NPASS Compound

Structure

CID90582 OpenBabel06191715432D 24 26 0 0 0 0 0 0 0 0999 V2000 3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 21 1 0 0 0 0 2 22 1 0 0 0 0 3 23 1 0 0 0 0 4 6 1 0 0 0 0 4 10 2 0 0 0 0 5 7 2 0 0 0 0 5 10 1 0 0 0 0 6 11 2 0 0 0 0 7 11 1 0 0 0 0 8 12 2 0 0 0 0 8 13 1 0 0 0 0 9 12 1 0 0 0 0 9 14 2 0 0 0 0 10 17 1 0 0 0 0 11 19 1 0 0 0 0 12 21 1 0 0 0 0 13 15 2 0 0 0 0 13 22 1 0 0 0 0 14 15 1 0 0 0 0 14 24 1 0 0 0 0 15 16 1 0 0 0 0 16 18 1 0 0 0 0 16 20 2 0 0 0 0 17 18 2 0 0 0 0 17 24 1 0 0 0 0 18 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	328.09
Volume:	325.865
LogP:	3.289
LogD:	2.923
LogS:	-4.034
# Rotatable Bonds:	4
TPSA:	78.13
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.792
Synthetic Accessibility Score:	2.213
Fsp3:	0.167
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:	-4.636
MDCK Permeability:	2.7932957891607657e-05
Pgp-inhibitor:	0.991
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.008

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.023
Plasma Protein Binding (PPB):	87.12279510498047%
Volume Distribution (VD):	0.836
Pgp-substrate:	11.01710319519043%

ADMET: Metabolism

CYP1A2-inhibitor:	0.943
CYP1A2-substrate:	0.959
CYP2C19-inhibitor:	0.899
CYP2C19-substrate:	0.22
CYP2C9-inhibitor:	0.815
CYP2C9-substrate:	0.938
CYP2D6-inhibitor:	0.623
CYP2D6-substrate:	0.917
CYP3A4-inhibitor:	0.805
CYP3A4-substrate:	0.256

ADMET: Excretion

Clearance (CL):	6.065
Half-life (T1/2):	0.763

ADMET: Toxicity

hERG Blockers:	0.032
Human Hepatotoxicity (H-HT):	0.161
Drug-inuced Liver Injury (DILI):	0.963
AMES Toxicity:	0.619
Rat Oral Acute Toxicity:	0.076
Maximum Recommended Daily Dose:	0.106
Skin Sensitization:	0.117
Carcinogencity:	0.082
Eye Corrosion:	0.004
Eye Irritation:	0.808
Respiratory Toxicity:	0.18

Download Data

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

Natural Product: NPC90582

Natural Product ID:	NPC90582
*Common Name:**	2-(4-Hydroxyphenyl)-3,5,7-Trimethoxychromen-4-One
IUPAC Name:	2-(4-hydroxyphenyl)-3,5,7-trimethoxychromen-4-one
Synonyms:
Standard InCHIKey:	NGOJYRXQNKPQOD-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C18H16O6/c1-21-12-8-13(22-2)15-14(9-12)24-17(18(23-3)16(15)20)10-4-6-11(19)7-5-10/h4-9,19H,1-3H3
SMILES:	COc1cc(OC)c2c(c1)oc(c(c2=O)OC)c1ccc(cc1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL166029
PubChem CID:	14414499
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
NPO11605	Senna italica	Species	Fabaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[24684761]
NPO15699	Damnacanthus indicus	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15699	Damnacanthus indicus	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15699	Damnacanthus indicus	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO16680	Citrus hanaju	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18312	Prochlorothrix hollandica	Species	Pseudanabaenaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO11605	Senna italica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23761	Cladosporium werneckii	Species	Cladosporiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15699	Damnacanthus indicus	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19060	Bulbophyllum gymnopus	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18570	Reseda muricata	Species	Resedaceae	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
Others	9

