NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	192.12
Volume:	214.586
LogP:	3.085
LogD:	2.96
LogS:	-3.179
# Rotatable Bonds:	5
TPSA:	26.3
# H-Bond Aceptor:	2
# H-Bond Donor:	0
# Rings:	1
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.685
Synthetic Accessibility Score:	1.619
Fsp3:	0.417
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:	-4.245
MDCK Permeability:	3.522694532875903e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.159
30% Bioavailability (F30%):	0.932

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.953
Plasma Protein Binding (PPB):	60.78791809082031%
Volume Distribution (VD):	2.929
Pgp-substrate:	30.960861206054688%

ADMET: Metabolism

CYP1A2-inhibitor:	0.965
CYP1A2-substrate:	0.409
CYP2C19-inhibitor:	0.942
CYP2C19-substrate:	0.435
CYP2C9-inhibitor:	0.505
CYP2C9-substrate:	0.338
CYP2D6-inhibitor:	0.061
CYP2D6-substrate:	0.265
CYP3A4-inhibitor:	0.074
CYP3A4-substrate:	0.452

ADMET: Excretion

Clearance (CL):	9.548
Half-life (T1/2):	0.701

ADMET: Toxicity

hERG Blockers:	0.067
Human Hepatotoxicity (H-HT):	0.042
Drug-inuced Liver Injury (DILI):	0.178
AMES Toxicity:	0.033
Rat Oral Acute Toxicity:	0.021
Maximum Recommended Daily Dose:	0.016
Skin Sensitization:	0.602
Carcinogencity:	0.418
Eye Corrosion:	0.322
Eye Irritation:	0.968
Respiratory Toxicity:	0.073

Download Data

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

Natural Product: NPC103387

Natural Product ID:	NPC103387
*Common Name:**	2-Phenylethyl 2-Methylpropanoate
IUPAC Name:	2-phenylethyl 2-methylpropanoate
Synonyms:
Standard InCHIKey:	JDQVBGQWADMTAM-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C12H16O2/c1-10(2)12(13)14-9-8-11-6-4-3-5-7-11/h3-7,10H,8-9H2,1-2H3
SMILES:	O=C(C(C)C)OCCc1ccccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3184929
PubChem CID:	7655
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives

*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]
NPO28276	Artemisia argyi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.jep.2005.01.054]
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.	leaf	n.a.	PMID[11312782]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	fruit	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]
NPO25094	Artemisia princeps	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17996677]
NPO4391	Hypericum perforatum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18220354]
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]
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]
NPO28276	Artemisia argyi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31181920]
NPO28276	Artemisia argyi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31418264]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31433178]
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]
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]
NPO25094	Artemisia princeps	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28276	Artemisia argyi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4391	Hypericum perforatum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[MetaboLights]
NPO4391	Hypericum perforatum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28276	Artemisia argyi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25094	Artemisia princeps	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17024	Vitis vinifera	Species	Vitaceae	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]
NPO28276	Artemisia argyi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4391	Hypericum perforatum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO25094	Artemisia princeps	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28276	Artemisia argyi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO10492	Artemisia montana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO4391	Hypericum perforatum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25094	Artemisia princeps	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10492	Artemisia montana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28276	Artemisia argyi	Species	Asteraceae	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	1

