NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	166.06
Volume:	171.489
LogP:	1.268
LogD:	1.211
LogS:	-2.014
# Rotatable Bonds:	2
TPSA:	57.53
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	1
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.646
Synthetic Accessibility Score:	1.926
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:	-4.371
MDCK Permeability:	1.0683198524930049e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.007
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.016
30% Bioavailability (F30%):	0.21

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.28
Plasma Protein Binding (PPB):	61.05720520019531%
Volume Distribution (VD):	0.947
Pgp-substrate:	52.14167785644531%

ADMET: Metabolism

CYP1A2-inhibitor:	0.826
CYP1A2-substrate:	0.374
CYP2C19-inhibitor:	0.187
CYP2C19-substrate:	0.089
CYP2C9-inhibitor:	0.096
CYP2C9-substrate:	0.487
CYP2D6-inhibitor:	0.311
CYP2D6-substrate:	0.536
CYP3A4-inhibitor:	0.066
CYP3A4-substrate:	0.268

ADMET: Excretion

Clearance (CL):	8.063
Half-life (T1/2):	0.876

ADMET: Toxicity

hERG Blockers:	0.037
Human Hepatotoxicity (H-HT):	0.043
Drug-inuced Liver Injury (DILI):	0.509
AMES Toxicity:	0.167
Rat Oral Acute Toxicity:	0.052
Maximum Recommended Daily Dose:	0.014
Skin Sensitization:	0.209
Carcinogencity:	0.045
Eye Corrosion:	0.023
Eye Irritation:	0.978
Respiratory Toxicity:	0.079

Download Data

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

Natural Product: NPC41567

Natural Product ID:	NPC41567
*Common Name:**	1-[2-Hydroxy-4-(Hydroxymethyl)Phenyl]Ethanone
IUPAC Name:	1-[2-hydroxy-4-(hydroxymethyl)phenyl]ethanone
Synonyms:
Standard InCHIKey:	CEKCNQSWPNISHG-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C9H10O3/c1-6(11)8-3-2-7(5-10)4-9(8)12/h2-4,10,12H,5H2,1H3
SMILES:	CC(=O)c1ccc(cc1O)CO
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1795999
PubChem CID:	56663527
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
NPO6414	Eupatorium cannabinum	Species	Asteraceae	Eukaryota	n.a.	aerial part	n.a.	PMID[21391659]
NPO6414	Eupatorium cannabinum	Species	Asteraceae	Eukaryota	Aerial Parts	n.a.	n.a.	PMID[30653318]
NPO6414	Eupatorium cannabinum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6414	Eupatorium cannabinum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6414	Eupatorium cannabinum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO6414	Eupatorium cannabinum	Species	Asteraceae	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

Activity Type	# Activity
NON-MOLECULAR	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	8130.0	nM	PMID[536888]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	6380.0	nM	PMID[536888]

