NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	107.04
Volume:	113.017
LogP:	0.267
LogD:	0.42
LogS:	0.366
# 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:	2.027
Fsp3:	0.0
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.216
MDCK Permeability:	2.1058256606920622e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.013
20% Bioavailability (F20%):	0.015
30% Bioavailability (F30%):	0.007

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.798
Plasma Protein Binding (PPB):	39.46261215209961%
Volume Distribution (VD):	1.099
Pgp-substrate:	73.77593231201172%

ADMET: Metabolism

CYP1A2-inhibitor:	0.729
CYP1A2-substrate:	0.496
CYP2C19-inhibitor:	0.076
CYP2C19-substrate:	0.33
CYP2C9-inhibitor:	0.016
CYP2C9-substrate:	0.264
CYP2D6-inhibitor:	0.009
CYP2D6-substrate:	0.283
CYP3A4-inhibitor:	0.027
CYP3A4-substrate:	0.244

ADMET: Excretion

Clearance (CL):	6.798
Half-life (T1/2):	0.746

ADMET: Toxicity

hERG Blockers:	0.039
Human Hepatotoxicity (H-HT):	0.027
Drug-inuced Liver Injury (DILI):	0.513
AMES Toxicity:	0.068
Rat Oral Acute Toxicity:	0.731
Maximum Recommended Daily Dose:	0.035
Skin Sensitization:	0.888
Carcinogencity:	0.102
Eye Corrosion:	0.968
Eye Irritation:	0.995
Respiratory Toxicity:	0.883

Download Data

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

Natural Product: NPC471589

Natural Product ID:	NPC471589
*Common Name:**	Nicotinaldehyde
IUPAC Name:	pyridine-3-carbaldehyde
Synonyms:	Pyridine-3-Carbaldehyde
Standard InCHIKey:	QJZUKDFHGGYHMC-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C6H5NO/c8-5-6-2-1-3-7-4-6/h1-5H
SMILES:	C1=CC(=CN=C1)C=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL268493
PubChem CID:	10371
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	4
Ki	1
MIC	2
Others	6

Activity Type	# Activity
Individual Protein	6
Organism	4
Others	4
Protein Complex	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2933	Individual Protein	Aldehyde oxidase	Oryctolagus cuniculus	Inhibition	=	5.0	%	PMID[485524]
NPT2933	Individual Protein	Aldehyde oxidase	Oryctolagus cuniculus	IC50	=	600000.0	nM	PMID[485524]
NPT43	Individual Protein	Tyrosinase	Agaricus bisporus	IC50	=	28000.0	nM	PMID[485524]
NPT2794	Individual Protein	Quinolone resistance protein norA	Staphylococcus aureus	Activity	>	128.0	ug ml-1	PMID[485526]
NPT805	Protein Complex	GABA-A receptor; anion channel	Rattus norvegicus	Ki	>	100000.0	nM	PMID[485523]
NPT2	Others	Unspecified		Inhibition	=	17.0	%	PMID[485524]
NPT2	Others	Unspecified		IC50	>	1000000.0	nM	PMID[485524]
NPT450	Organism	Meloidogyne incognita	Meloidogyne incognita	EC50	>	10.0	ug.mL-1	PMID[485525]
NPT450	Organism	Meloidogyne incognita	Meloidogyne incognita	EC50	>	250.0	ug.mL-1	PMID[485525]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	128.0	ug.mL-1	PMID[485526]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>=	64.0	ug.mL-1	PMID[485526]
NPT2	Others	Unspecified		IC50	=	54000.0	nM	PMID[485527]
NPT2	Others	Unspecified		Inhibition	=	16.0	%	PMID[485527]
NPT813	Individual Protein	GABA transporter 1	Mus musculus	Activity	=	57.0	%	PMID[485528]
NPT813	Individual Protein	GABA transporter 1	Mus musculus	Activity	=	94.0	%	PMID[485529]

