NPASS Compound

Structure

CID137264 OpenBabel06191715492D 21 23 0 0 0 0 0 0 0 0999 V2000 -4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 2.5000 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 -3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 3.0000 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 0.8660 -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 -0.8660 1.5000 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 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 2.5000 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 1.0000 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 1.7321 0.0000 0.0000 C 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 3.4641 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 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 2 2 0 0 0 0 1 4 1 0 0 0 0 2 5 1 0 0 0 0 3 6 2 0 0 0 0 3 7 1 0 0 0 0 4 11 2 0 0 0 0 5 13 2 0 0 0 0 6 14 1 0 0 0 0 7 16 2 0 0 0 0 8 9 1 0 0 0 0 8 11 1 0 0 0 0 9 12 1 0 0 0 0 10 12 2 0 0 0 0 10 15 1 0 0 0 0 11 13 1 0 0 0 0 12 21 1 0 0 0 0 13 18 1 0 0 0 0 14 17 2 0 0 0 0 14 19 1 0 0 0 0 15 17 1 0 0 0 0 15 20 2 0 0 0 0 16 17 1 0 0 0 0 16 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	282.09
Volume:	290.988
LogP:	3.535
LogD:	3.073
LogS:	-3.159
# Rotatable Bonds:	3
TPSA:	70.67
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.774
Synthetic Accessibility Score:	2.294
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:	-4.826
MDCK Permeability:	1.4401388398255222e-05
Pgp-inhibitor:	0.008
Pgp-substrate:	0.042
Human Intestinal Absorption (HIA):	0.051
20% Bioavailability (F20%):	0.999
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.093
Plasma Protein Binding (PPB):	98.79058074951172%
Volume Distribution (VD):	0.554
Pgp-substrate:	1.23434317111969%

ADMET: Metabolism

CYP1A2-inhibitor:	0.986
CYP1A2-substrate:	0.836
CYP2C19-inhibitor:	0.946
CYP2C19-substrate:	0.066
CYP2C9-inhibitor:	0.835
CYP2C9-substrate:	0.954
CYP2D6-inhibitor:	0.847
CYP2D6-substrate:	0.912
CYP3A4-inhibitor:	0.507
CYP3A4-substrate:	0.254

ADMET: Excretion

Clearance (CL):	4.874
Half-life (T1/2):	0.819

ADMET: Toxicity

hERG Blockers:	0.022
Human Hepatotoxicity (H-HT):	0.113
Drug-inuced Liver Injury (DILI):	0.311
AMES Toxicity:	0.762
Rat Oral Acute Toxicity:	0.247
Maximum Recommended Daily Dose:	0.082
Skin Sensitization:	0.934
Carcinogencity:	0.727
Eye Corrosion:	0.026
Eye Irritation:	0.968
Respiratory Toxicity:	0.07

Download Data

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

Natural Product: NPC137264

Natural Product ID:	NPC137264
*Common Name:**	5-Hydroxy-2-[2-(2-Hydroxyphenyl)Ethyl]Chromone
IUPAC Name:	5-hydroxy-2-[2-(2-hydroxyphenyl)ethyl]chromen-4-one
Synonyms:
Standard InCHIKey:	VJJIYNCAKZLESG-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C17H14O4/c18-13-5-2-1-4-11(13)8-9-12-10-15(20)17-14(19)6-3-7-16(17)21-12/h1-7,10,18-19H,8-9H2
SMILES:	c1ccc(c(c1)CCc1cc(=O)c2c(cccc2o1)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL479684
PubChem CID:	11822089
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]
NPO3345	Mylabris phalerata	Species	Meloidae	Eukaryota	n.a.	n.a.	n.a.	PMID[27458783]
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]
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]
NPO23628	Imperata cylindrica	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26919	Sanguisorba officinalis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26919	Sanguisorba officinalis	Species	Rosaceae	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]
NPO23628	Imperata cylindrica	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
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[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]
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
Others	4

