NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	220.07
Volume:	220.974
LogP:	2.443
LogD:	1.906
LogS:	-2.563
# Rotatable Bonds:	1
TPSA:	59.67
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.799
Synthetic Accessibility Score:	2.393
Fsp3:	0.25
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:	-4.772
MDCK Permeability:	1.3349497749004513e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.723
Human Intestinal Absorption (HIA):	0.014
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.044

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.085
Plasma Protein Binding (PPB):	86.12378692626953%
Volume Distribution (VD):	0.737
Pgp-substrate:	13.875116348266602%

ADMET: Metabolism

CYP1A2-inhibitor:	0.94
CYP1A2-substrate:	0.971
CYP2C19-inhibitor:	0.315
CYP2C19-substrate:	0.836
CYP2C9-inhibitor:	0.287
CYP2C9-substrate:	0.834
CYP2D6-inhibitor:	0.063
CYP2D6-substrate:	0.87
CYP3A4-inhibitor:	0.11
CYP3A4-substrate:	0.394

ADMET: Excretion

Clearance (CL):	5.501
Half-life (T1/2):	0.539

ADMET: Toxicity

hERG Blockers:	0.014
Human Hepatotoxicity (H-HT):	0.1
Drug-inuced Liver Injury (DILI):	0.401
AMES Toxicity:	0.434
Rat Oral Acute Toxicity:	0.215
Maximum Recommended Daily Dose:	0.344
Skin Sensitization:	0.647
Carcinogencity:	0.099
Eye Corrosion:	0.022
Eye Irritation:	0.942
Respiratory Toxicity:	0.305

Download Data

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

Natural Product: NPC125920

Natural Product ID:	NPC125920
*Common Name:**	Eugenitin
IUPAC Name:	5-hydroxy-7-methoxy-2,6-dimethylchromen-4-one
Synonyms:
Standard InCHIKey:	RGTSAUBIQAKKLC-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C12H12O4/c1-6-4-8(13)11-10(16-6)5-9(15-3)7(2)12(11)14/h4-5,14H,1-3H3
SMILES:	COc1cc2oc(C)cc(=O)c2c(c1C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3104955
PubChem CID:	3083581
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
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1402962]
NPO140	Coriaria japonica	Species	Coriariaceae	Eukaryota	n.a.	fruit	n.a.	PMID[16079545]
NPO17398	Cyperus teneriffae	Species	Cyperaceae	Eukaryota	n.a.	root	n.a.	PMID[21504148]
NPO501	Mycoleptodiscus indicus	Species	Magnaporthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24387625]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	Flower Buds	n.a.	n.a.	PMID[26977531]
NPO8622	Stauntonia hexaphylla	Species	Lardizabalaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[31301930]
NPO6783	Avrainvillea rawsonii	Species	Udoteaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7964790]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8904847]
NPO8622	Stauntonia hexaphylla	Species	Lardizabalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	Bark	n.a.	n.a.	Database[FooDB]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	Essential Oil	n.a.	n.a.	Database[FooDB]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	Stem	n.a.	n.a.	Database[FooDB]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO8622	Stauntonia hexaphylla	Species	Lardizabalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1934	Strychnos triplinervia	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1032	Piper attenuatum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9776	Tellima grandifolia	Species	Saxifragaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7626	Damnacanthus major	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO140	Coriaria japonica	Species	Coriariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1934	Strychnos triplinervia	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9776	Tellima grandifolia	Species	Saxifragaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO577	Lactifluus subvellereus	Species	Russulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1032	Piper attenuatum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8622	Stauntonia hexaphylla	Species	Lardizabalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7626	Damnacanthus major	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO140	Coriaria japonica	Species	Coriariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO140	Coriaria japonica	Species	Coriariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9776	Tellima grandifolia	Species	Saxifragaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO30949	Eugenia caryopyhllata	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO2395	Siphonaria australis	Species	Siphonariidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO501	Mycoleptodiscus indicus	Species	Magnaporthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17398	Cyperus teneriffae	Species	Cyperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6072	Andinobates bombetes	Species	Dendrobatidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1032	Piper attenuatum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12409	Artemisia jacutica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1934	Strychnos triplinervia	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5834	Pellicularia sasakii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO6041	Lithocolletis coryli	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO2562	Thymus membranaceus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4504	Cassia jahnii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9456	Rubus sanctus	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6783	Avrainvillea rawsonii	Species	Udoteaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15735	Galeocerdo arcticus	Species	Carcharhinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9718	Cyphelium chrysocephalum	Species	Caliciaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1456	Bersama abyssinica	Species	Melianthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO140	Coriaria japonica	Species	Coriariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7383	Puccinia lagenophorae	Species	Pucciniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO577	Lactifluus subvellereus	Species	Russulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7626	Damnacanthus major	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8622	Stauntonia hexaphylla	Species	Lardizabalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO173	Aconitum sajanense	Species	Ranunculaceae	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
IC50	7
LD50	1

