NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	245.11
Volume:	255.136
LogP:	1.378
LogD:	1.653
LogS:	-1.591
# Rotatable Bonds:	5
TPSA:	62.46
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.789
Synthetic Accessibility Score:	2.574
Fsp3:	0.214
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.691
MDCK Permeability:	7.698573426750954e-06
Pgp-inhibitor:	0.002
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.082
20% Bioavailability (F20%):	0.107
30% Bioavailability (F30%):	0.093

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.369
Plasma Protein Binding (PPB):	57.0159797668457%
Volume Distribution (VD):	0.896
Pgp-substrate:	41.080291748046875%

ADMET: Metabolism

CYP1A2-inhibitor:	0.811
CYP1A2-substrate:	0.072
CYP2C19-inhibitor:	0.713
CYP2C19-substrate:	0.088
CYP2C9-inhibitor:	0.506
CYP2C9-substrate:	0.564
CYP2D6-inhibitor:	0.331
CYP2D6-substrate:	0.881
CYP3A4-inhibitor:	0.15
CYP3A4-substrate:	0.333

ADMET: Excretion

Clearance (CL):	9.153
Half-life (T1/2):	0.932

ADMET: Toxicity

hERG Blockers:	0.01
Human Hepatotoxicity (H-HT):	0.047
Drug-inuced Liver Injury (DILI):	0.109
AMES Toxicity:	0.03
Rat Oral Acute Toxicity:	0.024
Maximum Recommended Daily Dose:	0.044
Skin Sensitization:	0.217
Carcinogencity:	0.34
Eye Corrosion:	0.004
Eye Irritation:	0.913
Respiratory Toxicity:	0.116

Download Data

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

Natural Product: NPC241025

Natural Product ID:	NPC241025
*Common Name:**	Pyrrolezanthine
IUPAC Name:	5-(hydroxymethyl)-1-[2-(4-hydroxyphenyl)ethyl]pyrrole-2-carbaldehyde
Synonyms:
Standard InCHIKey:	KPSZYAMCIRWUTK-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C14H15NO3/c16-9-12-3-4-13(10-17)15(12)8-7-11-1-5-14(18)6-2-11/h1-6,9,17-18H,7-8,10H2
SMILES:	c1cc(ccc1CCn1c(ccc1CO)C=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3357678
PubChem CID:	636825
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000134] Phenols [CHEMONTID:0004646] 1-hydroxy-2-unsubstituted benzenoids

*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
NPO26992	Sophora leachiana	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	DOI[10.1016/0031-9422(90)85209-X]
NPO26409	Plakortis simplex	Species	Plakinidae	Eukaryota	n.a.	Caribbean	n.a.	PMID[10021943]
NPO26409	Plakortis simplex	Species	Plakinidae	Eukaryota	n.a.	Taiwan	n.a.	PMID[11277748]
NPO26409	Plakortis simplex	Species	Plakinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15921424]
NPO26203	Dysidea villosa	Species	Dysideidae	Eukaryota	n.a.	Hainan, China	n.a.	PMID[19091557]
NPO26409	Plakortis simplex	Species	Plakinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[23806071]
NPO26409	Plakortis simplex	Species	Plakinidae	Eukaryota	n.a.	China	n.a.	PMID[25115700]
NPO33301	jiangella gansuensis	Species	Jiangellaceae	Bacteria	n.a.	n.a.	n.a.	PMID[25412141]
NPO26298	Zanthoxylum simulans	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26666037]
NPO25406	Celastrus monospermus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28006915]
NPO26298	Zanthoxylum simulans	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7798955]
NPO24478	Morinda coreia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25122	Conium maculatum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19672	Hosta sieboldiana	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26298	Zanthoxylum simulans	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26992	Sophora leachiana	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26298	Zanthoxylum simulans	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13313	Talipariti tiliaceum	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26992	Sophora leachiana	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25122	Conium maculatum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24478	Morinda coreia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19672	Hosta sieboldiana	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19672	Hosta sieboldiana	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26298	Zanthoxylum simulans	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO25122	Conium maculatum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO25714	Solanum spirale	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3005	Passiflora morifolia	Species	Passifloraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19672	Hosta sieboldiana	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26992	Sophora leachiana	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9324	0techis scutatus	Species	Elapidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28636	Vernonia lilacina	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26160	Thielavia terricola	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25358	Senecio gilliesi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26849	Parmelia zollingeri	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22264	Inula salsoloides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25833	Asclepias subulata	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25406	Celastrus monospermus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25259	Schrebera swietenoides	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26409	Plakortis simplex	Species	Plakinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24918	Jacobaea cannabifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22890	Eutrochium purpureum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25201	Aglaia pyramidata	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24547	Xanthoria parietina	Species	Teloschistaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26690	Lactarius subpiperatus	Species	Lactariidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24478	Morinda coreia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26789	Tephrosia bidwilli	Species	Geometridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26203	Dysidea villosa	Species	Dysideidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3963	Hortonia floribunda	Species	Monimiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1267	Acronychia laurifolia	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25802	Agave deserti	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25122	Conium maculatum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13313	Talipariti tiliaceum	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26298	Zanthoxylum simulans	Species	Rutaceae	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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	58800.0	nM	PMID[452628]

