NPASS Compound

Structure

CID205054 OpenBabel06191715592D 22 23 0 0 1 0 0 0 0 0999 V2000 2.5981 3.5000 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 4.3301 0.5000 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 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 6 1 0 0 0 0 2 3 2 0 0 0 0 2 7 1 0 0 0 0 3 8 1 0 0 0 0 4 7 2 0 0 0 0 4 9 1 0 0 0 0 5 15 1 0 0 0 0 6 7 1 0 0 0 0 6 16 2 0 0 0 0 8 9 2 0 0 0 0 8 17 1 0 0 0 0 9 21 1 0 0 0 0 10 5 1 6 0 0 0 10 11 1 0 0 0 0 10 22 1 0 0 0 0 11 12 1 0 0 0 0 11 18 1 1 0 0 0 12 13 1 0 0 0 0 12 19 1 6 0 0 0 13 14 1 0 0 0 0 13 20 1 1 0 0 0 14 21 1 6 0 0 0 14 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	314.1
Volume:	293.363
LogP:	-0.655
LogD:	-0.404
LogS:	-1.236
# Rotatable Bonds:	4
TPSA:	136.68
# H-Bond Aceptor:	8
# H-Bond Donor:	5
# Rings:	2
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.436
Synthetic Accessibility Score:	3.484
Fsp3:	0.5
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.061
MDCK Permeability:	4.112452734261751e-05
Pgp-inhibitor:	0.011
Pgp-substrate:	0.103
Human Intestinal Absorption (HIA):	0.749
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.956

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.49
Plasma Protein Binding (PPB):	59.98360061645508%
Volume Distribution (VD):	0.514
Pgp-substrate:	40.95269012451172%

ADMET: Metabolism

CYP1A2-inhibitor:	0.126
CYP1A2-substrate:	0.056
CYP2C19-inhibitor:	0.02
CYP2C19-substrate:	0.095
CYP2C9-inhibitor:	0.002
CYP2C9-substrate:	0.255
CYP2D6-inhibitor:	0.013
CYP2D6-substrate:	0.202
CYP3A4-inhibitor:	0.012
CYP3A4-substrate:	0.045

ADMET: Excretion

Clearance (CL):	1.939
Half-life (T1/2):	0.842

ADMET: Toxicity

hERG Blockers:	0.105
Human Hepatotoxicity (H-HT):	0.03
Drug-inuced Liver Injury (DILI):	0.455
AMES Toxicity:	0.312
Rat Oral Acute Toxicity:	0.024
Maximum Recommended Daily Dose:	0.003
Skin Sensitization:	0.091
Carcinogencity:	0.087
Eye Corrosion:	0.005
Eye Irritation:	0.374
Respiratory Toxicity:	0.026

Download Data

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

Natural Product: NPC205054

Natural Product ID:	NPC205054
*Common Name:**	Pungenin
IUPAC Name:	1-[4-hydroxy-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]ethanone
Synonyms:	Pungenin
Standard InCHIKey:	AOXMCWFZPZRDPE-RKQHYHRCSA-N
Standard InCHI:	InChI=1S/C14H18O8/c1-6(16)7-2-3-8(17)9(4-7)21-14-13(20)12(19)11(18)10(5-15)22-14/h2-4,10-15,17-20H,5H2,1H3/t10-,11-,12+,13-,14-/m1/s1
SMILES:	OC[C@H]1O[C@@H](Oc2cc(ccc2O)C(=O)C)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1092512
PubChem CID:	12314759
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000011] Carbohydrates and carbohydrate conjugates [CHEMONTID:0002105] Glycosyl compounds [CHEMONTID:0004165] Phenolic glycosides

