NPASS Compound

Structure

CID21461 OpenBabel06191715342D 44 48 0 0 1 0 0 0 0 0999 V2000 -5.5523 1.8041 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7433 1.2163 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4659 1.3973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 -2.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1410 -3.4343 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3239 -6.1996 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8479 0.2218 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5704 0.4028 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5000 -0.8660 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.0000 -3.7321 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.7251 -5.3906 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0878 -1.6750 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.4067 -4.6456 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.0388 -1.3660 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6636 -5.3147 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.0388 -0.3660 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.6762 -5.0816 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4840 -0.0039 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9820 -4.7215 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2024 -4.8147 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.4194 -5.7507 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -8.2930 0.5839 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.8841 -4.1034 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.1899 -3.7433 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.3184 -6.3041 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -5.7614 -0.1850 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.1160 -5.2215 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.7788 -2.6261 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3849 -4.8535 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8479 -1.9538 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7681 -6.3092 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.5885 -0.9985 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 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 1.0000 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0878 -0.0570 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0055 -3.8366 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 P 0 0 3 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 P 0 0 3 0 0 0 0 0 0 0 0 0 1 2 2 0 0 0 0 1 3 1 0 0 0 0 2 8 1 0 0 0 0 3 9 2 0 0 0 0 4 38 1 0 0 0 0 5 39 1 0 0 0 0 6 24 2 0 0 0 0 6 25 1 0 0 0 0 7 26 2 0 0 0 0 7 28 1 0 0 0 0 8 27 2 0 0 0 0 9 19 1 0 0 0 0 9 27 1 0 0 0 0 10 4 1 6 0 0 0 10 13 1 0 0 0 0 10 40 1 0 0 0 0 11 5 1 1 0 0 0 11 14 1 0 0 0 0 11 41 1 0 0 0 0 12 18 2 0 0 0 0 12 20 1 0 0 0 0 12 26 1 0 0 0 0 13 15 1 0 0 0 0 13 29 1 1 0 0 0 14 16 1 0 0 0 0 14 30 1 6 0 0 0 15 17 1 0 0 0 0 15 31 1 1 0 0 0 16 21 1 0 0 0 0 16 32 1 6 0 0 0 17 8 1 6 0 0 0 17 40 1 0 0 0 0 18 22 1 0 0 0 0 18 24 1 0 0 0 0 19 23 2 0 0 0 0 19 33 1 0 0 0 0 20 25 2 0 0 0 0 20 28 1 0 0 0 0 21 28 1 1 0 0 0 21 41 1 0 0 0 0 34 43 1 0 0 0 0 35 43 2 0 0 0 0 36 44 1 0 0 0 0 37 44 2 0 0 0 0 38 43 1 0 0 0 0 39 44 1 0 0 0 0 42 43 1 0 0 0 0 42 44 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	663.11
Volume:	547.593
LogP:	-3.029
LogD:	-1.506
LogS:	-0.838
# Rotatable Bonds:	11
TPSA:	321.68
# H-Bond Aceptor:	21
# H-Bond Donor:	8
# Rings:	5
# Heavy Atoms:	23

MedChem Properties

QED Drug-Likeness Score:	0.107
Synthetic Accessibility Score:	6.001
Fsp3:	0.476
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.439
MDCK Permeability:	5.327914550434798e-06
Pgp-inhibitor:	0.0
Pgp-substrate:	0.981
Human Intestinal Absorption (HIA):	0.884
20% Bioavailability (F20%):	0.989
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.509
Plasma Protein Binding (PPB):	30.65822982788086%
Volume Distribution (VD):	0.602
Pgp-substrate:	59.605934143066406%

ADMET: Metabolism

CYP1A2-inhibitor:	0.003
CYP1A2-substrate:	0.181
CYP2C19-inhibitor:	0.053
CYP2C19-substrate:	0.028
CYP2C9-inhibitor:	0.003
CYP2C9-substrate:	0.036
CYP2D6-inhibitor:	0.013
CYP2D6-substrate:	0.041
CYP3A4-inhibitor:	0.005
CYP3A4-substrate:	0.008