☑ 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 NPC241025 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	317
0.1-0.2	3032
0.2-0.3	13368
0.3-0.4	5572
0.4-0.5	14605
0.5-0.6	3795
0.6-0.7	1827
0.7-0.8	171
0.8-0.85	4
0.85-0.9	1
0.9-0.95	3
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9371	High Similarity	NPC472284
0.9011	High Similarity	NPC472287
0.9011	High Similarity	NPC472286
0.8851	High Similarity	NPC295158
0.7979	Intermediate Similarity	NPC473814
0.7979	Intermediate Similarity	NPC78767
0.7968	Intermediate Similarity	NPC93390
0.7967	Intermediate Similarity	NPC207851
0.7908	Intermediate Similarity	NPC146418
0.7819	Intermediate Similarity	NPC473821
0.7795	Intermediate Similarity	NPC53344
0.7795	Intermediate Similarity	NPC183777
0.7789	Intermediate Similarity	NPC74153
0.7719	Intermediate Similarity	NPC13432
0.7717	Intermediate Similarity	NPC159125
0.7704	Intermediate Similarity	NPC321428
0.7704	Intermediate Similarity	NPC283117
0.7685	Intermediate Similarity	NPC54066
0.7665	Intermediate Similarity	NPC210828
0.7665	Intermediate Similarity	NPC86834
0.7638	Intermediate Similarity	NPC294375
0.7626	Intermediate Similarity	NPC325297
0.7624	Intermediate Similarity	NPC472285
0.7614	Intermediate Similarity	NPC270918
0.7602	Intermediate Similarity	NPC472259
0.7598	Intermediate Similarity	NPC41717
0.759	Intermediate Similarity	NPC57398
0.7553	Intermediate Similarity	NPC206186
0.755	Intermediate Similarity	NPC23294
0.7539	Intermediate Similarity	NPC230403
0.7537	Intermediate Similarity	NPC293151
0.7529	Intermediate Similarity	NPC153769
0.7514	Intermediate Similarity	NPC325705
0.7514	Intermediate Similarity	NPC52831
0.75	Intermediate Similarity	NPC303951
0.7487	Intermediate Similarity	NPC171787
0.7474	Intermediate Similarity	NPC144381
0.7474	Intermediate Similarity	NPC306376
0.7472	Intermediate Similarity	NPC322644
0.7458	Intermediate Similarity	NPC116573
0.7426	Intermediate Similarity	NPC219087
0.74	Intermediate Similarity	NPC39679
0.7399	Intermediate Similarity	NPC161292
0.7391	Intermediate Similarity	NPC303225
0.7377	Intermediate Similarity	NPC273532
0.7376	Intermediate Similarity	NPC9894
0.7374	Intermediate Similarity	NPC134848
0.7374	Intermediate Similarity	NPC476098
0.7374	Intermediate Similarity	NPC165599
0.7368	Intermediate Similarity	NPC238242
0.7368	Intermediate Similarity	NPC179287
0.733	Intermediate Similarity	NPC284348
0.733	Intermediate Similarity	NPC247803
0.7317	Intermediate Similarity	NPC322064
0.7316	Intermediate Similarity	NPC194040
0.731	Intermediate Similarity	NPC213308
0.7287	Intermediate Similarity	NPC113626
0.7286	Intermediate Similarity	NPC317572
0.7283	Intermediate Similarity	NPC158129
0.7283	Intermediate Similarity	NPC253810
