NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	248.14
Volume:	266.708
LogP:	2.196
LogD:	1.31
LogS:	-3.063
# Rotatable Bonds:	2
TPSA:	57.53
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.79
Synthetic Accessibility Score:	3.752
Fsp3:	0.533
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.706
MDCK Permeability:	1.2508360669016838e-05
Pgp-inhibitor:	0.048
Pgp-substrate:	0.834
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.962
30% Bioavailability (F30%):	0.236

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.042
Plasma Protein Binding (PPB):	71.34828186035156%
Volume Distribution (VD):	1.394
Pgp-substrate:	11.362480163574219%

ADMET: Metabolism

CYP1A2-inhibitor:	0.051
CYP1A2-substrate:	0.296
CYP2C19-inhibitor:	0.022
CYP2C19-substrate:	0.73
CYP2C9-inhibitor:	0.015
CYP2C9-substrate:	0.865
CYP2D6-inhibitor:	0.03
CYP2D6-substrate:	0.41
CYP3A4-inhibitor:	0.011
CYP3A4-substrate:	0.222

ADMET: Excretion

Clearance (CL):	5.895
Half-life (T1/2):	0.705

ADMET: Toxicity

hERG Blockers:	0.008
Human Hepatotoxicity (H-HT):	0.128
Drug-inuced Liver Injury (DILI):	0.042
AMES Toxicity:	0.093
Rat Oral Acute Toxicity:	0.399
Maximum Recommended Daily Dose:	0.435
Skin Sensitization:	0.723
Carcinogencity:	0.051
Eye Corrosion:	0.008
Eye Irritation:	0.446
Respiratory Toxicity:	0.911

Download Data

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

Natural Product: NPC12818

Natural Product ID:	NPC12818
*Common Name:**	Onitin
IUPAC Name:	4-hydroxy-6-(2-hydroxyethyl)-2,2,5,7-tetramethyl-3H-inden-1-one
Synonyms:
Standard InCHIKey:	IWRJCMQFEMXOML-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C15H20O3/c1-8-10(5-6-16)9(2)13(17)11-7-15(3,4)14(18)12(8)11/h16-17H,5-7H2,1-4H3
SMILES:	Cc1c(CCO)c(C)c(c2CC(C)(C)C(=O)c12)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL261243
PubChem CID:	3085044
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000027] Indanes [CHEMONTID:0001151] Indanones

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO863	Rhaphidophora decursiva	Species	Araceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11421741]
NPO24811	Cibotium barometz	Species	Cibotiaceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[19739599]
NPO41007	Phomopsis sp. TJ507A	Strain	Valsaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29771527]
NPO22224	Caragana jubata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31577434]
NPO24811	Cibotium barometz	Species	Cibotiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7952	Commelina communis	Species	Commelinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10948	Guarea rhopalocarpa	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12472	Buddleja davidii	Species	Scrophulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22224	Caragana jubata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24811	Cibotium barometz	Species	Cibotiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7952	Commelina communis	Species	Commelinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22224	Caragana jubata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12472	Buddleja davidii	Species	Scrophulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10948	Guarea rhopalocarpa	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22224	Caragana jubata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO24811	Cibotium barometz	Species	Cibotiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO24811	Cibotium barometz	Species	Cibotiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO7952	Commelina communis	Species	Commelinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO12472	Buddleja davidii	Species	Scrophulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22224	Caragana jubata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24811	Cibotium barometz	Species	Cibotiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15080	Larix kamtschatica	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14654	Rhododendron ledebourii	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5050	Galium triflorum	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15211	Eriogonum brevicaule	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2059	Lactuca denticulata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13317	Geigeria acaulis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7952	Commelina communis	Species	Commelinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10948	Guarea rhopalocarpa	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO863	Rhaphidophora decursiva	Species	Araceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15590	Peperomia tetraphylla	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14315	Conostylis setosa	Species	Haemodoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8723	Ophiostoma piliferum	Species	Ophiostomataceae	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
EC50	1
Others	1

Activity Type	# Activity
Individual Protein	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		EC50	=	100000.0	nM	PMID[489288]
NPT740	Individual Protein	Beta-secretase 1	Homo sapiens	Inhibition	=	19.4	%	PMID[489289]

