NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	256.08
Volume:	236.21
LogP:	-0.721
LogD:	-0.729
LogS:	-0.84
# Rotatable Bonds:	3
TPSA:	111.1
# H-Bond Aceptor:	7
# H-Bond Donor:	4
# Rings:	2
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.479
Synthetic Accessibility Score:	3.845
Fsp3:	0.455
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.154
MDCK Permeability:	0.00015627453103661537
Pgp-inhibitor:	0.001
Pgp-substrate:	0.72
Human Intestinal Absorption (HIA):	0.959
20% Bioavailability (F20%):	0.931
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.46
Plasma Protein Binding (PPB):	8.556510925292969%
Volume Distribution (VD):	0.328
Pgp-substrate:	94.93936157226562%

ADMET: Metabolism

CYP1A2-inhibitor:	0.025
CYP1A2-substrate:	0.035
CYP2C19-inhibitor:	0.014
CYP2C19-substrate:	0.048
CYP2C9-inhibitor:	0.002
CYP2C9-substrate:	0.03
CYP2D6-inhibitor:	0.013
CYP2D6-substrate:	0.094
CYP3A4-inhibitor:	0.002
CYP3A4-substrate:	0.013

ADMET: Excretion

Clearance (CL):	3.647
Half-life (T1/2):	0.943

ADMET: Toxicity

hERG Blockers:	0.024
Human Hepatotoxicity (H-HT):	0.204
Drug-inuced Liver Injury (DILI):	0.947
AMES Toxicity:	0.036
Rat Oral Acute Toxicity:	0.015
Maximum Recommended Daily Dose:	0.002
Skin Sensitization:	0.063
Carcinogencity:	0.043
Eye Corrosion:	0.003
Eye Irritation:	0.45
Respiratory Toxicity:	0.015

Download Data

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

Natural Product: NPC317010

Natural Product ID:	NPC317010
*Common Name:**	3-Carboxy-1-((2R,3R,4S,5R)-3,4-Dihydroxy-5-Hydroxymethyl-Tetrahydro-Furan-2-Yl)-Pyridinium
IUPAC Name:	1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyridin-1-ium-3-carboxylic acid
Synonyms:
Standard InCHIKey:	PUEDDPCUCPRQNY-ZYUZMQFOSA-O
Standard InCHI:	InChI=1S/C11H13NO6/c13-5-7-8(14)9(15)10(18-7)12-3-1-2-6(4-12)11(16)17/h1-4,7-10,13-15H,5H2/p+1/t7-,8-,9-,10-/m1/s1
SMILES:	OC[C@H]1O[C@H]([C@@H]([C@@H]1O)O)[n+]1cccc(c1)C(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL396943
PubChem CID:	161234
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:0002203] Glycosylamines

*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
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1172/JCI16309]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1371/journal.pone.0115359]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[10557354]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[11034610]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[11419736]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[11530998]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[1175644]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[12391014]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[12812989]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[12840027]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[12878451]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[15084647]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[1521032]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[15230696]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[15314235]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[16112079]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[16770722]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[1687010]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[17116739]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[17190852]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[17875433]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[18311922]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[18544912]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[18799520]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[19425150]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[19961175]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[20506249]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[20601097]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	bile	n.a.	PMID[20708442]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	faeces	n.a.	PMID[20708442]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	urine	n.a.	PMID[20708442]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[20876113]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[21798258]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[2268561]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[22711758]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[23315938]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[23717534]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[23752203]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[23810710]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[23811455]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[23868375]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[23919613]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[24101735]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[24399466]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[24494566]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[24558969]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[24816727]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[25114169]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[25181601]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[25293588]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[25644343]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[26236990]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[27471436]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[3179836]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[347637]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[4696527]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[5432584]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[6121420]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[6780563]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[8600370]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[8987136]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[9192820]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[9800648]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	Database[MetaboLights]
NPO20338	Mus musculus	Species	Muridae	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
Others	6

