NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	111.03
Volume:	107.148
LogP:	0.892
LogD:	0.236
LogS:	-1.005
# Rotatable Bonds:	1
TPSA:	53.09
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	1
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.56
Synthetic Accessibility Score:	2.394
Fsp3:	0.0
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	2
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.012
MDCK Permeability:	7.110140359145589e-06
Pgp-inhibitor:	0.0
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.014
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.541

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.893
Plasma Protein Binding (PPB):	14.734630584716797%
Volume Distribution (VD):	0.25
Pgp-substrate:	76.8968734741211%

ADMET: Metabolism

CYP1A2-inhibitor:	0.024
CYP1A2-substrate:	0.098
CYP2C19-inhibitor:	0.052
CYP2C19-substrate:	0.05
CYP2C9-inhibitor:	0.021
CYP2C9-substrate:	0.406
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.141
CYP3A4-inhibitor:	0.015
CYP3A4-substrate:	0.045

ADMET: Excretion

Clearance (CL):	5.809
Half-life (T1/2):	0.92

ADMET: Toxicity

hERG Blockers:	0.032
Human Hepatotoxicity (H-HT):	0.241
Drug-inuced Liver Injury (DILI):	0.715
AMES Toxicity:	0.015
Rat Oral Acute Toxicity:	0.941
Maximum Recommended Daily Dose:	0.008
Skin Sensitization:	0.152
Carcinogencity:	0.054
Eye Corrosion:	0.122
Eye Irritation:	0.994
Respiratory Toxicity:	0.936

Download Data

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

Natural Product: NPC33229

Natural Product ID:	NPC33229
*Common Name:**	Pyrrole-2-Carboxylic Acid
IUPAC Name:	1H-pyrrole-2-carboxylic acid
Synonyms:
Standard InCHIKey:	WRHZVMBBRYBTKZ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C5H5NO2/c7-5(8)4-2-1-3-6-4/h1-3,6H,(H,7,8)
SMILES:	OC(=O)c1ccc[nH]1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL509027
PubChem CID:	12473
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000090] Pyrroles [CHEMONTID:0002554] Pyrrole carboxylic acids and derivatives [CHEMONTID:0002555] Pyrrole carboxylic acids [CHEMONTID:0002557] Pyrrole 2-carboxylic acids

*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
IC50	2
Kd	1
Others	9

Activity Type	# Activity
Individual Protein	12

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT645	Individual Protein	D-amino-acid oxidase	Homo sapiens	IC50	>	5000.0	nM	PMID[521348]
NPT569	Individual Protein	Matrix metalloproteinase 8	Homo sapiens	Inhibition	=	-24.0	%	PMID[521349]
NPT270	Individual Protein	Nitric oxide synthase, inducible	Mus musculus	Inhibition	=	7.0	%	PMID[521349]
NPT280	Individual Protein	Matrix metalloproteinase 9	Homo sapiens	Inhibition	=	-20.0	%	PMID[521349]
NPT570	Individual Protein	Arachidonate 5-lipoxygenase	Homo sapiens	Inhibition	=	48.0	%	PMID[521349]
NPT568	Individual Protein	Matrix metalloproteinase-2	Homo sapiens	Inhibition	=	1.0	%	PMID[521349]
NPT567	Individual Protein	Matrix metalloproteinase 3	Homo sapiens	Inhibition	=	-8.0	%	PMID[521349]
NPT150	Individual Protein	Anthrax lethal factor	Bacillus anthracis	Inhibition	=	11.0	%	PMID[521349]
NPT43	Individual Protein	Tyrosinase	Agaricus bisporus	Inhibition	=	69.0	%	PMID[521349]
NPT2587	Individual Protein	D-amino-acid oxidase	Sus scrofa	Kd	=	26000.0	nM	PMID[521350]
NPT2587	Individual Protein	D-amino-acid oxidase	Sus scrofa	IC50	<	10000.0	nM	PMID[521351]
NPT69	Individual Protein	Matrix metalloproteinase-1	Homo sapiens	Inhibition	=	8.0	%	PMID[521349]

