NPASS Compound

Structure

CID210048 OpenBabel06191716002D 32 36 0 0 1 0 0 0 0 0999 V2000 1.0464 -4.3729 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7244 -4.1969 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7288 0.3987 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2397 -0.4858 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2173 -0.4877 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3742 -0.0007 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7330 -2.8318 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3747 -1.9476 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2184 -1.4603 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8432 -2.4354 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3738 -1.9487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6869 0.0006 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8346 -3.8005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2171 -1.4620 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5309 -1.4606 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5304 -0.4874 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5307 -0.4864 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5302 -1.4616 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8433 -0.4867 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8435 -1.4610 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6873 -1.9479 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0004 -1.9480 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2182 -0.4860 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8434 -1.4613 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.8436 -0.4870 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 5.0830 -1.9621 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6875 -2.9694 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0007 -2.9480 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8438 0.5130 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3744 0.0009 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6870 -1.9483 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 13 1 0 0 0 0 2 13 1 0 0 0 0 3 23 1 0 0 0 0 4 23 1 0 0 0 0 5 6 2 0 0 0 0 5 14 1 0 0 0 0 6 16 1 0 0 0 0 7 10 1 0 0 0 0 7 13 2 0 0 0 0 8 9 2 0 0 0 0 8 15 1 0 0 0 0 9 23 1 0 0 0 0 10 24 1 0 0 0 0 11 14 2 0 0 0 0 11 18 1 0 0 0 0 12 17 2 0 0 0 0 12 19 1 0 0 0 0 14 26 1 0 0 0 0 15 17 1 0 0 0 0 15 21 2 0 0 0 0 16 18 2 0 0 0 0 16 25 1 0 0 0 0 17 30 1 0 0 0 0 18 31 1 0 0 0 0 19 20 2 0 0 0 0 19 32 1 0 0 0 0 20 21 1 0 0 0 0 20 22 1 0 0 0 0 21 27 1 0 0 0 0 22 24 1 0 0 0 0 22 28 2 0 0 0 0 23 30 1 0 0 0 0 24 25 1 0 0 0 0 24 31 1 0 0 0 0 25 29 1 0 0 0 0 25 32 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	436.15
Volume:	435.977
LogP:	5.361
LogD:	3.68
LogS:	-3.181
# Rotatable Bonds:	2
TPSA:	105.45
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.606
Synthetic Accessibility Score:	4.373
Fsp3:	0.32
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.787
MDCK Permeability:	1.6548388884984888e-05
Pgp-inhibitor:	0.125
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.375
20% Bioavailability (F20%):	0.281
30% Bioavailability (F30%):	0.52

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.023
Plasma Protein Binding (PPB):	96.36444854736328%
Volume Distribution (VD):	0.645
Pgp-substrate:	3.867826223373413%

ADMET: Metabolism

CYP1A2-inhibitor:	0.706
CYP1A2-substrate:	0.345
CYP2C19-inhibitor:	0.324
CYP2C19-substrate:	0.666
CYP2C9-inhibitor:	0.513
CYP2C9-substrate:	0.787
CYP2D6-inhibitor:	0.883
CYP2D6-substrate:	0.216
CYP3A4-inhibitor:	0.768
CYP3A4-substrate:	0.496

ADMET: Excretion

Clearance (CL):	4.996
Half-life (T1/2):	0.248

ADMET: Toxicity

hERG Blockers:	0.043
Human Hepatotoxicity (H-HT):	0.936
Drug-inuced Liver Injury (DILI):	0.937
AMES Toxicity:	0.113
Rat Oral Acute Toxicity:	0.741
Maximum Recommended Daily Dose:	0.747
Skin Sensitization:	0.479
Carcinogencity:	0.927
Eye Corrosion:	0.003
Eye Irritation:	0.028
Respiratory Toxicity:	0.175

Download Data

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

Natural Product: NPC210048

Natural Product ID:	NPC210048
*Common Name:**	GPSKVSZZHKDRDQ-UHFFFAOYSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	GPSKVSZZHKDRDQ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C25H24O7/c1-13(2)7-10-24-22(28)20-19(12-17-15(21(20)27)8-9-23(3,4)30-17)32-25(24,29)16-6-5-14(26)11-18(16)31-24/h5-9,11-12,26-27,29H,10H2,1-4H3
SMILES:	CC(=CCC12Oc3c(C2(O)Oc2c(C1=O)c(O)c1c(c2)OC(C=C1)(C)C)ccc(c3)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1517104
PubChem CID:	10342974
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0003543] Pyranochromenes

