NPASS Compound

Structure

NPC474960 OpenBabel07101718292D 26 29 0 0 0 0 0 0 0 0999 V2000 -0.2588 -1.9659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7934 -0.3912 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 2.0000 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 6.9282 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -1.5000 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 6.9282 -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 -0.0000 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 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 0.5000 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 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 1.5000 0.0000 O 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 4.3301 -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 20 1 0 0 0 0 2 20 1 0 0 0 0 3 4 2 0 0 0 0 3 11 1 0 0 0 0 4 14 1 0 0 0 0 5 6 1 0 0 0 0 5 12 1 0 0 0 0 6 20 1 0 0 0 0 7 10 2 0 0 0 0 7 15 1 0 0 0 0 8 10 1 0 0 0 0 8 16 2 0 0 0 0 9 13 2 0 0 0 0 9 25 1 0 0 0 0 10 21 1 0 0 0 0 11 12 2 0 0 0 0 11 13 1 0 0 0 0 12 19 1 0 0 0 0 13 18 1 0 0 0 0 14 19 2 0 0 0 0 14 22 1 0 0 0 0 15 17 2 0 0 0 0 15 23 1 0 0 0 0 16 17 1 0 0 0 0 16 25 1 0 0 0 0 17 18 1 0 0 0 0 18 24 2 0 0 0 0 19 26 1 0 0 0 0 20 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	354.11
Volume:	351.9
LogP:	4.11
LogD:	3.0
LogS:	-4.033
# Rotatable Bonds:	1
TPSA:	100.13
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.616
Synthetic Accessibility Score:	2.943
Fsp3:	0.25
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.84
MDCK Permeability:	1.585082100064028e-05
Pgp-inhibitor:	0.005
Pgp-substrate:	0.037
Human Intestinal Absorption (HIA):	0.016
20% Bioavailability (F20%):	0.013
30% Bioavailability (F30%):	0.005

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.009
Plasma Protein Binding (PPB):	99.21784973144531%
Volume Distribution (VD):	0.468
Pgp-substrate:	1.2250601053237915%

ADMET: Metabolism

CYP1A2-inhibitor:	0.944
CYP1A2-substrate:	0.642
CYP2C19-inhibitor:	0.783
CYP2C19-substrate:	0.055
CYP2C9-inhibitor:	0.786
CYP2C9-substrate:	0.947
CYP2D6-inhibitor:	0.802
CYP2D6-substrate:	0.573
CYP3A4-inhibitor:	0.386
CYP3A4-substrate:	0.112

ADMET: Excretion

Clearance (CL):	4.849
Half-life (T1/2):	0.73

ADMET: Toxicity

hERG Blockers:	0.026
Human Hepatotoxicity (H-HT):	0.203
Drug-inuced Liver Injury (DILI):	0.219
AMES Toxicity:	0.198
Rat Oral Acute Toxicity:	0.482
Maximum Recommended Daily Dose:	0.678
Skin Sensitization:	0.869
Carcinogencity:	0.198
Eye Corrosion:	0.004
Eye Irritation:	0.684
Respiratory Toxicity:	0.13

Download Data

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

Natural Product: NPC474960

Natural Product ID:	NPC474960
*Common Name:**	5,7-Dihydroxy-3-(8-Hydroxy-2,2-Dimethyl-3,4-Dihydrochromen-5-Yl)Chromen-4-One
IUPAC Name:	5,7-dihydroxy-3-(8-hydroxy-2,2-dimethyl-3,4-dihydrochromen-5-yl)chromen-4-one
Synonyms:
Standard InCHIKey:	CFGUDCVYJGCIHR-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C20H18O6/c1-20(2)6-5-12-11(3-4-14(22)19(12)26-20)13-9-25-16-8-10(21)7-15(23)17(16)18(13)24/h3-4,7-9,21-23H,5-6H2,1-2H3
SMILES:	Oc1cc(O)c2c(c1)occ(c2=O)c1ccc(c2c1CCC(O2)(C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL490311
PubChem CID:	11494111
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002506] Isoflavonoids [CHEMONTID:0002901] Isoflav-2-enes [CHEMONTID:0000494] Isoflavones [CHEMONTID:0003580] 2'-prenylated isoflavones

