NPASS Compound

Structure

CID231758 OpenBabel06191716032D 40 45 0 0 0 0 0 0 0 0999 V2000 -3.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5878 -2.5411 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3854 4.0057 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2514 3.5057 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0878 -3.4071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5878 0.9230 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0878 -1.6750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4807 2.5057 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0878 0.0570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0878 -1.6750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4807 3.5057 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2514 2.5057 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0878 0.0570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0878 -3.4071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5878 0.9230 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5878 -2.5411 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3854 2.0057 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0878 0.0570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9945 1.8366 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5878 0.9230 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3467 4.0057 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 0.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0878 0.0570 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5878 -4.2731 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0878 1.7891 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5878 -2.5411 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9727 2.0445 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3090 -2.5691 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5933 1.0276 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 7 2 0 0 0 0 1 13 1 0 0 0 0 2 8 2 0 0 0 0 2 14 1 0 0 0 0 3 5 2 0 0 0 0 3 15 1 0 0 0 0 4 6 2 0 0 0 0 4 16 1 0 0 0 0 5 17 1 0 0 0 0 6 18 1 0 0 0 0 7 19 1 0 0 0 0 8 20 1 0 0 0 0 9 13 2 0 0 0 0 9 21 1 0 0 0 0 10 14 2 0 0 0 0 10 22 1 0 0 0 0 11 15 2 0 0 0 0 11 23 1 0 0 0 0 12 16 2 0 0 0 0 12 24 1 0 0 0 0 13 25 1 0 0 0 0 14 26 1 0 0 0 0 15 31 1 0 0 0 0 16 32 1 0 0 0 0 17 23 2 0 0 0 0 17 27 1 0 0 0 0 18 24 2 0 0 0 0 18 28 1 0 0 0 0 19 21 2 0 0 0 0 19 33 1 0 0 0 0 20 22 2 0 0 0 0 20 34 1 0 0 0 0 21 35 1 0 0 0 0 22 36 1 0 0 0 0 23 39 1 0 0 0 0 24 40 1 0 0 0 0 25 26 1 0 0 0 0 25 29 2 0 0 0 0 26 30 2 0 0 0 0 27 29 1 0 0 0 0 27 37 2 0 0 0 0 28 30 1 0 0 0 0 28 38 2 0 0 0 0 29 39 1 0 0 0 0 30 40 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	538.09
Volume:	521.816
LogP:	3.925
LogD:	2.577
LogS:	-5.841
# Rotatable Bonds:	3
TPSA:	173.98
# H-Bond Aceptor:	10
# H-Bond Donor:	6
# Rings:	6
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.16
Synthetic Accessibility Score:	3.267
Fsp3:	0.0
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:	-5.693
MDCK Permeability:	1.3149778169463389e-05
Pgp-inhibitor:	0.019
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.02
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.01
Plasma Protein Binding (PPB):	100.97022247314453%
Volume Distribution (VD):	0.187
Pgp-substrate:	1.252781629562378%

ADMET: Metabolism

CYP1A2-inhibitor:	0.928
CYP1A2-substrate:	0.063
CYP2C19-inhibitor:	0.812
CYP2C19-substrate:	0.033
CYP2C9-inhibitor:	0.649
CYP2C9-substrate:	0.514
CYP2D6-inhibitor:	0.123
CYP2D6-substrate:	0.126
CYP3A4-inhibitor:	0.172
CYP3A4-substrate:	0.065

ADMET: Excretion

Clearance (CL):	7.688
Half-life (T1/2):	0.858

ADMET: Toxicity

hERG Blockers:	0.047
Human Hepatotoxicity (H-HT):	0.394
Drug-inuced Liver Injury (DILI):	0.972
AMES Toxicity:	0.683
Rat Oral Acute Toxicity:	0.679
Maximum Recommended Daily Dose:	0.93
Skin Sensitization:	0.944
Carcinogencity:	0.65
Eye Corrosion:	0.003
Eye Irritation:	0.9
Respiratory Toxicity:	0.019

