NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	136.05
Volume:	145.402
LogP:	2.035
LogD:	1.62
LogS:	-1.761
# Rotatable Bonds:	1
TPSA:	37.3
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.595
Synthetic Accessibility Score:	1.55
Fsp3:	0.125
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:	-4.383
MDCK Permeability:	2.5900186301441863e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.008
30% Bioavailability (F30%):	0.038

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.508
Plasma Protein Binding (PPB):	80.93433380126953%
Volume Distribution (VD):	0.774
Pgp-substrate:	19.99612808227539%

ADMET: Metabolism

CYP1A2-inhibitor:	0.934
CYP1A2-substrate:	0.734
CYP2C19-inhibitor:	0.562
CYP2C19-substrate:	0.126
CYP2C9-inhibitor:	0.227
CYP2C9-substrate:	0.675
CYP2D6-inhibitor:	0.338
CYP2D6-substrate:	0.579
CYP3A4-inhibitor:	0.032
CYP3A4-substrate:	0.234

ADMET: Excretion

Clearance (CL):	8.644
Half-life (T1/2):	0.861

ADMET: Toxicity

hERG Blockers:	0.022
Human Hepatotoxicity (H-HT):	0.041
Drug-inuced Liver Injury (DILI):	0.48
AMES Toxicity:	0.309
Rat Oral Acute Toxicity:	0.38
Maximum Recommended Daily Dose:	0.018
Skin Sensitization:	0.432
Carcinogencity:	0.579
Eye Corrosion:	0.923
Eye Irritation:	0.993
Respiratory Toxicity:	0.801

Download Data

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

Natural Product: NPC224584

Natural Product ID:	NPC224584
*Common Name:**	1-(2-Hydroxyphenyl)Ethanone
IUPAC Name:	1-(2-hydroxyphenyl)ethanone
Synonyms:
Standard InCHIKey:	JECYUBVRTQDVAT-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C8H8O2/c1-6(9)7-4-2-3-5-8(7)10/h2-5,10H,1H3
SMILES:	CC(=O)c1ccccc1O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3187012
PubChem CID:	8375
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
NPO31073	Ligusticum chuanxiong	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1320	Thalictrum ichangense	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1320	Thalictrum ichangense	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO31073	Ligusticum chuanxiong	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO1320	Thalictrum ichangense	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	4
Others	1
Potency	2

Activity Type	# Activity
Individual Protein	1
Others	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT43	Individual Protein	Tyrosinase	Agaricus bisporus	IC50	>	300000.0	nM	PMID[484917]
NPT2	Others	Unspecified		IC50	=	390000.0	nM	PMID[484915]
NPT2	Others	Unspecified		IC50	=	320000.0	nM	PMID[484915]
NPT35	Others	n.a.		IC50	=	154887000.0	nM	PMID[484916]
NPT35	Others	n.a.		Solubility	=	50000.0	nM	PMID[484918]
NPT2	Others	Unspecified		Potency	n.a.	977	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	68589.6	nM	PubChem BioAssay data set

