NPASS Compound

Structure

NPC202743 OpenBabel07101719522D 35 37 0 0 1 0 0 0 0 0999 V2000 -1.9474 -3.3729 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9474 -1.6865 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8421 -1.6865 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4868 -2.5297 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9211 -1.6865 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.6865 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3206 -4.6919 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4491 -5.9452 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5970 -5.3435 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7255 -6.5967 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4342 -0.8432 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4605 -2.5297 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9211 -3.3729 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4605 -2.5297 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4342 -2.5297 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2466 -4.9928 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9737 -1.6865 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7994 -6.2959 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4605 -0.8432 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9702 -4.3413 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9226 -4.5437 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4094 -3.7005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3816 -2.5297 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8684 -3.3729 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.0758 -6.9474 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.3186 -5.4332 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.3778 -3.5987 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4079 -2.5297 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.9737 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9737 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.9737 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8684 -1.6865 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.7579 -2.9769 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9737 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 1 14 1 0 0 0 0 2 14 1 0 0 0 0 3 32 1 0 0 0 0 4 6 1 0 0 0 0 4 14 2 0 0 0 0 5 11 2 0 0 0 0 5 15 1 0 0 0 0 6 17 1 0 0 0 0 7 9 1 0 0 0 0 7 16 2 0 0 0 0 8 10 2 0 0 0 0 8 16 1 0 0 0 0 9 18 2 0 0 0 0 10 18 1 0 0 0 0 11 19 1 0 0 0 0 12 15 2 0 0 0 0 12 17 1 0 0 0 0 13 15 1 0 0 0 0 16 20 1 0 0 0 0 17 19 2 0 0 0 0 18 25 1 0 0 0 0 19 34 1 0 0 0 0 20 21 2 0 0 0 0 20 24 1 0 0 0 0 21 22 1 0 0 0 0 21 26 1 0 0 0 0 22 27 2 0 0 0 0 22 33 1 0 0 0 0 23 24 1 0 0 0 0 23 28 2 0 0 0 0 23 32 1 0 0 0 0 24 13 1 1 0 0 0 24 33 1 0 0 0 0 29 35 1 0 0 0 0 30 35 2 0 0 0 0 31 35 2 0 0 0 0 34 35 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	504.11
Volume:	478.037
LogP:	2.836
LogD:	1.504
LogS:	-2.717
# Rotatable Bonds:	9
TPSA:	153.5
# H-Bond Aceptor:	10
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.237
Synthetic Accessibility Score:	3.932
Fsp3:	0.292
Lipinski Rule-of-5:	Accepted
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:	-5.162
MDCK Permeability:	1.2180998055555392e-05
Pgp-inhibitor:	0.014
Pgp-substrate:	0.006
Human Intestinal Absorption (HIA):	0.876
20% Bioavailability (F20%):	0.99
30% Bioavailability (F30%):	0.988

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.005
Plasma Protein Binding (PPB):	99.95753479003906%
Volume Distribution (VD):	0.365
Pgp-substrate:	0.6295645833015442%

ADMET: Metabolism

CYP1A2-inhibitor:	0.052
CYP1A2-substrate:	0.504
CYP2C19-inhibitor:	0.641
CYP2C19-substrate:	0.174
CYP2C9-inhibitor:	0.892
CYP2C9-substrate:	0.957
CYP2D6-inhibitor:	0.048
CYP2D6-substrate:	0.311
CYP3A4-inhibitor:	0.529
CYP3A4-substrate:	0.277

ADMET: Excretion

Clearance (CL):	7.452
Half-life (T1/2):	0.091

ADMET: Toxicity

hERG Blockers:	0.015
Human Hepatotoxicity (H-HT):	0.919
Drug-inuced Liver Injury (DILI):	0.582
AMES Toxicity:	0.005
Rat Oral Acute Toxicity:	0.368
Maximum Recommended Daily Dose:	0.92
Skin Sensitization:	0.102
Carcinogencity:	0.529
Eye Corrosion:	0.003
Eye Irritation:	0.021
Respiratory Toxicity:	0.1