Activity Type	# Activity
Cell Line	2
NON-MOLECULAR	2
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT71	Cell Line	HEK293	Homo sapiens	Activity	=	92.0	%	PMID[501131]
NPT71	Cell Line	HEK293	Homo sapiens	Activity	=	1.9	%	PMID[501131]
NPT27	Others	Unspecified		Activity	=	111.0	%	PMID[501131]
NPT27	Others	Unspecified		Activity	=	125.0	%	PMID[501131]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	1.5	%	PMID[501131]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	1.7	%	PMID[501131]

☑ 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 NPC317010 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	295
0.1-0.2	2288
0.2-0.3	11073
0.3-0.4	17197
0.4-0.5	7748
0.5-0.6	3161
0.6-0.7	708
0.7-0.8	213
0.8-0.85	11
0.85-0.9	2
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8938	High Similarity	NPC263455
0.8712	High Similarity	NPC138018
0.8642	High Similarity	NPC312860
0.85	High Similarity	NPC167400
0.8415	Intermediate Similarity	NPC107287
0.8407	Intermediate Similarity	NPC59033
0.8353	Intermediate Similarity	NPC319456
0.8323	Intermediate Similarity	NPC230085
0.8323	Intermediate Similarity	NPC159630
0.8306	Intermediate Similarity	NPC317672
0.8251	Intermediate Similarity	NPC329024
0.8216	Intermediate Similarity	NPC79223
0.8171	Intermediate Similarity	NPC112741
0.8138	Intermediate Similarity	NPC12944
0.8138	Intermediate Similarity	NPC25442
0.8108	Intermediate Similarity	NPC324245
0.8108	Intermediate Similarity	NPC320748
0.8107	Intermediate Similarity	NPC113812
0.8075	Intermediate Similarity	NPC32451
0.8075	Intermediate Similarity	NPC328559
0.8066	Intermediate Similarity	NPC75544
0.8053	Intermediate Similarity	NPC156044
0.8046	Intermediate Similarity	NPC273532
0.7969	Intermediate Similarity	NPC472752
0.7906	Intermediate Similarity	NPC309498
0.7846	Intermediate Similarity	NPC111732
0.784	Intermediate Similarity	NPC114310
0.7824	Intermediate Similarity	NPC63041
0.7809	Intermediate Similarity	NPC476419
0.7778	Intermediate Similarity	NPC474767
0.7778	Intermediate Similarity	NPC29702
0.7755	Intermediate Similarity	NPC476467
0.7747	Intermediate Similarity	NPC207851
0.7692	Intermediate Similarity	NPC304179
0.7692	Intermediate Similarity	NPC327373
0.7692	Intermediate Similarity	NPC325093
0.7692	Intermediate Similarity	NPC472550
0.7692	Intermediate Similarity	NPC48042
0.7688	Intermediate Similarity	NPC475408
0.7688	Intermediate Similarity	NPC471014
0.7665	Intermediate Similarity	NPC472553
0.765	Intermediate Similarity	NPC294579
0.765	Intermediate Similarity	NPC144779
0.764	Intermediate Similarity	NPC249614
0.7638	Intermediate Similarity	NPC477910
0.7638	Intermediate Similarity	NPC470306
0.7609	Intermediate Similarity	NPC318020
0.76	Intermediate Similarity	NPC6981
0.76	Intermediate Similarity	NPC471016
0.7596	Intermediate Similarity	NPC322043
0.7527	Intermediate Similarity	NPC328798
0.7526	Intermediate Similarity	NPC109922
0.7525	Intermediate Similarity	NPC216428
0.7525	Intermediate Similarity	NPC301368
