NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	206.09
Volume:	214.82
LogP:	2.526
LogD:	1.847
LogS:	-3.119
# Rotatable Bonds:	1
TPSA:	46.53
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.717
Synthetic Accessibility Score:	3.09
Fsp3:	0.417
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:	-4.586
MDCK Permeability:	2.7275360480416566e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.021
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.335

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.818
Plasma Protein Binding (PPB):	81.5751724243164%
Volume Distribution (VD):	0.671
Pgp-substrate:	19.48472785949707%

ADMET: Metabolism

CYP1A2-inhibitor:	0.859
CYP1A2-substrate:	0.687
CYP2C19-inhibitor:	0.782
CYP2C19-substrate:	0.631
CYP2C9-inhibitor:	0.242
CYP2C9-substrate:	0.807
CYP2D6-inhibitor:	0.252
CYP2D6-substrate:	0.797
CYP3A4-inhibitor:	0.43
CYP3A4-substrate:	0.402

ADMET: Excretion

Clearance (CL):	10.65
Half-life (T1/2):	0.876

ADMET: Toxicity

hERG Blockers:	0.037
Human Hepatotoxicity (H-HT):	0.219
Drug-inuced Liver Injury (DILI):	0.387
AMES Toxicity:	0.12
Rat Oral Acute Toxicity:	0.094
Maximum Recommended Daily Dose:	0.052
Skin Sensitization:	0.675
Carcinogencity:	0.542
Eye Corrosion:	0.082
Eye Irritation:	0.6
Respiratory Toxicity:	0.068

Download Data

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

Natural Product: NPC472593

Natural Product ID:	NPC472593
*Common Name:**	HNFTTYIOFJPHQE-GFCCVEGCSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	HNFTTYIOFJPHQE-GFCCVEGCSA-N
Standard InCHI:	InChI=1S/C12H14O3/c1-8-3-4-9(10(13)7-8)12(2)6-5-11(14)15-12/h3-4,7,13H,5-6H2,1-2H3/t12-/m1/s1
SMILES:	O=C1CC[C@](O1)(C)c1ccc(cc1O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3577363
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000134] Phenols [CHEMONTID:0001272] Cresols [CHEMONTID:0001273] Meta cresols

*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
NPO32607	penicillium aculeatum sd-321	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25763602]

☑ 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
LD50	1
MIC	13

Activity Type	# Activity
Organism	14

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	32.0	ug.mL-1	PMID[452722]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	32.0	ug.mL-1	PMID[452722]
NPT1843	Organism	Aeromonas hydrophila	Aeromonas hydrophila	MIC	>	32.0	ug.mL-1	PMID[452722]
NPT1844	Organism	Edwardsiella tarda	Edwardsiella tarda	MIC	>	32.0	ug.mL-1	PMID[452722]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	>	32.0	ug.mL-1	PMID[452722]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	>	32.0	ug.mL-1	PMID[452722]
NPT1845	Organism	Vibrio alginolyticus	Vibrio alginolyticus	MIC	>	32.0	ug.mL-1	PMID[452722]
NPT1311	Organism	Listonella anguillarum	Listonella anguillarum	MIC	>	32.0	ug.mL-1	PMID[452722]
NPT1726	Organism	Vibrio harveyi	Vibrio harveyi	MIC	=	4.0	ug.mL-1	PMID[452722]
NPT565	Organism	Vibrio parahaemolyticus	Vibrio parahaemolyticus	MIC	>	32.0	ug.mL-1	PMID[452722]
NPT1846	Organism	Alternaria brassicae	Alternaria brassicae	MIC	>	32.0	ug.mL-1	PMID[452722]
NPT562	Organism	Colletotrichum gloeosporioides	Colletotrichum gloeosporioides	MIC	=	32.0	ug.mL-1	PMID[452722]
NPT1847	Organism	Gaeumannomyces graminis	Gaeumannomyces graminis	MIC	=	32.0	ug.mL-1	PMID[452722]
NPT176	Organism	Artemia salina	Artemia salina	LD50	>	10.0	ug ml-1	PMID[452722]

