NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	206.09
Volume:	220.74
LogP:	3.696
LogD:	2.988
LogS:	-3.45
# Rotatable Bonds:	4
TPSA:	46.53
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.77
Synthetic Accessibility Score:	1.807
Fsp3:	0.25
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.827
MDCK Permeability:	1.962874193850439e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	0.099

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.31
Plasma Protein Binding (PPB):	89.9872817993164%
Volume Distribution (VD):	0.463
Pgp-substrate:	11.448044776916504%

ADMET: Metabolism

CYP1A2-inhibitor:	0.158
CYP1A2-substrate:	0.102
CYP2C19-inhibitor:	0.085
CYP2C19-substrate:	0.056
CYP2C9-inhibitor:	0.133
CYP2C9-substrate:	0.174
CYP2D6-inhibitor:	0.016
CYP2D6-substrate:	0.09
CYP3A4-inhibitor:	0.037
CYP3A4-substrate:	0.109

ADMET: Excretion

Clearance (CL):	7.601
Half-life (T1/2):	0.847

ADMET: Toxicity

hERG Blockers:	0.041
Human Hepatotoxicity (H-HT):	0.924
Drug-inuced Liver Injury (DILI):	0.937
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.073
Maximum Recommended Daily Dose:	0.008
Skin Sensitization:	0.158
Carcinogencity:	0.406
Eye Corrosion:	0.004
Eye Irritation:	0.952
Respiratory Toxicity:	0.154

Download Data

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

Natural Product: NPC291189

Natural Product ID:	NPC291189
*Common Name:**	Valencic Acid
IUPAC Name:	4-(3-methylbut-2-enoxy)benzoic acid
Synonyms:	Valencic Acid
Standard InCHIKey:	KLZJDQVTNOMAKU-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C12H14O3/c1-9(2)7-8-15-11-5-3-10(4-6-11)12(13)14/h3-7H,8H2,1-2H3,(H,13,14)
SMILES:	CC(=CCOc1ccc(cc1)C(=O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL376892
PubChem CID:	267137
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000176] Benzoic acids and derivatives [CHEMONTID:0002565] Benzoic 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
NPO26601	Zanthoxylum wutaiense	Species	Rutaceae	Eukaryota	root wood	n.a.	n.a.	PMID[18564877]
NPO26601	Zanthoxylum wutaiense	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22472691]
NPO14773	Uncaria perrottetii	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18677	Anagallis arvensis	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14773	Uncaria perrottetii	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14773	Uncaria perrottetii	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19014	Palythoa tuberculosa	Species	Sphenopidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18677	Anagallis arvensis	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26601	Zanthoxylum wutaiense	Species	Rutaceae	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	7
MIC	2
Others	7

Activity Type	# Activity
Cell Line	5
Individual Protein	7
NON-MOLECULAR	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	>	100000.0	nM	PMID[533607]
NPT306	Cell Line	PC-3	Homo sapiens	IC50	>	100000.0	nM	PMID[533607]
NPT170	Cell Line	SK-MEL-28	Homo sapiens	IC50	>	100000.0	nM	PMID[533607]
NPT114	Cell Line	LoVo	Homo sapiens	IC50	>	100000.0	nM	PMID[533607]
NPT540	Individual Protein	Bile acid receptor FXR	Homo sapiens	FC	=	1.107	n.a.	PMID[533608]
NPT540	Individual Protein	Bile acid receptor FXR	Homo sapiens	FC	=	1.063	n.a.	PMID[533608]
NPT540	Individual Protein	Bile acid receptor FXR	Homo sapiens	FC	=	1.196	n.a.	PMID[533608]
NPT540	Individual Protein	Bile acid receptor FXR	Homo sapiens	FC	=	1.677	n.a.	PMID[533608]
NPT540	Individual Protein	Bile acid receptor FXR	Homo sapiens	FC	=	2.315	n.a.	PMID[533608]
NPT540	Individual Protein	Bile acid receptor FXR	Homo sapiens	FC	=	3.023	n.a.	PMID[533608]
NPT540	Individual Protein	Bile acid receptor FXR	Homo sapiens	FC	=	4.18	n.a.	PMID[533608]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	>	200000.0	nM	PMID[533609]
NPT451	Organism	Helicobacter pylori	Helicobacter pylori	MIC	=	100.0	ug.mL-1	PMID[533605]
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC	=	45.0	ug.mL-1	PMID[533606]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	100000.0	nM	PMID[533607]