0.7282	Intermediate Similarity	NPC246658
0.7277	Intermediate Similarity	NPC61038
0.7268	Intermediate Similarity	NPC118228
0.7264	Intermediate Similarity	NPC244741
0.7264	Intermediate Similarity	NPC249583
0.7264	Intermediate Similarity	NPC194740
0.726	Intermediate Similarity	NPC150239
0.7255	Intermediate Similarity	NPC264176
0.7245	Intermediate Similarity	NPC141454
0.7231	Intermediate Similarity	NPC146724
0.7231	Intermediate Similarity	NPC276517
0.7222	Intermediate Similarity	NPC315491
0.7222	Intermediate Similarity	NPC45459
0.7219	Intermediate Similarity	NPC96890
0.7216	Intermediate Similarity	NPC471448
0.7214	Intermediate Similarity	NPC175602
0.7206	Intermediate Similarity	NPC87413
0.7202	Intermediate Similarity	NPC83111
0.72	Intermediate Similarity	NPC53144
0.72	Intermediate Similarity	NPC302159
0.7198	Intermediate Similarity	NPC27041
0.7188	Intermediate Similarity	NPC36498
0.7178	Intermediate Similarity	NPC88008
0.7177	Intermediate Similarity	NPC14686
0.7171	Intermediate Similarity	NPC12344
0.7159	Intermediate Similarity	NPC257142
0.7157	Intermediate Similarity	NPC124086
0.7156	Intermediate Similarity	NPC51388
0.7151	Intermediate Similarity	NPC263455
0.7151	Intermediate Similarity	NPC85443
0.715	Intermediate Similarity	NPC3207
0.715	Intermediate Similarity	NPC221873
0.7143	Intermediate Similarity	NPC121069
0.7143	Intermediate Similarity	NPC271792
0.7136	Intermediate Similarity	NPC250448
0.7136	Intermediate Similarity	NPC207866
0.7129	Intermediate Similarity	NPC208084
0.7129	Intermediate Similarity	NPC315804
0.7129	Intermediate Similarity	NPC269270
0.7129	Intermediate Similarity	NPC313804
0.7129	Intermediate Similarity	NPC45190
0.7127	Intermediate Similarity	NPC84508
0.7122	Intermediate Similarity	NPC187501
0.711	Intermediate Similarity	NPC15801
0.7098	Intermediate Similarity	NPC46580
0.709	Intermediate Similarity	NPC72980
0.7087	Intermediate Similarity	NPC110182
0.7087	Intermediate Similarity	NPC308137
0.7087	Intermediate Similarity	NPC310211
0.7085	Intermediate Similarity	NPC123395
0.7081	Intermediate Similarity	NPC264285
0.7081	Intermediate Similarity	NPC184408
0.7073	Intermediate Similarity	NPC309845
0.7071	Intermediate Similarity	NPC90229
0.7069	Intermediate Similarity	NPC60553
0.7065	Intermediate Similarity	NPC211813
0.7062	Intermediate Similarity	NPC183805
0.7062	Intermediate Similarity	NPC75544
0.7056	Intermediate Similarity	NPC63562
0.7053	Intermediate Similarity	NPC478032
0.7053	Intermediate Similarity	NPC89508
0.7042	Intermediate Similarity	NPC97746
0.7039	Intermediate Similarity	NPC109158
0.7039	Intermediate Similarity	NPC82370
0.7039	Intermediate Similarity	NPC220337
0.7037	Intermediate Similarity	NPC234987
