NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	167.06
Volume:	165.189
LogP:	-1.922
LogD:	-2.256
LogS:	0.691
# Rotatable Bonds:	3
TPSA:	64.24
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.547
Synthetic Accessibility Score:	3.402
Fsp3:	0.25
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:	-5.105
MDCK Permeability:	0.00011653344699880108
Pgp-inhibitor:	0.0
Pgp-substrate:	0.984
Human Intestinal Absorption (HIA):	0.893
20% Bioavailability (F20%):	0.731
30% Bioavailability (F30%):	0.96

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.442
Plasma Protein Binding (PPB):	9.398438453674316%
Volume Distribution (VD):	0.697
Pgp-substrate:	94.99454498291016%

ADMET: Metabolism

CYP1A2-inhibitor:	0.02
CYP1A2-substrate:	0.1
CYP2C19-inhibitor:	0.013
CYP2C19-substrate:	0.058
CYP2C9-inhibitor:	0.003
CYP2C9-substrate:	0.061
CYP2D6-inhibitor:	0.015
CYP2D6-substrate:	0.092
CYP3A4-inhibitor:	0.003
CYP3A4-substrate:	0.054

ADMET: Excretion

Clearance (CL):	2.844
Half-life (T1/2):	0.914

ADMET: Toxicity

hERG Blockers:	0.023
Human Hepatotoxicity (H-HT):	0.708
Drug-inuced Liver Injury (DILI):	0.182
AMES Toxicity:	0.02
Rat Oral Acute Toxicity:	0.022
Maximum Recommended Daily Dose:	0.01
Skin Sensitization:	0.391
Carcinogencity:	0.094
Eye Corrosion:	0.008
Eye Irritation:	0.971
Respiratory Toxicity:	0.091

Download Data

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

Natural Product: NPC263455

Natural Product ID:	NPC263455
*Common Name:**	Pyridinebetaine A
IUPAC Name:	1-(2-hydroxyethyl)pyridin-1-ium-3-carboxylate
Synonyms:
Standard InCHIKey:	NMLHUTLOFSMVHP-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C8H9NO3/c10-5-4-9-3-1-2-7(6-9)8(11)12/h1-3,6,10H,4-5H2
SMILES:	c1cc(c[n+](c1)CCO)C(=O)[O-]
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL447147
PubChem CID:	104238
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids 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
NPO27799	Agelas dispar	Species	Agelasidae	Eukaryota	n.a.	n.a.	n.a.	PMID[18800848]
NPO27799	Agelas dispar	Species	Agelasidae	Eukaryota	n.a.	n.a.	n.a.	PMID[9461661]
NPO27799	Agelas dispar	Species	Agelasidae	Eukaryota	n.a.	n.a.	n.a.	PMID[9748394]
NPO27799	Agelas dispar	Species	Agelasidae	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
MIC	2

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	3.5	ug.mL-1	PMID[548478]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	5.0	ug.mL-1	PMID[548478]

