NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	260.12
Volume:	260.213
LogP:	0.499
LogD:	0.72
LogS:	-1.815
# Rotatable Bonds:	2
TPSA:	69.64
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.81
Synthetic Accessibility Score:	2.888
Fsp3:	0.429
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.885
MDCK Permeability:	5.729103577323258e-06
Pgp-inhibitor:	0.0
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.026
20% Bioavailability (F20%):	0.794
30% Bioavailability (F30%):	0.599

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.229
Plasma Protein Binding (PPB):	34.02556610107422%
Volume Distribution (VD):	0.549
Pgp-substrate:	60.51322937011719%

ADMET: Metabolism

CYP1A2-inhibitor:	0.021
CYP1A2-substrate:	0.111
CYP2C19-inhibitor:	0.217
CYP2C19-substrate:	0.107
CYP2C9-inhibitor:	0.158
CYP2C9-substrate:	0.876
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.554
CYP3A4-inhibitor:	0.11
CYP3A4-substrate:	0.153

ADMET: Excretion

Clearance (CL):	10.215
Half-life (T1/2):	0.82

ADMET: Toxicity

hERG Blockers:	0.02
Human Hepatotoxicity (H-HT):	0.637
Drug-inuced Liver Injury (DILI):	0.14
AMES Toxicity:	0.017
Rat Oral Acute Toxicity:	0.614
Maximum Recommended Daily Dose:	0.383
Skin Sensitization:	0.32
Carcinogencity:	0.315
Eye Corrosion:	0.003
Eye Irritation:	0.016
Respiratory Toxicity:	0.04

Download Data

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

Natural Product: NPC242159

Natural Product ID:	NPC242159
*Common Name:**	Cyclo-L-Pro-L-Tyr
IUPAC Name:	(3S,8aS)-3-[(4-hydroxyphenyl)methyl]-2,3,6,7,8,8a-hexahydropyrrolo[1,2-a]pyrazine-1,4-dione
Synonyms:
Standard InCHIKey:	LSGOTAXPWMCUCK-RYUDHWBXSA-N
Standard InCHI:	InChI=1S/C14H16N2O3/c17-10-5-3-9(4-6-10)8-11-14(19)16-7-1-2-12(16)13(18)15-11/h3-6,11-12,17H,1-2,7-8H2,(H,15,18)/t11-,12-/m0/s1
SMILES:	Oc1ccc(cc1)C[C@@H]1N=C(O)[C@H]2N(C1=O)CCC2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL359788
PubChem CID:	119404
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0000013] Amino acids, peptides, and analogues [CHEMONTID:0000347] Amino acids and derivatives [CHEMONTID:0000060] Alpha amino acids and derivatives

