC255817
0.7803	Intermediate Similarity	NPC17348
0.7795	Intermediate Similarity	NPC120075
0.7794	Intermediate Similarity	NPC219671
0.7794	Intermediate Similarity	NPC104077
0.7794	Intermediate Similarity	NPC259742
0.7794	Intermediate Similarity	NPC147616
0.7794	Intermediate Similarity	NPC471505
0.7794	Intermediate Similarity	NPC227002
0.7794	Intermediate Similarity	NPC106739
0.7787	Intermediate Similarity	NPC146530
0.7786	Intermediate Similarity	NPC13020
0.7786	Intermediate Similarity	NPC140359
0.7778	Intermediate Similarity	NPC63574
0.7778	Intermediate Similarity	NPC181079
0.7778	Intermediate Similarity	NPC173308
0.7769	Intermediate Similarity	NPC193484
0.7754	Intermediate Similarity	NPC137172
0.7754	Intermediate Similarity	NPC145446
0.7754	Intermediate Similarity	NPC99078
0.7752	Intermediate Similarity	NPC263835
0.7744	Intermediate Similarity	NPC473960
0.7737	Intermediate Similarity	NPC169973
0.7717	Intermediate Similarity	NPC258992
0.771	Intermediate Similarity	NPC298486
0.7698	Intermediate Similarity	NPC248505
0.7698	Intermediate Similarity	NPC95366
0.7698	Intermediate Similarity	NPC252107
0.7698	Intermediate Similarity	NPC225745
0.7698	Intermediate Similarity	NPC28641
0.7698	Intermediate Similarity	NPC194359
0.7698	Intermediate Similarity	NPC220923
0.7687	Intermediate Similarity	NPC64948
0.7687	Intermediate Similarity	NPC158737
0.7687	Intermediate Similarity	NPC177167
0.7681	Intermediate Similarity	NPC264956
0.7674	Intermediate Similarity	NPC37858
0.7674	Intermediate Similarity	NPC310338
0.7674	Intermediate Similarity	NPC43275
0.7674	Intermediate Similarity	NPC281298
0.7669	Intermediate Similarity	NPC85830
0.7664	Intermediate Similarity	NPC97316
0.7664	Intermediate Similarity	NPC252833
0.766	Intermediate Similarity	NPC195814
0.7656	Intermediate Similarity	NPC293619
0.7656	Intermediate Similarity	NPC164386
0.7656	Intermediate Similarity	NPC280001
0.7652	Intermediate Similarity	NPC317769
0.7652	Intermediate Similarity	NPC31344
0.7647	Intermediate Similarity	NPC134764
0.7647	Intermediate Similarity	NPC184814
0.7647	Intermediate Similarity	NPC171550
0.7642	Intermediate Similarity	NPC309982
0.7634	Intermediate Similarity	NPC70752
0.763	Intermediate Similarity	NPC57119
0.763	Intermediate Similarity	NPC226862
0.763	Intermediate Similarity	NPC165128
0.763	Intermediate Similarity	NPC158471
0.7626	Intermediate Similarity	NPC174191
0.7626	Intermediate Similarity	NPC7018
0.7626	Intermediate Similarity	NPC135777
0.7626	Intermediate Similarity	NPC101624
0.7626	Intermediate Similarity	NPC142547
0.7626	Intermediate Similarity	NPC416184
0.7626	Intermediate Similarity	NPC184938
0.7626	Intermediate Similarity	NPC469808
0.7623	Intermediate Similarity	NPC41594
0.7619	Intermediate Similarity	NPC165106
0.7615	Intermediate Similarity	NPC289330
0.7615	Intermediate Similarity	NPC232316
0.7615	Intermediate Similarity	NPC53596
0.7615	Intermediate Similarity	NPC227217
0.7615	Intermediate Similarity	NPC17388
0.7615	Intermediate Similarity	NPC95614
0.7615	Intermediate Similarity	NPC471308
0.7615	Intermediate Similarity	NPC117780
0.7615	Intermediate Similarity	NPC165133
0.7615	Intermediate Similarity	NPC56214
0.7615	Intermediate Similarity	NPC242885
0.7615	Intermediate Similarity	NPC160120
0.7609	Intermediate Similarity	NPC25821
0.7609	Intermediate Similarity	NPC196937
0.7609	Intermediate Similarity	NPC471391
0.7609	Intermediate Similarity	NPC471390
0.7609	Intermediate Similarity	NPC6836

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 NPC300955 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	128
0.1-0.2	784
0.2-0.3	1364
0.3-0.4	2604
0.4-0.5	2365
0.5-0.6	1292
0.6-0.7	540
0.7-0.8	69
0.8-0.85	3
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8537	High Similarity	NPD1357	Approved
0.8321	Intermediate Similarity	NPD3145	Approved
0.8321	Intermediate Similarity	NPD3144	Approved
0.812	Intermediate Similarity	NPD2674	Phase 3
0.7985	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.7899	Intermediate Similarity	NPD2161	Phase 2
0.7886	Intermediate Similarity	NPD228	Approved
0.7863	Intermediate Similarity	NPD2922	Phase 1
0.7852	Intermediate Similarity	NPD1726	Clinical (unspecified phase)
0.7842	Intermediate Similarity	NPD1375	Discontinued
0.781	Intermediate Similarity	NPD2492	Phase 1
0.777	Intermediate Similarity	NPD5563	Clinical (unspecified phase)