☑ 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 NPC263455 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	314
0.1-0.2	5050
0.2-0.3	13272
0.3-0.4	16522
0.4-0.5	4092
0.5-0.6	2554
0.6-0.7	782
0.7-0.8	92
0.8-0.85	9
0.85-0.9	3
0.9-0.95	5
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9521	High Similarity	NPC312860
0.9306	High Similarity	NPC159630
0.9306	High Similarity	NPC230085
0.9241	High Similarity	NPC167400
0.9128	High Similarity	NPC107287
0.8986	High Similarity	NPC112741
0.8938	High Similarity	NPC317010
0.8645	High Similarity	NPC113812
0.8519	High Similarity	NPC476419
0.8447	Intermediate Similarity	NPC273532
0.8435	Intermediate Similarity	NPC29702
0.8378	Intermediate Similarity	NPC114310
0.8221	Intermediate Similarity	NPC249614
0.8207	Intermediate Similarity	NPC471589
0.8138	Intermediate Similarity	NPC165370
0.8107	Intermediate Similarity	NPC207851
0.8037	Intermediate Similarity	NPC41717
0.7949	Intermediate Similarity	NPC302159
0.7891	Intermediate Similarity	NPC212125
0.7867	Intermediate Similarity	NPC322488
0.7865	Intermediate Similarity	NPC59033
0.7778	Intermediate Similarity	NPC213914
0.7778	Intermediate Similarity	NPC79223
0.777	Intermediate Similarity	NPC306397
0.7765	Intermediate Similarity	NPC164340
0.7764	Intermediate Similarity	NPC209362
0.7709	Intermediate Similarity	NPC329024
0.7707	Intermediate Similarity	NPC471323
0.7669	Intermediate Similarity	NPC138018
0.7667	Intermediate Similarity	NPC317672
0.7667	Intermediate Similarity	NPC320748
0.7667	Intermediate Similarity	NPC324245
0.7614	Intermediate Similarity	NPC44354
0.7609	Intermediate Similarity	NPC12944
0.7609	Intermediate Similarity	NPC25442
0.7598	Intermediate Similarity	NPC135950
0.7597	Intermediate Similarity	NPC328029
0.7556	Intermediate Similarity	NPC109922
0.7541	Intermediate Similarity	NPC328559
0.7541	Intermediate Similarity	NPC32451
0.7528	Intermediate Similarity	NPC114974
0.7527	Intermediate Similarity	NPC103361
0.7527	Intermediate Similarity	NPC156044
0.7473	Intermediate Similarity	NPC309498
0.7443	Intermediate Similarity	NPC295158
0.7439	Intermediate Similarity	NPC33229
0.7394	Intermediate Similarity	NPC63041
0.7377	Intermediate Similarity	NPC474916
0.7354	Intermediate Similarity	NPC472752
0.7353	Intermediate Similarity	NPC319456
0.7346	Intermediate Similarity	NPC105811
0.7345	Intermediate Similarity	NPC282103
0.7337	Intermediate Similarity	NPC123395
0.733	Intermediate Similarity	NPC111732
0.7329	Intermediate Similarity	NPC467188
0.7312	Intermediate Similarity	NPC57398
0.7278	Intermediate Similarity	NPC469489
0.7263	Intermediate Similarity	NPC278434
0.7263	Intermediate Similarity	NPC48042
0.7263	Intermediate Similarity	NPC304179
0.7263	Intermediate Similarity	NPC472550
0.724	Intermediate Similarity	NPC476467
0.7234	Intermediate Similarity	NPC289086
0.7232	Intermediate Similarity	NPC327373
0.7232	Intermediate Similarity	NPC325093
0.7216	Intermediate Similarity	NPC52831
0.7216	Intermediate Similarity	NPC325705
0.7215	Intermediate Similarity	NPC472288
0.7212	Intermediate Similarity	NPC70406
0.7151	Intermediate Similarity	NPC241025
0.7151	Intermediate Similarity	NPC311282
0.7151	Intermediate Similarity	NPC318020
0.715	Intermediate Similarity	NPC472553
0.7143	Intermediate Similarity	NPC138370
0.7143	Intermediate Similarity	NPC313823
0.7135	Intermediate Similarity	NPC90229
0.7128	Intermediate Similarity	NPC477910
0.7127	Intermediate Similarity	NPC75544
0.7125	Intermediate Similarity	NPC85443
0.712	Intermediate Similarity	NPC146724
0.712	Intermediate Similarity	NPC470190
0.7115	Intermediate Similarity	NPC256893
0.7092	Intermediate Similarity	NPC475408
0.7092	Intermediate Similarity	NPC471014
0.7088	Intermediate Similarity	NPC83111
0.7077	Intermediate Similarity	NPC228331
0.7077	Intermediate Similarity	NPC319128
0.7072	Intermediate Similarity	NPC328798
0.707	Intermediate Similarity	NPC330326
0.7069	Intermediate Similarity	NPC302647
0.7069	Intermediate Similarity	NPC253810
