NPASS Compound

Structure

CID126492 OpenBabel06191715482D 28 32 0 0 1 0 0 0 0 0999 V2000 -5.9292 -0.3858 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8252 -2.8009 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7856 -2.8009 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4824 0.5646 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0298 -0.9750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5210 1.4458 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5202 0.4734 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6793 1.9327 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6777 -0.0121 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6593 -1.9006 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1285 -0.4750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3054 0.0002 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8362 -1.4254 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0137 1.9224 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6585 0.9726 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9292 -1.4254 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8368 1.4472 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8223 1.4476 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8359 0.4748 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4824 -1.4254 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6593 0.0002 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.1285 -1.4254 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3054 -1.9006 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4824 -0.4750 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8362 -0.4750 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -6.8295 -1.9452 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0289 -1.9452 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 16 1 0 0 0 0 2 23 1 0 0 0 0 3 23 1 0 0 0 0 6 7 2 0 0 0 0 6 8 1 0 0 0 0 7 9 1 0 0 0 0 8 17 2 0 0 0 0 9 19 2 0 0 0 0 10 13 1 0 0 0 0 10 20 1 0 0 0 0 11 12 1 0 0 0 0 11 22 1 0 0 0 0 12 24 1 0 0 0 0 13 25 1 0 0 0 0 14 17 1 0 0 0 0 14 18 2 0 0 0 0 15 18 1 0 0 0 0 15 21 1 0 0 0 0 16 27 2 0 0 0 0 16 28 1 0 0 0 0 17 19 1 0 0 0 0 18 26 1 0 0 0 0 19 26 1 0 0 0 0 20 23 1 0 0 0 0 20 24 1 1 0 0 0 21 24 1 1 0 0 0 21 25 1 0 0 0 0 22 23 1 0 0 0 0 22 28 1 1 0 0 0 24 4 1 1 0 0 0 25 5 1 1 0 0 0 25 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	379.25
Volume:	413.569
LogP:	5.704
LogD:	4.611
LogS:	-6.489
# Rotatable Bonds:	2
TPSA:	31.23
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.595
Synthetic Accessibility Score:	4.263
Fsp3:	0.64
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.825
MDCK Permeability:	2.292733006470371e-05
Pgp-inhibitor:	0.986
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.664
30% Bioavailability (F30%):	0.989

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.189
Plasma Protein Binding (PPB):	94.70316314697266%
Volume Distribution (VD):	0.917
Pgp-substrate:	6.187474727630615%

ADMET: Metabolism

CYP1A2-inhibitor:	0.139
CYP1A2-substrate:	0.139
CYP2C19-inhibitor:	0.484
CYP2C19-substrate:	0.853
CYP2C9-inhibitor:	0.471
CYP2C9-substrate:	0.503
CYP2D6-inhibitor:	0.191
CYP2D6-substrate:	0.351
CYP3A4-inhibitor:	0.615
CYP3A4-substrate:	0.655

ADMET: Excretion

Clearance (CL):	4.359
Half-life (T1/2):	0.135

ADMET: Toxicity

hERG Blockers:	0.033
Human Hepatotoxicity (H-HT):	0.264
Drug-inuced Liver Injury (DILI):	0.106
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.019
Maximum Recommended Daily Dose:	0.97
Skin Sensitization:	0.674
Carcinogencity:	0.024
Eye Corrosion:	0.004
Eye Irritation:	0.028
Respiratory Toxicity:	0.883

Download Data

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

Natural Product: NPC126492

Natural Product ID:	NPC126492
*Common Name:**	DRMMGUOJBQDCMO-LJDQNPOQSA-N
IUPAC Name:	n.a.
Synonyms:	3-O-Acetylgreenwayodendrin
Standard InCHIKey:	DRMMGUOJBQDCMO-LJDQNPOQSA-N
Standard InCHI:	InChI=1S/C25H33NO2/c1-16(27)28-22-11-12-24(4)20(23(22,2)3)10-13-25(5)21(24)15-18-14-17-8-6-7-9-19(17)26(18)25/h6-9,14,20-22H,10-13,15H2,1-5H3/t20-,21+,22-,24-,25+/m0/s1
SMILES:	CC(=O)O[C@H]1CC[C@@]2(C)[C@@H](CC[C@]3(C)[C@@H]2Cc2cc4ccccc4n32)C1(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1083629
PubChem CID:	46891355
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles and derivatives [CHEMONTID:0002497] Indoles