☑ 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 NPC41567 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	285
0.1-0.2	1523
0.2-0.3	3815
0.3-0.4	11195
0.4-0.5	8309
0.5-0.6	6300
0.6-0.7	8631
0.7-0.8	2359
0.8-0.85	225
0.85-0.9	45
0.9-0.95	9
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.955	High Similarity	NPC161304
0.9204	High Similarity	NPC240163
0.916	High Similarity	NPC287473
0.9091	High Similarity	NPC224584
0.9076	High Similarity	NPC152525
0.9076	High Similarity	NPC234890
0.9076	High Similarity	NPC68756
0.9076	High Similarity	NPC74507
0.9043	High Similarity	NPC269414
0.8974	High Similarity	NPC473662
0.8974	High Similarity	NPC216297
0.8974	High Similarity	NPC7151
0.8957	High Similarity	NPC477453
0.8908	High Similarity	NPC307174
0.8879	High Similarity	NPC160199
0.8829	High Similarity	NPC34715
0.8814	High Similarity	NPC285829
0.8814	High Similarity	NPC206778
0.879	High Similarity	NPC136588
0.879	High Similarity	NPC199253
0.8783	High Similarity	NPC163154
0.877	High Similarity	NPC136342
0.877	High Similarity	NPC295202
0.877	High Similarity	NPC49647
0.877	High Similarity	NPC227741
0.876	High Similarity	NPC117794
0.8729	High Similarity	NPC473767
0.8689	High Similarity	NPC472592
0.8689	High Similarity	NPC131799
0.8684	High Similarity	NPC114682
0.8678	High Similarity	NPC477153
0.8661	High Similarity	NPC303264
0.8655	High Similarity	NPC294964
0.8651	High Similarity	NPC242358
0.8651	High Similarity	NPC246693
0.8651	High Similarity	NPC70622
0.8651	High Similarity	NPC110609
0.8644	High Similarity	NPC171023
0.8632	High Similarity	NPC108288
0.8618	High Similarity	NPC306765
0.8607	High Similarity	NPC310540
0.8607	High Similarity	NPC173978
0.8607	High Similarity	NPC142956
0.8595	High Similarity	NPC300274
0.8583	High Similarity	NPC165197
0.8583	High Similarity	NPC52407
0.8559	High Similarity	NPC125252
0.8537	High Similarity	NPC167055
0.8537	High Similarity	NPC240744
0.8525	High Similarity	NPC375356
0.8512	High Similarity	NPC25168
0.8496	Intermediate Similarity	NPC141523
0.8492	Intermediate Similarity	NPC198305
0.8492	Intermediate Similarity	NPC31799
0.8487	Intermediate Similarity	NPC184527
0.848	Intermediate Similarity	NPC237225
0.848	Intermediate Similarity	NPC48248
0.848	Intermediate Similarity	NPC282923
0.8468	Intermediate Similarity	NPC51037
0.8468	Intermediate Similarity	NPC160499
0.8468	Intermediate Similarity	NPC3224
0.8468	Intermediate Similarity	NPC96915
0.8468	Intermediate Similarity	NPC231774
0.8462	Intermediate Similarity	NPC276111
0.8462	Intermediate Similarity	NPC118288
0.8455	Intermediate Similarity	NPC4012
0.8455	Intermediate Similarity	NPC174911
0.8443	Intermediate Similarity	NPC297193
0.8438	Intermediate Similarity	NPC314048
0.843	Intermediate Similarity	NPC244994
0.843	Intermediate Similarity	NPC272454
0.843	Intermediate Similarity	NPC292665
0.843	Intermediate Similarity	NPC115188
0.843	Intermediate Similarity	NPC26433
0.843	Intermediate Similarity	NPC159760
0.843	Intermediate Similarity	NPC35856
0.843	Intermediate Similarity	NPC179092
0.843	Intermediate Similarity	NPC178395
0.843	Intermediate Similarity	NPC301987
0.843	Intermediate Similarity	NPC222876
0.8425	Intermediate Similarity	NPC205992
0.8425	Intermediate Similarity	NPC85342
0.8417	Intermediate Similarity	NPC232178
0.8417	Intermediate Similarity	NPC233165
0.8417	Intermediate Similarity	NPC184579
0.8413	Intermediate Similarity	NPC146647
0.8413	Intermediate Similarity	NPC34414
0.8413	Intermediate Similarity	NPC109123
0.8403	Intermediate Similarity	NPC121259
0.8403	Intermediate Similarity	NPC28169
0.84	Intermediate Similarity	NPC470841
0.8387	Intermediate Similarity	NPC103540
0.8376	Intermediate Similarity	NPC211421
0.8376	Intermediate Similarity	NPC242136
0.8362	Intermediate Similarity	NPC212718
0.8359	Intermediate Similarity	NPC477406
0.8348	Intermediate Similarity	NPC95172
0.8346	Intermediate Similarity	NPC55949
0.8333	Intermediate Similarity	NPC249435
0.8333	Intermediate Similarity	NPC247250
0.8333	Intermediate Similarity	NPC94637
