NPASS Compound

Structure

NPC471515 OpenBabel07101719402D 24 26 0 0 1 0 0 0 0 0999 V2000 4.3301 -2.5000 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 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 -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 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 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 -0.8660 1.5000 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 0.8660 0.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 3 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 2.5981 -2.5000 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 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 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 22 1 0 0 0 0 2 23 1 0 0 0 0 3 4 2 0 0 0 0 3 8 1 0 0 0 0 4 12 1 0 0 0 0 5 8 2 0 0 0 0 5 10 1 0 0 0 0 6 9 2 0 0 0 0 6 11 1 0 0 0 0 7 9 1 0 0 0 0 7 13 2 0 0 0 0 8 16 1 0 0 0 0 9 18 1 0 0 0 0 10 12 2 0 0 0 0 10 19 1 0 0 0 0 11 14 2 0 0 0 0 11 20 1 0 0 0 0 12 22 1 0 0 0 0 13 14 1 0 0 0 0 13 24 1 0 0 0 0 14 15 1 0 0 0 0 15 17 1 0 0 0 0 15 21 2 0 0 0 0 16 17 1 0 0 0 0 16 24 1 0 0 0 0 17 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	332.09
Volume:	319.995
LogP:	1.757
LogD:	2.392
LogS:	-3.719
# Rotatable Bonds:	3
TPSA:	105.45
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.791
Synthetic Accessibility Score:	3.364
Fsp3:	0.235
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.045
MDCK Permeability:	7.397473382297903e-06
Pgp-inhibitor:	0.007
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.016
20% Bioavailability (F20%):	0.008
30% Bioavailability (F30%):	0.35

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.033
Plasma Protein Binding (PPB):	96.1141586303711%
Volume Distribution (VD):	0.617
Pgp-substrate:	5.663235664367676%

ADMET: Metabolism

CYP1A2-inhibitor:	0.309
CYP1A2-substrate:	0.676
CYP2C19-inhibitor:	0.064
CYP2C19-substrate:	0.072
CYP2C9-inhibitor:	0.405
CYP2C9-substrate:	0.76
CYP2D6-inhibitor:	0.508
CYP2D6-substrate:	0.486
CYP3A4-inhibitor:	0.847
CYP3A4-substrate:	0.269

ADMET: Excretion

Clearance (CL):	8.221
Half-life (T1/2):	0.501

ADMET: Toxicity

hERG Blockers:	0.04
Human Hepatotoxicity (H-HT):	0.108
Drug-inuced Liver Injury (DILI):	0.911
AMES Toxicity:	0.513
Rat Oral Acute Toxicity:	0.202
Maximum Recommended Daily Dose:	0.169
Skin Sensitization:	0.733
Carcinogencity:	0.181
Eye Corrosion:	0.003
Eye Irritation:	0.706
Respiratory Toxicity:	0.139

Download Data

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

Natural Product: NPC471515

Natural Product ID:	NPC471515
*Common Name:**	3,4'-O-Dimethylquercetin
IUPAC Name:	5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-3-methoxy-2,3-dihydrochromen-4-one
Synonyms:	3,4'-O-dimethylquercetin
Standard InCHIKey:	YMSMRPNRLZXMMQ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C17H16O7/c1-22-12-4-3-8(5-10(12)19)16-17(23-2)15(21)14-11(20)6-9(18)7-13(14)24-16/h3-7,16-20H,1-2H3
SMILES:	COC1C(OC2=CC(=CC(=C2C1=O)O)O)C3=CC(=C(C=C3)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL253946
PubChem CID:	44446550
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0002585] O-methylated flavonoids [CHEMONTID:0002596] 4'-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
NPO33126	siegesbeckia glabrescens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18178435]

