NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	225.08
Volume:	235.153
LogP:	2.681
LogD:	2.415
LogS:	-3.71
# Rotatable Bonds:	0
TPSA:	42.23
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.597
Synthetic Accessibility Score:	1.999
Fsp3:	0.071
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:	-4.805
MDCK Permeability:	2.3840928406571038e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.213
30% Bioavailability (F30%):	0.068

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.848
Plasma Protein Binding (PPB):	94.7778549194336%
Volume Distribution (VD):	0.717
Pgp-substrate:	2.2218902111053467%

ADMET: Metabolism

CYP1A2-inhibitor:	0.986
CYP1A2-substrate:	0.828
CYP2C19-inhibitor:	0.81
CYP2C19-substrate:	0.247
CYP2C9-inhibitor:	0.584
CYP2C9-substrate:	0.923
CYP2D6-inhibitor:	0.74
CYP2D6-substrate:	0.842
CYP3A4-inhibitor:	0.225
CYP3A4-substrate:	0.21

ADMET: Excretion

Clearance (CL):	1.977
Half-life (T1/2):	0.326

ADMET: Toxicity

hERG Blockers:	0.011
Human Hepatotoxicity (H-HT):	0.04
Drug-inuced Liver Injury (DILI):	0.249
AMES Toxicity:	0.892
Rat Oral Acute Toxicity:	0.076
Maximum Recommended Daily Dose:	0.344
Skin Sensitization:	0.795
Carcinogencity:	0.925
Eye Corrosion:	0.035
Eye Irritation:	0.98
Respiratory Toxicity:	0.631

Download Data

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

Natural Product: NPC204867

Natural Product ID:	NPC204867
*Common Name:**	1-Hydroxy-10-Methylacridin-9-One
IUPAC Name:	1-hydroxy-10-methylacridin-9-one
Synonyms:
Standard InCHIKey:	NHYDBJFGZCQFEO-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C14H11NO2/c1-15-10-6-3-2-5-9(10)14(17)13-11(15)7-4-8-12(13)16/h2-8,16H,1H3/p-1
SMILES:	Cn1c2ccccc2c(=O)c2c1cccc2[O-]
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1288799
PubChem CID:	5376484
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001253] Quinolines and derivatives [CHEMONTID:0001908] Benzoquinolines [CHEMONTID:0000274] Acridines [CHEMONTID:0001811] Acridones

*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
NPO28975	Thamnosma rhodesica	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28975	Thamnosma rhodesica	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28975	Thamnosma rhodesica	Species	Rutaceae	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
MIC	8
Others	2
Potency	4

Activity Type	# Activity
Cell Line	2
CELL-LINE	1
Individual Protein	3
Organism	9

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT941	Cell Line	HaCaT	Homo sapiens	IC50	>	50000.0	nM	PMID[491674]
NPT1197	Individual Protein	Huntingtin	Homo sapiens	Potency	=	15848.9	nM	PMID[491675]
NPT51	Individual Protein	Microtubule-associated protein tau	Homo sapiens	Potency	=	11220.2	nM	PMID[491675]
NPT2971	Individual Protein	DNA dC->dU-editing enzyme APOBEC-3F	Homo sapiens	Potency	n.a.	891.3	nM	PMID[491675]
NPT71	Cell Line	HEK293	Homo sapiens	CC50	>	20000.0	nM	PMID[491676]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	1651.1	nM	PMID[491675]
NPT20	Organism	Candida albicans	Candida albicans	MIC	>	20000.0	nM	PMID[491676]
NPT85	Organism	Filobasidiella neoformans	Cryptococcus neoformans	MIC	>	20000.0	nM	PMID[491676]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	20000.0	nM	PMID[491676]
NPT173	Organism	Klebsiella pneumoniae	Klebsiella pneumoniae	MIC	>	20000.0	nM	PMID[491676]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	>	20000.0	nM	PMID[491676]
NPT747	Organism	Acinetobacter baumannii	Acinetobacter baumannii	MIC	>	20000.0	nM	PMID[491676]
NPT2922	Organism	Staphylococcus aureus subsp. aureus	Staphylococcus aureus subsp. aureus	MIC	>	20000.0	nM	PMID[491676]
NPT20950	CELL-LINE	Erythrocyte	n.a.	HC10	>	20.0	uM	PMID[491676]