*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
NPO11841	Psorothamnus arborescens	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[16441066]
NPO11841	Psorothamnus arborescens	Species	Fabaceae	Eukaryota	root	n.a.	n.a.	PMID[16441066]
NPO11841	Psorothamnus arborescens	Species	Fabaceae	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	3

Activity Type	# Activity
Cell Line	1
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT306	Cell Line	PC-3	Homo sapiens	IC50	=	107000.0	nM	PMID[558760]
NPT633	Organism	Leishmania donovani	Leishmania donovani	IC50	=	38400.0	nM	PMID[558760]
NPT471	Organism	Trypanosoma brucei brucei	Trypanosoma brucei brucei	IC50	=	57900.0	nM	PMID[558760]

☑ 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 NPC474960 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	429
0.1-0.2	1859
0.2-0.3	4404
0.3-0.4	11031
0.4-0.5	6864
0.5-0.6	3567
0.6-0.7	5117
0.7-0.8	5210
0.8-0.85	2458
0.85-0.9	1319
0.9-0.95	405
0.95-1	34

Similarity Score	Similarity Level	Natural Product ID
0.9737	High Similarity	NPC472963
0.9677	High Similarity	NPC186686
0.9671	High Similarity	NPC472907
0.9669	High Similarity	NPC472905
0.9615	High Similarity	NPC303174
0.9613	High Similarity	NPC472964
0.961	High Similarity	NPC472902
0.961	High Similarity	NPC471973
0.9608	High Similarity	NPC52889
0.9554	High Similarity	NPC43319
0.9545	High Similarity	NPC74178
0.9545	High Similarity	NPC184755
0.9545	High Similarity	NPC204879
0.9542	High Similarity	NPC24640
0.9539	High Similarity	NPC469550
0.9494	High Similarity	NPC218226
0.949	High Similarity	NPC239752
0.949	High Similarity	NPC472450
0.949	High Similarity	NPC275780
0.949	High Similarity	NPC293319
0.9487	High Similarity	NPC474150
0.9487	High Similarity	NPC474162
0.9484	High Similarity	NPC36217
0.9484	High Similarity	NPC139036
0.9484	High Similarity	NPC118256
0.9484	High Similarity	NPC192686
0.9484	High Similarity	NPC119209
0.9481	High Similarity	NPC474681
0.9481	High Similarity	NPC218313
0.9481	High Similarity	NPC67876
0.9481	High Similarity	NPC129684
0.9481	High Similarity	NPC136674
0.9481	High Similarity	NPC299520
0.9477	High Similarity	NPC234255
0.9477	High Similarity	NPC67396
0.9474	High Similarity	NPC477231
0.9474	High Similarity	NPC257648
0.9474	High Similarity	NPC472912
0.9474	High Similarity	NPC260979
0.947	High Similarity	NPC85131
0.943	High Similarity	NPC477517
0.943	High Similarity	NPC39091
0.9427	High Similarity	NPC23298
0.9427	High Similarity	NPC189473
0.9423	High Similarity	NPC57715
0.9423	High Similarity	NPC472906
0.9423	High Similarity	NPC474038
0.9423	High Similarity	NPC234644
0.9419	High Similarity	NPC474290
0.9419	High Similarity	NPC476242
0.9419	High Similarity	NPC55738
0.9419	High Similarity	NPC280680
0.9416	High Similarity	NPC282307
0.9416	High Similarity	NPC133970
0.9416	High Similarity	NPC6633
0.9416	High Similarity	NPC170026
0.9416	High Similarity	NPC5322
0.9416	High Similarity	NPC472455
0.9412	High Similarity	NPC18727
0.9408	High Similarity	NPC31363
0.9363	High Similarity	NPC474034
0.9363	High Similarity	NPC474033
0.9363	High Similarity	NPC229632
0.9363	High Similarity	NPC201800
0.9363	High Similarity	NPC472448
0.9363	High Similarity	NPC83922
0.9363	High Similarity	NPC329760
0.9359	High Similarity	NPC200746
0.9359	High Similarity	NPC475784
0.9359	High Similarity	NPC188433
0.9355	High Similarity	NPC291508
0.9355	High Similarity	NPC473272
0.9355	High Similarity	NPC241904
0.9355	High Similarity	NPC27337
0.9355	High Similarity	NPC300727
0.9355	High Similarity	NPC284820
0.9355	High Similarity	NPC111969
0.9351	High Similarity	NPC117992
0.9351	High Similarity	NPC168247
0.9351	High Similarity	NPC255807
0.9351	High Similarity	NPC200246
0.9351	High Similarity	NPC472280
0.9351	High Similarity	NPC152951
0.9351	High Similarity	NPC31018