*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
NPO30270	Cordyceps sinensis	Species	Cordycipitaceae	Eukaryota	n.a.	mycelium	n.a.	PMID[10423860]
NPO21926	Pseudomonas aeruginosa	Species	Pseudomonadaceae	Bacteria	n.a.	n.a.	n.a.	PMID[10556916]
NPO1520	Callyspongia pseudoreticulata	Species	Callyspongiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[12828480]
NPO24252	Uvaria hamiltonii	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14552774]
NPO30270	Cordyceps sinensis	Species	Cordycipitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15863936]
NPO21926	Pseudomonas aeruginosa	Species	Pseudomonadaceae	Bacteria	n.a.	n.a.	n.a.	PMID[19406895]
NPO33480	leptoxyphium sp.	Species	Capnodiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19637889]
NPO21926	Pseudomonas aeruginosa	Species	Pseudomonadaceae	Bacteria	n.a.	n.a.	n.a.	PMID[19917748]
NPO2605	Pichia membranifaciens	Species	Pichiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19943625]
NPO21926	Pseudomonas aeruginosa	Species	Pseudomonadaceae	Bacteria	n.a.	n.a.	n.a.	PMID[20932054]
NPO30270	Cordyceps sinensis	Species	Cordycipitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21848266]
NPO30270	Cordyceps sinensis	Species	Cordycipitaceae	Eukaryota	n.a.	mycelium	n.a.	PMID[21848266]
NPO21926	Pseudomonas aeruginosa	Species	Pseudomonadaceae	Bacteria	n.a.	n.a.	n.a.	PMID[25043228]
NPO21926	Pseudomonas aeruginosa	Species	Pseudomonadaceae	Bacteria	n.a.	n.a.	n.a.	PMID[25960261]
NPO4554	Isatis tinctoria	Species	Brassicaceae	Eukaryota	Roots	n.a.	n.a.	PMID[32004936]
NPO21926	Pseudomonas aeruginosa	Species	Pseudomonadaceae	Bacteria	n.a.	n.a.	n.a.	PMID[32603106]
NPO21926	Pseudomonas aeruginosa	Species	Pseudomonadaceae	Bacteria	n.a.	Antarctic	n.a.	PMID[8882433]
NPO24252	Uvaria hamiltonii	Species	Annonaceae	Eukaryota	leaf and stem	n.a.	n.a.	PMID[9584399]
NPO30270	Cordyceps sinensis	Species	Cordycipitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4554	Isatis tinctoria	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4554	Isatis tinctoria	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO30270	Cordyceps sinensis	Species	Cordycipitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4554	Isatis tinctoria	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO24252	Uvaria hamiltonii	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2605	Pichia membranifaciens	Species	Pichiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28694	Sanguisorba tenuifolia	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4554	Isatis tinctoria	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23819	Baccharis peruviana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1520	Callyspongia pseudoreticulata	Species	Callyspongiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23277	Lobophora papenfussii	Species	Dictyotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24585	Ocotea macropoda	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21926	Pseudomonas aeruginosa	Species	Pseudomonadaceae	Bacteria	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	5
MIC	3
Others	5

Activity Type	# Activity
Individual Protein	1
NON-MOLECULAR	2
Organism	8
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT3966	Individual Protein	Phenol oxidase	Plutella xylostella	IC50	=	42480.0	nM	PMID[507489]
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	Cell aggregates	=	77.5	n.a.	PMID[507483]
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	Cell aggregates	=	33.9	n.a.	PMID[507483]
NPT1	Others	Radical scavenging activity		Activity	=	16.0	%	PMID[507486]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	11.72	ug.mL-1	PMID[507488]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	5.65	ug.mL-1	PMID[507488]
NPT849	Organism	Plutella xylostella	Plutella xylostella	LC50	=	5948.7	ppm	PMID[507489]
NPT2779	Organism	Spodoptera exigua	Spodoptera exigua	IC50	=	37710.0	nM	PMID[507489]
NPT2	Others	Unspecified		IC50	=	47790.0	nM	PMID[507489]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	10.2	ug.mL-1	PMID[507490]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	8.7	ug.mL-1	PMID[507490]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	20.0	ug.mL-1	PMID[507490]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	40.0	%	PMID[507491]

