NPASS Compound

Structure

NPC471982 OpenBabel07101718292D 32 34 0 0 0 0 0 0 0 0999 V2000 -2.5981 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 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 -5.1962 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -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 -2.5981 -2.5000 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 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -4.0000 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 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.0000 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 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -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 3.4641 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 0.5000 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 14 1 0 0 0 0 2 14 1 0 0 0 0 3 15 1 0 0 0 0 4 15 1 0 0 0 0 5 31 1 0 0 0 0 6 8 1 0 0 0 0 6 14 2 0 0 0 0 7 9 1 0 0 0 0 7 15 2 0 0 0 0 8 16 1 0 0 0 0 9 18 1 0 0 0 0 10 16 2 0 0 0 0 10 17 1 0 0 0 0 11 17 2 0 0 0 0 11 22 1 0 0 0 0 12 19 2 0 0 0 0 12 20 1 0 0 0 0 13 21 1 0 0 0 0 13 23 2 0 0 0 0 16 25 1 0 0 0 0 17 23 1 0 0 0 0 18 19 1 0 0 0 0 18 26 2 0 0 0 0 19 27 1 0 0 0 0 20 24 2 0 0 0 0 20 28 1 0 0 0 0 21 24 1 0 0 0 0 21 29 2 0 0 0 0 22 25 2 0 0 0 0 22 30 1 0 0 0 0 23 32 1 0 0 0 0 24 26 1 0 0 0 0 25 31 1 0 0 0 0 26 32 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	436.19
Volume:	458.959
LogP:	6.681
LogD:	3.651
LogS:	-2.547
# Rotatable Bonds:	6
TPSA:	100.13
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.435
Synthetic Accessibility Score:	3.148
Fsp3:	0.269
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:	-4.921
MDCK Permeability:	1.25901633509784e-05
Pgp-inhibitor:	0.796
Pgp-substrate:	0.882
Human Intestinal Absorption (HIA):	0.235
20% Bioavailability (F20%):	0.984
30% Bioavailability (F30%):	0.979

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001
Plasma Protein Binding (PPB):	85.37471771240234%
Volume Distribution (VD):	1.016
Pgp-substrate:	13.502718925476074%

ADMET: Metabolism

CYP1A2-inhibitor:	0.848
CYP1A2-substrate:	0.357
CYP2C19-inhibitor:	0.932
CYP2C19-substrate:	0.06
CYP2C9-inhibitor:	0.871
CYP2C9-substrate:	0.898
CYP2D6-inhibitor:	0.748
CYP2D6-substrate:	0.253
CYP3A4-inhibitor:	0.293
CYP3A4-substrate:	0.098

ADMET: Excretion

Clearance (CL):	8.262
Half-life (T1/2):	0.26

ADMET: Toxicity

hERG Blockers:	0.026
Human Hepatotoxicity (H-HT):	0.912
Drug-inuced Liver Injury (DILI):	0.886
AMES Toxicity:	0.225
Rat Oral Acute Toxicity:	0.224
Maximum Recommended Daily Dose:	0.421
Skin Sensitization:	0.921
Carcinogencity:	0.06
Eye Corrosion:	0.003
Eye Irritation:	0.646
Respiratory Toxicity:	0.687

Download Data

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

Natural Product: NPC471982

Natural Product ID:	NPC471982
*Common Name:**	HOPYPXDRQYCVEL-UHFFFAOYSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	HOPYPXDRQYCVEL-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C26H28O6/c1-14(2)6-8-16-10-17(11-22(30)25(16)31-5)23-13-21(29)24-20(28)12-19(27)18(26(24)32-23)9-7-15(3)4/h6-7,10-13,27-28,30H,8-9H2,1-5H3
SMILES:	CC(=CCC1=C(C(=CC(=C1)C2=CC(=O)C3=C(C=C(C(=C3O2)CC=C(C)C)O)O)O)OC)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3314706
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001615] Flavones [CHEMONTID:0003504] 8-prenylated flavones

