NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	204.04
Volume:	201.042
LogP:	1.804
LogD:	1.555
LogS:	-2.854
# Rotatable Bonds:	1
TPSA:	63.6
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.748
Synthetic Accessibility Score:	2.297
Fsp3:	0.091
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.635
MDCK Permeability:	2.3473627152270637e-05
Pgp-inhibitor:	0.008
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.301
30% Bioavailability (F30%):	0.466

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.375
Plasma Protein Binding (PPB):	94.1186752319336%
Volume Distribution (VD):	0.468
Pgp-substrate:	2.1840171813964844%

ADMET: Metabolism

CYP1A2-inhibitor:	0.982
CYP1A2-substrate:	0.809
CYP2C19-inhibitor:	0.652
CYP2C19-substrate:	0.086
CYP2C9-inhibitor:	0.663
CYP2C9-substrate:	0.77
CYP2D6-inhibitor:	0.854
CYP2D6-substrate:	0.269
CYP3A4-inhibitor:	0.709
CYP3A4-substrate:	0.167

ADMET: Excretion

Clearance (CL):	8.138
Half-life (T1/2):	0.647

ADMET: Toxicity

hERG Blockers:	0.014
Human Hepatotoxicity (H-HT):	0.586
Drug-inuced Liver Injury (DILI):	0.572
AMES Toxicity:	0.928
Rat Oral Acute Toxicity:	0.947
Maximum Recommended Daily Dose:	0.874
Skin Sensitization:	0.855
Carcinogencity:	0.881
Eye Corrosion:	0.116
Eye Irritation:	0.982
Respiratory Toxicity:	0.506

Download Data

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

Natural Product: NPC51037

Natural Product ID:	NPC51037
*Common Name:**	3-Methoxyjuglone
IUPAC Name:	8-hydroxy-2-methoxynaphthalene-1,4-dione
Synonyms:	3-Methoxyjuglone
Standard InCHIKey:	HOFSOQDUZIZMBA-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C11H8O4/c1-15-9-5-8(13)6-3-2-4-7(12)10(6)11(9)14/h2-5,12H,1H3
SMILES:	COC1=CC(=O)c2cccc(c2C1=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2204407
PubChem CID:	609303
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000023] Naphthalenes [CHEMONTID:0000153] Naphthoquinones

*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
NPO20411	Engelhardia roxburghiana	Species	Juglandaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20411	Engelhardia roxburghiana	Species	Juglandaceae	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	6
MIC	1
Others	2

Activity Type	# Activity
Cell Line	7
Organism	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	960.0	nM	PMID[490378]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	1040.0	nM	PMID[490378]
NPT165	Cell Line	HeLa	Homo sapiens	INCC50	=	0.61	uM	PMID[490378]
NPT165	Cell Line	HeLa	Homo sapiens	Ratio	=	1.7	n.a.	PMID[490378]
NPT407	Cell Line	COLO 205	Homo sapiens	IC50	>	10000.0	nM	PMID[490379]
NPT396	Cell Line	T47D	Homo sapiens	IC50	>	10000.0	nM	PMID[490379]
NPT111	Cell Line	K562	Homo sapiens	IC50	>	10000.0	nM	PMID[490379]
NPT790	Organism	Mycobacterium tuberculosis H37Rv	Mycobacterium tuberculosis H37Rv	MIC	=	3.125	ug.mL-1	PMID[490377]
NPT27	Others	Unspecified		IC50	=	1480.0	nM	PMID[490378]