0.8333	Intermediate Similarity	NPC767
0.8333	Intermediate Similarity	NPC226699
0.8321	Intermediate Similarity	NPC305060
0.8319	Intermediate Similarity	NPC312800
0.8319	Intermediate Similarity	NPC128825
0.8319	Intermediate Similarity	NPC163734
0.8306	Intermediate Similarity	NPC236189
0.8305	Intermediate Similarity	NPC81808
0.8305	Intermediate Similarity	NPC197513
0.8305	Intermediate Similarity	NPC41851
0.8304	Intermediate Similarity	NPC471228
0.8304	Intermediate Similarity	NPC235762
0.8293	Intermediate Similarity	NPC217756
0.8293	Intermediate Similarity	NPC282577
0.8291	Intermediate Similarity	NPC231717
0.8281	Intermediate Similarity	NPC471851
0.8268	Intermediate Similarity	NPC474546
0.8268	Intermediate Similarity	NPC99731
0.8268	Intermediate Similarity	NPC278928
0.8264	Intermediate Similarity	NPC90522
0.8264	Intermediate Similarity	NPC161617
0.8264	Intermediate Similarity	NPC328459
0.8261	Intermediate Similarity	NPC317305
0.8261	Intermediate Similarity	NPC100551
0.8258	Intermediate Similarity	NPC98395
0.8258	Intermediate Similarity	NPC173980
0.8254	Intermediate Similarity	NPC471530
0.8246	Intermediate Similarity	NPC187913
0.8246	Intermediate Similarity	NPC6984
0.8244	Intermediate Similarity	NPC315275
0.823	Intermediate Similarity	NPC475225
0.8226	Intermediate Similarity	NPC275145
0.822	Intermediate Similarity	NPC296144
0.822	Intermediate Similarity	NPC28784
0.822	Intermediate Similarity	NPC11824
0.8217	Intermediate Similarity	NPC309430
0.8203	Intermediate Similarity	NPC475741
0.8203	Intermediate Similarity	NPC62219
0.8203	Intermediate Similarity	NPC31539
0.8197	Intermediate Similarity	NPC72977
0.819	Intermediate Similarity	NPC98392
0.8189	Intermediate Similarity	NPC165257
0.8175	Intermediate Similarity	NPC8745
0.8175	Intermediate Similarity	NPC474264
0.8175	Intermediate Similarity	NPC71610
0.8175	Intermediate Similarity	NPC1991
0.8168	Intermediate Similarity	NPC281513
0.8168	Intermediate Similarity	NPC161632
0.8168	Intermediate Similarity	NPC22222
0.816	Intermediate Similarity	NPC13238
0.816	Intermediate Similarity	NPC56332
0.8154	Intermediate Similarity	NPC115458
0.8154	Intermediate Similarity	NPC225051
0.8154	Intermediate Similarity	NPC139074
0.8154	Intermediate Similarity	NPC213485
0.8154	Intermediate Similarity	NPC40524
0.8154	Intermediate Similarity	NPC171968
0.8154	Intermediate Similarity	NPC53896
0.8151	Intermediate Similarity	NPC474114
0.8151	Intermediate Similarity	NPC474050
0.8151	Intermediate Similarity	NPC285350
0.8151	Intermediate Similarity	NPC473931
0.8145	Intermediate Similarity	NPC244351
0.8145	Intermediate Similarity	NPC283514
0.8145	Intermediate Similarity	NPC309765
0.814	Intermediate Similarity	NPC93015
0.814	Intermediate Similarity	NPC324488
0.814	Intermediate Similarity	NPC474517
0.814	Intermediate Similarity	NPC7012
0.814	Intermediate Similarity	NPC72669
0.814	Intermediate Similarity	NPC41847
0.814	Intermediate Similarity	NPC244699
0.813	Intermediate Similarity	NPC190971
0.813	Intermediate Similarity	NPC146642
0.8125	Intermediate Similarity	NPC102829
0.8125	Intermediate Similarity	NPC120488
0.8115	Intermediate Similarity	NPC195262
0.8115	Intermediate Similarity	NPC188814
0.811	Intermediate Similarity	NPC71525
0.8106	Intermediate Similarity	NPC272268
0.8106	Intermediate Similarity	NPC474813
0.8106	Intermediate Similarity	NPC155211
0.8103	Intermediate Similarity	NPC68260
0.8103	Intermediate Similarity	NPC279887
0.8099	Intermediate Similarity	NPC150919
0.8095	Intermediate Similarity	NPC10926
0.8095	Intermediate Similarity	NPC123506
0.8095	Intermediate Similarity	NPC477454
0.8092	Intermediate Similarity	NPC288089
0.8092	Intermediate Similarity	NPC202225
0.8092	Intermediate Similarity	NPC474519
0.8092	Intermediate Similarity	NPC474394
0.8092	Intermediate Similarity	NPC474097
0.8092	Intermediate Similarity	NPC50924
0.8083	Intermediate Similarity	NPC23402
0.808	Intermediate Similarity	NPC135062
0.8077	Intermediate Similarity	NPC17843
0.8077	Intermediate Similarity	NPC58685
0.8067	Intermediate Similarity	NPC190212