☑ 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 NPC224584 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	275
0.1-0.2	2025
0.2-0.3	4952
0.3-0.4	12187
0.4-0.5	6520
0.5-0.6	7720
0.6-0.7	6826
0.7-0.8	1912
0.8-0.85	202
0.85-0.9	61
0.9-0.95	15
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9346	High Similarity	NPC161304
0.9346	High Similarity	NPC240163
0.932	High Similarity	NPC141523
0.9252	High Similarity	NPC276111
0.9252	High Similarity	NPC118288
0.9174	High Similarity	NPC269414
0.9135	High Similarity	NPC303264
0.9135	High Similarity	NPC226699
0.9135	High Similarity	NPC34715
0.9091	High Similarity	NPC41567
0.9083	High Similarity	NPC477453
0.9048	High Similarity	NPC100551
0.9038	High Similarity	NPC6984
0.9009	High Similarity	NPC161617
0.9	High Similarity	NPC121259
0.8981	High Similarity	NPC242136
0.8981	High Similarity	NPC211421
0.8972	High Similarity	NPC114682
0.8962	High Similarity	NPC95172
0.8929	High Similarity	NPC285829
0.8929	High Similarity	NPC206778
0.8909	High Similarity	NPC128825
0.8909	High Similarity	NPC108288
0.8829	High Similarity	NPC125252
0.8824	High Similarity	NPC280869
0.875	High Similarity	NPC40649
0.875	High Similarity	NPC184527
0.875	High Similarity	NPC94637
0.875	High Similarity	NPC209486
0.8725	High Similarity	NPC260000
0.8696	High Similarity	NPC309765
0.8696	High Similarity	NPC307174
0.8692	High Similarity	NPC17525
0.8684	High Similarity	NPC297186
0.8673	High Similarity	NPC188814
0.8673	High Similarity	NPC328459
0.8673	High Similarity	NPC90522
0.8673	High Similarity	NPC195262
0.8636	High Similarity	NPC11824
0.8624	High Similarity	NPC212718
0.8621	High Similarity	NPC477153
0.8609	High Similarity	NPC19174
0.8609	High Similarity	NPC143427
0.8609	High Similarity	NPC303737
0.8609	High Similarity	NPC73532
0.8609	High Similarity	NPC267552
0.8609	High Similarity	NPC45438
0.8609	High Similarity	NPC224273
0.8609	High Similarity	NPC156139
0.8609	High Similarity	NPC115159
0.8596	High Similarity	NPC294037
0.8596	High Similarity	NPC216297
0.8596	High Similarity	NPC72977
0.8596	High Similarity	NPC7151
0.8596	High Similarity	NPC473662
0.8571	High Similarity	NPC13426
0.8559	High Similarity	NPC163154
0.8547	High Similarity	NPC310540
0.8545	High Similarity	NPC231717
0.8534	High Similarity	NPC133909
0.8534	High Similarity	NPC32032
0.8534	High Similarity	NPC300274
0.8532	High Similarity	NPC116842
0.8522	High Similarity	NPC222876
0.8522	High Similarity	NPC301987
0.8522	High Similarity	NPC292665
0.8522	High Similarity	NPC115188
0.8522	High Similarity	NPC272454
0.8522	High Similarity	NPC244994
0.8522	High Similarity	NPC146642
0.8522	High Similarity	NPC26433
0.8522	High Similarity	NPC35856
0.8522	High Similarity	NPC149246
0.8522	High Similarity	NPC178395
0.8522	High Similarity	NPC159760
0.8522	High Similarity	NPC179092
0.8509	High Similarity	NPC184579
0.8509	High Similarity	NPC233165
0.8509	High Similarity	NPC232178
0.8509	High Similarity	NPC473767
0.8505	High Similarity	NPC29989
0.8505	High Similarity	NPC69332
0.8505	High Similarity	NPC95178
0.8496	Intermediate Similarity	NPC160199
0.8475	Intermediate Similarity	NPC287473
0.8468	Intermediate Similarity	NPC223004
0.8462	Intermediate Similarity	NPC375356
0.8455	Intermediate Similarity	NPC268388
0.8448	Intermediate Similarity	NPC242895
0.8448	Intermediate Similarity	NPC215392
0.8448	Intermediate Similarity	NPC196976
0.8435	Intermediate Similarity	NPC233282
0.8435	Intermediate Similarity	NPC470092
0.8426	Intermediate Similarity	NPC228737
0.8421	Intermediate Similarity	NPC474890
0.8421	Intermediate Similarity	NPC161943
0.8421	Intermediate Similarity	NPC249435
0.8421	Intermediate Similarity	NPC273282
0.8407	Intermediate Similarity	NPC312800
0.8403	Intermediate Similarity	NPC51037
0.8403	Intermediate Similarity	NPC306765
0.8403	Intermediate Similarity	NPC231774
0.8403	Intermediate Similarity	NPC473751
0.8403	Intermediate Similarity	NPC62952
