NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	254.09
Volume:	273.458
LogP:	2.971
LogD:	3.149
LogS:	-4.159
# Rotatable Bonds:	4
TPSA:	46.53
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.672
Synthetic Accessibility Score:	1.853
Fsp3:	0.062
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.759
MDCK Permeability:	1.322848220297601e-05
Pgp-inhibitor:	0.003
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.075
30% Bioavailability (F30%):	0.562

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.38
Plasma Protein Binding (PPB):	98.6905288696289%
Volume Distribution (VD):	0.57
Pgp-substrate:	1.1449131965637207%

ADMET: Metabolism

CYP1A2-inhibitor:	0.987
CYP1A2-substrate:	0.501
CYP2C19-inhibitor:	0.924
CYP2C19-substrate:	0.07
CYP2C9-inhibitor:	0.76
CYP2C9-substrate:	0.956
CYP2D6-inhibitor:	0.761
CYP2D6-substrate:	0.876
CYP3A4-inhibitor:	0.787
CYP3A4-substrate:	0.244

ADMET: Excretion

Clearance (CL):	11.775
Half-life (T1/2):	0.821

ADMET: Toxicity

hERG Blockers:	0.146
Human Hepatotoxicity (H-HT):	0.026
Drug-inuced Liver Injury (DILI):	0.557
AMES Toxicity:	0.37
Rat Oral Acute Toxicity:	0.034
Maximum Recommended Daily Dose:	0.26
Skin Sensitization:	0.882
Carcinogencity:	0.762
Eye Corrosion:	0.183
Eye Irritation:	0.991
Respiratory Toxicity:	0.527

Download Data

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

Natural Product: NPC308037

Natural Product ID:	NPC308037
*Common Name:**	2-Methoxyisoliquiritigenin
IUPAC Name:	(E)-1-(4-hydroxy-2-methoxyphenyl)-3-phenylprop-2-en-1-one
Synonyms:	2-Methoxyisoliquiritigenin
Standard InCHIKey:	VLEOOBKBMSIDKF-JXMROGBWSA-N
Standard InCHI:	InChI=1S/C16H14O3/c1-19-16-11-13(17)8-9-14(16)15(18)10-7-12-5-3-2-4-6-12/h2-11,17H,1H3/b10-7+
SMILES:	COc1cc(O)ccc1C(=O)/C=C/c1ccccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL445232
PubChem CID:	13842401
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0003467] Linear 1,3-diarylpropanoids [CHEMONTID:0003496] Cinnamylphenols

*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
NPO29428	Dalbergia cochinchinensis	Species	Fabaceae	Eukaryota	n.a.	seed	n.a.	DOI[10.1016/S0031-9422(98)00552-4]
NPO29428	Dalbergia cochinchinensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12932142]
NPO16886	Amorpha fruticosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18841906]
NPO16886	Amorpha fruticosa	Species	Fabaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[28075580]
NPO16886	Amorpha fruticosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8326318]
NPO16886	Amorpha fruticosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8350086]
NPO29428	Dalbergia cochinchinensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16886	Amorpha fruticosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16886	Amorpha fruticosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29428	Dalbergia cochinchinensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29428	Dalbergia cochinchinensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO16886	Amorpha fruticosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29428	Dalbergia cochinchinensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16886	Amorpha fruticosa	Species	Fabaceae	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	2
Others	3

Activity Type	# Activity
Others	5

Target ID	Target Type	Target Name	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified	IC50	>	50000.0	nM	PMID[466497]
NPT2	Others	Unspecified	IC50	=	24700.0	nM	PMID[466497]
NPT2	Others	Unspecified	Inhibition	=	19.5	%	PMID[466498]
NPT2	Others	Unspecified	Inhibition	=	20.7	%	PMID[466498]
NPT2	Others	Unspecified	Inhibition	=	22.8	%	PMID[466498]

☑ 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 NPC308037 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	341
0.1-0.2	1710
0.2-0.3	4661
0.3-0.4	11711
0.4-0.5	5885
0.5-0.6	4087
0.6-0.7	5994
0.7-0.8	5351
0.8-0.85	1780
0.85-0.9	804
0.9-0.95	292
0.95-1	81

