NPASS Compound

Structure

NPC173034 OpenBabel07101719162D 35 37 0 0 1 0 0 0 0 0999 V2000 9.4098 -1.1850 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5861 -2.8622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3799 -4.3624 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0454 -2.1763 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7443 -3.3711 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6494 -3.0658 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0328 -0.4239 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7795 0.7046 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6843 0.2997 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4310 1.4282 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3166 -4.1588 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1087 -2.3798 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5680 -1.6939 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.0137 -2.0745 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1403 -2.4816 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0804 -0.2214 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6810 -3.1675 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3834 1.2258 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2850 -4.0570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4289 -0.9450 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 1.0645 -1.7327 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2036 -2.6851 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6313 -1.8974 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.0350 1.9493 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.8573 -4.8448 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1121 -1.9352 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1720 -2.5834 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 2.8076 -3.5747 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7881 -2.3843 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 26 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 34 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:	3.153
LogD:	2.247
LogS:	-2.778
# Rotatable Bonds:	9
TPSA:	156.66
# H-Bond Aceptor:	10
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.277
Synthetic Accessibility Score:	3.66
Fsp3:	0.25
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:	-5.262
MDCK Permeability:	1.4192038179317024e-05
Pgp-inhibitor:	0.006
Pgp-substrate:	0.005
Human Intestinal Absorption (HIA):	0.913
20% Bioavailability (F20%):	0.997
30% Bioavailability (F30%):	0.99

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.005
Plasma Protein Binding (PPB):	100.30230712890625%
Volume Distribution (VD):	0.358
Pgp-substrate:	0.731964111328125%

ADMET: Metabolism

CYP1A2-inhibitor:	0.544
CYP1A2-substrate:	0.384
CYP2C19-inhibitor:	0.682
CYP2C19-substrate:	0.07
CYP2C9-inhibitor:	0.914
CYP2C9-substrate:	0.952
CYP2D6-inhibitor:	0.787
CYP2D6-substrate:	0.177
CYP3A4-inhibitor:	0.699
CYP3A4-substrate:	0.272

ADMET: Excretion

Clearance (CL):	8.342
Half-life (T1/2):	0.655

ADMET: Toxicity

hERG Blockers:	0.013
Human Hepatotoxicity (H-HT):	0.89
Drug-inuced Liver Injury (DILI):	0.954
AMES Toxicity:	0.004
Rat Oral Acute Toxicity:	0.115
Maximum Recommended Daily Dose:	0.633
Skin Sensitization:	0.084
Carcinogencity:	0.108
Eye Corrosion:	0.003
Eye Irritation:	0.072
Respiratory Toxicity:	0.072

Download Data

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

Natural Product: NPC173034

Natural Product ID:	NPC173034
*Common Name:**	Butyrolactone I 3-Sulfate
IUPAC Name:	methyl (2R)-2-[[4-hydroxy-3-(3-methylbut-2-enyl)phenyl]methyl]-3-(4-hydroxyphenyl)-5-oxo-4-sulfooxyfuran-2-carboxylate
Synonyms:	Butyrolactone I 3-Sulfate
Standard InCHIKey:	QRQVCSIFYBTLJW-XMMPIXPASA-N
Standard InCHI:	InChI=1S/C24H24O10S/c1-14(2)4-6-17-12-15(5-11-19(17)26)13-24(23(28)32-3)20(16-7-9-18(25)10-8-16)21(22(27)33-24)34-35(29,30)31/h4-5,7-12,25-26H,6,13H2,1-3H3,(H,29,30,31)/t24-/m1/s1
SMILES:	CC(=CCc1cc(ccc1O)C[C@@]1(C(=C(C(=O)O1)OS(=O)(=O)O)c1ccc(cc1)O)C(=O)OC)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL460464
PubChem CID:	24861908
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0000324] Fatty acid esters

*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
Others	1

Activity Type	# Activity
Cell Line	1
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[480744]
NPT165	Cell Line	HeLa	Homo sapiens	CC50	=	80700.0	nM	PMID[480744]
NPT22078	PROTEIN FAMILY	Glycogen synthase kinase-3	Sus scrofa	IC50	>	100000.0	nM	PMID[480744]
NPT2	Others	Unspecified		IC50	=	6000.0	nM	PMID[480744]
NPT2	Others	Unspecified		IC50	=	2400.0	nM	PMID[480744]
NPT2	Others	Unspecified		IC50	>	10000.0	nM	PMID[480744]