0.8403	Intermediate Similarity	NPC3224
0.839	Intermediate Similarity	NPC193805
0.839	Intermediate Similarity	NPC13238
0.839	Intermediate Similarity	NPC234890
0.839	Intermediate Similarity	NPC74507
0.839	Intermediate Similarity	NPC173978
0.839	Intermediate Similarity	NPC142956
0.8381	Intermediate Similarity	NPC52472
0.8376	Intermediate Similarity	NPC91105
0.835	Intermediate Similarity	NPC246679
0.8349	Intermediate Similarity	NPC317305
0.8348	Intermediate Similarity	NPC158222
0.8333	Intermediate Similarity	NPC72158
0.8333	Intermediate Similarity	NPC169250
0.8333	Intermediate Similarity	NPC181709
0.8333	Intermediate Similarity	NPC23126
0.8333	Intermediate Similarity	NPC28169
0.8333	Intermediate Similarity	NPC98254
0.8333	Intermediate Similarity	NPC103356
0.8333	Intermediate Similarity	NPC266689
0.8333	Intermediate Similarity	NPC150919
0.8333	Intermediate Similarity	NPC162612
0.8333	Intermediate Similarity	NPC70843
0.8333	Intermediate Similarity	NPC30501
0.8333	Intermediate Similarity	NPC105157
0.8333	Intermediate Similarity	NPC187913
0.8333	Intermediate Similarity	NPC100067
0.8333	Intermediate Similarity	NPC190043
0.8319	Intermediate Similarity	NPC103540
0.8319	Intermediate Similarity	NPC322197
0.8319	Intermediate Similarity	NPC23402
0.8305	Intermediate Similarity	NPC472029
0.8305	Intermediate Similarity	NPC65761
0.8304	Intermediate Similarity	NPC279916
0.8304	Intermediate Similarity	NPC53953
0.8291	Intermediate Similarity	NPC226275
0.8291	Intermediate Similarity	NPC198336
0.8286	Intermediate Similarity	NPC245561
0.8276	Intermediate Similarity	NPC159525
0.8276	Intermediate Similarity	NPC294964
0.8273	Intermediate Similarity	NPC88141
0.8269	Intermediate Similarity	NPC283711
0.8264	Intermediate Similarity	NPC237225
0.8264	Intermediate Similarity	NPC473017
0.8264	Intermediate Similarity	NPC221777
0.8264	Intermediate Similarity	NPC165257
0.8264	Intermediate Similarity	NPC282923
0.8264	Intermediate Similarity	NPC186098
0.8264	Intermediate Similarity	NPC80694
0.8264	Intermediate Similarity	NPC48248
0.8264	Intermediate Similarity	NPC21305
0.8261	Intermediate Similarity	NPC283844
0.8261	Intermediate Similarity	NPC241089
0.8261	Intermediate Similarity	NPC171023
0.8257	Intermediate Similarity	NPC29883
0.825	Intermediate Similarity	NPC8745
0.825	Intermediate Similarity	NPC96915
0.825	Intermediate Similarity	NPC160499
0.825	Intermediate Similarity	NPC267846
0.8246	Intermediate Similarity	NPC83718
0.8241	Intermediate Similarity	NPC219913
0.8241	Intermediate Similarity	NPC13495
0.8241	Intermediate Similarity	NPC163734
0.8235	Intermediate Similarity	NPC4012
0.8235	Intermediate Similarity	NPC68756
0.8235	Intermediate Similarity	NPC265910
0.8235	Intermediate Similarity	NPC91475
0.8235	Intermediate Similarity	NPC152525
0.823	Intermediate Similarity	NPC81808
0.823	Intermediate Similarity	NPC285350
0.822	Intermediate Similarity	NPC283514
0.822	Intermediate Similarity	NPC311219
0.822	Intermediate Similarity	NPC217756
0.822	Intermediate Similarity	NPC244351
0.8205	Intermediate Similarity	NPC165197
0.8205	Intermediate Similarity	NPC190971
0.82	Intermediate Similarity	NPC407
0.82	Intermediate Similarity	NPC307235
0.8198	Intermediate Similarity	NPC21162
0.8197	Intermediate Similarity	NPC99731
0.8197	Intermediate Similarity	NPC474998
0.8197	Intermediate Similarity	NPC34414
0.8197	Intermediate Similarity	NPC146647
0.8197	Intermediate Similarity	NPC109123
0.8182	Intermediate Similarity	NPC116513
0.8182	Intermediate Similarity	NPC22783
0.8174	Intermediate Similarity	NPC174087
0.8167	Intermediate Similarity	NPC167055
0.8167	Intermediate Similarity	NPC240744
0.8167	Intermediate Similarity	NPC10926
0.8167	Intermediate Similarity	NPC475733
0.8167	Intermediate Similarity	NPC477454
0.8167	Intermediate Similarity	NPC4164
0.8165	Intermediate Similarity	NPC184658
0.8158	Intermediate Similarity	NPC188907
0.8151	Intermediate Similarity	NPC93730

