NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	192.12
Volume:	214.586
LogP:	3.225
LogD:	3.115
LogS:	-3.31
# 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:	0.531
Synthetic Accessibility Score:	1.826
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:	-4.558
MDCK Permeability:	2.4391740225837566e-05
Pgp-inhibitor:	0.084
Pgp-substrate:	0.008
Human Intestinal Absorption (HIA):	0.016
20% Bioavailability (F20%):	0.907
30% Bioavailability (F30%):	0.969

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.991
Plasma Protein Binding (PPB):	89.95525360107422%
Volume Distribution (VD):	0.592
Pgp-substrate:	20.391324996948242%

ADMET: Metabolism

CYP1A2-inhibitor:	0.954
CYP1A2-substrate:	0.825
CYP2C19-inhibitor:	0.774
CYP2C19-substrate:	0.85
CYP2C9-inhibitor:	0.559
CYP2C9-substrate:	0.707
CYP2D6-inhibitor:	0.236
CYP2D6-substrate:	0.68
CYP3A4-inhibitor:	0.201
CYP3A4-substrate:	0.487

ADMET: Excretion

Clearance (CL):	3.375
Half-life (T1/2):	0.51

ADMET: Toxicity

hERG Blockers:	0.006
Human Hepatotoxicity (H-HT):	0.01
Drug-inuced Liver Injury (DILI):	0.629
AMES Toxicity:	0.031
Rat Oral Acute Toxicity:	0.051
Maximum Recommended Daily Dose:	0.031
Skin Sensitization:	0.313
Carcinogencity:	0.528
Eye Corrosion:	0.495
Eye Irritation:	0.974
Respiratory Toxicity:	0.222

Download Data

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

Natural Product: NPC280760

Natural Product ID:	NPC280760
*Common Name:**	O-Acetyl-Thymol
IUPAC Name:	(5-methyl-2-propan-2-ylphenyl) acetate
Synonyms:
Standard InCHIKey:	WFMIUXMJJBBOGJ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C12H16O2/c1-8(2)11-6-5-9(3)7-12(11)14-10(4)13/h5-8H,1-4H3
SMILES:	CC(C)c1ccc(C)cc1OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3343661
PubChem CID:	68252
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001549] Monoterpenoids [CHEMONTID:0000051] Aromatic monoterpenoids

