NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	268.07
Volume:	273.692
LogP:	3.665
LogD:	2.969
LogS:	-3.883
# Rotatable Bonds:	2
TPSA:	59.67
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.775
Synthetic Accessibility Score:	1.928
Fsp3:	0.062
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.651
MDCK Permeability:	1.5243274901877157e-05
Pgp-inhibitor:	0.008
Pgp-substrate:	0.672
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.373
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.046
Plasma Protein Binding (PPB):	97.09769439697266%
Volume Distribution (VD):	0.461
Pgp-substrate:	3.542463779449463%

ADMET: Metabolism

CYP1A2-inhibitor:	0.97
CYP1A2-substrate:	0.916
CYP2C19-inhibitor:	0.814
CYP2C19-substrate:	0.08
CYP2C9-inhibitor:	0.49
CYP2C9-substrate:	0.948
CYP2D6-inhibitor:	0.727
CYP2D6-substrate:	0.932
CYP3A4-inhibitor:	0.794
CYP3A4-substrate:	0.328

ADMET: Excretion

Clearance (CL):	5.89
Half-life (T1/2):	0.381

ADMET: Toxicity

hERG Blockers:	0.198
Human Hepatotoxicity (H-HT):	0.103
Drug-inuced Liver Injury (DILI):	0.906
AMES Toxicity:	0.585
Rat Oral Acute Toxicity:	0.159
Maximum Recommended Daily Dose:	0.547
Skin Sensitization:	0.761
Carcinogencity:	0.601
Eye Corrosion:	0.005
Eye Irritation:	0.949
Respiratory Toxicity:	0.253

Download Data

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

Natural Product: NPC250266

Natural Product ID:	NPC250266
*Common Name:**	2-(4-Hydroxyphenyl)-7-Methoxychromen-4-One
IUPAC Name:	2-(4-hydroxyphenyl)-7-methoxychromen-4-one
Synonyms:
Standard InCHIKey:	DZUKXCCSULKRJA-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C16H12O4/c1-19-12-6-7-13-14(18)9-15(20-16(13)8-12)10-2-4-11(17)5-3-10/h2-9,17H,1H3
SMILES:	COc1ccc2c(=O)cc(c3ccc(cc3)O)oc2c1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1600520
PubChem CID:	676307
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0002585] O-methylated flavonoids [CHEMONTID:0002592] 7-O-methylated flavonoids

*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
NPO12465	Glycyrrhiza yunnanensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12465	Glycyrrhiza yunnanensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12465	Glycyrrhiza yunnanensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12465	Glycyrrhiza yunnanensis	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
Potency	21

Activity Type	# Activity
Individual Protein	17
Others	3
Protein-Protein Interaction	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT149	Individual Protein	Endoplasmic reticulum-associated amyloid beta-peptide-binding protein	Homo sapiens	Potency	=	31622.8	nM	PMID[529789]
NPT48	Individual Protein	Lysine-specific demethylase 4D-like	Homo sapiens	Potency	=	31622.8	nM	PMID[529789]
NPT51	Individual Protein	Microtubule-associated protein tau	Homo sapiens	Potency	=	12589.3	nM	PMID[529789]
NPT213	Individual Protein	Cytochrome P450 2C19	Homo sapiens	Potency	=	7943.3	nM	PMID[529790]
NPT51	Individual Protein	Microtubule-associated protein tau	Homo sapiens	Potency	=	11220.2	nM	PMID[529789]
NPT51	Individual Protein	Microtubule-associated protein tau	Homo sapiens	Potency	=	44668.4	nM	PMID[529789]
NPT151	Individual Protein	15-hydroxyprostaglandin dehydrogenase [NAD+]	Homo sapiens	Potency	=	10000.0	nM	PMID[529789]
NPT539	Individual Protein	Cellular tumor antigen p53	Homo sapiens	Potency	=	12589.3	nM	PMID[529789]
NPT149	Individual Protein	Endoplasmic reticulum-associated amyloid beta-peptide-binding protein	Homo sapiens	Potency	=	31622.8	nM	PMID[529790]
NPT110	Individual Protein	Cytochrome P450 2D6	Homo sapiens	Potency	=	15848.9	nM	PMID[529790]
NPT109	Individual Protein	Cytochrome P450 3A4	Homo sapiens	Potency	=	3162.3	nM	PMID[529789]
NPT212	Individual Protein	Cytochrome P450 2C9	Homo sapiens	Potency	=	6309.6	nM	PMID[529790]
NPT61	Individual Protein	Beta-glucocerebrosidase	Homo sapiens	Potency	n.a.	15848.9	nM	PMID[529789]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	26608.6	nM	PMID[529791]
NPT49	Individual Protein	DNA-(apurinic or apyrimidinic site) lyase	Homo sapiens	Potency	n.a.	44668.4	nM	PMID[529789]
NPT197	Protein-Protein Interaction	Menin/Histone-lysine N-methyltransferase MLL	Homo sapiens	Potency	=	39810.7	nM	PMID[529789]
NPT2	Others	Unspecified		Potency	=	12589.3	nM	PMID[529789]
NPT94	Individual Protein	Aldehyde dehydrogenase 1A1	Homo sapiens	Potency	=	25118.9	nM	PMID[529789]
NPT2	Others	Unspecified		Potency	=	7943.3	nM	PMID[529789]
NPT2	Others	Unspecified		Potency	n.a.	14125.4	nM	PMID[529791]

