NPASS Compound

Structure

CID188785 OpenBabel06191715572D 26 26 0 0 1 0 0 0 0 0999 V2000 -2.4876 -9.3173 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2262 2.5983 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6324 -3.5497 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8135 -1.8271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4930 -9.4218 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7248 2.9074 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9052 -8.6128 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3120 -7.6993 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7242 -6.8902 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1309 -5.9767 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5431 -5.1677 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3090 0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9499 -4.2541 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 1.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3621 -3.4451 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1810 -1.7226 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.3090 0.9511 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7688 -2.5316 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2601 1.2601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.7634 -2.4271 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5823 -0.7045 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0032 0.5909 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4680 2.2382 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 5 1 0 0 0 0 2 6 1 0 0 0 0 3 16 1 0 0 0 0 5 7 1 0 0 0 0 6 26 1 0 0 0 0 7 8 1 0 0 0 0 8 9 1 0 0 0 0 9 10 1 0 0 0 0 10 11 1 0 0 0 0 11 13 1 0 0 0 0 12 14 1 0 0 0 0 12 15 1 0 0 0 0 13 16 2 0 0 0 0 14 18 1 0 0 0 0 15 22 1 0 0 0 0 16 19 1 0 0 0 0 17 4 1 6 0 0 0 17 19 1 0 0 0 0 17 20 1 0 0 0 0 18 21 1 6 0 0 0 18 22 1 0 0 0 0 19 23 1 1 0 0 0 20 22 1 0 0 0 0 20 24 2 0 0 0 0 21 25 2 0 0 0 0 21 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	367.27
Volume:	401.464
LogP:	4.17
LogD:	4.054
LogS:	-4.442
# Rotatable Bonds:	13
TPSA:	66.84
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.342
Synthetic Accessibility Score:	3.477
Fsp3:	0.81
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.611
MDCK Permeability:	3.1553205189993605e-05
Pgp-inhibitor:	0.957
Pgp-substrate:	0.03
Human Intestinal Absorption (HIA):	0.022
20% Bioavailability (F20%):	0.995
30% Bioavailability (F30%):	0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.841
Plasma Protein Binding (PPB):	93.74352264404297%
Volume Distribution (VD):	0.83
Pgp-substrate:	5.656996250152588%

ADMET: Metabolism

CYP1A2-inhibitor:	0.078
CYP1A2-substrate:	0.56
CYP2C19-inhibitor:	0.615
CYP2C19-substrate:	0.7
CYP2C9-inhibitor:	0.427
CYP2C9-substrate:	0.584
CYP2D6-inhibitor:	0.011
CYP2D6-substrate:	0.158
CYP3A4-inhibitor:	0.716
CYP3A4-substrate:	0.255

ADMET: Excretion

Clearance (CL):	7.853
Half-life (T1/2):	0.139

ADMET: Toxicity

hERG Blockers:	0.024
Human Hepatotoxicity (H-HT):	0.828
Drug-inuced Liver Injury (DILI):	0.478
AMES Toxicity:	0.003
Rat Oral Acute Toxicity:	0.026
Maximum Recommended Daily Dose:	0.648
Skin Sensitization:	0.915
Carcinogencity:	0.028
Eye Corrosion:	0.004
Eye Irritation:	0.014
Respiratory Toxicity:	0.106

Download Data

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

Natural Product: NPC188785

Natural Product ID:	NPC188785
*Common Name:**	Ethyl Tumonoate A
IUPAC Name:	ethyl (2S)-1-[(E,2R,3S)-3-hydroxy-2,4-dimethyldodec-4-enoyl]pyrrolidine-2-carboxylate
Synonyms:	Ethyl Tumonoate A
Standard InCHIKey:	ATSNGULFDLCUIL-BFJJTLHJSA-N
Standard InCHI:	InChI=1S/C21H37NO4/c1-5-7-8-9-10-11-13-16(3)19(23)17(4)20(24)22-15-12-14-18(22)21(25)26-6-2/h13,17-19,23H,5-12,14-15H2,1-4H3/b16-13+/t17-,18+,19-/m1/s1
SMILES:	CCCCCCC/C=C(/[C@H]([C@H](C(=O)N1CCC[C@H]1C(=O)OCC)C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1822612
PubChem CID:	53493313
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0000013] Amino acids, peptides, and analogues [CHEMONTID:0000347] Amino acids and derivatives [CHEMONTID:0000060] Alpha amino acids and derivatives [CHEMONTID:0001189] N-acyl-alpha amino acids and derivatives [CHEMONTID:0002402] N-acyl-alpha amino acids