*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
NPO15243	Pimenta dioica	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10869193]
NPO19472	Thymus vulgaris	Species	Lamiaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[12088434]
NPO27360	Pyracantha fortuneana	Species	Rosaceae	Eukaryota	fruit	n.a.	n.a.	PMID[16872137]
NPO15243	Pimenta dioica	Species	Myrtaceae	Eukaryota	Berries	n.a.	n.a.	PMID[18314960]
NPO11654	Eusynstyela misakiensis	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[19505081]
NPO19472	Thymus vulgaris	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21707257]
NPO15436	Brucea mollis	Species	Simaroubaceae	Eukaryota	n.a.	stem	n.a.	PMID[22070654]
NPO15436	Brucea mollis	Species	Simaroubaceae	Eukaryota	stems	n.a.	n.a.	PMID[22070654]
NPO15436	Brucea mollis	Species	Simaroubaceae	Eukaryota	n.a.	stem	n.a.	PMID[24199564]
NPO21355	Elsholtzia ciliata	Species	Lamiaceae	Eukaryota	Aerial Parts	n.a.	n.a.	PMID[32991171]
NPO11654	Eusynstyela misakiensis	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[7931370]
NPO15243	Pimenta dioica	Species	Myrtaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO15243	Pimenta dioica	Species	Myrtaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO19472	Thymus vulgaris	Species	Lamiaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO19472	Thymus vulgaris	Species	Lamiaceae	Eukaryota	Essential Oil	n.a.	n.a.	Database[FooDB]
NPO15243	Pimenta dioica	Species	Myrtaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO19472	Thymus vulgaris	Species	Lamiaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO15243	Pimenta dioica	Species	Myrtaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO15243	Pimenta dioica	Species	Myrtaceae	Eukaryota	Leaf Essent. Oil	n.a.	n.a.	Database[FooDB]
NPO17550	Origanum onites	Species	Lamiaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO19472	Thymus vulgaris	Species	Lamiaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO15243	Pimenta dioica	Species	Myrtaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO17550	Origanum onites	Species	Lamiaceae	Eukaryota	Shoot	n.a.	n.a.	Database[FooDB]
NPO19472	Thymus vulgaris	Species	Lamiaceae	Eukaryota	Shoot	n.a.	n.a.	Database[FooDB]
NPO19472	Thymus vulgaris	Species	Lamiaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO12935	Thymus quinquecostatus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23814	Elsholtzia splendens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19472	Thymus vulgaris	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21355	Elsholtzia ciliata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18046	Mosla chinensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15243	Pimenta dioica	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17550	Origanum onites	Species	Lamiaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO19472	Thymus vulgaris	Species	Lamiaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO18046	Mosla chinensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23814	Elsholtzia splendens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21355	Elsholtzia ciliata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15243	Pimenta dioica	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12935	Thymus quinquecostatus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19472	Thymus vulgaris	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18046	Mosla chinensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15243	Pimenta dioica	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO19472	Thymus vulgaris	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21355	Elsholtzia ciliata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12935	Thymus quinquecostatus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO21355	Elsholtzia ciliata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO18046	Mosla chinensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO19472	Thymus vulgaris	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO15152	Fagara leprieurii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO14275	Carissa opaca	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27360	Pyracantha fortuneana	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3904	Casearia esculenta	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14854	Stereocaulon ramulosum	Species	Stereocaulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15436	Brucea mollis	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18046	Mosla chinensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12504	Penstemon acuminatus	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15618	Teucrium luteum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6262	Rumphella aggregata	Species	Plexauridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21355	Elsholtzia ciliata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15243	Pimenta dioica	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23814	Elsholtzia splendens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1685	Mespilodaphne pretiosa	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO3209	Anchusa strigosa	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12935	Thymus quinquecostatus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19472	Thymus vulgaris	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17550	Origanum onites	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13652	Laurilia sulcata	Species	Corticiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15532	Polygala crotalarioides	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11654	Eusynstyela misakiensis	Species	n.a.	n.a.	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
NPO17550	NPC280760	Other	Shoot	0.01	0.01	0.01	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
EC50	2
Others	1

Activity Type	# Activity
Cell Line	1
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	Survival	>	100.0	%	PMID[538954]
NPT1021	Organism	Leishmania infantum	Leishmania infantum	EC50	=	9.07	ug.mL-1	PMID[538954]
NPT1021	Organism	Leishmania infantum	Leishmania infantum	EC50	=	10.95	ug.mL-1	PMID[538954]