*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
NPO23024	Epimedium koreanum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12081149]
NPO23024	Epimedium koreanum	Species	Berberidaceae	Eukaryota	n.a.	root	n.a.	PMID[22051934]
NPO23024	Epimedium koreanum	Species	Berberidaceae	Eukaryota	aerial parts	herbal garden of Chungbuk National University, Cheongju, Korea	2012-Oct	PMID[24963714]
NPO23024	Epimedium koreanum	Species	Berberidaceae	Eukaryota	n.a.	aerial part	n.a.	Database[Article]
NPO23024	Epimedium koreanum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23024	Epimedium koreanum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23024	Epimedium koreanum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO23024	Epimedium koreanum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO23024	Epimedium koreanum	Species	Berberidaceae	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	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	16800.0	nM	PMID[502926]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	8800.0	nM	PMID[502926]

☑ 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 NPC471982 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	434
0.1-0.2	1773
0.2-0.3	4499
0.3-0.4	10782
0.4-0.5	7118
0.5-0.6	3556
0.6-0.7	4825
0.7-0.8	4850
0.8-0.85	2387
0.85-0.9	1544
0.9-0.95	791
0.95-1	138

Similarity Score	Similarity Level	Natural Product ID
0.9793	High Similarity	NPC177298
0.9793	High Similarity	NPC48479
0.973	High Similarity	NPC45849
0.973	High Similarity	NPC200761
0.973	High Similarity	NPC477503
0.973	High Similarity	NPC234255
0.973	High Similarity	NPC470327
0.9726	High Similarity	NPC3825
0.9726	High Similarity	NPC88804
0.9724	High Similarity	NPC120464
0.9664	High Similarity	NPC195796
0.9664	High Similarity	NPC470328
0.9664	High Similarity	NPC291878
0.9664	High Similarity	NPC472455
0.9664	High Similarity	NPC278778
0.9664	High Similarity	NPC209614
0.9664	High Similarity	NPC35038
0.9664	High Similarity	NPC472626
0.9664	High Similarity	NPC471985
0.966	High Similarity	NPC205046
0.966	High Similarity	NPC59162
0.966	High Similarity	NPC304295
0.9658	High Similarity	NPC52005
0.9658	High Similarity	NPC223579
0.9658	High Similarity	NPC287101
0.9658	High Similarity	NPC183950
0.9658	High Similarity	NPC137062
0.9655	High Similarity	NPC33265
0.9655	High Similarity	NPC62536
0.9603	High Similarity	NPC476980
0.9603	High Similarity	NPC192686
0.9603	High Similarity	NPC118256
0.9603	High Similarity	NPC246478
0.9603	High Similarity	NPC119209
0.96	High Similarity	NPC472598
0.96	High Similarity	NPC291508
0.96	High Similarity	NPC474055
0.96	High Similarity	NPC223787
0.96	High Similarity	NPC262286
0.96	High Similarity	NPC52889
0.96	High Similarity	NPC78225
0.96	High Similarity	NPC27337
0.96	High Similarity	NPC36852
0.9597	High Similarity	NPC152951
0.9597	High Similarity	NPC133392
0.9597	High Similarity	NPC472280
0.9597	High Similarity	NPC168247
0.9597	High Similarity	NPC117992
0.9597	High Similarity	NPC230149
0.9597	High Similarity	NPC57674
0.9595	High Similarity	NPC106976
0.9595	High Similarity	NPC39732
0.9595	High Similarity	NPC249570
0.9595	High Similarity	NPC37684
0.9595	High Similarity	NPC237994
0.9595	High Similarity	NPC60972
0.9595	High Similarity	NPC157784
0.9595	High Similarity	NPC63187
0.9589	High Similarity	NPC195202
0.9539	High Similarity	NPC474038
0.9539	High Similarity	NPC26326
0.9539	High Similarity	NPC258331
0.9536	High Similarity	NPC184755
0.9536	High Similarity	NPC204879
0.9536	High Similarity	NPC74178
0.9533	High Similarity	NPC138243
0.9533	High Similarity	NPC191146
0.9533	High Similarity	NPC68093
0.953	High Similarity	NPC255350
0.953	High Similarity	NPC273462
0.953	High Similarity	NPC274327
0.953	High Similarity	NPC22519
0.953	High Similarity	NPC270620
0.953	High Similarity	NPC145379
0.953	High Similarity	NPC69394
0.953	High Similarity	NPC160951
0.953	High Similarity	NPC176775
0.953	High Similarity	NPC162351
0.953	High Similarity	NPC227337