Download Data

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

Natural Product: NPC202743

Natural Product ID:	NPC202743
*Common Name:**	Butyrolactone I 4''-Sulfate
IUPAC Name:	methyl (2R)-4-hydroxy-3-(4-hydroxyphenyl)-2-[[3-(3-methylbut-2-enyl)-4-sulfooxyphenyl]methyl]-5-oxofuran-2-carboxylate
Synonyms:
Standard InCHIKey:	NWSMSBOLLCRCSY-XMMPIXPASA-N
Standard InCHI:	InChI=1S/C24H24O10S/c1-14(2)4-6-17-12-15(5-11-19(17)34-35(29,30)31)13-24(23(28)32-3)20(21(26)22(27)33-24)16-7-9-18(25)10-8-16/h4-5,7-12,25-26H,6,13H2,1-3H3,(H,29,30,31)/t24-/m1/s1
SMILES:	COC(=O)[C@]1(Cc2ccc(c(c2)CC=C(C)C)OS(=O)(=O)O)OC(=O)C(=C1c1ccc(cc1)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL465047
PubChem CID:	24861909
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000403] Organic sulfuric acids and derivatives [CHEMONTID:0004258] Arylsulfates [CHEMONTID:0002626] Phenylsulfates

*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
NPO2595	Aspergillus terreus	Species	Aspergillaceae	Eukaryota	n.a.	from the rhizosphere of Opuntia versicolor of the Sonoran Desert	n.a.	PMID[14695798]
NPO2595	Aspergillus terreus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16124769]
NPO2595	Aspergillus terreus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18271552]
NPO2595	Aspergillus terreus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22360613]
NPO2595	Aspergillus terreus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24534845]
NPO2595	Aspergillus terreus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25671343]
NPO2595	Aspergillus terreus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2921224]
NPO2595	Aspergillus terreus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30207465]
NPO2595	Aspergillus terreus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32163285]
NPO2595	Aspergillus terreus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32897070]
NPO2595	Aspergillus terreus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8984154]
NPO2595	Aspergillus terreus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2595	Aspergillus terreus	Species	Aspergillaceae	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	5

Activity Type	# Activity
Individual Protein	1
Others	3
PROTEIN FAMILY	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT3114	Individual Protein	Dual-specificity tyrosine-phosphorylation regulated kinase 1A	Homo sapiens	IC50	>	100000.0	nM	PMID[450232]
NPT2	Others	Unspecified		IC50	>	10000.0	nM	PMID[450232]
NPT2	Others	Unspecified		IC50	>	100000.0	nM	PMID[450232]
NPT22078	PROTEIN FAMILY	Glycogen synthase kinase-3	Sus scrofa	IC50	>	100000.0	nM	PMID[450232]

