NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	164.08
Volume:	179.994
LogP:	2.393
LogD:	2.538
LogS:	-2.511
# 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:	0.637
Synthetic Accessibility Score:	1.312
Fsp3:	0.3
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:	-4.315
MDCK Permeability:	5.197021528147161e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.091

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.937
Plasma Protein Binding (PPB):	72.52651977539062%
Volume Distribution (VD):	0.677
Pgp-substrate:	18.6800594329834%

ADMET: Metabolism

CYP1A2-inhibitor:	0.965
CYP1A2-substrate:	0.192
CYP2C19-inhibitor:	0.926
CYP2C19-substrate:	0.353
CYP2C9-inhibitor:	0.528
CYP2C9-substrate:	0.226
CYP2D6-inhibitor:	0.029
CYP2D6-substrate:	0.15
CYP3A4-inhibitor:	0.075
CYP3A4-substrate:	0.414

ADMET: Excretion

Clearance (CL):	12.427
Half-life (T1/2):	0.869

ADMET: Toxicity

hERG Blockers:	0.047
Human Hepatotoxicity (H-HT):	0.039
Drug-inuced Liver Injury (DILI):	0.822
AMES Toxicity:	0.037
Rat Oral Acute Toxicity:	0.063
Maximum Recommended Daily Dose:	0.009
Skin Sensitization:	0.39
Carcinogencity:	0.3
Eye Corrosion:	0.835
Eye Irritation:	0.98
Respiratory Toxicity:	0.035