☑ 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 NPC250266 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	460
0.1-0.2	1973
0.2-0.3	5109
0.3-0.4	12298
0.4-0.5	5001
0.5-0.6	4565
0.6-0.7	5759
0.7-0.8	4055
0.8-0.85	1811
0.85-0.9	1207
0.9-0.95	404
0.95-1	55

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC266597
0.9924	High Similarity	NPC29353
0.9924	High Similarity	NPC127447
0.9924	High Similarity	NPC473887
0.9924	High Similarity	NPC234133
0.9924	High Similarity	NPC47815
0.9924	High Similarity	NPC124784
0.9924	High Similarity	NPC231772
0.9924	High Similarity	NPC194281
0.9776	High Similarity	NPC281207
0.9776	High Similarity	NPC269652
0.9774	High Similarity	NPC99333
0.9774	High Similarity	NPC280284
0.9774	High Similarity	NPC188947
0.9773	High Similarity	NPC13408
0.9771	High Similarity	NPC172262
0.9704	High Similarity	NPC110969
0.9704	High Similarity	NPC136840
0.9701	High Similarity	NPC78913
0.9701	High Similarity	NPC18260
0.9701	High Similarity	NPC143799
0.9701	High Similarity	NPC152042
0.9701	High Similarity	NPC241838
0.9699	High Similarity	NPC228661
0.9699	High Similarity	NPC275055
0.9699	High Similarity	NPC290291
0.9699	High Similarity	NPC188879
0.9695	High Similarity	NPC213216
0.9695	High Similarity	NPC274121
0.9695	High Similarity	NPC78540
0.9695	High Similarity	NPC50898
0.9695	High Similarity	NPC57601
0.9632	High Similarity	NPC226636
0.9632	High Similarity	NPC11561
0.963	High Similarity	NPC146679
0.963	High Similarity	NPC172986
0.963	High Similarity	NPC270883
0.963	High Similarity	NPC230285
0.963	High Similarity	NPC159275
0.963	High Similarity	NPC184536
0.963	High Similarity	NPC261227
0.963	High Similarity	NPC241100
0.963	High Similarity	NPC103342
0.963	High Similarity	NPC59951
0.963	High Similarity	NPC103904
0.9627	High Similarity	NPC124269
0.9627	High Similarity	NPC201395
0.9624	High Similarity	NPC240593
0.9618	High Similarity	NPC212631
0.9618	High Similarity	NPC129132
0.9618	High Similarity	NPC257756
0.9618	High Similarity	NPC205468
0.9618	High Similarity	NPC87231
0.9559	High Similarity	NPC90582
0.9559	High Similarity	NPC205006
0.9559	High Similarity	NPC103362
0.9559	High Similarity	NPC118840
0.9559	High Similarity	NPC3188
0.9559	High Similarity	NPC64908
0.9559	High Similarity	NPC282300
0.9559	High Similarity	NPC147688
0.9559	High Similarity	NPC156590
0.9559	High Similarity	NPC262094
0.9556	High Similarity	NPC225153
0.9556	High Similarity	NPC96565
0.9556	High Similarity	NPC222342
0.9556	High Similarity	NPC265871
0.9556	High Similarity	NPC329203
0.9556	High Similarity	NPC53181
0.9556	High Similarity	NPC274784
0.9556	High Similarity	NPC150648
0.9556	High Similarity	NPC216978
0.9556	High Similarity	NPC310135
0.9556	High Similarity	NPC301217
0.9556	High Similarity	NPC261234
0.9556	High Similarity	NPC220062
0.9556	High Similarity	NPC20709
0.9556	High Similarity	NPC303633
0.9556	High Similarity	NPC55018
0.9556	High Similarity	NPC217186
0.9552	High Similarity	NPC303644
0.9552	High Similarity	NPC162680
0.9552	High Similarity	NPC7013
0.9552	High Similarity	NPC209560
0.9552	High Similarity	NPC294409
0.9552	High Similarity	NPC181124
0.9552	High Similarity	NPC299379
0.9552	High Similarity	NPC116632
0.9549	High Similarity	NPC9985
0.9549	High Similarity	NPC239495
0.9545	High Similarity	NPC337373
0.9545	High Similarity	NPC312318
0.9545	High Similarity	NPC472365
0.9545	High Similarity	NPC263670
0.9545	High Similarity	NPC175098
