NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	192.04
Volume:	186.382
LogP:	1.626
LogD:	1.575
LogS:	-2.676
# Rotatable Bonds:	0
TPSA:	70.67
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.663
Synthetic Accessibility Score:	2.4
Fsp3:	0.1
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.761
MDCK Permeability:	1.1404730685171671e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.99
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.943
30% Bioavailability (F30%):	0.995

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.024
Plasma Protein Binding (PPB):	86.07632446289062%
Volume Distribution (VD):	0.748
Pgp-substrate:	21.826417922973633%

ADMET: Metabolism

CYP1A2-inhibitor:	0.98
CYP1A2-substrate:	0.906
CYP2C19-inhibitor:	0.176
CYP2C19-substrate:	0.07
CYP2C9-inhibitor:	0.232
CYP2C9-substrate:	0.922
CYP2D6-inhibitor:	0.458
CYP2D6-substrate:	0.739
CYP3A4-inhibitor:	0.204
CYP3A4-substrate:	0.174

ADMET: Excretion

Clearance (CL):	8.564
Half-life (T1/2):	0.875

ADMET: Toxicity

hERG Blockers:	0.016
Human Hepatotoxicity (H-HT):	0.059
Drug-inuced Liver Injury (DILI):	0.524
AMES Toxicity:	0.496
Rat Oral Acute Toxicity:	0.054
Maximum Recommended Daily Dose:	0.767
Skin Sensitization:	0.852
Carcinogencity:	0.049
Eye Corrosion:	0.318
Eye Irritation:	0.97
Respiratory Toxicity:	0.361

