NPASS Compound

Structure

NPC258331 OpenBabel07101718272D 26 28 0 0 0 0 0 0 0 0999 V2000 0.8660 1.5000 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 4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 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 1.7321 -2.0000 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 1.7321 1.0000 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 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 0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -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 1.7321 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 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 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 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 9 1 0 0 0 0 2 24 1 0 0 0 0 3 25 1 0 0 0 0 4 5 2 0 0 0 0 4 10 1 0 0 0 0 5 12 1 0 0 0 0 6 10 2 0 0 0 0 6 14 1 0 0 0 0 7 11 2 0 0 0 0 7 16 1 0 0 0 0 8 13 1 0 0 0 0 8 15 2 0 0 0 0 9 17 1 0 0 0 0 9 20 2 0 0 0 0 10 15 1 0 0 0 0 11 13 1 0 0 0 0 11 18 1 0 0 0 0 12 14 2 0 0 0 0 12 21 1 0 0 0 0 13 22 2 0 0 0 0 14 23 1 0 0 0 0 15 26 1 0 0 0 0 16 19 2 0 0 0 0 16 24 1 0 0 0 0 17 18 2 0 0 0 0 17 19 1 0 0 0 0 18 26 1 0 0 0 0 19 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	356.09
Volume:	349.314
LogP:	2.908
LogD:	2.452
LogS:	-4.234
# Rotatable Bonds:	4
TPSA:	106.2
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.546
Synthetic Accessibility Score:	2.518
Fsp3:	0.158
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.807
MDCK Permeability:	1.812197115214076e-05
Pgp-inhibitor:	0.185
Pgp-substrate:	0.005
Human Intestinal Absorption (HIA):	0.074
20% Bioavailability (F20%):	0.009
30% Bioavailability (F30%):	0.913

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.011
Plasma Protein Binding (PPB):	87.61100006103516%
Volume Distribution (VD):	0.786
Pgp-substrate:	12.878582954406738%

ADMET: Metabolism

CYP1A2-inhibitor:	0.824
CYP1A2-substrate:	0.94
CYP2C19-inhibitor:	0.313
CYP2C19-substrate:	0.066
CYP2C9-inhibitor:	0.66
CYP2C9-substrate:	0.762
CYP2D6-inhibitor:	0.19
CYP2D6-substrate:	0.549
CYP3A4-inhibitor:	0.485
CYP3A4-substrate:	0.217

ADMET: Excretion

Clearance (CL):	5.078
Half-life (T1/2):	0.771

ADMET: Toxicity

hERG Blockers:	0.012
Human Hepatotoxicity (H-HT):	0.183
Drug-inuced Liver Injury (DILI):	0.965
AMES Toxicity:	0.298
Rat Oral Acute Toxicity:	0.214
Maximum Recommended Daily Dose:	0.714
Skin Sensitization:	0.267
Carcinogencity:	0.139
Eye Corrosion:	0.003
Eye Irritation:	0.484
Respiratory Toxicity:	0.457

Download Data

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

Natural Product: NPC258331

Natural Product ID:	NPC258331
*Common Name:**	Rugosaflavonoid B
IUPAC Name:	8-acetyl-2-(3,4-dihydroxyphenyl)-6,7-dimethoxychromen-4-one
Synonyms:
Standard InCHIKey:	NZKPEOCLCJZICW-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C19H16O7/c1-9(20)17-18-11(7-16(24-2)19(17)25-3)13(22)8-15(26-18)10-4-5-12(21)14(23)6-10/h4-8,21,23H,1-3H3
SMILES:	COc1c(OC)cc2c(c1C(=O)C)oc(cc2=O)c1ccc(c(c1)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2429883
PubChem CID:	72701894
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0002585] O-methylated flavonoids [CHEMONTID:0002592] 7-O-methylated flavonoids

