NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	107.04
Volume:	113.017
LogP:	0.448
LogD:	0.646
LogS:	-0.224
# Rotatable Bonds:	1
TPSA:	29.96
# H-Bond Aceptor:	2
# H-Bond Donor:	0
# Rings:	1
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.499
Synthetic Accessibility Score:	2.158
Fsp3:	0.0
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	2
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.209
MDCK Permeability:	2.64407426584512e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.09
30% Bioavailability (F30%):	0.016

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.914
Plasma Protein Binding (PPB):	24.75997543334961%
Volume Distribution (VD):	1.186
Pgp-substrate:	74.2646484375%

ADMET: Metabolism

CYP1A2-inhibitor:	0.546
CYP1A2-substrate:	0.156
CYP2C19-inhibitor:	0.035
CYP2C19-substrate:	0.16
CYP2C9-inhibitor:	0.011
CYP2C9-substrate:	0.436
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.366
CYP3A4-inhibitor:	0.005
CYP3A4-substrate:	0.2

ADMET: Excretion

Clearance (CL):	3.337
Half-life (T1/2):	0.715

ADMET: Toxicity

hERG Blockers:	0.037
Human Hepatotoxicity (H-HT):	0.03
Drug-inuced Liver Injury (DILI):	0.08
AMES Toxicity:	0.058
Rat Oral Acute Toxicity:	0.169
Maximum Recommended Daily Dose:	0.029
Skin Sensitization:	0.423
Carcinogencity:	0.068
Eye Corrosion:	0.962
Eye Irritation:	0.996
Respiratory Toxicity:	0.971

Download Data

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

Natural Product: NPC313823

Natural Product ID:	NPC313823
*Common Name:**	2-Pyridinecarboxaldehyde
IUPAC Name:	pyridine-2-carbaldehyde
Synonyms:	Pyridine-2-Carbaldehyde
Standard InCHIKey:	CSDSSGBPEUDDEE-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C6H5NO/c8-5-6-3-1-2-4-7-6/h1-5H
SMILES:	O=Cc1ccccn1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL274794
PubChem CID:	14273
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000089] Pyridines and derivatives [CHEMONTID:0002212] Pyridine carboxaldehydes

*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
NPO1099	Capparis spinosa	Species	Capparaceae	Eukaryota	aerial parts and buds	Cagliari, Sardinia	2012-FEB	PMID[22769561]
NPO1099	Capparis spinosa	Species	Capparaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO1099	Capparis spinosa	Species	Capparaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO1099	Capparis spinosa	Species	Capparaceae	Eukaryota	Flower	n.a.	n.a.	Database[FooDB]
NPO1099	Capparis spinosa	Species	Capparaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO1099	Capparis spinosa	Species	Capparaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO1099	Capparis spinosa	Species	Capparaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO1099	Capparis spinosa	Species	Capparaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1099	Capparis spinosa	Species	Capparaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1099	Capparis spinosa	Species	Capparaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]

☑ 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
EC50	2
IC50	2
Kd	1
Ki	1
Others	3

Activity Type	# Activity
Cell Line	1
Individual Protein	2
Organism	3
Others	2
Protein Complex	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT169	Cell Line	B16-F10	Mus musculus	IC50	=	70740.0	nM	PMID[533136]
NPT805	Protein Complex	GABA-A receptor; anion channel	Rattus norvegicus	Ki	>	100000.0	nM	PMID[533131]
NPT2	Others	Unspecified		Kd	=	100000.0	nM	PMID[533132]
NPT2	Others	Unspecified		IC50	>	300000.0	nM	PMID[533132]
NPT450	Organism	Meloidogyne incognita	Meloidogyne incognita	mortality	=	100.0	%	PMID[533133]
NPT450	Organism	Meloidogyne incognita	Meloidogyne incognita	EC50	=	3.6	ug.mL-1	PMID[533133]
NPT450	Organism	Meloidogyne incognita	Meloidogyne incognita	EC50	=	25.0	ug.mL-1	PMID[533133]
NPT813	Individual Protein	GABA transporter 1	Mus musculus	Activity	=	48.0	%	PMID[533134]
NPT813	Individual Protein	GABA transporter 1	Mus musculus	Activity	=	85.0	%	PMID[533135]

