NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	149.08
Volume:	164.905
LogP:	1.105
LogD:	0.605
LogS:	-1.1
# Rotatable Bonds:	2
TPSA:	43.09
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	1
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.642
Synthetic Accessibility Score:	2.083
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:	-4.908
MDCK Permeability:	6.727255822625011e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.059
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.001

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.984
Plasma Protein Binding (PPB):	43.41297912597656%
Volume Distribution (VD):	2.914
Pgp-substrate:	69.34754180908203%

ADMET: Metabolism

CYP1A2-inhibitor:	0.736
CYP1A2-substrate:	0.103
CYP2C19-inhibitor:	0.061
CYP2C19-substrate:	0.35
CYP2C9-inhibitor:	0.014
CYP2C9-substrate:	0.065
CYP2D6-inhibitor:	0.424
CYP2D6-substrate:	0.557
CYP3A4-inhibitor:	0.079
CYP3A4-substrate:	0.228

ADMET: Excretion

Clearance (CL):	6.665
Half-life (T1/2):	0.753

ADMET: Toxicity

hERG Blockers:	0.096
Human Hepatotoxicity (H-HT):	0.139
Drug-inuced Liver Injury (DILI):	0.093
AMES Toxicity:	0.047
Rat Oral Acute Toxicity:	0.832
Maximum Recommended Daily Dose:	0.039
Skin Sensitization:	0.154
Carcinogencity:	0.075
Eye Corrosion:	0.012
Eye Irritation:	0.058
Respiratory Toxicity:	0.494

Download Data

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

Natural Product: NPC246757

Natural Product ID:	NPC246757
*Common Name:**	Cathinone
IUPAC Name:	(2S)-2-amino-1-phenylpropan-1-one
Synonyms:	Cathinone
Standard InCHIKey:	PUAQLLVFLMYYJJ-ZETCQYMHSA-N
Standard InCHI:	InChI=1S/C9H11NO/c1-7(10)9(11)8-5-3-2-4-6-8/h2-7H,10H2,1H3/t7-/m0/s1
SMILES:	C[C@@H](C(=O)c1ccccc1)N
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2104047
PubChem CID:	62258
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
NPO18176	Ephedra sinica	Species	Ephedraceae	Eukaryota	n.a.	root	n.a.	PMID[18975262]
NPO28125	Ephedra equisetina	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21465337]
NPO18176	Ephedra sinica	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24333010]
NPO18176	Ephedra sinica	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28125	Ephedra equisetina	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21507	Ephedra intermedia	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28125	Ephedra equisetina	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18176	Ephedra sinica	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21507	Ephedra intermedia	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21507	Ephedra intermedia	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18176	Ephedra sinica	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28125	Ephedra equisetina	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21507	Ephedra intermedia	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO18176	Ephedra sinica	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28125	Ephedra equisetina	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28125	Ephedra equisetina	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21507	Ephedra intermedia	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18176	Ephedra sinica	Species	Ephedraceae	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
ED50	4
Kd	1
Others	1
Potency	1

Activity Type	# Activity
Individual Protein	1
Organism	4
Protein Family	1
TISSUE	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT100	Individual Protein	Glutaminase kidney isoform, mitochondrial	Homo sapiens	Potency	n.a.	50118.7	nM	PMID[568191]
NPT1530	Protein Family	Serotonin (5-HT) receptor	Rattus norvegicus	Kd	=	3019.95	nM	PMID[568190]
NPT20913	TISSUE	Whole blood	Homo sapiens	Retention_time	=	2.09	min	PMID[568192]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	ED50	=	0.34	mg.kg-1	PMID[568193]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	ED50	=	0.17	mg.kg-1	PMID[568193]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	ED50	=	0.22	mg.kg-1	PMID[568193]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	ED50	=	0.32	mg.kg-1	PMID[568193]