*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
NPO4501	Caragana intermedia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15620236]
NPO24342	Lupinus albus	Species	Fabaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO24342	Lupinus albus	Species	Fabaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO16473	Araucaria bidwillii	Species	Araucariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23170	Orobanche coerulescens	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24342	Lupinus albus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23170	Orobanche coerulescens	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24342	Lupinus albus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16473	Araucaria bidwillii	Species	Araucariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24342	Lupinus albus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO23170	Orobanche coerulescens	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO23170	Orobanche coerulescens	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO24342	Lupinus albus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23170	Orobanche coerulescens	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21816	Calea jamaicensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25164	Polyalthia suaveolens	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24593	Campanula pyramidalis	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16473	Araucaria bidwillii	Species	Araucariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24561	Sesuvium portulacastrum	Species	Aizoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25009	Cystoseira myrica	Species	Sargassaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4501	Caragana intermedia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24939	Veronica officinalis	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13718	Poria tenuis	Species	Coccinellidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24123	Ramalina scopulorum	Species	Ramalinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12599.1	Pinus leiophylla var. chihuahuana	Varieties	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28729	Spirostachys africana	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14893	Streptomyces eurocidicus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO24723	Ophiorrhiza bracteata	Species	Rubiaceae	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	6
Others	1

Activity Type	# Activity
Individual Protein	4
Others	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT4419	Individual Protein	Glyceraldehyde-3-phosphate dehydrogenase	Oryctolagus cuniculus	IC50	=	2050000.0	nM	PMID[511976]
NPT4420	Individual Protein	6-phosphofructokinase, muscle type	Oryctolagus cuniculus	Inhibition	=	16.0	%	PMID[511976]
NPT62	Individual Protein	6-phospho-1-fructokinase	Trypanosoma brucei	IC50	=	170000.0	nM	PMID[511976]
NPT2	Others	Unspecified		IC50	=	110000.0	nM	PMID[511976]
NPT714	Individual Protein	Fructose-bisphosphate aldolase A	Oryctolagus cuniculus	IC50	=	150000.0	nM	PMID[511976]
NPT2	Others	Unspecified		IC50	=	500.0	nM	PMID[511976]

