NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	266.08
Volume:	261.77
LogP:	4.09
LogD:	1.348
LogS:	-3.675
# Rotatable Bonds:	5
TPSA:	111.9
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	1
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.552
Synthetic Accessibility Score:	3.003
Fsp3:	0.308
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.028
MDCK Permeability:	5.361439889384201e-06
Pgp-inhibitor:	0.002
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.04
20% Bioavailability (F20%):	0.082
30% Bioavailability (F30%):	0.047

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.021
Plasma Protein Binding (PPB):	95.92610931396484%
Volume Distribution (VD):	0.903
Pgp-substrate:	1.844147801399231%

ADMET: Metabolism

CYP1A2-inhibitor:	0.484
CYP1A2-substrate:	0.054
CYP2C19-inhibitor:	0.04
CYP2C19-substrate:	0.064
CYP2C9-inhibitor:	0.129
CYP2C9-substrate:	0.631
CYP2D6-inhibitor:	0.044
CYP2D6-substrate:	0.16
CYP3A4-inhibitor:	0.113
CYP3A4-substrate:	0.087

ADMET: Excretion

Clearance (CL):	2.048
Half-life (T1/2):	0.474

ADMET: Toxicity

hERG Blockers:	0.0
Human Hepatotoxicity (H-HT):	0.034
Drug-inuced Liver Injury (DILI):	0.208
AMES Toxicity:	0.197
Rat Oral Acute Toxicity:	0.013
Maximum Recommended Daily Dose:	0.415
Skin Sensitization:	0.686
Carcinogencity:	0.135
Eye Corrosion:	0.089
Eye Irritation:	0.915
Respiratory Toxicity:	0.767

Download Data

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

Natural Product: NPC218333

Natural Product ID:	NPC218333
*Common Name:**	Jensenone
IUPAC Name:	2,4,6-trihydroxy-5-(3-methylbutanoyl)benzene-1,3-dicarbaldehyde
Synonyms:	Jensenone
Standard InCHIKey:	LGXKQDDWMRYQJK-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C13H14O6/c1-6(2)3-9(16)10-12(18)7(4-14)11(17)8(5-15)13(10)19/h4-6,17-19H,3H2,1-2H3
SMILES:	CC(C)CC(=O)c1c(c(C=O)c(c(C=O)c1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL427087
PubChem CID:	11594161
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0001831] Carbonyl compounds [CHEMONTID:0000118] Ketones [CHEMONTID:0003670] Aryl ketones [CHEMONTID:0004296] Phenylketones [CHEMONTID:0004298] Alkyl-phenylketones

*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
NPO15388	Eucalyptus globulus	Species	Myrtaceae	Eukaryota	n.a.	fruit	n.a.	PMID[18020353]
NPO15388	Eucalyptus globulus	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22934600]
NPO15388	Eucalyptus globulus	Species	Myrtaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[23678820]
NPO15388	Eucalyptus globulus	Species	Myrtaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[30543429]
NPO15388	Eucalyptus globulus	Species	Myrtaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[30848923]
NPO15388	Eucalyptus globulus	Species	Myrtaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[8864235]
NPO15388	Eucalyptus globulus	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15388	Eucalyptus globulus	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15388	Eucalyptus globulus	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15388	Eucalyptus globulus	Species	Myrtaceae	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	3
Others	1

Activity Type	# Activity
Organism	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT633	Organism	Leishmania donovani	Leishmania donovani	IC50	=	19.0	ug.mL-1	PMID[521729]
NPT633	Organism	Leishmania donovani	Leishmania donovani	IC90	=	35.0	ug.mL-1	PMID[521729]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IC50	=	20.0	ug.mL-1	PMID[521729]
NPT20	Organism	Candida albicans	Candida albicans	IC50	=	5.5	ug.mL-1	PMID[521729]