*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
NPO6257	Ficus septica	Species	Moraceae	Eukaryota	Stems	Tainan Hsien, Taiwan, Republic of China	2000-JAN	PMID[16038551]
NPO2421	Picea glauca	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18636777]
NPO6257	Ficus septica	Species	Moraceae	Eukaryota	leaves	n.a.	n.a.	PMID[19938815]
NPO691	Tarchonanthus camphoratus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29244495]
NPO284	Albizia procera	Species	Fabaceae	Eukaryota	Bark	n.a.	n.a.	PMID[30520635]
NPO7770	Lactuca laciniata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO99	Artemisia porrecta	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5588	Bursera tonkinensis	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7155	Cypripedium calceolus	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6257	Ficus septica	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5588	Bursera tonkinensis	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6257	Ficus septica	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7155	Cypripedium calceolus	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7770	Lactuca laciniata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO99	Artemisia porrecta	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19432	Millettia pinnata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7155	Cypripedium calceolus	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO3415	Perymenium mendezii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15597	Calystegia pubescens	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19432	Millettia pinnata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29287	Alectoria ochroleuca	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7616	Melanargia galathea	Species	Nymphalidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO855	Elymnias thryallis	Species	Nymphalidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3263	Thea sasanqua	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO7770	Lactuca laciniata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO99	Artemisia porrecta	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5588	Bursera tonkinensis	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO691	Tarchonanthus camphoratus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7464	Uruparia lanosa	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO7155	Cypripedium calceolus	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2421	Picea glauca	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1539	Artemisia giraldii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6257	Ficus septica	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6844	Bulbophyllum protractum	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4421	Penicillium cyclopium	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3255	Lampranthus sociorum	Species	Aizoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5981	Achlys triphylla	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2963	Diospyros glaucifolia	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3963	Hortonia floribunda	Species	Monimiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO284	Albizia procera	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4117	Nauclea rhynchophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4952	Pertusaria amara	Species	Pertusariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

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

NP Quantity Composition/Concentration

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

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

Biological Activity

Activity Type	# Activity
IC50	2

Activity Type	# Activity
Cell Line	1
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT165	Cell Line	HeLa	Homo sapiens	IC50	>	160000.0	nM	PMID[475111]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	160000.0	nM	PMID[475111]