0.9351	High Similarity	NPC57674
0.9351	High Similarity	NPC230149
0.9351	High Similarity	NPC256925
0.9346	High Similarity	NPC60972
0.9346	High Similarity	NPC39732
0.9346	High Similarity	NPC219582
0.9346	High Similarity	NPC236637
0.9346	High Similarity	NPC474993
0.9346	High Similarity	NPC237994
0.9346	High Similarity	NPC302950
0.9342	High Similarity	NPC151473
0.9342	High Similarity	NPC29231
0.9338	High Similarity	NPC139364
0.9338	High Similarity	NPC194653
0.9338	High Similarity	NPC203747
0.9338	High Similarity	NPC80710
0.9338	High Similarity	NPC254702
0.9313	High Similarity	NPC288813
0.9308	High Similarity	NPC472449
0.9308	High Similarity	NPC272502
0.9308	High Similarity	NPC37870
0.9304	High Similarity	NPC472625
0.9304	High Similarity	NPC248638
0.9304	High Similarity	NPC236521
0.9304	High Similarity	NPC152659
0.9304	High Similarity	NPC475985
0.9299	High Similarity	NPC167678
0.9299	High Similarity	NPC26326
0.9299	High Similarity	NPC471210
0.9299	High Similarity	NPC173137
0.9299	High Similarity	NPC61010
0.9299	High Similarity	NPC472632
0.9299	High Similarity	NPC29876
0.9299	High Similarity	NPC134783
0.9295	High Similarity	NPC235448
0.9295	High Similarity	NPC210459
0.929	High Similarity	NPC471985
0.929	High Similarity	NPC472916
0.929	High Similarity	NPC274730
0.929	High Similarity	NPC474638
0.929	High Similarity	NPC470600
0.929	High Similarity	NPC291878
0.929	High Similarity	NPC278778
0.929	High Similarity	NPC35038
0.929	High Similarity	NPC195796
0.9286	High Similarity	NPC33051
0.9286	High Similarity	NPC227337
0.9286	High Similarity	NPC141212
0.9286	High Similarity	NPC49402
0.9286	High Similarity	NPC273462
0.9286	High Similarity	NPC70433
0.9281	High Similarity	NPC154345
0.9281	High Similarity	NPC256406
0.9276	High Similarity	NPC183950
0.9276	High Similarity	NPC40290
0.9276	High Similarity	NPC139293
0.9276	High Similarity	NPC177298
0.9276	High Similarity	NPC264550
0.9276	High Similarity	NPC137062
0.9276	High Similarity	NPC69430
0.9276	High Similarity	NPC195763
0.9276	High Similarity	NPC264289
0.9276	High Similarity	NPC200060
0.9276	High Similarity	NPC52005
0.9276	High Similarity	NPC223579
0.9276	High Similarity	NPC333691
0.9276	High Similarity	NPC287101
0.9276	High Similarity	NPC48479
0.9276	High Similarity	NPC142876
0.9276	High Similarity	NPC105512
0.9272	High Similarity	NPC95864
0.925	High Similarity	NPC117854
0.925	High Similarity	NPC474024
0.925	High Similarity	NPC6588
0.925	High Similarity	NPC477154
0.925	High Similarity	NPC476306
0.925	High Similarity	NPC150131
0.9245	High Similarity	NPC62261
0.9245	High Similarity	NPC234052
0.9245	High Similarity	NPC224280
0.9241	High Similarity	NPC476247
0.9241	High Similarity	NPC261470
0.9241	High Similarity	NPC25152
0.9236	High Similarity	NPC472624
0.9236	High Similarity	NPC204290
0.9236	High Similarity	NPC56085
0.9236	High Similarity	NPC299436
0.9236	High Similarity	NPC228785
0.9236	High Similarity	NPC14353
0.9236	High Similarity	NPC328102
0.9236	High Similarity	NPC28241
0.9236	High Similarity	NPC470183
0.9236	High Similarity	NPC174953
0.9236	High Similarity	NPC321399
0.9236	High Similarity	NPC476980
0.9231	High Similarity	NPC472598
0.9231	High Similarity	NPC219867
0.9231	High Similarity	NPC161960
0.9231	High Similarity	NPC210084
0.9231	High Similarity	NPC475267
0.9231	High Similarity	NPC304008
0.9231	High Similarity	NPC222814
0.9231	High Similarity	NPC472910
0.9231	High Similarity	NPC78071
0.9231	High Similarity	NPC245758
0.9231	High Similarity	NPC474836
0.9231	High Similarity	NPC469584
0.9231	High Similarity	NPC181960
0.9231	High Similarity	NPC52530
0.9231	High Similarity	NPC474208
0.9231	High Similarity	NPC472911
0.9231	High Similarity	NPC471515
0.9231	High Similarity	NPC156057
0.9231	High Similarity	NPC187745
0.9231	High Similarity	NPC96167
0.9231	High Similarity	NPC162869

