NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	204.08
Volume:	212.184
LogP:	2.967
LogD:	1.265
LogS:	-2.985
# Rotatable Bonds:	1
TPSA:	54.37
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.761
Synthetic Accessibility Score:	2.88
Fsp3:	0.333
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.729
MDCK Permeability:	1.4550855667039286e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.011

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.15
Plasma Protein Binding (PPB):	90.45427703857422%
Volume Distribution (VD):	0.219
Pgp-substrate:	3.6415536403656006%

ADMET: Metabolism

CYP1A2-inhibitor:	0.125
CYP1A2-substrate:	0.55
CYP2C19-inhibitor:	0.057
CYP2C19-substrate:	0.064
CYP2C9-inhibitor:	0.085
CYP2C9-substrate:	0.104
CYP2D6-inhibitor:	0.038
CYP2D6-substrate:	0.139
CYP3A4-inhibitor:	0.03
CYP3A4-substrate:	0.159

ADMET: Excretion

Clearance (CL):	1.209
Half-life (T1/2):	0.708

ADMET: Toxicity

hERG Blockers:	0.027
Human Hepatotoxicity (H-HT):	0.455
Drug-inuced Liver Injury (DILI):	0.964
AMES Toxicity:	0.013
Rat Oral Acute Toxicity:	0.234
Maximum Recommended Daily Dose:	0.1
Skin Sensitization:	0.094
Carcinogencity:	0.054
Eye Corrosion:	0.004
Eye Irritation:	0.148
Respiratory Toxicity:	0.48

Download Data

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

Natural Product: NPC476357

Natural Product ID:	NPC476357
*Common Name:**	2,6-Dimethyl-1-Oxo-4-Indanecarboxylic Acid
IUPAC Name:	2,6-dimethyl-1-oxo-2,3-dihydroindene-4-carboxylic acid
Synonyms:
Standard InCHIKey:	ASNYCVAGBSOWNP-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C12H12O3/c1-6-3-9-8(5-7(2)11(9)13)10(4-6)12(14)15/h3-4,7H,5H2,1-2H3,(H,14,15)
SMILES:	Cc1cc(C(=O)O)c2c(c1)C(=O)C(C2)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL577462
PubChem CID:	25157276
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000027] Indanes [CHEMONTID:0001151] Indanones

*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
NPO26587	Croton steenkampianus	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18855442]
NPO26587	Croton steenkampianus	Species	Euphorbiaceae	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	5

Activity Type	# Activity
Cell Line	1
Organism	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT189	Cell Line	Vero	Chlorocebus aethiops	IC50	=	1216.7	ug.mL-1	PMID[549984]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	>	49.0	ug.mL-1	PMID[549984]