Download Data

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

Natural Product: NPC270369

Natural Product ID:	NPC270369
*Common Name:**	Noreugenin
IUPAC Name:	5,7-dihydroxy-2-methylchromen-4-one
Synonyms:	Noreugenin
Standard InCHIKey:	NCUJRUDLFCGVOE-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C10H8O4/c1-5-2-7(12)10-8(13)3-6(11)4-9(10)14-5/h2-4,11,13H,1H3
SMILES:	Oc1cc(O)c2c(c1)oc(cc2=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL507707
PubChem CID:	5375252
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
NPO27978	Crossosoma bigelovii	Species	Crossosomataceae	Eukaryota	n.a.	fruit	n.a.	DOI[10.1021/np8006342]
NPO27978	Crossosoma bigelovii	Species	Crossosomataceae	Eukaryota	n.a.	leaf	n.a.	DOI[10.1021/np8006342]
NPO27978	Crossosoma bigelovii	Species	Crossosomataceae	Eukaryota	n.a.	flower	n.a.	DOI[10.1021/np8006342]
NPO27978	Crossosoma bigelovii	Species	Crossosomataceae	Eukaryota	n.a.	twig	n.a.	DOI[10.1021/np8006342]
NPO25825	Saussurea lappa	Species	Asteraceae	Eukaryota	Roots	n.a.	n.a.	PMID[14510592]
NPO29417	Fallopia multiflora	Species	Polygonaceae	Eukaryota	n.a.	root	n.a.	PMID[16564530]
NPO27978	Crossosoma bigelovii	Species	Crossosomataceae	Eukaryota	n.a.	fruit	n.a.	PMID[19405508]
NPO27978	Crossosoma bigelovii	Species	Crossosomataceae	Eukaryota	n.a.	leaf	n.a.	PMID[19405508]
NPO27978	Crossosoma bigelovii	Species	Crossosomataceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19405508]
NPO27978	Crossosoma bigelovii	Species	Crossosomataceae	Eukaryota	n.a.	flower	n.a.	PMID[19405508]
NPO27978	Crossosoma bigelovii	Species	Crossosomataceae	Eukaryota	n.a.	twig	n.a.	PMID[19405508]
NPO13784	Dalbergia candenatensis	Species	Fabaceae	Eukaryota	heartwood	n.a.	n.a.	PMID[19653666]
NPO12711	Ligularia altaica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20073490]
NPO25983	Pisonia aculeata	Species	Nyctaginaceae	Eukaryota	n.a.	stem	n.a.	PMID[21542597]
NPO25983	Pisonia aculeata	Species	Nyctaginaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21542597]
NPO25983	Pisonia aculeata	Species	Nyctaginaceae	Eukaryota	n.a.	root	n.a.	PMID[21542597]
NPO8872	Streptomyces rishiriensis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[24079980]
NPO4576	Corynandra viscosa	Species	Cleomaceae	Eukaryota	n.a.	leaf	n.a.	PMID[28135851]
NPO29417	Fallopia multiflora	Species	Polygonaceae	Eukaryota	Roots	n.a.	n.a.	PMID[29359942]
NPO29417	Fallopia multiflora	Species	Polygonaceae	Eukaryota	Roots	n.a.	n.a.	PMID[31944695]
NPO9601	Ptaeroxylon obliquum	Species	Rutaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[32790311]
NPO13784	Dalbergia candenatensis	Species	Fabaceae	Eukaryota	n.a.	Thai	n.a.	PMID[3430167]
NPO25825	Saussurea lappa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[3572418]
NPO29417	Fallopia multiflora	Species	Polygonaceae	Eukaryota	Roots; Tubers	n.a.	n.a.	PMID[7714535]
NPO8872	Streptomyces rishiriensis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[8931735]
NPO22560	Strychnos parvifolia	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4576	Corynandra viscosa	Species	Cleomaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29417	Fallopia multiflora	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22560	Strychnos parvifolia	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9601	Ptaeroxylon obliquum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25825	Saussurea lappa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29417	Fallopia multiflora	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO25825	Saussurea lappa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO10319	Calycodendron milnei	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO21220	Pulicaria uliginosa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22560	Strychnos parvifolia	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27978	Crossosoma bigelovii	Species	Crossosomataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13784	Dalbergia candenatensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22475.1	Brachylaena discolor var. rotundata	Varieties	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9612	Dryopteris dilatata	Species	Dryopteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4576	Corynandra viscosa	Species	Cleomaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16355	Phyllanthus acutifolius	Species	Leiothrichidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22818	Acritopappus confertus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12341	Axinyssa pitys	Species	Halichondriidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9601	Ptaeroxylon obliquum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8872	Streptomyces rishiriensis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO25983	Pisonia aculeata	Species	Nyctaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25825	Saussurea lappa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12711	Ligularia altaica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13842	Nepeta caesarea	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25680	Ramalina siliquosa	Species	Ramalinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17625	Colchicum hierosolymitanum	Species	Colchicaceae	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
GI50	3
IC50	1
MIC	5
Others	1

Activity Type	# Activity
Cell Line	4
Organism	6
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT759	Cell Line	H9	Homo sapiens	IC50	=	214000.0	nM	PMID[531193]
NPT81	Cell Line	A549	Homo sapiens	GI50	>	50000.0	nM	PMID[531194]
NPT83	Cell Line	MCF7	Homo sapiens	GI50	>	50000.0	nM	PMID[531194]
NPT139	Cell Line	HT-29	Homo sapiens	GI50	>	50000.0	nM	PMID[531194]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	49000.0	nM	PMID[531193]
NPT27	Others	Unspecified		TI	=	4.0	n.a.	PMID[531193]
NPT790	Organism	Mycobacterium tuberculosis H37Rv	Mycobacterium tuberculosis H37Rv	MIC	=	110.0	ug.mL-1	PMID[531195]
NPT20	Organism	Candida albicans	Candida albicans	MIC	=	16300.0	nM	PMID[531196]
NPT85	Organism	Filobasidiella neoformans	Cryptococcus neoformans	MIC	=	16300.0	nM	PMID[531196]

☑ 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 NPC270369 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	450
0.1-0.2	2220
0.2-0.3	5915
0.3-0.4	12494
0.4-0.5	4343
0.5-0.6	4951
0.6-0.7	5663
0.7-0.8	3957
0.8-0.85	1799
0.85-0.9	766
0.9-0.95	123
0.95-1	16