☑ 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 NPC280760 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	302
0.1-0.2	1765
0.2-0.3	4952
0.3-0.4	13264
0.4-0.5	4843
0.5-0.6	8527
0.6-0.7	7954
0.7-0.8	1015
0.8-0.85	60
0.85-0.9	12
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9204	High Similarity	NPC322569
0.9027	High Similarity	NPC98748
0.8952	High Similarity	NPC12870
0.8952	High Similarity	NPC24327
0.8879	High Similarity	NPC476332
0.8879	High Similarity	NPC473464
0.8814	High Similarity	NPC170749
0.8704	High Similarity	NPC30416
0.8679	High Similarity	NPC307425
0.8611	High Similarity	NPC473855
0.8585	High Similarity	NPC107101
0.8584	High Similarity	NPC87563
0.8583	High Similarity	NPC128321
0.8583	High Similarity	NPC329272
0.8522	High Similarity	NPC471503
0.8522	High Similarity	NPC471498
0.8496	Intermediate Similarity	NPC303522
0.8462	Intermediate Similarity	NPC14177
0.8443	Intermediate Similarity	NPC176590
0.8443	Intermediate Similarity	NPC81261
0.844	Intermediate Similarity	NPC473393
0.844	Intermediate Similarity	NPC139891
0.8407	Intermediate Similarity	NPC26615
0.8362	Intermediate Similarity	NPC238075
0.8349	Intermediate Similarity	NPC283546
0.8333	Intermediate Similarity	NPC470887
0.8333	Intermediate Similarity	NPC190212
0.8319	Intermediate Similarity	NPC233238
0.8319	Intermediate Similarity	NPC245552
0.8306	Intermediate Similarity	NPC249425
0.8305	Intermediate Similarity	NPC471504
0.8305	Intermediate Similarity	NPC473290
0.8304	Intermediate Similarity	NPC259554
0.8304	Intermediate Similarity	NPC149545
0.823	Intermediate Similarity	NPC25067
0.823	Intermediate Similarity	NPC88868
0.823	Intermediate Similarity	NPC473809
0.823	Intermediate Similarity	NPC231251
0.8224	Intermediate Similarity	NPC470161
0.822	Intermediate Similarity	NPC234956
0.822	Intermediate Similarity	NPC471449
0.822	Intermediate Similarity	NPC51341
0.8214	Intermediate Similarity	NPC291837
0.8211	Intermediate Similarity	NPC156298
0.8198	Intermediate Similarity	NPC176971
0.8158	Intermediate Similarity	NPC470723
0.8151	Intermediate Similarity	NPC328485
0.8136	Intermediate Similarity	NPC159916
0.8125	Intermediate Similarity	NPC151530
0.8125	Intermediate Similarity	NPC157473
0.812	Intermediate Similarity	NPC163398
0.812	Intermediate Similarity	NPC33717
0.8115	Intermediate Similarity	NPC474237
0.8108	Intermediate Similarity	NPC288760
0.8108	Intermediate Similarity	NPC128730
0.8108	Intermediate Similarity	NPC227255
0.8103	Intermediate Similarity	NPC41851
0.8099	Intermediate Similarity	NPC302211
0.8099	Intermediate Similarity	NPC188997
0.8087	Intermediate Similarity	NPC199462
0.8083	Intermediate Similarity	NPC267064
0.8083	Intermediate Similarity	NPC212559
0.807	Intermediate Similarity	NPC141068
0.8056	Intermediate Similarity	NPC95755
0.8051	Intermediate Similarity	NPC183154
0.8051	Intermediate Similarity	NPC263754
0.8036	Intermediate Similarity	NPC326801
0.8036	Intermediate Similarity	NPC326447
0.8034	Intermediate Similarity	NPC283169
0.8033	Intermediate Similarity	NPC261992
0.8033	Intermediate Similarity	NPC248786
0.8017	Intermediate Similarity	NPC168707
0.8017	Intermediate Similarity	NPC475839
0.8017	Intermediate Similarity	NPC48623
0.8017	Intermediate Similarity	NPC109241
0.8	Intermediate Similarity	NPC275627
0.8	Intermediate Similarity	NPC474636
0.8	Intermediate Similarity	NPC474874
0.7984	Intermediate Similarity	NPC101894
0.7983	Intermediate Similarity	NPC96705
0.7969	Intermediate Similarity	NPC472524
0.7967	Intermediate Similarity	NPC140521
0.7966	Intermediate Similarity	NPC128633
0.7966	Intermediate Similarity	NPC312105
0.7965	Intermediate Similarity	NPC233320
0.7951	Intermediate Similarity	NPC248429
0.7951	Intermediate Similarity	NPC96286
0.7949	Intermediate Similarity	NPC235250
0.7946	Intermediate Similarity	NPC238115
0.7934	Intermediate Similarity	NPC218753
0.7934	Intermediate Similarity	NPC45663
0.7934	Intermediate Similarity	NPC96423
0.7931	Intermediate Similarity	NPC474920
0.7931	Intermediate Similarity	NPC266116
0.7928	Intermediate Similarity	NPC179686
0.792	Intermediate Similarity	NPC474821
0.792	Intermediate Similarity	NPC474670
0.7917	Intermediate Similarity	NPC472593