0.953	High Similarity	NPC74924
0.953	High Similarity	NPC179126
0.953	High Similarity	NPC476631
0.953	High Similarity	NPC192083
0.953	High Similarity	NPC58382
0.953	High Similarity	NPC170492
0.953	High Similarity	NPC70433
0.953	High Similarity	NPC298692
0.953	High Similarity	NPC213896
0.953	High Similarity	NPC75279
0.953	High Similarity	NPC183878
0.953	High Similarity	NPC47781
0.953	High Similarity	NPC18727
0.953	High Similarity	NPC236223
0.953	High Similarity	NPC49402
0.953	High Similarity	NPC231018
0.953	High Similarity	NPC276409
0.953	High Similarity	NPC250822
0.953	High Similarity	NPC78326
0.953	High Similarity	NPC33051
0.9527	High Similarity	NPC133953
0.9527	High Similarity	NPC256406
0.9527	High Similarity	NPC125062
0.9527	High Similarity	NPC54394
0.9527	High Similarity	NPC252933
0.9527	High Similarity	NPC28274
0.9527	High Similarity	NPC200740
0.9527	High Similarity	NPC50403
0.9527	High Similarity	NPC154345
0.9524	High Similarity	NPC328119
0.9521	High Similarity	NPC12200
0.9521	High Similarity	NPC108406
0.9477	High Similarity	NPC83922
0.9477	High Similarity	NPC472448
0.9477	High Similarity	NPC474162
0.9477	High Similarity	NPC474150
0.9477	High Similarity	NPC81679
0.9474	High Similarity	NPC472624
0.9474	High Similarity	NPC472631
0.9474	High Similarity	NPC174953
0.9474	High Similarity	NPC475784
0.9474	High Similarity	NPC228785
0.9474	High Similarity	NPC282009
0.9474	High Similarity	NPC36217
0.9474	High Similarity	NPC328102
0.9474	High Similarity	NPC14353
0.9474	High Similarity	NPC56085
0.9474	High Similarity	NPC287328
0.9474	High Similarity	NPC472630
0.9474	High Similarity	NPC470326
0.9474	High Similarity	NPC204290
0.947	High Similarity	NPC476981
0.947	High Similarity	NPC218313
0.947	High Similarity	NPC284820
0.947	High Similarity	NPC473272
0.947	High Similarity	NPC474681
0.9467	High Similarity	NPC92659
0.9467	High Similarity	NPC134287
0.9467	High Similarity	NPC130589
0.9467	High Similarity	NPC163780
0.9467	High Similarity	NPC208197
0.9467	High Similarity	NPC213622
0.9467	High Similarity	NPC4455
0.9467	High Similarity	NPC2476
0.9467	High Similarity	NPC146165
0.9467	High Similarity	NPC256925
0.9467	High Similarity	NPC138360
0.9467	High Similarity	NPC226025
0.9467	High Similarity	NPC280339
0.9467	High Similarity	NPC20830
0.9467	High Similarity	NPC183597
0.9467	High Similarity	NPC128863
0.9467	High Similarity	NPC321779
0.9467	High Similarity	NPC113906
0.9467	High Similarity	NPC50715
0.9467	High Similarity	NPC196439
0.9467	High Similarity	NPC167815
0.9467	High Similarity	NPC227325
0.9467	High Similarity	NPC256612
0.9467	High Similarity	NPC201136
0.9463	High Similarity	NPC71334
0.9463	High Similarity	NPC82325
0.9463	High Similarity	NPC241498
0.9463	High Similarity	NPC219582
0.9463	High Similarity	NPC302950
0.9463	High Similarity	NPC188203
0.9463	High Similarity	NPC100887
0.9463	High Similarity	NPC472912
0.9463	High Similarity	NPC236637
0.9463	High Similarity	NPC120163
0.9463	High Similarity	NPC83508
0.9463	High Similarity	NPC222830
0.9463	High Similarity	NPC301323
0.9463	High Similarity	NPC275836
0.9463	High Similarity	NPC198826
0.9463	High Similarity	NPC293183
0.9463	High Similarity	NPC187498
0.9463	High Similarity	NPC162313
0.9463	High Similarity	NPC212678
0.9463	High Similarity	NPC279989
0.9463	High Similarity	NPC123886
0.9463	High Similarity	NPC131624
0.9463	High Similarity	NPC55205
0.9463	High Similarity	NPC57030
0.9463	High Similarity	NPC25270
0.9463	High Similarity	NPC275722
0.9463	High Similarity	NPC156222
0.9463	High Similarity	NPC239128
0.9463	High Similarity	NPC256283
0.9459	High Similarity	NPC50728
0.9459	High Similarity	NPC219330
0.9459	High Similarity	NPC166753
0.9459	High Similarity	NPC338131
0.9456	High Similarity	NPC238279
0.9456	High Similarity	NPC166036
0.9456	High Similarity	NPC203077
0.9416	High Similarity	NPC270837
0.9416	High Similarity	NPC470459
0.9416	High Similarity	NPC472625
0.9416	High Similarity	NPC186686
0.9412	High Similarity	NPC471212