☑ 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 NPC12818 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	264
0.1-0.2	1481
0.2-0.3	3348
0.3-0.4	9452
0.4-0.5	11123
0.5-0.6	8710
0.6-0.7	6864
0.7-0.8	1384
0.8-0.85	66
0.85-0.9	4
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.896	High Similarity	NPC19432
0.8769	High Similarity	NPC52368
0.8769	High Similarity	NPC218854
0.8548	High Similarity	NPC190971
0.8397	Intermediate Similarity	NPC471851
0.8346	Intermediate Similarity	NPC202225
0.8308	Intermediate Similarity	NPC3009
0.8295	Intermediate Similarity	NPC472047
0.8295	Intermediate Similarity	NPC254492
0.8271	Intermediate Similarity	NPC78307
0.8268	Intermediate Similarity	NPC282577
0.8248	Intermediate Similarity	NPC471853
0.8231	Intermediate Similarity	NPC69424
0.8231	Intermediate Similarity	NPC72667
0.8231	Intermediate Similarity	NPC176130
0.8231	Intermediate Similarity	NPC78364
0.8231	Intermediate Similarity	NPC84672
0.8182	Intermediate Similarity	NPC108129
0.8162	Intermediate Similarity	NPC475957
0.8162	Intermediate Similarity	NPC477592
0.814	Intermediate Similarity	NPC199273
0.8134	Intermediate Similarity	NPC477139
0.8129	Intermediate Similarity	NPC248068
0.812	Intermediate Similarity	NPC41847
0.812	Intermediate Similarity	NPC476847
0.811	Intermediate Similarity	NPC472046
0.8106	Intermediate Similarity	NPC276238
0.8106	Intermediate Similarity	NPC303910
0.8106	Intermediate Similarity	NPC171460
0.808	Intermediate Similarity	NPC174087
0.8077	Intermediate Similarity	NPC123506
0.8077	Intermediate Similarity	NPC87985
0.806	Intermediate Similarity	NPC474109
0.8045	Intermediate Similarity	NPC62219
0.8029	Intermediate Similarity	NPC119542
0.8015	Intermediate Similarity	NPC477596
0.8	Intermediate Similarity	NPC314048
0.8	Intermediate Similarity	NPC111845
0.8	Intermediate Similarity	NPC152525
0.8	Intermediate Similarity	NPC68756
0.8	Intermediate Similarity	NPC181334
0.8	Intermediate Similarity	NPC477209
0.8	Intermediate Similarity	NPC138472
0.7985	Intermediate Similarity	NPC17083
0.7985	Intermediate Similarity	NPC93015
0.7971	Intermediate Similarity	NPC477593
0.7971	Intermediate Similarity	NPC230811
0.7956	Intermediate Similarity	NPC315275
0.7956	Intermediate Similarity	NPC86524
0.7955	Intermediate Similarity	NPC83572
0.7953	Intermediate Similarity	NPC473767
0.7941	Intermediate Similarity	NPC477594
0.7941	Intermediate Similarity	NPC474519
0.7939	Intermediate Similarity	NPC137750
0.7923	Intermediate Similarity	NPC471187
0.7923	Intermediate Similarity	NPC273683
0.791	Intermediate Similarity	NPC296158
0.7907	Intermediate Similarity	NPC154696
0.7899	Intermediate Similarity	NPC147691
0.7899	Intermediate Similarity	NPC53001
0.7899	Intermediate Similarity	NPC36868
0.7895	Intermediate Similarity	NPC96024
0.7883	Intermediate Similarity	NPC153088