Activity Type	# Activity
Individual Protein	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT346	Individual Protein	Transient receptor potential cation channel subfamily A member 1	Homo sapiens	Activity	=	37.0	%	PMID[523561]
NPT2	Others	Unspecified		Potency	n.a.	5494.1	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 NPC103387 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	180
0.1-0.2	1043
0.2-0.3	3533
0.3-0.4	13547
0.4-0.5	16345
0.5-0.6	6567
0.6-0.7	1209
0.7-0.8	240
0.8-0.85	18
0.85-0.9	9
0.9-0.95	1
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.987	High Similarity	NPC270507
0.974	High Similarity	NPC323103
0.9737	High Similarity	NPC121800
0.9605	High Similarity	NPC170484
0.9136	High Similarity	NPC294134
0.8929	High Similarity	NPC220893
0.8889	High Similarity	NPC288903
0.8706	High Similarity	NPC9822
0.869	High Similarity	NPC89377
0.8675	High Similarity	NPC475710
0.8675	High Similarity	NPC58616
0.8588	High Similarity	NPC304760
0.8488	Intermediate Similarity	NPC173443
0.8391	Intermediate Similarity	NPC185501
0.8391	Intermediate Similarity	NPC240108
0.8391	Intermediate Similarity	NPC213156
0.8256	Intermediate Similarity	NPC322387
0.825	Intermediate Similarity	NPC175393
0.8214	Intermediate Similarity	NPC285773
0.8193	Intermediate Similarity	NPC303245
0.8182	Intermediate Similarity	NPC86670
0.8182	Intermediate Similarity	NPC274455
0.8182	Intermediate Similarity	NPC70940
0.8182	Intermediate Similarity	NPC84288
0.8111	Intermediate Similarity	NPC23453
0.8072	Intermediate Similarity	NPC127343
0.8065	Intermediate Similarity	NPC146351
0.8049	Intermediate Similarity	NPC224544
0.8046	Intermediate Similarity	NPC96625
0.8	Intermediate Similarity	NPC44830
0.8	Intermediate Similarity	NPC108218
0.7975	Intermediate Similarity	NPC155429
0.7957	Intermediate Similarity	NPC35448
0.7957	Intermediate Similarity	NPC225060
0.7957	Intermediate Similarity	NPC78701
0.7955	Intermediate Similarity	NPC329064
0.7952	Intermediate Similarity	NPC167577
0.7952	Intermediate Similarity	NPC78517
0.7889	Intermediate Similarity	NPC119631
0.7889	Intermediate Similarity	NPC317645
0.7849	Intermediate Similarity	NPC276775
0.7849	Intermediate Similarity	NPC325499
0.7849	Intermediate Similarity	NPC270654
0.7849	Intermediate Similarity	NPC249912
0.7849	Intermediate Similarity	NPC92754
0.7831	Intermediate Similarity	NPC176228
0.7789	Intermediate Similarity	NPC473325
0.7765	Intermediate Similarity	NPC89950
0.775	Intermediate Similarity	NPC208302
0.7711	Intermediate Similarity	NPC3672
0.7711	Intermediate Similarity	NPC287790
0.7684	Intermediate Similarity	NPC7435
0.7683	Intermediate Similarity	NPC189371
0.7674	Intermediate Similarity	NPC106313
0.7667	Intermediate Similarity	NPC231591
0.766	Intermediate Similarity	NPC226041
0.7647	Intermediate Similarity	NPC309279
0.764	Intermediate Similarity	NPC286608
0.764	Intermediate Similarity	NPC169050
0.7634	Intermediate Similarity	NPC130398
0.7629	Intermediate Similarity	NPC160382
0.7629	Intermediate Similarity	NPC474365
0.7629	Intermediate Similarity	NPC301943
0.7614	Intermediate Similarity	NPC95965
0.7614	Intermediate Similarity	NPC53299
0.7604	Intermediate Similarity	NPC70624
0.7604	Intermediate Similarity	NPC42211
0.7604	Intermediate Similarity	NPC469481
0.7586	Intermediate Similarity	NPC208183
0.7586	Intermediate Similarity	NPC308619
0.7586	Intermediate Similarity	NPC127491
0.7586	Intermediate Similarity	NPC243289
0.7586	Intermediate Similarity	NPC324835
0.7576	Intermediate Similarity	NPC477251
0.7558	Intermediate Similarity	NPC165212
0.7551	Intermediate Similarity	NPC19136
0.7531	Intermediate Similarity	NPC326200
0.7525	Intermediate Similarity	NPC214067
0.7525	Intermediate Similarity	NPC196246
0.75	Intermediate Similarity	NPC267704
0.75	Intermediate Similarity	NPC304538
0.75	Intermediate Similarity	NPC325497
0.75	Intermediate Similarity	NPC298023
0.75	Intermediate Similarity	NPC118343
0.75	Intermediate Similarity	NPC98911
0.75	Intermediate Similarity	NPC472318
0.75	Intermediate Similarity	NPC221825
0.75	Intermediate Similarity	NPC56493
0.7475	Intermediate Similarity	NPC473855
0.7471	Intermediate Similarity	NPC99240
0.7471	Intermediate Similarity	NPC87299
0.7471	Intermediate Similarity	NPC329319
0.7471	Intermediate Similarity	NPC99394
0.7471	Intermediate Similarity	NPC103326
