NPASS Compound

Structure

NPC471500 OpenBabel07101718282D 24 26 0 0 1 0 0 0 0 0999 V2000 3.4641 -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 -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 -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 -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 -3.4641 -1.0000 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 1.7321 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 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 -4.3301 -1.5000 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 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 3.4641 -0.0000 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 10 1 0 0 0 0 5 8 2 0 0 0 0 5 11 1 0 0 0 0 6 9 2 0 0 0 0 6 12 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 22 1 0 0 0 0 10 11 2 0 0 0 0 10 18 1 0 0 0 0 11 19 1 0 0 0 0 12 14 2 0 0 0 0 12 20 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:	2.147
LogD:	2.452
LogS:	-3.743
# 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:	0.74
Synthetic Accessibility Score:	3.355
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:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.01
MDCK Permeability:	7.607213319715811e-06
Pgp-inhibitor:	0.031
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.015
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.428

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.022
Plasma Protein Binding (PPB):	97.06319427490234%
Volume Distribution (VD):	0.59
Pgp-substrate:	4.955028533935547%

ADMET: Metabolism

CYP1A2-inhibitor:	0.245
CYP1A2-substrate:	0.67
CYP2C19-inhibitor:	0.056
CYP2C19-substrate:	0.069
CYP2C9-inhibitor:	0.422
CYP2C9-substrate:	0.688
CYP2D6-inhibitor:	0.406
CYP2D6-substrate:	0.509
CYP3A4-inhibitor:	0.697
CYP3A4-substrate:	0.239

ADMET: Excretion

Clearance (CL):	8.81
Half-life (T1/2):	0.385

ADMET: Toxicity

hERG Blockers:	0.027
Human Hepatotoxicity (H-HT):	0.085
Drug-inuced Liver Injury (DILI):	0.93
AMES Toxicity:	0.592
Rat Oral Acute Toxicity:	0.246
Maximum Recommended Daily Dose:	0.17
Skin Sensitization:	0.882
Carcinogencity:	0.286
Eye Corrosion:	0.003
Eye Irritation:	0.889
Respiratory Toxicity:	0.084

Download Data

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

Natural Product: NPC471500

Natural Product ID:	NPC471500
*Common Name:**	2-(3,4-Dihydroxyphenyl)-5-Hydroxy-3,7-Dimethoxy-2,3-Dihydrochromen-4-One
IUPAC Name:	2-(3,4-dihydroxyphenyl)-5-hydroxy-3,7-dimethoxy-2,3-dihydrochromen-4-one
Synonyms:
Standard InCHIKey:	KTQFOHHZQDGISL-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C17H16O7/c1-22-9-6-12(20)14-13(7-9)24-16(17(23-2)15(14)21)8-3-4-10(18)11(19)5-8/h3-7,16-20H,1-2H3
SMILES:	COC1C(OC2=CC(=CC(=C2C1=O)O)OC)C3=CC(=C(C=C3)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL253249
PubChem CID:	44446552
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
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	1

Activity Type	# Activity
Cell Line	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT34	Cell Line	BV-2	Mus musculus	IC50	=	4200.0	nM	PMID[451249]
NPT2	Others	Unspecified		SC50	=	1.75	uM	PMID[451249]

☑ 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 NPC471500 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	404
0.1-0.2	1642
0.2-0.3	4385
0.3-0.4	10292
0.4-0.5	7521
0.5-0.6	3457
0.6-0.7	4799
0.7-0.8	5369
0.8-0.85	2741
0.85-0.9	1512
0.9-0.95	506
0.95-1	69