☑ 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 NPC51037 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	303
0.1-0.2	1548
0.2-0.3	3922
0.3-0.4	10314
0.4-0.5	8673
0.5-0.6	5781
0.6-0.7	8420
0.7-0.8	3410
0.8-0.85	243
0.85-0.9	64
0.9-0.95	13
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9835	High Similarity	NPC237225
0.9672	High Similarity	NPC165257
0.9516	High Similarity	NPC198305
0.9504	High Similarity	NPC310540
0.9291	High Similarity	NPC171968
0.9213	High Similarity	NPC309430
0.9194	High Similarity	NPC231774
0.9134	High Similarity	NPC205360
0.9091	High Similarity	NPC285829
0.9091	High Similarity	NPC206778
0.9084	High Similarity	NPC173980
0.9076	High Similarity	NPC108288
0.904	High Similarity	NPC1991
0.9008	High Similarity	NPC232178
0.8992	High Similarity	NPC254603
0.8952	High Similarity	NPC135062
0.8889	High Similarity	NPC306765
0.8872	High Similarity	NPC477408
0.8871	High Similarity	NPC307174
0.8828	High Similarity	NPC278928
0.878	High Similarity	NPC7151
0.878	High Similarity	NPC473662
0.878	High Similarity	NPC216297
0.8769	High Similarity	NPC477406
0.8769	High Similarity	NPC88864
0.874	High Similarity	NPC3224
0.8731	High Similarity	NPC114620
0.8731	High Similarity	NPC103337
0.8712	High Similarity	NPC22222
0.8712	High Similarity	NPC281513
0.8702	High Similarity	NPC193169
0.8678	High Similarity	NPC240163
0.8661	High Similarity	NPC287473
0.8651	High Similarity	NPC375356
0.8626	High Similarity	NPC242358
0.8626	High Similarity	NPC246693
0.8626	High Similarity	NPC110609
0.8615	High Similarity	NPC117609
0.8615	High Similarity	NPC199253
0.8615	High Similarity	NPC136588
0.8615	High Similarity	NPC475741
0.8615	High Similarity	NPC27659
0.8607	High Similarity	NPC477453
0.8605	High Similarity	NPC179898
0.8594	High Similarity	NPC96915
0.8583	High Similarity	NPC234890
0.8583	High Similarity	NPC74507
0.8571	High Similarity	NPC164947
0.8571	High Similarity	NPC300274
0.8551	High Similarity	NPC477409
0.8538	High Similarity	NPC34414
0.8538	High Similarity	NPC146647
0.8537	High Similarity	NPC269414
0.8527	High Similarity	NPC45537
0.8527	High Similarity	NPC470841
0.8525	High Similarity	NPC161304
0.8516	High Similarity	NPC103540
0.8507	High Similarity	NPC232996
0.8504	High Similarity	NPC182646
0.8485	Intermediate Similarity	NPC17843
0.8485	Intermediate Similarity	NPC70622
0.8473	Intermediate Similarity	NPC55949
0.8468	Intermediate Similarity	NPC41567
0.8462	Intermediate Similarity	NPC247250
0.8462	Intermediate Similarity	NPC767
0.8462	Intermediate Similarity	NPC282923
0.8444	Intermediate Similarity	NPC284184
0.8444	Intermediate Similarity	NPC301341
0.8438	Intermediate Similarity	NPC68756