*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
NPO14875	Morus cathayana	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19338315]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20815207]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	root	n.a.	PMID[21319773]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	leaf	n.a.	PMID[21319773]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	bark	n.a.	PMID[21319773]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	leaf	n.a.	PMID[22207282]
NPO14875	Morus cathayana	Species	Moraceae	Eukaryota	Fruits	Zhenjiang, Jiangsu Province, China		PMID[23060696]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	root	n.a.	PMID[23806866]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	root bark	University of Veterinary and Pharmaceutical Sciences Brno (UVPS Brno), Brno, Czech Republic	2011-APR	PMID[24901948]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	Konya, Turkey	2007-APR	PMID[24901948]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	leaves	Chungbuk, Korea	n.a.	PMID[25935644]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	root	n.a.	PMID[25981820]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	latex	n.a.	PMID[27294120]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	Root barks	n.a.	n.a.	PMID[3097265]
NPO14875	Morus cathayana	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14875	Morus cathayana	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO14875	Morus cathayana	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28265	Morus alba	Species	Moraceae	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
EC50	3
Potency	14

Activity Type	# Activity
Cell Line	1
Individual Protein	14
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1254	Individual Protein	Streptokinase A	Streptococcus pyogenes serotype M1	EC50	=	2395.0	nM	PMID[514006]
NPT532	Individual Protein	Lysine-specific demethylase 4A	Homo sapiens	Potency	n.a.	56234.1	nM	PMID[514006]
NPT65	Cell Line	HepG2	Homo sapiens	Potency	n.a.	22387.2	nM	PMID[514006]
NPT154	Individual Protein	Mothers against decapentaplegic homolog 3	Homo sapiens	Potency	n.a.	35481.3	nM	PMID[514006]
NPT10	Individual Protein	Geminin	Homo sapiens	Potency	n.a.	366.3	nM	PMID[514006]
NPT478	Individual Protein	Ataxin-2	Homo sapiens	Potency	n.a.	28183.8	nM	PMID[514006]
NPT101	Individual Protein	Glucagon-like peptide 1 receptor	Homo sapiens	Potency	n.a.	28183.8	nM	PMID[514006]
NPT159	Individual Protein	Aberrant vpr protein	Human immunodeficiency virus 1	Potency	n.a.	50118.7	nM	PMID[514006]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	29092.9	nM	PMID[514006]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	25929.0	nM	PMID[514006]
NPT160	Individual Protein	TAR DNA-binding protein 43	Homo sapiens	Potency	n.a.	25118.9	nM	PMID[514006]
NPT161	Individual Protein	Rap guanine nucleotide exchange factor 4	Homo sapiens	Potency	n.a.	89125.1	nM	PMID[514006]
NPT446	Individual Protein	Rap guanine nucleotide exchange factor 3	Homo sapiens	Potency	n.a.	112201.8	nM	PMID[514006]
NPT174	Organism	Streptococcus	Streptococcus	EC50	=	3916.0	nM	PMID[514006]
NPT1252	Organism	Streptococcus sp. 'group A'	Streptococcus sp. 'group A'	EC50	=	3320.0	nM	PMID[514006]
NPT861	Individual Protein	Isocitrate dehydrogenase [NADP] cytoplasmic	Homo sapiens	Potency	n.a.	50118.7	nM	PMID[514006]
NPT920	Individual Protein	Alpha-synuclein	Homo sapiens	Potency	n.a.	35481.3	nM	PMID[514006]

