NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	268.11
Volume:	290.754
LogP:	3.181
LogD:	3.051
LogS:	-3.609
# Rotatable Bonds:	5
TPSA:	57.53
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.643
Synthetic Accessibility Score:	2.699
Fsp3:	0.118
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:	-4.612
MDCK Permeability:	1.4894897503836546e-05
Pgp-inhibitor:	0.052
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.116
30% Bioavailability (F30%):	0.014

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.05
Plasma Protein Binding (PPB):	96.91950988769531%
Volume Distribution (VD):	0.441
Pgp-substrate:	1.494519829750061%

ADMET: Metabolism

CYP1A2-inhibitor:	0.838
CYP1A2-substrate:	0.425
CYP2C19-inhibitor:	0.927
CYP2C19-substrate:	0.065
CYP2C9-inhibitor:	0.848
CYP2C9-substrate:	0.962
CYP2D6-inhibitor:	0.802
CYP2D6-substrate:	0.877
CYP3A4-inhibitor:	0.737
CYP3A4-substrate:	0.293

ADMET: Excretion

Clearance (CL):	8.907
Half-life (T1/2):	0.833

ADMET: Toxicity

hERG Blockers:	0.022
Human Hepatotoxicity (H-HT):	0.037
Drug-inuced Liver Injury (DILI):	0.056
AMES Toxicity:	0.185
Rat Oral Acute Toxicity:	0.311
Maximum Recommended Daily Dose:	0.796
Skin Sensitization:	0.308
Carcinogencity:	0.635
Eye Corrosion:	0.004
Eye Irritation:	0.829
Respiratory Toxicity:	0.073

Download Data

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

Natural Product: NPC322197

Natural Product ID:	NPC322197
*Common Name:**	1,3-Bis(4-Hydroxyphenyl)Pent-4-En-1-One
IUPAC Name:	1,3-bis(4-hydroxyphenyl)pent-4-en-1-one
Synonyms:
Standard InCHIKey:	AVGYGUNTLQSTKJ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C17H16O3/c1-2-12(13-3-7-15(18)8-4-13)11-17(20)14-5-9-16(19)10-6-14/h2-10,12,18-19H,1,11H2
SMILES:	C=CC(c1ccc(cc1)O)CC(=O)c1ccc(cc1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL471605
PubChem CID:	44575609
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds

*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
NPO11694	Asparagus cochinchinensis	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14987058]
NPO11694	Asparagus cochinchinensis	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11694	Asparagus cochinchinensis	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11694	Asparagus cochinchinensis	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11694	Asparagus cochinchinensis	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO11694	Asparagus cochinchinensis	Species	Asparagaceae	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
Others	1

Activity Type	# Activity
Cell Line	6
Organism	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	>	20.0	ug.mL-1	PMID[475039]
NPT1851	Cell Line	Col2	Homo sapiens	IC50	>	20.0	ug.mL-1	PMID[475039]
NPT858	Cell Line	LNCaP	Homo sapiens	IC50	>	20.0	ug.mL-1	PMID[475039]
NPT1034	Cell Line	Lu1	Homo sapiens	IC50	>	20.0	ug.mL-1	PMID[475039]
NPT737	Cell Line	HUVEC	Homo sapiens	IC50	>	20.0	ug.mL-1	PMID[475039]
NPT521	Cell Line	RBL-2H3	Rattus norvegicus	IC50	=	34600.0	nM	PMID[475040]
NPT27	Others	Unspecified		CC50	=	76800.0	nM	PMID[475039]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	IC50	=	74600.0	nM	PMID[475039]