☑ 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 NPC472593 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	256
0.1-0.2	1355
0.2-0.3	2959
0.3-0.4	8352
0.4-0.5	11130
0.5-0.6	6169
0.6-0.7	11026
0.7-0.8	1417
0.8-0.85	31
0.85-0.9	1
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8739	High Similarity	NPC328485
0.8667	High Similarity	NPC165197
0.8621	High Similarity	NPC190212
0.8595	High Similarity	NPC25168
0.8534	High Similarity	NPC26615
0.8525	High Similarity	NPC325301
0.8525	High Similarity	NPC297193
0.8516	High Similarity	NPC472591
0.8504	High Similarity	NPC7012
0.839	Intermediate Similarity	NPC41851
0.8387	Intermediate Similarity	NPC265910
0.8387	Intermediate Similarity	NPC117794
0.8387	Intermediate Similarity	NPC91475
0.8374	Intermediate Similarity	NPC327070
0.8374	Intermediate Similarity	NPC46634
0.8347	Intermediate Similarity	NPC160235
0.8333	Intermediate Similarity	NPC325295
0.8333	Intermediate Similarity	NPC160199
0.8333	Intermediate Similarity	NPC76308
0.832	Intermediate Similarity	NPC472592
0.8235	Intermediate Similarity	NPC81808
0.8231	Intermediate Similarity	NPC263817
0.823	Intermediate Similarity	NPC13426
0.8226	Intermediate Similarity	NPC477151
0.8226	Intermediate Similarity	NPC132518
0.822	Intermediate Similarity	NPC228452
0.8189	Intermediate Similarity	NPC181715
0.8182	Intermediate Similarity	NPC125252
0.816	Intermediate Similarity	NPC477152
0.813	Intermediate Similarity	NPC478121
0.8115	Intermediate Similarity	NPC94637
0.8099	Intermediate Similarity	NPC128825
0.808	Intermediate Similarity	NPC121168
0.808	Intermediate Similarity	NPC217756
0.8067	Intermediate Similarity	NPC17693
0.8065	Intermediate Similarity	NPC222876
0.8065	Intermediate Similarity	NPC35856
0.8065	Intermediate Similarity	NPC115188
0.8065	Intermediate Similarity	NPC178395
0.8065	Intermediate Similarity	NPC159760
0.8065	Intermediate Similarity	NPC241001
0.8065	Intermediate Similarity	NPC272454
0.8065	Intermediate Similarity	NPC26433
0.8065	Intermediate Similarity	NPC301987
0.8065	Intermediate Similarity	NPC244994
0.8065	Intermediate Similarity	NPC292665
0.8065	Intermediate Similarity	NPC179092
0.8062	Intermediate Similarity	NPC131684
0.8053	Intermediate Similarity	NPC72729
0.8049	Intermediate Similarity	NPC328459
0.8049	Intermediate Similarity	NPC184579
0.8049	Intermediate Similarity	NPC233165
0.8049	Intermediate Similarity	NPC90522
0.8017	Intermediate Similarity	NPC161304
0.8017	Intermediate Similarity	NPC317592
0.8	Intermediate Similarity	NPC109241
0.7984	Intermediate Similarity	NPC72977
0.7984	Intermediate Similarity	NPC474874
0.7967	Intermediate Similarity	NPC328694
0.7965	Intermediate Similarity	NPC245561
0.7949	Intermediate Similarity	NPC66834
0.7946	Intermediate Similarity	NPC259512
0.7946	Intermediate Similarity	NPC312132