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 NPC474960 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	407
0.1-0.2	985
0.2-0.3	1743
0.3-0.4	2675
0.4-0.5	1769
0.5-0.6	987
0.6-0.7	408
0.7-0.8	119
0.8-0.85	37
0.85-0.9	18
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9346	High Similarity	NPD1934	Approved
0.9161	High Similarity	NPD2393	Clinical (unspecified phase)
0.9161	High Similarity	NPD2801	Approved
0.9045	High Similarity	NPD3882	Suspended
0.9006	High Similarity	NPD6167	Clinical (unspecified phase)
0.9006	High Similarity	NPD6168	Clinical (unspecified phase)
0.9006	High Similarity	NPD6166	Phase 2
0.8947	High Similarity	NPD1511	Approved
0.8841	High Similarity	NPD7054	Approved
0.8831	High Similarity	NPD1512	Approved
0.8788	High Similarity	NPD7074	Phase 3
0.8788	High Similarity	NPD7472	Approved
0.878	High Similarity	NPD3818	Discontinued
0.8742	High Similarity	NPD3817	Phase 2
0.8726	High Similarity	NPD4380	Phase 2
0.8688	High Similarity	NPD4868	Clinical (unspecified phase)
0.8679	High Similarity	NPD7819	Suspended
0.8642	High Similarity	NPD5494	Approved
0.8634	High Similarity	NPD4381	Clinical (unspecified phase)
0.8623	High Similarity	NPD6797	Phase 2
0.8618	High Similarity	NPD1549	Phase 2
0.8571	High Similarity	NPD7251	Discontinued
0.8562	High Similarity	NPD1465	Phase 2
0.8553	High Similarity	NPD1552	Clinical (unspecified phase)
0.8553	High Similarity	NPD1550	Clinical (unspecified phase)
0.8543	High Similarity	NPD1510	Phase 2
0.8526	High Similarity	NPD7410	Clinical (unspecified phase)
0.8526	High Similarity	NPD4378	Clinical (unspecified phase)
0.8521	High Similarity	NPD4338	Clinical (unspecified phase)
0.8521	High Similarity	NPD7808	Phase 3
0.8519	High Similarity	NPD7075	Discontinued
0.8503	High Similarity	NPD5844	Phase 1
0.8487	Intermediate Similarity	NPD2796	Approved
0.8447	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8424	Intermediate Similarity	NPD6232	Discontinued
0.8395	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8387	Intermediate Similarity	NPD3750	Approved
0.8383	Intermediate Similarity	NPD7473	Discontinued
0.8364	Intermediate Similarity	NPD6959	Discontinued
0.8344	Intermediate Similarity	NPD6799	Approved
0.8323	Intermediate Similarity	NPD7411	Suspended
0.8293	Intermediate Similarity	NPD3749	Approved
0.8278	Intermediate Similarity	NPD1240	Approved
0.8272	Intermediate Similarity	NPD6801	Discontinued
0.8261	Intermediate Similarity	NPD6599	Discontinued
0.8258	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8187	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8176	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.817	Intermediate Similarity	NPD1607	Approved
0.8158	Intermediate Similarity	NPD943	Approved
0.8107	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8075	Intermediate Similarity	NPD5403	Approved
0.8065	Intermediate Similarity	NPD3748	Approved
0.8061	Intermediate Similarity	NPD5402	Approved
0.8047	Intermediate Similarity	NPD3926	Phase 2
0.8024	Intermediate Similarity	NPD919	Approved
0.8012	Intermediate Similarity	NPD7768	Phase 2
0.795	Intermediate Similarity	NPD5401	Approved
0.7931	Intermediate Similarity	NPD6559	Discontinued
0.7929	Intermediate Similarity	NPD1247	Approved