☑ 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 NPC242159 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	223
0.1-0.2	1432
0.2-0.3	7758
0.3-0.4	9458
0.4-0.5	15078
0.5-0.6	7242
0.6-0.7	1118
0.7-0.8	323
0.8-0.85	52
0.85-0.9	10
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC313694
0.9197	High Similarity	NPC16188
0.8873	High Similarity	NPC202198
0.8832	High Similarity	NPC476989
0.8671	High Similarity	NPC233702
0.8483	Intermediate Similarity	NPC261934
0.8483	Intermediate Similarity	NPC262166
0.8483	Intermediate Similarity	NPC56685
0.8483	Intermediate Similarity	NPC5194
0.8472	Intermediate Similarity	NPC473491
0.8456	Intermediate Similarity	NPC241794
0.8438	Intermediate Similarity	NPC285926
0.8438	Intermediate Similarity	NPC14672
0.8438	Intermediate Similarity	NPC315276
0.8367	Intermediate Similarity	NPC476268
0.8321	Intermediate Similarity	NPC257390
0.8235	Intermediate Similarity	NPC141957
0.8235	Intermediate Similarity	NPC328649
0.8134	Intermediate Similarity	NPC474082
0.8134	Intermediate Similarity	NPC175726
0.8121	Intermediate Similarity	NPC244509
0.8085	Intermediate Similarity	NPC109580
0.8082	Intermediate Similarity	NPC9373
0.8079	Intermediate Similarity	NPC244336
0.8077	Intermediate Similarity	NPC89831
0.8069	Intermediate Similarity	NPC81026
0.8065	Intermediate Similarity	NPC280022
0.8052	Intermediate Similarity	NPC61004
0.8025	Intermediate Similarity	NPC137627
0.8013	Intermediate Similarity	NPC323336
0.8013	Intermediate Similarity	NPC326349
0.8	Intermediate Similarity	NPC266741
0.8	Intermediate Similarity	NPC39822
0.8	Intermediate Similarity	NPC118202
0.8	Intermediate Similarity	NPC302597
0.7987	Intermediate Similarity	NPC63931
0.7975	Intermediate Similarity	NPC136797
0.7975	Intermediate Similarity	NPC26108
0.797	Intermediate Similarity	NPC319950
0.7949	Intermediate Similarity	NPC129486
0.7926	Intermediate Similarity	NPC27581
0.7914	Intermediate Similarity	NPC325651
0.7911	Intermediate Similarity	NPC475532
0.7908	Intermediate Similarity	NPC469243
0.7898	Intermediate Similarity	NPC475204
0.7898	Intermediate Similarity	NPC475123
0.7883	Intermediate Similarity	NPC171372
0.7881	Intermediate Similarity	NPC473580
0.7879	Intermediate Similarity	NPC82963
0.7863	Intermediate Similarity	NPC33742
0.7862	Intermediate Similarity	NPC165285
0.7862	Intermediate Similarity	NPC17698
0.7862	Intermediate Similarity	NPC251439
0.7852	Intermediate Similarity	NPC324081
0.7826	Intermediate Similarity	NPC119652
0.7826	Intermediate Similarity	NPC97526
0.782	Intermediate Similarity	NPC311737
0.782	Intermediate Similarity	NPC38458
0.7815	Intermediate Similarity	NPC39431
0.7792	Intermediate Similarity	NPC475544
0.7786	Intermediate Similarity	NPC478147
0.7785	Intermediate Similarity	NPC198254
0.7785	Intermediate Similarity	NPC274198
0.7778	Intermediate Similarity	NPC200964
0.7756	Intermediate Similarity	NPC223207
0.7755	Intermediate Similarity	NPC471680
0.775	Intermediate Similarity	NPC471165
0.7746	Intermediate Similarity	NPC244866
0.7727	Intermediate Similarity	NPC287757
0.7727	Intermediate Similarity	NPC319320
0.7714	Intermediate Similarity	NPC469666
0.7707	Intermediate Similarity	NPC471771
0.7707	Intermediate Similarity	NPC290755
0.7707	Intermediate Similarity	NPC304074
0.7707	Intermediate Similarity	NPC254700
0.7688	Intermediate Similarity	NPC306804
0.7673	Intermediate Similarity	NPC276506
0.7664	Intermediate Similarity	NPC142577
0.7658	Intermediate Similarity	NPC294516
0.7658	Intermediate Similarity	NPC107938
0.764	Intermediate Similarity	NPC159767
0.764	Intermediate Similarity	NPC279871
0.764	Intermediate Similarity	NPC155506
0.7625	Intermediate Similarity	NPC328494
0.7609	Intermediate Similarity	NPC6975
0.7606	Intermediate Similarity	NPC255447
0.7606	Intermediate Similarity	NPC120251
0.7603	Intermediate Similarity	NPC48202
0.7593	Intermediate Similarity	NPC196243
0.7591	Intermediate Similarity	NPC56634
0.7589	Intermediate Similarity	NPC296712
0.758	Intermediate Similarity	NPC191863
0.758	Intermediate Similarity	NPC289776
0.758	Intermediate Similarity	NPC133470
0.7562	Intermediate Similarity	NPC40234
0.7562	Intermediate Similarity	NPC46009
0.7552	Intermediate Similarity	NPC326966
