NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	104.04
Volume:	112.587
LogP:	0.418
LogD:	0.665
LogS:	-0.18
# Rotatable Bonds:	0
TPSA:	36.68
# H-Bond Aceptor:	2
# H-Bond Donor:	0
# Rings:	1
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.491
Synthetic Accessibility Score:	1.987
Fsp3:	0.0
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.076
MDCK Permeability:	3.1004623451735824e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.284
Plasma Protein Binding (PPB):	24.442241668701172%
Volume Distribution (VD):	1.723
Pgp-substrate:	69.68392181396484%

ADMET: Metabolism

CYP1A2-inhibitor:	0.894
CYP1A2-substrate:	0.557
CYP2C19-inhibitor:	0.46
CYP2C19-substrate:	0.104
CYP2C9-inhibitor:	0.08
CYP2C9-substrate:	0.138
CYP2D6-inhibitor:	0.309
CYP2D6-substrate:	0.351
CYP3A4-inhibitor:	0.164
CYP3A4-substrate:	0.288

ADMET: Excretion

Clearance (CL):	7.746
Half-life (T1/2):	0.791

ADMET: Toxicity

hERG Blockers:	0.083
Human Hepatotoxicity (H-HT):	0.879
Drug-inuced Liver Injury (DILI):	0.867
AMES Toxicity:	0.179
Rat Oral Acute Toxicity:	0.738
Maximum Recommended Daily Dose:	0.061
Skin Sensitization:	0.928
Carcinogencity:	0.355
Eye Corrosion:	0.919
Eye Irritation:	0.995
Respiratory Toxicity:	0.753

Download Data

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

Natural Product: NPC235843

Natural Product ID:	NPC235843
*Common Name:**	Isonicotinonitrile
IUPAC Name:	pyridine-4-carbonitrile
Synonyms:	Isonicotinonitrile
Standard InCHIKey:	GPHQHTOMRSGBNZ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C6H4N2/c7-5-6-1-3-8-4-2-6/h1-4H
SMILES:	N#Cc1ccncc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL504918
PubChem CID:	7506
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000089] Pyridines and derivatives

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1402962]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	Flower Buds	n.a.	n.a.	PMID[26977531]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8904847]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	Stem	n.a.	n.a.	Database[FooDB]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	Bark	n.a.	n.a.	Database[FooDB]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	Essential Oil	n.a.	n.a.	Database[FooDB]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	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	15
Potency	6

Activity Type	# Activity
Organism	7
Others	14

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT35	Others	n.a.		LogP	=	0.46	n.a.	PMID[484407]
NPT35	Others	n.a.		LogP	=	-0.59	n.a.	PMID[484407]
NPT352	Organism	Frankliniella occidentalis	Frankliniella occidentalis	Activity	=	39.0	%	PMID[484408]
NPT1280	Organism	Thrips tabaci	Thrips tabaci	Ratio	=	2.4	n.a.	PMID[484409]
NPT1281	Organism	Thrips obscuratus	Thrips obscuratus	Ratio	=	19.9	n.a.	PMID[484409]
NPT1281	Organism	Thrips obscuratus	Thrips obscuratus	Ratio	=	0.0	n.a.	PMID[484409]
NPT35	Others	n.a.		K	=	0.8837	n.a.	PMID[484410]
NPT35	Others	n.a.		T1/2	=	0.8	hr	PMID[484410]
NPT35	Others	n.a.		T1/2	>	1.0	hr	PMID[484410]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	Inhibition	=	16.06	%	PMID[484411]
NPT747	Organism	Acinetobacter baumannii	Acinetobacter baumannii	Inhibition	=	7.54	%	PMID[484411]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	Inhibition	=	18.89	%	PMID[484411]
NPT2	Others	Unspecified		Percent Effect	=	1.974	%	PMID[484412]
NPT2	Others	Unspecified		Percent Effect	=	0.0775	%	PMID[484412]
NPT2	Others	Unspecified		Percent Effect	=	12.05	%	PMID[484412]
NPT2	Others	Unspecified		Potency	n.a.	157.8	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	78407.9	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	87975.1	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	70477.2	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	28057.5	nM	PubChem BioAssay data set