☑ 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 NPC313823 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	1491
0.1-0.2	13635
0.2-0.3	17758
0.3-0.4	5201
0.4-0.5	2269
0.5-0.6	1741
0.6-0.7	502
0.7-0.8	92
0.8-0.85	4
0.85-0.9	3
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8984	High Similarity	NPC71236
0.8647	High Similarity	NPC23215
0.8615	High Similarity	NPC471589
0.8519	High Similarity	NPC472288
0.8298	Intermediate Similarity	NPC302159
0.8235	Intermediate Similarity	NPC291517
0.8115	Intermediate Similarity	NPC231655
0.7847	Intermediate Similarity	NPC467188
0.78	Intermediate Similarity	NPC80681
0.7769	Intermediate Similarity	NPC83987
0.7718	Intermediate Similarity	NPC209362
0.7703	Intermediate Similarity	NPC70406
0.7703	Intermediate Similarity	NPC472260
0.7698	Intermediate Similarity	NPC330326
0.7651	Intermediate Similarity	NPC251391
0.7635	Intermediate Similarity	NPC313889
0.7619	Intermediate Similarity	NPC105811
0.7582	Intermediate Similarity	NPC242116
0.7548	Intermediate Similarity	NPC41717
0.7535	Intermediate Similarity	NPC14448
0.7535	Intermediate Similarity	NPC167200
0.7535	Intermediate Similarity	NPC292434
0.7535	Intermediate Similarity	NPC138596
0.7535	Intermediate Similarity	NPC64661
0.7535	Intermediate Similarity	NPC200397
0.7535	Intermediate Similarity	NPC195704
0.7535	Intermediate Similarity	NPC98156
0.7516	Intermediate Similarity	NPC473706
0.75	Intermediate Similarity	NPC213914
0.75	Intermediate Similarity	NPC70949
0.7484	Intermediate Similarity	NPC42372
0.7483	Intermediate Similarity	NPC114310
0.745	Intermediate Similarity	NPC123906
0.7447	Intermediate Similarity	NPC322488
0.7436	Intermediate Similarity	NPC114637
0.7405	Intermediate Similarity	NPC273532
0.7402	Intermediate Similarity	NPC76540
0.74	Intermediate Similarity	NPC473878
0.7383	Intermediate Similarity	NPC100726
0.7379	Intermediate Similarity	NPC85443
0.7376	Intermediate Similarity	NPC256893
0.7368	Intermediate Similarity	NPC229055
0.7364	Intermediate Similarity	NPC27802
0.7362	Intermediate Similarity	NPC102755
0.7329	Intermediate Similarity	NPC59839
0.7329	Intermediate Similarity	NPC3698
0.7329	Intermediate Similarity	NPC74928
0.7329	Intermediate Similarity	NPC48171
0.7329	Intermediate Similarity	NPC302717
0.7329	Intermediate Similarity	NPC97230
0.7329	Intermediate Similarity	NPC169308
0.7329	Intermediate Similarity	NPC209281
0.7329	Intermediate Similarity	NPC77582
0.7329	Intermediate Similarity	NPC12831
0.7329	Intermediate Similarity	NPC129753
0.7329	Intermediate Similarity	NPC286529
0.7329	Intermediate Similarity	NPC205604
0.7329	Intermediate Similarity	NPC244087
0.732	Intermediate Similarity	NPC74357
0.7308	Intermediate Similarity	NPC265100
0.7297	Intermediate Similarity	NPC230085
0.7297	Intermediate Similarity	NPC159630
0.7296	Intermediate Similarity	NPC253810
0.7292	Intermediate Similarity	NPC328029
0.7285	Intermediate Similarity	NPC471655
0.7279	Intermediate Similarity	NPC58268
0.7279	Intermediate Similarity	NPC129412
0.7279	Intermediate Similarity	NPC114033
0.7279	Intermediate Similarity	NPC101130
0.7267	Intermediate Similarity	NPC112741
0.7255	Intermediate Similarity	NPC33229
0.7248	Intermediate Similarity	NPC167400
0.7241	Intermediate Similarity	NPC65408
0.7237	Intermediate Similarity	NPC217021
0.7237	Intermediate Similarity	NPC470679
0.7222	Intermediate Similarity	NPC237188
0.7212	Intermediate Similarity	NPC207851
0.7205	Intermediate Similarity	NPC293216
0.719	Intermediate Similarity	NPC312860
0.719	Intermediate Similarity	NPC107287
0.7177	Intermediate Similarity	NPC213774
0.7174	Intermediate Similarity	NPC46358
0.7143	Intermediate Similarity	NPC263455
0.7134	Intermediate Similarity	NPC73994
0.7121	Intermediate Similarity	NPC235843
0.7117	Intermediate Similarity	NPC157583
0.7117	Intermediate Similarity	NPC83774
0.7081	Intermediate Similarity	NPC249614
0.7068	Intermediate Similarity	NPC473901
