NPASS Compound

Structure

CID19157 OpenBabel06191715342D 26 29 0 0 0 0 0 0 0 0999 V2000 -2.5981 -2.5000 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 0.8660 -2.5000 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 -4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 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 -5.1962 -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 0.8660 -1.5000 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 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -0.0000 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 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 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 -0.8660 0.5000 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 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 23 1 0 0 0 0 2 24 1 0 0 0 0 3 6 2 0 0 0 0 3 11 1 0 0 0 0 4 7 2 0 0 0 0 4 11 1 0 0 0 0 5 8 2 0 0 0 0 5 12 1 0 0 0 0 6 14 1 0 0 0 0 7 18 1 0 0 0 0 8 17 1 0 0 0 0 9 12 2 0 0 0 0 9 13 1 0 0 0 0 10 15 2 0 0 0 0 10 16 1 0 0 0 0 11 20 2 0 0 0 0 12 15 1 0 0 0 0 13 16 2 0 0 0 0 13 19 1 0 0 0 0 14 19 2 0 0 0 0 14 23 1 0 0 0 0 15 25 1 0 0 0 0 16 24 1 0 0 0 0 17 21 2 0 0 0 0 17 25 1 0 0 0 0 18 22 2 0 0 0 0 18 26 1 0 0 0 0 19 20 1 0 0 0 0 20 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	350.08
Volume:	346.627
LogP:	2.55
LogD:	2.533
LogS:	-5.632
# Rotatable Bonds:	3
TPSA:	78.88
# H-Bond Aceptor:	6
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.526
Synthetic Accessibility Score:	2.463
Fsp3:	0.1
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.751
MDCK Permeability:	5.868492371519096e-05
Pgp-inhibitor:	0.425
Pgp-substrate:	0.037
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.206
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.02
Plasma Protein Binding (PPB):	77.0508041381836%
Volume Distribution (VD):	0.58
Pgp-substrate:	9.859930038452148%

ADMET: Metabolism

CYP1A2-inhibitor:	0.905
CYP1A2-substrate:	0.976
CYP2C19-inhibitor:	0.266
CYP2C19-substrate:	0.063
CYP2C9-inhibitor:	0.143
CYP2C9-substrate:	0.911
CYP2D6-inhibitor:	0.546
CYP2D6-substrate:	0.914
CYP3A4-inhibitor:	0.721
CYP3A4-substrate:	0.481

ADMET: Excretion

Clearance (CL):	10.799
Half-life (T1/2):	0.313

ADMET: Toxicity

hERG Blockers:	0.071
Human Hepatotoxicity (H-HT):	0.91
Drug-inuced Liver Injury (DILI):	0.969
AMES Toxicity:	0.141
Rat Oral Acute Toxicity:	0.142
Maximum Recommended Daily Dose:	0.401
Skin Sensitization:	0.046
Carcinogencity:	0.878
Eye Corrosion:	0.003
Eye Irritation:	0.043
Respiratory Toxicity:	0.067

Download Data

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

Natural Product: NPC19157

Natural Product ID:	NPC19157
*Common Name:**	7-Methoxy-8-(7-Methoxy-2-Oxochromen-6-Yl)Chromen-2-One
IUPAC Name:	7-methoxy-8-(7-methoxy-2-oxochromen-6-yl)chromen-2-one
Synonyms:
Standard InCHIKey:	NFNSSVSQSNJVCR-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C20H14O6/c1-23-14-6-3-11-4-7-18(22)26-20(11)19(14)13-9-12-5-8-17(21)25-15(12)10-16(13)24-2/h3-10H,1-2H3
SMILES:	COc1ccc2ccc(=O)oc2c1c1cc2ccc(=O)oc2cc1OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1877565
PubChem CID:	5319307
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000145] Coumarins and derivatives