☑ 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 NPC235843 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	3193
0.1-0.2	15125
0.2-0.3	16554
0.3-0.4	4003
0.4-0.5	2362
0.5-0.6	1078
0.6-0.7	286
0.7-0.8	79
0.8-0.85	13
0.85-0.9	2
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9159	High Similarity	NPC76540
0.9083	High Similarity	NPC27802
0.8952	High Similarity	NPC83987
0.8534	High Similarity	NPC471402
0.8534	High Similarity	NPC297486
0.8534	High Similarity	NPC240136
0.8468	Intermediate Similarity	NPC231655
0.8462	Intermediate Similarity	NPC91958
0.8462	Intermediate Similarity	NPC143603
0.8403	Intermediate Similarity	NPC265605
0.8403	Intermediate Similarity	NPC182570
0.8403	Intermediate Similarity	NPC48564
0.8264	Intermediate Similarity	NPC290094
0.8197	Intermediate Similarity	NPC476322
0.8197	Intermediate Similarity	NPC27740
0.813	Intermediate Similarity	NPC245244
0.813	Intermediate Similarity	NPC146373
0.813	Intermediate Similarity	NPC166424
0.8115	Intermediate Similarity	NPC46358
0.8065	Intermediate Similarity	NPC169625
0.8065	Intermediate Similarity	NPC202957
0.8051	Intermediate Similarity	NPC84268
0.8034	Intermediate Similarity	NPC473901
0.7937	Intermediate Similarity	NPC89490
0.7886	Intermediate Similarity	NPC329825
0.7874	Intermediate Similarity	NPC329896
0.7874	Intermediate Similarity	NPC476131
0.7874	Intermediate Similarity	NPC475090
0.7874	Intermediate Similarity	NPC475105
0.7857	Intermediate Similarity	NPC471311
0.7857	Intermediate Similarity	NPC306397
0.7857	Intermediate Similarity	NPC212125
0.7857	Intermediate Similarity	NPC471313
0.7812	Intermediate Similarity	NPC69914
0.7812	Intermediate Similarity	NPC282398
0.7752	Intermediate Similarity	NPC101165
0.7752	Intermediate Similarity	NPC324611
0.7727	Intermediate Similarity	NPC150259
0.7717	Intermediate Similarity	NPC165370
0.7692	Intermediate Similarity	NPC330326
0.7687	Intermediate Similarity	NPC230002
0.7674	Intermediate Similarity	NPC315320
0.7656	Intermediate Similarity	NPC471589
0.7642	Intermediate Similarity	NPC11863
0.7615	Intermediate Similarity	NPC256893
0.7615	Intermediate Similarity	NPC471322
0.7557	Intermediate Similarity	NPC322488
0.7556	Intermediate Similarity	NPC279081
0.7463	Intermediate Similarity	NPC65408
0.7463	Intermediate Similarity	NPC251722
0.7463	Intermediate Similarity	NPC314102
0.746	Intermediate Similarity	NPC56856
0.7434	Intermediate Similarity	NPC213774
0.7388	Intermediate Similarity	NPC29702
0.7364	Intermediate Similarity	NPC135488
0.7353	Intermediate Similarity	NPC315348
0.7353	Intermediate Similarity	NPC316811
0.7353	Intermediate Similarity	NPC32002
0.7348	Intermediate Similarity	NPC82295
0.7333	Intermediate Similarity	NPC114310
0.7333	Intermediate Similarity	NPC471312
0.7287	Intermediate Similarity	NPC151489
0.7279	Intermediate Similarity	NPC169433
0.7259	Intermediate Similarity	NPC96102
0.7246	Intermediate Similarity	NPC476454
0.7206	Intermediate Similarity	NPC84911
0.7206	Intermediate Similarity	NPC105127
0.7132	Intermediate Similarity	NPC29886
0.7132	Intermediate Similarity	NPC261195
0.7121	Intermediate Similarity	NPC313823
0.712	Intermediate Similarity	NPC148140
0.7101	Intermediate Similarity	NPC73767
0.7101	Intermediate Similarity	NPC110126
0.7092	Intermediate Similarity	NPC86288
0.7063	Intermediate Similarity	NPC81561
0.705	Intermediate Similarity	NPC469761
0.705	Intermediate Similarity	NPC469784
0.705	Intermediate Similarity	NPC469767
0.705	Intermediate Similarity	NPC469779
0.705	Intermediate Similarity	NPC469768
0.705	Intermediate Similarity	NPC469780
0.705	Intermediate Similarity	NPC469783
0.7042	Intermediate Similarity	NPC63545
0.7021	Intermediate Similarity	NPC471323
0.7008	Intermediate Similarity	NPC162689
0.7008	Intermediate Similarity	NPC54102
0.7	Intermediate Similarity	NPC469766
0.6993	Remote Similarity	NPC201380
0.6993	Remote Similarity	NPC179787