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC5515
0.992	High Similarity	NPC31872
0.992	High Similarity	NPC473584
0.992	High Similarity	NPC475589
0.9841	High Similarity	NPC25937
0.9841	High Similarity	NPC10971
0.9764	High Similarity	NPC223457
0.9764	High Similarity	NPC108113
0.9764	High Similarity	NPC93756
0.9688	High Similarity	NPC125920
0.9612	High Similarity	NPC60667
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	NPC174999
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	NPC47815
0.9538	High Similarity	NPC234133
0.9535	High Similarity	NPC172262
0.9531	High Similarity	NPC203817
0.952	High Similarity	NPC475496
0.952	High Similarity	NPC49852
0.952	High Similarity	NPC128428
0.952	High Similarity	NPC305518
0.9466	High Similarity	NPC266597
0.9466	High Similarity	NPC250266
0.9462	High Similarity	NPC242712
0.9462	High Similarity	NPC151113
0.9457	High Similarity	NPC57601
0.9453	High Similarity	NPC113006
0.9444	High Similarity	NPC473907
0.9394	High Similarity	NPC470669
0.9394	High Similarity	NPC131130
0.9394	High Similarity	NPC470668
0.9394	High Similarity	NPC201395
0.9394	High Similarity	NPC57380
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
0.9385	High Similarity	NPC144027
0.9385	High Similarity	NPC236974
0.937	High Similarity	NPC473894
0.937	High Similarity	NPC69235
0.937	High Similarity	NPC212379
0.937	High Similarity	NPC187907
0.9323	High Similarity	NPC471697
0.9323	High Similarity	NPC241838
0.9323	High Similarity	NPC23257
0.9323	High Similarity	NPC78913
0.9323	High Similarity	NPC139554
0.9323	High Similarity	NPC152042
0.9323	High Similarity	NPC143799
0.9323	High Similarity	NPC96565
0.9323	High Similarity	NPC301217
0.9323	High Similarity	NPC216978
0.9323	High Similarity	NPC303633
0.9323	High Similarity	NPC220062
0.9323	High Similarity	NPC55018
0.9323	High Similarity	NPC18260
0.9318	High Similarity	NPC160972
0.9318	High Similarity	NPC299379
0.9318	High Similarity	NPC188879
0.9318	High Similarity	NPC228661
0.9313	High Similarity	NPC9985
0.9313	High Similarity	NPC239495
0.9297	High Similarity	NPC185497
0.9291	High Similarity	NPC80694
0.9291	High Similarity	NPC186098
0.9254	High Similarity	NPC172986
0.9254	High Similarity	NPC103342
0.9254	High Similarity	NPC103904
0.9254	High Similarity	NPC471587
0.9254	High Similarity	NPC184536
0.9254	High Similarity	NPC270883
0.9254	High Similarity	NPC269652
0.9254	High Similarity	NPC241100
0.9254	High Similarity	NPC230285
0.9254	High Similarity	NPC159275
0.9254	High Similarity	NPC59951
0.9254	High Similarity	NPC281207
0.9254	High Similarity	NPC261227
0.9254	High Similarity	NPC146679
0.9248	High Similarity	NPC188947
0.9248	High Similarity	NPC474487
0.9248	High Similarity	NPC99333
0.9248	High Similarity	NPC124269
0.9248	High Similarity	NPC470672