☑ 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 NPC210048 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	397
0.1-0.2	1606
0.2-0.3	3929
0.3-0.4	9629
0.4-0.5	8685
0.5-0.6	3727
0.6-0.7	5683
0.7-0.8	5169
0.8-0.85	2774
0.85-0.9	991
0.9-0.95	102
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9933	High Similarity	NPC264932
0.9933	High Similarity	NPC311574
0.9868	High Similarity	NPC172687
0.9735	High Similarity	NPC161650
0.9408	High Similarity	NPC311579
0.9408	High Similarity	NPC236756
0.9367	High Similarity	NPC292233
0.9355	High Similarity	NPC306978
0.9346	High Similarity	NPC259710
0.9346	High Similarity	NPC217706
0.9346	High Similarity	NPC207809
0.9346	High Similarity	NPC304207
0.9346	High Similarity	NPC476169
0.9346	High Similarity	NPC48579
0.9333	High Similarity	NPC296869
0.9299	High Similarity	NPC179198
0.9299	High Similarity	NPC66087
0.9299	High Similarity	NPC278419
0.9299	High Similarity	NPC183672
0.9281	High Similarity	NPC248793
0.9281	High Similarity	NPC180301
0.9276	High Similarity	NPC471675
0.9276	High Similarity	NPC472636
0.9267	High Similarity	NPC14001
0.9267	High Similarity	NPC166757
0.9236	High Similarity	NPC150164
0.9236	High Similarity	NPC131745
0.9221	High Similarity	NPC304745
0.9221	High Similarity	NPC111341
0.9216	High Similarity	NPC473996
0.9216	High Similarity	NPC210597
0.9216	High Similarity	NPC327269
0.9216	High Similarity	NPC476238
0.9216	High Similarity	NPC31627
0.9205	High Similarity	NPC244407
0.92	High Similarity	NPC5820
0.92	High Similarity	NPC124729
0.92	High Similarity	NPC220418
0.92	High Similarity	NPC178343
0.92	High Similarity	NPC306488
0.9195	High Similarity	NPC190637
0.9195	High Similarity	NPC9117
0.9195	High Similarity	NPC212932
0.9195	High Similarity	NPC24821
0.9195	High Similarity	NPC293053
0.9195	High Similarity	NPC219915
0.9156	High Similarity	NPC268193
0.9156	High Similarity	NPC7989
0.9156	High Similarity	NPC472583
0.9156	High Similarity	NPC223701
0.9156	High Similarity	NPC209760
0.9156	High Similarity	NPC100134
0.915	High Similarity	NPC472580
0.915	High Similarity	NPC278476
0.915	High Similarity	NPC319910
0.915	High Similarity	NPC254412
0.915	High Similarity	NPC262039
0.915	High Similarity	NPC262038
0.9139	High Similarity	NPC472918
0.9136	High Similarity	NPC73899
0.9136	High Similarity	NPC474276
0.9136	High Similarity	NPC17105
0.9136	High Similarity	NPC147363
0.9133	High Similarity	NPC326500
0.9133	High Similarity	NPC71210
0.9133	High Similarity	NPC273538
0.9133	High Similarity	NPC216538
0.9128	High Similarity	NPC473042
0.9128	High Similarity	NPC200694
0.9119	High Similarity	NPC72016
0.9114	High Similarity	NPC259834
0.9114	High Similarity	NPC93215
0.9097	High Similarity	NPC279218
0.9097	High Similarity	NPC471116
0.9097	High Similarity	NPC108937
0.9097	High Similarity	NPC469934
0.9091	High Similarity	NPC161881
0.9091	High Similarity	NPC10807
0.9091	High Similarity	NPC243171
0.9091	High Similarity	NPC35567
0.9091	High Similarity	NPC477957
0.9091	High Similarity	NPC217149
0.9091	High Similarity	NPC216035
0.9091	High Similarity	NPC475790
0.9091	High Similarity	NPC142527
0.9091	High Similarity	NPC138288
0.9091	High Similarity	NPC244583
0.9091	High Similarity	NPC56232
0.9091	High Similarity	NPC171651
0.9091	High Similarity	NPC150123
0.9091	High Similarity	NPC285623
0.9085	High Similarity	NPC105136
0.9085	High Similarity	NPC472421
0.9085	High Similarity	NPC471984
0.9068	High Similarity	NPC5319