☑ 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 NPC218333 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	294
0.1-0.2	1555
0.2-0.3	4678
0.3-0.4	12515
0.4-0.5	7775
0.5-0.6	6915
0.6-0.7	5970
0.7-0.8	2730
0.8-0.85	197
0.85-0.9	63
0.9-0.95	3
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9914	High Similarity	NPC306288
0.9083	High Similarity	NPC226275
0.9048	High Similarity	NPC474109
0.9008	High Similarity	NPC232708
0.8968	High Similarity	NPC275504
0.8906	High Similarity	NPC474519
0.8846	High Similarity	NPC147691
0.8843	High Similarity	NPC146642
0.8843	High Similarity	NPC229649
0.8828	High Similarity	NPC103105
0.881	High Similarity	NPC476119
0.879	High Similarity	NPC475733
0.878	High Similarity	NPC65761
0.878	High Similarity	NPC472029
0.877	High Similarity	NPC215392
0.876	High Similarity	NPC474224
0.876	High Similarity	NPC474117
0.876	High Similarity	NPC294037
0.8712	High Similarity	NPC162939
0.8699	High Similarity	NPC91105
0.8699	High Similarity	NPC66252
0.8692	High Similarity	NPC474076
0.8692	High Similarity	NPC244640
0.8692	High Similarity	NPC279291
0.8692	High Similarity	NPC475917
0.8682	High Similarity	NPC285054
0.8626	High Similarity	NPC299734
0.8618	High Similarity	NPC303737
0.8595	High Similarity	NPC209486
0.8595	High Similarity	NPC40649
0.8594	High Similarity	NPC62219
0.8561	High Similarity	NPC222633
0.855	High Similarity	NPC278375
0.8548	High Similarity	NPC309765
0.8537	High Similarity	NPC149246
0.8516	High Similarity	NPC73203
0.8512	High Similarity	NPC230349
0.8492	Intermediate Similarity	NPC290466
0.8462	Intermediate Similarity	NPC27490
0.8438	Intermediate Similarity	NPC470981
0.8438	Intermediate Similarity	NPC473017
0.8425	Intermediate Similarity	NPC328983
0.8425	Intermediate Similarity	NPC267846
0.8397	Intermediate Similarity	NPC48036
0.8397	Intermediate Similarity	NPC213485
0.8397	Intermediate Similarity	NPC139074
0.8397	Intermediate Similarity	NPC40524
0.8385	Intermediate Similarity	NPC250057
0.8385	Intermediate Similarity	NPC324482
0.8385	Intermediate Similarity	NPC475042
0.8374	Intermediate Similarity	NPC161617
0.8372	Intermediate Similarity	NPC474998
0.8372	Intermediate Similarity	NPC230818
0.8359	Intermediate Similarity	NPC72158
0.8359	Intermediate Similarity	NPC23126
0.8359	Intermediate Similarity	NPC98254
0.8359	Intermediate Similarity	NPC316625
0.8359	Intermediate Similarity	NPC116513
0.8359	Intermediate Similarity	NPC266689
0.8359	Intermediate Similarity	NPC30501
0.8359	Intermediate Similarity	NPC103356
0.8359	Intermediate Similarity	NPC162612
0.8359	Intermediate Similarity	NPC329205
0.8359	Intermediate Similarity	NPC100067
0.8359	Intermediate Similarity	NPC105157
0.8359	Intermediate Similarity	NPC190043
