NPASS Compound

Structure

NPC261470 OpenBabel07101719252D 29 32 0 0 0 0 0 0 0 0999 V2000 -0.2588 -1.9659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7934 -0.3912 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 3.5000 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 4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 3.0000 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 5.1962 3.0000 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 6.9282 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 3.4641 2.0000 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 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 3.5000 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 3.4641 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 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 22 1 0 0 0 0 2 22 1 0 0 0 0 3 26 1 0 0 0 0 4 27 1 0 0 0 0 5 6 2 0 0 0 0 5 11 1 0 0 0 0 6 22 1 0 0 0 0 7 12 2 0 0 0 0 7 18 1 0 0 0 0 8 14 1 0 0 0 0 8 16 2 0 0 0 0 9 15 2 0 0 0 0 9 17 1 0 0 0 0 10 13 2 0 0 0 0 10 28 1 0 0 0 0 11 17 2 0 0 0 0 11 21 1 0 0 0 0 12 13 1 0 0 0 0 12 16 1 0 0 0 0 13 20 1 0 0 0 0 14 18 2 0 0 0 0 14 23 1 0 0 0 0 15 19 1 0 0 0 0 15 24 1 0 0 0 0 16 26 1 0 0 0 0 17 29 1 0 0 0 0 18 27 1 0 0 0 0 19 20 1 0 0 0 0 19 21 2 0 0 0 0 20 25 2 0 0 0 0 21 28 1 0 0 0 0 22 29 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	396.12
Volume:	392.646
LogP:	4.062
LogD:	3.229
LogS:	-3.673
# Rotatable Bonds:	3
TPSA:	98.36
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.688
Synthetic Accessibility Score:	3.023
Fsp3:	0.227
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:	-4.81
MDCK Permeability:	2.0352848878246732e-05
Pgp-inhibitor:	0.179
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.064
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.038

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.005
Plasma Protein Binding (PPB):	94.12104797363281%
Volume Distribution (VD):	0.464
Pgp-substrate:	7.576539993286133%

ADMET: Metabolism

CYP1A2-inhibitor:	0.651
CYP1A2-substrate:	0.914
CYP2C19-inhibitor:	0.588
CYP2C19-substrate:	0.075
CYP2C9-inhibitor:	0.858
CYP2C9-substrate:	0.874
CYP2D6-inhibitor:	0.729
CYP2D6-substrate:	0.722
CYP3A4-inhibitor:	0.53
CYP3A4-substrate:	0.226

ADMET: Excretion

Clearance (CL):	4.482
Half-life (T1/2):	0.519

ADMET: Toxicity

hERG Blockers:	0.017
Human Hepatotoxicity (H-HT):	0.806
Drug-inuced Liver Injury (DILI):	0.933
AMES Toxicity:	0.155
Rat Oral Acute Toxicity:	0.877
Maximum Recommended Daily Dose:	0.682
Skin Sensitization:	0.251
Carcinogencity:	0.758
Eye Corrosion:	0.003
Eye Irritation:	0.135
Respiratory Toxicity:	0.797

Download Data

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

Natural Product: NPC261470

Natural Product ID:	NPC261470
*Common Name:**	4-Demethyltoxicarol Isoflavone
IUPAC Name:	5-hydroxy-3-(4-hydroxy-2,5-dimethoxyphenyl)-8,8-dimethylpyrano[2,3-h]chromen-4-one
Synonyms:	4'-Demethyltoxicarol Isoflavone; 4-Demethyltoxicarol Isoflavone
Standard InCHIKey:	LKQBEBUFBFOQAS-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C22H20O7/c1-22(2)6-5-11-17(29-22)9-15(24)19-20(25)13(10-28-21(11)19)12-7-18(27-4)14(23)8-16(12)26-3/h5-10,23-24H,1-4H3
SMILES:	COc1cc(O)c(cc1c1coc2c(c1=O)c(O)cc1c2C=CC(O1)(C)C)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL250439
PubChem CID:	14057034
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002506] Isoflavonoids [CHEMONTID:0003530] Pyranoisoflavonoids