0.9067	High Similarity	NPC38219
0.9067	High Similarity	NPC158874
0.906	High Similarity	NPC310128
0.9045	High Similarity	NPC111929
0.9045	High Similarity	NPC472459
0.9045	High Similarity	NPC470607
0.9045	High Similarity	NPC41121
0.9045	High Similarity	NPC320283
0.9038	High Similarity	NPC146636
0.9038	High Similarity	NPC474738
0.9038	High Similarity	NPC475797
0.9038	High Similarity	NPC129053
0.9038	High Similarity	NPC109967
0.9038	High Similarity	NPC78554
0.9038	High Similarity	NPC469936
0.9038	High Similarity	NPC321372
0.9038	High Similarity	NPC20530
0.9038	High Similarity	NPC215917
0.9038	High Similarity	NPC474609
0.9038	High Similarity	NPC10754
0.9032	High Similarity	NPC244250
0.9032	High Similarity	NPC293286
0.9032	High Similarity	NPC20907
0.9032	High Similarity	NPC469405
0.9032	High Similarity	NPC88983
0.9026	High Similarity	NPC472423
0.9026	High Similarity	NPC244577
0.9026	High Similarity	NPC263384
0.9026	High Similarity	NPC474772
0.9026	High Similarity	NPC328740
0.9026	High Similarity	NPC471676
0.9026	High Similarity	NPC474023
0.9026	High Similarity	NPC472420
0.9026	High Similarity	NPC471229
0.9026	High Similarity	NPC209846
0.9026	High Similarity	NPC472422
0.9026	High Similarity	NPC474021
0.9026	High Similarity	NPC81474
0.9026	High Similarity	NPC471677
0.9026	High Similarity	NPC289774
0.9026	High Similarity	NPC474744
0.9026	High Similarity	NPC477897
0.902	High Similarity	NPC470461
0.902	High Similarity	NPC277032
0.9013	High Similarity	NPC296998
0.9013	High Similarity	NPC473077
0.9013	High Similarity	NPC140120
0.9012	High Similarity	NPC8704
0.9012	High Similarity	NPC287884
0.9	High Similarity	NPC62840
0.9	High Similarity	NPC78803
0.9	High Similarity	NPC59739
0.9	High Similarity	NPC299080
0.9	High Similarity	NPC204088
0.9	High Similarity	NPC144499
0.9	High Similarity	NPC259007
0.9	High Similarity	NPC266725
0.9	High Similarity	NPC217083
0.9	High Similarity	NPC329215
0.9	High Similarity	NPC214236
0.9	High Similarity	NPC471520
0.9	High Similarity	NPC293852
0.8994	High Similarity	NPC219861
0.8994	High Similarity	NPC44947
0.8987	High Similarity	NPC153342
0.8981	High Similarity	NPC135391
0.8981	High Similarity	NPC470606
0.8981	High Similarity	NPC237418
0.8981	High Similarity	NPC122809
0.8981	High Similarity	NPC78263
0.8981	High Similarity	NPC108831
0.8981	High Similarity	NPC197304
0.8981	High Similarity	NPC288084
0.8981	High Similarity	NPC77672
0.8981	High Similarity	NPC182634
0.8981	High Similarity	NPC133671
0.8981	High Similarity	NPC54802
0.8974	High Similarity	NPC133392
0.8974	High Similarity	NPC470681
0.8974	High Similarity	NPC87404
0.8974	High Similarity	NPC92395
0.8974	High Similarity	NPC275575
0.8974	High Similarity	NPC477958
0.8968	High Similarity	NPC157784
0.8968	High Similarity	NPC37684
0.8968	High Similarity	NPC63187
0.8968	High Similarity	NPC45934
0.8961	High Similarity	NPC472633
0.8961	High Similarity	NPC267117
0.8961	High Similarity	NPC29777
0.8961	High Similarity	NPC471115
0.8961	High Similarity	NPC61258
0.8957	High Similarity	NPC245452
0.8954	High Similarity	NPC470460
0.8954	High Similarity	NPC168085
0.8947	High Similarity	NPC246948
0.8947	High Similarity	NPC470458
0.8947	High Similarity	NPC83357
0.8947	High Similarity	NPC267375
0.8947	High Similarity	NPC20488
0.8947	High Similarity	NPC142405
0.8947	High Similarity	NPC301276
0.8947	High Similarity	NPC67805
0.8947	High Similarity	NPC329678
0.8947	High Similarity	NPC111786