0.8359	Intermediate Similarity	NPC169250
0.8346	Intermediate Similarity	NPC471690
0.832	Intermediate Similarity	NPC242895
0.8308	Intermediate Similarity	NPC84772
0.8308	Intermediate Similarity	NPC186628
0.8308	Intermediate Similarity	NPC296158
0.8295	Intermediate Similarity	NPC475553
0.8295	Intermediate Similarity	NPC21305
0.8295	Intermediate Similarity	NPC164894
0.8295	Intermediate Similarity	NPC221777
0.8295	Intermediate Similarity	NPC41263
0.8293	Intermediate Similarity	NPC283844
0.8284	Intermediate Similarity	NPC245058
0.8281	Intermediate Similarity	NPC62952
0.8273	Intermediate Similarity	NPC82534
0.8271	Intermediate Similarity	NPC130899
0.8271	Intermediate Similarity	NPC283590
0.8271	Intermediate Similarity	NPC61153
0.8271	Intermediate Similarity	NPC70859
0.8258	Intermediate Similarity	NPC470988
0.8254	Intermediate Similarity	NPC133909
0.8254	Intermediate Similarity	NPC32032
0.8248	Intermediate Similarity	NPC73061
0.8248	Intermediate Similarity	NPC157497
0.8248	Intermediate Similarity	NPC81337
0.8248	Intermediate Similarity	NPC285659
0.8244	Intermediate Similarity	NPC279566
0.8235	Intermediate Similarity	NPC99441
0.8231	Intermediate Similarity	NPC69235
0.8231	Intermediate Similarity	NPC212379
0.8217	Intermediate Similarity	NPC83572
0.8209	Intermediate Similarity	NPC84699
0.8209	Intermediate Similarity	NPC86524
0.8203	Intermediate Similarity	NPC477454
0.8203	Intermediate Similarity	NPC10926
0.8195	Intermediate Similarity	NPC470984
0.8195	Intermediate Similarity	NPC475088
0.8182	Intermediate Similarity	NPC175738
0.8182	Intermediate Similarity	NPC185624
0.8175	Intermediate Similarity	NPC115159
0.8175	Intermediate Similarity	NPC156139
0.8175	Intermediate Similarity	NPC19174
0.8175	Intermediate Similarity	NPC45438
0.8175	Intermediate Similarity	NPC37530
0.8175	Intermediate Similarity	NPC224273
0.8175	Intermediate Similarity	NPC143427
0.8175	Intermediate Similarity	NPC73532
0.8175	Intermediate Similarity	NPC267552
0.8168	Intermediate Similarity	NPC21378
0.8168	Intermediate Similarity	NPC470987
0.8162	Intermediate Similarity	NPC471620
0.816	Intermediate Similarity	NPC294964
0.8148	Intermediate Similarity	NPC178467
0.8148	Intermediate Similarity	NPC474849
0.8148	Intermediate Similarity	NPC149372
0.8148	Intermediate Similarity	NPC156910
0.8148	Intermediate Similarity	NPC474771
0.8148	Intermediate Similarity	NPC65837
0.814	Intermediate Similarity	NPC473691
0.814	Intermediate Similarity	NPC473751
0.814	Intermediate Similarity	NPC8745
0.8134	Intermediate Similarity	NPC470210
0.8134	Intermediate Similarity	NPC164136
0.8129	Intermediate Similarity	NPC5990
0.8125	Intermediate Similarity	NPC13238
0.812	Intermediate Similarity	NPC267205
0.812	Intermediate Similarity	NPC215875