*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
NPO1524	Rosa rugosa	Species	Rosaceae	Eukaryota	Flowers	n.a.	n.a.	DOI[10.1016/j.foodcont.2014.02.001]
NPO1524	Rosa rugosa	Species	Rosaceae	Eukaryota	Flowers	n.a.	n.a.	PMID[20467822]
NPO1524	Rosa rugosa	Species	Rosaceae	Eukaryota	flower buds	n.a.	n.a.	PMID[24063567]
NPO1524	Rosa rugosa	Species	Rosaceae	Eukaryota	Roots	n.a.	n.a.	PMID[24461297]
NPO1524	Rosa rugosa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1524	Rosa rugosa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1524	Rosa rugosa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO1524	Rosa rugosa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO1524	Rosa rugosa	Species	Rosaceae	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	5

Activity Type	# Activity
Cell Line	4
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	2800.0	nM	PMID[488081]
NPT306	Cell Line	PC-3	Homo sapiens	IC50	=	8400.0	nM	PMID[488081]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	1200.0	nM	PMID[488081]
NPT2678	Cell Line	NB-4	Homo sapiens	IC50	=	3600.0	nM	PMID[488081]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	4300.0	nM	PMID[488081]

☑ 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 NPC258331 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	1946
0.2-0.3	4986
0.3-0.4	11562
0.4-0.5	5864
0.5-0.6	3854
0.6-0.7	4981
0.7-0.8	4718
0.8-0.85	2177
0.85-0.9	1286
0.9-0.95	773
0.95-1	100