☑ 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 NPC204867 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	498
0.1-0.2	3513
0.2-0.3	12999
0.3-0.4	5660
0.4-0.5	13952
0.5-0.6	3810
0.6-0.7	1859
0.7-0.8	379
0.8-0.85	20
0.85-0.9	4
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9313	High Similarity	NPC298320
0.8765	High Similarity	NPC206109
0.8765	High Similarity	NPC114039
0.8701	High Similarity	NPC144691
0.84	Intermediate Similarity	NPC170333
0.8324	Intermediate Similarity	NPC15987
0.8256	Intermediate Similarity	NPC150308
0.8142	Intermediate Similarity	NPC198160
0.8132	Intermediate Similarity	NPC133156
0.8121	Intermediate Similarity	NPC299582
0.8022	Intermediate Similarity	NPC288759
0.8	Intermediate Similarity	NPC234933
0.7968	Intermediate Similarity	NPC295479
0.7968	Intermediate Similarity	NPC220241
0.7966	Intermediate Similarity	NPC1820
0.7946	Intermediate Similarity	NPC212123
0.7926	Intermediate Similarity	NPC116178
0.7892	Intermediate Similarity	NPC199737
0.7884	Intermediate Similarity	NPC217903
0.7884	Intermediate Similarity	NPC321166
0.7838	Intermediate Similarity	NPC301292
0.7838	Intermediate Similarity	NPC313112
0.7737	Intermediate Similarity	NPC305542
0.772	Intermediate Similarity	NPC134702
0.772	Intermediate Similarity	NPC182853
0.7696	Intermediate Similarity	NPC30749
0.7663	Intermediate Similarity	NPC241263
0.7656	Intermediate Similarity	NPC2905
0.7656	Intermediate Similarity	NPC148391
0.7619	Intermediate Similarity	NPC93653
0.7616	Intermediate Similarity	NPC112336
0.7616	Intermediate Similarity	NPC474814
0.7604	Intermediate Similarity	NPC114468
0.7602	Intermediate Similarity	NPC329830
0.7539	Intermediate Similarity	NPC474366
0.7513	Intermediate Similarity	NPC118189
0.75	Intermediate Similarity	NPC218303
0.7457	Intermediate Similarity	NPC471778
0.7453	Intermediate Similarity	NPC301702
0.7452	Intermediate Similarity	NPC253476
0.7424	Intermediate Similarity	NPC7560
0.7424	Intermediate Similarity	NPC76478
0.7418	Intermediate Similarity	NPC45389
0.7407	Intermediate Similarity	NPC41216
0.7386	Intermediate Similarity	NPC471743
0.7385	Intermediate Similarity	NPC176113
0.7372	Intermediate Similarity	NPC314098
0.7333	Intermediate Similarity	NPC268223
0.733	Intermediate Similarity	NPC470548
0.7314	Intermediate Similarity	NPC318183
0.7308	Intermediate Similarity	NPC206186
0.7273	Intermediate Similarity	NPC195120
0.7256	Intermediate Similarity	NPC297322
0.7247	Intermediate Similarity	NPC9475
0.7241	Intermediate Similarity	NPC13249
0.7237	Intermediate Similarity	NPC257490
0.7192	Intermediate Similarity	NPC285254
0.719	Intermediate Similarity	NPC268534
0.7186	Intermediate Similarity	NPC87560
0.7182	Intermediate Similarity	NPC470317
0.7179	Intermediate Similarity	NPC305717
0.7178	Intermediate Similarity	NPC43477
0.7167	Intermediate Similarity	NPC5167
0.7167	Intermediate Similarity	NPC85613
0.7152	Intermediate Similarity	NPC323798
0.7151	Intermediate Similarity	NPC56170
0.7151	Intermediate Similarity	NPC127082
0.7143	Intermediate Similarity	NPC220337
0.7135	Intermediate Similarity	NPC475594
0.7128	Intermediate Similarity	NPC303214
0.7114	Intermediate Similarity	NPC118154
0.7114	Intermediate Similarity	NPC157983
0.7113	Intermediate Similarity	NPC478075
0.7111	Intermediate Similarity	NPC474815
0.711	Intermediate Similarity	NPC27904
0.7097	Intermediate Similarity	NPC203628
0.7095	Intermediate Similarity	NPC475607
0.7077	Intermediate Similarity	NPC86834
0.7077	Intermediate Similarity	NPC210828
0.7059	Intermediate Similarity	NPC68967
0.7056	Intermediate Similarity	NPC477187
0.7056	Intermediate Similarity	NPC23294
0.7056	Intermediate Similarity	NPC474081
0.7053	Intermediate Similarity	NPC112937
0.7043	Intermediate Similarity	NPC474059
0.7039	Intermediate Similarity	NPC303225
0.7022	Intermediate Similarity	NPC469671
0.7022	Intermediate Similarity	NPC126676
0.7005	Intermediate Similarity	NPC303951