ADMET: Excretion

Clearance (CL):	1.462
Half-life (T1/2):	0.846

ADMET: Toxicity

hERG Blockers:	0.148
Human Hepatotoxicity (H-HT):	0.224
Drug-inuced Liver Injury (DILI):	0.984
AMES Toxicity:	0.049
Rat Oral Acute Toxicity:	0.027
Maximum Recommended Daily Dose:	0.946
Skin Sensitization:	0.131
Carcinogencity:	0.307
Eye Corrosion:	0.003
Eye Irritation:	0.008
Respiratory Toxicity:	0.829

Download Data

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

Natural Product: NPC21461

Natural Product ID:	NPC21461
*Common Name:**	5'-Ester With 1,4-Dihydro-1-Beta-D-Ribofuranosyl-2-Pyridinecarboxamide
IUPAC Name:	[[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [(2R,3S,4R,5S)-5-(6-carbamoylpyridin-1-ium-2-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphate
Synonyms:
Standard InCHIKey:	LFERELMXERXKKQ-KMXXXSRASA-N
Standard InCHI:	InChI=1S/C21H27N7O14P2/c22-18-12-20(25-6-24-18)28(7-26-12)21-16(32)14(30)11(41-21)5-39-44(36,37)42-43(34,35)38-4-10-13(29)15(31)17(40-10)8-2-1-3-9(27-8)19(23)33/h1-3,6-7,10-11,13-17,21,29-32H,4-5H2,(H2,23,33)(H,34,35)(H,36,37)(H2,22,24,25)/t10-,11-,13-,14-,15-,16-,17+,21-/m1/s1
SMILES:	c1cc([C@H]2[C@@H]([C@@H]([C@@H](COP(=O)(O)OP(=O)(O)OC[C@@H]3[C@H]([C@H]([C@H](n4cnc5c(N)ncnc45)O3)O)O)O2)O)O)nc(c1)C(=N)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1235132
PubChem CID:	5289104 444170
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000289] Nucleosides, nucleotides, and analogues [CHEMONTID:0001506] Purine nucleotides [CHEMONTID:0001293] Purine nucleotide sugars

*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
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11599360]
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	Eukaryota	n.a.	seed	n.a.	PMID[21381697]
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8210	Trigonella foenum-graecum	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
NPO8210	NPC21461	Other (raw)	Plant	18.25	9.8	26.7	mg/100g	Database [DUKE]

☑ 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
Ki	2

Activity Type	# Activity
Individual Protein	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1770	Individual Protein	Alcohol dehydrogenase alpha chain	Homo sapiens	Ki	=	21000.0	nM	PMID[570474]
NPT1771	Individual Protein	Glutamate dehydrogenase	Bos taurus	Ki	=	50000.0	nM	PMID[570474]

