NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	250.1
Volume:	273.408
LogP:	3.855
LogD:	3.533
LogS:	-4.881
# Rotatable Bonds:	3
TPSA:	30.21
# H-Bond Aceptor:	2
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.711
Synthetic Accessibility Score:	1.813
Fsp3:	0.118
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:	-4.806
MDCK Permeability:	1.5396561138913967e-05
Pgp-inhibitor:	0.991
Pgp-substrate:	0.119
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.999
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.131
Plasma Protein Binding (PPB):	98.25533294677734%
Volume Distribution (VD):	1.193
Pgp-substrate:	1.1697198152542114%

ADMET: Metabolism

CYP1A2-inhibitor:	0.976
CYP1A2-substrate:	0.766
CYP2C19-inhibitor:	0.961
CYP2C19-substrate:	0.158
CYP2C9-inhibitor:	0.872
CYP2C9-substrate:	0.866
CYP2D6-inhibitor:	0.117
CYP2D6-substrate:	0.784
CYP3A4-inhibitor:	0.126
CYP3A4-substrate:	0.422

ADMET: Excretion

Clearance (CL):	3.734
Half-life (T1/2):	0.3

ADMET: Toxicity

hERG Blockers:	0.244
Human Hepatotoxicity (H-HT):	0.251
Drug-inuced Liver Injury (DILI):	0.71
AMES Toxicity:	0.743
Rat Oral Acute Toxicity:	0.289
Maximum Recommended Daily Dose:	0.222
Skin Sensitization:	0.738
Carcinogencity:	0.771
Eye Corrosion:	0.017
Eye Irritation:	0.97
Respiratory Toxicity:	0.075

Download Data

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

Natural Product: NPC54243

Natural Product ID:	NPC54243
*Common Name:**	Flidersiachromone
IUPAC Name:	2-(2-phenylethyl)chromen-4-one
Synonyms:	Flidersiachromone
Standard InCHIKey:	VNZNWFQJBFLELF-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C17H14O2/c18-16-12-14(11-10-13-6-2-1-3-7-13)19-17-9-5-4-8-15(16)17/h1-9,12H,10-11H2
SMILES:	O=c1cc(CCc2ccccc2)oc2c1cccc2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL481060
PubChem CID:	441964
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0000144] Chromones

*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
NPO26919	Sanguisorba officinalis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11520216]
NPO23628	Imperata cylindrica	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16499335]
NPO14558	Aquilaria sinensis	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27128895]
NPO3345	Mylabris phalerata	Species	Meloidae	Eukaryota	n.a.	n.a.	n.a.	PMID[27458783]
NPO1692	Aquilaria malaccensis	Species	Thymelaeaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[28445049]
NPO1692	Aquilaria malaccensis	Species	Thymelaeaceae	Eukaryota	Agarwood	n.a.	n.a.	PMID[29083898]
NPO14558	Aquilaria sinensis	Species	Thymelaeaceae	Eukaryota	Resinous Wood	n.a.	n.a.	PMID[29227647]
NPO1692	Aquilaria malaccensis	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30672698]
NPO1692	Aquilaria malaccensis	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7320738]
NPO23628	Imperata cylindrica	Species	Poaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[7714541]
NPO23628	Imperata cylindrica	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7760071]
NPO23628	Imperata cylindrica	Species	Poaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[7798964]
NPO23628	Imperata cylindrica	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7964801]
NPO14558	Aquilaria sinensis	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29756	Aquilaria agallocha	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26919	Sanguisorba officinalis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23628	Imperata cylindrica	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3345	Mylabris phalerata	Species	Meloidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26919	Sanguisorba officinalis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23628	Imperata cylindrica	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14558	Aquilaria sinensis	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26919	Sanguisorba officinalis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29756	Aquilaria agallocha	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO3345	Mylabris phalerata	Species	Meloidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14558	Aquilaria sinensis	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO23628	Imperata cylindrica	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14558	Aquilaria sinensis	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO26919	Sanguisorba officinalis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO23628	Imperata cylindrica	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO26919	Sanguisorba officinalis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3345	Mylabris phalerata	Species	Meloidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1692	Aquilaria malaccensis	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14558	Aquilaria sinensis	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23628	Imperata cylindrica	Species	Poaceae	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
Ki	1
Others	2

