NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	258.09
Volume:	267.589
LogP:	3.417
LogD:	3.633
LogS:	-3.446
# Rotatable Bonds:	5
TPSA:	55.76
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.857
Synthetic Accessibility Score:	1.639
Fsp3:	0.133
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.714
MDCK Permeability:	3.167364775435999e-05
Pgp-inhibitor:	0.005
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.644

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.615
Plasma Protein Binding (PPB):	97.93253326416016%
Volume Distribution (VD):	0.642
Pgp-substrate:	3.086848258972168%

ADMET: Metabolism

CYP1A2-inhibitor:	0.986
CYP1A2-substrate:	0.889
CYP2C19-inhibitor:	0.97
CYP2C19-substrate:	0.136
CYP2C9-inhibitor:	0.739
CYP2C9-substrate:	0.674
CYP2D6-inhibitor:	0.868
CYP2D6-substrate:	0.874
CYP3A4-inhibitor:	0.613
CYP3A4-substrate:	0.302

ADMET: Excretion

Clearance (CL):	13.101
Half-life (T1/2):	0.902

ADMET: Toxicity

hERG Blockers:	0.065
Human Hepatotoxicity (H-HT):	0.027
Drug-inuced Liver Injury (DILI):	0.603
AMES Toxicity:	0.309
Rat Oral Acute Toxicity:	0.028
Maximum Recommended Daily Dose:	0.007
Skin Sensitization:	0.277
Carcinogencity:	0.73
Eye Corrosion:	0.073
Eye Irritation:	0.972
Respiratory Toxicity:	0.038

Download Data

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

Natural Product: NPC4164

Natural Product ID:	NPC4164
*Common Name:**	2-Hydroxybenzyl 2'-Methoxybenzoate
IUPAC Name:	(2-methoxyphenyl)methyl 2-hydroxybenzoate
Synonyms:	2-Hydroxybenzyl 2'-Methoxybenzoate
Standard InCHIKey:	YLHAQKVIXLQIFW-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C15H14O4/c1-18-14-9-5-2-6-11(14)10-19-15(17)12-7-3-4-8-13(12)16/h2-9,16H,10H2,1H3
SMILES:	COc1ccccc1COC(=O)c1ccccc1O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL495645
PubChem CID:	7798110
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000176] Benzoic acids and derivatives [CHEMONTID:0001350] Benzoic acid esters [CHEMONTID:0004700] o-Hydroxybenzoic acid esters

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO6984	Brickellia veronicaefolia	Species	Asteraceae	Eukaryota	essential oil	n.a.	n.a.	PMID[16933870]
NPO6984	Brickellia veronicaefolia	Species	Asteraceae	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
IC50	1

Activity Type	# Activity
Tissue	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT548	Tissue	Ileum	Cavia porcellus	IC50	=	1490.0	nM	PMID[447764]