0.7939	Intermediate Similarity	NPC470831
0.7939	Intermediate Similarity	NPC214702
0.792	Intermediate Similarity	NPC164852
0.7917	Intermediate Similarity	NPC280760
0.7907	Intermediate Similarity	NPC71525
0.7903	Intermediate Similarity	NPC20230
0.7903	Intermediate Similarity	NPC38181
0.7895	Intermediate Similarity	NPC211164
0.7895	Intermediate Similarity	NPC52472
0.7891	Intermediate Similarity	NPC287473
0.7886	Intermediate Similarity	NPC240664
0.7881	Intermediate Similarity	NPC31274
0.7879	Intermediate Similarity	NPC476389
0.7876	Intermediate Similarity	NPC79241
0.7876	Intermediate Similarity	NPC6597
0.7874	Intermediate Similarity	NPC275145
0.7869	Intermediate Similarity	NPC322358
0.7863	Intermediate Similarity	NPC310456
0.7857	Intermediate Similarity	NPC249340
0.7857	Intermediate Similarity	NPC322332
0.7857	Intermediate Similarity	NPC162935
0.7852	Intermediate Similarity	NPC62907
0.7851	Intermediate Similarity	NPC148969
0.7845	Intermediate Similarity	NPC130817
0.784	Intermediate Similarity	NPC233282
0.7836	Intermediate Similarity	NPC204257
0.7836	Intermediate Similarity	NPC176102
0.7836	Intermediate Similarity	NPC142027
0.7836	Intermediate Similarity	NPC71108
0.7836	Intermediate Similarity	NPC229638
0.7836	Intermediate Similarity	NPC267539
0.7836	Intermediate Similarity	NPC27407
0.7836	Intermediate Similarity	NPC29317
0.7836	Intermediate Similarity	NPC254832
0.7833	Intermediate Similarity	NPC228609
0.7826	Intermediate Similarity	NPC94343
0.7823	Intermediate Similarity	NPC206205
0.782	Intermediate Similarity	NPC157478
0.782	Intermediate Similarity	NPC289572
0.782	Intermediate Similarity	NPC295406
0.782	Intermediate Similarity	NPC200422
0.782	Intermediate Similarity	NPC43627
0.7815	Intermediate Similarity	NPC234639
0.7812	Intermediate Similarity	NPC236189
0.7812	Intermediate Similarity	NPC111088
0.7807	Intermediate Similarity	NPC299762
0.7807	Intermediate Similarity	NPC33675
0.7805	Intermediate Similarity	NPC123559
0.7797	Intermediate Similarity	NPC228737
0.7797	Intermediate Similarity	NPC34715
0.7795	Intermediate Similarity	NPC302211
0.7795	Intermediate Similarity	NPC469927
0.7795	Intermediate Similarity	NPC283514
0.7795	Intermediate Similarity	NPC244351
0.7787	Intermediate Similarity	NPC221870
0.7778	Intermediate Similarity	NPC158481
0.7778	Intermediate Similarity	NPC291454
0.7769	Intermediate Similarity	NPC257947
0.7769	Intermediate Similarity	NPC66331
0.7761	Intermediate Similarity	NPC68779
0.7761	Intermediate Similarity	NPC474097
0.7761	Intermediate Similarity	NPC4982
0.7761	Intermediate Similarity	NPC5310
0.7761	Intermediate Similarity	NPC274876
0.7761	Intermediate Similarity	NPC300776
0.7761	Intermediate Similarity	NPC176814
0.776	Intermediate Similarity	NPC42657
0.7754	Intermediate Similarity	NPC149533
0.7752	Intermediate Similarity	NPC240744