0.7451	Intermediate Similarity	NPC305912
0.7451	Intermediate Similarity	NPC1082
0.7449	Intermediate Similarity	NPC234305
0.7442	Intermediate Similarity	NPC157055
0.7442	Intermediate Similarity	NPC328178
0.7439	Intermediate Similarity	NPC271437
0.7426	Intermediate Similarity	NPC469511
0.7426	Intermediate Similarity	NPC31274
0.7426	Intermediate Similarity	NPC10251
0.7426	Intermediate Similarity	NPC17417
0.7426	Intermediate Similarity	NPC469636
0.7419	Intermediate Similarity	NPC77273
0.7412	Intermediate Similarity	NPC76455
0.7412	Intermediate Similarity	NPC137847
0.7407	Intermediate Similarity	NPC95289
0.74	Intermediate Similarity	NPC142326
0.74	Intermediate Similarity	NPC472316
0.74	Intermediate Similarity	NPC94751
0.74	Intermediate Similarity	NPC474376
0.74	Intermediate Similarity	NPC119271
0.74	Intermediate Similarity	NPC329705
0.74	Intermediate Similarity	NPC136962
0.74	Intermediate Similarity	NPC474111
0.74	Intermediate Similarity	NPC475203
0.74	Intermediate Similarity	NPC472315
0.7396	Intermediate Similarity	NPC210529
0.7396	Intermediate Similarity	NPC271475
0.7396	Intermediate Similarity	NPC160548
0.7396	Intermediate Similarity	NPC175852
0.7391	Intermediate Similarity	NPC258627
0.7386	Intermediate Similarity	NPC172984
0.7386	Intermediate Similarity	NPC477770
0.7379	Intermediate Similarity	NPC270699
0.7379	Intermediate Similarity	NPC82899
0.7374	Intermediate Similarity	NPC85977
0.7368	Intermediate Similarity	NPC261947
0.7356	Intermediate Similarity	NPC117180
0.7353	Intermediate Similarity	NPC93084
0.7353	Intermediate Similarity	NPC174099
0.7353	Intermediate Similarity	NPC251854
0.7353	Intermediate Similarity	NPC158854
0.7349	Intermediate Similarity	NPC208075
0.7347	Intermediate Similarity	NPC188895
0.7347	Intermediate Similarity	NPC474112
0.7333	Intermediate Similarity	NPC93843
0.7333	Intermediate Similarity	NPC318107
0.7327	Intermediate Similarity	NPC21929
0.732	Intermediate Similarity	NPC476042
0.732	Intermediate Similarity	NPC203925
0.732	Intermediate Similarity	NPC171843
0.7317	Intermediate Similarity	NPC74458
0.7312	Intermediate Similarity	NPC86987
0.7312	Intermediate Similarity	NPC476484
0.7312	Intermediate Similarity	NPC110704
0.7308	Intermediate Similarity	NPC26615
0.7308	Intermediate Similarity	NPC128368
0.7303	Intermediate Similarity	NPC95429
0.73	Intermediate Similarity	NPC269457
0.73	Intermediate Similarity	NPC472919
0.73	Intermediate Similarity	NPC238115
0.7294	Intermediate Similarity	NPC66655
0.7294	Intermediate Similarity	NPC329318
0.7292	Intermediate Similarity	NPC477767
0.7284	Intermediate Similarity	NPC16190
0.7284	Intermediate Similarity	NPC235059
0.7284	Intermediate Similarity	NPC169222
0.7284	Intermediate Similarity	NPC98880
0.7283	Intermediate Similarity	NPC1793
0.7282	Intermediate Similarity	NPC474157
0.7273	Intermediate Similarity	NPC230068
0.7273	Intermediate Similarity	NPC89886
0.7273	Intermediate Similarity	NPC73637
0.7273	Intermediate Similarity	NPC91820
0.7273	Intermediate Similarity	NPC121478
0.7273	Intermediate Similarity	NPC82426
0.7263	Intermediate Similarity	NPC172925
0.7263	Intermediate Similarity	NPC5472
0.7262	Intermediate Similarity	NPC206800
0.7262	Intermediate Similarity	NPC32203
0.7255	Intermediate Similarity	NPC83628
0.7255	Intermediate Similarity	NPC265407
0.7241	Intermediate Similarity	NPC184030
0.7241	Intermediate Similarity	NPC164449
0.7238	Intermediate Similarity	NPC153053
0.7238	Intermediate Similarity	NPC190212
0.7229	Intermediate Similarity	NPC285679
0.7228	Intermediate Similarity	NPC326447
0.7216	Intermediate Similarity	NPC229242
0.7216	Intermediate Similarity	NPC179411
0.7216	Intermediate Similarity	NPC145052
0.7212	Intermediate Similarity	NPC321852
0.7209	Intermediate Similarity	NPC50192
0.7209	Intermediate Similarity	NPC103488
0.7204	Intermediate Similarity	NPC108026
0.72	Intermediate Similarity	NPC242913
0.72	Intermediate Similarity	NPC31786
0.72	Intermediate Similarity	NPC280616
0.72	Intermediate Similarity	NPC171831
0.7184	Intermediate Similarity	NPC273837
0.7174	Intermediate Similarity	NPC325441
0.7172	Intermediate Similarity	NPC304873
0.717	Intermediate Similarity	NPC210092
0.716	Intermediate Similarity	NPC311343
0.7159	Intermediate Similarity	NPC133050
0.7159	Intermediate Similarity	NPC71795
0.7158	Intermediate Similarity	NPC261181