Download Data

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

Natural Product: NPC294134

Natural Product ID:	NPC294134
*Common Name:**	Ethyl 2-Phenylacetate
IUPAC Name:	ethyl 2-phenylacetate
Synonyms:
Standard InCHIKey:	DULCUDSUACXJJC-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C10H12O2/c1-2-12-10(11)8-9-6-4-3-5-7-9/h3-7H,2,8H2,1H3
SMILES:	CCOC(=O)Cc1ccccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3183476
PubChem CID:	7590
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
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	Eukaryota	Flowers	n.a.	n.a.	DOI[10.1016/j.foodchem.2009.03.042]
NPO15810	Zea mays	Species	Poaceae	Eukaryota		n.a.	n.a.	DOI[10.1021/jf00055a023]
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	Eukaryota	Flowers	n.a.	n.a.	DOI[10.3136/fstr.15.499]
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	Eukaryota	Flowers	n.a.	n.a.	DOI[10.5897/AJB10.140]
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	Eukaryota	Flowers	n.a.	n.a.	DOI[10.5897/AJB2010.000-3252]
NPO15810	Zea mays	Species	Poaceae	Eukaryota	n.a.	seed	n.a.	PMID[11539687]
NPO15810	Zea mays	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12713418]
NPO9290	Zanthoxylum piperitum	Species	Rutaceae	Eukaryota	n.a.	leaf	n.a.	PMID[15388977]
NPO15095	Hippophae rhamnoides	Species	Elaeagnaceae	Eukaryota	n.a.	fruit	n.a.	PMID[16417304]
NPO9290	Zanthoxylum piperitum	Species	Rutaceae	Eukaryota	n.a.	stem	n.a.	PMID[17202689]
NPO15095	Hippophae rhamnoides	Species	Elaeagnaceae	Eukaryota	n.a.	branch	n.a.	PMID[17202693]
NPO9290	Zanthoxylum piperitum	Species	Rutaceae	Eukaryota	n.a.	pericarp	n.a.	PMID[20628994]
NPO15810	Zea mays	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21080643]
NPO15810	Zea mays	Species	Poaceae	Eukaryota	n.a.	leaf	n.a.	PMID[21574561]
NPO15810	Zea mays	Species	Poaceae	Eukaryota	n.a.	husk	n.a.	PMID[21574561]
NPO15810	Zea mays	Species	Poaceae	Eukaryota	n.a.	seed	n.a.	PMID[23292602]
NPO5315	Zanthoxylum bungeanum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24175626]
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	Eukaryota	Flowers	Tongxiang, China	n.a.	PMID[24621197]
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	Eukaryota	Flowers	n.a.	n.a.	PMID[28248102]
NPO15810	Zea mays	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29762032]
NPO15810	Zea mays	Species	Poaceae	Eukaryota	n.a.	pollen	n.a.	PMID[8987503]
NPO15095	Hippophae rhamnoides	Species	Elaeagnaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO15095	Hippophae rhamnoides	Species	Elaeagnaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO15810	Zea mays	Species	Poaceae	Eukaryota	Oil	n.a.	n.a.	Database[FooDB]
NPO15810	Zea mays	Species	Poaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO15810	Zea mays	Species	Poaceae	Eukaryota	Pollen Or Spore	n.a.	n.a.	Database[FooDB]
NPO15095	Hippophae rhamnoides	Species	Elaeagnaceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO15810	Zea mays	Species	Poaceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO15095	Hippophae rhamnoides	Species	Elaeagnaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO15810	Zea mays	Species	Poaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO15810	Zea mays	Species	Poaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO15810	Zea mays	Species	Poaceae	Eukaryota	Seed Essent. Oil	n.a.	n.a.	Database[FooDB]
NPO15095	Hippophae rhamnoides	Species	Elaeagnaceae	Eukaryota	Bark	n.a.	n.a.	Database[FooDB]
NPO15810	Zea mays	Species	Poaceae	Eukaryota	Shoot	n.a.	n.a.	Database[FooDB]
NPO15810	Zea mays	Species	Poaceae	Eukaryota	Cob	n.a.	n.a.	Database[FooDB]
NPO15810	Zea mays	Species	Poaceae	Eukaryota	Silk Essent. Oil	n.a.	n.a.	Database[FooDB]
NPO15095	Hippophae rhamnoides	Species	Elaeagnaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO15810	Zea mays	Species	Poaceae	Eukaryota	Silk Stigma Style	n.a.	n.a.	Database[FooDB]
NPO15810	Zea mays	Species	Poaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO15810	Zea mays	Species	Poaceae	Eukaryota	Husk Essent. Oil	n.a.	n.a.	Database[FooDB]
NPO15810	Zea mays	Species	Poaceae	Eukaryota	Stem	n.a.	n.a.	Database[FooDB]
NPO5315	Zanthoxylum bungeanum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15095	Hippophae rhamnoides	Species	Elaeagnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9290	Zanthoxylum piperitum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15810	Zea mays	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8698	Zanthoxylum schinifolium	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15810	Zea mays	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15095	Hippophae rhamnoides	Species	Elaeagnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5315	Zanthoxylum bungeanum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9290	Zanthoxylum piperitum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8698	Zanthoxylum schinifolium	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15810	Zea mays	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15095	Hippophae rhamnoides	Species	Elaeagnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9290	Zanthoxylum piperitum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5315	Zanthoxylum bungeanum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8698	Zanthoxylum schinifolium	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO15810	Zea mays	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO5315	Zanthoxylum bungeanum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO8698	Zanthoxylum schinifolium	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO15095	Hippophae rhamnoides	Species	Elaeagnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO9290	Zanthoxylum piperitum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO8698	Zanthoxylum schinifolium	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5315	Zanthoxylum bungeanum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9290	Zanthoxylum piperitum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15095	Hippophae rhamnoides	Species	Elaeagnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15810	Zea mays	Species	Poaceae	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
NPO15810	NPC294134	Raw	Silk Essent. Oil	49500	25000	74000	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	6