☑ 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	1
Others	9

Activity Type	# Activity
Cell Line	1
CELL-LINE	6
Others	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT34	Cell Line	BV-2	Mus musculus	IC50	=	11100.0	nM	PMID[490264]
NPT27	Others	Unspecified		Activity	=	50.0	%	PMID[490265]
NPT27	Others	Unspecified		Activity	=	63.2	%	PMID[490265]
NPT22995	CELL-LINE	B16-F0	Mus musculus	Activity	=	346.7	%	PMID[490265]
NPT27	Others	Unspecified		Activity	=	75.6	%	PMID[490265]
NPT22995	CELL-LINE	B16-F0	Mus musculus	Activity	=	132.3	%	PMID[490265]
NPT22995	CELL-LINE	B16-F0	Mus musculus	Activity	=	178.8	%	PMID[490265]
NPT22995	CELL-LINE	B16-F0	Mus musculus	Activity	=	309.5	%	PMID[490265]
NPT22995	CELL-LINE	B16-F0	Mus musculus	Activity	=	229.5	%	PMID[490265]
NPT22995	CELL-LINE	B16-F0	Mus musculus	Activity	=	166.6	%	PMID[490265]

☑ 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 NPC471515 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	410
0.1-0.2	1653
0.2-0.3	4455
0.3-0.4	10519
0.4-0.5	7246
0.5-0.6	3513
0.6-0.7	4737
0.7-0.8	5378
0.8-0.85	2649
0.85-0.9	1511
0.9-0.95	532
0.95-1	94