Activity Type	# Activity
Cell Line	1
Organism	6
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT189	Cell Line	Vero	Chlorocebus aethiops	CyD50	=	100.0	ug ml-1	PMID[490697]
NPT1048	Organism	Poliovirus	Human enterovirus C	Max non-toxic dose	=	100.0	ug ml-1	PMID[490697]
NPT1048	Organism	Poliovirus	Human enterovirus C	Reduction factor	=	100000.0	n.a.	PMID[490697]
NPT1048	Organism	Poliovirus	Human enterovirus C	Minimal dose	=	5.0	ug ml-1	PMID[490697]
NPT1048	Organism	Poliovirus	Human enterovirus C	ED99	=	10.0	ug ml-1	PMID[490697]
NPT1538	Organism	Human rhinovirus sp.	Human rhinovirus sp.	CyD50	=	100.0	ug ml-1	PMID[490697]
NPT1538	Organism	Human rhinovirus sp.	Human rhinovirus sp.	ED99	=	20.0	ug ml-1	PMID[490697]
NPT27	Others	Unspecified		Therapeutic index 99	=	10.0	n.a.	PMID[490697]
NPT27	Others	Unspecified		Therapeutic index 99	=	5.0	n.a.	PMID[490697]

☑ 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 NPC90582 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	438
0.1-0.2	1903
0.2-0.3	5033
0.3-0.4	11227
0.4-0.5	6190
0.5-0.6	4177
0.6-0.7	5677
0.7-0.8	3945
0.8-0.85	2182
0.85-0.9	1448
0.9-0.95	428
0.95-1	49