☑ 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 NPC33229 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	1286
0.1-0.2	10836
0.2-0.3	16731
0.3-0.4	8394
0.4-0.5	2380
0.5-0.6	2248
0.6-0.7	711
0.7-0.8	102
0.8-0.85	7
0.85-0.9	1
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8667	High Similarity	NPC302159
0.8431	Intermediate Similarity	NPC13432
0.8377	Intermediate Similarity	NPC52110
0.8367	Intermediate Similarity	NPC23215
0.8367	Intermediate Similarity	NPC291517
0.8221	Intermediate Similarity	NPC302647
0.8057	Intermediate Similarity	NPC77061
0.8	Intermediate Similarity	NPC273532
0.7975	Intermediate Similarity	NPC109158
0.7927	Intermediate Similarity	NPC41717
0.7874	Intermediate Similarity	NPC83111
0.7829	Intermediate Similarity	NPC328029
0.7826	Intermediate Similarity	NPC142688
0.7792	Intermediate Similarity	NPC85443
0.7771	Intermediate Similarity	NPC167400
0.7759	Intermediate Similarity	NPC278434
0.7746	Intermediate Similarity	NPC311282
0.7702	Intermediate Similarity	NPC312860
0.7679	Intermediate Similarity	NPC253810
0.7667	Intermediate Similarity	NPC71236
0.7662	Intermediate Similarity	NPC114310
0.7662	Intermediate Similarity	NPC472288
0.7561	Intermediate Similarity	NPC212742
0.7553	Intermediate Similarity	NPC82370
0.7516	Intermediate Similarity	NPC194541
0.7514	Intermediate Similarity	NPC209917
0.7486	Intermediate Similarity	NPC207851
0.747	Intermediate Similarity	NPC473706
0.7442	Intermediate Similarity	NPC476419
0.7439	Intermediate Similarity	NPC263455
0.7439	Intermediate Similarity	NPC298288
0.7381	Intermediate Similarity	NPC162268
0.7375	Intermediate Similarity	NPC230085
0.7375	Intermediate Similarity	NPC159630
0.7356	Intermediate Similarity	NPC126709
0.7356	Intermediate Similarity	NPC248041
0.7356	Intermediate Similarity	NPC283219
0.7348	Intermediate Similarity	NPC473821
0.7322	Intermediate Similarity	NPC74153
0.7308	Intermediate Similarity	NPC202812
0.7305	Intermediate Similarity	NPC113812
0.7299	Intermediate Similarity	NPC111275
0.7283	Intermediate Similarity	NPC110500
0.7283	Intermediate Similarity	NPC149155
0.7283	Intermediate Similarity	NPC203468
0.7261	Intermediate Similarity	NPC29702
0.7255	Intermediate Similarity	NPC313823
0.7251	Intermediate Similarity	NPC78020
0.7241	Intermediate Similarity	NPC267885
0.7239	Intermediate Similarity	NPC112741
0.7238	Intermediate Similarity	NPC210123
0.7238	Intermediate Similarity	NPC138370
0.7235	Intermediate Similarity	NPC233380
0.7222	Intermediate Similarity	NPC229893
0.7219	Intermediate Similarity	NPC57398
0.7179	Intermediate Similarity	NPC472285
0.7152	Intermediate Similarity	NPC471655
0.7151	Intermediate Similarity	NPC295158
0.715	Intermediate Similarity	NPC118940
0.7143	Intermediate Similarity	NPC27296
0.7135	Intermediate Similarity	NPC141454
0.7126	Intermediate Similarity	NPC75135
0.7119	Intermediate Similarity	NPC317010
0.7112	Intermediate Similarity	NPC315491
0.7112	Intermediate Similarity	NPC45459
0.7102	Intermediate Similarity	NPC14113
0.7102	Intermediate Similarity	NPC145885
0.7102	Intermediate Similarity	NPC84827
0.7083	Intermediate Similarity	NPC169586
0.707	Intermediate Similarity	NPC20021
0.7069	Intermediate Similarity	NPC54214
0.7066	Intermediate Similarity	NPC107287
0.7062	Intermediate Similarity	NPC55772
0.7059	Intermediate Similarity	NPC322644
0.7059	Intermediate Similarity	NPC131718
0.7056	Intermediate Similarity	NPC469717
0.7044	Intermediate Similarity	NPC64661
0.7044	Intermediate Similarity	NPC138596
0.7044	Intermediate Similarity	NPC98156
0.7044	Intermediate Similarity	NPC200397
0.7044	Intermediate Similarity	NPC14448
0.7044	Intermediate Similarity	NPC195704
0.7044	Intermediate Similarity	NPC292434
0.7044	Intermediate Similarity	NPC167200
0.7043	Intermediate Similarity	NPC473814
0.7043	Intermediate Similarity	NPC78767
0.7041	Intermediate Similarity	NPC36405
0.7031	Intermediate Similarity	NPC266249
0.7027	Intermediate Similarity	NPC93390