*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
NPO28005	Panax japonicus	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12350149]
NPO5066	Oscillatoria margaritifera	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[21488639]
NPO5066	Oscillatoria margaritifera	Species	Oscillatoriaceae	Bacteria	n.a.	Isla Canales de Afuera on the Pacific coast of Panama (741.617'N, 8138.379'E)	n.a.	PMID[21488639]
NPO5066	Oscillatoria margaritifera	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[21751786]
NPO5066.1	Oscillatoria margaritifera nac8-54	Subspecies	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[21751786]
NPO5066.2	Oscillatoria margaritifera nac8-55	Subspecies	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[21751786]
NPO28005	Panax japonicus	Species	Araliaceae	Eukaryota	Roots	n.a.	n.a.	PMID[28006911]
NPO28005	Panax japonicus	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28202328]
NPO15028	Lespedeza cuneata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15028	Lespedeza cuneata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1614	Silene baccifera	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27391	Ammopiptanthus mongolicus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15028	Lespedeza cuneata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28005	Panax japonicus	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28005	Panax japonicus	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO20342	Lichtheimia corymbifera	Species	Lichtheimiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28005	Panax japonicus	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29477	Hymenopellis radicata	Species	Physalacriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16336	Magnolia tomentosa	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5066	Oscillatoria margaritifera	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO25587	Pearsonia sessilifolia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16059	Lobelia polyphylla	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27391	Ammopiptanthus mongolicus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15028	Lespedeza cuneata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2278	Serenoa serrulata	Species	Arecaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18009	Cicer flexuosum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12359	Rhodotorula toruloides	Species	Sporidiobolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1614	Silene baccifera	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16825	Scabiosa columbaria	Species	Caprifoliaceae	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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	9800.0	nM	PMID[505358]