☑ 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 NPC4164 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	290
0.1-0.2	1572
0.2-0.3	4537
0.3-0.4	10089
0.4-0.5	7704
0.5-0.6	4140
0.6-0.7	8144
0.7-0.8	5649
0.8-0.85	511
0.85-0.9	47
0.9-0.95	13
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9492	High Similarity	NPC233282
0.9435	High Similarity	NPC12694
0.9322	High Similarity	NPC94637
0.9256	High Similarity	NPC311219
0.9244	High Similarity	NPC328459
0.9244	High Similarity	NPC90522
0.9237	High Similarity	NPC217423
0.9237	High Similarity	NPC45104
0.9167	High Similarity	NPC72977
0.9153	High Similarity	NPC128825
0.9068	High Similarity	NPC188907
0.9048	High Similarity	NPC238309
0.904	High Similarity	NPC71525
0.9008	High Similarity	NPC230951
0.8952	High Similarity	NPC193805
0.8952	High Similarity	NPC6888
0.8889	High Similarity	NPC264428
0.8828	High Similarity	NPC42292
0.8828	High Similarity	NPC307732
0.8769	High Similarity	NPC287533
0.8692	High Similarity	NPC262359
0.8672	High Similarity	NPC2596
0.8672	High Similarity	NPC293453
0.8651	High Similarity	NPC91475
0.8651	High Similarity	NPC265910
0.8626	High Similarity	NPC205468
0.8626	High Similarity	NPC87231
0.8626	High Similarity	NPC257756
0.8626	High Similarity	NPC212631
0.8626	High Similarity	NPC129132
0.8583	High Similarity	NPC53953
0.8582	High Similarity	NPC188879
0.8561	High Similarity	NPC56031
0.8561	High Similarity	NPC175098
0.8561	High Similarity	NPC472365
0.8561	High Similarity	NPC337373
0.8561	High Similarity	NPC242294
0.8561	High Similarity	NPC188646
0.8561	High Similarity	NPC139813
0.8561	High Similarity	NPC312318
0.8561	High Similarity	NPC263670
0.8561	High Similarity	NPC192304
0.855	High Similarity	NPC475008
0.855	High Similarity	NPC64359
0.855	High Similarity	NPC186097
0.855	High Similarity	NPC470160
0.855	High Similarity	NPC475009
0.855	High Similarity	NPC308037
0.855	High Similarity	NPC313618
0.8519	High Similarity	NPC99333
0.8519	High Similarity	NPC188947
0.8519	High Similarity	NPC124269
0.8519	High Similarity	NPC280284
0.8516	High Similarity	NPC95309
0.8507	High Similarity	NPC240593
0.8504	High Similarity	NPC4012
0.8496	Intermediate Similarity	NPC286336
0.8475	Intermediate Similarity	NPC100551
0.8473	Intermediate Similarity	NPC137264
0.8468	Intermediate Similarity	NPC201284
0.8462	Intermediate Similarity	NPC197425
0.8462	Intermediate Similarity	NPC78662
0.8462	Intermediate Similarity	NPC8005
0.8462	Intermediate Similarity	NPC473019
0.8455	Intermediate Similarity	NPC240664
0.845	Intermediate Similarity	NPC22783
0.845	Intermediate Similarity	NPC181715
0.8444	Intermediate Similarity	NPC7013
0.8444	Intermediate Similarity	NPC209560
0.8444	Intermediate Similarity	NPC181124
0.8444	Intermediate Similarity	NPC162680
0.8444	Intermediate Similarity	NPC332594
0.8444	Intermediate Similarity	NPC250266
0.8444	Intermediate Similarity	NPC116632
0.8444	Intermediate Similarity	NPC266597
0.8444	Intermediate Similarity	NPC303644
0.8444	Intermediate Similarity	NPC290291
0.8444	Intermediate Similarity	NPC294409
0.8444	Intermediate Similarity	NPC275055
0.8433	Intermediate Similarity	NPC234560
0.8433	Intermediate Similarity	NPC39426
0.8433	Intermediate Similarity	NPC131039
0.843	Intermediate Similarity	NPC211421
0.843	Intermediate Similarity	NPC279916
0.8425	Intermediate Similarity	NPC93730
0.8421	Intermediate Similarity	NPC294593
0.8421	Intermediate Similarity	NPC18877
0.8421	Intermediate Similarity	NPC159623
0.8421	Intermediate Similarity	NPC144051
0.8421	Intermediate Similarity	NPC28753
0.8421	Intermediate Similarity	NPC82225
0.8421	Intermediate Similarity	NPC204960
0.8421	Intermediate Similarity	NPC20560
0.8413	Intermediate Similarity	NPC314329
0.8409	Intermediate Similarity	NPC113006
0.84	Intermediate Similarity	NPC470092
0.84	Intermediate Similarity	NPC31314
0.84	Intermediate Similarity	NPC193193
0.84	Intermediate Similarity	NPC474874
0.8397	Intermediate Similarity	NPC115998
0.8397	Intermediate Similarity	NPC39753
0.8397	Intermediate Similarity	NPC247779
