NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	180.08
Volume:	188.785
LogP:	2.35
LogD:	2.123
LogS:	-2.465
# Rotatable Bonds:	4
TPSA:	35.53
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	1
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.666
Synthetic Accessibility Score:	1.343
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:	-4.33
MDCK Permeability:	3.269368608016521e-05
Pgp-inhibitor:	0.015
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.061
30% Bioavailability (F30%):	0.885

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.432
Plasma Protein Binding (PPB):	75.58683013916016%
Volume Distribution (VD):	0.956
Pgp-substrate:	13.289168357849121%

ADMET: Metabolism

CYP1A2-inhibitor:	0.985
CYP1A2-substrate:	0.929
CYP2C19-inhibitor:	0.927
CYP2C19-substrate:	0.557
CYP2C9-inhibitor:	0.401
CYP2C9-substrate:	0.793
CYP2D6-inhibitor:	0.137
CYP2D6-substrate:	0.755
CYP3A4-inhibitor:	0.107
CYP3A4-substrate:	0.299

ADMET: Excretion

Clearance (CL):	10.555
Half-life (T1/2):	0.785

ADMET: Toxicity

hERG Blockers:	0.091
Human Hepatotoxicity (H-HT):	0.012
Drug-inuced Liver Injury (DILI):	0.298
AMES Toxicity:	0.012
Rat Oral Acute Toxicity:	0.013
Maximum Recommended Daily Dose:	0.008
Skin Sensitization:	0.387
Carcinogencity:	0.198
Eye Corrosion:	0.168
Eye Irritation:	0.988
Respiratory Toxicity:	0.076

Download Data

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

Natural Product: NPC217423

Natural Product ID:	NPC217423
*Common Name:**	Ethyl 2-Methoxybenzoate
IUPAC Name:	ethyl 2-methoxybenzoate
Synonyms:
Standard InCHIKey:	FNODWEPAWIJGPM-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C10H12O3/c1-3-13-10(11)8-6-4-5-7-9(8)12-2/h4-7H,3H2,1-2H3
SMILES:	CCOC(=O)c1ccccc1OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3183817
PubChem CID:	81784
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000176] Benzoic acids and derivatives [CHEMONTID:0002344] Methoxybenzoic acids and derivatives [CHEMONTID:0002345] O-methoxybenzoic acids and 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
NPO1524	Rosa rugosa	Species	Rosaceae	Eukaryota	Flowers	n.a.	n.a.	DOI[10.1016/j.foodcont.2014.02.001]
NPO9130	Phyllospongia papyracea	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[17455979]
NPO9130	Phyllospongia papyracea	Species	Thorectidae	Eukaryota	n.a.	Papua New Guinea, at depths of 60 ft (914948? S, 15046808? E)	n.a.	PMID[17455979]
NPO1524	Rosa rugosa	Species	Rosaceae	Eukaryota	Flowers	n.a.	n.a.	PMID[20467822]
NPO1524	Rosa rugosa	Species	Rosaceae	Eukaryota	flower buds	n.a.	n.a.	PMID[24063567]
NPO1524	Rosa rugosa	Species	Rosaceae	Eukaryota	Roots	n.a.	n.a.	PMID[24461297]
NPO18491	Hyacinthus orientalis	Species	Hyacinthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9599261]
NPO27293	Sus scrofa	Species	Suidae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO13822	Aconitum fischeri	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18491	Hyacinthus orientalis	Species	Hyacinthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4156	Apocynum androsaemifolium	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1524	Rosa rugosa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18491	Hyacinthus orientalis	Species	Hyacinthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13822	Aconitum fischeri	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1524	Rosa rugosa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4156	Apocynum androsaemifolium	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27293	Sus scrofa	Species	Suidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1524	Rosa rugosa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO13822	Aconitum fischeri	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4156	Apocynum androsaemifolium	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO1524	Rosa rugosa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO18491	Hyacinthus orientalis	Species	Hyacinthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1524	Rosa rugosa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17182	Pulmonaria mollis	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4156	Apocynum androsaemifolium	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27293	Sus scrofa	Species	Suidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18743	Lagascea mollis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9130	Phyllospongia papyracea	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19349	Phlegmariurus yunnanensis	Species	Lycopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13822	Aconitum fischeri	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6288	Talaromyces islandicus	Species	Trichocomaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11751	Tetracera alnifolia	Species	Dilleniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18982	Espeletia grandiflora	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19066	Pisolithus arhizus	Species	Pisolithaceae	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
Potency	1

