NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	282.15
Volume:	292.845
LogP:	2.064
LogD:	1.204
LogS:	-2.894
# Rotatable Bonds:	6
TPSA:	97.99
# H-Bond Aceptor:	5
# H-Bond Donor:	4
# Rings:	1
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.64
Synthetic Accessibility Score:	3.275
Fsp3:	0.533
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:	-5.026
MDCK Permeability:	6.748124633304542e-06
Pgp-inhibitor:	0.002
Pgp-substrate:	0.084
Human Intestinal Absorption (HIA):	0.012
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.119

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.14
Plasma Protein Binding (PPB):	39.763328552246094%
Volume Distribution (VD):	0.387
Pgp-substrate:	51.87860107421875%

ADMET: Metabolism

CYP1A2-inhibitor:	0.033
CYP1A2-substrate:	0.455
CYP2C19-inhibitor:	0.019
CYP2C19-substrate:	0.057
CYP2C9-inhibitor:	0.038
CYP2C9-substrate:	0.128
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.117
CYP3A4-inhibitor:	0.048
CYP3A4-substrate:	0.115

ADMET: Excretion

Clearance (CL):	8.397
Half-life (T1/2):	0.847

ADMET: Toxicity

hERG Blockers:	0.037
Human Hepatotoxicity (H-HT):	0.279
Drug-inuced Liver Injury (DILI):	0.778
AMES Toxicity:	0.011
Rat Oral Acute Toxicity:	0.022
Maximum Recommended Daily Dose:	0.029
Skin Sensitization:	0.051
Carcinogencity:	0.015
Eye Corrosion:	0.004
Eye Irritation:	0.325
Respiratory Toxicity:	0.031

Download Data

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

Natural Product: NPC472592

Natural Product ID:	NPC472592
*Common Name:**	CUDGWHYJFVSILF-CVRLYYSRSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	CUDGWHYJFVSILF-CVRLYYSRSA-N
Standard InCHI:	InChI=1S/C15H22O5/c1-9(2)12(16)6-7-15(3,20)11-5-4-10(14(18)19)8-13(11)17/h4-5,8-9,12,16-17,20H,6-7H2,1-3H3,(H,18,19)/t12?,15-/m0/s1
SMILES:	CC(C(CC[C@@](c1ccc(cc1O)C(=O)O)(O)C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3577362
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids

*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[522396]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	32.0	ug.mL-1	PMID[522396]
NPT1843	Organism	Aeromonas hydrophila	Aeromonas hydrophila	MIC	=	32.0	ug.mL-1	PMID[522396]
NPT1844	Organism	Edwardsiella tarda	Edwardsiella tarda	MIC	>	32.0	ug.mL-1	PMID[522396]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	>	32.0	ug.mL-1	PMID[522396]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	>	32.0	ug.mL-1	PMID[522396]
NPT1845	Organism	Vibrio alginolyticus	Vibrio alginolyticus	MIC	>	32.0	ug.mL-1	PMID[522396]
NPT1311	Organism	Listonella anguillarum	Listonella anguillarum	MIC	>	32.0	ug.mL-1	PMID[522396]
NPT1726	Organism	Vibrio harveyi	Vibrio harveyi	MIC	=	8.0	ug.mL-1	PMID[522396]
NPT565	Organism	Vibrio parahaemolyticus	Vibrio parahaemolyticus	MIC	=	32.0	ug.mL-1	PMID[522396]
NPT1846	Organism	Alternaria brassicae	Alternaria brassicae	MIC	>	32.0	ug.mL-1	PMID[522396]
NPT562	Organism	Colletotrichum gloeosporioides	Colletotrichum gloeosporioides	MIC	>	32.0	ug.mL-1	PMID[522396]
NPT1847	Organism	Gaeumannomyces graminis	Gaeumannomyces graminis	MIC	>	32.0	ug.mL-1	PMID[522396]
NPT176	Organism	Artemia salina	Artemia salina	LD50	>	10.0	ug ml-1	PMID[522396]

