NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	93.06
Volume:	106.863
LogP:	1.125
LogD:	1.099
LogS:	0.82
# Rotatable Bonds:	0
TPSA:	12.89
# H-Bond Aceptor:	1
# H-Bond Donor:	0
# Rings:	1
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.472
Synthetic Accessibility Score:	1.637
Fsp3:	0.167
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:	-4.093
MDCK Permeability:	3.845402898150496e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.016
30% Bioavailability (F30%):	0.004

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.861
Plasma Protein Binding (PPB):	41.74787139892578%
Volume Distribution (VD):	1.374
Pgp-substrate:	61.45299530029297%

ADMET: Metabolism

CYP1A2-inhibitor:	0.875
CYP1A2-substrate:	0.655
CYP2C19-inhibitor:	0.443
CYP2C19-substrate:	0.849
CYP2C9-inhibitor:	0.041
CYP2C9-substrate:	0.484
CYP2D6-inhibitor:	0.104
CYP2D6-substrate:	0.621
CYP3A4-inhibitor:	0.171
CYP3A4-substrate:	0.369

ADMET: Excretion

Clearance (CL):	12.98
Half-life (T1/2):	0.802

ADMET: Toxicity

hERG Blockers:	0.026
Human Hepatotoxicity (H-HT):	0.12
Drug-inuced Liver Injury (DILI):	0.527
AMES Toxicity:	0.015
Rat Oral Acute Toxicity:	0.827
Maximum Recommended Daily Dose:	0.029
Skin Sensitization:	0.919
Carcinogencity:	0.372
Eye Corrosion:	0.979
Eye Irritation:	0.994
Respiratory Toxicity:	0.629

Download Data

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

Natural Product: NPC76540

Natural Product ID:	NPC76540
*Common Name:**	3-Methylpyridine
IUPAC Name:	3-methylpyridine
Synonyms:	3-Picoline
Standard InCHIKey:	ITQTTZVARXURQS-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C6H7N/c1-6-3-2-4-7-5-6/h2-5H,1H3
SMILES:	Cc1cccnc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL15722
PubChem CID:	7970
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000089] Pyridines and derivatives [CHEMONTID:0004152] Methylpyridines

*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

☑ 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
Kd	1
Others	4
Potency	16

Activity Type	# Activity
Individual Protein	7
Organism	2
Others	10
Protein Complex	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT300	Individual Protein	Thromboxane-A synthase	Homo sapiens	Inhibition	=	66.4	%	PMID[453811]
NPT63	Individual Protein	Bromodomain adjacent to zinc finger domain protein 2B	Homo sapiens	Potency	n.a.	707.9	nM	PMID[453813]
NPT135	Individual Protein	Chromobox protein homolog 1	Homo sapiens	Potency	n.a.	79432.8	nM	PMID[453813]
NPT46	Individual Protein	Thyroid hormone receptor beta-1	Homo sapiens	Potency	n.a.	0.7	nM	PMID[453814]
NPT10	Individual Protein	Geminin	Homo sapiens	Potency	n.a.	1458.1	nM	PMID[453813]
NPT2	Others	Unspecified		Potency	n.a.	9926.8	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	34665.4	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	55822.8	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	6164.5	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	21872.4	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	620.6	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	68589.6	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	5448.3	nM	PubChem BioAssay data set
NPT413	Protein Complex	Neuronal acetylcholine receptor	Rattus norvegicus	Kd	=	1800000.0	nM	PMID[453812]
NPT413	Protein Complex	Neuronal acetylcholine receptor	Rattus norvegicus	Inhibition	=	121.0	%	PMID[453812]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	5858.4	nM	PMID[453813]
NPT8	Individual Protein	DNA polymerase iota	Homo sapiens	Potency	n.a.	89125.1	nM	PMID[453813]
NPT99	Individual Protein	Peroxisome proliferator-activated receptor gamma	Homo sapiens	Potency	n.a.	50118.7	nM	PMID[453814]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	827.5	nM	PMID[453813]
NPT35	Others	n.a.		LogP	=	1.2	n.a.	PMID[453815]