☑ 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 NPC476357 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	251
0.1-0.2	1328
0.2-0.3	2932
0.3-0.4	8837
0.4-0.5	13779
0.5-0.6	10901
0.6-0.7	4063
0.7-0.8	555
0.8-0.85	35
0.85-0.9	12
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9099	High Similarity	NPC274839
0.9065	High Similarity	NPC37914
0.8772	High Similarity	NPC158157
0.8692	High Similarity	NPC25458
0.8692	High Similarity	NPC304873
0.8661	High Similarity	NPC66208
0.8644	High Similarity	NPC269923
0.8644	High Similarity	NPC167323
0.8636	High Similarity	NPC249811
0.8596	High Similarity	NPC186933
0.8571	High Similarity	NPC474057
0.8559	High Similarity	NPC318327
0.8545	High Similarity	NPC185763
0.8545	High Similarity	NPC83409
0.8505	High Similarity	NPC217621
0.85	High Similarity	NPC85511
0.8411	Intermediate Similarity	NPC229242
0.8349	Intermediate Similarity	NPC284477
0.8348	Intermediate Similarity	NPC471721
0.8319	Intermediate Similarity	NPC133302
0.8318	Intermediate Similarity	NPC253423
0.8304	Intermediate Similarity	NPC112903
0.8288	Intermediate Similarity	NPC105899
0.8273	Intermediate Similarity	NPC255676
0.8261	Intermediate Similarity	NPC93287
0.8235	Intermediate Similarity	NPC472708
0.8197	Intermediate Similarity	NPC228739
0.819	Intermediate Similarity	NPC196673
0.8182	Intermediate Similarity	NPC18785
0.8165	Intermediate Similarity	NPC228435
0.8108	Intermediate Similarity	NPC329556
0.8056	Intermediate Similarity	NPC61944
0.7965	Intermediate Similarity	NPC172483
0.7946	Intermediate Similarity	NPC247976
0.7937	Intermediate Similarity	NPC115797
0.7937	Intermediate Similarity	NPC51448
0.7931	Intermediate Similarity	NPC210089
0.7931	Intermediate Similarity	NPC475002
0.7931	Intermediate Similarity	NPC95126
0.7928	Intermediate Similarity	NPC282895
0.7903	Intermediate Similarity	NPC275145
0.7895	Intermediate Similarity	NPC244933
0.7895	Intermediate Similarity	NPC85560
0.7876	Intermediate Similarity	NPC329282
0.7863	Intermediate Similarity	NPC280789
0.7863	Intermediate Similarity	NPC292834
0.7823	Intermediate Similarity	NPC282577
0.7815	Intermediate Similarity	NPC93181
0.7815	Intermediate Similarity	NPC306740
0.7812	Intermediate Similarity	NPC82712
0.7805	Intermediate Similarity	NPC472981
0.7805	Intermediate Similarity	NPC190971
0.7788	Intermediate Similarity	NPC274443
0.776	Intermediate Similarity	NPC472704
0.7759	Intermediate Similarity	NPC85493
0.7757	Intermediate Similarity	NPC62765
0.7739	Intermediate Similarity	NPC100767
0.7727	Intermediate Similarity	NPC477596
0.7724	Intermediate Similarity	NPC470585
0.7719	Intermediate Similarity	NPC472221
0.7719	Intermediate Similarity	NPC472222
0.7699	Intermediate Similarity	NPC244427
0.7699	Intermediate Similarity	NPC222390
0.7699	Intermediate Similarity	NPC320891