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC64359
0.9921	High Similarity	NPC212631
0.9921	High Similarity	NPC257756
0.9921	High Similarity	NPC205468
0.9921	High Similarity	NPC87231
0.9921	High Similarity	NPC129132
0.9843	High Similarity	NPC263670
0.9843	High Similarity	NPC192304
0.9843	High Similarity	NPC472365
0.9843	High Similarity	NPC139813
0.9843	High Similarity	NPC175098
0.9843	High Similarity	NPC188646
0.9843	High Similarity	NPC337373
0.9843	High Similarity	NPC242294
0.9843	High Similarity	NPC312318
0.9843	High Similarity	NPC56031
0.9841	High Similarity	NPC262359
0.9841	High Similarity	NPC313618
0.9766	High Similarity	NPC286336
0.9688	High Similarity	NPC18877
0.9688	High Similarity	NPC20560
0.9688	High Similarity	NPC159623
0.9688	High Similarity	NPC144051
0.9688	High Similarity	NPC294593
0.9688	High Similarity	NPC28753
0.9688	High Similarity	NPC204960
0.9688	High Similarity	NPC82225
0.9683	High Similarity	NPC247779
0.968	High Similarity	NPC186098
0.968	High Similarity	NPC80694
0.9615	High Similarity	NPC1486
0.9615	High Similarity	NPC186838
0.9615	High Similarity	NPC41461
0.9615	High Similarity	NPC473391
0.9615	High Similarity	NPC477244
0.9615	High Similarity	NPC477242
0.9615	High Similarity	NPC168105
0.9615	High Similarity	NPC25287
0.9615	High Similarity	NPC150399
0.9615	High Similarity	NPC12165
0.9615	High Similarity	NPC477243
0.9615	High Similarity	NPC274109
0.9615	High Similarity	NPC476333
0.9615	High Similarity	NPC240593
0.9615	High Similarity	NPC66349
0.9615	High Similarity	NPC249606
0.9615	High Similarity	NPC98115
0.9615	High Similarity	NPC472367
0.9615	High Similarity	NPC472364
0.9542	High Similarity	NPC317119
0.9542	High Similarity	NPC188879
0.9542	High Similarity	NPC116632
0.9542	High Similarity	NPC250266
0.9542	High Similarity	NPC303644
0.9542	High Similarity	NPC472419
0.9542	High Similarity	NPC266597
0.9542	High Similarity	NPC162680
0.9542	High Similarity	NPC7013
0.9542	High Similarity	NPC209560
0.9542	High Similarity	NPC181124
0.9542	High Similarity	NPC294409
0.9542	High Similarity	NPC153979
0.9538	High Similarity	NPC156092
0.9538	High Similarity	NPC13575
0.9538	High Similarity	NPC131039
0.9531	High Similarity	NPC112192
0.9531	High Similarity	NPC66384
0.9531	High Similarity	NPC186097
0.9531	High Similarity	NPC475009
0.9531	High Similarity	NPC189106
0.9531	High Similarity	NPC164236
0.9531	High Similarity	NPC309717
0.9531	High Similarity	NPC475008
0.9531	High Similarity	NPC128348
0.947	High Similarity	NPC279668
0.947	High Similarity	NPC278323
0.947	High Similarity	NPC21350
0.947	High Similarity	NPC55162
0.947	High Similarity	NPC309154
0.947	High Similarity	NPC280284
0.947	High Similarity	NPC12175
0.947	High Similarity	NPC472368
0.947	High Similarity	NPC188947
0.947	High Similarity	NPC90665
0.947	High Similarity	NPC124269
0.947	High Similarity	NPC99333
0.9466	High Similarity	NPC234133
0.9466	High Similarity	NPC194281
0.9466	High Similarity	NPC47815
0.9466	High Similarity	NPC213603
0.9466	High Similarity	NPC124784
0.9466	High Similarity	NPC29353
0.9466	High Similarity	NPC473887
0.9466	High Similarity	NPC127447
0.9466	High Similarity	NPC231772
0.9462	High Similarity	NPC103842
0.9449	High Similarity	NPC211120
0.9449	High Similarity	NPC60558
0.9444	High Similarity	NPC305518
0.9444	High Similarity	NPC128428