☑ 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 NPC246757 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	171
0.1-0.2	2671
0.2-0.3	10144
0.3-0.4	15688
0.4-0.5	11597
0.5-0.6	2006
0.6-0.7	326
0.7-0.8	85
0.8-0.85	6
0.85-0.9	0
0.9-0.95	0
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC291070
0.8276	Intermediate Similarity	NPC2785
0.8276	Intermediate Similarity	NPC285470
0.8276	Intermediate Similarity	NPC36342
0.8208	Intermediate Similarity	NPC113099
0.8182	Intermediate Similarity	NPC300205
0.8161	Intermediate Similarity	NPC245966
0.809	Intermediate Similarity	NPC164086
0.809	Intermediate Similarity	NPC190567
0.8	Intermediate Similarity	NPC145053
0.7889	Intermediate Similarity	NPC71664
0.7885	Intermediate Similarity	NPC172170
0.7879	Intermediate Similarity	NPC122493
0.7879	Intermediate Similarity	NPC293628
0.7879	Intermediate Similarity	NPC10781
0.7864	Intermediate Similarity	NPC167336
0.7816	Intermediate Similarity	NPC122327
0.7816	Intermediate Similarity	NPC112609
0.7816	Intermediate Similarity	NPC113000
0.7802	Intermediate Similarity	NPC12936
0.7802	Intermediate Similarity	NPC273033
0.7701	Intermediate Similarity	NPC285679
0.77	Intermediate Similarity	NPC324569
0.7634	Intermediate Similarity	NPC273758
0.7609	Intermediate Similarity	NPC73978
0.7586	Intermediate Similarity	NPC74458
0.7579	Intermediate Similarity	NPC307
0.7579	Intermediate Similarity	NPC160339
0.7556	Intermediate Similarity	NPC98269
0.7556	Intermediate Similarity	NPC325662
0.7556	Intermediate Similarity	NPC290638
0.7524	Intermediate Similarity	NPC67043
0.75	Intermediate Similarity	NPC69057
0.75	Intermediate Similarity	NPC43945
0.7471	Intermediate Similarity	NPC229235
0.7447	Intermediate Similarity	NPC215008
0.7447	Intermediate Similarity	NPC39600
0.7447	Intermediate Similarity	NPC324624
0.7447	Intermediate Similarity	NPC197581
0.7423	Intermediate Similarity	NPC157778
0.7419	Intermediate Similarity	NPC100039
0.7391	Intermediate Similarity	NPC151405
0.7391	Intermediate Similarity	NPC139901
0.7356	Intermediate Similarity	NPC98880
0.7333	Intermediate Similarity	NPC276699
0.7333	Intermediate Similarity	NPC164859
0.7312	Intermediate Similarity	NPC95868
0.7312	Intermediate Similarity	NPC17408
0.7312	Intermediate Similarity	NPC285716
0.7292	Intermediate Similarity	NPC252067
0.7283	Intermediate Similarity	NPC76455
0.7283	Intermediate Similarity	NPC137847
0.7282	Intermediate Similarity	NPC322598
0.7273	Intermediate Similarity	NPC173413
0.7273	Intermediate Similarity	NPC95289
0.7273	Intermediate Similarity	NPC277277
0.7253	Intermediate Similarity	NPC139658
0.7253	Intermediate Similarity	NPC78500
0.7245	Intermediate Similarity	NPC267262
0.7245	Intermediate Similarity	NPC473345
0.7241	Intermediate Similarity	NPC311343
0.7212	Intermediate Similarity	NPC12730
0.72	Intermediate Similarity	NPC133461
0.72	Intermediate Similarity	NPC284475
0.7174	Intermediate Similarity	NPC329318
0.7172	Intermediate Similarity	NPC418308
0.7172	Intermediate Similarity	NPC113307
0.7167	Intermediate Similarity	NPC72473
0.7167	Intermediate Similarity	NPC58827
0.7167	Intermediate Similarity	NPC307437
0.7157	Intermediate Similarity	NPC256452
0.7155	Intermediate Similarity	NPC27833
0.713	Intermediate Similarity	NPC327481
0.7129	Intermediate Similarity	NPC155232
0.7129	Intermediate Similarity	NPC59677
0.7129	Intermediate Similarity	NPC1682
0.7129	Intermediate Similarity	NPC153885
0.7129	Intermediate Similarity	NPC188844
0.7103	Intermediate Similarity	NPC38262
0.71	Intermediate Similarity	NPC19256
0.7097	Intermediate Similarity	NPC103488
0.7083	Intermediate Similarity	NPC149263
0.7071	Intermediate Similarity	NPC153308
0.7059	Intermediate Similarity	NPC71140
0.7059	Intermediate Similarity	NPC289883
0.7059	Intermediate Similarity	NPC238219
0.7054	Intermediate Similarity	NPC474584
0.7043	Intermediate Similarity	NPC476440
0.7037	Intermediate Similarity	NPC476198