Activity Type	# Activity
Individual Protein	3
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT292	Individual Protein	Serotonin 2c (5-HT2c) receptor	Homo sapiens	Inhibition	=	23.8	%	PMID[569880]
NPT291	Individual Protein	Serotonin 2b (5-HT2b) receptor	Homo sapiens	Inhibition	=	12.8	%	PMID[569880]
NPT290	Individual Protein	Serotonin 2a (5-HT2a) receptor	Homo sapiens	Inhibition	=	24.3	%	PMID[569880]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	63.6	%	PMID[569879]

☑ 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 NPC137264 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	435
0.1-0.2	2029
0.2-0.3	5362
0.3-0.4	12361
0.4-0.5	4929
0.5-0.6	4848
0.6-0.7	5734
0.7-0.8	4046
0.8-0.85	1734
0.85-0.9	999
0.9-0.95	187
0.95-1	33

Similarity Score	Similarity Level	Natural Product ID
0.9919	High Similarity	NPC39753
0.9919	High Similarity	NPC115998
0.9839	High Similarity	NPC197425
0.9762	High Similarity	NPC113006
0.9685	High Similarity	NPC128216
0.9609	High Similarity	NPC50898
0.9609	High Similarity	NPC78540
0.9609	High Similarity	NPC274121
0.9609	High Similarity	NPC213216
0.9538	High Similarity	NPC231772
0.9538	High Similarity	NPC473887
0.9538	High Similarity	NPC29353
0.9538	High Similarity	NPC13408
0.9538	High Similarity	NPC127447
0.9538	High Similarity	NPC124784
0.9538	High Similarity	NPC194281
0.9538	High Similarity	NPC234133
0.9538	High Similarity	NPC47815
0.9535	High Similarity	NPC172262
0.9535	High Similarity	NPC248872
0.9524	High Similarity	NPC187907
0.9466	High Similarity	NPC266597
0.9466	High Similarity	NPC250266
0.9457	High Similarity	NPC57601
0.9394	High Similarity	NPC201395
0.9389	High Similarity	NPC187432
0.9389	High Similarity	NPC256042
0.9389	High Similarity	NPC116775
0.9389	High Similarity	NPC216361
0.9389	High Similarity	NPC281917
0.9365	High Similarity	NPC41721
0.9323	High Similarity	NPC241838
0.9323	High Similarity	NPC143799
0.9323	High Similarity	NPC78913
0.9323	High Similarity	NPC152042
0.9323	High Similarity	NPC216978
0.9323	High Similarity	NPC96565
0.9323	High Similarity	NPC301217
0.9323	High Similarity	NPC303633
0.9323	High Similarity	NPC220062
0.9323	High Similarity	NPC55018
0.9323	High Similarity	NPC18260
0.9318	High Similarity	NPC275055
0.9318	High Similarity	NPC290291
0.9318	High Similarity	NPC299379
0.9318	High Similarity	NPC228661
0.9313	High Similarity	NPC9985
0.9313	High Similarity	NPC239495
0.928	High Similarity	NPC193805
0.9254	High Similarity	NPC184536
0.9254	High Similarity	NPC103342
0.9254	High Similarity	NPC103904
0.9254	High Similarity	NPC241100
0.9254	High Similarity	NPC146679
0.9254	High Similarity	NPC270883
0.9254	High Similarity	NPC269652
0.9254	High Similarity	NPC230285
0.9254	High Similarity	NPC159275
0.9254	High Similarity	NPC59951
0.9254	High Similarity	NPC281207
0.9254	High Similarity	NPC172986
0.9254	High Similarity	NPC261227
0.9248	High Similarity	NPC99333
0.9248	High Similarity	NPC188947
0.9248	High Similarity	NPC280284
0.9248	High Similarity	NPC118813
0.9231	High Similarity	NPC10971
0.9225	High Similarity	NPC270369
0.9225	High Similarity	NPC5515
0.9213	High Similarity	NPC22783
0.9185	High Similarity	NPC14871
0.9185	High Similarity	NPC110969
0.9185	High Similarity	NPC156590
0.9185	High Similarity	NPC90582
0.9185	High Similarity	NPC64908
0.9185	High Similarity	NPC118840
0.9185	High Similarity	NPC136840
0.9185	High Similarity	NPC147688
0.9185	High Similarity	NPC282300
0.9185	High Similarity	NPC262094
0.9185	High Similarity	NPC205006
0.9179	High Similarity	NPC265871
0.9179	High Similarity	NPC261234
0.9179	High Similarity	NPC329203
0.9179	High Similarity	NPC225153
0.9179	High Similarity	NPC217186
0.9179	High Similarity	NPC310135