0.7005	Intermediate Similarity	NPC92803
0.6994	Remote Similarity	NPC316574
0.6994	Remote Similarity	NPC469428
0.6993	Remote Similarity	NPC177684
0.6993	Remote Similarity	NPC291962
0.6989	Remote Similarity	NPC18890
0.6982	Remote Similarity	NPC300596
0.6982	Remote Similarity	NPC237649
0.6978	Remote Similarity	NPC166169
0.6975	Remote Similarity	NPC173295
0.6964	Remote Similarity	NPC146370
0.6959	Remote Similarity	NPC317572
0.6959	Remote Similarity	NPC134848
0.6952	Remote Similarity	NPC313293
0.6949	Remote Similarity	NPC182131
0.6948	Remote Similarity	NPC161956
0.6948	Remote Similarity	NPC258531
0.6948	Remote Similarity	NPC112373
0.6943	Remote Similarity	NPC232600
0.694	Remote Similarity	NPC327005
0.6937	Remote Similarity	NPC316746
0.6935	Remote Similarity	NPC473815
0.6927	Remote Similarity	NPC317727
0.6923	Remote Similarity	NPC474041
0.6923	Remote Similarity	NPC475761
0.6915	Remote Similarity	NPC3207
0.6915	Remote Similarity	NPC28510
0.6911	Remote Similarity	NPC90229
0.6909	Remote Similarity	NPC472243
0.6893	Remote Similarity	NPC471130
0.689	Remote Similarity	NPC43218
0.6889	Remote Similarity	NPC477185
0.6886	Remote Similarity	NPC308197
0.6882	Remote Similarity	NPC242000
0.6882	Remote Similarity	NPC194040
0.6879	Remote Similarity	NPC285394
0.6878	Remote Similarity	NPC220851
0.6875	Remote Similarity	NPC17677
0.6875	Remote Similarity	NPC88970
0.6875	Remote Similarity	NPC475983
0.6872	Remote Similarity	NPC472118
0.6865	Remote Similarity	NPC471742
0.6847	Remote Similarity	NPC247803
0.6842	Remote Similarity	NPC241392
0.6842	Remote Similarity	NPC254957
0.6839	Remote Similarity	NPC130931
0.6824	Remote Similarity	NPC476444
0.6818	Remote Similarity	NPC207873
0.6818	Remote Similarity	NPC100573
0.6807	Remote Similarity	NPC181526
0.6796	Remote Similarity	NPC73280
0.6793	Remote Similarity	NPC283810
0.6789	Remote Similarity	NPC473004
0.6788	Remote Similarity	NPC100863
0.678	Remote Similarity	NPC476231
0.678	Remote Similarity	NPC150239
0.6774	Remote Similarity	NPC302235
0.6772	Remote Similarity	NPC5630
0.6768	Remote Similarity	NPC183777
0.6752	Remote Similarity	NPC39818
0.675	Remote Similarity	NPC309845
0.675	Remote Similarity	NPC25961
0.6742	Remote Similarity	NPC313757
0.674	Remote Similarity	NPC292265
0.6739	Remote Similarity	NPC164340
0.6734	Remote Similarity	NPC39679
0.6733	Remote Similarity	NPC250448
0.6731	Remote Similarity	NPC115588
0.6731	Remote Similarity	NPC122886
0.673	Remote Similarity	NPC472244
0.673	Remote Similarity	NPC470343
0.6726	Remote Similarity	NPC472241
0.6725	Remote Similarity	NPC315829
0.6722	Remote Similarity	NPC33507
0.672	Remote Similarity	NPC183805
0.6711	Remote Similarity	NPC224584
0.6707	Remote Similarity	NPC242933
0.6707	Remote Similarity	NPC315051
0.6707	Remote Similarity	NPC238108
0.6705	Remote Similarity	NPC264400
0.6703	Remote Similarity	NPC70092
0.6703	Remote Similarity	NPC475685
0.6703	Remote Similarity	NPC39822
0.6701	Remote Similarity	NPC200836
0.6701	Remote Similarity	NPC138615
0.6701	Remote Similarity	NPC218733
0.6701	Remote Similarity	NPC132874
0.6701	Remote Similarity	NPC265642
0.6701	Remote Similarity	NPC71124
0.67	Remote Similarity	NPC237740
0.6699	Remote Similarity	NPC174760
0.6687	Remote Similarity	NPC166667
0.6684	Remote Similarity	NPC155792
0.6684	Remote Similarity	NPC471489
0.6684	Remote Similarity	NPC144381
0.6683	Remote Similarity	NPC12344
0.6683	Remote Similarity	NPC308943
0.6667	Remote Similarity	NPC184161
0.6667	Remote Similarity	NPC472114
0.6667	Remote Similarity	NPC268077
0.6667	Remote Similarity	NPC226143
0.6667	Remote Similarity	NPC280714
0.6667	Remote Similarity	NPC472115
0.6667	Remote Similarity	NPC330009
0.6667	Remote Similarity	NPC470002
0.6667	Remote Similarity	NPC194562
0.6667	Remote Similarity	NPC470001
0.6649	Remote Similarity	NPC22476
0.6649	Remote Similarity	NPC472331
0.6649	Remote Similarity	NPC126515
0.6649	Remote Similarity	NPC274002

