NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	258.13
Volume:	278.731
LogP:	1.918
LogD:	2.189
LogS:	-3.559
# Rotatable Bonds:	4
TPSA:	46.53
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.903
Synthetic Accessibility Score:	3.235
Fsp3:	0.312
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:	-4.647
MDCK Permeability:	1.822060949052684e-05
Pgp-inhibitor:	0.873
Pgp-substrate:	0.005
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.103

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.872
Plasma Protein Binding (PPB):	90.86668395996094%
Volume Distribution (VD):	0.303
Pgp-substrate:	3.5544190406799316%

ADMET: Metabolism

CYP1A2-inhibitor:	0.418
CYP1A2-substrate:	0.828
CYP2C19-inhibitor:	0.241
CYP2C19-substrate:	0.811
CYP2C9-inhibitor:	0.059
CYP2C9-substrate:	0.656
CYP2D6-inhibitor:	0.021
CYP2D6-substrate:	0.349
CYP3A4-inhibitor:	0.055
CYP3A4-substrate:	0.603

ADMET: Excretion

Clearance (CL):	8.437
Half-life (T1/2):	0.736

ADMET: Toxicity

hERG Blockers:	0.061
Human Hepatotoxicity (H-HT):	0.749
Drug-inuced Liver Injury (DILI):	0.165
AMES Toxicity:	0.12
Rat Oral Acute Toxicity:	0.03
Maximum Recommended Daily Dose:	0.409
Skin Sensitization:	0.92
Carcinogencity:	0.817
Eye Corrosion:	0.009
Eye Irritation:	0.8
Respiratory Toxicity:	0.306

Download Data

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

Natural Product: NPC474308

Natural Product ID:	NPC474308
*Common Name:**	4-Cinnamyl-4-Hydroxy-3-Methoxycyclohex-2-Enone
IUPAC Name:	4-hydroxy-3-methoxy-4-[(E)-3-phenylprop-2-enyl]cyclohex-2-en-1-one
Synonyms:
Standard InCHIKey:	UMSXFHQOERKWAU-VMPITWQZSA-N
Standard InCHI:	InChI=1S/C16H18O3/c1-19-15-12-14(17)9-11-16(15,18)10-5-8-13-6-3-2-4-7-13/h2-8,12,18H,9-11H2,1H3/b8-5+
SMILES:	COC1=CC(=O)CCC1(O)C/C=C/c1ccccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL464986
PubChem CID:	11334412
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000037] Styrenes

*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
NPO29804	Nepalese propolis	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[15974608]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	1

Activity Type	# Activity
CELL-LINE	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20763	CELL-LINE	J774.1	Mus musculus	IC50	=	19200.0	nM	PMID[456535]