Activity Type	# Activity
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		Potency	n.a.	27306	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 NPC217423 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	299
0.1-0.2	2049
0.2-0.3	4935
0.3-0.4	10792
0.4-0.5	6975
0.5-0.6	5661
0.6-0.7	8527
0.7-0.8	3275
0.8-0.85	155
0.85-0.9	17
0.9-0.95	9
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9817	High Similarity	NPC188907
0.9558	High Similarity	NPC230951
0.9464	High Similarity	NPC45104
0.9279	High Similarity	NPC53953
0.9237	High Similarity	NPC4164
0.9211	High Similarity	NPC94637
0.9145	High Similarity	NPC311219
0.913	High Similarity	NPC328459
0.913	High Similarity	NPC90522
0.9052	High Similarity	NPC72977
0.9035	High Similarity	NPC128825
0.8938	High Similarity	NPC279916
0.8926	High Similarity	NPC264428
0.8889	High Similarity	NPC233282
0.8833	High Similarity	NPC470162
0.8833	High Similarity	NPC6888
0.8833	High Similarity	NPC470163
0.877	High Similarity	NPC71525
0.877	High Similarity	NPC293387
0.8718	High Similarity	NPC171023
0.871	High Similarity	NPC12694
0.871	High Similarity	NPC473271
0.8678	High Similarity	NPC255073
0.8644	High Similarity	NPC201284
0.8621	High Similarity	NPC220540
0.8583	High Similarity	NPC314329
0.8571	High Similarity	NPC470092
0.856	High Similarity	NPC307732
0.856	High Similarity	NPC42292
0.8559	High Similarity	NPC32298
0.8487	Intermediate Similarity	NPC35744
0.8487	Intermediate Similarity	NPC54243
0.8482	Intermediate Similarity	NPC1065
0.848	Intermediate Similarity	NPC238309
0.8475	Intermediate Similarity	NPC240664
0.8455	Intermediate Similarity	NPC65041
0.8435	Intermediate Similarity	NPC57879
0.8435	Intermediate Similarity	NPC54626
0.8435	Intermediate Similarity	NPC23332
0.8425	Intermediate Similarity	NPC470160
0.8421	Intermediate Similarity	NPC149545
0.84	Intermediate Similarity	NPC293453
0.8393	Intermediate Similarity	NPC227255
0.839	Intermediate Similarity	NPC470860
0.8378	Intermediate Similarity	NPC179686
0.8376	Intermediate Similarity	NPC252004
0.8374	Intermediate Similarity	NPC4012
0.8374	Intermediate Similarity	NPC193805
0.8374	Intermediate Similarity	NPC91475
0.8374	Intermediate Similarity	NPC265910
0.8372	Intermediate Similarity	NPC470844
0.8361	Intermediate Similarity	NPC291189
0.8361	Intermediate Similarity	NPC69403
0.8348	Intermediate Similarity	NPC183648
0.8333	Intermediate Similarity	NPC473019
0.8333	Intermediate Similarity	NPC78662
0.8333	Intermediate Similarity	NPC8005
0.8333	Intermediate Similarity	NPC66246
0.8333	Intermediate Similarity	NPC100551
0.8333	Intermediate Similarity	NPC61779
0.8333	Intermediate Similarity	NPC170546
0.832	Intermediate Similarity	NPC41721
0.8306	Intermediate Similarity	NPC224657
0.8306	Intermediate Similarity	NPC165556
0.8306	Intermediate Similarity	NPC2771
0.8293	Intermediate Similarity	NPC472888
0.8293	Intermediate Similarity	NPC182646
0.8291	Intermediate Similarity	NPC211421
0.8288	Intermediate Similarity	NPC84325
0.8268	Intermediate Similarity	NPC228184
0.8268	Intermediate Similarity	NPC282230
0.8268	Intermediate Similarity	NPC183348
0.8264	Intermediate Similarity	NPC474874
0.8261	Intermediate Similarity	NPC234639
0.8257	Intermediate Similarity	NPC92754
0.8257	Intermediate Similarity	NPC276775
0.8257	Intermediate Similarity	NPC249912
0.8254	Intermediate Similarity	NPC80694
0.8254	Intermediate Similarity	NPC186098
0.825	Intermediate Similarity	NPC293424
0.8244	Intermediate Similarity	NPC472516
0.824	Intermediate Similarity	NPC95309
0.824	Intermediate Similarity	NPC474264
0.8231	Intermediate Similarity	NPC66705
0.823	Intermediate Similarity	NPC128730
0.8226	Intermediate Similarity	NPC221798
0.8226	Intermediate Similarity	NPC56332
0.8217	Intermediate Similarity	NPC287533
0.8203	Intermediate Similarity	NPC196979
0.8203	Intermediate Similarity	NPC470976
0.8203	Intermediate Similarity	NPC15083
0.8203	Intermediate Similarity	NPC470977
0.8195	Intermediate Similarity	NPC136095
0.8189	Intermediate Similarity	NPC211120
0.8182	Intermediate Similarity	NPC233780
0.8182	Intermediate Similarity	NPC253616
0.8182	Intermediate Similarity	NPC35448
0.8182	Intermediate Similarity	NPC225060