0.7909	Intermediate Similarity	NPC72729
0.7907	Intermediate Similarity	NPC211164
0.7903	Intermediate Similarity	NPC471827
0.7903	Intermediate Similarity	NPC471828
0.7903	Intermediate Similarity	NPC249836
0.7899	Intermediate Similarity	NPC238176
0.7899	Intermediate Similarity	NPC25648
0.7899	Intermediate Similarity	NPC187993
0.789	Intermediate Similarity	NPC79241
0.789	Intermediate Similarity	NPC6597
0.7886	Intermediate Similarity	NPC320287
0.7886	Intermediate Similarity	NPC96940
0.7886	Intermediate Similarity	NPC472518
0.7881	Intermediate Similarity	NPC473718
0.7876	Intermediate Similarity	NPC1065
0.7874	Intermediate Similarity	NPC474617
0.7874	Intermediate Similarity	NPC475102
0.7869	Intermediate Similarity	NPC14287
0.7857	Intermediate Similarity	NPC108875
0.7857	Intermediate Similarity	NPC109637
0.7857	Intermediate Similarity	NPC38079
0.7851	Intermediate Similarity	NPC193193
0.7851	Intermediate Similarity	NPC31314
0.784	Intermediate Similarity	NPC474632
0.7838	Intermediate Similarity	NPC300166
0.7838	Intermediate Similarity	NPC84325
0.7833	Intermediate Similarity	NPC265547
0.7833	Intermediate Similarity	NPC124916
0.7833	Intermediate Similarity	NPC283616
0.7833	Intermediate Similarity	NPC293424
0.7833	Intermediate Similarity	NPC171023
0.7833	Intermediate Similarity	NPC152306
0.7823	Intermediate Similarity	NPC78446
0.7823	Intermediate Similarity	NPC470162
0.7823	Intermediate Similarity	NPC27671
0.7823	Intermediate Similarity	NPC470163
0.7823	Intermediate Similarity	NPC111088
0.7823	Intermediate Similarity	NPC111347
0.7823	Intermediate Similarity	NPC73413
0.7823	Intermediate Similarity	NPC61685
0.7823	Intermediate Similarity	NPC89630
0.7823	Intermediate Similarity	NPC201667
0.7823	Intermediate Similarity	NPC248557
0.7823	Intermediate Similarity	NPC75432
0.782	Intermediate Similarity	NPC472523
0.7815	Intermediate Similarity	NPC69539
0.7807	Intermediate Similarity	NPC258171
0.7805	Intermediate Similarity	NPC325301
0.7798	Intermediate Similarity	NPC259512
0.7798	Intermediate Similarity	NPC312132
0.7788	Intermediate Similarity	NPC475269
0.7788	Intermediate Similarity	NPC470393
0.7787	Intermediate Similarity	NPC307253
0.7787	Intermediate Similarity	NPC163200
0.7787	Intermediate Similarity	NPC180006
0.7787	Intermediate Similarity	NPC235190
0.7786	Intermediate Similarity	NPC265515
0.7786	Intermediate Similarity	NPC115861
0.7778	Intermediate Similarity	NPC98372
0.7778	Intermediate Similarity	NPC142087
0.7778	Intermediate Similarity	NPC228452
0.7778	Intermediate Similarity	NPC95034
0.7769	Intermediate Similarity	NPC85895
0.7769	Intermediate Similarity	NPC37858
0.7769	Intermediate Similarity	NPC160235
0.7769	Intermediate Similarity	NPC281356
0.7769	Intermediate Similarity	NPC137294
0.7769	Intermediate Similarity	NPC298796
0.776	Intermediate Similarity	NPC279118
0.776	Intermediate Similarity	NPC252962
0.7757	Intermediate Similarity	NPC321956
0.7752	Intermediate Similarity	NPC474635
0.7744	Intermediate Similarity	NPC476191
0.7742	Intermediate Similarity	NPC279379
0.7742	Intermediate Similarity	NPC315807
0.7742	Intermediate Similarity	NPC273772
0.7742	Intermediate Similarity	NPC109675
0.7739	Intermediate Similarity	NPC75440
0.7734	Intermediate Similarity	NPC2989
0.7731	Intermediate Similarity	NPC322358
0.7731	Intermediate Similarity	NPC51345
0.7727	Intermediate Similarity	NPC476171
0.7724	Intermediate Similarity	NPC52247
0.7717	Intermediate Similarity	NPC185066
0.7717	Intermediate Similarity	NPC474616
0.7717	Intermediate Similarity	NPC474651
0.7717	Intermediate Similarity	NPC474623
0.7712	Intermediate Similarity	NPC90903
0.7712	Intermediate Similarity	NPC165106
0.771	Intermediate Similarity	NPC252095
0.7705	Intermediate Similarity	NPC474131
0.7705	Intermediate Similarity	NPC230951
0.7699	Intermediate Similarity	NPC292792
0.7699	Intermediate Similarity	NPC475225
0.7699	Intermediate Similarity	NPC241224
0.7699	Intermediate Similarity	NPC2518
0.7698	Intermediate Similarity	NPC471826
0.7698	Intermediate Similarity	NPC234109
0.7698	Intermediate Similarity	NPC188327
0.7686	Intermediate Similarity	NPC190514
0.7686	Intermediate Similarity	NPC63010
0.7686	Intermediate Similarity	NPC139047

