NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	333.11
Volume:	330.031
LogP:	2.059
LogD:	2.108
LogS:	-3.707
# Rotatable Bonds:	1
TPSA:	83.82
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.516
Synthetic Accessibility Score:	3.731
Fsp3:	0.158
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:	-4.961
MDCK Permeability:	1.418893771187868e-05
Pgp-inhibitor:	0.003
Pgp-substrate:	0.785
Human Intestinal Absorption (HIA):	0.023
20% Bioavailability (F20%):	0.021
30% Bioavailability (F30%):	0.351

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.065
Plasma Protein Binding (PPB):	97.33110809326172%
Volume Distribution (VD):	0.613
Pgp-substrate:	3.814342498779297%

ADMET: Metabolism

CYP1A2-inhibitor:	0.977
CYP1A2-substrate:	0.574
CYP2C19-inhibitor:	0.079
CYP2C19-substrate:	0.066
CYP2C9-inhibitor:	0.266
CYP2C9-substrate:	0.793
CYP2D6-inhibitor:	0.52
CYP2D6-substrate:	0.222
CYP3A4-inhibitor:	0.041
CYP3A4-substrate:	0.115

ADMET: Excretion

Clearance (CL):	1.505
Half-life (T1/2):	0.594

ADMET: Toxicity

hERG Blockers:	0.018
Human Hepatotoxicity (H-HT):	0.257
Drug-inuced Liver Injury (DILI):	0.958
AMES Toxicity:	0.792
Rat Oral Acute Toxicity:	0.466
Maximum Recommended Daily Dose:	0.884
Skin Sensitization:	0.229
Carcinogencity:	0.935
Eye Corrosion:	0.003
Eye Irritation:	0.075
Respiratory Toxicity:	0.867

Download Data

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

Natural Product: NPC207851

Natural Product ID:	NPC207851
*Common Name:**	Vertilecanin A
IUPAC Name:	5-[(R)-hydroxy(phenyl)methyl]pyridine-2-carboxylic acid
Synonyms:
Standard InCHIKey:	BMTGCDDXYNEVRV-GFCCVEGCSA-N
Standard InCHI:	InChI=1S/C13H11NO3/c15-12(9-4-2-1-3-5-9)10-6-7-11(13(16)17)14-8-10/h1-8,12,15H,(H,16,17)/t12-/m1/s1
SMILES:	O[C@H](c1ccccc1)c1ccc(nc1)C(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL459095
PubChem CID:	10263201
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000089] Pyridines and derivatives [CHEMONTID:0001322] Pyridinecarboxylic acids and derivatives [CHEMONTID:0002414] Pyridinecarboxylic acids [CHEMONTID:0004624] Pyridine-2-carboxylic acids [CHEMONTID:0004627] 5-alkyl-2-carboxypyrimidines

*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
NPO5954	Petroselinum crispum	Species	Apiaceae	Eukaryota	n.a.	callus	n.a.	PMID[10552648]
NPO33206	verticillium lecanii	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	PMID[11429997]
NPO5954	Petroselinum crispum	Species	Apiaceae	Eukaryota	n.a.	leaf	n.a.	PMID[18214349]
NPO5954	Petroselinum crispum	Species	Apiaceae	Eukaryota	n.a.	seed	n.a.	PMID[21049975]
NPO5954	Petroselinum crispum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21800857]
NPO8234	Vernonia galamensis	Species	Asteraceae	Eukaryota	n.a.	seed	n.a.	PMID[9930408]
NPO5954	Petroselinum crispum	Species	Apiaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO5954	Petroselinum crispum	Species	Apiaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO5954	Petroselinum crispum	Species	Apiaceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO5954	Petroselinum crispum	Species	Apiaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO5954	Petroselinum crispum	Species	Apiaceae	Eukaryota	Shoot	n.a.	n.a.	Database[FooDB]
NPO5954	Petroselinum crispum	Species	Apiaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO5954	Petroselinum crispum	Species	Apiaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO5954	Petroselinum crispum	Species	Apiaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO9455	Uncaria orientalis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5954	Petroselinum crispum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5954	Petroselinum crispum	Species	Apiaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO5954	Petroselinum crispum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9455	Uncaria orientalis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8620	Caesalpinia major	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5954	Petroselinum crispum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8234	Vernonia galamensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2389	Pinus japonica	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4875	Ugni molinae	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3668	Kalanchoe delagoensis	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4072	Anacyclus radiatus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9072	Bolocera tuediae	Species	Actiniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8771	Heterodermia dissecta	Species	Physciaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8009	Arctotis venusta	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7188	Zieria granulata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9455	Uncaria orientalis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6292	Teucrium brevifolium	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5832	Acacia nelsonii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5540	Amorpha canescens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4321	Siphula ceratites	Species	Icmadophilaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8620	Caesalpinia major	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24536	Senecio cylindricus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5954	Petroselinum crispum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9330	Odinia antillensis	Species	Odiniidae	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
Others	2