Activity Type	# Activity
Cell Line	4
NON-MOLECULAR	1
Organism	2
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT399	Cell Line	SF-295	Homo sapiens	IC50	>	113000.0	nM	PMID[469795]
NPT306	Cell Line	PC-3	Homo sapiens	IC50	>	113000.0	nM	PMID[469795]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	113000.0	nM	PMID[469795]
NPT400	Cell Line	MDA-MB-435	Homo sapiens	IC50	>	113000.0	nM	PMID[469795]
NPT27	Others	Unspecified		IC50	>	113000.0	nM	PMID[469795]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	113000.0	nM	PMID[469795]
NPT633	Organism	Leishmania donovani	Leishmania donovani	IC50	>	181000.0	nM	PMID[469795]
NPT841	Organism	Leishmania major	Leishmania major	LD50	=	39.9	uM	PMID[469795]

☑ 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 NPC125920 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	395
0.1-0.2	1861
0.2-0.3	5029
0.3-0.4	12354
0.4-0.5	5344
0.5-0.6	4654
0.6-0.7	5632
0.7-0.8	4045
0.8-0.85	1891
0.85-0.9	1078
0.9-0.95	386
0.95-1	28

Similarity Score	Similarity Level	Natural Product ID
0.9922	High Similarity	NPC60667
0.9922	High Similarity	NPC93756
0.9922	High Similarity	NPC108113
0.9846	High Similarity	NPC174999
0.9766	High Similarity	NPC475589
0.9766	High Similarity	NPC31872
0.9766	High Similarity	NPC473584
0.9697	High Similarity	NPC131130
0.969	High Similarity	NPC25937
0.9688	High Similarity	NPC5515
0.9688	High Similarity	NPC270369
0.9624	High Similarity	NPC139554
0.9624	High Similarity	NPC78913
0.9624	High Similarity	NPC18260
0.9624	High Similarity	NPC23257
0.9624	High Similarity	NPC471697
0.9618	High Similarity	NPC151113
0.9615	High Similarity	NPC223457
0.9552	High Similarity	NPC159275
0.9552	High Similarity	NPC471587
0.9552	High Similarity	NPC241100
0.9549	High Similarity	NPC470668
0.9549	High Similarity	NPC201395
0.9549	High Similarity	NPC470669
0.9545	High Similarity	NPC156910
0.9538	High Similarity	NPC10971
0.9531	High Similarity	NPC230818
0.9481	High Similarity	NPC282300
0.9481	High Similarity	NPC110969
0.9478	High Similarity	NPC217186
0.9478	High Similarity	NPC96565
0.9478	High Similarity	NPC220062
0.9478	High Similarity	NPC216978
0.9478	High Similarity	NPC55018
0.9478	High Similarity	NPC53181
0.9478	High Similarity	NPC473076
0.9478	High Similarity	NPC301217
0.9478	High Similarity	NPC303633
0.947	High Similarity	NPC101752
0.9457	High Similarity	NPC84772
0.9412	High Similarity	NPC226636
0.9412	High Similarity	NPC11561
0.9407	High Similarity	NPC261227
0.9407	High Similarity	NPC270883
0.9407	High Similarity	NPC150522
0.9407	High Similarity	NPC172986
0.9403	High Similarity	NPC470671
0.9403	High Similarity	NPC474504
0.9403	High Similarity	NPC470672
0.9403	High Similarity	NPC474487
0.9398	High Similarity	NPC231772
0.9398	High Similarity	NPC127447
0.9398	High Similarity	NPC29353
0.9398	High Similarity	NPC124784
0.9398	High Similarity	NPC47815
0.9398	High Similarity	NPC234133
0.9398	High Similarity	NPC473887
0.9398	High Similarity	NPC194281
0.9394	High Similarity	NPC236974
0.9394	High Similarity	NPC144027
0.9389	High Similarity	NPC203817
0.9385	High Similarity	NPC324482
0.938	High Similarity	NPC69235
0.938	High Similarity	NPC212379
0.9375	High Similarity	NPC475496
0.9375	High Similarity	NPC49852
0.9375	High Similarity	NPC305518
0.9375	High Similarity	NPC128428
0.9343	High Similarity	NPC242100
0.9343	High Similarity	NPC255133
0.9343	High Similarity	NPC158874
0.9338	High Similarity	NPC4743
0.9338	High Similarity	NPC3188
0.9338	High Similarity	NPC213322
0.9338	High Similarity	NPC103362
0.9338	High Similarity	NPC324386
0.9338	High Similarity	NPC258630
0.9338	High Similarity	NPC156590
0.9338	High Similarity	NPC147688
0.9338	High Similarity	NPC205006
0.9338	High Similarity	NPC17170
0.9338	High Similarity	NPC118840
0.9338	High Similarity	NPC156190
0.9338	High Similarity	NPC312391