☑ 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 NPC291189 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	274
0.1-0.2	1535
0.2-0.3	4396
0.3-0.4	9779
0.4-0.5	8087
0.5-0.6	4133
0.6-0.7	8685
0.7-0.8	5328
0.8-0.85	437
0.85-0.9	29
0.9-0.95	9
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC69403
0.9829	High Similarity	NPC221798
0.9664	High Similarity	NPC475236
0.9652	High Similarity	NPC61779
0.9397	High Similarity	NPC94298
0.9397	High Similarity	NPC27633
0.9304	High Similarity	NPC220540
0.9224	High Similarity	NPC131192
0.9187	High Similarity	NPC2596
0.9187	High Similarity	NPC2401
0.912	High Similarity	NPC104854
0.904	High Similarity	NPC109778
0.8976	High Similarity	NPC66158
0.8943	High Similarity	NPC165556
0.8898	High Similarity	NPC470860
0.8889	High Similarity	NPC86774
0.8889	High Similarity	NPC252004
0.8889	High Similarity	NPC327457
0.8862	High Similarity	NPC184219
0.88	High Similarity	NPC121104
0.879	High Similarity	NPC49938
0.874	High Similarity	NPC285776
0.874	High Similarity	NPC307732
0.874	High Similarity	NPC42292
0.872	High Similarity	NPC204579
0.872	High Similarity	NPC110211
0.8699	High Similarity	NPC67300
0.8667	High Similarity	NPC240664
0.8655	High Similarity	NPC322358
0.8651	High Similarity	NPC37512
0.8632	High Similarity	NPC23332
0.8632	High Similarity	NPC57879
0.8621	High Similarity	NPC234639
0.8583	High Similarity	NPC293453
0.8582	High Similarity	NPC184053
0.8571	High Similarity	NPC235250
0.8548	High Similarity	NPC311219
0.8547	High Similarity	NPC183648
0.8538	High Similarity	NPC283823
0.8538	High Similarity	NPC159418
0.8522	High Similarity	NPC184658
0.8516	High Similarity	NPC226855
0.8516	High Similarity	NPC78662
0.8516	High Similarity	NPC8005
0.8516	High Similarity	NPC194979
0.8516	High Similarity	NPC939
0.8507	High Similarity	NPC326065
0.8462	Intermediate Similarity	NPC111888
0.8456	Intermediate Similarity	NPC473090
0.8448	Intermediate Similarity	NPC29883
0.8443	Intermediate Similarity	NPC293424
0.8438	Intermediate Similarity	NPC80694
0.8438	Intermediate Similarity	NPC186098
0.8438	Intermediate Similarity	NPC473744
0.8435	Intermediate Similarity	NPC238115
0.8435	Intermediate Similarity	NPC128730
0.8433	Intermediate Similarity	NPC473988
0.8425	Intermediate Similarity	NPC154275
0.8425	Intermediate Similarity	NPC474476
0.8425	Intermediate Similarity	NPC95309
0.8421	Intermediate Similarity	NPC240593
0.8413	Intermediate Similarity	NPC6888
0.8413	Intermediate Similarity	NPC145134
0.8397	Intermediate Similarity	NPC203817
0.8376	Intermediate Similarity	NPC291837
0.8374	Intermediate Similarity	NPC264976
0.8372	Intermediate Similarity	NPC238309
0.8372	Intermediate Similarity	NPC66246
0.8372	Intermediate Similarity	NPC170546
0.837	Intermediate Similarity	NPC80098
0.8362	Intermediate Similarity	NPC1065
0.8362	Intermediate Similarity	NPC176971
0.8361	Intermediate Similarity	NPC45104
0.8361	Intermediate Similarity	NPC217423
0.8359	Intermediate Similarity	NPC158654
0.8359	Intermediate Similarity	NPC22783
0.8358	Intermediate Similarity	NPC188879
0.8358	Intermediate Similarity	NPC207516
0.8348	Intermediate Similarity	NPC2518
0.8346	Intermediate Similarity	NPC4164
0.8346	Intermediate Similarity	NPC294470
0.8333	Intermediate Similarity	NPC141252
0.8333	Intermediate Similarity	NPC155098
0.8333	Intermediate Similarity	NPC109241
0.8333	Intermediate Similarity	NPC223457
0.8333	Intermediate Similarity	NPC11799
0.8321	Intermediate Similarity	NPC302844
0.8321	Intermediate Similarity	NPC31872
0.8321	Intermediate Similarity	NPC473584
0.8321	Intermediate Similarity	NPC475589
0.8309	Intermediate Similarity	NPC307990
0.8309	Intermediate Similarity	NPC16455
0.8308	Intermediate Similarity	NPC183348
0.8308	Intermediate Similarity	NPC298268
0.8308	Intermediate Similarity	NPC282230
0.8308	Intermediate Similarity	NPC12694
0.8308	Intermediate Similarity	NPC247779
0.8306	Intermediate Similarity	NPC230951
0.8305	Intermediate Similarity	NPC259554
0.8296	Intermediate Similarity	NPC188947
0.8296	Intermediate Similarity	NPC124269