0.9398	High Similarity	NPC470211
0.9398	High Similarity	NPC295384
0.9398	High Similarity	NPC472366
0.9398	High Similarity	NPC477956
0.9394	High Similarity	NPC228661
0.9394	High Similarity	NPC290291
0.9394	High Similarity	NPC275055
0.9389	High Similarity	NPC39426
0.9389	High Similarity	NPC234560
0.9385	High Similarity	NPC57601
0.9385	High Similarity	NPC27643
0.9375	High Similarity	NPC185497
0.9328	High Similarity	NPC101366
0.9328	High Similarity	NPC269652
0.9328	High Similarity	NPC11056
0.9328	High Similarity	NPC213659
0.9328	High Similarity	NPC204985
0.9328	High Similarity	NPC281207
0.9328	High Similarity	NPC215311
0.9328	High Similarity	NPC259166
0.9328	High Similarity	NPC48624
0.9328	High Similarity	NPC172250
0.9328	High Similarity	NPC144118
0.9328	High Similarity	NPC326109
0.9328	High Similarity	NPC80962
0.9328	High Similarity	NPC219917
0.9323	High Similarity	NPC471620
0.9323	High Similarity	NPC243528
0.9323	High Similarity	NPC251681
0.9318	High Similarity	NPC87545
0.9318	High Similarity	NPC13408
0.9318	High Similarity	NPC235428
0.9313	High Similarity	NPC172262
0.9297	High Similarity	NPC8005
0.9297	High Similarity	NPC78662
0.9297	High Similarity	NPC212379
0.9297	High Similarity	NPC69235
0.9259	High Similarity	NPC136840
0.9259	High Similarity	NPC268204
0.9259	High Similarity	NPC470087
0.9259	High Similarity	NPC470089
0.9259	High Similarity	NPC49108
0.9259	High Similarity	NPC55832
0.9259	High Similarity	NPC110969
0.9259	High Similarity	NPC469404
0.9259	High Similarity	NPC284556
0.9259	High Similarity	NPC301178
0.9259	High Similarity	NPC26051
0.9259	High Similarity	NPC321980
0.9259	High Similarity	NPC3188
0.9259	High Similarity	NPC52789
0.9254	High Similarity	NPC78913
0.9254	High Similarity	NPC20709
0.9254	High Similarity	NPC143799
0.9254	High Similarity	NPC261234
0.9254	High Similarity	NPC283429
0.9254	High Similarity	NPC241838
0.9254	High Similarity	NPC109232
0.9254	High Similarity	NPC329203
0.9254	High Similarity	NPC310135
0.9254	High Similarity	NPC150648
0.9254	High Similarity	NPC152042
0.9254	High Similarity	NPC18260
0.9254	High Similarity	NPC225153
0.9254	High Similarity	NPC274784
0.9254	High Similarity	NPC222342
0.9254	High Similarity	NPC265871
0.9248	High Similarity	NPC212767
0.9248	High Similarity	NPC84585
0.9248	High Similarity	NPC476480
0.9242	High Similarity	NPC239495
0.9242	High Similarity	NPC9985
0.9237	High Similarity	NPC50898
0.9237	High Similarity	NPC78540
0.9237	High Similarity	NPC213216
0.9237	High Similarity	NPC274121
0.9231	High Similarity	NPC475589
0.9231	High Similarity	NPC284424
0.9231	High Similarity	NPC31872
0.9231	High Similarity	NPC473584
0.9225	High Similarity	NPC307732
0.9225	High Similarity	NPC42292
0.9191	High Similarity	NPC202981
0.9191	High Similarity	NPC226636
0.9191	High Similarity	NPC11561
0.9191	High Similarity	NPC119663
0.9191	High Similarity	NPC471417
0.9185	High Similarity	NPC159275
0.9185	High Similarity	NPC184536
0.9185	High Similarity	NPC146679
0.9185	High Similarity	NPC230285
0.9185	High Similarity	NPC253822
0.9185	High Similarity	NPC129853
0.9185	High Similarity	NPC305355
0.9185	High Similarity	NPC110228
0.9185	High Similarity	NPC76445
0.9185	High Similarity	NPC265178
0.9185	High Similarity	NPC69769
0.9185	High Similarity	NPC241100
0.9185	High Similarity	NPC59951