0.7769	Intermediate Similarity	NPD3705	Approved
0.7769	Intermediate Similarity	NPD776	Approved
0.7708	Intermediate Similarity	NPD4739	Approved
0.7698	Intermediate Similarity	NPD4108	Discontinued
0.7676	Intermediate Similarity	NPD6331	Phase 2
0.7652	Intermediate Similarity	NPD1669	Approved
0.7619	Intermediate Similarity	NPD5283	Phase 1
0.7616	Intermediate Similarity	NPD5604	Discontinued
0.7584	Intermediate Similarity	NPD7945	Clinical (unspecified phase)
0.7556	Intermediate Similarity	NPD1712	Approved
0.7535	Intermediate Similarity	NPD7153	Discontinued
0.7519	Intermediate Similarity	NPD3676	Clinical (unspecified phase)
0.7519	Intermediate Similarity	NPD3685	Discontinued
0.7518	Intermediate Similarity	NPD5109	Approved
0.7518	Intermediate Similarity	NPD5111	Phase 2
0.7518	Intermediate Similarity	NPD5110	Phase 2
0.75	Intermediate Similarity	NPD709	Approved
0.75	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD2157	Approved
0.7402	Intermediate Similarity	NPD821	Approved
0.7379	Intermediate Similarity	NPD2219	Phase 1
0.7372	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD4123	Phase 3
0.7329	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7319	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD2977	Approved
0.7303	Intermediate Similarity	NPD2978	Approved
0.7297	Intermediate Similarity	NPD52	Approved
0.7297	Intermediate Similarity	NPD7527	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD7526	Approved
0.7286	Intermediate Similarity	NPD1558	Phase 1
0.7279	Intermediate Similarity	NPD4357	Discontinued
0.7266	Intermediate Similarity	NPD5718	Phase 2
0.7259	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7252	Intermediate Similarity	NPD5536	Phase 2
0.7248	Intermediate Similarity	NPD2122	Discontinued
0.7241	Intermediate Similarity	NPD4237	Approved
0.7241	Intermediate Similarity	NPD4236	Phase 3
0.7218	Intermediate Similarity	NPD2668	Approved
0.7218	Intermediate Similarity	NPD2667	Approved
0.719	Intermediate Similarity	NPD5773	Approved
0.719	Intermediate Similarity	NPD5772	Approved
0.7185	Intermediate Similarity	NPD2230	Approved
0.7185	Intermediate Similarity	NPD2232	Approved
0.7185	Intermediate Similarity	NPD2233	Approved
0.7183	Intermediate Similarity	NPD2653	Approved
0.7183	Intermediate Similarity	NPD1772	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD2040	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD4993	Discontinued
0.7172	Intermediate Similarity	NPD1044	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1048	Approved
0.7133	Intermediate Similarity	NPD6896	Approved
0.7133	Intermediate Similarity	NPD6895	Approved
0.7123	Intermediate Similarity	NPD3060	Approved
0.7114	Intermediate Similarity	NPD1771	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD4675	Approved
0.7105	Intermediate Similarity	NPD4678	Approved
0.7101	Intermediate Similarity	NPD6584	Phase 3
0.7092	Intermediate Similarity	NPD840	Approved
0.7092	Intermediate Similarity	NPD839	Approved
0.7087	Intermediate Similarity	NPD2684	Approved
0.7083	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD1024	Discontinued
0.7055	Intermediate Similarity	NPD1372	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD5837	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD556	Approved
0.7027	Intermediate Similarity	NPD5241	Discontinued
0.7014	Intermediate Similarity	NPD6111	Discontinued
0.7008	Intermediate Similarity	NPD1358	Approved
0.7007	Intermediate Similarity	NPD4162	Approved
0.7007	Intermediate Similarity	NPD5177	Phase 3
0.7007	Intermediate Similarity	NPD2982	Phase 2
0.7007	Intermediate Similarity	NPD2983	Phase 2
0.6986	Remote Similarity	NPD3656	Approved
0.6972	Remote Similarity	NPD1423	Approved
0.6959	Remote Similarity	NPD4110	Phase 3
0.6959	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.695	Remote Similarity	NPD3027	Phase 3
0.6944	Remote Similarity	NPD4097	Suspended
0.6942	Remote Similarity	NPD9296	Approved
0.694	Remote Similarity	NPD1182	Approved
0.6939	Remote Similarity	NPD2808	Discontinued
0.6934	Remote Similarity	NPD2981	Phase 2
0.6934	Remote Similarity	NPD2337	Clinical (unspecified phase)
0.6934	Remote Similarity	NPD2231	Phase 2
0.6934	Remote Similarity	NPD2235	Phase 2
0.6929	Remote Similarity	NPD9494	Approved
0.6929	Remote Similarity	NPD3134	Approved
0.6928	Remote Similarity	NPD4005	Discontinued