☑ 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 NPC472592 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	247
0.1-0.2	1068
0.2-0.3	2750
0.3-0.4	6942
0.4-0.5	12378
0.5-0.6	5061
0.6-0.7	11254
0.7-0.8	2788
0.8-0.85	163
0.85-0.9	36
0.9-0.95	6
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9915	High Similarity	NPC117794
0.9661	High Similarity	NPC25168
0.9576	High Similarity	NPC165197
0.9417	High Similarity	NPC297193
0.9237	High Similarity	NPC160199
0.9062	High Similarity	NPC472591
0.888	High Similarity	NPC240744
0.888	High Similarity	NPC167055
0.872	High Similarity	NPC275145
0.8689	High Similarity	NPC41567
0.8583	High Similarity	NPC287473
0.8571	High Similarity	NPC477153
0.8561	High Similarity	NPC474394
0.8512	High Similarity	NPC197513
0.8504	High Similarity	NPC74507
0.8504	High Similarity	NPC234890
0.8492	Intermediate Similarity	NPC325301
0.8492	Intermediate Similarity	NPC327070
0.848	Intermediate Similarity	NPC159760
0.848	Intermediate Similarity	NPC244994
0.848	Intermediate Similarity	NPC272454
0.848	Intermediate Similarity	NPC115188
0.848	Intermediate Similarity	NPC179092
0.848	Intermediate Similarity	NPC26433
0.848	Intermediate Similarity	NPC292665
0.848	Intermediate Similarity	NPC35856
0.848	Intermediate Similarity	NPC178395
0.848	Intermediate Similarity	NPC301987
0.848	Intermediate Similarity	NPC222876
0.8473	Intermediate Similarity	NPC7012
0.8468	Intermediate Similarity	NPC233165
0.8468	Intermediate Similarity	NPC160235
0.8468	Intermediate Similarity	NPC184579
0.8455	Intermediate Similarity	NPC125252
0.845	Intermediate Similarity	NPC209959
0.8443	Intermediate Similarity	NPC161304
0.84	Intermediate Similarity	NPC328485
0.8397	Intermediate Similarity	NPC31539
0.839	Intermediate Similarity	NPC66834
0.8374	Intermediate Similarity	NPC312800
0.8361	Intermediate Similarity	NPC81808
0.8361	Intermediate Similarity	NPC41851
0.8359	Intermediate Similarity	NPC68756
0.8359	Intermediate Similarity	NPC152525
0.8358	Intermediate Similarity	NPC229638
0.8358	Intermediate Similarity	NPC267539
0.8358	Intermediate Similarity	NPC204257
0.8358	Intermediate Similarity	NPC71108
0.8358	Intermediate Similarity	NPC254832
0.8358	Intermediate Similarity	NPC29317
0.8358	Intermediate Similarity	NPC176102
0.8346	Intermediate Similarity	NPC217756
0.8346	Intermediate Similarity	NPC475192
0.832	Intermediate Similarity	NPC473767
0.832	Intermediate Similarity	NPC472593
0.8305	Intermediate Similarity	NPC187913
0.8284	Intermediate Similarity	NPC202225
0.8284	Intermediate Similarity	NPC204582
0.8284	Intermediate Similarity	NPC474097
0.8279	Intermediate Similarity	NPC190212
0.8271	Intermediate Similarity	NPC470160
0.8271	Intermediate Similarity	NPC246693
0.8271	Intermediate Similarity	NPC110609
0.8271	Intermediate Similarity	NPC242358