Activity Type	# Activity
Individual Protein	2
NON-MOLECULAR	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	36.1	%	PMID[479291]
NPT99	Individual Protein	Peroxisome proliferator-activated receptor gamma	Homo sapiens	Inhibition	=	37.7	%	PMID[479292]
NPT2	Others	Unspecified		EC50	=	25300.0	nM	PMID[479292]
NPT99	Individual Protein	Peroxisome proliferator-activated receptor gamma	Homo sapiens	Ki	=	54000.0	nM	PMID[479292]

☑ 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 NPC54243 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	606
0.1-0.2	2519
0.2-0.3	6125
0.3-0.4	12068
0.4-0.5	4382
0.5-0.6	6984
0.6-0.7	6419
0.7-0.8	3379
0.8-0.85	167
0.85-0.9	33
0.9-0.95	12
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.991	High Similarity	NPC32298
0.9646	High Similarity	NPC35744
0.9407	High Similarity	NPC2771
0.9402	High Similarity	NPC93730
0.9397	High Similarity	NPC314329
0.9322	High Similarity	NPC193805
0.9304	High Similarity	NPC201284
0.925	High Similarity	NPC298884
0.9174	High Similarity	NPC125887
0.9115	High Similarity	NPC279916
0.9091	High Similarity	NPC22783
0.9091	High Similarity	NPC41721
0.9024	High Similarity	NPC7569
0.9016	High Similarity	NPC196034
0.8952	High Similarity	NPC301717
0.8917	High Similarity	NPC472888
0.8898	High Similarity	NPC470092
0.888	High Similarity	NPC284424
0.8871	High Similarity	NPC39753
0.8871	High Similarity	NPC115998
0.8852	High Similarity	NPC474264
0.88	High Similarity	NPC137264
0.879	High Similarity	NPC197425
0.874	High Similarity	NPC292998
0.8739	High Similarity	NPC246214
0.873	High Similarity	NPC278556
0.872	High Similarity	NPC278787
0.872	High Similarity	NPC228184
0.8689	High Similarity	NPC56332
0.8661	High Similarity	NPC101294
0.8661	High Similarity	NPC473655
0.8651	High Similarity	NPC141549
0.8621	High Similarity	NPC53953
0.8618	High Similarity	NPC224657
0.8605	High Similarity	NPC77955
0.8594	High Similarity	NPC57601
0.8583	High Similarity	NPC113006
0.8583	High Similarity	NPC230951
0.8571	High Similarity	NPC171023
0.8548	High Similarity	NPC237868
0.8538	High Similarity	NPC254741
0.8537	High Similarity	NPC107846
0.8527	High Similarity	NPC172262
0.8527	High Similarity	NPC125269
0.8527	High Similarity	NPC66705
0.8516	High Similarity	NPC128216
0.8516	High Similarity	NPC287533
0.8504	High Similarity	NPC11173
0.8492	Intermediate Similarity	NPC187907
0.8487	Intermediate Similarity	NPC217423
0.8487	Intermediate Similarity	NPC45104
0.8487	Intermediate Similarity	NPC469954
0.8475	Intermediate Similarity	NPC188907
0.8473	Intermediate Similarity	NPC250266
0.8473	Intermediate Similarity	NPC266597
0.8473	Intermediate Similarity	NPC157855
0.8473	Intermediate Similarity	NPC103001
0.8473	Intermediate Similarity	NPC228661
0.845	Intermediate Similarity	NPC78540
0.845	Intermediate Similarity	NPC274121
0.845	Intermediate Similarity	NPC213216
