NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	95.04
Volume:	98.358
LogP:	0.921
LogD:	0.754
LogS:	-0.903
# Rotatable Bonds:	1
TPSA:	32.86
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.515
Synthetic Accessibility Score:	3.023
Fsp3:	0.0
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.284
MDCK Permeability:	1.5739258742542006e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.012
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.02

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.996
Plasma Protein Binding (PPB):	27.647541046142578%
Volume Distribution (VD):	1.183
Pgp-substrate:	79.6519546508789%

ADMET: Metabolism

CYP1A2-inhibitor:	0.564
CYP1A2-substrate:	0.416
CYP2C19-inhibitor:	0.06
CYP2C19-substrate:	0.13
CYP2C9-inhibitor:	0.014
CYP2C9-substrate:	0.858
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.477
CYP3A4-inhibitor:	0.007
CYP3A4-substrate:	0.157

ADMET: Excretion

Clearance (CL):	8.065
Half-life (T1/2):	0.876

ADMET: Toxicity

hERG Blockers:	0.024
Human Hepatotoxicity (H-HT):	0.057
Drug-inuced Liver Injury (DILI):	0.03
AMES Toxicity:	0.088
Rat Oral Acute Toxicity:	0.845
Maximum Recommended Daily Dose:	0.074
Skin Sensitization:	0.405
Carcinogencity:	0.24
Eye Corrosion:	0.98
Eye Irritation:	0.994
Respiratory Toxicity:	0.982

Download Data

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

Natural Product: NPC23215

Natural Product ID:	NPC23215
*Common Name:**	Pyrrole-2-Carboxylate
IUPAC Name:	1H-pyrrole-2-carbaldehyde
Synonyms:
Standard InCHIKey:	ZSKGQVFRTSEPJT-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C5H5NO/c7-4-5-2-1-3-6-5/h1-4,6H
SMILES:	O=Cc1ccc[nH]1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2229658
PubChem CID:	13854
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0001831] Carbonyl compounds [CHEMONTID:0000124] Aldehydes [CHEMONTID:0003213] Aryl-aldehydes

*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
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.foodchem.2013.08.121]
NPO23656	Typha latifolia	Species	Typhaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1021/np50070a031]
NPO11438	Angelica gigas	Species	Apiaceae	Eukaryota	n.a.	root	n.a.	PMID[11374978]
NPO11438	Angelica gigas	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15679317]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	Flowers	n.a.	n.a.	PMID[16180814]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	seeds	Shizuoka prefecture, Japan	n.a.	PMID[16499314]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	roots	purchased from Kiu Shun Trading Ltd., Vancouver, Canada	2000	PMID[16643021]
NPO11438	Angelica gigas	Species	Apiaceae	Eukaryota	n.a.	root	n.a.	PMID[17997069]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18068204]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	leaf	n.a.	PMID[18409045]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	flower buds	n.a.	n.a.	PMID[19926279]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	root	n.a.	PMID[2092947]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	berry	n.a.	n.a.	PMID[21216145]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21434603]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	n.a.	flower	n.a.	PMID[21922925]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	flower buds	n.a.	n.a.	PMID[21925888]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	leaves	n.a.	n.a.	PMID[22377672]
NPO1099	Capparis spinosa	Species	Capparaceae	Eukaryota	aerial parts and buds	Cagliari, Sardinia	2012-FEB	PMID[22769561]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	n.a.	leaf	n.a.	PMID[23265489]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	Leaves	Bandung, West Java, Indonesia		PMID[23621359]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	leaves	n.a.	n.a.	PMID[24290061]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24968750]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25152999]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25538068]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	stems-leaves	n.a.	n.a.	PMID[26420067]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27400088]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	stem	n.a.	PMID[27914541]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	Flower Buds	n.a.	n.a.	PMID[28345906]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32129622]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	Cotyledon	n.a.	n.a.	Database[FooDB]
NPO1099	Capparis spinosa	Species	Capparaceae	Eukaryota	Flower	n.a.	n.a.	Database[FooDB]
NPO1099	Capparis spinosa	Species	Capparaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO1099	Capparis spinosa	Species	Capparaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	Leaf Essent. Oil	n.a.	n.a.	Database[FooDB]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO1099	Capparis spinosa	Species	Capparaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	Seed Oil	n.a.	n.a.	Database[FooDB]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	Shoot	n.a.	n.a.	Database[FooDB]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	Stem	n.a.	n.a.	Database[FooDB]
NPO1099	Capparis spinosa	Species	Capparaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO1099	Capparis spinosa	Species	Capparaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO1099	Capparis spinosa	Species	Capparaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2921	Angelica acutiloba	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23656	Typha latifolia	Species	Typhaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11438	Angelica gigas	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[MetaboLights]
NPO24062	Radix pseudostellariae	Species	Lymnaeidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2921	Angelica acutiloba	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11438	Angelica gigas	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1099	Capparis spinosa	Species	Capparaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23656	Typha latifolia	Species	Typhaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1099	Capparis spinosa	Species	Capparaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO23656	Typha latifolia	Species	Typhaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11438	Angelica gigas	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2921	Angelica acutiloba	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2921	Angelica acutiloba	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO11438	Angelica gigas	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23656	Typha latifolia	Species	Typhaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2921	Angelica acutiloba	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11438	Angelica gigas	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29141	Panax ginseng	Species	Araliaceae	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
EC50	2
Ki	1
Others	5