0.8296	Intermediate Similarity	NPC280284
0.8296	Intermediate Similarity	NPC99333
0.8293	Intermediate Similarity	NPC94637
0.8291	Intermediate Similarity	NPC151530
0.8291	Intermediate Similarity	NPC157473
0.8284	Intermediate Similarity	NPC187826
0.8284	Intermediate Similarity	NPC135837
0.8276	Intermediate Similarity	NPC8302
0.8271	Intermediate Similarity	NPC212729
0.8271	Intermediate Similarity	NPC236974
0.8271	Intermediate Similarity	NPC144027
0.8268	Intermediate Similarity	NPC255073
0.8264	Intermediate Similarity	NPC81808
0.8261	Intermediate Similarity	NPC113397
0.8261	Intermediate Similarity	NPC179686
0.8258	Intermediate Similarity	NPC114116
0.8258	Intermediate Similarity	NPC25937
0.8244	Intermediate Similarity	NPC196979
0.8244	Intermediate Similarity	NPC470977
0.8244	Intermediate Similarity	NPC15083
0.8244	Intermediate Similarity	NPC5515
0.8244	Intermediate Similarity	NPC470976
0.8244	Intermediate Similarity	NPC270369
0.8244	Intermediate Similarity	NPC473777
0.8235	Intermediate Similarity	NPC231251
0.8235	Intermediate Similarity	NPC88868
0.8235	Intermediate Similarity	NPC25067
0.8235	Intermediate Similarity	NPC137009
0.8235	Intermediate Similarity	NPC230902
0.8235	Intermediate Similarity	NPC51181
0.8235	Intermediate Similarity	NPC254994
0.8231	Intermediate Similarity	NPC60558
0.8231	Intermediate Similarity	NPC473019
0.8226	Intermediate Similarity	NPC328459
0.8226	Intermediate Similarity	NPC90522
0.8222	Intermediate Similarity	NPC266597
0.8222	Intermediate Similarity	NPC290291
0.8222	Intermediate Similarity	NPC250266
0.8222	Intermediate Similarity	NPC476480
0.8222	Intermediate Similarity	NPC332594
0.8222	Intermediate Similarity	NPC275055
0.8222	Intermediate Similarity	NPC84585
0.8217	Intermediate Similarity	NPC128428
0.8217	Intermediate Similarity	NPC305518
0.8217	Intermediate Similarity	NPC281020
0.8214	Intermediate Similarity	NPC66991
0.8214	Intermediate Similarity	NPC472969
0.8211	Intermediate Similarity	NPC469954
0.8209	Intermediate Similarity	NPC223616
0.8209	Intermediate Similarity	NPC163029
0.8209	Intermediate Similarity	NPC60667
0.8209	Intermediate Similarity	NPC151113
0.8203	Intermediate Similarity	NPC470858
0.8203	Intermediate Similarity	NPC2771
0.8203	Intermediate Similarity	NPC52035
0.8201	Intermediate Similarity	NPC291153
0.8197	Intermediate Similarity	NPC51345
0.8197	Intermediate Similarity	NPC188907
0.8195	Intermediate Similarity	NPC57601
0.8195	Intermediate Similarity	NPC45404
0.8195	Intermediate Similarity	NPC311339
0.8188	Intermediate Similarity	NPC469615
0.8182	Intermediate Similarity	NPC309717
0.8182	Intermediate Similarity	NPC470859
0.8182	Intermediate Similarity	NPC313618
0.8182	Intermediate Similarity	NPC128348
0.8182	Intermediate Similarity	NPC112192
0.8182	Intermediate Similarity	NPC64359
0.8182	Intermediate Similarity	NPC66384
0.8182	Intermediate Similarity	NPC164236
0.8182	Intermediate Similarity	NPC11824
0.8182	Intermediate Similarity	NPC308037
0.8182	Intermediate Similarity	NPC189106
0.8168	Intermediate Similarity	NPC185497
0.8162	Intermediate Similarity	NPC147686
0.8162	Intermediate Similarity	NPC472460
0.8162	Intermediate Similarity	NPC475045
0.8162	Intermediate Similarity	NPC329225
0.816	Intermediate Similarity	NPC474874
0.816	Intermediate Similarity	NPC72977
0.8156	Intermediate Similarity	NPC98809
0.8156	Intermediate Similarity	NPC476394
0.8148	Intermediate Similarity	NPC231772
0.8148	Intermediate Similarity	NPC110899
0.8148	Intermediate Similarity	NPC470397
0.8148	Intermediate Similarity	NPC47815
0.8148	Intermediate Similarity	NPC112068
0.8148	Intermediate Similarity	NPC240147
0.8148	Intermediate Similarity	NPC125417
0.8148	Intermediate Similarity	NPC95679
0.8148	Intermediate Similarity	NPC121243
0.8148	Intermediate Similarity	NPC29353
0.8148	Intermediate Similarity	NPC194281
0.8148	Intermediate Similarity	NPC234133
0.8148	Intermediate Similarity	NPC124784
0.8148	Intermediate Similarity	NPC156910
0.8148	Intermediate Similarity	NPC473887
0.8148	Intermediate Similarity	NPC127447
0.8148	Intermediate Similarity	NPC470398