☑ 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 NPC173034 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	277
0.1-0.2	1301
0.2-0.3	3015
0.3-0.4	7658
0.4-0.5	11546
0.5-0.6	5383
0.6-0.7	11991
0.7-0.8	1496
0.8-0.85	17
0.85-0.9	5
0.9-0.95	4
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9921	High Similarity	NPC202743
0.9524	High Similarity	NPC217431
0.9127	High Similarity	NPC14141
0.8444	Intermediate Similarity	NPC108553
0.8359	Intermediate Similarity	NPC471033
0.8359	Intermediate Similarity	NPC311091
0.8346	Intermediate Similarity	NPC128249
0.8188	Intermediate Similarity	NPC168799
0.8188	Intermediate Similarity	NPC155209
0.8116	Intermediate Similarity	NPC18074
0.8116	Intermediate Similarity	NPC5419
0.8116	Intermediate Similarity	NPC25581
0.8116	Intermediate Similarity	NPC61
0.8085	Intermediate Similarity	NPC279676
0.8085	Intermediate Similarity	NPC67349
0.806	Intermediate Similarity	NPC89630
0.806	Intermediate Similarity	NPC288945
0.8043	Intermediate Similarity	NPC198388
0.8031	Intermediate Similarity	NPC17693
0.8	Intermediate Similarity	NPC137416
0.7986	Intermediate Similarity	NPC323379
0.7986	Intermediate Similarity	NPC327204
0.7986	Intermediate Similarity	NPC302844
0.7985	Intermediate Similarity	NPC473942
0.7972	Intermediate Similarity	NPC156709
0.7972	Intermediate Similarity	NPC179505
0.7937	Intermediate Similarity	NPC79543
0.7937	Intermediate Similarity	NPC471954
0.7937	Intermediate Similarity	NPC75272
0.7917	Intermediate Similarity	NPC38473
0.7899	Intermediate Similarity	NPC131684
0.7895	Intermediate Similarity	NPC164852
0.7891	Intermediate Similarity	NPC48525
0.7877	Intermediate Similarity	NPC122491
0.7877	Intermediate Similarity	NPC304956
0.7877	Intermediate Similarity	NPC32
0.7874	Intermediate Similarity	NPC183700
0.7847	Intermediate Similarity	NPC289690
0.7847	Intermediate Similarity	NPC288452
0.7846	Intermediate Similarity	NPC296526
0.7823	Intermediate Similarity	NPC53884
0.7823	Intermediate Similarity	NPC258671
0.782	Intermediate Similarity	NPC478121
0.782	Intermediate Similarity	NPC473136
0.7817	Intermediate Similarity	NPC233350
0.7817	Intermediate Similarity	NPC70680
0.7817	Intermediate Similarity	NPC182217
0.7801	Intermediate Similarity	NPC477281
0.7801	Intermediate Similarity	NPC477280
0.7801	Intermediate Similarity	NPC19719
0.78	Intermediate Similarity	NPC32197
0.7794	Intermediate Similarity	NPC474803
0.7794	Intermediate Similarity	NPC184219
0.7793	Intermediate Similarity	NPC469911
0.7786	Intermediate Similarity	NPC28951
0.7786	Intermediate Similarity	NPC325646
0.7786	Intermediate Similarity	NPC473777
0.7778	Intermediate Similarity	NPC24295
0.7778	Intermediate Similarity	NPC283560
0.7778	Intermediate Similarity	NPC67300
0.7778	Intermediate Similarity	NPC121168
0.7778	Intermediate Similarity	NPC284409