0.7525	Intermediate Similarity	NPC84815
0.7512	Intermediate Similarity	NPC475137
0.7512	Intermediate Similarity	NPC475498
0.75	Intermediate Similarity	NPC319128
0.75	Intermediate Similarity	NPC228331
0.75	Intermediate Similarity	NPC114974
0.75	Intermediate Similarity	NPC165370
0.7487	Intermediate Similarity	NPC182814
0.7476	Intermediate Similarity	NPC473506
0.7475	Intermediate Similarity	NPC62367
0.7472	Intermediate Similarity	NPC41717
0.7463	Intermediate Similarity	NPC477907
0.7463	Intermediate Similarity	NPC471980
0.7463	Intermediate Similarity	NPC42678
0.7463	Intermediate Similarity	NPC477909
0.7463	Intermediate Similarity	NPC76565
0.7438	Intermediate Similarity	NPC472555
0.7435	Intermediate Similarity	NPC292361
0.7433	Intermediate Similarity	NPC325775
0.7427	Intermediate Similarity	NPC477902
0.7427	Intermediate Similarity	NPC473850
0.7426	Intermediate Similarity	NPC477908
0.7426	Intermediate Similarity	NPC206343
0.7415	Intermediate Similarity	NPC127026
0.7415	Intermediate Similarity	NPC127720
0.7407	Intermediate Similarity	NPC127647
0.7404	Intermediate Similarity	NPC471190
0.7404	Intermediate Similarity	NPC475644
0.7404	Intermediate Similarity	NPC470486
0.7404	Intermediate Similarity	NPC471977
0.7404	Intermediate Similarity	NPC475362
0.7401	Intermediate Similarity	NPC71079
0.74	Intermediate Similarity	NPC323551
0.74	Intermediate Similarity	NPC280473
0.7379	Intermediate Similarity	NPC57797
0.7379	Intermediate Similarity	NPC250807
0.7368	Intermediate Similarity	NPC302159
0.7366	Intermediate Similarity	NPC477912
0.7363	Intermediate Similarity	NPC165837
0.7363	Intermediate Similarity	NPC41724
0.7363	Intermediate Similarity	NPC51008
0.736	Intermediate Similarity	NPC474217
0.7356	Intermediate Similarity	NPC124029
0.7356	Intermediate Similarity	NPC476110
0.7356	Intermediate Similarity	NPC475631
0.7356	Intermediate Similarity	NPC146824
0.7356	Intermediate Similarity	NPC475600
0.7356	Intermediate Similarity	NPC87152
0.7356	Intermediate Similarity	NPC211920
0.735	Intermediate Similarity	NPC40919
0.735	Intermediate Similarity	NPC470189
0.7346	Intermediate Similarity	NPC471589
0.7343	Intermediate Similarity	NPC328154
0.7343	Intermediate Similarity	NPC233727
0.7337	Intermediate Similarity	NPC164340
0.733	Intermediate Similarity	NPC477911
0.7327	Intermediate Similarity	NPC4421
0.7327	Intermediate Similarity	NPC264674
0.7318	Intermediate Similarity	NPC85918
0.7311	Intermediate Similarity	NPC170751
0.7302	Intermediate Similarity	NPC44354
0.7299	Intermediate Similarity	NPC30456
0.7292	Intermediate Similarity	NPC20593
0.7292	Intermediate Similarity	NPC135950
0.7291	Intermediate Similarity	NPC62844
0.7291	Intermediate Similarity	NPC193361
0.7286	Intermediate Similarity	NPC470190
0.7284	Intermediate Similarity	NPC212125
0.7278	Intermediate Similarity	NPC127730
0.7278	Intermediate Similarity	NPC278366
0.7273	Intermediate Similarity	NPC475601
0.7273	Intermediate Similarity	NPC477787
0.7273	Intermediate Similarity	NPC228377