☑ 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 NPC21461 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	589
0.1-0.2	5853
0.2-0.3	18836
0.3-0.4	11308
0.4-0.5	3612
0.5-0.6	2217
0.6-0.7	264
0.7-0.8	15
0.8-0.85	0
0.85-0.9	1
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9014	High Similarity	NPC107160
0.7895	Intermediate Similarity	NPC160666
0.7848	Intermediate Similarity	NPC250178
0.7792	Intermediate Similarity	NPC158055
0.7696	Intermediate Similarity	NPC103388
0.7209	Intermediate Similarity	NPC313514
0.7062	Intermediate Similarity	NPC326529
0.7028	Intermediate Similarity	NPC324198
0.7028	Intermediate Similarity	NPC319100
0.6952	Remote Similarity	NPC326082
0.6929	Remote Similarity	NPC150447
0.6912	Remote Similarity	NPC174802
0.6863	Remote Similarity	NPC212551
0.6863	Remote Similarity	NPC130586
0.6863	Remote Similarity	NPC302778
0.6863	Remote Similarity	NPC164952
0.6845	Remote Similarity	NPC226245
0.6842	Remote Similarity	NPC323091
0.6796	Remote Similarity	NPC224076
0.6792	Remote Similarity	NPC319456
0.6765	Remote Similarity	NPC85689
0.6765	Remote Similarity	NPC185991
0.6765	Remote Similarity	NPC161224
0.6765	Remote Similarity	NPC211025
0.6761	Remote Similarity	NPC222174
0.6745	Remote Similarity	NPC125659
0.6745	Remote Similarity	NPC168702
0.6732	Remote Similarity	NPC321814
0.6712	Remote Similarity	NPC472289
0.6683	Remote Similarity	NPC316618
0.6667	Remote Similarity	NPC226202
0.6667	Remote Similarity	NPC321458
0.6667	Remote Similarity	NPC324033
0.6636	Remote Similarity	NPC189261
0.6634	Remote Similarity	NPC150853
0.662	Remote Similarity	NPC261595
0.6618	Remote Similarity	NPC121222
0.6612	Remote Similarity	NPC130570
0.6598	Remote Similarity	NPC476492
0.6591	Remote Similarity	NPC161887
0.6591	Remote Similarity	NPC219963
0.6588	Remote Similarity	NPC472067
0.6588	Remote Similarity	NPC472066
0.6588	Remote Similarity	NPC472031
0.6587	Remote Similarity	NPC477805
0.6587	Remote Similarity	NPC477806
0.6587	Remote Similarity	NPC477796
0.6587	Remote Similarity	NPC477795
0.6577	Remote Similarity	NPC62510
0.6575	Remote Similarity	NPC472068
0.657	Remote Similarity	NPC207633
0.654	Remote Similarity	NPC471603
0.6524	Remote Similarity	NPC239737
0.6488	Remote Similarity	NPC309832
0.6481	Remote Similarity	NPC157821
0.6471	Remote Similarity	NPC21448
0.6471	Remote Similarity	NPC107374
0.6471	Remote Similarity	NPC156461
0.6462	Remote Similarity	NPC138018
0.6461	Remote Similarity	NPC471506
0.6449	Remote Similarity	NPC98371
0.6449	Remote Similarity	NPC313884
0.6441	Remote Similarity	NPC314394
0.6441	Remote Similarity	NPC266551
0.6439	Remote Similarity	NPC189068
0.6439	Remote Similarity	NPC164665
0.6438	Remote Similarity	NPC5802
0.6431	Remote Similarity	NPC472434
0.6429	Remote Similarity	NPC242923
0.642	Remote Similarity	NPC471564
0.6417	Remote Similarity	NPC50511
0.6408	Remote Similarity	NPC269827
0.6408	Remote Similarity	NPC219313
0.6395	Remote Similarity	NPC276373
0.6375	Remote Similarity	NPC282247
0.6373	Remote Similarity	NPC229974
0.6364	Remote Similarity	NPC313897
0.6364	Remote Similarity	NPC30540
0.6364	Remote Similarity	NPC317054
0.6353	Remote Similarity	NPC39092
0.6353	Remote Similarity	NPC171393
0.6353	Remote Similarity	NPC295452
0.6346	Remote Similarity	NPC476493
0.6345	Remote Similarity	NPC469589
0.6337	Remote Similarity	NPC469594
0.6331	Remote Similarity	NPC244536
0.6325	Remote Similarity	NPC54537
0.6314	Remote Similarity	NPC81175
0.6311	Remote Similarity	NPC308906
0.6309	Remote Similarity	NPC187558
0.6305	Remote Similarity	NPC314954
0.6295	Remote Similarity	NPC469554
0.6291	Remote Similarity	NPC311197
0.6291	Remote Similarity	NPC313754
0.6291	Remote Similarity	NPC54320