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC262094
0.9926	High Similarity	NPC59951
0.9926	High Similarity	NPC230285
0.9926	High Similarity	NPC184536
0.9926	High Similarity	NPC103342
0.9926	High Similarity	NPC146679
0.9926	High Similarity	NPC103904
0.9853	High Similarity	NPC136840
0.9852	High Similarity	NPC143799
0.9852	High Similarity	NPC241838
0.9852	High Similarity	NPC152042
0.9779	High Similarity	NPC281207
0.9779	High Similarity	NPC269652
0.9778	High Similarity	NPC276905
0.9712	High Similarity	NPC5820
0.9712	High Similarity	NPC178343
0.9712	High Similarity	NPC306488
0.971	High Similarity	NPC158874
0.971	High Similarity	NPC470216
0.964	High Similarity	NPC216538
0.964	High Similarity	NPC273538
0.9638	High Similarity	NPC200694
0.963	High Similarity	NPC473887
0.963	High Similarity	NPC29353
0.963	High Similarity	NPC124784
0.963	High Similarity	NPC47815
0.963	High Similarity	NPC216361
0.963	High Similarity	NPC281917
0.963	High Similarity	NPC72452
0.963	High Similarity	NPC13408
0.963	High Similarity	NPC194281
0.963	High Similarity	NPC61546
0.963	High Similarity	NPC116775
0.963	High Similarity	NPC231772
0.963	High Similarity	NPC256042
0.963	High Similarity	NPC234133
0.963	High Similarity	NPC187432
0.963	High Similarity	NPC127447
0.9571	High Similarity	NPC470458
0.9571	High Similarity	NPC124729
0.9571	High Similarity	NPC153758
0.9568	High Similarity	NPC9117
0.9568	High Similarity	NPC190637
0.9568	High Similarity	NPC212932
0.9568	High Similarity	NPC293053
0.9568	High Similarity	NPC24821
0.9559	High Similarity	NPC250266
0.9559	High Similarity	NPC266597
0.9559	High Similarity	NPC299379
0.9507	High Similarity	NPC470461
0.9504	High Similarity	NPC259632
0.95	High Similarity	NPC326500
0.9496	High Similarity	NPC473042
0.9493	High Similarity	NPC159275
0.9493	High Similarity	NPC241100
0.9481	High Similarity	NPC248872
0.9437	High Similarity	NPC244407
0.9437	High Similarity	NPC296869
0.9437	High Similarity	NPC470460
0.9424	High Similarity	NPC282300
0.9424	High Similarity	NPC110969
0.942	High Similarity	NPC53181
0.942	High Similarity	NPC220062
0.942	High Similarity	NPC217186
0.942	High Similarity	NPC18260
0.942	High Similarity	NPC216978
0.942	High Similarity	NPC78913
0.942	High Similarity	NPC55018
0.942	High Similarity	NPC96565
0.942	High Similarity	NPC301217
0.942	High Similarity	NPC303633
0.9416	High Similarity	NPC188879
0.9407	High Similarity	NPC274121
0.9407	High Similarity	NPC78540
0.9407	High Similarity	NPC213216
0.9407	High Similarity	NPC50898
0.9375	High Similarity	NPC236769
0.9366	High Similarity	NPC14001
0.9366	High Similarity	NPC166757
0.9366	High Similarity	NPC472918
0.9362	High Similarity	NPC71210
0.9357	High Similarity	NPC11561
0.9357	High Similarity	NPC226636
0.9353	High Similarity	NPC261227
0.9353	High Similarity	NPC6407
0.9353	High Similarity	NPC129853
0.9353	High Similarity	NPC110228
0.9353	High Similarity	NPC150522
0.9353	High Similarity	NPC188243
0.9353	High Similarity	NPC270883
0.9353	High Similarity	NPC284550
0.9353	High Similarity	NPC172986
0.9353	High Similarity	NPC76445
0.9348	High Similarity	NPC280284
0.9348	High Similarity	NPC99333
0.9348	High Similarity	NPC188947
0.9348	High Similarity	NPC201395
0.9348	High Similarity	NPC124269
0.9343	High Similarity	NPC240593
0.9343	High Similarity	NPC121243