0.812	Intermediate Similarity	NPC15834
0.8115	Intermediate Similarity	NPC276111
0.8115	Intermediate Similarity	NPC118288
0.8095	Intermediate Similarity	NPC297186
0.8092	Intermediate Similarity	NPC102829
0.8092	Intermediate Similarity	NPC120488
0.8088	Intermediate Similarity	NPC475974
0.8088	Intermediate Similarity	NPC322301
0.8088	Intermediate Similarity	NPC255801
0.8088	Intermediate Similarity	NPC472403
0.8077	Intermediate Similarity	NPC128428
0.8077	Intermediate Similarity	NPC305518
0.8074	Intermediate Similarity	NPC156967
0.8074	Intermediate Similarity	NPC60667
0.8071	Intermediate Similarity	NPC110776
0.8071	Intermediate Similarity	NPC473692
0.8071	Intermediate Similarity	NPC271590
0.8065	Intermediate Similarity	NPC121259
0.8062	Intermediate Similarity	NPC201728
0.8062	Intermediate Similarity	NPC262671
0.806	Intermediate Similarity	NPC16197
0.806	Intermediate Similarity	NPC282780
0.806	Intermediate Similarity	NPC166480
0.806	Intermediate Similarity	NPC474394
0.8043	Intermediate Similarity	NPC307990
0.8043	Intermediate Similarity	NPC16455
0.8031	Intermediate Similarity	NPC196976
0.803	Intermediate Similarity	NPC147757
0.8029	Intermediate Similarity	NPC88269
0.8029	Intermediate Similarity	NPC474655
0.8016	Intermediate Similarity	NPC159525
0.8015	Intermediate Similarity	NPC470985
0.8015	Intermediate Similarity	NPC470989
0.8014	Intermediate Similarity	NPC476153
0.8014	Intermediate Similarity	NPC215885
0.8014	Intermediate Similarity	NPC2416
0.8	Intermediate Similarity	NPC290803
0.8	Intermediate Similarity	NPC125920
0.8	Intermediate Similarity	NPC144027
0.8	Intermediate Similarity	NPC103842
0.8	Intermediate Similarity	NPC236974
0.7986	Intermediate Similarity	NPC476508
0.7986	Intermediate Similarity	NPC193555
0.7985	Intermediate Similarity	NPC37299
0.7985	Intermediate Similarity	NPC180261
0.7972	Intermediate Similarity	NPC214493
0.7971	Intermediate Similarity	NPC477956
0.7971	Intermediate Similarity	NPC295384
0.7971	Intermediate Similarity	NPC283429
0.7971	Intermediate Similarity	NPC37206
0.797	Intermediate Similarity	NPC198249
0.797	Intermediate Similarity	NPC41847
0.7958	Intermediate Similarity	NPC304351
0.7958	Intermediate Similarity	NPC245757
0.7956	Intermediate Similarity	NPC9121
0.7956	Intermediate Similarity	NPC177307
0.7956	Intermediate Similarity	NPC153979
0.7956	Intermediate Similarity	NPC473622
0.7955	Intermediate Similarity	NPC109123
0.7955	Intermediate Similarity	NPC78662
0.7955	Intermediate Similarity	NPC8005
0.7955	Intermediate Similarity	NPC92624
0.7941	Intermediate Similarity	NPC158481
0.7941	Intermediate Similarity	NPC254847
0.7941	Intermediate Similarity	NPC131039
0.7941	Intermediate Similarity	NPC101752
0.7941	Intermediate Similarity	NPC472599