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 NPC210048 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	354
0.1-0.2	905
0.2-0.3	1665
0.3-0.4	2681
0.4-0.5	1881
0.5-0.6	1076
0.6-0.7	394
0.7-0.8	150
0.8-0.85	35
0.85-0.9	8
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9133	High Similarity	NPD4378	Clinical (unspecified phase)
0.9068	High Similarity	NPD7804	Clinical (unspecified phase)
0.8981	High Similarity	NPD7075	Discontinued
0.891	High Similarity	NPD7096	Clinical (unspecified phase)
0.8861	High Similarity	NPD4381	Clinical (unspecified phase)
0.8839	High Similarity	NPD4380	Phase 2
0.8758	High Similarity	NPD7410	Clinical (unspecified phase)
0.8726	High Similarity	NPD6801	Discontinued
0.8671	High Similarity	NPD2393	Clinical (unspecified phase)
0.8614	High Similarity	NPD6797	Phase 2
0.8581	High Similarity	NPD1512	Approved
0.8571	High Similarity	NPD6799	Approved
0.8563	High Similarity	NPD7251	Discontinued
0.8562	High Similarity	NPD3882	Suspended
0.8512	High Similarity	NPD7808	Phase 3
0.85	High Similarity	NPD3817	Phase 2
0.8491	Intermediate Similarity	NPD1934	Approved
0.8452	Intermediate Similarity	NPD1511	Approved
0.8438	Intermediate Similarity	NPD2801	Approved
0.8434	Intermediate Similarity	NPD3818	Discontinued
0.8428	Intermediate Similarity	NPD7411	Suspended
0.8424	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8424	Intermediate Similarity	NPD6166	Phase 2
0.8424	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8421	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8421	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8402	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8385	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8383	Intermediate Similarity	NPD7054	Approved
0.8366	Intermediate Similarity	NPD1549	Phase 2
0.8365	Intermediate Similarity	NPD6599	Discontinued
0.8343	Intermediate Similarity	NPD6559	Discontinued
0.8333	Intermediate Similarity	NPD7472	Approved
0.8333	Intermediate Similarity	NPD7074	Phase 3
0.8291	Intermediate Similarity	NPD5403	Approved
0.8289	Intermediate Similarity	NPD1510	Phase 2
0.8282	Intermediate Similarity	NPD3749	Approved
0.8235	Intermediate Similarity	NPD2796	Approved
0.821	Intermediate Similarity	NPD7819	Suspended
0.8194	Intermediate Similarity	NPD2800	Approved
0.8182	Intermediate Similarity	NPD5494	Approved
0.8165	Intermediate Similarity	NPD5401	Approved
0.816	Intermediate Similarity	NPD5402	Approved
0.8146	Intermediate Similarity	NPD1240	Approved
0.8141	Intermediate Similarity	NPD3750	Approved
0.8095	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8077	Intermediate Similarity	NPD1243	Approved
0.8039	Intermediate Similarity	NPD1607	Approved
0.8024	Intermediate Similarity	NPD6959	Discontinued
0.8012	Intermediate Similarity	NPD919	Approved
0.8	Intermediate Similarity	NPD7768	Phase 2
0.8	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.795	Intermediate Similarity	NPD920	Approved
0.7921	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7917	Intermediate Similarity	NPD1247	Approved
0.787	Intermediate Similarity	NPD6232	Discontinued
0.7848	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7836	Intermediate Similarity	NPD7473	Discontinued
0.7826	Intermediate Similarity	NPD2533	Approved
0.7826	Intermediate Similarity	NPD2532	Approved
0.7826	Intermediate Similarity	NPD2534	Approved
0.7826	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD3748	Approved
0.7812	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD3751	Discontinued
0.7785	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD2313	Discontinued
0.7771	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD2935	Discontinued
0.7765	Intermediate Similarity	NPD3787	Discontinued
0.7759	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7747	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7746	Intermediate Similarity	NPD5844	Phase 1
0.7722	Intermediate Similarity	NPD2344	Approved
0.7707	Intermediate Similarity	NPD2799	Discontinued
0.7688	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7665	Intermediate Similarity	NPD1465	Phase 2
0.7662	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.766	Intermediate Similarity	NPD7584	Approved
0.7658	Intermediate Similarity	NPD1551	Phase 2
0.7632	Intermediate Similarity	NPD2798	Approved
0.7622	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD3926	Phase 2
0.758	Intermediate Similarity	NPD6651	Approved
0.7578	Intermediate Similarity	NPD4628	Phase 3
0.7557	Intermediate Similarity	NPD5953	Discontinued
0.7548	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD6099	Approved
0.7547	Intermediate Similarity	NPD6100	Approved
0.7543	Intermediate Similarity	NPD7286	Phase 2
0.7542	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD2309	Approved
0.753	Intermediate Similarity	NPD3226	Approved