Activity Type	# Activity
Others	6

Target ID	Target Type	Target Name	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified	Potency	n.a.	5494.1	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	Potency	n.a.	1737.4	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	Potency	n.a.	19331.2	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	Potency	n.a.	61644.8	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	Potency	n.a.	1.5	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 NPC294134 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	191
0.1-0.2	1050
0.2-0.3	3393
0.3-0.4	12066
0.4-0.5	15729
0.5-0.6	8446
0.6-0.7	1476
0.7-0.8	292
0.8-0.85	32
0.85-0.9	14
0.9-0.95	6
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9747	High Similarity	NPC288903
0.9375	High Similarity	NPC323103
0.9367	High Similarity	NPC121800
0.9286	High Similarity	NPC9822
0.9259	High Similarity	NPC270507
0.9241	High Similarity	NPC170484
0.9136	High Similarity	NPC103387
0.9024	High Similarity	NPC285773
0.8824	High Similarity	NPC322387
0.8721	High Similarity	NPC329064
0.8659	High Similarity	NPC127343
0.8605	High Similarity	NPC89377
0.8571	High Similarity	NPC92754
0.8571	High Similarity	NPC270654
0.8571	High Similarity	NPC249912
0.8571	High Similarity	NPC276775
0.8523	High Similarity	NPC274455
0.8523	High Similarity	NPC86670
0.8523	High Similarity	NPC70940
0.8478	Intermediate Similarity	NPC78701
0.8478	Intermediate Similarity	NPC35448
0.8478	Intermediate Similarity	NPC225060
0.8427	Intermediate Similarity	NPC317645
0.8409	Intermediate Similarity	NPC220893
0.8387	Intermediate Similarity	NPC146351
0.8372	Intermediate Similarity	NPC95965
0.8372	Intermediate Similarity	NPC58616
0.8353	Intermediate Similarity	NPC44830
0.8352	Intermediate Similarity	NPC130398
0.8316	Intermediate Similarity	NPC160382
0.8315	Intermediate Similarity	NPC84288
0.8298	Intermediate Similarity	NPC42211
0.8298	Intermediate Similarity	NPC70624
0.8298	Intermediate Similarity	NPC473325
0.8295	Intermediate Similarity	NPC304760
0.8202	Intermediate Similarity	NPC173443
0.8191	Intermediate Similarity	NPC118343
0.8161	Intermediate Similarity	NPC475710
0.8148	Intermediate Similarity	NPC208075
0.8125	Intermediate Similarity	NPC474365
0.8125	Intermediate Similarity	NPC301943
0.8111	Intermediate Similarity	NPC185501
0.8085	Intermediate Similarity	NPC160548
0.8085	Intermediate Similarity	NPC210529
0.8085	Intermediate Similarity	NPC175852
0.8068	Intermediate Similarity	NPC318107
0.8061	Intermediate Similarity	NPC119271
0.8025	Intermediate Similarity	NPC285679
0.8025	Intermediate Similarity	NPC271437
0.8022	Intermediate Similarity	NPC110704
0.8021	Intermediate Similarity	NPC188895
0.8	Intermediate Similarity	NPC203925
0.8	Intermediate Similarity	NPC231591
0.8	Intermediate Similarity	NPC325497
0.798	Intermediate Similarity	NPC56493
0.7957	Intermediate Similarity	NPC172925
0.7952	Intermediate Similarity	NPC175393
0.7938	Intermediate Similarity	NPC89886
0.7912	Intermediate Similarity	NPC213156
0.7912	Intermediate Similarity	NPC240108
0.7901	Intermediate Similarity	NPC74458
0.79	Intermediate Similarity	NPC17417
0.79	Intermediate Similarity	NPC83628
0.79	Intermediate Similarity	NPC10251
0.79	Intermediate Similarity	NPC265407
0.79	Intermediate Similarity	NPC469636
0.7895	Intermediate Similarity	NPC229242
0.7857	Intermediate Similarity	NPC31786
0.7857	Intermediate Similarity	NPC298023
0.7849	Intermediate Similarity	NPC261181
0.7826	Intermediate Similarity	NPC476484
0.7822	Intermediate Similarity	NPC93084
0.7822	Intermediate Similarity	NPC251854
0.7822	Intermediate Similarity	NPC174099
0.7822	Intermediate Similarity	NPC158854
0.7822	Intermediate Similarity	NPC214067
0.7822	Intermediate Similarity	NPC196246
0.7812	Intermediate Similarity	NPC7435
0.7812	Intermediate Similarity	NPC217621
0.7789	Intermediate Similarity	NPC253423
0.7789	Intermediate Similarity	NPC226041
0.7778	Intermediate Similarity	NPC269457
0.7778	Intermediate Similarity	NPC96625
0.7778	Intermediate Similarity	NPC209632
0.7765	Intermediate Similarity	NPC76455
0.7765	Intermediate Similarity	NPC137847
0.7755	Intermediate Similarity	NPC60679
0.7745	Intermediate Similarity	NPC1082
0.7745	Intermediate Similarity	NPC305912
0.7745	Intermediate Similarity	NPC210089
0.7745	Intermediate Similarity	NPC260818
0.7745	Intermediate Similarity	NPC474157
0.7742	Intermediate Similarity	NPC77273