☑ 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 NPC474308 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	183
0.1-0.2	975
0.2-0.3	3287
0.3-0.4	9706
0.4-0.5	12590
0.5-0.6	12988
0.6-0.7	2783
0.7-0.8	172
0.8-0.85	7
0.85-0.9	5
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8824	High Similarity	NPC475282
0.8602	High Similarity	NPC194326
0.8557	High Similarity	NPC473347
0.8485	Intermediate Similarity	NPC476120
0.8384	Intermediate Similarity	NPC278228
0.8317	Intermediate Similarity	NPC158623
0.83	Intermediate Similarity	NPC179411
0.8182	Intermediate Similarity	NPC108532
0.8125	Intermediate Similarity	NPC477693
0.8125	Intermediate Similarity	NPC477704
0.7845	Intermediate Similarity	NPC139171
0.7843	Intermediate Similarity	NPC289201
0.7838	Intermediate Similarity	NPC114144
0.7812	Intermediate Similarity	NPC123476
0.7778	Intermediate Similarity	NPC281604
0.7767	Intermediate Similarity	NPC329387
0.7767	Intermediate Similarity	NPC317280
0.7757	Intermediate Similarity	NPC51174
0.7727	Intermediate Similarity	NPC470355
0.77	Intermediate Similarity	NPC476484
0.7685	Intermediate Similarity	NPC156648
0.767	Intermediate Similarity	NPC103048
0.7596	Intermediate Similarity	NPC145052
0.7593	Intermediate Similarity	NPC193640
0.7593	Intermediate Similarity	NPC475905
0.7593	Intermediate Similarity	NPC25385
0.7573	Intermediate Similarity	NPC12695
0.7568	Intermediate Similarity	NPC477250
0.7549	Intermediate Similarity	NPC34243
0.7524	Intermediate Similarity	NPC54647
0.7522	Intermediate Similarity	NPC469509
0.7478	Intermediate Similarity	NPC471553
0.7476	Intermediate Similarity	NPC5472
0.7476	Intermediate Similarity	NPC206764
0.7456	Intermediate Similarity	NPC471616
0.7429	Intermediate Similarity	NPC154517
0.7429	Intermediate Similarity	NPC135951
0.7426	Intermediate Similarity	NPC67585
0.7426	Intermediate Similarity	NPC110420
0.7426	Intermediate Similarity	NPC303967
0.7395	Intermediate Similarity	NPC286573
0.7373	Intermediate Similarity	NPC158949
0.7364	Intermediate Similarity	NPC20485
0.7358	Intermediate Similarity	NPC80115
0.7358	Intermediate Similarity	NPC476042
0.7333	Intermediate Similarity	NPC240042
0.7321	Intermediate Similarity	NPC474057
0.7321	Intermediate Similarity	NPC222905
0.7315	Intermediate Similarity	NPC160382
0.7297	Intermediate Similarity	NPC469511
0.7295	Intermediate Similarity	NPC81135
0.729	Intermediate Similarity	NPC112552
0.7288	Intermediate Similarity	NPC105709
0.7288	Intermediate Similarity	NPC243059
0.7288	Intermediate Similarity	NPC280827
0.7281	Intermediate Similarity	NPC474363
0.7273	Intermediate Similarity	NPC29989
0.7273	Intermediate Similarity	NPC53299
0.7273	Intermediate Similarity	NPC69332
0.7273	Intermediate Similarity	NPC70843
0.7273	Intermediate Similarity	NPC477251