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT915	Organism	Helicoverpa zea	Helicoverpa zea	Activity	=	49.0	%	PMID[565758]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	IZ	=	8.0	mm	PMID[565758]

☑ 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 NPC207851 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	300
0.1-0.2	2016
0.2-0.3	9947
0.3-0.4	12976
0.4-0.5	12192
0.5-0.6	2878
0.6-0.7	1994
0.7-0.8	369
0.8-0.85	18
0.85-0.9	5
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9146	High Similarity	NPC41717
0.8538	High Similarity	NPC273532
0.8486	Intermediate Similarity	NPC57398
0.8452	Intermediate Similarity	NPC322644
0.8424	Intermediate Similarity	NPC123395
0.8405	Intermediate Similarity	NPC302159
0.8289	Intermediate Similarity	NPC328596
0.8289	Intermediate Similarity	NPC328318
0.8107	Intermediate Similarity	NPC263455
0.8063	Intermediate Similarity	NPC317373
0.8053	Intermediate Similarity	NPC165599
0.8051	Intermediate Similarity	NPC317752
0.801	Intermediate Similarity	NPC327592
0.8	Intermediate Similarity	NPC318299
0.7967	Intermediate Similarity	NPC295158
0.7967	Intermediate Similarity	NPC241025
0.7941	Intermediate Similarity	NPC312860
0.7927	Intermediate Similarity	NPC85443
0.7927	Intermediate Similarity	NPC244741
0.7926	Intermediate Similarity	NPC90229
0.791	Intermediate Similarity	NPC249614
0.7908	Intermediate Similarity	NPC118940
0.7904	Intermediate Similarity	NPC167400
0.7892	Intermediate Similarity	NPC83111
0.7889	Intermediate Similarity	NPC164340
0.7884	Intermediate Similarity	NPC472284
0.7857	Intermediate Similarity	NPC82370
0.7839	Intermediate Similarity	NPC472285
0.7796	Intermediate Similarity	NPC469489
0.7789	Intermediate Similarity	NPC474916
0.7784	Intermediate Similarity	NPC278434
0.7783	Intermediate Similarity	NPC229893
0.7754	Intermediate Similarity	NPC114974
0.7749	Intermediate Similarity	NPC103361
0.7747	Intermediate Similarity	NPC317010
0.7744	Intermediate Similarity	NPC29702
0.7744	Intermediate Similarity	NPC328029
0.7742	Intermediate Similarity	NPC44354
0.7737	Intermediate Similarity	NPC141454
0.7725	Intermediate Similarity	NPC135950
0.7725	Intermediate Similarity	NPC146724
0.7722	Intermediate Similarity	NPC139763
0.7716	Intermediate Similarity	NPC123839
0.7716	Intermediate Similarity	NPC309845
0.7704	Intermediate Similarity	NPC266249
0.7701	Intermediate Similarity	NPC144381
0.7697	Intermediate Similarity	NPC114310
0.7697	Intermediate Similarity	NPC470894
0.7688	Intermediate Similarity	NPC89508
0.7684	Intermediate Similarity	NPC109922
0.768	Intermediate Similarity	NPC84347
0.7676	Intermediate Similarity	NPC282103
0.7672	Intermediate Similarity	NPC230403
0.7653	Intermediate Similarity	NPC193238
0.7641	Intermediate Similarity	NPC472259
0.7638	Intermediate Similarity	NPC111732
0.7634	Intermediate Similarity	NPC315555
0.7634	Intermediate Similarity	NPC118084
0.763	Intermediate Similarity	NPC107287