Activity Type	# Activity
Individual Protein	5
Organism	2
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1818	Individual Protein	Proline racemase	Clostridium sticklandii	Inhibition	=	98.0	%	PMID[489549]
NPT1818	Individual Protein	Proline racemase	Clostridium sticklandii	Inhibition	=	50.0	%	PMID[489549]
NPT1818	Individual Protein	Proline racemase	Clostridium sticklandii	Ki	=	5800.0	nM	PMID[489549]
NPT450	Organism	Meloidogyne incognita	Meloidogyne incognita	EC50	=	392.0	ug.mL-1	PMID[489548]
NPT450	Organism	Meloidogyne incognita	Meloidogyne incognita	EC50	>	1000.0	ug.mL-1	PMID[489548]
NPT2	Others	Unspecified		Inhibition	=	3.2	%	PMID[489550]
NPT813	Individual Protein	GABA transporter 1	Mus musculus	Activity	=	85.0	%	PMID[489551]
NPT813	Individual Protein	GABA transporter 1	Mus musculus	Activity	=	107.0	%	PMID[489552]

☑ 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 NPC23215 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	2362
0.1-0.2	15154
0.2-0.3	17555
0.3-0.4	3410
0.4-0.5	1952
0.5-0.6	1571
0.6-0.7	586
0.7-0.8	72
0.8-0.85	28
0.85-0.9	4
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9389	High Similarity	NPC291517
0.9154	High Similarity	NPC71236
0.8686	High Similarity	NPC472288
0.8647	High Similarity	NPC313823
0.8367	Intermediate Similarity	NPC33229
0.8345	Intermediate Similarity	NPC167200
0.8345	Intermediate Similarity	NPC138596
0.8345	Intermediate Similarity	NPC200397
0.8345	Intermediate Similarity	NPC98156
0.8345	Intermediate Similarity	NPC64661
0.8345	Intermediate Similarity	NPC292434
0.8345	Intermediate Similarity	NPC195704
0.8345	Intermediate Similarity	NPC14448
0.8112	Intermediate Similarity	NPC3698
0.8112	Intermediate Similarity	NPC205604
0.8112	Intermediate Similarity	NPC12831
0.8112	Intermediate Similarity	NPC97230
0.8112	Intermediate Similarity	NPC48171
0.8112	Intermediate Similarity	NPC209281
0.8112	Intermediate Similarity	NPC77582
0.8112	Intermediate Similarity	NPC286529
0.8112	Intermediate Similarity	NPC59839
0.8112	Intermediate Similarity	NPC169308
0.8112	Intermediate Similarity	NPC74928
0.8112	Intermediate Similarity	NPC129753
0.8112	Intermediate Similarity	NPC244087
0.8112	Intermediate Similarity	NPC302717
0.8056	Intermediate Similarity	NPC58268
0.8056	Intermediate Similarity	NPC129412
0.8056	Intermediate Similarity	NPC101130
0.8056	Intermediate Similarity	NPC114033
0.7987	Intermediate Similarity	NPC42372
0.7919	Intermediate Similarity	NPC471655
0.7908	Intermediate Similarity	NPC473706
0.7872	Intermediate Similarity	NPC20021
0.7871	Intermediate Similarity	NPC233380
0.7842	Intermediate Similarity	NPC471589
0.7785	Intermediate Similarity	NPC54214
0.7733	Intermediate Similarity	NPC13432
0.7692	Intermediate Similarity	NPC150592
0.7688	Intermediate Similarity	NPC293216
0.7651	Intermediate Similarity	NPC260041
0.7533	Intermediate Similarity	NPC467188
0.7516	Intermediate Similarity	NPC472260