0.768	Intermediate Similarity	NPC223351
0.768	Intermediate Similarity	NPC472703
0.7672	Intermediate Similarity	NPC211439
0.7667	Intermediate Similarity	NPC215419
0.7667	Intermediate Similarity	NPC474095
0.7652	Intermediate Similarity	NPC477594
0.7647	Intermediate Similarity	NPC143768
0.7647	Intermediate Similarity	NPC306977
0.7647	Intermediate Similarity	NPC287055
0.7647	Intermediate Similarity	NPC242957
0.7647	Intermediate Similarity	NPC206414
0.7638	Intermediate Similarity	NPC123506
0.7627	Intermediate Similarity	NPC265513
0.7627	Intermediate Similarity	NPC167504
0.7627	Intermediate Similarity	NPC260818
0.7627	Intermediate Similarity	NPC133308
0.7623	Intermediate Similarity	NPC228318
0.7623	Intermediate Similarity	NPC160199
0.7611	Intermediate Similarity	NPC469481
0.7607	Intermediate Similarity	NPC83628
0.7607	Intermediate Similarity	NPC265407
0.7603	Intermediate Similarity	NPC135730
0.7593	Intermediate Similarity	NPC70940
0.7593	Intermediate Similarity	NPC274455
0.7593	Intermediate Similarity	NPC86670
0.7586	Intermediate Similarity	NPC30594
0.7586	Intermediate Similarity	NPC37622
0.7583	Intermediate Similarity	NPC153053
0.7581	Intermediate Similarity	NPC232958
0.7576	Intermediate Similarity	NPC48036
0.757	Intermediate Similarity	NPC329064
0.7563	Intermediate Similarity	NPC321852
0.7563	Intermediate Similarity	NPC471188
0.7561	Intermediate Similarity	NPC472698
0.7561	Intermediate Similarity	NPC328694
0.7561	Intermediate Similarity	NPC472697
0.7559	Intermediate Similarity	NPC199273
0.7559	Intermediate Similarity	NPC236189
0.7557	Intermediate Similarity	NPC125153
0.7541	Intermediate Similarity	NPC469843
0.7541	Intermediate Similarity	NPC212891
0.7541	Intermediate Similarity	NPC83718
0.754	Intermediate Similarity	NPC307174
0.7537	Intermediate Similarity	NPC472308
0.7523	Intermediate Similarity	NPC110704
0.7522	Intermediate Similarity	NPC203925
0.7521	Intermediate Similarity	NPC221275
0.752	Intermediate Similarity	NPC144547
0.7519	Intermediate Similarity	NPC176130
0.7519	Intermediate Similarity	NPC84672
0.7519	Intermediate Similarity	NPC72667
0.7519	Intermediate Similarity	NPC19432
0.7519	Intermediate Similarity	NPC78364
0.7519	Intermediate Similarity	NPC288089
0.7519	Intermediate Similarity	NPC69424
0.75	Intermediate Similarity	NPC134120
0.75	Intermediate Similarity	NPC272524
0.75	Intermediate Similarity	NPC478107
0.75	Intermediate Similarity	NPC231717
0.75	Intermediate Similarity	NPC204784
0.75	Intermediate Similarity	NPC209632
0.75	Intermediate Similarity	NPC202015
0.75	Intermediate Similarity	NPC470649
0.75	Intermediate Similarity	NPC13784
0.7481	Intermediate Similarity	NPC471452
0.7481	Intermediate Similarity	NPC477592
0.7481	Intermediate Similarity	NPC72915
0.748	Intermediate Similarity	NPC318067