☑ 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 NPC202743 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	275
0.1-0.2	1282
0.2-0.3	3024
0.3-0.4	7640
0.4-0.5	11558
0.5-0.6	5329
0.6-0.7	12030
0.7-0.8	1525
0.8-0.85	21
0.85-0.9	5
0.9-0.95	5
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9921	High Similarity	NPC173034
0.9603	High Similarity	NPC217431
0.9206	High Similarity	NPC14141
0.8519	High Similarity	NPC108553
0.8438	Intermediate Similarity	NPC471033
0.8438	Intermediate Similarity	NPC311091
0.8281	Intermediate Similarity	NPC128249
0.8261	Intermediate Similarity	NPC168799
0.8261	Intermediate Similarity	NPC155209
0.8188	Intermediate Similarity	NPC61
0.8188	Intermediate Similarity	NPC25581
0.8188	Intermediate Similarity	NPC5419
0.8188	Intermediate Similarity	NPC18074
0.8156	Intermediate Similarity	NPC279676
0.8156	Intermediate Similarity	NPC67349
0.8134	Intermediate Similarity	NPC288945
0.8116	Intermediate Similarity	NPC198388
0.8058	Intermediate Similarity	NPC302844
0.8042	Intermediate Similarity	NPC179505
0.8042	Intermediate Similarity	NPC156709
0.8	Intermediate Similarity	NPC89630
0.7986	Intermediate Similarity	NPC38473
0.7969	Intermediate Similarity	NPC17693
0.7969	Intermediate Similarity	NPC48525
0.7945	Intermediate Similarity	NPC32
0.7945	Intermediate Similarity	NPC304956
0.7945	Intermediate Similarity	NPC122491
0.7941	Intermediate Similarity	NPC137416
0.7929	Intermediate Similarity	NPC327204
0.7929	Intermediate Similarity	NPC323379
0.7926	Intermediate Similarity	NPC473942
0.7917	Intermediate Similarity	NPC289690
0.7917	Intermediate Similarity	NPC288452
0.7891	Intermediate Similarity	NPC258671
0.7891	Intermediate Similarity	NPC53884
0.7887	Intermediate Similarity	NPC182217
0.7887	Intermediate Similarity	NPC70680
0.7887	Intermediate Similarity	NPC233350
0.7874	Intermediate Similarity	NPC79543
0.7874	Intermediate Similarity	NPC471954
0.7874	Intermediate Similarity	NPC75272
0.7872	Intermediate Similarity	NPC477281
0.7872	Intermediate Similarity	NPC477280
0.7872	Intermediate Similarity	NPC19719
0.7867	Intermediate Similarity	NPC32197
0.7862	Intermediate Similarity	NPC469911
0.7857	Intermediate Similarity	NPC473777
0.7847	Intermediate Similarity	NPC284409
0.7847	Intermediate Similarity	NPC283560
0.7847	Intermediate Similarity	NPC24295
0.7842	Intermediate Similarity	NPC131684
0.7836	Intermediate Similarity	NPC164852
0.7832	Intermediate Similarity	NPC90431
0.7817	Intermediate Similarity	NPC68517
0.7812	Intermediate Similarity	NPC183700
0.7793	Intermediate Similarity	NPC256162
0.7793	Intermediate Similarity	NPC59775
0.7786	Intermediate Similarity	NPC296526
0.7785	Intermediate Similarity	NPC283081
0.7785	Intermediate Similarity	NPC221383
0.7785	Intermediate Similarity	NPC143892
0.7785	Intermediate Similarity	NPC299090