0.7752	Intermediate Similarity	NPC320847
0.7752	Intermediate Similarity	NPC167055
0.7752	Intermediate Similarity	NPC170749
0.775	Intermediate Similarity	NPC222084
0.7748	Intermediate Similarity	NPC231150
0.7744	Intermediate Similarity	NPC477406
0.7744	Intermediate Similarity	NPC470160
0.7739	Intermediate Similarity	NPC174911
0.7737	Intermediate Similarity	NPC112757
0.7737	Intermediate Similarity	NPC147379
0.7737	Intermediate Similarity	NPC275356
0.7734	Intermediate Similarity	NPC236981
0.7731	Intermediate Similarity	NPC306295
0.7727	Intermediate Similarity	NPC31539
0.7727	Intermediate Similarity	NPC475102
0.7724	Intermediate Similarity	NPC232165
0.7719	Intermediate Similarity	NPC260000
0.7717	Intermediate Similarity	NPC194416
0.7717	Intermediate Similarity	NPC177291
0.7717	Intermediate Similarity	NPC198336
0.7712	Intermediate Similarity	NPC53740
0.7712	Intermediate Similarity	NPC187913
0.771	Intermediate Similarity	NPC217431
0.7705	Intermediate Similarity	NPC211421
0.7704	Intermediate Similarity	NPC475011
0.7698	Intermediate Similarity	NPC14177
0.7692	Intermediate Similarity	NPC244513
0.7692	Intermediate Similarity	NPC227458
0.7692	Intermediate Similarity	NPC218879
0.7692	Intermediate Similarity	NPC475225
0.7687	Intermediate Similarity	NPC153783
0.768	Intermediate Similarity	NPC41567
0.768	Intermediate Similarity	NPC63010
0.768	Intermediate Similarity	NPC205502
0.7676	Intermediate Similarity	NPC53362
0.7676	Intermediate Similarity	NPC166583
0.7674	Intermediate Similarity	NPC184219
0.7674	Intermediate Similarity	NPC470162
0.7674	Intermediate Similarity	NPC474237
0.7674	Intermediate Similarity	NPC470163
0.7672	Intermediate Similarity	NPC252105
0.7669	Intermediate Similarity	NPC219892
0.7669	Intermediate Similarity	NPC189823
0.7669	Intermediate Similarity	NPC258073
0.7669	Intermediate Similarity	NPC191395
0.7669	Intermediate Similarity	NPC324488
0.7667	Intermediate Similarity	NPC471954
0.7667	Intermediate Similarity	NPC75272
0.7664	Intermediate Similarity	NPC61590
0.7664	Intermediate Similarity	NPC73078
0.7664	Intermediate Similarity	NPC319870
0.7664	Intermediate Similarity	NPC148738
0.7664	Intermediate Similarity	NPC197666
0.7664	Intermediate Similarity	NPC126739
0.7664	Intermediate Similarity	NPC327612
0.7661	Intermediate Similarity	NPC312800
0.7661	Intermediate Similarity	NPC477453
0.7661	Intermediate Similarity	NPC33717
0.7661	Intermediate Similarity	NPC128249
0.7656	Intermediate Similarity	NPC311219
0.7656	Intermediate Similarity	NPC67300
0.7656	Intermediate Similarity	NPC307174
0.7655	Intermediate Similarity	NPC271681
0.7652	Intermediate Similarity	NPC171843
0.7652	Intermediate Similarity	NPC280869
0.7652	Intermediate Similarity	NPC214246
0.7647	Intermediate Similarity	NPC475955
0.7647	Intermediate Similarity	NPC326847