0.8182	Intermediate Similarity	NPC78701
0.8175	Intermediate Similarity	NPC181715
0.8175	Intermediate Similarity	NPC49852
0.8175	Intermediate Similarity	NPC298884
0.8175	Intermediate Similarity	NPC475496
0.8158	Intermediate Similarity	NPC326447
0.8158	Intermediate Similarity	NPC176971
0.8145	Intermediate Similarity	NPC93730
0.8145	Intermediate Similarity	NPC141252
0.8145	Intermediate Similarity	NPC11799
0.8142	Intermediate Similarity	NPC38209
0.814	Intermediate Similarity	NPC284424
0.8134	Intermediate Similarity	NPC470856
0.812	Intermediate Similarity	NPC233238
0.812	Intermediate Similarity	NPC36414
0.8115	Intermediate Similarity	NPC31314
0.8115	Intermediate Similarity	NPC193193
0.811	Intermediate Similarity	NPC125887
0.811	Intermediate Similarity	NPC475017
0.811	Intermediate Similarity	NPC473907
0.8108	Intermediate Similarity	NPC146351
0.8106	Intermediate Similarity	NPC268081
0.8106	Intermediate Similarity	NPC135837
0.8103	Intermediate Similarity	NPC259554
0.8099	Intermediate Similarity	NPC94298
0.8099	Intermediate Similarity	NPC206007
0.8099	Intermediate Similarity	NPC166591
0.8099	Intermediate Similarity	NPC27633
0.8095	Intermediate Similarity	NPC237868
0.8095	Intermediate Similarity	NPC475236
0.8092	Intermediate Similarity	NPC125269
0.8087	Intermediate Similarity	NPC151530
0.8087	Intermediate Similarity	NPC157473
0.8083	Intermediate Similarity	NPC33717
0.8083	Intermediate Similarity	NPC316062
0.8083	Intermediate Similarity	NPC128633
0.808	Intermediate Similarity	NPC145134
0.808	Intermediate Similarity	NPC107846
0.8077	Intermediate Similarity	NPC289572
0.8077	Intermediate Similarity	NPC182428
0.8077	Intermediate Similarity	NPC200422
0.8077	Intermediate Similarity	NPC157478
0.8077	Intermediate Similarity	NPC295406
0.8077	Intermediate Similarity	NPC229646
0.8077	Intermediate Similarity	NPC43627
0.8073	Intermediate Similarity	NPC130398
0.807	Intermediate Similarity	NPC139891
0.807	Intermediate Similarity	NPC238115
0.8067	Intermediate Similarity	NPC81808
0.8062	Intermediate Similarity	NPC7012
0.8062	Intermediate Similarity	NPC214702
0.8062	Intermediate Similarity	NPC470831
0.8053	Intermediate Similarity	NPC474365
0.8053	Intermediate Similarity	NPC301943
0.8053	Intermediate Similarity	NPC298224
0.8047	Intermediate Similarity	NPC261759
0.8047	Intermediate Similarity	NPC60558
0.8047	Intermediate Similarity	NPC187907
0.8047	Intermediate Similarity	NPC473894
0.8045	Intermediate Similarity	NPC332594
0.8045	Intermediate Similarity	NPC103001
0.8036	Intermediate Similarity	NPC70624
0.8034	Intermediate Similarity	NPC474157
0.8034	Intermediate Similarity	NPC473809
0.8033	Intermediate Similarity	NPC281356
0.8031	Intermediate Similarity	NPC470841
0.8031	Intermediate Similarity	NPC128428
0.8031	Intermediate Similarity	NPC45537
0.8031	Intermediate Similarity	NPC305518
0.8031	Intermediate Similarity	NPC37512
0.803	Intermediate Similarity	NPC160425
0.8017	Intermediate Similarity	NPC469954
0.8017	Intermediate Similarity	NPC474364
0.8017	Intermediate Similarity	NPC224584
0.8017	Intermediate Similarity	NPC125252
0.8016	Intermediate Similarity	NPC470858
0.8015	Intermediate Similarity	NPC247743
0.8015	Intermediate Similarity	NPC292998
0.8015	Intermediate Similarity	NPC223354
0.8015	Intermediate Similarity	NPC474097
0.8	Intermediate Similarity	NPC308037
0.8	Intermediate Similarity	NPC64359
0.8	Intermediate Similarity	NPC313618
0.8	Intermediate Similarity	NPC262359
0.8	Intermediate Similarity	NPC278556
0.8	Intermediate Similarity	NPC175159
0.7984	Intermediate Similarity	NPC185497
0.7983	Intermediate Similarity	NPC109241
0.7982	Intermediate Similarity	NPC2518
0.7982	Intermediate Similarity	NPC109637
0.797	Intermediate Similarity	NPC254741
0.797	Intermediate Similarity	NPC240593
0.7969	Intermediate Similarity	NPC2596
0.7969	Intermediate Similarity	NPC2401
0.7955	Intermediate Similarity	NPC176102
0.7955	Intermediate Similarity	NPC217914
0.7955	Intermediate Similarity	NPC71108
0.7955	Intermediate Similarity	NPC204257
0.7955	Intermediate Similarity	NPC180905
0.7955	Intermediate Similarity	NPC164136
0.7955	Intermediate Similarity	NPC254832
0.7955	Intermediate Similarity	NPC182496

