NPASS Compound

Structure

NPC186847 OpenBabel07101718242D 42 47 0 0 1 0 0 0 0 0999 V2000 -4.2399 -0.4896 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0879 0.9792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6960 0.9792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0879 -0.9792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9359 0.4896 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5439 1.4688 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5439 -0.4896 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.9167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6960 3.9167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5439 -1.4688 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2399 0.4896 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6960 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9359 -0.4896 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8480 4.4063 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3919 0.9792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3919 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.9375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5439 -0.4896 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6960 -1.9583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6960 2.9375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8480 2.4479 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6960 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8480 -1.4688 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6960 0.9792 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8480 1.4687 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.9583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8480 -1.4687 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5439 1.4687 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8480 -0.4896 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8480 -0.4896 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7839 -0.9792 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8480 5.3854 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2399 1.4688 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2399 -0.4896 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8480 2.4479 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3919 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6960 -2.9375 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 0.9792 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.9375 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6960 -1.9583 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5439 2.4479 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 4 1 0 0 0 0 1 11 2 0 0 0 0 2 5 2 0 0 0 0 2 11 1 0 0 0 0 3 6 2 0 0 0 0 3 12 1 0 0 0 0 4 13 2 0 0 0 0 5 13 1 0 0 0 0 6 15 1 0 0 0 0 7 12 2 0 0 0 0 7 16 1 0 0 0 0 8 14 2 0 0 0 0 8 17 1 0 0 0 0 9 14 1 0 0 0 0 9 20 2 0 0 0 0 10 18 2 0 0 0 0 10 19 1 0 0 0 0 13 31 1 0 0 0 0 14 32 1 0 0 0 0 15 16 2 0 0 0 0 15 33 1 0 0 0 0 16 34 1 0 0 0 0 17 21 2 0 0 0 0 17 35 1 0 0 0 0 18 22 1 0 0 0 0 18 36 1 0 0 0 0 19 23 2 0 0 0 0 19 37 1 0 0 0 0 20 21 1 0 0 0 0 20 41 1 0 0 0 0 21 25 1 0 0 0 0 22 30 2 0 0 0 0 23 26 1 0 0 0 0 23 30 1 0 0 0 0 24 22 1 6 0 0 0 24 25 1 0 0 0 0 24 28 1 0 0 0 0 25 38 2 0 0 0 0 26 27 1 0 0 0 0 26 39 2 0 0 0 0 27 29 1 0 0 0 0 27 40 1 1 0 0 0 28 11 1 1 0 0 0 28 41 1 0 0 0 0 29 12 1 6 0 0 0 29 42 1 0 0 0 0 30 42 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	574.11
Volume:	544.67
LogP:	3.046
LogD:	1.875
LogS:	-5.291
# Rotatable Bonds:	3
TPSA:	221.51
# H-Bond Aceptor:	12
# H-Bond Donor:	9
# Rings:	6
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.141
Synthetic Accessibility Score:	4.199
Fsp3:	0.1
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.401
MDCK Permeability:	5.1239539970993064e-06
Pgp-inhibitor:	0.016
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.783
20% Bioavailability (F20%):	0.912
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.002
Plasma Protein Binding (PPB):	94.73596954345703%
Volume Distribution (VD):	0.445
Pgp-substrate:	6.373703479766846%

ADMET: Metabolism

CYP1A2-inhibitor:	0.359
CYP1A2-substrate:	0.063
CYP2C19-inhibitor:	0.05
CYP2C19-substrate:	0.038
CYP2C9-inhibitor:	0.623
CYP2C9-substrate:	0.788
CYP2D6-inhibitor:	0.025
CYP2D6-substrate:	0.205
CYP3A4-inhibitor:	0.112
CYP3A4-substrate:	0.043

ADMET: Excretion

Clearance (CL):	5.576
Half-life (T1/2):	0.751

ADMET: Toxicity

hERG Blockers:	0.082
Human Hepatotoxicity (H-HT):	0.2
Drug-inuced Liver Injury (DILI):	0.989
AMES Toxicity:	0.679
Rat Oral Acute Toxicity:	0.114
Maximum Recommended Daily Dose:	0.083
Skin Sensitization:	0.56
Carcinogencity:	0.024
Eye Corrosion:	0.003
Eye Irritation:	0.877
Respiratory Toxicity:	0.015