0.7044	Intermediate Similarity	NPC233380
0.703	Intermediate Similarity	NPC61011
0.7024	Intermediate Similarity	NPC118084
0.7006	Intermediate Similarity	NPC474492
0.6993	Remote Similarity	NPC13432
0.6988	Remote Similarity	NPC191415
0.6988	Remote Similarity	NPC470677
0.6985	Remote Similarity	NPC471402
0.6985	Remote Similarity	NPC297486
0.6985	Remote Similarity	NPC240136
0.6972	Remote Similarity	NPC165370
0.6963	Remote Similarity	NPC84268
0.6962	Remote Similarity	NPC100104
0.6962	Remote Similarity	NPC470680
0.6934	Remote Similarity	NPC91958
0.6934	Remote Similarity	NPC143603
0.6923	Remote Similarity	NPC474236
0.6909	Remote Similarity	NPC284775
0.6906	Remote Similarity	NPC48564
0.6906	Remote Similarity	NPC265605
0.6906	Remote Similarity	NPC182570
0.6905	Remote Similarity	NPC110158
0.6905	Remote Similarity	NPC46895
0.6884	Remote Similarity	NPC11863
0.6883	Remote Similarity	NPC102664
0.6864	Remote Similarity	NPC295158
0.6853	Remote Similarity	NPC471311
0.6853	Remote Similarity	NPC471313
0.6849	Remote Similarity	NPC20021
0.6845	Remote Similarity	NPC159125
0.6831	Remote Similarity	NPC151489
0.6809	Remote Similarity	NPC290094
0.6806	Remote Similarity	NPC89490
0.6792	Remote Similarity	NPC113812
0.6788	Remote Similarity	NPC469529
0.6781	Remote Similarity	NPC324611
0.6768	Remote Similarity	NPC54214
0.6761	Remote Similarity	NPC27740
0.6759	Remote Similarity	NPC329896
0.6759	Remote Similarity	NPC475090
0.6759	Remote Similarity	NPC475105
0.6753	Remote Similarity	NPC220523
0.6744	Remote Similarity	NPC255909
0.6744	Remote Similarity	NPC103119
0.6738	Remote Similarity	NPC56856
0.6736	Remote Similarity	NPC212125
0.6736	Remote Similarity	NPC306397
0.6726	Remote Similarity	NPC477042
0.6724	Remote Similarity	NPC216550
0.6713	Remote Similarity	NPC166424
0.6713	Remote Similarity	NPC245244
0.6713	Remote Similarity	NPC146373
0.6712	Remote Similarity	NPC315320
0.6711	Remote Similarity	NPC29702
0.6706	Remote Similarity	NPC477003
0.6689	Remote Similarity	NPC150592
0.6687	Remote Similarity	NPC293487
0.6686	Remote Similarity	NPC326422
0.6685	Remote Similarity	NPC474767
0.6667	Remote Similarity	NPC169625
0.6667	Remote Similarity	NPC106824
0.6667	Remote Similarity	NPC274981
0.6667	Remote Similarity	NPC202957
0.6648	Remote Similarity	NPC135950
0.6646	Remote Similarity	NPC322644
0.6643	Remote Similarity	NPC476322
0.6625	Remote Similarity	NPC76982
0.661	Remote Similarity	NPC128244
0.661	Remote Similarity	NPC77061
0.6609	Remote Similarity	NPC469489
0.6605	Remote Similarity	NPC478185
0.6599	Remote Similarity	NPC282398
0.6592	Remote Similarity	NPC123395
0.6592	Remote Similarity	NPC81535
0.6592	Remote Similarity	NPC284338
0.6592	Remote Similarity	NPC103361
0.6585	Remote Similarity	NPC56233
0.6581	Remote Similarity	NPC260041
0.6571	Remote Similarity	NPC114974
0.657	Remote Similarity	NPC282103
0.657	Remote Similarity	NPC241025
0.6566	Remote Similarity	NPC262338
0.6564	Remote Similarity	NPC478182
0.6556	Remote Similarity	NPC314102
0.6556	Remote Similarity	NPC251722
0.6554	Remote Similarity	NPC174421
0.6554	Remote Similarity	NPC471322
0.6554	Remote Similarity	NPC82295
0.6552	Remote Similarity	NPC209917
0.6552	Remote Similarity	NPC135488
0.6548	Remote Similarity	NPC476419
0.6529	Remote Similarity	NPC471997
0.6514	Remote Similarity	NPC154339
0.6513	Remote Similarity	NPC169433
0.6513	Remote Similarity	NPC104049
0.65	Remote Similarity	NPC477045
0.65	Remote Similarity	NPC75135
0.6497	Remote Similarity	NPC477974
0.6488	Remote Similarity	NPC139763
0.6485	Remote Similarity	NPC478183
0.6484	Remote Similarity	NPC472063
0.6484	Remote Similarity	NPC328596
0.6484	Remote Similarity	NPC328318
0.6484	Remote Similarity	NPC472069
0.6484	Remote Similarity	NPC472062
0.648	Remote Similarity	NPC167710
0.6477	Remote Similarity	NPC476460
0.6471	Remote Similarity	NPC315348
0.6471	Remote Similarity	NPC316811
0.6471	Remote Similarity	NPC32002
0.6463	Remote Similarity	NPC478184