0.7537	Intermediate Similarity	NPC317254
0.7533	Intermediate Similarity	NPC125852
0.7532	Intermediate Similarity	NPC472923
0.7531	Intermediate Similarity	NPC476227
0.7517	Intermediate Similarity	NPC473360
0.7516	Intermediate Similarity	NPC230611
0.75	Intermediate Similarity	NPC269750
0.75	Intermediate Similarity	NPC194671
0.75	Intermediate Similarity	NPC94862
0.75	Intermediate Similarity	NPC315388
0.7481	Intermediate Similarity	NPC106551
0.7481	Intermediate Similarity	NPC281686
0.7481	Intermediate Similarity	NPC188867
0.7469	Intermediate Similarity	NPC273755
0.7469	Intermediate Similarity	NPC248670
0.7467	Intermediate Similarity	NPC473804
0.7466	Intermediate Similarity	NPC6913
0.7465	Intermediate Similarity	NPC473322
0.7464	Intermediate Similarity	NPC202521
0.7455	Intermediate Similarity	NPC153554
0.7455	Intermediate Similarity	NPC32064
0.7448	Intermediate Similarity	NPC248283
0.7438	Intermediate Similarity	NPC209463
0.7434	Intermediate Similarity	NPC476444
0.7432	Intermediate Similarity	NPC150712
0.7431	Intermediate Similarity	NPC45191
0.7426	Intermediate Similarity	NPC470545
0.7423	Intermediate Similarity	NPC164608
0.7423	Intermediate Similarity	NPC473402
0.7423	Intermediate Similarity	NPC473354
0.7417	Intermediate Similarity	NPC119569
0.7413	Intermediate Similarity	NPC200589
0.741	Intermediate Similarity	NPC474862
0.741	Intermediate Similarity	NPC252878
0.7394	Intermediate Similarity	NPC305717
0.7394	Intermediate Similarity	NPC476353
0.7391	Intermediate Similarity	NPC476990
0.7388	Intermediate Similarity	NPC35850
0.7388	Intermediate Similarity	NPC276949
0.7385	Intermediate Similarity	NPC231705
0.7379	Intermediate Similarity	NPC328070
0.7378	Intermediate Similarity	NPC50016
0.7372	Intermediate Similarity	NPC220698
0.7372	Intermediate Similarity	NPC470546
0.7357	Intermediate Similarity	NPC46427
0.7353	Intermediate Similarity	NPC470544
0.7348	Intermediate Similarity	NPC258056
0.7343	Intermediate Similarity	NPC111428
0.7329	Intermediate Similarity	NPC473502
0.7321	Intermediate Similarity	NPC294951
0.7319	Intermediate Similarity	NPC283760
0.7319	Intermediate Similarity	NPC239697
0.7305	Intermediate Similarity	NPC477637
0.7303	Intermediate Similarity	NPC311658
0.7297	Intermediate Similarity	NPC473052
0.7297	Intermediate Similarity	NPC473055
0.7293	Intermediate Similarity	NPC474149
0.7289	Intermediate Similarity	NPC475421
0.7289	Intermediate Similarity	NPC45037
0.7287	Intermediate Similarity	NPC178902
0.7279	Intermediate Similarity	NPC151706
0.7279	Intermediate Similarity	NPC475598
0.7279	Intermediate Similarity	NPC90194
0.7279	Intermediate Similarity	NPC474855
0.7279	Intermediate Similarity	NPC476102
0.7279	Intermediate Similarity	NPC474787
0.7279	Intermediate Similarity	NPC260045
0.7279	Intermediate Similarity	NPC293377
0.7279	Intermediate Similarity	NPC79465
0.7279	Intermediate Similarity	NPC9687
0.7279	Intermediate Similarity	NPC118099
0.7279	Intermediate Similarity	NPC76785
0.7279	Intermediate Similarity	NPC273907
0.7279	Intermediate Similarity	NPC474811
0.7279	Intermediate Similarity	NPC475318
0.7279	Intermediate Similarity	NPC49577
0.7278	Intermediate Similarity	NPC138083
0.7273	Intermediate Similarity	NPC153690
0.7273	Intermediate Similarity	NPC96224
0.7273	Intermediate Similarity	NPC24101
0.7248	Intermediate Similarity	NPC322526
0.7248	Intermediate Similarity	NPC238412
0.7241	Intermediate Similarity	NPC130309
0.7239	Intermediate Similarity	NPC196091
0.7237	Intermediate Similarity	NPC297322
0.7235	Intermediate Similarity	NPC276120
0.723	Intermediate Similarity	NPC6570
0.7219	Intermediate Similarity	NPC471050
0.7219	Intermediate Similarity	NPC471049
0.7219	Intermediate Similarity	NPC471048
0.7214	Intermediate Similarity	NPC71684
0.7211	Intermediate Similarity	NPC267237
0.7202	Intermediate Similarity	NPC473404
0.7202	Intermediate Similarity	NPC476321
0.7197	Intermediate Similarity	NPC142297
0.7193	Intermediate Similarity	NPC4910
0.7193	Intermediate Similarity	NPC329731
0.7193	Intermediate Similarity	NPC96275
0.7178	Intermediate Similarity	NPC66490
0.7172	Intermediate Similarity	NPC300315
0.7171	Intermediate Similarity	NPC209509
0.7163	Intermediate Similarity	NPC268348
0.716	Intermediate Similarity	NPC167763