0.6283	Remote Similarity	NPC20249
0.628	Remote Similarity	NPC69843
0.6275	Remote Similarity	NPC161659
0.6275	Remote Similarity	NPC209525
0.6267	Remote Similarity	NPC48938
0.6265	Remote Similarity	NPC316756
0.6265	Remote Similarity	NPC110151
0.6256	Remote Similarity	NPC472816
0.6255	Remote Similarity	NPC472027
0.6255	Remote Similarity	NPC471891
0.6255	Remote Similarity	NPC324815
0.625	Remote Similarity	NPC5145
0.625	Remote Similarity	NPC14590
0.6245	Remote Similarity	NPC56271
0.6244	Remote Similarity	NPC52238
0.624	Remote Similarity	NPC471080
0.624	Remote Similarity	NPC469592
0.6239	Remote Similarity	NPC284678
0.6239	Remote Similarity	NPC24589
0.6239	Remote Similarity	NPC284559
0.6239	Remote Similarity	NPC33382
0.6233	Remote Similarity	NPC211997
0.623	Remote Similarity	NPC238945
0.623	Remote Similarity	NPC89987
0.623	Remote Similarity	NPC312645
0.6228	Remote Similarity	NPC282458
0.6228	Remote Similarity	NPC78941
0.6225	Remote Similarity	NPC132631
0.6225	Remote Similarity	NPC103687
0.6223	Remote Similarity	NPC208751
0.6218	Remote Similarity	NPC471736
0.6215	Remote Similarity	NPC115595
0.6214	Remote Similarity	NPC314152
0.6202	Remote Similarity	NPC232408
0.6202	Remote Similarity	NPC64705
0.6198	Remote Similarity	NPC314882
0.6195	Remote Similarity	NPC317821
0.6192	Remote Similarity	NPC314774
0.6192	Remote Similarity	NPC107836
0.6192	Remote Similarity	NPC315126
0.6189	Remote Similarity	NPC63109
0.6188	Remote Similarity	NPC134586
0.6187	Remote Similarity	NPC99891
0.6182	Remote Similarity	NPC290959
0.6176	Remote Similarity	NPC30326
0.6176	Remote Similarity	NPC470500
0.6175	Remote Similarity	NPC25899
0.6173	Remote Similarity	NPC473757
0.617	Remote Similarity	NPC474767
0.6167	Remote Similarity	NPC308392
0.6165	Remote Similarity	NPC477633
0.6165	Remote Similarity	NPC74619
0.6165	Remote Similarity	NPC472436
0.6154	Remote Similarity	NPC274384
0.6154	Remote Similarity	NPC177169
0.6154	Remote Similarity	NPC317746
0.6154	Remote Similarity	NPC89147
0.6151	Remote Similarity	NPC472111
0.615	Remote Similarity	NPC477891
0.6147	Remote Similarity	NPC48192
0.6133	Remote Similarity	NPC141377
0.6133	Remote Similarity	NPC133261
0.6128	Remote Similarity	NPC239954
0.6126	Remote Similarity	NPC14651
0.6126	Remote Similarity	NPC121658
0.6123	Remote Similarity	NPC472109
0.6123	Remote Similarity	NPC472110
0.6118	Remote Similarity	NPC223223
0.6116	Remote Similarity	NPC24594
0.6116	Remote Similarity	NPC472122
0.6113	Remote Similarity	NPC472435
0.6111	Remote Similarity	NPC33949
0.6107	Remote Similarity	NPC89508
0.6106	Remote Similarity	NPC211820
0.6106	Remote Similarity	NPC318590
0.6106	Remote Similarity	NPC251233
0.6105	Remote Similarity	NPC478006
0.6102	Remote Similarity	NPC101543
0.6098	Remote Similarity	NPC472285
0.6094	Remote Similarity	NPC84853
0.6094	Remote Similarity	NPC198673
0.6089	Remote Similarity	NPC326575
0.6089	Remote Similarity	NPC315467
0.6085	Remote Similarity	NPC477861
0.6085	Remote Similarity	NPC471614
0.6081	Remote Similarity	NPC164664
0.6081	Remote Similarity	NPC476518
0.6073	Remote Similarity	NPC71079
0.6071	Remote Similarity	NPC475258
0.6066	Remote Similarity	NPC478009
0.6066	Remote Similarity	NPC26679
0.6066	Remote Similarity	NPC478010
0.6065	Remote Similarity	NPC120070
0.6064	Remote Similarity	NPC310118
0.6063	Remote Similarity	NPC475969
0.6063	Remote Similarity	NPC475859
0.6059	Remote Similarity	NPC149708
0.6059	Remote Similarity	NPC212213
0.6059	Remote Similarity	NPC168911
0.6058	Remote Similarity	NPC166492
0.6058	Remote Similarity	NPC473362
0.6057	Remote Similarity	NPC8022
0.6057	Remote Similarity	NPC288349
0.6057	Remote Similarity	NPC470799
0.6056	Remote Similarity	NPC35761