0.7883	Intermediate Similarity	NPC244640
0.7883	Intermediate Similarity	NPC279291
0.7879	Intermediate Similarity	NPC269598
0.7879	Intermediate Similarity	NPC71610
0.7872	Intermediate Similarity	NPC308572
0.7872	Intermediate Similarity	NPC135524
0.7872	Intermediate Similarity	NPC474961
0.7868	Intermediate Similarity	NPC59459
0.7868	Intermediate Similarity	NPC52407
0.7868	Intermediate Similarity	NPC114183
0.7847	Intermediate Similarity	NPC5568
0.7846	Intermediate Similarity	NPC475192
0.7842	Intermediate Similarity	NPC87723
0.7826	Intermediate Similarity	NPC38158
0.7826	Intermediate Similarity	NPC299734
0.7817	Intermediate Similarity	NPC100242
0.781	Intermediate Similarity	NPC474117
0.781	Intermediate Similarity	NPC474394
0.781	Intermediate Similarity	NPC474224
0.781	Intermediate Similarity	NPC12070
0.781	Intermediate Similarity	NPC270899
0.7803	Intermediate Similarity	NPC131799
0.7803	Intermediate Similarity	NPC477454
0.7801	Intermediate Similarity	NPC204045
0.7801	Intermediate Similarity	NPC477595
0.7801	Intermediate Similarity	NPC305845
0.7801	Intermediate Similarity	NPC477275
0.7801	Intermediate Similarity	NPC92079
0.7794	Intermediate Similarity	NPC88864
0.7794	Intermediate Similarity	NPC165612
0.7794	Intermediate Similarity	NPC70622
0.7786	Intermediate Similarity	NPC162939
0.7786	Intermediate Similarity	NPC190457
0.7786	Intermediate Similarity	NPC198014
0.7786	Intermediate Similarity	NPC306288
0.7778	Intermediate Similarity	NPC475741
0.776	Intermediate Similarity	NPC242136
0.7754	Intermediate Similarity	NPC249272
0.7754	Intermediate Similarity	NPC474076
0.7754	Intermediate Similarity	NPC278375
0.7752	Intermediate Similarity	NPC133302
0.7744	Intermediate Similarity	NPC473691
0.7744	Intermediate Similarity	NPC227741
0.7744	Intermediate Similarity	NPC49647
0.7744	Intermediate Similarity	NPC136342
0.7744	Intermediate Similarity	NPC295202
0.7744	Intermediate Similarity	NPC15837
0.774	Intermediate Similarity	NPC142654
0.7737	Intermediate Similarity	NPC49742
0.7737	Intermediate Similarity	NPC267205
0.7737	Intermediate Similarity	NPC37299
0.7737	Intermediate Similarity	NPC263817
0.7737	Intermediate Similarity	NPC180261
0.7737	Intermediate Similarity	NPC48036
0.7737	Intermediate Similarity	NPC4170
0.7727	Intermediate Similarity	NPC234890
0.7727	Intermediate Similarity	NPC173978
0.7727	Intermediate Similarity	NPC74507
0.7721	Intermediate Similarity	NPC291001
0.7717	Intermediate Similarity	NPC83718
0.7714	Intermediate Similarity	NPC123714
0.771	Intermediate Similarity	NPC11250
0.771	Intermediate Similarity	NPC307174
0.771	Intermediate Similarity	NPC218333
0.771	Intermediate Similarity	NPC66252
0.771	Intermediate Similarity	NPC176208
0.7708	Intermediate Similarity	NPC225351
0.7705	Intermediate Similarity	NPC112903
0.7704	Intermediate Similarity	NPC278928
