NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	180.04
Volume:	177.642
LogP:	1.411
LogD:	4.981
LogS:	-1.261
# Rotatable Bonds:	3
TPSA:	74.6
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	1
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.727
Synthetic Accessibility Score:	1.615
Fsp3:	0.111
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:	-5.793
MDCK Permeability:	7.190689211711287e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.033
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.006

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.225
Plasma Protein Binding (PPB):	66.93075561523438%
Volume Distribution (VD):	0.203
Pgp-substrate:	24.71111488342285%

ADMET: Metabolism

CYP1A2-inhibitor:	0.023
CYP1A2-substrate:	0.043
CYP2C19-inhibitor:	0.041
CYP2C19-substrate:	0.046
CYP2C9-inhibitor:	0.035
CYP2C9-substrate:	0.32
CYP2D6-inhibitor:	0.049
CYP2D6-substrate:	0.083
CYP3A4-inhibitor:	0.017
CYP3A4-substrate:	0.045

ADMET: Excretion

Clearance (CL):	2.439
Half-life (T1/2):	0.921

ADMET: Toxicity

hERG Blockers:	0.019
Human Hepatotoxicity (H-HT):	0.432
Drug-inuced Liver Injury (DILI):	0.943
AMES Toxicity:	0.018
Rat Oral Acute Toxicity:	0.059
Maximum Recommended Daily Dose:	0.003
Skin Sensitization:	0.516
Carcinogencity:	0.025
Eye Corrosion:	0.53
Eye Irritation:	0.989
Respiratory Toxicity:	0.056

Download Data

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

Natural Product: NPC284477

Natural Product ID:	NPC284477
*Common Name:**	2-Carboxybenzeneacetic Acid
IUPAC Name:	2-(carboxymethyl)benzoic acid
Synonyms:
Standard InCHIKey:	ZHQLTKAVLJKSKR-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C9H8O4/c10-8(11)5-6-3-1-2-4-7(6)9(12)13/h1-4H,5H2,(H,10,11)(H,12,13)
SMILES:	c1ccc(c(c1)CC(=O)O)C(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1229545
PubChem CID:	66643
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000176] Benzoic acids and derivatives [CHEMONTID:0002565] Benzoic 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
NPO3806	Garcinia morella	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0040-4039(00)90246-6]
NPO6617	Chirita eburnea	Species	Gesneriaceae	Eukaryota	whole plant	Guangxi Province, China	2002-AUG	PMID[15921435]
NPO3806	Garcinia morella	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6202	Aglaomorpha coronans	Species	Polypodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3806	Garcinia morella	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5523	Picria felterrae	Species	Linderniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3806	Garcinia morella	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5660	Scleropyrum maingayi	Species	Cervantesiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO64	Lysidice brevicalyx	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6202	Aglaomorpha coronans	Species	Polypodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3806	Garcinia morella	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6617	Chirita eburnea	Species	Gesneriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1917	Prosopis nigra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4723	Phanerochaete velutina	Species	Phanerochaetaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5523	Picria felterrae	Species	Linderniaceae	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
IC50	1
Others	1
Potency	3

Activity Type	# Activity
Cell Line	1
Individual Protein	2
Organism	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT71	Cell Line	HEK293	Homo sapiens	Potency	n.a.	6510.4	nM	PMID[471416]
NPT49	Individual Protein	DNA-(apurinic or apyrimidinic site) lyase	Homo sapiens	Potency	n.a.	2818.4	nM	PMID[471416]
NPT670	Individual Protein	Thrombin	Homo sapiens	IC50	>	50000.0	nM	PMID[471416]
NPT2	Others	Unspecified		Potency	=	29092.9	nM	PMID[471416]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	pLD50	=	6.21	n.a.	PMID[471417]