0.845	Intermediate Similarity	NPC50898
0.8438	Intermediate Similarity	NPC474340
0.843	Intermediate Similarity	NPC168050
0.8417	Intermediate Similarity	NPC206007
0.8403	Intermediate Similarity	NPC316062
0.8397	Intermediate Similarity	NPC124784
0.8397	Intermediate Similarity	NPC13408
0.8397	Intermediate Similarity	NPC231772
0.8397	Intermediate Similarity	NPC234133
0.8397	Intermediate Similarity	NPC61546
0.8397	Intermediate Similarity	NPC473887
0.8397	Intermediate Similarity	NPC29353
0.8397	Intermediate Similarity	NPC47815
0.8397	Intermediate Similarity	NPC127447
0.8397	Intermediate Similarity	NPC72452
0.8397	Intermediate Similarity	NPC194281
0.8397	Intermediate Similarity	NPC161196
0.8385	Intermediate Similarity	NPC248872
0.8374	Intermediate Similarity	NPC311219
0.8372	Intermediate Similarity	NPC182428
0.8347	Intermediate Similarity	NPC43435
0.8346	Intermediate Similarity	NPC211120
0.8346	Intermediate Similarity	NPC57552
0.8346	Intermediate Similarity	NPC136095
0.8346	Intermediate Similarity	NPC238309
0.8346	Intermediate Similarity	NPC473019
0.8333	Intermediate Similarity	NPC299379
0.8333	Intermediate Similarity	NPC475496
0.8333	Intermediate Similarity	NPC290291
0.8333	Intermediate Similarity	NPC275055
0.8333	Intermediate Similarity	NPC49852
0.8321	Intermediate Similarity	NPC239495
0.8321	Intermediate Similarity	NPC9985
0.8321	Intermediate Similarity	NPC99854
0.832	Intermediate Similarity	NPC4164
0.8308	Intermediate Similarity	NPC223354
0.8306	Intermediate Similarity	NPC182646
0.8295	Intermediate Similarity	NPC472882
0.8291	Intermediate Similarity	NPC23332
0.8284	Intermediate Similarity	NPC172986
0.8284	Intermediate Similarity	NPC472409
0.8284	Intermediate Similarity	NPC475680
0.8284	Intermediate Similarity	NPC270883
0.8284	Intermediate Similarity	NPC281207
0.8284	Intermediate Similarity	NPC235239
0.8284	Intermediate Similarity	NPC269652
0.8284	Intermediate Similarity	NPC261227
0.8284	Intermediate Similarity	NPC305355
0.8271	Intermediate Similarity	NPC280284
0.8271	Intermediate Similarity	NPC17848
0.8271	Intermediate Similarity	NPC201395
0.8271	Intermediate Similarity	NPC188947
0.8271	Intermediate Similarity	NPC276905
0.8271	Intermediate Similarity	NPC99333
0.8268	Intermediate Similarity	NPC475017
0.8268	Intermediate Similarity	NPC473907
0.8264	Intermediate Similarity	NPC152159
0.8258	Intermediate Similarity	NPC240593
0.8258	Intermediate Similarity	NPC116775
0.8258	Intermediate Similarity	NPC187432
0.8258	Intermediate Similarity	NPC281917
0.8258	Intermediate Similarity	NPC216361
0.8258	Intermediate Similarity	NPC256042
0.825	Intermediate Similarity	NPC470860
0.8244	Intermediate Similarity	NPC298900
0.8231	Intermediate Similarity	NPC229646
0.8222	Intermediate Similarity	NPC156590
0.8222	Intermediate Similarity	NPC118840
0.8222	Intermediate Similarity	NPC64908
0.8222	Intermediate Similarity	NPC103362