0.9179	High Similarity	NPC274784
0.9179	High Similarity	NPC53181
0.9179	High Similarity	NPC222342
0.9179	High Similarity	NPC150648
0.9179	High Similarity	NPC20709
0.9173	High Similarity	NPC12296
0.9173	High Similarity	NPC107586
0.9173	High Similarity	NPC188879
0.9173	High Similarity	NPC295261
0.9173	High Similarity	NPC296490
0.9173	High Similarity	NPC32441
0.9173	High Similarity	NPC243083
0.9173	High Similarity	NPC79943
0.9173	High Similarity	NPC13768
0.9173	High Similarity	NPC287246
0.9154	High Similarity	NPC475009
0.9154	High Similarity	NPC473584
0.9154	High Similarity	NPC475589
0.9154	High Similarity	NPC475008
0.9154	High Similarity	NPC278556
0.9154	High Similarity	NPC186097
0.9154	High Similarity	NPC31872
0.9118	High Similarity	NPC59739
0.9118	High Similarity	NPC62840
0.9118	High Similarity	NPC214236
0.9118	High Similarity	NPC11561
0.9118	High Similarity	NPC217083
0.9118	High Similarity	NPC293852
0.9118	High Similarity	NPC226636
0.9118	High Similarity	NPC200694
0.9118	High Similarity	NPC473042
0.9118	High Similarity	NPC1534
0.9118	High Similarity	NPC299080
0.9118	High Similarity	NPC78803
0.9111	High Similarity	NPC69769
0.9111	High Similarity	NPC284550
0.9111	High Similarity	NPC76445
0.9111	High Similarity	NPC6407
0.9111	High Similarity	NPC110228
0.9111	High Similarity	NPC305355
0.9111	High Similarity	NPC150522
0.9111	High Similarity	NPC475680
0.9111	High Similarity	NPC235239
0.9111	High Similarity	NPC188243
0.9111	High Similarity	NPC129853
0.9104	High Similarity	NPC472460
0.9104	High Similarity	NPC276905
0.9104	High Similarity	NPC329225
0.9104	High Similarity	NPC147686
0.9104	High Similarity	NPC18457
0.9104	High Similarity	NPC124269
0.9098	High Similarity	NPC240593
0.9084	High Similarity	NPC129132
0.9084	High Similarity	NPC473655
0.9084	High Similarity	NPC212631
0.9084	High Similarity	NPC257756
0.9084	High Similarity	NPC25937
0.9084	High Similarity	NPC101294
0.9084	High Similarity	NPC205468
0.9084	High Similarity	NPC87231
0.9051	High Similarity	NPC9117
0.9051	High Similarity	NPC11700
0.9051	High Similarity	NPC470216
0.9051	High Similarity	NPC24821
0.9051	High Similarity	NPC190637
0.9051	High Similarity	NPC293053
0.9051	High Similarity	NPC219915
0.9051	High Similarity	NPC212932
0.9051	High Similarity	NPC38219
0.9044	High Similarity	NPC312391
0.9044	High Similarity	NPC213322
0.9044	High Similarity	NPC103362
0.9044	High Similarity	NPC4743
0.9044	High Similarity	NPC324386
0.9044	High Similarity	NPC3188
0.9037	High Similarity	NPC140890
0.9037	High Similarity	NPC316480
0.903	High Similarity	NPC84585
0.903	High Similarity	NPC116632
0.903	High Similarity	NPC7013
0.903	High Similarity	NPC160972
0.903	High Similarity	NPC294409
0.903	High Similarity	NPC181124
0.903	High Similarity	NPC303644
0.903	High Similarity	NPC254841
0.903	High Similarity	NPC209560
0.903	High Similarity	NPC162680
0.903	High Similarity	NPC476480
0.9023	High Similarity	NPC39426
0.9023	High Similarity	NPC234560
0.9015	High Similarity	NPC18877
0.9015	High Similarity	NPC159623
0.9015	High Similarity	NPC144051
0.9015	High Similarity	NPC223457
0.9015	High Similarity	NPC472365
0.9015	High Similarity	NPC139813
0.9015	High Similarity	NPC28753
0.9015	High Similarity	NPC108113
0.9015	High Similarity	NPC294593
0.9015	High Similarity	NPC93756
0.9015	High Similarity	NPC175098
0.9015	High Similarity	NPC188646
0.9015	High Similarity	NPC312318
0.9015	High Similarity	NPC192304
0.9015	High Similarity	NPC242294
0.9015	High Similarity	NPC82225
0.9015	High Similarity	NPC337373
0.9015	High Similarity	NPC56031
0.9015	High Similarity	NPC204960
0.9015	High Similarity	NPC20560
0.9015	High Similarity	NPC263670
0.9008	High Similarity	NPC284424
0.9008	High Similarity	NPC308037