☑ 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 NPC471589 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	1306
0.1-0.2	11909
0.2-0.3	15647
0.3-0.4	8885
0.4-0.5	2614
0.5-0.6	1707
0.6-0.7	527
0.7-0.8	88
0.8-0.85	12
0.85-0.9	1
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8615	High Similarity	NPC313823
0.8417	Intermediate Similarity	NPC230085
0.8417	Intermediate Similarity	NPC159630
0.8369	Intermediate Similarity	NPC112741
0.8357	Intermediate Similarity	NPC167400
0.8264	Intermediate Similarity	NPC107287
0.8227	Intermediate Similarity	NPC467188
0.8222	Intermediate Similarity	NPC330326
0.8207	Intermediate Similarity	NPC263455
0.8134	Intermediate Similarity	NPC71236
0.8115	Intermediate Similarity	NPC76540
0.8112	Intermediate Similarity	NPC105811
0.8082	Intermediate Similarity	NPC209362
0.8014	Intermediate Similarity	NPC312860
0.7986	Intermediate Similarity	NPC114310
0.7973	Intermediate Similarity	NPC213914
0.7945	Intermediate Similarity	NPC70406
0.792	Intermediate Similarity	NPC27802
0.7877	Intermediate Similarity	NPC313889
0.7842	Intermediate Similarity	NPC23215
0.7838	Intermediate Similarity	NPC229055
0.7826	Intermediate Similarity	NPC322488
0.7815	Intermediate Similarity	NPC242116
0.78	Intermediate Similarity	NPC113812
0.7785	Intermediate Similarity	NPC74357
0.777	Intermediate Similarity	NPC251391
0.7769	Intermediate Similarity	NPC83987
0.773	Intermediate Similarity	NPC472288
0.7712	Intermediate Similarity	NPC42372
0.7662	Intermediate Similarity	NPC114637
0.7656	Intermediate Similarity	NPC235843
0.7647	Intermediate Similarity	NPC265100
0.7591	Intermediate Similarity	NPC165370
0.7568	Intermediate Similarity	NPC123906
0.75	Intermediate Similarity	NPC240136
0.75	Intermediate Similarity	NPC471402
0.75	Intermediate Similarity	NPC297486
0.75	Intermediate Similarity	NPC70949
0.7483	Intermediate Similarity	NPC65408
0.7467	Intermediate Similarity	NPC472260
0.7451	Intermediate Similarity	NPC80681
0.7444	Intermediate Similarity	NPC143603
0.7444	Intermediate Similarity	NPC91958
0.7421	Intermediate Similarity	NPC293216
0.7405	Intermediate Similarity	NPC273532
0.7405	Intermediate Similarity	NPC249614
0.7402	Intermediate Similarity	NPC231655
0.7376	Intermediate Similarity	NPC256893
0.7346	Intermediate Similarity	NPC317010
0.7343	Intermediate Similarity	NPC291517
0.7338	Intermediate Similarity	NPC471313
0.7338	Intermediate Similarity	NPC306397
0.7338	Intermediate Similarity	NPC471311
0.7338	Intermediate Similarity	NPC212125
0.7299	Intermediate Similarity	NPC290094
0.7286	Intermediate Similarity	NPC89490
0.7279	Intermediate Similarity	NPC265605
0.7279	Intermediate Similarity	NPC182570
0.7279	Intermediate Similarity	NPC48564
0.7267	Intermediate Similarity	NPC476419
0.7256	Intermediate Similarity	NPC102755
0.7234	Intermediate Similarity	NPC475090
0.7234	Intermediate Similarity	NPC329896
0.7234	Intermediate Similarity	NPC475105
0.72	Intermediate Similarity	NPC302159
0.7195	Intermediate Similarity	NPC470677
0.7183	Intermediate Similarity	NPC315320
0.7174	Intermediate Similarity	NPC46358
0.7172	Intermediate Similarity	NPC29702
0.7143	Intermediate Similarity	NPC169625
0.7143	Intermediate Similarity	NPC202957
0.7134	Intermediate Similarity	NPC73994
0.7133	Intermediate Similarity	NPC324611
0.7124	Intermediate Similarity	NPC217021
0.7124	Intermediate Similarity	NPC470679
0.7122	Intermediate Similarity	NPC27740
0.7122	Intermediate Similarity	NPC476322
0.7117	Intermediate Similarity	NPC83774
0.7108	Intermediate Similarity	NPC110158
0.7107	Intermediate Similarity	NPC41717
0.7099	Intermediate Similarity	NPC469529
0.7071	Intermediate Similarity	NPC245244
0.7071	Intermediate Similarity	NPC146373
0.7071	Intermediate Similarity	NPC166424
0.7068	Intermediate Similarity	NPC473901
0.7059	Intermediate Similarity	NPC473878
0.7044	Intermediate Similarity	NPC233380
0.7039	Intermediate Similarity	NPC100726