0.9343	High Similarity	NPC240147
0.9338	High Similarity	NPC172262
0.9333	High Similarity	NPC473655
0.9333	High Similarity	NPC128216
0.9333	High Similarity	NPC101294
0.9333	High Similarity	NPC10971
0.9306	High Similarity	NPC61258
0.9306	High Similarity	NPC188871
0.9306	High Similarity	NPC166753
0.9306	High Similarity	NPC50728
0.9306	High Similarity	NPC149127
0.9306	High Similarity	NPC286342
0.9296	High Similarity	NPC220418
0.9286	High Similarity	NPC147688
0.9286	High Similarity	NPC64908
0.9286	High Similarity	NPC205006
0.9286	High Similarity	NPC156590
0.9286	High Similarity	NPC118840
0.9286	High Similarity	NPC103362
0.9281	High Similarity	NPC225153
0.9281	High Similarity	NPC150648
0.9281	High Similarity	NPC20709
0.9281	High Similarity	NPC329203
0.9281	High Similarity	NPC310135
0.9281	High Similarity	NPC265871
0.9281	High Similarity	NPC222342
0.9281	High Similarity	NPC274784
0.9281	High Similarity	NPC140890
0.9275	High Similarity	NPC275055
0.9275	High Similarity	NPC228661
0.9275	High Similarity	NPC254841
0.9275	High Similarity	NPC290291
0.9265	High Similarity	NPC192304
0.9265	High Similarity	NPC159623
0.9265	High Similarity	NPC294593
0.9265	High Similarity	NPC204960
0.9265	High Similarity	NPC472365
0.9265	High Similarity	NPC188646
0.9265	High Similarity	NPC337373
0.9265	High Similarity	NPC82225
0.9265	High Similarity	NPC242294
0.9265	High Similarity	NPC56031
0.9265	High Similarity	NPC175098
0.9265	High Similarity	NPC57601
0.9265	High Similarity	NPC144051
0.9265	High Similarity	NPC18877
0.9265	High Similarity	NPC263670
0.9265	High Similarity	NPC28753
0.9265	High Similarity	NPC312318
0.9265	High Similarity	NPC139813
0.9265	High Similarity	NPC20560
0.9259	High Similarity	NPC113006
0.9259	High Similarity	NPC278556
0.9259	High Similarity	NPC31872
0.9259	High Similarity	NPC473584
0.9259	High Similarity	NPC475589
0.9247	High Similarity	NPC236756
0.9247	High Similarity	NPC311579
0.9247	High Similarity	NPC179126
0.9247	High Similarity	NPC236223
0.9247	High Similarity	NPC78326
0.9247	High Similarity	NPC270620
0.9241	High Similarity	NPC295650
0.9241	High Similarity	NPC260895
0.9241	High Similarity	NPC76376
0.9236	High Similarity	NPC87125
0.9236	High Similarity	NPC159103
0.9236	High Similarity	NPC270465
0.9236	High Similarity	NPC477941
0.9236	High Similarity	NPC269420
0.9231	High Similarity	NPC122828
0.9231	High Similarity	NPC211466
0.9231	High Similarity	NPC44721
0.9231	High Similarity	NPC40086
0.9231	High Similarity	NPC176869
0.9231	High Similarity	NPC3779
0.9231	High Similarity	NPC476182
0.9225	High Similarity	NPC311144
0.9225	High Similarity	NPC234629
0.9225	High Similarity	NPC224714
0.9225	High Similarity	NPC319752
0.9225	High Similarity	NPC311741
0.922	High Similarity	NPC76338
0.922	High Similarity	NPC324134
0.922	High Similarity	NPC293852
0.922	High Similarity	NPC161506
0.922	High Similarity	NPC328164
0.922	High Similarity	NPC66515
0.922	High Similarity	NPC148757
0.922	High Similarity	NPC296917
0.922	High Similarity	NPC324436
0.922	High Similarity	NPC182852
0.922	High Similarity	NPC1089
0.922	High Similarity	NPC37496
0.922	High Similarity	NPC40833
0.922	High Similarity	NPC78803
0.922	High Similarity	NPC166934
0.922	High Similarity	NPC217083
0.922	High Similarity	NPC306829
0.922	High Similarity	NPC299080