☑ 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 NPC205054 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	359
0.1-0.2	1423
0.2-0.3	3585
0.3-0.4	8404
0.4-0.5	9734
0.5-0.6	4086
0.6-0.7	5944
0.7-0.8	7295
0.8-0.85	1546
0.85-0.9	277
0.9-0.95	41
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9595	High Similarity	NPC471405
0.9527	High Similarity	NPC10205
0.9459	High Similarity	NPC327032
0.9459	High Similarity	NPC194095
0.9459	High Similarity	NPC191046
0.9392	High Similarity	NPC105827
0.9392	High Similarity	NPC310661
0.9392	High Similarity	NPC157898
0.9392	High Similarity	NPC137813
0.9324	High Similarity	NPC289438
0.9324	High Similarity	NPC36130
0.9324	High Similarity	NPC134905
0.9276	High Similarity	NPC203020
0.9276	High Similarity	NPC239966
0.9272	High Similarity	NPC133984
0.9211	High Similarity	NPC289811
0.9211	High Similarity	NPC160780
0.9189	High Similarity	NPC227980
0.9184	High Similarity	NPC472969
0.9156	High Similarity	NPC148273
0.9145	High Similarity	NPC226759
0.9145	High Similarity	NPC472860
0.9145	High Similarity	NPC1913
0.9122	High Similarity	NPC98809
0.9122	High Similarity	NPC111785
0.9122	High Similarity	NPC476394
0.9097	High Similarity	NPC88043
0.9091	High Similarity	NPC25389
0.9091	High Similarity	NPC311803
0.9091	High Similarity	NPC472859
0.9085	High Similarity	NPC294470
0.9048	High Similarity	NPC9370
0.9048	High Similarity	NPC287495
0.9045	High Similarity	NPC116745
0.9038	High Similarity	NPC165720
0.9032	High Similarity	NPC33298
0.9032	High Similarity	NPC285108
0.9026	High Similarity	NPC166277
0.9026	High Similarity	NPC119125
0.8993	High Similarity	NPC478242
0.8987	High Similarity	NPC229687
0.8974	High Similarity	NPC94777
0.8966	High Similarity	NPC79908
0.8961	High Similarity	NPC287872
0.8961	High Similarity	NPC74319
0.894	High Similarity	NPC75695
0.8931	High Similarity	NPC212748
0.8924	High Similarity	NPC229729
0.8924	High Similarity	NPC45400
0.8919	High Similarity	NPC291153
0.8919	High Similarity	NPC473867
0.8917	High Similarity	NPC311830
0.8917	High Similarity	NPC22832
0.8917	High Similarity	NPC180586
0.8912	High Similarity	NPC473090
0.891	High Similarity	NPC41009
0.891	High Similarity	NPC127782
0.891	High Similarity	NPC300537
0.8903	High Similarity	NPC289346
0.8875	High Similarity	NPC48773
0.8875	High Similarity	NPC205076
0.8875	High Similarity	NPC307518
0.8868	High Similarity	NPC58053
0.8868	High Similarity	NPC226294
0.8868	High Similarity	NPC93337
0.8868	High Similarity	NPC45638
0.8868	High Similarity	NPC105025
0.8868	High Similarity	NPC475942
0.8868	High Similarity	NPC186807
0.8868	High Similarity	NPC201292
0.8868	High Similarity	NPC469931
0.8861	High Similarity	NPC236934
0.8861	High Similarity	NPC99957
0.8861	High Similarity	NPC181616
0.8861	High Similarity	NPC5778
0.8854	High Similarity	NPC243930
0.8854	High Similarity	NPC147596
0.8854	High Similarity	NPC309025
0.8854	High Similarity	NPC284960
0.8854	High Similarity	NPC191306
0.8854	High Similarity	NPC19709
0.8854	High Similarity	NPC270335
0.8854	High Similarity	NPC88023
0.8854	High Similarity	NPC222936
0.8854	High Similarity	NPC168822
0.8851	High Similarity	NPC108455
0.8828	High Similarity	NPC100389
0.882	High Similarity	NPC172033
0.882	High Similarity	NPC175230
0.882	High Similarity	NPC88560
0.8819	High Similarity	NPC186418
0.8812	High Similarity	NPC51326
0.8812	High Similarity	NPC72249
0.8812	High Similarity	NPC231194
0.8812	High Similarity	NPC21190