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC471479
0.9933	High Similarity	NPC471500
0.98	High Similarity	NPC320825
0.98	High Similarity	NPC326037
0.98	High Similarity	NPC13858
0.9799	High Similarity	NPC18727
0.9737	High Similarity	NPC282009
0.9737	High Similarity	NPC287328
0.9735	High Similarity	NPC52530
0.9735	High Similarity	NPC67876
0.9732	High Similarity	NPC236637
0.9732	High Similarity	NPC219582
0.9732	High Similarity	NPC302950
0.9673	High Similarity	NPC471499
0.9673	High Similarity	NPC112418
0.9671	High Similarity	NPC22192
0.9669	High Similarity	NPC195796
0.9669	High Similarity	NPC291878
0.9669	High Similarity	NPC250922
0.9669	High Similarity	NPC278778
0.9669	High Similarity	NPC35038
0.9667	High Similarity	NPC270620
0.9667	High Similarity	NPC236223
0.9667	High Similarity	NPC179126
0.9667	High Similarity	NPC78326
0.961	High Similarity	NPC471745
0.9608	High Similarity	NPC263449
0.9608	High Similarity	NPC470326
0.9608	High Similarity	NPC471744
0.9608	High Similarity	NPC470183
0.9605	High Similarity	NPC48208
0.9605	High Similarity	NPC474208
0.9605	High Similarity	NPC291508
0.9605	High Similarity	NPC474055
0.9605	High Similarity	NPC27337
0.9605	High Similarity	NPC475267
0.9605	High Similarity	NPC474836
0.9605	High Similarity	NPC472598
0.9605	High Similarity	NPC156057
0.9605	High Similarity	NPC162869
0.9603	High Similarity	NPC470327
0.9603	High Similarity	NPC477503
0.9603	High Similarity	NPC45849
0.9603	High Similarity	NPC200761
0.96	High Similarity	NPC82325
0.96	High Similarity	NPC260491
0.96	High Similarity	NPC36835
0.96	High Similarity	NPC472912
0.96	High Similarity	NPC246162
0.96	High Similarity	NPC61506
0.96	High Similarity	NPC279989
0.96	High Similarity	NPC240476
0.96	High Similarity	NPC9743
0.9597	High Similarity	NPC338131
0.9551	High Similarity	NPC477517
0.9548	High Similarity	NPC472625
0.9545	High Similarity	NPC173137
0.9545	High Similarity	NPC308992
0.9542	High Similarity	NPC152904
0.9542	High Similarity	NPC55738
0.9539	High Similarity	NPC472626
0.9539	High Similarity	NPC235165
0.9539	High Similarity	NPC255106
0.9539	High Similarity	NPC265511
0.9539	High Similarity	NPC209614
0.9539	High Similarity	NPC470328
0.9539	High Similarity	NPC474638
0.9536	High Similarity	NPC246328
0.9536	High Similarity	NPC58382
0.9536	High Similarity	NPC325028
0.9536	High Similarity	NPC256346
0.9536	High Similarity	NPC213896
0.9536	High Similarity	NPC141212
0.9536	High Similarity	NPC162351
0.9536	High Similarity	NPC192083
0.9536	High Similarity	NPC27532
0.9533	High Similarity	NPC200740
0.9533	High Similarity	NPC236769
0.9533	High Similarity	NPC125062
0.9533	High Similarity	NPC54394
0.9533	High Similarity	NPC252933
0.9487	High Similarity	NPC36916
0.9487	High Similarity	NPC7154
0.9487	High Similarity	NPC7688
0.9487	High Similarity	NPC72787
0.9487	High Similarity	NPC224280
0.9487	High Similarity	NPC36
0.9487	High Similarity	NPC125039
0.9487	High Similarity	NPC62261
0.9487	High Similarity	NPC58223
0.9481	High Similarity	NPC36217
0.9481	High Similarity	NPC118256
0.9481	High Similarity	NPC192686
0.9481	High Similarity	NPC119209
0.9481	High Similarity	NPC472624
0.9477	High Similarity	NPC472910
0.9477	High Similarity	NPC129684
0.9477	High Similarity	NPC472913
0.9477	High Similarity	NPC222814