☑ 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 NPC322197 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	307
0.1-0.2	1551
0.2-0.3	3784
0.3-0.4	10520
0.4-0.5	8432
0.5-0.6	6390
0.6-0.7	8637
0.7-0.8	2780
0.8-0.85	237
0.85-0.9	43
0.9-0.95	14
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9533	High Similarity	NPC116842
0.9346	High Similarity	NPC17525
0.9259	High Similarity	NPC95172
0.9204	High Similarity	NPC249435
0.9159	High Similarity	NPC29989
0.9159	High Similarity	NPC95178
0.9159	High Similarity	NPC69332
0.9091	High Similarity	NPC268388
0.9083	High Similarity	NPC88141
0.9074	High Similarity	NPC226699
0.8981	High Similarity	NPC70843
0.8981	High Similarity	NPC6984
0.8974	High Similarity	NPC68167
0.8972	High Similarity	NPC120693
0.8972	High Similarity	NPC261573
0.8972	High Similarity	NPC8931
0.8966	High Similarity	NPC216216
0.8929	High Similarity	NPC242136
0.8899	High Similarity	NPC141523
0.8889	High Similarity	NPC295034
0.8889	High Similarity	NPC120545
0.8843	High Similarity	NPC96024
0.8839	High Similarity	NPC231717
0.8814	High Similarity	NPC91478
0.8807	High Similarity	NPC188677
0.8803	High Similarity	NPC248363
0.875	High Similarity	NPC212718
0.875	High Similarity	NPC114682
0.8718	High Similarity	NPC159525
0.8684	High Similarity	NPC285350
0.8673	High Similarity	NPC286222
0.8667	High Similarity	NPC199273
0.8661	High Similarity	NPC21162
0.8655	High Similarity	NPC282577
0.8655	High Similarity	NPC139171
0.8632	High Similarity	NPC473767
0.8632	High Similarity	NPC158222
0.8618	High Similarity	NPC276238
0.8609	High Similarity	NPC23402
0.8607	High Similarity	NPC176130
0.8607	High Similarity	NPC78364
0.8607	High Similarity	NPC84672
0.8607	High Similarity	NPC69424
0.8607	High Similarity	NPC72667
0.8596	High Similarity	NPC11824
0.8571	High Similarity	NPC156139
0.8559	High Similarity	NPC34715
0.8547	High Similarity	NPC474890
0.8547	High Similarity	NPC161943
0.8547	High Similarity	NPC273282
0.8537	High Similarity	NPC473017
0.8537	High Similarity	NPC229894
0.8534	High Similarity	NPC325646
0.8534	High Similarity	NPC299252
0.8534	High Similarity	NPC277394
0.8534	High Similarity	NPC61062
0.8534	High Similarity	NPC28951
0.8532	High Similarity	NPC68269
0.8532	High Similarity	NPC135784
0.8525	High Similarity	NPC254492
0.8525	High Similarity	NPC62952
0.8512	High Similarity	NPC164014
0.8505	High Similarity	NPC201967
0.85	High Similarity	NPC133909
0.85	High Similarity	NPC32032
0.8496	Intermediate Similarity	NPC252544
0.8496	Intermediate Similarity	NPC321252
0.8487	Intermediate Similarity	NPC297186
0.8468	Intermediate Similarity	NPC117899
0.8468	Intermediate Similarity	NPC474998
0.8468	Intermediate Similarity	NPC92624
0.8468	Intermediate Similarity	NPC171460
0.8462	Intermediate Similarity	NPC469954
0.8462	Intermediate Similarity	NPC150919
0.8455	Intermediate Similarity	NPC169250
0.8455	Intermediate Similarity	NPC23126
0.8455	Intermediate Similarity	NPC105157
0.8455	Intermediate Similarity	NPC103356
0.8455	Intermediate Similarity	NPC98254
0.8455	Intermediate Similarity	NPC100067
0.8455	Intermediate Similarity	NPC30501
0.8455	Intermediate Similarity	NPC190043
0.8455	Intermediate Similarity	NPC266689
0.8455	Intermediate Similarity	NPC162612
0.8455	Intermediate Similarity	NPC72158
0.8443	Intermediate Similarity	NPC123506
0.8426	Intermediate Similarity	NPC280869
0.8426	Intermediate Similarity	NPC130193
0.8421	Intermediate Similarity	NPC177576
0.8417	Intermediate Similarity	NPC19174
0.8417	Intermediate Similarity	NPC143427
0.8417	Intermediate Similarity	NPC73532
0.8417	Intermediate Similarity	NPC115159
0.8417	Intermediate Similarity	NPC196976
0.8417	Intermediate Similarity	NPC267552
0.8417	Intermediate Similarity	NPC242895
0.8417	Intermediate Similarity	NPC45438
0.8417	Intermediate Similarity	NPC224273
0.8413	Intermediate Similarity	NPC175738
0.8411	Intermediate Similarity	NPC216520
0.8411	Intermediate Similarity	NPC82664
0.8411	Intermediate Similarity	NPC292730
0.8411	Intermediate Similarity	NPC132271