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 NPC471982 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	387
0.1-0.2	955
0.2-0.3	1817
0.3-0.4	2679
0.4-0.5	1768
0.5-0.6	971
0.6-0.7	397
0.7-0.8	111
0.8-0.85	41
0.85-0.9	15
0.9-0.95	8
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.953	High Similarity	NPD2801	Approved
0.953	High Similarity	NPD2393	Clinical (unspecified phase)
0.9463	High Similarity	NPD1934	Approved
0.9315	High Similarity	NPD1511	Approved
0.9189	High Similarity	NPD1512	Approved
0.9122	High Similarity	NPD4378	Clinical (unspecified phase)
0.9026	High Similarity	NPD3882	Suspended
0.8987	High Similarity	NPD6166	Phase 2
0.8987	High Similarity	NPD6168	Clinical (unspecified phase)
0.8987	High Similarity	NPD6167	Clinical (unspecified phase)
0.8961	High Similarity	NPD3817	Phase 2
0.8875	High Similarity	NPD3818	Discontinued
0.8824	High Similarity	NPD4380	Phase 2
0.882	High Similarity	NPD7054	Approved
0.8765	High Similarity	NPD7074	Phase 3
0.8765	High Similarity	NPD7472	Approved
0.8662	High Similarity	NPD4868	Clinical (unspecified phase)
0.8625	High Similarity	NPD6232	Discontinued
0.8618	High Similarity	NPD7410	Clinical (unspecified phase)
0.8616	High Similarity	NPD5494	Approved
0.8608	High Similarity	NPD7075	Discontinued
0.8598	High Similarity	NPD6797	Phase 2
0.858	High Similarity	NPD7473	Discontinued
0.8545	High Similarity	NPD7251	Discontinued
0.8535	High Similarity	NPD7096	Clinical (unspecified phase)
0.8523	High Similarity	NPD1550	Clinical (unspecified phase)
0.8523	High Similarity	NPD1552	Clinical (unspecified phase)
0.8514	High Similarity	NPD1510	Phase 2
0.8494	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8494	Intermediate Similarity	NPD7808	Phase 3
0.8491	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8471	Intermediate Similarity	NPD6801	Discontinued
0.8467	Intermediate Similarity	NPD1549	Phase 2
0.8456	Intermediate Similarity	NPD2796	Approved
0.8418	Intermediate Similarity	NPD7819	Suspended
0.8367	Intermediate Similarity	NPD1240	Approved
0.8365	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8364	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD6959	Discontinued
0.8312	Intermediate Similarity	NPD6799	Approved
0.8302	Intermediate Similarity	NPD1465	Phase 2
0.8291	Intermediate Similarity	NPD7411	Suspended
0.8255	Intermediate Similarity	NPD1607	Approved
0.8253	Intermediate Similarity	NPD5844	Phase 1
0.8243	Intermediate Similarity	NPD943	Approved
0.8224	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8221	Intermediate Similarity	NPD1247	Approved
0.821	Intermediate Similarity	NPD919	Approved
0.817	Intermediate Similarity	NPD2800	Approved
0.8155	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8151	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8113	Intermediate Similarity	NPD6599	Discontinued
0.8107	Intermediate Similarity	NPD6559	Discontinued
0.8095	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8092	Intermediate Similarity	NPD2935	Discontinued
0.8025	Intermediate Similarity	NPD2532	Approved
0.8025	Intermediate Similarity	NPD2534	Approved
0.8025	Intermediate Similarity	NPD2533	Approved
0.8025	Intermediate Similarity	NPD5402	Approved
0.8012	Intermediate Similarity	NPD3926	Phase 2