0.7624	Intermediate Similarity	NPC303225
0.7611	Intermediate Similarity	NPC253810
0.7607	Intermediate Similarity	NPC256893
0.7606	Intermediate Similarity	NPC154339
0.7602	Intermediate Similarity	NPC472286
0.7602	Intermediate Similarity	NPC472287
0.7582	Intermediate Similarity	NPC150048
0.7582	Intermediate Similarity	NPC203754
0.7579	Intermediate Similarity	NPC267343
0.7574	Intermediate Similarity	NPC312645
0.7562	Intermediate Similarity	NPC237740
0.7557	Intermediate Similarity	NPC80681
0.7554	Intermediate Similarity	NPC52831
0.7554	Intermediate Similarity	NPC325705
0.7553	Intermediate Similarity	NPC75544
0.755	Intermediate Similarity	NPC476467
0.754	Intermediate Similarity	NPC194040
0.7539	Intermediate Similarity	NPC202812
0.7529	Intermediate Similarity	NPC230085
0.7529	Intermediate Similarity	NPC159630
0.7514	Intermediate Similarity	NPC302647
0.75	Intermediate Similarity	NPC283219
0.75	Intermediate Similarity	NPC112741
0.75	Intermediate Similarity	NPC248041
0.75	Intermediate Similarity	NPC317572
0.75	Intermediate Similarity	NPC126709
0.7488	Intermediate Similarity	NPC473850
0.7487	Intermediate Similarity	NPC472752
0.7486	Intermediate Similarity	NPC33229
0.7474	Intermediate Similarity	NPC138370
0.7473	Intermediate Similarity	NPC159125
0.7462	Intermediate Similarity	NPC314648
0.7459	Intermediate Similarity	NPC471997
0.7458	Intermediate Similarity	NPC113812
0.7455	Intermediate Similarity	NPC322488
0.7452	Intermediate Similarity	NPC473506
0.7451	Intermediate Similarity	NPC314270
0.7447	Intermediate Similarity	NPC90415
0.7446	Intermediate Similarity	NPC111275
0.744	Intermediate Similarity	NPC57797
0.744	Intermediate Similarity	NPC250807
0.7438	Intermediate Similarity	NPC36405
0.7437	Intermediate Similarity	NPC63041
0.7432	Intermediate Similarity	NPC110500
0.7432	Intermediate Similarity	NPC149155
0.7432	Intermediate Similarity	NPC203468
0.7424	Intermediate Similarity	NPC309498
0.7423	Intermediate Similarity	NPC248782
0.7418	Intermediate Similarity	NPC158129
0.7416	Intermediate Similarity	NPC328186
0.7416	Intermediate Similarity	NPC122968
0.7416	Intermediate Similarity	NPC228377
0.7416	Intermediate Similarity	NPC477787
0.7415	Intermediate Similarity	NPC315804
0.7415	Intermediate Similarity	NPC313804
0.7404	Intermediate Similarity	NPC475137
0.7404	Intermediate Similarity	NPC475498
0.7403	Intermediate Similarity	NPC70949
0.7403	Intermediate Similarity	NPC78020
0.7391	Intermediate Similarity	NPC267885
0.7387	Intermediate Similarity	NPC88008
0.7387	Intermediate Similarity	NPC183777
0.7386	Intermediate Similarity	NPC209362
0.7385	Intermediate Similarity	NPC160127
0.7385	Intermediate Similarity	NPC50997
0.7385	Intermediate Similarity	NPC474767
0.7381	Intermediate Similarity	NPC471977
0.7381	Intermediate Similarity	NPC471190
0.7381	Intermediate Similarity	NPC470486
0.7381	Intermediate Similarity	NPC475644