0.7527	Intermediate Similarity	NPD6782	Approved
0.7527	Intermediate Similarity	NPD6778	Approved
0.7527	Intermediate Similarity	NPD6776	Approved
0.7527	Intermediate Similarity	NPD6777	Approved
0.7527	Intermediate Similarity	NPD6779	Approved
0.7527	Intermediate Similarity	NPD6781	Approved
0.7527	Intermediate Similarity	NPD6780	Approved
0.75	Intermediate Similarity	NPD2346	Discontinued
0.75	Intermediate Similarity	NPD7435	Discontinued
0.7484	Intermediate Similarity	NPD7033	Discontinued
0.7471	Intermediate Similarity	NPD2403	Approved
0.7469	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD5049	Phase 3
0.7452	Intermediate Similarity	NPD943	Approved
0.7451	Intermediate Similarity	NPD1203	Approved
0.7446	Intermediate Similarity	NPD4360	Phase 2
0.7446	Intermediate Similarity	NPD4363	Phase 3
0.7439	Intermediate Similarity	NPD7390	Discontinued
0.7439	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD6798	Discontinued
0.7436	Intermediate Similarity	NPD3268	Approved
0.743	Intermediate Similarity	NPD8312	Approved
0.743	Intermediate Similarity	NPD8313	Approved
0.7425	Intermediate Similarity	NPD7458	Discontinued
0.7423	Intermediate Similarity	NPD2354	Approved
0.7419	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD4908	Phase 1
0.7405	Intermediate Similarity	NPD5124	Phase 1
0.7405	Intermediate Similarity	NPD6355	Discontinued
0.7405	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD1933	Approved
0.7403	Intermediate Similarity	NPD8434	Phase 2
0.7399	Intermediate Similarity	NPD7199	Phase 2
0.7375	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD4308	Phase 3
0.7356	Intermediate Similarity	NPD5711	Approved
0.7356	Intermediate Similarity	NPD5710	Approved
0.7355	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD8455	Phase 2
0.7338	Intermediate Similarity	NPD2797	Approved
0.7322	Intermediate Similarity	NPD4287	Approved
0.7316	Intermediate Similarity	NPD7696	Phase 3
0.7316	Intermediate Similarity	NPD7697	Approved
0.7316	Intermediate Similarity	NPD7698	Approved
0.7312	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD4361	Phase 2
0.7303	Intermediate Similarity	NPD422	Phase 1
0.7284	Intermediate Similarity	NPD1471	Phase 3
0.7283	Intermediate Similarity	NPD6234	Discontinued
0.7278	Intermediate Similarity	NPD6233	Phase 2
0.7277	Intermediate Similarity	NPD7871	Phase 2
0.7277	Intermediate Similarity	NPD7870	Phase 2
0.7273	Intermediate Similarity	NPD3225	Approved
0.7273	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD7874	Approved
0.7261	Intermediate Similarity	NPD4625	Phase 3
0.7258	Intermediate Similarity	NPD6535	Approved
0.7258	Intermediate Similarity	NPD6534	Approved
0.7255	Intermediate Similarity	NPD9717	Approved
0.7254	Intermediate Similarity	NPD7701	Phase 2
0.7254	Intermediate Similarity	NPD7585	Approved
0.7239	Intermediate Similarity	NPD2424	Discontinued
0.7235	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD4060	Phase 1
0.7233	Intermediate Similarity	NPD1613	Approved
0.7233	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7228	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD3764	Approved
0.7213	Intermediate Similarity	NPD8150	Discontinued
0.7209	Intermediate Similarity	NPD4288	Approved
0.7202	Intermediate Similarity	NPD7583	Approved
0.7197	Intermediate Similarity	NPD6832	Phase 2
0.7195	Intermediate Similarity	NPD2654	Approved
0.7193	Intermediate Similarity	NPD37	Approved
0.7191	Intermediate Similarity	NPD7228	Approved
0.719	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD1610	Phase 2
0.7188	Intermediate Similarity	NPD447	Suspended
0.7186	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD2353	Approved
0.7176	Intermediate Similarity	NPD6585	Discontinued
0.7168	Intermediate Similarity	NPD4967	Phase 2
0.7168	Intermediate Similarity	NPD4965	Approved
0.7168	Intermediate Similarity	NPD4966	Approved
0.716	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD7229	Phase 3
0.7152	Intermediate Similarity	NPD1548	Phase 1
0.7152	Intermediate Similarity	NPD7095	Approved
0.7143	Intermediate Similarity	NPD7783	Phase 2
0.7143	Intermediate Similarity	NPD7700	Phase 2
0.7143	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7699	Phase 2
0.7143	Intermediate Similarity	NPD7801	Approved
0.7128	Intermediate Similarity	NPD8151	Discontinued
0.7127	Intermediate Similarity	NPD7685	Pre-registration
0.7125	Intermediate Similarity	NPD4307	Phase 2
0.7115	Intermediate Similarity	NPD3267	Approved
0.7115	Intermediate Similarity	NPD3266	Approved
0.7111	Intermediate Similarity	NPD1729	Discontinued
0.7108	Intermediate Similarity	NPD3887	Approved
0.7108	Intermediate Similarity	NPD6190	Approved
0.7098	Intermediate Similarity	NPD8319	Approved
0.7098	Intermediate Similarity	NPD8320	Phase 1
0.7091	Intermediate Similarity	NPD1652	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