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 NPC224584 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	308
0.1-0.2	997
0.2-0.3	1356
0.3-0.4	2799
0.4-0.5	2121
0.5-0.6	1126
0.6-0.7	354
0.7-0.8	73
0.8-0.85	8
0.85-0.9	6
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9048	High Similarity	NPD9266	Approved
0.9048	High Similarity	NPD74	Approved
0.8952	High Similarity	NPD9267	Approved
0.8952	High Similarity	NPD9263	Approved
0.8952	High Similarity	NPD9264	Approved
0.8909	High Similarity	NPD9493	Approved
0.8909	High Similarity	NPD405	Clinical (unspecified phase)
0.8571	High Similarity	NPD9261	Approved
0.8448	Intermediate Similarity	NPD1201	Approved
0.8393	Intermediate Similarity	NPD9281	Approved
0.8319	Intermediate Similarity	NPD1470	Approved
0.8257	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.822	Intermediate Similarity	NPD9717	Approved
0.819	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.8167	Intermediate Similarity	NPD1164	Approved
0.8017	Intermediate Similarity	NPD1203	Approved
0.8	Intermediate Similarity	NPD1240	Approved
0.7951	Intermediate Similarity	NPD2798	Approved
0.7949	Intermediate Similarity	NPD9545	Approved
0.7874	Intermediate Similarity	NPD1607	Approved
0.7864	Intermediate Similarity	NPD9256	Approved
0.7864	Intermediate Similarity	NPD9258	Approved
0.7857	Intermediate Similarity	NPD943	Approved
0.7833	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7818	Intermediate Similarity	NPD1237	Approved
0.7664	Intermediate Similarity	NPD844	Approved
0.7642	Intermediate Similarity	NPD845	Approved
0.7638	Intermediate Similarity	NPD520	Approved
0.7634	Intermediate Similarity	NPD2344	Approved
0.7615	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7615	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7615	Intermediate Similarity	NPD1510	Phase 2
0.7593	Intermediate Similarity	NPD288	Approved
0.757	Intermediate Similarity	NPD2933	Approved
0.757	Intermediate Similarity	NPD2934	Approved
0.7559	Intermediate Similarity	NPD2313	Discontinued
0.7559	Intermediate Similarity	NPD411	Approved
0.7557	Intermediate Similarity	NPD2935	Discontinued
0.7549	Intermediate Similarity	NPD111	Approved
0.7545	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7521	Intermediate Similarity	NPD1241	Discontinued
0.7519	Intermediate Similarity	NPD447	Suspended
0.75	Intermediate Similarity	NPD2859	Approved
0.75	Intermediate Similarity	NPD2860	Approved
0.7481	Intermediate Similarity	NPD2799	Discontinued
0.7477	Intermediate Similarity	NPD940	Approved
0.7477	Intermediate Similarity	NPD846	Approved
0.7476	Intermediate Similarity	NPD9257	Approved
0.7476	Intermediate Similarity	NPD9259	Approved
0.7463	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD1549	Phase 2
0.7407	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD2309	Approved
0.7402	Intermediate Similarity	NPD6832	Phase 2
0.7395	Intermediate Similarity	NPD256	Approved
0.7395	Intermediate Similarity	NPD255	Approved
0.7391	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD1019	Discontinued