0.8264	Intermediate Similarity	NPC228609
0.8261	Intermediate Similarity	NPC257003
0.8254	Intermediate Similarity	NPC7151
0.8254	Intermediate Similarity	NPC473662
0.8254	Intermediate Similarity	NPC216297
0.8254	Intermediate Similarity	NPC72977
0.8244	Intermediate Similarity	NPC473744
0.8235	Intermediate Similarity	NPC34715
0.8231	Intermediate Similarity	NPC49647
0.8231	Intermediate Similarity	NPC136342
0.8231	Intermediate Similarity	NPC227741
0.8231	Intermediate Similarity	NPC295202
0.8222	Intermediate Similarity	NPC142027
0.8222	Intermediate Similarity	NPC161632
0.8217	Intermediate Similarity	NPC236189
0.8209	Intermediate Similarity	NPC200422
0.8209	Intermediate Similarity	NPC157478
0.8209	Intermediate Similarity	NPC289572
0.8209	Intermediate Similarity	NPC43627
0.8209	Intermediate Similarity	NPC295406
0.8203	Intermediate Similarity	NPC46634
0.8203	Intermediate Similarity	NPC477151
0.8203	Intermediate Similarity	NPC283514
0.8203	Intermediate Similarity	NPC132518
0.8203	Intermediate Similarity	NPC244351
0.8197	Intermediate Similarity	NPC26615
0.8195	Intermediate Similarity	NPC93015
0.8195	Intermediate Similarity	NPC473777
0.8188	Intermediate Similarity	NPC220496
0.8188	Intermediate Similarity	NPC37992
0.8188	Intermediate Similarity	NPC147542
0.8188	Intermediate Similarity	NPC42262
0.8188	Intermediate Similarity	NPC327916
0.8188	Intermediate Similarity	NPC241349
0.8188	Intermediate Similarity	NPC32749
0.8175	Intermediate Similarity	NPC90522
0.8175	Intermediate Similarity	NPC328459
0.8168	Intermediate Similarity	NPC71525
0.816	Intermediate Similarity	NPC269414
0.8154	Intermediate Similarity	NPC131799
0.8145	Intermediate Similarity	NPC240163
0.8136	Intermediate Similarity	NPC475225
0.813	Intermediate Similarity	NPC211421
0.813	Intermediate Similarity	NPC98543
0.8125	Intermediate Similarity	NPC198336
0.812	Intermediate Similarity	NPC163169
0.812	Intermediate Similarity	NPC136588
0.812	Intermediate Similarity	NPC123
0.812	Intermediate Similarity	NPC199253
0.812	Intermediate Similarity	NPC31799
0.8116	Intermediate Similarity	NPC216312
0.8116	Intermediate Similarity	NPC295339
0.8116	Intermediate Similarity	NPC476477
0.8116	Intermediate Similarity	NPC299405
0.8116	Intermediate Similarity	NPC29771
0.8116	Intermediate Similarity	NPC306835
0.8116	Intermediate Similarity	NPC111422
0.8116	Intermediate Similarity	NPC471602
0.8116	Intermediate Similarity	NPC256463
0.811	Intermediate Similarity	NPC260837
0.8099	Intermediate Similarity	NPC120536
0.8095	Intermediate Similarity	NPC94637
0.8092	Intermediate Similarity	NPC306765
0.8092	Intermediate Similarity	NPC474944
0.8088	Intermediate Similarity	NPC27407
0.8085	Intermediate Similarity	NPC103910
0.8082	Intermediate Similarity	NPC182921
0.8082	Intermediate Similarity	NPC474824
