NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	178.1
Volume:	197.29
LogP:	3.426
LogD:	3.767
LogS:	-3.617
# Rotatable Bonds:	4
TPSA:	26.3
# H-Bond Aceptor:	2
# H-Bond Donor:	0
# Rings:	1
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.665
Synthetic Accessibility Score:	1.429
Fsp3:	0.364
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.244
MDCK Permeability:	3.542708873283118e-05
Pgp-inhibitor:	0.005
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.912

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.189
Plasma Protein Binding (PPB):	94.51049041748047%
Volume Distribution (VD):	1.722
Pgp-substrate:	5.279306411743164%

ADMET: Metabolism

CYP1A2-inhibitor:	0.921
CYP1A2-substrate:	0.371
CYP2C19-inhibitor:	0.792
CYP2C19-substrate:	0.204
CYP2C9-inhibitor:	0.638
CYP2C9-substrate:	0.476
CYP2D6-inhibitor:	0.01
CYP2D6-substrate:	0.084
CYP3A4-inhibitor:	0.019
CYP3A4-substrate:	0.211

ADMET: Excretion

Clearance (CL):	11.226
Half-life (T1/2):	0.845

ADMET: Toxicity

hERG Blockers:	0.038
Human Hepatotoxicity (H-HT):	0.015
Drug-inuced Liver Injury (DILI):	0.511
AMES Toxicity:	0.007
Rat Oral Acute Toxicity:	0.019
Maximum Recommended Daily Dose:	0.008
Skin Sensitization:	0.579
Carcinogencity:	0.119
Eye Corrosion:	0.341
Eye Irritation:	0.99
Respiratory Toxicity:	0.169

Download Data

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

Natural Product: NPC225060

Natural Product ID:	NPC225060
*Common Name:**	Benzoic Acid 2-Methylpropyl Ester
IUPAC Name:	2-methylpropyl benzoate
Synonyms:
Standard InCHIKey:	KYZHGEFMXZOSJN-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C11H14O2/c1-9(2)8-13-11(12)10-6-4-3-5-7-10/h3-7,9H,8H2,1-2H3
SMILES:	CC(COC(=O)c1ccccc1)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2260714
PubChem CID:	61048
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000176] Benzoic acids and derivatives [CHEMONTID:0001350] Benzoic 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
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	Nigeria(latitude 80°N and longitude 4°E)	2005; 2006	DOI[10.1002/ejlt.201000080]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1007/s11306-010-0259-y]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1007/s11306-014-0638-x]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1007/s11746-997-0093-1]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.phytol.2008.07.007]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	Seeds	Plovdiv, Plovdiv region in South Bulgaria		DOI[10.1051/CTV/20163101031]
NPO4391	Hypericum perforatum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1078/0176-1617-00195]
NPO4391	Hypericum perforatum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10757735]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11170689]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	fruit	n.a.	PMID[11312782]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	leaf	n.a.	PMID[11312782]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11408943]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	fruit	n.a.	PMID[12105962]
NPO4391	Hypericum perforatum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14735439]
NPO4391	Hypericum perforatum	Species	Hypericaceae	Eukaryota	n.a.	callus	n.a.	PMID[15715262]
NPO4391	Hypericum perforatum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18220354]
NPO18176	Ephedra sinica	Species	Ephedraceae	Eukaryota	n.a.	root	n.a.	PMID[18975262]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	Esuela Tecnica Superior de Ingenieros Agrónomos de Albacete	2007	PMID[19256538]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20826702]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22537213]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23759170]
NPO18176	Ephedra sinica	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24333010]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	Stalks	n.a.	n.a.	PMID[24521157]
NPO4391	Hypericum perforatum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28445039]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	Seeds	Benedictine Pannonhalma Archabbey, Hungary		PMID[29803478]
NPO4391	Hypericum perforatum	Species	Hypericaceae	Eukaryota	Roots	n.a.	n.a.	PMID[30024167]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31433178]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	Leaf Essent. Oil	n.a.	n.a.	Database[FooDB]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	Stem	n.a.	n.a.	Database[FooDB]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	Fruits	n.a.		Database[FooDB]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO4391	Hypericum perforatum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18176	Ephedra sinica	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[MetaboLights]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4391	Hypericum perforatum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18176	Ephedra sinica	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18176	Ephedra sinica	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4391	Hypericum perforatum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18176	Ephedra sinica	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO4391	Hypericum perforatum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO18176	Ephedra sinica	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4391	Hypericum perforatum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