0.9248	High Similarity	NPC474504
0.9248	High Similarity	NPC280284
0.9248	High Similarity	NPC470671
0.9242	High Similarity	NPC156910
0.9242	High Similarity	NPC240147
0.9242	High Similarity	NPC187826
0.9242	High Similarity	NPC240593
0.9242	High Similarity	NPC470397
0.9242	High Similarity	NPC121243
0.9242	High Similarity	NPC470398
0.9237	High Similarity	NPC248872
0.9231	High Similarity	NPC212631
0.9231	High Similarity	NPC205468
0.9231	High Similarity	NPC87231
0.9231	High Similarity	NPC129132
0.9231	High Similarity	NPC257756
0.9225	High Similarity	NPC137264
0.9219	High Similarity	NPC60558
0.9219	High Similarity	NPC197425
0.9219	High Similarity	NPC230818
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	NPC329203
0.9179	High Similarity	NPC150648
0.9179	High Similarity	NPC225153
0.9179	High Similarity	NPC217186
0.9179	High Similarity	NPC310135
0.9179	High Similarity	NPC53181
0.9179	High Similarity	NPC222342
0.9179	High Similarity	NPC473076
0.9179	High Similarity	NPC274784
0.9179	High Similarity	NPC20709
0.9179	High Similarity	NPC140890
0.9173	High Similarity	NPC12296
0.9173	High Similarity	NPC290291
0.9173	High Similarity	NPC332594
0.9173	High Similarity	NPC107586
0.9173	High Similarity	NPC275055
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	NPC254841
0.9173	High Similarity	NPC287246
0.9167	High Similarity	NPC101752
0.916	High Similarity	NPC82225
0.916	High Similarity	NPC18877
0.916	High Similarity	NPC188646
0.916	High Similarity	NPC56031
0.916	High Similarity	NPC472365
0.916	High Similarity	NPC312318
0.916	High Similarity	NPC263670
0.916	High Similarity	NPC28753
0.916	High Similarity	NPC144051
0.916	High Similarity	NPC204960
0.916	High Similarity	NPC20560
0.916	High Similarity	NPC175098
0.916	High Similarity	NPC139813
0.916	High Similarity	NPC294593
0.916	High Similarity	NPC242294
0.916	High Similarity	NPC337373
0.916	High Similarity	NPC192304
0.916	High Similarity	NPC159623
0.9154	High Similarity	NPC65060
0.9154	High Similarity	NPC313618
0.9154	High Similarity	NPC308037
0.9154	High Similarity	NPC64359
0.9154	High Similarity	NPC278556
0.9154	High Similarity	NPC262359
0.9147	High Similarity	NPC39753
0.9147	High Similarity	NPC115998
0.9147	High Similarity	NPC84772
0.9141	High Similarity	NPC293453
0.9118	High Similarity	NPC59739
0.9118	High Similarity	NPC62840
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	NPC214236
0.9118	High Similarity	NPC299080
0.9118	High Similarity	NPC204469
0.9118	High Similarity	NPC78803
0.9111	High Similarity	NPC477272
0.9111	High Similarity	NPC475680
0.9111	High Similarity	NPC69769
0.9111	High Similarity	NPC235239
0.9111	High Similarity	NPC284550
0.9111	High Similarity	NPC6407
0.9111	High Similarity	NPC275734
0.9111	High Similarity	NPC110228