0.777	Intermediate Similarity	NPC478215
0.7762	Intermediate Similarity	NPC311742
0.7761	Intermediate Similarity	NPC473136
0.7761	Intermediate Similarity	NPC478121
0.774	Intermediate Similarity	NPC477279
0.7737	Intermediate Similarity	NPC474803
0.7737	Intermediate Similarity	NPC231767
0.7737	Intermediate Similarity	NPC184219
0.7727	Intermediate Similarity	NPC28951
0.7727	Intermediate Similarity	NPC325646
0.7721	Intermediate Similarity	NPC67300
0.7721	Intermediate Similarity	NPC327070
0.7721	Intermediate Similarity	NPC121168
0.7721	Intermediate Similarity	NPC469927
0.7718	Intermediate Similarity	NPC474309
0.7714	Intermediate Similarity	NPC477300
0.7704	Intermediate Similarity	NPC470848
0.7704	Intermediate Similarity	NPC470849
0.7703	Intermediate Similarity	NPC474692
0.7698	Intermediate Similarity	NPC473993
0.7692	Intermediate Similarity	NPC4982
0.7692	Intermediate Similarity	NPC473054
0.7692	Intermediate Similarity	NPC5310
0.7692	Intermediate Similarity	NPC176814
0.7692	Intermediate Similarity	NPC300776
0.7692	Intermediate Similarity	NPC286222
0.7692	Intermediate Similarity	NPC106406
0.7692	Intermediate Similarity	NPC68779
0.7687	Intermediate Similarity	NPC141791
0.7687	Intermediate Similarity	NPC477278
0.7687	Intermediate Similarity	NPC263386
0.7687	Intermediate Similarity	NPC253722
0.7687	Intermediate Similarity	NPC253481
0.7687	Intermediate Similarity	NPC184053
0.7687	Intermediate Similarity	NPC31751
0.7687	Intermediate Similarity	NPC477277
0.7681	Intermediate Similarity	NPC127975
0.7681	Intermediate Similarity	NPC88403
0.7671	Intermediate Similarity	NPC295492
0.7671	Intermediate Similarity	NPC476820
0.7671	Intermediate Similarity	NPC303683
0.7671	Intermediate Similarity	NPC274891
0.7671	Intermediate Similarity	NPC474875
0.7671	Intermediate Similarity	NPC476819
0.7671	Intermediate Similarity	NPC26241
0.7671	Intermediate Similarity	NPC205751
0.7669	Intermediate Similarity	NPC325295
0.7669	Intermediate Similarity	NPC76308
0.7667	Intermediate Similarity	NPC229264
0.7664	Intermediate Similarity	NPC236981
0.7662	Intermediate Similarity	NPC477299
0.766	Intermediate Similarity	NPC32626
0.766	Intermediate Similarity	NPC237506
0.766	Intermediate Similarity	NPC329344
0.766	Intermediate Similarity	NPC172673
0.766	Intermediate Similarity	NPC253488
0.766	Intermediate Similarity	NPC217052
0.7656	Intermediate Similarity	NPC31274
0.7656	Intermediate Similarity	NPC281604
0.7652	Intermediate Similarity	NPC23402
0.7647	Intermediate Similarity	NPC472271
0.7647	Intermediate Similarity	NPC31936
0.7643	Intermediate Similarity	NPC79332
0.7643	Intermediate Similarity	NPC473744
0.7638	Intermediate Similarity	NPC70843
0.7635	Intermediate Similarity	NPC37331
0.7635	Intermediate Similarity	NPC472016
0.7635	Intermediate Similarity	NPC43158
0.7635	Intermediate Similarity	NPC277315