Similarity Score	Similarity Level	Natural Product ID
0.9804	High Similarity	NPC476980
0.9677	High Similarity	NPC472448
0.9677	High Similarity	NPC83922
0.9673	High Similarity	NPC78225
0.9673	High Similarity	NPC36852
0.9673	High Similarity	NPC262286
0.9673	High Similarity	NPC476981
0.9671	High Similarity	NPC256612
0.9671	High Similarity	NPC20830
0.9613	High Similarity	NPC167678
0.9613	High Similarity	NPC29876
0.9613	High Similarity	NPC259456
0.9608	High Similarity	NPC191146
0.9608	High Similarity	NPC472455
0.9608	High Similarity	NPC68093
0.9608	High Similarity	NPC138243
0.9605	High Similarity	NPC183878
0.9605	High Similarity	NPC231018
0.9605	High Similarity	NPC22519
0.9605	High Similarity	NPC255350
0.9605	High Similarity	NPC176775
0.9605	High Similarity	NPC274327
0.9605	High Similarity	NPC145379
0.9605	High Similarity	NPC47781
0.9605	High Similarity	NPC160951
0.9605	High Similarity	NPC69394
0.9551	High Similarity	NPC81679
0.9551	High Similarity	NPC261470
0.9548	High Similarity	NPC246478
0.9548	High Similarity	NPC204290
0.9542	High Similarity	NPC213622
0.9542	High Similarity	NPC113906
0.9542	High Similarity	NPC2476
0.9542	High Similarity	NPC208197
0.9542	High Similarity	NPC57674
0.9542	High Similarity	NPC138360
0.9542	High Similarity	NPC280339
0.9542	High Similarity	NPC39184
0.9542	High Similarity	NPC152951
0.9542	High Similarity	NPC130589
0.9542	High Similarity	NPC4455
0.9542	High Similarity	NPC230149
0.9542	High Similarity	NPC168247
0.9542	High Similarity	NPC50715
0.9542	High Similarity	NPC163780
0.9542	High Similarity	NPC183597
0.9542	High Similarity	NPC128863
0.9542	High Similarity	NPC234255
0.9542	High Similarity	NPC117992
0.9542	High Similarity	NPC201136
0.9542	High Similarity	NPC227325
0.9542	High Similarity	NPC472280
0.9542	High Similarity	NPC196439
0.9542	High Similarity	NPC146165
0.9542	High Similarity	NPC167815
0.9542	High Similarity	NPC92659
0.9542	High Similarity	NPC134287
0.9539	High Similarity	NPC100887
0.9539	High Similarity	NPC188203
0.9539	High Similarity	NPC239128
0.9539	High Similarity	NPC198826
0.9539	High Similarity	NPC293183
0.9539	High Similarity	NPC39732
0.9539	High Similarity	NPC57030
0.9539	High Similarity	NPC83508
0.9539	High Similarity	NPC212678
0.9539	High Similarity	NPC301323
0.9539	High Similarity	NPC162313
0.9539	High Similarity	NPC25270
0.9539	High Similarity	NPC187498
0.9539	High Similarity	NPC222830
0.9539	High Similarity	NPC156222
0.9539	High Similarity	NPC60972
0.9539	High Similarity	NPC256283
0.9539	High Similarity	NPC471982
0.9539	High Similarity	NPC131624
0.9539	High Similarity	NPC71334
0.9539	High Similarity	NPC120163
0.9539	High Similarity	NPC275836
0.9539	High Similarity	NPC241498
0.9539	High Similarity	NPC275722
0.9487	High Similarity	NPC266314
0.9484	High Similarity	NPC250214
0.9484	High Similarity	NPC204879
0.9484	High Similarity	NPC95936
0.9481	High Similarity	NPC472916
0.9481	High Similarity	NPC49824
0.9477	High Similarity	NPC227337
0.9477	High Similarity	NPC167091
0.9477	High Similarity	NPC88645
0.9477	High Similarity	NPC250822
0.9477	High Similarity	NPC273462
0.9477	High Similarity	NPC280937
0.9477	High Similarity	NPC124714
0.9477	High Similarity	NPC276409
0.9477	High Similarity	NPC206238
0.9477	High Similarity	NPC70433
0.9477	High Similarity	NPC49402
0.9477	High Similarity	NPC33051