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 NPC90582 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	416
0.1-0.2	967
0.2-0.3	1691
0.3-0.4	2701
0.4-0.5	1828
0.5-0.6	1037
0.6-0.7	346
0.7-0.8	103
0.8-0.85	37
0.85-0.9	18
0.9-0.95	5
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.964	High Similarity	NPD4378	Clinical (unspecified phase)
0.9137	High Similarity	NPD1550	Clinical (unspecified phase)
0.9137	High Similarity	NPD1552	Clinical (unspecified phase)
0.9071	High Similarity	NPD1549	Phase 2
0.9028	High Similarity	NPD1512	Approved
0.9021	High Similarity	NPD6799	Approved
0.8993	High Similarity	NPD1510	Phase 2
0.8978	High Similarity	NPD1240	Approved
0.8958	High Similarity	NPD7410	Clinical (unspecified phase)
0.8929	High Similarity	NPD2796	Approved
0.8889	High Similarity	NPD1511	Approved
0.8859	High Similarity	NPD2801	Approved
0.8849	High Similarity	NPD1607	Approved
0.8808	High Similarity	NPD7075	Discontinued
0.88	High Similarity	NPD3817	Phase 2
0.8792	High Similarity	NPD6801	Discontinued
0.8742	High Similarity	NPD3882	Suspended
0.8733	High Similarity	NPD2393	Clinical (unspecified phase)
0.8733	High Similarity	NPD7096	Clinical (unspecified phase)
0.8667	High Similarity	NPD1934	Approved
0.8658	High Similarity	NPD6599	Discontinued
0.8658	High Similarity	NPD4380	Phase 2
0.86	High Similarity	NPD7411	Suspended
0.8581	High Similarity	NPD5403	Approved
0.8562	High Similarity	NPD4381	Clinical (unspecified phase)
0.8553	High Similarity	NPD8443	Clinical (unspecified phase)
0.8544	High Similarity	NPD7804	Clinical (unspecified phase)
0.8471	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8471	Intermediate Similarity	NPD6166	Phase 2
0.8471	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8446	Intermediate Similarity	NPD5401	Approved
0.8438	Intermediate Similarity	NPD6797	Phase 2
0.8429	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8425	Intermediate Similarity	NPD3750	Approved
0.8414	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8385	Intermediate Similarity	NPD7251	Discontinued
0.8366	Intermediate Similarity	NPD7819	Suspended
0.8333	Intermediate Similarity	NPD7808	Phase 3
0.8312	Intermediate Similarity	NPD5402	Approved
0.8276	Intermediate Similarity	NPD1551	Phase 2
0.8231	Intermediate Similarity	NPD2800	Approved
0.8231	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8221	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8199	Intermediate Similarity	NPD7054	Approved
0.8165	Intermediate Similarity	NPD6959	Discontinued
0.8148	Intermediate Similarity	NPD7472	Approved
0.8141	Intermediate Similarity	NPD7768	Phase 2
0.8137	Intermediate Similarity	NPD3818	Discontinued
0.8125	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8089	Intermediate Similarity	NPD3749	Approved
0.8082	Intermediate Similarity	NPD3748	Approved
0.8071	Intermediate Similarity	NPD1203	Approved
0.8069	Intermediate Similarity	NPD6651	Approved
0.8054	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8037	Intermediate Similarity	NPD7074	Phase 3
0.8027	Intermediate Similarity	NPD2935	Discontinued
0.8015	Intermediate Similarity	NPD1548	Phase 1
0.7987	Intermediate Similarity	NPD1243	Approved
0.7974	Intermediate Similarity	NPD920	Approved
0.7973	Intermediate Similarity	NPD2344	Approved
0.7917	Intermediate Similarity	NPD3268	Approved
0.7917	Intermediate Similarity	NPD2313	Discontinued
0.7914	Intermediate Similarity	NPD422	Phase 1
0.7911	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7902	Intermediate Similarity	NPD6832	Phase 2
0.7892	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7888	Intermediate Similarity	NPD6232	Discontinued
0.7875	Intermediate Similarity	NPD5494	Approved
0.7866	Intermediate Similarity	NPD7286	Phase 2
0.7857	Intermediate Similarity	NPD9717	Approved
0.7853	Intermediate Similarity	NPD7473	Discontinued
0.7843	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7843	Intermediate Similarity	NPD2533	Approved
0.7843	Intermediate Similarity	NPD2532	Approved
0.7843	Intermediate Similarity	NPD2534	Approved
0.7838	Intermediate Similarity	NPD2799	Discontinued
0.7838	Intermediate Similarity	NPD7033	Discontinued
0.7829	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7826	Intermediate Similarity	NPD1247	Approved
0.7817	Intermediate Similarity	NPD2797	Approved
0.7812	Intermediate Similarity	NPD919	Approved
0.7786	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD6099	Approved
0.7785	Intermediate Similarity	NPD6100	Approved
0.7778	Intermediate Similarity	NPD4908	Phase 1
0.7771	Intermediate Similarity	NPD5953	Discontinued
0.7763	Intermediate Similarity	NPD2309	Approved
0.7762	Intermediate Similarity	NPD2798	Approved
0.7748	Intermediate Similarity	NPD2654	Approved
0.7746	Intermediate Similarity	NPD3225	Approved
0.773	Intermediate Similarity	NPD3926	Phase 2
0.7725	Intermediate Similarity	NPD6559	Discontinued
0.7697	Intermediate Similarity	NPD4628	Phase 3
