NPASS Compound

Structure

NPC164527 OpenBabel07101718272D 27 28 0 0 0 0 0 0 0 0999 V2000 2.5981 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 5 1 0 0 0 0 2 10 1 0 0 0 0 3 24 1 0 0 0 0 4 25 1 0 0 0 0 5 26 1 0 0 0 0 6 10 2 0 0 0 0 6 13 1 0 0 0 0 7 10 1 0 0 0 0 7 14 2 0 0 0 0 8 11 2 0 0 0 0 8 12 1 0 0 0 0 9 11 1 0 0 0 0 9 15 2 0 0 0 0 11 20 1 0 0 0 0 12 17 2 0 0 0 0 12 18 1 0 0 0 0 13 16 2 0 0 0 0 13 21 1 0 0 0 0 14 16 1 0 0 0 0 14 27 1 0 0 0 0 15 17 1 0 0 0 0 15 24 1 0 0 0 0 16 19 1 0 0 0 0 17 27 1 0 0 0 0 18 22 2 0 0 0 0 18 25 1 0 0 0 0 19 23 2 0 0 0 0 19 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	376.12
Volume:	369.297
LogP:	3.822
LogD:	3.182
LogS:	-4.115
# Rotatable Bonds:	8
TPSA:	111.52
# H-Bond Aceptor:	8
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.74
Synthetic Accessibility Score:	2.44
Fsp3:	0.263
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.869
MDCK Permeability:	2.41443940467434e-05
Pgp-inhibitor:	0.016
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.027
20% Bioavailability (F20%):	0.016
30% Bioavailability (F30%):	0.077

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.087
Plasma Protein Binding (PPB):	97.96663665771484%
Volume Distribution (VD):	0.626
Pgp-substrate:	4.500380992889404%

ADMET: Metabolism

CYP1A2-inhibitor:	0.949
CYP1A2-substrate:	0.874
CYP2C19-inhibitor:	0.954
CYP2C19-substrate:	0.102
CYP2C9-inhibitor:	0.827
CYP2C9-substrate:	0.893
CYP2D6-inhibitor:	0.764
CYP2D6-substrate:	0.578
CYP3A4-inhibitor:	0.732
CYP3A4-substrate:	0.19

ADMET: Excretion

Clearance (CL):	12.95
Half-life (T1/2):	0.795

ADMET: Toxicity

hERG Blockers:	0.021
Human Hepatotoxicity (H-HT):	0.015
Drug-inuced Liver Injury (DILI):	0.32
AMES Toxicity:	0.041
Rat Oral Acute Toxicity:	0.083
Maximum Recommended Daily Dose:	0.659
Skin Sensitization:	0.424
Carcinogencity:	0.017
Eye Corrosion:	0.004
Eye Irritation:	0.908
Respiratory Toxicity:	0.283

Download Data

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

Natural Product: NPC164527

Natural Product ID:	NPC164527
*Common Name:**	Ethyl Asterrate
IUPAC Name:	ethyl 2-hydroxy-6-(4-hydroxy-2-methoxy-6-methoxycarbonylphenoxy)-4-methylbenzoate
Synonyms:	Ethyl Asterrate
Standard InCHIKey:	JIPGWTAQJPIOCX-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C19H20O8/c1-5-26-19(23)16-13(21)6-10(2)7-14(16)27-17-12(18(22)25-4)8-11(20)9-15(17)24-3/h6-9,20-21H,5H2,1-4H3
SMILES:	CCOC(=O)c1c(cc(C)cc1Oc1c(cc(cc1OC)O)C(=O)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL499049
PubChem CID:	44210512
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0004155] Diphenylethers

*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
NPO32625	geomyces sp.	Species	Pseudeurotiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18720971]

☑ 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	4

Activity Type	# Activity
Organism	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT87	Organism	Aspergillus fumigatus	Aspergillus fumigatus	IC50	>	50000.0	nM	PMID[467810]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IC50	>	50000.0	nM	PMID[467810]
NPT1118	Organism	Streptococcus pneumoniae	Streptococcus pneumoniae	IC50	>	50000.0	nM	PMID[467810]
NPT19	Organism	Escherichia coli	Escherichia coli	IC50	>	50000.0	nM	PMID[467810]