*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
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10654410]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[10843587]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	Roots	n.a.	n.a.	PMID[15568770]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[16392664]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[16933887]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	roots	Hualien Hsien, Taiwan	2003-JUL	PMID[16933887]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[17951038]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18175961]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24295087]
NPO20471	Sophora alopecuroides	Species	Fabaceae	Eukaryota	root bark	Mongolian	n.a.	PMID[26073007]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27575476]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	Roots	n.a.	n.a.	PMID[30298740]
NPO20471	Sophora alopecuroides	Species	Fabaceae	Eukaryota	Aerial Parts	n.a.	n.a.	PMID[31747283]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	Roots	n.a.	n.a.	PMID[9868163]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	Database[Article]
NPO9683	Sophora chrysophylla	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20471	Sophora alopecuroides	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO442	Boenninghausenia japonica	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO27572	Sophora subprostrata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26788	Sophora viciifolia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO27666	Sophora tetraptera	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24771	Boenninghausenia albiflora	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20471	Sophora alopecuroides	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO442	Boenninghausenia japonica	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26788	Sophora viciifolia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27572	Sophora subprostrata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27666	Sophora tetraptera	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24771	Boenninghausenia albiflora	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9683	Sophora chrysophylla	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24771	Boenninghausenia albiflora	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9683	Sophora chrysophylla	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO442	Boenninghausenia japonica	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO20471	Sophora alopecuroides	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO27572	Sophora subprostrata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO27666	Sophora tetraptera	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO26788	Sophora viciifolia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24771	Boenninghausenia albiflora	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27666	Sophora tetraptera	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27572	Sophora subprostrata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO442	Boenninghausenia japonica	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20471	Sophora alopecuroides	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
Potency	6

Activity Type	# Activity
Individual Protein	4
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT477	Individual Protein	DNA dC->dU-editing enzyme APOBEC-3G	Homo sapiens	Potency	n.a.	25118.9	nM	PMID[502864]
NPT478	Individual Protein	Ataxin-2	Homo sapiens	Potency	n.a.	10621.3	nM	PMID[502864]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	29092.9	nM	PMID[502864]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	18356.4	nM	PMID[502864]
NPT2	Others	Unspecified		Potency	n.a.	8912.5	nM	PMID[502864]
NPT2	Others	Unspecified		Potency	n.a.	22387.2	nM	PMID[502864]