0.7704	Intermediate Similarity	NPC99731
0.7704	Intermediate Similarity	NPC117899
0.7698	Intermediate Similarity	NPC472599
0.7698	Intermediate Similarity	NPC474311
0.7698	Intermediate Similarity	NPC156967
0.7698	Intermediate Similarity	NPC191976
0.7698	Intermediate Similarity	NPC254847
0.7692	Intermediate Similarity	NPC259703
0.7692	Intermediate Similarity	NPC32322
0.7687	Intermediate Similarity	NPC262936
0.7687	Intermediate Similarity	NPC30491
0.7681	Intermediate Similarity	NPC282780
0.7681	Intermediate Similarity	NPC166480
0.768	Intermediate Similarity	NPC231717
0.7676	Intermediate Similarity	NPC106519
0.7676	Intermediate Similarity	NPC2681
0.7676	Intermediate Similarity	NPC91019
0.7676	Intermediate Similarity	NPC272907
0.7674	Intermediate Similarity	NPC79933
0.7674	Intermediate Similarity	NPC473974
0.7674	Intermediate Similarity	NPC258366
0.7674	Intermediate Similarity	NPC31296
0.7667	Intermediate Similarity	NPC276815
0.7667	Intermediate Similarity	NPC25850
0.7664	Intermediate Similarity	NPC242358
0.7664	Intermediate Similarity	NPC246693
0.7664	Intermediate Similarity	NPC110609
0.7664	Intermediate Similarity	NPC477407
0.7664	Intermediate Similarity	NPC309430
0.766	Intermediate Similarity	NPC138099
0.766	Intermediate Similarity	NPC242994
0.7655	Intermediate Similarity	NPC477208
0.7655	Intermediate Similarity	NPC143685
0.7652	Intermediate Similarity	NPC174991
0.7652	Intermediate Similarity	NPC275145
0.7647	Intermediate Similarity	NPC199253
0.7647	Intermediate Similarity	NPC147757
0.7647	Intermediate Similarity	NPC31799
0.7647	Intermediate Similarity	NPC136588
0.7647	Intermediate Similarity	NPC253488
0.7643	Intermediate Similarity	NPC53414
0.7643	Intermediate Similarity	NPC53206
0.7643	Intermediate Similarity	NPC471905
0.7643	Intermediate Similarity	NPC245058
0.7643	Intermediate Similarity	NPC471452
0.7643	Intermediate Similarity	NPC277559
0.7643	Intermediate Similarity	NPC49911
0.7639	Intermediate Similarity	NPC471906
0.7639	Intermediate Similarity	NPC244691
0.7639	Intermediate Similarity	NPC471451
0.7634	Intermediate Similarity	NPC120545
0.7634	Intermediate Similarity	NPC253627
0.763	Intermediate Similarity	NPC282923
0.763	Intermediate Similarity	NPC247250
0.763	Intermediate Similarity	NPC767
0.763	Intermediate Similarity	NPC193203
0.763	Intermediate Similarity	NPC229894
0.7626	Intermediate Similarity	NPC290803
0.7626	Intermediate Similarity	NPC283088
0.7626	Intermediate Similarity	NPC475917
0.7622	Intermediate Similarity	NPC85310
0.7616	Intermediate Similarity	NPC283301
0.7615	Intermediate Similarity	NPC190501
0.7615	Intermediate Similarity	NPC318552
0.7612	Intermediate Similarity	NPC160499
0.7612	Intermediate Similarity	NPC231774
0.7609	Intermediate Similarity	NPC254603
0.7609	Intermediate Similarity	NPC310662