0.7762	Intermediate Similarity	NPC90431
0.7752	Intermediate Similarity	NPC286222
0.7746	Intermediate Similarity	NPC68517
0.7727	Intermediate Similarity	NPC325295
0.7727	Intermediate Similarity	NPC76308
0.7724	Intermediate Similarity	NPC59775
0.7724	Intermediate Similarity	NPC256162
0.7721	Intermediate Similarity	NPC236981
0.7718	Intermediate Similarity	NPC299090
0.7718	Intermediate Similarity	NPC283081
0.7718	Intermediate Similarity	NPC143892
0.7718	Intermediate Similarity	NPC221383
0.7717	Intermediate Similarity	NPC31274
0.7714	Intermediate Similarity	NPC253488
0.771	Intermediate Similarity	NPC23402
0.7704	Intermediate Similarity	NPC31936
0.7698	Intermediate Similarity	NPC70843
0.7698	Intermediate Similarity	NPC478215
0.7698	Intermediate Similarity	NPC473744
0.7698	Intermediate Similarity	NPC79332
0.7692	Intermediate Similarity	NPC311742
0.7676	Intermediate Similarity	NPC472591
0.7671	Intermediate Similarity	NPC477279
0.7671	Intermediate Similarity	NPC275903
0.7671	Intermediate Similarity	NPC170812
0.7669	Intermediate Similarity	NPC474890
0.7669	Intermediate Similarity	NPC161943
0.7669	Intermediate Similarity	NPC273282
0.7664	Intermediate Similarity	NPC265413
0.7664	Intermediate Similarity	NPC10154
0.7664	Intermediate Similarity	NPC231767
0.7656	Intermediate Similarity	NPC88141
0.7652	Intermediate Similarity	NPC19290
0.7651	Intermediate Similarity	NPC475923
0.7651	Intermediate Similarity	NPC474309
0.7647	Intermediate Similarity	NPC327070
0.7647	Intermediate Similarity	NPC325301
0.7647	Intermediate Similarity	NPC469927
0.7647	Intermediate Similarity	NPC477151
0.7647	Intermediate Similarity	NPC132518
0.7643	Intermediate Similarity	NPC477300
0.7643	Intermediate Similarity	NPC214246
0.7638	Intermediate Similarity	NPC260952
0.7635	Intermediate Similarity	NPC474692
0.763	Intermediate Similarity	NPC241001
0.763	Intermediate Similarity	NPC470849
0.763	Intermediate Similarity	NPC470848
0.7626	Intermediate Similarity	NPC473993
0.7626	Intermediate Similarity	NPC121104
0.7622	Intermediate Similarity	NPC176814
0.7622	Intermediate Similarity	NPC194970
0.7622	Intermediate Similarity	NPC68779
0.7622	Intermediate Similarity	NPC106406
0.7622	Intermediate Similarity	NPC4982
0.7622	Intermediate Similarity	NPC473054
0.7622	Intermediate Similarity	NPC5310
0.7622	Intermediate Similarity	NPC300776
0.7619	Intermediate Similarity	NPC303141
0.7619	Intermediate Similarity	NPC243677
0.7619	Intermediate Similarity	NPC184053
0.7619	Intermediate Similarity	NPC477278
0.7619	Intermediate Similarity	NPC253481
0.7619	Intermediate Similarity	NPC253722
0.7619	Intermediate Similarity	NPC477277
0.7619	Intermediate Similarity	NPC31751
0.7612	Intermediate Similarity	NPC263386
0.7612	Intermediate Similarity	NPC264976
0.7612	Intermediate Similarity	NPC141791
0.7612	Intermediate Similarity	NPC182240