☑ 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 NPC284477 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	277
0.1-0.2	1576
0.2-0.3	3854
0.3-0.4	10951
0.4-0.5	11236
0.5-0.6	10780
0.6-0.7	3493
0.7-0.8	482
0.8-0.85	30
0.85-0.9	12
0.9-0.95	5
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9474	High Similarity	NPC229242
0.9278	High Similarity	NPC282895
0.9175	High Similarity	NPC228435
0.9091	High Similarity	NPC255676
0.8936	High Similarity	NPC62765
0.8866	High Similarity	NPC61944
0.8835	High Similarity	NPC85493
0.88	High Similarity	NPC304873
0.8788	High Similarity	NPC217621
0.8776	High Similarity	NPC253423
0.8667	High Similarity	NPC260818
0.8654	High Similarity	NPC318327
0.8614	High Similarity	NPC25458
0.8585	High Similarity	NPC321852
0.8544	High Similarity	NPC105899
0.8532	High Similarity	NPC158157
0.8519	High Similarity	NPC306740
0.8511	High Similarity	NPC318107
0.8469	Intermediate Similarity	NPC261181
0.8447	Intermediate Similarity	NPC31786
0.8426	Intermediate Similarity	NPC153053
0.8411	Intermediate Similarity	NPC66208
0.8381	Intermediate Similarity	NPC249811
0.8349	Intermediate Similarity	NPC476357
0.8286	Intermediate Similarity	NPC119271
0.8269	Intermediate Similarity	NPC114594
0.8265	Intermediate Similarity	NPC110704
0.8252	Intermediate Similarity	NPC45613
0.8208	Intermediate Similarity	NPC211439
0.8208	Intermediate Similarity	NPC56493
0.82	Intermediate Similarity	NPC130398
0.8191	Intermediate Similarity	NPC285773
0.819	Intermediate Similarity	NPC209632
0.8182	Intermediate Similarity	NPC186933
0.8173	Intermediate Similarity	NPC89886
0.8173	Intermediate Similarity	NPC60679
0.8165	Intermediate Similarity	NPC272524
0.8148	Intermediate Similarity	NPC167504
0.8131	Intermediate Similarity	NPC17417
0.8131	Intermediate Similarity	NPC10251
0.8113	Intermediate Similarity	NPC30594
0.8113	Intermediate Similarity	NPC37622
0.8113	Intermediate Similarity	NPC184658
0.8091	Intermediate Similarity	NPC237366
0.8087	Intermediate Similarity	NPC167323
0.8087	Intermediate Similarity	NPC269923
0.8077	Intermediate Similarity	NPC320891
0.8058	Intermediate Similarity	NPC203925
0.8056	Intermediate Similarity	NPC214067
0.8056	Intermediate Similarity	NPC196246
0.8056	Intermediate Similarity	NPC174099
0.8056	Intermediate Similarity	NPC93084
0.8056	Intermediate Similarity	NPC251854
0.8041	Intermediate Similarity	NPC322387
0.8039	Intermediate Similarity	NPC249912
0.8039	Intermediate Similarity	NPC156021
0.8039	Intermediate Similarity	NPC92754
0.8039	Intermediate Similarity	NPC276775
0.8037	Intermediate Similarity	NPC29883
0.8017	Intermediate Similarity	NPC223351
0.8	Intermediate Similarity	NPC291426
0.7982	Intermediate Similarity	NPC474057
0.7982	Intermediate Similarity	NPC305912
0.7982	Intermediate Similarity	NPC1082
0.7982	Intermediate Similarity	NPC210089
0.7981	Intermediate Similarity	NPC42211
0.7963	Intermediate Similarity	NPC83628
0.7963	Intermediate Similarity	NPC99846
0.7963	Intermediate Similarity	NPC269023
0.7963	Intermediate Similarity	NPC265407
0.7961	Intermediate Similarity	NPC210529
0.7961	Intermediate Similarity	NPC160548
0.7961	Intermediate Similarity	NPC225060
0.7961	Intermediate Similarity	NPC35448
0.7961	Intermediate Similarity	NPC175852
0.7961	Intermediate Similarity	NPC78701
0.7949	Intermediate Similarity	NPC85511
0.7949	Intermediate Similarity	NPC228739
0.7928	Intermediate Similarity	NPC196673
0.7925	Intermediate Similarity	NPC329282
0.7925	Intermediate Similarity	NPC249067
0.7925	Intermediate Similarity	NPC324786
0.7909	Intermediate Similarity	NPC82899
0.7909	Intermediate Similarity	NPC270699
0.7909	Intermediate Similarity	NPC79496
0.7909	Intermediate Similarity	NPC158282
0.7905	Intermediate Similarity	NPC244427
0.7905	Intermediate Similarity	NPC222390
0.7885	Intermediate Similarity	NPC146351
0.7885	Intermediate Similarity	NPC118343
0.7885	Intermediate Similarity	NPC325497
0.7872	Intermediate Similarity	NPC127343
0.787	Intermediate Similarity	NPC226699
0.7857	Intermediate Similarity	NPC474685
0.7843	Intermediate Similarity	NPC172925
0.7838	Intermediate Similarity	NPC231717
0.783	Intermediate Similarity	NPC301943
0.783	Intermediate Similarity	NPC474365