0.7515	Intermediate Similarity	NPC102755
0.75	Intermediate Similarity	NPC474492
0.7455	Intermediate Similarity	NPC470677
0.7434	Intermediate Similarity	NPC100726
0.7419	Intermediate Similarity	NPC209362
0.7396	Intermediate Similarity	NPC209917
0.7394	Intermediate Similarity	NPC477042
0.7378	Intermediate Similarity	NPC284775
0.7365	Intermediate Similarity	NPC110158
0.7365	Intermediate Similarity	NPC104049
0.7358	Intermediate Similarity	NPC206148
0.7342	Intermediate Similarity	NPC470680
0.7342	Intermediate Similarity	NPC100104
0.7325	Intermediate Similarity	NPC213914
0.732	Intermediate Similarity	NPC105811
0.7308	Intermediate Similarity	NPC474236
0.7308	Intermediate Similarity	NPC75135
0.7278	Intermediate Similarity	NPC476527
0.7262	Intermediate Similarity	NPC477003
0.7261	Intermediate Similarity	NPC169586
0.7255	Intermediate Similarity	NPC302159
0.7244	Intermediate Similarity	NPC251391
0.7239	Intermediate Similarity	NPC262338
0.7226	Intermediate Similarity	NPC473878
0.7192	Intermediate Similarity	NPC82295
0.7188	Intermediate Similarity	NPC242116
0.7143	Intermediate Similarity	NPC274981
0.7143	Intermediate Similarity	NPC330326
0.7143	Intermediate Similarity	NPC191415
0.7119	Intermediate Similarity	NPC477045
0.7107	Intermediate Similarity	NPC76982
0.7101	Intermediate Similarity	NPC270834
0.7089	Intermediate Similarity	NPC229055
0.7083	Intermediate Similarity	NPC314281
0.7083	Intermediate Similarity	NPC40530
0.707	Intermediate Similarity	NPC70406
0.7068	Intermediate Similarity	NPC231655
0.7063	Intermediate Similarity	NPC80681
0.7059	Intermediate Similarity	NPC190296
0.7055	Intermediate Similarity	NPC114637
0.7051	Intermediate Similarity	NPC123906
0.7045	Intermediate Similarity	NPC77061
0.7044	Intermediate Similarity	NPC74357
0.7011	Intermediate Similarity	NPC210123
0.7011	Intermediate Similarity	NPC476460
0.7006	Intermediate Similarity	NPC313889
0.7	Intermediate Similarity	NPC27296
0.7	Intermediate Similarity	NPC29886
0.7	Intermediate Similarity	NPC96102
0.7	Intermediate Similarity	NPC261195
0.6994	Remote Similarity	NPC2414
0.6988	Remote Similarity	NPC80528
0.6982	Remote Similarity	NPC79777
0.6968	Remote Similarity	NPC314372
0.6968	Remote Similarity	NPC159856
0.6966	Remote Similarity	NPC477044
0.6966	Remote Similarity	NPC477041
0.6954	Remote Similarity	NPC84911
0.6954	Remote Similarity	NPC105127
0.6954	Remote Similarity	NPC154339
0.6943	Remote Similarity	NPC102664
0.6937	Remote Similarity	NPC142688
0.6932	Remote Similarity	NPC304203
0.6932	Remote Similarity	NPC326422
0.6909	Remote Similarity	NPC78020
0.6899	Remote Similarity	NPC52110
0.6882	Remote Similarity	NPC234403
0.687	Remote Similarity	NPC83987
0.6864	Remote Similarity	NPC145885
0.6864	Remote Similarity	NPC14113
0.6864	Remote Similarity	NPC84827
0.6863	Remote Similarity	NPC110126
0.6863	Remote Similarity	NPC73767
0.6857	Remote Similarity	NPC83111