☑ 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 NPC126492 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	309
0.1-0.2	1419
0.2-0.3	5235
0.3-0.4	22780
0.4-0.5	8479
0.5-0.6	2743
0.6-0.7	1525
0.7-0.8	194
0.8-0.85	11
0.85-0.9	1
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.85	High Similarity	NPC200743
0.8304	Intermediate Similarity	NPC6093
0.8192	Intermediate Similarity	NPC206967
0.8176	Intermediate Similarity	NPC97525
0.8114	Intermediate Similarity	NPC165201
0.8046	Intermediate Similarity	NPC198339
0.8011	Intermediate Similarity	NPC181502
0.8011	Intermediate Similarity	NPC85066
0.8	Intermediate Similarity	NPC154293
0.7989	Intermediate Similarity	NPC475151
0.7978	Intermediate Similarity	NPC119700
0.7978	Intermediate Similarity	NPC473747
0.7898	Intermediate Similarity	NPC302191
0.7841	Intermediate Similarity	NPC300688
0.7833	Intermediate Similarity	NPC34271
0.7801	Intermediate Similarity	NPC475165
0.7778	Intermediate Similarity	NPC18661
0.776	Intermediate Similarity	NPC250129
0.768	Intermediate Similarity	NPC473547
0.7676	Intermediate Similarity	NPC231342
0.7654	Intermediate Similarity	NPC472104
0.7641	Intermediate Similarity	NPC97388
0.7624	Intermediate Similarity	NPC99428
0.7611	Intermediate Similarity	NPC472119
0.7604	Intermediate Similarity	NPC470280
0.7592	Intermediate Similarity	NPC187456
0.7581	Intermediate Similarity	NPC205403
0.7571	Intermediate Similarity	NPC56618
0.7556	Intermediate Similarity	NPC19679
0.7528	Intermediate Similarity	NPC151939
0.7526	Intermediate Similarity	NPC123019
0.7473	Intermediate Similarity	NPC476319
0.7471	Intermediate Similarity	NPC477975
0.7463	Intermediate Similarity	NPC41318
0.7463	Intermediate Similarity	NPC469312
0.7459	Intermediate Similarity	NPC472097
0.7435	Intermediate Similarity	NPC162730
0.7421	Intermediate Similarity	NPC79129
0.7421	Intermediate Similarity	NPC249150
0.7421	Intermediate Similarity	NPC49196
0.7421	Intermediate Similarity	NPC195461
0.7421	Intermediate Similarity	NPC81654
0.7421	Intermediate Similarity	NPC313985
0.7405	Intermediate Similarity	NPC329858
0.7399	Intermediate Similarity	NPC81229
0.7399	Intermediate Similarity	NPC255229
0.7398	Intermediate Similarity	NPC204303
0.7389	Intermediate Similarity	NPC213468
0.7386	Intermediate Similarity	NPC201700
0.7381	Intermediate Similarity	NPC477134
0.7378	Intermediate Similarity	NPC104483
0.7374	Intermediate Similarity	NPC160527
0.7374	Intermediate Similarity	NPC472122
0.7374	Intermediate Similarity	NPC24594
0.7374	Intermediate Similarity	NPC473650
0.7351	Intermediate Similarity	NPC46413
0.7344	Intermediate Similarity	NPC474116
0.7316	Intermediate Similarity	NPC50503
0.7306	Intermediate Similarity	NPC477135
0.7304	Intermediate Similarity	NPC245756
0.7297	Intermediate Similarity	NPC473177
0.7296	Intermediate Similarity	NPC284102
0.7294	Intermediate Similarity	NPC33421
0.7287	Intermediate Similarity	NPC473178
0.7283	Intermediate Similarity	NPC473189
0.7283	Intermediate Similarity	NPC79062
0.7283	Intermediate Similarity	NPC472107
0.7282	Intermediate Similarity	NPC477065
0.7273	Intermediate Similarity	NPC235900
0.7273	Intermediate Similarity	NPC475778
0.7268	Intermediate Similarity	NPC79107
0.7268	Intermediate Similarity	NPC475424
0.7263	Intermediate Similarity	NPC34508
0.7259	Intermediate Similarity	NPC126066
0.7259	Intermediate Similarity	NPC234999
0.7254	Intermediate Similarity	NPC193761
0.7253	Intermediate Similarity	NPC472105
0.7253	Intermediate Similarity	NPC187827
0.7247	Intermediate Similarity	NPC280548
0.7233	Intermediate Similarity	NPC183426
0.7228	Intermediate Similarity	NPC475476
0.7228	Intermediate Similarity	NPC242446
0.7225	Intermediate Similarity	NPC51054
0.7222	Intermediate Similarity	NPC329688
0.7222	Intermediate Similarity	NPC189812
0.7219	Intermediate Similarity	NPC314333
0.7214	Intermediate Similarity	NPC96131
0.7204	Intermediate Similarity	NPC472323
0.72	Intermediate Similarity	NPC471284
0.7198	Intermediate Similarity	NPC133261
0.7175	Intermediate Similarity	NPC470508
0.7174	Intermediate Similarity	NPC472109