Similarity Score	Similarity Level	Natural Product ID
0.9933	High Similarity	NPC471479
0.9933	High Similarity	NPC471515
0.9737	High Similarity	NPC112418
0.9735	High Similarity	NPC22192
0.9733	High Similarity	NPC320825
0.9733	High Similarity	NPC326037
0.9733	High Similarity	NPC13858
0.9732	High Similarity	NPC18727
0.9673	High Similarity	NPC471745
0.9671	High Similarity	NPC282009
0.9671	High Similarity	NPC471744
0.9671	High Similarity	NPC470183
0.9671	High Similarity	NPC287328
0.9669	High Similarity	NPC52530
0.9669	High Similarity	NPC67876
0.9664	High Similarity	NPC219582
0.9664	High Similarity	NPC36835
0.9664	High Similarity	NPC240476
0.9664	High Similarity	NPC246162
0.9664	High Similarity	NPC260491
0.9664	High Similarity	NPC302950
0.9664	High Similarity	NPC236637
0.9664	High Similarity	NPC9743
0.9664	High Similarity	NPC61506
0.9608	High Similarity	NPC471499
0.9603	High Similarity	NPC291878
0.9603	High Similarity	NPC195796
0.9603	High Similarity	NPC250922
0.9603	High Similarity	NPC278778
0.9603	High Similarity	NPC35038
0.96	High Similarity	NPC27532
0.96	High Similarity	NPC213896
0.96	High Similarity	NPC270620
0.96	High Similarity	NPC256346
0.96	High Similarity	NPC192083
0.96	High Similarity	NPC325028
0.96	High Similarity	NPC78326
0.96	High Similarity	NPC236223
0.96	High Similarity	NPC179126
0.96	High Similarity	NPC141212
0.96	High Similarity	NPC246328
0.9542	High Similarity	NPC263449
0.9542	High Similarity	NPC470326
0.9539	High Similarity	NPC27337
0.9539	High Similarity	NPC474836
0.9539	High Similarity	NPC291508
0.9539	High Similarity	NPC162869
0.9539	High Similarity	NPC472598
0.9539	High Similarity	NPC48208
0.9539	High Similarity	NPC474208
0.9539	High Similarity	NPC156057
0.9539	High Similarity	NPC475267
0.9539	High Similarity	NPC474055
0.9536	High Similarity	NPC321779
0.9536	High Similarity	NPC477503
0.9536	High Similarity	NPC133392
0.9536	High Similarity	NPC470327
0.9536	High Similarity	NPC67396
0.9536	High Similarity	NPC45849
0.9536	High Similarity	NPC200761
0.9533	High Similarity	NPC19721
0.9533	High Similarity	NPC279989
0.9533	High Similarity	NPC106976
0.9533	High Similarity	NPC472912
0.9533	High Similarity	NPC82325
0.953	High Similarity	NPC149127
0.953	High Similarity	NPC286342
0.953	High Similarity	NPC188871
0.953	High Similarity	NPC338131
0.9527	High Similarity	NPC294852
0.9527	High Similarity	NPC188679
0.9527	High Similarity	NPC321011
0.9487	High Similarity	NPC477517
0.9484	High Similarity	NPC472625
0.9481	High Similarity	NPC308992
0.9481	High Similarity	NPC289771
0.9481	High Similarity	NPC173137
0.9477	High Similarity	NPC152904
0.9477	High Similarity	NPC55738
0.9474	High Similarity	NPC235165
0.9474	High Similarity	NPC201837
0.9474	High Similarity	NPC472626
0.9474	High Similarity	NPC474638
0.9474	High Similarity	NPC255106
0.9474	High Similarity	NPC265511
0.9474	High Similarity	NPC470328
0.9474	High Similarity	NPC24640
0.9474	High Similarity	NPC209614
0.947	High Similarity	NPC298692
0.947	High Similarity	NPC58382
0.947	High Similarity	NPC162351
0.947	High Similarity	NPC74924
0.9467	High Similarity	NPC125062
0.9467	High Similarity	NPC236769
0.9467	High Similarity	NPC260895
0.9467	High Similarity	NPC252933
0.9467	High Similarity	NPC54394
0.9467	High Similarity	NPC200740
0.9463	High Similarity	NPC183959