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 NPC313823 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	356
0.1-0.2	1133
0.2-0.3	1182
0.3-0.4	2596
0.4-0.5	2402
0.5-0.6	1208
0.6-0.7	238
0.7-0.8	32
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8264	Intermediate Similarity	NPD180	Clinical (unspecified phase)
0.8115	Intermediate Similarity	NPD9098	Phase 3
0.8115	Intermediate Similarity	NPD9099	Clinical (unspecified phase)
0.8069	Intermediate Similarity	NPD9343	Clinical (unspecified phase)
0.7714	Intermediate Similarity	NPD272	Approved
0.7698	Intermediate Similarity	NPD9100	Approved
0.7571	Intermediate Similarity	NPD1627	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD9392	Approved
0.75	Intermediate Similarity	NPD9396	Approved
0.7448	Intermediate Similarity	NPD107	Approved
0.7448	Intermediate Similarity	NPD9599	Approved
0.7383	Intermediate Similarity	NPD1270	Approved
0.7365	Intermediate Similarity	NPD175	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD1783	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD9271	Approved
0.7261	Intermediate Similarity	NPD1568	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD569	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD4804	Approved
0.7252	Intermediate Similarity	NPD4824	Approved
0.7252	Intermediate Similarity	NPD4823	Approved
0.7248	Intermediate Similarity	NPD9074	Approved
0.7248	Intermediate Similarity	NPD9075	Approved
0.7241	Intermediate Similarity	NPD200	Phase 2
0.7241	Intermediate Similarity	NPD201	Phase 2
0.7237	Intermediate Similarity	NPD5965	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD1096	Discontinued
0.717	Intermediate Similarity	NPD1292	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD1031	Discontinued
0.7162	Intermediate Similarity	NPD4805	Approved
0.7134	Intermediate Similarity	NPD5400	Approved
0.7122	Intermediate Similarity	NPD9357	Approved
0.709	Intermediate Similarity	NPD60	Approved
0.7075	Intermediate Similarity	NPD2896	Discontinued
0.7075	Intermediate Similarity	NPD9076	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD1343	Approved
0.7051	Intermediate Similarity	NPD820	Phase 3
0.7042	Intermediate Similarity	NPD1095	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD9583	Approved
0.6985	Remote Similarity	NPD8840	Approved
0.6972	Remote Similarity	NPD2118	Approved
0.6972	Remote Similarity	NPD992	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD2119	Approved
0.6972	Remote Similarity	NPD991	Phase 2
0.6963	Remote Similarity	NPD269	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD3238	Discontinued
0.6946	Remote Similarity	NPD7401	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD2061	Approved
0.6909	Remote Similarity	NPD2753	Discontinued
0.6906	Remote Similarity	NPD270	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD268	Approved
0.6906	Remote Similarity	NPD9598	Discontinued
0.6906	Remote Similarity	NPD271	Approved
0.6875	Remote Similarity	NPD9305	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD751	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD7913	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD3475	Approved
0.6828	Remote Similarity	NPD3476	Approved
0.6828	Remote Similarity	NPD715	Phase 3
0.6826	Remote Similarity	NPD3927	Phase 2
0.6826	Remote Similarity	NPD1291	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD2809	Approved