0.7273	Intermediate Similarity	NPC328186
0.7273	Intermediate Similarity	NPC322488
0.7273	Intermediate Similarity	NPC122968
0.7268	Intermediate Similarity	NPC149708
0.7264	Intermediate Similarity	NPC237702
0.7251	Intermediate Similarity	NPC96801
0.7251	Intermediate Similarity	NPC475303
0.7251	Intermediate Similarity	NPC473689
0.7251	Intermediate Similarity	NPC150698
0.7251	Intermediate Similarity	NPC292416
0.7251	Intermediate Similarity	NPC477906
0.7251	Intermediate Similarity	NPC475596
0.7234	Intermediate Similarity	NPC295158
0.7234	Intermediate Similarity	NPC62510
0.7231	Intermediate Similarity	NPC50997
0.7231	Intermediate Similarity	NPC160127
0.7231	Intermediate Similarity	NPC103361
0.7225	Intermediate Similarity	NPC148860
0.7222	Intermediate Similarity	NPC289086
0.722	Intermediate Similarity	NPC473089
0.722	Intermediate Similarity	NPC212768
0.722	Intermediate Similarity	NPC158020
0.722	Intermediate Similarity	NPC6576
0.722	Intermediate Similarity	NPC473115
0.722	Intermediate Similarity	NPC75600
0.7217	Intermediate Similarity	NPC244839
0.7217	Intermediate Similarity	NPC469748
0.7217	Intermediate Similarity	NPC320324
0.7217	Intermediate Similarity	NPC319880
0.7206	Intermediate Similarity	NPC207531
0.7179	Intermediate Similarity	NPC472284
0.7178	Intermediate Similarity	NPC306397
0.717	Intermediate Similarity	NPC316841
0.715	Intermediate Similarity	NPC475406
0.715	Intermediate Similarity	NPC475426
0.715	Intermediate Similarity	NPC477901
0.715	Intermediate Similarity	NPC327769
0.715	Intermediate Similarity	NPC35208
0.7143	Intermediate Similarity	NPC292517
0.7136	Intermediate Similarity	NPC319556
0.7136	Intermediate Similarity	NPC187494
0.7135	Intermediate Similarity	NPC213914
0.7119	Intermediate Similarity	NPC33229
0.7119	Intermediate Similarity	NPC209362
0.7116	Intermediate Similarity	NPC327904
0.7116	Intermediate Similarity	NPC38959
0.7115	Intermediate Similarity	NPC477903
0.7113	Intermediate Similarity	NPC146724
0.7103	Intermediate Similarity	NPC238278
0.71	Intermediate Similarity	NPC472287
0.71	Intermediate Similarity	NPC472286
0.7092	Intermediate Similarity	NPC474916
0.7087	Intermediate Similarity	NPC472285
0.7081	Intermediate Similarity	NPC477788
0.7081	Intermediate Similarity	NPC235364
0.7077	Intermediate Similarity	NPC77061
0.7068	Intermediate Similarity	NPC278434
0.7056	Intermediate Similarity	NPC123395
0.7053	Intermediate Similarity	NPC282103
0.7052	Intermediate Similarity	NPC471323
0.7041	Intermediate Similarity	NPC328029
0.7039	Intermediate Similarity	NPC30570
0.7035	Intermediate Similarity	NPC57398
0.7031	Intermediate Similarity	NPC209917
0.7021	Intermediate Similarity	NPC325705
0.7021	Intermediate Similarity	NPC52831
0.7018	Intermediate Similarity	NPC253482
0.7014	Intermediate Similarity	NPC26881
0.7014	Intermediate Similarity	NPC477899
0.7014	Intermediate Similarity	NPC477900
0.7005	Intermediate Similarity	NPC162812
0.6986	Remote Similarity	NPC54066
0.6985	Remote Similarity	NPC155792