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 NPC204867 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	334
0.1-0.2	654
0.2-0.3	895
0.3-0.4	1264
0.4-0.5	2859
0.5-0.6	2207
0.6-0.7	834
0.7-0.8	96
0.8-0.85	5
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8125	Intermediate Similarity	NPD5937	Approved
0.753	Intermediate Similarity	NPD3229	Phase 2
0.7516	Intermediate Similarity	NPD1625	Approved
0.7514	Intermediate Similarity	NPD1913	Phase 1
0.7453	Intermediate Similarity	NPD9277	Approved
0.7453	Intermediate Similarity	NPD75	Approved
0.7429	Intermediate Similarity	NPD7449	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD5194	Approved
0.7419	Intermediate Similarity	NPD5197	Approved
0.7419	Intermediate Similarity	NPD5196	Approved
0.7411	Intermediate Similarity	NPD2899	Discontinued
0.7394	Intermediate Similarity	NPD4888	Discontinued
0.7391	Intermediate Similarity	NPD9278	Suspended
0.7391	Intermediate Similarity	NPD9274	Approved
0.7391	Intermediate Similarity	NPD9276	Approved
0.7391	Intermediate Similarity	NPD9275	Approved
0.7389	Intermediate Similarity	NPD1527	Phase 2
0.7384	Intermediate Similarity	NPD1168	Approved
0.7366	Intermediate Similarity	NPD5195	Discontinued
0.7356	Intermediate Similarity	NPD5183	Approved
0.7356	Intermediate Similarity	NPD5186	Approved
0.7356	Intermediate Similarity	NPD1839	Phase 1
0.7346	Intermediate Similarity	NPD1189	Approved
0.7318	Intermediate Similarity	NPD5637	Discontinued
0.7267	Intermediate Similarity	NPD1626	Approved
0.7256	Intermediate Similarity	NPD1196	Approved
0.7247	Intermediate Similarity	NPD3793	Phase 3
0.7236	Intermediate Similarity	NPD5496	Approved
0.7229	Intermediate Similarity	NPD1543	Discontinued
0.7225	Intermediate Similarity	NPD955	Approved
0.7196	Intermediate Similarity	NPD6874	Approved
0.7195	Intermediate Similarity	NPD1195	Approved
0.7188	Intermediate Similarity	NPD2791	Discontinued
0.7188	Intermediate Similarity	NPD3298	Approved
0.7173	Intermediate Similarity	NPD7071	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD1161	Approved
0.7143	Intermediate Similarity	NPD5823	Approved
0.7143	Intermediate Similarity	NPD4668	Phase 2
0.7135	Intermediate Similarity	NPD5928	Phase 1
0.7112	Intermediate Similarity	NPD4539	Phase 1
0.711	Intermediate Similarity	NPD2506	Approved
0.7105	Intermediate Similarity	NPD3297	Approved
0.7101	Intermediate Similarity	NPD1230	Approved
0.7095	Intermediate Similarity	NPD2361	Approved
0.7092	Intermediate Similarity	NPD5860	Discontinued
0.7086	Intermediate Similarity	NPD313	Approved
0.7083	Intermediate Similarity	NPD956	Clinical (unspecified phase)
0.7072	Intermediate Similarity	NPD4329	Approved
0.7072	Intermediate Similarity	NPD4330	Approved
0.7066	Intermediate Similarity	NPD6884	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD3792	Approved
0.7056	Intermediate Similarity	NPD1170	Approved
0.7041	Intermediate Similarity	NPD2737	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD2359	Approved
0.7031	Intermediate Similarity	NPD7566	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD5610	Approved
0.701	Intermediate Similarity	NPD1294	Discontinued
0.701	Intermediate Similarity	NPD4465	Phase 2
0.701	Intermediate Similarity	NPD4467	Phase 2
0.7006	Intermediate Similarity	NPD6017	Discontinued
0.7	Intermediate Similarity	NPD4979	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD9279	Approved