☑ 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 NPC76540 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	2773
0.1-0.2	14734
0.2-0.3	16739
0.3-0.4	4209
0.4-0.5	2412
0.5-0.6	1289
0.6-0.7	385
0.7-0.8	115
0.8-0.85	25
0.85-0.9	11
0.9-0.95	3
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9709	High Similarity	NPC27802
0.94	High Similarity	NPC83987
0.9159	High Similarity	NPC235843
0.9048	High Similarity	NPC231655
0.8919	High Similarity	NPC240136
0.8919	High Similarity	NPC297486
0.8919	High Similarity	NPC471402
0.8839	High Similarity	NPC143603
0.8839	High Similarity	NPC91958
0.8772	High Similarity	NPC182570
0.8772	High Similarity	NPC265605
0.8772	High Similarity	NPC48564
0.8621	High Similarity	NPC290094
0.8559	High Similarity	NPC473901
0.8462	Intermediate Similarity	NPC46358
0.8403	Intermediate Similarity	NPC202957
0.8403	Intermediate Similarity	NPC169625
0.839	Intermediate Similarity	NPC27740
0.839	Intermediate Similarity	NPC476322
0.8333	Intermediate Similarity	NPC212125
0.8333	Intermediate Similarity	NPC471311
0.8333	Intermediate Similarity	NPC471313
0.8319	Intermediate Similarity	NPC146373
0.8319	Intermediate Similarity	NPC245244
0.8319	Intermediate Similarity	NPC166424
0.8264	Intermediate Similarity	NPC89490
0.8246	Intermediate Similarity	NPC84268
0.8197	Intermediate Similarity	NPC329896
0.8197	Intermediate Similarity	NPC475105
0.8197	Intermediate Similarity	NPC475090
0.8182	Intermediate Similarity	NPC165370
0.8182	Intermediate Similarity	NPC306397
0.812	Intermediate Similarity	NPC11863
0.8115	Intermediate Similarity	NPC471589
0.8067	Intermediate Similarity	NPC329825
0.8065	Intermediate Similarity	NPC471322
0.8049	Intermediate Similarity	NPC476131
0.7984	Intermediate Similarity	NPC282398
0.7984	Intermediate Similarity	NPC315320
0.7984	Intermediate Similarity	NPC69914
0.7944	Intermediate Similarity	NPC213774
0.792	Intermediate Similarity	NPC256893
0.792	Intermediate Similarity	NPC101165
0.792	Intermediate Similarity	NPC324611
0.7917	Intermediate Similarity	NPC56856
0.7857	Intermediate Similarity	NPC322488
0.7752	Intermediate Similarity	NPC65408
0.7752	Intermediate Similarity	NPC471312
0.7752	Intermediate Similarity	NPC314102
0.7752	Intermediate Similarity	NPC251722
0.7717	Intermediate Similarity	NPC330326
0.7674	Intermediate Similarity	NPC29702
0.7638	Intermediate Similarity	NPC82295
0.7634	Intermediate Similarity	NPC315348
0.7634	Intermediate Similarity	NPC32002
0.7634	Intermediate Similarity	NPC316811
0.7581	Intermediate Similarity	NPC151489
0.7563	Intermediate Similarity	NPC148140
0.7557	Intermediate Similarity	NPC169433
0.7538	Intermediate Similarity	NPC29886
0.7538	Intermediate Similarity	NPC261195
0.752	Intermediate Similarity	NPC135488
0.75	Intermediate Similarity	NPC81561
0.7481	Intermediate Similarity	NPC150259
0.7481	Intermediate Similarity	NPC84911
0.7481	Intermediate Similarity	NPC114310
0.7417	Intermediate Similarity	NPC476566
0.7407	Intermediate Similarity	NPC230085
0.7407	Intermediate Similarity	NPC471323
0.7407	Intermediate Similarity	NPC159630
0.7405	Intermediate Similarity	NPC96102
0.7402	Intermediate Similarity	NPC313823
0.7388	Intermediate Similarity	NPC476454
0.7368	Intermediate Similarity	NPC110126
0.7368	Intermediate Similarity	NPC73767
0.7348	Intermediate Similarity	NPC105127
0.7333	Intermediate Similarity	NPC14223
0.7317	Intermediate Similarity	NPC215519
0.7313	Intermediate Similarity	NPC469780
0.7313	Intermediate Similarity	NPC469784
0.7313	Intermediate Similarity	NPC469761
0.7313	Intermediate Similarity	NPC469767
0.7313	Intermediate Similarity	NPC469768
0.7313	Intermediate Similarity	NPC469779
0.7313	Intermediate Similarity	NPC469783
0.7295	Intermediate Similarity	NPC162689
0.7295	Intermediate Similarity	NPC54102
0.7259	Intermediate Similarity	NPC469766
0.7246	Intermediate Similarity	NPC477974
0.7246	Intermediate Similarity	NPC470111
0.7246	Intermediate Similarity	NPC201380