0.7033	Intermediate Similarity	NPC208075
0.7027	Intermediate Similarity	NPC319579
0.7019	Intermediate Similarity	NPC472788
0.7009	Intermediate Similarity	NPC179605
0.7009	Intermediate Similarity	NPC279385
0.7009	Intermediate Similarity	NPC202613
0.699	Remote Similarity	NPC260233
0.6989	Remote Similarity	NPC9796
0.6964	Remote Similarity	NPC329011
0.6961	Remote Similarity	NPC323420
0.6949	Remote Similarity	NPC103292
0.6931	Remote Similarity	NPC58872
0.6923	Remote Similarity	NPC185208
0.6923	Remote Similarity	NPC271437
0.6923	Remote Similarity	NPC219573
0.6909	Remote Similarity	NPC55529
0.6907	Remote Similarity	NPC119677
0.6889	Remote Similarity	NPC219246
0.6881	Remote Similarity	NPC473418
0.687	Remote Similarity	NPC197470
0.6869	Remote Similarity	NPC164526
0.6863	Remote Similarity	NPC110704
0.6857	Remote Similarity	NPC239185
0.6857	Remote Similarity	NPC240042
0.6852	Remote Similarity	NPC471317
0.6842	Remote Similarity	NPC272260
0.6832	Remote Similarity	NPC325709
0.6827	Remote Similarity	NPC472880
0.6814	Remote Similarity	NPC275410
0.6813	Remote Similarity	NPC326200
0.681	Remote Similarity	NPC188867
0.681	Remote Similarity	NPC106551
0.681	Remote Similarity	NPC281686
0.6809	Remote Similarity	NPC179726
0.6809	Remote Similarity	NPC298023
0.6803	Remote Similarity	NPC119326
0.6792	Remote Similarity	NPC108606
0.6792	Remote Similarity	NPC75724
0.6792	Remote Similarity	NPC164514
0.6792	Remote Similarity	NPC226096
0.6792	Remote Similarity	NPC49994
0.6792	Remote Similarity	NPC134882
0.6792	Remote Similarity	NPC290515
0.6792	Remote Similarity	NPC303611
0.678	Remote Similarity	NPC177684
0.678	Remote Similarity	NPC291962
0.678	Remote Similarity	NPC226143
0.6777	Remote Similarity	NPC192533
0.6771	Remote Similarity	NPC477703
0.6768	Remote Similarity	NPC123476
0.6765	Remote Similarity	NPC303967
0.6765	Remote Similarity	NPC110420
0.6765	Remote Similarity	NPC67585
0.675	Remote Similarity	NPC268534
0.6737	Remote Similarity	NPC12857
0.6723	Remote Similarity	NPC258531
0.6723	Remote Similarity	NPC161956
0.6723	Remote Similarity	NPC112373
0.672	Remote Similarity	NPC126458
0.6699	Remote Similarity	NPC476484
0.6699	Remote Similarity	NPC103346
0.6698	Remote Similarity	NPC265220
0.6696	Remote Similarity	NPC57051
0.6694	Remote Similarity	NPC254698
0.6667	Remote Similarity	NPC109514
0.6667	Remote Similarity	NPC322433
0.6667	Remote Similarity	NPC476993
0.6667	Remote Similarity	NPC473498
0.6667	Remote Similarity	NPC257490
0.6667	Remote Similarity	NPC112552
0.6639	Remote Similarity	NPC285394
0.6639	Remote Similarity	NPC239697
0.6636	Remote Similarity	NPC275467
0.6635	Remote Similarity	NPC473661
0.6634	Remote Similarity	NPC305602
0.6634	Remote Similarity	NPC17497
0.6606	Remote Similarity	NPC222390
0.6606	Remote Similarity	NPC25458
0.6606	Remote Similarity	NPC244427
0.6604	Remote Similarity	NPC12695
0.66	Remote Similarity	NPC95965
0.6598	Remote Similarity	NPC157055
0.6593	Remote Similarity	NPC235059
0.6593	Remote Similarity	NPC16190
0.6593	Remote Similarity	NPC169222
0.6579	Remote Similarity	NPC313981
0.6569	Remote Similarity	NPC477704
0.6569	Remote Similarity	NPC477693
0.6566	Remote Similarity	NPC288903
0.6566	Remote Similarity	NPC474088
0.656	Remote Similarity	NPC209389
0.6559	Remote Similarity	NPC244738
0.6557	Remote Similarity	NPC35996
0.6555	Remote Similarity	NPC142638
0.6555	Remote Similarity	NPC314992
0.6555	Remote Similarity	NPC317784
0.6545	Remote Similarity	NPC472691
0.6545	Remote Similarity	NPC247976
0.6545	Remote Similarity	NPC471829
0.6545	Remote Similarity	NPC274443
0.6545	Remote Similarity	NPC329556
0.6545	Remote Similarity	NPC475939
0.6545	Remote Similarity	NPC474866
0.6542	Remote Similarity	NPC156021
0.6535	Remote Similarity	NPC40364
0.6535	Remote Similarity	NPC318107
0.6529	Remote Similarity	NPC326079
0.6525	Remote Similarity	NPC2265
0.6522	Remote Similarity	NPC181390
0.6514	Remote Similarity	NPC472879
0.6509	Remote Similarity	NPC130398