0.6989	Remote Similarity	NPD6608	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD4430	Phase 2
0.6978	Remote Similarity	NPD5445	Approved
0.6954	Remote Similarity	NPD2427	Approved
0.6936	Remote Similarity	NPD2672	Discontinued
0.6935	Remote Similarity	NPD4515	Suspended
0.6927	Remote Similarity	NPD5609	Approved
0.6927	Remote Similarity	NPD5608	Approved
0.6923	Remote Similarity	NPD3782	Discontinued
0.6919	Remote Similarity	NPD648	Clinical (unspecified phase)
0.691	Remote Similarity	NPD2037	Approved
0.6902	Remote Similarity	NPD3253	Clinical (unspecified phase)
0.6898	Remote Similarity	NPD5620	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD5158	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD5159	Phase 2
0.6879	Remote Similarity	NPD5157	Phase 1
0.6868	Remote Similarity	NPD6020	Phase 2
0.6852	Remote Similarity	NPD1541	Approved
0.685	Remote Similarity	NPD7301	Phase 3
0.6836	Remote Similarity	NPD6533	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD6320	Approved
0.6831	Remote Similarity	NPD3239	Clinical (unspecified phase)
0.6823	Remote Similarity	NPD7238	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD4082	Approved
0.68	Remote Similarity	NPD308	Approved
0.68	Remote Similarity	NPD1945	Phase 1
0.6798	Remote Similarity	NPD3252	Approved
0.6796	Remote Similarity	NPD2248	Approved
0.6796	Remote Similarity	NPD1220	Phase 1
0.6796	Remote Similarity	NPD2246	Approved
0.6793	Remote Similarity	NPD6293	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD7064	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD4161	Discontinued
0.6782	Remote Similarity	NPD4562	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD5417	Clinical (unspecified phase)
0.678	Remote Similarity	NPD3783	Clinical (unspecified phase)
0.678	Remote Similarity	NPD1210	Approved
0.6776	Remote Similarity	NPD1221	Approved
0.6769	Remote Similarity	NPD5552	Discontinued
0.6765	Remote Similarity	NPD3141	Discontinued
0.6758	Remote Similarity	NPD5466	Approved
0.6758	Remote Similarity	NPD3423	Phase 2
0.6758	Remote Similarity	NPD3422	Phase 3
0.6743	Remote Similarity	NPD2469	Approved
0.6743	Remote Similarity	NPD2468	Approved
0.6743	Remote Similarity	NPD2366	Approved
0.674	Remote Similarity	NPD2431	Approved
0.674	Remote Similarity	NPD3975	Discontinued
0.674	Remote Similarity	NPD2432	Approved
0.6739	Remote Similarity	NPD7479	Phase 2
0.6738	Remote Similarity	NPD6021	Clinical (unspecified phase)
0.6737	Remote Similarity	NPD5504	Discontinued
0.6737	Remote Similarity	NPD2336	Approved
0.6735	Remote Similarity	NPD6795	Clinical (unspecified phase)
0.6734	Remote Similarity	NPD2916	Discontinued
0.673	Remote Similarity	NPD1574	Approved
0.6726	Remote Similarity	NPD2365	Approved
0.6722	Remote Similarity	NPD2454	Approved
0.6722	Remote Similarity	NPD2821	Approved
0.6722	Remote Similarity	NPD2455	Approved
0.6721	Remote Similarity	NPD5603	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD2083	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD3377	Discontinued
0.6687	Remote Similarity	NPD1593	Approved
0.6687	Remote Similarity	NPD6636	Phase 3
0.6687	Remote Similarity	NPD2670	Approved
0.6686	Remote Similarity	NPD2820	Phase 3
0.6684	Remote Similarity	NPD6321	Discontinued
0.6682	Remote Similarity	NPD4981	Phase 2
0.6667	Remote Similarity	NPD33	Approved
0.6667	Remote Similarity	NPD4456	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3446	Phase 1