0.9477	High Similarity	NPC96167
0.9477	High Similarity	NPC472914
0.9477	High Similarity	NPC203891
0.9477	High Similarity	NPC299520
0.9477	High Similarity	NPC99597
0.9477	High Similarity	NPC245758
0.9477	High Similarity	NPC101830
0.9477	High Similarity	NPC472911
0.9477	High Similarity	NPC110070
0.9477	High Similarity	NPC210084
0.9477	High Similarity	NPC223787
0.9474	High Similarity	NPC321779
0.9474	High Similarity	NPC37392
0.9474	High Similarity	NPC226025
0.9474	High Similarity	NPC67396
0.9474	High Similarity	NPC133392
0.947	High Similarity	NPC260979
0.947	High Similarity	NPC477231
0.947	High Similarity	NPC106976
0.947	High Similarity	NPC123886
0.947	High Similarity	NPC19721
0.947	High Similarity	NPC257648
0.947	High Similarity	NPC55205
0.9467	High Similarity	NPC149127
0.9467	High Similarity	NPC188871
0.9467	High Similarity	NPC286342
0.9467	High Similarity	NPC50728
0.9467	High Similarity	NPC166753
0.9463	High Similarity	NPC321011
0.9463	High Similarity	NPC294852
0.9463	High Similarity	NPC188679
0.9427	High Similarity	NPC471213
0.9419	High Similarity	NPC474038
0.9419	High Similarity	NPC472632
0.9419	High Similarity	NPC472634
0.9419	High Similarity	NPC471210
0.9419	High Similarity	NPC26326
0.9419	High Similarity	NPC158188
0.9419	High Similarity	NPC289771
0.9416	High Similarity	NPC143828
0.9416	High Similarity	NPC152166
0.9416	High Similarity	NPC22472
0.9416	High Similarity	NPC115798
0.9416	High Similarity	NPC176300
0.9416	High Similarity	NPC95936
0.9416	High Similarity	NPC130894
0.9416	High Similarity	NPC18607
0.9416	High Similarity	NPC7846
0.9416	High Similarity	NPC300943
0.9416	High Similarity	NPC105242
0.9416	High Similarity	NPC4481
0.9416	High Similarity	NPC191459
0.9416	High Similarity	NPC18772
0.9416	High Similarity	NPC288669
0.9416	High Similarity	NPC250214
0.9416	High Similarity	NPC25495
0.9416	High Similarity	NPC253634
0.9416	High Similarity	NPC261004
0.9416	High Similarity	NPC9609
0.9416	High Similarity	NPC204854
0.9416	High Similarity	NPC19687
0.9412	High Similarity	NPC201837
0.9412	High Similarity	NPC303255
0.9412	High Similarity	NPC245546
0.9412	High Similarity	NPC100916
0.9412	High Similarity	NPC472916
0.9412	High Similarity	NPC43243
0.9412	High Similarity	NPC55619
0.9412	High Similarity	NPC200388
0.9412	High Similarity	NPC24640
0.9412	High Similarity	NPC49824
0.9412	High Similarity	NPC266960
0.9412	High Similarity	NPC292107
0.9408	High Similarity	NPC298692
0.9408	High Similarity	NPC469550
0.9408	High Similarity	NPC74924
0.9404	High Similarity	NPC76376
0.9404	High Similarity	NPC260895
0.9404	High Similarity	NPC50403
0.9404	High Similarity	NPC28274
0.9404	High Similarity	NPC133953
0.9404	High Similarity	NPC31363
0.94	High Similarity	NPC137062
0.94	High Similarity	NPC183950
0.94	High Similarity	NPC183959
0.94	High Similarity	NPC270465
0.94	High Similarity	NPC159103
0.94	High Similarity	NPC48479
0.94	High Similarity	NPC52005
0.94	High Similarity	NPC1612
0.94	High Similarity	NPC177298
0.94	High Similarity	NPC223579
0.94	High Similarity	NPC87125
0.94	High Similarity	NPC287101
0.9363	High Similarity	NPC475888
0.9363	High Similarity	NPC234052
0.9363	High Similarity	NPC470457
0.9359	High Similarity	NPC472635
0.9359	High Similarity	NPC476247
0.9359	High Similarity	NPC474033
0.9359	High Similarity	NPC201800

