NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	142.1
Volume:	153.312
LogP:	2.369
LogD:	1.787
LogS:	-2.205
# Rotatable Bonds:	3
TPSA:	26.3
# H-Bond Aceptor:	2
# H-Bond Donor:	0
# Rings:	1
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.562
Synthetic Accessibility Score:	2.822
Fsp3:	0.875
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.406
MDCK Permeability:	5.6505836255382746e-05
Pgp-inhibitor:	0.783
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.64

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.976
Plasma Protein Binding (PPB):	76.57938385009766%
Volume Distribution (VD):	0.633
Pgp-substrate:	29.599241256713867%

ADMET: Metabolism

CYP1A2-inhibitor:	0.19
CYP1A2-substrate:	0.174
CYP2C19-inhibitor:	0.048
CYP2C19-substrate:	0.457
CYP2C9-inhibitor:	0.018
CYP2C9-substrate:	0.855
CYP2D6-inhibitor:	0.022
CYP2D6-substrate:	0.451
CYP3A4-inhibitor:	0.08
CYP3A4-substrate:	0.24

ADMET: Excretion

Clearance (CL):	9.815
Half-life (T1/2):	0.77

ADMET: Toxicity

hERG Blockers:	0.013
Human Hepatotoxicity (H-HT):	0.14
Drug-inuced Liver Injury (DILI):	0.142
AMES Toxicity:	0.036
Rat Oral Acute Toxicity:	0.015
Maximum Recommended Daily Dose:	0.779
Skin Sensitization:	0.881
Carcinogencity:	0.816
Eye Corrosion:	0.952
Eye Irritation:	0.916
Respiratory Toxicity:	0.084

Download Data

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

Natural Product: NPC273545

Natural Product ID:	NPC273545
*Common Name:**	5-Butyloxolan-2-One
IUPAC Name:	5-butyloxolan-2-one
Synonyms:
Standard InCHIKey:	IPBFYZQJXZJBFQ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C8H14O2/c1-2-3-4-7-5-6-8(9)10-7/h7H,2-6H2,1H3
SMILES:	CCCCC1CCC(=O)O1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3559967
PubChem CID:	7704
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000050] Lactones [CHEMONTID:0001245] Gamma butyrolactones