0.6855	Remote Similarity	NPC217021
0.6855	Remote Similarity	NPC470679
0.6854	Remote Similarity	NPC476526
0.6854	Remote Similarity	NPC329765
0.6854	Remote Similarity	NPC48117
0.685	Remote Similarity	NPC196580
0.6845	Remote Similarity	NPC149155
0.6845	Remote Similarity	NPC110500
0.6845	Remote Similarity	NPC203468
0.6839	Remote Similarity	NPC278434
0.6836	Remote Similarity	NPC267343
0.6832	Remote Similarity	NPC469785
0.6829	Remote Similarity	NPC306160
0.6829	Remote Similarity	NPC476418
0.6828	Remote Similarity	NPC27740
0.6826	Remote Similarity	NPC302647
0.6824	Remote Similarity	NPC248041
0.6824	Remote Similarity	NPC283219
0.6824	Remote Similarity	NPC126709
0.6818	Remote Similarity	NPC230002
0.6818	Remote Similarity	NPC469761
0.6818	Remote Similarity	NPC279081
0.6818	Remote Similarity	NPC469779
0.6818	Remote Similarity	NPC469768
0.6818	Remote Similarity	NPC469767
0.6818	Remote Similarity	NPC138370
0.6818	Remote Similarity	NPC469780
0.6818	Remote Similarity	NPC469784
0.6818	Remote Similarity	NPC469783
0.6816	Remote Similarity	NPC174281
0.6816	Remote Similarity	NPC167710
0.6816	Remote Similarity	NPC475286
0.6805	Remote Similarity	NPC267885
0.6792	Remote Similarity	NPC24678
0.6792	Remote Similarity	NPC105818
0.679	Remote Similarity	NPC469762
0.6788	Remote Similarity	NPC474383
0.6788	Remote Similarity	NPC115232
0.6774	Remote Similarity	NPC469766
0.6772	Remote Similarity	NPC471957
0.677	Remote Similarity	NPC477815
0.6765	Remote Similarity	NPC240088
0.6765	Remote Similarity	NPC111275
0.6765	Remote Similarity	NPC473380
0.6761	Remote Similarity	NPC475874
0.6748	Remote Similarity	NPC230869
0.6743	Remote Similarity	NPC474259
0.6743	Remote Similarity	NPC477415
0.6743	Remote Similarity	NPC23476
0.6742	Remote Similarity	NPC473821
0.674	Remote Similarity	NPC19696
0.674	Remote Similarity	NPC477004
0.674	Remote Similarity	NPC136957
0.6739	Remote Similarity	NPC477043
0.6732	Remote Similarity	NPC114310
0.6725	Remote Similarity	NPC265710
0.6725	Remote Similarity	NPC11126
0.6725	Remote Similarity	NPC55772
0.6724	Remote Similarity	NPC295158
0.6722	Remote Similarity	NPC74153
0.6708	Remote Similarity	NPC25008
0.6708	Remote Similarity	NPC469760
0.6708	Remote Similarity	NPC469765
0.6708	Remote Similarity	NPC200214
0.6708	Remote Similarity	NPC469786
0.6708	Remote Similarity	NPC73952
0.6708	Remote Similarity	NPC469763
0.6708	Remote Similarity	NPC259644
0.6707	Remote Similarity	NPC70949
0.6705	Remote Similarity	NPC473628
0.6704	Remote Similarity	NPC202812
0.6688	Remote Similarity	NPC159630
0.6688	Remote Similarity	NPC230085
0.6686	Remote Similarity	NPC16659
0.6686	Remote Similarity	NPC63571
0.6685	Remote Similarity	NPC317701
0.6667	Remote Similarity	NPC112741
0.6667	Remote Similarity	NPC212376
0.6667	Remote Similarity	NPC70922
0.6667	Remote Similarity	NPC80597
0.6667	Remote Similarity	NPC75540
0.6667	Remote Similarity	NPC211572