0.7381	Intermediate Similarity	NPC475362
0.738	Intermediate Similarity	NPC48938
0.7379	Intermediate Similarity	NPC54066
0.7377	Intermediate Similarity	NPC191310
0.7377	Intermediate Similarity	NPC477976
0.7376	Intermediate Similarity	NPC219087
0.7371	Intermediate Similarity	NPC153769
0.7368	Intermediate Similarity	NPC209917
0.7362	Intermediate Similarity	NPC165370
0.7356	Intermediate Similarity	NPC76565
0.7353	Intermediate Similarity	NPC477907
0.7353	Intermediate Similarity	NPC42678
0.7353	Intermediate Similarity	NPC477909
0.7351	Intermediate Similarity	NPC219848
0.7347	Intermediate Similarity	NPC315491
0.7347	Intermediate Similarity	NPC45459
0.7347	Intermediate Similarity	NPC213308
0.734	Intermediate Similarity	NPC236668
0.734	Intermediate Similarity	NPC320394
0.7333	Intermediate Similarity	NPC475631
0.7333	Intermediate Similarity	NPC87152
0.7333	Intermediate Similarity	NPC476110
0.7333	Intermediate Similarity	NPC146824
0.7333	Intermediate Similarity	NPC475600
0.733	Intermediate Similarity	NPC216428
0.7326	Intermediate Similarity	NPC71037
0.7324	Intermediate Similarity	NPC237702
0.732	Intermediate Similarity	NPC77061
0.7316	Intermediate Similarity	NPC206186
0.7313	Intermediate Similarity	NPC48042
0.7313	Intermediate Similarity	NPC304179
0.7313	Intermediate Similarity	NPC472550
0.7312	Intermediate Similarity	NPC55772
0.7312	Intermediate Similarity	NPC256268
0.7311	Intermediate Similarity	NPC316841
0.7311	Intermediate Similarity	NPC292416
0.7311	Intermediate Similarity	NPC260434
0.7311	Intermediate Similarity	NPC473689
0.731	Intermediate Similarity	NPC98864
0.7308	Intermediate Similarity	NPC477788
0.7304	Intermediate Similarity	NPC146976
0.7304	Intermediate Similarity	NPC477979
0.7303	Intermediate Similarity	NPC213914
0.73	Intermediate Similarity	NPC314297
0.73	Intermediate Similarity	NPC315545
0.7296	Intermediate Similarity	NPC81535
0.7293	Intermediate Similarity	NPC471178
0.729	Intermediate Similarity	NPC182222
0.7288	Intermediate Similarity	NPC63562
0.7287	Intermediate Similarity	NPC243058
0.7286	Intermediate Similarity	NPC132539
0.7286	Intermediate Similarity	NPC12944
0.7286	Intermediate Similarity	NPC25442
0.7286	Intermediate Similarity	NPC289086
0.7282	Intermediate Similarity	NPC62367
0.7282	Intermediate Similarity	NPC106824
0.7277	Intermediate Similarity	NPC244839
0.7277	Intermediate Similarity	NPC319880
0.7277	Intermediate Similarity	NPC30456
0.7277	Intermediate Similarity	NPC320324
0.7277	Intermediate Similarity	NPC183805
0.7268	Intermediate Similarity	NPC473764
0.7268	Intermediate Similarity	NPC314940
0.7264	Intermediate Similarity	NPC171787
0.7259	Intermediate Similarity	NPC470279
0.7258	Intermediate Similarity	NPC183662
0.7258	Intermediate Similarity	NPC217372
0.7258	Intermediate Similarity	NPC157583
0.7258	Intermediate Similarity	NPC84827
0.7258	Intermediate Similarity	NPC15573
0.7258	Intermediate Similarity	NPC145885