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 NPC41567 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	284
0.1-0.2	993
0.2-0.3	1423
0.3-0.4	2737
0.4-0.5	2084
0.5-0.6	1113
0.6-0.7	447
0.7-0.8	60
0.8-0.85	7
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8632	High Similarity	NPD405	Clinical (unspecified phase)
0.8512	High Similarity	NPD1201	Approved
0.8387	Intermediate Similarity	NPD1470	Approved
0.8319	Intermediate Similarity	NPD9493	Approved
0.8261	Intermediate Similarity	NPD9266	Approved
0.8261	Intermediate Similarity	NPD74	Approved
0.8174	Intermediate Similarity	NPD9267	Approved
0.8174	Intermediate Similarity	NPD9263	Approved
0.8174	Intermediate Similarity	NPD9264	Approved
0.7928	Intermediate Similarity	NPD844	Approved
0.7857	Intermediate Similarity	NPD288	Approved
0.7836	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7826	Intermediate Similarity	NPD9261	Approved
0.782	Intermediate Similarity	NPD1607	Approved
0.7812	Intermediate Similarity	NPD1164	Approved
0.7803	Intermediate Similarity	NPD943	Approved
0.7778	Intermediate Similarity	NPD2935	Discontinued
0.7759	Intermediate Similarity	NPD1237	Approved
0.7705	Intermediate Similarity	NPD9281	Approved
0.768	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7669	Intermediate Similarity	NPD1240	Approved
0.7652	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7652	Intermediate Similarity	NPD411	Approved
0.7638	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7615	Intermediate Similarity	NPD2798	Approved
0.76	Intermediate Similarity	NPD9545	Approved
0.7591	Intermediate Similarity	NPD2346	Discontinued
0.7578	Intermediate Similarity	NPD9717	Approved
0.7574	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7574	Intermediate Similarity	NPD1510	Phase 2
0.7563	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7518	Intermediate Similarity	NPD5406	Approved
0.7518	Intermediate Similarity	NPD5408	Approved
0.7518	Intermediate Similarity	NPD5404	Approved
0.7518	Intermediate Similarity	NPD5405	Approved
0.7481	Intermediate Similarity	NPD447	Suspended
0.7429	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD1203	Approved
0.7394	Intermediate Similarity	NPD7390	Discontinued
0.7391	Intermediate Similarity	NPD1551	Phase 2
0.7388	Intermediate Similarity	NPD2313	Discontinued
0.7344	Intermediate Similarity	NPD2932	Approved
0.7344	Intermediate Similarity	NPD3019	Approved
0.7343	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD2344	Approved
0.7333	Intermediate Similarity	NPD520	Approved
0.7324	Intermediate Similarity	NPD3300	Phase 2
0.7293	Intermediate Similarity	NPD9494	Approved
0.7286	Intermediate Similarity	NPD1549	Phase 2
0.726	Intermediate Similarity	NPD3226	Approved
0.7226	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7218	Intermediate Similarity	NPD1019	Discontinued
0.7214	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7214	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD1241	Discontinued
0.7194	Intermediate Similarity	NPD2799	Discontinued
0.7176	Intermediate Similarity	NPD3972	Approved
0.7168	Intermediate Similarity	NPD9256	Approved