Download Data

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

Natural Product: NPC186847

Natural Product ID:	NPC186847
*Common Name:**	(2S,2'r,3R,3'r)-2'-(3,4-Dihydroxyphenyl)-3',5,5',7,7'-Pentahydroxy-2-(4-Hydroxyphenyl)-3,8'-Bichroman-4,4'-Dione
IUPAC Name:	(2R,3R)-8-[(2S,3R)-5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-2,3-dihydrochromen-3-yl]-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-2,3-dihydrochromen-4-one
Synonyms:
Standard InCHIKey:	SNFOQVRNAHJPMU-BENTYHEHSA-N
Standard InCHI:	InChI=1S/C30H22O12/c31-13-4-1-11(2-5-13)28-24(25(38)21-17(35)8-14(32)9-20(21)41-28)22-18(36)10-19(37)23-26(39)27(40)29(42-30(22)23)12-3-6-15(33)16(34)7-12/h1-10,24,27-29,31-37,40H/t24-,27-,28+,29+/m0/s1
SMILES:	c1cc(ccc1[C@@H]1[C@@H](c2c(cc(c3C(=O)[C@@H]([C@@H](c4ccc(c(c4)O)O)Oc23)O)O)O)C(=O)c2c(cc(cc2O1)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL508885
PubChem CID:	161259
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001586] Biflavonoids and polyflavonoids

*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
NPO32446	calophyllum panciflorum	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10654415]
NPO19087	Garcinia kola	Species	Clusiaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[32644811]
NPO19087	Garcinia kola	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19087	Garcinia kola	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19087	Garcinia kola	Species	Clusiaceae	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
MIC	2
Others	10

Activity Type	# Activity
Cell Line	4
NON-MOLECULAR	4
Organism	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT80	Cell Line	Raji	Homo sapiens	Activity	=	70.0	%	PMID[518279]
NPT80	Cell Line	Raji	Homo sapiens	Activity	>	80.0	%	PMID[518279]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	28.7	%	PMID[518279]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	63.9	%	PMID[518279]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	90.3	%	PMID[518279]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	100.0	%	PMID[518279]
NPT1127	Organism	Porphyromonas gingivalis	Porphyromonas gingivalis	MIC	>	1000000.0	nM	PMID[518280]
NPT1127	Organism	Porphyromonas gingivalis	Porphyromonas gingivalis	MBC	>	1000.0	uM	PMID[518280]
NPT1483	Organism	Streptococcus sobrinus	Streptococcus sobrinus	MIC	=	250000.0	nM	PMID[518280]
NPT1483	Organism	Streptococcus sobrinus	Streptococcus sobrinus	MBC	=	1000.0	uM	PMID[518280]

☑ 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 NPC186847 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	474
0.1-0.2	1780
0.2-0.3	4026
0.3-0.4	10075
0.4-0.5	8147
0.5-0.6	3785
0.6-0.7	4970
0.7-0.8	5290
0.8-0.85	2649
0.85-0.9	1355
0.9-0.95	134
0.95-1	12