Download Data

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

Natural Product: NPC231758

Natural Product ID:	NPC231758
*Common Name:**	2,2'-[1,2-Bis(3,4-Dihydroxyphenyl)-1,2-Ethanedylidene]Bis[6-Hydroxy-3(2H)-Benzofuranone]
IUPAC Name:	(2Z)-2-[(2Z)-1,2-bis(3,4-dihydroxyphenyl)-2-(6-hydroxy-3-oxo-1-benzofuran-2-ylidene)ethylidene]-6-hydroxy-1-benzofuran-3-one
Synonyms:
Standard InCHIKey:	MZVYXDUSVXNKLC-IDDWGTJGSA-N
Standard InCHI:	InChI=1S/C30H18O10/c31-15-3-5-17-23(11-15)39-29(27(17)37)25(13-1-7-19(33)21(35)9-13)26(14-2-8-20(34)22(36)10-14)30-28(38)18-6-4-16(32)12-24(18)40-30/h1-12,31-36H/b29-25-,30-26-
SMILES:	c1cc(c(cc1/C(=C/1C(=O)c2ccc(cc2O1)O)/C(=C1/C(=O)c2ccc(cc2O1)O)/c1ccc(c(c1)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL523383
PubChem CID:	10007411
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0001631] Aurone 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
NPO24559	Cotinus coggygria	Species	Anacardiaceae	Eukaryota	Whole plant	n.a.	n.a.	PMID[11141121]
NPO24559	Cotinus coggygria	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24559	Cotinus coggygria	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24559	Cotinus coggygria	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO24559	Cotinus coggygria	Species	Anacardiaceae	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	1

Activity Type	# Activity
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1	Others	Radical scavenging activity		IC50	=	9.7	ug.mL-1	PMID[465760]