*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
NPO31008	Ardisia colorata	Species	Primulaceae	Eukaryota	n.a.	fruit	n.a.	PMID[11767097]
NPO24609	Millettia brandisiana	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18039011]
NPO31008	Ardisia colorata	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19124248]
NPO24609	Millettia brandisiana	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19124248]
NPO31008	Ardisia colorata	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24609	Millettia brandisiana	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	2
Others	13

Activity Type	# Activity
Cell Line	15

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT579	Cell Line	DLD-1	Homo sapiens	IC50	>	25000.0	nM	PMID[484513]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	>	25000.0	nM	PMID[484513]
NPT579	Cell Line	DLD-1	Homo sapiens	Fold change	=	2.4	n.a.	PMID[484513]
NPT196	Cell Line	AGS	Homo sapiens	Activity	=	5.6	%	PMID[484514]
NPT196	Cell Line	AGS	Homo sapiens	Activity	=	9.6	%	PMID[484514]
NPT196	Cell Line	AGS	Homo sapiens	Activity	=	3.9	%	PMID[484514]
NPT196	Cell Line	AGS	Homo sapiens	Activity	=	15.2	%	PMID[484514]
NPT196	Cell Line	AGS	Homo sapiens	Activity	=	6.9	%	PMID[484514]
NPT196	Cell Line	AGS	Homo sapiens	Activity	=	17.4	%	PMID[484514]
NPT196	Cell Line	AGS	Homo sapiens	Activity	=	12.9	%	PMID[484514]
NPT196	Cell Line	AGS	Homo sapiens	Activity	=	12.1	%	PMID[484514]
NPT196	Cell Line	AGS	Homo sapiens	Activity	=	19.5	%	PMID[484514]
NPT196	Cell Line	AGS	Homo sapiens	Activity	=	16.3	%	PMID[484514]
NPT196	Cell Line	AGS	Homo sapiens	Activity	=	44.1	%	PMID[484514]
NPT196	Cell Line	AGS	Homo sapiens	Activity	=	23.4	%	PMID[484514]

☑ 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 NPC261470 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	443
0.1-0.2	1956
0.2-0.3	4764
0.3-0.4	11288
0.4-0.5	6431
0.5-0.6	3812
0.6-0.7	5121
0.7-0.8	4873
0.8-0.85	2172
0.85-0.9	1117
0.9-0.95	683
0.95-1	37