0.703	Intermediate Similarity	NPC61011
0.7014	Intermediate Similarity	NPC471322
0.6963	Remote Similarity	NPC84268
0.6948	Remote Similarity	NPC471655
0.6909	Remote Similarity	NPC284775
0.6905	Remote Similarity	NPC46895
0.6899	Remote Similarity	NPC474492
0.6892	Remote Similarity	NPC471312
0.6886	Remote Similarity	NPC191415
0.6884	Remote Similarity	NPC11863
0.6875	Remote Similarity	NPC476131
0.6867	Remote Similarity	NPC164340
0.686	Remote Similarity	NPC114974
0.6857	Remote Similarity	NPC329825
0.6855	Remote Similarity	NPC470680
0.6855	Remote Similarity	NPC100104
0.6855	Remote Similarity	NPC473706
0.6842	Remote Similarity	NPC471323
0.6839	Remote Similarity	NPC135950
0.6831	Remote Similarity	NPC151489
0.6828	Remote Similarity	NPC282398
0.6828	Remote Similarity	NPC69914
0.6826	Remote Similarity	NPC471997
0.6807	Remote Similarity	NPC237188
0.6805	Remote Similarity	NPC207851
0.6805	Remote Similarity	NPC477003
0.6781	Remote Similarity	NPC101165
0.6765	Remote Similarity	NPC282103
0.6738	Remote Similarity	NPC56856
0.6711	Remote Similarity	NPC129412
0.6711	Remote Similarity	NPC58268
0.6711	Remote Similarity	NPC114033
0.6711	Remote Similarity	NPC101130
0.671	Remote Similarity	NPC477974
0.6707	Remote Similarity	NPC157583
0.6705	Remote Similarity	NPC154339
0.6705	Remote Similarity	NPC109922
0.6687	Remote Similarity	NPC293487
0.6685	Remote Similarity	NPC103361
0.6667	Remote Similarity	NPC295158
0.6647	Remote Similarity	NPC44354
0.6628	Remote Similarity	NPC118084
0.6625	Remote Similarity	NPC76982
0.661	Remote Similarity	NPC128244
0.6609	Remote Similarity	NPC469489
0.6605	Remote Similarity	NPC478185
0.6604	Remote Similarity	NPC33229
0.66	Remote Similarity	NPC292434
0.66	Remote Similarity	NPC195704
0.66	Remote Similarity	NPC200397
0.66	Remote Similarity	NPC167200
0.66	Remote Similarity	NPC138596
0.66	Remote Similarity	NPC64661
0.66	Remote Similarity	NPC328029
0.66	Remote Similarity	NPC98156
0.66	Remote Similarity	NPC14448
0.6591	Remote Similarity	NPC326422
0.6591	Remote Similarity	NPC267343
0.659	Remote Similarity	NPC278434
0.6585	Remote Similarity	NPC56233
0.6571	Remote Similarity	NPC138370
0.6571	Remote Similarity	NPC476460
0.6564	Remote Similarity	NPC274981
0.6564	Remote Similarity	NPC478184
0.6564	Remote Similarity	NPC478182
0.6561	Remote Similarity	NPC102664
0.6556	Remote Similarity	NPC314102
0.6556	Remote Similarity	NPC251722
0.6554	Remote Similarity	NPC174421
0.6554	Remote Similarity	NPC82295
0.6552	Remote Similarity	NPC135488
0.655	Remote Similarity	NPC159125
0.655	Remote Similarity	NPC327373
0.6534	Remote Similarity	NPC216550
0.6513	Remote Similarity	NPC169433
0.6512	Remote Similarity	NPC213774
0.6503	Remote Similarity	NPC289086
0.65	Remote Similarity	NPC81535
0.6497	Remote Similarity	NPC304203
0.6496	Remote Similarity	NPC57051
0.6485	Remote Similarity	NPC478183
0.648	Remote Similarity	NPC329024
0.648	Remote Similarity	NPC90229
0.6471	Remote Similarity	NPC315348
0.6471	Remote Similarity	NPC316811
0.6471	Remote Similarity	NPC32002
0.6467	Remote Similarity	NPC309498
0.6461	Remote Similarity	NPC202812
0.6453	Remote Similarity	NPC322043
0.6453	Remote Similarity	NPC325093
0.6452	Remote Similarity	NPC190296
0.6446	Remote Similarity	NPC470894
0.6444	Remote Similarity	NPC474916
0.6444	Remote Similarity	NPC317672
0.6444	Remote Similarity	NPC324245
0.6444	Remote Similarity	NPC59033
0.6444	Remote Similarity	NPC320748
0.6433	Remote Similarity	NPC52831
0.6433	Remote Similarity	NPC24864
0.6433	Remote Similarity	NPC477042
0.6433	Remote Similarity	NPC325705
0.6429	Remote Similarity	NPC244087
0.6429	Remote Similarity	NPC302717
0.6429	Remote Similarity	NPC3698
0.6429	Remote Similarity	NPC286529
0.6429	Remote Similarity	NPC209281
0.6429	Remote Similarity	NPC59839
0.6429	Remote Similarity	NPC48171
0.6429	Remote Similarity	NPC205604
0.6429	Remote Similarity	NPC74928
0.6429	Remote Similarity	NPC169308
0.6429	Remote Similarity	NPC77582