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 NPC21461 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	217
0.1-0.2	795
0.2-0.3	1286
0.3-0.4	2555
0.4-0.5	2054
0.5-0.6	1825
0.6-0.7	383
0.7-0.8	34
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
0.8	Intermediate Similarity	NPD5080	Phase 2
0.7955	Intermediate Similarity	NPD5079	Phase 2
0.7928	Intermediate Similarity	NPD4555	Clinical (unspecified phase)
0.7792	Intermediate Similarity	NPD6840	Approved
0.7788	Intermediate Similarity	NPD2876	Phase 3
0.7788	Intermediate Similarity	NPD2877	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD2965	Clinical (unspecified phase)
0.7717	Intermediate Similarity	NPD2824	Phase 2
0.7658	Intermediate Similarity	NPD2903	Clinical (unspecified phase)
0.7658	Intermediate Similarity	NPD2902	Phase 2
0.754	Intermediate Similarity	NPD7273	Clinical (unspecified phase)
0.7443	Intermediate Similarity	NPD4458	Phase 2
0.7443	Intermediate Similarity	NPD4459	Clinical (unspecified phase)
0.7416	Intermediate Similarity	NPD4716	Approved
0.7415	Intermediate Similarity	NPD7502	Clinical (unspecified phase)
0.7397	Intermediate Similarity	NPD8250	Phase 2
0.7381	Intermediate Similarity	NPD4744	Clinical (unspecified phase)
0.7364	Intermediate Similarity	NPD6992	Phase 2
0.7336	Intermediate Similarity	NPD2152	Clinical (unspecified phase)
0.7316	Intermediate Similarity	NPD4187	Clinical (unspecified phase)
0.7277	Intermediate Similarity	NPD2451	Phase 2
0.7277	Intermediate Similarity	NPD2450	Phase 2
0.7277	Intermediate Similarity	NPD2452	Phase 2
0.7277	Intermediate Similarity	NPD2453	Phase 2
0.7244	Intermediate Similarity	NPD4612	Discontinued
0.7224	Intermediate Similarity	NPD6351	Discovery
0.7209	Intermediate Similarity	NPD7138	Phase 2
0.7188	Intermediate Similarity	NPD1915	Phase 1
0.7181	Intermediate Similarity	NPD4495	Phase 1
0.7175	Intermediate Similarity	NPD5486	Discontinued
0.7143	Intermediate Similarity	NPD2544	Clinical (unspecified phase)
0.7137	Intermediate Similarity	NPD6036	Suspended
0.7105	Intermediate Similarity	NPD8321	Discontinued
0.7097	Intermediate Similarity	NPD207	Discontinued
0.7082	Intermediate Similarity	NPD537	Phase 2
0.7082	Intermediate Similarity	NPD534	Phase 2
0.708	Intermediate Similarity	NPD5458	Discontinued
0.7067	Intermediate Similarity	NPD34	Approved
0.7067	Intermediate Similarity	NPD4715	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD4714	Approved
0.7067	Intermediate Similarity	NPD4713	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD6307	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD9582	Phase 3
0.7028	Intermediate Similarity	NPD4171	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD6381	Phase 2
0.7012	Intermediate Similarity	NPD4080	Discontinued
0.6955	Remote Similarity	NPD4654	Phase 1
0.6948	Remote Similarity	NPD4896	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD5171	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD6326	Phase 2
0.6942	Remote Similarity	NPD4306	Phase 1
0.6935	Remote Similarity	NPD7486	Phase 1
0.6912	Remote Similarity	NPD339	Approved
0.6899	Remote Similarity	NPD6023	Discontinued
0.6878	Remote Similarity	NPD4414	Discontinued
0.6875	Remote Similarity	NPD6327	Phase 1
0.6867	Remote Similarity	NPD8291	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD338	Approved
0.6862	Remote Similarity	NPD5703	Discontinued