0.9545	High Similarity	NPC56031
0.9545	High Similarity	NPC139813
0.9545	High Similarity	NPC242294
0.9545	High Similarity	NPC192304
0.9545	High Similarity	NPC188646
0.9542	High Similarity	NPC473584
0.9542	High Similarity	NPC308037
0.9542	High Similarity	NPC475589
0.9542	High Similarity	NPC262359
0.9542	High Similarity	NPC113006
0.9542	High Similarity	NPC64359
0.9542	High Similarity	NPC278556
0.9542	High Similarity	NPC284424
0.9542	High Similarity	NPC31872
0.9493	High Similarity	NPC234629
0.9493	High Similarity	NPC311741
0.9489	High Similarity	NPC202981
0.9485	High Similarity	NPC129853
0.9485	High Similarity	NPC188243
0.9485	High Similarity	NPC150522
0.9485	High Similarity	NPC69769
0.9485	High Similarity	NPC6407
0.9485	High Similarity	NPC110228
0.9485	High Similarity	NPC76445
0.9485	High Similarity	NPC284550
0.9485	High Similarity	NPC305355
0.9485	High Similarity	NPC235239
0.9485	High Similarity	NPC475680
0.9481	High Similarity	NPC147686
0.9481	High Similarity	NPC472460
0.9481	High Similarity	NPC309154
0.9481	High Similarity	NPC329225
0.9481	High Similarity	NPC118813
0.9481	High Similarity	NPC90665
0.9481	High Similarity	NPC12175
0.9481	High Similarity	NPC55162
0.9481	High Similarity	NPC278323
0.9481	High Similarity	NPC276905
0.9481	High Similarity	NPC279668
0.9478	High Similarity	NPC256042
0.9478	High Similarity	NPC216361
0.9478	High Similarity	NPC116775
0.9478	High Similarity	NPC281917
0.9478	High Similarity	NPC187432
0.9474	High Similarity	NPC286336
0.947	High Similarity	NPC473655
0.947	High Similarity	NPC10971
0.947	High Similarity	NPC101294
0.947	High Similarity	NPC25937
0.9466	High Similarity	NPC270369
0.9466	High Similarity	NPC137264
0.9466	High Similarity	NPC5515
0.942	High Similarity	NPC164980
0.942	High Similarity	NPC470216
0.942	High Similarity	NPC221432
0.942	High Similarity	NPC166138
0.942	High Similarity	NPC310130
0.942	High Similarity	NPC106985
0.942	High Similarity	NPC75049
0.942	High Similarity	NPC91560
0.942	High Similarity	NPC68104
0.942	High Similarity	NPC257097
0.942	High Similarity	NPC149026
0.942	High Similarity	NPC39329
0.942	High Similarity	NPC150408
0.942	High Similarity	NPC143896
0.942	High Similarity	NPC169591
0.942	High Similarity	NPC38219
0.942	High Similarity	NPC175504
0.942	High Similarity	NPC18585
0.9416	High Similarity	NPC324386
0.9416	High Similarity	NPC312391
0.9416	High Similarity	NPC213322
0.9416	High Similarity	NPC4743
0.9412	High Similarity	NPC140890
0.9412	High Similarity	NPC295384
0.9407	High Similarity	NPC79943
0.9407	High Similarity	NPC107586
0.9407	High Similarity	NPC476480
0.9407	High Similarity	NPC295261
0.9407	High Similarity	NPC84585
0.9407	High Similarity	NPC296490
0.9407	High Similarity	NPC32441
0.9407	High Similarity	NPC287246
0.9407	High Similarity	NPC243083
0.9407	High Similarity	NPC13768
0.9407	High Similarity	NPC12296
0.9403	High Similarity	NPC234560
0.9403	High Similarity	NPC39426
0.9398	High Similarity	NPC82225
0.9398	High Similarity	NPC292998
0.9398	High Similarity	NPC18877
0.9398	High Similarity	NPC144051
0.9398	High Similarity	NPC159623
0.9398	High Similarity	NPC28753
0.9398	High Similarity	NPC223457
0.9398	High Similarity	NPC20560
0.9398	High Similarity	NPC294593
0.9398	High Similarity	NPC204960
0.9394	High Similarity	NPC313618
0.9389	High Similarity	NPC39753
0.9389	High Similarity	NPC247779
0.9389	High Similarity	NPC115998
0.9357	High Similarity	NPC237635
0.9357	High Similarity	NPC23728