0.7723	Intermediate Similarity	NPC31274
0.7723	Intermediate Similarity	NPC281604
0.7723	Intermediate Similarity	NPC474364
0.7717	Intermediate Similarity	NPC62765
0.7711	Intermediate Similarity	NPC108218
0.7708	Intermediate Similarity	NPC271475
0.77	Intermediate Similarity	NPC30594
0.77	Intermediate Similarity	NPC37622
0.77	Intermediate Similarity	NPC1065
0.7684	Intermediate Similarity	NPC12695
0.7684	Intermediate Similarity	NPC261947
0.7683	Intermediate Similarity	NPC155429
0.7677	Intermediate Similarity	NPC19136
0.7677	Intermediate Similarity	NPC269644
0.7677	Intermediate Similarity	NPC114594
0.7674	Intermediate Similarity	NPC300205
0.7674	Intermediate Similarity	NPC78517
0.7674	Intermediate Similarity	NPC167577
0.767	Intermediate Similarity	NPC82899
0.767	Intermediate Similarity	NPC270699
0.767	Intermediate Similarity	NPC321852
0.766	Intermediate Similarity	NPC23453
0.7653	Intermediate Similarity	NPC45613
0.7653	Intermediate Similarity	NPC304873
0.7653	Intermediate Similarity	NPC25458
0.7647	Intermediate Similarity	NPC329318
0.7634	Intermediate Similarity	NPC119631
0.7634	Intermediate Similarity	NPC86987
0.7629	Intermediate Similarity	NPC221825
0.7629	Intermediate Similarity	NPC476042
0.7604	Intermediate Similarity	NPC103048
0.7604	Intermediate Similarity	NPC325499
0.7596	Intermediate Similarity	NPC272524
0.7596	Intermediate Similarity	NPC128368
0.7586	Intermediate Similarity	NPC157055
0.7586	Intermediate Similarity	NPC164086
0.7576	Intermediate Similarity	NPC329556
0.7573	Intermediate Similarity	NPC476003
0.7573	Intermediate Similarity	NPC167504
0.7558	Intermediate Similarity	NPC176228
0.7558	Intermediate Similarity	NPC224544
0.7558	Intermediate Similarity	NPC285470
0.7558	Intermediate Similarity	NPC2785
0.7558	Intermediate Similarity	NPC36342
0.7553	Intermediate Similarity	NPC323164
0.7551	Intermediate Similarity	NPC52472
0.7551	Intermediate Similarity	NPC112552
0.7549	Intermediate Similarity	NPC85493
0.7549	Intermediate Similarity	NPC99846
0.7549	Intermediate Similarity	NPC269023
0.7528	Intermediate Similarity	NPC197581
0.7528	Intermediate Similarity	NPC39600
0.7525	Intermediate Similarity	NPC474111
0.7525	Intermediate Similarity	NPC329705
0.7525	Intermediate Similarity	NPC142326
0.7525	Intermediate Similarity	NPC94751
0.7524	Intermediate Similarity	NPC153053
0.7524	Intermediate Similarity	NPC307651
0.7524	Intermediate Similarity	NPC308744
0.75	Intermediate Similarity	NPC158282
0.75	Intermediate Similarity	NPC61944
0.75	Intermediate Similarity	NPC79496
0.75	Intermediate Similarity	NPC89950
0.75	Intermediate Similarity	NPC100039
0.75	Intermediate Similarity	NPC303245
0.75	Intermediate Similarity	NPC73978
0.7476	Intermediate Similarity	NPC234639
0.7475	Intermediate Similarity	NPC284477
0.7475	Intermediate Similarity	NPC474112
0.747	Intermediate Similarity	NPC208302
0.7453	Intermediate Similarity	NPC210092
0.7453	Intermediate Similarity	NPC474685
0.7451	Intermediate Similarity	NPC156648
0.7451	Intermediate Similarity	NPC470391
0.7449	Intermediate Similarity	NPC245561
0.7447	Intermediate Similarity	NPC187725
0.7447	Intermediate Similarity	NPC141607
0.7442	Intermediate Similarity	NPC245966
0.7442	Intermediate Similarity	NPC3672
0.7442	Intermediate Similarity	NPC287790
0.7429	Intermediate Similarity	NPC161611
0.7426	Intermediate Similarity	NPC476198
0.7426	Intermediate Similarity	NPC105899
0.7423	Intermediate Similarity	NPC289201
0.7423	Intermediate Similarity	NPC477767
0.7416	Intermediate Similarity	NPC106313
0.7416	Intermediate Similarity	NPC230068
0.7412	Intermediate Similarity	NPC189371
0.74	Intermediate Similarity	NPC13426
0.74	Intermediate Similarity	NPC255676
0.7391	Intermediate Similarity	NPC169050
0.7391	Intermediate Similarity	NPC286608
0.7386	Intermediate Similarity	NPC190567
0.7386	Intermediate Similarity	NPC309279
0.7383	Intermediate Similarity	NPC149691
0.7379	Intermediate Similarity	NPC40178
0.7374	Intermediate Similarity	NPC282895
0.7363	Intermediate Similarity	NPC252067
0.7358	Intermediate Similarity	NPC474363
0.7356	Intermediate Similarity	NPC103488
0.7347	Intermediate Similarity	NPC322598
0.7347	Intermediate Similarity	NPC145052
0.7333	Intermediate Similarity	NPC474314
0.7333	Intermediate Similarity	NPC308619
0.7333	Intermediate Similarity	NPC324835
0.7333	Intermediate Similarity	NPC127491
0.7327	Intermediate Similarity	NPC38209