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

Biological Activity

Activity Type	# Activity
Others	1
Potency	10

Activity Type	# Activity
Individual Protein	1
Organism	1
Others	9

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT152	Individual Protein	Nuclear factor erythroid 2-related factor 2	Homo sapiens	Potency	n.a.	61130.6	nM	PubChem BioAssay data set
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	pLD50	=	8.63	n.a.	PMID[468404]
NPT2	Others	Unspecified		Potency	n.a.	3.1	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	61130.6	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	21872.4	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	54482.7	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	54941	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	61644.8	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	48557.7	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	68589.6	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 NPC225060 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	225
0.1-0.2	1513
0.2-0.3	3888
0.3-0.4	9942
0.4-0.5	11078
0.5-0.6	11416
0.6-0.7	4003
0.7-0.8	517
0.8-0.85	53
0.85-0.9	36
0.9-0.95	15
0.95-1	11

Similarity Score	Similarity Level	Natural Product ID
0.9891	High Similarity	NPC146351
0.989	High Similarity	NPC249912
0.989	High Similarity	NPC92754
0.989	High Similarity	NPC276775
0.9783	High Similarity	NPC35448
0.9783	High Similarity	NPC78701
0.967	High Similarity	NPC130398
0.9574	High Similarity	NPC70624
0.9468	High Similarity	NPC118343
0.9375	High Similarity	NPC301943
0.9375	High Similarity	NPC474365
0.9368	High Similarity	NPC42211
0.9271	High Similarity	NPC188895
0.9263	High Similarity	NPC203925
0.9263	High Similarity	NPC325497
0.9121	High Similarity	NPC173443
0.9091	High Similarity	NPC119271
0.901	High Similarity	NPC196246
0.901	High Similarity	NPC214067
0.9	High Similarity	NPC56493
0.899	High Similarity	NPC269457
0.898	High Similarity	NPC89886
0.8922	High Similarity	NPC305912
0.8922	High Similarity	NPC1082
0.8913	High Similarity	NPC220893
0.8911	High Similarity	NPC265407
0.8911	High Similarity	NPC10251
0.8911	High Similarity	NPC83628
0.8911	High Similarity	NPC17417
0.8911	High Similarity	NPC474364
0.8911	High Similarity	NPC469636
0.8901	High Similarity	NPC89377
0.8889	High Similarity	NPC31786
0.8835	High Similarity	NPC82899
0.8835	High Similarity	NPC270699
0.8824	High Similarity	NPC174099
0.8824	High Similarity	NPC251854
0.8824	High Similarity	NPC93084
0.88	High Similarity	NPC209632
0.8791	High Similarity	NPC318107
0.8788	High Similarity	NPC60679
0.875	High Similarity	NPC128368
0.8738	High Similarity	NPC260818
0.8738	High Similarity	NPC474157
0.8738	High Similarity	NPC476003
0.8738	High Similarity	NPC210089
0.8713	High Similarity	NPC30594
0.8713	High Similarity	NPC37622
0.87	High Similarity	NPC114594
0.8687	High Similarity	NPC45613
0.8681	High Similarity	NPC58616
0.8667	High Similarity	NPC153053
0.8654	High Similarity	NPC321852