☑ 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 NPC164527 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	360
0.1-0.2	1703
0.2-0.3	4888
0.3-0.4	10489
0.4-0.5	7204
0.5-0.6	3683
0.6-0.7	5389
0.7-0.8	7137
0.8-0.85	1597
0.85-0.9	236
0.9-0.95	5
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC213382
0.993	High Similarity	NPC106334
0.993	High Similarity	NPC285527
0.9589	High Similarity	NPC225129
0.9404	High Similarity	NPC287458
0.9342	High Similarity	NPC98892
0.92	High Similarity	NPC289968
0.9073	High Similarity	NPC75069
0.9032	High Similarity	NPC217950
0.9013	High Similarity	NPC280937
0.9013	High Similarity	NPC472915
0.8993	High Similarity	NPC46941
0.8968	High Similarity	NPC130955
0.8954	High Similarity	NPC208197
0.8947	High Similarity	NPC199773
0.8931	High Similarity	NPC99613
0.8931	High Similarity	NPC49487
0.8924	High Similarity	NPC20216
0.8917	High Similarity	NPC156082
0.8917	High Similarity	NPC300984
0.8896	High Similarity	NPC472916
0.8896	High Similarity	NPC54928
0.8889	High Similarity	NPC298802
0.8889	High Similarity	NPC276409
0.8889	High Similarity	NPC250822
0.8889	High Similarity	NPC75279
0.8882	High Similarity	NPC181523
0.8882	High Similarity	NPC208043
0.8882	High Similarity	NPC308451
0.8882	High Similarity	NPC226973
0.8875	High Similarity	NPC17219
0.8875	High Similarity	NPC10576
0.8875	High Similarity	NPC124470
0.8875	High Similarity	NPC109827
0.8875	High Similarity	NPC72696
0.8875	High Similarity	NPC246716
0.8874	High Similarity	NPC328119
0.8874	High Similarity	NPC294502
0.8874	High Similarity	NPC200221
0.8867	High Similarity	NPC119660
0.8867	High Similarity	NPC93034
0.8861	High Similarity	NPC112981
0.8839	High Similarity	NPC181960
0.8831	High Similarity	NPC183597
0.8831	High Similarity	NPC37392
0.8831	High Similarity	NPC163780
0.8831	High Similarity	NPC128863
0.8831	High Similarity	NPC2476
0.8831	High Similarity	NPC50715
0.8831	High Similarity	NPC2928
0.8831	High Similarity	NPC201136
0.8831	High Similarity	NPC92659
0.8831	High Similarity	NPC286052
0.8831	High Similarity	NPC227325
0.8831	High Similarity	NPC256612
0.8831	High Similarity	NPC471800
0.8831	High Similarity	NPC196439
0.8831	High Similarity	NPC213622
0.8831	High Similarity	NPC472909
0.8831	High Similarity	NPC20830
0.8831	High Similarity	NPC138360
0.8831	High Similarity	NPC280339
0.8831	High Similarity	NPC167815
0.8831	High Similarity	NPC4455
0.8831	High Similarity	NPC146165
0.882	High Similarity	NPC158226
0.882	High Similarity	NPC188618
0.8816	High Similarity	NPC239363
0.8816	High Similarity	NPC306821
0.8816	High Similarity	NPC179183
0.8812	High Similarity	NPC476279
0.8812	High Similarity	NPC26568
0.8805	High Similarity	NPC29160
0.8797	High Similarity	NPC474350
0.879	High Similarity	NPC303565
0.8784	High Similarity	NPC214919
0.8784	High Similarity	NPC124467
0.8782	High Similarity	NPC154304
0.8782	High Similarity	NPC238381
0.8782	High Similarity	NPC190487
0.8782	High Similarity	NPC168616
0.8782	High Similarity	NPC83763
0.8774	High Similarity	NPC474520
0.8774	High Similarity	NPC178854
0.8766	High Similarity	NPC274327
0.8766	High Similarity	NPC471981
0.8766	High Similarity	NPC145379
0.8766	High Similarity	NPC250557
0.8766	High Similarity	NPC176775
0.8766	High Similarity	NPC183878
0.8766	High Similarity	NPC299435
0.8766	High Similarity	NPC86485
0.8766	High Similarity	NPC475895
0.8766	High Similarity	NPC260604
0.8766	High Similarity	NPC186507
0.8766	High Similarity	NPC246204