0.7174	Intermediate Similarity	NPC472110
0.7174	Intermediate Similarity	NPC143533
0.7172	Intermediate Similarity	NPC475422
0.7159	Intermediate Similarity	NPC16667
0.7158	Intermediate Similarity	NPC15840
0.7157	Intermediate Similarity	NPC87755
0.7151	Intermediate Similarity	NPC66210
0.715	Intermediate Similarity	NPC11017
0.7143	Intermediate Similarity	NPC6436
0.7143	Intermediate Similarity	NPC326575
0.7143	Intermediate Similarity	NPC67056
0.7143	Intermediate Similarity	NPC55493
0.7135	Intermediate Similarity	NPC258480
0.7128	Intermediate Similarity	NPC95783
0.7127	Intermediate Similarity	NPC469938
0.7126	Intermediate Similarity	NPC184476
0.7126	Intermediate Similarity	NPC285469
0.7119	Intermediate Similarity	NPC8104
0.7119	Intermediate Similarity	NPC311276
0.7108	Intermediate Similarity	NPC61813
0.7104	Intermediate Similarity	NPC270009
0.7098	Intermediate Similarity	NPC32200
0.7083	Intermediate Similarity	NPC277157
0.7081	Intermediate Similarity	NPC472108
0.7081	Intermediate Similarity	NPC139291
0.7077	Intermediate Similarity	NPC137589
0.7076	Intermediate Similarity	NPC477974
0.7071	Intermediate Similarity	NPC61637
0.7069	Intermediate Similarity	NPC207726
0.7066	Intermediate Similarity	NPC312092
0.7062	Intermediate Similarity	NPC214428
0.7055	Intermediate Similarity	NPC475450
0.7049	Intermediate Similarity	NPC211997
0.7049	Intermediate Similarity	NPC14325
0.7049	Intermediate Similarity	NPC234987
0.7049	Intermediate Similarity	NPC28848
0.7047	Intermediate Similarity	NPC102008
0.7044	Intermediate Similarity	NPC122718
0.7043	Intermediate Similarity	NPC472294
0.7035	Intermediate Similarity	NPC124005
0.7033	Intermediate Similarity	NPC472586
0.7031	Intermediate Similarity	NPC245916
0.7027	Intermediate Similarity	NPC192270
0.7024	Intermediate Similarity	NPC238499
0.7018	Intermediate Similarity	NPC212799
0.7018	Intermediate Similarity	NPC129042
0.7017	Intermediate Similarity	NPC158129
0.7012	Intermediate Similarity	NPC473930
0.701	Intermediate Similarity	NPC476175
0.7006	Intermediate Similarity	NPC473320
0.7	Intermediate Similarity	NPC242556
0.6995	Remote Similarity	NPC84347
0.6995	Remote Similarity	NPC134586
0.6994	Remote Similarity	NPC475428
0.6989	Remote Similarity	NPC472444
0.6989	Remote Similarity	NPC129721
0.6985	Remote Similarity	NPC470931
0.6984	Remote Similarity	NPC63199
0.6984	Remote Similarity	NPC196251
0.6984	Remote Similarity	NPC111602
0.6984	Remote Similarity	NPC175474
0.6984	Remote Similarity	NPC102338
0.6979	Remote Similarity	NPC289299
0.6979	Remote Similarity	NPC57994
0.6978	Remote Similarity	NPC477976
0.6977	Remote Similarity	NPC471782
0.6977	Remote Similarity	NPC471583
0.6971	Remote Similarity	NPC471458
0.6971	Remote Similarity	NPC235885
0.697	Remote Similarity	NPC277350
0.6967	Remote Similarity	NPC282033
0.6959	Remote Similarity	NPC52557
0.6957	Remote Similarity	NPC64436
0.6957	Remote Similarity	NPC293472
0.6951	Remote Similarity	NPC179365
0.695	Remote Similarity	NPC478158
0.6949	Remote Similarity	NPC41257
0.6946	Remote Similarity	NPC478157
0.6944	Remote Similarity	NPC470509
0.6941	Remote Similarity	NPC20144
0.6939	Remote Similarity	NPC300183
0.6938	Remote Similarity	NPC472762
0.6933	Remote Similarity	NPC473587
0.693	Remote Similarity	NPC278540
0.693	Remote Similarity	NPC473565
0.6927	Remote Similarity	NPC472587
0.6927	Remote Similarity	NPC40779
0.6923	Remote Similarity	NPC81561
0.6919	Remote Similarity	NPC478186
0.6919	Remote Similarity	NPC472443
0.6919	Remote Similarity	NPC473806
0.6919	Remote Similarity	NPC471634
0.6915	Remote Similarity	NPC62510
0.6914	Remote Similarity	NPC281094
0.6912	Remote Similarity	NPC251936
0.6907	Remote Similarity	NPC229332
0.6901	Remote Similarity	NPC116519
0.6899	Remote Similarity	NPC215519
0.6898	Remote Similarity	NPC469358
0.6897	Remote Similarity	NPC475602
0.6893	Remote Similarity	NPC286427
0.6893	Remote Similarity	NPC469762
0.6888	Remote Similarity	NPC470279
0.6885	Remote Similarity	NPC472123
0.6882	Remote Similarity	NPC469896
0.6879	Remote Similarity	NPC162689
0.6879	Remote Similarity	NPC54102
0.6878	Remote Similarity	NPC160381