0.8222	Intermediate Similarity	NPC136840
0.8222	Intermediate Similarity	NPC110969
0.8222	Intermediate Similarity	NPC24075
0.8222	Intermediate Similarity	NPC205006
0.8222	Intermediate Similarity	NPC147688
0.8209	Intermediate Similarity	NPC78913
0.8209	Intermediate Similarity	NPC261234
0.8209	Intermediate Similarity	NPC96565
0.8209	Intermediate Similarity	NPC152042
0.8209	Intermediate Similarity	NPC220062
0.8209	Intermediate Similarity	NPC143799
0.8209	Intermediate Similarity	NPC241838
0.8209	Intermediate Similarity	NPC301217
0.8209	Intermediate Similarity	NPC55018
0.8209	Intermediate Similarity	NPC11566
0.8209	Intermediate Similarity	NPC303633
0.8209	Intermediate Similarity	NPC216978
0.8209	Intermediate Similarity	NPC18260
0.8205	Intermediate Similarity	NPC183648
0.8203	Intermediate Similarity	NPC473894
0.8197	Intermediate Similarity	NPC264976
0.8195	Intermediate Similarity	NPC84585
0.8195	Intermediate Similarity	NPC476480
0.8195	Intermediate Similarity	NPC259685
0.8195	Intermediate Similarity	NPC188879
0.8189	Intermediate Similarity	NPC264428
0.8189	Intermediate Similarity	NPC161322
0.8182	Intermediate Similarity	NPC46869
0.8168	Intermediate Similarity	NPC1249
0.8162	Intermediate Similarity	NPC226636
0.8162	Intermediate Similarity	NPC1534
0.8162	Intermediate Similarity	NPC11561
0.816	Intermediate Similarity	NPC141252
0.816	Intermediate Similarity	NPC11799
0.8154	Intermediate Similarity	NPC64359
0.8154	Intermediate Similarity	NPC262359
0.8154	Intermediate Similarity	NPC118253
0.8154	Intermediate Similarity	NPC308037
0.8148	Intermediate Similarity	NPC69769
0.8148	Intermediate Similarity	NPC171094
0.8148	Intermediate Similarity	NPC474037
0.8148	Intermediate Similarity	NPC241100
0.8148	Intermediate Similarity	NPC184536
0.8148	Intermediate Similarity	NPC103342
0.8148	Intermediate Similarity	NPC103904
0.8148	Intermediate Similarity	NPC230285
0.8148	Intermediate Similarity	NPC146679
0.8148	Intermediate Similarity	NPC150522
0.8148	Intermediate Similarity	NPC159275
0.8148	Intermediate Similarity	NPC59951
0.8136	Intermediate Similarity	NPC233238
0.8134	Intermediate Similarity	NPC472460
0.8134	Intermediate Similarity	NPC124269
0.8134	Intermediate Similarity	NPC329225
0.8134	Intermediate Similarity	NPC147686
0.8134	Intermediate Similarity	NPC18457
0.8134	Intermediate Similarity	NPC118813
0.813	Intermediate Similarity	NPC474874
0.813	Intermediate Similarity	NPC233282
0.8103	Intermediate Similarity	NPC141523
0.8102	Intermediate Similarity	NPC38219
0.8102	Intermediate Similarity	NPC113089
0.8102	Intermediate Similarity	NPC17262
0.8102	Intermediate Similarity	NPC59522
0.8099	Intermediate Similarity	NPC19290
0.8095	Intermediate Similarity	NPC89630
0.8092	Intermediate Similarity	NPC212631
0.8092	Intermediate Similarity	NPC129132
0.8092	Intermediate Similarity	NPC205468

