NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	176.08
Volume:	194.654
LogP:	1.96
LogD:	2.042
LogS:	-2.909
# Rotatable Bonds:	3
TPSA:	26.3
# H-Bond Aceptor:	2
# H-Bond Donor:	0
# Rings:	1
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.66
Synthetic Accessibility Score:	1.704
Fsp3:	0.182
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.554
MDCK Permeability:	1.686791074462235e-05
Pgp-inhibitor:	0.008
Pgp-substrate:	0.014
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.496

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.696
Plasma Protein Binding (PPB):	89.74503326416016%
Volume Distribution (VD):	0.594
Pgp-substrate:	7.225489616394043%

ADMET: Metabolism

CYP1A2-inhibitor:	0.978
CYP1A2-substrate:	0.921
CYP2C19-inhibitor:	0.702
CYP2C19-substrate:	0.401
CYP2C9-inhibitor:	0.113
CYP2C9-substrate:	0.932
CYP2D6-inhibitor:	0.369
CYP2D6-substrate:	0.877
CYP3A4-inhibitor:	0.095
CYP3A4-substrate:	0.479

ADMET: Excretion

Clearance (CL):	7.874
Half-life (T1/2):	0.767

ADMET: Toxicity

hERG Blockers:	0.18
Human Hepatotoxicity (H-HT):	0.088
Drug-inuced Liver Injury (DILI):	0.647
AMES Toxicity:	0.752
Rat Oral Acute Toxicity:	0.02
Maximum Recommended Daily Dose:	0.074
Skin Sensitization:	0.949
Carcinogencity:	0.888
Eye Corrosion:	0.952
Eye Irritation:	0.995
Respiratory Toxicity:	0.572

Download Data

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

Natural Product: NPC175298

Natural Product ID:	NPC175298
*Common Name:**	4-(4-Methoxyphenyl)But-3-En-2-One
IUPAC Name:	(E)-4-(4-methoxyphenyl)but-3-en-2-one
Synonyms:
Standard InCHIKey:	WRRZKDVBPZBNJN-ONEGZZNKSA-N
Standard InCHI:	InChI=1S/C11H12O2/c1-9(12)3-4-10-5-7-11(13-2)8-6-10/h3-8H,1-2H3/b4-3+
SMILES:	COc1ccc(cc1)/C=C/C(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL72155
PubChem CID:	736889
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
NPO26469	Thalictrum delavayi	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26469	Thalictrum delavayi	Species	Ranunculaceae	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	2
Others	2

Activity Type	# Activity
Cell Line	1
Organism	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT111	Cell Line	K562	Homo sapiens	IC50	=	79000.0	nM	PMID[479930]
NPT19	Organism	Escherichia coli	Escherichia coli	IC50	=	1584893.19	nM	PMID[479929]
NPT849	Organism	Plutella xylostella	Plutella xylostella	mortality	=	26.6	%	PMID[479931]
NPT849	Organism	Plutella xylostella	Plutella xylostella	mortality	=	30.0	%	PMID[479931]