0.748	Intermediate Similarity	NPC328107
0.7477	Intermediate Similarity	NPC172925
0.7477	Intermediate Similarity	NPC322387
0.7462	Intermediate Similarity	NPC96024
0.746	Intermediate Similarity	NPC25168
0.7456	Intermediate Similarity	NPC225079
0.7456	Intermediate Similarity	NPC70624
0.7444	Intermediate Similarity	NPC126516
0.7444	Intermediate Similarity	NPC203486
0.7444	Intermediate Similarity	NPC477139
0.7444	Intermediate Similarity	NPC329913
0.7442	Intermediate Similarity	NPC472706
0.7442	Intermediate Similarity	NPC473751
0.7442	Intermediate Similarity	NPC254492
0.7442	Intermediate Similarity	NPC474106
0.744	Intermediate Similarity	NPC988
0.744	Intermediate Similarity	NPC183339
0.744	Intermediate Similarity	NPC234337
0.744	Intermediate Similarity	NPC289432
0.744	Intermediate Similarity	NPC133389
0.7438	Intermediate Similarity	NPC242136
0.7438	Intermediate Similarity	NPC307651
0.7438	Intermediate Similarity	NPC211421
0.7426	Intermediate Similarity	NPC477593
0.7426	Intermediate Similarity	NPC4214
0.7422	Intermediate Similarity	NPC295664
0.7422	Intermediate Similarity	NPC142956
0.7419	Intermediate Similarity	NPC273282
0.7419	Intermediate Similarity	NPC318173
0.7419	Intermediate Similarity	NPC474890
0.7419	Intermediate Similarity	NPC161943
0.7417	Intermediate Similarity	NPC186128
0.7417	Intermediate Similarity	NPC79496
0.7414	Intermediate Similarity	NPC31786
0.7414	Intermediate Similarity	NPC249067
0.7414	Intermediate Similarity	NPC315794
0.7414	Intermediate Similarity	NPC114594
0.7411	Intermediate Similarity	NPC261947
0.7405	Intermediate Similarity	NPC117899
0.7405	Intermediate Similarity	NPC171460
0.7395	Intermediate Similarity	NPC95172
0.7391	Intermediate Similarity	NPC45613
0.7391	Intermediate Similarity	NPC188895
0.7388	Intermediate Similarity	NPC474659
0.7383	Intermediate Similarity	NPC307
0.7383	Intermediate Similarity	NPC160339
0.7383	Intermediate Similarity	NPC318107
0.7381	Intermediate Similarity	NPC165197
0.7377	Intermediate Similarity	NPC228936
0.7373	Intermediate Similarity	NPC226699
0.7373	Intermediate Similarity	NPC34715
0.7372	Intermediate Similarity	NPC26924
0.7364	Intermediate Similarity	NPC133461
0.7355	Intermediate Similarity	NPC128368
0.7355	Intermediate Similarity	NPC470253
0.7353	Intermediate Similarity	NPC156393
0.735	Intermediate Similarity	NPC471133
0.7348	Intermediate Similarity	NPC108129
0.7345	Intermediate Similarity	NPC156021
0.7344	Intermediate Similarity	NPC273683
0.7344	Intermediate Similarity	NPC51079
0.7339	Intermediate Similarity	NPC45794
0.7339	Intermediate Similarity	NPC323440
0.7339	Intermediate Similarity	NPC80605
0.7339	Intermediate Similarity	NPC125252
0.7339	Intermediate Similarity	NPC222968
0.7328	Intermediate Similarity	NPC3009
0.7328	Intermediate Similarity	NPC95537