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 NPC207851 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	193
0.1-0.2	562
0.2-0.3	773
0.3-0.4	1318
0.4-0.5	2823
0.5-0.6	2345
0.6-0.7	984
0.7-0.8	150
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8207	Intermediate Similarity	NPD5975	Clinical (unspecified phase)
0.8202	Intermediate Similarity	NPD3178	Discontinued
0.7912	Intermediate Similarity	NPD1096	Discontinued
0.7904	Intermediate Similarity	NPD9075	Approved
0.7904	Intermediate Similarity	NPD9074	Approved
0.7901	Intermediate Similarity	NPD1783	Clinical (unspecified phase)
0.7829	Intermediate Similarity	NPD5088	Discontinued
0.7829	Intermediate Similarity	NPD1631	Approved
0.779	Intermediate Similarity	NPD8304	Clinical (unspecified phase)
0.7758	Intermediate Similarity	NPD2896	Discontinued
0.7753	Intermediate Similarity	NPD1575	Approved
0.7753	Intermediate Similarity	NPD1573	Approved
0.7733	Intermediate Similarity	NPD180	Clinical (unspecified phase)
0.7701	Intermediate Similarity	NPD3321	Discontinued
0.7672	Intermediate Similarity	NPD4526	Approved
0.7672	Intermediate Similarity	NPD4529	Approved
0.7672	Intermediate Similarity	NPD4528	Approved
0.7665	Intermediate Similarity	NPD107	Approved
0.766	Intermediate Similarity	NPD2336	Approved
0.7657	Intermediate Similarity	NPD1630	Approved
0.7657	Intermediate Similarity	NPD5255	Approved
0.7651	Intermediate Similarity	NPD203	Clinical (unspecified phase)
0.7641	Intermediate Similarity	NPD5901	Discontinued
0.7624	Intermediate Similarity	NPD4736	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD6665	Discontinued
0.7614	Intermediate Similarity	NPD2511	Approved
0.7606	Intermediate Similarity	NPD8063	Discontinued
0.76	Intermediate Similarity	NPD3795	Approved
0.76	Intermediate Similarity	NPD3794	Approved
0.759	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.7554	Intermediate Similarity	NPD9510	Approved
0.7529	Intermediate Similarity	NPD3813	Approved
0.75	Intermediate Similarity	NPD2581	Approved
0.75	Intermediate Similarity	NPD1587	Approved
0.75	Intermediate Similarity	NPD2307	Discontinued
0.75	Intermediate Similarity	NPD9271	Approved
0.75	Intermediate Similarity	NPD820	Phase 3
0.75	Intermediate Similarity	NPD2582	Approved
0.75	Intermediate Similarity	NPD4948	Discontinued
0.7473	Intermediate Similarity	NPD750	Phase 2
0.7471	Intermediate Similarity	NPD3525	Discontinued
0.7447	Intermediate Similarity	NPD3315	Phase 3
0.7438	Intermediate Similarity	NPD3393	Approved
0.7438	Intermediate Similarity	NPD3394	Approved
0.7438	Intermediate Similarity	NPD3389	Approved
0.7437	Intermediate Similarity	NPD2510	Approved
0.7437	Intermediate Similarity	NPD2509	Approved
0.7435	Intermediate Similarity	NPD4376	Phase 3
0.7432	Intermediate Similarity	NPD482	Approved
0.7424	Intermediate Similarity	NPD7001	Phase 3
0.7418	Intermediate Similarity	NPD485	Clinical (unspecified phase)
0.7413	Intermediate Similarity	NPD3779	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD5398	Clinical (unspecified phase)
0.7401	Intermediate Similarity	NPD4670	Clinical (unspecified phase)
0.7401	Intermediate Similarity	NPD4669	Clinical (unspecified phase)
0.7401	Intermediate Similarity	NPD4671	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD1173	Approved
0.7391	Intermediate Similarity	NPD5100	Phase 3
0.7391	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD2809	Approved
0.7374	Intermediate Similarity	NPD6323	Clinical (unspecified phase)
0.7374	Intermediate Similarity	NPD3947	Discontinued
0.7371	Intermediate Similarity	NPD5965	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD6641	Approved