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 NPC471589 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	347
0.1-0.2	1025
0.2-0.3	1022
0.3-0.4	2573
0.4-0.5	2673
0.5-0.6	1199
0.6-0.7	269
0.7-0.8	33
0.8-0.85	8
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8931	High Similarity	NPD272	Approved
0.8603	High Similarity	NPD107	Approved
0.8369	Intermediate Similarity	NPD9271	Approved
0.8357	Intermediate Similarity	NPD9075	Approved
0.8357	Intermediate Similarity	NPD175	Clinical (unspecified phase)
0.8357	Intermediate Similarity	NPD9074	Approved
0.8239	Intermediate Similarity	NPD1270	Approved
0.8222	Intermediate Similarity	NPD9100	Approved
0.8095	Intermediate Similarity	NPD820	Phase 3
0.8088	Intermediate Similarity	NPD1627	Clinical (unspecified phase)
0.7817	Intermediate Similarity	NPD9599	Approved
0.7622	Intermediate Similarity	NPD569	Clinical (unspecified phase)
0.7615	Intermediate Similarity	NPD269	Clinical (unspecified phase)
0.7584	Intermediate Similarity	NPD5965	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD201	Phase 2
0.7483	Intermediate Similarity	NPD200	Phase 2
0.7431	Intermediate Similarity	NPD2896	Discontinued
0.7415	Intermediate Similarity	NPD751	Clinical (unspecified phase)
0.7402	Intermediate Similarity	NPD9099	Clinical (unspecified phase)
0.7402	Intermediate Similarity	NPD9098	Phase 3
0.7391	Intermediate Similarity	NPD8304	Clinical (unspecified phase)
0.7376	Intermediate Similarity	NPD9726	Discontinued
0.7368	Intermediate Similarity	NPD2061	Approved
0.7338	Intermediate Similarity	NPD9284	Approved
0.7338	Intermediate Similarity	NPD9080	Approved
0.731	Intermediate Similarity	NPD203	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD206	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD268	Approved
0.7279	Intermediate Similarity	NPD270	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD271	Approved
0.7278	Intermediate Similarity	NPD1343	Approved
0.719	Intermediate Similarity	NPD180	Clinical (unspecified phase)
0.7183	Intermediate Similarity	NPD9206	Approved
0.7183	Intermediate Similarity	NPD9207	Approved
0.717	Intermediate Similarity	NPD1292	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD1291	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD9506	Approved
0.7122	Intermediate Similarity	NPD9357	Approved
0.7121	Intermediate Similarity	NPD4823	Approved
0.7121	Intermediate Similarity	NPD4824	Approved
0.7107	Intermediate Similarity	NPD6446	Discontinued
0.7091	Intermediate Similarity	NPD4011	Clinical (unspecified phase)
0.709	Intermediate Similarity	NPD60	Approved
0.7075	Intermediate Similarity	NPD1380	Discovery
0.7032	Intermediate Similarity	NPD2809	Approved
0.703	Intermediate Similarity	NPD2481	Approved
0.703	Intermediate Similarity	NPD1618	Phase 2
0.703	Intermediate Similarity	NPD2479	Phase 3
0.7027	Intermediate Similarity	NPD4804	Approved
0.7025	Intermediate Similarity	NPD5400	Approved
0.7021	Intermediate Similarity	NPD9583	Approved
0.7013	Intermediate Similarity	NPD9343	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD8840	Approved
0.6981	Remote Similarity	NPD5088	Discontinued
0.698	Remote Similarity	NPD1395	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD1598	Discontinued
0.6972	Remote Similarity	NPD2118	Approved
0.6972	Remote Similarity	NPD991	Phase 2