0.84	Intermediate Similarity	NPC108129
0.84	Intermediate Similarity	NPC245395
0.84	Intermediate Similarity	NPC259942
0.8393	Intermediate Similarity	NPC29883
0.8393	Intermediate Similarity	NPC228737
0.839	Intermediate Similarity	NPC184527
0.8387	Intermediate Similarity	NPC3009
0.8387	Intermediate Similarity	NPC234175
0.8387	Intermediate Similarity	NPC95537
0.8387	Intermediate Similarity	NPC21305
0.8387	Intermediate Similarity	NPC221777
0.8387	Intermediate Similarity	NPC193203
0.8378	Intermediate Similarity	NPC219913
0.8376	Intermediate Similarity	NPC477453
0.8376	Intermediate Similarity	NPC19290
0.8376	Intermediate Similarity	NPC83718
0.8374	Intermediate Similarity	NPC267846
0.8374	Intermediate Similarity	NPC15837
0.8374	Intermediate Similarity	NPC8745
0.8361	Intermediate Similarity	NPC13238
0.8333	Intermediate Similarity	NPC190971
0.8333	Intermediate Similarity	NPC471851
0.8333	Intermediate Similarity	NPC236520
0.8333	Intermediate Similarity	NPC18798
0.8333	Intermediate Similarity	NPC294361
0.8333	Intermediate Similarity	NPC260000
0.832	Intermediate Similarity	NPC109123
0.832	Intermediate Similarity	NPC303910
0.8319	Intermediate Similarity	NPC188814
0.8319	Intermediate Similarity	NPC224584
0.8319	Intermediate Similarity	NPC195262
0.8306	Intermediate Similarity	NPC107672
0.8306	Intermediate Similarity	NPC116513
0.8305	Intermediate Similarity	NPC174087
0.8304	Intermediate Similarity	NPC184658
0.8293	Intermediate Similarity	NPC10926
0.8281	Intermediate Similarity	NPC166480
0.8281	Intermediate Similarity	NPC282780
0.8279	Intermediate Similarity	NPC174991
0.8273	Intermediate Similarity	NPC472585
0.8241	Intermediate Similarity	NPC473388
0.8231	Intermediate Similarity	NPC213603
0.8231	Intermediate Similarity	NPC24394
0.8226	Intermediate Similarity	NPC473751
0.8224	Intermediate Similarity	NPC151715
0.8217	Intermediate Similarity	NPC477596
0.8203	Intermediate Similarity	NPC477139
0.8203	Intermediate Similarity	NPC213485
0.8203	Intermediate Similarity	NPC40524
0.8203	Intermediate Similarity	NPC139074
0.8203	Intermediate Similarity	NPC78307
0.8197	Intermediate Similarity	NPC244351
0.8197	Intermediate Similarity	NPC309765
0.8197	Intermediate Similarity	NPC86900
0.8197	Intermediate Similarity	NPC283514
0.8197	Intermediate Similarity	NPC300274
0.819	Intermediate Similarity	NPC228988
0.8189	Intermediate Similarity	NPC93015
0.8189	Intermediate Similarity	NPC475042
0.8182	Intermediate Similarity	NPC52472
0.8182	Intermediate Similarity	NPC149246
0.8182	Intermediate Similarity	NPC146642
0.8175	Intermediate Similarity	NPC25736
0.8174	Intermediate Similarity	NPC222905
0.8168	Intermediate Similarity	NPC20210
0.8167	Intermediate Similarity	NPC258366
0.8167	Intermediate Similarity	NPC31296
0.8167	Intermediate Similarity	NPC473974
0.8167	Intermediate Similarity	NPC79933
0.8167	Intermediate Similarity	NPC161617
0.8167	Intermediate Similarity	NPC182240
0.8158	Intermediate Similarity	NPC317305
0.8154	Intermediate Similarity	NPC7464
0.8151	Intermediate Similarity	NPC160199
0.8151	Intermediate Similarity	NPC269414
0.8148	Intermediate Similarity	NPC26244
0.8145	Intermediate Similarity	NPC49938
0.8145	Intermediate Similarity	NPC475733
0.8145	Intermediate Similarity	NPC477454
0.814	Intermediate Similarity	NPC202225
0.814	Intermediate Similarity	NPC477594
0.814	Intermediate Similarity	NPC475088
0.814	Intermediate Similarity	NPC50924
0.8136	Intermediate Similarity	NPC161304
0.813	Intermediate Similarity	NPC472029
0.813	Intermediate Similarity	NPC273683
0.813	Intermediate Similarity	NPC375356
0.813	Intermediate Similarity	NPC275145
0.813	Intermediate Similarity	NPC65761
0.8125	Intermediate Similarity	NPC309717
0.8125	Intermediate Similarity	NPC128348
0.8125	Intermediate Similarity	NPC112192
0.8125	Intermediate Similarity	NPC66384
0.8125	Intermediate Similarity	NPC164236
0.8125	Intermediate Similarity	NPC189106
0.8115	Intermediate Similarity	NPC303737
0.8115	Intermediate Similarity	NPC198336