0.8	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD3750	Approved
0.8	Intermediate Similarity	NPD1613	Approved
0.7975	Intermediate Similarity	NPD7768	Phase 2
0.7964	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7947	Intermediate Similarity	NPD230	Phase 1
0.7935	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7935	Intermediate Similarity	NPD1243	Approved
0.7925	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7925	Intermediate Similarity	NPD5403	Approved
0.7919	Intermediate Similarity	NPD3027	Phase 3
0.7895	Intermediate Similarity	NPD6651	Approved
0.7829	Intermediate Similarity	NPD447	Suspended
0.7812	Intermediate Similarity	NPD920	Approved
0.7799	Intermediate Similarity	NPD5401	Approved
0.7792	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD6234	Discontinued
0.7748	Intermediate Similarity	NPD2313	Discontinued
0.7748	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7746	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD1551	Phase 2
0.7742	Intermediate Similarity	NPD6100	Approved
0.7742	Intermediate Similarity	NPD6099	Approved
0.7736	Intermediate Similarity	NPD7390	Discontinued
0.7736	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7716	Intermediate Similarity	NPD3226	Approved
0.7711	Intermediate Similarity	NPD3749	Approved
0.7692	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7684	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7679	Intermediate Similarity	NPD7199	Phase 2
0.7677	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD3748	Approved
0.7677	Intermediate Similarity	NPD2799	Discontinued
0.7673	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7658	Intermediate Similarity	NPD4628	Phase 3
0.7635	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.763	Intermediate Similarity	NPD5953	Discontinued
0.7616	Intermediate Similarity	NPD7286	Phase 2
0.7597	Intermediate Similarity	NPD1933	Approved
0.7588	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.758	Intermediate Similarity	NPD2346	Discontinued
0.758	Intermediate Similarity	NPD2344	Approved
0.7576	Intermediate Similarity	NPD37	Approved
0.755	Intermediate Similarity	NPD9494	Approved
0.7547	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7546	Intermediate Similarity	NPD1653	Approved
0.7545	Intermediate Similarity	NPD4966	Approved
0.7545	Intermediate Similarity	NPD4967	Phase 2
0.7545	Intermediate Similarity	NPD4965	Approved
0.7516	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7469	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7457	Intermediate Similarity	NPD7228	Approved
0.7432	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7427	Intermediate Similarity	NPD5711	Approved
0.7427	Intermediate Similarity	NPD5710	Approved
0.7418	Intermediate Similarity	NPD4363	Phase 3
0.7418	Intermediate Similarity	NPD4360	Phase 2
0.7417	Intermediate Similarity	NPD1203	Approved
0.7416	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD3268	Approved
0.7391	Intermediate Similarity	NPD2309	Approved
0.7391	Intermediate Similarity	NPD6190	Approved
0.7386	Intermediate Similarity	NPD4908	Phase 1
0.7368	Intermediate Similarity	NPD2798	Approved
0.7356	Intermediate Similarity	NPD3751	Discontinued
0.7347	Intermediate Similarity	NPD1548	Phase 1
0.7342	Intermediate Similarity	NPD7033	Discontinued