0.8766	High Similarity	NPC47781
0.8766	High Similarity	NPC255350
0.8766	High Similarity	NPC22519
0.8766	High Similarity	NPC231018
0.8766	High Similarity	NPC160951
0.8766	High Similarity	NPC69394
0.8758	High Similarity	NPC474663
0.8758	High Similarity	NPC117579
0.8758	High Similarity	NPC149614
0.8758	High Similarity	NPC262623
0.8758	High Similarity	NPC239440
0.8758	High Similarity	NPC20543
0.8758	High Similarity	NPC1827
0.8758	High Similarity	NPC75695
0.875	High Similarity	NPC234331
0.875	High Similarity	NPC473091
0.875	High Similarity	NPC92722
0.875	High Similarity	NPC102003
0.875	High Similarity	NPC292788
0.875	High Similarity	NPC272485
0.8742	High Similarity	NPC33265
0.8742	High Similarity	NPC62536
0.8742	High Similarity	NPC267153
0.8734	High Similarity	NPC93739
0.8733	High Similarity	NPC472917
0.8726	High Similarity	NPC188967
0.8718	High Similarity	NPC470402
0.8718	High Similarity	NPC36852
0.8718	High Similarity	NPC78302
0.8718	High Similarity	NPC96167
0.8718	High Similarity	NPC75215
0.8718	High Similarity	NPC29841
0.8718	High Similarity	NPC472911
0.8718	High Similarity	NPC469584
0.8718	High Similarity	NPC222814
0.8718	High Similarity	NPC235215
0.8718	High Similarity	NPC156057
0.8718	High Similarity	NPC472913
0.8718	High Similarity	NPC474836
0.8718	High Similarity	NPC262286
0.8718	High Similarity	NPC227192
0.8718	High Similarity	NPC7973
0.8718	High Similarity	NPC476981
0.8718	High Similarity	NPC475267
0.8718	High Similarity	NPC210084
0.8718	High Similarity	NPC93376
0.8718	High Similarity	NPC472910
0.8718	High Similarity	NPC245758
0.8718	High Similarity	NPC48208
0.8718	High Similarity	NPC474208
0.8718	High Similarity	NPC472438
0.8718	High Similarity	NPC108456
0.8718	High Similarity	NPC162869
0.8718	High Similarity	NPC189179
0.8718	High Similarity	NPC472914
0.8718	High Similarity	NPC224137
0.8718	High Similarity	NPC99597
0.8712	High Similarity	NPC139350
0.871	High Similarity	NPC476642
0.871	High Similarity	NPC31018
0.871	High Similarity	NPC255807
0.871	High Similarity	NPC189960
0.871	High Similarity	NPC32557
0.8701	High Similarity	NPC281272
0.8701	High Similarity	NPC101996
0.8701	High Similarity	NPC212678
0.8701	High Similarity	NPC120163
0.8701	High Similarity	NPC25270
0.8701	High Similarity	NPC477231
0.8701	High Similarity	NPC156222
0.8701	High Similarity	NPC142540
0.8701	High Similarity	NPC60972
0.8701	High Similarity	NPC293183
0.8701	High Similarity	NPC134677
0.8701	High Similarity	NPC83508
0.8701	High Similarity	NPC100887
0.8701	High Similarity	NPC301323
0.8701	High Similarity	NPC239128
0.8701	High Similarity	NPC222830
0.8701	High Similarity	NPC131624
0.8701	High Similarity	NPC71334
0.8701	High Similarity	NPC301123
0.8701	High Similarity	NPC187498
0.8701	High Similarity	NPC275722
0.8701	High Similarity	NPC188203
0.8701	High Similarity	NPC39732
0.8701	High Similarity	NPC241498
0.8701	High Similarity	NPC257648
0.8701	High Similarity	NPC256283
0.8701	High Similarity	NPC162313
0.8701	High Similarity	NPC275836
0.8701	High Similarity	NPC198826
0.8701	High Similarity	NPC57030
0.8696	High Similarity	NPC163130
0.8696	High Similarity	NPC280493
0.8696	High Similarity	NPC165979
0.8693	High Similarity	NPC29056
0.8693	High Similarity	NPC338131
0.8693	High Similarity	NPC156953
0.8693	High Similarity	NPC219330
0.8684	High Similarity	NPC195202
0.8684	High Similarity	NPC15329
0.8684	High Similarity	NPC107636
0.8684	High Similarity	NPC55327