0.6993	Remote Similarity	NPC470111
0.6993	Remote Similarity	NPC469811
0.6984	Remote Similarity	NPC476566
0.6972	Remote Similarity	NPC467188
0.6963	Remote Similarity	NPC174421
0.695	Remote Similarity	NPC190296
0.6944	Remote Similarity	NPC321911
0.6901	Remote Similarity	NPC230085
0.6901	Remote Similarity	NPC159630
0.6899	Remote Similarity	NPC215519
0.6897	Remote Similarity	NPC40070
0.6884	Remote Similarity	NPC328029
0.6875	Remote Similarity	NPC477974
0.6875	Remote Similarity	NPC105811
0.6853	Remote Similarity	NPC285731
0.6853	Remote Similarity	NPC314372
0.6853	Remote Similarity	NPC159856
0.6853	Remote Similarity	NPC167400
0.6849	Remote Similarity	NPC470233
0.6847	Remote Similarity	NPC14223
0.6806	Remote Similarity	NPC143872
0.6806	Remote Similarity	NPC288838
0.6803	Remote Similarity	NPC138842
0.6803	Remote Similarity	NPC325903
0.6759	Remote Similarity	NPC112741
0.6759	Remote Similarity	NPC471957
0.6735	Remote Similarity	NPC472260
0.6735	Remote Similarity	NPC70406
0.6711	Remote Similarity	NPC476464
0.6693	Remote Similarity	NPC143156
0.6692	Remote Similarity	NPC122718
0.6691	Remote Similarity	NPC198988
0.669	Remote Similarity	NPC316069
0.6667	Remote Similarity	NPC53947
0.6667	Remote Similarity	NPC469897
0.6667	Remote Similarity	NPC105818
0.6667	Remote Similarity	NPC236711
0.6667	Remote Similarity	NPC129721
0.6667	Remote Similarity	NPC24678
0.6667	Remote Similarity	NPC313889
0.6644	Remote Similarity	NPC229055
0.6644	Remote Similarity	NPC209362
0.6643	Remote Similarity	NPC325252
0.6623	Remote Similarity	NPC293487
0.6623	Remote Similarity	NPC477591
0.6623	Remote Similarity	NPC56765
0.6622	Remote Similarity	NPC470823
0.6622	Remote Similarity	NPC216713
0.662	Remote Similarity	NPC104483
0.66	Remote Similarity	NPC74357
0.6597	Remote Similarity	NPC20144
0.6597	Remote Similarity	NPC477977
0.6593	Remote Similarity	NPC476140
0.6579	Remote Similarity	NPC122141
0.6579	Remote Similarity	NPC44773
0.6579	Remote Similarity	NPC215584
0.6579	Remote Similarity	NPC470204
0.6577	Remote Similarity	NPC469760
0.6577	Remote Similarity	NPC469765
0.6577	Remote Similarity	NPC107287
0.6577	Remote Similarity	NPC25008
0.6577	Remote Similarity	NPC73952
0.6577	Remote Similarity	NPC251391
0.6577	Remote Similarity	NPC469763
0.6577	Remote Similarity	NPC259644
0.6577	Remote Similarity	NPC312860
0.6577	Remote Similarity	NPC141926
0.6577	Remote Similarity	NPC469786
0.6577	Remote Similarity	NPC200214
0.6573	Remote Similarity	NPC318935
0.6569	Remote Similarity	NPC71236
0.6556	Remote Similarity	NPC138018
0.6556	Remote Similarity	NPC286427
0.6556	Remote Similarity	NPC213914
0.6552	Remote Similarity	NPC196580
0.6549	Remote Similarity	NPC104049
0.6544	Remote Similarity	NPC278451
0.6541	Remote Similarity	NPC41174
0.6536	Remote Similarity	NPC71079
0.6536	Remote Similarity	NPC470203
0.6536	Remote Similarity	NPC59779
0.6536	Remote Similarity	NPC478185
0.6536	Remote Similarity	NPC225018
0.6536	Remote Similarity	NPC124542
0.6536	Remote Similarity	NPC471177
0.6533	Remote Similarity	NPC263455
0.6533	Remote Similarity	NPC34844
0.6533	Remote Similarity	NPC212376
0.6533	Remote Similarity	NPC75540
0.6533	Remote Similarity	NPC211572
0.6533	Remote Similarity	NPC80597
0.6533	Remote Similarity	NPC70922
0.6522	Remote Similarity	NPC22079
0.6513	Remote Similarity	NPC41257
0.6513	Remote Similarity	NPC80681
0.6503	Remote Similarity	NPC88097
0.6494	Remote Similarity	NPC478184
0.6494	Remote Similarity	NPC317105
0.6494	Remote Similarity	NPC97367
0.6494	Remote Similarity	NPC474217
0.6494	Remote Similarity	NPC478182
0.6494	Remote Similarity	NPC90723
0.649	Remote Similarity	NPC51054
0.649	Remote Similarity	NPC469785
0.6479	Remote Similarity	NPC125746
0.6458	Remote Similarity	NPC59084
0.6458	Remote Similarity	NPC2949
0.6452	Remote Similarity	NPC471178
0.6452	Remote Similarity	NPC274229
0.6452	Remote Similarity	NPC85918
0.6447	Remote Similarity	NPC469762