0.8397	Intermediate Similarity	NPC185497
0.8387	Intermediate Similarity	NPC32298
0.8385	Intermediate Similarity	NPC80694
0.8385	Intermediate Similarity	NPC186098
0.8382	Intermediate Similarity	NPC55162
0.8382	Intermediate Similarity	NPC309154
0.8382	Intermediate Similarity	NPC279668
0.8382	Intermediate Similarity	NPC329225
0.8382	Intermediate Similarity	NPC147686
0.8382	Intermediate Similarity	NPC90665
0.8382	Intermediate Similarity	NPC278323
0.8382	Intermediate Similarity	NPC12175
0.8382	Intermediate Similarity	NPC472460
0.837	Intermediate Similarity	NPC472364
0.837	Intermediate Similarity	NPC1486
0.837	Intermediate Similarity	NPC186838
0.837	Intermediate Similarity	NPC135837
0.837	Intermediate Similarity	NPC249606
0.837	Intermediate Similarity	NPC98115
0.837	Intermediate Similarity	NPC235428
0.837	Intermediate Similarity	NPC47815
0.837	Intermediate Similarity	NPC213603
0.837	Intermediate Similarity	NPC473887
0.837	Intermediate Similarity	NPC231772
0.837	Intermediate Similarity	NPC477242
0.837	Intermediate Similarity	NPC472367
0.837	Intermediate Similarity	NPC234133
0.837	Intermediate Similarity	NPC477243
0.837	Intermediate Similarity	NPC41461
0.837	Intermediate Similarity	NPC87545
0.837	Intermediate Similarity	NPC12165
0.837	Intermediate Similarity	NPC127447
0.837	Intermediate Similarity	NPC194281
0.837	Intermediate Similarity	NPC274109
0.837	Intermediate Similarity	NPC29353
0.837	Intermediate Similarity	NPC66349
0.837	Intermediate Similarity	NPC477244
0.837	Intermediate Similarity	NPC476333
0.837	Intermediate Similarity	NPC150399
0.837	Intermediate Similarity	NPC25287
0.837	Intermediate Similarity	NPC473391
0.837	Intermediate Similarity	NPC124784
0.837	Intermediate Similarity	NPC168105
0.8358	Intermediate Similarity	NPC172262
0.8346	Intermediate Similarity	NPC200422
0.8346	Intermediate Similarity	NPC291189
0.8346	Intermediate Similarity	NPC472591
0.8346	Intermediate Similarity	NPC157478
0.8346	Intermediate Similarity	NPC128216
0.8346	Intermediate Similarity	NPC69403
0.8346	Intermediate Similarity	NPC295406
0.8346	Intermediate Similarity	NPC43627
0.8346	Intermediate Similarity	NPC289572
0.8345	Intermediate Similarity	NPC470216
0.8333	Intermediate Similarity	NPC470831
0.8333	Intermediate Similarity	NPC250755
0.8333	Intermediate Similarity	NPC3188
0.8333	Intermediate Similarity	NPC214702
0.8333	Intermediate Similarity	NPC141549
0.8321	Intermediate Similarity	NPC261234
0.8321	Intermediate Similarity	NPC222342
0.8321	Intermediate Similarity	NPC187907
0.8321	Intermediate Similarity	NPC225153
0.8321	Intermediate Similarity	NPC150648
0.8321	Intermediate Similarity	NPC329203
0.8321	Intermediate Similarity	NPC265871
0.8321	Intermediate Similarity	NPC274784
0.8321	Intermediate Similarity	NPC60558
0.8321	Intermediate Similarity	NPC470211
0.8321	Intermediate Similarity	NPC20709
0.8321	Intermediate Similarity	NPC310135
0.8321	Intermediate Similarity	NPC295384
0.832	Intermediate Similarity	NPC54243
0.832	Intermediate Similarity	NPC61779
0.832	Intermediate Similarity	NPC35744
0.8309	Intermediate Similarity	NPC153979
0.8309	Intermediate Similarity	NPC243083
0.8309	Intermediate Similarity	NPC476480
0.8309	Intermediate Similarity	NPC296490
0.8309	Intermediate Similarity	NPC212767
0.8309	Intermediate Similarity	NPC79943
0.8309	Intermediate Similarity	NPC13768
0.8309	Intermediate Similarity	NPC287246
0.8309	Intermediate Similarity	NPC472419
0.8309	Intermediate Similarity	NPC84585
0.8309	Intermediate Similarity	NPC295261
0.8309	Intermediate Similarity	NPC12296
0.8309	Intermediate Similarity	NPC107586
0.8309	Intermediate Similarity	NPC32441
0.8309	Intermediate Similarity	NPC317119
0.8308	Intermediate Similarity	NPC128428
0.8308	Intermediate Similarity	NPC293387
0.8308	Intermediate Similarity	NPC305518
0.8308	Intermediate Similarity	NPC470841
0.8296	Intermediate Similarity	NPC223616
0.8296	Intermediate Similarity	NPC13575
0.8296	Intermediate Similarity	NPC9985
0.8296	Intermediate Similarity	NPC156092