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 NPC12818 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	272
0.1-0.2	1080
0.2-0.3	1918
0.3-0.4	2892
0.4-0.5	1869
0.5-0.6	903
0.6-0.7	200
0.7-0.8	16
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
0.7812	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7698	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7615	Intermediate Similarity	NPD3019	Approved
0.7615	Intermediate Similarity	NPD2932	Approved
0.7586	Intermediate Similarity	NPD2532	Approved
0.7586	Intermediate Similarity	NPD2533	Approved
0.7586	Intermediate Similarity	NPD2534	Approved
0.75	Intermediate Similarity	NPD1201	Approved
0.7407	Intermediate Similarity	NPD1470	Approved
0.7279	Intermediate Similarity	NPD7390	Discontinued
0.723	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7183	Intermediate Similarity	NPD6651	Approved
0.7176	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD5404	Approved
0.7153	Intermediate Similarity	NPD5406	Approved
0.7153	Intermediate Similarity	NPD5405	Approved
0.7153	Intermediate Similarity	NPD5408	Approved
0.7123	Intermediate Similarity	NPD2800	Approved
0.7092	Intermediate Similarity	NPD6663	Approved
0.7068	Intermediate Similarity	NPD3091	Approved
0.705	Intermediate Similarity	NPD5736	Approved
0.7037	Intermediate Similarity	NPD3026	Approved
0.7037	Intermediate Similarity	NPD3023	Approved
0.7015	Intermediate Similarity	NPD3024	Approved
0.7015	Intermediate Similarity	NPD3025	Approved
0.6985	Remote Similarity	NPD3092	Approved
0.6966	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.694	Remote Similarity	NPD9545	Approved
0.6923	Remote Similarity	NPD943	Approved
0.6901	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD1809	Phase 2
0.6875	Remote Similarity	NPD5710	Approved
0.6875	Remote Similarity	NPD5711	Approved
0.6875	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD7003	Approved
0.6846	Remote Similarity	NPD4628	Phase 3
0.6842	Remote Similarity	NPD6273	Approved
0.6838	Remote Similarity	NPD4626	Approved
0.6828	Remote Similarity	NPD1607	Approved
0.6824	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD6959	Discontinued
0.6812	Remote Similarity	NPD3972	Approved
0.6786	Remote Similarity	NPD3094	Phase 2
0.6767	Remote Similarity	NPD5951	Approved
0.6765	Remote Similarity	NPD1651	Approved
0.6715	Remote Similarity	NPD4059	Approved
0.6715	Remote Similarity	NPD3095	Discontinued
0.6714	Remote Similarity	NPD1283	Approved
0.6714	Remote Similarity	NPD1876	Approved
0.671	Remote Similarity	NPD7458	Discontinued
0.669	Remote Similarity	NPD1240	Approved
0.6689	Remote Similarity	NPD7910	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD6099	Approved
0.6689	Remote Similarity	NPD6100	Approved
0.6667	Remote Similarity	NPD6232	Discontinued
0.6667	Remote Similarity	NPD3764	Approved
0.6667	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1164	Approved
0.6646	Remote Similarity	NPD7819	Suspended
0.6646	Remote Similarity	NPD7473	Discontinued
0.6644	Remote Similarity	NPD2346	Discontinued
0.6644	Remote Similarity	NPD230	Phase 1
0.6643	Remote Similarity	NPD1755	Approved
0.6642	Remote Similarity	NPD5691	Approved
0.6622	Remote Similarity	NPD1510	Phase 2
0.6617	Remote Similarity	NPD7635	Approved
0.6613	Remote Similarity	NPD844	Approved
0.6603	Remote Similarity	NPD3226	Approved
0.6596	Remote Similarity	NPD6696	Suspended
0.6577	Remote Similarity	NPD2935	Discontinued
0.6573	Remote Similarity	NPD9494	Approved
0.6573	Remote Similarity	NPD4208	Discontinued
0.6571	Remote Similarity	NPD9269	Phase 2
0.6567	Remote Similarity	NPD1398	Phase 1
0.656	Remote Similarity	NPD288	Approved
0.6558	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6558	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6541	Remote Similarity	NPD6124	Clinical (unspecified phase)
0.6541	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6536	Remote Similarity	NPD7236	Approved
0.6536	Remote Similarity	NPD3300	Phase 2
0.6535	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6533	Remote Similarity	NPD2344	Approved
0.6532	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD9268	Approved
0.6515	Remote Similarity	NPD4750	Phase 3
0.6513	Remote Similarity	NPD8166	Discontinued
0.651	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.65	Remote Similarity	NPD1281	Approved
0.6496	Remote Similarity	NPD7610	Discontinued
0.6489	Remote Similarity	NPD2342	Discontinued
0.6483	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6475	Remote Similarity	NPD1778	Approved
0.6475	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6467	Remote Similarity	NPD5844	Phase 1
0.6466	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6456	Remote Similarity	NPD4380	Phase 2