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 NPC291189 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	242
0.1-0.2	945
0.2-0.3	1584
0.3-0.4	2513
0.4-0.5	1862
0.5-0.6	1264
0.6-0.7	537
0.7-0.8	183
0.8-0.85	17
0.85-0.9	2
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9397	High Similarity	NPD9545	Approved
0.8647	High Similarity	NPD7421	Clinical (unspecified phase)
0.8582	High Similarity	NPD4628	Phase 3
0.8548	High Similarity	NPD9717	Approved
0.8487	Intermediate Similarity	NPD1241	Discontinued
0.8448	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.84	Intermediate Similarity	NPD1608	Approved
0.8308	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8203	Intermediate Similarity	NPD1203	Approved
0.8182	Intermediate Similarity	NPD1240	Approved
0.8162	Intermediate Similarity	NPD1549	Phase 2
0.816	Intermediate Similarity	NPD17	Approved
0.816	Intermediate Similarity	NPD1778	Approved
0.8148	Intermediate Similarity	NPD1551	Phase 2
0.8145	Intermediate Similarity	NPD1894	Discontinued
0.813	Intermediate Similarity	NPD9493	Approved
0.8129	Intermediate Similarity	NPD6799	Approved
0.812	Intermediate Similarity	NPD230	Phase 1
0.8088	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8088	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8077	Intermediate Similarity	NPD9494	Approved
0.806	Intermediate Similarity	NPD1607	Approved
0.8051	Intermediate Similarity	NPD3134	Approved
0.8031	Intermediate Similarity	NPD422	Phase 1
0.8029	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD1019	Discontinued
0.7986	Intermediate Similarity	NPD7411	Suspended
0.7983	Intermediate Similarity	NPD1358	Approved
0.7969	Intermediate Similarity	NPD1481	Phase 2
0.7941	Intermediate Similarity	NPD1510	Phase 2
0.7914	Intermediate Similarity	NPD3750	Approved
0.7895	Intermediate Similarity	NPD411	Approved
0.7891	Intermediate Similarity	NPD1535	Discovery
0.7883	Intermediate Similarity	NPD2796	Approved
0.7879	Intermediate Similarity	NPD6832	Phase 2
0.7852	Intermediate Similarity	NPD447	Suspended
0.7846	Intermediate Similarity	NPD3225	Approved
0.7829	Intermediate Similarity	NPD3972	Approved
0.781	Intermediate Similarity	NPD2799	Discontinued
0.7803	Intermediate Similarity	NPD454	Approved
0.7793	Intermediate Similarity	NPD6599	Discontinued
0.7786	Intermediate Similarity	NPD2797	Approved
0.7778	Intermediate Similarity	NPD3142	Approved
0.7778	Intermediate Similarity	NPD3140	Approved
0.7762	Intermediate Similarity	NPD2186	Approved
0.7761	Intermediate Similarity	NPD3764	Approved
0.7755	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7755	Intermediate Similarity	NPD7819	Suspended
0.7752	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD2354	Approved
0.7718	Intermediate Similarity	NPD7075	Discontinued
0.7714	Intermediate Similarity	NPD1243	Approved
0.7698	Intermediate Similarity	NPD2344	Approved
0.7692	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7687	Intermediate Similarity	NPD6801	Discontinued
0.7681	Intermediate Similarity	NPD3748	Approved
0.7681	Intermediate Similarity	NPD7033	Discontinued
0.7681	Intermediate Similarity	NPD4308	Phase 3
0.7676	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7676	Intermediate Similarity	NPD7440	Discontinued
0.7667	Intermediate Similarity	NPD9697	Approved