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 NPC250266 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	444
0.1-0.2	1006
0.2-0.3	1528
0.3-0.4	2723
0.4-0.5	1823
0.5-0.6	1129
0.6-0.7	322
0.7-0.8	111
0.8-0.85	41
0.85-0.9	14
0.9-0.95	9
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9481	High Similarity	NPD1549	Phase 2
0.9407	High Similarity	NPD1552	Clinical (unspecified phase)
0.9407	High Similarity	NPD1550	Clinical (unspecified phase)
0.9403	High Similarity	NPD1510	Phase 2
0.9394	High Similarity	NPD1240	Approved
0.9353	High Similarity	NPD4378	Clinical (unspecified phase)
0.9254	High Similarity	NPD1607	Approved
0.9214	High Similarity	NPD7410	Clinical (unspecified phase)
0.9191	High Similarity	NPD2796	Approved
0.9007	High Similarity	NPD1511	Approved
0.8881	High Similarity	NPD1512	Approved
0.8873	High Similarity	NPD6799	Approved
0.8844	High Similarity	NPD2801	Approved
0.8836	High Similarity	NPD7411	Suspended
0.8794	High Similarity	NPD3750	Approved
0.8776	High Similarity	NPD1934	Approved
0.8767	High Similarity	NPD4380	Phase 2
0.8716	High Similarity	NPD2393	Clinical (unspecified phase)
0.8667	High Similarity	NPD4381	Clinical (unspecified phase)
0.8667	High Similarity	NPD7075	Discontinued
0.8658	High Similarity	NPD8443	Clinical (unspecified phase)
0.8652	High Similarity	NPD970	Clinical (unspecified phase)
0.8649	High Similarity	NPD6801	Discontinued
0.8643	High Similarity	NPD1551	Phase 2
0.86	High Similarity	NPD3882	Suspended
0.8591	High Similarity	NPD7819	Suspended
0.8591	High Similarity	NPD7096	Clinical (unspecified phase)
0.854	High Similarity	NPD6859	Clinical (unspecified phase)
0.8514	High Similarity	NPD6599	Discontinued
0.8462	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8444	Intermediate Similarity	NPD1203	Approved
0.844	Intermediate Similarity	NPD3748	Approved
0.8435	Intermediate Similarity	NPD5403	Approved
0.8425	Intermediate Similarity	NPD5401	Approved
0.8421	Intermediate Similarity	NPD3749	Approved
0.8411	Intermediate Similarity	NPD3817	Phase 2
0.8403	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8355	Intermediate Similarity	NPD7768	Phase 2
0.8333	Intermediate Similarity	NPD2800	Approved
0.8333	Intermediate Similarity	NPD1243	Approved
0.8333	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8322	Intermediate Similarity	NPD2344	Approved
0.8258	Intermediate Similarity	NPD1548	Phase 1
0.8228	Intermediate Similarity	NPD3818	Discontinued
0.8222	Intermediate Similarity	NPD9717	Approved
0.8217	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8217	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8217	Intermediate Similarity	NPD6166	Phase 2
0.8188	Intermediate Similarity	NPD920	Approved
0.8176	Intermediate Similarity	NPD7054	Approved
0.8176	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8169	Intermediate Similarity	NPD6651	Approved
0.8163	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8148	Intermediate Similarity	NPD422	Phase 1
0.8148	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.8143	Intermediate Similarity	NPD2313	Discontinued
0.8141	Intermediate Similarity	NPD6959	Discontinued
0.8129	Intermediate Similarity	NPD6832	Phase 2
0.8125	Intermediate Similarity	NPD2935	Discontinued
0.8125	Intermediate Similarity	NPD7472	Approved
0.8095	Intermediate Similarity	NPD2309	Approved