0.9338	High Similarity	NPC279650
0.9338	High Similarity	NPC166689
0.9338	High Similarity	NPC64908
0.9338	High Similarity	NPC96408
0.9333	High Similarity	NPC37206
0.9328	High Similarity	NPC266597
0.9328	High Similarity	NPC332594
0.9328	High Similarity	NPC250266
0.9323	High Similarity	NPC13575
0.9318	High Similarity	NPC78540
0.9318	High Similarity	NPC50898
0.9318	High Similarity	NPC213216
0.9318	High Similarity	NPC274121
0.9313	High Similarity	NPC27490
0.9302	High Similarity	NPC473907
0.9275	High Similarity	NPC311741
0.9275	High Similarity	NPC216538
0.9275	High Similarity	NPC297788
0.9275	High Similarity	NPC224714
0.9275	High Similarity	NPC234629
0.9275	High Similarity	NPC273538
0.9275	High Similarity	NPC319752
0.927	High Similarity	NPC162476
0.927	High Similarity	NPC76338
0.927	High Similarity	NPC324134
0.927	High Similarity	NPC293852
0.927	High Similarity	NPC161506
0.927	High Similarity	NPC217083
0.927	High Similarity	NPC328164
0.927	High Similarity	NPC325346
0.927	High Similarity	NPC148757
0.927	High Similarity	NPC296917
0.927	High Similarity	NPC324436
0.927	High Similarity	NPC66515
0.927	High Similarity	NPC182852
0.927	High Similarity	NPC177354
0.927	High Similarity	NPC37496
0.927	High Similarity	NPC40833
0.927	High Similarity	NPC78803
0.927	High Similarity	NPC166934
0.927	High Similarity	NPC306829
0.927	High Similarity	NPC299080
0.927	High Similarity	NPC473042
0.927	High Similarity	NPC1089
0.927	High Similarity	NPC220998
0.927	High Similarity	NPC265040
0.927	High Similarity	NPC194432
0.927	High Similarity	NPC214236
0.927	High Similarity	NPC227579
0.927	High Similarity	NPC223500
0.927	High Similarity	NPC64915
0.927	High Similarity	NPC166482
0.927	High Similarity	NPC107572
0.927	High Similarity	NPC10937
0.927	High Similarity	NPC76372
0.927	High Similarity	NPC78
0.927	High Similarity	NPC204469
0.927	High Similarity	NPC59739
0.927	High Similarity	NPC125855
0.927	High Similarity	NPC32739
0.927	High Similarity	NPC200694
0.927	High Similarity	NPC228504
0.927	High Similarity	NPC167624
0.927	High Similarity	NPC62840
0.9265	High Similarity	NPC477272
0.9265	High Similarity	NPC305355
0.9265	High Similarity	NPC307990
0.9265	High Similarity	NPC16455
0.9265	High Similarity	NPC235239
0.9265	High Similarity	NPC69769
0.9265	High Similarity	NPC475680
0.9259	High Similarity	NPC124269
0.9254	High Similarity	NPC150399
0.9254	High Similarity	NPC168105
0.9254	High Similarity	NPC470397
0.9254	High Similarity	NPC13408
0.9254	High Similarity	NPC274109
0.9254	High Similarity	NPC186838
0.9254	High Similarity	NPC477243
0.9254	High Similarity	NPC470398
0.9254	High Similarity	NPC66349
0.9254	High Similarity	NPC98115
0.9254	High Similarity	NPC477244
0.9254	High Similarity	NPC187826
0.9254	High Similarity	NPC477242
0.9254	High Similarity	NPC12165
0.9254	High Similarity	NPC41461
0.9254	High Similarity	NPC25287
0.9254	High Similarity	NPC1486
0.9254	High Similarity	NPC249606
0.9248	High Similarity	NPC172262
0.9248	High Similarity	NPC103842
0.9248	High Similarity	NPC164136
0.9242	High Similarity	NPC229646
0.9237	High Similarity	NPC250057
0.9231	High Similarity	NPC473894
0.9209	High Similarity	NPC306488
0.9209	High Similarity	NPC301276
0.9209	High Similarity	NPC214774
0.9209	High Similarity	NPC470458
0.9209	High Similarity	NPC195621
0.9209	High Similarity	NPC476088
0.9209	High Similarity	NPC312973
0.9209	High Similarity	NPC142405
0.9209	High Similarity	NPC20488
0.9209	High Similarity	NPC176229
0.9209	High Similarity	NPC178343
0.9209	High Similarity	NPC246948
0.9209	High Similarity	NPC67805
0.9209	High Similarity	NPC474161
0.9209	High Similarity	NPC88964
0.9209	High Similarity	NPC54577
0.9209	High Similarity	NPC111786
0.9209	High Similarity	NPC470647
0.9209	High Similarity	NPC267375
0.9209	High Similarity	NPC475052