0.9477	High Similarity	NPC75279
0.9477	High Similarity	NPC271779
0.9477	High Similarity	NPC292214
0.9474	High Similarity	NPC226973
0.9474	High Similarity	NPC308451
0.9474	High Similarity	NPC208043
0.943	High Similarity	NPC239752
0.943	High Similarity	NPC472450
0.943	High Similarity	NPC275780
0.943	High Similarity	NPC50960
0.9423	High Similarity	NPC14353
0.9423	High Similarity	NPC56085
0.9423	High Similarity	NPC228785
0.9419	High Similarity	NPC474836
0.9419	High Similarity	NPC110070
0.9419	High Similarity	NPC472913
0.9419	High Similarity	NPC472910
0.9419	High Similarity	NPC48208
0.9419	High Similarity	NPC78103
0.9419	High Similarity	NPC222814
0.9419	High Similarity	NPC189179
0.9419	High Similarity	NPC218313
0.9419	High Similarity	NPC472914
0.9419	High Similarity	NPC224137
0.9419	High Similarity	NPC291508
0.9419	High Similarity	NPC227192
0.9419	High Similarity	NPC99597
0.9419	High Similarity	NPC203891
0.9419	High Similarity	NPC156057
0.9419	High Similarity	NPC472911
0.9419	High Similarity	NPC96167
0.9419	High Similarity	NPC101830
0.9419	High Similarity	NPC223787
0.9419	High Similarity	NPC93376
0.9419	High Similarity	NPC162869
0.9419	High Similarity	NPC474681
0.9419	High Similarity	NPC245758
0.9419	High Similarity	NPC75215
0.9419	High Similarity	NPC470402
0.9419	High Similarity	NPC474208
0.9419	High Similarity	NPC475267
0.9419	High Similarity	NPC210084
0.9416	High Similarity	NPC26227
0.9416	High Similarity	NPC2928
0.9416	High Similarity	NPC201451
0.9416	High Similarity	NPC256925
0.9416	High Similarity	NPC44079
0.9412	High Similarity	NPC269451
0.9412	High Similarity	NPC209487
0.9412	High Similarity	NPC101996
0.9412	High Similarity	NPC39007
0.9412	High Similarity	NPC291802
0.9412	High Similarity	NPC35763
0.9412	High Similarity	NPC237994
0.9412	High Similarity	NPC131266
0.9412	High Similarity	NPC120537
0.9412	High Similarity	NPC161277
0.9412	High Similarity	NPC100263
0.9412	High Similarity	NPC216769
0.9412	High Similarity	NPC245382
0.9412	High Similarity	NPC100971
0.9412	High Similarity	NPC142540
0.9412	High Similarity	NPC249570
0.9412	High Similarity	NPC199100
0.9412	High Similarity	NPC180234
0.9412	High Similarity	NPC181209
0.9412	High Similarity	NPC121522
0.9408	High Similarity	NPC306821
0.9408	High Similarity	NPC88804
0.9408	High Similarity	NPC3825
0.9408	High Similarity	NPC45873
0.9408	High Similarity	NPC184136
0.9371	High Similarity	NPC39091
0.9367	High Similarity	NPC189473
0.9367	High Similarity	NPC470459
0.9367	High Similarity	NPC220313
0.9367	High Similarity	NPC270837
0.9367	High Similarity	NPC23298
0.9367	High Similarity	NPC303460
0.9367	High Similarity	NPC306321
0.9363	High Similarity	NPC40491
0.9363	High Similarity	NPC61010
0.9363	High Similarity	NPC278052
0.9363	High Similarity	NPC472275
0.9359	High Similarity	NPC105242
0.9359	High Similarity	NPC130894
0.9359	High Similarity	NPC4481
0.9359	High Similarity	NPC9609
0.9359	High Similarity	NPC22472
0.9359	High Similarity	NPC18607
0.9359	High Similarity	NPC184755
0.9359	High Similarity	NPC143828
0.9359	High Similarity	NPC172770
0.9359	High Similarity	NPC18772
0.9359	High Similarity	NPC253634
0.9359	High Similarity	NPC74178
0.9359	High Similarity	NPC100123
0.9359	High Similarity	NPC7846
0.9359	High Similarity	NPC300943
0.9359	High Similarity	NPC176300
0.9359	High Similarity	NPC191459