0.7037	Intermediate Similarity	NPC474701
0.7033	Intermediate Similarity	NPC113812
0.7031	Intermediate Similarity	NPC320394
0.703	Intermediate Similarity	NPC200836
0.7029	Intermediate Similarity	NPC470404
0.7029	Intermediate Similarity	NPC470403
0.7029	Intermediate Similarity	NPC470394
0.7028	Intermediate Similarity	NPC220851
0.7026	Intermediate Similarity	NPC154339
0.7019	Intermediate Similarity	NPC190401
0.7019	Intermediate Similarity	NPC237740
0.7019	Intermediate Similarity	NPC50562
0.7019	Intermediate Similarity	NPC239763
0.7018	Intermediate Similarity	NPC39370
0.7014	Intermediate Similarity	NPC225279
0.7014	Intermediate Similarity	NPC276657
0.701	Intermediate Similarity	NPC4687
0.7005	Intermediate Similarity	NPC473186
0.7	Intermediate Similarity	NPC164340
0.7	Intermediate Similarity	NPC312860
0.7	Intermediate Similarity	NPC280714
0.7	Intermediate Similarity	NPC303658
0.699	Remote Similarity	NPC85273
0.699	Remote Similarity	NPC114974
0.6989	Remote Similarity	NPC470894
0.6986	Remote Similarity	NPC330009
0.6986	Remote Similarity	NPC67658
0.6984	Remote Similarity	NPC134586
0.698	Remote Similarity	NPC295898
0.6978	Remote Similarity	NPC269919
0.6978	Remote Similarity	NPC132680
0.6973	Remote Similarity	NPC471178
0.6972	Remote Similarity	NPC172222
0.6971	Remote Similarity	NPC236668
0.6968	Remote Similarity	NPC471294
0.6967	Remote Similarity	NPC74360
0.6967	Remote Similarity	NPC168209
0.6963	Remote Similarity	NPC317010
0.6963	Remote Similarity	NPC15840
0.6961	Remote Similarity	NPC33229
0.6955	Remote Similarity	NPC477587
0.6955	Remote Similarity	NPC477589
0.6954	Remote Similarity	NPC56170
0.6952	Remote Similarity	NPC268393
0.6952	Remote Similarity	NPC298840
0.6952	Remote Similarity	NPC13599
0.6952	Remote Similarity	NPC314940
0.6952	Remote Similarity	NPC303384
0.6952	Remote Similarity	NPC312645
0.6952	Remote Similarity	NPC3214
0.6952	Remote Similarity	NPC191088
0.6952	Remote Similarity	NPC473764
0.6949	Remote Similarity	NPC470395
0.6947	Remote Similarity	NPC211997
0.6947	Remote Similarity	NPC184964
0.6942	Remote Similarity	NPC469589
0.6938	Remote Similarity	NPC146976
0.6936	Remote Similarity	NPC472288
0.6934	Remote Similarity	NPC174760
0.6931	Remote Similarity	NPC471944
0.693	Remote Similarity	NPC214142
0.693	Remote Similarity	NPC24370
0.693	Remote Similarity	NPC319232
0.6927	Remote Similarity	NPC144691
0.6923	Remote Similarity	NPC118940
0.6923	Remote Similarity	NPC474183
0.6919	Remote Similarity	NPC46561
0.6919	Remote Similarity	NPC267343
0.6915	Remote Similarity	NPC302647
0.6915	Remote Similarity	NPC474767
0.691	Remote Similarity	NPC220523
0.6909	Remote Similarity	NPC477549
0.6907	Remote Similarity	NPC314002
0.6902	Remote Similarity	NPC63338