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC472454
1.0	High Similarity	NPC257667
0.9752	High Similarity	NPC107627
0.975	High Similarity	NPC224851
0.9627	High Similarity	NPC171985
0.9627	High Similarity	NPC320741
0.9625	High Similarity	NPC63438
0.9568	High Similarity	NPC260266
0.9451	High Similarity	NPC102277
0.9451	High Similarity	NPC279209
0.9444	High Similarity	NPC125039
0.9444	High Similarity	NPC36916
0.9444	High Similarity	NPC7688
0.9444	High Similarity	NPC7154
0.9444	High Similarity	NPC58223
0.9444	High Similarity	NPC72787
0.9444	High Similarity	NPC36
0.9441	High Similarity	NPC477841
0.939	High Similarity	NPC475212
0.9379	High Similarity	NPC289771
0.9379	High Similarity	NPC142252
0.9375	High Similarity	NPC123544
0.9349	High Similarity	NPC132111
0.9345	High Similarity	NPC324742
0.9325	High Similarity	NPC477840
0.9325	High Similarity	NPC62261
0.9321	High Similarity	NPC219927
0.9286	High Similarity	NPC265380
0.9277	High Similarity	NPC81332
0.9277	High Similarity	NPC262580
0.9277	High Similarity	NPC271848
0.9277	High Similarity	NPC289396
0.9277	High Similarity	NPC212038
0.9268	High Similarity	NPC471213
0.9268	High Similarity	NPC272560
0.9259	High Similarity	NPC471499
0.9255	High Similarity	NPC53545
0.9255	High Similarity	NPC22192
0.9255	High Similarity	NPC295090
0.9255	High Similarity	NPC117418
0.925	High Similarity	NPC69531
0.9235	High Similarity	NPC321916
0.9231	High Similarity	NPC185275
0.9212	High Similarity	NPC14662
0.9212	High Similarity	NPC295082
0.9202	High Similarity	NPC476247
0.9198	High Similarity	NPC287328
0.9198	High Similarity	NPC282009
0.9198	High Similarity	NPC470326
0.9193	High Similarity	NPC475184
0.9181	High Similarity	NPC318119
0.9172	High Similarity	NPC471789
0.9162	High Similarity	NPC65333
0.9162	High Similarity	NPC4200
0.9157	High Similarity	NPC177480
0.9157	High Similarity	NPC300307
0.9157	High Similarity	NPC326877
0.9146	High Similarity	NPC472625
0.9141	High Similarity	NPC165970
0.9141	High Similarity	NPC158188
0.9141	High Similarity	NPC472632
0.9141	High Similarity	NPC113163
0.9141	High Similarity	NPC288131
0.9141	High Similarity	NPC66618
0.9141	High Similarity	NPC305987
0.9141	High Similarity	NPC173137
0.9141	High Similarity	NPC228383
0.9141	High Similarity	NPC84324
0.9141	High Similarity	NPC26326
0.913	High Similarity	NPC32867
0.9128	High Similarity	NPC112380
0.9125	High Similarity	NPC244250
0.9125	High Similarity	NPC20907
0.9123	High Similarity	NPC150977
0.9107	High Similarity	NPC98583
0.9102	High Similarity	NPC287884
0.9102	High Similarity	NPC103307
0.9102	High Similarity	NPC8704
0.9102	High Similarity	NPC74559
0.9096	High Similarity	NPC243877
0.9091	High Similarity	NPC471788
0.9091	High Similarity	NPC224280
0.9091	High Similarity	NPC259757
0.9085	High Similarity	NPC474033
0.9085	High Similarity	NPC474150
0.9085	High Similarity	NPC474162
0.9085	High Similarity	NPC474034
0.9085	High Similarity	NPC220912
0.9085	High Similarity	NPC211107
0.908	High Similarity	NPC470183
0.908	High Similarity	NPC174953
0.908	High Similarity	NPC101731
0.9075	High Similarity	NPC179947
0.9075	High Similarity	NPC64755
0.9074	High Similarity	NPC474055
0.9074	High Similarity	NPC471209
0.9074	High Similarity	NPC472598
0.9068	High Similarity	NPC321779
0.9068	High Similarity	NPC134171
0.9068	High Similarity	NPC258474