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 NPC280760 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	309
0.1-0.2	1067
0.2-0.3	1479
0.3-0.4	2704
0.4-0.5	1791
0.5-0.6	1131
0.6-0.7	535
0.7-0.8	124
0.8-0.85	8
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8793	High Similarity	NPD1611	Approved
0.8696	High Similarity	NPD5691	Approved
0.8512	High Similarity	NPD2237	Approved
0.8462	Intermediate Similarity	NPD4626	Approved
0.8462	Intermediate Similarity	NPD1778	Approved
0.844	Intermediate Similarity	NPD9697	Approved
0.8407	Intermediate Similarity	NPD5535	Approved
0.8362	Intermediate Similarity	NPD7644	Approved
0.8305	Intermediate Similarity	NPD17	Approved
0.8235	Intermediate Similarity	NPD3496	Discontinued
0.822	Intermediate Similarity	NPD5585	Approved
0.8099	Intermediate Similarity	NPD1608	Approved
0.8049	Intermediate Similarity	NPD2797	Approved
0.8036	Intermediate Similarity	NPD3134	Approved
0.8034	Intermediate Similarity	NPD6671	Approved
0.8017	Intermediate Similarity	NPD1281	Approved
0.7953	Intermediate Similarity	NPD8032	Phase 2
0.7903	Intermediate Similarity	NPD3266	Approved
0.7903	Intermediate Similarity	NPD3267	Approved
0.7891	Intermediate Similarity	NPD4140	Approved
0.7891	Intermediate Similarity	NPD4060	Phase 1
0.7886	Intermediate Similarity	NPD4749	Approved
0.7886	Intermediate Similarity	NPD4359	Approved
0.7823	Intermediate Similarity	NPD1283	Approved
0.7807	Intermediate Similarity	NPD1358	Approved
0.7798	Intermediate Similarity	NPD288	Approved
0.7769	Intermediate Similarity	NPD1651	Approved
0.7739	Intermediate Similarity	NPD2684	Approved
0.7734	Intermediate Similarity	NPD3268	Approved
0.7724	Intermediate Similarity	NPD422	Phase 1
0.7712	Intermediate Similarity	NPD5283	Phase 1
0.7706	Intermediate Similarity	NPD844	Approved
0.7692	Intermediate Similarity	NPD1137	Approved
0.7692	Intermediate Similarity	NPD1139	Approved
0.7669	Intermediate Similarity	NPD5763	Approved
0.7669	Intermediate Similarity	NPD5762	Approved
0.7656	Intermediate Similarity	NPD7095	Approved
0.7652	Intermediate Similarity	NPD290	Approved
0.7627	Intermediate Similarity	NPD1138	Approved
0.7619	Intermediate Similarity	NPD987	Approved
0.7615	Intermediate Similarity	NPD4307	Phase 2
0.7615	Intermediate Similarity	NPD2979	Phase 3
0.76	Intermediate Similarity	NPD5327	Phase 3
0.7597	Intermediate Similarity	NPD411	Approved
0.7583	Intermediate Similarity	NPD709	Approved
0.7583	Intermediate Similarity	NPD7157	Approved
0.7563	Intermediate Similarity	NPD1398	Phase 1
0.7557	Intermediate Similarity	NPD6355	Discontinued
0.754	Intermediate Similarity	NPD6696	Suspended
0.7538	Intermediate Similarity	NPD4870	Approved
0.7521	Intermediate Similarity	NPD7340	Approved
0.752	Intermediate Similarity	NPD9717	Approved
0.7519	Intermediate Similarity	NPD4625	Phase 3
0.75	Intermediate Similarity	NPD1712	Approved
0.75	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.748	Intermediate Similarity	NPD3445	Approved
0.748	Intermediate Similarity	NPD3444	Approved
0.748	Intermediate Similarity	NPD3443	Approved
0.7479	Intermediate Similarity	NPD7843	Approved
0.7464	Intermediate Similarity	NPD7837	Clinical (unspecified phase)
0.7462	Intermediate Similarity	NPD7985	Registered
0.7462	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD6832	Phase 2