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 NPC246757 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	138
0.1-0.2	878
0.2-0.3	1159
0.3-0.4	3254
0.4-0.5	2443
0.5-0.6	1016
0.6-0.7	220
0.7-0.8	37
0.8-0.85	3
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.883	High Similarity	NPD1099	Approved
0.883	High Similarity	NPD1100	Approved
0.8218	Intermediate Similarity	NPD2192	Approved
0.8218	Intermediate Similarity	NPD2197	Approved
0.8208	Intermediate Similarity	NPD1073	Approved
0.8208	Intermediate Similarity	NPD1074	Approved
0.8208	Intermediate Similarity	NPD1075	Approved
0.7879	Intermediate Similarity	NPD9566	Approved
0.7816	Intermediate Similarity	NPD9591	Approved
0.7816	Intermediate Similarity	NPD9593	Approved
0.7816	Intermediate Similarity	NPD9592	Approved
0.7816	Intermediate Similarity	NPD9594	Approved
0.7816	Intermediate Similarity	NPD9589	Approved
0.7816	Intermediate Similarity	NPD9590	Approved
0.7816	Intermediate Similarity	NPD9588	Approved
0.7816	Intermediate Similarity	NPD80	Approved
0.7802	Intermediate Similarity	NPD942	Approved
0.7745	Intermediate Similarity	NPD2171	Approved
0.7745	Intermediate Similarity	NPD2196	Discontinued
0.7745	Intermediate Similarity	NPD2193	Phase 2
0.7745	Intermediate Similarity	NPD2648	Phase 3
0.7565	Intermediate Similarity	NPD1077	Clinical (unspecified phase)
0.7545	Intermediate Similarity	NPD853	Approved
0.7545	Intermediate Similarity	NPD851	Approved
0.7525	Intermediate Similarity	NPD4657	Approved
0.7525	Intermediate Similarity	NPD4655	Approved
0.7524	Intermediate Similarity	NPD1677	Discontinued
0.75	Intermediate Similarity	NPD506	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD650	Approved
0.7477	Intermediate Similarity	NPD1323	Discontinued
0.7473	Intermediate Similarity	NPD296	Approved
0.7473	Intermediate Similarity	NPD293	Approved
0.7473	Intermediate Similarity	NPD295	Approved
0.7429	Intermediate Similarity	NPD2577	Clinical (unspecified phase)
0.7404	Intermediate Similarity	NPD813	Approved
0.7327	Intermediate Similarity	NPD4094	Approved
0.7312	Intermediate Similarity	NPD1507	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD9564	Approved
0.7283	Intermediate Similarity	NPD79	Approved
0.7283	Intermediate Similarity	NPD9563	Approved
0.7282	Intermediate Similarity	NPD253	Approved
0.7238	Intermediate Similarity	NPD6024	Approved
0.7238	Intermediate Similarity	NPD6027	Approved
0.72	Intermediate Similarity	NPD7609	Phase 3
0.7196	Intermediate Similarity	NPD1766	Approved
0.7196	Intermediate Similarity	NPD1763	Approved
0.7196	Intermediate Similarity	NPD1761	Approved
0.7196	Intermediate Similarity	NPD1767	Approved
0.7196	Intermediate Similarity	NPD1765	Approved
0.7191	Intermediate Similarity	NPD294	Approved
0.7191	Intermediate Similarity	NPD292	Approved
0.717	Intermediate Similarity	NPD3357	Discontinued
0.7155	Intermediate Similarity	NPD1727	Approved
0.7129	Intermediate Similarity	NPD7631	Approved
0.7117	Intermediate Similarity	NPD9508	Approved
0.7083	Intermediate Similarity	NPD830	Approved
0.7083	Intermediate Similarity	NPD831	Approved
0.708	Intermediate Similarity	NPD1023	Approved
0.708	Intermediate Similarity	NPD1021	Approved
0.708	Intermediate Similarity	NPD1020	Approved