0.6792	Remote Similarity	NPD1630	Approved
0.679	Remote Similarity	NPD6446	Discontinued
0.6788	Remote Similarity	NPD4883	Approved
0.6786	Remote Similarity	NPD4011	Clinical (unspecified phase)
0.6781	Remote Similarity	NPD9726	Discontinued
0.6736	Remote Similarity	NPD9080	Approved
0.6736	Remote Similarity	NPD9284	Approved
0.6733	Remote Similarity	NPD203	Clinical (unspecified phase)
0.6712	Remote Similarity	NPD9207	Approved
0.6712	Remote Similarity	NPD9206	Approved
0.6711	Remote Similarity	NPD206	Clinical (unspecified phase)
0.6706	Remote Similarity	NPD7564	Discontinued
0.6689	Remote Similarity	NPD4029	Approved
0.6689	Remote Similarity	NPD4028	Approved
0.6689	Remote Similarity	NPD3942	Approved
0.6689	Remote Similarity	NPD4030	Approved
0.6689	Remote Similarity	NPD3944	Approved
0.6667	Remote Similarity	NPD5088	Discontinued
0.6667	Remote Similarity	NPD8304	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1631	Approved
0.6667	Remote Similarity	NPD3717	Discontinued
0.6667	Remote Similarity	NPD3583	Phase 2
0.6646	Remote Similarity	NPD6454	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD2511	Approved
0.6645	Remote Similarity	NPD2222	Discontinued
0.6628	Remote Similarity	NPD4426	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD1618	Phase 2
0.6609	Remote Similarity	NPD5686	Approved
0.6609	Remote Similarity	NPD5685	Approved
0.6606	Remote Similarity	NPD1573	Approved
0.6606	Remote Similarity	NPD1575	Approved
0.6604	Remote Similarity	NPD4436	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD460	Discontinued
0.659	Remote Similarity	NPD4988	Discontinued
0.6588	Remote Similarity	NPD3178	Discontinued
0.6587	Remote Similarity	NPD4736	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD4174	Clinical (unspecified phase)
0.6582	Remote Similarity	NPD510	Phase 1
0.6556	Remote Similarity	NPD9506	Approved
0.6554	Remote Similarity	NPD803	Phase 1
0.6548	Remote Similarity	NPD4385	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD7469	Discontinued
0.6536	Remote Similarity	NPD1395	Clinical (unspecified phase)
0.6532	Remote Similarity	NPD5820	Clinical (unspecified phase)
0.6529	Remote Similarity	NPD2479	Phase 3
0.6529	Remote Similarity	NPD2481	Approved
0.6517	Remote Similarity	NPD2290	Phase 3
0.6517	Remote Similarity	NPD2289	Phase 3
0.6513	Remote Similarity	NPD1380	Discovery
0.6512	Remote Similarity	NPD3607	Clinical (unspecified phase)
0.6507	Remote Similarity	NPD1598	Discontinued
0.6503	Remote Similarity	NPD3247	Clinical (unspecified phase)
0.6503	Remote Similarity	NPD6771	Discontinued
0.65	Remote Similarity	NPD2405	Phase 3
0.6497	Remote Similarity	NPD1661	Suspended
0.6497	Remote Similarity	NPD4702	Approved
0.6497	Remote Similarity	NPD4703	Approved
0.6494	Remote Similarity	NPD5020	Approved
0.6485	Remote Similarity	NPD4643	Clinical (unspecified phase)
0.6479	Remote Similarity	NPD4811	Discontinued
0.6471	Remote Similarity	NPD2070	Approved
0.6471	Remote Similarity	NPD2073	Approved
0.6471	Remote Similarity	NPD2075	Approved
0.6471	Remote Similarity	NPD2069	Approved
0.6471	Remote Similarity	NPD2068	Approved
0.6471	Remote Similarity	NPD2074	Approved
0.6471	Remote Similarity	NPD2072	Approved
0.6471	Remote Similarity	NPD174	Discontinued
0.6471	Remote Similarity	NPD2071	Approved
0.6463	Remote Similarity	NPD1545	Discontinued
0.6456	Remote Similarity	NPD1183	Approved
0.6444	Remote Similarity	NPD7204	Clinical (unspecified phase)