0.8438	Intermediate Similarity	NPC152525
0.8438	Intermediate Similarity	NPC142956
0.8425	Intermediate Similarity	NPC46634
0.8425	Intermediate Similarity	NPC217756
0.8421	Intermediate Similarity	NPC52407
0.8417	Intermediate Similarity	NPC29932
0.8409	Intermediate Similarity	NPC205992
0.8409	Intermediate Similarity	NPC244699
0.8403	Intermediate Similarity	NPC224584
0.8397	Intermediate Similarity	NPC99731
0.8387	Intermediate Similarity	NPC125252
0.8385	Intermediate Similarity	NPC471530
0.837	Intermediate Similarity	NPC86524
0.837	Intermediate Similarity	NPC38158
0.837	Intermediate Similarity	NPC141934
0.8369	Intermediate Similarity	NPC476821
0.8359	Intermediate Similarity	NPC477153
0.8358	Intermediate Similarity	NPC50924
0.8357	Intermediate Similarity	NPC474630
0.8346	Intermediate Similarity	NPC478190
0.8333	Intermediate Similarity	NPC84273
0.8333	Intermediate Similarity	NPC110810
0.8333	Intermediate Similarity	NPC283292
0.8333	Intermediate Similarity	NPC31799
0.8321	Intermediate Similarity	NPC476477
0.8321	Intermediate Similarity	NPC256463
0.8321	Intermediate Similarity	NPC306835
0.8321	Intermediate Similarity	NPC299405
0.8321	Intermediate Similarity	NPC471602
0.8321	Intermediate Similarity	NPC111422
0.8321	Intermediate Similarity	NPC216312
0.8321	Intermediate Similarity	NPC48248
0.8321	Intermediate Similarity	NPC29771
0.8319	Intermediate Similarity	NPC34715
0.8308	Intermediate Similarity	NPC15837
0.8306	Intermediate Similarity	NPC325646
0.8306	Intermediate Similarity	NPC28951
0.8298	Intermediate Similarity	NPC136878
0.8295	Intermediate Similarity	NPC265910
0.8295	Intermediate Similarity	NPC91475
0.8295	Intermediate Similarity	NPC474766
0.8284	Intermediate Similarity	NPC225051
0.8284	Intermediate Similarity	NPC53896
0.8279	Intermediate Similarity	NPC231717
0.8261	Intermediate Similarity	NPC42262
0.8261	Intermediate Similarity	NPC147542
0.8261	Intermediate Similarity	NPC241349
0.8261	Intermediate Similarity	NPC156872
0.8261	Intermediate Similarity	NPC327916
0.8261	Intermediate Similarity	NPC32749
0.8261	Intermediate Similarity	NPC220496
0.8261	Intermediate Similarity	NPC37992
0.8248	Intermediate Similarity	NPC61590
0.8244	Intermediate Similarity	NPC473787
0.8239	Intermediate Similarity	NPC252208
0.8235	Intermediate Similarity	NPC315275
0.8235	Intermediate Similarity	NPC155211
0.8235	Intermediate Similarity	NPC474311
0.8231	Intermediate Similarity	NPC123506
0.8227	Intermediate Similarity	NPC28632
0.8222	Intermediate Similarity	NPC288089
0.8211	Intermediate Similarity	NPC11824
0.8209	Intermediate Similarity	NPC58685
0.8203	Intermediate Similarity	NPC198336
0.8201	Intermediate Similarity	NPC257003
0.8201	Intermediate Similarity	NPC124365