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 NPC270369 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	442
0.1-0.2	1032
0.2-0.3	1760
0.3-0.4	2763
0.4-0.5	1706
0.5-0.6	1018
0.6-0.7	281
0.7-0.8	103
0.8-0.85	34
0.85-0.9	10
0.9-0.95	1
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)
0.9154	High Similarity	NPD1240	Approved
0.9104	High Similarity	NPD1549	Phase 2
0.9023	High Similarity	NPD1510	Phase 2
0.9015	High Similarity	NPD1607	Approved
0.8986	High Similarity	NPD4378	Clinical (unspecified phase)
0.8963	High Similarity	NPD970	Clinical (unspecified phase)
0.8913	High Similarity	NPD1511	Approved
0.8849	High Similarity	NPD7410	Clinical (unspecified phase)
0.8786	High Similarity	NPD1512	Approved
0.8676	High Similarity	NPD2796	Approved
0.8623	High Similarity	NPD2800	Approved
0.8511	High Similarity	NPD6799	Approved
0.8493	Intermediate Similarity	NPD2801	Approved
0.8489	Intermediate Similarity	NPD1243	Approved
0.845	Intermediate Similarity	NPD422	Phase 1
0.8429	Intermediate Similarity	NPD3750	Approved
0.8425	Intermediate Similarity	NPD1934	Approved
0.8406	Intermediate Similarity	NPD1551	Phase 2
0.8385	Intermediate Similarity	NPD9717	Approved
0.8367	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8356	Intermediate Similarity	NPD7411	Suspended
0.8333	Intermediate Similarity	NPD1203	Approved
0.8321	Intermediate Similarity	NPD6651	Approved
0.8311	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8298	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8296	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8288	Intermediate Similarity	NPD4380	Phase 2
0.8255	Intermediate Similarity	NPD3882	Suspended
0.82	Intermediate Similarity	NPD7075	Discontinued
0.82	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8176	Intermediate Similarity	NPD6801	Discontinued
0.8163	Intermediate Similarity	NPD6599	Discontinued
0.8121	Intermediate Similarity	NPD7819	Suspended
0.8121	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8085	Intermediate Similarity	NPD2344	Approved
0.8082	Intermediate Similarity	NPD920	Approved
0.8079	Intermediate Similarity	NPD3749	Approved
0.8071	Intermediate Similarity	NPD3748	Approved
0.8067	Intermediate Similarity	NPD3817	Phase 2
0.8056	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD1548	Phase 1
0.7972	Intermediate Similarity	NPD2654	Approved
0.7972	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7959	Intermediate Similarity	NPD5403	Approved
0.7945	Intermediate Similarity	NPD2534	Approved
0.7945	Intermediate Similarity	NPD2532	Approved
0.7945	Intermediate Similarity	NPD5401	Approved
0.7945	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7945	Intermediate Similarity	NPD2533	Approved
0.7922	Intermediate Similarity	NPD6959	Discontinued
0.7914	Intermediate Similarity	NPD943	Approved
0.7899	Intermediate Similarity	NPD1296	Phase 2
0.7895	Intermediate Similarity	NPD7768	Phase 2
0.7887	Intermediate Similarity	NPD6099	Approved
0.7887	Intermediate Similarity	NPD6100	Approved
0.7885	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7885	Intermediate Similarity	NPD6166	Phase 2
0.7885	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7885	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7863	Intermediate Similarity	NPD9545	Approved
0.7862	Intermediate Similarity	NPD2309	Approved
0.7848	Intermediate Similarity	NPD7054	Approved
0.7848	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7846	Intermediate Similarity	NPD9493	Approved
0.7817	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7817	Intermediate Similarity	NPD2799	Discontinued
0.7799	Intermediate Similarity	NPD7472	Approved
0.7785	Intermediate Similarity	NPD3818	Discontinued
0.777	Intermediate Similarity	NPD3268	Approved
0.777	Intermediate Similarity	NPD2313	Discontinued
0.777	Intermediate Similarity	NPD411	Approved
0.7762	Intermediate Similarity	NPD2935	Discontinued
0.7761	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7754	Intermediate Similarity	NPD6832	Phase 2
0.7752	Intermediate Similarity	NPD1241	Discontinued
0.775	Intermediate Similarity	NPD6797	Phase 2
0.773	Intermediate Similarity	NPD230	Phase 1
0.773	Intermediate Similarity	NPD447	Suspended
0.7721	Intermediate Similarity	NPD3225	Approved
0.7702	Intermediate Similarity	NPD7251	Discontinued
0.7688	Intermediate Similarity	NPD7074	Phase 3
0.7677	Intermediate Similarity	NPD919	Approved
0.7671	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7664	Intermediate Similarity	NPD2797	Approved
0.7662	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD7808	Phase 3
0.7654	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD5953	Discontinued
0.763	Intermediate Similarity	NPD1610	Phase 2
0.7626	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7625	Intermediate Similarity	NPD7286	Phase 2