0.8082	Intermediate Similarity	NPC470408
0.8082	Intermediate Similarity	NPC218870
0.808	Intermediate Similarity	NPC128825
0.808	Intermediate Similarity	NPC477453
0.8065	Intermediate Similarity	NPC114918
0.8062	Intermediate Similarity	NPC282577
0.8062	Intermediate Similarity	NPC307174
0.806	Intermediate Similarity	NPC471851
0.8058	Intermediate Similarity	NPC183345
0.8051	Intermediate Similarity	NPC471228
0.8051	Intermediate Similarity	NPC235762
0.8051	Intermediate Similarity	NPC13426
0.8049	Intermediate Similarity	NPC228452
0.8047	Intermediate Similarity	NPC164852
0.8045	Intermediate Similarity	NPC474546
0.8045	Intermediate Similarity	NPC109123
0.8043	Intermediate Similarity	NPC126739
0.8043	Intermediate Similarity	NPC61590
0.8043	Intermediate Similarity	NPC173980
0.8043	Intermediate Similarity	NPC197666
0.8042	Intermediate Similarity	NPC81835
0.8029	Intermediate Similarity	NPC475111
0.8017	Intermediate Similarity	NPC100551
0.8016	Intermediate Similarity	NPC240664
0.8016	Intermediate Similarity	NPC325295
0.8016	Intermediate Similarity	NPC76308
0.8015	Intermediate Similarity	NPC123506
0.8	Intermediate Similarity	NPC130485
0.8	Intermediate Similarity	NPC471444
0.8	Intermediate Similarity	NPC70622
0.7986	Intermediate Similarity	NPC94781
0.7986	Intermediate Similarity	NPC86744
0.7985	Intermediate Similarity	NPC108129
0.7985	Intermediate Similarity	NPC17840
0.7985	Intermediate Similarity	NPC247477
0.7973	Intermediate Similarity	NPC474861
0.7972	Intermediate Similarity	NPC314437
0.7971	Intermediate Similarity	NPC71256
0.7971	Intermediate Similarity	NPC475957
0.797	Intermediate Similarity	NPC3009
0.797	Intermediate Similarity	NPC95537
0.797	Intermediate Similarity	NPC48248
0.797	Intermediate Similarity	NPC476024
0.7969	Intermediate Similarity	NPC206778
0.7969	Intermediate Similarity	NPC478121
0.7969	Intermediate Similarity	NPC294964
0.7969	Intermediate Similarity	NPC285829
0.7966	Intermediate Similarity	NPC304873
0.7956	Intermediate Similarity	NPC278375
0.7956	Intermediate Similarity	NPC290803
0.7955	Intermediate Similarity	NPC474945
0.7955	Intermediate Similarity	NPC3224
0.7955	Intermediate Similarity	NPC472047
0.7955	Intermediate Similarity	NPC476022
0.7953	Intermediate Similarity	NPC474890
0.7953	Intermediate Similarity	NPC161943
0.7953	Intermediate Similarity	NPC206205
0.7953	Intermediate Similarity	NPC273282
0.7953	Intermediate Similarity	NPC104514
0.7943	Intermediate Similarity	NPC474300
0.7941	Intermediate Similarity	NPC78307
0.7941	Intermediate Similarity	NPC37299
0.7941	Intermediate Similarity	NPC314048
0.7941	Intermediate Similarity	NPC52407
0.7941	Intermediate Similarity	NPC180261
0.7939	Intermediate Similarity	NPC91475
0.7939	Intermediate Similarity	NPC310540
0.7939	Intermediate Similarity	NPC265910