0.6928	Remote Similarity	NPD3111	Phase 1
0.6923	Remote Similarity	NPD2358	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD3620	Phase 2
0.6923	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD1820	Approved
0.6906	Remote Similarity	NPD1819	Approved
0.6906	Remote Similarity	NPD1817	Approved
0.6906	Remote Similarity	NPD1818	Approved
0.6905	Remote Similarity	NPD7243	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD1039	Discontinued
0.6884	Remote Similarity	NPD6583	Phase 3
0.6884	Remote Similarity	NPD6582	Phase 2
0.6883	Remote Similarity	NPD1642	Discontinued
0.687	Remote Similarity	NPD9379	Approved
0.687	Remote Similarity	NPD7843	Approved
0.687	Remote Similarity	NPD9377	Approved
0.6863	Remote Similarity	NPD3687	Approved
0.6863	Remote Similarity	NPD3686	Approved
0.6863	Remote Similarity	NPD4210	Discontinued
0.6846	Remote Similarity	NPD9280	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD7157	Approved
0.6839	Remote Similarity	NPD5090	Approved
0.6839	Remote Similarity	NPD5089	Approved
0.6838	Remote Similarity	NPD2423	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD4626	Approved
0.6831	Remote Similarity	NPD3164	Approved
0.6831	Remote Similarity	NPD3167	Approved
0.6831	Remote Similarity	NPD3166	Approved
0.6831	Remote Similarity	NPD3165	Approved
0.6828	Remote Similarity	NPD4579	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD4664	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD5297	Approved
0.6809	Remote Similarity	NPD3018	Phase 2
0.6809	Remote Similarity	NPD2250	Discontinued
0.6806	Remote Similarity	NPD2238	Phase 2
0.6797	Remote Similarity	NPD1444	Approved
0.6797	Remote Similarity	NPD1445	Approved
0.6791	Remote Similarity	NPD3596	Phase 2
0.6776	Remote Similarity	NPD1754	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD7028	Phase 2
0.6769	Remote Similarity	NPD3022	Approved
0.6769	Remote Similarity	NPD3021	Approved
0.6755	Remote Similarity	NPD7124	Phase 2
0.675	Remote Similarity	NPD2644	Approved
0.6744	Remote Similarity	NPD290	Approved
0.6742	Remote Similarity	NPD1138	Approved
0.6739	Remote Similarity	NPD1091	Approved
0.6738	Remote Similarity	NPD558	Phase 2
0.6736	Remote Similarity	NPD3058	Clinical (unspecified phase)
0.6732	Remote Similarity	NPD1350	Approved
0.6732	Remote Similarity	NPD1349	Approved
0.6732	Remote Similarity	NPD1351	Approved
0.673	Remote Similarity	NPD4055	Discovery
0.6728	Remote Similarity	NPD4083	Discontinued
0.6713	Remote Similarity	NPD3179	Approved
0.6713	Remote Similarity	NPD3180	Approved
0.6711	Remote Similarity	NPD7037	Approved
0.6711	Remote Similarity	NPD4149	Clinical (unspecified phase)
0.671	Remote Similarity	NPD824	Approved
0.6709	Remote Similarity	NPD2560	Approved
0.6709	Remote Similarity	NPD2563	Approved
0.6708	Remote Similarity	NPD2821	Approved
0.6691	Remote Similarity	NPD6581	Approved
0.6691	Remote Similarity	NPD1840	Phase 2
0.6691	Remote Similarity	NPD6580	Approved
0.669	Remote Similarity	NPD2407	Clinical (unspecified phase)
0.6688	Remote Similarity	NPD37	Approved
0.6688	Remote Similarity	NPD5722	Discontinued
0.6667	Remote Similarity	NPD3408	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1794	Approved
0.6667	Remote Similarity	NPD7119	Phase 2
0.6667	Remote Similarity	NPD1139	Approved
0.6667	Remote Similarity	NPD3688	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1770	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3146	Approved
0.6667	Remote Similarity	NPD1137	Approved
0.6667	Remote Similarity	NPD3847	Discontinued
0.6646	Remote Similarity	NPD7201	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD5602	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD5756	Phase 2
0.6644	Remote Similarity	NPD3657	Discovery
0.6643	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6643	Remote Similarity	NPD1420	Approved
0.6643	Remote Similarity	NPD1421	Approved
0.6643	Remote Similarity	NPD596	Approved
0.6643	Remote Similarity	NPD682	Discontinued
0.6643	Remote Similarity	NPD600	Approved
0.6642	Remote Similarity	NPD6830	Clinical (unspecified phase)
0.6642	Remote Similarity	NPD595	Approved
0.6642	Remote Similarity	NPD1798	Approved
0.6642	Remote Similarity	NPD1797	Approved
0.6642	Remote Similarity	NPD593	Approved
0.6641	Remote Similarity	NPD1792	Phase 2
0.6625	Remote Similarity	NPD7832	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