0.8812	High Similarity	NPC22195
0.8812	High Similarity	NPC183357
0.8812	High Similarity	NPC224462
0.8812	High Similarity	NPC471416
0.8812	High Similarity	NPC34287
0.8812	High Similarity	NPC204937
0.8812	High Similarity	NPC44558
0.8812	High Similarity	NPC206123
0.8812	High Similarity	NPC149011
0.8812	High Similarity	NPC474434
0.8812	High Similarity	NPC105511
0.8808	High Similarity	NPC88886
0.8808	High Similarity	NPC473091
0.8808	High Similarity	NPC104172
0.8805	High Similarity	NPC45618
0.8805	High Similarity	NPC58716
0.8805	High Similarity	NPC146792
0.88	High Similarity	NPC116229
0.8797	High Similarity	NPC475738
0.8792	High Similarity	NPC474044
0.879	High Similarity	NPC189142
0.879	High Similarity	NPC476011
0.879	High Similarity	NPC77660
0.879	High Similarity	NPC61594
0.879	High Similarity	NPC90905
0.879	High Similarity	NPC4013
0.879	High Similarity	NPC56735
0.879	High Similarity	NPC473043
0.8784	High Similarity	NPC229036
0.8758	High Similarity	NPC211594
0.8758	High Similarity	NPC117260
0.8758	High Similarity	NPC476405
0.8758	High Similarity	NPC44730
0.8758	High Similarity	NPC172807
0.8758	High Similarity	NPC235575
0.8758	High Similarity	NPC254540
0.875	High Similarity	NPC219904
0.875	High Similarity	NPC658
0.875	High Similarity	NPC197708
0.875	High Similarity	NPC212729
0.875	High Similarity	NPC120099
0.875	High Similarity	NPC170675
0.875	High Similarity	NPC225434
0.875	High Similarity	NPC195257
0.875	High Similarity	NPC209296
0.875	High Similarity	NPC139519
0.875	High Similarity	NPC472383
0.875	High Similarity	NPC112755
0.875	High Similarity	NPC471457
0.875	High Similarity	NPC95855
0.875	High Similarity	NPC203050
0.875	High Similarity	NPC183036
0.875	High Similarity	NPC140151
0.875	High Similarity	NPC472381
0.875	High Similarity	NPC223747
0.875	High Similarity	NPC210042
0.8742	High Similarity	NPC210073
0.8742	High Similarity	NPC21100
0.8742	High Similarity	NPC115674
0.8742	High Similarity	NPC197285
0.8734	High Similarity	NPC29830
0.8726	High Similarity	NPC182045
0.8725	High Similarity	NPC469683
0.8716	High Similarity	NPC242756
0.8716	High Similarity	NPC478239
0.8707	High Similarity	NPC326065
0.8707	High Similarity	NPC80098
0.8704	High Similarity	NPC45522
0.8704	High Similarity	NPC24043
0.8704	High Similarity	NPC472993
0.8704	High Similarity	NPC4390
0.8704	High Similarity	NPC204693
0.8704	High Similarity	NPC42773
0.8704	High Similarity	NPC316539
0.8704	High Similarity	NPC239549
0.8704	High Similarity	NPC169977
0.8704	High Similarity	NPC51774
0.8704	High Similarity	NPC21666
0.8704	High Similarity	NPC199357
0.8704	High Similarity	NPC236191
0.8704	High Similarity	NPC101026
0.8699	High Similarity	NPC325625
0.8696	High Similarity	NPC177731
0.8696	High Similarity	NPC79056
0.8696	High Similarity	NPC245014
0.8696	High Similarity	NPC84265
0.8696	High Similarity	NPC105095
0.8696	High Similarity	NPC282987
0.8696	High Similarity	NPC44328
0.869	High Similarity	NPC37468
0.869	High Similarity	NPC157554
0.8688	High Similarity	NPC135345
0.8688	High Similarity	NPC93099
0.8688	High Similarity	NPC52550
0.8688	High Similarity	NPC84362
0.8688	High Similarity	NPC226304
0.8688	High Similarity	NPC317489
0.8688	High Similarity	NPC325555
0.8688	High Similarity	NPC265530
0.8688	High Similarity	NPC223424
0.8688	High Similarity	NPC48640
0.8688	High Similarity	NPC477502
0.8688	High Similarity	NPC298847
0.8688	High Similarity	NPC173637
0.8688	High Similarity	NPC127546