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 NPC217423 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	280
0.1-0.2	1006
0.2-0.3	1533
0.3-0.4	2642
0.4-0.5	1895
0.5-0.6	1194
0.6-0.7	448
0.7-0.8	128
0.8-0.85	16
0.85-0.9	5
0.9-0.95	3
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.916	High Similarity	NPD1019	Discontinued
0.9145	High Similarity	NPD9717	Approved
0.9035	High Similarity	NPD9493	Approved
0.9008	High Similarity	NPD6832	Phase 2
0.876	High Similarity	NPD1203	Approved
0.8716	High Similarity	NPD9261	Approved
0.8651	High Similarity	NPD1899	Clinical (unspecified phase)
0.8583	High Similarity	NPD1547	Clinical (unspecified phase)
0.8504	High Similarity	NPD1933	Approved
0.8413	Intermediate Similarity	NPD411	Approved
0.8407	Intermediate Similarity	NPD9264	Approved
0.8407	Intermediate Similarity	NPD9267	Approved
0.8407	Intermediate Similarity	NPD9263	Approved
0.8359	Intermediate Similarity	NPD447	Suspended
0.8333	Intermediate Similarity	NPD9266	Approved
0.8333	Intermediate Similarity	NPD74	Approved
0.8291	Intermediate Similarity	NPD1241	Discontinued
0.8244	Intermediate Similarity	NPD1551	Phase 2
0.8158	Intermediate Similarity	NPD3134	Approved
0.8106	Intermediate Similarity	NPD2935	Discontinued
0.8099	Intermediate Similarity	NPD9545	Approved
0.8095	Intermediate Similarity	NPD2798	Approved
0.8087	Intermediate Similarity	NPD1358	Approved
0.807	Intermediate Similarity	NPD9697	Approved
0.8	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD1240	Approved
0.8	Intermediate Similarity	NPD4307	Phase 2
0.7984	Intermediate Similarity	NPD2313	Discontinued
0.797	Intermediate Similarity	NPD2796	Approved
0.7956	Intermediate Similarity	NPD6799	Approved
0.7946	Intermediate Similarity	NPD1238	Approved
0.7917	Intermediate Similarity	NPD9281	Approved
0.7895	Intermediate Similarity	NPD2799	Discontinued
0.7879	Intermediate Similarity	NPD1607	Approved
0.7874	Intermediate Similarity	NPD3267	Approved
0.7874	Intermediate Similarity	NPD2797	Approved
0.7874	Intermediate Similarity	NPD3266	Approved
0.7852	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7794	Intermediate Similarity	NPD1243	Approved
0.777	Intermediate Similarity	NPD5401	Approved
0.7761	Intermediate Similarity	NPD1510	Phase 2
0.7761	Intermediate Similarity	NPD4308	Phase 3
0.7754	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7721	Intermediate Similarity	NPD1549	Phase 2
0.768	Intermediate Similarity	NPD1778	Approved
0.766	Intermediate Similarity	NPD5403	Approved
0.766	Intermediate Similarity	NPD920	Approved
0.7652	Intermediate Similarity	NPD520	Approved
0.7647	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD2346	Discontinued
0.7647	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7638	Intermediate Similarity	NPD3972	Approved
0.763	Intermediate Similarity	NPD3748	Approved
0.7622	Intermediate Similarity	NPD6599	Discontinued
0.76	Intermediate Similarity	NPD5691	Approved
0.7583	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD3268	Approved
0.7569	Intermediate Similarity	NPD7411	Suspended
0.7563	Intermediate Similarity	NPD2182	Approved
0.754	Intermediate Similarity	NPD17	Approved