☑ 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 NPC231758 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	467
0.1-0.2	2067
0.2-0.3	5097
0.3-0.4	11722
0.4-0.5	5490
0.5-0.6	4077
0.6-0.7	5367
0.7-0.8	5273
0.8-0.85	2320
0.85-0.9	791
0.9-0.95	25
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9325	High Similarity	NPC156955
0.9226	High Similarity	NPC189130
0.9211	High Similarity	NPC140840
0.9211	High Similarity	NPC86847
0.915	High Similarity	NPC19545
0.9051	High Similarity	NPC185526
0.9051	High Similarity	NPC112954
0.9038	High Similarity	NPC304954
0.9032	High Similarity	NPC260582
0.9006	High Similarity	NPC472582
0.8974	High Similarity	NPC260895
0.897	High Similarity	NPC149846
0.8961	High Similarity	NPC51443
0.8961	High Similarity	NPC74881
0.8944	High Similarity	NPC477841
0.8944	High Similarity	NPC272722
0.8944	High Similarity	NPC219927
0.8929	High Similarity	NPC47883
0.8924	High Similarity	NPC133392
0.8917	High Similarity	NPC63187
0.8917	High Similarity	NPC37684
0.8917	High Similarity	NPC157784
0.891	High Similarity	NPC188871
0.891	High Similarity	NPC149127
0.891	High Similarity	NPC286342
0.8909	High Similarity	NPC476370
0.8902	High Similarity	NPC107627
0.8896	High Similarity	NPC179271
0.8896	High Similarity	NPC169749
0.8896	High Similarity	NPC20791
0.8882	High Similarity	NPC34089
0.8882	High Similarity	NPC196179
0.8875	High Similarity	NPC195832
0.8875	High Similarity	NPC154304
0.8875	High Similarity	NPC190487
0.8868	High Similarity	NPC471500
0.8868	High Similarity	NPC472461
0.8868	High Similarity	NPC265511
0.8861	High Similarity	NPC58382
0.8861	High Similarity	NPC270620
0.8861	High Similarity	NPC141212
0.8861	High Similarity	NPC179126
0.8861	High Similarity	NPC78326
0.8861	High Similarity	NPC162351
0.8861	High Similarity	NPC236223
0.8855	High Similarity	NPC216842
0.8855	High Similarity	NPC476640
0.8855	High Similarity	NPC82217
0.8855	High Similarity	NPC476374
0.8855	High Similarity	NPC117450
0.8854	High Similarity	NPC205046
0.8854	High Similarity	NPC304295
0.8854	High Similarity	NPC154345
0.8854	High Similarity	NPC59162
0.8848	High Similarity	NPC102277
0.8848	High Similarity	NPC279209
0.8846	High Similarity	NPC270465
0.8846	High Similarity	NPC105512
0.8846	High Similarity	NPC87125
0.8841	High Similarity	NPC470704
0.8841	High Similarity	NPC260266
0.8839	High Similarity	NPC95864
0.8834	High Similarity	NPC36320
0.8834	High Similarity	NPC7688
0.8834	High Similarity	NPC36
0.8834	High Similarity	NPC259757
0.8834	High Similarity	NPC58223
0.8834	High Similarity	NPC72787
0.8834	High Similarity	NPC7154
0.8834	High Similarity	NPC125039
0.8834	High Similarity	NPC36916
0.8834	High Similarity	NPC477840
0.8831	High Similarity	NPC70136
0.882	High Similarity	NPC188967
0.8812	High Similarity	NPC183
0.8812	High Similarity	NPC471515
0.8812	High Similarity	NPC67876
0.8812	High Similarity	NPC471479
0.8812	High Similarity	NPC237418
0.8805	High Similarity	NPC80534
0.8805	High Similarity	NPC214138
0.8805	High Similarity	NPC56786
0.8802	High Similarity	NPC99591
0.8802	High Similarity	NPC287243
0.8797	High Similarity	NPC82325
0.8797	High Similarity	NPC279989
0.8797	High Similarity	NPC55205
0.8797	High Similarity	NPC123886
0.8795	High Similarity	NPC472454
0.8795	High Similarity	NPC186847
0.8795	High Similarity	NPC230619
0.8795	High Similarity	NPC257667
0.8795	High Similarity	NPC174700
0.8795	High Similarity	NPC54098
0.879	High Similarity	NPC77858