0.7273	Intermediate Similarity	NPC95178
0.7241	Intermediate Similarity	NPC19290
0.7241	Intermediate Similarity	NPC325646
0.7241	Intermediate Similarity	NPC28951
0.7222	Intermediate Similarity	NPC244427
0.7222	Intermediate Similarity	NPC222390
0.7222	Intermediate Similarity	NPC472585
0.7217	Intermediate Similarity	NPC217111
0.7217	Intermediate Similarity	NPC228936
0.7213	Intermediate Similarity	NPC328997
0.7213	Intermediate Similarity	NPC294050
0.7213	Intermediate Similarity	NPC236405
0.7207	Intermediate Similarity	NPC470007
0.7207	Intermediate Similarity	NPC47536
0.7207	Intermediate Similarity	NPC470391
0.719	Intermediate Similarity	NPC242372
0.719	Intermediate Similarity	NPC4181
0.719	Intermediate Similarity	NPC164778
0.719	Intermediate Similarity	NPC257976
0.7184	Intermediate Similarity	NPC187725
0.7184	Intermediate Similarity	NPC472319
0.7184	Intermediate Similarity	NPC141607
0.7172	Intermediate Similarity	NPC44546
0.717	Intermediate Similarity	NPC156021
0.7168	Intermediate Similarity	NPC116842
0.7165	Intermediate Similarity	NPC327410
0.7157	Intermediate Similarity	NPC231591
0.7156	Intermediate Similarity	NPC274443
0.7156	Intermediate Similarity	NPC68269
0.7156	Intermediate Similarity	NPC247976
0.7155	Intermediate Similarity	NPC23402
0.7154	Intermediate Similarity	NPC303680
0.7154	Intermediate Similarity	NPC276014
0.7154	Intermediate Similarity	NPC84076
0.7154	Intermediate Similarity	NPC90128
0.7154	Intermediate Similarity	NPC179777
0.7143	Intermediate Similarity	NPC475827
0.7143	Intermediate Similarity	NPC40178
0.7143	Intermediate Similarity	NPC474223
0.7131	Intermediate Similarity	NPC273686
0.7131	Intermediate Similarity	NPC246166
0.7131	Intermediate Similarity	NPC312404
0.7129	Intermediate Similarity	NPC96625
0.7117	Intermediate Similarity	NPC6984
0.7117	Intermediate Similarity	NPC136962
0.7115	Intermediate Similarity	NPC77273
0.7107	Intermediate Similarity	NPC114298
0.7105	Intermediate Similarity	NPC474689
0.7105	Intermediate Similarity	NPC292834
0.7105	Intermediate Similarity	NPC212415
0.7105	Intermediate Similarity	NPC158282
0.7105	Intermediate Similarity	NPC474314
0.7103	Intermediate Similarity	NPC210529
0.7103	Intermediate Similarity	NPC271475
0.7103	Intermediate Similarity	NPC175852
0.7103	Intermediate Similarity	NPC160548
0.7103	Intermediate Similarity	NPC260000
0.7103	Intermediate Similarity	NPC201967
0.7097	Intermediate Similarity	NPC123228
0.7097	Intermediate Similarity	NPC316553
0.7097	Intermediate Similarity	NPC5018
0.7097	Intermediate Similarity	NPC276466
0.7097	Intermediate Similarity	NPC151167
0.7097	Intermediate Similarity	NPC123722
0.7094	Intermediate Similarity	NPC277394
0.7094	Intermediate Similarity	NPC61062
0.7094	Intermediate Similarity	NPC268317
0.7094	Intermediate Similarity	NPC299252