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 NPC294134 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	166
0.1-0.2	851
0.2-0.3	1380
0.3-0.4	3194
0.4-0.5	2144
0.5-0.6	1044
0.6-0.7	298
0.7-0.8	52
0.8-0.85	9
0.85-0.9	10
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9241	High Similarity	NPD9490	Approved
0.9024	High Similarity	NPD9491	Approved
0.8876	High Similarity	NPD1989	Approved
0.8875	High Similarity	NPD227	Approved
0.8875	High Similarity	NPD225	Approved
0.8824	High Similarity	NPD1087	Approved
0.8736	High Similarity	NPD3672	Approved
0.8736	High Similarity	NPD3673	Approved
0.8621	High Similarity	NPD800	Approved
0.8554	High Similarity	NPD226	Approved
0.8523	High Similarity	NPD1090	Approved
0.8523	High Similarity	NPD1086	Approved
0.8523	High Similarity	NPD1089	Approved
0.8333	Intermediate Similarity	NPD1088	Approved
0.8242	Intermediate Similarity	NPD1563	Approved
0.8222	Intermediate Similarity	NPD1239	Approved
0.8191	Intermediate Similarity	NPD1238	Approved
0.8152	Intermediate Similarity	NPD1693	Approved
0.8085	Intermediate Similarity	NPD9495	Approved
0.8068	Intermediate Similarity	NPD9257	Approved
0.8068	Intermediate Similarity	NPD9259	Approved
0.8	Intermediate Similarity	NPD5347	Phase 2
0.8	Intermediate Similarity	NPD5346	Phase 2
0.7979	Intermediate Similarity	NPD1564	Approved
0.7979	Intermediate Similarity	NPD1565	Approved
0.7979	Intermediate Similarity	NPD1566	Phase 3
0.7978	Intermediate Similarity	NPD4793	Discontinued
0.7957	Intermediate Similarity	NPD688	Clinical (unspecified phase)
0.79	Intermediate Similarity	NPD2182	Approved
0.7857	Intermediate Similarity	NPD164	Approved
0.7849	Intermediate Similarity	NPD1202	Approved
0.7822	Intermediate Similarity	NPD4233	Approved
0.7822	Intermediate Similarity	NPD1756	Approved
0.7822	Intermediate Similarity	NPD4234	Approved
0.7822	Intermediate Similarity	NPD1752	Approved
0.7812	Intermediate Similarity	NPD2066	Phase 3
0.7812	Intermediate Similarity	NPD7798	Approved
0.7745	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7717	Intermediate Similarity	NPD9256	Approved
0.7717	Intermediate Similarity	NPD9258	Approved
0.766	Intermediate Similarity	NPD5122	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD3646	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD2067	Discontinued
0.7596	Intermediate Similarity	NPD2607	Approved
0.7576	Intermediate Similarity	NPD1930	Approved
0.7576	Intermediate Similarity	NPD1929	Approved
0.7576	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7524	Intermediate Similarity	NPD2652	Approved
0.7524	Intermediate Similarity	NPD2650	Approved
0.7474	Intermediate Similarity	NPD1066	Discontinued
0.7453	Intermediate Similarity	NPD4766	Approved
0.7453	Intermediate Similarity	NPD2629	Approved
0.74	Intermediate Similarity	NPD6647	Phase 2
0.7396	Intermediate Similarity	NPD9260	Approved
0.7391	Intermediate Similarity	NPD1282	Approved
0.7327	Intermediate Similarity	NPD5909	Discontinued
0.732	Intermediate Similarity	NPD5206	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD4574	Approved
0.7315	Intermediate Similarity	NPD4576	Approved
0.7264	Intermediate Similarity	NPD1279	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD2347	Approved