0.879	High Similarity	NPC3825
0.879	High Similarity	NPC88804
0.8788	High Similarity	NPC280493
0.8782	High Similarity	NPC196277
0.8782	High Similarity	NPC43669
0.8782	High Similarity	NPC272721
0.8782	High Similarity	NPC3036
0.878	High Similarity	NPC82330
0.878	High Similarity	NPC224851
0.878	High Similarity	NPC171985
0.878	High Similarity	NPC320741
0.8773	High Similarity	NPC272064
0.8772	High Similarity	NPC226725
0.8766	High Similarity	NPC279121
0.8765	High Similarity	NPC112418
0.8765	High Similarity	NPC142252
0.8765	High Similarity	NPC289771
0.8765	High Similarity	NPC158188
0.8758	High Similarity	NPC476410
0.8758	High Similarity	NPC143828
0.8758	High Similarity	NPC115798
0.8758	High Similarity	NPC7846
0.8758	High Similarity	NPC300943
0.8758	High Similarity	NPC191459
0.8758	High Similarity	NPC288669
0.8758	High Similarity	NPC25495
0.8758	High Similarity	NPC253634
0.8758	High Similarity	NPC261004
0.8758	High Similarity	NPC19687
0.8758	High Similarity	NPC4481
0.8758	High Similarity	NPC18772
0.8758	High Similarity	NPC18607
0.8758	High Similarity	NPC193842
0.8758	High Similarity	NPC176300
0.8758	High Similarity	NPC9609
0.8758	High Similarity	NPC22472
0.8758	High Similarity	NPC172202
0.8758	High Similarity	NPC105242
0.8758	High Similarity	NPC284127
0.8758	High Similarity	NPC204854
0.8758	High Similarity	NPC152166
0.8758	High Similarity	NPC130894
0.875	High Similarity	NPC3980
0.875	High Similarity	NPC296018
0.875	High Similarity	NPC100916
0.875	High Similarity	NPC137100
0.875	High Similarity	NPC55619
0.875	High Similarity	NPC474638
0.875	High Similarity	NPC471841
0.875	High Similarity	NPC200388
0.875	High Similarity	NPC282307
0.875	High Similarity	NPC153512
0.875	High Similarity	NPC154741
0.875	High Similarity	NPC8127
0.875	High Similarity	NPC170026
0.875	High Similarity	NPC49667
0.8742	High Similarity	NPC33051
0.8742	High Similarity	NPC49402
0.8742	High Similarity	NPC325028
0.8742	High Similarity	NPC170492
0.8742	High Similarity	NPC246328
0.8742	High Similarity	NPC27532
0.8742	High Similarity	NPC273462
0.8742	High Similarity	NPC227337
0.8742	High Similarity	NPC256346
0.8742	High Similarity	NPC70433
0.8735	High Similarity	NPC476641
0.8735	High Similarity	NPC476365
0.8734	High Similarity	NPC200740
0.8734	High Similarity	NPC133953
0.8734	High Similarity	NPC236769
0.8734	High Similarity	NPC54394
0.8734	High Similarity	NPC76376
0.8734	High Similarity	NPC50403
0.8734	High Similarity	NPC28274
0.8734	High Similarity	NPC125062
0.8734	High Similarity	NPC252933
0.8727	High Similarity	NPC50394
0.8727	High Similarity	NPC48640
0.8727	High Similarity	NPC149244
0.8726	High Similarity	NPC1612
0.8726	High Similarity	NPC183959
0.8726	High Similarity	NPC195351
0.8721	High Similarity	NPC248315
0.872	High Similarity	NPC45449
0.872	High Similarity	NPC300053
0.8718	High Similarity	NPC77378
0.8718	High Similarity	NPC168803
0.8718	High Similarity	NPC108406
0.8713	High Similarity	NPC154527
0.8712	High Similarity	NPC471745
0.8712	High Similarity	NPC476247
0.8704	High Similarity	NPC471744
0.8704	High Similarity	NPC328102
0.8701	High Similarity	NPC175013
0.8701	High Similarity	NPC471417
0.8698	High Similarity	NPC98546
0.8698	High Similarity	NPC297807
0.8698	High Similarity	NPC475783
0.8698	High Similarity	NPC476773
0.8696	High Similarity	NPC29841
0.8696	High Similarity	NPC75215
0.8696	High Similarity	NPC63454
0.8696	High Similarity	NPC78302
0.8696	High Similarity	NPC110070