0.7091	Intermediate Similarity	NPC261573
0.7091	Intermediate Similarity	NPC269644
0.7091	Intermediate Similarity	NPC19136
0.7091	Intermediate Similarity	NPC8931
0.7091	Intermediate Similarity	NPC249067
0.7091	Intermediate Similarity	NPC120693
0.7087	Intermediate Similarity	NPC108026
0.708	Intermediate Similarity	NPC95172
0.708	Intermediate Similarity	NPC88141
0.7071	Intermediate Similarity	NPC44830
0.7069	Intermediate Similarity	NPC93181
0.7064	Intermediate Similarity	NPC25458
0.7063	Intermediate Similarity	NPC172673
0.7059	Intermediate Similarity	NPC204784
0.7054	Intermediate Similarity	NPC226699
0.7054	Intermediate Similarity	NPC211439
0.7054	Intermediate Similarity	NPC34715
0.7049	Intermediate Similarity	NPC229084
0.7049	Intermediate Similarity	NPC14141
0.7049	Intermediate Similarity	NPC471466
0.7049	Intermediate Similarity	NPC160900
0.7049	Intermediate Similarity	NPC106659
0.7049	Intermediate Similarity	NPC18984
0.7048	Intermediate Similarity	NPC23453
0.7048	Intermediate Similarity	NPC181709
0.7043	Intermediate Similarity	NPC13784
0.7043	Intermediate Similarity	NPC51698
0.7037	Intermediate Similarity	NPC130193
0.7037	Intermediate Similarity	NPC280869
0.7037	Intermediate Similarity	NPC325497
0.7034	Intermediate Similarity	NPC150919
0.7027	Intermediate Similarity	NPC172483
0.7027	Intermediate Similarity	NPC321670
0.7025	Intermediate Similarity	NPC201777
0.7019	Intermediate Similarity	NPC317645
0.7018	Intermediate Similarity	NPC21162
0.7018	Intermediate Similarity	NPC291799
0.7018	Intermediate Similarity	NPC477247
0.7018	Intermediate Similarity	NPC476003
0.7016	Intermediate Similarity	NPC146239
0.701	Intermediate Similarity	NPC469894
0.701	Intermediate Similarity	NPC139901
0.701	Intermediate Similarity	NPC151405
0.7009	Intermediate Similarity	NPC253423
0.7009	Intermediate Similarity	NPC472788
0.7	Intermediate Similarity	NPC474365
0.7	Intermediate Similarity	NPC82426
0.7	Intermediate Similarity	NPC474222
0.7	Intermediate Similarity	NPC91820
0.7	Intermediate Similarity	NPC301943
0.7	Intermediate Similarity	NPC475804
0.6992	Remote Similarity	NPC474803
0.6992	Remote Similarity	NPC244454
0.6991	Remote Similarity	NPC474364
0.6991	Remote Similarity	NPC17525
0.6991	Remote Similarity	NPC317305
0.6991	Remote Similarity	NPC31274
0.6984	Remote Similarity	NPC304622
0.6984	Remote Similarity	NPC262819
0.6983	Remote Similarity	NPC87069
0.6983	Remote Similarity	NPC474641
0.6983	Remote Similarity	NPC11824
0.6983	Remote Similarity	NPC477411
0.6983	Remote Similarity	NPC196075
0.6979	Remote Similarity	NPC179726
0.6975	Remote Similarity	NPC311091
0.6975	Remote Similarity	NPC471033
0.697	Remote Similarity	NPC283012
0.697	Remote Similarity	NPC99240
0.697	Remote Similarity	NPC475199
0.6967	Remote Similarity	NPC65627