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 NPC241025 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	207
0.1-0.2	639
0.2-0.3	891
0.3-0.4	1077
0.4-0.5	2928
0.5-0.6	2615
0.6-0.7	761
0.7-0.8	32
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7978	Intermediate Similarity	NPD4736	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD1631	Approved
0.7709	Intermediate Similarity	NPD1575	Approved
0.7709	Intermediate Similarity	NPD1573	Approved
0.7614	Intermediate Similarity	NPD1630	Approved
0.7609	Intermediate Similarity	NPD1643	Phase 3
0.7514	Intermediate Similarity	NPD9510	Approved
0.7512	Intermediate Similarity	NPD5866	Approved
0.738	Intermediate Similarity	NPD3178	Discontinued
0.7366	Intermediate Similarity	NPD1587	Approved
0.7354	Intermediate Similarity	NPD6344	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD2433	Clinical (unspecified phase)
0.7277	Intermediate Similarity	NPD2383	Phase 1
0.7222	Intermediate Similarity	NPD484	Approved
0.7217	Intermediate Similarity	NPD3259	Approved
0.7204	Intermediate Similarity	NPD1586	Approved
0.7188	Intermediate Similarity	NPD9363	Approved
0.7188	Intermediate Similarity	NPD9364	Phase 2
0.7177	Intermediate Similarity	NPD7180	Phase 3
0.7143	Intermediate Similarity	NPD6376	Discontinued
0.7143	Intermediate Similarity	NPD6452	Discontinued
0.712	Intermediate Similarity	NPD1096	Discontinued
0.7098	Intermediate Similarity	NPD4948	Discontinued
0.7083	Intermediate Similarity	NPD7031	Phase 1
0.7075	Intermediate Similarity	NPD7547	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD3392	Approved
0.7065	Intermediate Similarity	NPD1568	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD4845	Discontinued
0.7052	Intermediate Similarity	NPD569	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD3315	Phase 3
0.7039	Intermediate Similarity	NPD3779	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD3326	Clinical (unspecified phase)
0.7016	Intermediate Similarity	NPD9362	Approved
0.7016	Intermediate Similarity	NPD1783	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD7453	Approved
0.701	Intermediate Similarity	NPD7452	Approved
0.701	Intermediate Similarity	NPD7222	Phase 2
0.6995	Remote Similarity	NPD6138	Clinical (unspecified phase)
0.6991	Remote Similarity	NPD5479	Discontinued
0.6991	Remote Similarity	NPD5801	Clinical (unspecified phase)
0.699	Remote Similarity	NPD1166	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD6716	Phase 1
0.6978	Remote Similarity	NPD9383	Approved
0.6978	Remote Similarity	NPD9382	Approved
0.6976	Remote Similarity	NPD2916	Discontinued
0.6971	Remote Similarity	NPD3243	Approved
0.6963	Remote Similarity	NPD5445	Approved
0.6961	Remote Similarity	NPD7001	Phase 3
0.6959	Remote Similarity	NPD1867	Approved
0.6948	Remote Similarity	NPD8356	Approved
0.6938	Remote Similarity	NPD7538	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD7417	Discontinued
0.6935	Remote Similarity	NPD5512	Phase 3
0.6919	Remote Similarity	NPD8405	Clinical (unspecified phase)
0.6912	Remote Similarity	NPD3947	Discontinued
0.6912	Remote Similarity	NPD5901	Discontinued
0.6912	Remote Similarity	NPD1659	Phase 1
0.6902	Remote Similarity	NPD9398	Clinical (unspecified phase)
0.6898	Remote Similarity	NPD7268	Clinical (unspecified phase)
0.6898	Remote Similarity	NPD7994	Phase 2
0.6897	Remote Similarity	NPD2779	Approved