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 NPC472593 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	232
0.1-0.2	862
0.2-0.3	1400
0.3-0.4	2589
0.4-0.5	2170
0.5-0.6	1315
0.6-0.7	503
0.7-0.8	79
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
0.8099	Intermediate Similarity	NPD9493	Approved
0.7946	Intermediate Similarity	NPD288	Approved
0.7891	Intermediate Similarity	NPD2797	Approved
0.7857	Intermediate Similarity	NPD844	Approved
0.784	Intermediate Similarity	NPD1778	Approved
0.7812	Intermediate Similarity	NPD1283	Approved
0.7795	Intermediate Similarity	NPD1608	Approved
0.7754	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD3764	Approved
0.7727	Intermediate Similarity	NPD411	Approved
0.7698	Intermediate Similarity	NPD4626	Approved
0.7656	Intermediate Similarity	NPD9717	Approved
0.7647	Intermediate Similarity	NPD4308	Phase 3
0.7594	Intermediate Similarity	NPD3268	Approved
0.7591	Intermediate Similarity	NPD6099	Approved
0.7591	Intermediate Similarity	NPD6100	Approved
0.7586	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7583	Intermediate Similarity	NPD74	Approved
0.7583	Intermediate Similarity	NPD9266	Approved
0.7578	Intermediate Similarity	NPD1281	Approved
0.7559	Intermediate Similarity	NPD17	Approved
0.7556	Intermediate Similarity	NPD447	Suspended
0.754	Intermediate Similarity	NPD9545	Approved
0.7521	Intermediate Similarity	NPD4750	Phase 3
0.75	Intermediate Similarity	NPD9263	Approved
0.75	Intermediate Similarity	NPD9267	Approved
0.75	Intermediate Similarity	NPD9264	Approved
0.7481	Intermediate Similarity	NPD1203	Approved
0.748	Intermediate Similarity	NPD5691	Approved
0.7464	Intermediate Similarity	NPD2935	Discontinued
0.7462	Intermediate Similarity	NPD4749	Approved
0.744	Intermediate Similarity	NPD6671	Approved
0.7422	Intermediate Similarity	NPD2932	Approved
0.7422	Intermediate Similarity	NPD3019	Approved
0.7413	Intermediate Similarity	NPD2532	Approved
0.7413	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7413	Intermediate Similarity	NPD2534	Approved
0.7413	Intermediate Similarity	NPD2533	Approved
0.741	Intermediate Similarity	NPD2346	Discontinued
0.7407	Intermediate Similarity	NPD6663	Approved
0.7402	Intermediate Similarity	NPD1759	Phase 1
0.7381	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD5736	Approved
0.736	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7357	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD4307	Phase 2
0.7348	Intermediate Similarity	NPD1164	Approved
0.7348	Intermediate Similarity	NPD3267	Approved
0.7348	Intermediate Similarity	NPD3266	Approved
0.7344	Intermediate Similarity	NPD1651	Approved
0.7333	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7323	Intermediate Similarity	NPD1758	Phase 1
0.7308	Intermediate Similarity	NPD1201	Approved
0.7308	Intermediate Similarity	NPD1535	Discovery
0.7308	Intermediate Similarity	NPD422	Phase 1
0.7308	Intermediate Similarity	NPD1611	Approved
0.7302	Intermediate Similarity	NPD256	Approved
0.7302	Intermediate Similarity	NPD255	Approved
0.7299	Intermediate Similarity	NPD6355	Discontinued
0.7299	Intermediate Similarity	NPD230	Phase 1
0.7286	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7286	Intermediate Similarity	NPD6002	Phase 3
0.7286	Intermediate Similarity	NPD6004	Phase 3
0.7286	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7286	Intermediate Similarity	NPD6005	Phase 3
0.7273	Intermediate Similarity	NPD6696	Suspended
0.7259	Intermediate Similarity	NPD4625	Phase 3
0.7252	Intermediate Similarity	NPD1481	Phase 2
0.7231	Intermediate Similarity	NPD3496	Discontinued
0.7227	Intermediate Similarity	NPD846	Approved
0.7227	Intermediate Similarity	NPD940	Approved
0.7218	Intermediate Similarity	NPD1470	Approved
0.7217	Intermediate Similarity	NPD845	Approved
0.7214	Intermediate Similarity	NPD1551	Phase 2
0.7206	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7177	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD9261	Approved
0.7163	Intermediate Similarity	NPD2344	Approved
0.7163	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7155	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7155	Intermediate Similarity	NPD1693	Approved
0.7153	Intermediate Similarity	NPD8032	Phase 2
0.7143	Intermediate Similarity	NPD7033	Discontinued
0.7143	Intermediate Similarity	NPD2799	Discontinued
0.7143	Intermediate Similarity	NPD3225	Approved
0.7133	Intermediate Similarity	NPD3750	Approved
0.7132	Intermediate Similarity	NPD1894	Discontinued
0.7132	Intermediate Similarity	NPD7095	Approved
0.7122	Intermediate Similarity	NPD6653	Approved
0.7122	Intermediate Similarity	NPD1607	Approved
0.7105	Intermediate Similarity	NPD1090	Approved
0.7105	Intermediate Similarity	NPD1086	Approved