0.7246	Intermediate Similarity	NPC112741
0.7246	Intermediate Similarity	NPC179787
0.7231	Intermediate Similarity	NPC174421
0.7226	Intermediate Similarity	NPC86288
0.7226	Intermediate Similarity	NPC467188
0.7226	Intermediate Similarity	NPC167400
0.7206	Intermediate Similarity	NPC190296
0.7194	Intermediate Similarity	NPC321911
0.7185	Intermediate Similarity	NPC230002
0.7185	Intermediate Similarity	NPC279081
0.7174	Intermediate Similarity	NPC63545
0.7143	Intermediate Similarity	NPC40070
0.7122	Intermediate Similarity	NPC105811
0.7122	Intermediate Similarity	NPC469811
0.7101	Intermediate Similarity	NPC285731
0.7101	Intermediate Similarity	NPC314372
0.7092	Intermediate Similarity	NPC470233
0.7087	Intermediate Similarity	NPC122718
0.7042	Intermediate Similarity	NPC107287
0.7015	Intermediate Similarity	NPC328029
0.7	Intermediate Similarity	NPC471957
0.6978	Remote Similarity	NPC159856
0.6977	Remote Similarity	NPC476140
0.6972	Remote Similarity	NPC70406
0.6957	Remote Similarity	NPC477977
0.6947	Remote Similarity	NPC71236
0.6944	Remote Similarity	NPC476464
0.694	Remote Similarity	NPC198988
0.6929	Remote Similarity	NPC143872
0.6929	Remote Similarity	NPC316069
0.6929	Remote Similarity	NPC288838
0.6929	Remote Similarity	NPC41174
0.6923	Remote Similarity	NPC312860
0.6923	Remote Similarity	NPC325903
0.6923	Remote Similarity	NPC278451
0.6923	Remote Similarity	NPC138842
0.6901	Remote Similarity	NPC105818
0.6901	Remote Similarity	NPC313889
0.6901	Remote Similarity	NPC53947
0.6901	Remote Similarity	NPC24678
0.6897	Remote Similarity	NPC236711
0.6897	Remote Similarity	NPC129721
0.6897	Remote Similarity	NPC469897
0.6889	Remote Similarity	NPC325252
0.6875	Remote Similarity	NPC263455
0.6875	Remote Similarity	NPC229055
0.6875	Remote Similarity	NPC209362
0.6861	Remote Similarity	NPC104483
0.6853	Remote Similarity	NPC470823
0.6853	Remote Similarity	NPC472260
0.6849	Remote Similarity	NPC477591
0.6849	Remote Similarity	NPC56765
0.6849	Remote Similarity	NPC80681
0.6847	Remote Similarity	NPC196580
0.6835	Remote Similarity	NPC20144
0.6829	Remote Similarity	NPC143156
0.6828	Remote Similarity	NPC74357
0.6812	Remote Similarity	NPC318935
0.6806	Remote Similarity	NPC469763
0.6806	Remote Similarity	NPC469786
0.6806	Remote Similarity	NPC73952
0.6806	Remote Similarity	NPC251391
0.6806	Remote Similarity	NPC469765
0.6806	Remote Similarity	NPC141926
0.6806	Remote Similarity	NPC25008
0.6806	Remote Similarity	NPC259644
0.6806	Remote Similarity	NPC469760
0.6806	Remote Similarity	NPC200214
0.6803	Remote Similarity	NPC215584
0.6803	Remote Similarity	NPC44773
0.6788	Remote Similarity	NPC104049
0.6781	Remote Similarity	NPC138018
0.6767	Remote Similarity	NPC22079
0.6759	Remote Similarity	NPC212376
0.6759	Remote Similarity	NPC211572
0.6759	Remote Similarity	NPC34844
0.6759	Remote Similarity	NPC70922
0.6759	Remote Similarity	NPC75540
0.6759	Remote Similarity	NPC80597
0.6757	Remote Similarity	NPC71079
0.6736	Remote Similarity	NPC216713
0.6735	Remote Similarity	NPC293487
0.6735	Remote Similarity	NPC113812
0.6712	Remote Similarity	NPC51054
0.6711	Remote Similarity	NPC478182
0.6711	Remote Similarity	NPC473057
0.6711	Remote Similarity	NPC474217
0.6711	Remote Similarity	NPC265100
0.6711	Remote Similarity	NPC90723
0.6691	Remote Similarity	NPC59084
0.6691	Remote Similarity	NPC2949
0.6691	Remote Similarity	NPC291517
0.6689	Remote Similarity	NPC470204
0.6689	Remote Similarity	NPC122141
0.6667	Remote Similarity	NPC213914
0.6667	Remote Similarity	NPC477975
0.6667	Remote Similarity	NPC85918
0.6667	Remote Similarity	NPC286427
0.6644	Remote Similarity	NPC124542
0.6644	Remote Similarity	NPC478185
0.6644	Remote Similarity	NPC225018
0.6644	Remote Similarity	NPC59779
0.6644	Remote Similarity	NPC470203
0.6644	Remote Similarity	NPC471177
0.6643	Remote Similarity	NPC473868
0.6643	Remote Similarity	NPC63157
0.6623	Remote Similarity	NPC278366
0.6623	Remote Similarity	NPC127730
0.6623	Remote Similarity	NPC41717