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 NPC242159 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	151
0.1-0.2	445
0.2-0.3	793
0.3-0.4	1570
0.4-0.5	3270
0.5-0.6	2278
0.6-0.7	582
0.7-0.8	60
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8503	High Similarity	NPD7118	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD7131	Phase 3
0.7935	Intermediate Similarity	NPD8303	Discontinued
0.7793	Intermediate Similarity	NPD7450	Phase 2
0.7756	Intermediate Similarity	NPD2098	Approved
0.7755	Intermediate Similarity	NPD6860	Clinical (unspecified phase)
0.7682	Intermediate Similarity	NPD7303	Discontinued
0.7676	Intermediate Similarity	NPD1330	Phase 2
0.7676	Intermediate Similarity	NPD1329	Clinical (unspecified phase)
0.7628	Intermediate Similarity	NPD2097	Approved
0.7562	Intermediate Similarity	NPD4652	Approved
0.7518	Intermediate Similarity	NPD5339	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD5137	Approved
0.75	Intermediate Similarity	NPD2890	Approved
0.75	Intermediate Similarity	NPD2017	Approved
0.75	Intermediate Similarity	NPD2889	Approved
0.75	Intermediate Similarity	NPD2888	Approved
0.7483	Intermediate Similarity	NPD3136	Phase 2
0.7481	Intermediate Similarity	NPD9568	Approved
0.7412	Intermediate Similarity	NPD7617	Discontinued
0.7397	Intermediate Similarity	NPD7113	Clinical (unspecified phase)
0.7376	Intermediate Similarity	NPD3125	Approved
0.7357	Intermediate Similarity	NPD2584	Suspended
0.7347	Intermediate Similarity	NPD8173	Phase 2
0.7347	Intermediate Similarity	NPD8172	Phase 2
0.7333	Intermediate Similarity	NPD3655	Clinical (unspecified phase)
0.7324	Intermediate Similarity	NPD2585	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD5200	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD999	Phase 2
0.7292	Intermediate Similarity	NPD4125	Approved
0.729	Intermediate Similarity	NPD7523	Phase 3
0.7278	Intermediate Similarity	NPD7495	Discontinued
0.726	Intermediate Similarity	NPD5729	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD6884	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD1759	Phase 1
0.7226	Intermediate Similarity	NPD7613	Discontinued
0.7174	Intermediate Similarity	NPD1758	Phase 1
0.717	Intermediate Similarity	NPD8019	Approved
0.7163	Intermediate Similarity	NPD4762	Approved
0.7163	Intermediate Similarity	NPD4761	Approved
0.716	Intermediate Similarity	NPD7132	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD255	Approved
0.7153	Intermediate Similarity	NPD256	Approved
0.7133	Intermediate Similarity	NPD6867	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD6866	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD1968	Approved
0.7124	Intermediate Similarity	NPD5481	Discontinued
0.7124	Intermediate Similarity	NPD1967	Approved
0.7123	Intermediate Similarity	NPD4497	Clinical (unspecified phase)
0.7122	Intermediate Similarity	NPD5304	Approved
0.7122	Intermediate Similarity	NPD5303	Approved
0.7113	Intermediate Similarity	NPD3073	Approved
0.7113	Intermediate Similarity	NPD3071	Approved
0.7113	Intermediate Similarity	NPD3072	Approved
0.7101	Intermediate Similarity	NPD3123	Discovery
0.7097	Intermediate Similarity	NPD6682	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD4791	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD7695	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD5967	Approved