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 NPC322197 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	318
0.1-0.2	951
0.2-0.3	1120
0.3-0.4	2538
0.4-0.5	2308
0.5-0.6	1328
0.6-0.7	476
0.7-0.8	101
0.8-0.85	9
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8475	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.8426	Intermediate Similarity	NPD3020	Approved
0.8393	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.8197	Intermediate Similarity	NPD3972	Approved
0.8148	Intermediate Similarity	NPD2859	Approved
0.8148	Intermediate Similarity	NPD2860	Approved
0.8145	Intermediate Similarity	NPD1164	Approved
0.8115	Intermediate Similarity	NPD1201	Approved
0.8099	Intermediate Similarity	NPD3019	Approved
0.8099	Intermediate Similarity	NPD2932	Approved
0.8067	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.8056	Intermediate Similarity	NPD2933	Approved
0.8056	Intermediate Similarity	NPD2934	Approved
0.8	Intermediate Similarity	NPD1470	Approved
0.7984	Intermediate Similarity	NPD943	Approved
0.7969	Intermediate Similarity	NPD3764	Approved
0.7965	Intermediate Similarity	NPD1237	Approved
0.7937	Intermediate Similarity	NPD2798	Approved
0.7934	Intermediate Similarity	NPD9545	Approved
0.792	Intermediate Similarity	NPD1876	Approved
0.7895	Intermediate Similarity	NPD2344	Approved
0.7876	Intermediate Similarity	NPD1929	Approved
0.7876	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7876	Intermediate Similarity	NPD1930	Approved
0.7846	Intermediate Similarity	NPD1240	Approved
0.7778	Intermediate Similarity	NPD3022	Approved
0.7778	Intermediate Similarity	NPD3021	Approved
0.7744	Intermediate Similarity	NPD2799	Discontinued
0.7744	Intermediate Similarity	NPD1510	Phase 2
0.7744	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD1607	Approved
0.7692	Intermediate Similarity	NPD74	Approved
0.7692	Intermediate Similarity	NPD9266	Approved
0.7664	Intermediate Similarity	NPD2309	Approved
0.7619	Intermediate Similarity	NPD4878	Approved
0.7611	Intermediate Similarity	NPD2066	Phase 3
0.7607	Intermediate Similarity	NPD9263	Approved
0.7607	Intermediate Similarity	NPD9267	Approved
0.7607	Intermediate Similarity	NPD9264	Approved
0.7603	Intermediate Similarity	NPD5951	Approved
0.7591	Intermediate Similarity	NPD4628	Phase 3
0.7559	Intermediate Similarity	NPD1755	Approved
0.7556	Intermediate Similarity	NPD5406	Approved
0.7556	Intermediate Similarity	NPD5404	Approved
0.7556	Intermediate Similarity	NPD2935	Discontinued
0.7556	Intermediate Similarity	NPD5405	Approved
0.7556	Intermediate Similarity	NPD5408	Approved
0.7518	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.748	Intermediate Similarity	NPD9493	Approved
0.748	Intermediate Similarity	NPD1608	Approved
0.7478	Intermediate Similarity	NPD1932	Approved
0.7464	Intermediate Similarity	NPD3750	Approved
0.7464	Intermediate Similarity	NPD7003	Approved
0.746	Intermediate Similarity	NPD3023	Approved
0.746	Intermediate Similarity	NPD3026	Approved
0.7445	Intermediate Similarity	NPD1549	Phase 2
0.7442	Intermediate Similarity	NPD2797	Approved
0.744	Intermediate Similarity	NPD3024	Approved
0.744	Intermediate Similarity	NPD3025	Approved