☑ 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 NPC19157 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	507
0.1-0.2	1989
0.2-0.3	4618
0.3-0.4	10818
0.4-0.5	7304
0.5-0.6	4572
0.6-0.7	5700
0.7-0.8	4751
0.8-0.85	1772
0.85-0.9	584
0.9-0.95	81
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.928	High Similarity	NPC315807
0.9206	High Similarity	NPC73413
0.9206	High Similarity	NPC201667
0.916	High Similarity	NPC472524
0.9134	High Similarity	NPC471827
0.9134	High Similarity	NPC471828
0.9127	High Similarity	NPC472518
0.9127	High Similarity	NPC290605
0.9127	High Similarity	NPC273772
0.9127	High Similarity	NPC173350
0.9127	High Similarity	NPC109675
0.9127	High Similarity	NPC154176
0.9084	High Similarity	NPC469956
0.907	High Similarity	NPC199204
0.9062	High Similarity	NPC471826
0.9055	High Similarity	NPC27671
0.9055	High Similarity	NPC291899
0.9055	High Similarity	NPC111347
0.9048	High Similarity	NPC13007
0.9048	High Similarity	NPC96286
0.9048	High Similarity	NPC257188
0.9048	High Similarity	NPC248429
0.9015	High Similarity	NPC133956
0.9015	High Similarity	NPC207002
0.9015	High Similarity	NPC167111
0.9015	High Similarity	NPC469955
0.9015	High Similarity	NPC318400
0.9015	High Similarity	NPC296624
0.9015	High Similarity	NPC469952
0.9015	High Similarity	NPC471910
0.9	High Similarity	NPC168710
0.8992	High Similarity	NPC289316
0.8976	High Similarity	NPC50720
0.8971	High Similarity	NPC472523
0.8968	High Similarity	NPC144418
0.8947	High Similarity	NPC127888
0.8947	High Similarity	NPC84894
0.8947	High Similarity	NPC195343
0.8947	High Similarity	NPC166672
0.8947	High Similarity	NPC267412
0.8947	High Similarity	NPC198381
0.8947	High Similarity	NPC287182
0.8947	High Similarity	NPC47163
0.8947	High Similarity	NPC131950
0.8947	High Similarity	NPC18804
0.8947	High Similarity	NPC100986
0.8947	High Similarity	NPC260265
0.8947	High Similarity	NPC74655
0.8947	High Similarity	NPC164269
0.8947	High Similarity	NPC319859
0.8931	High Similarity	NPC80170
0.8931	High Similarity	NPC32463
0.8923	High Similarity	NPC472519
0.8923	High Similarity	NPC185066
0.8915	High Similarity	NPC188327
0.8915	High Similarity	NPC234109
0.8915	High Similarity	NPC163248
0.8913	High Similarity	NPC36732
0.8898	High Similarity	NPC150214
0.8889	High Similarity	NPC306365
0.8881	High Similarity	NPC471909
0.8881	High Similarity	NPC471625
0.8881	High Similarity	NPC86892
0.8881	High Similarity	NPC281241
0.8881	High Similarity	NPC472424
0.888	High Similarity	NPC298796
0.8872	High Similarity	NPC31849
0.8828	High Similarity	NPC143725
0.8815	High Similarity	NPC149320
0.8815	High Similarity	NPC128529
0.8815	High Similarity	NPC476455
0.8815	High Similarity	NPC283019
0.8815	High Similarity	NPC471630
0.8815	High Similarity	NPC55615
0.8815	High Similarity	NPC177281
0.8815	High Similarity	NPC160727
0.8806	High Similarity	NPC307412
0.8806	High Similarity	NPC55149
0.88	High Similarity	NPC152306
0.88	High Similarity	NPC96705
0.88	High Similarity	NPC265547
0.8797	High Similarity	NPC14248
0.8797	High Similarity	NPC194277
0.8779	High Similarity	NPC139595
0.8779	High Similarity	NPC293642
0.8779	High Similarity	NPC157212
0.8779	High Similarity	NPC60704
0.8759	High Similarity	NPC71903
0.8741	High Similarity	NPC234865
0.8741	High Similarity	NPC469675
0.874	High Similarity	NPC163200
0.874	High Similarity	NPC235190
0.874	High Similarity	NPC180006
0.8731	High Similarity	NPC163557
0.8731	High Similarity	NPC222036
0.8731	High Similarity	NPC7526
0.873	High Similarity	NPC281356
0.8714	High Similarity	NPC71739
0.8714	High Similarity	NPC101255