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 NPC137264 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	429
0.1-0.2	997
0.2-0.3	1474
0.3-0.4	2753
0.4-0.5	1920
0.5-0.6	1107
0.6-0.7	298
0.7-0.8	114
0.8-0.85	36
0.85-0.9	17
0.9-0.95	5
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9173	High Similarity	NPD1552	Clinical (unspecified phase)
0.9173	High Similarity	NPD1550	Clinical (unspecified phase)
0.9104	High Similarity	NPD1549	Phase 2
0.9023	High Similarity	NPD1510	Phase 2
0.8986	High Similarity	NPD4378	Clinical (unspecified phase)
0.8913	High Similarity	NPD1511	Approved
0.8864	High Similarity	NPD1240	Approved
0.8849	High Similarity	NPD7410	Clinical (unspecified phase)
0.8832	High Similarity	NPD3750	Approved
0.8815	High Similarity	NPD1551	Phase 2
0.8786	High Similarity	NPD1512	Approved
0.876	High Similarity	NPD1203	Approved
0.8731	High Similarity	NPD1607	Approved
0.8676	High Similarity	NPD2796	Approved
0.8592	High Similarity	NPD5403	Approved
0.8582	High Similarity	NPD5401	Approved
0.8493	Intermediate Similarity	NPD2801	Approved
0.8467	Intermediate Similarity	NPD3748	Approved
0.8433	Intermediate Similarity	NPD2313	Discontinued
0.8429	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8425	Intermediate Similarity	NPD1934	Approved
0.8414	Intermediate Similarity	NPD4380	Phase 2
0.8385	Intermediate Similarity	NPD9717	Approved
0.838	Intermediate Similarity	NPD6799	Approved
0.8367	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8356	Intermediate Similarity	NPD7411	Suspended
0.8322	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8311	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8308	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.8286	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8281	Intermediate Similarity	NPD1548	Phase 1
0.8258	Intermediate Similarity	NPD3225	Approved
0.82	Intermediate Similarity	NPD3749	Approved
0.82	Intermediate Similarity	NPD7075	Discontinued
0.8195	Intermediate Similarity	NPD2797	Approved
0.8188	Intermediate Similarity	NPD5402	Approved
0.8176	Intermediate Similarity	NPD6801	Discontinued
0.8168	Intermediate Similarity	NPD422	Phase 1
0.8162	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8162	Intermediate Similarity	NPD3268	Approved
0.8148	Intermediate Similarity	NPD6832	Phase 2
0.8134	Intermediate Similarity	NPD2798	Approved
0.8133	Intermediate Similarity	NPD3882	Suspended
0.8133	Intermediate Similarity	NPD7768	Phase 2
0.8121	Intermediate Similarity	NPD7819	Suspended
0.8121	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8099	Intermediate Similarity	NPD2800	Approved
0.8071	Intermediate Similarity	NPD4308	Phase 3
0.8067	Intermediate Similarity	NPD3817	Phase 2
0.8041	Intermediate Similarity	NPD6599	Discontinued
0.7972	Intermediate Similarity	NPD1243	Approved
0.7972	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7958	Intermediate Similarity	NPD2344	Approved
0.7943	Intermediate Similarity	NPD2799	Discontinued
0.7926	Intermediate Similarity	NPD3266	Approved
0.7926	Intermediate Similarity	NPD3267	Approved
0.7898	Intermediate Similarity	NPD3818	Discontinued
0.7895	Intermediate Similarity	NPD1610	Phase 2
0.7887	Intermediate Similarity	NPD6099	Approved
0.7887	Intermediate Similarity	NPD2935	Discontinued