0.6443	Remote Similarity	NPD809	Discontinued
0.6441	Remote Similarity	NPD4376	Phase 3
0.6441	Remote Similarity	NPD7098	Clinical (unspecified phase)
0.6433	Remote Similarity	NPD9510	Approved
0.6429	Remote Similarity	NPD5017	Discontinued
0.6429	Remote Similarity	NPD1037	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD4524	Discontinued
0.642	Remote Similarity	NPD1905	Clinical (unspecified phase)
0.642	Remote Similarity	NPD2581	Approved
0.642	Remote Similarity	NPD2582	Approved
0.64	Remote Similarity	NPD2770	Discontinued
0.6395	Remote Similarity	NPD9362	Approved
0.6391	Remote Similarity	NPD1586	Approved
0.6389	Remote Similarity	NPD748	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD5787	Discontinued
0.6387	Remote Similarity	NPD1383	Phase 3
0.6387	Remote Similarity	NPD1382	Phase 2
0.6387	Remote Similarity	NPD1722	Approved
0.6382	Remote Similarity	NPD198	Clinical (unspecified phase)
0.6369	Remote Similarity	NPD7024	Clinical (unspecified phase)
0.6369	Remote Similarity	NPD5975	Clinical (unspecified phase)
0.6353	Remote Similarity	NPD6471	Clinical (unspecified phase)
0.6351	Remote Similarity	NPD5352	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD1427	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD2006	Phase 2
0.6346	Remote Similarity	NPD2007	Clinical (unspecified phase)
0.6335	Remote Similarity	NPD2012	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD1851	Clinical (unspecified phase)
0.6331	Remote Similarity	NPD750	Phase 2
0.6324	Remote Similarity	NPD6288	Clinical (unspecified phase)
0.6323	Remote Similarity	NPD1649	Discontinued
0.6306	Remote Similarity	NPD3813	Approved
0.6306	Remote Similarity	NPD1918	Clinical (unspecified phase)
0.6306	Remote Similarity	NPD1352	Discontinued
0.6303	Remote Similarity	NPD4384	Clinical (unspecified phase)
0.6298	Remote Similarity	NPD5446	Phase 2
0.6296	Remote Similarity	NPD5358	Clinical (unspecified phase)
0.6294	Remote Similarity	NPD482	Approved
0.6292	Remote Similarity	NPD2336	Approved
0.6292	Remote Similarity	NPD6180	Clinical (unspecified phase)
0.6291	Remote Similarity	NPD1995	Approved
0.6291	Remote Similarity	NPD1994	Approved
0.6291	Remote Similarity	NPD1993	Approved
0.6287	Remote Similarity	NPD5611	Phase 2
0.6282	Remote Similarity	NPD461	Approved
0.6279	Remote Similarity	NPD1587	Approved
0.6275	Remote Similarity	NPD792	Discontinued
0.6272	Remote Similarity	NPD485	Clinical (unspecified phase)
0.627	Remote Similarity	NPD5513	Phase 2
0.627	Remote Similarity	NPD2121	Clinical (unspecified phase)
0.6264	Remote Similarity	NPD5728	Clinical (unspecified phase)
0.6258	Remote Similarity	NPD786	Approved
0.6258	Remote Similarity	NPD945	Clinical (unspecified phase)
0.6257	Remote Similarity	NPD749	Clinical (unspecified phase)
0.625	Remote Similarity	NPD3315	Phase 3
0.625	Remote Similarity	NPD5809	Phase 3
0.6243	Remote Similarity	NPD4848	Phase 1
0.623	Remote Similarity	NPD6137	Clinical (unspecified phase)
0.6221	Remote Similarity	NPD5755	Clinical (unspecified phase)
0.6215	Remote Similarity	NPD9364	Phase 2
0.6215	Remote Similarity	NPD9363	Approved
0.6213	Remote Similarity	NPD4973	Approved
0.6209	Remote Similarity	NPD2141	Approved
0.6209	Remote Similarity	NPD2142	Approved
0.6209	Remote Similarity	NPD2140	Approved
0.6203	Remote Similarity	NPD649	Clinical (unspecified phase)
0.6201	Remote Similarity	NPD1658	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