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 NPC205054 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	300
0.1-0.2	851
0.2-0.3	1799
0.3-0.4	2578
0.4-0.5	1931
0.5-0.6	1031
0.6-0.7	513
0.7-0.8	128
0.8-0.85	15
0.85-0.9	4
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8805	High Similarity	NPD3818	Discontinued
0.875	High Similarity	NPD7054	Approved
0.8696	High Similarity	NPD7472	Approved
0.8696	High Similarity	NPD7074	Phase 3
0.8537	High Similarity	NPD4338	Clinical (unspecified phase)
0.8528	High Similarity	NPD6797	Phase 2
0.8476	Intermediate Similarity	NPD7251	Discontinued
0.8424	Intermediate Similarity	NPD7808	Phase 3
0.8418	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8397	Intermediate Similarity	NPD1934	Approved
0.8364	Intermediate Similarity	NPD7685	Pre-registration
0.8354	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8258	Intermediate Similarity	NPD1653	Approved
0.8239	Intermediate Similarity	NPD3882	Suspended
0.8228	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8228	Intermediate Similarity	NPD2801	Approved
0.8221	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8221	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8221	Intermediate Similarity	NPD6166	Phase 2
0.8194	Intermediate Similarity	NPD9494	Approved
0.8108	Intermediate Similarity	NPD230	Phase 1
0.8079	Intermediate Similarity	NPD7266	Discontinued
0.8039	Intermediate Similarity	NPD4628	Phase 3
0.8	Intermediate Similarity	NPD1511	Approved
0.8	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7976	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7964	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7962	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.795	Intermediate Similarity	NPD3817	Phase 2
0.7929	Intermediate Similarity	NPD6559	Discontinued
0.7898	Intermediate Similarity	NPD1512	Approved
0.7888	Intermediate Similarity	NPD1465	Phase 2
0.7871	Intermediate Similarity	NPD6190	Approved
0.7849	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7812	Intermediate Similarity	NPD4380	Phase 2
0.7751	Intermediate Similarity	NPD5844	Phase 1
0.7748	Intermediate Similarity	NPD447	Suspended
0.7744	Intermediate Similarity	NPD7075	Discontinued
0.7697	Intermediate Similarity	NPD6234	Discontinued
0.7692	Intermediate Similarity	NPD7228	Approved
0.7677	Intermediate Similarity	NPD1549	Phase 2
0.7671	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7655	Intermediate Similarity	NPD1091	Approved
0.7651	Intermediate Similarity	NPD5494	Approved
0.763	Intermediate Similarity	NPD8312	Approved
0.763	Intermediate Similarity	NPD8313	Approved
0.7614	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7613	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7613	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7607	Intermediate Similarity	NPD37	Approved
0.7605	Intermediate Similarity	NPD7199	Phase 2
0.76	Intermediate Similarity	NPD3027	Phase 3
0.7576	Intermediate Similarity	NPD4966	Approved
0.7576	Intermediate Similarity	NPD4965	Approved
0.7576	Intermediate Similarity	NPD4967	Phase 2
0.7566	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7566	Intermediate Similarity	NPD1613	Approved
0.7561	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD6799	Approved
0.7528	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD5402	Approved
0.75	Intermediate Similarity	NPD9545	Approved
0.75	Intermediate Similarity	NPD6801	Discontinued
0.7485	Intermediate Similarity	NPD3751	Discontinued
0.7468	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD6232	Discontinued
0.7455	Intermediate Similarity	NPD8455	Phase 2
0.7455	Intermediate Similarity	NPD7819	Suspended
0.7439	Intermediate Similarity	NPD6385	Approved
0.7439	Intermediate Similarity	NPD6386	Approved
0.7427	Intermediate Similarity	NPD7473	Discontinued
0.7412	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD5353	Approved
0.7403	Intermediate Similarity	NPD1933	Approved
0.7391	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD1510	Phase 2
0.7365	Intermediate Similarity	NPD9269	Phase 2
0.7353	Intermediate Similarity	NPD3787	Discontinued
0.7342	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD1240	Approved
0.7338	Intermediate Similarity	NPD943	Approved
0.7333	Intermediate Similarity	NPD7411	Suspended
0.7329	Intermediate Similarity	NPD1357	Approved
0.7325	Intermediate Similarity	NPD2796	Approved
0.7305	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD5403	Approved
0.7297	Intermediate Similarity	NPD3705	Approved
0.7296	Intermediate Similarity	NPD6674	Discontinued
0.7294	Intermediate Similarity	NPD1247	Approved
0.7278	Intermediate Similarity	NPD919	Approved
0.7273	Intermediate Similarity	NPD1241	Discontinued
0.7273	Intermediate Similarity	NPD6599	Discontinued