0.7021	Intermediate Similarity	NPC213308
0.6995	Remote Similarity	NPC154339
0.6984	Remote Similarity	NPC471944
0.6983	Remote Similarity	NPC71037
0.6977	Remote Similarity	NPC102423
0.6968	Remote Similarity	NPC103361
0.6968	Remote Similarity	NPC306397
0.6962	Remote Similarity	NPC322488
0.6961	Remote Similarity	NPC241025
0.6959	Remote Similarity	NPC123839
0.6941	Remote Similarity	NPC213914
0.694	Remote Similarity	NPC75544
0.6936	Remote Similarity	NPC474383
0.6932	Remote Similarity	NPC80528
0.6927	Remote Similarity	NPC314281
0.6927	Remote Similarity	NPC40530
0.6923	Remote Similarity	NPC209362
0.6923	Remote Similarity	NPC315555
0.6923	Remote Similarity	NPC235684
0.6923	Remote Similarity	NPC474236
0.6918	Remote Similarity	NPC150592
0.6911	Remote Similarity	NPC165599
0.6909	Remote Similarity	NPC260041
0.6905	Remote Similarity	NPC472260
0.6901	Remote Similarity	NPC474492
0.6891	Remote Similarity	NPC183777
0.6882	Remote Similarity	NPC267343
0.6871	Remote Similarity	NPC77582
0.6871	Remote Similarity	NPC169308
0.6871	Remote Similarity	NPC129753
0.6871	Remote Similarity	NPC302717
0.6871	Remote Similarity	NPC209281
0.6871	Remote Similarity	NPC48171
0.6871	Remote Similarity	NPC59839
0.6871	Remote Similarity	NPC74928
0.6871	Remote Similarity	NPC205604
0.6871	Remote Similarity	NPC12831
0.6871	Remote Similarity	NPC244087
0.6871	Remote Similarity	NPC3698
0.6871	Remote Similarity	NPC97230
0.6871	Remote Similarity	NPC286529
0.6862	Remote Similarity	NPC156704
0.6856	Remote Similarity	NPC171787
0.6848	Remote Similarity	NPC321708
0.6848	Remote Similarity	NPC221873
0.6845	Remote Similarity	NPC135950
0.6839	Remote Similarity	NPC42372
0.6839	Remote Similarity	NPC151489
0.6833	Remote Similarity	NPC477042
0.6829	Remote Similarity	NPC114033
0.6829	Remote Similarity	NPC101130
0.6829	Remote Similarity	NPC58268
0.6829	Remote Similarity	NPC129412
0.6825	Remote Similarity	NPC131887
0.6811	Remote Similarity	NPC469489
0.6809	Remote Similarity	NPC179701
0.6807	Remote Similarity	NPC467188
0.6807	Remote Similarity	NPC159856
0.6804	Remote Similarity	NPC244741
0.6804	Remote Similarity	NPC321428
0.678	Remote Similarity	NPC249614
0.6778	Remote Similarity	NPC213468
0.6776	Remote Similarity	NPC280290
0.6772	Remote Similarity	NPC262898
0.6769	Remote Similarity	NPC476524
0.6766	Remote Similarity	NPC74360
0.6766	Remote Similarity	NPC220523
0.6763	Remote Similarity	NPC470680
0.6763	Remote Similarity	NPC100104
0.6762	Remote Similarity	NPC15801
0.6753	Remote Similarity	NPC82053
0.6752	Remote Similarity	NPC212125
0.6752	Remote Similarity	NPC165370
0.6748	Remote Similarity	NPC104049
0.6744	Remote Similarity	NPC475870
0.6742	Remote Similarity	NPC313791
0.6739	Remote Similarity	NPC476527
0.6737	Remote Similarity	NPC248782
0.6737	Remote Similarity	NPC67288
0.6737	Remote Similarity	NPC477044
0.6737	Remote Similarity	NPC477041
0.6726	Remote Similarity	NPC100726
0.6726	Remote Similarity	NPC105811
0.6722	Remote Similarity	NPC15573
0.6722	Remote Similarity	NPC96890
0.6722	Remote Similarity	NPC284775
0.6722	Remote Similarity	NPC184964
0.6722	Remote Similarity	NPC217372
0.6722	Remote Similarity	NPC183662
0.6721	Remote Similarity	NPC477003
0.6721	Remote Similarity	NPC228835
0.6718	Remote Similarity	NPC88008
0.6717	Remote Similarity	NPC219087
0.6705	Remote Similarity	NPC230869
0.6704	Remote Similarity	NPC37268
0.6703	Remote Similarity	NPC17059
0.6702	Remote Similarity	NPC477045
0.6702	Remote Similarity	NPC123395
0.6701	Remote Similarity	NPC477043
0.6699	Remote Similarity	NPC192712
0.6687	Remote Similarity	NPC174421
0.6686	Remote Similarity	NPC141353
0.6686	Remote Similarity	NPC206148
0.6685	Remote Similarity	NPC42979
0.6685	Remote Similarity	NPC262338
0.6685	Remote Similarity	NPC282103
0.6685	Remote Similarity	NPC11126
0.6685	Remote Similarity	NPC219336
0.6667	Remote Similarity	NPC27041
0.6667	Remote Similarity	NPC48938
0.6667	Remote Similarity	NPC224764