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 NPC76540 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	596
0.1-0.2	1030
0.2-0.3	1178
0.3-0.4	2502
0.4-0.5	2354
0.5-0.6	1102
0.6-0.7	284
0.7-0.8	81
0.8-0.85	15
0.85-0.9	6
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9259	High Similarity	NPD269	Clinical (unspecified phase)
0.9048	High Similarity	NPD9098	Phase 3
0.9048	High Similarity	NPD9099	Clinical (unspecified phase)
0.8772	High Similarity	NPD271	Approved
0.8772	High Similarity	NPD268	Approved
0.8772	High Similarity	NPD270	Clinical (unspecified phase)
0.8636	High Similarity	NPD4824	Approved
0.8636	High Similarity	NPD4823	Approved
0.8547	High Similarity	NPD9357	Approved
0.8403	Intermediate Similarity	NPD9583	Approved
0.8333	Intermediate Similarity	NPD9284	Approved
0.8333	Intermediate Similarity	NPD2119	Approved
0.8333	Intermediate Similarity	NPD2118	Approved
0.8261	Intermediate Similarity	NPD9396	Approved
0.8261	Intermediate Similarity	NPD9392	Approved
0.8246	Intermediate Similarity	NPD60	Approved
0.8182	Intermediate Similarity	NPD991	Phase 2
0.8182	Intermediate Similarity	NPD1598	Discontinued
0.8182	Intermediate Similarity	NPD992	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD9080	Approved
0.813	Intermediate Similarity	NPD3476	Approved
0.813	Intermediate Similarity	NPD715	Phase 3
0.813	Intermediate Similarity	NPD3475	Approved
0.8103	Intermediate Similarity	NPD8840	Approved
0.8067	Intermediate Similarity	NPD748	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD1993	Approved
0.8	Intermediate Similarity	NPD1627	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD1995	Approved
0.8	Intermediate Similarity	NPD1994	Approved
0.7984	Intermediate Similarity	NPD9206	Approved
0.7984	Intermediate Similarity	NPD9207	Approved
0.7937	Intermediate Similarity	NPD4029	Approved
0.7937	Intermediate Similarity	NPD4028	Approved
0.7937	Intermediate Similarity	NPD3944	Approved
0.7937	Intermediate Similarity	NPD3942	Approved
0.7937	Intermediate Similarity	NPD4030	Approved
0.792	Intermediate Similarity	NPD9726	Discontinued
0.7874	Intermediate Similarity	NPD272	Approved
0.7874	Intermediate Similarity	NPD2141	Approved
0.7874	Intermediate Similarity	NPD2142	Approved
0.7874	Intermediate Similarity	NPD2140	Approved
0.7833	Intermediate Similarity	NPD9598	Discontinued
0.7812	Intermediate Similarity	NPD792	Discontinued
0.7812	Intermediate Similarity	NPD206	Clinical (unspecified phase)
0.7752	Intermediate Similarity	NPD200	Phase 2
0.7752	Intermediate Similarity	NPD201	Phase 2
0.7717	Intermediate Similarity	NPD9100	Approved
0.7638	Intermediate Similarity	NPD803	Phase 1
0.7638	Intermediate Similarity	NPD809	Discontinued
0.7634	Intermediate Similarity	NPD2071	Approved
0.7634	Intermediate Similarity	NPD2068	Approved
0.7634	Intermediate Similarity	NPD2069	Approved
0.7634	Intermediate Similarity	NPD2072	Approved
0.7634	Intermediate Similarity	NPD2074	Approved
0.7634	Intermediate Similarity	NPD2070	Approved
0.7634	Intermediate Similarity	NPD2075	Approved
0.7634	Intermediate Similarity	NPD2073	Approved
0.7615	Intermediate Similarity	NPD9506	Approved
0.7576	Intermediate Similarity	NPD1649	Discontinued
0.7557	Intermediate Similarity	NPD203	Clinical (unspecified phase)
0.7557	Intermediate Similarity	NPD1380	Discovery
0.7557	Intermediate Similarity	NPD2896	Discontinued
0.75	Intermediate Similarity	NPD768	Clinical (unspecified phase)