0.7168	Intermediate Similarity	NPD9258	Approved
0.7163	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7154	Intermediate Similarity	NPD4750	Phase 3
0.7133	Intermediate Similarity	NPD2309	Approved
0.713	Intermediate Similarity	NPD845	Approved
0.7121	Intermediate Similarity	NPD1755	Approved
0.712	Intermediate Similarity	NPD7635	Approved
0.7114	Intermediate Similarity	NPD1934	Approved
0.7111	Intermediate Similarity	NPD6832	Phase 2
0.7103	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD2533	Approved
0.7103	Intermediate Similarity	NPD2532	Approved
0.7103	Intermediate Similarity	NPD2534	Approved
0.7101	Intermediate Similarity	NPD230	Phase 1
0.7095	Intermediate Similarity	NPD4380	Phase 2
0.7077	Intermediate Similarity	NPD4626	Approved
0.7077	Intermediate Similarity	NPD1778	Approved
0.7071	Intermediate Similarity	NPD4308	Phase 3
0.7069	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD1283	Approved
0.7067	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD9269	Phase 2
0.7034	Intermediate Similarity	NPD1511	Approved
0.7034	Intermediate Similarity	NPD9495	Approved
0.7021	Intermediate Similarity	NPD2796	Approved
0.7009	Intermediate Similarity	NPD2860	Approved
0.7009	Intermediate Similarity	NPD2859	Approved
0.7008	Intermediate Similarity	NPD5951	Approved
0.7	Intermediate Similarity	NPD1651	Approved
0.7	Intermediate Similarity	NPD9268	Approved
0.7	Intermediate Similarity	NPD6844	Discontinued
0.7	Intermediate Similarity	NPD846	Approved
0.7	Intermediate Similarity	NPD940	Approved
0.6992	Remote Similarity	NPD2342	Discontinued
0.6975	Remote Similarity	NPD3020	Approved
0.6975	Remote Similarity	NPD2066	Phase 3
0.6972	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.696	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6953	Remote Similarity	NPD255	Approved
0.6953	Remote Similarity	NPD256	Approved
0.6944	Remote Similarity	NPD4628	Phase 3
0.6944	Remote Similarity	NPD7003	Approved
0.6942	Remote Similarity	NPD1929	Approved
0.6942	Remote Similarity	NPD1930	Approved
0.6942	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.694	Remote Similarity	NPD1876	Approved
0.6939	Remote Similarity	NPD1512	Approved
0.6935	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD2933	Approved
0.6923	Remote Similarity	NPD2934	Approved
0.6913	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD3496	Discontinued
0.6884	Remote Similarity	NPD3764	Approved
0.6875	Remote Similarity	NPD111	Approved
0.6875	Remote Similarity	NPD9614	Approved
0.6875	Remote Similarity	NPD9618	Approved
0.6875	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD4662	Approved
0.6871	Remote Similarity	NPD4661	Approved
0.687	Remote Similarity	NPD5691	Approved
0.6864	Remote Similarity	NPD1809	Phase 2
0.6863	Remote Similarity	NPD3882	Suspended
0.686	Remote Similarity	NPD1932	Approved
0.6849	Remote Similarity	NPD6884	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD1281	Approved
0.6842	Remote Similarity	NPD7819	Suspended
0.6842	Remote Similarity	NPD2801	Approved
0.6835	Remote Similarity	NPD6663	Approved
0.6832	Remote Similarity	NPD6559	Discontinued
0.6831	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD8166	Discontinued