0.7635	Intermediate Similarity	NPC258469
0.7635	Intermediate Similarity	NPC220664
0.7635	Intermediate Similarity	NPC303090
0.7635	Intermediate Similarity	NPC192831
0.7635	Intermediate Similarity	NPC319628
0.7635	Intermediate Similarity	NPC284948
0.7632	Intermediate Similarity	NPC103116
0.7626	Intermediate Similarity	NPC90128
0.7626	Intermediate Similarity	NPC303680
0.7626	Intermediate Similarity	NPC84076
0.7622	Intermediate Similarity	NPC472591
0.7619	Intermediate Similarity	NPC170812
0.7619	Intermediate Similarity	NPC275903
0.7619	Intermediate Similarity	NPC304110
0.7619	Intermediate Similarity	NPC27518
0.7619	Intermediate Similarity	NPC9218
0.7616	Intermediate Similarity	NPC192568
0.7616	Intermediate Similarity	NPC471076
0.7615	Intermediate Similarity	NPC470355
0.7612	Intermediate Similarity	NPC474890
0.7612	Intermediate Similarity	NPC161943
0.7612	Intermediate Similarity	NPC273282
0.7609	Intermediate Similarity	NPC265413
0.7609	Intermediate Similarity	NPC10154
0.7606	Intermediate Similarity	NPC318799
0.7603	Intermediate Similarity	NPC278068
0.7603	Intermediate Similarity	NPC219428
0.7603	Intermediate Similarity	NPC37250
0.7603	Intermediate Similarity	NPC302857
0.7603	Intermediate Similarity	NPC152942
0.7603	Intermediate Similarity	NPC142703
0.76	Intermediate Similarity	NPC475923
0.7597	Intermediate Similarity	NPC88141
0.7597	Intermediate Similarity	NPC326187
0.7594	Intermediate Similarity	NPC19290
0.7591	Intermediate Similarity	NPC132518
0.7591	Intermediate Similarity	NPC325301
0.7591	Intermediate Similarity	NPC477151
0.7591	Intermediate Similarity	NPC139171
0.7589	Intermediate Similarity	NPC304622
0.7589	Intermediate Similarity	NPC241354
0.7589	Intermediate Similarity	NPC214246
0.7586	Intermediate Similarity	NPC255428
0.7584	Intermediate Similarity	NPC25491
0.7584	Intermediate Similarity	NPC160378
0.7578	Intermediate Similarity	NPC156648
0.7578	Intermediate Similarity	NPC260952
0.7576	Intermediate Similarity	NPC221870
0.7574	Intermediate Similarity	NPC241001
0.7571	Intermediate Similarity	NPC151167
0.7571	Intermediate Similarity	NPC121104
0.7571	Intermediate Similarity	NPC123722
0.7571	Intermediate Similarity	NPC5018
0.7571	Intermediate Similarity	NPC276466
0.7571	Intermediate Similarity	NPC123228
0.7569	Intermediate Similarity	NPC248150
0.7569	Intermediate Similarity	NPC194970
0.7568	Intermediate Similarity	NPC224389
0.7568	Intermediate Similarity	NPC13818
0.7568	Intermediate Similarity	NPC206095
0.7568	Intermediate Similarity	NPC471027
0.7568	Intermediate Similarity	NPC297517
0.7568	Intermediate Similarity	NPC35702
0.7568	Intermediate Similarity	NPC477335
0.7559	Intermediate Similarity	NPC303141
0.7559	Intermediate Similarity	NPC243677
0.7556	Intermediate Similarity	NPC264976
0.7556	Intermediate Similarity	NPC182240
0.7556	Intermediate Similarity	NPC70084