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 NPC218333 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	281
0.1-0.2	1122
0.2-0.3	2157
0.3-0.4	3047
0.4-0.5	1644
0.5-0.6	707
0.6-0.7	151
0.7-0.8	40
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8195	Intermediate Similarity	NPD6651	Approved
0.7941	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.781	Intermediate Similarity	NPD1510	Phase 2
0.7778	Intermediate Similarity	NPD943	Approved
0.7778	Intermediate Similarity	NPD1240	Approved
0.7714	Intermediate Similarity	NPD2800	Approved
0.7664	Intermediate Similarity	NPD1607	Approved
0.7584	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7571	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7571	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7569	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7569	Intermediate Similarity	NPD2534	Approved
0.7569	Intermediate Similarity	NPD2532	Approved
0.7569	Intermediate Similarity	NPD2533	Approved
0.7518	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7518	Intermediate Similarity	NPD1549	Phase 2
0.75	Intermediate Similarity	NPD7390	Discontinued
0.7429	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7385	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD7411	Suspended
0.7329	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD4380	Phase 2
0.7285	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7259	Intermediate Similarity	NPD1164	Approved
0.723	Intermediate Similarity	NPD920	Approved
0.7218	Intermediate Similarity	NPD1201	Approved
0.7154	Intermediate Similarity	NPD9493	Approved
0.7143	Intermediate Similarity	NPD7075	Discontinued
0.7133	Intermediate Similarity	NPD1551	Phase 2
0.7133	Intermediate Similarity	NPD2796	Approved
0.7132	Intermediate Similarity	NPD1470	Approved
0.7105	Intermediate Similarity	NPD1934	Approved
0.7095	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD230	Phase 1
0.7089	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD9266	Approved
0.7063	Intermediate Similarity	NPD74	Approved
0.7059	Intermediate Similarity	NPD7819	Suspended
0.7059	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD9545	Approved
0.7037	Intermediate Similarity	NPD9269	Phase 2
0.7027	Intermediate Similarity	NPD1511	Approved
0.7014	Intermediate Similarity	NPD5405	Approved
0.7014	Intermediate Similarity	NPD2935	Discontinued
0.7014	Intermediate Similarity	NPD5406	Approved
0.7014	Intermediate Similarity	NPD5404	Approved
0.7014	Intermediate Similarity	NPD5408	Approved
0.7006	Intermediate Similarity	NPD6959	Discontinued
0.6993	Remote Similarity	NPD6801	Discontinued
0.6992	Remote Similarity	NPD940	Approved
0.6992	Remote Similarity	NPD9268	Approved
0.6992	Remote Similarity	NPD846	Approved
0.6986	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD1243	Approved
0.6984	Remote Similarity	NPD9264	Approved
0.6984	Remote Similarity	NPD9267	Approved
0.6984	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD9263	Approved
0.698	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD1512	Approved
0.6913	Remote Similarity	NPD6799	Approved
0.6899	Remote Similarity	NPD1247	Approved
0.6894	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD3882	Suspended
0.6859	Remote Similarity	NPD7768	Phase 2
0.6855	Remote Similarity	NPD5710	Approved
0.6855	Remote Similarity	NPD5711	Approved
0.6839	Remote Similarity	NPD2801	Approved
0.6832	Remote Similarity	NPD7473	Discontinued
0.6815	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD919	Approved
0.6757	Remote Similarity	NPD2654	Approved
0.6753	Remote Similarity	NPD6599	Discontinued
0.675	Remote Similarity	NPD6232	Discontinued
0.6748	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD9281	Approved
0.6712	Remote Similarity	NPD2799	Discontinued
0.6711	Remote Similarity	NPD3750	Approved
0.6687	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD9717	Approved
0.6667	Remote Similarity	NPD9261	Approved
0.6667	Remote Similarity	NPD6166	Phase 2
0.6667	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5953	Discontinued
0.6646	Remote Similarity	NPD7286	Phase 2
0.6643	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD6559	Discontinued
0.6625	Remote Similarity	NPD5494	Approved
0.6622	Remote Similarity	NPD2344	Approved
0.6615	Remote Similarity	NPD4750	Phase 3
0.6604	Remote Similarity	NPD3749	Approved
0.6582	Remote Similarity	NPD3817	Phase 2
0.6549	Remote Similarity	NPD9494	Approved
0.6528	Remote Similarity	NPD2313	Discontinued
0.6525	Remote Similarity	NPD1203	Approved
0.6507	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6507	Remote Similarity	NPD5124	Phase 1