0.7066	Intermediate Similarity	NPC251391
0.7059	Intermediate Similarity	NPC151489
0.7059	Intermediate Similarity	NPC322644
0.7056	Intermediate Similarity	NPC294579
0.7056	Intermediate Similarity	NPC144779
0.7052	Intermediate Similarity	NPC470894
0.7051	Intermediate Similarity	NPC315320
0.7048	Intermediate Similarity	NPC313889
0.7041	Intermediate Similarity	NPC477907
0.7041	Intermediate Similarity	NPC470306
0.7041	Intermediate Similarity	NPC42678
0.7041	Intermediate Similarity	NPC477909
0.7039	Intermediate Similarity	NPC322043
0.7033	Intermediate Similarity	NPC182814
0.7024	Intermediate Similarity	NPC229055
0.701	Intermediate Similarity	NPC40919
0.701	Intermediate Similarity	NPC470189
0.7006	Intermediate Similarity	NPC472260
0.7005	Intermediate Similarity	NPC477908
0.7005	Intermediate Similarity	NPC6981
0.7005	Intermediate Similarity	NPC206343
0.7005	Intermediate Similarity	NPC471016
0.6995	Remote Similarity	NPC154339
0.6994	Remote Similarity	NPC114637
0.6987	Remote Similarity	NPC71236
0.6982	Remote Similarity	NPC74357
0.6974	Remote Similarity	NPC280473
0.6974	Remote Similarity	NPC323551
0.697	Remote Similarity	NPC62367
0.6968	Remote Similarity	NPC471313
0.6968	Remote Similarity	NPC474767
0.6968	Remote Similarity	NPC471311
0.6963	Remote Similarity	NPC472259
0.6962	Remote Similarity	NPC194541
0.6959	Remote Similarity	NPC309845
0.6957	Remote Similarity	NPC127647
0.6939	Remote Similarity	NPC41724
0.6939	Remote Similarity	NPC165837
0.6939	Remote Similarity	NPC51008
0.6936	Remote Similarity	NPC477975
0.6935	Remote Similarity	NPC84815
0.6935	Remote Similarity	NPC301368
0.6935	Remote Similarity	NPC202812
0.6935	Remote Similarity	NPC216428
0.6935	Remote Similarity	NPC472555
0.6932	Remote Similarity	NPC191310
0.6927	Remote Similarity	NPC471997
0.6923	Remote Similarity	NPC63562
0.6923	Remote Similarity	NPC90415
0.6919	Remote Similarity	NPC242116
0.6919	Remote Similarity	NPC56170
0.691	Remote Similarity	NPC219848
0.6906	Remote Similarity	NPC285923
0.6905	Remote Similarity	NPC109158
0.6904	Remote Similarity	NPC4421
0.6904	Remote Similarity	NPC264674
0.6898	Remote Similarity	NPC77061
0.6895	Remote Similarity	NPC155792
0.6886	Remote Similarity	NPC123906
0.6885	Remote Similarity	NPC36498
0.6885	Remote Similarity	NPC325775
0.6882	Remote Similarity	NPC267343
0.6881	Remote Similarity	NPC471980
0.6879	Remote Similarity	NPC265100
0.6875	Remote Similarity	NPC76540
0.6872	Remote Similarity	NPC123839
0.6872	Remote Similarity	NPC256268
0.6869	Remote Similarity	NPC193361
0.6869	Remote Similarity	NPC207531
0.6869	Remote Similarity	NPC62844
0.6867	Remote Similarity	NPC297486
0.6867	Remote Similarity	NPC240136
0.6867	Remote Similarity	NPC471402
0.6866	Remote Similarity	NPC477912
0.6857	Remote Similarity	NPC70949
0.6856	Remote Similarity	NPC266249
0.6849	Remote Similarity	NPC27802
0.6847	Remote Similarity	NPC475498
0.6847	Remote Similarity	NPC477902
0.6847	Remote Similarity	NPC475137
0.6847	Remote Similarity	NPC473850
0.6842	Remote Similarity	NPC132680
0.6842	Remote Similarity	NPC269919
0.6839	Remote Similarity	NPC471178
0.6833	Remote Similarity	NPC61011
0.6832	Remote Similarity	NPC127026
0.6832	Remote Similarity	NPC477911
0.6832	Remote Similarity	NPC127720
0.6826	Remote Similarity	NPC477974
0.6825	Remote Similarity	NPC472284
0.6814	Remote Similarity	NPC473506
0.6802	Remote Similarity	NPC118940
0.68	Remote Similarity	NPC6576
0.68	Remote Similarity	NPC473115
0.68	Remote Similarity	NPC473089
0.68	Remote Similarity	NPC75600
0.68	Remote Similarity	NPC319556
0.68	Remote Similarity	NPC158020
0.68	Remote Similarity	NPC212768
0.68	Remote Similarity	NPC187494
0.6798	Remote Similarity	NPC57797
0.6798	Remote Similarity	NPC76565
0.6798	Remote Similarity	NPC250807
0.6792	Remote Similarity	NPC174421
0.6792	Remote Similarity	NPC324611
0.679	Remote Similarity	NPC65408
0.678	Remote Similarity	NPC124029
0.678	Remote Similarity	NPC211920
0.6771	Remote Similarity	NPC328596