☑ 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 NPC188785 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	83
0.1-0.2	584
0.2-0.3	12263
0.3-0.4	17593
0.4-0.5	9881
0.5-0.6	2026
0.6-0.7	235
0.7-0.8	31
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.7727	Intermediate Similarity	NPC476875
0.7677	Intermediate Similarity	NPC322966
0.7627	Intermediate Similarity	NPC309525
0.7603	Intermediate Similarity	NPC120335
0.7523	Intermediate Similarity	NPC271562
0.7407	Intermediate Similarity	NPC476877
0.74	Intermediate Similarity	NPC324506
0.7273	Intermediate Similarity	NPC476876
0.7193	Intermediate Similarity	NPC314550
0.7184	Intermediate Similarity	NPC476019
0.7156	Intermediate Similarity	NPC475149
0.7156	Intermediate Similarity	NPC471097
0.7143	Intermediate Similarity	NPC315188
0.713	Intermediate Similarity	NPC13175
0.713	Intermediate Similarity	NPC475791
0.71	Intermediate Similarity	NPC475975
0.7069	Intermediate Similarity	NPC472536
0.7069	Intermediate Similarity	NPC103391
0.7037	Intermediate Similarity	NPC475758
0.7027	Intermediate Similarity	NPC64168
0.7	Intermediate Similarity	NPC474244
0.6991	Remote Similarity	NPC171734
0.6991	Remote Similarity	NPC474099
0.6937	Remote Similarity	NPC173690
0.6937	Remote Similarity	NPC80439
0.6937	Remote Similarity	NPC279833
0.6937	Remote Similarity	NPC6271
0.6857	Remote Similarity	NPC47230
0.6857	Remote Similarity	NPC17143
0.6833	Remote Similarity	NPC470788
0.6822	Remote Similarity	NPC313265
0.681	Remote Similarity	NPC316984
0.681	Remote Similarity	NPC30911
0.6786	Remote Similarity	NPC265094
0.678	Remote Similarity	NPC272166
0.6759	Remote Similarity	NPC150041
0.675	Remote Similarity	NPC476155
0.675	Remote Similarity	NPC17581
0.675	Remote Similarity	NPC235625
0.6726	Remote Similarity	NPC205176
0.6726	Remote Similarity	NPC469604
0.6724	Remote Similarity	NPC469603
0.6723	Remote Similarity	NPC66007
0.6699	Remote Similarity	NPC264014
0.6698	Remote Similarity	NPC474576
0.6695	Remote Similarity	NPC469597
0.6691	Remote Similarity	NPC314358
0.6667	Remote Similarity	NPC273185
0.6667	Remote Similarity	NPC26597
0.6667	Remote Similarity	NPC120420
0.664	Remote Similarity	NPC474371
0.6639	Remote Similarity	NPC474984
0.6639	Remote Similarity	NPC11379
0.6637	Remote Similarity	NPC474827
0.6637	Remote Similarity	NPC68001
0.6637	Remote Similarity	NPC199831
0.6637	Remote Similarity	NPC474828
0.6636	Remote Similarity	NPC173763
0.6636	Remote Similarity	NPC471098
0.6636	Remote Similarity	NPC62263
0.6636	Remote Similarity	NPC52820
0.6636	Remote Similarity	NPC476344
0.6632	Remote Similarity	NPC97614
0.6618	Remote Similarity	NPC313867
0.6618	Remote Similarity	NPC316008
0.6615	Remote Similarity	NPC99864
0.6612	Remote Similarity	NPC201889
0.6612	Remote Similarity	NPC106791
0.661	Remote Similarity	NPC474995
0.6606	Remote Similarity	NPC469739
0.6604	Remote Similarity	NPC475801
0.6604	Remote Similarity	NPC474593
0.6571	Remote Similarity	NPC314050
0.6571	Remote Similarity	NPC315809
0.6552	Remote Similarity	NPC207820
0.6544	Remote Similarity	NPC314388
0.6544	Remote Similarity	NPC315283
0.6538	Remote Similarity	NPC319913
0.6525	Remote Similarity	NPC181510
0.6525	Remote Similarity	NPC474431
0.6525	Remote Similarity	NPC168758
0.6525	Remote Similarity	NPC58281
0.6525	Remote Similarity	NPC47857
0.6525	Remote Similarity	NPC59249
0.6525	Remote Similarity	NPC474411
0.6522	Remote Similarity	NPC471259
0.6518	Remote Similarity	NPC474985
0.6504	Remote Similarity	NPC470652
0.6479	Remote Similarity	NPC475342
0.6476	Remote Similarity	NPC322672
0.6475	Remote Similarity	NPC174463
0.6471	Remote Similarity	NPC226982
0.6471	Remote Similarity	NPC277341
0.646	Remote Similarity	NPC77703