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 NPC235843 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	598
0.1-0.2	1059
0.2-0.3	1289
0.3-0.4	2635
0.4-0.5	2343
0.5-0.6	934
0.6-0.7	222
0.7-0.8	62
0.8-0.85	7
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8684	High Similarity	NPD269	Clinical (unspecified phase)
0.8468	Intermediate Similarity	NPD9098	Phase 3
0.8468	Intermediate Similarity	NPD9099	Clinical (unspecified phase)
0.8403	Intermediate Similarity	NPD270	Clinical (unspecified phase)
0.8403	Intermediate Similarity	NPD268	Approved
0.8403	Intermediate Similarity	NPD271	Approved
0.8197	Intermediate Similarity	NPD9357	Approved
0.8145	Intermediate Similarity	NPD1598	Discontinued
0.8103	Intermediate Similarity	NPD4823	Approved
0.8103	Intermediate Similarity	NPD4824	Approved
0.8065	Intermediate Similarity	NPD9583	Approved
0.8	Intermediate Similarity	NPD2118	Approved
0.8	Intermediate Similarity	NPD992	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD991	Phase 2
0.8	Intermediate Similarity	NPD2119	Approved
0.7917	Intermediate Similarity	NPD9396	Approved
0.7917	Intermediate Similarity	NPD9392	Approved
0.7899	Intermediate Similarity	NPD60	Approved
0.7857	Intermediate Similarity	NPD9284	Approved
0.7857	Intermediate Similarity	NPD9080	Approved
0.7812	Intermediate Similarity	NPD3476	Approved
0.7812	Intermediate Similarity	NPD3475	Approved
0.7786	Intermediate Similarity	NPD490	Clinical (unspecified phase)
0.7769	Intermediate Similarity	NPD8840	Approved
0.7752	Intermediate Similarity	NPD9726	Discontinued
0.7742	Intermediate Similarity	NPD748	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD1993	Approved
0.7692	Intermediate Similarity	NPD1994	Approved
0.7692	Intermediate Similarity	NPD1995	Approved
0.7692	Intermediate Similarity	NPD9100	Approved
0.7674	Intermediate Similarity	NPD9207	Approved
0.7674	Intermediate Similarity	NPD9206	Approved
0.7674	Intermediate Similarity	NPD715	Phase 3
0.7661	Intermediate Similarity	NPD9598	Discontinued
0.7634	Intermediate Similarity	NPD3944	Approved
0.7634	Intermediate Similarity	NPD3942	Approved
0.7634	Intermediate Similarity	NPD4030	Approved
0.7634	Intermediate Similarity	NPD4029	Approved
0.7634	Intermediate Similarity	NPD4028	Approved
0.7576	Intermediate Similarity	NPD2142	Approved
0.7576	Intermediate Similarity	NPD2141	Approved
0.7576	Intermediate Similarity	NPD2140	Approved
0.7557	Intermediate Similarity	NPD1627	Clinical (unspecified phase)
0.7519	Intermediate Similarity	NPD792	Discontinued
0.7481	Intermediate Similarity	NPD809	Discontinued
0.7481	Intermediate Similarity	NPD803	Phase 1
0.7463	Intermediate Similarity	NPD200	Phase 2
0.7463	Intermediate Similarity	NPD201	Phase 2
0.7444	Intermediate Similarity	NPD272	Approved
0.7388	Intermediate Similarity	NPD206	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD2071	Approved
0.7353	Intermediate Similarity	NPD2072	Approved
0.7353	Intermediate Similarity	NPD2075	Approved
0.7353	Intermediate Similarity	NPD2073	Approved
0.7353	Intermediate Similarity	NPD2068	Approved
0.7353	Intermediate Similarity	NPD2069	Approved
0.7353	Intermediate Similarity	NPD945	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD2070	Approved
0.7353	Intermediate Similarity	NPD2074	Approved
0.7353	Intermediate Similarity	NPD768	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD9506	Approved