Similarity Score	Similarity Level	Natural Product ID
0.9871	High Similarity	NPC50960
0.9805	High Similarity	NPC259456
0.9742	High Similarity	NPC83922
0.9742	High Similarity	NPC472448
0.974	High Similarity	NPC476980
0.9677	High Similarity	NPC40037
0.9677	High Similarity	NPC167678
0.9677	High Similarity	NPC29876
0.9675	High Similarity	NPC74178
0.9675	High Similarity	NPC184755
0.9613	High Similarity	NPC204290
0.961	High Similarity	NPC476981
0.9554	High Similarity	NPC306321
0.9554	High Similarity	NPC303460
0.9551	High Similarity	NPC258331
0.9551	High Similarity	NPC198829
0.9548	High Similarity	NPC204879
0.9545	High Similarity	NPC276444
0.9545	High Similarity	NPC170026
0.9545	High Similarity	NPC471985
0.9545	High Similarity	NPC282307
0.9545	High Similarity	NPC472455
0.9542	High Similarity	NPC128961
0.95	High Similarity	NPC472276
0.9494	High Similarity	NPC239752
0.9494	High Similarity	NPC472450
0.9494	High Similarity	NPC275780
0.949	High Similarity	NPC474162
0.949	High Similarity	NPC474150
0.949	High Similarity	NPC81679
0.949	High Similarity	NPC194427
0.9487	High Similarity	NPC119209
0.9487	High Similarity	NPC118256
0.9487	High Similarity	NPC192686
0.9484	High Similarity	NPC474681
0.9484	High Similarity	NPC218313
0.9484	High Similarity	NPC218871
0.9484	High Similarity	NPC36852
0.9484	High Similarity	NPC52889
0.9484	High Similarity	NPC78225
0.9484	High Similarity	NPC476630
0.9484	High Similarity	NPC262286
0.9481	High Similarity	NPC200246
0.9481	High Similarity	NPC256925
0.9481	High Similarity	NPC213622
0.9481	High Similarity	NPC20830
0.9481	High Similarity	NPC256612
0.9481	High Similarity	NPC39184
0.9481	High Similarity	NPC234255
0.9481	High Similarity	NPC472280
0.9481	High Similarity	NPC134287
0.9481	High Similarity	NPC130589
0.9437	High Similarity	NPC471287
0.9434	High Similarity	NPC39091
0.943	High Similarity	NPC189473
0.943	High Similarity	NPC23298
0.9427	High Similarity	NPC134783
0.9427	High Similarity	NPC57715
0.9427	High Similarity	NPC474038
0.9427	High Similarity	NPC266314
0.9423	High Similarity	NPC469658
0.9423	High Similarity	NPC250214
0.9423	High Similarity	NPC95936
0.9419	High Similarity	NPC133970
0.9419	High Similarity	NPC138243
0.9419	High Similarity	NPC6633
0.9419	High Similarity	NPC191146
0.9419	High Similarity	NPC472916
0.9419	High Similarity	NPC470600
0.9419	High Similarity	NPC5322
0.9419	High Similarity	NPC68093
0.9419	High Similarity	NPC180340
0.9416	High Similarity	NPC69394
0.9416	High Similarity	NPC183878
0.9416	High Similarity	NPC145379
0.9416	High Similarity	NPC170492
0.9416	High Similarity	NPC255350
0.9416	High Similarity	NPC124714
0.9416	High Similarity	NPC280937
0.9416	High Similarity	NPC231018
0.9416	High Similarity	NPC47781
0.9416	High Similarity	NPC22519
0.9416	High Similarity	NPC176775
0.9416	High Similarity	NPC472408
0.9416	High Similarity	NPC274327
0.9416	High Similarity	NPC160951
0.9383	High Similarity	NPC310794
0.9375	High Similarity	NPC8965
0.9375	High Similarity	NPC471288
0.9371	High Similarity	NPC303174
0.9367	High Similarity	NPC474034
0.9367	High Similarity	NPC474033
0.9367	High Similarity	NPC229632
0.9367	High Similarity	NPC329760
0.9367	High Similarity	NPC220912
0.9363	High Similarity	NPC328102
0.9363	High Similarity	NPC188433
0.9363	High Similarity	NPC246478
0.9363	High Similarity	NPC28241