0.8585	High Similarity	NPC210092
0.8571	High Similarity	NPC161611
0.8571	High Similarity	NPC272524
0.8558	High Similarity	NPC167504
0.8544	High Similarity	NPC85493
0.8544	High Similarity	NPC99846
0.8544	High Similarity	NPC269023
0.8542	High Similarity	NPC261181
0.8526	High Similarity	NPC119631
0.8491	Intermediate Similarity	NPC474363
0.8491	Intermediate Similarity	NPC308744
0.8491	Intermediate Similarity	NPC307651
0.8478	Intermediate Similarity	NPC294134
0.8476	Intermediate Similarity	NPC79496
0.8476	Intermediate Similarity	NPC158282
0.8476	Intermediate Similarity	NPC474314
0.8469	Intermediate Similarity	NPC253423
0.8469	Intermediate Similarity	NPC270654
0.8421	Intermediate Similarity	NPC62765
0.8411	Intermediate Similarity	NPC474685
0.8404	Intermediate Similarity	NPC304760
0.8396	Intermediate Similarity	NPC474176
0.8384	Intermediate Similarity	NPC229242
0.8333	Intermediate Similarity	NPC149691
0.8317	Intermediate Similarity	NPC304873
0.83	Intermediate Similarity	NPC217621
0.8261	Intermediate Similarity	NPC288903
0.8241	Intermediate Similarity	NPC306740
0.8218	Intermediate Similarity	NPC473325
0.8182	Intermediate Similarity	NPC61944
0.8182	Intermediate Similarity	NPC45104
0.8182	Intermediate Similarity	NPC217423
0.8165	Intermediate Similarity	NPC100353
0.8148	Intermediate Similarity	NPC237366
0.8137	Intermediate Similarity	NPC25458
0.8125	Intermediate Similarity	NPC473243
0.8125	Intermediate Similarity	NPC72977
0.8108	Intermediate Similarity	NPC27633
0.8108	Intermediate Similarity	NPC94637
0.8108	Intermediate Similarity	NPC94298
0.8073	Intermediate Similarity	NPC81808
0.8065	Intermediate Similarity	NPC270507
0.8053	Intermediate Similarity	NPC50872
0.8043	Intermediate Similarity	NPC303245
0.8041	Intermediate Similarity	NPC213156
0.8041	Intermediate Similarity	NPC240108
0.8037	Intermediate Similarity	NPC243355
0.8036	Intermediate Similarity	NPC328459
0.8036	Intermediate Similarity	NPC90522
0.8022	Intermediate Similarity	NPC78517
0.8022	Intermediate Similarity	NPC167577
0.8018	Intermediate Similarity	NPC469574
0.8	Intermediate Similarity	NPC220540
0.8	Intermediate Similarity	NPC188907
0.7982	Intermediate Similarity	NPC477411
0.7982	Intermediate Similarity	NPC196075
0.7961	Intermediate Similarity	NPC284477
0.7957	Intermediate Similarity	NPC103387
0.7957	Intermediate Similarity	NPC323103
0.7941	Intermediate Similarity	NPC228435
0.7941	Intermediate Similarity	NPC472318
0.7941	Intermediate Similarity	NPC98911
0.7938	Intermediate Similarity	NPC9822
0.7935	Intermediate Similarity	NPC121800
0.7928	Intermediate Similarity	NPC131192
0.7928	Intermediate Similarity	NPC128825
0.7925	Intermediate Similarity	NPC470391
0.7912	Intermediate Similarity	NPC176228
0.7909	Intermediate Similarity	NPC474095
0.7905	Intermediate Similarity	NPC105899
0.7885	Intermediate Similarity	NPC234305
0.7885	Intermediate Similarity	NPC255676
0.7885	Intermediate Similarity	NPC160382
0.7879	Intermediate Similarity	NPC77273