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 NPC23215 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	401
0.1-0.2	1127
0.2-0.3	1571
0.3-0.4	2528
0.4-0.5	2234
0.5-0.6	1104
0.6-0.7	173
0.7-0.8	12
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7632	Intermediate Similarity	NPD9343	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD3178	Discontinued
0.7244	Intermediate Similarity	NPD180	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD1031	Discontinued
0.72	Intermediate Similarity	NPD569	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD9392	Approved
0.7174	Intermediate Similarity	NPD9396	Approved
0.7152	Intermediate Similarity	NPD9599	Approved
0.7143	Intermediate Similarity	NPD9100	Approved
0.7099	Intermediate Similarity	NPD1568	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD9099	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD9098	Phase 3
0.7059	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD272	Approved
0.7	Intermediate Similarity	NPD198	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD9598	Discontinued
0.6941	Remote Similarity	NPD1783	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD1291	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD4426	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD786	Approved
0.686	Remote Similarity	NPD1096	Discontinued
0.6859	Remote Similarity	NPD175	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD5685	Approved
0.6857	Remote Similarity	NPD5686	Approved
0.6845	Remote Similarity	NPD482	Approved
0.6818	Remote Similarity	NPD107	Approved
0.6805	Remote Similarity	NPD749	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD269	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD1722	Approved
0.6742	Remote Similarity	NPD460	Discontinued
0.6728	Remote Similarity	NPD276	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD6180	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD1627	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD9271	Approved
0.6649	Remote Similarity	NPD6288	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD4736	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD9075	Approved
0.6646	Remote Similarity	NPD9074	Approved
0.6623	Remote Similarity	NPD201	Phase 2
0.6623	Remote Similarity	NPD803	Phase 1
0.6623	Remote Similarity	NPD200	Phase 2
0.6609	Remote Similarity	NPD2094	Phase 2
0.6609	Remote Similarity	NPD2092	Phase 2
0.6609	Remote Similarity	NPD2095	Phase 2
0.6577	Remote Similarity	NPD991	Phase 2
0.6577	Remote Similarity	NPD992	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD2091	Phase 2
0.6571	Remote Similarity	NPD2096	Phase 2
0.6564	Remote Similarity	NPD2061	Approved
0.6562	Remote Similarity	NPD1270	Approved
0.6545	Remote Similarity	NPD1630	Approved
0.6522	Remote Similarity	NPD4374	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD3100	Discontinued
0.6514	Remote Similarity	NPD5728	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD1343	Approved
0.6509	Remote Similarity	NPD5069	Clinical (unspecified phase)
0.6505	Remote Similarity	NPD2121	Clinical (unspecified phase)
0.6503	Remote Similarity	NPD7459	Phase 2
0.6497	Remote Similarity	NPD5820	Clinical (unspecified phase)
0.6491	Remote Similarity	NPD750	Phase 2
0.6486	Remote Similarity	NPD9357	Approved
0.6485	Remote Similarity	NPD820	Phase 3