0.7105	Intermediate Similarity	NPD1089	Approved
0.7101	Intermediate Similarity	NPD2979	Phase 3
0.7101	Intermediate Similarity	NPD4060	Phase 1
0.7095	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD3226	Approved
0.7092	Intermediate Similarity	NPD5405	Approved
0.7092	Intermediate Similarity	NPD5404	Approved
0.7092	Intermediate Similarity	NPD5408	Approved
0.7092	Intermediate Similarity	NPD5406	Approved
0.7087	Intermediate Similarity	NPD9281	Approved
0.708	Intermediate Similarity	NPD2313	Discontinued
0.708	Intermediate Similarity	NPD6798	Discontinued
0.708	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7077	Intermediate Similarity	NPD5585	Approved
0.7073	Intermediate Similarity	NPD2342	Discontinued
0.7073	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD7635	Approved
0.7059	Intermediate Similarity	NPD3020	Approved
0.7037	Intermediate Similarity	NPD2798	Approved
0.7037	Intermediate Similarity	NPD258	Approved
0.7037	Intermediate Similarity	NPD257	Approved
0.7037	Intermediate Similarity	NPD5647	Approved
0.7021	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD800	Approved
0.7014	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD8166	Discontinued
0.7014	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD7003	Approved
0.7014	Intermediate Similarity	NPD4110	Phase 3
0.7008	Intermediate Similarity	NPD1398	Phase 1
0.6984	Remote Similarity	NPD228	Approved
0.6983	Remote Similarity	NPD1088	Approved
0.6978	Remote Similarity	NPD1240	Approved
0.6978	Remote Similarity	NPD826	Approved
0.6978	Remote Similarity	NPD825	Approved
0.6977	Remote Similarity	NPD9568	Approved
0.6972	Remote Similarity	NPD4477	Approved
0.6972	Remote Similarity	NPD4476	Approved
0.6972	Remote Similarity	NPD2438	Suspended
0.697	Remote Similarity	NPD3847	Discontinued
0.6967	Remote Similarity	NPD5909	Discontinued
0.6966	Remote Similarity	NPD2309	Approved
0.6963	Remote Similarity	NPD987	Approved
0.6954	Remote Similarity	NPD37	Approved
0.6949	Remote Similarity	NPD2859	Approved
0.6949	Remote Similarity	NPD1809	Phase 2
0.6949	Remote Similarity	NPD2860	Approved
0.6948	Remote Similarity	NPD6234	Discontinued
0.694	Remote Similarity	NPD1755	Approved
0.6935	Remote Similarity	NPD290	Approved
0.6934	Remote Similarity	NPD2614	Approved
0.6934	Remote Similarity	NPD6832	Phase 2
0.6929	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD4966	Approved
0.6928	Remote Similarity	NPD4965	Approved
0.6928	Remote Similarity	NPD4967	Phase 2
0.6917	Remote Similarity	NPD1610	Phase 2
0.6913	Remote Similarity	NPD2370	Clinical (unspecified phase)
0.6912	Remote Similarity	NPD1019	Discontinued
0.6912	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6911	Remote Similarity	NPD9697	Approved
0.6899	Remote Similarity	NPD4198	Discontinued
0.6899	Remote Similarity	NPD709	Approved
0.6897	Remote Similarity	NPD1239	Approved
0.6897	Remote Similarity	NPD4628	Phase 3
0.6884	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6883	Remote Similarity	NPD3749	Approved
0.6875	Remote Similarity	NPD1241	Discontinued
0.6871	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD9269	Phase 2
0.6864	Remote Similarity	NPD2934	Approved
0.6864	Remote Similarity	NPD2933	Approved
0.6861	Remote Similarity	NPD9494	Approved
0.6861	Remote Similarity	NPD2237	Approved
0.686	Remote Similarity	NPD1242	Phase 1
0.6857	Remote Similarity	NPD4140	Approved
0.6857	Remote Similarity	NPD943	Approved
0.6855	Remote Similarity	NPD1444	Approved
0.6855	Remote Similarity	NPD1445	Approved
0.6853	Remote Similarity	NPD6032	Approved
0.6853	Remote Similarity	NPD2531	Phase 2
0.685	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD7340	Approved
0.6842	Remote Similarity	NPD1087	Approved
0.6842	Remote Similarity	NPD3026	Approved
0.6842	Remote Similarity	NPD3023	Approved
0.6838	Remote Similarity	NPD6362	Approved
0.6835	Remote Similarity	NPD1296	Phase 2
0.6833	Remote Similarity	NPD9495	Approved
0.6831	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD164	Approved
0.6825	Remote Similarity	NPD3022	Approved
0.6825	Remote Similarity	NPD3021	Approved
0.6824	Remote Similarity	NPD1578	Phase 2
0.6822	Remote Similarity	NPD2629	Approved
0.6818	Remote Similarity	NPD9268	Approved
0.6818	Remote Similarity	NPD3024	Approved
0.6818	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD3025	Approved
0.6815	Remote Similarity	NPD6232	Discontinued
0.6815	Remote Similarity	NPD4359	Approved
0.6815	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6814	Remote Similarity	NPD111	Approved
0.6809	Remote Similarity	NPD555	Phase 2
0.6809	Remote Similarity	NPD1184	Approved
0.6809	Remote Similarity	NPD4618	Approved
0.6809	Remote Similarity	NPD4622	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