0.9068	High Similarity	NPC201227
0.9068	High Similarity	NPC300668
0.9062	High Similarity	NPC19721
0.9062	High Similarity	NPC260491
0.9062	High Similarity	NPC61506
0.9062	High Similarity	NPC246162
0.9062	High Similarity	NPC36835
0.9062	High Similarity	NPC240476
0.9062	High Similarity	NPC9743
0.9053	High Similarity	NPC108202
0.9053	High Similarity	NPC99591
0.9053	High Similarity	NPC294629
0.9048	High Similarity	NPC100251
0.9048	High Similarity	NPC121333
0.9042	High Similarity	NPC188079
0.9036	High Similarity	NPC207575
0.9036	High Similarity	NPC120593
0.9036	High Similarity	NPC477517
0.9036	High Similarity	NPC82330
0.9036	High Similarity	NPC13481
0.903	High Similarity	NPC290160
0.903	High Similarity	NPC41301
0.903	High Similarity	NPC476295
0.9024	High Similarity	NPC266314
0.9024	High Similarity	NPC471210
0.9024	High Similarity	NPC472634
0.9024	High Similarity	NPC301256
0.9024	High Similarity	NPC471211
0.9024	High Similarity	NPC471212
0.9024	High Similarity	NPC134783
0.9024	High Similarity	NPC474038
0.9024	High Similarity	NPC312273
0.9023	High Similarity	NPC473618
0.9018	High Similarity	NPC172202
0.9018	High Similarity	NPC476410
0.9018	High Similarity	NPC51247
0.9018	High Similarity	NPC284127
0.9018	High Similarity	NPC473990
0.9012	High Similarity	NPC61112
0.9012	High Similarity	NPC291878
0.9012	High Similarity	NPC250922
0.9012	High Similarity	NPC201837
0.9012	High Similarity	NPC208152
0.9012	High Similarity	NPC78492
0.9012	High Similarity	NPC471500
0.9012	High Similarity	NPC195796
0.9012	High Similarity	NPC35038
0.9012	High Similarity	NPC309648
0.9012	High Similarity	NPC320825
0.9012	High Similarity	NPC13858
0.9012	High Similarity	NPC278778
0.9012	High Similarity	NPC326037
0.9012	High Similarity	NPC198489
0.9006	High Similarity	NPC213896
0.9006	High Similarity	NPC27532
0.9006	High Similarity	NPC325028
0.9006	High Similarity	NPC109594
0.9006	High Similarity	NPC256346
0.9006	High Similarity	NPC268193
0.9006	High Similarity	NPC326592
0.9006	High Similarity	NPC112701
0.9006	High Similarity	NPC246328
0.9006	High Similarity	NPC192083
0.9006	High Similarity	NPC244903
0.8994	High Similarity	NPC476374
0.8994	High Similarity	NPC168789
0.8988	High Similarity	NPC218488
0.8988	High Similarity	NPC78734
0.8988	High Similarity	NPC150767
0.8988	High Similarity	NPC476365
0.8982	High Similarity	NPC92565
0.8982	High Similarity	NPC8965
0.8982	High Similarity	NPC160156
0.8982	High Similarity	NPC470456
0.8982	High Similarity	NPC477154
0.8982	High Similarity	NPC117854
0.8982	High Similarity	NPC474024
0.8982	High Similarity	NPC6588
0.8976	High Similarity	NPC234052
0.8976	High Similarity	NPC293319
0.8976	High Similarity	NPC475888
0.8976	High Similarity	NPC473010
0.8976	High Similarity	NPC470457
0.897	High Similarity	NPC473011
0.897	High Similarity	NPC472635
0.897	High Similarity	NPC473012
0.8963	High Similarity	NPC472631
0.8963	High Similarity	NPC119209
0.8963	High Similarity	NPC118256
0.8963	High Similarity	NPC321399
0.8963	High Similarity	NPC475784
0.8963	High Similarity	NPC472630
0.8963	High Similarity	NPC263449
0.8963	High Similarity	NPC36217
0.8963	High Similarity	NPC192686
0.8957	High Similarity	NPC52530
0.8957	High Similarity	NPC471515
0.8957	High Similarity	NPC1796
0.8957	High Similarity	NPC291508
0.8957	High Similarity	NPC27337