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 NPC4164 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	262
0.1-0.2	939
0.2-0.3	1460
0.3-0.4	2502
0.4-0.5	1937
0.5-0.6	1336
0.6-0.7	526
0.7-0.8	151
0.8-0.85	24
0.85-0.9	9
0.9-0.95	4
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9504	High Similarity	NPD1203	Approved
0.9256	High Similarity	NPD9717	Approved
0.9153	High Similarity	NPD9493	Approved
0.8968	High Similarity	NPD6832	Phase 2
0.8931	High Similarity	NPD1551	Phase 2
0.8788	High Similarity	NPD2935	Discontinued
0.8661	High Similarity	NPD1019	Discontinued
0.8626	High Similarity	NPD1899	Clinical (unspecified phase)
0.855	High Similarity	NPD1240	Approved
0.8538	High Similarity	NPD411	Approved
0.8485	Intermediate Similarity	NPD1933	Approved
0.8485	Intermediate Similarity	NPD447	Suspended
0.8475	Intermediate Similarity	NPD74	Approved
0.8475	Intermediate Similarity	NPD9266	Approved
0.8433	Intermediate Similarity	NPD1510	Phase 2
0.8421	Intermediate Similarity	NPD1607	Approved
0.8413	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.8397	Intermediate Similarity	NPD2313	Discontinued
0.8394	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.839	Intermediate Similarity	NPD9267	Approved
0.839	Intermediate Similarity	NPD9263	Approved
0.839	Intermediate Similarity	NPD9264	Approved
0.8382	Intermediate Similarity	NPD1549	Phase 2
0.8309	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8309	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8296	Intermediate Similarity	NPD2799	Discontinued
0.8296	Intermediate Similarity	NPD4308	Phase 3
0.8295	Intermediate Similarity	NPD2797	Approved
0.8248	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.824	Intermediate Similarity	NPD9545	Approved
0.8231	Intermediate Similarity	NPD2798	Approved
0.8214	Intermediate Similarity	NPD6799	Approved
0.812	Intermediate Similarity	NPD3268	Approved
0.8077	Intermediate Similarity	NPD3225	Approved
0.8069	Intermediate Similarity	NPD7411	Suspended
0.8065	Intermediate Similarity	NPD9281	Approved
0.806	Intermediate Similarity	NPD520	Approved
0.8058	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8051	Intermediate Similarity	NPD9261	Approved
0.8043	Intermediate Similarity	NPD2346	Discontinued
0.8042	Intermediate Similarity	NPD5403	Approved
0.8028	Intermediate Similarity	NPD5401	Approved
0.8015	Intermediate Similarity	NPD1164	Approved
0.8	Intermediate Similarity	NPD4307	Phase 2
0.8	Intermediate Similarity	NPD3750	Approved
0.7985	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7973	Intermediate Similarity	NPD7768	Phase 2
0.7923	Intermediate Similarity	NPD1481	Phase 2
0.7919	Intermediate Similarity	NPD7075	Discontinued
0.7914	Intermediate Similarity	NPD2344	Approved
0.7902	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7879	Intermediate Similarity	NPD3267	Approved
0.7879	Intermediate Similarity	NPD3266	Approved
0.7877	Intermediate Similarity	NPD6599	Discontinued
0.7846	Intermediate Similarity	NPD1535	Discovery
0.7842	Intermediate Similarity	NPD2796	Approved
0.784	Intermediate Similarity	NPD1241	Discontinued
0.7838	Intermediate Similarity	NPD7819	Suspended
0.7838	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7812	Intermediate Similarity	NPD1894	Discontinued