0.6895	Remote Similarity	NPD5040	Clinical (unspecified phase)
0.689	Remote Similarity	NPD3945	Discontinued
0.6887	Remote Similarity	NPD6974	Phase 3
0.6887	Remote Similarity	NPD3258	Approved
0.6887	Remote Similarity	NPD7203	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD5975	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD1505	Phase 2
0.6878	Remote Similarity	NPD6732	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD7703	Clinical (unspecified phase)
0.6869	Remote Similarity	NPD6209	Approved
0.6857	Remote Similarity	NPD5417	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD5316	Approved
0.684	Remote Similarity	NPD5632	Approved
0.684	Remote Similarity	NPD7395	Discontinued
0.6833	Remote Similarity	NPD7853	Phase 2
0.6832	Remote Similarity	NPD2177	Approved
0.6832	Remote Similarity	NPD2175	Phase 3
0.6832	Remote Similarity	NPD2176	Approved
0.6828	Remote Similarity	NPD862	Approved
0.6828	Remote Similarity	NPD861	Approved
0.6828	Remote Similarity	NPD863	Approved
0.682	Remote Similarity	NPD8430	Approved
0.6818	Remote Similarity	NPD4373	Phase 2
0.6816	Remote Similarity	NPD7948	Phase 1
0.6802	Remote Similarity	NPD6965	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD4368	Phase 2
0.68	Remote Similarity	NPD4418	Discontinued
0.6796	Remote Similarity	NPD2715	Clinical (unspecified phase)
0.6793	Remote Similarity	NPD4671	Clinical (unspecified phase)
0.6793	Remote Similarity	NPD4669	Clinical (unspecified phase)
0.6793	Remote Similarity	NPD4670	Clinical (unspecified phase)
0.6791	Remote Similarity	NPD6824	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD750	Phase 2
0.6789	Remote Similarity	NPD7710	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD5898	Approved
0.6788	Remote Similarity	NPD5897	Approved
0.6788	Remote Similarity	NPD5899	Approved
0.6784	Remote Similarity	NPD6665	Discontinued
0.6782	Remote Similarity	NPD772	Phase 3
0.6782	Remote Similarity	NPD7777	Approved
0.6782	Remote Similarity	NPD7778	Approved
0.6782	Remote Similarity	NPD53	Approved
0.678	Remote Similarity	NPD5513	Phase 2
0.678	Remote Similarity	NPD5020	Approved
0.6777	Remote Similarity	NPD3257	Approved
0.6776	Remote Similarity	NPD5850	Phase 3
0.6771	Remote Similarity	NPD5751	Clinical (unspecified phase)
0.676	Remote Similarity	NPD9075	Approved
0.676	Remote Similarity	NPD9074	Approved
0.6758	Remote Similarity	NPD4952	Phase 3
0.6758	Remote Similarity	NPD4898	Clinical (unspecified phase)
0.6758	Remote Similarity	NPD9706	Clinical (unspecified phase)
0.6754	Remote Similarity	NPD9690	Approved
0.6749	Remote Similarity	NPD2778	Approved
0.6749	Remote Similarity	NPD6999	Discontinued
0.6749	Remote Similarity	NPD7000	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD3946	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD2721	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD648	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD3525	Discontinued
0.6741	Remote Similarity	NPD2921	Clinical (unspecified phase)
0.6729	Remote Similarity	NPD4312	Approved
0.6727	Remote Similarity	NPD1467	Approved
0.6727	Remote Similarity	NPD1466	Phase 3
0.672	Remote Similarity	NPD9705	Discontinued
0.672	Remote Similarity	NPD2844	Phase 3
0.672	Remote Similarity	NPD112	Approved
0.672	Remote Similarity	NPD6872	Clinical (unspecified phase)
0.672	Remote Similarity	NPD2781	Approved
0.6714	Remote Similarity	NPD5416	Discontinued