0.7687	Intermediate Similarity	NPD943	Approved
0.7671	Intermediate Similarity	NPD6798	Discontinued
0.7671	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7665	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.766	Intermediate Similarity	NPD1610	Phase 2
0.7657	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD3226	Approved
0.7619	Intermediate Similarity	NPD6233	Phase 2
0.76	Intermediate Similarity	NPD4308	Phase 3
0.76	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7569	Intermediate Similarity	NPD3267	Approved
0.7569	Intermediate Similarity	NPD3266	Approved
0.7548	Intermediate Similarity	NPD7390	Discontinued
0.7545	Intermediate Similarity	NPD5844	Phase 1
0.7543	Intermediate Similarity	NPD4360	Phase 2
0.7543	Intermediate Similarity	NPD4363	Phase 3
0.7517	Intermediate Similarity	NPD1933	Approved
0.7517	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2346	Discontinued
0.75	Intermediate Similarity	NPD9545	Approved
0.7485	Intermediate Similarity	NPD3751	Discontinued
0.7483	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD3972	Approved
0.7482	Intermediate Similarity	NPD9493	Approved
0.747	Intermediate Similarity	NPD2403	Approved
0.7468	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD3787	Discontinued
0.7453	Intermediate Similarity	NPD1465	Phase 2
0.7438	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD1296	Phase 2
0.7419	Intermediate Similarity	NPD2354	Approved
0.7415	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD4288	Approved
0.7405	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7401	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7401	Intermediate Similarity	NPD4361	Phase 2
0.74	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD6355	Discontinued
0.74	Intermediate Similarity	NPD447	Suspended
0.74	Intermediate Similarity	NPD230	Phase 1
0.74	Intermediate Similarity	NPD5124	Phase 1
0.7397	Intermediate Similarity	NPD1019	Discontinued
0.7391	Intermediate Similarity	NPD1241	Discontinued
0.7386	Intermediate Similarity	NPD1471	Phase 3
0.7361	Intermediate Similarity	NPD1608	Approved
0.7361	Intermediate Similarity	NPD1481	Phase 2
0.7347	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD4307	Phase 2
0.7333	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD1613	Approved
0.733	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD411	Approved
0.7308	Intermediate Similarity	NPD3887	Approved
0.7305	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD1729	Discontinued
0.7292	Intermediate Similarity	NPD1535	Discovery
0.729	Intermediate Similarity	NPD1652	Phase 2
0.7285	Intermediate Similarity	NPD4340	Discontinued
0.7284	Intermediate Similarity	NPD6844	Discontinued
0.7278	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD2353	Approved
0.7273	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD4062	Phase 3
0.7248	Intermediate Similarity	NPD4625	Phase 3
0.7246	Intermediate Similarity	NPD5711	Approved
0.7246	Intermediate Similarity	NPD5710	Approved
0.7233	Intermediate Similarity	NPD5049	Phase 3
0.7215	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD6104	Discontinued
0.72	Intermediate Similarity	NPD3764	Approved
0.7197	Intermediate Similarity	NPD6190	Approved
0.7195	Intermediate Similarity	NPD2296	Approved
0.7192	Intermediate Similarity	NPD4749	Approved
0.7181	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD1201	Approved
0.7153	Intermediate Similarity	NPD17	Approved
0.7152	Intermediate Similarity	NPD7440	Discontinued
0.7143	Intermediate Similarity	NPD7229	Phase 3
0.7133	Intermediate Similarity	NPD3027	Phase 3
0.7133	Intermediate Similarity	NPD1894	Discontinued
0.7119	Intermediate Similarity	NPD4287	Approved
0.7117	Intermediate Similarity	NPD5889	Approved
0.7117	Intermediate Similarity	NPD5890	Approved
0.7114	Intermediate Similarity	NPD2861	Phase 2
0.7108	Intermediate Similarity	NPD6971	Discontinued
0.7107	Intermediate Similarity	NPD7213	Phase 3
0.7107	Intermediate Similarity	NPD7212	Phase 2
0.7105	Intermediate Similarity	NPD3140	Approved
0.7105	Intermediate Similarity	NPD4060	Phase 1
0.7105	Intermediate Similarity	NPD3142	Approved
0.7102	Intermediate Similarity	NPD8434	Phase 2
0.7099	Intermediate Similarity	NPD7458	Discontinued
0.7097	Intermediate Similarity	NPD7584	Approved
0.7095	Intermediate Similarity	NPD1470	Approved
0.7083	Intermediate Similarity	NPD7199	Phase 2
0.7076	Intermediate Similarity	NPD5940	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD7447	Phase 1
0.7063	Intermediate Similarity	NPD4661	Approved
0.7063	Intermediate Similarity	NPD4662	Approved
0.7055	Intermediate Similarity	NPD6585	Discontinued
0.7051	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD1876	Approved
0.7025	Intermediate Similarity	NPD7003	Approved
0.702	Intermediate Similarity	NPD7095	Approved
0.6994	Remote Similarity	NPD5808	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