0.783	Intermediate Similarity	NPC329556
0.783	Intermediate Similarity	NPC274443
0.7826	Intermediate Similarity	NPC472708
0.7818	Intermediate Similarity	NPC474157
0.7818	Intermediate Similarity	NPC476003
0.781	Intermediate Similarity	NPC52472
0.781	Intermediate Similarity	NPC70624
0.7807	Intermediate Similarity	NPC125252
0.78	Intermediate Similarity	NPC274455
0.78	Intermediate Similarity	NPC70940
0.78	Intermediate Similarity	NPC86670
0.7778	Intermediate Similarity	NPC6984
0.7778	Intermediate Similarity	NPC187913
0.7778	Intermediate Similarity	NPC317592
0.7778	Intermediate Similarity	NPC329064
0.7768	Intermediate Similarity	NPC307651
0.7768	Intermediate Similarity	NPC471721
0.7748	Intermediate Similarity	NPC474314
0.7739	Intermediate Similarity	NPC474890
0.7739	Intermediate Similarity	NPC273282
0.7739	Intermediate Similarity	NPC161943
0.7736	Intermediate Similarity	NPC188895
0.7732	Intermediate Similarity	NPC44546
0.7731	Intermediate Similarity	NPC246166
0.7727	Intermediate Similarity	NPC95172
0.7719	Intermediate Similarity	NPC83718
0.7719	Intermediate Similarity	NPC131192
0.7714	Intermediate Similarity	NPC245561
0.7706	Intermediate Similarity	NPC34715
0.7706	Intermediate Similarity	NPC141523
0.7699	Intermediate Similarity	NPC274839
0.7699	Intermediate Similarity	NPC210092
0.7685	Intermediate Similarity	NPC172483
0.7685	Intermediate Similarity	NPC13495
0.7685	Intermediate Similarity	NPC269457
0.7672	Intermediate Similarity	NPC233165
0.7672	Intermediate Similarity	NPC184579
0.7672	Intermediate Similarity	NPC204784
0.7664	Intermediate Similarity	NPC160382
0.7664	Intermediate Similarity	NPC13426
0.7658	Intermediate Similarity	NPC243355
0.7653	Intermediate Similarity	NPC95965
0.7652	Intermediate Similarity	NPC228318
0.7636	Intermediate Similarity	NPC100551
0.7636	Intermediate Similarity	NPC17525
0.7636	Intermediate Similarity	NPC224584
0.7636	Intermediate Similarity	NPC469636
0.7632	Intermediate Similarity	NPC100353
0.7632	Intermediate Similarity	NPC149691
0.7629	Intermediate Similarity	NPC44830
0.7629	Intermediate Similarity	NPC288903
0.7627	Intermediate Similarity	NPC198336
0.7623	Intermediate Similarity	NPC95537
0.7615	Intermediate Similarity	NPC37914
0.7611	Intermediate Similarity	NPC474363
0.7611	Intermediate Similarity	NPC211421
0.7611	Intermediate Similarity	NPC308744
0.7589	Intermediate Similarity	NPC212718
0.7589	Intermediate Similarity	NPC114682
0.7586	Intermediate Similarity	NPC94298
0.7586	Intermediate Similarity	NPC27633
0.7583	Intermediate Similarity	NPC295664
0.7568	Intermediate Similarity	NPC216122
0.7563	Intermediate Similarity	NPC283514
0.7563	Intermediate Similarity	NPC46634
0.7563	Intermediate Similarity	NPC297193
0.7563	Intermediate Similarity	NPC472703
0.7545	Intermediate Similarity	NPC156648
0.7544	Intermediate Similarity	NPC81808
0.7542	Intermediate Similarity	NPC179092
0.7542	Intermediate Similarity	NPC35856
0.7542	Intermediate Similarity	NPC292665
0.7542	Intermediate Similarity	NPC26433
0.7542	Intermediate Similarity	NPC244994
0.7542	Intermediate Similarity	NPC159760
0.7542	Intermediate Similarity	NPC165197
0.7542	Intermediate Similarity	NPC272454
0.7542	Intermediate Similarity	NPC178395
0.7542	Intermediate Similarity	NPC301987
0.7542	Intermediate Similarity	NPC115188
0.7542	Intermediate Similarity	NPC222876
0.7541	Intermediate Similarity	NPC115797
0.7541	Intermediate Similarity	NPC51448
0.7524	Intermediate Similarity	NPC289201
0.7523	Intermediate Similarity	NPC134120
0.7522	Intermediate Similarity	NPC93287
0.7522	Intermediate Similarity	NPC17693
0.7521	Intermediate Similarity	NPC61779
0.7521	Intermediate Similarity	NPC262671
0.7521	Intermediate Similarity	NPC201728
0.75	Intermediate Similarity	NPC475002
0.75	Intermediate Similarity	NPC174991
0.75	Intermediate Similarity	NPC95126
0.75	Intermediate Similarity	NPC116842
0.75	Intermediate Similarity	NPC472704
0.75	Intermediate Similarity	NPC160199
0.748	Intermediate Similarity	NPC41263
0.7479	Intermediate Similarity	NPC25168
0.7478	Intermediate Similarity	NPC322197
0.7477	Intermediate Similarity	NPC473325
0.7477	Intermediate Similarity	NPC112552
0.7477	Intermediate Similarity	NPC474364