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 NPC263455 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	192
0.1-0.2	692
0.2-0.3	897
0.3-0.4	1974
0.4-0.5	3169
0.5-0.6	1732
0.6-0.7	438
0.7-0.8	49
0.8-0.85	2
0.85-0.9	2
0.9-0.95	3
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9241	High Similarity	NPD9075	Approved
0.9241	High Similarity	NPD9074	Approved
0.9231	High Similarity	NPD107	Approved
0.8986	High Similarity	NPD9271	Approved
0.8947	High Similarity	NPD820	Phase 3
0.8446	Intermediate Similarity	NPD203	Clinical (unspecified phase)
0.8193	Intermediate Similarity	NPD8304	Clinical (unspecified phase)
0.8013	Intermediate Similarity	NPD9506	Approved
0.8	Intermediate Similarity	NPD272	Approved
0.7892	Intermediate Similarity	NPD485	Clinical (unspecified phase)
0.7891	Intermediate Similarity	NPD9284	Approved
0.777	Intermediate Similarity	NPD9080	Approved
0.764	Intermediate Similarity	NPD1173	Approved
0.7598	Intermediate Similarity	NPD5975	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD1096	Discontinued
0.7572	Intermediate Similarity	NPD1783	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD510	Phase 1
0.7516	Intermediate Similarity	NPD1649	Discontinued
0.75	Intermediate Similarity	NPD2896	Discontinued
0.7468	Intermediate Similarity	NPD4805	Approved
0.7438	Intermediate Similarity	NPD175	Clinical (unspecified phase)
0.7433	Intermediate Similarity	NPD3371	Approved
0.7423	Intermediate Similarity	NPD5965	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD7396	Approved
0.7381	Intermediate Similarity	NPD5088	Discontinued
0.7375	Intermediate Similarity	NPD1352	Discontinued
0.7346	Intermediate Similarity	NPD1270	Approved
0.7342	Intermediate Similarity	NPD4804	Approved
0.7293	Intermediate Similarity	NPD4376	Phase 3
0.729	Intermediate Similarity	NPD1627	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD3178	Discontinued
0.7267	Intermediate Similarity	NPD3813	Approved
0.7267	Intermediate Similarity	NPD751	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD2511	Approved
0.7238	Intermediate Similarity	NPD2336	Approved
0.7234	Intermediate Similarity	NPD2831	Approved
0.7234	Intermediate Similarity	NPD944	Approved
0.7216	Intermediate Similarity	NPD9510	Approved
0.7198	Intermediate Similarity	NPD981	Phase 2
0.7193	Intermediate Similarity	NPD4174	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD1380	Discovery
0.7143	Intermediate Similarity	NPD1623	Approved
0.7143	Intermediate Similarity	NPD3947	Discontinued
0.7126	Intermediate Similarity	NPD2809	Approved
0.7125	Intermediate Similarity	NPD569	Clinical (unspecified phase)
0.7104	Intermediate Similarity	NPD6665	Discontinued
0.7081	Intermediate Similarity	NPD2307	Discontinued
0.7076	Intermediate Similarity	NPD1631	Approved
0.707	Intermediate Similarity	NPD9100	Approved
0.7066	Intermediate Similarity	NPD180	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD9207	Approved
0.7051	Intermediate Similarity	NPD9206	Approved
0.7037	Intermediate Similarity	NPD1383	Phase 3
0.7037	Intermediate Similarity	NPD1382	Phase 2
0.7024	Intermediate Similarity	NPD2061	Approved
0.7022	Intermediate Similarity	NPD1618	Phase 2
0.7022	Intermediate Similarity	NPD1643	Phase 3
0.7011	Intermediate Similarity	NPD1573	Approved
0.7011	Intermediate Similarity	NPD1575	Approved
0.701	Intermediate Similarity	NPD4417	Approved