0.6972	Remote Similarity	NPD992	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD2119	Approved
0.6962	Remote Similarity	NPD2511	Approved
0.6951	Remote Similarity	NPD3238	Discontinued
0.6933	Remote Similarity	NPD1383	Phase 3
0.6933	Remote Similarity	NPD1382	Phase 2
0.6933	Remote Similarity	NPD4805	Approved
0.6909	Remote Similarity	NPD2753	Discontinued
0.689	Remote Similarity	NPD4883	Approved
0.6887	Remote Similarity	NPD1427	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD1783	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD4988	Discontinued
0.6882	Remote Similarity	NPD2770	Discontinued
0.6871	Remote Similarity	NPD485	Clinical (unspecified phase)
0.6861	Remote Similarity	NPD9392	Approved
0.6861	Remote Similarity	NPD9396	Approved
0.6832	Remote Similarity	NPD1568	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD3475	Approved
0.6828	Remote Similarity	NPD3476	Approved
0.6828	Remote Similarity	NPD715	Phase 3
0.6821	Remote Similarity	NPD7098	Clinical (unspecified phase)
0.6805	Remote Similarity	NPD1096	Discontinued
0.6795	Remote Similarity	NPD510	Phase 1
0.679	Remote Similarity	NPD4174	Clinical (unspecified phase)
0.677	Remote Similarity	NPD1545	Discontinued
0.6763	Remote Similarity	NPD2336	Approved
0.6755	Remote Similarity	NPD1649	Discontinued
0.675	Remote Similarity	NPD6454	Clinical (unspecified phase)
0.6738	Remote Similarity	NPD748	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD1993	Approved
0.6735	Remote Similarity	NPD1995	Approved
0.6735	Remote Similarity	NPD1994	Approved
0.6726	Remote Similarity	NPD3927	Phase 2
0.6711	Remote Similarity	NPD792	Discontinued
0.6705	Remote Similarity	NPD1905	Clinical (unspecified phase)
0.669	Remote Similarity	NPD1031	Discontinued
0.669	Remote Similarity	NPD1095	Clinical (unspecified phase)
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
0.6686	Remote Similarity	NPD1173	Approved
0.6685	Remote Similarity	NPD7049	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD9598	Discontinued
0.6648	Remote Similarity	NPD5975	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD5855	Phase 3
0.6648	Remote Similarity	NPD5853	Phase 3
0.6644	Remote Similarity	NPD2141	Approved
0.6644	Remote Similarity	NPD2142	Approved
0.6644	Remote Similarity	NPD2140	Approved
0.6623	Remote Similarity	NPD3813	Approved
0.6623	Remote Similarity	NPD1352	Discontinued
0.661	Remote Similarity	NPD1851	Clinical (unspecified phase)
0.661	Remote Similarity	NPD2307	Discontinued
0.6608	Remote Similarity	NPD7564	Discontinued
0.6591	Remote Similarity	NPD460	Discontinued
0.659	Remote Similarity	NPD3246	Discontinued
0.6584	Remote Similarity	NPD1630	Approved
0.6564	Remote Similarity	NPD3583	Phase 2
0.6554	Remote Similarity	NPD803	Phase 1
0.655	Remote Similarity	NPD7401	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD6148	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD7469	Discontinued
0.6536	Remote Similarity	NPD2222	Discontinued
0.6534	Remote Similarity	NPD4376	Phase 3
0.6532	Remote Similarity	NPD4426	Clinical (unspecified phase)
0.6513	Remote Similarity	NPD9076	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD3607	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD5755	Clinical (unspecified phase)
0.6503	Remote Similarity	NPD7396	Approved
0.6503	Remote Similarity	NPD2831	Approved
0.65	Remote Similarity	NPD5854	Approved
0.6497	Remote Similarity	NPD4703	Approved