0.6712	Remote Similarity	NPD2951	Discontinued
0.6711	Remote Similarity	NPD6790	Phase 1
0.6702	Remote Similarity	NPD2780	Approved
0.6702	Remote Similarity	NPD2782	Approved
0.67	Remote Similarity	NPD4987	Clinical (unspecified phase)
0.67	Remote Similarity	NPD6569	Phase 2
0.6698	Remote Similarity	NPD4667	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD4394	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD6159	Phase 2
0.6683	Remote Similarity	NPD3321	Discontinued
0.6683	Remote Similarity	NPD5017	Discontinued
0.6682	Remote Similarity	NPD7878	Phase 2
0.6667	Remote Similarity	NPD6323	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4328	Approved
0.6667	Remote Similarity	NPD4204	Approved
0.6667	Remote Similarity	NPD5255	Approved
0.6667	Remote Similarity	NPD1768	Approved
0.6667	Remote Similarity	NPD4203	Approved
0.6667	Remote Similarity	NPD6987	Phase 1
0.6667	Remote Similarity	NPD5575	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6137	Clinical (unspecified phase)
0.6652	Remote Similarity	NPD6962	Phase 2
0.6652	Remote Similarity	NPD946	Discontinued
0.6651	Remote Similarity	NPD6247	Clinical (unspecified phase)
0.665	Remote Similarity	NPD1229	Phase 2
0.6638	Remote Similarity	NPD8463	Approved
0.6636	Remote Similarity	NPD6160	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD6995	Phase 1
0.6635	Remote Similarity	NPD6567	Clinical (unspecified phase)
0.6634	Remote Similarity	NPD4602	Approved
0.6634	Remote Similarity	NPD5497	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD2792	Approved
0.663	Remote Similarity	NPD3229	Phase 2
0.6623	Remote Similarity	NPD5483	Clinical (unspecified phase)
0.6622	Remote Similarity	NPD1961	Clinical (unspecified phase)
0.6621	Remote Similarity	NPD5640	Discontinued
0.6621	Remote Similarity	NPD3263	Phase 3
0.662	Remote Similarity	NPD1638	Discovery
0.662	Remote Similarity	NPD6242	Discontinued
0.6615	Remote Similarity	NPD4524	Discontinued
0.6614	Remote Similarity	NPD925	Approved
0.6614	Remote Similarity	NPD926	Approved
0.6603	Remote Similarity	NPD6290	Phase 2
0.66	Remote Similarity	NPD1213	Phase 3
0.6599	Remote Similarity	NPD5083	Clinical (unspecified phase)
0.6599	Remote Similarity	NPD721	Approved
0.6592	Remote Similarity	NPD6741	Clinical (unspecified phase)
0.659	Remote Similarity	NPD4923	Phase 1
0.6588	Remote Similarity	NPD4900	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD3814	Phase 1
0.6583	Remote Similarity	NPD6141	Clinical (unspecified phase)
0.6583	Remote Similarity	NPD6393	Clinical (unspecified phase)
0.658	Remote Similarity	NPD482	Approved
0.658	Remote Similarity	NPD3986	Discontinued
0.658	Remote Similarity	NPD6525	Clinical (unspecified phase)
0.6578	Remote Similarity	NPD604	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD7467	Discontinued
0.657	Remote Similarity	NPD6975	Discontinued
0.6567	Remote Similarity	NPD2336	Approved
0.6565	Remote Similarity	NPD3328	Phase 2
0.6558	Remote Similarity	NPD4989	Phase 2
0.6557	Remote Similarity	NPD5936	Approved
0.6557	Remote Similarity	NPD5939	Approved
0.6555	Remote Similarity	NPD7568	Phase 1
0.6553	Remote Similarity	NPD4396	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD3395	Approved
0.6552	Remote Similarity	NPD7944	Discontinued
0.6552	Remote Similarity	NPD6861	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD3396	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