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 NPC186847 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	443
0.1-0.2	938
0.2-0.3	1874
0.3-0.4	2614
0.4-0.5	1780
0.5-0.6	922
0.6-0.7	399
0.7-0.8	130
0.8-0.85	33
0.85-0.9	13
0.9-0.95	4
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9444	High Similarity	NPD6168	Clinical (unspecified phase)
0.9444	High Similarity	NPD6167	Clinical (unspecified phase)
0.9444	High Similarity	NPD6166	Phase 2
0.9048	High Similarity	NPD7993	Clinical (unspecified phase)
0.9006	High Similarity	NPD2393	Clinical (unspecified phase)
0.8827	High Similarity	NPD1934	Approved
0.8824	High Similarity	NPD6797	Phase 2
0.8795	High Similarity	NPD6959	Discontinued
0.878	High Similarity	NPD4868	Clinical (unspecified phase)
0.8772	High Similarity	NPD7251	Discontinued
0.8765	High Similarity	NPD7074	Phase 3
0.8706	High Similarity	NPD7054	Approved
0.8704	High Similarity	NPD4380	Phase 2
0.8655	High Similarity	NPD7472	Approved
0.8623	High Similarity	NPD5494	Approved
0.8613	High Similarity	NPD7808	Phase 3
0.8613	High Similarity	NPD4338	Clinical (unspecified phase)
0.8606	High Similarity	NPD8443	Clinical (unspecified phase)
0.8596	High Similarity	NPD7804	Clinical (unspecified phase)
0.8571	High Similarity	NPD1512	Approved
0.8554	High Similarity	NPD3882	Suspended
0.8545	High Similarity	NPD2801	Approved
0.8538	High Similarity	NPD3818	Discontinued
0.8503	High Similarity	NPD7075	Discontinued
0.8447	Intermediate Similarity	NPD1511	Approved
0.8395	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8393	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8383	Intermediate Similarity	NPD3817	Phase 2
0.8372	Intermediate Similarity	NPD7473	Discontinued
0.8323	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8314	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8304	Intermediate Similarity	NPD6232	Discontinued
0.8276	Intermediate Similarity	NPD5844	Phase 1
0.8263	Intermediate Similarity	NPD6801	Discontinued
0.8249	Intermediate Similarity	NPD8313	Approved
0.8249	Intermediate Similarity	NPD8312	Approved
0.8204	Intermediate Similarity	NPD7411	Suspended
0.8187	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8187	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8171	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8166	Intermediate Similarity	NPD5402	Approved
0.8137	Intermediate Similarity	NPD1549	Phase 2
0.8107	Intermediate Similarity	NPD1465	Phase 2
0.8107	Intermediate Similarity	NPD7819	Suspended
0.8034	Intermediate Similarity	NPD6559	Discontinued
0.8033	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8022	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD7768	Phase 2
0.7989	Intermediate Similarity	NPD3787	Discontinued
0.7964	Intermediate Similarity	NPD5403	Approved
0.791	Intermediate Similarity	NPD3751	Discontinued
0.7892	Intermediate Similarity	NPD6799	Approved
0.7861	Intermediate Similarity	NPD3749	Approved
0.7844	Intermediate Similarity	NPD5401	Approved
0.7841	Intermediate Similarity	NPD3926	Phase 2
0.784	Intermediate Similarity	NPD1510	Phase 2
0.7824	Intermediate Similarity	NPD6599	Discontinued
0.7812	Intermediate Similarity	NPD1613	Approved
0.7812	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7809	Intermediate Similarity	NPD7228	Approved
0.7791	Intermediate Similarity	NPD2796	Approved
0.7791	Intermediate Similarity	NPD8455	Phase 2
0.7784	Intermediate Similarity	NPD7390	Discontinued
0.776	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7738	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7737	Intermediate Similarity	NPD6777	Approved
0.7737	Intermediate Similarity	NPD6778	Approved
0.7737	Intermediate Similarity	NPD6776	Approved
0.7737	Intermediate Similarity	NPD6780	Approved
0.7737	Intermediate Similarity	NPD6782	Approved
0.7737	Intermediate Similarity	NPD6781	Approved
0.7737	Intermediate Similarity	NPD6779	Approved
0.7727	Intermediate Similarity	NPD1247	Approved
0.7717	Intermediate Similarity	NPD8150	Discontinued
0.7702	Intermediate Similarity	NPD943	Approved
0.7692	Intermediate Similarity	NPD8151	Discontinued
0.7665	Intermediate Similarity	NPD6190	Approved
0.764	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7627	Intermediate Similarity	NPD7199	Phase 2
0.7617	Intermediate Similarity	NPD7697	Approved
0.7617	Intermediate Similarity	NPD7435	Discontinued
0.7617	Intermediate Similarity	NPD7698	Approved
0.7617	Intermediate Similarity	NPD7696	Phase 3
0.7614	Intermediate Similarity	NPD919	Approved
0.7614	Intermediate Similarity	NPD6234	Discontinued
0.7593	Intermediate Similarity	NPD1240	Approved
0.7579	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7577	Intermediate Similarity	NPD7871	Phase 2
0.7577	Intermediate Similarity	NPD7870	Phase 2
0.7562	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD7701	Phase 2
0.7545	Intermediate Similarity	NPD2800	Approved