0.708	Intermediate Similarity	NPD1022	Approved
0.7059	Intermediate Similarity	NPD182	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD589	Approved
0.7021	Intermediate Similarity	NPD590	Approved
0.701	Intermediate Similarity	NPD9395	Approved
0.701	Intermediate Similarity	NPD785	Approved
0.7	Intermediate Similarity	NPD2056	Discontinued
0.6991	Remote Similarity	NPD1370	Approved
0.6991	Remote Similarity	NPD1373	Approved
0.6991	Remote Similarity	NPD1371	Approved
0.6991	Remote Similarity	NPD1374	Approved
0.6961	Remote Similarity	NPD1814	Approved
0.6961	Remote Similarity	NPD1812	Approved
0.6961	Remote Similarity	NPD1508	Approved
0.6949	Remote Similarity	NPD3836	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD1123	Approved
0.6949	Remote Similarity	NPD1124	Approved
0.6937	Remote Similarity	NPD664	Approved
0.6915	Remote Similarity	NPD9397	Approved
0.6915	Remote Similarity	NPD9393	Approved
0.687	Remote Similarity	NPD1348	Approved
0.687	Remote Similarity	NPD1025	Discontinued
0.6864	Remote Similarity	NPD4733	Approved
0.686	Remote Similarity	NPD2198	Approved
0.686	Remote Similarity	NPD2199	Approved
0.6857	Remote Similarity	NPD3495	Discontinued
0.6848	Remote Similarity	NPD505	Clinical (unspecified phase)
0.681	Remote Similarity	NPD9568	Approved
0.68	Remote Similarity	NPD781	Approved
0.68	Remote Similarity	NPD782	Approved
0.68	Remote Similarity	NPD780	Approved
0.68	Remote Similarity	NPD783	Approved
0.6792	Remote Similarity	NPD9609	Approved
0.6792	Remote Similarity	NPD9612	Approved
0.6792	Remote Similarity	NPD9611	Approved
0.6792	Remote Similarity	NPD466	Approved
0.6777	Remote Similarity	NPD9541	Approved
0.6777	Remote Similarity	NPD9539	Approved
0.6771	Remote Similarity	NPD260	Discontinued
0.6762	Remote Similarity	NPD1843	Approved
0.6759	Remote Similarity	NPD4803	Discontinued
0.6752	Remote Similarity	NPD997	Clinical (unspecified phase)
0.6729	Remote Similarity	NPD742	Approved
0.6723	Remote Similarity	NPD5836	Discontinued
0.672	Remote Similarity	NPD486	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1321	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1053	Approved
0.6667	Remote Similarity	NPD9540	Approved
0.6667	Remote Similarity	NPD1052	Approved
0.6667	Remote Similarity	NPD1051	Approved
0.6639	Remote Similarity	NPD5159	Phase 2
0.6639	Remote Similarity	NPD5157	Phase 1
0.6639	Remote Similarity	NPD5158	Clinical (unspecified phase)
0.6638	Remote Similarity	NPD747	Discontinued
0.6634	Remote Similarity	NPD4146	Approved
0.6634	Remote Similarity	NPD4145	Approved
0.661	Remote Similarity	NPD3806	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD480	Approved
0.6607	Remote Similarity	NPD3420	Clinical (unspecified phase)
0.6602	Remote Similarity	NPD5915	Approved
0.6598	Remote Similarity	NPD1617	Discontinued
0.6589	Remote Similarity	NPD3528	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD6330	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD3644	Approved
0.6579	Remote Similarity	NPD3642	Approved
0.6579	Remote Similarity	NPD189	Phase 3
0.6579	Remote Similarity	NPD3643	Approved
0.6579	Remote Similarity	NPD188	Approved
0.6574	Remote Similarity	NPD787	Suspended
0.6566	Remote Similarity	NPD2001	Discontinued
0.6562	Remote Similarity	NPD3373	Approved