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 NPC471515 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	367
0.1-0.2	951
0.2-0.3	1807
0.3-0.4	2599
0.4-0.5	1780
0.5-0.6	970
0.6-0.7	487
0.7-0.8	132
0.8-0.85	33
0.85-0.9	13
0.9-0.95	6
0.95-1	5

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9732	High Similarity	NPD1934	Approved
0.9536	High Similarity	NPD2393	Clinical (unspecified phase)
0.9487	High Similarity	NPD6166	Phase 2
0.9487	High Similarity	NPD6167	Clinical (unspecified phase)
0.9487	High Similarity	NPD6168	Clinical (unspecified phase)
0.9412	High Similarity	NPD3882	Suspended
0.9281	High Similarity	NPD2801	Approved
0.9221	High Similarity	NPD3817	Phase 2
0.92	High Similarity	NPD1512	Approved
0.9074	High Similarity	NPD6797	Phase 2
0.9067	High Similarity	NPD1511	Approved
0.9018	High Similarity	NPD7251	Discontinued
0.9012	High Similarity	NPD7074	Phase 3
0.8981	High Similarity	NPD7075	Discontinued
0.8963	High Similarity	NPD7808	Phase 3
0.8963	High Similarity	NPD4338	Clinical (unspecified phase)
0.8951	High Similarity	NPD7054	Approved
0.891	High Similarity	NPD7096	Clinical (unspecified phase)
0.8896	High Similarity	NPD7472	Approved
0.8889	High Similarity	NPD3818	Discontinued
0.8882	High Similarity	NPD4378	Clinical (unspecified phase)
0.8797	High Similarity	NPD4868	Clinical (unspecified phase)
0.8792	High Similarity	NPD1550	Clinical (unspecified phase)
0.8792	High Similarity	NPD1552	Clinical (unspecified phase)
0.8733	High Similarity	NPD1549	Phase 2
0.8718	High Similarity	NPD4380	Phase 2
0.8693	High Similarity	NPD6799	Approved
0.8634	High Similarity	NPD5494	Approved
0.8625	High Similarity	NPD4381	Clinical (unspecified phase)
0.8608	High Similarity	NPD6801	Discontinued
0.8606	High Similarity	NPD7804	Clinical (unspecified phase)
0.8503	High Similarity	NPD7993	Clinical (unspecified phase)
0.8481	Intermediate Similarity	NPD6599	Discontinued
0.8477	Intermediate Similarity	NPD2796	Approved
0.8411	Intermediate Similarity	NPD1510	Phase 2
0.8385	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8385	Intermediate Similarity	NPD5402	Approved
0.8323	Intermediate Similarity	NPD7819	Suspended
0.8303	Intermediate Similarity	NPD6232	Discontinued
0.8291	Intermediate Similarity	NPD5403	Approved
0.8274	Intermediate Similarity	NPD5844	Phase 1
0.8267	Intermediate Similarity	NPD1240	Approved
0.8267	Intermediate Similarity	NPD1613	Approved
0.8267	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8263	Intermediate Similarity	NPD7473	Discontinued
0.8242	Intermediate Similarity	NPD1247	Approved
0.8242	Intermediate Similarity	NPD6959	Discontinued
0.8232	Intermediate Similarity	NPD919	Approved
0.821	Intermediate Similarity	NPD1465	Phase 2
0.8199	Intermediate Similarity	NPD7411	Suspended
0.8165	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8165	Intermediate Similarity	NPD5401	Approved
0.8158	Intermediate Similarity	NPD1607	Approved
0.8146	Intermediate Similarity	NPD943	Approved
0.8144	Intermediate Similarity	NPD3926	Phase 2
0.8129	Intermediate Similarity	NPD6559	Discontinued
0.8121	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8067	Intermediate Similarity	NPD3027	Phase 3
0.8054	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7929	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7898	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD3751	Discontinued
0.7882	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.787	Intermediate Similarity	NPD3787	Discontinued
0.7862	Intermediate Similarity	NPD6190	Approved
0.7857	Intermediate Similarity	NPD230	Phase 1
0.784	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7799	Intermediate Similarity	NPD3750	Approved
0.7799	Intermediate Similarity	NPD4628	Phase 3
0.7784	Intermediate Similarity	NPD7768	Phase 2
0.7778	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD1551	Phase 2
0.7771	Intermediate Similarity	NPD2935	Discontinued
0.7742	Intermediate Similarity	NPD447	Suspended
0.774	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7738	Intermediate Similarity	NPD3749	Approved
0.7736	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7736	Intermediate Similarity	NPD2800	Approved
0.7722	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7716	Intermediate Similarity	NPD2534	Approved
0.7716	Intermediate Similarity	NPD2533	Approved
0.7716	Intermediate Similarity	NPD2532	Approved
0.7706	Intermediate Similarity	NPD7199	Phase 2
0.7692	Intermediate Similarity	NPD6234	Discontinued
0.7683	Intermediate Similarity	NPD1653	Approved
0.7662	Intermediate Similarity	NPD6798	Discontinued
0.7658	Intermediate Similarity	NPD6100	Approved
0.7658	Intermediate Similarity	NPD6099	Approved
0.7654	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7628	Intermediate Similarity	NPD1933	Approved
0.7622	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7611	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD9494	Approved