0.7545	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD2533	Approved
0.7529	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD2534	Approved
0.7529	Intermediate Similarity	NPD37	Approved
0.7529	Intermediate Similarity	NPD2532	Approved
0.7515	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3750	Approved
0.75	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4965	Approved
0.75	Intermediate Similarity	NPD4967	Phase 2
0.75	Intermediate Similarity	NPD4966	Approved
0.75	Intermediate Similarity	NPD1607	Approved
0.7485	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7474	Intermediate Similarity	NPD6534	Approved
0.7474	Intermediate Similarity	NPD6535	Approved
0.7461	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7457	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7457	Intermediate Similarity	NPD3226	Approved
0.7453	Intermediate Similarity	NPD4908	Phase 1
0.7448	Intermediate Similarity	NPD7699	Phase 2
0.7448	Intermediate Similarity	NPD7700	Phase 2
0.7442	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7437	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7437	Intermediate Similarity	NPD7801	Approved
0.7437	Intermediate Similarity	NPD7783	Phase 2
0.7433	Intermediate Similarity	NPD8434	Phase 2
0.7407	Intermediate Similarity	NPD3027	Phase 3
0.7405	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7398	Intermediate Similarity	NPD8319	Approved
0.7398	Intermediate Similarity	NPD8320	Phase 1
0.7396	Intermediate Similarity	NPD4628	Phase 3
0.7387	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7387	Intermediate Similarity	NPD7874	Approved
0.7382	Intermediate Similarity	NPD4363	Phase 3
0.7382	Intermediate Similarity	NPD4360	Phase 2
0.7365	Intermediate Similarity	NPD2935	Discontinued
0.7351	Intermediate Similarity	NPD7685	Pre-registration
0.7351	Intermediate Similarity	NPD7240	Approved
0.7333	Intermediate Similarity	NPD230	Phase 1
0.7305	Intermediate Similarity	NPD2799	Discontinued
0.7305	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD1653	Approved
0.7297	Intermediate Similarity	NPD5953	Discontinued
0.7296	Intermediate Similarity	NPD6823	Phase 2
0.7289	Intermediate Similarity	NPD6651	Approved
0.7262	Intermediate Similarity	NPD1551	Phase 2
0.7262	Intermediate Similarity	NPD6100	Approved
0.7262	Intermediate Similarity	NPD6099	Approved
0.7257	Intermediate Similarity	NPD7458	Discontinued
0.7241	Intermediate Similarity	NPD920	Approved
0.7225	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD2346	Discontinued
0.7219	Intermediate Similarity	NPD2344	Approved
0.7202	Intermediate Similarity	NPD3748	Approved
0.7198	Intermediate Similarity	NPD7229	Phase 3
0.7189	Intermediate Similarity	NPD7286	Phase 2
0.7168	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD5405	Approved
0.716	Intermediate Similarity	NPD5406	Approved
0.716	Intermediate Similarity	NPD5408	Approved
0.716	Intermediate Similarity	NPD5404	Approved
0.7152	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD2313	Discontinued
0.7152	Intermediate Similarity	NPD6798	Discontinued
0.715	Intermediate Similarity	NPD7584	Approved
0.7143	Intermediate Similarity	NPD8127	Discontinued
0.7126	Intermediate Similarity	NPD447	Suspended
0.7125	Intermediate Similarity	NPD1610	Phase 2
0.7115	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7104	Intermediate Similarity	NPD5710	Approved
0.7104	Intermediate Similarity	NPD5711	Approved
0.7093	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7085	Intermediate Similarity	NPD7680	Approved
0.7079	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD4060	Phase 1
0.7062	Intermediate Similarity	NPD6212	Phase 3
0.7062	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD6213	Phase 3
0.7056	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7052	Intermediate Similarity	NPD2309	Approved
0.7035	Intermediate Similarity	NPD1243	Approved
0.7027	Intermediate Similarity	NPD2403	Approved
0.7024	Intermediate Similarity	NPD5124	Phase 1
0.7024	Intermediate Similarity	NPD6355	Discontinued
0.7024	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD4665	Approved
0.7019	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD4111	Phase 1
0.7018	Intermediate Similarity	NPD7266	Discontinued
0.7006	Intermediate Similarity	NPD6233	Phase 2
0.7	Intermediate Similarity	NPD4004	Approved
0.7	Intermediate Similarity	NPD4002	Approved
0.6995	Remote Similarity	NPD4287	Approved
0.6994	Remote Similarity	NPD8166	Discontinued
0.6994	Remote Similarity	NPD7003	Approved
0.699	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.699	Remote Similarity	NPD4361	Phase 2
0.6989	Remote Similarity	NPD6273	Approved
0.6985	Remote Similarity	NPD3450	Approved
0.6985	Remote Similarity	NPD2493	Approved
0.6985	Remote Similarity	NPD2494	Approved
0.6985	Remote Similarity	NPD3452	Approved
0.6977	Remote Similarity	NPD2424	Discontinued
0.697	Remote Similarity	NPD9494	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