0.9363	High Similarity	NPC475784
0.9359	High Similarity	NPC210084
0.9359	High Similarity	NPC475267
0.9359	High Similarity	NPC78103
0.9359	High Similarity	NPC78071
0.9359	High Similarity	NPC470402
0.9359	High Similarity	NPC472910
0.9359	High Similarity	NPC48208
0.9359	High Similarity	NPC474208
0.9359	High Similarity	NPC291508
0.9359	High Similarity	NPC473272
0.9359	High Similarity	NPC223787
0.9359	High Similarity	NPC474836
0.9359	High Similarity	NPC96167
0.9359	High Similarity	NPC472914
0.9359	High Similarity	NPC156057
0.9359	High Similarity	NPC284820
0.9359	High Similarity	NPC245758
0.9359	High Similarity	NPC99597
0.9359	High Similarity	NPC472911
0.9359	High Similarity	NPC27337
0.9359	High Similarity	NPC162869
0.9359	High Similarity	NPC472913
0.9359	High Similarity	NPC222814
0.9355	High Similarity	NPC183597
0.9355	High Similarity	NPC227325
0.9355	High Similarity	NPC117992
0.9355	High Similarity	NPC163780
0.9355	High Similarity	NPC50715
0.9355	High Similarity	NPC128863
0.9355	High Similarity	NPC2476
0.9355	High Similarity	NPC201136
0.9355	High Similarity	NPC208197
0.9355	High Similarity	NPC4455
0.9355	High Similarity	NPC92659
0.9355	High Similarity	NPC152951
0.9355	High Similarity	NPC167815
0.9355	High Similarity	NPC196439
0.9355	High Similarity	NPC138360
0.9355	High Similarity	NPC280339
0.9355	High Similarity	NPC57674
0.9355	High Similarity	NPC230149
0.9355	High Similarity	NPC146165
0.9355	High Similarity	NPC113906
0.9355	High Similarity	NPC168247
0.9355	High Similarity	NPC2928
0.9351	High Similarity	NPC275836
0.9351	High Similarity	NPC239128
0.9351	High Similarity	NPC471982
0.9351	High Similarity	NPC131266
0.9351	High Similarity	NPC142540
0.9351	High Similarity	NPC60972
0.9351	High Similarity	NPC57030
0.9351	High Similarity	NPC35763
0.9351	High Similarity	NPC25270
0.9351	High Similarity	NPC83508
0.9351	High Similarity	NPC245382
0.9351	High Similarity	NPC269451
0.9351	High Similarity	NPC100887
0.9351	High Similarity	NPC156222
0.9351	High Similarity	NPC166201
0.9351	High Similarity	NPC301323
0.9351	High Similarity	NPC237994
0.9351	High Similarity	NPC39007
0.9351	High Similarity	NPC216769
0.9351	High Similarity	NPC187498
0.9351	High Similarity	NPC188203
0.9351	High Similarity	NPC212678
0.9351	High Similarity	NPC71334
0.9351	High Similarity	NPC100971
0.9351	High Similarity	NPC222830
0.9351	High Similarity	NPC131624
0.9351	High Similarity	NPC181209
0.9351	High Similarity	NPC241498
0.9351	High Similarity	NPC293183
0.9351	High Similarity	NPC39732
0.9351	High Similarity	NPC256283
0.9351	High Similarity	NPC162313
0.9351	High Similarity	NPC120163
0.9351	High Similarity	NPC291802
0.9351	High Similarity	NPC161277
0.9351	High Similarity	NPC209487
0.9351	High Similarity	NPC275722
0.9351	High Similarity	NPC121522
0.9351	High Similarity	NPC100263
0.9351	High Similarity	NPC198826
0.9317	High Similarity	NPC177480
0.9317	High Similarity	NPC288813
0.9313	High Similarity	NPC120593
0.9313	High Similarity	NPC37870
0.9313	High Similarity	NPC472449
0.9308	High Similarity	NPC472625
0.9308	High Similarity	NPC248638
0.9308	High Similarity	NPC470459
0.9308	High Similarity	NPC236521
0.9308	High Similarity	NPC152659
0.9308	High Similarity	NPC186686
0.9308	High Similarity	NPC124038
0.9308	High Similarity	NPC41301
0.9304	High Similarity	NPC61010
0.9304	High Similarity	NPC26326