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 NPC103387 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	161
0.1-0.2	859
0.2-0.3	1416
0.3-0.4	3327
0.4-0.5	2050
0.5-0.6	1044
0.6-0.7	231
0.7-0.8	50
0.8-0.85	10
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8605	High Similarity	NPD3673	Approved
0.8605	High Similarity	NPD3672	Approved
0.8471	Intermediate Similarity	NPD1087	Approved
0.8395	Intermediate Similarity	NPD9490	Approved
0.8333	Intermediate Similarity	NPD1989	Approved
0.8276	Intermediate Similarity	NPD800	Approved
0.8272	Intermediate Similarity	NPD227	Approved
0.8272	Intermediate Similarity	NPD225	Approved
0.8214	Intermediate Similarity	NPD9491	Approved
0.8182	Intermediate Similarity	NPD1090	Approved
0.8182	Intermediate Similarity	NPD1089	Approved
0.8182	Intermediate Similarity	NPD1086	Approved
0.8	Intermediate Similarity	NPD1088	Approved
0.7976	Intermediate Similarity	NPD226	Approved
0.7865	Intermediate Similarity	NPD5347	Phase 2
0.7865	Intermediate Similarity	NPD5346	Phase 2
0.7826	Intermediate Similarity	NPD1693	Approved
0.7766	Intermediate Similarity	NPD5926	Approved
0.7717	Intermediate Similarity	NPD1563	Approved
0.7717	Intermediate Similarity	NPD1066	Discontinued
0.764	Intermediate Similarity	NPD4793	Discontinued
0.764	Intermediate Similarity	NPD1282	Approved
0.7629	Intermediate Similarity	NPD6647	Phase 2
0.7556	Intermediate Similarity	NPD531	Approved
0.7527	Intermediate Similarity	NPD5122	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2066	Phase 3
0.75	Intermediate Similarity	NPD1238	Approved
0.75	Intermediate Similarity	NPD7798	Approved
0.75	Intermediate Similarity	NPD1239	Approved
0.7474	Intermediate Similarity	NPD1565	Approved
0.7474	Intermediate Similarity	NPD1564	Approved
0.7474	Intermediate Similarity	NPD1566	Phase 3
0.7426	Intermediate Similarity	NPD2182	Approved
0.74	Intermediate Similarity	NPD5706	Approved
0.74	Intermediate Similarity	NPD5704	Approved
0.74	Intermediate Similarity	NPD6685	Approved
0.74	Intermediate Similarity	NPD5705	Approved
0.7396	Intermediate Similarity	NPD9495	Approved
0.7353	Intermediate Similarity	NPD1756	Approved
0.7353	Intermediate Similarity	NPD1752	Approved
0.7353	Intermediate Similarity	NPD2067	Discontinued
0.7353	Intermediate Similarity	NPD4234	Approved
0.7353	Intermediate Similarity	NPD4233	Approved
0.7333	Intermediate Similarity	NPD9257	Approved
0.7333	Intermediate Similarity	NPD9259	Approved
0.7294	Intermediate Similarity	NPD9294	Approved
0.7282	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD5738	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD688	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD9716	Approved
0.7238	Intermediate Similarity	NPD2650	Approved
0.7238	Intermediate Similarity	NPD2652	Approved
0.7228	Intermediate Similarity	NPD3134	Approved
0.72	Intermediate Similarity	NPD164	Approved
0.72	Intermediate Similarity	NPD5909	Discontinued
0.7191	Intermediate Similarity	NPD3971	Phase 1
0.7184	Intermediate Similarity	NPD5236	Approved
0.7184	Intermediate Similarity	NPD5240	Approved
0.7184	Intermediate Similarity	NPD5237	Approved
0.7184	Intermediate Similarity	NPD5239	Approved