0.6452	Remote Similarity	NPD845	Approved
0.6444	Remote Similarity	NPD7159	Clinical (unspecified phase)
0.6439	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6433	Remote Similarity	NPD7239	Suspended
0.6424	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6424	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6423	Remote Similarity	NPD7340	Approved
0.6423	Remote Similarity	NPD9493	Approved
0.6414	Remote Similarity	NPD4207	Discontinued
0.6405	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.64	Remote Similarity	NPD2799	Discontinued
0.6398	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6398	Remote Similarity	NPD8438	Clinical (unspecified phase)
0.6395	Remote Similarity	NPD8032	Phase 2
0.6392	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6385	Remote Similarity	NPD1237	Approved
0.6382	Remote Similarity	NPD1549	Phase 2
0.637	Remote Similarity	NPD7008	Discontinued
0.6364	Remote Similarity	NPD2309	Approved
0.6358	Remote Similarity	NPD3882	Suspended
0.6357	Remote Similarity	NPD846	Approved
0.6357	Remote Similarity	NPD940	Approved
0.6352	Remote Similarity	NPD6599	Discontinued
0.6351	Remote Similarity	NPD3620	Phase 2
0.6351	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6351	Remote Similarity	NPD4140	Approved
0.6346	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6335	Remote Similarity	NPD5761	Phase 2
0.6335	Remote Similarity	NPD5760	Phase 2
0.6327	Remote Similarity	NPD7985	Registered
0.6316	Remote Similarity	NPD6002	Phase 3
0.6316	Remote Similarity	NPD6005	Phase 3
0.6316	Remote Similarity	NPD74	Approved
0.6316	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD6004	Phase 3
0.6316	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD9266	Approved
0.6316	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6303	Remote Similarity	NPD8127	Discontinued
0.6299	Remote Similarity	NPD3750	Approved
0.6296	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6276	Remote Similarity	NPD4624	Approved
0.6273	Remote Similarity	NPD1934	Approved
0.6264	Remote Similarity	NPD8150	Discontinued
0.6257	Remote Similarity	NPD3658	Clinical (unspecified phase)
0.625	Remote Similarity	NPD2796	Approved
0.625	Remote Similarity	NPD7028	Phase 2
0.6242	Remote Similarity	NPD2979	Phase 3
0.6241	Remote Similarity	NPD9267	Approved
0.6241	Remote Similarity	NPD9263	Approved
0.6241	Remote Similarity	NPD9264	Approved
0.6235	Remote Similarity	NPD2801	Approved
0.6224	Remote Similarity	NPD1608	Approved
0.6222	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.622	Remote Similarity	NPD7075	Discontinued
0.6216	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6215	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6214	Remote Similarity	NPD7009	Phase 2
0.6213	Remote Similarity	NPD7177	Discontinued
0.6211	Remote Similarity	NPD7411	Suspended
0.6209	Remote Similarity	NPD5763	Approved
0.6209	Remote Similarity	NPD1471	Phase 3
0.6209	Remote Similarity	NPD5762	Approved
0.6202	Remote Similarity	NPD3020	Approved
0.62	Remote Similarity	NPD5735	Approved
0.6197	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6194	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6193	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6184	Remote Similarity	NPD7742	Approved
0.6184	Remote Similarity	NPD7743	Approved
0.6181	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6178	Remote Similarity	NPD1511	Approved
0.6176	Remote Similarity	NPD6020	Phase 2
0.6174	Remote Similarity	NPD7961	Discontinued
0.6173	Remote Similarity	NPD6801	Discontinued
0.6173	Remote Similarity	NPD37	Approved
0.6164	Remote Similarity	NPD2798	Approved
0.6164	Remote Similarity	NPD920	Approved
0.6163	Remote Similarity	NPD6559	Discontinued
0.6159	Remote Similarity	NPD2629	Approved
0.6159	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6159	Remote Similarity	NPD4097	Suspended
0.6145	Remote Similarity	NPD5494	Approved
0.6145	Remote Similarity	NPD6534	Approved
0.6145	Remote Similarity	NPD6535	Approved
0.6144	Remote Similarity	NPD4476	Approved
0.6144	Remote Similarity	NPD4477	Approved
0.6142	Remote Similarity	NPD1693	Approved
0.6135	Remote Similarity	NPD1465	Phase 2
0.6135	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6133	Remote Similarity	NPD4060	Phase 1
0.6129	Remote Similarity	NPD1243	Approved
0.6127	Remote Similarity	NPD1751	Approved
0.6122	Remote Similarity	NPD4212	Discontinued
0.6122	Remote Similarity	NPD2861	Phase 2
0.6121	Remote Similarity	NPD3749	Approved
0.6118	Remote Similarity	NPD3818	Discontinued
0.6111	Remote Similarity	NPD4878	Approved
0.6108	Remote Similarity	NPD7199	Phase 2
0.6107	Remote Similarity	NPD2313	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