0.7864	Intermediate Similarity	NPC282895
0.7857	Intermediate Similarity	NPC185501
0.7857	Intermediate Similarity	NPC240664
0.7849	Intermediate Similarity	NPC89950
0.7838	Intermediate Similarity	NPC226093
0.7838	Intermediate Similarity	NPC135730
0.783	Intermediate Similarity	NPC1065
0.7826	Intermediate Similarity	NPC26285
0.7826	Intermediate Similarity	NPC170484
0.7818	Intermediate Similarity	NPC53953
0.781	Intermediate Similarity	NPC85977
0.7807	Intermediate Similarity	NPC230951
0.7807	Intermediate Similarity	NPC233282
0.7802	Intermediate Similarity	NPC3672
0.7802	Intermediate Similarity	NPC287790
0.7798	Intermediate Similarity	NPC54626
0.7798	Intermediate Similarity	NPC23332
0.7798	Intermediate Similarity	NPC212415
0.7798	Intermediate Similarity	NPC57879
0.7788	Intermediate Similarity	NPC293424
0.7778	Intermediate Similarity	NPC110704
0.7768	Intermediate Similarity	NPC470860
0.7766	Intermediate Similarity	NPC106313
0.7759	Intermediate Similarity	NPC472703
0.7759	Intermediate Similarity	NPC291189
0.7759	Intermediate Similarity	NPC69403
0.7759	Intermediate Similarity	NPC223351
0.7757	Intermediate Similarity	NPC249811
0.7748	Intermediate Similarity	NPC252004
0.7745	Intermediate Similarity	NPC325499
0.7732	Intermediate Similarity	NPC322387
0.7732	Intermediate Similarity	NPC96625
0.7727	Intermediate Similarity	NPC17693
0.7727	Intermediate Similarity	NPC13784
0.7723	Intermediate Similarity	NPC5472
0.7719	Intermediate Similarity	NPC61779
0.7714	Intermediate Similarity	NPC179686
0.7712	Intermediate Similarity	NPC476599
0.7712	Intermediate Similarity	NPC49938
0.7712	Intermediate Similarity	NPC275576
0.7712	Intermediate Similarity	NPC470765
0.7706	Intermediate Similarity	NPC183648
0.7699	Intermediate Similarity	NPC228318
0.7692	Intermediate Similarity	NPC175393
0.7692	Intermediate Similarity	NPC472704
0.7685	Intermediate Similarity	NPC281604
0.7684	Intermediate Similarity	NPC127491
0.7684	Intermediate Similarity	NPC308619
0.7684	Intermediate Similarity	NPC285773
0.7684	Intermediate Similarity	NPC324835
0.767	Intermediate Similarity	NPC210529
0.767	Intermediate Similarity	NPC175852
0.767	Intermediate Similarity	NPC160548
0.7664	Intermediate Similarity	NPC474376
0.7664	Intermediate Similarity	NPC326447
0.7664	Intermediate Similarity	NPC472315
0.7664	Intermediate Similarity	NPC472316
0.7664	Intermediate Similarity	NPC475203
0.766	Intermediate Similarity	NPC165212
0.7647	Intermediate Similarity	NPC473220
0.7647	Intermediate Similarity	NPC169913
0.7647	Intermediate Similarity	NPC475236
0.7647	Intermediate Similarity	NPC470753
0.7642	Intermediate Similarity	NPC269644
0.7642	Intermediate Similarity	NPC249067
0.7636	Intermediate Similarity	NPC66208
0.7627	Intermediate Similarity	NPC246166
0.7627	Intermediate Similarity	NPC125053
0.7627	Intermediate Similarity	NPC295664
0.7627	Intermediate Similarity	NPC184219
0.7627	Intermediate Similarity	NPC221798
0.7624	Intermediate Similarity	NPC23453
0.7615	Intermediate Similarity	NPC234639