0.7442	Intermediate Similarity	NPD2614	Approved
0.7438	Intermediate Similarity	NPD2557	Approved
0.7438	Intermediate Similarity	NPD6387	Discontinued
0.7424	Intermediate Similarity	NPD4622	Approved
0.7424	Intermediate Similarity	NPD4618	Approved
0.7417	Intermediate Similarity	NPD1241	Discontinued
0.7407	Intermediate Similarity	NPD2346	Discontinued
0.7388	Intermediate Similarity	NPD2799	Discontinued
0.7388	Intermediate Similarity	NPD4308	Phase 3
0.7368	Intermediate Similarity	NPD2653	Approved
0.7368	Intermediate Similarity	NPD6653	Approved
0.7364	Intermediate Similarity	NPD2861	Phase 2
0.7333	Intermediate Similarity	NPD821	Approved
0.7333	Intermediate Similarity	NPD6100	Approved
0.7333	Intermediate Similarity	NPD2531	Phase 2
0.7333	Intermediate Similarity	NPD6099	Approved
0.7333	Intermediate Similarity	NPD2438	Suspended
0.7333	Intermediate Similarity	NPD6032	Approved
0.7328	Intermediate Similarity	NPD6798	Discontinued
0.7328	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7323	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7313	Intermediate Similarity	NPD5689	Approved
0.7313	Intermediate Similarity	NPD5688	Approved
0.7308	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7302	Intermediate Similarity	NPD1610	Phase 2
0.7293	Intermediate Similarity	NPD447	Suspended
0.7293	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7287	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7287	Intermediate Similarity	NPD1019	Discontinued
0.7287	Intermediate Similarity	NPD2798	Approved
0.7286	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7286	Intermediate Similarity	NPD7446	Clinical (unspecified phase)
0.7281	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.728	Intermediate Similarity	NPD2423	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD592	Approved
0.7273	Intermediate Similarity	NPD594	Approved
0.7266	Intermediate Similarity	NPD3225	Approved
0.7265	Intermediate Similarity	NPD968	Approved
0.7258	Intermediate Similarity	NPD1894	Discontinued
0.725	Intermediate Similarity	NPD228	Approved
0.7246	Intermediate Similarity	NPD4110	Phase 3
0.7246	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD2232	Approved
0.7244	Intermediate Similarity	NPD2230	Approved
0.7244	Intermediate Similarity	NPD2233	Approved
0.7239	Intermediate Similarity	NPD4579	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD2675	Approved
0.7234	Intermediate Similarity	NPD2676	Approved
0.7227	Intermediate Similarity	NPD5451	Approved
0.7227	Intermediate Similarity	NPD4750	Phase 3
0.7222	Intermediate Similarity	NPD3847	Discontinued
0.7209	Intermediate Similarity	NPD6362	Approved
0.7209	Intermediate Similarity	NPD1203	Approved
0.7207	Intermediate Similarity	NPD845	Approved
0.7206	Intermediate Similarity	NPD4476	Approved
0.7206	Intermediate Similarity	NPD4477	Approved
0.72	Intermediate Similarity	NPD3049	Approved
0.7197	Intermediate Similarity	NPD6812	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD1296	Phase 2
0.7197	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD1420	Approved
0.7188	Intermediate Similarity	NPD1421	Approved
0.7176	Intermediate Similarity	NPD4908	Phase 1
0.7165	Intermediate Similarity	NPD1535	Discovery
0.7165	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD6002	Phase 3