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 NPC125920 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	397
0.1-0.2	1003
0.2-0.3	1666
0.3-0.4	2767
0.4-0.5	1756
0.5-0.6	1072
0.6-0.7	328
0.7-0.8	109
0.8-0.85	35
0.85-0.9	14
0.9-0.95	3
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9275	High Similarity	NPD4378	Clinical (unspecified phase)
0.9185	High Similarity	NPD1552	Clinical (unspecified phase)
0.9185	High Similarity	NPD1550	Clinical (unspecified phase)
0.9167	High Similarity	NPD1240	Approved
0.9118	High Similarity	NPD1549	Phase 2
0.9037	High Similarity	NPD1510	Phase 2
0.903	High Similarity	NPD1607	Approved
0.9	High Similarity	NPD7410	Clinical (unspecified phase)
0.8841	High Similarity	NPD970	Clinical (unspecified phase)
0.8777	High Similarity	NPD2800	Approved
0.8696	High Similarity	NPD2796	Approved
0.8662	High Similarity	NPD1511	Approved
0.8643	High Similarity	NPD1243	Approved
0.8639	High Similarity	NPD2393	Clinical (unspecified phase)
0.863	High Similarity	NPD7411	Suspended
0.8613	High Similarity	NPD6651	Approved
0.8581	High Similarity	NPD8443	Clinical (unspecified phase)
0.8562	High Similarity	NPD4380	Phase 2
0.8542	High Similarity	NPD1512	Approved
0.8467	Intermediate Similarity	NPD7075	Discontinued
0.8446	Intermediate Similarity	NPD6801	Discontinued
0.8446	Intermediate Similarity	NPD1934	Approved
0.8403	Intermediate Similarity	NPD6799	Approved
0.8389	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8389	Intermediate Similarity	NPD2801	Approved
0.8389	Intermediate Similarity	NPD7819	Suspended
0.8356	Intermediate Similarity	NPD920	Approved
0.8333	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8322	Intermediate Similarity	NPD3750	Approved
0.8298	Intermediate Similarity	NPD1551	Phase 2
0.8252	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8224	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8219	Intermediate Similarity	NPD2533	Approved
0.8219	Intermediate Similarity	NPD2534	Approved
0.8219	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8219	Intermediate Similarity	NPD2532	Approved
0.8195	Intermediate Similarity	NPD422	Phase 1
0.8194	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8188	Intermediate Similarity	NPD6599	Discontinued
0.8188	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD6959	Discontinued
0.8158	Intermediate Similarity	NPD7768	Phase 2
0.8158	Intermediate Similarity	NPD3882	Suspended
0.8141	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8134	Intermediate Similarity	NPD9717	Approved
0.8101	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8088	Intermediate Similarity	NPD1203	Approved
0.8042	Intermediate Similarity	NPD2935	Discontinued
0.7987	Intermediate Similarity	NPD3749	Approved
0.7986	Intermediate Similarity	NPD2344	Approved
0.7974	Intermediate Similarity	NPD3817	Phase 2
0.7972	Intermediate Similarity	NPD2799	Discontinued
0.7972	Intermediate Similarity	NPD3748	Approved
0.7972	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7935	Intermediate Similarity	NPD919	Approved
0.7929	Intermediate Similarity	NPD2313	Discontinued
0.7911	Intermediate Similarity	NPD6166	Phase 2
