NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	166.06
Volume:	171.489
LogP:	0.88
LogD:	1.058
LogS:	-1.579
# Rotatable Bonds:	3
TPSA:	46.53
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.687
Synthetic Accessibility Score:	1.694
Fsp3:	0.222
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:	-4.414
MDCK Permeability:	1.8403288777335547e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.039
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.52

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.18
Plasma Protein Binding (PPB):	31.487865447998047%
Volume Distribution (VD):	0.862
Pgp-substrate:	64.36515808105469%

ADMET: Metabolism

CYP1A2-inhibitor:	0.391
CYP1A2-substrate:	0.674
CYP2C19-inhibitor:	0.108
CYP2C19-substrate:	0.092
CYP2C9-inhibitor:	0.042
CYP2C9-substrate:	0.293
CYP2D6-inhibitor:	0.023
CYP2D6-substrate:	0.369
CYP3A4-inhibitor:	0.029
CYP3A4-substrate:	0.293

ADMET: Excretion

Clearance (CL):	8.827
Half-life (T1/2):	0.827

ADMET: Toxicity

hERG Blockers:	0.044
Human Hepatotoxicity (H-HT):	0.049
Drug-inuced Liver Injury (DILI):	0.809
AMES Toxicity:	0.566
Rat Oral Acute Toxicity:	0.836
Maximum Recommended Daily Dose:	0.017
Skin Sensitization:	0.444
Carcinogencity:	0.684
Eye Corrosion:	0.75
Eye Irritation:	0.991
Respiratory Toxicity:	0.242

Download Data

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

Natural Product: NPC11824

Natural Product ID:	NPC11824
*Common Name:**	2-Methoxy-4'-Hydroxyacetophenone
IUPAC Name:	1-(4-hydroxyphenyl)-2-methoxyethanone
Synonyms:
Standard InCHIKey:	HUXGFSJRCMJOAK-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C9H10O3/c1-12-6-9(11)7-2-4-8(10)5-3-7/h2-5,10H,6H2,1H3
SMILES:	COCC(=O)c1ccc(cc1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1761958
PubChem CID:	3015614
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0001831] Carbonyl compounds [CHEMONTID:0000118] Ketones [CHEMONTID:0003670] Aryl ketones [CHEMONTID:0004296] Phenylketones [CHEMONTID:0004298] Alkyl-phenylketones

*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
NPO1103	Dioscorea japonica	Species	Dioscoreaceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[21353549]
NPO1103	Dioscorea japonica	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1103	Dioscorea japonica	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1103	Dioscorea japonica	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO1103	Dioscorea japonica	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

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

NP Quantity Composition/Concentration

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

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

Biological Activity

Activity Type	# Activity
Others	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT76	Cell Line	C6	Rattus norvegicus	Activity	=	105.6	%	PMID[550523]
NPT76	Cell Line	C6	Rattus norvegicus	Activity	=	99.8	%	PMID[550523]