☑ 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 NPC175298 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	268
0.1-0.2	3004
0.2-0.3	6594
0.3-0.4	11576
0.4-0.5	4495
0.5-0.6	9271
0.6-0.7	6441
0.7-0.8	926
0.8-0.85	84
0.85-0.9	21
0.9-0.95	15
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9574	High Similarity	NPC13755
0.9375	High Similarity	NPC179686
0.9278	High Similarity	NPC2518
0.9231	High Similarity	NPC99886
0.9231	High Similarity	NPC259134
0.9231	High Similarity	NPC8002
0.9231	High Similarity	NPC177844
0.9184	High Similarity	NPC128730
0.913	High Similarity	NPC71853
0.9091	High Similarity	NPC176971
0.9091	High Similarity	NPC326447
0.9082	High Similarity	NPC109637
0.9072	High Similarity	NPC84325
0.9032	High Similarity	NPC321956
0.9	High Similarity	NPC151530
0.9	High Similarity	NPC157473
0.898	High Similarity	NPC298224
0.8922	High Similarity	NPC183648
0.8889	High Similarity	NPC38209
0.8842	High Similarity	NPC471581
0.8835	High Similarity	NPC23332
0.88	High Similarity	NPC227255
0.88	High Similarity	NPC288760
0.8776	High Similarity	NPC107101
0.8738	High Similarity	NPC473809
0.8738	High Similarity	NPC179309
0.87	High Similarity	NPC283546
0.8687	High Similarity	NPC307425
0.8673	High Similarity	NPC100870
0.8654	High Similarity	NPC57879
0.8614	High Similarity	NPC473855
0.8614	High Similarity	NPC238115
0.8586	High Similarity	NPC253746
0.8571	High Similarity	NPC199462
0.8542	High Similarity	NPC181709
0.8529	High Similarity	NPC1065
0.85	High Similarity	NPC51633
0.85	High Similarity	NPC12714
0.85	High Similarity	NPC300166
0.85	High Similarity	NPC310905
0.8491	Intermediate Similarity	NPC90903
0.8485	Intermediate Similarity	NPC471576
0.8431	Intermediate Similarity	NPC473393
0.8426	Intermediate Similarity	NPC268317
0.8426	Intermediate Similarity	NPC19290
0.8416	Intermediate Similarity	NPC192596
0.8416	Intermediate Similarity	NPC305205
0.8416	Intermediate Similarity	NPC304638
0.8411	Intermediate Similarity	NPC294941
0.8411	Intermediate Similarity	NPC252004
0.8365	Intermediate Similarity	NPC291837
0.8349	Intermediate Similarity	NPC185738
0.8349	Intermediate Similarity	NPC469954
0.8349	Intermediate Similarity	NPC280001
0.8333	Intermediate Similarity	NPC220540
0.8333	Intermediate Similarity	NPC474603
0.8333	Intermediate Similarity	NPC108875
0.8333	Intermediate Similarity	NPC292792
0.8333	Intermediate Similarity	NPC38079
0.8333	Intermediate Similarity	NPC12987
0.8302	Intermediate Similarity	NPC54626
0.8286	Intermediate Similarity	NPC234639
0.8286	Intermediate Similarity	NPC259554
0.8257	Intermediate Similarity	NPC470860
0.8252	Intermediate Similarity	NPC127676
0.8252	Intermediate Similarity	NPC139891
0.8252	Intermediate Similarity	NPC470393
0.8241	Intermediate Similarity	NPC114144
0.8208	Intermediate Similarity	NPC25067
0.8208	Intermediate Similarity	NPC231251
0.8208	Intermediate Similarity	NPC88868
0.82	Intermediate Similarity	NPC470161
0.8182	Intermediate Similarity	NPC286006
0.8182	Intermediate Similarity	NPC39793
0.8182	Intermediate Similarity	NPC199209
0.8182	Intermediate Similarity	NPC212643
0.8173	Intermediate Similarity	NPC113457
0.8165	Intermediate Similarity	NPC296526
0.8155	Intermediate Similarity	NPC241224
0.8148	Intermediate Similarity	NPC53953
0.8137	Intermediate Similarity	NPC94343
0.8132	Intermediate Similarity	NPC124576
0.8131	Intermediate Similarity	NPC245552
0.8119	Intermediate Similarity	NPC171843
0.8113	Intermediate Similarity	NPC149545
0.8108	Intermediate Similarity	NPC164706
0.8108	Intermediate Similarity	NPC272471
0.8108	Intermediate Similarity	NPC265547
0.8108	Intermediate Similarity	NPC277460
0.8108	Intermediate Similarity	NPC107588
0.8108	Intermediate Similarity	NPC124916
0.8108	Intermediate Similarity	NPC70744
0.8108	Intermediate Similarity	NPC137537
0.8095	Intermediate Similarity	NPC251306
0.8095	Intermediate Similarity	NPC258171
0.8095	Intermediate Similarity	NPC227894
0.8091	Intermediate Similarity	NPC111225
0.8085	Intermediate Similarity	NPC23837
0.8081	Intermediate Similarity	NPC81010
0.8081	Intermediate Similarity	NPC32977