0.7368	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD1759	Phase 1
0.7339	Intermediate Similarity	NPD1809	Phase 2
0.7315	Intermediate Similarity	NPD1202	Approved
0.7297	Intermediate Similarity	NPD3020	Approved
0.7293	Intermediate Similarity	NPD5408	Approved
0.7293	Intermediate Similarity	NPD5404	Approved
0.7293	Intermediate Similarity	NPD5406	Approved
0.7293	Intermediate Similarity	NPD1551	Phase 2
0.7293	Intermediate Similarity	NPD5405	Approved
0.7273	Intermediate Similarity	NPD1758	Phase 1
0.7257	Intermediate Similarity	NPD1929	Approved
0.7257	Intermediate Similarity	NPD1930	Approved
0.7257	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD2346	Discontinued
0.7236	Intermediate Similarity	NPD3019	Approved
0.7236	Intermediate Similarity	NPD2932	Approved
0.7207	Intermediate Similarity	NPD9495	Approved
0.72	Intermediate Similarity	NPD3972	Approved
0.719	Intermediate Similarity	NPD9568	Approved
0.7188	Intermediate Similarity	NPD9494	Approved
0.7185	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD9491	Approved
0.7165	Intermediate Similarity	NPD2797	Approved
0.7154	Intermediate Similarity	NPD3764	Approved
0.7143	Intermediate Similarity	NPD2066	Phase 3
0.7143	Intermediate Similarity	NPD9279	Approved
0.7143	Intermediate Similarity	NPD1755	Approved
0.7122	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7122	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD3300	Phase 2
0.709	Intermediate Similarity	NPD4308	Phase 3
0.7087	Intermediate Similarity	NPD1876	Approved
0.708	Intermediate Similarity	NPD1196	Approved
0.7063	Intermediate Similarity	NPD9269	Phase 2
0.7059	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD9273	Approved
0.705	Intermediate Similarity	NPD1511	Approved
0.705	Intermediate Similarity	NPD7390	Discontinued
0.705	Intermediate Similarity	NPD1543	Discontinued
0.7043	Intermediate Similarity	NPD164	Approved
0.7037	Intermediate Similarity	NPD2796	Approved
0.7025	Intermediate Similarity	NPD5951	Approved
0.7025	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7023	Intermediate Similarity	NPD3268	Approved
0.7016	Intermediate Similarity	NPD9268	Approved
0.7007	Intermediate Similarity	NPD1195	Approved
0.7007	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5277	Phase 2
0.6992	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD1933	Approved
0.6991	Remote Similarity	NPD1238	Approved
0.6957	Remote Similarity	NPD3750	Approved
0.695	Remote Similarity	NPD1512	Approved
0.6944	Remote Similarity	NPD800	Approved
0.6937	Remote Similarity	NPD1693	Approved
0.6937	Remote Similarity	NPD9260	Approved
0.6934	Remote Similarity	NPD75	Approved
0.6934	Remote Similarity	NPD9277	Approved
0.6929	Remote Similarity	NPD6799	Approved
0.6929	Remote Similarity	NPD1481	Phase 2
0.6923	Remote Similarity	NPD3226	Approved
0.6917	Remote Similarity	NPD9508	Approved
0.6897	Remote Similarity	NPD9608	Approved
0.6897	Remote Similarity	NPD9610	Approved
0.6891	Remote Similarity	NPD4750	Phase 3
0.6881	Remote Similarity	NPD1086	Approved
0.6881	Remote Similarity	NPD1090	Approved
0.6881	Remote Similarity	NPD1089	Approved