☑ 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 NPC11824 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	258
0.1-0.2	1743
0.2-0.3	4455
0.3-0.4	11335
0.4-0.5	7474
0.5-0.6	7144
0.6-0.7	8119
0.7-0.8	2020
0.8-0.85	115
0.85-0.9	28
0.9-0.95	4
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9623	High Similarity	NPC212718
0.9429	High Similarity	NPC226699
0.9333	High Similarity	NPC6984
0.9259	High Similarity	NPC114682
0.9252	High Similarity	NPC95172
0.8981	High Similarity	NPC17525
0.8919	High Similarity	NPC242136
0.8879	High Similarity	NPC219913
0.8829	High Similarity	NPC231717
0.8818	High Similarity	NPC116842
0.8783	High Similarity	NPC473767
0.8762	High Similarity	NPC280869
0.8739	High Similarity	NPC268388
0.8716	High Similarity	NPC34715
0.8696	High Similarity	NPC249435
0.8696	High Similarity	NPC27633
0.8696	High Similarity	NPC94298
0.8684	High Similarity	NPC131192
0.8684	High Similarity	NPC28951
0.8684	High Similarity	NPC325646
0.8667	High Similarity	NPC260000
0.8636	High Similarity	NPC224584
0.8609	High Similarity	NPC150919
0.8596	High Similarity	NPC322197
0.8571	High Similarity	NPC23332
0.8545	High Similarity	NPC141523
0.8545	High Similarity	NPC29883
0.8532	High Similarity	NPC13495
0.8496	Intermediate Similarity	NPC48525
0.8487	Intermediate Similarity	NPC139171
0.8482	Intermediate Similarity	NPC21162
0.8482	Intermediate Similarity	NPC183648
0.8468	Intermediate Similarity	NPC198249
0.8462	Intermediate Similarity	NPC161617
0.8455	Intermediate Similarity	NPC69332
0.8455	Intermediate Similarity	NPC95178
0.8455	Intermediate Similarity	NPC184658
0.8455	Intermediate Similarity	NPC29989
0.8448	Intermediate Similarity	NPC174087
0.8435	Intermediate Similarity	NPC23402
0.8376	Intermediate Similarity	NPC474890
0.8376	Intermediate Similarity	NPC161943
0.8376	Intermediate Similarity	NPC273282
0.8347	Intermediate Similarity	NPC184219
0.8333	Intermediate Similarity	NPC164947
0.8333	Intermediate Similarity	NPC67300
0.8333	Intermediate Similarity	NPC52472
0.8319	Intermediate Similarity	NPC216216
0.8305	Intermediate Similarity	NPC61779
0.8305	Intermediate Similarity	NPC158222
0.8304	Intermediate Similarity	NPC31274
0.8304	Intermediate Similarity	NPC317305
0.8288	Intermediate Similarity	NPC70843
0.8286	Intermediate Similarity	NPC181709
0.8279	Intermediate Similarity	NPC287473
0.825	Intermediate Similarity	NPC295034
0.8246	Intermediate Similarity	NPC57879
0.8241	Intermediate Similarity	NPC245561
0.824	Intermediate Similarity	NPC27659
0.8235	Intermediate Similarity	NPC159525
0.823	Intermediate Similarity	NPC326187
0.823	Intermediate Similarity	NPC88141
0.822	Intermediate Similarity	NPC209486
0.822	Intermediate Similarity	NPC184527
0.822	Intermediate Similarity	NPC41567