0.6452	Remote Similarity	NPC23963
0.6446	Remote Similarity	NPC296043
0.6429	Remote Similarity	NPC470654
0.6429	Remote Similarity	NPC220234
0.6429	Remote Similarity	NPC470650
0.6429	Remote Similarity	NPC470653
0.6417	Remote Similarity	NPC193471
0.6417	Remote Similarity	NPC130124
0.6415	Remote Similarity	NPC473525
0.6393	Remote Similarity	NPC329216
0.6389	Remote Similarity	NPC159568
0.6372	Remote Similarity	NPC233932
0.6371	Remote Similarity	NPC230849
0.637	Remote Similarity	NPC476133
0.637	Remote Similarity	NPC92784
0.637	Remote Similarity	NPC178662
0.637	Remote Similarity	NPC98424
0.637	Remote Similarity	NPC470884
0.633	Remote Similarity	NPC472264
0.632	Remote Similarity	NPC160688
0.6306	Remote Similarity	NPC40663
0.6303	Remote Similarity	NPC251122
0.6299	Remote Similarity	NPC36254
0.6299	Remote Similarity	NPC97580
0.6296	Remote Similarity	NPC471265
0.6296	Remote Similarity	NPC471264
0.6293	Remote Similarity	NPC323720
0.629	Remote Similarity	NPC471261
0.6271	Remote Similarity	NPC67009
0.6261	Remote Similarity	NPC471258
0.6261	Remote Similarity	NPC473289
0.6239	Remote Similarity	NPC93179
0.6214	Remote Similarity	NPC477523
0.6212	Remote Similarity	NPC133089
0.621	Remote Similarity	NPC470300
0.621	Remote Similarity	NPC284656
0.6207	Remote Similarity	NPC471260
0.6202	Remote Similarity	NPC247902
0.6202	Remote Similarity	NPC262880
0.6198	Remote Similarity	NPC76660
0.6198	Remote Similarity	NPC276995
0.6187	Remote Similarity	NPC52748
0.6183	Remote Similarity	NPC41162
0.6179	Remote Similarity	NPC30196
0.6168	Remote Similarity	NPC469861
0.6168	Remote Similarity	NPC469860
0.6168	Remote Similarity	NPC130436
0.6162	Remote Similarity	NPC263281
0.6159	Remote Similarity	NPC263493
0.6159	Remote Similarity	NPC269398
0.6154	Remote Similarity	NPC476921
0.6154	Remote Similarity	NPC477524
0.6154	Remote Similarity	NPC471086
0.6154	Remote Similarity	NPC44514
0.6154	Remote Similarity	NPC133420
0.6154	Remote Similarity	NPC470655
0.6154	Remote Similarity	NPC470651
0.6143	Remote Similarity	NPC209509
0.614	Remote Similarity	NPC475440
0.6134	Remote Similarity	NPC476276
0.6132	Remote Similarity	NPC277918
0.6129	Remote Similarity	NPC6531
0.6127	Remote Similarity	NPC471821
0.6127	Remote Similarity	NPC240848
0.6127	Remote Similarity	NPC471820
0.6124	Remote Similarity	NPC471263
0.6121	Remote Similarity	NPC5864
0.6121	Remote Similarity	NPC124554
0.6121	Remote Similarity	NPC301148
0.6117	Remote Similarity	NPC471768
0.6111	Remote Similarity	NPC52533
0.61	Remote Similarity	NPC327272
0.6099	Remote Similarity	NPC262077
0.6095	Remote Similarity	NPC474312
0.6095	Remote Similarity	NPC473810
0.6094	Remote Similarity	NPC50520
0.6087	Remote Similarity	NPC163392
0.6087	Remote Similarity	NPC239762
0.6078	Remote Similarity	NPC473741
0.6078	Remote Similarity	NPC477145
0.6077	Remote Similarity	NPC476951
0.6075	Remote Similarity	NPC69374
0.6075	Remote Similarity	NPC90476
0.6074	Remote Similarity	NPC82129
0.6071	Remote Similarity	NPC476978
0.6068	Remote Similarity	NPC198344
0.6066	Remote Similarity	NPC261750
0.6066	Remote Similarity	NPC1111
0.6066	Remote Similarity	NPC60432
0.6066	Remote Similarity	NPC469466
0.6066	Remote Similarity	NPC478024
0.6061	Remote Similarity	NPC477988
0.6056	Remote Similarity	NPC145113
0.6053	Remote Similarity	NPC167380
0.6047	Remote Similarity	NPC314512
0.6047	Remote Similarity	NPC313342
0.6047	Remote Similarity	NPC313333
0.6047	Remote Similarity	NPC314451
0.6042	Remote Similarity	NPC7817
0.6042	Remote Similarity	NPC475168
0.6033	Remote Similarity	NPC63511
0.6028	Remote Similarity	NPC5620
0.6028	Remote Similarity	NPC315266
0.602	Remote Similarity	NPC45060
0.602	Remote Similarity	NPC280065
0.6019	Remote Similarity	NPC258824