0.8201	Intermediate Similarity	NPC471444
0.8195	Intermediate Similarity	NPC147757
0.8188	Intermediate Similarity	NPC1268
0.8188	Intermediate Similarity	NPC26924
0.8188	Intermediate Similarity	NPC295339
0.8188	Intermediate Similarity	NPC52358
0.8182	Intermediate Similarity	NPC95537
0.8175	Intermediate Similarity	NPC305060
0.8175	Intermediate Similarity	NPC264022
0.8175	Intermediate Similarity	NPC471452
0.8175	Intermediate Similarity	NPC477534
0.8168	Intermediate Similarity	NPC136342
0.8168	Intermediate Similarity	NPC295202
0.8168	Intermediate Similarity	NPC160499
0.8168	Intermediate Similarity	NPC49647
0.8168	Intermediate Similarity	NPC227741
0.8162	Intermediate Similarity	NPC283088
0.8162	Intermediate Similarity	NPC80035
0.8162	Intermediate Similarity	NPC161632
0.8156	Intermediate Similarity	NPC89664
0.8156	Intermediate Similarity	NPC475201
0.8156	Intermediate Similarity	NPC274085
0.8154	Intermediate Similarity	NPC173978
0.8154	Intermediate Similarity	NPC4012
0.8148	Intermediate Similarity	NPC43627
0.8148	Intermediate Similarity	NPC294226
0.8148	Intermediate Similarity	NPC59459
0.8148	Intermediate Similarity	NPC115458
0.8145	Intermediate Similarity	NPC163154
0.8143	Intermediate Similarity	NPC474300
0.8143	Intermediate Similarity	NPC69755
0.814	Intermediate Similarity	NPC91478
0.814	Intermediate Similarity	NPC282577
0.814	Intermediate Similarity	NPC283514
0.8134	Intermediate Similarity	NPC198249
0.8134	Intermediate Similarity	NPC17083
0.8134	Intermediate Similarity	NPC477412
0.8129	Intermediate Similarity	NPC315578
0.8129	Intermediate Similarity	NPC477537
0.8125	Intermediate Similarity	NPC26433
0.8125	Intermediate Similarity	NPC115188
0.8125	Intermediate Similarity	NPC472046
0.8125	Intermediate Similarity	NPC120171
0.8125	Intermediate Similarity	NPC222876
0.8125	Intermediate Similarity	NPC159760
0.8125	Intermediate Similarity	NPC244994
0.8125	Intermediate Similarity	NPC272454
0.8125	Intermediate Similarity	NPC301987
0.8125	Intermediate Similarity	NPC35856
0.8125	Intermediate Similarity	NPC179092
0.8125	Intermediate Similarity	NPC190971
0.8125	Intermediate Similarity	NPC292665
0.8125	Intermediate Similarity	NPC178395
0.811	Intermediate Similarity	NPC233165
0.811	Intermediate Similarity	NPC184579
0.8106	Intermediate Similarity	NPC324209
0.8106	Intermediate Similarity	NPC71525
0.8106	Intermediate Similarity	NPC181715
0.8102	Intermediate Similarity	NPC272268
0.8102	Intermediate Similarity	NPC475549
0.8102	Intermediate Similarity	NPC474813
0.8102	Intermediate Similarity	NPC193358
0.8092	Intermediate Similarity	NPC240744
0.8092	Intermediate Similarity	NPC131799
0.8092	Intermediate Similarity	NPC167055