0.822	Intermediate Similarity	NPC40649
0.8214	Intermediate Similarity	NPC303264
0.8211	Intermediate Similarity	NPC204579
0.8211	Intermediate Similarity	NPC110211
0.8211	Intermediate Similarity	NPC51037
0.8205	Intermediate Similarity	NPC19290
0.8205	Intermediate Similarity	NPC83718
0.8198	Intermediate Similarity	NPC163734
0.8197	Intermediate Similarity	NPC474803
0.819	Intermediate Similarity	NPC81808
0.819	Intermediate Similarity	NPC285350
0.8182	Intermediate Similarity	NPC69403
0.8182	Intermediate Similarity	NPC291189
0.8182	Intermediate Similarity	NPC309765
0.8174	Intermediate Similarity	NPC17693
0.8167	Intermediate Similarity	NPC248363
0.8167	Intermediate Similarity	NPC297186
0.8167	Intermediate Similarity	NPC190971
0.816	Intermediate Similarity	NPC120488
0.816	Intermediate Similarity	NPC102829
0.8145	Intermediate Similarity	NPC16651
0.8145	Intermediate Similarity	NPC32163
0.814	Intermediate Similarity	NPC38158
0.8136	Intermediate Similarity	NPC469954
0.8131	Intermediate Similarity	NPC286006
0.813	Intermediate Similarity	NPC49938
0.813	Intermediate Similarity	NPC123506
0.812	Intermediate Similarity	NPC161304
0.812	Intermediate Similarity	NPC240163
0.812	Intermediate Similarity	NPC278102
0.8108	Intermediate Similarity	NPC8931
0.8108	Intermediate Similarity	NPC261573
0.8108	Intermediate Similarity	NPC249067
0.8108	Intermediate Similarity	NPC120693
0.8099	Intermediate Similarity	NPC224273
0.8099	Intermediate Similarity	NPC115159
0.8099	Intermediate Similarity	NPC303737
0.8099	Intermediate Similarity	NPC45438
0.8099	Intermediate Similarity	NPC267552
0.8099	Intermediate Similarity	NPC19174
0.8099	Intermediate Similarity	NPC156139
0.8099	Intermediate Similarity	NPC143427
0.8099	Intermediate Similarity	NPC73532
0.8099	Intermediate Similarity	NPC120545
0.8091	Intermediate Similarity	NPC472585
0.8083	Intermediate Similarity	NPC294037
0.808	Intermediate Similarity	NPC165257
0.808	Intermediate Similarity	NPC80694
0.808	Intermediate Similarity	NPC237225
0.808	Intermediate Similarity	NPC473744
0.808	Intermediate Similarity	NPC186098
0.808	Intermediate Similarity	NPC2596
0.8067	Intermediate Similarity	NPC283844
0.8067	Intermediate Similarity	NPC94637
0.8065	Intermediate Similarity	NPC15837
0.8062	Intermediate Similarity	NPC139519
0.8053	Intermediate Similarity	NPC228737
0.8051	Intermediate Similarity	NPC128825
0.8051	Intermediate Similarity	NPC128249
0.8049	Intermediate Similarity	NPC474766
0.8049	Intermediate Similarity	NPC221798
0.8034	Intermediate Similarity	NPC118288
0.8034	Intermediate Similarity	NPC276111
0.8034	Intermediate Similarity	NPC252004
0.8033	Intermediate Similarity	NPC32032
0.8033	Intermediate Similarity	NPC217756
0.8033	Intermediate Similarity	NPC282577
0.8033	Intermediate Similarity	NPC475192