0.6822	Remote Similarity	NPD6671	Approved
0.6818	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6814	Remote Similarity	NPD9257	Approved
0.6814	Remote Similarity	NPD9259	Approved
0.68	Remote Similarity	NPD7458	Discontinued
0.6797	Remote Similarity	NPD5402	Approved
0.6795	Remote Similarity	NPD6959	Discontinued
0.6794	Remote Similarity	NPD1759	Phase 1
0.6794	Remote Similarity	NPD3091	Approved
0.6791	Remote Similarity	NPD1608	Approved
0.6788	Remote Similarity	NPD5736	Approved
0.6786	Remote Similarity	NPD4307	Phase 2
0.6783	Remote Similarity	NPD800	Approved
0.678	Remote Similarity	NPD1693	Approved
0.6774	Remote Similarity	NPD1444	Approved
0.6774	Remote Similarity	NPD1445	Approved
0.6772	Remote Similarity	NPD9508	Approved
0.6772	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD6166	Phase 2
0.6772	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6767	Remote Similarity	NPD3023	Approved
0.6767	Remote Similarity	NPD3026	Approved
0.6765	Remote Similarity	NPD2797	Approved
0.6757	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6755	Remote Similarity	NPD6599	Discontinued
0.6752	Remote Similarity	NPD6232	Discontinued
0.6748	Remote Similarity	NPD164	Approved
0.6746	Remote Similarity	NPD3021	Approved
0.6746	Remote Similarity	NPD3022	Approved
0.6744	Remote Similarity	NPD2629	Approved
0.6742	Remote Similarity	NPD3025	Approved
0.6742	Remote Similarity	NPD3024	Approved
0.6741	Remote Similarity	NPD5158	Clinical (unspecified phase)
0.6741	Remote Similarity	NPD5157	Phase 1
0.6741	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6741	Remote Similarity	NPD5159	Phase 2
0.6736	Remote Similarity	NPD1471	Phase 3
0.673	Remote Similarity	NPD7473	Discontinued
0.6724	Remote Similarity	NPD1089	Approved
0.6724	Remote Similarity	NPD1086	Approved
0.6724	Remote Similarity	NPD1090	Approved
0.6718	Remote Similarity	NPD9613	Approved
0.6718	Remote Similarity	NPD9616	Approved
0.6718	Remote Similarity	NPD1758	Phase 1
0.6718	Remote Similarity	NPD9615	Approved
0.6715	Remote Similarity	NPD258	Approved
0.6715	Remote Similarity	NPD257	Approved
0.6712	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6712	Remote Similarity	NPD3750	Approved
0.6711	Remote Similarity	NPD6273	Approved
0.6711	Remote Similarity	NPD7411	Suspended
0.671	Remote Similarity	NPD7075	Discontinued
0.6695	Remote Similarity	NPD1202	Approved
0.6694	Remote Similarity	NPD1238	Approved
0.6693	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6692	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD6799	Approved
0.6688	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD3818	Discontinued
0.6667	Remote Similarity	NPD2182	Approved
0.6667	Remote Similarity	NPD5403	Approved
0.6667	Remote Similarity	NPD6099	Approved
0.6667	Remote Similarity	NPD826	Approved
0.6667	Remote Similarity	NPD2329	Discontinued
0.6667	Remote Similarity	NPD9570	Approved
0.6667	Remote Similarity	NPD825	Approved
0.6667	Remote Similarity	NPD6100	Approved
0.6667	Remote Similarity	NPD316	Approved
0.6646	Remote Similarity	NPD8313	Approved
0.6646	Remote Similarity	NPD8312	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