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 NPC476357 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	251
0.1-0.2	911
0.2-0.3	1473
0.3-0.4	2738
0.4-0.5	2458
0.5-0.6	1041
0.6-0.7	227
0.7-0.8	46
0.8-0.85	5
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8276	Intermediate Similarity	NPD5951	Approved
0.8108	Intermediate Similarity	NPD1929	Approved
0.8108	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.8108	Intermediate Similarity	NPD1930	Approved
0.7963	Intermediate Similarity	NPD1693	Approved
0.7913	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7869	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7838	Intermediate Similarity	NPD2066	Phase 3
0.7757	Intermediate Similarity	NPD9258	Approved
0.7757	Intermediate Similarity	NPD9256	Approved
0.7619	Intermediate Similarity	NPD182	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD1086	Approved
0.7593	Intermediate Similarity	NPD1090	Approved
0.7593	Intermediate Similarity	NPD1089	Approved
0.7544	Intermediate Similarity	NPD1932	Approved
0.7538	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD800	Approved
0.7479	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7479	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.7477	Intermediate Similarity	NPD688	Clinical (unspecified phase)
0.7458	Intermediate Similarity	NPD2329	Discontinued
0.7455	Intermediate Similarity	NPD1088	Approved
0.7414	Intermediate Similarity	NPD1237	Approved
0.7414	Intermediate Similarity	NPD164	Approved
0.7405	Intermediate Similarity	NPD7008	Discontinued
0.7383	Intermediate Similarity	NPD9259	Approved
0.7383	Intermediate Similarity	NPD9257	Approved
0.7339	Intermediate Similarity	NPD7610	Discontinued
0.7315	Intermediate Similarity	NPD1087	Approved
0.7308	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7302	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.728	Intermediate Similarity	NPD7009	Phase 2
0.7273	Intermediate Similarity	NPD9508	Approved
0.7273	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD1317	Discontinued
0.7236	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD1202	Approved
0.7232	Intermediate Similarity	NPD5122	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD1239	Approved
0.7193	Intermediate Similarity	NPD1566	Phase 3
0.7193	Intermediate Similarity	NPD1565	Approved
0.7193	Intermediate Similarity	NPD1564	Approved
0.7167	Intermediate Similarity	NPD2182	Approved
0.7165	Intermediate Similarity	NPD3019	Approved
0.7165	Intermediate Similarity	NPD2932	Approved
0.7143	Intermediate Similarity	NPD1508	Approved
0.7132	Intermediate Similarity	NPD4878	Approved
0.713	Intermediate Similarity	NPD9495	Approved
0.7103	Intermediate Similarity	NPD9491	Approved
0.7087	Intermediate Similarity	NPD1245	Approved
0.7083	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD1201	Approved
0.7043	Intermediate Similarity	NPD3495	Discontinued
0.7042	Intermediate Similarity	NPD7236	Approved
0.7034	Intermediate Similarity	NPD6647	Phase 2
0.7031	Intermediate Similarity	NPD2345	Approved
0.7023	Intermediate Similarity	NPD1283	Approved
0.7023	Intermediate Similarity	NPD1876	Approved
0.7	Intermediate Similarity	NPD650	Approved
0.6991	Remote Similarity	NPD7631	Approved
0.6984	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.697	Remote Similarity	NPD1164	Approved
0.697	Remote Similarity	NPD1470	Approved
0.696	Remote Similarity	NPD1246	Approved
0.696	Remote Similarity	NPD2629	Approved
0.6957	Remote Similarity	NPD1843	Approved
0.6942	Remote Similarity	NPD9264	Approved
0.6942	Remote Similarity	NPD9263	Approved
0.6942	Remote Similarity	NPD9267	Approved
0.6935	Remote Similarity	NPD5277	Phase 2
0.693	Remote Similarity	NPD1563	Approved
0.6929	Remote Similarity	NPD2346	Discontinued
0.6923	Remote Similarity	NPD1238	Approved
0.6918	Remote Similarity	NPD7239	Suspended
0.6917	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD6085	Phase 2
0.6916	Remote Similarity	NPD226	Approved
0.6912	Remote Similarity	NPD7961	Discontinued
0.6906	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD7609	Phase 3
0.6901	Remote Similarity	NPD7003	Approved
0.6899	Remote Similarity	NPD1362	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD6966	Discovery
0.6885	Remote Similarity	NPD74	Approved
0.6885	Remote Similarity	NPD9266	Approved
0.6875	Remote Similarity	NPD9545	Approved
0.6871	Remote Similarity	NPD3226	Approved
0.687	Remote Similarity	NPD9260	Approved
0.6857	Remote Similarity	NPD5408	Approved
0.6857	Remote Similarity	NPD5405	Approved
0.6857	Remote Similarity	NPD5404	Approved
0.6857	Remote Similarity	NPD5406	Approved
0.685	Remote Similarity	NPD9493	Approved
0.6838	Remote Similarity	NPD3764	Approved
0.6833	Remote Similarity	NPD5909	Discontinued