0.701	Intermediate Similarity	NPD5475	Discontinued
0.7	Intermediate Similarity	NPD1630	Approved
0.6994	Remote Similarity	NPD1427	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD5322	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD9362	Approved
0.6978	Remote Similarity	NPD4948	Discontinued
0.6975	Remote Similarity	NPD9599	Approved
0.6957	Remote Similarity	NPD9076	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD5490	Discontinued
0.6943	Remote Similarity	NPD2509	Approved
0.6943	Remote Similarity	NPD2510	Approved
0.6939	Remote Similarity	NPD3795	Approved
0.6939	Remote Similarity	NPD3794	Approved
0.6931	Remote Similarity	NPD4491	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD4987	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD721	Approved
0.6885	Remote Similarity	NPD9364	Phase 2
0.6885	Remote Similarity	NPD9363	Approved
0.6882	Remote Similarity	NPD4526	Approved
0.6882	Remote Similarity	NPD4529	Approved
0.6882	Remote Similarity	NPD4528	Approved
0.6842	Remote Similarity	NPD9383	Approved
0.6842	Remote Similarity	NPD2581	Approved
0.6842	Remote Similarity	NPD2582	Approved
0.6842	Remote Similarity	NPD9382	Approved
0.6839	Remote Similarity	NPD1568	Clinical (unspecified phase)
0.6836	Remote Similarity	NPD750	Phase 2
0.6811	Remote Similarity	NPD3321	Discontinued
0.6809	Remote Similarity	NPD7061	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD5255	Approved
0.6792	Remote Similarity	NPD9726	Discontinued
0.679	Remote Similarity	NPD200	Phase 2
0.679	Remote Similarity	NPD201	Phase 2
0.6788	Remote Similarity	NPD6987	Phase 1
0.6788	Remote Similarity	NPD5901	Discontinued
0.6774	Remote Similarity	NPD1977	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD7404	Approved
0.6763	Remote Similarity	NPD9398	Clinical (unspecified phase)
0.6754	Remote Similarity	NPD5228	Phase 3
0.6738	Remote Similarity	NPD3406	Suspended
0.6735	Remote Similarity	NPD6529	Discontinued
0.6733	Remote Similarity	NPD3280	Approved
0.6733	Remote Similarity	NPD269	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD5020	Approved
0.6721	Remote Similarity	NPD3569	Discontinued
0.6706	Remote Similarity	NPD9595	Approved
0.6706	Remote Similarity	NPD9596	Approved
0.6705	Remote Similarity	NPD704	Clinical (unspecified phase)
0.6704	Remote Similarity	NPD4736	Clinical (unspecified phase)
0.6704	Remote Similarity	NPD4883	Approved
0.6702	Remote Similarity	NPD6137	Clinical (unspecified phase)
0.67	Remote Similarity	NPD3394	Approved
0.67	Remote Similarity	NPD3389	Approved
0.67	Remote Similarity	NPD3393	Approved
0.67	Remote Similarity	NPD4301	Approved
0.6685	Remote Similarity	NPD2814	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD1587	Approved
0.6667	Remote Similarity	NPD7010	Phase 3
0.6667	Remote Similarity	NPD4396	Clinical (unspecified phase)
0.6635	Remote Similarity	NPD5891	Approved
0.6631	Remote Similarity	NPD2544	Clinical (unspecified phase)
0.6631	Remote Similarity	NPD8063	Discontinued
0.663	Remote Similarity	NPD5751	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD4702	Approved
0.6627	Remote Similarity	NPD4703	Approved
0.6626	Remote Similarity	NPD206	Clinical (unspecified phase)
0.6612	Remote Similarity	NPD4011	Clinical (unspecified phase)
0.6611	Remote Similarity	NPD1586	Approved
0.6611	Remote Similarity	NPD482	Approved
0.661	Remote Similarity	NPD5611	Phase 2
0.6599	Remote Similarity	NPD1367	Phase 2