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 NPC33229 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	293
0.1-0.2	941
0.2-0.3	1039
0.3-0.4	2628
0.4-0.5	2513
0.5-0.6	1486
0.6-0.7	238
0.7-0.8	11
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8765	High Similarity	NPD3178	Discontinued
0.7771	Intermediate Similarity	NPD9075	Approved
0.7771	Intermediate Similarity	NPD9074	Approved
0.7586	Intermediate Similarity	NPD1096	Discontinued
0.7516	Intermediate Similarity	NPD107	Approved
0.7471	Intermediate Similarity	NPD1783	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD5901	Discontinued
0.7289	Intermediate Similarity	NPD276	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD482	Approved
0.7241	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD9271	Approved
0.717	Intermediate Similarity	NPD203	Clinical (unspecified phase)
0.7112	Intermediate Similarity	NPD484	Approved
0.7039	Intermediate Similarity	NPD2094	Phase 2
0.7039	Intermediate Similarity	NPD2095	Phase 2
0.7039	Intermediate Similarity	NPD2092	Phase 2
0.7035	Intermediate Similarity	NPD1568	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD2096	Phase 2
0.7	Intermediate Similarity	NPD2091	Phase 2
0.6968	Remote Similarity	NPD9080	Approved
0.6964	Remote Similarity	NPD180	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD9076	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD820	Phase 3
0.6932	Remote Similarity	NPD750	Phase 2
0.6919	Remote Similarity	NPD6665	Discontinued
0.6905	Remote Similarity	NPD9343	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD510	Phase 1
0.6882	Remote Similarity	NPD1173	Approved
0.6879	Remote Similarity	NPD1631	Approved
0.6851	Remote Similarity	NPD5728	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD1573	Approved
0.6818	Remote Similarity	NPD1575	Approved
0.6802	Remote Similarity	NPD604	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD7998	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD4862	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD2715	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD9284	Approved
0.6751	Remote Similarity	NPD7470	Discontinued
0.6705	Remote Similarity	NPD1630	Approved
0.6704	Remote Similarity	NPD158	Discontinued
0.6704	Remote Similarity	NPD5065	Approved
0.6701	Remote Similarity	NPD2721	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD2509	Approved
0.6684	Remote Similarity	NPD2510	Approved
0.6667	Remote Similarity	NPD5975	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD706	Phase 1
0.6633	Remote Similarity	NPD3916	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD3917	Approved
0.6633	Remote Similarity	NPD3918	Approved
0.6617	Remote Similarity	NPD3394	Approved
0.6617	Remote Similarity	NPD3389	Approved
0.6617	Remote Similarity	NPD3393	Approved
0.6615	Remote Similarity	NPD3947	Discontinued
0.6611	Remote Similarity	NPD4736	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD9506	Approved
0.6583	Remote Similarity	NPD3915	Approved
0.6582	Remote Similarity	NPD4559	Clinical (unspecified phase)
0.6573	Remote Similarity	NPD2844	Phase 3
0.6536	Remote Similarity	NPD565	Phase 2
0.6531	Remote Similarity	NPD944	Approved
0.6524	Remote Similarity	NPD4948	Discontinued
0.6503	Remote Similarity	NPD1587	Approved
0.65	Remote Similarity	NPD1031	Discontinued
0.6488	Remote Similarity	NPD1996	Discontinued