0.8075	Intermediate Similarity	NPD6797	Phase 2
0.8056	Intermediate Similarity	NPD2799	Discontinued
0.8054	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8052	Intermediate Similarity	NPD5402	Approved
0.8028	Intermediate Similarity	NPD943	Approved
0.8025	Intermediate Similarity	NPD7251	Discontinued
0.8014	Intermediate Similarity	NPD3268	Approved
0.8012	Intermediate Similarity	NPD7074	Phase 3
0.8	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7986	Intermediate Similarity	NPD2798	Approved
0.7975	Intermediate Similarity	NPD7808	Phase 3
0.7975	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7971	Intermediate Similarity	NPD3225	Approved
0.7963	Intermediate Similarity	NPD5953	Discontinued
0.7962	Intermediate Similarity	NPD5494	Approved
0.795	Intermediate Similarity	NPD7286	Phase 2
0.7931	Intermediate Similarity	NPD7033	Discontinued
0.7931	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7931	Intermediate Similarity	NPD4308	Phase 3
0.7914	Intermediate Similarity	NPD2797	Approved
0.7905	Intermediate Similarity	NPD4628	Phase 3
0.7883	Intermediate Similarity	NPD1610	Phase 2
0.7877	Intermediate Similarity	NPD6100	Approved
0.7877	Intermediate Similarity	NPD6099	Approved
0.7872	Intermediate Similarity	NPD4908	Phase 1
0.7866	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7862	Intermediate Similarity	NPD6232	Discontinued
0.7852	Intermediate Similarity	NPD9545	Approved
0.7847	Intermediate Similarity	NPD1933	Approved
0.7843	Intermediate Similarity	NPD3226	Approved
0.7838	Intermediate Similarity	NPD2654	Approved
0.7836	Intermediate Similarity	NPD9493	Approved
0.7826	Intermediate Similarity	NPD7473	Discontinued
0.7815	Intermediate Similarity	NPD2533	Approved
0.7815	Intermediate Similarity	NPD2532	Approved
0.7815	Intermediate Similarity	NPD2534	Approved
0.7805	Intermediate Similarity	NPD6559	Discontinued
0.7786	Intermediate Similarity	NPD3266	Approved
0.7786	Intermediate Similarity	NPD3267	Approved
0.7785	Intermediate Similarity	NPD919	Approved
0.7762	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD1241	Discontinued
0.7724	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7707	Intermediate Similarity	NPD4288	Approved
0.7703	Intermediate Similarity	NPD2346	Discontinued
0.7702	Intermediate Similarity	NPD3926	Phase 2
0.7698	Intermediate Similarity	NPD3972	Approved
0.7688	Intermediate Similarity	NPD1247	Approved
0.7667	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7655	Intermediate Similarity	NPD4307	Phase 2
0.7643	Intermediate Similarity	NPD1465	Phase 2
0.7639	Intermediate Similarity	NPD1296	Phase 2
0.7639	Intermediate Similarity	NPD411	Approved
0.7622	Intermediate Similarity	NPD5844	Phase 1
0.7606	Intermediate Similarity	NPD1019	Discontinued
0.7603	Intermediate Similarity	NPD447	Suspended
0.7603	Intermediate Similarity	NPD230	Phase 1
0.7597	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7571	Intermediate Similarity	NPD1608	Approved
0.753	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD3764	Approved
0.7516	Intermediate Similarity	NPD7390	Discontinued
0.7514	Intermediate Similarity	NPD4363	Phase 3
0.7514	Intermediate Similarity	NPD4360	Phase 2
0.75	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD2296	Approved
0.7483	Intermediate Similarity	NPD5124	Phase 1
0.7483	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD4361	Phase 2