0.6595	Remote Similarity	NPD3082	Discontinued
0.6587	Remote Similarity	NPD3717	Discontinued
0.6582	Remote Similarity	NPD7001	Phase 3
0.6581	Remote Similarity	NPD268	Approved
0.6581	Remote Similarity	NPD270	Clinical (unspecified phase)
0.6581	Remote Similarity	NPD271	Approved
0.6575	Remote Similarity	NPD749	Clinical (unspecified phase)
0.6573	Remote Similarity	NPD1343	Approved
0.6573	Remote Similarity	NPD5862	Discovery
0.6573	Remote Similarity	NPD1292	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD5583	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD1395	Clinical (unspecified phase)
0.6564	Remote Similarity	NPD5513	Phase 2
0.6556	Remote Similarity	NPD1599	Approved
0.6546	Remote Similarity	NPD5017	Discontinued
0.6533	Remote Similarity	NPD4823	Approved
0.6533	Remote Similarity	NPD4824	Approved
0.6531	Remote Similarity	NPD4906	Approved
0.6531	Remote Similarity	NPD4905	Approved
0.6531	Remote Similarity	NPD6323	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD4903	Approved
0.6528	Remote Similarity	NPD6999	Discontinued
0.6528	Remote Similarity	NPD7049	Clinical (unspecified phase)
0.6528	Remote Similarity	NPD7000	Clinical (unspecified phase)
0.6519	Remote Similarity	NPD158	Discontinued
0.6517	Remote Similarity	NPD424	Approved
0.6517	Remote Similarity	NPD425	Approved
0.6515	Remote Similarity	NPD7467	Discontinued
0.6513	Remote Similarity	NPD5721	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD9706	Clinical (unspecified phase)
0.65	Remote Similarity	NPD1095	Clinical (unspecified phase)
0.65	Remote Similarity	NPD3779	Clinical (unspecified phase)
0.6497	Remote Similarity	NPD4904	Approved
0.6497	Remote Similarity	NPD7289	Clinical (unspecified phase)
0.6497	Remote Similarity	NPD6635	Approved
0.6497	Remote Similarity	NPD6732	Clinical (unspecified phase)
0.6494	Remote Similarity	NPD276	Clinical (unspecified phase)
0.6488	Remote Similarity	NPD1996	Discontinued
0.6488	Remote Similarity	NPD8479	Phase 2
0.6484	Remote Similarity	NPD5100	Phase 3
0.648	Remote Similarity	NPD6872	Clinical (unspecified phase)
0.6477	Remote Similarity	NPD687	Clinical (unspecified phase)
0.6474	Remote Similarity	NPD5505	Discontinued
0.6474	Remote Similarity	NPD3288	Approved
0.6473	Remote Similarity	NPD6173	Approved
0.6468	Remote Similarity	NPD6657	Clinical (unspecified phase)
0.6467	Remote Similarity	NPD1291	Clinical (unspecified phase)
0.6467	Remote Similarity	NPD2479	Phase 3
0.6467	Remote Similarity	NPD2481	Approved
0.6465	Remote Similarity	NPD6135	Phase 1
0.6464	Remote Similarity	NPD2077	Approved
0.6464	Remote Similarity	NPD2076	Approved
0.6461	Remote Similarity	NPD925	Approved
0.6461	Remote Similarity	NPD926	Approved
0.6458	Remote Similarity	NPD2290	Phase 3
0.6458	Remote Similarity	NPD6226	Phase 3
0.6458	Remote Similarity	NPD2289	Phase 3
0.6455	Remote Similarity	NPD4081	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD2417	Approved
0.6452	Remote Similarity	NPD2416	Approved
0.645	Remote Similarity	NPD6204	Clinical (unspecified phase)
0.6441	Remote Similarity	NPD5400	Approved
0.6439	Remote Similarity	NPD6770	Approved
0.6436	Remote Similarity	NPD4988	Discontinued
0.6425	Remote Similarity	NPD6446	Discontinued
0.6422	Remote Similarity	NPD8000	Clinical (unspecified phase)
0.6422	Remote Similarity	NPD3805	Clinical (unspecified phase)
0.6421	Remote Similarity	NPD4699	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