0.8077	Intermediate Similarity	NPC42383
0.8077	Intermediate Similarity	NPC8302
0.8073	Intermediate Similarity	NPC87563
0.8053	Intermediate Similarity	NPC224814
0.8053	Intermediate Similarity	NPC14007
0.8053	Intermediate Similarity	NPC60962
0.8053	Intermediate Similarity	NPC189844
0.8053	Intermediate Similarity	NPC109083
0.8053	Intermediate Similarity	NPC225245
0.8053	Intermediate Similarity	NPC269843
0.8036	Intermediate Similarity	NPC298796
0.8036	Intermediate Similarity	NPC281356
0.8036	Intermediate Similarity	NPC37858
0.8036	Intermediate Similarity	NPC69670
0.8036	Intermediate Similarity	NPC61779
0.802	Intermediate Similarity	NPC201967
0.802	Intermediate Similarity	NPC95755
0.8019	Intermediate Similarity	NPC201959
0.8019	Intermediate Similarity	NPC146530
0.8019	Intermediate Similarity	NPC75440
0.8019	Intermediate Similarity	NPC206341
0.8019	Intermediate Similarity	NPC309982
0.8	Intermediate Similarity	NPC188907
0.7982	Intermediate Similarity	NPC109241
0.7982	Intermediate Similarity	NPC303522
0.7982	Intermediate Similarity	NPC279916
0.7965	Intermediate Similarity	NPC222175
0.7965	Intermediate Similarity	NPC202474
0.7946	Intermediate Similarity	NPC96705
0.7946	Intermediate Similarity	NPC171023
0.7946	Intermediate Similarity	NPC152159
0.7946	Intermediate Similarity	NPC152306
0.7946	Intermediate Similarity	NPC293424
0.7944	Intermediate Similarity	NPC82016
0.7944	Intermediate Similarity	NPC7097
0.7944	Intermediate Similarity	NPC127326
0.7944	Intermediate Similarity	NPC471954
0.7944	Intermediate Similarity	NPC75272
0.7944	Intermediate Similarity	NPC36108
0.7944	Intermediate Similarity	NPC233731
0.7944	Intermediate Similarity	NPC474272
0.7944	Intermediate Similarity	NPC246358
0.7941	Intermediate Similarity	NPC130193
0.7928	Intermediate Similarity	NPC128633
0.7925	Intermediate Similarity	NPC260952
0.7913	Intermediate Similarity	NPC286573
0.7913	Intermediate Similarity	NPC256167
0.7913	Intermediate Similarity	NPC114298
0.7909	Intermediate Similarity	NPC235250
0.79	Intermediate Similarity	NPC5472
0.7895	Intermediate Similarity	NPC204466
0.7895	Intermediate Similarity	NPC235190
0.7895	Intermediate Similarity	NPC295317
0.7895	Intermediate Similarity	NPC163200
0.7895	Intermediate Similarity	NPC158949
0.7895	Intermediate Similarity	NPC471877
0.7895	Intermediate Similarity	NPC131868
0.7895	Intermediate Similarity	NPC180006
0.7885	Intermediate Similarity	NPC24327
0.7885	Intermediate Similarity	NPC12870
0.7876	Intermediate Similarity	NPC57501
0.787	Intermediate Similarity	NPC137685
0.787	Intermediate Similarity	NPC106141
0.787	Intermediate Similarity	NPC46844
0.787	Intermediate Similarity	NPC475852
0.7857	Intermediate Similarity	NPC240664
0.7857	Intermediate Similarity	NPC263754
0.7857	Intermediate Similarity	NPC183154
0.7857	Intermediate Similarity	NPC45104
0.7857	Intermediate Similarity	NPC217423
0.785	Intermediate Similarity	NPC97811
0.7845	Intermediate Similarity	NPC11799
0.7845	Intermediate Similarity	NPC242372
0.7845	Intermediate Similarity	NPC238810
0.7845	Intermediate Similarity	NPC106659
0.7845	Intermediate Similarity	NPC141252
0.7845	Intermediate Similarity	NPC160900
0.7845	Intermediate Similarity	NPC164778
0.7845	Intermediate Similarity	NPC4181
0.7845	Intermediate Similarity	NPC18984
0.7845	Intermediate Similarity	NPC474691
0.7845	Intermediate Similarity	NPC257976
0.7845	Intermediate Similarity	NPC229084
0.7843	Intermediate Similarity	NPC140619
0.7835	Intermediate Similarity	NPC206876
0.7826	Intermediate Similarity	NPC144418
0.7826	Intermediate Similarity	NPC251259
0.7826	Intermediate Similarity	NPC70752
0.7826	Intermediate Similarity	NPC310373
0.7826	Intermediate Similarity	NPC114845
0.7812	Intermediate Similarity	NPC248817
0.781	Intermediate Similarity	NPC79672
0.7807	Intermediate Similarity	NPC2058
0.7798	Intermediate Similarity	NPC8547
0.7798	Intermediate Similarity	NPC173746
0.7798	Intermediate Similarity	NPC296920
0.7798	Intermediate Similarity	NPC78918
0.7798	Intermediate Similarity	NPC166837
0.7798	Intermediate Similarity	NPC139946
0.7798	Intermediate Similarity	NPC90520