0.766	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.763	Intermediate Similarity	NPD3268	Approved
0.763	Intermediate Similarity	NPD2313	Discontinued
0.763	Intermediate Similarity	NPD6798	Discontinued
0.7626	Intermediate Similarity	NPD2935	Discontinued
0.7622	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7606	Intermediate Similarity	NPD3887	Approved
0.7591	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD920	Approved
0.7576	Intermediate Similarity	NPD1283	Approved
0.7574	Intermediate Similarity	NPD4062	Phase 3
0.7574	Intermediate Similarity	NPD6233	Phase 2
0.7571	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7571	Intermediate Similarity	NPD2353	Approved
0.7571	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7569	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7569	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7542	Intermediate Similarity	NPD1238	Approved
0.7541	Intermediate Similarity	NPD9267	Approved
0.7541	Intermediate Similarity	NPD9263	Approved
0.7541	Intermediate Similarity	NPD9264	Approved
0.7538	Intermediate Similarity	NPD3496	Discontinued
0.7533	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7533	Intermediate Similarity	NPD7768	Phase 2
0.7517	Intermediate Similarity	NPD6273	Approved
0.75	Intermediate Similarity	NPD1296	Phase 2
0.75	Intermediate Similarity	NPD1511	Approved
0.7483	Intermediate Similarity	NPD3226	Approved
0.7483	Intermediate Similarity	NPD2309	Approved
0.748	Intermediate Similarity	NPD9266	Approved
0.748	Intermediate Similarity	NPD74	Approved
0.748	Intermediate Similarity	NPD2684	Approved
0.7467	Intermediate Similarity	NPD3817	Phase 2
0.7466	Intermediate Similarity	NPD5403	Approved
0.7464	Intermediate Similarity	NPD6355	Discontinued
0.7464	Intermediate Similarity	NPD1933	Approved
0.7459	Intermediate Similarity	NPD968	Approved
0.745	Intermediate Similarity	NPD1934	Approved
0.7448	Intermediate Similarity	NPD2534	Approved
0.7448	Intermediate Similarity	NPD2533	Approved
0.7448	Intermediate Similarity	NPD5401	Approved
0.7448	Intermediate Similarity	NPD2532	Approved
0.7444	Intermediate Similarity	NPD1876	Approved
0.7442	Intermediate Similarity	NPD1548	Phase 1
0.7419	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD3451	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD3882	Suspended
0.7413	Intermediate Similarity	NPD7003	Approved
0.7405	Intermediate Similarity	NPD3847	Discontinued
0.74	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7398	Intermediate Similarity	NPD290	Approved
0.7397	Intermediate Similarity	NPD1512	Approved
0.7391	Intermediate Similarity	NPD4307	Phase 2
0.7388	Intermediate Similarity	NPD3266	Approved
0.7388	Intermediate Similarity	NPD3267	Approved
0.7385	Intermediate Similarity	NPD9268	Approved
0.7385	Intermediate Similarity	NPD5585	Approved
0.7383	Intermediate Similarity	NPD958	Approved
0.7381	Intermediate Similarity	NPD821	Approved
0.7381	Intermediate Similarity	NPD5535	Approved
0.7376	Intermediate Similarity	NPD4477	Approved
0.7376	Intermediate Similarity	NPD4476	Approved
0.7368	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD3749	Approved
0.7365	Intermediate Similarity	NPD7458	Discontinued
0.7353	Intermediate Similarity	NPD2614	Approved
0.7351	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7348	Intermediate Similarity	NPD1281	Approved