0.7929	Intermediate Similarity	NPD7199	Phase 2
0.7923	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7922	Intermediate Similarity	NPD1613	Approved
0.7922	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7907	Intermediate Similarity	NPD3751	Discontinued
0.7898	Intermediate Similarity	NPD6100	Approved
0.7898	Intermediate Similarity	NPD6099	Approved
0.7895	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7853	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.784	Intermediate Similarity	NPD2533	Approved
0.784	Intermediate Similarity	NPD2532	Approved
0.784	Intermediate Similarity	NPD2534	Approved
0.7836	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7834	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7829	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7812	Intermediate Similarity	NPD4628	Phase 3
0.7785	Intermediate Similarity	NPD1551	Phase 2
0.7778	Intermediate Similarity	NPD3787	Discontinued
0.7756	Intermediate Similarity	NPD230	Phase 1
0.7753	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.775	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7735	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD3027	Phase 3
0.7722	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7706	Intermediate Similarity	NPD6234	Discontinued
0.7677	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7673	Intermediate Similarity	NPD2935	Discontinued
0.7662	Intermediate Similarity	NPD4908	Phase 1
0.7651	Intermediate Similarity	NPD3226	Approved
0.7643	Intermediate Similarity	NPD447	Suspended
0.7643	Intermediate Similarity	NPD1933	Approved
0.764	Intermediate Similarity	NPD2800	Approved
0.7627	Intermediate Similarity	NPD7685	Pre-registration
0.7625	Intermediate Similarity	NPD2346	Discontinued
0.7625	Intermediate Similarity	NPD2344	Approved
0.76	Intermediate Similarity	NPD7228	Approved
0.7597	Intermediate Similarity	NPD9494	Approved
0.7593	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD1653	Approved
0.7584	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7566	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7564	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD7390	Discontinued
0.7542	Intermediate Similarity	NPD8313	Approved
0.7542	Intermediate Similarity	NPD8312	Approved
0.7531	Intermediate Similarity	NPD1243	Approved
0.753	Intermediate Similarity	NPD920	Approved
0.7515	Intermediate Similarity	NPD37	Approved
0.75	Intermediate Similarity	NPD4625	Phase 3
0.75	Intermediate Similarity	NPD2799	Discontinued
0.75	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD4965	Approved
0.7485	Intermediate Similarity	NPD4966	Approved
0.7485	Intermediate Similarity	NPD4967	Phase 2
0.7472	Intermediate Similarity	NPD5953	Discontinued
0.7447	Intermediate Similarity	NPD6778	Approved
0.7447	Intermediate Similarity	NPD6780	Approved
0.7447	Intermediate Similarity	NPD6776	Approved
0.7447	Intermediate Similarity	NPD6782	Approved
0.7447	Intermediate Similarity	NPD6781	Approved
0.7447	Intermediate Similarity	NPD6777	Approved
0.7447	Intermediate Similarity	NPD6779	Approved
0.744	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD2309	Approved
0.7439	Intermediate Similarity	NPD6190	Approved
0.7434	Intermediate Similarity	NPD1610	Phase 2