0.8714	High Similarity	NPC475719
0.8714	High Similarity	NPC43716
0.8714	High Similarity	NPC295696
0.8702	High Similarity	NPC243688
0.8696	High Similarity	NPC183642
0.8696	High Similarity	NPC310370
0.8696	High Similarity	NPC170812
0.8696	High Similarity	NPC138149
0.8692	High Similarity	NPC93219
0.8692	High Similarity	NPC168259
0.8692	High Similarity	NPC232692
0.8692	High Similarity	NPC244495
0.8692	High Similarity	NPC202594
0.8686	High Similarity	NPC307883
0.8686	High Similarity	NPC37428
0.8686	High Similarity	NPC47040
0.8686	High Similarity	NPC279573
0.8686	High Similarity	NPC211110
0.8686	High Similarity	NPC137262
0.8686	High Similarity	NPC144512
0.8686	High Similarity	NPC278600
0.8686	High Similarity	NPC35501
0.8676	High Similarity	NPC224543
0.8676	High Similarity	NPC78746
0.8676	High Similarity	NPC167517
0.8676	High Similarity	NPC286843
0.8676	High Similarity	NPC38099
0.8676	High Similarity	NPC26954
0.8676	High Similarity	NPC188380
0.8667	High Similarity	NPC62366
0.8667	High Similarity	NPC180716
0.8667	High Similarity	NPC326600
0.8667	High Similarity	NPC204353
0.8667	High Similarity	NPC50896
0.8667	High Similarity	NPC224475
0.8667	High Similarity	NPC213173
0.8657	High Similarity	NPC123954
0.8643	High Similarity	NPC471824
0.864	High Similarity	NPC128633
0.8633	High Similarity	NPC20631
0.8633	High Similarity	NPC93640
0.8626	High Similarity	NPC101894
0.8623	High Similarity	NPC312881
0.8613	High Similarity	NPC155963
0.8613	High Similarity	NPC131198
0.8613	High Similarity	NPC153818
0.8613	High Similarity	NPC184861
0.8613	High Similarity	NPC294456
0.8613	High Similarity	NPC225106
0.8613	High Similarity	NPC232246
0.8613	High Similarity	NPC212124
0.8613	High Similarity	NPC281014
0.8603	High Similarity	NPC33986
0.8603	High Similarity	NPC472525
0.8593	High Similarity	NPC54503
0.8593	High Similarity	NPC55147
0.8582	High Similarity	NPC86069
0.8582	High Similarity	NPC108994
0.8582	High Similarity	NPC66430
0.8582	High Similarity	NPC37009
0.8582	High Similarity	NPC469701
0.8582	High Similarity	NPC106126
0.8571	High Similarity	NPC134360
0.8561	High Similarity	NPC155552
0.8561	High Similarity	NPC152771
0.8561	High Similarity	NPC287286
0.8561	High Similarity	NPC195357
0.8551	High Similarity	NPC151946
0.8551	High Similarity	NPC270256
0.854	High Similarity	NPC283331
0.8529	High Similarity	NPC253574
0.8529	High Similarity	NPC184677
0.8529	High Similarity	NPC98179
0.8519	High Similarity	NPC281558
0.8519	High Similarity	NPC175159
0.8511	High Similarity	NPC251372
0.8478	Intermediate Similarity	NPC14697
0.8478	Intermediate Similarity	NPC474886
0.8467	Intermediate Similarity	NPC66705
0.8456	Intermediate Similarity	NPC141822
0.8456	Intermediate Similarity	NPC472522
0.8456	Intermediate Similarity	NPC77196
0.8456	Intermediate Similarity	NPC205797
0.8456	Intermediate Similarity	NPC241165
0.8456	Intermediate Similarity	NPC83535
0.8456	Intermediate Similarity	NPC1220
0.8456	Intermediate Similarity	NPC291551
0.8456	Intermediate Similarity	NPC142563
0.8444	Intermediate Similarity	NPC472517
0.8444	Intermediate Similarity	NPC250727
0.8444	Intermediate Similarity	NPC211413
0.8444	Intermediate Similarity	NPC68205
0.8444	Intermediate Similarity	NPC164804
0.8444	Intermediate Similarity	NPC293203
0.8444	Intermediate Similarity	NPC118683
0.8444	Intermediate Similarity	NPC244888
0.844	Intermediate Similarity	NPC119640
0.844	Intermediate Similarity	NPC183646
0.8429	Intermediate Similarity	NPC136095
0.8425	Intermediate Similarity	NPC189773
0.8421	Intermediate Similarity	NPC224774