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 NPC175298 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	266
0.1-0.2	1195
0.2-0.3	1356
0.3-0.4	2815
0.4-0.5	1854
0.5-0.6	1109
0.6-0.7	485
0.7-0.8	64
0.8-0.85	3
0.85-0.9	2
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9091	High Similarity	NPD3134	Approved
0.9	High Similarity	NPD1358	Approved
0.8667	High Similarity	NPD1241	Discontinued
0.8349	Intermediate Similarity	NPD5536	Phase 2
0.8252	Intermediate Similarity	NPD9697	Approved
0.8019	Intermediate Similarity	NPD2684	Approved
0.7944	Intermediate Similarity	NPD5451	Approved
0.7913	Intermediate Similarity	NPD3972	Approved
0.789	Intermediate Similarity	NPD5535	Approved
0.7876	Intermediate Similarity	NPD5691	Approved
0.7845	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7807	Intermediate Similarity	NPD4626	Approved
0.7798	Intermediate Similarity	NPD228	Approved
0.7778	Intermediate Similarity	NPD1876	Approved
0.7757	Intermediate Similarity	NPD290	Approved
0.7727	Intermediate Similarity	NPD821	Approved
0.7727	Intermediate Similarity	NPD7843	Approved
0.7719	Intermediate Similarity	NPD1651	Approved
0.7708	Intermediate Similarity	NPD111	Approved
0.7664	Intermediate Similarity	NPD968	Approved
0.7658	Intermediate Similarity	NPD5283	Phase 1
0.7576	Intermediate Similarity	NPD9295	Approved
0.7522	Intermediate Similarity	NPD7157	Approved
0.7521	Intermediate Similarity	NPD422	Phase 1
0.7521	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7478	Intermediate Similarity	NPD9545	Approved
0.7438	Intermediate Similarity	NPD9494	Approved
0.7436	Intermediate Similarity	NPD3847	Discontinued
0.7436	Intermediate Similarity	NPD3496	Discontinued
0.7426	Intermediate Similarity	NPD9365	Approved
0.7379	Intermediate Similarity	NPD2933	Approved
0.7379	Intermediate Similarity	NPD2934	Approved
0.7373	Intermediate Similarity	NPD1281	Approved
0.7328	Intermediate Similarity	NPD1894	Discontinued
0.7321	Intermediate Similarity	NPD1139	Approved
0.7321	Intermediate Similarity	NPD1137	Approved
0.7311	Intermediate Similarity	NPD9717	Approved
0.7308	Intermediate Similarity	NPD2859	Approved
0.7308	Intermediate Similarity	NPD2860	Approved
0.7304	Intermediate Similarity	NPD9493	Approved
0.7304	Intermediate Similarity	NPD3596	Phase 2
0.728	Intermediate Similarity	NPD3142	Approved
0.728	Intermediate Similarity	NPD3140	Approved
0.728	Intermediate Similarity	NPD1240	Approved
0.7265	Intermediate Similarity	NPD5585	Approved
0.7265	Intermediate Similarity	NPD1357	Approved
0.7257	Intermediate Similarity	NPD1138	Approved
0.7213	Intermediate Similarity	NPD1019	Discontinued
0.7213	Intermediate Similarity	NPD2798	Approved
0.7212	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD9296	Approved
0.7203	Intermediate Similarity	NPD2668	Approved
0.7203	Intermediate Similarity	NPD1778	Approved
0.7203	Intermediate Similarity	NPD2667	Approved
0.72	Intermediate Similarity	NPD1282	Approved
0.719	Intermediate Similarity	NPD1283	Approved
0.7179	Intermediate Similarity	NPD1182	Approved
0.7179	Intermediate Similarity	NPD6581	Approved
0.7179	Intermediate Similarity	NPD6580	Approved