0.7554	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.755	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7533	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD4908	Phase 1
0.7516	Intermediate Similarity	NPD6355	Discontinued
0.7515	Intermediate Similarity	NPD920	Approved
0.75	Intermediate Similarity	NPD2344	Approved
0.75	Intermediate Similarity	NPD6233	Phase 2
0.75	Intermediate Similarity	NPD37	Approved
0.7486	Intermediate Similarity	NPD7228	Approved
0.7484	Intermediate Similarity	NPD3748	Approved
0.7472	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD4965	Approved
0.7471	Intermediate Similarity	NPD4967	Phase 2
0.7471	Intermediate Similarity	NPD4966	Approved
0.7469	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD6651	Approved
0.7458	Intermediate Similarity	NPD5953	Discontinued
0.7443	Intermediate Similarity	NPD7286	Phase 2
0.7436	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7425	Intermediate Similarity	NPD3226	Approved
0.7417	Intermediate Similarity	NPD1610	Phase 2
0.7416	Intermediate Similarity	NPD7685	Pre-registration
0.7407	Intermediate Similarity	NPD1243	Approved
0.7403	Intermediate Similarity	NPD8434	Phase 2
0.7394	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD2346	Discontinued
0.7378	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD7033	Discontinued
0.7375	Intermediate Similarity	NPD2799	Discontinued
0.7371	Intermediate Similarity	NPD2403	Approved
0.7362	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD4360	Phase 2
0.7351	Intermediate Similarity	NPD4363	Phase 3
0.7342	Intermediate Similarity	NPD4060	Phase 1
0.734	Intermediate Similarity	NPD6776	Approved
0.734	Intermediate Similarity	NPD6780	Approved
0.734	Intermediate Similarity	NPD6781	Approved
0.734	Intermediate Similarity	NPD6779	Approved
0.734	Intermediate Similarity	NPD6778	Approved
0.734	Intermediate Similarity	NPD6782	Approved
0.734	Intermediate Similarity	NPD6777	Approved
0.7338	Intermediate Similarity	NPD1203	Approved
0.7333	Intermediate Similarity	NPD8313	Approved
0.7333	Intermediate Similarity	NPD7390	Discontinued
0.7333	Intermediate Similarity	NPD8312	Approved
0.7325	Intermediate Similarity	NPD2313	Discontinued
0.7317	Intermediate Similarity	NPD2309	Approved
0.7316	Intermediate Similarity	NPD7435	Discontinued
0.7314	Intermediate Similarity	NPD5242	Approved
0.731	Intermediate Similarity	NPD5353	Approved
0.7308	Intermediate Similarity	NPD8150	Discontinued
0.7308	Intermediate Similarity	NPD6832	Phase 2
0.7296	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7288	Intermediate Similarity	NPD2163	Approved
0.7273	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD1548	Phase 1
0.7257	Intermediate Similarity	NPD5711	Approved
0.7257	Intermediate Similarity	NPD5710	Approved
0.7244	Intermediate Similarity	NPD2861	Phase 2
0.7235	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD3268	Approved
0.7212	Intermediate Similarity	NPD2354	Approved
0.7212	Intermediate Similarity	NPD3887	Approved
0.7211	Intermediate Similarity	NPD2493	Approved
0.7211	Intermediate Similarity	NPD2494	Approved
0.7202	Intermediate Similarity	NPD7584	Approved
0.7195	Intermediate Similarity	NPD1652	Phase 2
0.7193	Intermediate Similarity	NPD6844	Discontinued
0.7186	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD2798	Approved
0.7178	Intermediate Similarity	NPD7266	Discontinued
0.717	Intermediate Similarity	NPD4062	Phase 3
0.7152	Intermediate Similarity	NPD4625	Phase 3
0.7152	Intermediate Similarity	NPD7095	Approved
0.7143	Intermediate Similarity	NPD1608	Approved
0.7143	Intermediate Similarity	NPD9717	Approved
0.7143	Intermediate Similarity	NPD9269	Phase 2
0.7135	Intermediate Similarity	NPD6386	Approved
0.7135	Intermediate Similarity	NPD7698	Approved
0.7135	Intermediate Similarity	NPD7696	Phase 3
0.7135	Intermediate Similarity	NPD6385	Approved
0.7135	Intermediate Similarity	NPD7697	Approved
0.7134	Intermediate Similarity	NPD2424	Discontinued
0.7134	Intermediate Similarity	NPD3018	Phase 2
0.7128	Intermediate Similarity	NPD8151	Discontinued
0.712	Intermediate Similarity	NPD3452	Approved
0.712	Intermediate Similarity	NPD3450	Approved
0.7118	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD2797	Approved
0.7098	Intermediate Similarity	NPD4582	Approved
0.7098	Intermediate Similarity	NPD7870	Phase 2
0.7098	Intermediate Similarity	NPD7871	Phase 2
0.7098	Intermediate Similarity	NPD4583	Approved
0.7097	Intermediate Similarity	NPD2490	Approved
0.7097	Intermediate Similarity	NPD4749	Approved
0.7097	Intermediate Similarity	NPD2488	Approved
0.7092	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD7874	Approved
0.7091	Intermediate Similarity	NPD2654	Approved
0.7086	Intermediate Similarity	NPD5536	Phase 2
0.7083	Intermediate Similarity	NPD3688	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD4661	Approved
0.7083	Intermediate Similarity	NPD3146	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