0.7073	Intermediate Similarity	NPD7484	Phase 3
0.7073	Intermediate Similarity	NPD7485	Phase 3
0.707	Intermediate Similarity	NPD1670	Discontinued
0.7063	Intermediate Similarity	NPD7011	Discontinued
0.7063	Intermediate Similarity	NPD1755	Approved
0.7063	Intermediate Similarity	NPD4659	Approved
0.7042	Intermediate Similarity	NPD4706	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD7451	Discontinued
0.7027	Intermediate Similarity	NPD941	Approved
0.7007	Intermediate Similarity	NPD2234	Approved
0.7007	Intermediate Similarity	NPD2228	Approved
0.7007	Intermediate Similarity	NPD2229	Approved
0.7	Intermediate Similarity	NPD4782	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD2561	Approved
0.6993	Remote Similarity	NPD2562	Approved
0.6986	Remote Similarity	NPD9569	Approved
0.698	Remote Similarity	NPD6346	Approved
0.6974	Remote Similarity	NPD6897	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD3421	Phase 3
0.6968	Remote Similarity	NPD7910	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD4104	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD4103	Phase 2
0.6959	Remote Similarity	NPD3632	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD4207	Discontinued
0.6939	Remote Similarity	NPD5263	Approved
0.6929	Remote Similarity	NPD856	Approved
0.6929	Remote Similarity	NPD317	Approved
0.6929	Remote Similarity	NPD318	Approved
0.6929	Remote Similarity	NPD16	Approved
0.6928	Remote Similarity	NPD7608	Discontinued
0.6928	Remote Similarity	NPD7978	Discontinued
0.6928	Remote Similarity	NPD6809	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD3608	Clinical (unspecified phase)
0.6913	Remote Similarity	NPD5745	Approved
0.6913	Remote Similarity	NPD7086	Phase 2
0.6908	Remote Similarity	NPD7728	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD3400	Discontinued
0.6897	Remote Similarity	NPD2031	Discontinued
0.6892	Remote Similarity	NPD6919	Clinical (unspecified phase)
0.6883	Remote Similarity	NPD5341	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD5485	Approved
0.6882	Remote Similarity	NPD5484	Approved
0.6871	Remote Similarity	NPD4175	Approved
0.6871	Remote Similarity	NPD4177	Approved
0.6863	Remote Similarity	NPD1725	Approved
0.6849	Remote Similarity	NPD3055	Approved
0.6849	Remote Similarity	NPD3053	Approved
0.6846	Remote Similarity	NPD4621	Approved
0.6846	Remote Similarity	NPD4619	Approved
0.6842	Remote Similarity	NPD3555	Approved
0.6842	Remote Similarity	NPD9608	Approved
0.6842	Remote Similarity	NPD3552	Approved
0.6842	Remote Similarity	NPD743	Approved
0.6842	Remote Similarity	NPD9610	Approved
0.6842	Remote Similarity	NPD3554	Approved
0.6842	Remote Similarity	NPD5445	Approved
0.6842	Remote Similarity	NPD3553	Approved
0.6835	Remote Similarity	NPD5556	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD2874	Phase 2
0.6835	Remote Similarity	NPD1791	Approved
0.6835	Remote Similarity	NPD1793	Approved
0.6828	Remote Similarity	NPD3676	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD4676	Approved
0.6824	Remote Similarity	NPD6020	Phase 2
0.681	Remote Similarity	NPD5772	Approved
0.681	Remote Similarity	NPD5773	Approved
0.6803	Remote Similarity	NPD3604	Clinical (unspecified phase)
0.68	Remote Similarity	NPD259	Phase 1