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 NPC19157 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	447
0.1-0.2	975
0.2-0.3	1652
0.3-0.4	2716
0.4-0.5	1928
0.5-0.6	977
0.6-0.7	297
0.7-0.8	101
0.8-0.85	39
0.85-0.9	17
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.854	High Similarity	NPD3748	Approved
0.8456	Intermediate Similarity	NPD5124	Phase 1
0.8456	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.8385	Intermediate Similarity	NPD422	Phase 1
0.8239	Intermediate Similarity	NPD3750	Approved
0.8235	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8088	Intermediate Similarity	NPD4908	Phase 1
0.8088	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.806	Intermediate Similarity	NPD3225	Approved
0.8042	Intermediate Similarity	NPD1243	Approved
0.8031	Intermediate Similarity	NPD5535	Approved
0.8027	Intermediate Similarity	NPD920	Approved
0.8	Intermediate Similarity	NPD3267	Approved
0.8	Intermediate Similarity	NPD3266	Approved
0.7971	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7971	Intermediate Similarity	NPD1296	Phase 2
0.797	Intermediate Similarity	NPD1610	Phase 2
0.797	Intermediate Similarity	NPD1611	Approved
0.7961	Intermediate Similarity	NPD7768	Phase 2
0.7958	Intermediate Similarity	NPD2796	Approved
0.7939	Intermediate Similarity	NPD1548	Phase 1
0.7891	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7891	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7877	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7868	Intermediate Similarity	NPD2797	Approved
0.7829	Intermediate Similarity	NPD7819	Suspended
0.7815	Intermediate Similarity	NPD7411	Suspended
0.7793	Intermediate Similarity	NPD1652	Phase 2
0.777	Intermediate Similarity	NPD4625	Phase 3
0.776	Intermediate Similarity	NPD9697	Approved
0.7744	Intermediate Similarity	NPD5691	Approved
0.773	Intermediate Similarity	NPD4307	Phase 2
0.7714	Intermediate Similarity	NPD3268	Approved
0.7712	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD5844	Phase 1
0.7671	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD5401	Approved
0.7651	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD6801	Discontinued
0.7619	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.761	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7589	Intermediate Similarity	NPD2313	Discontinued
0.7584	Intermediate Similarity	NPD6799	Approved
0.7571	Intermediate Similarity	NPD6832	Phase 2
0.7571	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7566	Intermediate Similarity	NPD8158	Clinical (unspecified phase)
0.7564	Intermediate Similarity	NPD7075	Discontinued
0.7564	Intermediate Similarity	NPD3749	Approved
0.7556	Intermediate Similarity	NPD4626	Approved
0.755	Intermediate Similarity	NPD5403	Approved
0.7548	Intermediate Similarity	NPD4288	Approved
0.7517	Intermediate Similarity	NPD4308	Phase 3
0.7517	Intermediate Similarity	NPD1510	Phase 2
0.7517	Intermediate Similarity	NPD2799	Discontinued
0.7516	Intermediate Similarity	NPD4380	Phase 2
0.7516	Intermediate Similarity	NPD919	Approved
0.7516	Intermediate Similarity	NPD6599	Discontinued
0.75	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD4060	Phase 1
0.7483	Intermediate Similarity	NPD1549	Phase 2
0.7483	Intermediate Similarity	NPD1613	Approved
0.7483	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD5494	Approved
0.7468	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7466	Intermediate Similarity	NPD2935	Discontinued
0.7466	Intermediate Similarity	NPD1551	Phase 2
0.7436	Intermediate Similarity	NPD5402	Approved
0.7436	Intermediate Similarity	NPD3817	Phase 2
0.7436	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7431	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7426	Intermediate Similarity	NPD17	Approved
0.7422	Intermediate Similarity	NPD3134	Approved
0.7415	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7415	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD1653	Approved
0.7375	Intermediate Similarity	NPD7229	Phase 3
0.7372	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD1465	Phase 2
0.7372	Intermediate Similarity	NPD3496	Discontinued
0.7368	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7364	Intermediate Similarity	NPD1358	Approved
0.7361	Intermediate Similarity	NPD1240	Approved
0.7342	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD3226	Approved
0.7338	Intermediate Similarity	NPD4749	Approved
0.7319	Intermediate Similarity	NPD1281	Approved
0.731	Intermediate Similarity	NPD4340	Discontinued
0.7297	Intermediate Similarity	NPD2346	Discontinued
0.7297	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD7549	Discontinued
0.7286	Intermediate Similarity	NPD8651	Approved