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 NPC472592 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	231
0.1-0.2	817
0.2-0.3	1493
0.3-0.4	2499
0.4-0.5	2246
0.5-0.6	1212
0.6-0.7	562
0.7-0.8	90
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
0.808	Intermediate Similarity	NPD9493	Approved
0.8017	Intermediate Similarity	NPD9266	Approved
0.8017	Intermediate Similarity	NPD74	Approved
0.7934	Intermediate Similarity	NPD9263	Approved
0.7934	Intermediate Similarity	NPD9264	Approved
0.7934	Intermediate Similarity	NPD9267	Approved
0.7842	Intermediate Similarity	NPD2935	Discontinued
0.7795	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD1470	Approved
0.7744	Intermediate Similarity	NPD1164	Approved
0.7714	Intermediate Similarity	NPD5406	Approved
0.7714	Intermediate Similarity	NPD5404	Approved
0.7714	Intermediate Similarity	NPD5408	Approved
0.7714	Intermediate Similarity	NPD5405	Approved
0.7687	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7638	Intermediate Similarity	NPD9281	Approved
0.7627	Intermediate Similarity	NPD288	Approved
0.7603	Intermediate Similarity	NPD9261	Approved
0.7591	Intermediate Similarity	NPD411	Approved
0.7576	Intermediate Similarity	NPD1201	Approved
0.7554	Intermediate Similarity	NPD447	Suspended
0.7554	Intermediate Similarity	NPD230	Phase 1
0.7542	Intermediate Similarity	NPD844	Approved
0.7538	Intermediate Similarity	NPD9545	Approved
0.7519	Intermediate Similarity	NPD9717	Approved
0.7519	Intermediate Similarity	NPD9269	Phase 2
0.7518	Intermediate Similarity	NPD4308	Phase 3
0.7518	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7481	Intermediate Similarity	NPD9268	Approved
0.7415	Intermediate Similarity	NPD2532	Approved
0.7415	Intermediate Similarity	NPD2534	Approved
0.7415	Intermediate Similarity	NPD2533	Approved
0.7413	Intermediate Similarity	NPD2346	Discontinued
0.7381	Intermediate Similarity	NPD4750	Phase 3
0.7379	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD4628	Phase 3
0.7361	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7357	Intermediate Similarity	NPD943	Approved
0.7353	Intermediate Similarity	NPD1203	Approved
0.7353	Intermediate Similarity	NPD2797	Approved
0.7348	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7343	Intermediate Similarity	NPD1551	Phase 2
0.7338	Intermediate Similarity	NPD3764	Approved
0.7299	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7295	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD4626	Approved
0.7286	Intermediate Similarity	NPD6663	Approved
0.7286	Intermediate Similarity	NPD520	Approved
0.7279	Intermediate Similarity	NPD1283	Approved
0.7273	Intermediate Similarity	NPD2799	Discontinued
0.7273	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD1759	Phase 1
0.7273	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD7003	Approved
0.7258	Intermediate Similarity	NPD1237	Approved
0.7246	Intermediate Similarity	NPD5736	Approved
0.7234	Intermediate Similarity	NPD4307	Phase 2
0.7231	Intermediate Similarity	NPD5951	Approved
0.7214	Intermediate Similarity	NPD3268	Approved
0.7213	Intermediate Similarity	NPD2066	Phase 3
0.7197	Intermediate Similarity	NPD1758	Phase 1
0.7194	Intermediate Similarity	NPD6832	Phase 2
0.7188	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.7183	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD1019	Discontinued
0.7174	Intermediate Similarity	NPD2798	Approved
0.7172	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7165	Intermediate Similarity	NPD2182	Approved
0.7165	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7164	Intermediate Similarity	NPD3019	Approved
0.7164	Intermediate Similarity	NPD1778	Approved
0.7164	Intermediate Similarity	NPD2932	Approved
0.7143	Intermediate Similarity	NPD8166	Discontinued
0.7133	Intermediate Similarity	NPD6273	Approved
0.7133	Intermediate Similarity	NPD1607	Approved
0.7131	Intermediate Similarity	NPD9495	Approved
0.712	Intermediate Similarity	NPD164	Approved
0.7119	Intermediate Similarity	NPD1089	Approved
0.7119	Intermediate Similarity	NPD9256	Approved
0.7119	Intermediate Similarity	NPD1086	Approved
0.7119	Intermediate Similarity	NPD9258	Approved
0.7119	Intermediate Similarity	NPD1090	Approved
0.7114	Intermediate Similarity	NPD7390	Discontinued
0.7111	Intermediate Similarity	NPD3496	Discontinued
0.7108	Intermediate Similarity	NPD8150	Discontinued
0.7105	Intermediate Similarity	NPD3226	Approved
0.7105	Intermediate Similarity	NPD7458	Discontinued
0.7099	Intermediate Similarity	NPD2629	Approved