0.7245	Intermediate Similarity	NPD9566	Approved
0.7212	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7196	Intermediate Similarity	NPD1373	Approved
0.7196	Intermediate Similarity	NPD1370	Approved
0.7196	Intermediate Similarity	NPD1374	Approved
0.7196	Intermediate Similarity	NPD1371	Approved
0.7191	Intermediate Similarity	NPD1507	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD6685	Approved
0.7172	Intermediate Similarity	NPD253	Approved
0.7172	Intermediate Similarity	NPD5926	Approved
0.7157	Intermediate Similarity	NPD1237	Approved
0.713	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7129	Intermediate Similarity	NPD1932	Approved
0.7128	Intermediate Similarity	NPD531	Approved
0.7111	Intermediate Similarity	NPD942	Approved
0.7103	Intermediate Similarity	NPD7094	Approved
0.7103	Intermediate Similarity	NPD6858	Approved
0.71	Intermediate Similarity	NPD3097	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD5048	Discontinued
0.7059	Intermediate Similarity	NPD5738	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD5306	Approved
0.7054	Intermediate Similarity	NPD5305	Approved
0.7045	Intermediate Similarity	NPD9294	Approved
0.7037	Intermediate Similarity	NPD1241	Discontinued
0.7027	Intermediate Similarity	NPD9545	Approved
0.7021	Intermediate Similarity	NPD650	Approved
0.7019	Intermediate Similarity	NPD5706	Approved
0.7019	Intermediate Similarity	NPD5704	Approved
0.7019	Intermediate Similarity	NPD5705	Approved
0.7019	Intermediate Similarity	NPD467	Phase 1
0.7011	Intermediate Similarity	NPD9716	Approved
0.6991	Remote Similarity	NPD4136	Approved
0.6991	Remote Similarity	NPD4135	Approved
0.6991	Remote Similarity	NPD4106	Approved
0.6944	Remote Similarity	NPD181	Approved
0.693	Remote Similarity	NPD2610	Approved
0.693	Remote Similarity	NPD3131	Approved
0.693	Remote Similarity	NPD7437	Approved
0.693	Remote Similarity	NPD2608	Approved
0.693	Remote Similarity	NPD4217	Approved
0.693	Remote Similarity	NPD2609	Approved
0.693	Remote Similarity	NPD7436	Approved
0.693	Remote Similarity	NPD2611	Approved
0.693	Remote Similarity	NPD4806	Approved
0.693	Remote Similarity	NPD4215	Approved
0.693	Remote Similarity	NPD4218	Approved
0.693	Remote Similarity	NPD3132	Approved
0.693	Remote Similarity	NPD2612	Approved
0.693	Remote Similarity	NPD4216	Approved
0.693	Remote Similarity	NPD4807	Approved
0.6893	Remote Similarity	NPD5765	Approved
0.6893	Remote Similarity	NPD9261	Approved
0.6887	Remote Similarity	NPD2329	Discontinued
0.6881	Remote Similarity	NPD1280	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD689	Discontinued
0.6875	Remote Similarity	NPD1894	Discontinued
0.6852	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6847	Remote Similarity	NPD9493	Approved
0.6842	Remote Similarity	NPD506	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD1317	Discontinued
0.6818	Remote Similarity	NPD1246	Approved
0.6818	Remote Similarity	NPD5951	Approved
0.6814	Remote Similarity	NPD4105	Approved
0.6814	Remote Similarity	NPD4102	Approved
0.6789	Remote Similarity	NPD5277	Phase 2
0.6786	Remote Similarity	NPD6065	Approved
0.6783	Remote Similarity	NPD6287	Discontinued