0.7471	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD1729	Discontinued
0.745	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD1481	Phase 2
0.7439	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7431	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7415	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7415	Intermediate Similarity	NPD1613	Approved
0.7413	Intermediate Similarity	NPD1470	Approved
0.7405	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7397	Intermediate Similarity	NPD6798	Discontinued
0.7386	Intermediate Similarity	NPD2354	Approved
0.7384	Intermediate Similarity	NPD4287	Approved
0.7381	Intermediate Similarity	NPD6104	Discontinued
0.7379	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7376	Intermediate Similarity	NPD1201	Approved
0.7376	Intermediate Similarity	NPD1535	Discovery
0.7358	Intermediate Similarity	NPD6844	Discontinued
0.7357	Intermediate Similarity	NPD17	Approved
0.7355	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD1471	Phase 3
0.7349	Intermediate Similarity	NPD3751	Discontinued
0.7343	Intermediate Similarity	NPD1876	Approved
0.7338	Intermediate Similarity	NPD1894	Discontinued
0.7329	Intermediate Similarity	NPD4625	Phase 3
0.7297	Intermediate Similarity	NPD3140	Approved
0.7297	Intermediate Similarity	NPD3142	Approved
0.7296	Intermediate Similarity	NPD5889	Approved
0.7296	Intermediate Similarity	NPD5890	Approved
0.7292	Intermediate Similarity	NPD1164	Approved
0.729	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD6971	Discontinued
0.7278	Intermediate Similarity	NPD7458	Discontinued
0.7273	Intermediate Similarity	NPD4749	Approved
0.7255	Intermediate Similarity	NPD1652	Phase 2
0.7246	Intermediate Similarity	NPD5940	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD4661	Approved
0.7244	Intermediate Similarity	NPD4662	Approved
0.7239	Intermediate Similarity	NPD9266	Approved
0.7239	Intermediate Similarity	NPD74	Approved
0.7237	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD2353	Approved
0.7237	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD6585	Discontinued
0.723	Intermediate Similarity	NPD6233	Phase 2
0.7226	Intermediate Similarity	NPD7440	Discontinued
0.7212	Intermediate Similarity	NPD5711	Approved
0.7212	Intermediate Similarity	NPD5710	Approved
0.7208	Intermediate Similarity	NPD7003	Approved
0.7207	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD9494	Approved
0.7179	Intermediate Similarity	NPD7212	Phase 2
0.7179	Intermediate Similarity	NPD7213	Phase 3
0.7171	Intermediate Similarity	NPD5408	Approved
0.7171	Intermediate Similarity	NPD5406	Approved
0.7171	Intermediate Similarity	NPD5404	Approved
0.7171	Intermediate Similarity	NPD5405	Approved
0.717	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7164	Intermediate Similarity	NPD9267	Approved
0.7164	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7164	Intermediate Similarity	NPD9264	Approved
0.7164	Intermediate Similarity	NPD9263	Approved
0.7161	Intermediate Similarity	NPD3887	Approved
0.7158	Intermediate Similarity	NPD7584	Approved
0.7153	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD7199	Phase 2
0.7143	Intermediate Similarity	NPD7577	Discontinued
0.7143	Intermediate Similarity	NPD6280	Approved
0.7143	Intermediate Similarity	NPD6279	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