0.7429	Intermediate Similarity	NPD7390	Discontinued
0.7424	Intermediate Similarity	NPD3268	Approved
0.7413	Intermediate Similarity	NPD7458	Discontinued
0.7395	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7377	Intermediate Similarity	NPD2229	Approved
0.7377	Intermediate Similarity	NPD2228	Approved
0.7377	Intermediate Similarity	NPD2234	Approved
0.7377	Intermediate Similarity	NPD1241	Discontinued
0.7376	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7364	Intermediate Similarity	NPD9258	Approved
0.7364	Intermediate Similarity	NPD9256	Approved
0.7364	Intermediate Similarity	NPD1283	Approved
0.7353	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7344	Intermediate Similarity	NPD9269	Phase 2
0.7328	Intermediate Similarity	NPD9494	Approved
0.7321	Intermediate Similarity	NPD845	Approved
0.7321	Intermediate Similarity	NPD1202	Approved
0.7308	Intermediate Similarity	NPD1203	Approved
0.7302	Intermediate Similarity	NPD9268	Approved
0.7302	Intermediate Similarity	NPD1651	Approved
0.7299	Intermediate Similarity	NPD2796	Approved
0.7293	Intermediate Similarity	NPD2313	Discontinued
0.7287	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7281	Intermediate Similarity	NPD288	Approved
0.7266	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7265	Intermediate Similarity	NPD9261	Approved
0.7258	Intermediate Similarity	NPD255	Approved
0.7258	Intermediate Similarity	NPD256	Approved
0.7254	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD2329	Discontinued
0.7244	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD17	Approved
0.7241	Intermediate Similarity	NPD1242	Phase 1
0.7241	Intermediate Similarity	NPD4380	Phase 2
0.7239	Intermediate Similarity	NPD6663	Approved
0.7234	Intermediate Similarity	NPD3300	Phase 2
0.7226	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD111	Approved
0.7214	Intermediate Similarity	NPD8166	Discontinued
0.7213	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD1481	Phase 2
0.7203	Intermediate Similarity	NPD5909	Discontinued
0.7197	Intermediate Similarity	NPD5736	Approved
0.7193	Intermediate Similarity	NPD1809	Phase 2
0.7193	Intermediate Similarity	NPD844	Approved
0.7179	Intermediate Similarity	NPD940	Approved
0.7179	Intermediate Similarity	NPD846	Approved
0.7177	Intermediate Similarity	NPD9281	Approved
0.7168	Intermediate Similarity	NPD5122	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD2354	Approved
0.7162	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7154	Intermediate Similarity	NPD7635	Approved
0.7143	Intermediate Similarity	NPD7577	Discontinued
0.7132	Intermediate Similarity	NPD1535	Discovery
0.7132	Intermediate Similarity	NPD1281	Approved
0.7122	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD3748	Approved
0.7101	Intermediate Similarity	NPD4308	Phase 3
0.7094	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7094	Intermediate Similarity	NPD3028	Approved
0.7087	Intermediate Similarity	NPD1894	Discontinued
0.7087	Intermediate Similarity	NPD3091	Approved
0.7083	Intermediate Similarity	NPD6273	Approved
0.7071	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD9568	Approved
0.7063	Intermediate Similarity	NPD1511	Approved