0.7351	Intermediate Similarity	NPD6642	Approved
0.7347	Intermediate Similarity	NPD484	Approved
0.7337	Intermediate Similarity	NPD6732	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD1586	Approved
0.7327	Intermediate Similarity	NPD5475	Discontinued
0.7317	Intermediate Similarity	NPD3326	Clinical (unspecified phase)
0.7313	Intermediate Similarity	NPD6529	Discontinued
0.7296	Intermediate Similarity	NPD6137	Clinical (unspecified phase)
0.7295	Intermediate Similarity	NPD3280	Approved
0.7293	Intermediate Similarity	NPD1568	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD4699	Discontinued
0.7287	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7286	Intermediate Similarity	NPD8289	Discontinued
0.7278	Intermediate Similarity	NPD9506	Approved
0.7273	Intermediate Similarity	NPD6452	Discontinued
0.7273	Intermediate Similarity	NPD5721	Clinical (unspecified phase)
0.7259	Intermediate Similarity	NPD4396	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD3243	Approved
0.7246	Intermediate Similarity	NPD1627	Clinical (unspecified phase)
0.7245	Intermediate Similarity	NPD7778	Approved
0.7245	Intermediate Similarity	NPD7777	Approved
0.7245	Intermediate Similarity	NPD53	Approved
0.7241	Intermediate Similarity	NPD4417	Approved
0.724	Intermediate Similarity	NPD1213	Phase 3
0.7235	Intermediate Similarity	NPD2921	Clinical (unspecified phase)
0.7231	Intermediate Similarity	NPD7061	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD9364	Phase 2
0.7225	Intermediate Similarity	NPD9363	Approved
0.7211	Intermediate Similarity	NPD3082	Discontinued
0.7208	Intermediate Similarity	NPD7000	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD6999	Discontinued
0.7207	Intermediate Similarity	NPD9382	Approved
0.7207	Intermediate Similarity	NPD9383	Approved
0.72	Intermediate Similarity	NPD4703	Approved
0.72	Intermediate Similarity	NPD6987	Phase 1
0.72	Intermediate Similarity	NPD7712	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD4702	Approved
0.7198	Intermediate Similarity	NPD925	Approved
0.7198	Intermediate Similarity	NPD926	Approved
0.7196	Intermediate Similarity	NPD2092	Phase 2
0.7196	Intermediate Similarity	NPD2095	Phase 2
0.7196	Intermediate Similarity	NPD2094	Phase 2
0.7189	Intermediate Similarity	NPD2077	Approved
0.7189	Intermediate Similarity	NPD2076	Approved
0.7188	Intermediate Similarity	NPD7233	Approved
0.7188	Intermediate Similarity	NPD7234	Approved
0.7179	Intermediate Similarity	NPD4427	Phase 2
0.7164	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.7164	Intermediate Similarity	NPD7010	Phase 3
0.7158	Intermediate Similarity	NPD4554	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD721	Approved
0.7158	Intermediate Similarity	NPD2091	Phase 2
0.7158	Intermediate Similarity	NPD2096	Phase 2
0.7157	Intermediate Similarity	NPD7470	Discontinued
0.7157	Intermediate Similarity	NPD7927	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD9284	Approved
0.7151	Intermediate Similarity	NPD9690	Approved
0.7151	Intermediate Similarity	NPD1649	Discontinued
0.715	Intermediate Similarity	NPD5513	Phase 2
0.7143	Intermediate Similarity	NPD8356	Approved
0.7143	Intermediate Similarity	NPD9362	Approved
0.7136	Intermediate Similarity	NPD5417	Clinical (unspecified phase)
0.7129	Intermediate Similarity	NPD1996	Discontinued
0.7127	Intermediate Similarity	NPD112	Approved
0.7127	Intermediate Similarity	NPD9705	Discontinued
0.7127	Intermediate Similarity	NPD9398	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD751	Clinical (unspecified phase)