0.7797	Intermediate Similarity	NPD1238	Approved
0.7786	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.777	Intermediate Similarity	NPD7033	Discontinued
0.777	Intermediate Similarity	NPD6801	Discontinued
0.7755	Intermediate Similarity	NPD4380	Phase 2
0.7746	Intermediate Similarity	NPD4628	Phase 3
0.7721	Intermediate Similarity	NPD6798	Discontinued
0.771	Intermediate Similarity	NPD422	Phase 1
0.7708	Intermediate Similarity	NPD1511	Approved
0.7692	Intermediate Similarity	NPD2309	Approved
0.7687	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7687	Intermediate Similarity	NPD3226	Approved
0.7667	Intermediate Similarity	NPD5402	Approved
0.7652	Intermediate Similarity	NPD1608	Approved
0.7651	Intermediate Similarity	NPD1934	Approved
0.7643	Intermediate Similarity	NPD3748	Approved
0.7642	Intermediate Similarity	NPD1358	Approved
0.7623	Intermediate Similarity	NPD9697	Approved
0.7622	Intermediate Similarity	NPD7003	Approved
0.7616	Intermediate Similarity	NPD3882	Suspended
0.7613	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7603	Intermediate Similarity	NPD1512	Approved
0.76	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7591	Intermediate Similarity	NPD3764	Approved
0.7584	Intermediate Similarity	NPD2366	Approved
0.7566	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7566	Intermediate Similarity	NPD3749	Approved
0.7561	Intermediate Similarity	NPD968	Approved
0.7561	Intermediate Similarity	NPD3134	Approved
0.7557	Intermediate Similarity	NPD1778	Approved
0.7554	Intermediate Similarity	NPD6355	Discontinued
0.7554	Intermediate Similarity	NPD230	Phase 1
0.7552	Intermediate Similarity	NPD1243	Approved
0.7551	Intermediate Similarity	NPD920	Approved
0.755	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.755	Intermediate Similarity	NPD3817	Phase 2
0.7537	Intermediate Similarity	NPD1283	Approved
0.7536	Intermediate Similarity	NPD6233	Phase 2
0.7534	Intermediate Similarity	NPD2534	Approved
0.7534	Intermediate Similarity	NPD2533	Approved
0.7534	Intermediate Similarity	NPD2532	Approved
0.7519	Intermediate Similarity	NPD3972	Approved
0.7519	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD7440	Discontinued
0.75	Intermediate Similarity	NPD9494	Approved
0.75	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3496	Discontinued
0.75	Intermediate Similarity	NPD3847	Discontinued
0.7483	Intermediate Similarity	NPD2801	Approved
0.7481	Intermediate Similarity	NPD1470	Approved
0.7467	Intermediate Similarity	NPD5890	Approved
0.7467	Intermediate Similarity	NPD5889	Approved
0.7451	Intermediate Similarity	NPD955	Approved
0.745	Intermediate Similarity	NPD7458	Discontinued
0.7444	Intermediate Similarity	NPD1201	Approved
0.7424	Intermediate Similarity	NPD17	Approved
0.7415	Intermediate Similarity	NPD4661	Approved
0.7415	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7415	Intermediate Similarity	NPD4662	Approved
0.741	Intermediate Similarity	NPD4062	Phase 3
0.7407	Intermediate Similarity	NPD1876	Approved
0.7405	Intermediate Similarity	NPD1548	Phase 1
0.7386	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD5953	Discontinued
0.7372	Intermediate Similarity	NPD6232	Discontinued
0.736	Intermediate Similarity	NPD290	Approved
0.7358	Intermediate Similarity	NPD7286	Phase 2