0.7095	Intermediate Similarity	NPD6190	Approved
0.7092	Intermediate Similarity	NPD2313	Discontinued
0.709	Intermediate Similarity	NPD5691	Approved
0.7083	Intermediate Similarity	NPD845	Approved
0.7077	Intermediate Similarity	NPD7635	Approved
0.7059	Intermediate Similarity	NPD1281	Approved
0.7055	Intermediate Similarity	NPD6004	Phase 3
0.7055	Intermediate Similarity	NPD6002	Phase 3
0.7055	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD6005	Phase 3
0.7055	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD3300	Phase 2
0.7044	Intermediate Similarity	NPD6232	Discontinued
0.704	Intermediate Similarity	NPD1930	Approved
0.704	Intermediate Similarity	NPD6647	Phase 2
0.704	Intermediate Similarity	NPD1929	Approved
0.704	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD5844	Phase 1
0.7034	Intermediate Similarity	NPD1510	Phase 2
0.7034	Intermediate Similarity	NPD800	Approved
0.7027	Intermediate Similarity	NPD3750	Approved
0.7025	Intermediate Similarity	NPD1693	Approved
0.7019	Intermediate Similarity	NPD7473	Discontinued
0.7014	Intermediate Similarity	NPD6653	Approved
0.7007	Intermediate Similarity	NPD1608	Approved
0.7	Intermediate Similarity	NPD1088	Approved
0.7	Intermediate Similarity	NPD9494	Approved
0.6993	Remote Similarity	NPD1240	Approved
0.6993	Remote Similarity	NPD2979	Phase 3
0.6987	Remote Similarity	NPD5402	Approved
0.6977	Remote Similarity	NPD1317	Discontinued
0.696	Remote Similarity	NPD940	Approved
0.696	Remote Similarity	NPD1932	Approved
0.696	Remote Similarity	NPD846	Approved
0.6959	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD6355	Discontinued
0.6935	Remote Similarity	NPD3020	Approved
0.6933	Remote Similarity	NPD7236	Approved
0.6928	Remote Similarity	NPD8312	Approved
0.6928	Remote Similarity	NPD8313	Approved
0.6923	Remote Similarity	NPD7819	Suspended
0.6917	Remote Similarity	NPD255	Approved
0.6917	Remote Similarity	NPD256	Approved
0.6913	Remote Similarity	NPD3400	Discontinued
0.6912	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD2672	Discontinued
0.6901	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD7008	Discontinued
0.6899	Remote Similarity	NPD2329	Discontinued
0.6892	Remote Similarity	NPD1549	Phase 2
0.6889	Remote Similarity	NPD3091	Approved
0.6885	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD3972	Approved
0.6875	Remote Similarity	NPD826	Approved
0.6875	Remote Similarity	NPD825	Approved
0.6871	Remote Similarity	NPD2438	Suspended
0.6871	Remote Similarity	NPD6100	Approved
0.6871	Remote Similarity	NPD6099	Approved
0.6864	Remote Similarity	NPD1087	Approved
0.6859	Remote Similarity	NPD37	Approved
0.6857	Remote Similarity	NPD3094	Phase 2
0.6857	Remote Similarity	NPD3267	Approved
0.6857	Remote Similarity	NPD3266	Approved
0.6853	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD3021	Approved
0.6846	Remote Similarity	NPD3022	Approved
0.6842	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD4380	Phase 2
0.6839	Remote Similarity	NPD6599	Discontinued
0.6835	Remote Similarity	NPD7768	Phase 2
0.6835	Remote Similarity	NPD1755	Approved
0.6824	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD7239	Suspended
0.6815	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6812	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD257	Approved
0.6809	Remote Similarity	NPD5647	Approved
0.6809	Remote Similarity	NPD258	Approved
0.6807	Remote Similarity	NPD6559	Discontinued
0.6803	Remote Similarity	NPD1202	Approved
0.6803	Remote Similarity	NPD7033	Discontinued
0.6803	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD7075	Discontinued
0.6788	Remote Similarity	NPD17	Approved
0.678	Remote Similarity	NPD9259	Approved
0.678	Remote Similarity	NPD9257	Approved
0.6774	Remote Similarity	NPD3455	Phase 2
0.6772	Remote Similarity	NPD2379	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD4060	Phase 1
0.6757	Remote Similarity	NPD9570	Approved
0.6753	Remote Similarity	NPD5403	Approved
0.6752	Remote Similarity	NPD1934	Approved
0.6744	Remote Similarity	NPD1445	Approved
0.6744	Remote Similarity	NPD1444	Approved
0.6742	Remote Similarity	NPD9508	Approved
0.6739	Remote Similarity	NPD3023	Approved
0.6739	Remote Similarity	NPD3026	Approved
0.6738	Remote Similarity	NPD6362	Approved
0.6736	Remote Similarity	NPD6798	Discontinued
0.6736	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6732	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.673	Remote Similarity	NPD4967	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