0.648	Remote Similarity	NPD5069	Clinical (unspecified phase)
0.6474	Remote Similarity	NPD4376	Phase 3
0.6474	Remote Similarity	NPD981	Phase 2
0.6473	Remote Similarity	NPD6753	Phase 1
0.6473	Remote Similarity	NPD6752	Phase 1
0.6473	Remote Similarity	NPD6173	Approved
0.6467	Remote Similarity	NPD1649	Discontinued
0.6467	Remote Similarity	NPD1643	Phase 3
0.6467	Remote Similarity	NPD9599	Approved
0.6465	Remote Similarity	NPD6838	Clinical (unspecified phase)
0.6462	Remote Similarity	NPD5017	Discontinued
0.6452	Remote Similarity	NPD3607	Clinical (unspecified phase)
0.645	Remote Similarity	NPD1352	Discontinued
0.6446	Remote Similarity	NPD2896	Discontinued
0.6444	Remote Similarity	NPD4184	Clinical (unspecified phase)
0.6443	Remote Similarity	NPD7621	Clinical (unspecified phase)
0.6442	Remote Similarity	NPD9100	Approved
0.644	Remote Similarity	NPD460	Discontinued
0.6429	Remote Similarity	NPD9396	Approved
0.6429	Remote Similarity	NPD4805	Approved
0.6429	Remote Similarity	NPD9392	Approved
0.642	Remote Similarity	NPD704	Clinical (unspecified phase)
0.6418	Remote Similarity	NPD5475	Discontinued
0.6418	Remote Similarity	NPD3779	Clinical (unspecified phase)
0.6413	Remote Similarity	NPD8304	Clinical (unspecified phase)
0.6409	Remote Similarity	NPD485	Clinical (unspecified phase)
0.6407	Remote Similarity	NPD569	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD3757	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD5088	Discontinued
0.6392	Remote Similarity	NPD7459	Phase 2
0.6386	Remote Similarity	NPD8093	Discontinued
0.6378	Remote Similarity	NPD6452	Discontinued
0.6378	Remote Similarity	NPD9510	Approved
0.6364	Remote Similarity	NPD272	Approved
0.6364	Remote Similarity	NPD6323	Clinical (unspecified phase)
0.635	Remote Similarity	NPD7947	Clinical (unspecified phase)
0.6349	Remote Similarity	NPD6141	Clinical (unspecified phase)
0.6343	Remote Similarity	NPD2061	Approved
0.634	Remote Similarity	NPD7948	Phase 1
0.6339	Remote Similarity	NPD1586	Approved
0.6339	Remote Similarity	NPD4883	Approved
0.6335	Remote Similarity	NPD5592	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD4174	Clinical (unspecified phase)
0.6331	Remote Similarity	NPD1592	Phase 3
0.6331	Remote Similarity	NPD5020	Approved
0.6328	Remote Similarity	NPD5255	Approved
0.6327	Remote Similarity	NPD8248	Clinical (unspecified phase)
0.6325	Remote Similarity	NPD198	Clinical (unspecified phase)
0.6322	Remote Similarity	NPD5965	Clinical (unspecified phase)
0.6313	Remote Similarity	NPD2921	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD1623	Approved
0.6311	Remote Similarity	NPD8405	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD6578	Clinical (unspecified phase)
0.631	Remote Similarity	NPD4804	Approved
0.6309	Remote Similarity	NPD9099	Clinical (unspecified phase)
0.6309	Remote Similarity	NPD9098	Phase 3
0.6305	Remote Similarity	NPD8097	Phase 3
0.6305	Remote Similarity	NPD8096	Phase 3
0.63	Remote Similarity	NPD3371	Approved
0.6296	Remote Similarity	NPD4426	Clinical (unspecified phase)
0.6293	Remote Similarity	NPD3353	Approved
0.629	Remote Similarity	NPD1291	Clinical (unspecified phase)
0.6283	Remote Similarity	NPD5686	Approved
0.6283	Remote Similarity	NPD5685	Approved
0.6276	Remote Similarity	NPD6137	Clinical (unspecified phase)
0.627	Remote Similarity	NPD6203	Clinical (unspecified phase)