0.7357	Intermediate Similarity	NPD943	Approved
0.7348	Intermediate Similarity	NPD5585	Approved
0.7343	Intermediate Similarity	NPD5404	Approved
0.7343	Intermediate Similarity	NPD5405	Approved
0.7343	Intermediate Similarity	NPD4476	Approved
0.7343	Intermediate Similarity	NPD5406	Approved
0.7343	Intermediate Similarity	NPD4477	Approved
0.7343	Intermediate Similarity	NPD5408	Approved
0.7333	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD2354	Approved
0.732	Intermediate Similarity	NPD2379	Clinical (unspecified phase)
0.7313	Intermediate Similarity	NPD1281	Approved
0.7303	Intermediate Similarity	NPD6844	Discontinued
0.7299	Intermediate Similarity	NPD5647	Approved
0.7297	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD6585	Discontinued
0.726	Intermediate Similarity	NPD1196	Approved
0.7254	Intermediate Similarity	NPD6651	Approved
0.7248	Intermediate Similarity	NPD5049	Phase 3
0.7248	Intermediate Similarity	NPD6273	Approved
0.7234	Intermediate Similarity	NPD4060	Phase 1
0.7233	Intermediate Similarity	NPD7473	Discontinued
0.7227	Intermediate Similarity	NPD1202	Approved
0.7222	Intermediate Similarity	NPD6559	Discontinued
0.7214	Intermediate Similarity	NPD1296	Phase 2
0.7211	Intermediate Similarity	NPD3887	Approved
0.7209	Intermediate Similarity	NPD5535	Approved
0.7192	Intermediate Similarity	NPD1195	Approved
0.7192	Intermediate Similarity	NPD2800	Approved
0.7188	Intermediate Similarity	NPD3818	Discontinued
0.7185	Intermediate Similarity	NPD1610	Phase 2
0.7183	Intermediate Similarity	NPD4618	Approved
0.7183	Intermediate Similarity	NPD4622	Approved
0.7183	Intermediate Similarity	NPD1184	Approved
0.7179	Intermediate Similarity	NPD919	Approved
0.7172	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD1471	Phase 3
0.7172	Intermediate Similarity	NPD2353	Approved
0.717	Intermediate Similarity	NPD6166	Phase 2
0.717	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7165	Intermediate Similarity	NPD2182	Approved
0.7164	Intermediate Similarity	NPD4626	Approved
0.7153	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7054	Approved
0.7143	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7122	Intermediate Similarity	NPD454	Approved
0.712	Intermediate Similarity	NPD164	Approved
0.712	Intermediate Similarity	NPD1237	Approved
0.7119	Intermediate Similarity	NPD9256	Approved
0.7119	Intermediate Similarity	NPD9258	Approved
0.7115	Intermediate Similarity	NPD8005	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD1543	Discontinued
0.7113	Intermediate Similarity	NPD2979	Phase 3
0.7099	Intermediate Similarity	NPD7472	Approved
0.7099	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD7074	Phase 3
0.7097	Intermediate Similarity	NPD4288	Approved
0.7097	Intermediate Similarity	NPD2296	Approved
0.7095	Intermediate Similarity	NPD3295	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD1048	Approved
0.709	Intermediate Similarity	NPD5691	Approved
0.7089	Intermediate Similarity	NPD6959	Discontinued
0.7083	Intermediate Similarity	NPD5689	Approved
0.7083	Intermediate Similarity	NPD5688	Approved
0.708	Intermediate Similarity	NPD4359	Approved
0.7075	Intermediate Similarity	NPD2976	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD4908	Phase 1

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