0.6497	Remote Similarity	NPD1661	Suspended
0.6497	Remote Similarity	NPD4702	Approved
0.6494	Remote Similarity	NPD5020	Approved
0.6488	Remote Similarity	NPD5322	Clinical (unspecified phase)
0.6485	Remote Similarity	NPD5611	Phase 2
0.6485	Remote Similarity	NPD5636	Discontinued
0.6485	Remote Similarity	NPD4643	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD2070	Approved
0.6471	Remote Similarity	NPD768	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD2073	Approved
0.6471	Remote Similarity	NPD2072	Approved
0.6471	Remote Similarity	NPD2069	Approved
0.6471	Remote Similarity	NPD2068	Approved
0.6471	Remote Similarity	NPD2075	Approved
0.6471	Remote Similarity	NPD2074	Approved
0.6471	Remote Similarity	NPD2071	Approved
0.6467	Remote Similarity	NPD7289	Clinical (unspecified phase)
0.6464	Remote Similarity	NPD4491	Clinical (unspecified phase)
0.6463	Remote Similarity	NPD1631	Approved
0.6463	Remote Similarity	NPD6635	Approved
0.646	Remote Similarity	NPD6026	Approved
0.6456	Remote Similarity	NPD1183	Approved
0.6452	Remote Similarity	NPD3717	Discontinued
0.645	Remote Similarity	NPD6471	Clinical (unspecified phase)
0.6448	Remote Similarity	NPD2121	Clinical (unspecified phase)
0.6443	Remote Similarity	NPD809	Discontinued
0.6437	Remote Similarity	NPD5820	Clinical (unspecified phase)
0.6433	Remote Similarity	NPD9510	Approved
0.6432	Remote Similarity	NPD3371	Approved
0.6429	Remote Similarity	NPD4524	Discontinued
0.6425	Remote Similarity	NPD6226	Phase 3
0.6425	Remote Similarity	NPD2290	Phase 3
0.6425	Remote Similarity	NPD4848	Phase 1
0.6425	Remote Similarity	NPD2289	Phase 3
0.642	Remote Similarity	NPD2581	Approved
0.642	Remote Similarity	NPD2582	Approved
0.6416	Remote Similarity	NPD721	Approved
0.6407	Remote Similarity	NPD1573	Approved
0.6407	Remote Similarity	NPD1575	Approved
0.6398	Remote Similarity	NPD5358	Clinical (unspecified phase)
0.6395	Remote Similarity	NPD9362	Approved
0.6387	Remote Similarity	NPD1722	Approved
0.6382	Remote Similarity	NPD198	Clinical (unspecified phase)
0.6382	Remote Similarity	NPD490	Clinical (unspecified phase)
0.6375	Remote Similarity	NPD3262	Approved
0.6374	Remote Similarity	NPD5228	Phase 3
0.6364	Remote Similarity	NPD945	Clinical (unspecified phase)
0.6348	Remote Similarity	NPD981	Phase 2
0.6348	Remote Similarity	NPD4922	Phase 2
0.6346	Remote Similarity	NPD4510	Discontinued
0.6346	Remote Similarity	NPD2006	Phase 2
0.6346	Remote Similarity	NPD2007	Clinical (unspecified phase)
0.6335	Remote Similarity	NPD2012	Clinical (unspecified phase)
0.6328	Remote Similarity	NPD5686	Approved
0.6328	Remote Similarity	NPD5685	Approved
0.6324	Remote Similarity	NPD944	Approved
0.6324	Remote Similarity	NPD3947	Discontinued
0.6324	Remote Similarity	NPD4299	Phase 1
0.6322	Remote Similarity	NPD3569	Discontinued
0.6319	Remote Similarity	NPD2548	Clinical (unspecified phase)
0.6312	Remote Similarity	NPD7913	Clinical (unspecified phase)
0.631	Remote Similarity	NPD2509	Approved
0.631	Remote Similarity	NPD2510	Approved
0.6309	Remote Similarity	NPD9305	Clinical (unspecified phase)
0.6306	Remote Similarity	NPD649	Clinical (unspecified phase)
0.6306	Remote Similarity	NPD1918	Clinical (unspecified phase)
0.6303	Remote Similarity	NPD4384	Clinical (unspecified phase)
0.6303	Remote Similarity	NPD6771	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