0.7122	Intermediate Similarity	NPD7069	Discontinued
0.712	Intermediate Similarity	NPD5862	Discovery
0.711	Intermediate Similarity	NPD4805	Approved
0.711	Intermediate Similarity	NPD5020	Approved
0.7109	Intermediate Similarity	NPD6173	Approved
0.7109	Intermediate Similarity	NPD6752	Phase 1
0.7109	Intermediate Similarity	NPD6753	Phase 1
0.7107	Intermediate Similarity	NPD1229	Phase 2
0.7095	Intermediate Similarity	NPD5257	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD7944	Discontinued
0.709	Intermediate Similarity	NPD1643	Phase 3
0.7081	Intermediate Similarity	NPD7404	Approved
0.7077	Intermediate Similarity	NPD5505	Discontinued
0.7074	Intermediate Similarity	NPD5751	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD4987	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD4174	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD7818	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD1274	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD7538	Clinical (unspecified phase)
0.705	Intermediate Similarity	NPD7727	Phase 2
0.7048	Intermediate Similarity	NPD9080	Approved
0.7048	Intermediate Similarity	NPD8479	Phase 2
0.7039	Intermediate Similarity	NPD5866	Approved
0.7039	Intermediate Similarity	NPD6657	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD9076	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD6661	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD7878	Phase 2
0.703	Intermediate Similarity	NPD944	Approved
0.7027	Intermediate Similarity	NPD5483	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD2781	Approved
0.7024	Intermediate Similarity	NPD7998	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD5003	Discontinued
0.7011	Intermediate Similarity	NPD2780	Approved
0.7011	Intermediate Similarity	NPD2782	Approved
0.7009	Intermediate Similarity	NPD8430	Approved
0.7006	Intermediate Similarity	NPD1270	Approved
0.7005	Intermediate Similarity	NPD2823	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD2715	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD4804	Approved
0.699	Remote Similarity	NPD5317	Clinical (unspecified phase)
0.699	Remote Similarity	NPD5416	Discontinued
0.699	Remote Similarity	NPD6569	Phase 2
0.6986	Remote Similarity	NPD2787	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD8122	Approved
0.6984	Remote Similarity	NPD8123	Approved
0.6983	Remote Similarity	NPD9706	Clinical (unspecified phase)
0.6979	Remote Similarity	NPD6178	Phase 3
0.6974	Remote Similarity	NPD2565	Phase 2
0.6974	Remote Similarity	NPD2564	Approved
0.697	Remote Similarity	NPD5512	Phase 3
0.6968	Remote Similarity	NPD4883	Approved
0.6967	Remote Similarity	NPD5827	Discontinued
0.6965	Remote Similarity	NPD7817	Phase 1
0.6963	Remote Similarity	NPD5640	Discontinued
0.6961	Remote Similarity	NPD3371	Approved
0.6959	Remote Similarity	NPD6791	Phase 2
0.6952	Remote Similarity	NPD7395	Discontinued
0.6952	Remote Similarity	NPD6578	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD3222	Phase 2
0.6946	Remote Similarity	NPD8115	Approved
0.6946	Remote Similarity	NPD3247	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD2721	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD7396	Approved
0.6946	Remote Similarity	NPD8114	Approved
0.6943	Remote Similarity	NPD4889	Approved
0.6942	Remote Similarity	NPD4900	Clinical (unspecified phase)
0.6942	Remote Similarity	NPD6204	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD6872	Clinical (unspecified phase)
0.6932	Remote Similarity	NPD1352	Discontinued

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