0.6774	Remote Similarity	NPD3971	Phase 1
0.6762	Remote Similarity	NPD1040	Phase 2
0.6754	Remote Similarity	NPD17	Approved
0.6752	Remote Similarity	NPD5667	Approved
0.6739	Remote Similarity	NPD9250	Approved
0.6735	Remote Similarity	NPD7609	Phase 3
0.6727	Remote Similarity	NPD6010	Discontinued
0.6726	Remote Similarity	NPD2617	Discontinued
0.6699	Remote Similarity	NPD3135	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD3134	Approved
0.6697	Remote Similarity	NPD9508	Approved
0.6697	Remote Similarity	NPD6912	Phase 3
0.6695	Remote Similarity	NPD2159	Approved
0.6695	Remote Similarity	NPD2625	Approved
0.6695	Remote Similarity	NPD2626	Approved
0.6695	Remote Similarity	NPD2627	Approved
0.6695	Remote Similarity	NPD2160	Approved
0.6695	Remote Similarity	NPD2628	Approved
0.6667	Remote Similarity	NPD5240	Approved
0.6667	Remote Similarity	NPD5236	Approved
0.6667	Remote Similarity	NPD5239	Approved
0.6667	Remote Similarity	NPD5278	Discontinued
0.6667	Remote Similarity	NPD5237	Approved
0.6667	Remote Similarity	NPD5235	Approved
0.6667	Remote Similarity	NPD5981	Approved
0.6667	Remote Similarity	NPD7631	Approved
0.6638	Remote Similarity	NPD518	Clinical (unspecified phase)
0.6638	Remote Similarity	NPD1281	Approved
0.6636	Remote Similarity	NPD9263	Approved
0.6636	Remote Similarity	NPD1358	Approved
0.6636	Remote Similarity	NPD9264	Approved
0.6636	Remote Similarity	NPD9267	Approved
0.6636	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD5734	Clinical (unspecified phase)
0.661	Remote Similarity	NPD2198	Approved
0.661	Remote Similarity	NPD2199	Approved
0.6607	Remote Similarity	NPD1348	Approved
0.6607	Remote Similarity	NPD255	Approved
0.6607	Remote Similarity	NPD256	Approved
0.6607	Remote Similarity	NPD4198	Discontinued
0.6606	Remote Similarity	NPD3642	Approved
0.6606	Remote Similarity	NPD2201	Approved
0.6606	Remote Similarity	NPD3643	Approved
0.6606	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD3644	Approved
0.6604	Remote Similarity	NPD1018	Approved
0.6598	Remote Similarity	NPD1101	Approved
0.6583	Remote Similarity	NPD3662	Phase 3
0.6583	Remote Similarity	NPD5204	Approved
0.6583	Remote Similarity	NPD3661	Approved
0.6583	Remote Similarity	NPD3663	Approved
0.6583	Remote Similarity	NPD3664	Approved
0.6581	Remote Similarity	NPD1608	Approved
0.6579	Remote Similarity	NPD4479	Discontinued
0.6574	Remote Similarity	NPD74	Approved
0.6574	Remote Similarity	NPD9266	Approved
0.6555	Remote Similarity	NPD552	Approved
0.6555	Remote Similarity	NPD9567	Approved
0.6555	Remote Similarity	NPD553	Approved
0.6529	Remote Similarity	NPD2613	Approved
0.6529	Remote Similarity	NPD4617	Approved
0.6529	Remote Similarity	NPD4620	Approved
0.6529	Remote Similarity	NPD5201	Approved
0.6529	Remote Similarity	NPD6832	Phase 2
0.6529	Remote Similarity	NPD5203	Approved
0.6529	Remote Similarity	NPD5202	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD5585	Approved
0.6522	Remote Similarity	NPD1245	Approved
0.65	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.65	Remote Similarity	NPD1508	Approved
0.65	Remote Similarity	NPD1019	Discontinued
0.6496	Remote Similarity	NPD3603	Phase 3

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