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 NPC261470 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	418
0.1-0.2	1008
0.2-0.3	1934
0.3-0.4	2671
0.4-0.5	1701
0.5-0.6	936
0.6-0.7	320
0.7-0.8	112
0.8-0.85	30
0.85-0.9	18
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9416	High Similarity	NPD2801	Approved
0.9167	High Similarity	NPD2393	Clinical (unspecified phase)
0.9103	High Similarity	NPD1934	Approved
0.8931	High Similarity	NPD3882	Suspended
0.8882	High Similarity	NPD5494	Approved
0.8831	High Similarity	NPD1511	Approved
0.8788	High Similarity	NPD3818	Discontinued
0.878	High Similarity	NPD6167	Clinical (unspecified phase)
0.878	High Similarity	NPD6168	Clinical (unspecified phase)
0.878	High Similarity	NPD6166	Phase 2
0.8734	High Similarity	NPD4380	Phase 2
0.8718	High Similarity	NPD1512	Approved
0.8654	High Similarity	NPD4378	Clinical (unspecified phase)
0.8639	High Similarity	NPD4338	Clinical (unspecified phase)
0.8634	High Similarity	NPD3817	Phase 2
0.8623	High Similarity	NPD7054	Approved
0.858	High Similarity	NPD4868	Clinical (unspecified phase)
0.8571	High Similarity	NPD7074	Phase 3
0.8571	High Similarity	NPD7472	Approved
0.8535	High Similarity	NPD7410	Clinical (unspecified phase)
0.8415	Intermediate Similarity	NPD7075	Discontinued
0.8415	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8412	Intermediate Similarity	NPD6797	Phase 2
0.8405	Intermediate Similarity	NPD5402	Approved
0.8402	Intermediate Similarity	NPD5844	Phase 1
0.8395	Intermediate Similarity	NPD6801	Discontinued
0.8373	Intermediate Similarity	NPD1247	Approved
0.8363	Intermediate Similarity	NPD7251	Discontinued
0.8344	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8323	Intermediate Similarity	NPD6232	Discontinued
0.8314	Intermediate Similarity	NPD7808	Phase 3
0.8312	Intermediate Similarity	NPD1510	Phase 2
0.8284	Intermediate Similarity	NPD7473	Discontinued
0.8269	Intermediate Similarity	NPD1549	Phase 2
0.8258	Intermediate Similarity	NPD2796	Approved
0.8232	Intermediate Similarity	NPD7819	Suspended
0.8232	Intermediate Similarity	NPD1465	Phase 2
0.8221	Intermediate Similarity	NPD7411	Suspended
0.8205	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8205	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8187	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8155	Intermediate Similarity	NPD6959	Discontinued
0.8125	Intermediate Similarity	NPD6799	Approved
0.8092	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8052	Intermediate Similarity	NPD1240	Approved
0.8052	Intermediate Similarity	NPD943	Approved
0.8036	Intermediate Similarity	NPD919	Approved
0.8025	Intermediate Similarity	NPD2935	Discontinued
0.7975	Intermediate Similarity	NPD5403	Approved
0.7949	Intermediate Similarity	NPD1607	Approved
0.7943	Intermediate Similarity	NPD6559	Discontinued
0.7939	Intermediate Similarity	NPD6599	Discontinued
0.7933	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7917	Intermediate Similarity	NPD7768	Phase 2
0.7907	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7875	Intermediate Similarity	NPD2800	Approved
0.7866	Intermediate Similarity	NPD920	Approved
0.7853	Intermediate Similarity	NPD5401	Approved
0.7849	Intermediate Similarity	NPD3926	Phase 2
0.7826	Intermediate Similarity	NPD3750	Approved
0.7771	Intermediate Similarity	NPD230	Phase 1
0.7765	Intermediate Similarity	NPD3749	Approved
0.7764	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7747	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD2533	Approved
0.7744	Intermediate Similarity	NPD2532	Approved
0.7744	Intermediate Similarity	NPD2534	Approved
0.7707	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7707	Intermediate Similarity	NPD1613	Approved
0.7702	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.767	Intermediate Similarity	NPD7286	Phase 2
0.7667	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7658	Intermediate Similarity	NPD447	Suspended
0.7651	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7636	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7628	Intermediate Similarity	NPD3027	Phase 3
0.7614	Intermediate Similarity	NPD3751	Discontinued
0.7613	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7605	Intermediate Similarity	NPD1653	Approved
0.7584	Intermediate Similarity	NPD5953	Discontinued
0.758	Intermediate Similarity	NPD2313	Discontinued
0.7578	Intermediate Similarity	NPD1551	Phase 2
0.7561	Intermediate Similarity	NPD6190	Approved
0.756	Intermediate Similarity	NPD3226	Approved
0.7546	Intermediate Similarity	NPD1243	Approved
0.7516	Intermediate Similarity	NPD3748	Approved
0.7516	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD2799	Discontinued
0.7515	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD6234	Discontinued