0.6667	Remote Similarity	NPD6138	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4393	Approved
0.6667	Remote Similarity	NPD7324	Discontinued
0.665	Remote Similarity	NPD7300	Phase 3
0.665	Remote Similarity	NPD7302	Phase 3
0.6649	Remote Similarity	NPD4423	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD2836	Approved
0.6636	Remote Similarity	NPD6790	Phase 1
0.6634	Remote Similarity	NPD683	Approved
0.6634	Remote Similarity	NPD6567	Clinical (unspecified phase)
0.6634	Remote Similarity	NPD3949	Clinical (unspecified phase)
0.663	Remote Similarity	NPD1544	Phase 1
0.6629	Remote Similarity	NPD5086	Approved
0.6619	Remote Similarity	NPD7186	Phase 3
0.6618	Remote Similarity	NPD5433	Clinical (unspecified phase)
0.6613	Remote Similarity	NPD6654	Clinical (unspecified phase)
0.661	Remote Similarity	NPD3784	Discontinued
0.6609	Remote Similarity	NPD3277	Phase 3
0.6607	Remote Similarity	NPD3391	Approved
0.6604	Remote Similarity	NPD6199	Discontinued
0.66	Remote Similarity	NPD4596	Phase 1
0.66	Remote Similarity	NPD5143	Clinical (unspecified phase)
0.66	Remote Similarity	NPD7043	Discontinued
0.6598	Remote Similarity	NPD2307	Discontinued
0.6597	Remote Similarity	NPD5896	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD5923	Phase 1
0.6593	Remote Similarity	NPD3376	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD6744	Clinical (unspecified phase)
0.6583	Remote Similarity	NPD5102	Clinical (unspecified phase)
0.6578	Remote Similarity	NPD3470	Approved
0.6578	Remote Similarity	NPD3471	Approved
0.6567	Remote Similarity	NPD2906	Approved
0.6567	Remote Similarity	NPD3472	Approved
0.6567	Remote Similarity	NPD4022	Approved
0.6567	Remote Similarity	NPD2907	Approved
0.6562	Remote Similarity	NPD6656	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD1755	Approved
0.6561	Remote Similarity	NPD8167	Discontinued
0.6557	Remote Similarity	NPD1165	Clinical (unspecified phase)
0.6554	Remote Similarity	NPD1208	Approved
0.6554	Remote Similarity	NPD1211	Clinical (unspecified phase)
0.6548	Remote Similarity	NPD7255	Clinical (unspecified phase)
0.6546	Remote Similarity	NPD5975	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD6740	Clinical (unspecified phase)
0.6541	Remote Similarity	NPD3004	Clinical (unspecified phase)
0.6524	Remote Similarity	NPD486	Clinical (unspecified phase)
0.6524	Remote Similarity	NPD6211	Clinical (unspecified phase)
0.6517	Remote Similarity	NPD6844	Discontinued
0.6516	Remote Similarity	NPD5488	Discontinued
0.6513	Remote Similarity	NPD9376	Approved
0.6509	Remote Similarity	NPD3259	Approved
0.6505	Remote Similarity	NPD5521	Clinical (unspecified phase)
0.6503	Remote Similarity	NPD2369	Discontinued
0.6502	Remote Similarity	NPD3372	Discontinued
0.6502	Remote Similarity	NPD6525	Clinical (unspecified phase)
0.6502	Remote Similarity	NPD3986	Discontinued
0.6497	Remote Similarity	NPD1668	Clinical (unspecified phase)
0.6493	Remote Similarity	NPD3925	Approved
0.6492	Remote Similarity	NPD4948	Discontinued
0.6488	Remote Similarity	NPD6342	Discontinued
0.6485	Remote Similarity	NPD6593	Clinical (unspecified phase)
0.648	Remote Similarity	NPD6060	Clinical (unspecified phase)
0.6474	Remote Similarity	NPD160	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD4493	Discontinued
0.6471	Remote Similarity	NPD5900	Clinical (unspecified phase)
0.6465	Remote Similarity	NPD5151	Clinical (unspecified phase)

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