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 NPC474308 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	166
0.1-0.2	802
0.2-0.3	1321
0.3-0.4	3107
0.4-0.5	2455
0.5-0.6	1107
0.6-0.7	180
0.7-0.8	12
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7549	Intermediate Similarity	NPD5122	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD5909	Discontinued
0.7315	Intermediate Similarity	NPD6647	Phase 2
0.7232	Intermediate Similarity	NPD2067	Discontinued
0.7217	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7196	Intermediate Similarity	NPD2066	Phase 3
0.7182	Intermediate Similarity	NPD5048	Discontinued
0.7168	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD9495	Approved
0.7091	Intermediate Similarity	NPD1237	Approved
0.7069	Intermediate Similarity	NPD2629	Approved
0.7049	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.6991	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD1282	Approved
0.6923	Remote Similarity	NPD9258	Approved
0.6923	Remote Similarity	NPD9256	Approved
0.69	Remote Similarity	NPD3971	Phase 1
0.69	Remote Similarity	NPD9491	Approved
0.6869	Remote Similarity	NPD226	Approved
0.686	Remote Similarity	NPD5306	Approved
0.686	Remote Similarity	NPD5305	Approved
0.6847	Remote Similarity	NPD1930	Approved
0.6847	Remote Similarity	NPD1929	Approved
0.6847	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6827	Remote Similarity	NPD5347	Phase 2
0.6827	Remote Similarity	NPD5346	Phase 2
0.6827	Remote Similarity	NPD800	Approved
0.6825	Remote Similarity	NPD9494	Approved
0.6822	Remote Similarity	NPD1693	Approved
0.6803	Remote Similarity	NPD4136	Approved
0.6803	Remote Similarity	NPD4135	Approved
0.6803	Remote Similarity	NPD4106	Approved
0.6796	Remote Similarity	NPD4793	Discontinued
0.6777	Remote Similarity	NPD4105	Approved
0.6777	Remote Similarity	NPD4102	Approved
0.6771	Remote Similarity	NPD9716	Approved
0.6762	Remote Similarity	NPD1089	Approved
0.6762	Remote Similarity	NPD1086	Approved
0.6762	Remote Similarity	NPD1090	Approved
0.6757	Remote Similarity	NPD1932	Approved
0.675	Remote Similarity	NPD5536	Phase 2
0.6748	Remote Similarity	NPD4806	Approved
0.6748	Remote Similarity	NPD4807	Approved
0.6721	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD7609	Phase 3
0.6696	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6695	Remote Similarity	NPD1241	Discontinued
0.6695	Remote Similarity	NPD6010	Discontinued
0.6694	Remote Similarity	NPD4878	Approved
0.6667	Remote Similarity	NPD2933	Approved
0.6667	Remote Similarity	NPD2934	Approved
0.6636	Remote Similarity	NPD1088	Approved
0.6636	Remote Similarity	NPD7631	Approved
0.6635	Remote Similarity	NPD650	Approved
0.6633	Remote Similarity	NPD9294	Approved
0.6606	Remote Similarity	NPD1989	Approved
0.6606	Remote Similarity	NPD2860	Approved
0.6606	Remote Similarity	NPD2859	Approved
0.6604	Remote Similarity	NPD3673	Approved
0.6604	Remote Similarity	NPD3672	Approved
0.6602	Remote Similarity	NPD5734	Clinical (unspecified phase)
0.66	Remote Similarity	NPD1507	Clinical (unspecified phase)
0.6583	Remote Similarity	NPD4198	Discontinued
0.6581	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD7798	Approved
0.6577	Remote Similarity	NPD1238	Approved
0.6574	Remote Similarity	NPD1202	Approved
0.6566	Remote Similarity	NPD227	Approved
0.6566	Remote Similarity	NPD225	Approved
0.6557	Remote Similarity	NPD9545	Approved
0.6552	Remote Similarity	NPD2329	Discontinued
0.6552	Remote Similarity	NPD2182	Approved
0.6542	Remote Similarity	NPD1239	Approved
0.6538	Remote Similarity	NPD9257	Approved
0.6538	Remote Similarity	NPD9259	Approved
0.6535	Remote Similarity	NPD942	Approved
0.6529	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6529	Remote Similarity	NPD9493	Approved
0.6529	Remote Similarity	NPD694	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD689	Discontinued
0.6504	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.65	Remote Similarity	NPD5951	Approved
0.65	Remote Similarity	NPD9490	Approved
0.6491	Remote Similarity	NPD164	Approved
0.6486	Remote Similarity	NPD5926	Approved
0.6484	Remote Similarity	NPD5647	Approved
0.6476	Remote Similarity	NPD1087	Approved
0.6471	Remote Similarity	NPD5277	Phase 2
0.6466	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6466	Remote Similarity	NPD1358	Approved
0.6455	Remote Similarity	NPD5206	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD2932	Approved
0.6442	Remote Similarity	NPD111	Approved
0.6439	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6434	Remote Similarity	NPD5204	Approved
0.6429	Remote Similarity	NPD3972	Approved
0.6429	Remote Similarity	NPD3020	Approved