0.6506	Remote Similarity	NPD7074	Phase 3
0.6506	Remote Similarity	NPD1729	Discontinued
0.6485	Remote Similarity	NPD3818	Discontinued
0.6483	Remote Similarity	NPD520	Approved
0.6479	Remote Similarity	NPD2798	Approved
0.6474	Remote Similarity	NPD3226	Approved
0.6452	Remote Similarity	NPD1809	Phase 2
0.6447	Remote Similarity	NPD2309	Approved
0.6446	Remote Similarity	NPD7054	Approved
0.6446	Remote Similarity	NPD6020	Phase 2
0.6443	Remote Similarity	NPD6099	Approved
0.6443	Remote Similarity	NPD6100	Approved
0.6438	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6423	Remote Similarity	NPD845	Approved
0.6414	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6414	Remote Similarity	NPD3268	Approved
0.6414	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6407	Remote Similarity	NPD7472	Approved
0.6405	Remote Similarity	NPD3300	Phase 2
0.64	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6382	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6378	Remote Similarity	NPD1242	Phase 1
0.6376	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6376	Remote Similarity	NPD3748	Approved
0.6369	Remote Similarity	NPD6797	Phase 2
0.6369	Remote Similarity	NPD7458	Discontinued
0.6364	Remote Similarity	NPD2403	Approved
0.6357	Remote Similarity	NPD1237	Approved
0.6357	Remote Similarity	NPD422	Phase 1
0.6357	Remote Similarity	NPD1610	Phase 2
0.6357	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD5403	Approved
0.6331	Remote Similarity	NPD2932	Approved
0.6331	Remote Similarity	NPD3019	Approved
0.6331	Remote Similarity	NPD7251	Discontinued
0.6323	Remote Similarity	NPD5401	Approved
0.6307	Remote Similarity	NPD4363	Phase 3
0.6307	Remote Similarity	NPD4360	Phase 2
0.6301	Remote Similarity	NPD411	Approved
0.6301	Remote Similarity	NPD3764	Approved
0.6294	Remote Similarity	NPD7808	Phase 3
0.6291	Remote Similarity	NPD2346	Discontinued
0.6284	Remote Similarity	NPD447	Suspended
0.6276	Remote Similarity	NPD6832	Phase 2
0.6276	Remote Similarity	NPD4908	Phase 1
0.6275	Remote Similarity	NPD4628	Phase 3
0.6275	Remote Similarity	NPD3400	Discontinued
0.6271	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.6271	Remote Similarity	NPD4361	Phase 2
0.6269	Remote Similarity	NPD6124	Clinical (unspecified phase)
0.625	Remote Similarity	NPD5844	Phase 1
0.625	Remote Similarity	NPD1019	Discontinued
0.6222	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6211	Remote Similarity	NPD1465	Phase 2
0.6199	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6197	Remote Similarity	NPD3972	Approved
0.6187	Remote Similarity	NPD1548	Phase 1
0.6184	Remote Similarity	NPD1471	Phase 3
0.6181	Remote Similarity	NPD3266	Approved
0.6181	Remote Similarity	NPD3267	Approved
0.6176	Remote Similarity	NPD1241	Discontinued
0.6176	Remote Similarity	NPD7159	Clinical (unspecified phase)
0.6173	Remote Similarity	NPD5402	Approved
0.6173	Remote Similarity	NPD8438	Clinical (unspecified phase)
0.6172	Remote Similarity	NPD3020	Approved
0.6169	Remote Similarity	NPD7003	Approved
0.6165	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6159	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD1929	Approved
0.6154	Remote Similarity	NPD1930	Approved
0.6142	Remote Similarity	NPD288	Approved
0.614	Remote Similarity	NPD6104	Discontinued
0.6139	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6138	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD1283	Approved
0.6111	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD1876	Approved
0.6108	Remote Similarity	NPD3926	Phase 2
0.6096	Remote Similarity	NPD4208	Discontinued
0.6087	Remote Similarity	NPD255	Approved
0.6087	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD5889	Approved
0.6087	Remote Similarity	NPD5890	Approved
0.6087	Remote Similarity	NPD256	Approved
0.6084	Remote Similarity	NPD1608	Approved
0.6082	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6081	Remote Similarity	NPD1296	Phase 2
0.6078	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6078	Remote Similarity	NPD6005	Phase 3
0.6078	Remote Similarity	NPD6004	Phase 3
0.6078	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6078	Remote Similarity	NPD6002	Phase 3
0.6071	Remote Similarity	NPD1759	Phase 1
0.6069	Remote Similarity	NPD2797	Approved
0.6067	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6063	Remote Similarity	NPD2859	Approved
0.6063	Remote Similarity	NPD2860	Approved
0.6063	Remote Similarity	NPD844	Approved
0.6057	Remote Similarity	NPD8150	Discontinued

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