0.7911	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7911	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7901	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD1548	Phase 1
0.7888	Intermediate Similarity	NPD5953	Discontinued
0.7877	Intermediate Similarity	NPD2654	Approved
0.7875	Intermediate Similarity	NPD7286	Phase 2
0.7867	Intermediate Similarity	NPD5403	Approved
0.7852	Intermediate Similarity	NPD5401	Approved
0.7834	Intermediate Similarity	NPD1247	Approved
0.7817	Intermediate Similarity	NPD943	Approved
0.7812	Intermediate Similarity	NPD3818	Discontinued
0.7801	Intermediate Similarity	NPD1296	Phase 2
0.7794	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7793	Intermediate Similarity	NPD6100	Approved
0.7793	Intermediate Similarity	NPD6099	Approved
0.7785	Intermediate Similarity	NPD6232	Discontinued
0.7771	Intermediate Similarity	NPD5494	Approved
0.777	Intermediate Similarity	NPD2309	Approved
0.7764	Intermediate Similarity	NPD7054	Approved
0.7761	Intermediate Similarity	NPD9545	Approved
0.775	Intermediate Similarity	NPD7473	Discontinued
0.7744	Intermediate Similarity	NPD9493	Approved
0.7716	Intermediate Similarity	NPD7472	Approved
0.7716	Intermediate Similarity	NPD7074	Phase 3
0.7703	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7676	Intermediate Similarity	NPD3268	Approved
0.7676	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7669	Intermediate Similarity	NPD6797	Phase 2
0.7664	Intermediate Similarity	NPD1610	Phase 2
0.766	Intermediate Similarity	NPD6832	Phase 2
0.7652	Intermediate Similarity	NPD1241	Discontinued
0.7647	Intermediate Similarity	NPD3226	Approved
0.7639	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7639	Intermediate Similarity	NPD5124	Phase 1
0.7639	Intermediate Similarity	NPD230	Phase 1
0.7622	Intermediate Similarity	NPD6559	Discontinued
0.7622	Intermediate Similarity	NPD7251	Discontinued
0.7607	Intermediate Similarity	NPD1729	Discontinued
0.7603	Intermediate Similarity	NPD7033	Discontinued
0.7584	Intermediate Similarity	NPD4628	Phase 3
0.7576	Intermediate Similarity	NPD7808	Phase 3
0.7571	Intermediate Similarity	NPD2797	Approved
0.7562	Intermediate Similarity	NPD5711	Approved
0.7562	Intermediate Similarity	NPD5710	Approved
0.7552	Intermediate Similarity	NPD411	Approved
0.755	Intermediate Similarity	NPD7390	Discontinued
0.7535	Intermediate Similarity	NPD4908	Phase 1
0.7518	Intermediate Similarity	NPD1019	Discontinued
0.7518	Intermediate Similarity	NPD2798	Approved
0.7517	Intermediate Similarity	NPD447	Suspended
0.7516	Intermediate Similarity	NPD5402	Approved
0.75	Intermediate Similarity	NPD2346	Discontinued
0.75	Intermediate Similarity	NPD3225	Approved
0.7483	Intermediate Similarity	NPD4308	Phase 3
0.7482	Intermediate Similarity	NPD1608	Approved
0.747	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD1465	Phase 2
0.7447	Intermediate Similarity	NPD3266	Approved
0.7447	Intermediate Similarity	NPD3267	Approved
0.7442	Intermediate Similarity	NPD4360	Phase 2
0.7442	Intermediate Similarity	NPD4363	Phase 3
0.7439	Intermediate Similarity	NPD5844	Phase 1
0.7413	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD3926	Phase 2
0.7399	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7399	Intermediate Similarity	NPD4361	Phase 2