0.6269	Remote Similarity	NPD5575	Clinical (unspecified phase)
0.6266	Remote Similarity	NPD9598	Discontinued
0.6264	Remote Similarity	NPD1326	Approved
0.6264	Remote Similarity	NPD1325	Approved
0.6257	Remote Similarity	NPD751	Clinical (unspecified phase)
0.6257	Remote Similarity	NPD3813	Approved
0.625	Remote Similarity	NPD5322	Clinical (unspecified phase)
0.625	Remote Similarity	NPD6180	Clinical (unspecified phase)
0.6244	Remote Similarity	NPD2547	Discontinued
0.6243	Remote Similarity	NPD5611	Phase 2
0.6243	Remote Similarity	NPD2814	Clinical (unspecified phase)
0.6224	Remote Similarity	NPD772	Phase 3
0.6222	Remote Similarity	NPD5138	Approved
0.6222	Remote Similarity	NPD5140	Approved
0.6221	Remote Similarity	NPD175	Clinical (unspecified phase)
0.6219	Remote Similarity	NPD3411	Phase 2
0.6219	Remote Similarity	NPD3410	Approved
0.6213	Remote Similarity	NPD786	Approved
0.6212	Remote Similarity	NPD7903	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD7825	Clinical (unspecified phase)
0.6203	Remote Similarity	NPD6595	Phase 3
0.6203	Remote Similarity	NPD1618	Phase 2
0.6201	Remote Similarity	NPD9398	Clinical (unspecified phase)
0.62	Remote Similarity	NPD6987	Phase 1
0.62	Remote Similarity	NPD6288	Clinical (unspecified phase)
0.62	Remote Similarity	NPD8098	Approved
0.62	Remote Similarity	NPD5426	Phase 3
0.6199	Remote Similarity	NPD3717	Discontinued
0.6199	Remote Similarity	NPD5483	Clinical (unspecified phase)
0.6196	Remote Similarity	NPD1037	Clinical (unspecified phase)
0.6196	Remote Similarity	NPD1095	Clinical (unspecified phase)
0.6195	Remote Similarity	NPD3794	Approved
0.6195	Remote Similarity	NPD3243	Approved
0.6195	Remote Similarity	NPD3795	Approved
0.6195	Remote Similarity	NPD8094	Discontinued
0.619	Remote Similarity	NPD3569	Discontinued
0.6186	Remote Similarity	NPD1038	Approved
0.6183	Remote Similarity	NPD2144	Approved
0.6181	Remote Similarity	NPD8073	Approved
0.6179	Remote Similarity	NPD7603	Discontinued
0.6178	Remote Similarity	NPD9364	Phase 2
0.6178	Remote Similarity	NPD9363	Approved
0.6176	Remote Similarity	NPD8013	Clinical (unspecified phase)
0.6173	Remote Similarity	NPD5003	Discontinued
0.6172	Remote Similarity	NPD6242	Discontinued
0.6169	Remote Similarity	NPD7289	Clinical (unspecified phase)
0.6166	Remote Similarity	NPD2336	Approved
0.6165	Remote Similarity	NPD7971	Clinical (unspecified phase)
0.6165	Remote Similarity	NPD7970	Approved
0.6158	Remote Similarity	NPD2809	Approved
0.6158	Remote Similarity	NPD3968	Approved
0.6154	Remote Similarity	NPD7618	Phase 3
0.6154	Remote Similarity	NPD425	Approved
0.6154	Remote Similarity	NPD7619	Phase 3
0.6154	Remote Similarity	NPD424	Approved
0.615	Remote Similarity	NPD4845	Discontinued
0.615	Remote Similarity	NPD4076	Approved
0.615	Remote Similarity	NPD4079	Approved
0.615	Remote Similarity	NPD8072	Approved
0.6145	Remote Similarity	NPD1627	Clinical (unspecified phase)
0.614	Remote Similarity	NPD1722	Approved
0.6139	Remote Similarity	NPD8493	Clinical (unspecified phase)
0.6134	Remote Similarity	NPD3288	Approved
0.6133	Remote Similarity	NPD861	Approved
0.6133	Remote Similarity	NPD863	Approved
0.6133	Remote Similarity	NPD862	Approved
0.6126	Remote Similarity	NPD3315	Phase 3
0.6122	Remote Similarity	NPD2290	Phase 3
0.6122	Remote Similarity	NPD2289	Phase 3

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