0.9463	High Similarity	NPC87125
0.9463	High Similarity	NPC270465
0.9463	High Similarity	NPC1612
0.9423	High Similarity	NPC36916
0.9423	High Similarity	NPC72787
0.9423	High Similarity	NPC224280
0.9423	High Similarity	NPC7688
0.9423	High Similarity	NPC7154
0.9423	High Similarity	NPC58223
0.9423	High Similarity	NPC125039
0.9423	High Similarity	NPC36
0.9423	High Similarity	NPC62261
0.9419	High Similarity	NPC211107
0.9416	High Similarity	NPC192686
0.9416	High Similarity	NPC36217
0.9416	High Similarity	NPC119209
0.9416	High Similarity	NPC118256
0.9416	High Similarity	NPC472624
0.9412	High Similarity	NPC110070
0.9412	High Similarity	NPC129684
0.9412	High Similarity	NPC222814
0.9412	High Similarity	NPC472913
0.9412	High Similarity	NPC472914
0.9412	High Similarity	NPC99597
0.9412	High Similarity	NPC471209
0.9412	High Similarity	NPC96167
0.9412	High Similarity	NPC472910
0.9412	High Similarity	NPC299520
0.9412	High Similarity	NPC101830
0.9412	High Similarity	NPC203891
0.9412	High Similarity	NPC223787
0.9412	High Similarity	NPC472911
0.9412	High Similarity	NPC245758
0.9412	High Similarity	NPC210084
0.9408	High Similarity	NPC80534
0.9408	High Similarity	NPC37392
0.9408	High Similarity	NPC226025
0.9408	High Similarity	NPC56786
0.9404	High Similarity	NPC37684
0.9404	High Similarity	NPC257648
0.9404	High Similarity	NPC63187
0.9404	High Similarity	NPC477231
0.9404	High Similarity	NPC123886
0.9404	High Similarity	NPC260979
0.9404	High Similarity	NPC55205
0.9404	High Similarity	NPC157784
0.94	High Similarity	NPC166753
0.94	High Similarity	NPC50728
0.9396	High Similarity	NPC3036
0.9396	High Similarity	NPC218569
0.9367	High Similarity	NPC52382
0.9367	High Similarity	NPC270578
0.9363	High Similarity	NPC471213
0.9359	High Similarity	NPC472582
0.9355	High Similarity	NPC472632
0.9355	High Similarity	NPC472634
0.9355	High Similarity	NPC471210
0.9355	High Similarity	NPC142252
0.9355	High Similarity	NPC26326
0.9355	High Similarity	NPC158188
0.9355	High Similarity	NPC474038
0.9351	High Similarity	NPC105242
0.9351	High Similarity	NPC152166
0.9351	High Similarity	NPC9609
0.9351	High Similarity	NPC4481
0.9351	High Similarity	NPC53545
0.9351	High Similarity	NPC22472
0.9351	High Similarity	NPC18607
0.9351	High Similarity	NPC143828
0.9351	High Similarity	NPC117418
0.9351	High Similarity	NPC130894
0.9351	High Similarity	NPC18772
0.9351	High Similarity	NPC176300
0.9351	High Similarity	NPC253634
0.9351	High Similarity	NPC250214
0.9351	High Similarity	NPC95936
0.9351	High Similarity	NPC7846
0.9351	High Similarity	NPC300943
0.9351	High Similarity	NPC261004
0.9351	High Similarity	NPC19687
0.9351	High Similarity	NPC288669
0.9351	High Similarity	NPC191459
0.9351	High Similarity	NPC115798
0.9351	High Similarity	NPC25495
0.9351	High Similarity	NPC210459
0.9351	High Similarity	NPC204854
0.9346	High Similarity	NPC303255
0.9346	High Similarity	NPC43243
0.9346	High Similarity	NPC266960
0.9346	High Similarity	NPC292107
0.9346	High Similarity	NPC200388
0.9346	High Similarity	NPC472916
0.9346	High Similarity	NPC245546
0.9346	High Similarity	NPC55619
0.9346	High Similarity	NPC100916
0.9346	High Similarity	NPC49824
0.9342	High Similarity	NPC469550
0.9338	High Similarity	NPC319910
0.9338	High Similarity	NPC254412
0.9338	High Similarity	NPC50403
0.9338	High Similarity	NPC31363