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 NPC284477 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	257
0.1-0.2	921
0.2-0.3	1477
0.3-0.4	2861
0.4-0.5	2293
0.5-0.6	1020
0.6-0.7	249
0.7-0.8	61
0.8-0.85	8
0.85-0.9	2
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8936	High Similarity	NPD9258	Approved
0.8936	High Similarity	NPD9256	Approved
0.8511	High Similarity	NPD9259	Approved
0.8511	High Similarity	NPD9257	Approved
0.8476	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.8469	Intermediate Similarity	NPD1202	Approved
0.8447	Intermediate Similarity	NPD164	Approved
0.8191	Intermediate Similarity	NPD9491	Approved
0.8182	Intermediate Similarity	NPD5951	Approved
0.8131	Intermediate Similarity	NPD2182	Approved
0.8037	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7961	Intermediate Similarity	NPD9495	Approved
0.7925	Intermediate Similarity	NPD1237	Approved
0.7885	Intermediate Similarity	NPD1238	Approved
0.7843	Intermediate Similarity	NPD9260	Approved
0.7843	Intermediate Similarity	NPD688	Clinical (unspecified phase)
0.783	Intermediate Similarity	NPD1930	Approved
0.783	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.783	Intermediate Similarity	NPD1929	Approved
0.7818	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.78	Intermediate Similarity	NPD1090	Approved
0.78	Intermediate Similarity	NPD1086	Approved
0.78	Intermediate Similarity	NPD1089	Approved
0.7789	Intermediate Similarity	NPD226	Approved
0.7766	Intermediate Similarity	NPD9490	Approved
0.7759	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7748	Intermediate Similarity	NPD9508	Approved
0.7723	Intermediate Similarity	NPD1239	Approved
0.7714	Intermediate Similarity	NPD2066	Phase 3
0.7706	Intermediate Similarity	NPD9267	Approved
0.7706	Intermediate Similarity	NPD9264	Approved
0.7706	Intermediate Similarity	NPD9263	Approved
0.77	Intermediate Similarity	NPD800	Approved
0.7679	Intermediate Similarity	NPD5277	Phase 2
0.7647	Intermediate Similarity	NPD1088	Approved
0.7647	Intermediate Similarity	NPD182	Clinical (unspecified phase)
0.7636	Intermediate Similarity	NPD9266	Approved
0.7636	Intermediate Similarity	NPD74	Approved
0.7586	Intermediate Similarity	NPD9545	Approved
0.7573	Intermediate Similarity	NPD5122	Clinical (unspecified phase)
0.757	Intermediate Similarity	NPD1932	Approved
0.7544	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1087	Approved
0.75	Intermediate Similarity	NPD1693	Approved
0.7474	Intermediate Similarity	NPD225	Approved
0.7474	Intermediate Similarity	NPD227	Approved
0.7434	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7414	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7414	Intermediate Similarity	NPD9493	Approved
0.7391	Intermediate Similarity	NPD9281	Approved
0.736	Intermediate Similarity	NPD3764	Approved
0.7358	Intermediate Similarity	NPD1566	Phase 3
0.7358	Intermediate Similarity	NPD1564	Approved
0.7358	Intermediate Similarity	NPD1565	Approved
0.734	Intermediate Similarity	NPD9716	Approved
0.7339	Intermediate Similarity	NPD6647	Phase 2
0.7339	Intermediate Similarity	NPD9261	Approved
0.7327	Intermediate Similarity	NPD4793	Discontinued