0.7184	Intermediate Similarity	NPD3646	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD5235	Approved
0.7174	Intermediate Similarity	NPD1101	Approved
0.717	Intermediate Similarity	NPD2629	Approved
0.717	Intermediate Similarity	NPD4766	Approved
0.7158	Intermediate Similarity	NPD1202	Approved
0.7143	Intermediate Similarity	NPD2607	Approved
0.7115	Intermediate Similarity	NPD2201	Approved
0.71	Intermediate Similarity	NPD1929	Approved
0.71	Intermediate Similarity	NPD5765	Approved
0.71	Intermediate Similarity	NPD1930	Approved
0.71	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD689	Discontinued
0.7037	Intermediate Similarity	NPD4574	Approved
0.7037	Intermediate Similarity	NPD4576	Approved
0.7033	Intermediate Similarity	NPD5734	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD9258	Approved
0.7021	Intermediate Similarity	NPD9256	Approved
0.701	Intermediate Similarity	NPD5206	Clinical (unspecified phase)
0.699	Remote Similarity	NPD1358	Approved
0.6981	Remote Similarity	NPD6858	Approved
0.6981	Remote Similarity	NPD7094	Approved
0.697	Remote Similarity	NPD1067	Discontinued
0.6966	Remote Similarity	NPD9250	Approved
0.6961	Remote Similarity	NPD5048	Discontinued
0.6944	Remote Similarity	NPD4198	Discontinued
0.6916	Remote Similarity	NPD1373	Approved
0.6916	Remote Similarity	NPD1374	Approved
0.6916	Remote Similarity	NPD1371	Approved
0.6916	Remote Similarity	NPD1370	Approved
0.6887	Remote Similarity	NPD6912	Phase 3
0.6869	Remote Similarity	NPD253	Approved
0.6822	Remote Similarity	NPD1279	Clinical (unspecified phase)
0.6804	Remote Similarity	NPD1409	Phase 3
0.68	Remote Similarity	NPD3097	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD5306	Approved
0.6786	Remote Similarity	NPD5305	Approved
0.6771	Remote Similarity	NPD530	Approved
0.6768	Remote Similarity	NPD9566	Approved
0.6762	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD4479	Discontinued
0.6735	Remote Similarity	NPD4814	Discontinued
0.6735	Remote Similarity	NPD9260	Approved
0.6733	Remote Similarity	NPD2553	Approved
0.6733	Remote Similarity	NPD2552	Approved
0.6733	Remote Similarity	NPD2549	Approved
0.6733	Remote Similarity	NPD2550	Approved
0.6733	Remote Similarity	NPD2555	Approved
0.6733	Remote Similarity	NPD2558	Approved
0.6702	Remote Similarity	NPD9538	Approved
0.6696	Remote Similarity	NPD5585	Approved
0.6667	Remote Similarity	NPD2612	Approved
0.6667	Remote Similarity	NPD2609	Approved
0.6667	Remote Similarity	NPD2611	Approved
0.6667	Remote Similarity	NPD6065	Approved
0.6667	Remote Similarity	NPD4807	Approved
0.6667	Remote Similarity	NPD5535	Approved
0.6667	Remote Similarity	NPD2608	Approved
0.6667	Remote Similarity	NPD4806	Approved
0.6667	Remote Similarity	NPD4215	Approved
0.6667	Remote Similarity	NPD2347	Approved
0.6667	Remote Similarity	NPD3132	Approved
0.6667	Remote Similarity	NPD4189	Approved
0.6667	Remote Similarity	NPD2610	Approved
0.6667	Remote Similarity	NPD4217	Approved
0.6667	Remote Similarity	NPD4216	Approved
0.6667	Remote Similarity	NPD4188	Approved
0.6667	Remote Similarity	NPD3131	Approved
0.6667	Remote Similarity	NPD4218	Approved
0.6635	Remote Similarity	NPD1040	Phase 2