0.7179	Intermediate Similarity	NPD1548	Phase 1
0.7165	Intermediate Similarity	NPD1607	Approved
0.7131	Intermediate Similarity	NPD3267	Approved
0.7131	Intermediate Similarity	NPD3266	Approved
0.713	Intermediate Similarity	NPD593	Approved
0.713	Intermediate Similarity	NPD595	Approved
0.7119	Intermediate Similarity	NPD6830	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD3020	Approved
0.7097	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD6832	Phase 2
0.7083	Intermediate Similarity	NPD1535	Discovery
0.7069	Intermediate Similarity	NPD709	Approved
0.7069	Intermediate Similarity	NPD2557	Approved
0.7069	Intermediate Similarity	NPD6671	Approved
0.7059	Intermediate Similarity	NPD2423	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD6516	Phase 2
0.7059	Intermediate Similarity	NPD17	Approved
0.7059	Intermediate Similarity	NPD5846	Approved
0.7049	Intermediate Similarity	NPD196	Phase 1
0.7043	Intermediate Similarity	NPD592	Approved
0.7043	Intermediate Similarity	NPD594	Approved
0.7037	Intermediate Similarity	NPD3028	Approved
0.7025	Intermediate Similarity	NPD2981	Phase 2
0.7025	Intermediate Similarity	NPD1481	Phase 2
0.7	Intermediate Similarity	NPD2796	Approved
0.6992	Remote Similarity	NPD987	Approved
0.6992	Remote Similarity	NPD1203	Approved
0.6992	Remote Similarity	NPD2797	Approved
0.6977	Remote Similarity	NPD743	Approved
0.6972	Remote Similarity	NPD846	Approved
0.6972	Remote Similarity	NPD940	Approved
0.6972	Remote Similarity	NPD291	Approved
0.6967	Remote Similarity	NPD2983	Phase 2
0.6967	Remote Similarity	NPD6583	Phase 3
0.6967	Remote Similarity	NPD4359	Approved
0.6967	Remote Similarity	NPD6582	Phase 2
0.6967	Remote Similarity	NPD5327	Phase 3
0.6967	Remote Similarity	NPD1669	Approved
0.6967	Remote Similarity	NPD2982	Phase 2
0.6967	Remote Similarity	NPD3676	Clinical (unspecified phase)
0.6967	Remote Similarity	NPD3685	Discontinued
0.6967	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD1238	Approved
0.6942	Remote Similarity	NPD3705	Approved
0.6942	Remote Similarity	NPD1611	Approved
0.6942	Remote Similarity	NPD1610	Phase 2
0.6923	Remote Similarity	NPD2799	Discontinued
0.6923	Remote Similarity	NPD6387	Discontinued
0.6923	Remote Similarity	NPD1510	Phase 2
0.6911	Remote Similarity	NPD7258	Clinical (unspecified phase)
0.6911	Remote Similarity	NPD3225	Approved
0.6909	Remote Similarity	NPD9261	Approved
0.6905	Remote Similarity	NPD5746	Approved
0.6905	Remote Similarity	NPD5163	Phase 2
0.6899	Remote Similarity	NPD2492	Phase 1
0.6885	Remote Similarity	NPD1608	Approved
0.6885	Remote Similarity	NPD1840	Phase 2
0.6881	Remote Similarity	NPD1242	Phase 1
0.688	Remote Similarity	NPD454	Approved
0.687	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.687	Remote Similarity	NPD2935	Discontinued
0.6855	Remote Similarity	NPD1819	Approved
0.6855	Remote Similarity	NPD1820	Approved
0.6855	Remote Similarity	NPD1817	Approved
0.6855	Remote Similarity	NPD1818	Approved
0.685	Remote Similarity	NPD6798	Discontinued
0.685	Remote Similarity	NPD3268	Approved
0.685	Remote Similarity	NPD1296	Phase 2