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 NPC54243 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	525
0.1-0.2	991
0.2-0.3	1260
0.3-0.4	2745
0.4-0.5	2022
0.5-0.6	1130
0.6-0.7	350
0.7-0.8	109
0.8-0.85	11
0.85-0.9	6
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9397	High Similarity	NPD1547	Clinical (unspecified phase)
0.8871	High Similarity	NPD2313	Discontinued
0.8852	High Similarity	NPD2798	Approved
0.871	High Similarity	NPD6832	Phase 2
0.8618	High Similarity	NPD1203	Approved
0.8538	High Similarity	NPD2796	Approved
0.8462	Intermediate Similarity	NPD1241	Discontinued
0.8374	Intermediate Similarity	NPD9717	Approved
0.8372	Intermediate Similarity	NPD1933	Approved
0.8321	Intermediate Similarity	NPD2799	Discontinued
0.832	Intermediate Similarity	NPD3266	Approved
0.832	Intermediate Similarity	NPD3267	Approved
0.8295	Intermediate Similarity	NPD4307	Phase 2
0.8231	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.8195	Intermediate Similarity	NPD2346	Discontinued
0.8195	Intermediate Similarity	NPD2344	Approved
0.8182	Intermediate Similarity	NPD3748	Approved
0.8175	Intermediate Similarity	NPD2797	Approved
0.8134	Intermediate Similarity	NPD1549	Phase 2
0.811	Intermediate Similarity	NPD1019	Discontinued
0.8087	Intermediate Similarity	NPD9697	Approved
0.808	Intermediate Similarity	NPD3972	Approved
0.806	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.806	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8045	Intermediate Similarity	NPD4308	Phase 3
0.8045	Intermediate Similarity	NPD1510	Phase 2
0.8043	Intermediate Similarity	NPD5401	Approved
0.8015	Intermediate Similarity	NPD1240	Approved
0.8	Intermediate Similarity	NPD3268	Approved
0.7956	Intermediate Similarity	NPD2309	Approved
0.7953	Intermediate Similarity	NPD1876	Approved
0.7929	Intermediate Similarity	NPD5403	Approved
0.7914	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7914	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD1607	Approved
0.7883	Intermediate Similarity	NPD3750	Approved
0.7852	Intermediate Similarity	NPD1551	Phase 2
0.7842	Intermediate Similarity	NPD6799	Approved
0.7842	Intermediate Similarity	NPD1511	Approved
0.7826	Intermediate Similarity	NPD3295	Clinical (unspecified phase)
0.7812	Intermediate Similarity	NPD3225	Approved
0.781	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.781	Intermediate Similarity	NPD1243	Approved
0.7805	Intermediate Similarity	NPD9493	Approved
0.7794	Intermediate Similarity	NPD1471	Phase 3
0.7786	Intermediate Similarity	NPD4662	Approved
0.7786	Intermediate Similarity	NPD4661	Approved
0.7759	Intermediate Similarity	NPD9261	Approved
0.773	Intermediate Similarity	NPD1512	Approved
0.7727	Intermediate Similarity	NPD411	Approved
0.7721	Intermediate Similarity	NPD2935	Discontinued
0.7698	Intermediate Similarity	NPD17	Approved
0.7692	Intermediate Similarity	NPD3226	Approved
0.7687	Intermediate Similarity	NPD447	Suspended
0.768	Intermediate Similarity	NPD1894	Discontinued
0.7664	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7655	Intermediate Similarity	NPD6844	Discontinued
0.7643	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7639	Intermediate Similarity	NPD6585	Discontinued
0.7623	Intermediate Similarity	NPD5535	Approved
0.7612	Intermediate Similarity	NPD3140	Approved
0.7612	Intermediate Similarity	NPD3142	Approved
0.7586	Intermediate Similarity	NPD7411	Suspended
0.7586	Intermediate Similarity	NPD5890	Approved
0.7586	Intermediate Similarity	NPD5889	Approved
0.7578	Intermediate Similarity	NPD1201	Approved
0.7551	Intermediate Similarity	NPD5402	Approved
0.7541	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7536	Intermediate Similarity	NPD2353	Approved
0.7536	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7535	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7534	Intermediate Similarity	NPD6801	Discontinued
0.752	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7519	Intermediate Similarity	NPD1481	Phase 2
0.7519	Intermediate Similarity	NPD1608	Approved
0.7517	Intermediate Similarity	NPD4380	Phase 2
0.7517	Intermediate Similarity	NPD6599	Discontinued
0.75	Intermediate Similarity	NPD9264	Approved
0.75	Intermediate Similarity	NPD9263	Approved
0.75	Intermediate Similarity	NPD1238	Approved
0.75	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD9267	Approved
0.7483	Intermediate Similarity	NPD7819	Suspended
0.7483	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD2801	Approved
0.7481	Intermediate Similarity	NPD1470	Approved
0.7463	Intermediate Similarity	NPD6798	Discontinued
0.745	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD1535	Discovery
0.7438	Intermediate Similarity	NPD74	Approved
0.7438	Intermediate Similarity	NPD9266	Approved
0.7432	Intermediate Similarity	NPD3817	Phase 2
0.7431	Intermediate Similarity	NPD920	Approved
0.7426	Intermediate Similarity	NPD4622	Approved