0.7338	Intermediate Similarity	NPD4625	Phase 3
0.7333	Intermediate Similarity	NPD9269	Phase 2
0.7326	Intermediate Similarity	NPD3787	Discontinued
0.7303	Intermediate Similarity	NPD8313	Approved
0.7303	Intermediate Similarity	NPD8312	Approved
0.7303	Intermediate Similarity	NPD2797	Approved
0.7288	Intermediate Similarity	NPD7685	Pre-registration
0.7283	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD4361	Phase 2
0.7283	Intermediate Similarity	NPD5242	Approved
0.7273	Intermediate Similarity	NPD6832	Phase 2
0.7267	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD1610	Phase 2
0.7267	Intermediate Similarity	NPD2654	Approved
0.7267	Intermediate Similarity	NPD422	Phase 1
0.7263	Intermediate Similarity	NPD7584	Approved
0.7261	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD2403	Approved
0.7233	Intermediate Similarity	NPD4308	Phase 3
0.7225	Intermediate Similarity	NPD7229	Phase 3
0.7219	Intermediate Similarity	NPD9717	Approved
0.7219	Intermediate Similarity	NPD1608	Approved
0.7208	Intermediate Similarity	NPD3018	Phase 2
0.7202	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD4060	Phase 1
0.7188	Intermediate Similarity	NPD8151	Discontinued
0.7186	Intermediate Similarity	NPD7458	Discontinued
0.7182	Intermediate Similarity	NPD8434	Phase 2
0.7179	Intermediate Similarity	NPD6798	Discontinued
0.7176	Intermediate Similarity	NPD5353	Approved
0.7171	Intermediate Similarity	NPD4749	Approved
0.7162	Intermediate Similarity	NPD5536	Phase 2
0.7152	Intermediate Similarity	NPD5124	Phase 1
0.7152	Intermediate Similarity	NPD1201	Approved
0.7152	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD6778	Approved
0.7128	Intermediate Similarity	NPD6780	Approved
0.7128	Intermediate Similarity	NPD6776	Approved
0.7128	Intermediate Similarity	NPD6782	Approved
0.7128	Intermediate Similarity	NPD6777	Approved
0.7128	Intermediate Similarity	NPD6781	Approved
0.7128	Intermediate Similarity	NPD6779	Approved
0.7124	Intermediate Similarity	NPD3225	Approved
0.7101	Intermediate Similarity	NPD6386	Approved
0.7101	Intermediate Similarity	NPD6385	Approved
0.7099	Intermediate Similarity	NPD2424	Discontinued
0.7091	Intermediate Similarity	NPD4357	Discontinued
0.7088	Intermediate Similarity	NPD8150	Discontinued
0.7083	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD5405	Approved
0.7081	Intermediate Similarity	NPD5404	Approved
0.7081	Intermediate Similarity	NPD5408	Approved
0.7081	Intermediate Similarity	NPD5406	Approved
0.7079	Intermediate Similarity	NPD1729	Discontinued
0.7078	Intermediate Similarity	NPD3266	Approved
0.7078	Intermediate Similarity	NPD3267	Approved
0.7078	Intermediate Similarity	NPD1470	Approved
0.7076	Intermediate Similarity	NPD4288	Approved
0.707	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD411	Approved
0.7067	Intermediate Similarity	NPD9268	Approved
0.7059	Intermediate Similarity	NPD6844	Discontinued
0.7059	Intermediate Similarity	NPD2982	Phase 2
0.7059	Intermediate Similarity	NPD2983	Phase 2
0.7055	Intermediate Similarity	NPD1652	Phase 2
0.7044	Intermediate Similarity	NPD6355	Discontinued
0.7025	Intermediate Similarity	NPD6233	Phase 2
0.702	Intermediate Similarity	NPD17	Approved
0.7018	Intermediate Similarity	NPD8455	Phase 2

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