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 NPC308037 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	337
0.1-0.2	989
0.2-0.3	1474
0.3-0.4	2656
0.4-0.5	1887
0.5-0.6	1208
0.6-0.7	413
0.7-0.8	138
0.8-0.85	37
0.85-0.9	6
0.9-0.95	3
0.95-1	2

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9841	High Similarity	NPD1240	Approved
0.9688	High Similarity	NPD1607	Approved
0.9389	High Similarity	NPD1510	Phase 2
0.9179	High Similarity	NPD1549	Phase 2
0.9104	High Similarity	NPD1552	Clinical (unspecified phase)
0.9104	High Similarity	NPD1550	Clinical (unspecified phase)
0.8921	High Similarity	NPD4378	Clinical (unspecified phase)
0.8889	High Similarity	NPD2796	Approved
0.8786	High Similarity	NPD7410	Clinical (unspecified phase)
0.8714	High Similarity	NPD6799	Approved
0.8623	High Similarity	NPD970	Clinical (unspecified phase)
0.8611	High Similarity	NPD4380	Phase 2
0.8582	High Similarity	NPD1511	Approved
0.8552	High Similarity	NPD7411	Suspended
0.85	High Similarity	NPD1878	Clinical (unspecified phase)
0.8493	Intermediate Similarity	NPD1934	Approved
0.8478	Intermediate Similarity	NPD1551	Phase 2
0.8462	Intermediate Similarity	NPD1512	Approved
0.8446	Intermediate Similarity	NPD3882	Suspended
0.8435	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8435	Intermediate Similarity	NPD2801	Approved
0.8394	Intermediate Similarity	NPD6651	Approved
0.8389	Intermediate Similarity	NPD7075	Discontinued
0.8378	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.837	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8369	Intermediate Similarity	NPD3750	Approved
0.8356	Intermediate Similarity	NPD6599	Discontinued
0.8345	Intermediate Similarity	NPD2935	Discontinued
0.8311	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8311	Intermediate Similarity	NPD7819	Suspended
0.8286	Intermediate Similarity	NPD2344	Approved
0.8271	Intermediate Similarity	NPD1203	Approved
0.8267	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8248	Intermediate Similarity	NPD943	Approved
0.8243	Intermediate Similarity	NPD6801	Discontinued
0.8203	Intermediate Similarity	NPD9493	Approved
0.8169	Intermediate Similarity	NPD2800	Approved
0.8169	Intermediate Similarity	NPD1243	Approved
0.8169	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8146	Intermediate Similarity	NPD3749	Approved
0.8079	Intermediate Similarity	NPD7768	Phase 2
0.8077	Intermediate Similarity	NPD9545	Approved
0.8074	Intermediate Similarity	NPD2798	Approved
0.8065	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8056	Intermediate Similarity	NPD2309	Approved
0.8045	Intermediate Similarity	NPD3972	Approved
0.8045	Intermediate Similarity	NPD9717	Approved
0.8042	Intermediate Similarity	NPD2654	Approved
0.8027	Intermediate Similarity	NPD5403	Approved
0.8014	Intermediate Similarity	NPD5401	Approved
0.8014	Intermediate Similarity	NPD3748	Approved
0.8014	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8013	Intermediate Similarity	NPD3817	Phase 2
0.8	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.797	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.797	Intermediate Similarity	NPD422	Phase 1
0.7956	Intermediate Similarity	NPD6832	Phase 2
0.7949	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7949	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7949	Intermediate Similarity	NPD6166	Phase 2
0.7939	Intermediate Similarity	NPD1548	Phase 1
0.7935	Intermediate Similarity	NPD6232	Discontinued
0.7905	Intermediate Similarity	NPD920	Approved
0.7898	Intermediate Similarity	NPD7473	Discontinued
0.7891	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7891	Intermediate Similarity	NPD2532	Approved
0.7891	Intermediate Similarity	NPD2533	Approved
0.7891	Intermediate Similarity	NPD2534	Approved
0.7887	Intermediate Similarity	NPD2799	Discontinued
0.7871	Intermediate Similarity	NPD6959	Discontinued
0.7848	Intermediate Similarity	NPD3818	Discontinued
0.7812	Intermediate Similarity	NPD5953	Discontinued
0.7799	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7799	Intermediate Similarity	NPD7286	Phase 2
0.7799	Intermediate Similarity	NPD7054	Approved
0.775	Intermediate Similarity	NPD7074	Phase 3
0.775	Intermediate Similarity	NPD7472	Approved
0.774	Intermediate Similarity	NPD4628	Phase 3
0.7727	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7714	Intermediate Similarity	NPD2313	Discontinued
0.7708	Intermediate Similarity	NPD6100	Approved
0.7708	Intermediate Similarity	NPD6099	Approved
0.7704	Intermediate Similarity	NPD1610	Phase 2
0.7702	Intermediate Similarity	NPD6797	Phase 2
0.7692	Intermediate Similarity	NPD5494	Approved
0.7692	Intermediate Similarity	NPD1241	Discontinued
0.7676	Intermediate Similarity	NPD230	Phase 1
0.7667	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7664	Intermediate Similarity	NPD1876	Approved
0.7662	Intermediate Similarity	NPD5402	Approved
0.7654	Intermediate Similarity	NPD7251	Discontinued