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 NPC225060 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	213
0.1-0.2	937
0.2-0.3	1284
0.3-0.4	2912
0.4-0.5	2285
0.5-0.6	1099
0.6-0.7	344
0.7-0.8	66
0.8-0.85	4
0.85-0.9	5
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9468	High Similarity	NPD1238	Approved
0.8911	High Similarity	NPD2182	Approved
0.8889	High Similarity	NPD164	Approved
0.8791	High Similarity	NPD9257	Approved
0.8791	High Similarity	NPD9259	Approved
0.8738	High Similarity	NPD2181	Clinical (unspecified phase)
0.8542	High Similarity	NPD1202	Approved
0.8421	Intermediate Similarity	NPD9256	Approved
0.8421	Intermediate Similarity	NPD9258	Approved
0.8108	Intermediate Similarity	NPD9545	Approved
0.8081	Intermediate Similarity	NPD9260	Approved
0.7928	Intermediate Similarity	NPD9493	Approved
0.7826	Intermediate Similarity	NPD9490	Approved
0.7798	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7748	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7732	Intermediate Similarity	NPD1087	Approved
0.7685	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7684	Intermediate Similarity	NPD9491	Approved
0.7677	Intermediate Similarity	NPD3673	Approved
0.7677	Intermediate Similarity	NPD3672	Approved
0.7672	Intermediate Similarity	NPD6287	Discontinued
0.767	Intermediate Similarity	NPD9495	Approved
0.7664	Intermediate Similarity	NPD3134	Approved
0.7658	Intermediate Similarity	NPD1241	Discontinued
0.7647	Intermediate Similarity	NPD1989	Approved
0.7642	Intermediate Similarity	NPD1237	Approved
0.7627	Intermediate Similarity	NPD2198	Approved
0.7627	Intermediate Similarity	NPD2199	Approved
0.7615	Intermediate Similarity	NPD2067	Discontinued
0.7576	Intermediate Similarity	NPD800	Approved
0.7563	Intermediate Similarity	NPD552	Approved
0.7563	Intermediate Similarity	NPD553	Approved
0.7563	Intermediate Similarity	NPD9567	Approved
0.7551	Intermediate Similarity	NPD1282	Approved
0.7547	Intermediate Similarity	NPD1929	Approved
0.7547	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD9261	Approved
0.7547	Intermediate Similarity	NPD1930	Approved
0.7527	Intermediate Similarity	NPD227	Approved
0.7527	Intermediate Similarity	NPD225	Approved
0.7521	Intermediate Similarity	NPD518	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1090	Approved
0.75	Intermediate Similarity	NPD1019	Discontinued
0.75	Intermediate Similarity	NPD1086	Approved
0.75	Intermediate Similarity	NPD1089	Approved
0.7477	Intermediate Similarity	NPD5909	Discontinued
0.7458	Intermediate Similarity	NPD9717	Approved
0.7431	Intermediate Similarity	NPD1358	Approved
0.7429	Intermediate Similarity	NPD2066	Phase 3
0.7411	Intermediate Similarity	NPD5277	Phase 2
0.7383	Intermediate Similarity	NPD6647	Phase 2
0.7377	Intermediate Similarity	NPD6832	Phase 2
0.7353	Intermediate Similarity	NPD1088	Approved
0.735	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD5926	Approved
0.7321	Intermediate Similarity	NPD9508	Approved
0.7317	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD226	Approved
0.7282	Intermediate Similarity	NPD1563	Approved
0.7281	Intermediate Similarity	NPD2629	Approved
0.7281	Intermediate Similarity	NPD5951	Approved
0.7273	Intermediate Similarity	NPD9263	Approved
0.7273	Intermediate Similarity	NPD9267	Approved
0.7273	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD9264	Approved
0.7241	Intermediate Similarity	NPD2347	Approved
0.7227	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD1693	Approved
0.7207	Intermediate Similarity	NPD9266	Approved
0.7207	Intermediate Similarity	NPD74	Approved
0.7177	Intermediate Similarity	NPD7008	Discontinued
0.7143	Intermediate Similarity	NPD3373	Approved
0.7131	Intermediate Similarity	NPD1203	Approved
0.7115	Intermediate Similarity	NPD5122	Clinical (unspecified phase)
0.7109	Intermediate Similarity	NPD2670	Approved
0.7109	Intermediate Similarity	NPD2567	Approved
0.7109	Intermediate Similarity	NPD2569	Approved
0.7091	Intermediate Similarity	NPD9697	Approved
0.7087	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD1239	Approved
0.7075	Intermediate Similarity	NPD1565	Approved
0.7075	Intermediate Similarity	NPD1566	Phase 3
0.7075	Intermediate Similarity	NPD1564	Approved
0.7073	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD5347	Phase 2
0.7059	Intermediate Similarity	NPD17	Approved
0.7059	Intermediate Similarity	NPD689	Discontinued
0.7059	Intermediate Similarity	NPD5346	Phase 2
0.7049	Intermediate Similarity	NPD1876	Approved
0.704	Intermediate Similarity	NPD6039	Approved
0.7034	Intermediate Similarity	NPD1894	Discontinued
0.7025	Intermediate Similarity	NPD3972	Approved
0.7021	Intermediate Similarity	NPD9716	Approved
0.7018	Intermediate Similarity	NPD969	Suspended