0.6858	Remote Similarity	NPD4599	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD6573	Phase 3
0.6855	Remote Similarity	NPD6572	Phase 2
0.6849	Remote Similarity	NPD2591	Phase 2
0.6849	Remote Similarity	NPD3913	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD3590	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD1273	Discontinued
0.6826	Remote Similarity	NPD796	Phase 2
0.6822	Remote Similarity	NPD5949	Phase 3
0.6811	Remote Similarity	NPD8442	Discontinued
0.68	Remote Similarity	NPD8375	Approved
0.6796	Remote Similarity	NPD169	Phase 2
0.6795	Remote Similarity	NPD3343	Phase 3
0.6787	Remote Similarity	NPD4440	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD7323	Phase 2
0.6781	Remote Similarity	NPD2540	Clinical (unspecified phase)
0.6777	Remote Similarity	NPD7988	Suspended
0.6765	Remote Similarity	NPD283	Approved
0.6761	Remote Similarity	NPD2414	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD6605	Phase 3
0.6753	Remote Similarity	NPD8410	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD1197	Approved
0.675	Remote Similarity	NPD7202	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD8371	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD5644	Phase 1
0.6744	Remote Similarity	NPD7706	Clinical (unspecified phase)
0.6737	Remote Similarity	NPD6958	Approved
0.6737	Remote Similarity	NPD6711	Approved
0.6737	Remote Similarity	NPD6957	Approved
0.6719	Remote Similarity	NPD5911	Clinical (unspecified phase)
0.6712	Remote Similarity	NPD7504	Discontinued
0.6711	Remote Similarity	NPD2536	Discontinued
0.6709	Remote Similarity	NPD6763	Discontinued
0.6709	Remote Similarity	NPD4563	Phase 2
0.6708	Remote Similarity	NPD1571	Phase 2
0.6707	Remote Similarity	NPD6970	Phase 2
0.6699	Remote Similarity	NPD242	Approved
0.6697	Remote Similarity	NPD5757	Discontinued
0.6696	Remote Similarity	NPD1234	Discontinued
0.6696	Remote Similarity	NPD2127	Suspended
0.6695	Remote Similarity	NPD6856	Discontinued
0.6692	Remote Similarity	NPD7198	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3403	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5665	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD516	Clinical (unspecified phase)
0.6653	Remote Similarity	NPD8004	Discontinued
0.6653	Remote Similarity	NPD7068	Approved
0.6653	Remote Similarity	NPD7067	Approved
0.6627	Remote Similarity	NPD3849	Clinical (unspecified phase)
0.6626	Remote Similarity	NPD7051	Phase 3
0.6626	Remote Similarity	NPD7050	Clinical (unspecified phase)
0.6626	Remote Similarity	NPD6352	Phase 2
0.6626	Remote Similarity	NPD1572	Phase 2
0.6622	Remote Similarity	NPD706	Phase 1
0.6622	Remote Similarity	NPD1063	Phase 2
0.662	Remote Similarity	NPD247	Clinical (unspecified phase)
0.662	Remote Similarity	NPD1333	Phase 3
0.6617	Remote Similarity	NPD6175	Phase 3
0.66	Remote Similarity	NPD4858	Phase 2
0.6598	Remote Similarity	NPD2349	Phase 3
0.6597	Remote Similarity	NPD6643	Discontinued
0.6589	Remote Similarity	NPD8373	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD6244	Phase 3
0.6588	Remote Similarity	NPD6243	Phase 3
0.6584	Remote Similarity	NPD4403	Phase 3
0.6584	Remote Similarity	NPD4401	Phase 2
0.6579	Remote Similarity	NPD691	Discontinued
0.6574	Remote Similarity	NPD3418	Clinical (unspecified phase)
0.6573	Remote Similarity	NPD2757	Phase 2
0.6573	Remote Similarity	NPD3838	Phase 3