0.7426	Intermediate Similarity	NPD4618	Approved
0.7415	Intermediate Similarity	NPD1934	Approved
0.7415	Intermediate Similarity	NPD6279	Approved
0.7415	Intermediate Similarity	NPD6280	Approved
0.7391	Intermediate Similarity	NPD7033	Discontinued
0.7365	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7344	Intermediate Similarity	NPD1651	Approved
0.7344	Intermediate Similarity	NPD5585	Approved
0.7333	Intermediate Similarity	NPD7075	Discontinued
0.7333	Intermediate Similarity	NPD1296	Phase 2
0.7333	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD3749	Approved
0.7324	Intermediate Similarity	NPD3887	Approved
0.7324	Intermediate Similarity	NPD2354	Approved
0.7323	Intermediate Similarity	NPD5536	Phase 2
0.7319	Intermediate Similarity	NPD5689	Approved
0.7319	Intermediate Similarity	NPD5688	Approved
0.7315	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD2296	Approved
0.7273	Intermediate Similarity	NPD7440	Discontinued
0.7273	Intermediate Similarity	NPD3134	Approved
0.7273	Intermediate Similarity	NPD968	Approved
0.7267	Intermediate Similarity	NPD7768	Phase 2
0.7267	Intermediate Similarity	NPD3882	Suspended
0.7266	Intermediate Similarity	NPD1548	Phase 1
0.7254	Intermediate Similarity	NPD7003	Approved
0.7254	Intermediate Similarity	NPD4628	Phase 3
0.7241	Intermediate Similarity	NPD5049	Phase 3
0.7237	Intermediate Similarity	NPD5494	Approved
0.7234	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD2366	Approved
0.7218	Intermediate Similarity	NPD1164	Approved
0.7211	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7206	Intermediate Similarity	NPD3764	Approved
0.7176	Intermediate Similarity	NPD422	Phase 1
0.7176	Intermediate Similarity	NPD1281	Approved
0.7174	Intermediate Similarity	NPD6355	Discontinued
0.7174	Intermediate Similarity	NPD1184	Approved
0.7165	Intermediate Similarity	NPD2557	Approved
0.7161	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD8032	Phase 2
0.7153	Intermediate Similarity	NPD6233	Phase 2
0.7132	Intermediate Similarity	NPD9545	Approved
0.7123	Intermediate Similarity	NPD6273	Approved
0.7113	Intermediate Similarity	NPD2897	Discontinued
0.7099	Intermediate Similarity	NPD3496	Discontinued
0.7097	Intermediate Similarity	NPD5451	Approved
0.7095	Intermediate Similarity	NPD2651	Approved
0.7095	Intermediate Similarity	NPD2649	Approved
0.7092	Intermediate Similarity	NPD4476	Approved
0.7092	Intermediate Similarity	NPD4477	Approved
0.7087	Intermediate Similarity	NPD9281	Approved
0.7086	Intermediate Similarity	NPD4288	Approved
0.7086	Intermediate Similarity	NPD5616	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD3869	Phase 3
0.7075	Intermediate Similarity	NPD3873	Phase 3
0.7075	Intermediate Similarity	NPD5586	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD1358	Approved
0.7073	Intermediate Similarity	NPD290	Approved
0.707	Intermediate Similarity	NPD3818	Discontinued
0.7069	Intermediate Similarity	NPD1202	Approved
0.7068	Intermediate Similarity	NPD4359	Approved
0.7067	Intermediate Similarity	NPD7317	Phase 3
0.7063	Intermediate Similarity	NPD2800	Approved
0.7063	Intermediate Similarity	NPD2654	Approved
0.7059	Intermediate Similarity	NPD919	Approved
0.7059	Intermediate Similarity	NPD2614	Approved
0.7059	Intermediate Similarity	NPD3252	Approved
0.7051	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD1611	Approved
0.7032	Intermediate Similarity	NPD6808	Phase 2
0.7031	Intermediate Similarity	NPD6671	Approved
0.7029	Intermediate Similarity	NPD4062	Phase 3
0.7023	Intermediate Similarity	NPD1778	Approved
0.7016	Intermediate Similarity	NPD2684	Approved
0.7015	Intermediate Similarity	NPD1283	Approved
0.7	Intermediate Similarity	NPD2486	Discontinued
0.6987	Remote Similarity	NPD3926	Phase 2
0.698	Remote Similarity	NPD7458	Discontinued
0.6978	Remote Similarity	NPD943	Approved
0.6974	Remote Similarity	NPD7318	Phase 3
0.6972	Remote Similarity	NPD6100	Approved
0.6972	Remote Similarity	NPD6099	Approved
0.697	Remote Similarity	NPD3847	Discontinued
0.6968	Remote Similarity	NPD1247	Approved
0.6967	Remote Similarity	NPD5909	Discontinued
0.6967	Remote Similarity	NPD1237	Approved
0.6954	Remote Similarity	NPD7577	Discontinued
0.6947	Remote Similarity	NPD3444	Approved
0.6947	Remote Similarity	NPD3049	Approved
0.6947	Remote Similarity	NPD3443	Approved
0.6947	Remote Similarity	NPD5691	Approved
0.6947	Remote Similarity	NPD3445	Approved
0.6943	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD6166	Phase 2
0.694	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6934	Remote Similarity	NPD1008	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD7054	Approved
0.6918	Remote Similarity	NPD160	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD1610	Phase 2
0.6912	Remote Similarity	NPD5647	Approved
0.6905	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD3412	Clinical (unspecified phase)

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