0.8033	Intermediate Similarity	NPC91478
0.8033	Intermediate Similarity	NPC133909
0.8033	Intermediate Similarity	NPC68167
0.8018	Intermediate Similarity	NPC304638
0.8017	Intermediate Similarity	NPC146642
0.8017	Intermediate Similarity	NPC149246
0.8017	Intermediate Similarity	NPC236520
0.8017	Intermediate Similarity	NPC294361
0.8016	Intermediate Similarity	NPC194979
0.8016	Intermediate Similarity	NPC939
0.8	Intermediate Similarity	NPC253746
0.8	Intermediate Similarity	NPC90522
0.8	Intermediate Similarity	NPC252544
0.8	Intermediate Similarity	NPC321252
0.8	Intermediate Similarity	NPC328459
0.8	Intermediate Similarity	NPC222905
0.7983	Intermediate Similarity	NPC269414
0.7969	Intermediate Similarity	NPC323379
0.7969	Intermediate Similarity	NPC477407
0.7969	Intermediate Similarity	NPC327204
0.7969	Intermediate Similarity	NPC50763
0.7967	Intermediate Similarity	NPC174991
0.7967	Intermediate Similarity	NPC135062
0.7966	Intermediate Similarity	NPC220540
0.7965	Intermediate Similarity	NPC187913
0.7965	Intermediate Similarity	NPC188677
0.7965	Intermediate Similarity	NPC317592
0.7955	Intermediate Similarity	NPC52358
0.7953	Intermediate Similarity	NPC247779
0.7953	Intermediate Similarity	NPC245395
0.7951	Intermediate Similarity	NPC215392
0.7951	Intermediate Similarity	NPC242895
0.7951	Intermediate Similarity	NPC472892
0.7946	Intermediate Similarity	NPC38209
0.7944	Intermediate Similarity	NPC138117
0.7944	Intermediate Similarity	NPC325292
0.7939	Intermediate Similarity	NPC264022
0.7934	Intermediate Similarity	NPC72977
0.7931	Intermediate Similarity	NPC177576
0.7925	Intermediate Similarity	NPC300017
0.7923	Intermediate Similarity	NPC130899
0.7923	Intermediate Similarity	NPC283590
0.7923	Intermediate Similarity	NPC61153
0.7923	Intermediate Similarity	NPC70859
0.792	Intermediate Similarity	NPC473751
0.792	Intermediate Similarity	NPC62952
0.792	Intermediate Similarity	NPC475236
0.792	Intermediate Similarity	NPC305717
0.792	Intermediate Similarity	NPC95309
0.7913	Intermediate Similarity	NPC234639
0.7907	Intermediate Similarity	NPC78307
0.7907	Intermediate Similarity	NPC477280
0.7907	Intermediate Similarity	NPC477281
0.7907	Intermediate Similarity	NPC19719
0.7903	Intermediate Similarity	NPC164014
0.7903	Intermediate Similarity	NPC13238
0.7903	Intermediate Similarity	NPC310540
0.7899	Intermediate Similarity	NPC477453
0.7899	Intermediate Similarity	NPC470860
0.7895	Intermediate Similarity	NPC49242
0.7891	Intermediate Similarity	NPC475042
0.7891	Intermediate Similarity	NPC473777
0.789	Intermediate Similarity	NPC283711
0.7886	Intermediate Similarity	NPC91105
0.7879	Intermediate Similarity	NPC325625
0.7874	Intermediate Similarity	NPC171460
0.7874	Intermediate Similarity	NPC226855