0.6634	Remote Similarity	NPD9712	Approved
0.6633	Remote Similarity	NPD720	Approved
0.6633	Remote Similarity	NPD845	Approved
0.6633	Remote Similarity	NPD3719	Approved
0.6633	Remote Similarity	NPD3718	Approved
0.6633	Remote Similarity	NPD719	Approved
0.6606	Remote Similarity	NPD6010	Discontinued
0.6579	Remote Similarity	NPD4106	Approved
0.6579	Remote Similarity	NPD4135	Approved
0.6579	Remote Similarity	NPD4136	Approved
0.6577	Remote Similarity	NPD694	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD5291	Approved
0.6577	Remote Similarity	NPD5292	Approved
0.6574	Remote Similarity	NPD969	Suspended
0.6571	Remote Similarity	NPD467	Phase 1
0.6569	Remote Similarity	NPD3135	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD6049	Phase 2
0.6566	Remote Similarity	NPD7343	Discovery
0.6566	Remote Similarity	NPD2933	Approved
0.6566	Remote Similarity	NPD7344	Phase 1
0.6566	Remote Similarity	NPD6048	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD2934	Approved
0.6549	Remote Similarity	NPD5981	Approved
0.6549	Remote Similarity	NPD5691	Approved
0.6549	Remote Similarity	NPD4209	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6542	Remote Similarity	NPD1317	Discontinued
0.6538	Remote Similarity	NPD1237	Approved
0.6538	Remote Similarity	NPD3048	Approved
0.6538	Remote Similarity	NPD3047	Approved
0.6538	Remote Similarity	NPD3046	Approved
0.6535	Remote Similarity	NPD9710	Approved
0.6535	Remote Similarity	NPD9711	Approved
0.6531	Remote Similarity	NPD752	Approved
0.6522	Remote Similarity	NPD4480	Approved
0.6522	Remote Similarity	NPD7436	Approved
0.6522	Remote Similarity	NPD7437	Approved
0.6522	Remote Similarity	NPD5618	Discontinued
0.6505	Remote Similarity	NPD1932	Approved
0.65	Remote Similarity	NPD2859	Approved
0.65	Remote Similarity	NPD2860	Approved
0.6491	Remote Similarity	NPD1778	Approved
0.6484	Remote Similarity	NPD1507	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD3643	Approved
0.6481	Remote Similarity	NPD3642	Approved
0.6481	Remote Similarity	NPD3644	Approved
0.6476	Remote Similarity	NPD9697	Approved
0.6471	Remote Similarity	NPD3020	Approved
0.6471	Remote Similarity	NPD9497	Clinical (unspecified phase)
0.6463	Remote Similarity	NPD675	Discontinued
0.646	Remote Similarity	NPD9545	Approved
0.646	Remote Similarity	NPD1894	Discontinued
0.646	Remote Similarity	NPD2617	Discontinued
0.6455	Remote Similarity	NPD1280	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD1241	Discontinued
0.6449	Remote Similarity	NPD2329	Discontinued
0.6449	Remote Similarity	NPD2684	Approved
0.6442	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.6435	Remote Similarity	NPD3496	Discontinued
0.6415	Remote Similarity	NPD3526	Approved
0.6415	Remote Similarity	NPD810	Approved
0.6415	Remote Similarity	NPD811	Approved
0.6415	Remote Similarity	NPD812	Approved
0.6415	Remote Similarity	NPD2559	Approved
0.6415	Remote Similarity	NPD2551	Approved
0.6415	Remote Similarity	NPD3524	Approved
0.6413	Remote Similarity	NPD942	Approved
0.641	Remote Similarity	NPD4359	Approved
0.6404	Remote Similarity	NPD4105	Approved
0.6404	Remote Similarity	NPD4102	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