0.7609	Intermediate Similarity	NPD1019	Discontinued
0.7609	Intermediate Similarity	NPD2798	Approved
0.7597	Intermediate Similarity	NPD5402	Approved
0.758	Intermediate Similarity	NPD1247	Approved
0.7574	Intermediate Similarity	NPD1608	Approved
0.7569	Intermediate Similarity	NPD7033	Discontinued
0.7569	Intermediate Similarity	NPD4308	Phase 3
0.7569	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD4628	Phase 3
0.7546	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7536	Intermediate Similarity	NPD3267	Approved
0.7536	Intermediate Similarity	NPD3266	Approved
0.7532	Intermediate Similarity	NPD6232	Discontinued
0.7532	Intermediate Similarity	NPD1465	Phase 2
0.7516	Intermediate Similarity	NPD5494	Approved
0.75	Intermediate Similarity	NPD3226	Approved
0.75	Intermediate Similarity	NPD7473	Discontinued
0.75	Intermediate Similarity	NPD4908	Phase 1
0.7445	Intermediate Similarity	NPD1481	Phase 2
0.7429	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD7390	Discontinued
0.7394	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD4749	Approved
0.7378	Intermediate Similarity	NPD6559	Discontinued
0.7376	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD3926	Phase 2
0.7372	Intermediate Similarity	NPD4288	Approved
0.7372	Intermediate Similarity	NPD1535	Discovery
0.7364	Intermediate Similarity	NPD9266	Approved
0.7364	Intermediate Similarity	NPD74	Approved
0.7362	Intermediate Similarity	NPD1729	Discontinued
0.7361	Intermediate Similarity	NPD5124	Phase 1
0.7361	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7361	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7361	Intermediate Similarity	NPD1933	Approved
0.7353	Intermediate Similarity	NPD17	Approved
0.7347	Intermediate Similarity	NPD2346	Discontinued
0.7319	Intermediate Similarity	NPD3972	Approved
0.7312	Intermediate Similarity	NPD5711	Approved
0.7312	Intermediate Similarity	NPD5710	Approved
0.7292	Intermediate Similarity	NPD4307	Phase 2
0.7287	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7287	Intermediate Similarity	NPD9264	Approved
0.7287	Intermediate Similarity	NPD9263	Approved
0.7287	Intermediate Similarity	NPD9267	Approved
0.7273	Intermediate Similarity	NPD6104	Discontinued
0.7261	Intermediate Similarity	NPD2296	Approved
0.7248	Intermediate Similarity	NPD1652	Phase 2
0.7246	Intermediate Similarity	NPD1201	Approved
0.723	Intermediate Similarity	NPD1471	Phase 3
0.7222	Intermediate Similarity	NPD2403	Approved
0.7212	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD4363	Phase 3
0.7209	Intermediate Similarity	NPD4360	Phase 2
0.7195	Intermediate Similarity	NPD5844	Phase 1
0.7194	Intermediate Similarity	NPD9269	Phase 2
0.7185	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7183	Intermediate Similarity	NPD9494	Approved
0.7172	Intermediate Similarity	NPD3142	Approved
0.7172	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD3140	Approved
0.7172	Intermediate Similarity	NPD1613	Approved
0.7168	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD4361	Phase 2
0.7165	Intermediate Similarity	NPD940	Approved
0.7165	Intermediate Similarity	NPD846	Approved
0.7163	Intermediate Similarity	NPD1164	Approved
0.7163	Intermediate Similarity	NPD1470	Approved
0.7153	Intermediate Similarity	NPD3764	Approved
0.7153	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD9268	Approved
0.7152	Intermediate Similarity	NPD2354	Approved
0.7143	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD1778	Approved
0.7083	Intermediate Similarity	NPD4625	Phase 3
0.708	Intermediate Similarity	NPD1894	Discontinued
0.7076	Intermediate Similarity	NPD4287	Approved
0.707	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD9281	Approved
0.7034	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD6798	Discontinued
0.7013	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD9697	Approved
0.7	Intermediate Similarity	NPD2353	Approved
0.6977	Remote Similarity	NPD9261	Approved
0.6972	Remote Similarity	NPD1876	Approved
0.6948	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD5940	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD3751	Discontinued
0.6918	Remote Similarity	NPD6844	Discontinued
0.6903	Remote Similarity	NPD4661	Approved
0.6903	Remote Similarity	NPD4662	Approved
0.6899	Remote Similarity	NPD6585	Discontinued
0.6894	Remote Similarity	NPD290	Approved
0.6892	Remote Similarity	NPD6355	Discontinued
0.6887	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD1653	Approved
0.6879	Remote Similarity	NPD1091	Approved
0.6871	Remote Similarity	NPD6233	Phase 2
0.6871	Remote Similarity	NPD520	Approved
0.6864	Remote Similarity	NPD3658	Clinical (unspecified phase)
0.6861	Remote Similarity	NPD6671	Approved
0.6859	Remote Similarity	NPD5049	Phase 3
0.6855	Remote Similarity	NPD5890	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