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 NPC126492 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	215
0.1-0.2	581
0.2-0.3	621
0.3-0.4	1791
0.4-0.5	3197
0.5-0.6	2143
0.6-0.7	570
0.7-0.8	31
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7838	Intermediate Similarity	NPD6661	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD5721	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD6635	Approved
0.7554	Intermediate Similarity	NPD6630	Clinical (unspecified phase)
0.7541	Intermediate Similarity	NPD7234	Approved
0.7541	Intermediate Similarity	NPD7233	Approved
0.7472	Intermediate Similarity	NPD6375	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD4600	Approved
0.7421	Intermediate Similarity	NPD4601	Approved
0.7371	Intermediate Similarity	NPD5744	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD6281	Approved
0.7288	Intermediate Similarity	NPD4638	Approved
0.7288	Intermediate Similarity	NPD4639	Approved
0.7288	Intermediate Similarity	NPD5021	Discontinued
0.7288	Intermediate Similarity	NPD4640	Approved
0.7283	Intermediate Similarity	NPD4326	Phase 2
0.7278	Intermediate Similarity	NPD5104	Approved
0.7278	Intermediate Similarity	NPD5501	Discontinued
0.7268	Intermediate Similarity	NPD4345	Clinical (unspecified phase)
0.7253	Intermediate Similarity	NPD5899	Approved
0.7253	Intermediate Similarity	NPD5897	Approved
0.7253	Intermediate Similarity	NPD5898	Approved
0.7231	Intermediate Similarity	NPD7957	Phase 1
0.7231	Intermediate Similarity	NPD7958	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD4499	Approved
0.7213	Intermediate Similarity	NPD4383	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD6739	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD3385	Approved
0.7175	Intermediate Similarity	NPD4550	Clinical (unspecified phase)
0.7175	Intermediate Similarity	NPD2915	Discontinued
0.7174	Intermediate Similarity	NPD5522	Clinical (unspecified phase)
0.7157	Intermediate Similarity	NPD7947	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD7707	Approved
0.7111	Intermediate Similarity	NPD5472	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD6344	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD7424	Clinical (unspecified phase)
0.709	Intermediate Similarity	NPD5913	Phase 3
0.709	Intermediate Similarity	NPD5912	Clinical (unspecified phase)
0.7072	Intermediate Similarity	NPD6183	Clinical (unspecified phase)
0.7072	Intermediate Similarity	NPD43	Approved
0.7072	Intermediate Similarity	NPD6182	Approved
0.7068	Intermediate Similarity	NPD4418	Discontinued
0.7056	Intermediate Similarity	NPD7474	Suspended
0.7053	Intermediate Similarity	NPD6619	Phase 3
0.7047	Intermediate Similarity	NPD53	Approved
0.7047	Intermediate Similarity	NPD7778	Approved
0.7047	Intermediate Similarity	NPD7777	Approved
0.7037	Intermediate Similarity	NPD3654	Approved
0.7005	Intermediate Similarity	NPD5075	Discontinued
0.7	Intermediate Similarity	NPD5254	Discontinued
0.7	Intermediate Similarity	NPD4779	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD5471	Phase 3
0.6995	Remote Similarity	NPD5003	Discontinued
0.6982	Remote Similarity	NPD5020	Approved
0.6979	Remote Similarity	NPD7944	Discontinued
0.6979	Remote Similarity	NPD4602	Approved
0.6978	Remote Similarity	NPD7418	Discontinued
0.6973	Remote Similarity	NPD6452	Discontinued
0.6973	Remote Similarity	NPD8464	Clinical (unspecified phase)