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 NPC202743 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	246
0.1-0.2	806
0.2-0.3	1412
0.3-0.4	2590
0.4-0.5	2188
0.5-0.6	1316
0.6-0.7	551
0.7-0.8	40
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
0.8129	Intermediate Similarity	NPD6355	Discontinued
0.8043	Intermediate Similarity	NPD6798	Discontinued
0.7986	Intermediate Similarity	NPD4062	Phase 3
0.7929	Intermediate Similarity	NPD4060	Phase 1
0.7667	Intermediate Similarity	NPD5049	Phase 3
0.7655	Intermediate Similarity	NPD2935	Discontinued
0.7635	Intermediate Similarity	NPD6190	Approved
0.7628	Intermediate Similarity	NPD7075	Discontinued
0.7606	Intermediate Similarity	NPD6233	Phase 2
0.7589	Intermediate Similarity	NPD7095	Approved
0.7576	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7535	Intermediate Similarity	NPD3764	Approved
0.7466	Intermediate Similarity	NPD2799	Discontinued
0.7436	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD2797	Approved
0.7383	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD6801	Discontinued
0.7333	Intermediate Similarity	NPD8166	Discontinued
0.7333	Intermediate Similarity	NPD4628	Phase 3
0.7328	Intermediate Similarity	NPD2067	Discontinued
0.7315	Intermediate Similarity	NPD4534	Discontinued
0.7315	Intermediate Similarity	NPD5958	Discontinued
0.7313	Intermediate Similarity	NPD2629	Approved
0.7305	Intermediate Similarity	NPD1164	Approved
0.7303	Intermediate Similarity	NPD6799	Approved
0.7303	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD3268	Approved
0.7285	Intermediate Similarity	NPD2354	Approved
0.7259	Intermediate Similarity	NPD4198	Discontinued
0.7255	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD4626	Approved
0.7234	Intermediate Similarity	NPD1283	Approved
0.7226	Intermediate Similarity	NPD9545	Approved
0.7219	Intermediate Similarity	NPD7003	Approved
0.7206	Intermediate Similarity	NPD9493	Approved
0.7194	Intermediate Similarity	NPD3847	Discontinued
0.7181	Intermediate Similarity	NPD4476	Approved
0.7181	Intermediate Similarity	NPD4477	Approved
0.7179	Intermediate Similarity	NPD7458	Discontinued
0.7172	Intermediate Similarity	NPD2313	Discontinued
0.7172	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1535	Discovery
0.7143	Intermediate Similarity	NPD4340	Discontinued
0.7134	Intermediate Similarity	NPD6599	Discontinued
0.7134	Intermediate Similarity	NPD4380	Phase 2
0.7123	Intermediate Similarity	NPD6663	Approved
0.7114	Intermediate Similarity	NPD4308	Phase 3
0.7103	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD1894	Discontinued
0.7092	Intermediate Similarity	NPD1481	Phase 2
0.7086	Intermediate Similarity	NPD2424	Discontinued
0.7083	Intermediate Similarity	NPD5736	Approved
0.7071	Intermediate Similarity	NPD3026	Approved
0.7071	Intermediate Similarity	NPD3023	Approved
0.7067	Intermediate Similarity	NPD2438	Suspended
0.7063	Intermediate Similarity	NPD2859	Approved
0.7063	Intermediate Similarity	NPD1203	Approved
0.7063	Intermediate Similarity	NPD3817	Phase 2
0.7063	Intermediate Similarity	NPD2860	Approved
0.7059	Intermediate Similarity	NPD3887	Approved
0.7051	Intermediate Similarity	NPD5403	Approved
0.705	Intermediate Similarity	NPD5691	Approved
0.7047	Intermediate Similarity	NPD7097	Phase 1
0.7034	Intermediate Similarity	NPD6832	Phase 2
0.7031	Intermediate Similarity	NPD3020	Approved
0.7021	Intermediate Similarity	NPD1281	Approved
0.702	Intermediate Similarity	NPD2353	Approved
0.702	Intermediate Similarity	NPD5762	Approved
0.702	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD7266	Discontinued
0.702	Intermediate Similarity	NPD5763	Approved
0.7019	Intermediate Similarity	NPD3882	Suspended
0.7006	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD2932	Approved
0.7	Intermediate Similarity	NPD3019	Approved
0.7	Intermediate Similarity	NPD7033	Discontinued
0.6993	Remote Similarity	NPD3750	Approved
0.6984	Remote Similarity	NPD2934	Approved
0.6984	Remote Similarity	NPD2933	Approved
0.6981	Remote Similarity	NPD7411	Suspended
0.6962	Remote Similarity	NPD3455	Phase 2
0.6959	Remote Similarity	NPD2979	Phase 3
0.6954	Remote Similarity	NPD2531	Phase 2
0.6954	Remote Similarity	NPD5405	Approved
0.6954	Remote Similarity	NPD5408	Approved
0.6954	Remote Similarity	NPD5404	Approved
0.6954	Remote Similarity	NPD5406	Approved
0.695	Remote Similarity	NPD4136	Approved
0.695	Remote Similarity	NPD4135	Approved
0.695	Remote Similarity	NPD4106	Approved
0.6947	Remote Similarity	NPD5909	Discontinued