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 NPC317010 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	178
0.1-0.2	515
0.2-0.3	955
0.3-0.4	1870
0.4-0.5	3263
0.5-0.6	1935
0.6-0.7	413
0.7-0.8	14
0.8-0.85	7
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.85	High Similarity	NPD9074	Approved
0.85	High Similarity	NPD9075	Approved
0.8485	Intermediate Similarity	NPD820	Phase 3
0.825	Intermediate Similarity	NPD107	Approved
0.8229	Intermediate Similarity	NPD8304	Clinical (unspecified phase)
0.8171	Intermediate Similarity	NPD9271	Approved
0.8042	Intermediate Similarity	NPD7396	Approved
0.7901	Intermediate Similarity	NPD203	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD9506	Approved
0.7447	Intermediate Similarity	NPD2544	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD485	Clinical (unspecified phase)
0.7366	Intermediate Similarity	NPD1096	Discontinued
0.7351	Intermediate Similarity	NPD1783	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD9284	Approved
0.72	Intermediate Similarity	NPD510	Phase 1
0.7192	Intermediate Similarity	NPD3795	Approved
0.7192	Intermediate Similarity	NPD3794	Approved
0.7186	Intermediate Similarity	NPD272	Approved
0.7178	Intermediate Similarity	NPD9080	Approved
0.7167	Intermediate Similarity	NPD5088	Discontinued
0.715	Intermediate Similarity	NPD1173	Approved
0.7136	Intermediate Similarity	NPD2831	Approved
0.7113	Intermediate Similarity	NPD5975	Clinical (unspecified phase)
0.7098	Intermediate Similarity	NPD981	Phase 2
0.7088	Intermediate Similarity	NPD4174	Clinical (unspecified phase)
0.7085	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.705	Intermediate Similarity	NPD3947	Discontinued
0.7021	Intermediate Similarity	NPD1643	Phase 3
0.7021	Intermediate Similarity	NPD9510	Approved
0.7015	Intermediate Similarity	NPD6732	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD3280	Approved
0.6984	Remote Similarity	NPD3178	Discontinued
0.698	Remote Similarity	NPD3371	Approved
0.6977	Remote Similarity	NPD1649	Discontinued
0.6971	Remote Similarity	NPD1623	Approved
0.6954	Remote Similarity	NPD1352	Discontinued
0.6946	Remote Similarity	NPD2510	Approved
0.6946	Remote Similarity	NPD2509	Approved
0.6936	Remote Similarity	NPD4805	Approved
0.6923	Remote Similarity	NPD6665	Discontinued
0.6872	Remote Similarity	NPD2336	Approved
0.6869	Remote Similarity	NPD4086	Phase 1
0.686	Remote Similarity	NPD1380	Discovery
0.686	Remote Similarity	NPD2896	Discontinued
0.685	Remote Similarity	NPD5228	Phase 3
0.6842	Remote Similarity	NPD1618	Phase 2
0.6828	Remote Similarity	NPD1575	Approved
0.6828	Remote Similarity	NPD1573	Approved
0.6821	Remote Similarity	NPD4804	Approved
0.6818	Remote Similarity	NPD175	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD5965	Clinical (unspecified phase)
0.6804	Remote Similarity	NPD9364	Phase 2
0.6804	Remote Similarity	NPD9363	Approved
0.6802	Remote Similarity	NPD4529	Approved
0.6802	Remote Similarity	NPD4526	Approved
0.6802	Remote Similarity	NPD4528	Approved
0.6798	Remote Similarity	NPD944	Approved
0.6793	Remote Similarity	NPD1631	Approved
0.6786	Remote Similarity	NPD8468	Phase 2
0.6782	Remote Similarity	NPD5721	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD180	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD7001	Phase 3
0.6763	Remote Similarity	NPD5475	Discontinued
0.6761	Remote Similarity	NPD3813	Approved