0.7536	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7521	Intermediate Similarity	NPD164	Approved
0.752	Intermediate Similarity	NPD1894	Discontinued
0.7519	Intermediate Similarity	NPD3225	Approved
0.7519	Intermediate Similarity	NPD1876	Approved
0.7518	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.748	Intermediate Similarity	NPD3496	Discontinued
0.7479	Intermediate Similarity	NPD290	Approved
0.7466	Intermediate Similarity	NPD7819	Suspended
0.7466	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7462	Intermediate Similarity	NPD1164	Approved
0.746	Intermediate Similarity	NPD5585	Approved
0.7448	Intermediate Similarity	NPD5889	Approved
0.7448	Intermediate Similarity	NPD5890	Approved
0.7444	Intermediate Similarity	NPD1296	Phase 2
0.7422	Intermediate Similarity	NPD1281	Approved
0.7422	Intermediate Similarity	NPD422	Phase 1
0.7397	Intermediate Similarity	NPD6801	Discontinued
0.7391	Intermediate Similarity	NPD2344	Approved
0.7365	Intermediate Similarity	NPD7768	Phase 2
0.7364	Intermediate Similarity	NPD1608	Approved
0.7357	Intermediate Similarity	NPD3750	Approved
0.7348	Intermediate Similarity	NPD9494	Approved
0.7339	Intermediate Similarity	NPD9257	Approved
0.7339	Intermediate Similarity	NPD9259	Approved
0.7333	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD3140	Approved
0.7333	Intermediate Similarity	NPD3142	Approved
0.7329	Intermediate Similarity	NPD2366	Approved
0.7315	Intermediate Similarity	NPD7075	Discontinued
0.7313	Intermediate Similarity	NPD6798	Discontinued
0.7297	Intermediate Similarity	NPD5402	Approved
0.7297	Intermediate Similarity	NPD3817	Phase 2
0.7286	Intermediate Similarity	NPD2654	Approved
0.7279	Intermediate Similarity	NPD230	Phase 1
0.7279	Intermediate Similarity	NPD4618	Approved
0.7279	Intermediate Similarity	NPD4622	Approved
0.7273	Intermediate Similarity	NPD2534	Approved
0.7273	Intermediate Similarity	NPD2533	Approved
0.7273	Intermediate Similarity	NPD4662	Approved
0.7273	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD4661	Approved
0.7273	Intermediate Similarity	NPD2532	Approved
0.7267	Intermediate Similarity	NPD919	Approved
0.7266	Intermediate Similarity	NPD4626	Approved
0.726	Intermediate Similarity	NPD6585	Discontinued
0.7252	Intermediate Similarity	NPD1283	Approved
0.7246	Intermediate Similarity	NPD7033	Discontinued
0.7234	Intermediate Similarity	NPD7003	Approved
0.7234	Intermediate Similarity	NPD4628	Phase 3
0.7231	Intermediate Similarity	NPD1481	Phase 2
0.7222	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7218	Intermediate Similarity	NPD454	Approved
0.7193	Intermediate Similarity	NPD1202	Approved
0.7192	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD3226	Approved
0.7183	Intermediate Similarity	NPD3295	Clinical (unspecified phase)
0.7183	Intermediate Similarity	NPD2309	Approved
0.7183	Intermediate Similarity	NPD3887	Approved
0.7177	Intermediate Similarity	NPD5535	Approved
0.7176	Intermediate Similarity	NPD4359	Approved
0.7174	Intermediate Similarity	NPD5688	Approved
0.7174	Intermediate Similarity	NPD5689	Approved
0.7164	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7154	Intermediate Similarity	NPD1535	Discovery