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 NPC51037 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	286
0.1-0.2	973
0.2-0.3	1428
0.3-0.4	2706
0.4-0.5	2096
0.5-0.6	1154
0.6-0.7	432
0.7-0.8	72
0.8-0.85	1
0.85-0.9	1
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9076	High Similarity	NPD405	Clinical (unspecified phase)
0.8516	High Similarity	NPD1470	Approved
0.8203	Intermediate Similarity	NPD1201	Approved
0.8102	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7971	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7874	Intermediate Similarity	NPD9493	Approved
0.773	Intermediate Similarity	NPD2346	Discontinued
0.7708	Intermediate Similarity	NPD3300	Phase 2
0.7681	Intermediate Similarity	NPD943	Approved
0.7676	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7661	Intermediate Similarity	NPD9266	Approved
0.7661	Intermediate Similarity	NPD74	Approved
0.766	Intermediate Similarity	NPD2935	Discontinued
0.7635	Intermediate Similarity	NPD3226	Approved
0.7606	Intermediate Similarity	NPD1471	Phase 3
0.7606	Intermediate Similarity	NPD2344	Approved
0.7581	Intermediate Similarity	NPD9267	Approved
0.7581	Intermediate Similarity	NPD9264	Approved
0.7581	Intermediate Similarity	NPD9263	Approved
0.7554	Intermediate Similarity	NPD1240	Approved
0.75	Intermediate Similarity	NPD2798	Approved
0.75	Intermediate Similarity	NPD447	Suspended
0.7465	Intermediate Similarity	NPD1510	Phase 2
0.7463	Intermediate Similarity	NPD9717	Approved
0.7448	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD1607	Approved
0.7426	Intermediate Similarity	NPD1164	Approved
0.7426	Intermediate Similarity	NPD1203	Approved
0.741	Intermediate Similarity	NPD2313	Discontinued
0.7397	Intermediate Similarity	NPD2309	Approved
0.7365	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7343	Intermediate Similarity	NPD2799	Discontinued
0.7338	Intermediate Similarity	NPD3882	Suspended
0.7315	Intermediate Similarity	NPD1512	Approved
0.7308	Intermediate Similarity	NPD9281	Approved
0.7297	Intermediate Similarity	NPD7390	Discontinued
0.7293	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD5408	Approved
0.7292	Intermediate Similarity	NPD5404	Approved
0.7292	Intermediate Similarity	NPD5406	Approved
0.7292	Intermediate Similarity	NPD5405	Approved
0.7286	Intermediate Similarity	NPD411	Approved
0.7259	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7258	Intermediate Similarity	NPD9261	Approved
0.7239	Intermediate Similarity	NPD2932	Approved
0.7226	Intermediate Similarity	NPD1876	Approved
0.7222	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7218	Intermediate Similarity	NPD9545	Approved
0.7209	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD164	Approved
0.72	Intermediate Similarity	NPD1237	Approved
0.7194	Intermediate Similarity	NPD9494	Approved
0.7192	Intermediate Similarity	NPD1549	Phase 2
0.7181	Intermediate Similarity	NPD1511	Approved
0.7165	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD3764	Approved
0.7133	Intermediate Similarity	NPD2533	Approved
0.7133	Intermediate Similarity	NPD2534	Approved
0.7133	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD2532	Approved
0.7133	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD520	Approved
0.7111	Intermediate Similarity	NPD3019	Approved
0.7107	Intermediate Similarity	NPD6232	Discontinued
0.7099	Intermediate Similarity	NPD1241	Discontinued
0.7097	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD7819	Suspended
0.7097	Intermediate Similarity	NPD2801	Approved
0.7095	Intermediate Similarity	NPD3750	Approved
0.7081	Intermediate Similarity	NPD7473	Discontinued
0.7067	Intermediate Similarity	NPD6799	Approved
0.7055	Intermediate Similarity	NPD1551	Phase 2
0.7051	Intermediate Similarity	NPD5402	Approved
0.7032	Intermediate Similarity	NPD1934	Approved
0.7027	Intermediate Similarity	NPD2800	Approved
0.7021	Intermediate Similarity	NPD6832	Phase 2
0.7014	Intermediate Similarity	NPD230	Phase 1
0.7007	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD1019	Discontinued
0.6992	Remote Similarity	NPD288	Approved
0.6987	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD1283	Approved
0.6977	Remote Similarity	NPD2182	Approved
0.6962	Remote Similarity	NPD7075	Discontinued
0.6957	Remote Similarity	NPD9269	Phase 2
0.6957	Remote Similarity	NPD3972	Approved
0.6943	Remote Similarity	NPD3817	Phase 2
0.6933	Remote Similarity	NPD3751	Discontinued
0.6923	Remote Similarity	NPD6844	Discontinued
0.6917	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6912	Remote Similarity	NPD9268	Approved