0.6879	Remote Similarity	NPD4662	Approved
0.6879	Remote Similarity	NPD4661	Approved
0.6875	Remote Similarity	NPD4380	Phase 2
0.687	Remote Similarity	NPD1932	Approved
0.6866	Remote Similarity	NPD230	Phase 1
0.6861	Remote Similarity	NPD9274	Approved
0.6861	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6861	Remote Similarity	NPD9275	Approved
0.6861	Remote Similarity	NPD9276	Approved
0.6861	Remote Similarity	NPD9278	Suspended
0.685	Remote Similarity	NPD422	Phase 1
0.685	Remote Similarity	NPD1535	Discovery
0.6847	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD9697	Approved
0.6835	Remote Similarity	NPD7003	Approved
0.6833	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD7411	Suspended
0.6827	Remote Similarity	NPD942	Approved
0.6827	Remote Similarity	NPD226	Approved
0.6815	Remote Similarity	NPD6651	Approved
0.6807	Remote Similarity	NPD2182	Approved
0.6803	Remote Similarity	NPD2296	Approved
0.68	Remote Similarity	NPD9087	Approved
0.6797	Remote Similarity	NPD4878	Approved
0.6797	Remote Similarity	NPD1608	Approved
0.6796	Remote Similarity	NPD9490	Approved
0.6791	Remote Similarity	NPD4307	Phase 2
0.6783	Remote Similarity	NPD5403	Approved
0.6783	Remote Similarity	NPD1242	Phase 1
0.6781	Remote Similarity	NPD1934	Approved
0.678	Remote Similarity	NPD1445	Approved
0.678	Remote Similarity	NPD1444	Approved
0.6769	Remote Similarity	NPD3267	Approved
0.6769	Remote Similarity	NPD3266	Approved
0.6763	Remote Similarity	NPD2800	Approved
0.6763	Remote Similarity	NPD1243	Approved
0.6761	Remote Similarity	NPD5401	Approved
0.6761	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD650	Approved
0.6757	Remote Similarity	NPD3882	Suspended
0.6757	Remote Similarity	NPD1088	Approved
0.675	Remote Similarity	NPD3021	Approved
0.675	Remote Similarity	NPD3022	Approved
0.6744	Remote Similarity	NPD5158	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD5157	Phase 1
0.6744	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD5159	Phase 2
0.6739	Remote Similarity	NPD1471	Phase 3
0.6735	Remote Similarity	NPD2801	Approved
0.6735	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD2342	Discontinued
0.6723	Remote Similarity	NPD290	Approved
0.6721	Remote Similarity	NPD7635	Approved
0.6718	Remote Similarity	NPD257	Approved
0.6718	Remote Similarity	NPD258	Approved
0.6715	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD7075	Discontinued
0.6699	Remote Similarity	NPD9088	Approved
0.6694	Remote Similarity	NPD6671	Approved
0.6693	Remote Similarity	NPD4626	Approved
0.6693	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6693	Remote Similarity	NPD1778	Approved
0.6692	Remote Similarity	NPD3225	Approved
0.6692	Remote Similarity	NPD1283	Approved
0.6689	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3142	Approved
0.6667	Remote Similarity	NPD4208	Discontinued
0.6667	Remote Similarity	NPD6647	Phase 2
0.6667	Remote Similarity	NPD2329	Discontinued
0.6667	Remote Similarity	NPD1894	Discontinued
0.6667	Remote Similarity	NPD3140	Approved
0.6667	Remote Similarity	NPD1239	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