0.6967	Remote Similarity	NPD7688	Phase 1
0.6966	Remote Similarity	NPD5315	Discontinued
0.6959	Remote Similarity	NPD6846	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD2144	Approved
0.6954	Remote Similarity	NPD6476	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD6158	Phase 2
0.6954	Remote Similarity	NPD6176	Phase 1
0.6946	Remote Similarity	NPD6554	Approved
0.6946	Remote Similarity	NPD8112	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD45	Approved
0.6943	Remote Similarity	NPD6550	Discontinued
0.6935	Remote Similarity	NPD3038	Discontinued
0.6935	Remote Similarity	NPD5429	Discontinued
0.6932	Remote Similarity	NPD6026	Approved
0.6919	Remote Similarity	NPD4076	Approved
0.6919	Remote Similarity	NPD4079	Approved
0.6919	Remote Similarity	NPD6987	Phase 1
0.6919	Remote Similarity	NPD1683	Approved
0.6911	Remote Similarity	NPD4918	Discontinued
0.6897	Remote Similarity	NPD7276	Approved
0.6897	Remote Similarity	NPD7277	Approved
0.6888	Remote Similarity	NPD6479	Discontinued
0.6885	Remote Similarity	NPD4112	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD750	Phase 2
0.6882	Remote Similarity	NPD6595	Phase 3
0.6875	Remote Similarity	NPD6995	Phase 1
0.6865	Remote Similarity	NPD4398	Clinical (unspecified phase)
0.6865	Remote Similarity	NPD3505	Approved
0.6865	Remote Similarity	NPD8122	Approved
0.6865	Remote Similarity	NPD8123	Approved
0.6865	Remote Similarity	NPD3506	Approved
0.6857	Remote Similarity	NPD2882	Phase 1
0.6856	Remote Similarity	NPD7935	Phase 2
0.6856	Remote Similarity	NPD5512	Phase 3
0.6842	Remote Similarity	NPD4637	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD3323	Discontinued
0.6831	Remote Similarity	NPD5934	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD8036	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD8037	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD5398	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD4880	Discontinued
0.6825	Remote Similarity	NPD6610	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD3943	Clinical (unspecified phase)
0.6811	Remote Similarity	NPD4075	Phase 2
0.6809	Remote Similarity	NPD5728	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD4334	Discontinued
0.6802	Remote Similarity	NPD4501	Approved
0.6802	Remote Similarity	NPD4500	Approved
0.68	Remote Similarity	NPD3833	Phase 3
0.68	Remote Similarity	NPD4462	Approved
0.68	Remote Similarity	NPD3835	Phase 3
0.68	Remote Similarity	NPD2172	Phase 1
0.68	Remote Similarity	NPD4463	Approved
0.6789	Remote Similarity	NPD5444	Phase 1
0.6782	Remote Similarity	NPD2125	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD4547	Phase 3
0.678	Remote Similarity	NPD5257	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD1326	Approved
0.6776	Remote Similarity	NPD1325	Approved
0.6774	Remote Similarity	NPD6203	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD4957	Phase 2
0.6771	Remote Similarity	NPD2564	Approved
0.6771	Remote Similarity	NPD2565	Phase 2
0.676	Remote Similarity	NPD1630	Approved
0.6758	Remote Similarity	NPD4554	Clinical (unspecified phase)
0.6755	Remote Similarity	NPD4399	Phase 2
0.6754	Remote Similarity	NPD8431	Approved
0.6754	Remote Similarity	NPD3002	Clinical (unspecified phase)
0.675	Remote Similarity	NPD6138	Clinical (unspecified phase)
0.675	Remote Similarity	NPD7103	Approved
0.6738	Remote Similarity	NPD8386	Phase 2
0.6733	Remote Similarity	NPD2510	Approved