0.6912	Remote Similarity	NPD1651	Approved
0.6911	Remote Similarity	NPD844	Approved
0.6906	Remote Similarity	NPD1755	Approved
0.6903	Remote Similarity	NPD4380	Phase 2
0.6903	Remote Similarity	NPD6599	Discontinued
0.6901	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD7003	Approved
0.6864	Remote Similarity	NPD8150	Discontinued
0.6861	Remote Similarity	NPD4626	Approved
0.6855	Remote Similarity	NPD3749	Approved
0.6846	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD1608	Approved
0.6835	Remote Similarity	NPD2296	Approved
0.6832	Remote Similarity	NPD6959	Discontinued
0.6828	Remote Similarity	NPD4060	Phase 1
0.6826	Remote Similarity	NPD4954	Approved
0.6826	Remote Similarity	NPD4955	Approved
0.6826	Remote Similarity	NPD5026	Approved
0.6826	Remote Similarity	NPD5034	Approved
0.6826	Remote Similarity	NPD5028	Approved
0.6826	Remote Similarity	NPD36	Approved
0.6824	Remote Similarity	NPD2796	Approved
0.6818	Remote Similarity	NPD5403	Approved
0.681	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.681	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.681	Remote Similarity	NPD6166	Phase 2
0.6806	Remote Similarity	NPD3268	Approved
0.68	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD5401	Approved
0.6797	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6767	Remote Similarity	NPD7635	Approved
0.6766	Remote Similarity	NPD5027	Approved
0.6766	Remote Similarity	NPD5029	Approved
0.6766	Remote Similarity	NPD5030	Phase 2
0.6766	Remote Similarity	NPD5031	Approved
0.6763	Remote Similarity	NPD1281	Approved
0.6757	Remote Similarity	NPD3748	Approved
0.6757	Remote Similarity	NPD4308	Phase 3
0.6755	Remote Similarity	NPD8166	Discontinued
0.6739	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD6651	Approved
0.6731	Remote Similarity	NPD2651	Approved
0.6731	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD2649	Approved
0.673	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6728	Remote Similarity	NPD1247	Approved
0.6714	Remote Similarity	NPD4878	Approved
0.6711	Remote Similarity	NPD6190	Approved
0.6709	Remote Similarity	NPD6801	Discontinued
0.6707	Remote Similarity	NPD6797	Phase 2
0.6691	Remote Similarity	NPD3026	Approved
0.6691	Remote Similarity	NPD3496	Discontinued
0.6691	Remote Similarity	NPD3023	Approved
0.669	Remote Similarity	NPD2797	Approved
0.6686	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6355	Discontinued
0.6667	Remote Similarity	NPD3025	Approved
0.6667	Remote Similarity	NPD1933	Approved
0.6667	Remote Similarity	NPD5951	Approved
0.6667	Remote Similarity	NPD3024	Approved
0.6667	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4750	Phase 3
0.6667	Remote Similarity	NPD7251	Discontinued
0.6667	Remote Similarity	NPD5038	Approved
0.6667	Remote Similarity	NPD5037	Approved
0.6646	Remote Similarity	NPD7411	Suspended
0.6646	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD3926	Phase 2
0.6645	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD4628	Phase 3
0.6644	Remote Similarity	NPD6663	Approved
0.6641	Remote Similarity	NPD2342	Discontinued
0.6639	Remote Similarity	NPD9256	Approved
0.6639	Remote Similarity	NPD9258	Approved
0.6627	Remote Similarity	NPD7808	Phase 3
0.6627	Remote Similarity	NPD3818	Discontinued
0.6627	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6624	Remote Similarity	NPD7458	Discontinued
0.6619	Remote Similarity	NPD17	Approved
0.6619	Remote Similarity	NPD1778	Approved
0.6618	Remote Similarity	NPD6671	Approved
0.6617	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6617	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6614	Remote Similarity	NPD3020	Approved
0.6613	Remote Similarity	NPD845	Approved
0.6608	Remote Similarity	NPD5036	Approved
0.6605	Remote Similarity	NPD919	Approved
0.6603	Remote Similarity	NPD920	Approved
0.6601	Remote Similarity	NPD2354	Approved
0.66	Remote Similarity	NPD6099	Approved
0.66	Remote Similarity	NPD6100	Approved
0.6597	Remote Similarity	NPD5736	Approved
0.6596	Remote Similarity	NPD1481	Phase 2
0.6589	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6589	Remote Similarity	NPD1930	Approved
0.6589	Remote Similarity	NPD1929	Approved
0.6588	Remote Similarity	NPD8313	Approved
0.6588	Remote Similarity	NPD8312	Approved
0.6587	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD5711	Approved
0.6585	Remote Similarity	NPD5710	Approved
0.6584	Remote Similarity	NPD7768	Phase 2
0.6575	Remote Similarity	NPD6798	Discontinued
0.6573	Remote Similarity	NPD3266	Approved
0.6573	Remote Similarity	NPD3267	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