*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
NPO4795	Prunus armeniaca	Species	Rosaceae	Eukaryota	n.a.	kernel	n.a.	PMID[10670815]
NPO7156	Vaccinium myrtillus	Species	Ericaceae	Eukaryota	n.a.	fruit	n.a.	PMID[16417304]
NPO4795	Prunus armeniaca	Species	Rosaceae	Eukaryota	Fruits	Malatya Fruit Research Institute	between the first and third weeks of 2005-Jul.	PMID[18038980]
NPO1493	Hericium erinaceus	Species	Hericiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25565282]
NPO29401	Bupleurum chinense	Species	Apiaceae	Eukaryota	roots	n.a.	n.a.	PMID[26259802]
NPO1493	Hericium erinaceus	Species	Hericiaceae	Eukaryota	Mycelia	n.a.	n.a.	PMID[26807743]
NPO1493	Hericium erinaceus	Species	Hericiaceae	Eukaryota	Fruiting Bodies	n.a.	n.a.	PMID[33246107]
NPO19649	Akebia quinata	Species	Lardizabalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]
NPO29401	Bupleurum chinense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]
NPO15670	Ananas comosus	Species	Bromeliaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO4795	Prunus armeniaca	Species	Rosaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO4795	Prunus armeniaca	Species	Rosaceae	Eukaryota	Fruits	n.a.		Database[FooDB]
NPO15670	Ananas comosus	Species	Bromeliaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO7156	Vaccinium myrtillus	Species	Ericaceae	Eukaryota	Fruits	n.a.		Database[FooDB]
NPO7156	Vaccinium myrtillus	Species	Ericaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO15670	Ananas comosus	Species	Bromeliaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO4795	Prunus armeniaca	Species	Rosaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO7156	Vaccinium myrtillus	Species	Ericaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO7156	Vaccinium myrtillus	Species	Ericaceae	Eukaryota	Fruit Juice	n.a.	n.a.	Database[FooDB]
NPO4795	Prunus armeniaca	Species	Rosaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO7156	Vaccinium myrtillus	Species	Ericaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO15670	Ananas comosus	Species	Bromeliaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO7156	Vaccinium myrtillus	Species	Ericaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO4795	Prunus armeniaca	Species	Rosaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO7156	Vaccinium myrtillus	Species	Ericaceae	Eukaryota	Shoot	n.a.	n.a.	Database[FooDB]
NPO4795	Prunus armeniaca	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29401	Bupleurum chinense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11170	Akebia trifoliata	Species	Lardizabalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1493	Hericium erinaceus	Species	Hericiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19649	Akebia quinata	Species	Lardizabalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15670	Ananas comosus	Species	Bromeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11170	Akebia trifoliata	Species	Lardizabalaceae	Eukaryota	n.a.	pericarp	n.a.	PMID[p25172756]
NPO15670	Ananas comosus	Species	Bromeliaceae	Eukaryota	Fruits	n.a.		Database[Phenol-Explorer]
NPO15670	Ananas comosus	Species	Bromeliaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO4795	Prunus armeniaca	Species	Rosaceae	Eukaryota	Fruits	n.a.		Database[Phenol-Explorer]
NPO7156	Vaccinium myrtillus	Species	Ericaceae	Eukaryota	Fruits	n.a.		Database[Phenol-Explorer]
NPO19649	Akebia quinata	Species	Lardizabalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1493	Hericium erinaceus	Species	Hericiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11170	Akebia trifoliata	Species	Lardizabalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15670	Ananas comosus	Species	Bromeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29401	Bupleurum chinense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4795	Prunus armeniaca	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4795	Prunus armeniaca	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29401	Bupleurum chinense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO19649	Akebia quinata	Species	Lardizabalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11170	Akebia trifoliata	Species	Lardizabalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15670	Ananas comosus	Species	Bromeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO1493	Hericium erinaceus	Species	Hericiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4795	Prunus armeniaca	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO19649	Akebia quinata	Species	Lardizabalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO11170	Akebia trifoliata	Species	Lardizabalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO29401	Bupleurum chinense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO11170	Akebia trifoliata	Species	Lardizabalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7156	Vaccinium myrtillus	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1493	Hericium erinaceus	Species	Hericiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15670	Ananas comosus	Species	Bromeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29401	Bupleurum chinense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19649	Akebia quinata	Species	Lardizabalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4795	Prunus armeniaca	Species	Rosaceae	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
NPO15670	NPC273545	Raw	Fruit	0.03	0.03	0.03	mg/100g	Database [DUKE]
NPO7156	NPC273545	Raw	Fruit Juice	0.0045	0.0045	0.0045	mg/100g	Database [DUKE]

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
Potency	1

Activity Type	# Activity
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		Potency	n.a.	76958.8	nM	PubChem BioAssay data set