0.7059	Intermediate Similarity	NPD3140	Approved
0.7059	Intermediate Similarity	NPD3142	Approved
0.7054	Intermediate Similarity	NPD4879	Approved
0.7054	Intermediate Similarity	NPD3847	Discontinued
0.7049	Intermediate Similarity	NPD4750	Phase 3
0.7049	Intermediate Similarity	NPD1792	Phase 2
0.7047	Intermediate Similarity	NPD2296	Approved
0.7045	Intermediate Similarity	NPD3266	Approved
0.7045	Intermediate Similarity	NPD3267	Approved
0.7031	Intermediate Similarity	NPD4093	Discontinued
0.7025	Intermediate Similarity	NPD2342	Discontinued
0.7023	Intermediate Similarity	NPD5157	Phase 1
0.7023	Intermediate Similarity	NPD5159	Phase 2
0.7023	Intermediate Similarity	NPD5158	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD1238	Approved
0.7009	Intermediate Similarity	NPD942	Approved
0.7008	Intermediate Similarity	NPD5536	Phase 2
0.7007	Intermediate Similarity	NPD230	Phase 1
0.7007	Intermediate Similarity	NPD6355	Discontinued
0.7	Intermediate Similarity	NPD9259	Approved
0.7	Intermediate Similarity	NPD9257	Approved
0.7	Intermediate Similarity	NPD2346	Discontinued
0.7	Intermediate Similarity	NPD2353	Approved
0.7	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD6884	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD4980	Approved
0.6992	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6991	Remote Similarity	NPD1239	Approved
0.698	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.698	Remote Similarity	NPD7819	Suspended
0.6977	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD4059	Approved
0.6966	Remote Similarity	NPD1512	Approved
0.6959	Remote Similarity	NPD7411	Suspended
0.6957	Remote Similarity	NPD688	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD1693	Approved
0.6954	Remote Similarity	NPD7075	Discontinued
0.6954	Remote Similarity	NPD3749	Approved
0.6954	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6953	Remote Similarity	NPD5303	Approved
0.6953	Remote Similarity	NPD5304	Approved
0.6947	Remote Similarity	NPD9717	Approved
0.6944	Remote Similarity	NPD6799	Approved
0.6944	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6942	Remote Similarity	NPD1444	Approved
0.6942	Remote Similarity	NPD1445	Approved
0.6929	Remote Similarity	NPD6100	Approved
0.6929	Remote Similarity	NPD6099	Approved
0.6923	Remote Similarity	NPD3887	Approved
0.6923	Remote Similarity	NPD6190	Approved
0.6913	Remote Similarity	NPD1934	Approved
0.6912	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD2629	Approved
0.6903	Remote Similarity	NPD1089	Approved
0.6903	Remote Similarity	NPD1086	Approved
0.6903	Remote Similarity	NPD1090	Approved
0.6894	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD6599	Discontinued
0.6889	Remote Similarity	NPD2614	Approved
0.6889	Remote Similarity	NPD6832	Phase 2
0.6887	Remote Similarity	NPD3882	Suspended
0.6879	Remote Similarity	NPD1471	Phase 3
0.6875	Remote Similarity	NPD7440	Discontinued
0.6875	Remote Similarity	NPD7610	Discontinued
0.687	Remote Similarity	NPD3092	Approved
0.6867	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD2801	Approved
0.6855	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD2286	Discontinued

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