0.6944	Remote Similarity	NPD3266	Approved
0.6944	Remote Similarity	NPD3267	Approved
0.6944	Remote Similarity	NPD987	Approved
0.694	Remote Similarity	NPD3021	Approved
0.694	Remote Similarity	NPD3022	Approved
0.6929	Remote Similarity	NPD3025	Approved
0.6929	Remote Similarity	NPD1651	Approved
0.6929	Remote Similarity	NPD3024	Approved
0.6929	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD4102	Approved
0.6929	Remote Similarity	NPD4105	Approved
0.6923	Remote Similarity	NPD5401	Approved
0.6923	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD1358	Approved
0.6914	Remote Similarity	NPD7768	Phase 2
0.6914	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6912	Remote Similarity	NPD5535	Approved
0.6909	Remote Similarity	NPD6232	Discontinued
0.6908	Remote Similarity	NPD2346	Discontinued
0.6908	Remote Similarity	NPD2344	Approved
0.6897	Remote Similarity	NPD2798	Approved
0.6894	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD8455	Phase 2
0.6894	Remote Similarity	NPD7819	Suspended
0.6892	Remote Similarity	NPD4248	Discontinued
0.6883	Remote Similarity	NPD3400	Discontinued
0.6883	Remote Similarity	NPD4110	Phase 3
0.6883	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6883	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD5306	Approved
0.6879	Remote Similarity	NPD5305	Approved
0.6875	Remote Similarity	NPD3225	Approved
0.6867	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD2897	Discontinued
0.6853	Remote Similarity	NPD1608	Approved
0.6853	Remote Similarity	NPD9717	Approved
0.6852	Remote Similarity	NPD5402	Approved
0.6846	Remote Similarity	NPD1240	Approved
0.6846	Remote Similarity	NPD825	Approved
0.6846	Remote Similarity	NPD826	Approved
0.6846	Remote Similarity	NPD4307	Phase 2
0.6831	Remote Similarity	NPD3496	Discontinued
0.6829	Remote Similarity	NPD6234	Discontinued
0.6824	Remote Similarity	NPD1296	Phase 2
0.6821	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD2614	Approved
0.68	Remote Similarity	NPD230	Phase 1
0.6797	Remote Similarity	NPD6004	Phase 3
0.6797	Remote Similarity	NPD6800	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD6005	Phase 3
0.6797	Remote Similarity	NPD6002	Phase 3
0.6797	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6791	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD7843	Approved
0.6786	Remote Similarity	NPD7473	Discontinued
0.6786	Remote Similarity	NPD5536	Phase 2
0.6784	Remote Similarity	NPD6559	Discontinued
0.6783	Remote Similarity	NPD422	Phase 1
0.6783	Remote Similarity	NPD1201	Approved
0.6783	Remote Similarity	NPD4806	Approved
0.6783	Remote Similarity	NPD4807	Approved
0.6781	Remote Similarity	NPD5647	Approved
0.6776	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD1510	Phase 2
0.6772	Remote Similarity	NPD6273	Approved
0.6768	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD7157	Approved
0.6763	Remote Similarity	NPD255	Approved
0.6763	Remote Similarity	NPD256	Approved
0.6759	Remote Similarity	NPD1876	Approved
0.6755	Remote Similarity	NPD1607	Approved
0.6753	Remote Similarity	NPD970	Clinical (unspecified phase)
0.675	Remote Similarity	NPD3226	Approved
0.675	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6741	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6741	Remote Similarity	NPD74	Approved
0.6741	Remote Similarity	NPD9266	Approved
0.6741	Remote Similarity	NPD2684	Approved
0.6739	Remote Similarity	NPD1241	Discontinued
0.6736	Remote Similarity	NPD3972	Approved
0.6735	Remote Similarity	NPD5204	Approved
0.6733	Remote Similarity	NPD943	Approved
0.6732	Remote Similarity	NPD1551	Phase 2
0.6732	Remote Similarity	NPD1501	Clinical (unspecified phase)
0.6732	Remote Similarity	NPD6032	Approved
0.6731	Remote Similarity	NPD2309	Approved
0.6728	Remote Similarity	NPD37	Approved
0.6728	Remote Similarity	NPD1934	Approved
0.6726	Remote Similarity	NPD6166	Phase 2
0.6726	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6725	Remote Similarity	NPD5953	Discontinued
0.6723	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6716	Remote Similarity	NPD3134	Approved
0.6712	Remote Similarity	NPD1470	Approved
0.6711	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6709	Remote Similarity	NPD2534	Approved
0.6709	Remote Similarity	NPD2532	Approved
0.6709	Remote Similarity	NPD2533	Approved
0.6709	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6708	Remote Similarity	NPD6502	Phase 2
0.6707	Remote Similarity	NPD4967	Phase 2
0.6707	Remote Similarity	NPD4965	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