☑ 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 NPC273545 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	680
0.1-0.2	10400
0.2-0.3	16684
0.3-0.4	9704
0.4-0.5	4142
0.5-0.6	891
0.6-0.7	130
0.7-0.8	44
0.8-0.85	13
0.85-0.9	3
0.9-0.95	0
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9762	High Similarity	NPC145045
0.9762	High Similarity	NPC105329
0.9762	High Similarity	NPC52700
0.9762	High Similarity	NPC63182
0.9512	High Similarity	NPC176500
0.878	High Similarity	NPC94368
0.8636	High Similarity	NPC47363
0.8636	High Similarity	NPC287231
0.8571	High Similarity	NPC250028
0.8571	High Similarity	NPC149299
0.8571	High Similarity	NPC256163
0.8571	High Similarity	NPC40597
0.8372	Intermediate Similarity	NPC53541
0.8333	Intermediate Similarity	NPC223249
0.8333	Intermediate Similarity	NPC80234
0.8261	Intermediate Similarity	NPC326957
0.8182	Intermediate Similarity	NPC203531
0.8182	Intermediate Similarity	NPC236579
0.814	Intermediate Similarity	NPC165533
0.8125	Intermediate Similarity	NPC305182
0.8095	Intermediate Similarity	NPC201622
0.8095	Intermediate Similarity	NPC54980
0.8095	Intermediate Similarity	NPC22903
0.8095	Intermediate Similarity	NPC305660
0.8049	Intermediate Similarity	NPC321699
0.8043	Intermediate Similarity	NPC282440
0.7907	Intermediate Similarity	NPC31551
0.7907	Intermediate Similarity	NPC219536
0.7805	Intermediate Similarity	NPC156630
0.7755	Intermediate Similarity	NPC55678
0.7727	Intermediate Similarity	NPC28598
0.7727	Intermediate Similarity	NPC161097
0.7727	Intermediate Similarity	NPC12156
0.7708	Intermediate Similarity	NPC106872
0.7619	Intermediate Similarity	NPC80641
0.7619	Intermediate Similarity	NPC80396
0.7619	Intermediate Similarity	NPC154642
0.7609	Intermediate Similarity	NPC317128
0.76	Intermediate Similarity	NPC314084
0.76	Intermediate Similarity	NPC287811
0.75	Intermediate Similarity	NPC328497
0.75	Intermediate Similarity	NPC324004
0.7381	Intermediate Similarity	NPC301398
0.7381	Intermediate Similarity	NPC86545
0.7381	Intermediate Similarity	NPC223374
0.7381	Intermediate Similarity	NPC196442
0.7347	Intermediate Similarity	NPC131770
0.7347	Intermediate Similarity	NPC200618
0.7292	Intermediate Similarity	NPC30195
0.7292	Intermediate Similarity	NPC12438
0.72	Intermediate Similarity	NPC26253
0.72	Intermediate Similarity	NPC304162
0.717	Intermediate Similarity	NPC469937
0.717	Intermediate Similarity	NPC53463
0.717	Intermediate Similarity	NPC23155
0.717	Intermediate Similarity	NPC320588
0.7143	Intermediate Similarity	NPC57499
0.7143	Intermediate Similarity	NPC154396
0.7143	Intermediate Similarity	NPC286498
0.7111	Intermediate Similarity	NPC279026
0.7111	Intermediate Similarity	NPC261080
0.7111	Intermediate Similarity	NPC14227
0.7111	Intermediate Similarity	NPC113928
0.7111	Intermediate Similarity	NPC154186
0.7111	Intermediate Similarity	NPC301585
0.7111	Intermediate Similarity	NPC81263
0.7111	Intermediate Similarity	NPC201844
0.7111	Intermediate Similarity	NPC301696
0.7059	Intermediate Similarity	NPC90904
0.7045	Intermediate Similarity	NPC128996
0.6977	Remote Similarity	NPC289344
0.6905	Remote Similarity	NPC286695
0.6905	Remote Similarity	NPC322892
0.6889	Remote Similarity	NPC268826
0.6875	Remote Similarity	NPC74845
0.6863	Remote Similarity	NPC250919
0.6842	Remote Similarity	NPC17935
0.6833	Remote Similarity	NPC469926
0.6833	Remote Similarity	NPC157518
0.6818	Remote Similarity	NPC155263
0.6809	Remote Similarity	NPC307783
0.6809	Remote Similarity	NPC171736
0.6809	Remote Similarity	NPC149184
0.6809	Remote Similarity	NPC209970
0.6809	Remote Similarity	NPC216630
0.6809	Remote Similarity	NPC196924
0.68	Remote Similarity	NPC249754
0.6792	Remote Similarity	NPC310746
0.6739	Remote Similarity	NPC294085
0.6739	Remote Similarity	NPC214610
0.6739	Remote Similarity	NPC118968