0.7463	Intermediate Similarity	NPD4510	Discontinued
0.7463	Intermediate Similarity	NPD2006	Phase 2
0.7444	Intermediate Similarity	NPD9599	Approved
0.7444	Intermediate Similarity	NPD107	Approved
0.7444	Intermediate Similarity	NPD1395	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD1352	Discontinued
0.7407	Intermediate Similarity	NPD649	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD751	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD1918	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD198	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD490	Clinical (unspecified phase)
0.7402	Intermediate Similarity	NPD1095	Clinical (unspecified phase)
0.7388	Intermediate Similarity	NPD1383	Phase 3
0.7388	Intermediate Similarity	NPD1382	Phase 2
0.7388	Intermediate Similarity	NPD1722	Approved
0.7368	Intermediate Similarity	NPD945	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD786	Approved
0.7353	Intermediate Similarity	NPD175	Clinical (unspecified phase)
0.7344	Intermediate Similarity	NPD9305	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD2007	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD1427	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD6148	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD7469	Discontinued
0.7279	Intermediate Similarity	NPD3813	Approved
0.7246	Intermediate Similarity	NPD4702	Approved
0.7246	Intermediate Similarity	NPD4703	Approved
0.7246	Intermediate Similarity	NPD2110	Approved
0.7246	Intermediate Similarity	NPD1270	Approved
0.7246	Intermediate Similarity	NPD4547	Phase 3
0.7246	Intermediate Similarity	NPD9271	Approved
0.7226	Intermediate Similarity	NPD9074	Approved
0.7226	Intermediate Similarity	NPD9075	Approved
0.7206	Intermediate Similarity	NPD3717	Discontinued
0.7194	Intermediate Similarity	NPD2430	Phase 2
0.7143	Intermediate Similarity	NPD2465	Approved
0.7143	Intermediate Similarity	NPD2462	Phase 3
0.7143	Intermediate Similarity	NPD2466	Phase 3
0.7122	Intermediate Similarity	NPD1661	Suspended
0.7121	Intermediate Similarity	NPD3385	Approved
0.7092	Intermediate Similarity	NPD4641	Discontinued
0.7077	Intermediate Similarity	NPD3654	Approved
0.7071	Intermediate Similarity	NPD1183	Approved
0.7063	Intermediate Similarity	NPD1561	Phase 2
0.7042	Intermediate Similarity	NPD2012	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD1031	Discontinued
0.7	Intermediate Similarity	NPD2089	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD2165	Phase 1
0.6985	Remote Similarity	NPD4804	Approved
0.6985	Remote Similarity	NPD174	Discontinued
0.6972	Remote Similarity	NPD5965	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD3262	Approved
0.695	Remote Similarity	NPD3100	Discontinued
0.6944	Remote Similarity	NPD6026	Approved
0.6944	Remote Similarity	NPD3114	Approved
0.6944	Remote Similarity	NPD3113	Approved
0.6944	Remote Similarity	NPD3115	Approved
0.6944	Remote Similarity	NPD3112	Approved
0.6934	Remote Similarity	NPD2222	Discontinued
0.6929	Remote Similarity	NPD5787	Discontinued
0.6923	Remote Similarity	NPD2837	Discontinued
0.6923	Remote Similarity	NPD3339	Approved
0.6923	Remote Similarity	NPD1917	Discontinued
0.6912	Remote Similarity	NPD9076	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD4811	Discontinued
0.6901	Remote Similarity	NPD2172	Phase 1
0.6897	Remote Similarity	NPD820	Phase 3
0.6897	Remote Similarity	NPD2582	Approved