0.6758	Remote Similarity	NPD9383	Approved
0.6758	Remote Similarity	NPD9382	Approved
0.6751	Remote Similarity	NPD4376	Phase 3
0.6748	Remote Similarity	NPD6529	Discontinued
0.6743	Remote Similarity	NPD1383	Phase 3
0.6743	Remote Similarity	NPD1382	Phase 2
0.6742	Remote Similarity	NPD1270	Approved
0.6734	Remote Similarity	NPD2307	Discontinued
0.6719	Remote Similarity	NPD9362	Approved
0.6718	Remote Similarity	NPD4948	Discontinued
0.6715	Remote Similarity	NPD4900	Clinical (unspecified phase)
0.6714	Remote Similarity	NPD3394	Approved
0.6714	Remote Similarity	NPD3389	Approved
0.6714	Remote Similarity	NPD3393	Approved
0.6714	Remote Similarity	NPD5490	Discontinued
0.6705	Remote Similarity	NPD1427	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD1977	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD2511	Approved
0.6683	Remote Similarity	NPD4901	Clinical (unspecified phase)
0.6683	Remote Similarity	NPD4427	Phase 2
0.6683	Remote Similarity	NPD4491	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD751	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1627	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5640	Discontinued
0.6667	Remote Similarity	NPD1568	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4987	Clinical (unspecified phase)
0.6652	Remote Similarity	NPD5891	Approved
0.6648	Remote Similarity	NPD2809	Approved
0.6647	Remote Similarity	NPD9207	Approved
0.6647	Remote Similarity	NPD9206	Approved
0.6636	Remote Similarity	NPD4301	Approved
0.6634	Remote Similarity	NPD6137	Clinical (unspecified phase)
0.6634	Remote Similarity	NPD6987	Phase 1
0.663	Remote Similarity	NPD1630	Approved
0.6629	Remote Similarity	NPD569	Clinical (unspecified phase)
0.6605	Remote Similarity	NPD8356	Approved
0.6603	Remote Similarity	NPD4417	Approved
0.6595	Remote Similarity	NPD9398	Clinical (unspecified phase)
0.6589	Remote Similarity	NPD8479	Phase 2
0.6584	Remote Similarity	NPD7778	Approved
0.6584	Remote Similarity	NPD53	Approved
0.6584	Remote Similarity	NPD7777	Approved
0.6573	Remote Similarity	NPD7878	Phase 2
0.6566	Remote Similarity	NPD3321	Discontinued
0.6564	Remote Similarity	NPD3569	Discontinued
0.6564	Remote Similarity	NPD721	Approved
0.6553	Remote Similarity	NPD5901	Discontinued
0.6545	Remote Similarity	NPD5322	Clinical (unspecified phase)
0.6542	Remote Similarity	NPD6770	Approved
0.6541	Remote Similarity	NPD704	Clinical (unspecified phase)
0.6541	Remote Similarity	NPD5255	Approved
0.6531	Remote Similarity	NPD2814	Clinical (unspecified phase)
0.6528	Remote Similarity	NPD8037	Clinical (unspecified phase)
0.6528	Remote Similarity	NPD8036	Clinical (unspecified phase)
0.6526	Remote Similarity	NPD8327	Clinical (unspecified phase)
0.6526	Remote Similarity	NPD8325	Phase 3
0.6526	Remote Similarity	NPD8326	Phase 3
0.652	Remote Similarity	NPD4396	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD5149	Phase 2
0.6509	Remote Similarity	NPD5148	Clinical (unspecified phase)
0.6507	Remote Similarity	NPD4506	Discontinued
0.6492	Remote Similarity	NPD750	Phase 2
0.6486	Remote Similarity	NPD2582	Approved
0.6486	Remote Similarity	NPD2581	Approved
0.6484	Remote Similarity	NPD8430	Approved
0.6484	Remote Similarity	NPD7913	Clinical (unspecified phase)
0.6482	Remote Similarity	NPD8063	Discontinued
0.6477	Remote Similarity	NPD5751	Clinical (unspecified phase)