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 NPC164527 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	319
0.1-0.2	962
0.2-0.3	1996
0.3-0.4	2564
0.4-0.5	1724
0.5-0.6	1039
0.6-0.7	381
0.7-0.8	137
0.8-0.85	24
0.85-0.9	4
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8766	High Similarity	NPD2801	Approved
0.8699	High Similarity	NPD1551	Phase 2
0.859	High Similarity	NPD5402	Approved
0.859	High Similarity	NPD3817	Phase 2
0.8552	High Similarity	NPD447	Suspended
0.8535	High Similarity	NPD3882	Suspended
0.8535	High Similarity	NPD4868	Clinical (unspecified phase)
0.85	High Similarity	NPD6232	Discontinued
0.8462	Intermediate Similarity	NPD1934	Approved
0.8373	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8354	Intermediate Similarity	NPD5844	Phase 1
0.8344	Intermediate Similarity	NPD7473	Discontinued
0.8293	Intermediate Similarity	NPD3818	Discontinued
0.8291	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.82	Intermediate Similarity	NPD2935	Discontinued
0.8182	Intermediate Similarity	NPD6799	Approved
0.8182	Intermediate Similarity	NPD1511	Approved
0.8171	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8171	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8171	Intermediate Similarity	NPD6166	Phase 2
0.8148	Intermediate Similarity	NPD5494	Approved
0.8141	Intermediate Similarity	NPD5403	Approved
0.8137	Intermediate Similarity	NPD7075	Discontinued
0.8133	Intermediate Similarity	NPD7054	Approved
0.8101	Intermediate Similarity	NPD6599	Discontinued
0.8084	Intermediate Similarity	NPD7472	Approved
0.8084	Intermediate Similarity	NPD7074	Phase 3
0.8077	Intermediate Similarity	NPD1512	Approved
0.8063	Intermediate Similarity	NPD1465	Phase 2
0.8063	Intermediate Similarity	NPD7819	Suspended
0.8054	Intermediate Similarity	NPD1933	Approved
0.8054	Intermediate Similarity	NPD230	Phase 1
0.8013	Intermediate Similarity	NPD5401	Approved
0.8013	Intermediate Similarity	NPD2532	Approved
0.8013	Intermediate Similarity	NPD2533	Approved
0.8013	Intermediate Similarity	NPD2534	Approved
0.8	Intermediate Similarity	NPD1203	Approved
0.7988	Intermediate Similarity	NPD6559	Discontinued
0.7987	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7974	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7959	Intermediate Similarity	NPD6832	Phase 2
0.795	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7941	Intermediate Similarity	NPD7808	Phase 3
0.7937	Intermediate Similarity	NPD7411	Suspended
0.7933	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7929	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7929	Intermediate Similarity	NPD6797	Phase 2
0.7925	Intermediate Similarity	NPD3226	Approved
0.7914	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7898	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7888	Intermediate Similarity	NPD6801	Discontinued
0.7882	Intermediate Similarity	NPD7251	Discontinued
0.7881	Intermediate Similarity	NPD1607	Approved
0.7875	Intermediate Similarity	NPD4380	Phase 2
0.7871	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7862	Intermediate Similarity	NPD1653	Approved
0.7857	Intermediate Similarity	NPD1549	Phase 2
0.7853	Intermediate Similarity	NPD7768	Phase 2
0.7852	Intermediate Similarity	NPD411	Approved
0.7793	Intermediate Similarity	NPD9717	Approved
0.7792	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7792	Intermediate Similarity	NPD2346	Discontinued
0.7792	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD1510	Phase 2
0.7778	Intermediate Similarity	NPD37	Approved
0.7771	Intermediate Similarity	NPD6959	Discontinued
0.7771	Intermediate Similarity	NPD1247	Approved
0.7771	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7758	Intermediate Similarity	NPD919	Approved
0.7758	Intermediate Similarity	NPD6234	Discontinued
0.7756	Intermediate Similarity	NPD4628	Phase 3
0.7756	Intermediate Similarity	NPD3750	Approved
0.7748	Intermediate Similarity	NPD1240	Approved
0.7744	Intermediate Similarity	NPD4966	Approved
0.7744	Intermediate Similarity	NPD4967	Phase 2
0.7744	Intermediate Similarity	NPD4965	Approved
0.7733	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD2796	Approved
0.7688	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7679	Intermediate Similarity	NPD3926	Phase 2
0.7673	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7633	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD2313	Discontinued
0.7595	Intermediate Similarity	NPD6190	Approved
0.7586	Intermediate Similarity	NPD8312	Approved
0.7586	Intermediate Similarity	NPD8313	Approved
0.7584	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7548	Intermediate Similarity	NPD2799	Discontinued
0.7548	Intermediate Similarity	NPD4308	Phase 3
0.7516	Intermediate Similarity	NPD943	Approved