0.7153	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD6355	Discontinued
0.7143	Intermediate Similarity	NPD4380	Phase 2
0.7143	Intermediate Similarity	NPD2353	Approved
0.7143	Intermediate Similarity	NPD1471	Phase 3
0.7143	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5647	Approved
0.7133	Intermediate Similarity	NPD160	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD6233	Phase 2
0.7111	Intermediate Similarity	NPD2598	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD1511	Approved
0.708	Intermediate Similarity	NPD9258	Approved
0.708	Intermediate Similarity	NPD2979	Phase 3
0.708	Intermediate Similarity	NPD9256	Approved
0.7077	Intermediate Similarity	NPD3847	Discontinued
0.7071	Intermediate Similarity	NPD4476	Approved
0.7071	Intermediate Similarity	NPD4477	Approved
0.7063	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD1651	Approved
0.7047	Intermediate Similarity	NPD7317	Phase 3
0.7047	Intermediate Similarity	NPD1934	Approved
0.7032	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD2246	Approved
0.7032	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD2248	Approved
0.7031	Intermediate Similarity	NPD5536	Phase 2
0.702	Intermediate Similarity	NPD3882	Suspended
0.7014	Intermediate Similarity	NPD7440	Discontinued
0.7013	Intermediate Similarity	NPD6808	Phase 2
0.7007	Intermediate Similarity	NPD4062	Phase 3
0.7	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD196	Phase 1
0.6992	Remote Similarity	NPD2684	Approved
0.6986	Remote Similarity	NPD6273	Approved
0.6986	Remote Similarity	NPD1512	Approved
0.6986	Remote Similarity	NPD2186	Approved
0.6974	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD3749	Approved
0.6974	Remote Similarity	NPD955	Approved
0.6972	Remote Similarity	NPD2897	Discontinued
0.6967	Remote Similarity	NPD968	Approved
0.6964	Remote Similarity	NPD1282	Approved
0.6959	Remote Similarity	NPD7458	Discontinued
0.6954	Remote Similarity	NPD7318	Phase 3
0.6954	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.695	Remote Similarity	NPD2438	Suspended
0.6944	Remote Similarity	NPD2354	Approved
0.694	Remote Similarity	NPD6362	Approved
0.6939	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD2067	Discontinued
0.6934	Remote Similarity	NPD3764	Approved
0.6934	Remote Similarity	NPD1048	Approved
0.6933	Remote Similarity	NPD6844	Discontinued
0.6933	Remote Similarity	NPD6280	Approved
0.6933	Remote Similarity	NPD6279	Approved
0.6906	Remote Similarity	NPD1184	Approved
0.6901	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD6004	Phase 3
0.6901	Remote Similarity	NPD6005	Phase 3
0.6901	Remote Similarity	NPD6002	Phase 3
0.6897	Remote Similarity	NPD6652	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD1611	Approved
0.6894	Remote Similarity	NPD1201	Approved
0.6892	Remote Similarity	NPD957	Approved
0.6887	Remote Similarity	NPD2801	Approved
0.6883	Remote Similarity	NPD5494	Approved
0.6871	Remote Similarity	NPD5049	Phase 3
0.6857	Remote Similarity	NPD6651	Approved
0.6846	Remote Similarity	NPD1548	Phase 1
0.6842	Remote Similarity	NPD2379	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