0.6477	Remote Similarity	NPD9076	Clinical (unspecified phase)
0.6473	Remote Similarity	NPD7712	Clinical (unspecified phase)
0.6467	Remote Similarity	NPD2061	Approved
0.6458	Remote Similarity	NPD4736	Clinical (unspecified phase)
0.6449	Remote Similarity	NPD4989	Phase 2
0.6449	Remote Similarity	NPD8000	Clinical (unspecified phase)
0.6448	Remote Similarity	NPD9596	Approved
0.6448	Remote Similarity	NPD9595	Approved
0.6443	Remote Similarity	NPD1587	Approved
0.6442	Remote Similarity	NPD7289	Clinical (unspecified phase)
0.6438	Remote Similarity	NPD8289	Discontinued
0.6432	Remote Similarity	NPD4334	Discontinued
0.6429	Remote Similarity	NPD5583	Clinical (unspecified phase)
0.6425	Remote Similarity	NPD5801	Clinical (unspecified phase)
0.6422	Remote Similarity	NPD6173	Approved
0.6419	Remote Similarity	NPD6578	Clinical (unspecified phase)
0.6415	Remote Similarity	NPD6657	Clinical (unspecified phase)
0.6415	Remote Similarity	NPD5866	Approved
0.641	Remote Similarity	NPD5899	Approved
0.641	Remote Similarity	NPD5897	Approved
0.641	Remote Similarity	NPD5898	Approved
0.6404	Remote Similarity	NPD7061	Clinical (unspecified phase)
0.64	Remote Similarity	NPD4081	Clinical (unspecified phase)
0.6392	Remote Similarity	NPD6642	Approved
0.6392	Remote Similarity	NPD1032	Phase 2
0.6392	Remote Similarity	NPD6641	Approved
0.639	Remote Similarity	NPD7000	Clinical (unspecified phase)
0.639	Remote Similarity	NPD6661	Clinical (unspecified phase)
0.639	Remote Similarity	NPD6999	Discontinued
0.6389	Remote Similarity	NPD7404	Approved
0.6383	Remote Similarity	NPD4239	Clinical (unspecified phase)
0.6381	Remote Similarity	NPD1367	Phase 2
0.6379	Remote Similarity	NPD9100	Approved
0.6373	Remote Similarity	NPD6206	Phase 1
0.6373	Remote Similarity	NPD158	Discontinued
0.6373	Remote Similarity	NPD1229	Phase 2
0.6369	Remote Similarity	NPD5020	Approved
0.6368	Remote Similarity	NPD3779	Clinical (unspecified phase)
0.6368	Remote Similarity	NPD4699	Discontinued
0.6368	Remote Similarity	NPD3785	Clinical (unspecified phase)
0.6368	Remote Similarity	NPD7470	Discontinued
0.6364	Remote Similarity	NPD3082	Discontinued
0.636	Remote Similarity	NPD1483	Discontinued
0.6359	Remote Similarity	NPD484	Approved
0.6351	Remote Similarity	NPD5022	Discontinued
0.635	Remote Similarity	NPD4021	Phase 2
0.6349	Remote Similarity	NPD6635	Approved
0.6345	Remote Similarity	NPD2092	Phase 2
0.6345	Remote Similarity	NPD2095	Phase 2
0.6345	Remote Similarity	NPD2094	Phase 2
0.6344	Remote Similarity	NPD276	Clinical (unspecified phase)
0.6337	Remote Similarity	NPD3406	Suspended
0.6337	Remote Similarity	NPD5317	Clinical (unspecified phase)
0.6328	Remote Similarity	NPD201	Phase 2
0.6328	Remote Similarity	NPD200	Phase 2
0.6324	Remote Similarity	NPD2290	Phase 3
0.6324	Remote Similarity	NPD2289	Phase 3
0.6316	Remote Similarity	NPD4905	Approved
0.6316	Remote Similarity	NPD4903	Approved
0.6316	Remote Similarity	NPD4906	Approved
0.6316	Remote Similarity	NPD6323	Clinical (unspecified phase)
0.6313	Remote Similarity	NPD9599	Approved
0.6313	Remote Similarity	NPD2096	Phase 2
0.6313	Remote Similarity	NPD2091	Phase 2
0.631	Remote Similarity	NPD4669	Clinical (unspecified phase)
0.631	Remote Similarity	NPD4671	Clinical (unspecified phase)
0.631	Remote Similarity	NPD4670	Clinical (unspecified phase)
0.63	Remote Similarity	NPD8020	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