0.68	Remote Similarity	NPD6858	Approved
0.68	Remote Similarity	NPD7094	Approved
0.6794	Remote Similarity	NPD6287	Discontinued
0.6794	Remote Similarity	NPD1281	Approved
0.6788	Remote Similarity	NPD6663	Approved
0.675	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.675	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6741	Remote Similarity	NPD5736	Approved
0.6729	Remote Similarity	NPD9490	Approved
0.6726	Remote Similarity	NPD5347	Phase 2
0.6726	Remote Similarity	NPD5346	Phase 2
0.6724	Remote Similarity	NPD6048	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD6049	Phase 2
0.6718	Remote Similarity	NPD3026	Approved
0.6718	Remote Similarity	NPD4879	Approved
0.6718	Remote Similarity	NPD3023	Approved
0.6692	Remote Similarity	NPD3025	Approved
0.6692	Remote Similarity	NPD3024	Approved
0.669	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6273	Approved
0.6667	Remote Similarity	NPD7305	Phase 1
0.6667	Remote Similarity	NPD1989	Approved
0.6667	Remote Similarity	NPD5618	Discontinued
0.6667	Remote Similarity	NPD2799	Discontinued
0.6641	Remote Similarity	NPD4626	Approved
0.6636	Remote Similarity	NPD225	Approved
0.6636	Remote Similarity	NPD227	Approved
0.6612	Remote Similarity	NPD9261	Approved
0.6597	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6594	Remote Similarity	NPD3268	Approved
0.6594	Remote Similarity	NPD2313	Discontinued
0.6562	Remote Similarity	NPD9281	Approved
0.6562	Remote Similarity	NPD4766	Approved
0.6549	Remote Similarity	NPD4793	Discontinued
0.6544	Remote Similarity	NPD2798	Approved
0.6544	Remote Similarity	NPD4980	Approved
0.6533	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6533	Remote Similarity	NPD7458	Discontinued
0.6525	Remote Similarity	NPD3528	Clinical (unspecified phase)
0.6519	Remote Similarity	NPD1888	Phase 1
0.6518	Remote Similarity	NPD5734	Clinical (unspecified phase)
0.6515	Remote Similarity	NPD5305	Approved
0.6515	Remote Similarity	NPD1104	Approved
0.6515	Remote Similarity	NPD5306	Approved
0.6496	Remote Similarity	NPD845	Approved
0.6494	Remote Similarity	NPD7057	Phase 3
0.6494	Remote Similarity	NPD7058	Phase 2
0.6493	Remote Similarity	NPD3972	Approved
0.6493	Remote Similarity	NPD1608	Approved
0.6493	Remote Similarity	NPD9717	Approved
0.6486	Remote Similarity	NPD2533	Approved
0.6486	Remote Similarity	NPD2532	Approved
0.6486	Remote Similarity	NPD2534	Approved
0.6486	Remote Similarity	NPD3971	Phase 1
0.6484	Remote Similarity	NPD1280	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD2652	Approved
0.6484	Remote Similarity	NPD2650	Approved
0.6475	Remote Similarity	NPD5765	Approved
0.6471	Remote Similarity	NPD288	Approved
0.6458	Remote Similarity	NPD1471	Phase 3
0.6455	Remote Similarity	NPD942	Approved
0.6452	Remote Similarity	NPD6685	Approved
0.6444	Remote Similarity	NPD5157	Phase 1
0.6444	Remote Similarity	NPD5159	Phase 2
0.6444	Remote Similarity	NPD5158	Clinical (unspecified phase)
0.6439	Remote Similarity	NPD4102	Approved
0.6439	Remote Similarity	NPD4105	Approved
0.6439	Remote Similarity	NPD9268	Approved
0.6439	Remote Similarity	NPD1651	Approved
0.6438	Remote Similarity	NPD4628	Phase 3
0.6434	Remote Similarity	NPD4308	Phase 3
0.6429	Remote Similarity	NPD8438	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD8032	Phase 2
0.6424	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6419	Remote Similarity	NPD7390	Discontinued
0.6418	Remote Similarity	NPD4806	Approved
0.6418	Remote Similarity	NPD518	Clinical (unspecified phase)
0.6418	Remote Similarity	NPD4807	Approved
0.6414	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6406	Remote Similarity	NPD7635	Approved
0.6405	Remote Similarity	NPD3589	Clinical (unspecified phase)
0.6397	Remote Similarity	NPD1574	Approved
0.6397	Remote Similarity	NPD6330	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD2935	Discontinued
0.6385	Remote Similarity	NPD3317	Approved
0.6385	Remote Similarity	NPD255	Approved
0.6385	Remote Similarity	NPD256	Approved
0.6379	Remote Similarity	NPD3673	Approved
0.6379	Remote Similarity	NPD3672	Approved
0.6377	Remote Similarity	NPD3662	Phase 3
0.6377	Remote Similarity	NPD3664	Approved
0.6377	Remote Similarity	NPD3661	Approved
0.6377	Remote Similarity	NPD3663	Approved
0.637	Remote Similarity	NPD9269	Phase 2
0.6364	Remote Similarity	NPD4479	Discontinued
0.6357	Remote Similarity	NPD411	Approved
0.6355	Remote Similarity	NPD9716	Approved
0.635	Remote Similarity	NPD3267	Approved
0.635	Remote Similarity	NPD3266	Approved
0.635	Remote Similarity	NPD2797	Approved
0.6345	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6343	Remote Similarity	NPD4135	Approved
0.6343	Remote Similarity	NPD4106	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