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 NPC231758 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	432
0.1-0.2	1039
0.2-0.3	1731
0.3-0.4	2759
0.4-0.5	1717
0.5-0.6	997
0.6-0.7	323
0.7-0.8	104
0.8-0.85	35
0.85-0.9	10
0.9-0.95	3
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8987	High Similarity	NPD3882	Suspended
0.8896	High Similarity	NPD1512	Approved
0.8834	High Similarity	NPD6166	Phase 2
0.8834	High Similarity	NPD6168	Clinical (unspecified phase)
0.8834	High Similarity	NPD6167	Clinical (unspecified phase)
0.8766	High Similarity	NPD1511	Approved
0.8625	High Similarity	NPD2393	Clinical (unspecified phase)
0.8562	High Similarity	NPD1934	Approved
0.8519	High Similarity	NPD4868	Clinical (unspecified phase)
0.8509	High Similarity	NPD2801	Approved
0.8503	High Similarity	NPD3818	Discontinued
0.8471	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8462	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8457	Intermediate Similarity	NPD3817	Phase 2
0.8354	Intermediate Similarity	NPD7075	Discontinued
0.8354	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8353	Intermediate Similarity	NPD6797	Phase 2
0.8304	Intermediate Similarity	NPD7251	Discontinued
0.8256	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8242	Intermediate Similarity	NPD3749	Approved
0.821	Intermediate Similarity	NPD4380	Phase 2
0.8205	Intermediate Similarity	NPD1549	Phase 2
0.8187	Intermediate Similarity	NPD7074	Phase 3
0.8176	Intermediate Similarity	NPD6799	Approved
0.8171	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.816	Intermediate Similarity	NPD7411	Suspended
0.815	Intermediate Similarity	NPD7808	Phase 3
0.8141	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8141	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8133	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8129	Intermediate Similarity	NPD1510	Phase 2
0.8129	Intermediate Similarity	NPD7054	Approved
0.8121	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.811	Intermediate Similarity	NPD6801	Discontinued
0.8107	Intermediate Similarity	NPD3926	Phase 2
0.8105	Intermediate Similarity	NPD943	Approved
0.8095	Intermediate Similarity	NPD6959	Discontinued
0.8081	Intermediate Similarity	NPD7472	Approved
0.8059	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8036	Intermediate Similarity	NPD5494	Approved
0.8025	Intermediate Similarity	NPD5403	Approved
0.8012	Intermediate Similarity	NPD5402	Approved
0.7988	Intermediate Similarity	NPD6599	Discontinued
0.7987	Intermediate Similarity	NPD1240	Approved
0.7964	Intermediate Similarity	NPD7768	Phase 2
0.7962	Intermediate Similarity	NPD2796	Approved
0.7952	Intermediate Similarity	NPD1465	Phase 2
0.7952	Intermediate Similarity	NPD7819	Suspended
0.7941	Intermediate Similarity	NPD6232	Discontinued
0.7919	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7914	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7907	Intermediate Similarity	NPD7473	Discontinued
0.7901	Intermediate Similarity	NPD5401	Approved
0.7895	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7885	Intermediate Similarity	NPD1607	Approved
0.7875	Intermediate Similarity	NPD3750	Approved
0.787	Intermediate Similarity	NPD919	Approved
0.7784	Intermediate Similarity	NPD6559	Discontinued
0.7778	Intermediate Similarity	NPD1247	Approved
0.7714	Intermediate Similarity	NPD5844	Phase 1
0.7688	Intermediate Similarity	NPD2344	Approved
0.7674	Intermediate Similarity	NPD7199	Phase 2
0.7673	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD7390	Discontinued
0.7613	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD2800	Approved
0.7562	Intermediate Similarity	NPD3748	Approved
0.7548	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD1551	Phase 2
0.7514	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2309	Approved
0.75	Intermediate Similarity	NPD6190	Approved
0.7486	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD1243	Approved
0.7458	Intermediate Similarity	NPD3751	Discontinued
0.7457	Intermediate Similarity	NPD6234	Discontinued
0.7433	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD3787	Discontinued
0.7421	Intermediate Similarity	NPD1613	Approved
0.7421	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD2935	Discontinued
0.7405	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD3226	Approved
0.7375	Intermediate Similarity	NPD230	Phase 1
0.7365	Intermediate Similarity	NPD2533	Approved
0.7365	Intermediate Similarity	NPD2534	Approved
0.7365	Intermediate Similarity	NPD2532	Approved
0.7349	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD8313	Approved