0.6733	Remote Similarity	NPD2509	Approved
0.6731	Remote Similarity	NPD6455	Phase 3
0.6721	Remote Similarity	NPD2844	Phase 3
0.672	Remote Similarity	NPD749	Clinical (unspecified phase)
0.6717	Remote Similarity	NPD8248	Clinical (unspecified phase)
0.6716	Remote Similarity	NPD7470	Discontinued
0.6716	Remote Similarity	NPD7001	Phase 3
0.6704	Remote Similarity	NPD4671	Clinical (unspecified phase)
0.6704	Remote Similarity	NPD4669	Clinical (unspecified phase)
0.6704	Remote Similarity	NPD4670	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD5809	Phase 3
0.6701	Remote Similarity	NPD4987	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD6717	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD972	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD1575	Approved
0.6685	Remote Similarity	NPD1573	Approved
0.6684	Remote Similarity	NPD7818	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD5083	Clinical (unspecified phase)
0.6683	Remote Similarity	NPD7222	Phase 2
0.6683	Remote Similarity	NPD7452	Approved
0.6683	Remote Similarity	NPD7453	Approved
0.6682	Remote Similarity	NPD7770	Phase 3
0.6682	Remote Similarity	NPD7824	Approved
0.6682	Remote Similarity	NPD5891	Approved
0.6667	Remote Similarity	NPD7621	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4948	Discontinued
0.6667	Remote Similarity	NPD3486	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7268	Clinical (unspecified phase)
0.6651	Remote Similarity	NPD6976	Clinical (unspecified phase)
0.6651	Remote Similarity	NPD7271	Approved
0.665	Remote Similarity	NPD6988	Phase 1
0.665	Remote Similarity	NPD6975	Discontinued
0.665	Remote Similarity	NPD2916	Discontinued
0.6649	Remote Similarity	NPD3785	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD1631	Approved
0.6647	Remote Similarity	NPD1251	Discontinued
0.6647	Remote Similarity	NPD3525	Discontinued
0.6647	Remote Similarity	NPD1262	Discovery
0.6634	Remote Similarity	NPD6732	Clinical (unspecified phase)
0.6634	Remote Similarity	NPD8013	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD6965	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD1534	Approved
0.663	Remote Similarity	NPD5862	Discovery
0.6619	Remote Similarity	NPD7678	Clinical (unspecified phase)
0.6617	Remote Similarity	NPD8072	Approved
0.6617	Remote Similarity	NPD2920	Discontinued
0.6615	Remote Similarity	NPD4315	Phase 2
0.6614	Remote Similarity	NPD5473	Discontinued
0.6602	Remote Similarity	NPD7455	Approved
0.6602	Remote Similarity	NPD7454	Approved
0.6602	Remote Similarity	NPD7069	Discontinued
0.6601	Remote Similarity	NPD8322	Phase 2
0.66	Remote Similarity	NPD7931	Approved
0.66	Remote Similarity	NPD7934	Discovery
0.66	Remote Similarity	NPD7933	Approved
0.66	Remote Similarity	NPD7932	Clinical (unspecified phase)
0.66	Remote Similarity	NPD7903	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD4181	Approved
0.6595	Remote Similarity	NPD4184	Clinical (unspecified phase)
0.659	Remote Similarity	NPD1592	Phase 3
0.6589	Remote Similarity	NPD7730	Approved
0.6589	Remote Similarity	NPD7731	Approved
0.6589	Remote Similarity	NPD6978	Phase 2
0.6589	Remote Similarity	NPD6977	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD1255	Approved
0.6588	Remote Similarity	NPD1254	Approved
0.6588	Remote Similarity	NPD1256	Approved
0.6588	Remote Similarity	NPD1253	Approved
0.6587	Remote Similarity	NPD6733	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