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 NPC11824 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	264
0.1-0.2	1000
0.2-0.3	1387
0.3-0.4	2710
0.4-0.5	2095
0.5-0.6	1216
0.6-0.7	410
0.7-0.8	64
0.8-0.85	2
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8696	High Similarity	NPD9545	Approved
0.8545	High Similarity	NPD9265	Clinical (unspecified phase)
0.8151	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.8108	Intermediate Similarity	NPD1237	Approved
0.8051	Intermediate Similarity	NPD9493	Approved
0.7949	Intermediate Similarity	NPD1241	Discontinued
0.7857	Intermediate Similarity	NPD9494	Approved
0.7829	Intermediate Similarity	NPD1240	Approved
0.7826	Intermediate Similarity	NPD74	Approved
0.7826	Intermediate Similarity	NPD9266	Approved
0.775	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD3972	Approved
0.7739	Intermediate Similarity	NPD9267	Approved
0.7739	Intermediate Similarity	NPD9264	Approved
0.7739	Intermediate Similarity	NPD9263	Approved
0.771	Intermediate Similarity	NPD1607	Approved
0.7594	Intermediate Similarity	NPD1510	Phase 2
0.7545	Intermediate Similarity	NPD2933	Approved
0.7545	Intermediate Similarity	NPD2934	Approved
0.7524	Intermediate Similarity	NPD111	Approved
0.75	Intermediate Similarity	NPD9495	Approved
0.75	Intermediate Similarity	NPD9258	Approved
0.75	Intermediate Similarity	NPD9256	Approved
0.75	Intermediate Similarity	NPD230	Phase 1
0.7477	Intermediate Similarity	NPD2859	Approved
0.7477	Intermediate Similarity	NPD2860	Approved
0.7463	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7426	Intermediate Similarity	NPD1549	Phase 2
0.7424	Intermediate Similarity	NPD943	Approved
0.7422	Intermediate Similarity	NPD1164	Approved
0.7391	Intermediate Similarity	NPD9261	Approved
0.7387	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD1201	Approved
0.7377	Intermediate Similarity	NPD255	Approved
0.7377	Intermediate Similarity	NPD256	Approved
0.7372	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD2344	Approved
0.7344	Intermediate Similarity	NPD1876	Approved
0.7323	Intermediate Similarity	NPD9269	Phase 2
0.7323	Intermediate Similarity	NPD9717	Approved
0.7295	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7295	Intermediate Similarity	NPD9281	Approved
0.7293	Intermediate Similarity	NPD3140	Approved
0.7293	Intermediate Similarity	NPD3142	Approved
0.7287	Intermediate Similarity	NPD1470	Approved
0.7286	Intermediate Similarity	NPD6799	Approved
0.7281	Intermediate Similarity	NPD3020	Approved
0.728	Intermediate Similarity	NPD9268	Approved
0.7273	Intermediate Similarity	NPD3764	Approved
0.7266	Intermediate Similarity	NPD2354	Approved
0.7244	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD2932	Approved
0.7222	Intermediate Similarity	NPD3019	Approved
0.7206	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7194	Intermediate Similarity	NPD4628	Phase 3
0.719	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7177	Intermediate Similarity	NPD9568	Approved
0.7155	Intermediate Similarity	NPD940	Approved
0.7155	Intermediate Similarity	NPD846	Approved
0.7154	Intermediate Similarity	NPD1203	Approved
0.7153	Intermediate Similarity	NPD2935	Discontinued
0.7143	Intermediate Similarity	NPD3887	Approved
0.7143	Intermediate Similarity	NPD2309	Approved
0.7132	Intermediate Similarity	NPD1755	Approved
0.713	Intermediate Similarity	NPD9259	Approved
0.713	Intermediate Similarity	NPD1238	Approved
0.713	Intermediate Similarity	NPD9257	Approved
0.7101	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD2353	Approved
0.7099	Intermediate Similarity	NPD2798	Approved
0.7095	Intermediate Similarity	NPD3882	Suspended
0.709	Intermediate Similarity	NPD520	Approved
0.7083	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD1894	Discontinued
0.7059	Intermediate Similarity	NPD3134	Approved
0.7054	Intermediate Similarity	NPD1481	Phase 2
0.705	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD7075	Discontinued
0.7034	Intermediate Similarity	NPD164	Approved
0.7029	Intermediate Similarity	NPD2796	Approved
0.7021	Intermediate Similarity	NPD6190	Approved
0.7018	Intermediate Similarity	NPD844	Approved
0.7018	Intermediate Similarity	NPD1809	Phase 2
0.7015	Intermediate Similarity	NPD6798	Discontinued
0.7	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD1358	Approved
0.6991	Remote Similarity	NPD1202	Approved
0.6991	Remote Similarity	NPD845	Approved
0.6986	Remote Similarity	NPD6599	Discontinued
0.6977	Remote Similarity	NPD1535	Discovery
0.6967	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD4062	Phase 3