0.7317	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7311	Intermediate Similarity	NPD1104	Approved
0.728	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD4878	Approved
0.7273	Intermediate Similarity	NPD3971	Phase 1
0.7236	Intermediate Similarity	NPD1470	Approved
0.719	Intermediate Similarity	NPD1201	Approved
0.7184	Intermediate Similarity	NPD5347	Phase 2
0.7184	Intermediate Similarity	NPD5346	Phase 2
0.7168	Intermediate Similarity	NPD2329	Discontinued
0.7167	Intermediate Similarity	NPD1362	Clinical (unspecified phase)
0.7157	Intermediate Similarity	NPD650	Approved
0.7143	Intermediate Similarity	NPD7008	Discontinued
0.7131	Intermediate Similarity	NPD9717	Approved
0.7117	Intermediate Similarity	NPD5909	Discontinued
0.7105	Intermediate Similarity	NPD1317	Discontinued
0.7097	Intermediate Similarity	NPD1164	Approved
0.7083	Intermediate Similarity	NPD9268	Approved
0.7083	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD1563	Approved
0.7049	Intermediate Similarity	NPD518	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD5738	Clinical (unspecified phase)
0.7016	Intermediate Similarity	NPD1888	Phase 1
0.701	Intermediate Similarity	NPD9294	Approved
0.6992	Remote Similarity	NPD9269	Phase 2
0.697	Remote Similarity	NPD5404	Approved
0.697	Remote Similarity	NPD5406	Approved
0.697	Remote Similarity	NPD5408	Approved
0.697	Remote Similarity	NPD5405	Approved
0.696	Remote Similarity	NPD1203	Approved
0.6949	Remote Similarity	NPD1246	Approved
0.6949	Remote Similarity	NPD2629	Approved
0.6944	Remote Similarity	NPD1989	Approved
0.6903	Remote Similarity	NPD5048	Discontinued
0.69	Remote Similarity	NPD942	Approved
0.6887	Remote Similarity	NPD7609	Phase 3
0.6885	Remote Similarity	NPD9272	Approved
0.6822	Remote Similarity	NPD7631	Approved
0.6822	Remote Similarity	NPD1508	Approved
0.6818	Remote Similarity	NPD253	Approved
0.6803	Remote Similarity	NPD4102	Approved
0.6803	Remote Similarity	NPD4105	Approved
0.6803	Remote Similarity	NPD1245	Approved
0.6796	Remote Similarity	NPD5734	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD3673	Approved
0.6792	Remote Similarity	NPD3672	Approved
0.6789	Remote Similarity	NPD5206	Clinical (unspecified phase)
0.6777	Remote Similarity	NPD1758	Phase 1
0.6774	Remote Similarity	NPD6287	Discontinued
0.6767	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD3750	Approved
0.6757	Remote Similarity	NPD9712	Approved
0.6754	Remote Similarity	NPD1040	Phase 2
0.675	Remote Similarity	NPD255	Approved
0.675	Remote Similarity	NPD256	Approved
0.6748	Remote Similarity	NPD5305	Approved
0.6748	Remote Similarity	NPD2345	Approved
0.6748	Remote Similarity	NPD5306	Approved
0.6744	Remote Similarity	NPD6966	Discovery
0.6741	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD9566	Approved
0.6721	Remote Similarity	NPD1759	Phase 1
0.672	Remote Similarity	NPD1608	Approved
0.6694	Remote Similarity	NPD9568	Approved
0.6694	Remote Similarity	NPD4879	Approved
0.6694	Remote Similarity	NPD1889	Phase 1
0.6694	Remote Similarity	NPD4135	Approved
0.6694	Remote Similarity	NPD4136	Approved
0.6694	Remote Similarity	NPD4106	Approved
0.6692	Remote Similarity	NPD2313	Discontinued
0.6692	Remote Similarity	NPD3268	Approved