0.6412	Remote Similarity	NPD3268	Approved
0.641	Remote Similarity	NPD2684	Approved
0.6406	Remote Similarity	NPD2625	Approved
0.6406	Remote Similarity	NPD2628	Approved
0.6406	Remote Similarity	NPD2797	Approved
0.6406	Remote Similarity	NPD2160	Approved
0.6406	Remote Similarity	NPD2627	Approved
0.6406	Remote Similarity	NPD2626	Approved
0.6406	Remote Similarity	NPD2159	Approved
0.6396	Remote Similarity	NPD3495	Discontinued
0.6396	Remote Similarity	NPD1566	Phase 3
0.6396	Remote Similarity	NPD1564	Approved
0.6396	Remote Similarity	NPD1565	Approved
0.6387	Remote Similarity	NPD969	Suspended
0.6387	Remote Similarity	NPD228	Approved
0.6385	Remote Similarity	NPD4617	Approved
0.6385	Remote Similarity	NPD5203	Approved
0.6385	Remote Similarity	NPD4620	Approved
0.6385	Remote Similarity	NPD5201	Approved
0.6385	Remote Similarity	NPD5202	Clinical (unspecified phase)
0.6379	Remote Similarity	NPD3134	Approved
0.6378	Remote Similarity	NPD5159	Phase 2
0.6378	Remote Similarity	NPD5157	Phase 1
0.6378	Remote Similarity	NPD5158	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD688	Clinical (unspecified phase)
0.6357	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6356	Remote Similarity	NPD3022	Approved
0.6356	Remote Similarity	NPD3021	Approved
0.6356	Remote Similarity	NPD1317	Discontinued
0.6336	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD7094	Approved
0.6333	Remote Similarity	NPD6858	Approved
0.6331	Remote Similarity	NPD6190	Approved
0.6325	Remote Similarity	NPD9267	Approved
0.6325	Remote Similarity	NPD9263	Approved
0.6325	Remote Similarity	NPD9264	Approved
0.6325	Remote Similarity	NPD290	Approved
0.632	Remote Similarity	NPD3019	Approved
0.632	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD3317	Approved
0.6308	Remote Similarity	NPD3663	Approved
0.6308	Remote Similarity	NPD3664	Approved
0.6308	Remote Similarity	NPD3661	Approved
0.6308	Remote Similarity	NPD3662	Phase 3
0.629	Remote Similarity	NPD1894	Discontinued
0.629	Remote Similarity	NPD7009	Phase 2
0.6288	Remote Similarity	NPD4619	Approved
0.6288	Remote Similarity	NPD4621	Approved
0.6288	Remote Similarity	NPD6798	Discontinued
0.6281	Remote Similarity	NPD2652	Approved
0.6281	Remote Similarity	NPD2650	Approved
0.6273	Remote Similarity	NPD845	Approved
0.6273	Remote Similarity	NPD1066	Discontinued
0.6271	Remote Similarity	NPD74	Approved
0.6271	Remote Similarity	NPD9266	Approved
0.627	Remote Similarity	NPD4879	Approved
0.627	Remote Similarity	NPD3847	Discontinued
0.627	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6259	Remote Similarity	NPD4628	Phase 3
0.6259	Remote Similarity	NPD8166	Discontinued
0.6241	Remote Similarity	NPD4062	Phase 3
0.6241	Remote Similarity	NPD6233	Phase 2
0.6239	Remote Similarity	NPD6685	Approved
0.6232	Remote Similarity	NPD2424	Discontinued
0.6231	Remote Similarity	NPD2798	Approved
0.6216	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6216	Remote Similarity	NPD6049	Phase 2
0.6216	Remote Similarity	NPD6048	Clinical (unspecified phase)
0.621	Remote Similarity	NPD7610	Discontinued
0.6202	Remote Similarity	NPD3225	Approved
0.6198	Remote Similarity	NPD7843	Approved
0.6194	Remote Similarity	NPD5119	Approved
0.6194	Remote Similarity	NPD5120	Approved
0.6194	Remote Similarity	NPD943	Approved
0.6194	Remote Similarity	NPD1240	Approved
0.6194	Remote Similarity	NPD5121	Approved
0.619	Remote Similarity	NPD1778	Approved
0.6174	Remote Similarity	NPD4817	Approved
0.6174	Remote Similarity	NPD4818	Approved
0.6172	Remote Similarity	NPD9717	Approved
0.6168	Remote Similarity	NPD506	Clinical (unspecified phase)
0.6161	Remote Similarity	NPD844	Approved
0.6148	Remote Similarity	NPD447	Suspended
0.6148	Remote Similarity	NPD230	Phase 1
0.6148	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6148	Remote Similarity	NPD6355	Discontinued
0.614	Remote Similarity	NPD3097	Clinical (unspecified phase)
0.6127	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6126	Remote Similarity	NPD1563	Approved
0.6124	Remote Similarity	NPD1755	Approved
0.6121	Remote Similarity	NPD5765	Approved
0.6121	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.6116	Remote Similarity	NPD9508	Approved
0.6111	Remote Similarity	NPD1651	Approved
0.6107	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6107	Remote Similarity	NPD6085	Phase 2
0.6107	Remote Similarity	NPD4980	Approved
0.6107	Remote Similarity	NPD2788	Approved
0.6103	Remote Similarity	NPD1607	Approved
0.6102	Remote Similarity	NPD968	Approved
0.6099	Remote Similarity	NPD2354	Approved
0.6095	Remote Similarity	NPD6110	Phase 1

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