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 NPC258331 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	419
0.1-0.2	995
0.2-0.3	1844
0.3-0.4	2708
0.4-0.5	1714
0.5-0.6	969
0.6-0.7	340
0.7-0.8	102
0.8-0.85	39
0.85-0.9	12
0.9-0.95	7
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9605	High Similarity	NPD2801	Approved
0.9226	High Similarity	NPD2393	Clinical (unspecified phase)
0.9161	High Similarity	NPD1934	Approved
0.9013	High Similarity	NPD1511	Approved
0.8987	High Similarity	NPD3882	Suspended
0.8896	High Similarity	NPD1512	Approved
0.8841	High Similarity	NPD3818	Discontinued
0.8831	High Similarity	NPD4378	Clinical (unspecified phase)
0.882	High Similarity	NPD5494	Approved
0.872	High Similarity	NPD6168	Clinical (unspecified phase)
0.872	High Similarity	NPD6167	Clinical (unspecified phase)
0.872	High Similarity	NPD6166	Phase 2
0.8688	High Similarity	NPD3817	Phase 2
0.8671	High Similarity	NPD4380	Phase 2
0.865	High Similarity	NPD1247	Approved
0.858	High Similarity	NPD4338	Clinical (unspecified phase)
0.8563	High Similarity	NPD7054	Approved
0.8519	High Similarity	NPD4868	Clinical (unspecified phase)
0.8512	High Similarity	NPD7074	Phase 3
0.8512	High Similarity	NPD7472	Approved
0.8485	Intermediate Similarity	NPD6232	Discontinued
0.8471	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8466	Intermediate Similarity	NPD7075	Discontinued
0.8443	Intermediate Similarity	NPD7473	Discontinued
0.8395	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8385	Intermediate Similarity	NPD7411	Suspended
0.8366	Intermediate Similarity	NPD1510	Phase 2
0.8354	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8353	Intermediate Similarity	NPD6797	Phase 2
0.8344	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8343	Intermediate Similarity	NPD5844	Phase 1
0.8333	Intermediate Similarity	NPD6801	Discontinued
0.8323	Intermediate Similarity	NPD1549	Phase 2
0.8312	Intermediate Similarity	NPD2796	Approved
0.8304	Intermediate Similarity	NPD7251	Discontinued
0.8282	Intermediate Similarity	NPD7819	Suspended
0.8258	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8258	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8256	Intermediate Similarity	NPD7808	Phase 3
0.8232	Intermediate Similarity	NPD5402	Approved
0.8224	Intermediate Similarity	NPD1240	Approved
0.8224	Intermediate Similarity	NPD943	Approved
0.8194	Intermediate Similarity	NPD2935	Discontinued
0.8176	Intermediate Similarity	NPD6799	Approved
0.8171	Intermediate Similarity	NPD1465	Phase 2
0.8129	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8117	Intermediate Similarity	NPD1607	Approved
0.8084	Intermediate Similarity	NPD919	Approved
0.8059	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8038	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8035	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD3926	Phase 2
0.7989	Intermediate Similarity	NPD6559	Discontinued
0.7988	Intermediate Similarity	NPD6599	Discontinued
0.7988	Intermediate Similarity	NPD6959	Discontinued
0.7927	Intermediate Similarity	NPD3226	Approved
0.7925	Intermediate Similarity	NPD2800	Approved
0.788	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7877	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7875	Intermediate Similarity	NPD3750	Approved
0.7862	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD7768	Phase 2
0.7843	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD447	Suspended
0.7821	Intermediate Similarity	NPD230	Phase 1
0.7805	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7805	Intermediate Similarity	NPD5403	Approved
0.7805	Intermediate Similarity	NPD920	Approved
0.7791	Intermediate Similarity	NPD2533	Approved
0.7791	Intermediate Similarity	NPD2534	Approved
0.7791	Intermediate Similarity	NPD2532	Approved
0.7778	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7756	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7756	Intermediate Similarity	NPD1613	Approved
0.7742	Intermediate Similarity	NPD2313	Discontinued
0.7706	Intermediate Similarity	NPD3749	Approved
0.7702	Intermediate Similarity	NPD1243	Approved
0.7683	Intermediate Similarity	NPD5401	Approved
0.7683	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD3027	Phase 3
0.7673	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7673	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7673	Intermediate Similarity	NPD2799	Discontinued
0.7651	Intermediate Similarity	NPD1653	Approved
0.7627	Intermediate Similarity	NPD5953	Discontinued
0.7625	Intermediate Similarity	NPD1551	Phase 2
0.7614	Intermediate Similarity	NPD7286	Phase 2
0.7596	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD2346	Discontinued
0.7578	Intermediate Similarity	NPD2344	Approved
0.7562	Intermediate Similarity	NPD3748	Approved