0.7254	Intermediate Similarity	NPD228	Approved
0.7248	Intermediate Similarity	NPD1608	Approved
0.7244	Intermediate Similarity	NPD1607	Approved
0.7243	Intermediate Similarity	NPD6779	Approved
0.7243	Intermediate Similarity	NPD6776	Approved
0.7243	Intermediate Similarity	NPD6782	Approved
0.7243	Intermediate Similarity	NPD6780	Approved
0.7243	Intermediate Similarity	NPD6778	Approved
0.7243	Intermediate Similarity	NPD6777	Approved
0.7243	Intermediate Similarity	NPD6781	Approved
0.7237	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD7038	Approved
0.7216	Intermediate Similarity	NPD7039	Approved
0.7216	Intermediate Similarity	NPD7240	Approved
0.7215	Intermediate Similarity	NPD2935	Discontinued
0.7212	Intermediate Similarity	NPD7458	Discontinued
0.7209	Intermediate Similarity	NPD3926	Phase 2
0.7208	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD8127	Discontinued
0.7193	Intermediate Similarity	NPD6959	Discontinued
0.7192	Intermediate Similarity	NPD5536	Phase 2
0.7178	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD5401	Approved
0.7161	Intermediate Similarity	NPD6233	Phase 2
0.7152	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4110	Phase 3
0.7143	Intermediate Similarity	NPD3750	Approved
0.7143	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD7435	Discontinued
0.7125	Intermediate Similarity	NPD2424	Discontinued
0.7111	Intermediate Similarity	NPD8434	Phase 2
0.711	Intermediate Similarity	NPD5242	Approved
0.7108	Intermediate Similarity	NPD3226	Approved
0.7108	Intermediate Similarity	NPD824	Approved
0.7108	Intermediate Similarity	NPD3455	Phase 2
0.7107	Intermediate Similarity	NPD1551	Phase 2
0.7095	Intermediate Similarity	NPD9268	Approved
0.7086	Intermediate Similarity	NPD2163	Approved
0.7073	Intermediate Similarity	NPD2534	Approved
0.7073	Intermediate Similarity	NPD2533	Approved
0.7073	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD3688	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD2532	Approved
0.7073	Intermediate Similarity	NPD3146	Approved
0.7069	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD2344	Approved
0.7047	Intermediate Similarity	NPD17	Approved
0.7044	Intermediate Similarity	NPD2799	Discontinued
0.7037	Intermediate Similarity	NPD7696	Phase 3
0.7037	Intermediate Similarity	NPD7698	Approved
0.7037	Intermediate Similarity	NPD7697	Approved
0.7031	Intermediate Similarity	NPD8151	Discontinued
0.7025	Intermediate Similarity	NPD6653	Approved
0.702	Intermediate Similarity	NPD9717	Approved
0.7016	Intermediate Similarity	NPD7584	Approved
0.7006	Intermediate Similarity	NPD3142	Approved
0.7006	Intermediate Similarity	NPD3140	Approved
0.7	Intermediate Similarity	NPD7871	Phase 2
0.7	Intermediate Similarity	NPD7870	Phase 2
0.7	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD3887	Approved
0.6994	Remote Similarity	NPD2354	Approved
0.6993	Remote Similarity	NPD1203	Approved
0.6988	Remote Similarity	NPD920	Approved
0.6987	Remote Similarity	NPD6798	Discontinued
0.6984	Remote Similarity	NPD6823	Phase 2
0.6981	Remote Similarity	NPD7097	Phase 1
0.6979	Remote Similarity	NPD7701	Phase 2
0.6978	Remote Similarity	NPD6842	Approved
0.6978	Remote Similarity	NPD6841	Approved
0.6978	Remote Similarity	NPD6843	Phase 3
0.6975	Remote Similarity	NPD2800	Approved
0.6975	Remote Similarity	NPD1652	Phase 2
0.6973	Remote Similarity	NPD6535	Approved
0.6973	Remote Similarity	NPD6534	Approved
0.6968	Remote Similarity	NPD6832	Phase 2
0.6964	Remote Similarity	NPD7028	Phase 2
0.6962	Remote Similarity	NPD6355	Discontinued
0.6959	Remote Similarity	NPD7783	Phase 2
0.6959	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD2346	Discontinued
0.6954	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD5647	Approved
0.6946	Remote Similarity	NPD3686	Approved
0.6946	Remote Similarity	NPD3687	Approved
0.6943	Remote Similarity	NPD4062	Phase 3
0.6941	Remote Similarity	NPD1006	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD7033	Discontinued
0.6933	Remote Similarity	NPD1778	Approved
0.6933	Remote Similarity	NPD8166	Discontinued
0.6933	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD6273	Approved
0.6919	Remote Similarity	NPD3749	Approved
0.6915	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD1481	Phase 2
0.6908	Remote Similarity	NPD3972	Approved
0.6907	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6907	Remote Similarity	NPD7874	Approved
0.6905	Remote Similarity	NPD2649	Approved
0.6905	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD2651	Approved
0.6899	Remote Similarity	NPD1558	Phase 1
0.6894	Remote Similarity	NPD6099	Approved
0.6894	Remote Similarity	NPD6100	Approved
0.6891	Remote Similarity	NPD7585	Approved
0.689	Remote Similarity	NPD2309	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