0.7365	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7357	Intermediate Similarity	NPD3972	Approved
0.7356	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7343	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7324	Intermediate Similarity	NPD1164	Approved
0.7319	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD4749	Approved
0.7305	Intermediate Similarity	NPD6104	Discontinued
0.7296	Intermediate Similarity	NPD4288	Approved
0.7292	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7286	Intermediate Similarity	NPD1201	Approved
0.7279	Intermediate Similarity	NPD1933	Approved
0.7279	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD1471	Phase 3
0.7266	Intermediate Similarity	NPD17	Approved
0.7256	Intermediate Similarity	NPD2403	Approved
0.7246	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD4625	Phase 3
0.7234	Intermediate Similarity	NPD1481	Phase 2
0.7211	Intermediate Similarity	NPD1613	Approved
0.7211	Intermediate Similarity	NPD4307	Phase 2
0.7211	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD1470	Approved
0.7192	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD2296	Approved
0.7179	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD1652	Phase 2
0.7163	Intermediate Similarity	NPD1535	Discovery
0.7152	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD74	Approved
0.7143	Intermediate Similarity	NPD9266	Approved
0.7107	Intermediate Similarity	NPD5889	Approved
0.7107	Intermediate Similarity	NPD5890	Approved
0.7105	Intermediate Similarity	NPD2424	Discontinued
0.7103	Intermediate Similarity	NPD9494	Approved
0.7095	Intermediate Similarity	NPD3140	Approved
0.7095	Intermediate Similarity	NPD3142	Approved
0.7089	Intermediate Similarity	NPD7458	Discontinued
0.7078	Intermediate Similarity	NPD2354	Approved
0.7077	Intermediate Similarity	NPD940	Approved
0.7077	Intermediate Similarity	NPD846	Approved
0.7075	Intermediate Similarity	NPD6798	Discontinued
0.7075	Intermediate Similarity	NPD3764	Approved
0.7068	Intermediate Similarity	NPD9264	Approved
0.7068	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD9263	Approved
0.7068	Intermediate Similarity	NPD9267	Approved
0.7051	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD6585	Discontinued
0.7039	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD6002	Phase 3
0.7039	Intermediate Similarity	NPD6005	Phase 3
0.7039	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD6004	Phase 3
0.7039	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD7229	Phase 3
0.7021	Intermediate Similarity	NPD1778	Approved
0.7014	Intermediate Similarity	NPD1283	Approved
0.7014	Intermediate Similarity	NPD1876	Approved
0.7013	Intermediate Similarity	NPD7003	Approved
0.7011	Intermediate Similarity	NPD4287	Approved
0.7006	Intermediate Similarity	NPD5049	Phase 3
0.7	Intermediate Similarity	NPD1894	Discontinued
0.6995	Remote Similarity	NPD7584	Approved
0.6993	Remote Similarity	NPD9269	Phase 2
0.6987	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD4476	Approved
0.6974	Remote Similarity	NPD5408	Approved
0.6974	Remote Similarity	NPD5404	Approved
0.6974	Remote Similarity	NPD5406	Approved
0.6974	Remote Similarity	NPD4477	Approved
0.6974	Remote Similarity	NPD5405	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