0.7609	Intermediate Similarity	NPC127975
0.7609	Intermediate Similarity	NPC88403
0.7606	Intermediate Similarity	NPC329427
0.7606	Intermediate Similarity	NPC317601
0.7603	Intermediate Similarity	NPC476819
0.7603	Intermediate Similarity	NPC26241
0.7603	Intermediate Similarity	NPC303683
0.7603	Intermediate Similarity	NPC19622
0.7603	Intermediate Similarity	NPC476820
0.7603	Intermediate Similarity	NPC112789
0.7603	Intermediate Similarity	NPC205751
0.7603	Intermediate Similarity	NPC295492
0.7603	Intermediate Similarity	NPC71903
0.7603	Intermediate Similarity	NPC274891
0.7603	Intermediate Similarity	NPC474875
0.76	Intermediate Similarity	NPC229264
0.7597	Intermediate Similarity	NPC21162
0.7597	Intermediate Similarity	NPC63345
0.7597	Intermediate Similarity	NPC477299
0.7591	Intermediate Similarity	NPC477152
0.7589	Intermediate Similarity	NPC172673
0.7589	Intermediate Similarity	NPC237506
0.7589	Intermediate Similarity	NPC32626
0.7589	Intermediate Similarity	NPC329344
0.7589	Intermediate Similarity	NPC217052
0.7589	Intermediate Similarity	NPC245395
0.7584	Intermediate Similarity	NPC295696
0.7578	Intermediate Similarity	NPC206341
0.7578	Intermediate Similarity	NPC281604
0.7576	Intermediate Similarity	NPC51345
0.7574	Intermediate Similarity	NPC251259
0.7574	Intermediate Similarity	NPC472271
0.7571	Intermediate Similarity	NPC2596
0.7571	Intermediate Similarity	NPC219923
0.7569	Intermediate Similarity	NPC173569
0.7569	Intermediate Similarity	NPC477874
0.7568	Intermediate Similarity	NPC303090
0.7568	Intermediate Similarity	NPC43158
0.7568	Intermediate Similarity	NPC37331
0.7568	Intermediate Similarity	NPC472016
0.7568	Intermediate Similarity	NPC277315
0.7568	Intermediate Similarity	NPC319628
0.7568	Intermediate Similarity	NPC284948
0.7568	Intermediate Similarity	NPC258469
0.7568	Intermediate Similarity	NPC220664
0.7568	Intermediate Similarity	NPC192831
0.7566	Intermediate Similarity	NPC103116
0.7559	Intermediate Similarity	NPC188677
0.7559	Intermediate Similarity	NPC95178
0.7559	Intermediate Similarity	NPC69332
0.7559	Intermediate Similarity	NPC29989
0.7554	Intermediate Similarity	NPC84076
0.7554	Intermediate Similarity	NPC473751
0.7554	Intermediate Similarity	NPC303680
0.7554	Intermediate Similarity	NPC90128
0.7551	Intermediate Similarity	NPC9218
0.7551	Intermediate Similarity	NPC27518
0.7551	Intermediate Similarity	NPC310370
0.7551	Intermediate Similarity	NPC183642
0.7551	Intermediate Similarity	NPC304110
0.755	Intermediate Similarity	NPC192568
0.755	Intermediate Similarity	NPC471076
0.754	Intermediate Similarity	NPC120693
0.754	Intermediate Similarity	NPC261573
0.754	Intermediate Similarity	NPC8931
0.7538	Intermediate Similarity	NPC470355
0.7536	Intermediate Similarity	NPC474766
0.7535	Intermediate Similarity	NPC318799
0.7534	Intermediate Similarity	NPC248287