0.6897	Remote Similarity	NPD2865	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD2581	Approved
0.6897	Remote Similarity	NPD6497	Approved
0.6889	Remote Similarity	NPD1256	Approved
0.6889	Remote Similarity	NPD1253	Approved
0.6889	Remote Similarity	NPD1255	Approved
0.6889	Remote Similarity	NPD1254	Approved
0.6884	Remote Similarity	NPD4805	Approved
0.6875	Remote Similarity	NPD2061	Approved
0.6875	Remote Similarity	NPD977	Approved
0.6875	Remote Similarity	NPD1328	Approved
0.6875	Remote Similarity	NPD975	Approved
0.6875	Remote Similarity	NPD976	Approved
0.6875	Remote Similarity	NPD2809	Approved
0.6849	Remote Similarity	NPD5255	Approved
0.6838	Remote Similarity	NPD6554	Approved
0.6838	Remote Similarity	NPD45	Approved
0.6831	Remote Similarity	NPD4374	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD2748	Clinical (unspecified phase)
0.6812	Remote Similarity	NPD165	Phase 2
0.6803	Remote Similarity	NPD2511	Approved
0.6786	Remote Similarity	NPD1988	Phase 1
0.6781	Remote Similarity	NPD1192	Clinical (unspecified phase)
0.6781	Remote Similarity	NPD5541	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD461	Approved
0.6759	Remote Similarity	NPD5358	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD2385	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD8026	Phase 1
0.6757	Remote Similarity	NPD5315	Discontinued
0.6757	Remote Similarity	NPD4384	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD6771	Discontinued
0.6738	Remote Similarity	NPD1366	Approved
0.6738	Remote Similarity	NPD1364	Approved
0.6738	Remote Similarity	NPD1365	Approved
0.6736	Remote Similarity	NPD510	Phase 1
0.6735	Remote Similarity	NPD704	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD5418	Discontinued
0.6714	Remote Similarity	NPD4637	Clinical (unspecified phase)
0.6712	Remote Similarity	NPD473	Clinical (unspecified phase)
0.6712	Remote Similarity	NPD2580	Discontinued
0.6711	Remote Similarity	NPD3323	Discontinued
0.6711	Remote Similarity	NPD6635	Approved
0.6711	Remote Similarity	NPD3583	Phase 2
0.6711	Remote Similarity	NPD5088	Discontinued
0.6692	Remote Similarity	NPD947	Approved
0.6689	Remote Similarity	NPD112	Approved
0.6689	Remote Similarity	NPD6454	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD9705	Discontinued
0.6667	Remote Similarity	NPD925	Approved
0.6667	Remote Similarity	NPD926	Approved
0.6667	Remote Similarity	NPD2323	Clinical (unspecified phase)
0.6644	Remote Similarity	NPD1853	Clinical (unspecified phase)
0.6644	Remote Similarity	NPD5400	Approved
0.6643	Remote Similarity	NPD5020	Approved
0.6623	Remote Similarity	NPD3929	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD5611	Phase 2
0.6623	Remote Similarity	NPD4174	Clinical (unspecified phase)
0.6621	Remote Similarity	NPD9706	Clinical (unspecified phase)
0.6597	Remote Similarity	NPD2102	Approved
0.6597	Remote Similarity	NPD2104	Approved
0.6593	Remote Similarity	NPD1251	Discontinued
0.6579	Remote Similarity	NPD2640	Approved
0.6579	Remote Similarity	NPD7287	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD1343	Approved
0.6579	Remote Similarity	NPD2390	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD2641	Approved
0.6579	Remote Similarity	NPD6872	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD4779	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD1403	Approved
0.6577	Remote Similarity	NPD1404	Approved

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data