0.7308	Intermediate Similarity	NPD1203	Approved
0.7308	Intermediate Similarity	NPD8312	Approved
0.7301	Intermediate Similarity	NPD5404	Approved
0.7301	Intermediate Similarity	NPD6100	Approved
0.7301	Intermediate Similarity	NPD5405	Approved
0.7301	Intermediate Similarity	NPD5406	Approved
0.7301	Intermediate Similarity	NPD5408	Approved
0.7301	Intermediate Similarity	NPD6099	Approved
0.7297	Intermediate Similarity	NPD4287	Approved
0.7296	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD4908	Phase 1
0.7278	Intermediate Similarity	NPD920	Approved
0.7267	Intermediate Similarity	NPD447	Suspended
0.7263	Intermediate Similarity	NPD7228	Approved
0.7262	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7253	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD4967	Phase 2
0.7241	Intermediate Similarity	NPD4966	Approved
0.7241	Intermediate Similarity	NPD4965	Approved
0.7239	Intermediate Similarity	NPD2799	Discontinued
0.7238	Intermediate Similarity	NPD5953	Discontinued
0.7229	Intermediate Similarity	NPD4628	Phase 3
0.7222	Intermediate Similarity	NPD6651	Approved
0.7188	Intermediate Similarity	NPD2313	Discontinued
0.7188	Intermediate Similarity	NPD6798	Discontinued
0.7188	Intermediate Similarity	NPD3764	Approved
0.7188	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD1471	Phase 3
0.7135	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD3027	Phase 3
0.7097	Intermediate Similarity	NPD8434	Phase 2
0.707	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD37	Approved
0.7063	Intermediate Similarity	NPD6832	Phase 2
0.7056	Intermediate Similarity	NPD2403	Approved
0.7055	Intermediate Similarity	NPD1933	Approved
0.7051	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD2346	Discontinued
0.7047	Intermediate Similarity	NPD6777	Approved
0.7047	Intermediate Similarity	NPD6776	Approved
0.7047	Intermediate Similarity	NPD6779	Approved
0.7047	Intermediate Similarity	NPD6780	Approved
0.7047	Intermediate Similarity	NPD6778	Approved
0.7047	Intermediate Similarity	NPD6781	Approved
0.7047	Intermediate Similarity	NPD6782	Approved
0.7044	Intermediate Similarity	NPD2798	Approved
0.7035	Intermediate Similarity	NPD1653	Approved
0.7033	Intermediate Similarity	NPD7286	Phase 2
0.7026	Intermediate Similarity	NPD7435	Discontinued
0.7006	Intermediate Similarity	NPD9717	Approved
0.7006	Intermediate Similarity	NPD9269	Phase 2
0.7	Intermediate Similarity	NPD9494	Approved
0.6994	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD2296	Approved
0.6989	Remote Similarity	NPD4288	Approved
0.6982	Remote Similarity	NPD2354	Approved
0.6981	Remote Similarity	NPD1470	Approved
0.6975	Remote Similarity	NPD3268	Approved
0.6964	Remote Similarity	NPD2654	Approved
0.6961	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD6355	Discontinued
0.6944	Remote Similarity	NPD7229	Phase 3
0.6943	Remote Similarity	NPD1201	Approved
0.6943	Remote Similarity	NPD1610	Phase 2
0.6935	Remote Similarity	NPD8151	Discontinued
0.6933	Remote Similarity	NPD6233	Phase 2
0.6932	Remote Similarity	NPD8455	Phase 2
0.6928	Remote Similarity	NPD7033	Discontinued
0.6928	Remote Similarity	NPD4308	Phase 3
0.6919	Remote Similarity	NPD7685	Pre-registration
0.6918	Remote Similarity	NPD3225	Approved
0.6915	Remote Similarity	NPD8150	Discontinued
0.6914	Remote Similarity	NPD7095	Approved
0.691	Remote Similarity	NPD6971	Discontinued
0.6904	Remote Similarity	NPD7870	Phase 2
0.6904	Remote Similarity	NPD7871	Phase 2
0.6903	Remote Similarity	NPD1548	Phase 1
0.6899	Remote Similarity	NPD1608	Approved
0.6897	Remote Similarity	NPD7458	Discontinued
0.6885	Remote Similarity	NPD2163	Approved
0.6885	Remote Similarity	NPD7177	Discontinued
0.6875	Remote Similarity	NPD2797	Approved
0.6871	Remote Similarity	NPD411	Approved
0.6853	Remote Similarity	NPD7698	Approved
0.6853	Remote Similarity	NPD7697	Approved
0.6853	Remote Similarity	NPD7696	Phase 3
0.6851	Remote Similarity	NPD5711	Approved
0.6851	Remote Similarity	NPD5710	Approved
0.6848	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD4361	Phase 2
0.6835	Remote Similarity	NPD422	Phase 1
0.6828	Remote Similarity	NPD7240	Approved
0.6824	Remote Similarity	NPD8166	Discontinued
0.6824	Remote Similarity	NPD7003	Approved
0.6821	Remote Similarity	NPD5049	Phase 3
0.6821	Remote Similarity	NPD6273	Approved
0.6816	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD7874	Approved
0.6811	Remote Similarity	NPD1729	Discontinued
0.681	Remote Similarity	NPD4625	Phase 3
0.68	Remote Similarity	NPD7701	Phase 2
0.6796	Remote Similarity	NPD8127	Discontinued

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