0.6963	Remote Similarity	NPD6233	Phase 2
0.6959	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD2799	Discontinued
0.6957	Remote Similarity	NPD288	Approved
0.695	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD1929	Approved
0.6949	Remote Similarity	NPD1930	Approved
0.6949	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD1283	Approved
0.6944	Remote Similarity	NPD1512	Approved
0.6942	Remote Similarity	NPD2182	Approved
0.6939	Remote Similarity	NPD958	Approved
0.6923	Remote Similarity	NPD1608	Approved
0.6923	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD7458	Discontinued
0.6911	Remote Similarity	NPD228	Approved
0.6892	Remote Similarity	NPD6801	Discontinued
0.6891	Remote Similarity	NPD9608	Approved
0.6891	Remote Similarity	NPD9610	Approved
0.6889	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD9380	Clinical (unspecified phase)
0.688	Remote Similarity	NPD2629	Approved
0.6875	Remote Similarity	NPD1651	Approved
0.6875	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD4380	Phase 2
0.6866	Remote Similarity	NPD6832	Phase 2
0.6861	Remote Similarity	NPD6355	Discontinued
0.6857	Remote Similarity	NPD1471	Phase 3
0.6852	Remote Similarity	NPD9491	Approved
0.6849	Remote Similarity	NPD957	Approved
0.6842	Remote Similarity	NPD1019	Discontinued
0.6838	Remote Similarity	NPD6663	Approved
0.6838	Remote Similarity	NPD2066	Phase 3
0.6831	Remote Similarity	NPD3750	Approved
0.6831	Remote Similarity	NPD8166	Discontinued
0.6831	Remote Similarity	NPD7003	Approved
0.6828	Remote Similarity	NPD9509	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD7411	Suspended
0.6807	Remote Similarity	NPD6647	Phase 2
0.6806	Remote Similarity	NPD1511	Approved
0.6803	Remote Similarity	NPD2684	Approved
0.6797	Remote Similarity	NPD1759	Phase 1
0.6791	Remote Similarity	NPD454	Approved
0.6791	Remote Similarity	NPD5736	Approved
0.6788	Remote Similarity	NPD825	Approved
0.6788	Remote Similarity	NPD826	Approved
0.6786	Remote Similarity	NPD1551	Phase 2
0.678	Remote Similarity	NPD1242	Phase 1
0.6779	Remote Similarity	NPD1934	Approved
0.6779	Remote Similarity	NPD7577	Discontinued
0.6777	Remote Similarity	NPD968	Approved
0.6769	Remote Similarity	NPD3847	Discontinued
0.6767	Remote Similarity	NPD2797	Approved
0.6765	Remote Similarity	NPD2313	Discontinued
0.6765	Remote Similarity	NPD3268	Approved
0.6765	Remote Similarity	NPD411	Approved
0.6748	Remote Similarity	NPD3021	Approved
0.6748	Remote Similarity	NPD2067	Discontinued
0.6748	Remote Similarity	NPD3022	Approved
0.6746	Remote Similarity	NPD5951	Approved
0.6742	Remote Similarity	NPD5158	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD5157	Phase 1
0.6742	Remote Similarity	NPD5159	Phase 2
0.6739	Remote Similarity	NPD447	Suspended
0.6739	Remote Similarity	NPD555	Phase 2
0.6738	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD7440	Discontinued
0.6733	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.672	Remote Similarity	NPD5277	Phase 2
0.672	Remote Similarity	NPD821	Approved
0.6719	Remote Similarity	NPD5536	Phase 2
0.6719	Remote Similarity	NPD1758	Phase 1
0.6718	Remote Similarity	NPD422	Phase 1
0.6718	Remote Similarity	NPD1281	Approved
0.6716	Remote Similarity	NPD258	Approved
0.6716	Remote Similarity	NPD257	Approved
0.6715	Remote Similarity	NPD259	Phase 1
0.6714	Remote Similarity	NPD4308	Phase 3
0.6712	Remote Similarity	NPD5049	Phase 3
0.6692	Remote Similarity	NPD196	Phase 1
0.6692	Remote Similarity	NPD17	Approved
0.6692	Remote Similarity	NPD4626	Approved
0.6692	Remote Similarity	NPD1778	Approved
0.6691	Remote Similarity	NPD6651	Approved
0.669	Remote Similarity	NPD7390	Discontinued
0.6689	Remote Similarity	NPD3817	Phase 2
0.6689	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD3455	Phase 2
0.6667	Remote Similarity	NPD5403	Approved
0.6667	Remote Similarity	NPD5408	Approved
0.6667	Remote Similarity	NPD4208	Discontinued
0.6667	Remote Similarity	NPD4878	Approved
0.6667	Remote Similarity	NPD5404	Approved
0.6667	Remote Similarity	NPD5405	Approved
0.6667	Remote Similarity	NPD5406	Approved
0.6644	Remote Similarity	NPD5401	Approved
0.6643	Remote Similarity	NPD743	Approved
0.6641	Remote Similarity	NPD3023	Approved
0.6641	Remote Similarity	NPD3026	Approved
0.664	Remote Similarity	NPD6124	Clinical (unspecified phase)
0.664	Remote Similarity	NPD9508	Approved
0.6639	Remote Similarity	NPD3028	Approved
0.6638	Remote Similarity	NPD9260	Approved
0.6638	Remote Similarity	NPD1693	Approved
0.6637	Remote Similarity	NPD800	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