0.75	Intermediate Similarity	NPD9494	Approved
0.75	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4628	Phase 3
0.75	Intermediate Similarity	NPD6651	Approved
0.75	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD3787	Discontinued
0.7468	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.746	Intermediate Similarity	NPD6780	Approved
0.746	Intermediate Similarity	NPD6779	Approved
0.746	Intermediate Similarity	NPD6782	Approved
0.746	Intermediate Similarity	NPD6777	Approved
0.746	Intermediate Similarity	NPD6776	Approved
0.746	Intermediate Similarity	NPD6781	Approved
0.746	Intermediate Similarity	NPD6778	Approved
0.7444	Intermediate Similarity	NPD7685	Pre-registration
0.7429	Intermediate Similarity	NPD7199	Phase 2
0.7423	Intermediate Similarity	NPD2346	Discontinued
0.7423	Intermediate Similarity	NPD2344	Approved
0.7394	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD7390	Discontinued
0.7363	Intermediate Similarity	NPD8312	Approved
0.7363	Intermediate Similarity	NPD8313	Approved
0.7362	Intermediate Similarity	NPD6099	Approved
0.7362	Intermediate Similarity	NPD6100	Approved
0.7358	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7345	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7344	Intermediate Similarity	NPD7435	Discontinued
0.7337	Intermediate Similarity	NPD8150	Discontinued
0.7337	Intermediate Similarity	NPD8434	Phase 2
0.7329	Intermediate Similarity	NPD1933	Approved
0.7326	Intermediate Similarity	NPD6844	Discontinued
0.7326	Intermediate Similarity	NPD37	Approved
0.7321	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD7584	Approved
0.7318	Intermediate Similarity	NPD7228	Approved
0.7299	Intermediate Similarity	NPD4967	Phase 2
0.7299	Intermediate Similarity	NPD4966	Approved
0.7299	Intermediate Similarity	NPD4965	Approved
0.7289	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7287	Intermediate Similarity	NPD4363	Phase 3
0.7287	Intermediate Similarity	NPD4360	Phase 2
0.7254	Intermediate Similarity	NPD7696	Phase 3
0.7254	Intermediate Similarity	NPD7698	Approved
0.7254	Intermediate Similarity	NPD7697	Approved
0.7247	Intermediate Similarity	NPD5242	Approved
0.7246	Intermediate Similarity	NPD2309	Approved
0.7233	Intermediate Similarity	NPD4908	Phase 1
0.7222	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD5124	Phase 1
0.7216	Intermediate Similarity	NPD7871	Phase 2
0.7216	Intermediate Similarity	NPD7870	Phase 2
0.7213	Intermediate Similarity	NPD7549	Discontinued
0.7202	Intermediate Similarity	NPD6823	Phase 2
0.7196	Intermediate Similarity	NPD6535	Approved
0.7196	Intermediate Similarity	NPD6534	Approved
0.7195	Intermediate Similarity	NPD7033	Discontinued
0.7194	Intermediate Similarity	NPD7701	Phase 2
0.7191	Intermediate Similarity	NPD5710	Approved
0.7191	Intermediate Similarity	NPD5711	Approved
0.7172	Intermediate Similarity	NPD7783	Phase 2
0.7172	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7157	Intermediate Similarity	NPD8151	Discontinued
0.7152	Intermediate Similarity	NPD1203	Approved
0.7151	Intermediate Similarity	NPD7458	Discontinued
0.7125	Intermediate Similarity	NPD6832	Phase 2
0.7121	Intermediate Similarity	NPD7874	Approved
0.7121	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD2403	Approved
0.7107	Intermediate Similarity	NPD2798	Approved
0.7095	Intermediate Similarity	NPD7229	Phase 3
0.7091	Intermediate Similarity	NPD4308	Phase 3
0.7085	Intermediate Similarity	NPD7801	Approved
0.7083	Intermediate Similarity	NPD7700	Phase 2
0.7083	Intermediate Similarity	NPD7699	Phase 2
0.7081	Intermediate Similarity	NPD4625	Phase 3
0.7078	Intermediate Similarity	NPD1548	Phase 1
0.707	Intermediate Similarity	NPD9269	Phase 2
0.7069	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD6386	Approved
0.7069	Intermediate Similarity	NPD6385	Approved
0.7068	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD4361	Phase 2
0.7066	Intermediate Similarity	NPD2424	Discontinued
0.7052	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD1729	Discontinued
0.7045	Intermediate Similarity	NPD5353	Approved
0.7037	Intermediate Similarity	NPD3268	Approved
0.7018	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7017	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD2899	Discontinued
0.7006	Intermediate Similarity	NPD1610	Phase 2
0.6994	Remote Similarity	NPD6233	Phase 2
0.6981	Remote Similarity	NPD3225	Approved
0.6962	Remote Similarity	NPD9717	Approved
0.6959	Remote Similarity	NPD4357	Discontinued
0.6957	Remote Similarity	NPD2861	Phase 2
0.6951	Remote Similarity	NPD4060	Phase 1
0.6949	Remote Similarity	NPD4288	Approved
0.6946	Remote Similarity	NPD5404	Approved
0.6946	Remote Similarity	NPD5405	Approved
0.6946	Remote Similarity	NPD5406	Approved
0.6946	Remote Similarity	NPD5408	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