0.7299	Intermediate Similarity	NPD9599	Approved
0.7279	Intermediate Similarity	NPD203	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD1380	Discovery
0.7279	Intermediate Similarity	NPD2896	Discontinued
0.7259	Intermediate Similarity	NPD198	Clinical (unspecified phase)
0.7252	Intermediate Similarity	NPD1095	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD1722	Approved
0.7197	Intermediate Similarity	NPD9305	Clinical (unspecified phase)
0.7194	Intermediate Similarity	NPD2007	Clinical (unspecified phase)
0.7194	Intermediate Similarity	NPD4510	Discontinued
0.7194	Intermediate Similarity	NPD2006	Phase 2
0.7174	Intermediate Similarity	NPD1649	Discontinued
0.7174	Intermediate Similarity	NPD1395	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3813	Approved
0.7143	Intermediate Similarity	NPD751	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1918	Clinical (unspecified phase)
0.7122	Intermediate Similarity	NPD1383	Phase 3
0.7122	Intermediate Similarity	NPD1382	Phase 2
0.7101	Intermediate Similarity	NPD786	Approved
0.7095	Intermediate Similarity	NPD5400	Approved
0.7071	Intermediate Similarity	NPD1427	Clinical (unspecified phase)
0.705	Intermediate Similarity	NPD107	Approved
0.7042	Intermediate Similarity	NPD7469	Discontinued
0.7042	Intermediate Similarity	NPD6148	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD649	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD1352	Discontinued
0.7	Intermediate Similarity	NPD925	Approved
0.7	Intermediate Similarity	NPD926	Approved
0.6993	Remote Similarity	NPD4547	Phase 3
0.6993	Remote Similarity	NPD4703	Approved
0.6993	Remote Similarity	NPD4702	Approved
0.6993	Remote Similarity	NPD2110	Approved
0.6993	Remote Similarity	NPD1270	Approved
0.6993	Remote Similarity	NPD1661	Suspended
0.698	Remote Similarity	NPD6771	Discontinued
0.6972	Remote Similarity	NPD175	Clinical (unspecified phase)
0.695	Remote Similarity	NPD3717	Discontinued
0.6944	Remote Similarity	NPD2430	Phase 2
0.6944	Remote Similarity	NPD1183	Approved
0.6906	Remote Similarity	NPD2323	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD2465	Approved
0.6897	Remote Similarity	NPD2462	Phase 3
0.6897	Remote Similarity	NPD2466	Phase 3
0.6861	Remote Similarity	NPD3385	Approved
0.6853	Remote Similarity	NPD9074	Approved
0.6853	Remote Similarity	NPD9075	Approved
0.6849	Remote Similarity	NPD3262	Approved
0.6849	Remote Similarity	NPD4641	Discontinued
0.6849	Remote Similarity	NPD5965	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD1257	Approved
0.6815	Remote Similarity	NPD3654	Approved
0.6803	Remote Similarity	NPD3339	Approved
0.6803	Remote Similarity	NPD1917	Discontinued
0.6803	Remote Similarity	NPD2837	Discontinued
0.6803	Remote Similarity	NPD2012	Clinical (unspecified phase)
0.6794	Remote Similarity	NPD1561	Phase 2
0.6769	Remote Similarity	NPD4811	Discontinued
0.6759	Remote Similarity	NPD2089	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD9271	Approved
0.6757	Remote Similarity	NPD2809	Approved
0.6757	Remote Similarity	NPD975	Approved
0.6757	Remote Similarity	NPD1328	Approved
0.6757	Remote Similarity	NPD2165	Phase 1
0.6757	Remote Similarity	NPD976	Approved
0.6757	Remote Similarity	NPD977	Approved
0.6757	Remote Similarity	NPD2061	Approved
0.6741	Remote Similarity	NPD1031	Discontinued
0.6738	Remote Similarity	NPD4804	Approved
0.6738	Remote Similarity	NPD174	Discontinued