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 NPC188785 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	85
0.1-0.2	491
0.2-0.3	3228
0.3-0.4	3908
0.4-0.5	1163
0.5-0.6	254
0.6-0.7	21
0.7-0.8	0
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
0.6983	Remote Similarity	NPD1376	Discontinued
0.6891	Remote Similarity	NPD1773	Discontinued
0.6833	Remote Similarity	NPD3159	Discontinued
0.681	Remote Similarity	NPD2204	Approved
0.678	Remote Similarity	NPD1000	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD9512	Approved
0.6692	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.664	Remote Similarity	NPD3677	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD2645	Approved
0.6615	Remote Similarity	NPD8415	Approved
0.6602	Remote Similarity	NPD9511	Approved
0.6486	Remote Similarity	NPD3715	Approved
0.6486	Remote Similarity	NPD3713	Approved
0.6486	Remote Similarity	NPD3714	Approved
0.6379	Remote Similarity	NPD777	Phase 3
0.6324	Remote Similarity	NPD8384	Approved
0.627	Remote Similarity	NPD1748	Approved
0.627	Remote Similarity	NPD1806	Approved
0.626	Remote Similarity	NPD4177	Approved
0.626	Remote Similarity	NPD4175	Approved
0.625	Remote Similarity	NPD2584	Suspended
0.625	Remote Similarity	NPD8273	Phase 1
0.6176	Remote Similarity	NPD6073	Approved
0.6176	Remote Similarity	NPD5725	Approved
0.6126	Remote Similarity	NPD5781	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD805	Approved
0.6111	Remote Similarity	NPD806	Approved
0.6096	Remote Similarity	NPD8414	Discontinued
0.6058	Remote Similarity	NPD8172	Phase 2
0.6058	Remote Similarity	NPD8173	Phase 2
0.6047	Remote Similarity	NPD8341	Approved
0.6047	Remote Similarity	NPD8340	Approved
0.6047	Remote Similarity	NPD8342	Approved
0.6047	Remote Similarity	NPD8299	Approved
0.6045	Remote Similarity	NPD4794	Discontinued
0.604	Remote Similarity	NPD1452	Discontinued
0.6032	Remote Similarity	NPD2495	Phase 3
0.602	Remote Similarity	NPD2220	Clinical (unspecified phase)
0.6	Remote Similarity	NPD961	Discontinued
0.6	Remote Similarity	NPD2148	Clinical (unspecified phase)
0.5985	Remote Similarity	NPD5767	Discontinued
0.5966	Remote Similarity	NPD7333	Discontinued
0.5965	Remote Similarity	NPD4228	Discovery
0.5965	Remote Similarity	NPD5349	Clinical (unspecified phase)
0.5956	Remote Similarity	NPD7634	Clinical (unspecified phase)
0.595	Remote Similarity	NPD6413	Approved
0.5946	Remote Similarity	NPD2682	Approved
0.5929	Remote Similarity	NPD7512	Approved
0.5929	Remote Similarity	NPD7511	Approved
0.5926	Remote Similarity	NPD3723	Clinical (unspecified phase)
0.5878	Remote Similarity	NPD3072	Approved
0.5878	Remote Similarity	NPD3071	Approved
0.5878	Remote Similarity	NPD8451	Approved
0.5878	Remote Similarity	NPD3073	Approved
0.5873	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.5865	Remote Similarity	NPD3732	Approved
0.5859	Remote Similarity	NPD2695	Approved
0.5859	Remote Similarity	NPD2696	Approved
0.5859	Remote Similarity	NPD2697	Approved
0.5859	Remote Similarity	NPD9649	Approved
0.5859	Remote Similarity	NPD2694	Approved
0.5852	Remote Similarity	NPD2613	Approved
0.5839	Remote Similarity	NPD3089	Approved
0.5839	Remote Similarity	NPD3616	Approved
0.5839	Remote Similarity	NPD4746	Phase 3
0.5839	Remote Similarity	NPD2574	Discontinued
0.5839	Remote Similarity	NPD3090	Approved
0.5839	Remote Similarity	NPD5747	Discontinued