0.7153	Intermediate Similarity	NPD6005	Phase 3
0.7153	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD6004	Phase 3
0.7143	Intermediate Similarity	NPD6667	Approved
0.7143	Intermediate Similarity	NPD6666	Approved
0.7143	Intermediate Similarity	NPD2107	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD2486	Discontinued
0.7113	Intermediate Similarity	NPD3647	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD6273	Approved
0.7111	Intermediate Similarity	NPD2157	Approved
0.7109	Intermediate Similarity	NPD2235	Phase 2
0.7109	Intermediate Similarity	NPD3972	Approved
0.7109	Intermediate Similarity	NPD1481	Phase 2
0.7109	Intermediate Similarity	NPD2231	Phase 2
0.7101	Intermediate Similarity	NPD2897	Discontinued
0.7097	Intermediate Similarity	NPD3596	Phase 2
0.709	Intermediate Similarity	NPD2203	Discontinued
0.7083	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD3226	Approved
0.7068	Intermediate Similarity	NPD1048	Approved
0.7068	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD2313	Discontinued
0.7059	Intermediate Similarity	NPD7097	Phase 1
0.7054	Intermediate Similarity	NPD3685	Discontinued
0.7049	Intermediate Similarity	NPD7635	Approved
0.7043	Intermediate Similarity	NPD3020	Approved
0.7042	Intermediate Similarity	NPD1578	Phase 2
0.704	Intermediate Similarity	NPD5536	Phase 2
0.7037	Intermediate Similarity	NPD5735	Approved
0.7037	Intermediate Similarity	NPD5124	Phase 1
0.7037	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD3705	Approved
0.7029	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7023	Intermediate Similarity	NPD3691	Phase 2
0.7023	Intermediate Similarity	NPD3690	Phase 2
0.7023	Intermediate Similarity	NPD4624	Approved
0.7023	Intermediate Similarity	NPD5647	Approved
0.7023	Intermediate Similarity	NPD6584	Phase 3
0.7014	Intermediate Similarity	NPD2370	Clinical (unspecified phase)
0.7008	Intermediate Similarity	NPD2667	Approved
0.7008	Intermediate Similarity	NPD2554	Approved
0.7008	Intermediate Similarity	NPD2556	Approved
0.7008	Intermediate Similarity	NPD2668	Approved
0.7007	Intermediate Similarity	NPD7033	Discontinued
0.7007	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD3748	Approved
0.7	Intermediate Similarity	NPD7003	Approved
0.7	Intermediate Similarity	NPD4628	Phase 3
0.7	Intermediate Similarity	NPD8651	Approved
0.6992	Remote Similarity	NPD5746	Approved
0.6992	Remote Similarity	NPD5163	Phase 2
0.6991	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD6353	Approved
0.6985	Remote Similarity	NPD4097	Suspended
0.6984	Remote Similarity	NPD1182	Approved
0.6984	Remote Similarity	NPD6580	Approved
0.6984	Remote Similarity	NPD6581	Approved
0.6984	Remote Similarity	NPD1548	Phase 1
0.6978	Remote Similarity	NPD1391	Approved
0.6977	Remote Similarity	NPD1840	Phase 2
0.6977	Remote Similarity	NPD1244	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD2935	Discontinued
0.6953	Remote Similarity	NPD3294	Phase 2
0.6947	Remote Similarity	NPD4098	Discontinued
0.694	Remote Similarity	NPD3374	Clinical (unspecified phase)
0.694	Remote Similarity	NPD1336	Approved
0.6935	Remote Similarity	NPD593	Approved
0.6935	Remote Similarity	NPD595	Approved
0.6929	Remote Similarity	NPD5698	Clinical (unspecified phase)

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