0.6739	Remote Similarity	NPC183424
0.6735	Remote Similarity	NPC469781
0.6667	Remote Similarity	NPC12904
0.6667	Remote Similarity	NPC67462
0.6667	Remote Similarity	NPC14608
0.6667	Remote Similarity	NPC40965
0.6667	Remote Similarity	NPC314103
0.6667	Remote Similarity	NPC289686
0.6667	Remote Similarity	NPC216130
0.6613	Remote Similarity	NPC469925
0.661	Remote Similarity	NPC306750
0.6604	Remote Similarity	NPC100096
0.66	Remote Similarity	NPC308301
0.66	Remote Similarity	NPC166287
0.6591	Remote Similarity	NPC155872
0.6557	Remote Similarity	NPC295256
0.6552	Remote Similarity	NPC470363
0.6545	Remote Similarity	NPC319589
0.6531	Remote Similarity	NPC255837
0.6531	Remote Similarity	NPC76051
0.6531	Remote Similarity	NPC19305
0.6508	Remote Similarity	NPC82315
0.6508	Remote Similarity	NPC119838
0.6452	Remote Similarity	NPC315525
0.6452	Remote Similarity	NPC135043
0.6444	Remote Similarity	NPC134782
0.6441	Remote Similarity	NPC478126
0.6429	Remote Similarity	NPC223677
0.6429	Remote Similarity	NPC10316
0.6429	Remote Similarity	NPC28779
0.6429	Remote Similarity	NPC200845
0.6429	Remote Similarity	NPC128061
0.6406	Remote Similarity	NPC296522
0.6406	Remote Similarity	NPC199557
0.6406	Remote Similarity	NPC5714
0.6406	Remote Similarity	NPC144511
0.64	Remote Similarity	NPC8219
0.64	Remote Similarity	NPC55023
0.6364	Remote Similarity	NPC71761
0.6364	Remote Similarity	NPC473784
0.6346	Remote Similarity	NPC13105
0.6341	Remote Similarity	NPC234005
0.6308	Remote Similarity	NPC472955
0.6275	Remote Similarity	NPC314679
0.6275	Remote Similarity	NPC172042
0.6271	Remote Similarity	NPC472019
0.6271	Remote Similarity	NPC472020
0.6271	Remote Similarity	NPC226602
0.623	Remote Similarity	NPC54925
0.6222	Remote Similarity	NPC317203
0.6212	Remote Similarity	NPC470243
0.6182	Remote Similarity	NPC161366
0.617	Remote Similarity	NPC316546
0.6167	Remote Similarity	NPC229252
0.6167	Remote Similarity	NPC143857
0.6167	Remote Similarity	NPC472021
0.6154	Remote Similarity	NPC21844
0.6154	Remote Similarity	NPC28526
0.6136	Remote Similarity	NPC175342
0.6136	Remote Similarity	NPC99700
0.6136	Remote Similarity	NPC147054
0.6136	Remote Similarity	NPC108238
0.6129	Remote Similarity	NPC68343
0.6129	Remote Similarity	NPC328089
0.6122	Remote Similarity	NPC103286
0.6122	Remote Similarity	NPC163746
0.6119	Remote Similarity	NPC474100
0.6119	Remote Similarity	NPC474755
0.6119	Remote Similarity	NPC475232
0.6119	Remote Similarity	NPC109510
0.6119	Remote Similarity	NPC473775
0.6119	Remote Similarity	NPC473699
0.6119	Remote Similarity	NPC51249
0.6119	Remote Similarity	NPC472956
0.6119	Remote Similarity	NPC475260
0.6098	Remote Similarity	NPC248233
0.6098	Remote Similarity	NPC143211
0.6087	Remote Similarity	NPC301919
0.6071	Remote Similarity	NPC309606
0.6071	Remote Similarity	NPC39633
0.6071	Remote Similarity	NPC139545
0.6066	Remote Similarity	NPC201939
0.6066	Remote Similarity	NPC469922
0.6047	Remote Similarity	NPC168982
0.6038	Remote Similarity	NPC68577
0.6038	Remote Similarity	NPC477878
0.6038	Remote Similarity	NPC324793
0.6032	Remote Similarity	NPC306805
0.6032	Remote Similarity	NPC215987
0.6032	Remote Similarity	NPC322319
0.6032	Remote Similarity	NPC326651
0.6032	Remote Similarity	NPC325117
0.6029	Remote Similarity	NPC55508
0.6029	Remote Similarity	NPC469643
0.6029	Remote Similarity	NPC472966
0.6029	Remote Similarity	NPC215030
0.6029	Remote Similarity	NPC469641
0.6	Remote Similarity	NPC274261
0.6	Remote Similarity	NPC475821
0.6	Remote Similarity	NPC291724
0.6	Remote Similarity	NPC71317
0.6	Remote Similarity	NPC218477
0.6	Remote Similarity	NPC301528
0.6	Remote Similarity	NPC129972
0.597	Remote Similarity	NPC477641
0.597	Remote Similarity	NPC184550
0.597	Remote Similarity	NPC185419
0.597	Remote Similarity	NPC477643
0.597	Remote Similarity	NPC320865