0.7561	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7558	Intermediate Similarity	NPD6234	Discontinued
0.7548	Intermediate Similarity	NPD9494	Approved
0.7547	Intermediate Similarity	NPD6651	Approved
0.7546	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7546	Intermediate Similarity	NPD4628	Phase 3
0.7542	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6190	Approved
0.7484	Intermediate Similarity	NPD1933	Approved
0.7471	Intermediate Similarity	NPD7199	Phase 2
0.7458	Intermediate Similarity	NPD3751	Discontinued
0.741	Intermediate Similarity	NPD7390	Discontinued
0.7407	Intermediate Similarity	NPD6099	Approved
0.7407	Intermediate Similarity	NPD6100	Approved
0.7405	Intermediate Similarity	NPD3268	Approved
0.7394	Intermediate Similarity	NPD2309	Approved
0.7386	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7377	Intermediate Similarity	NPD8434	Phase 2
0.7368	Intermediate Similarity	NPD37	Approved
0.7341	Intermediate Similarity	NPD4965	Approved
0.7341	Intermediate Similarity	NPD4967	Phase 2
0.7341	Intermediate Similarity	NPD4966	Approved
0.734	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD3787	Discontinued
0.7316	Intermediate Similarity	NPD6777	Approved
0.7316	Intermediate Similarity	NPD6780	Approved
0.7316	Intermediate Similarity	NPD6779	Approved
0.7316	Intermediate Similarity	NPD6776	Approved
0.7316	Intermediate Similarity	NPD6778	Approved
0.7316	Intermediate Similarity	NPD6781	Approved
0.7316	Intermediate Similarity	NPD6782	Approved
0.7308	Intermediate Similarity	NPD8313	Approved
0.7308	Intermediate Similarity	NPD1203	Approved
0.7308	Intermediate Similarity	NPD8312	Approved
0.7296	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD7685	Pre-registration
0.7288	Intermediate Similarity	NPD5242	Approved
0.7267	Intermediate Similarity	NPD6844	Discontinued
0.7263	Intermediate Similarity	NPD7228	Approved
0.7262	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD2798	Approved
0.7247	Intermediate Similarity	NPD2403	Approved
0.7234	Intermediate Similarity	NPD4360	Phase 2
0.7234	Intermediate Similarity	NPD4363	Phase 3
0.7232	Intermediate Similarity	NPD5710	Approved
0.7232	Intermediate Similarity	NPD5711	Approved
0.7226	Intermediate Similarity	NPD9269	Phase 2
0.7202	Intermediate Similarity	NPD7435	Discontinued
0.7189	Intermediate Similarity	NPD8150	Discontinued
0.7179	Intermediate Similarity	NPD7584	Approved
0.717	Intermediate Similarity	NPD6832	Phase 2
0.717	Intermediate Similarity	NPD4908	Phase 1
0.7161	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD1471	Phase 3
0.7135	Intermediate Similarity	NPD7229	Phase 3
0.7134	Intermediate Similarity	NPD4308	Phase 3
0.7134	Intermediate Similarity	NPD7033	Discontinued
0.7125	Intermediate Similarity	NPD4625	Phase 3
0.7124	Intermediate Similarity	NPD1548	Phase 1
0.7115	Intermediate Similarity	NPD9717	Approved
0.7113	Intermediate Similarity	NPD7698	Approved
0.7113	Intermediate Similarity	NPD7696	Phase 3
0.7113	Intermediate Similarity	NPD7697	Approved
0.711	Intermediate Similarity	NPD6386	Approved
0.711	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD6385	Approved
0.7107	Intermediate Similarity	NPD8151	Discontinued
0.7105	Intermediate Similarity	NPD4361	Phase 2
0.7105	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD4357	Discontinued
0.7093	Intermediate Similarity	NPD7458	Discontinued
0.7089	Intermediate Similarity	NPD1470	Approved
0.7089	Intermediate Similarity	NPD3266	Approved
0.7089	Intermediate Similarity	NPD3267	Approved
0.7089	Intermediate Similarity	NPD2797	Approved
0.7086	Intermediate Similarity	NPD5353	Approved
0.7077	Intermediate Similarity	NPD7870	Phase 2
0.7077	Intermediate Similarity	NPD7871	Phase 2
0.7065	Intermediate Similarity	NPD7549	Discontinued
0.7062	Intermediate Similarity	NPD6823	Phase 2
0.7059	Intermediate Similarity	NPD5536	Phase 2
0.7056	Intermediate Similarity	NPD7701	Phase 2
0.7053	Intermediate Similarity	NPD6535	Approved
0.7053	Intermediate Similarity	NPD6534	Approved
0.7051	Intermediate Similarity	NPD1610	Phase 2
0.7051	Intermediate Similarity	NPD422	Phase 1
0.7044	Intermediate Similarity	NPD2899	Discontinued
0.7037	Intermediate Similarity	NPD6233	Phase 2
0.7035	Intermediate Similarity	NPD7783	Phase 2
0.7035	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD3225	Approved
0.7011	Intermediate Similarity	NPD5890	Approved
0.7011	Intermediate Similarity	NPD5889	Approved
0.7006	Intermediate Similarity	NPD1608	Approved
0.7006	Intermediate Similarity	NPD2424	Discontinued
0.7	Intermediate Similarity	NPD3018	Phase 2
0.7	Intermediate Similarity	NPD2861	Phase 2
0.6995	Remote Similarity	NPD1729	Discontinued
0.6994	Remote Similarity	NPD4060	Phase 1
0.6994	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD4288	Approved
0.6988	Remote Similarity	NPD5404	Approved
0.6988	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