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 NPC173034 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	242
0.1-0.2	819
0.2-0.3	1392
0.3-0.4	2547
0.4-0.5	2204
0.5-0.6	1344
0.6-0.7	557
0.7-0.8	45
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8058	Intermediate Similarity	NPD6355	Discontinued
0.7971	Intermediate Similarity	NPD6798	Discontinued
0.7914	Intermediate Similarity	NPD4062	Phase 3
0.7857	Intermediate Similarity	NPD4060	Phase 1
0.7708	Intermediate Similarity	NPD2935	Discontinued
0.76	Intermediate Similarity	NPD5049	Phase 3
0.7589	Intermediate Similarity	NPD3764	Approved
0.7568	Intermediate Similarity	NPD6190	Approved
0.7564	Intermediate Similarity	NPD7075	Discontinued
0.7535	Intermediate Similarity	NPD6233	Phase 2
0.7518	Intermediate Similarity	NPD7095	Approved
0.7517	Intermediate Similarity	NPD2799	Discontinued
0.75	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7482	Intermediate Similarity	NPD2797	Approved
0.7432	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7385	Intermediate Similarity	NPD2067	Discontinued
0.7372	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7357	Intermediate Similarity	NPD1164	Approved
0.7351	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7343	Intermediate Similarity	NPD3268	Approved
0.7308	Intermediate Similarity	NPD6801	Discontinued
0.7303	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD4626	Approved
0.7286	Intermediate Similarity	NPD1283	Approved
0.7279	Intermediate Similarity	NPD9545	Approved
0.7267	Intermediate Similarity	NPD8166	Discontinued
0.7267	Intermediate Similarity	NPD7003	Approved
0.7267	Intermediate Similarity	NPD4628	Phase 3
0.7259	Intermediate Similarity	NPD9493	Approved
0.7248	Intermediate Similarity	NPD4534	Discontinued
0.7248	Intermediate Similarity	NPD5958	Discontinued
0.7246	Intermediate Similarity	NPD3847	Discontinued
0.7239	Intermediate Similarity	NPD2629	Approved
0.7237	Intermediate Similarity	NPD6799	Approved
0.723	Intermediate Similarity	NPD4477	Approved
0.723	Intermediate Similarity	NPD4476	Approved
0.7226	Intermediate Similarity	NPD7458	Discontinued
0.7222	Intermediate Similarity	NPD2313	Discontinued
0.7222	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD2354	Approved
0.7194	Intermediate Similarity	NPD1535	Discovery
0.7185	Intermediate Similarity	NPD4198	Discontinued
0.7172	Intermediate Similarity	NPD6663	Approved
0.7162	Intermediate Similarity	NPD4308	Phase 3
0.7153	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD1894	Discontinued
0.7143	Intermediate Similarity	NPD1481	Phase 2
0.7133	Intermediate Similarity	NPD5736	Approved
0.7122	Intermediate Similarity	NPD3026	Approved
0.7122	Intermediate Similarity	NPD3023	Approved
0.712	Intermediate Similarity	NPD2859	Approved
0.712	Intermediate Similarity	NPD2860	Approved
0.7114	Intermediate Similarity	NPD2438	Suspended
0.7113	Intermediate Similarity	NPD1203	Approved
0.7105	Intermediate Similarity	NPD3887	Approved
0.7101	Intermediate Similarity	NPD5691	Approved
0.7095	Intermediate Similarity	NPD7097	Phase 1
0.7092	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD3020	Approved
0.7083	Intermediate Similarity	NPD6832	Phase 2
0.7075	Intermediate Similarity	NPD4340	Discontinued
0.7071	Intermediate Similarity	NPD1281	Approved
0.707	Intermediate Similarity	NPD4380	Phase 2
0.707	Intermediate Similarity	NPD6599	Discontinued
0.7067	Intermediate Similarity	NPD2353	Approved
0.7067	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.705	Intermediate Similarity	NPD3019	Approved
0.705	Intermediate Similarity	NPD2932	Approved
0.7047	Intermediate Similarity	NPD7033	Discontinued
0.704	Intermediate Similarity	NPD2934	Approved
0.704	Intermediate Similarity	NPD2933	Approved
0.7039	Intermediate Similarity	NPD3750	Approved
0.7025	Intermediate Similarity	NPD7411	Suspended
0.702	Intermediate Similarity	NPD2424	Discontinued
0.7007	Intermediate Similarity	NPD2979	Phase 3
0.7	Intermediate Similarity	NPD2531	Phase 2
0.7	Intermediate Similarity	NPD5408	Approved
0.7	Intermediate Similarity	NPD5405	Approved
0.7	Intermediate Similarity	NPD5909	Discontinued
0.7	Intermediate Similarity	NPD3817	Phase 2
0.7	Intermediate Similarity	NPD5404	Approved
0.7	Intermediate Similarity	NPD5406	Approved
0.6993	Remote Similarity	NPD3267	Approved
0.6993	Remote Similarity	NPD3266	Approved
0.6987	Remote Similarity	NPD5403	Approved
0.6978	Remote Similarity	NPD1651	Approved
0.6978	Remote Similarity	NPD3025	Approved
0.6978	Remote Similarity	NPD3024	Approved
0.6978	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.697	Remote Similarity	NPD1358	Approved