0.7434	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7427	Intermediate Similarity	NPD4288	Approved
0.7419	Intermediate Similarity	NPD2798	Approved
0.7418	Intermediate Similarity	NPD8150	Discontinued
0.741	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD7033	Discontinued
0.738	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD6651	Approved
0.7371	Intermediate Similarity	NPD5710	Approved
0.7371	Intermediate Similarity	NPD5711	Approved
0.7366	Intermediate Similarity	NPD4363	Phase 3
0.7366	Intermediate Similarity	NPD4360	Phase 2
0.736	Intermediate Similarity	NPD7286	Phase 2
0.7355	Intermediate Similarity	NPD1203	Approved
0.7342	Intermediate Similarity	NPD3268	Approved
0.7342	Intermediate Similarity	NPD2313	Discontinued
0.7337	Intermediate Similarity	NPD4287	Approved
0.733	Intermediate Similarity	NPD7435	Discontinued
0.733	Intermediate Similarity	NPD5242	Approved
0.7325	Intermediate Similarity	NPD6832	Phase 2
0.7322	Intermediate Similarity	NPD8434	Phase 2
0.732	Intermediate Similarity	NPD8151	Discontinued
0.7306	Intermediate Similarity	NPD7584	Approved
0.7293	Intermediate Similarity	NPD7549	Discontinued
0.7285	Intermediate Similarity	NPD1548	Phase 1
0.7284	Intermediate Similarity	NPD4308	Phase 3
0.725	Intermediate Similarity	NPD4060	Phase 1
0.7244	Intermediate Similarity	NPD1470	Approved
0.7244	Intermediate Similarity	NPD2797	Approved
0.724	Intermediate Similarity	NPD7698	Approved
0.724	Intermediate Similarity	NPD7697	Approved
0.724	Intermediate Similarity	NPD7696	Phase 3
0.7239	Intermediate Similarity	NPD5404	Approved
0.7239	Intermediate Similarity	NPD5405	Approved
0.7239	Intermediate Similarity	NPD5406	Approved
0.7239	Intermediate Similarity	NPD5408	Approved
0.7235	Intermediate Similarity	NPD7458	Discontinued
0.7233	Intermediate Similarity	NPD3764	Approved
0.7226	Intermediate Similarity	NPD4749	Approved
0.7209	Intermediate Similarity	NPD6844	Discontinued
0.7208	Intermediate Similarity	NPD1201	Approved
0.7205	Intermediate Similarity	NPD5124	Phase 1
0.7205	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD7870	Phase 2
0.7202	Intermediate Similarity	NPD7871	Phase 2
0.7188	Intermediate Similarity	NPD6823	Phase 2
0.7181	Intermediate Similarity	NPD6534	Approved
0.7181	Intermediate Similarity	NPD6535	Approved
0.7179	Intermediate Similarity	NPD7701	Phase 2
0.7175	Intermediate Similarity	NPD7229	Phase 3
0.7169	Intermediate Similarity	NPD8166	Discontinued
0.7161	Intermediate Similarity	NPD1608	Approved
0.7161	Intermediate Similarity	NPD9717	Approved
0.716	Intermediate Similarity	NPD6273	Approved
0.7157	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7157	Intermediate Similarity	NPD7783	Phase 2
0.7143	Intermediate Similarity	NPD7240	Approved
0.7143	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4361	Phase 2
0.7135	Intermediate Similarity	NPD2494	Approved
0.7135	Intermediate Similarity	NPD2493	Approved
0.7126	Intermediate Similarity	NPD5353	Approved
0.7125	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD6798	Discontinued
0.7119	Intermediate Similarity	NPD8127	Discontinued
0.7111	Intermediate Similarity	NPD7177	Discontinued
0.7107	Intermediate Similarity	NPD7874	Approved
0.7107	Intermediate Similarity	NPD7875	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