0.6691	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5157	Phase 1
0.6667	Remote Similarity	NPD9711	Approved
0.6667	Remote Similarity	NPD2067	Discontinued
0.6667	Remote Similarity	NPD5159	Phase 2
0.6667	Remote Similarity	NPD2346	Discontinued
0.6667	Remote Similarity	NPD230	Phase 1
0.6667	Remote Similarity	NPD5158	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD9710	Approved
0.6642	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6642	Remote Similarity	NPD4628	Phase 3
0.6641	Remote Similarity	NPD4980	Approved
0.6641	Remote Similarity	NPD520	Approved
0.664	Remote Similarity	NPD4807	Approved
0.664	Remote Similarity	NPD4806	Approved
0.6636	Remote Similarity	NPD1843	Approved
0.662	Remote Similarity	NPD3226	Approved
0.6614	Remote Similarity	NPD1283	Approved
0.6614	Remote Similarity	NPD3225	Approved
0.6613	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD3097	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD943	Approved
0.6587	Remote Similarity	NPD1481	Phase 2
0.6587	Remote Similarity	NPD6637	Approved
0.6579	Remote Similarity	NPD5765	Approved
0.6577	Remote Similarity	NPD3495	Discontinued
0.6569	Remote Similarity	NPD1625	Approved
0.6565	Remote Similarity	NPD411	Approved
0.6562	Remote Similarity	NPD2797	Approved
0.656	Remote Similarity	NPD9692	Approved
0.656	Remote Similarity	NPD9693	Approved
0.6545	Remote Similarity	NPD6048	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD6049	Phase 2
0.6542	Remote Similarity	NPD689	Discontinued
0.6541	Remote Similarity	NPD447	Suspended
0.6522	Remote Similarity	NPD7003	Approved
0.6519	Remote Similarity	NPD3748	Approved
0.6519	Remote Similarity	NPD4308	Phase 3
0.6519	Remote Similarity	NPD2799	Discontinued
0.6514	Remote Similarity	NPD159	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD2798	Approved
0.6509	Remote Similarity	NPD506	Clinical (unspecified phase)
0.6508	Remote Similarity	NPD1535	Discovery
0.6493	Remote Similarity	NPD3528	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD1876	Approved
0.648	Remote Similarity	NPD3019	Approved
0.648	Remote Similarity	NPD17	Approved
0.648	Remote Similarity	NPD2932	Approved
0.6471	Remote Similarity	NPD1507	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD2935	Discontinued
0.6471	Remote Similarity	NPD1551	Phase 2
0.6466	Remote Similarity	NPD1240	Approved
0.6457	Remote Similarity	NPD3972	Approved
0.6455	Remote Similarity	NPD845	Approved
0.6455	Remote Similarity	NPD1066	Discontinued
0.6452	Remote Similarity	NPD1894	Discontinued
0.6446	Remote Similarity	NPD1280	Clinical (unspecified phase)
0.6446	Remote Similarity	NPD2650	Approved
0.6446	Remote Similarity	NPD1241	Discontinued
0.6446	Remote Similarity	NPD2652	Approved
0.6434	Remote Similarity	NPD3267	Approved
0.6434	Remote Similarity	NPD3266	Approved
0.6429	Remote Similarity	NPD7236	Approved
0.6423	Remote Similarity	NPD694	Clinical (unspecified phase)
0.6423	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6417	Remote Similarity	NPD969	Suspended
0.6412	Remote Similarity	NPD6832	Phase 2
0.641	Remote Similarity	NPD6685	Approved
0.6403	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6397	Remote Similarity	NPD1510	Phase 2

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