0.6968	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD5535	Approved
0.6957	Remote Similarity	NPD7768	Phase 2
0.6957	Remote Similarity	NPD3882	Suspended
0.6954	Remote Similarity	NPD7266	Discontinued
0.6954	Remote Similarity	NPD5763	Approved
0.6954	Remote Similarity	NPD5762	Approved
0.6954	Remote Similarity	NPD2346	Discontinued
0.6954	Remote Similarity	NPD2344	Approved
0.6951	Remote Similarity	NPD6232	Discontinued
0.6946	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD2798	Approved
0.6937	Remote Similarity	NPD7819	Suspended
0.6928	Remote Similarity	NPD3400	Discontinued
0.6928	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD4110	Phase 3
0.6928	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD3225	Approved
0.6908	Remote Similarity	NPD2897	Discontinued
0.6901	Remote Similarity	NPD9717	Approved
0.6901	Remote Similarity	NPD1608	Approved
0.6899	Remote Similarity	NPD3455	Phase 2
0.6892	Remote Similarity	NPD1240	Approved
0.6892	Remote Similarity	NPD4307	Phase 2
0.6879	Remote Similarity	NPD4106	Approved
0.6879	Remote Similarity	NPD4136	Approved
0.6879	Remote Similarity	NPD4135	Approved
0.6879	Remote Similarity	NPD3496	Discontinued
0.6875	Remote Similarity	NPD987	Approved
0.6871	Remote Similarity	NPD1296	Phase 2
0.6866	Remote Similarity	NPD3022	Approved
0.6866	Remote Similarity	NPD3021	Approved
0.6859	Remote Similarity	NPD5401	Approved
0.6857	Remote Similarity	NPD4102	Approved
0.6857	Remote Similarity	NPD4105	Approved
0.6852	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD2614	Approved
0.6842	Remote Similarity	NPD6002	Phase 3
0.6842	Remote Similarity	NPD6005	Phase 3
0.6842	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD6004	Phase 3
0.6842	Remote Similarity	NPD6800	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD5536	Phase 2
0.6832	Remote Similarity	NPD8455	Phase 2
0.6832	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6831	Remote Similarity	NPD1201	Approved
0.6831	Remote Similarity	NPD422	Phase 1
0.6826	Remote Similarity	NPD7473	Discontinued
0.6824	Remote Similarity	NPD4248	Discontinued
0.6821	Remote Similarity	NPD1510	Phase 2
0.6821	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD6273	Approved
0.6812	Remote Similarity	NPD256	Approved
0.6812	Remote Similarity	NPD255	Approved
0.6809	Remote Similarity	NPD5306	Approved
0.6809	Remote Similarity	NPD5305	Approved
0.6807	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD1876	Approved
0.68	Remote Similarity	NPD1607	Approved
0.6797	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD3226	Approved
0.6792	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6791	Remote Similarity	NPD9266	Approved
0.6791	Remote Similarity	NPD74	Approved
0.6791	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.679	Remote Similarity	NPD5402	Approved
0.679	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD1241	Discontinued
0.6783	Remote Similarity	NPD3972	Approved
0.6779	Remote Similarity	NPD826	Approved
0.6779	Remote Similarity	NPD825	Approved
0.6776	Remote Similarity	NPD6032	Approved
0.6776	Remote Similarity	NPD1551	Phase 2
0.6774	Remote Similarity	NPD2309	Approved
0.677	Remote Similarity	NPD37	Approved
0.6768	Remote Similarity	NPD6234	Discontinued
0.6767	Remote Similarity	NPD3134	Approved
0.6766	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD5953	Discontinued
0.6763	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD1470	Approved
0.6757	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD2533	Approved
0.6752	Remote Similarity	NPD2532	Approved
0.6752	Remote Similarity	NPD2534	Approved
0.675	Remote Similarity	NPD6502	Phase 2
0.6748	Remote Similarity	NPD4965	Approved
0.6748	Remote Similarity	NPD4967	Phase 2
0.6748	Remote Similarity	NPD4966	Approved
0.6739	Remote Similarity	NPD5951	Approved
0.6733	Remote Similarity	NPD447	Suspended
0.6733	Remote Similarity	NPD230	Phase 1
0.6733	Remote Similarity	NPD5124	Phase 1
0.6733	Remote Similarity	NPD1933	Approved
0.6733	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6732	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6732	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD7440	Discontinued
0.673	Remote Similarity	NPD2370	Clinical (unspecified phase)
0.6725	Remote Similarity	NPD6559	Discontinued
0.6719	Remote Similarity	NPD1809	Phase 2
0.6716	Remote Similarity	NPD9267	Approved
0.6716	Remote Similarity	NPD9264	Approved
0.6716	Remote Similarity	NPD9263	Approved
0.6715	Remote Similarity	NPD7843	Approved
0.6713	Remote Similarity	NPD4807	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