0.7887	Intermediate Similarity	NPD6100	Approved
0.7885	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7885	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7885	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7885	Intermediate Similarity	NPD6166	Phase 2
0.7857	Intermediate Similarity	NPD1933	Approved
0.7852	Intermediate Similarity	NPD3226	Approved
0.7848	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7848	Intermediate Similarity	NPD7054	Approved
0.7846	Intermediate Similarity	NPD9493	Approved
0.7832	Intermediate Similarity	NPD2346	Discontinued
0.7817	Intermediate Similarity	NPD7033	Discontinued
0.7808	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7806	Intermediate Similarity	NPD6959	Discontinued
0.7801	Intermediate Similarity	NPD6651	Approved
0.7799	Intermediate Similarity	NPD7472	Approved
0.7793	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7786	Intermediate Similarity	NPD943	Approved
0.7786	Intermediate Similarity	NPD4307	Phase 2
0.777	Intermediate Similarity	NPD1296	Phase 2
0.777	Intermediate Similarity	NPD411	Approved
0.7761	Intermediate Similarity	NPD1201	Approved
0.7754	Intermediate Similarity	NPD4908	Phase 1
0.775	Intermediate Similarity	NPD6797	Phase 2
0.774	Intermediate Similarity	NPD2309	Approved
0.773	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD447	Suspended
0.7718	Intermediate Similarity	NPD920	Approved
0.7712	Intermediate Similarity	NPD4288	Approved
0.7703	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7702	Intermediate Similarity	NPD7251	Discontinued
0.7688	Intermediate Similarity	NPD7074	Phase 3
0.7664	Intermediate Similarity	NPD1470	Approved
0.7662	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD7808	Phase 3
0.7654	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7626	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7609	Intermediate Similarity	NPD1019	Discontinued
0.7593	Intermediate Similarity	NPD6559	Discontinued
0.7574	Intermediate Similarity	NPD1481	Phase 2
0.7574	Intermediate Similarity	NPD1608	Approved
0.7571	Intermediate Similarity	NPD4625	Phase 3
0.7569	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7554	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD6232	Discontinued
0.7531	Intermediate Similarity	NPD5953	Discontinued
0.7518	Intermediate Similarity	NPD4749	Approved
0.7518	Intermediate Similarity	NPD3764	Approved
0.7516	Intermediate Similarity	NPD5494	Approved
0.7516	Intermediate Similarity	NPD7286	Phase 2
0.75	Intermediate Similarity	NPD7473	Discontinued
0.75	Intermediate Similarity	NPD74	Approved
0.75	Intermediate Similarity	NPD9266	Approved
0.75	Intermediate Similarity	NPD1535	Discovery
0.7483	Intermediate Similarity	NPD2654	Approved
0.7481	Intermediate Similarity	NPD1241	Discontinued
0.7467	Intermediate Similarity	NPD2534	Approved
0.7467	Intermediate Similarity	NPD2532	Approved
0.7467	Intermediate Similarity	NPD2533	Approved
0.7438	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD4628	Phase 3
0.7422	Intermediate Similarity	NPD9264	Approved
0.7422	Intermediate Similarity	NPD9263	Approved
0.7422	Intermediate Similarity	NPD9267	Approved
0.7419	Intermediate Similarity	NPD1465	Phase 2
0.7413	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7413	Intermediate Similarity	NPD1613	Approved