0.6481	Remote Similarity	NPD2172	Phase 1
0.6442	Remote Similarity	NPD510	Phase 1
0.6429	Remote Similarity	NPD1631	Approved
0.642	Remote Similarity	NPD3319	Phase 1
0.642	Remote Similarity	NPD3320	Approved
0.642	Remote Similarity	NPD3318	Approved
0.6416	Remote Similarity	NPD4075	Phase 2
0.6412	Remote Similarity	NPD1292	Clinical (unspecified phase)
0.6405	Remote Similarity	NPD9726	Discontinued
0.6402	Remote Similarity	NPD1506	Discontinued
0.64	Remote Similarity	NPD3927	Phase 2
0.64	Remote Similarity	NPD9583	Approved
0.64	Remote Similarity	NPD1618	Phase 2
0.6395	Remote Similarity	NPD268	Approved
0.6395	Remote Similarity	NPD270	Clinical (unspecified phase)
0.6395	Remote Similarity	NPD271	Approved
0.6393	Remote Similarity	NPD4848	Phase 1
0.6384	Remote Similarity	NPD7564	Discontinued
0.6383	Remote Similarity	NPD5901	Discontinued
0.6382	Remote Similarity	NPD9305	Clinical (unspecified phase)
0.6374	Remote Similarity	NPD1575	Approved
0.6374	Remote Similarity	NPD1573	Approved
0.6368	Remote Similarity	NPD2510	Approved
0.6368	Remote Similarity	NPD2509	Approved
0.6364	Remote Similarity	NPD4011	Clinical (unspecified phase)
0.6358	Remote Similarity	NPD4883	Approved
0.6349	Remote Similarity	NPD2008	Discontinued
0.6346	Remote Similarity	NPD206	Clinical (unspecified phase)
0.6341	Remote Similarity	NPD5965	Clinical (unspecified phase)
0.634	Remote Similarity	NPD3476	Approved
0.634	Remote Similarity	NPD3475	Approved
0.6338	Remote Similarity	NPD4823	Approved
0.6338	Remote Similarity	NPD4824	Approved
0.6337	Remote Similarity	NPD3347	Clinical (unspecified phase)
0.6335	Remote Similarity	NPD1600	Suspended
0.6331	Remote Similarity	NPD3583	Phase 2
0.6329	Remote Similarity	NPD4804	Approved
0.6324	Remote Similarity	NPD1982	Phase 1
0.6319	Remote Similarity	NPD60	Approved
0.6319	Remote Similarity	NPD4922	Phase 2
0.631	Remote Similarity	NPD1404	Approved
0.631	Remote Similarity	NPD1403	Approved
0.6308	Remote Similarity	NPD3389	Approved
0.6308	Remote Similarity	NPD3393	Approved
0.6308	Remote Similarity	NPD3394	Approved
0.6307	Remote Similarity	NPD2479	Phase 3
0.6307	Remote Similarity	NPD5473	Discontinued
0.6307	Remote Similarity	NPD2481	Approved
0.6303	Remote Similarity	NPD2837	Discontinued
0.6302	Remote Similarity	NPD7998	Clinical (unspecified phase)
0.6286	Remote Similarity	NPD2144	Approved
0.6286	Remote Similarity	NPD3505	Approved
0.6286	Remote Similarity	NPD3506	Approved
0.6283	Remote Similarity	NPD6459	Phase 2
0.6279	Remote Similarity	NPD4184	Clinical (unspecified phase)
0.6272	Remote Similarity	NPD5400	Approved
0.6266	Remote Similarity	NPD9076	Clinical (unspecified phase)
0.6263	Remote Similarity	NPD7289	Clinical (unspecified phase)
0.6257	Remote Similarity	NPD4174	Clinical (unspecified phase)
0.625	Remote Similarity	NPD4079	Approved
0.625	Remote Similarity	NPD7704	Clinical (unspecified phase)
0.625	Remote Similarity	NPD9080	Approved
0.625	Remote Similarity	NPD4076	Approved
0.625	Remote Similarity	NPD7618	Phase 3
0.625	Remote Similarity	NPD4805	Approved
0.625	Remote Similarity	NPD7619	Phase 3
0.6242	Remote Similarity	NPD490	Clinical (unspecified phase)
0.6233	Remote Similarity	NPD8840	Approved
0.6229	Remote Similarity	NPD3238	Discontinued
0.6226	Remote Similarity	NPD768	Clinical (unspecified phase)
0.6223	Remote Similarity	NPD5017	Discontinued