0.7338	Intermediate Similarity	NPD4340	Discontinued
0.7333	Intermediate Similarity	NPD2798	Approved
0.7333	Intermediate Similarity	NPD5647	Approved
0.7329	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7328	Intermediate Similarity	NPD4626	Approved
0.7324	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7324	Intermediate Similarity	NPD2346	Discontinued
0.7324	Intermediate Similarity	NPD6004	Phase 3
0.7324	Intermediate Similarity	NPD6002	Phase 3
0.7324	Intermediate Similarity	NPD6005	Phase 3
0.7324	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD4380	Phase 2
0.7313	Intermediate Similarity	NPD196	Phase 1
0.7304	Intermediate Similarity	NPD9256	Approved
0.7304	Intermediate Similarity	NPD9258	Approved
0.7297	Intermediate Similarity	NPD957	Approved
0.7293	Intermediate Similarity	NPD9269	Phase 2
0.7292	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD2801	Approved
0.7279	Intermediate Similarity	NPD9509	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD5844	Phase 1
0.7267	Intermediate Similarity	NPD6385	Approved
0.7267	Intermediate Similarity	NPD6386	Approved
0.7252	Intermediate Similarity	NPD5691	Approved
0.7244	Intermediate Similarity	NPD7843	Approved
0.723	Intermediate Similarity	NPD1670	Discontinued
0.723	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD2976	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD2800	Approved
0.7219	Intermediate Similarity	NPD7577	Discontinued
0.7218	Intermediate Similarity	NPD1610	Phase 2
0.7214	Intermediate Similarity	NPD5124	Phase 1
0.7214	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7213	Intermediate Similarity	NPD9261	Approved
0.7211	Intermediate Similarity	NPD3146	Approved
0.7211	Intermediate Similarity	NPD3688	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD919	Approved
0.72	Intermediate Similarity	NPD2182	Approved
0.7188	Intermediate Similarity	NPD5953	Discontinued
0.7174	Intermediate Similarity	NPD5163	Phase 2
0.7171	Intermediate Similarity	NPD1006	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD1465	Phase 2
0.717	Intermediate Similarity	NPD7286	Phase 2
0.7162	Intermediate Similarity	NPD5049	Phase 3
0.7154	Intermediate Similarity	NPD164	Approved
0.7153	Intermediate Similarity	NPD4534	Discontinued
0.7133	Intermediate Similarity	NPD2240	Approved
0.7133	Intermediate Similarity	NPD2239	Approved
0.7133	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD6362	Approved
0.7132	Intermediate Similarity	NPD9281	Approved
0.7132	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD987	Approved
0.7124	Intermediate Similarity	NPD5402	Approved
0.7124	Intermediate Similarity	NPD4288	Approved
0.7123	Intermediate Similarity	NPD6190	Approved
0.7121	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD2249	Approved
0.7115	Intermediate Similarity	NPD2247	Approved
0.7111	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD4359	Approved
0.7107	Intermediate Similarity	NPD7177	Discontinued
0.7103	Intermediate Similarity	NPD1652	Phase 2
0.7099	Intermediate Similarity	NPD9092	Discovery
0.709	Intermediate Similarity	NPD1091	Approved
0.7077	Intermediate Similarity	NPD7157	Approved
0.7055	Intermediate Similarity	NPD4110	Phase 3
0.7055	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.705	Intermediate Similarity	NPD7095	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