0.6562	Remote Similarity	NPD227	Approved
0.6562	Remote Similarity	NPD225	Approved
0.656	Remote Similarity	NPD1781	Discontinued
0.6559	Remote Similarity	NPD9728	Phase 1
0.6555	Remote Similarity	NPD2217	Approved
0.6555	Remote Similarity	NPD2218	Phase 2
0.6545	Remote Similarity	NPD1929	Approved
0.6545	Remote Similarity	NPD1930	Approved
0.6545	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6542	Remote Similarity	NPD528	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD9257	Approved
0.6535	Remote Similarity	NPD9259	Approved
0.6531	Remote Similarity	NPD472	Approved
0.6529	Remote Similarity	NPD1079	Discontinued
0.6525	Remote Similarity	NPD5162	Approved
0.6514	Remote Similarity	NPD5630	Phase 1
0.65	Remote Similarity	NPD4504	Clinical (unspecified phase)
0.65	Remote Similarity	NPD1217	Clinical (unspecified phase)
0.6496	Remote Similarity	NPD2319	Discontinued
0.6496	Remote Similarity	NPD1711	Phase 2
0.6495	Remote Similarity	NPD9490	Approved
0.6491	Remote Similarity	NPD3581	Discontinued
0.6486	Remote Similarity	NPD315	Approved
0.6486	Remote Similarity	NPD10	Approved
0.6486	Remote Similarity	NPD9608	Approved
0.6486	Remote Similarity	NPD309	Approved
0.6486	Remote Similarity	NPD314	Approved
0.6486	Remote Similarity	NPD311	Approved
0.6486	Remote Similarity	NPD9610	Approved
0.6486	Remote Similarity	NPD310	Approved
0.6466	Remote Similarity	NPD167	Phase 2
0.6466	Remote Similarity	NPD168	Phase 1
0.6466	Remote Similarity	NPD2607	Approved
0.6462	Remote Similarity	NPD5227	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD1932	Approved
0.6452	Remote Similarity	NPD2634	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD1574	Approved
0.6449	Remote Similarity	NPD2507	Clinical (unspecified phase)
0.6441	Remote Similarity	NPD255	Approved
0.6441	Remote Similarity	NPD256	Approved
0.6429	Remote Similarity	NPD1040	Phase 2
0.6422	Remote Similarity	NPD2066	Phase 3
0.6415	Remote Similarity	NPD1202	Approved
0.6415	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6412	Remote Similarity	NPD4705	Clinical (unspecified phase)
0.6412	Remote Similarity	NPD6342	Discontinued
0.641	Remote Similarity	NPD1175	Approved
0.64	Remote Similarity	NPD1593	Approved
0.64	Remote Similarity	NPD263	Approved
0.64	Remote Similarity	NPD262	Approved
0.64	Remote Similarity	NPD9491	Approved
0.64	Remote Similarity	NPD5653	Discontinued
0.6393	Remote Similarity	NPD3881	Discontinued
0.6391	Remote Similarity	NPD4461	Discontinued
0.6381	Remote Similarity	NPD4543	Discontinued
0.6379	Remote Similarity	NPD753	Approved
0.6373	Remote Similarity	NPD305	Approved
0.6373	Remote Similarity	NPD304	Approved
0.6371	Remote Similarity	NPD1640	Clinical (unspecified phase)
0.6371	Remote Similarity	NPD3550	Clinical (unspecified phase)
0.6371	Remote Similarity	NPD3549	Approved
0.6371	Remote Similarity	NPD3547	Approved
0.6364	Remote Similarity	NPD3035	Approved
0.6364	Remote Similarity	NPD226	Approved
0.6364	Remote Similarity	NPD4158	Clinical (unspecified phase)
0.6357	Remote Similarity	NPD1874	Clinical (unspecified phase)
0.6355	Remote Similarity	NPD5554	Approved
0.6346	Remote Similarity	NPD771	Phase 3
0.6341	Remote Similarity	NPD3624	Phase 2

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