0.7514	Intermediate Similarity	NPD5953	Discontinued
0.75	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD3749	Approved
0.747	Intermediate Similarity	NPD5353	Approved
0.7469	Intermediate Similarity	NPD920	Approved
0.7468	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD1019	Discontinued
0.7456	Intermediate Similarity	NPD7199	Phase 2
0.7442	Intermediate Similarity	NPD7228	Approved
0.7436	Intermediate Similarity	NPD3748	Approved
0.7434	Intermediate Similarity	NPD3027	Phase 3
0.7431	Intermediate Similarity	NPD9493	Approved
0.7417	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7412	Intermediate Similarity	NPD5711	Approved
0.7412	Intermediate Similarity	NPD5710	Approved
0.7403	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD1613	Approved
0.7399	Intermediate Similarity	NPD7286	Phase 2
0.7391	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD6099	Approved
0.7389	Intermediate Similarity	NPD6100	Approved
0.7378	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD5242	Approved
0.7358	Intermediate Similarity	NPD1243	Approved
0.7358	Intermediate Similarity	NPD2800	Approved
0.7347	Intermediate Similarity	NPD1778	Approved
0.7346	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD9269	Phase 2
0.7303	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD9494	Approved
0.7297	Intermediate Similarity	NPD3496	Discontinued
0.729	Intermediate Similarity	NPD4307	Phase 2
0.7289	Intermediate Similarity	NPD6386	Approved
0.7289	Intermediate Similarity	NPD6385	Approved
0.7285	Intermediate Similarity	NPD2797	Approved
0.7279	Intermediate Similarity	NPD9268	Approved
0.7273	Intermediate Similarity	NPD7038	Approved
0.7273	Intermediate Similarity	NPD7685	Pre-registration
0.7273	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7039	Approved
0.7267	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD8434	Phase 2
0.7263	Intermediate Similarity	NPD8150	Discontinued
0.7248	Intermediate Similarity	NPD422	Phase 1
0.7246	Intermediate Similarity	NPD6844	Discontinued
0.7241	Intermediate Similarity	NPD3751	Discontinued
0.7226	Intermediate Similarity	NPD6233	Phase 2
0.7225	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD3225	Approved
0.7215	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD7033	Discontinued
0.7204	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD1608	Approved
0.719	Intermediate Similarity	NPD3018	Phase 2
0.7181	Intermediate Similarity	NPD7435	Discontinued
0.7178	Intermediate Similarity	NPD4357	Discontinued
0.7161	Intermediate Similarity	NPD3268	Approved
0.7152	Intermediate Similarity	NPD4749	Approved
0.7151	Intermediate Similarity	NPD8127	Discontinued
0.7135	Intermediate Similarity	NPD7549	Discontinued
0.7134	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD2344	Approved
0.7125	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD2798	Approved
0.7112	Intermediate Similarity	NPD6777	Approved
0.7112	Intermediate Similarity	NPD6776	Approved
0.7112	Intermediate Similarity	NPD6778	Approved
0.7112	Intermediate Similarity	NPD6782	Approved
0.7112	Intermediate Similarity	NPD6780	Approved
0.7112	Intermediate Similarity	NPD6781	Approved
0.7112	Intermediate Similarity	NPD6779	Approved
0.711	Intermediate Similarity	NPD3787	Discontinued
0.7107	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD4110	Phase 3
0.7097	Intermediate Similarity	NPD4625	Phase 3
0.7095	Intermediate Similarity	NPD9545	Approved
0.7091	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD6651	Approved
0.7086	Intermediate Similarity	NPD1481	Phase 2
0.7083	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD8151	Discontinued
0.7079	Intermediate Similarity	NPD7240	Approved
0.7073	Intermediate Similarity	NPD7390	Discontinued
0.7063	Intermediate Similarity	NPD5406	Approved
0.7063	Intermediate Similarity	NPD5404	Approved
0.7063	Intermediate Similarity	NPD5405	Approved
0.7063	Intermediate Similarity	NPD5408	Approved
0.7051	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD6798	Discontinued
0.7039	Intermediate Similarity	NPD2983	Phase 2
0.7039	Intermediate Similarity	NPD2982	Phase 2
0.7037	Intermediate Similarity	NPD6823	Phase 2
0.7032	Intermediate Similarity	NPD4908	Phase 1
0.7027	Intermediate Similarity	NPD5536	Phase 2
0.7025	Intermediate Similarity	NPD6355	Discontinued
0.702	Intermediate Similarity	NPD1535	Discovery
0.7019	Intermediate Similarity	NPD7266	Discontinued
0.701	Intermediate Similarity	NPD7783	Phase 2
0.701	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD17	Approved
0.7	Intermediate Similarity	NPD7698	Approved
0.7	Intermediate Similarity	NPD7696	Phase 3
0.7	Intermediate Similarity	NPD7697	Approved

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data