0.7639	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7609	Intermediate Similarity	NPD1164	Approved
0.7609	Intermediate Similarity	NPD2797	Approved
0.7607	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7607	Intermediate Similarity	NPD7808	Phase 3
0.7589	Intermediate Similarity	NPD3268	Approved
0.7584	Intermediate Similarity	NPD7390	Discontinued
0.7578	Intermediate Similarity	NPD74	Approved
0.7578	Intermediate Similarity	NPD9266	Approved
0.7574	Intermediate Similarity	NPD1201	Approved
0.7571	Intermediate Similarity	NPD4908	Phase 1
0.7566	Intermediate Similarity	NPD3226	Approved
0.7552	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7552	Intermediate Similarity	NPD1933	Approved
0.7547	Intermediate Similarity	NPD3926	Phase 2
0.7546	Intermediate Similarity	NPD6559	Discontinued
0.7536	Intermediate Similarity	NPD3225	Approved
0.7518	Intermediate Similarity	NPD1608	Approved
0.7517	Intermediate Similarity	NPD7033	Discontinued
0.7517	Intermediate Similarity	NPD4308	Phase 3
0.7516	Intermediate Similarity	NPD919	Approved
0.75	Intermediate Similarity	NPD9263	Approved
0.75	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD9494	Approved
0.75	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD9267	Approved
0.75	Intermediate Similarity	NPD9264	Approved
0.7482	Intermediate Similarity	NPD1470	Approved
0.7465	Intermediate Similarity	NPD3764	Approved
0.7465	Intermediate Similarity	NPD411	Approved
0.7465	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD2296	Approved
0.7431	Intermediate Similarity	NPD447	Suspended
0.7429	Intermediate Similarity	NPD1019	Discontinued
0.7423	Intermediate Similarity	NPD1729	Discontinued
0.7421	Intermediate Similarity	NPD1247	Approved
0.7415	Intermediate Similarity	NPD2346	Discontinued
0.7388	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD7003	Approved
0.7372	Intermediate Similarity	NPD1465	Phase 2
0.7362	Intermediate Similarity	NPD5844	Phase 1
0.7357	Intermediate Similarity	NPD3266	Approved
0.7357	Intermediate Similarity	NPD3267	Approved
0.7353	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7343	Intermediate Similarity	NPD1296	Phase 2
0.7338	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD7458	Discontinued
0.7325	Intermediate Similarity	NPD4288	Approved
0.7299	Intermediate Similarity	NPD17	Approved
0.7279	Intermediate Similarity	NPD1894	Discontinued
0.7273	Intermediate Similarity	NPD3027	Phase 3
0.7273	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD5711	Approved
0.7267	Intermediate Similarity	NPD5710	Approved
0.7266	Intermediate Similarity	NPD1481	Phase 2
0.7244	Intermediate Similarity	NPD940	Approved
0.7244	Intermediate Similarity	NPD846	Approved
0.7241	Intermediate Similarity	NPD3140	Approved
0.7241	Intermediate Similarity	NPD4307	Phase 2
0.7241	Intermediate Similarity	NPD3142	Approved
0.7237	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD5406	Approved
0.723	Intermediate Similarity	NPD5408	Approved
0.723	Intermediate Similarity	NPD5405	Approved
0.723	Intermediate Similarity	NPD5404	Approved
0.7229	Intermediate Similarity	NPD6104	Discontinued
0.7219	Intermediate Similarity	NPD2354	Approved
0.7203	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7194	Intermediate Similarity	NPD1535	Discovery
0.719	Intermediate Similarity	NPD4662	Approved
0.719	Intermediate Similarity	NPD4661	Approved
0.7188	Intermediate Similarity	NPD9261	Approved
0.7184	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD1471	Phase 3
0.7181	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD4360	Phase 2
0.7168	Intermediate Similarity	NPD4363	Phase 3
0.7163	Intermediate Similarity	NPD1283	Approved
0.7153	Intermediate Similarity	NPD4625	Phase 3
0.7143	Intermediate Similarity	NPD9269	Phase 2
0.7135	Intermediate Similarity	NPD4287	Approved
0.7134	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD4361	Phase 2
0.7126	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD1613	Approved
0.7123	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7122	Intermediate Similarity	NPD3847	Discontinued
0.7111	Intermediate Similarity	NPD9281	Approved
0.7103	Intermediate Similarity	NPD6798	Discontinued
0.7101	Intermediate Similarity	NPD9268	Approved
0.7101	Intermediate Similarity	NPD1651	Approved
0.7092	Intermediate Similarity	NPD4749	Approved
0.7091	Intermediate Similarity	NPD3751	Discontinued
0.7089	Intermediate Similarity	NPD6280	Approved
0.7089	Intermediate Similarity	NPD6279	Approved
0.7083	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD5536	Phase 2
0.7078	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD5124	Phase 1
0.7073	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD2353	Approved
0.7067	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7052	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD1242	Phase 1
0.7019	Intermediate Similarity	NPD6971	Discontinued
0.7014	Intermediate Similarity	NPD3018	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