0.685	Remote Similarity	NPD3374	Clinical (unspecified phase)
0.685	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6847	Remote Similarity	NPD164	Approved
0.6842	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD3049	Approved
0.6833	Remote Similarity	NPD6382	Discontinued
0.6833	Remote Similarity	NPD2595	Approved
0.6833	Remote Similarity	NPD2594	Approved
0.6833	Remote Similarity	NPD3445	Approved
0.6833	Remote Similarity	NPD3443	Approved
0.6833	Remote Similarity	NPD3444	Approved
0.6829	Remote Similarity	NPD4129	Approved
0.6829	Remote Similarity	NPD6539	Approved
0.6829	Remote Similarity	NPD6540	Phase 3
0.6829	Remote Similarity	NPD2429	Approved
0.6829	Remote Similarity	NPD6543	Approved
0.6829	Remote Similarity	NPD6542	Approved
0.6829	Remote Similarity	NPD2428	Approved
0.6822	Remote Similarity	NPD4340	Discontinued
0.6822	Remote Similarity	NPD1809	Phase 2
0.6822	Remote Similarity	NPD844	Approved
0.6822	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD1933	Approved
0.6818	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD2344	Approved
0.6818	Remote Similarity	NPD2353	Approved
0.681	Remote Similarity	NPD769	Approved
0.68	Remote Similarity	NPD6584	Phase 3
0.68	Remote Similarity	NPD4624	Approved
0.68	Remote Similarity	NPD3690	Phase 2
0.68	Remote Similarity	NPD3691	Phase 2
0.6797	Remote Similarity	NPD8032	Phase 2
0.6797	Remote Similarity	NPD5745	Approved
0.6797	Remote Similarity	NPD4062	Phase 3
0.6797	Remote Similarity	NPD6233	Phase 2
0.6794	Remote Similarity	NPD3748	Approved
0.6792	Remote Similarity	NPD845	Approved
0.6777	Remote Similarity	NPD2554	Approved
0.6777	Remote Similarity	NPD2556	Approved
0.6774	Remote Similarity	NPD6541	Approved
0.6774	Remote Similarity	NPD6538	Approved
0.6772	Remote Similarity	NPD7095	Approved
0.6767	Remote Similarity	NPD2424	Discontinued
0.6767	Remote Similarity	NPD1549	Phase 2
0.6759	Remote Similarity	NPD288	Approved
0.675	Remote Similarity	NPD2486	Discontinued
0.6748	Remote Similarity	NPD2233	Approved
0.6748	Remote Similarity	NPD2232	Approved
0.6748	Remote Similarity	NPD2230	Approved
0.6746	Remote Similarity	NPD3018	Phase 2
0.6746	Remote Similarity	NPD4993	Discontinued
0.6744	Remote Similarity	NPD2979	Phase 3
0.6744	Remote Similarity	NPD4140	Approved
0.6744	Remote Similarity	NPD4060	Phase 1
0.6744	Remote Similarity	NPD4307	Phase 2
0.6741	Remote Similarity	NPD3887	Approved
0.6727	Remote Similarity	NPD289	Clinical (unspecified phase)
0.672	Remote Similarity	NPD3568	Approved
0.672	Remote Similarity	NPD3567	Approved
0.6719	Remote Similarity	NPD2313	Discontinued
0.6719	Remote Similarity	NPD411	Approved
0.6696	Remote Similarity	NPD9501	Approved
0.6696	Remote Similarity	NPD9608	Approved
0.6696	Remote Similarity	NPD9610	Approved
0.6695	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD1421	Approved
0.6694	Remote Similarity	NPD1420	Approved
0.6693	Remote Similarity	NPD2614	Approved
0.6693	Remote Similarity	NPD682	Discontinued
0.6693	Remote Similarity	NPD4908	Phase 1
0.6693	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.6692	Remote Similarity	NPD6355	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