0.6796	Remote Similarity	NPD7810	Phase 3
0.6796	Remote Similarity	NPD7811	Phase 3
0.6795	Remote Similarity	NPD6676	Phase 2
0.6795	Remote Similarity	NPD7066	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD6390	Discontinued
0.6781	Remote Similarity	NPD5310	Approved
0.6781	Remote Similarity	NPD5311	Approved
0.6781	Remote Similarity	NPD196	Phase 1
0.6779	Remote Similarity	NPD2051	Approved
0.6779	Remote Similarity	NPD2046	Approved
0.6779	Remote Similarity	NPD2048	Approved
0.6779	Remote Similarity	NPD21	Approved
0.6779	Remote Similarity	NPD9537	Phase 1
0.6779	Remote Similarity	NPD9536	Phase 1
0.6779	Remote Similarity	NPD2049	Clinical (unspecified phase)
0.6779	Remote Similarity	NPD2045	Approved
0.6779	Remote Similarity	NPD2044	Approved
0.6779	Remote Similarity	NPD5746	Approved
0.6779	Remote Similarity	NPD2050	Clinical (unspecified phase)
0.6779	Remote Similarity	NPD2043	Approved
0.6779	Remote Similarity	NPD2047	Approved
0.6774	Remote Similarity	NPD7596	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD998	Approved
0.6761	Remote Similarity	NPD2226	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD316	Approved
0.6759	Remote Similarity	NPD5108	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD6297	Approved
0.6741	Remote Similarity	NPD1445	Approved
0.6741	Remote Similarity	NPD1444	Approved
0.6733	Remote Similarity	NPD598	Approved
0.6733	Remote Similarity	NPD601	Approved
0.6733	Remote Similarity	NPD597	Approved
0.6724	Remote Similarity	NPD7281	Phase 3
0.6724	Remote Similarity	NPD7280	Phase 3
0.6721	Remote Similarity	NPD6256	Approved
0.6721	Remote Similarity	NPD6254	Approved
0.6721	Remote Similarity	NPD6255	Approved
0.6715	Remote Similarity	NPD1792	Phase 2
0.6713	Remote Similarity	NPD4504	Clinical (unspecified phase)
0.6713	Remote Similarity	NPD4093	Discontinued
0.6711	Remote Similarity	NPD555	Phase 2
0.6711	Remote Similarity	NPD8643	Discontinued
0.671	Remote Similarity	NPD2022	Approved
0.671	Remote Similarity	NPD2087	Approved
0.671	Remote Similarity	NPD2088	Approved
0.6707	Remote Similarity	NPD5823	Approved
0.6692	Remote Similarity	NPD854	Approved
0.6692	Remote Similarity	NPD855	Approved
0.669	Remote Similarity	NPD9616	Approved
0.669	Remote Similarity	NPD9615	Approved
0.669	Remote Similarity	NPD9613	Approved
0.6689	Remote Similarity	NPD257	Approved
0.6689	Remote Similarity	NPD1130	Approved
0.6689	Remote Similarity	NPD258	Approved
0.6689	Remote Similarity	NPD1132	Approved
0.6689	Remote Similarity	NPD1136	Approved
0.6689	Remote Similarity	NPD3561	Clinical (unspecified phase)
0.6688	Remote Similarity	NPD1753	Discontinued
0.6687	Remote Similarity	NPD6078	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD5946	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD6505	Approved
0.6685	Remote Similarity	NPD6504	Approved
0.6667	Remote Similarity	NPD6681	Discovery
0.6667	Remote Similarity	NPD2013	Approved
0.6667	Remote Similarity	NPD2568	Approved
0.6667	Remote Similarity	NPD2436	Approved
0.6667	Remote Similarity	NPD6253	Approved
0.6667	Remote Similarity	NPD2014	Approved
0.6667	Remote Similarity	NPD2437	Approved
0.6667	Remote Similarity	NPD817	Approved
0.6667	Remote Similarity	NPD2016	Approved
0.6667	Remote Similarity	NPD823	Approved
0.6667	Remote Similarity	NPD6073	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