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 NPC273545 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	1055
0.1-0.2	5120
0.2-0.3	1911
0.3-0.4	739
0.4-0.5	250
0.5-0.6	56
0.6-0.7	16
0.7-0.8	2
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8636	High Similarity	NPD2699	Approved
0.7708	Intermediate Similarity	NPD6125	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD3206	Approved
0.717	Intermediate Similarity	NPD3730	Approved
0.717	Intermediate Similarity	NPD3728	Approved
0.7111	Intermediate Similarity	NPD633	Phase 3
0.7111	Intermediate Similarity	NPD9448	Phase 2
0.6809	Remote Similarity	NPD2270	Approved
0.6739	Remote Similarity	NPD9655	Approved
0.6667	Remote Similarity	NPD387	Clinical (unspecified phase)
0.66	Remote Similarity	NPD9430	Approved
0.66	Remote Similarity	NPD9431	Approved
0.6557	Remote Similarity	NPD9496	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.6508	Remote Similarity	NPD229	Approved
0.64	Remote Similarity	NPD3199	Clinical (unspecified phase)
0.6304	Remote Similarity	NPD9449	Clinical (unspecified phase)
0.6275	Remote Similarity	NPD634	Phase 3
0.6271	Remote Similarity	NPD3198	Approved
0.6038	Remote Similarity	NPD2266	Phase 2
0.6	Remote Similarity	NPD900	Approved
0.597	Remote Similarity	NPD2256	Clinical (unspecified phase)
0.5965	Remote Similarity	NPD615	Clinical (unspecified phase)
0.587	Remote Similarity	NPD9447	Approved
0.5854	Remote Similarity	NPD8989	Approved
0.5814	Remote Similarity	NPD62	Approved
0.5789	Remote Similarity	NPD631	Approved
0.5789	Remote Similarity	NPD630	Approved
0.5763	Remote Similarity	NPD73	Approved
0.5758	Remote Similarity	NPD8278	Approved
0.5745	Remote Similarity	NPD370	Phase 3
0.5741	Remote Similarity	NPD622	Approved
0.5735	Remote Similarity	NPD5777	Approved
0.5714	Remote Similarity	NPD29	Approved
0.5714	Remote Similarity	NPD28	Approved
0.5672	Remote Similarity	NPD8277	Approved
0.5652	Remote Similarity	NPD8857	Approved
0.5625	Remote Similarity	NPD3197	Phase 1
0.5625	Remote Similarity	NPD7909	Approved
0.5614	Remote Similarity	NPD3186	Phase 1

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