0.7285	Intermediate Similarity	NPD6666	Approved
0.7285	Intermediate Similarity	NPD6667	Approved
0.7279	Intermediate Similarity	NPD7033	Discontinued
0.7267	Intermediate Similarity	NPD7466	Approved
0.7267	Intermediate Similarity	NPD7003	Approved
0.7267	Intermediate Similarity	NPD4628	Phase 3
0.7267	Intermediate Similarity	NPD6232	Discontinued
0.7266	Intermediate Similarity	NPD1608	Approved
0.7261	Intermediate Similarity	NPD8455	Phase 2
0.726	Intermediate Similarity	NPD1607	Approved
0.7254	Intermediate Similarity	NPD2861	Phase 2
0.7241	Intermediate Similarity	NPD2979	Phase 3
0.7237	Intermediate Similarity	NPD1511	Approved
0.7234	Intermediate Similarity	NPD1203	Approved
0.7226	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD5585	Approved
0.7222	Intermediate Similarity	NPD6798	Discontinued
0.7222	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD6959	Discontinued
0.72	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD1934	Approved
0.7192	Intermediate Similarity	NPD1933	Approved
0.7192	Intermediate Similarity	NPD6355	Discontinued
0.719	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD7447	Phase 1
0.7183	Intermediate Similarity	NPD1019	Discontinued
0.7164	Intermediate Similarity	NPD1241	Discontinued
0.7163	Intermediate Similarity	NPD1283	Approved
0.7153	Intermediate Similarity	NPD7095	Approved
0.7153	Intermediate Similarity	NPD3027	Phase 3
0.7152	Intermediate Similarity	NPD2801	Approved
0.7152	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD9717	Approved
0.7143	Intermediate Similarity	NPD1512	Approved
0.7134	Intermediate Similarity	NPD7473	Discontinued
0.7133	Intermediate Similarity	NPD3018	Phase 2
0.7126	Intermediate Similarity	NPD6559	Discontinued
0.7124	Intermediate Similarity	NPD7213	Phase 3
0.7124	Intermediate Similarity	NPD7212	Phase 2
0.7124	Intermediate Similarity	NPD7837	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD4140	Approved
0.7114	Intermediate Similarity	NPD4476	Approved
0.7114	Intermediate Similarity	NPD4477	Approved
0.7101	Intermediate Similarity	NPD1651	Approved
0.7099	Intermediate Similarity	NPD1247	Approved
0.7095	Intermediate Similarity	NPD7097	Phase 1
0.7086	Intermediate Similarity	NPD2800	Approved
0.7078	Intermediate Similarity	NPD2534	Approved
0.7078	Intermediate Similarity	NPD2533	Approved
0.7078	Intermediate Similarity	NPD2532	Approved
0.7071	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD6004	Phase 3
0.7067	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD6005	Phase 3
0.7067	Intermediate Similarity	NPD6002	Phase 3
0.7063	Intermediate Similarity	NPD2798	Approved
0.7055	Intermediate Similarity	NPD8032	Phase 2
0.7055	Intermediate Similarity	NPD6233	Phase 2
0.7037	Intermediate Similarity	NPD5283	Phase 1
0.7032	Intermediate Similarity	NPD6273	Approved
0.7029	Intermediate Similarity	NPD1894	Discontinued
0.7021	Intermediate Similarity	NPD2981	Phase 2
0.702	Intermediate Similarity	NPD2424	Discontinued
0.7019	Intermediate Similarity	NPD6971	Discontinued
0.7	Intermediate Similarity	NPD6099	Approved
0.7	Intermediate Similarity	NPD2438	Suspended
0.7	Intermediate Similarity	NPD6100	Approved
0.7	Intermediate Similarity	NPD3847	Discontinued
0.6994	Remote Similarity	NPD7199	Phase 2
0.6992	Remote Similarity	NPD5451	Approved
0.6986	Remote Similarity	NPD3764	Approved
0.6981	Remote Similarity	NPD37	Approved
0.698	Remote Similarity	NPD4536	Approved
0.698	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.698	Remote Similarity	NPD4538	Approved
0.6972	Remote Similarity	NPD2983	Phase 2
0.6972	Remote Similarity	NPD4359	Approved
0.6972	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD2982	Phase 2
0.697	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD5953	Discontinued
0.6959	Remote Similarity	NPD4622	Approved
0.6959	Remote Similarity	NPD4618	Approved
0.6957	Remote Similarity	NPD7644	Approved
0.6957	Remote Similarity	NPD5536	Phase 2
0.6957	Remote Similarity	NPD4966	Approved
0.6957	Remote Similarity	NPD4965	Approved
0.6957	Remote Similarity	NPD4967	Phase 2
0.6954	Remote Similarity	NPD5763	Approved
0.6954	Remote Similarity	NPD5762	Approved
0.695	Remote Similarity	NPD1535	Discovery
0.6946	Remote Similarity	NPD7286	Phase 2
0.6944	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6934	Remote Similarity	NPD7157	Approved
0.6934	Remote Similarity	NPD6387	Discontinued
0.6929	Remote Similarity	NPD1778	Approved
0.6923	Remote Similarity	NPD1876	Approved
0.6918	Remote Similarity	NPD5889	Approved
0.6918	Remote Similarity	NPD5890	Approved
0.6917	Remote Similarity	NPD2684	Approved
0.6909	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD3926	Phase 2
0.6901	Remote Similarity	NPD1481	Phase 2

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