0.6216	Remote Similarity	NPD2290	Phase 3
0.6216	Remote Similarity	NPD2289	Phase 3
0.6216	Remote Similarity	NPD4811	Discontinued
0.6212	Remote Similarity	NPD5198	Approved
0.6212	Remote Similarity	NPD5199	Approved
0.6211	Remote Similarity	NPD2007	Clinical (unspecified phase)
0.6211	Remote Similarity	NPD3947	Discontinued
0.6209	Remote Similarity	NPD1095	Clinical (unspecified phase)
0.6209	Remote Similarity	NPD1905	Clinical (unspecified phase)
0.6194	Remote Similarity	NPD809	Discontinued
0.6193	Remote Similarity	NPD2753	Discontinued
0.6188	Remote Similarity	NPD4988	Discontinued
0.6188	Remote Similarity	NPD3961	Discontinued
0.6185	Remote Similarity	NPD565	Phase 2
0.618	Remote Similarity	NPD3038	Discontinued
0.6176	Remote Similarity	NPD6771	Discontinued
0.6173	Remote Similarity	NPD751	Clinical (unspecified phase)
0.6171	Remote Similarity	NPD1586	Approved
0.6171	Remote Similarity	NPD5065	Approved
0.617	Remote Similarity	NPD8248	Clinical (unspecified phase)
0.6168	Remote Similarity	NPD4436	Clinical (unspecified phase)
0.6164	Remote Similarity	NPD2896	Discontinued
0.6163	Remote Similarity	NPD2639	Approved
0.6163	Remote Similarity	NPD2642	Approved
0.6154	Remote Similarity	NPD2214	Approved
0.6154	Remote Similarity	NPD2411	Approved
0.6154	Remote Similarity	NPD2213	Approved
0.6145	Remote Similarity	NPD7401	Clinical (unspecified phase)
0.6144	Remote Similarity	NPD2119	Approved
0.6144	Remote Similarity	NPD2118	Approved
0.614	Remote Similarity	NPD3323	Discontinued
0.6133	Remote Similarity	NPD5787	Discontinued
0.6129	Remote Similarity	NPD1851	Clinical (unspecified phase)
0.6127	Remote Similarity	NPD2641	Approved
0.6127	Remote Similarity	NPD2185	Clinical (unspecified phase)
0.6127	Remote Similarity	NPD2640	Approved
0.6126	Remote Similarity	NPD3247	Clinical (unspecified phase)
0.6124	Remote Similarity	NPD6595	Phase 3
0.6118	Remote Similarity	NPD6454	Clinical (unspecified phase)
0.6117	Remote Similarity	NPD2405	Phase 3
0.6111	Remote Similarity	NPD3717	Discontinued
0.6102	Remote Similarity	NPD6203	Clinical (unspecified phase)
0.6099	Remote Similarity	NPD3246	Discontinued
0.6096	Remote Similarity	NPD6664	Approved
0.6094	Remote Similarity	NPD4862	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD165	Phase 2
0.6087	Remote Similarity	NPD1395	Clinical (unspecified phase)
0.6085	Remote Similarity	NPD484	Approved
0.6084	Remote Similarity	NPD4462	Approved
0.6084	Remote Similarity	NPD7913	Clinical (unspecified phase)
0.6084	Remote Similarity	NPD4463	Approved
0.6082	Remote Similarity	NPD1853	Clinical (unspecified phase)
0.608	Remote Similarity	NPD4128	Approved
0.608	Remote Similarity	NPD2928	Phase 2
0.6075	Remote Similarity	NPD7024	Clinical (unspecified phase)
0.6075	Remote Similarity	NPD5853	Phase 3
0.6075	Remote Similarity	NPD5855	Phase 3
0.6075	Remote Similarity	NPD953	Approved
0.6071	Remote Similarity	NPD2809	Approved
0.6069	Remote Similarity	NPD4643	Clinical (unspecified phase)
0.6069	Remote Similarity	NPD1248	Discontinued
0.6067	Remote Similarity	NPD1587	Approved
0.6062	Remote Similarity	NPD203	Clinical (unspecified phase)
0.6056	Remote Similarity	NPD1745	Approved
0.6054	Remote Similarity	NPD4376	Phase 3
0.6049	Remote Similarity	NPD3834	Clinical (unspecified phase)
0.6049	Remote Similarity	NPD5020	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