0.5839	Remote Similarity	NPD3614	Approved
0.5839	Remote Similarity	NPD2573	Approved
0.5839	Remote Similarity	NPD3087	Approved
0.5839	Remote Similarity	NPD3615	Approved
0.5839	Remote Similarity	NPD2570	Approved
0.5839	Remote Similarity	NPD2571	Approved
0.5839	Remote Similarity	NPD4745	Approved
0.5839	Remote Similarity	NPD2572	Clinical (unspecified phase)
0.5839	Remote Similarity	NPD3088	Approved
0.5839	Remote Similarity	NPD2566	Approved
0.5833	Remote Similarity	NPD8448	Approved
0.5827	Remote Similarity	NPD7756	Clinical (unspecified phase)
0.5818	Remote Similarity	NPD3177	Phase 3
0.5804	Remote Similarity	NPD4261	Phase 1
0.5804	Remote Similarity	NPD4780	Clinical (unspecified phase)
0.5802	Remote Similarity	NPD2610	Approved
0.5802	Remote Similarity	NPD3131	Approved
0.5802	Remote Similarity	NPD4215	Approved
0.5802	Remote Similarity	NPD2609	Approved
0.5802	Remote Similarity	NPD2612	Approved
0.5802	Remote Similarity	NPD4761	Approved
0.5802	Remote Similarity	NPD2611	Approved
0.5802	Remote Similarity	NPD3132	Approved
0.5802	Remote Similarity	NPD4216	Approved
0.5802	Remote Similarity	NPD4217	Approved
0.5802	Remote Similarity	NPD2608	Approved
0.5802	Remote Similarity	NPD4218	Approved
0.5802	Remote Similarity	NPD4762	Approved
0.5797	Remote Similarity	NPD4153	Approved
0.5794	Remote Similarity	NPD882	Phase 2
0.5794	Remote Similarity	NPD883	Phase 2
0.5781	Remote Similarity	NPD2132	Phase 3
0.5778	Remote Similarity	NPD5759	Approved
0.5772	Remote Similarity	NPD6420	Discontinued
0.5772	Remote Similarity	NPD6421	Discontinued
0.5758	Remote Similarity	NPD7840	Approved
0.5755	Remote Similarity	NPD7113	Clinical (unspecified phase)
0.5755	Remote Similarity	NPD4684	Phase 3
0.5755	Remote Similarity	NPD4686	Approved
0.5755	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.5755	Remote Similarity	NPD4685	Phase 3
0.5755	Remote Similarity	NPD4252	Approved
0.5746	Remote Similarity	NPD2585	Clinical (unspecified phase)
0.5741	Remote Similarity	NPD7154	Phase 3
0.5735	Remote Similarity	NPD5263	Approved
0.5735	Remote Similarity	NPD4676	Approved
0.5725	Remote Similarity	NPD7642	Approved
0.5714	Remote Similarity	NPD7510	Approved
0.5704	Remote Similarity	NPD8390	Approved
0.5704	Remote Similarity	NPD8392	Approved
0.5704	Remote Similarity	NPD8391	Approved
0.5703	Remote Similarity	NPD7641	Discontinued
0.5702	Remote Similarity	NPD1385	Discontinued
0.5694	Remote Similarity	NPD5264	Approved
0.5694	Remote Similarity	NPD5265	Approved
0.5692	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.5667	Remote Similarity	NPD6122	Discontinued
0.5667	Remote Similarity	NPD2258	Approved
0.5667	Remote Similarity	NPD2259	Approved
0.5655	Remote Similarity	NPD2575	Approved
0.5652	Remote Similarity	NPD4621	Approved
0.5652	Remote Similarity	NPD4619	Approved
0.5648	Remote Similarity	NPD4269	Approved
0.5648	Remote Similarity	NPD4270	Approved
0.5636	Remote Similarity	NPD7759	Phase 2
0.5636	Remote Similarity	NPD7760	Phase 2
0.563	Remote Similarity	NPD2626	Approved
0.563	Remote Similarity	NPD2625	Approved
0.563	Remote Similarity	NPD2159	Approved
0.563	Remote Similarity	NPD2160	Approved
0.563	Remote Similarity	NPD2628	Approved
0.563	Remote Similarity	NPD2627	Approved
0.5607	Remote Similarity	NPD7763	Phase 2
0.5607	Remote Similarity	NPD7762	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