0.6731	Remote Similarity	NPD1923	Clinical (unspecified phase)
0.6712	Remote Similarity	NPD3100	Discontinued
0.6712	Remote Similarity	NPD4374	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD2748	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD3113	Approved
0.6711	Remote Similarity	NPD3114	Approved
0.6711	Remote Similarity	NPD3115	Approved
0.6711	Remote Similarity	NPD3112	Approved
0.669	Remote Similarity	NPD165	Phase 2
0.669	Remote Similarity	NPD2222	Discontinued
0.6667	Remote Similarity	NPD5541	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5787	Discontinued
0.6667	Remote Similarity	NPD2172	Phase 1
0.6667	Remote Similarity	NPD1988	Phase 1
0.6667	Remote Similarity	NPD2581	Approved
0.6667	Remote Similarity	NPD9076	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2582	Approved
0.6667	Remote Similarity	NPD6497	Approved
0.6667	Remote Similarity	NPD2865	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1192	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD2753	Discontinued
0.6643	Remote Similarity	NPD461	Approved
0.6643	Remote Similarity	NPD1256	Approved
0.6643	Remote Similarity	NPD1253	Approved
0.6643	Remote Similarity	NPD4805	Approved
0.6643	Remote Similarity	NPD1254	Approved
0.6643	Remote Similarity	NPD1255	Approved
0.6623	Remote Similarity	NPD5418	Discontinued
0.6623	Remote Similarity	NPD704	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD5255	Approved
0.6604	Remote Similarity	NPD1167	Phase 3
0.66	Remote Similarity	NPD6026	Approved
0.6596	Remote Similarity	NPD45	Approved
0.6596	Remote Similarity	NPD6554	Approved
0.6579	Remote Similarity	NPD6454	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD2511	Approved
0.6569	Remote Similarity	NPD947	Approved
0.6536	Remote Similarity	NPD8026	Phase 1
0.6536	Remote Similarity	NPD1853	Clinical (unspecified phase)
0.6536	Remote Similarity	NPD4384	Clinical (unspecified phase)
0.6536	Remote Similarity	NPD5315	Discontinued
0.6536	Remote Similarity	NPD2385	Clinical (unspecified phase)
0.6533	Remote Similarity	NPD5358	Clinical (unspecified phase)
0.6516	Remote Similarity	NPD5611	Phase 2
0.651	Remote Similarity	NPD510	Phase 1
0.6507	Remote Similarity	NPD1366	Approved
0.6507	Remote Similarity	NPD1364	Approved
0.6507	Remote Similarity	NPD1365	Approved
0.6494	Remote Similarity	NPD3323	Discontinued
0.6494	Remote Similarity	NPD3583	Phase 2
0.649	Remote Similarity	NPD473	Clinical (unspecified phase)
0.649	Remote Similarity	NPD939	Clinical (unspecified phase)
0.649	Remote Similarity	NPD2580	Discontinued
0.6483	Remote Similarity	NPD4637	Clinical (unspecified phase)
0.6475	Remote Similarity	NPD1251	Discontinued
0.6471	Remote Similarity	NPD9705	Discontinued
0.6471	Remote Similarity	NPD112	Approved
0.6452	Remote Similarity	NPD2719	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD2720	Phase 1
0.6447	Remote Similarity	NPD820	Phase 3
0.6442	Remote Similarity	NPD4957	Phase 2
0.6414	Remote Similarity	NPD5020	Approved
0.641	Remote Similarity	NPD6446	Discontinued
0.641	Remote Similarity	NPD3929	Clinical (unspecified phase)
0.641	Remote Similarity	NPD425	Approved
0.641	Remote Similarity	NPD5636	Discontinued
0.641	Remote Similarity	NPD4174	Clinical (unspecified phase)
0.641	Remote Similarity	NPD424	Approved
0.6405	Remote Similarity	NPD3433	Clinical (unspecified phase)
0.6402	Remote Similarity	NPD6241	Phase 1

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