0.6991	Remote Similarity	NPD5236	Approved
0.6991	Remote Similarity	NPD5235	Approved
0.6991	Remote Similarity	NPD5239	Approved
0.6991	Remote Similarity	NPD5240	Approved
0.6991	Remote Similarity	NPD5237	Approved
0.6975	Remote Similarity	NPD5585	Approved
0.6972	Remote Similarity	NPD1932	Approved
0.6953	Remote Similarity	NPD1933	Approved
0.6953	Remote Similarity	NPD230	Phase 1
0.6947	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6942	Remote Similarity	NPD1281	Approved
0.6939	Remote Similarity	NPD942	Approved
0.6935	Remote Similarity	NPD2798	Approved
0.693	Remote Similarity	NPD2201	Approved
0.6923	Remote Similarity	NPD3170	Approved
0.6923	Remote Similarity	NPD1110	Approved
0.6923	Remote Similarity	NPD1109	Approved
0.6917	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD5306	Approved
0.6917	Remote Similarity	NPD1104	Approved
0.6917	Remote Similarity	NPD1362	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD5305	Approved
0.6911	Remote Similarity	NPD5667	Approved
0.6903	Remote Similarity	NPD2329	Discontinued
0.6899	Remote Similarity	NPD3528	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD1654	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD688	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD1608	Approved
0.6875	Remote Similarity	NPD9294	Approved
0.6875	Remote Similarity	NPD4307	Phase 2
0.6863	Remote Similarity	NPD4793	Discontinued
0.6863	Remote Similarity	NPD650	Approved
0.686	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD2797	Approved
0.6855	Remote Similarity	NPD3267	Approved
0.6855	Remote Similarity	NPD3266	Approved
0.685	Remote Similarity	NPD3764	Approved
0.685	Remote Similarity	NPD2313	Discontinued
0.685	Remote Similarity	NPD411	Approved
0.6842	Remote Similarity	NPD4233	Approved
0.6842	Remote Similarity	NPD1752	Approved
0.6842	Remote Similarity	NPD4234	Approved
0.6842	Remote Similarity	NPD1756	Approved
0.6842	Remote Similarity	NPD1317	Discontinued
0.6838	Remote Similarity	NPD9281	Approved
0.6838	Remote Similarity	NPD1246	Approved
0.6822	Remote Similarity	NPD447	Suspended
0.6818	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD4806	Approved
0.6803	Remote Similarity	NPD4807	Approved
0.6797	Remote Similarity	NPD7713	Phase 3
0.6794	Remote Similarity	NPD2799	Discontinued
0.6789	Remote Similarity	NPD7798	Approved
0.678	Remote Similarity	NPD4198	Discontinued
0.6777	Remote Similarity	NPD1778	Approved
0.6774	Remote Similarity	NPD1283	Approved
0.6752	Remote Similarity	NPD2652	Approved
0.6752	Remote Similarity	NPD2650	Approved
0.6748	Remote Similarity	NPD6637	Approved
0.6746	Remote Similarity	NPD9494	Approved
0.6744	Remote Similarity	NPD3142	Approved
0.6744	Remote Similarity	NPD3140	Approved
0.6742	Remote Similarity	NPD1551	Phase 2
0.6723	Remote Similarity	NPD694	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD1889	Phase 1
0.6721	Remote Similarity	NPD4106	Approved
0.6721	Remote Similarity	NPD4136	Approved
0.6721	Remote Similarity	NPD4135	Approved
0.6719	Remote Similarity	NPD9471	Clinical (unspecified phase)
0.6716	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD506	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD7631	Approved
0.6696	Remote Similarity	NPD3646	Clinical (unspecified phase)
0.6695	Remote Similarity	NPD4766	Approved
0.6694	Remote Similarity	NPD4359	Approved
0.6694	Remote Similarity	NPD5691	Approved
0.6694	Remote Similarity	NPD182	Clinical (unspecified phase)
0.6691	Remote Similarity	NPD7236	Approved
0.6667	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD520	Approved
0.6667	Remote Similarity	NPD4628	Phase 3
0.6667	Remote Similarity	NPD6085	Phase 2
0.6667	Remote Similarity	NPD6858	Approved
0.6667	Remote Similarity	NPD4308	Phase 3
0.6667	Remote Similarity	NPD7094	Approved
0.6667	Remote Similarity	NPD2607	Approved
0.6642	Remote Similarity	NPD6414	Clinical (unspecified phase)
0.6638	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6618	Remote Similarity	NPD3887	Approved
0.6617	Remote Similarity	NPD2935	Discontinued
0.6615	Remote Similarity	NPD2979	Phase 3
0.6614	Remote Similarity	NPD454	Approved
0.6613	Remote Similarity	NPD5108	Clinical (unspecified phase)
0.6613	Remote Similarity	NPD1481	Phase 2
0.6607	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD7609	Phase 3
0.66	Remote Similarity	NPD9250	Approved
0.6589	Remote Similarity	NPD3268	Approved
0.6585	Remote Similarity	NPD3496	Discontinued
0.6583	Remote Similarity	NPD4574	Approved
0.6583	Remote Similarity	NPD5291	Approved
0.6583	Remote Similarity	NPD4576	Approved
0.6583	Remote Similarity	NPD5292	Approved
0.6577	Remote Similarity	NPD2553	Approved
0.6577	Remote Similarity	NPD2555	Approved
0.6577	Remote Similarity	NPD2558	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