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 NPC471500 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	364
0.1-0.2	941
0.2-0.3	1787
0.3-0.4	2599
0.4-0.5	1770
0.5-0.6	1009
0.6-0.7	483
0.7-0.8	140
0.8-0.85	35
0.85-0.9	14
0.9-0.95	6
0.95-1	2

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9664	High Similarity	NPD1934	Approved
0.96	High Similarity	NPD2393	Clinical (unspecified phase)
0.9423	High Similarity	NPD6167	Clinical (unspecified phase)
0.9423	High Similarity	NPD6166	Phase 2
0.9423	High Similarity	NPD6168	Clinical (unspecified phase)
0.9346	High Similarity	NPD3882	Suspended
0.9262	High Similarity	NPD1512	Approved
0.9216	High Similarity	NPD2801	Approved
0.9156	High Similarity	NPD3817	Phase 2
0.913	High Similarity	NPD6797	Phase 2
0.9128	High Similarity	NPD1511	Approved
0.9074	High Similarity	NPD7251	Discontinued
0.9038	High Similarity	NPD7075	Discontinued
0.8968	High Similarity	NPD7096	Clinical (unspecified phase)
0.8951	High Similarity	NPD7074	Phase 3
0.894	High Similarity	NPD4378	Clinical (unspecified phase)
0.8902	High Similarity	NPD4338	Clinical (unspecified phase)
0.8902	High Similarity	NPD7808	Phase 3
0.8889	High Similarity	NPD7054	Approved
0.8854	High Similarity	NPD4868	Clinical (unspecified phase)
0.8851	High Similarity	NPD1552	Clinical (unspecified phase)
0.8851	High Similarity	NPD1550	Clinical (unspecified phase)
0.8834	High Similarity	NPD7472	Approved
0.8827	High Similarity	NPD3818	Discontinued
0.8792	High Similarity	NPD1549	Phase 2
0.8774	High Similarity	NPD4380	Phase 2
0.875	High Similarity	NPD6799	Approved
0.8679	High Similarity	NPD4381	Clinical (unspecified phase)
0.8662	High Similarity	NPD6801	Discontinued
0.8659	High Similarity	NPD7804	Clinical (unspecified phase)
0.8571	High Similarity	NPD5494	Approved
0.8554	High Similarity	NPD7993	Clinical (unspecified phase)
0.8535	High Similarity	NPD6599	Discontinued
0.8533	High Similarity	NPD2796	Approved
0.8467	Intermediate Similarity	NPD1510	Phase 2
0.8438	Intermediate Similarity	NPD5402	Approved
0.8438	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8375	Intermediate Similarity	NPD7819	Suspended
0.8344	Intermediate Similarity	NPD5403	Approved
0.8322	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8322	Intermediate Similarity	NPD1240	Approved
0.8322	Intermediate Similarity	NPD1613	Approved
0.8293	Intermediate Similarity	NPD6959	Discontinued
0.825	Intermediate Similarity	NPD7411	Suspended
0.8242	Intermediate Similarity	NPD6232	Discontinued
0.8217	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8217	Intermediate Similarity	NPD5401	Approved
0.8214	Intermediate Similarity	NPD5844	Phase 1
0.8212	Intermediate Similarity	NPD1607	Approved
0.8204	Intermediate Similarity	NPD7473	Discontinued
0.82	Intermediate Similarity	NPD943	Approved
0.8182	Intermediate Similarity	NPD1247	Approved
0.8176	Intermediate Similarity	NPD6559	Discontinued
0.8176	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8171	Intermediate Similarity	NPD919	Approved
0.8148	Intermediate Similarity	NPD1465	Phase 2
0.8108	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8084	Intermediate Similarity	NPD3926	Phase 2
0.8	Intermediate Similarity	NPD3027	Phase 3
0.7949	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7941	Intermediate Similarity	NPD3751	Discontinued
0.7929	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7917	Intermediate Similarity	NPD3787	Discontinued
0.7911	Intermediate Similarity	NPD6190	Approved
0.7908	Intermediate Similarity	NPD230	Phase 1
0.7871	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.787	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7848	Intermediate Similarity	NPD4628	Phase 3
0.7848	Intermediate Similarity	NPD3750	Approved
0.7831	Intermediate Similarity	NPD7768	Phase 2
0.7829	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD2935	Discontinued
0.7821	Intermediate Similarity	NPD1551	Phase 2
0.7785	Intermediate Similarity	NPD2800	Approved
0.7785	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD3749	Approved
0.7778	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7765	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7764	Intermediate Similarity	NPD2534	Approved
0.7764	Intermediate Similarity	NPD2532	Approved
0.7764	Intermediate Similarity	NPD2533	Approved
0.7712	Intermediate Similarity	NPD6798	Discontinued
0.7707	Intermediate Similarity	NPD6099	Approved
0.7707	Intermediate Similarity	NPD6100	Approved
0.7684	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD447	Suspended
0.7647	Intermediate Similarity	NPD7199	Phase 2
0.7633	Intermediate Similarity	NPD6234	Discontinued
0.7622	Intermediate Similarity	NPD1653	Approved
0.7596	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7584	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD4908	Phase 1