0.7376	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7361	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7361	Intermediate Similarity	NPD5124	Phase 1
0.7355	Intermediate Similarity	NPD6844	Discontinued
0.7353	Intermediate Similarity	NPD17	Approved
0.7351	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD5940	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD919	Approved
0.7333	Intermediate Similarity	NPD9545	Approved
0.7333	Intermediate Similarity	NPD1894	Discontinued
0.7313	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7286	Intermediate Similarity	NPD1164	Approved
0.7285	Intermediate Similarity	NPD7390	Discontinued
0.7273	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD6798	Discontinued
0.7267	Intermediate Similarity	NPD3926	Phase 2
0.725	Intermediate Similarity	NPD1247	Approved
0.7237	Intermediate Similarity	NPD4661	Approved
0.7237	Intermediate Similarity	NPD4662	Approved
0.723	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD6585	Discontinued
0.7212	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD4360	Phase 2
0.7209	Intermediate Similarity	NPD968	Approved
0.7209	Intermediate Similarity	NPD4363	Phase 3
0.7195	Intermediate Similarity	NPD5844	Phase 1
0.7194	Intermediate Similarity	NPD3972	Approved
0.7179	Intermediate Similarity	NPD5890	Approved
0.7179	Intermediate Similarity	NPD5889	Approved
0.7176	Intermediate Similarity	NPD4287	Approved
0.7168	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD4361	Phase 2
0.7164	Intermediate Similarity	NPD9281	Approved
0.7162	Intermediate Similarity	NPD5405	Approved
0.7162	Intermediate Similarity	NPD5404	Approved
0.7162	Intermediate Similarity	NPD5408	Approved
0.7162	Intermediate Similarity	NPD5406	Approved
0.7153	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD2296	Approved
0.7143	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD3751	Discontinued
0.7133	Intermediate Similarity	NPD1652	Phase 2
0.7132	Intermediate Similarity	NPD9697	Approved
0.7126	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD230	Phase 1
0.7114	Intermediate Similarity	NPD1471	Phase 3
0.7109	Intermediate Similarity	NPD9261	Approved
0.7105	Intermediate Similarity	NPD7440	Discontinued
0.7103	Intermediate Similarity	NPD6233	Phase 2
0.7092	Intermediate Similarity	NPD1876	Approved
0.7083	Intermediate Similarity	NPD8312	Approved
0.7083	Intermediate Similarity	NPD8313	Approved
0.707	Intermediate Similarity	NPD2366	Approved
0.7063	Intermediate Similarity	NPD6971	Discontinued
0.7063	Intermediate Similarity	NPD2861	Phase 2
0.7059	Intermediate Similarity	NPD7212	Phase 2
0.7059	Intermediate Similarity	NPD7213	Phase 3
0.7048	Intermediate Similarity	NPD1729	Discontinued
0.7039	Intermediate Similarity	NPD3295	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD2354	Approved
0.7015	Intermediate Similarity	NPD5535	Approved
0.7013	Intermediate Similarity	NPD7447	Phase 1
0.7007	Intermediate Similarity	NPD4340	Discontinued
0.7007	Intermediate Similarity	NPD6355	Discontinued
0.7	Intermediate Similarity	NPD5019	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD1091	Approved
0.6994	Remote Similarity	NPD3787	Discontinued
0.6986	Remote Similarity	NPD520	Approved
0.6985	Remote Similarity	NPD6671	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