0.6567	Remote Similarity	NPD6403	Clinical (unspecified phase)
0.6567	Remote Similarity	NPD6754	Phase 3
0.656	Remote Similarity	NPD6750	Phase 2
0.6557	Remote Similarity	NPD3083	Approved
0.6542	Remote Similarity	NPD1623	Approved
0.6538	Remote Similarity	NPD1369	Phase 2
0.6538	Remote Similarity	NPD3107	Discontinued
0.6531	Remote Similarity	NPD6978	Phase 2
0.6531	Remote Similarity	NPD6977	Clinical (unspecified phase)
0.6529	Remote Similarity	NPD7726	Phase 1
0.6526	Remote Similarity	NPD1016	Phase 2
0.6526	Remote Similarity	NPD1015	Phase 2
0.6525	Remote Similarity	NPD3014	Clinical (unspecified phase)
0.6525	Remote Similarity	NPD3013	Phase 3
0.6525	Remote Similarity	NPD6192	Phase 3
0.6524	Remote Similarity	NPD2646	Discontinued
0.6524	Remote Similarity	NPD2624	Phase 2
0.6522	Remote Similarity	NPD5534	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD5802	Phase 2
0.6518	Remote Similarity	NPD3002	Clinical (unspecified phase)
0.6518	Remote Similarity	NPD2062	Phase 2
0.6513	Remote Similarity	NPD8488	Clinical (unspecified phase)
0.6507	Remote Similarity	NPD3261	Phase 1
0.6498	Remote Similarity	NPD3265	Phase 1
0.6494	Remote Similarity	NPD5584	Clinical (unspecified phase)
0.6488	Remote Similarity	NPD6717	Clinical (unspecified phase)
0.6483	Remote Similarity	NPD7409	Clinical (unspecified phase)
0.6483	Remote Similarity	NPD6545	Clinical (unspecified phase)
0.6482	Remote Similarity	NPD7856	Phase 2
0.6482	Remote Similarity	NPD7857	Phase 3
0.648	Remote Similarity	NPD3338	Clinical (unspecified phase)
0.6476	Remote Similarity	NPD4615	Phase 2
0.6475	Remote Similarity	NPD6829	Phase 2
0.6475	Remote Similarity	NPD6197	Approved
0.6473	Remote Similarity	NPD3811	Discontinued
0.6471	Remote Similarity	NPD8458	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD250	Approved
0.6471	Remote Similarity	NPD249	Approved
0.6468	Remote Similarity	NPD1037	Clinical (unspecified phase)
0.6459	Remote Similarity	NPD7851	Phase 1
0.6459	Remote Similarity	NPD7850	Discontinued
0.6457	Remote Similarity	NPD1692	Approved
0.6456	Remote Similarity	NPD4990	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD5018	Phase 3
0.6453	Remote Similarity	NPD5425	Phase 1
0.6453	Remote Similarity	NPD2130	Discontinued
0.6453	Remote Similarity	NPD4442	Phase 2
0.645	Remote Similarity	NPD5116	Phase 1
0.6449	Remote Similarity	NPD6976	Clinical (unspecified phase)
0.6448	Remote Similarity	NPD1480	Clinical (unspecified phase)
0.6447	Remote Similarity	NPD3485	Clinical (unspecified phase)
0.6447	Remote Similarity	NPD5428	Discontinued
0.6446	Remote Similarity	NPD6455	Phase 3
0.644	Remote Similarity	NPD6760	Discontinued
0.6435	Remote Similarity	NPD3830	Phase 1
0.6435	Remote Similarity	NPD4673	Phase 2
0.6435	Remote Similarity	NPD1215	Discontinued
0.6434	Remote Similarity	NPD5878	Approved
0.6434	Remote Similarity	NPD5875	Approved
0.6429	Remote Similarity	NPD5172	Phase 2
0.6426	Remote Similarity	NPD5627	Approved
0.6423	Remote Similarity	NPD1603	Discontinued
0.642	Remote Similarity	NPD5572	Phase 3
0.6419	Remote Similarity	NPD5925	Phase 1
0.6419	Remote Similarity	NPD4999	Phase 3
0.6419	Remote Similarity	NPD4998	Phase 3
0.6417	Remote Similarity	NPD2547	Discontinued
0.6417	Remote Similarity	NPD429	Approved
0.6417	Remote Similarity	NPD7188	Phase 3
0.641	Remote Similarity	NPD2364	Suspended
0.6409	Remote Similarity	NPD6742	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