0.7568	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7564	Intermediate Similarity	NPD6355	Discontinued
0.7564	Intermediate Similarity	NPD1933	Approved
0.7561	Intermediate Similarity	NPD920	Approved
0.7556	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7548	Intermediate Similarity	NPD6233	Phase 2
0.7547	Intermediate Similarity	NPD2344	Approved
0.7532	Intermediate Similarity	NPD3748	Approved
0.7516	Intermediate Similarity	NPD6651	Approved
0.7516	Intermediate Similarity	NPD9494	Approved
0.7516	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5953	Discontinued
0.7486	Intermediate Similarity	NPD7286	Phase 2
0.7484	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD3226	Approved
0.7467	Intermediate Similarity	NPD1610	Phase 2
0.7453	Intermediate Similarity	NPD1243	Approved
0.7444	Intermediate Similarity	NPD8434	Phase 2
0.744	Intermediate Similarity	NPD37	Approved
0.7439	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD2346	Discontinued
0.7429	Intermediate Similarity	NPD7228	Approved
0.7423	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD2799	Discontinued
0.7421	Intermediate Similarity	NPD7033	Discontinued
0.7414	Intermediate Similarity	NPD2403	Approved
0.7412	Intermediate Similarity	NPD4965	Approved
0.7412	Intermediate Similarity	NPD4967	Phase 2
0.7412	Intermediate Similarity	NPD4966	Approved
0.7407	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD4360	Phase 2
0.7391	Intermediate Similarity	NPD4363	Phase 3
0.7389	Intermediate Similarity	NPD4060	Phase 1
0.7386	Intermediate Similarity	NPD1203	Approved
0.738	Intermediate Similarity	NPD6776	Approved
0.738	Intermediate Similarity	NPD6779	Approved
0.738	Intermediate Similarity	NPD6780	Approved
0.738	Intermediate Similarity	NPD6781	Approved
0.738	Intermediate Similarity	NPD6778	Approved
0.738	Intermediate Similarity	NPD6782	Approved
0.738	Intermediate Similarity	NPD6777	Approved
0.7378	Intermediate Similarity	NPD7390	Discontinued
0.7374	Intermediate Similarity	NPD8313	Approved
0.7374	Intermediate Similarity	NPD8312	Approved
0.7372	Intermediate Similarity	NPD2313	Discontinued
0.7362	Intermediate Similarity	NPD2309	Approved
0.736	Intermediate Similarity	NPD7685	Pre-registration
0.7355	Intermediate Similarity	NPD6832	Phase 2
0.7354	Intermediate Similarity	NPD7435	Discontinued
0.7348	Intermediate Similarity	NPD8150	Discontinued
0.7342	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD1548	Phase 1
0.7314	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD5710	Approved
0.7299	Intermediate Similarity	NPD5711	Approved
0.729	Intermediate Similarity	NPD2861	Phase 2
0.7278	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD3268	Approved
0.7257	Intermediate Similarity	NPD5242	Approved
0.7256	Intermediate Similarity	NPD3887	Approved
0.7256	Intermediate Similarity	NPD2354	Approved
0.7251	Intermediate Similarity	NPD5353	Approved
0.724	Intermediate Similarity	NPD7584	Approved
0.7239	Intermediate Similarity	NPD1652	Phase 2
0.7235	Intermediate Similarity	NPD6844	Discontinued
0.7232	Intermediate Similarity	NPD2163	Approved
0.7229	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD2798	Approved
0.7222	Intermediate Similarity	NPD7266	Discontinued
0.7215	Intermediate Similarity	NPD4062	Phase 3
0.7197	Intermediate Similarity	NPD7095	Approved
0.7197	Intermediate Similarity	NPD4625	Phase 3
0.719	Intermediate Similarity	NPD9717	Approved
0.719	Intermediate Similarity	NPD9269	Phase 2
0.719	Intermediate Similarity	NPD1608	Approved
0.7178	Intermediate Similarity	NPD2424	Discontinued
0.7173	Intermediate Similarity	NPD7696	Phase 3
0.7173	Intermediate Similarity	NPD7698	Approved
0.7173	Intermediate Similarity	NPD7697	Approved
0.7165	Intermediate Similarity	NPD8151	Discontinued
0.7161	Intermediate Similarity	NPD2797	Approved
0.716	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD2494	Approved
0.7158	Intermediate Similarity	NPD2493	Approved
0.7143	Intermediate Similarity	NPD4749	Approved
0.7135	Intermediate Similarity	NPD7871	Phase 2
0.7135	Intermediate Similarity	NPD7870	Phase 2
0.7134	Intermediate Similarity	NPD2654	Approved
0.7128	Intermediate Similarity	NPD7874	Approved
0.7128	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD4662	Approved
0.7126	Intermediate Similarity	NPD4661	Approved
0.7125	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD5124	Phase 1
0.7124	Intermediate Similarity	NPD422	Phase 1
0.7117	Intermediate Similarity	NPD1471	Phase 3
0.7113	Intermediate Similarity	NPD7701	Phase 2
0.7112	Intermediate Similarity	NPD6534	Approved
0.7112	Intermediate Similarity	NPD6535	Approved
0.7102	Intermediate Similarity	NPD7229	Phase 3
0.7099	Intermediate Similarity	NPD4308	Phase 3
0.7093	Intermediate Similarity	NPD8455	Phase 2
0.7083	Intermediate Similarity	NPD5049	Phase 3

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