NPASS Compound

Structure

NPC285527 OpenBabel07101718192D 26 27 0 0 0 0 0 0 0 0999 V2000 -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 2.5981 -1.5000 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 -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 9 1 0 0 0 0 2 23 1 0 0 0 0 3 24 1 0 0 0 0 4 25 1 0 0 0 0 5 9 2 0 0 0 0 5 12 1 0 0 0 0 6 9 1 0 0 0 0 6 13 2 0 0 0 0 7 10 2 0 0 0 0 7 11 1 0 0 0 0 8 10 1 0 0 0 0 8 14 2 0 0 0 0 10 19 1 0 0 0 0 11 16 2 0 0 0 0 11 17 1 0 0 0 0 12 15 2 0 0 0 0 12 20 1 0 0 0 0 13 15 1 0 0 0 0 13 26 1 0 0 0 0 14 16 1 0 0 0 0 14 23 1 0 0 0 0 15 18 1 0 0 0 0 16 26 1 0 0 0 0 17 21 2 0 0 0 0 17 24 1 0 0 0 0 18 22 2 0 0 0 0 18 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	362.1
Volume:	352.001
LogP:	3.47
LogD:	3.029
LogS:	-3.929
# Rotatable Bonds:	7
TPSA:	111.52
# H-Bond Aceptor:	8
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.781
Synthetic Accessibility Score:	2.44
Fsp3:	0.222
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:	-4.854
MDCK Permeability:	2.0604789824574254e-05
Pgp-inhibitor:	0.013
Pgp-substrate:	0.012
Human Intestinal Absorption (HIA):	0.171
20% Bioavailability (F20%):	0.008
30% Bioavailability (F30%):	0.098

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.141
Plasma Protein Binding (PPB):	95.39346313476562%
Volume Distribution (VD):	0.605
Pgp-substrate:	8.528304100036621%

ADMET: Metabolism

CYP1A2-inhibitor:	0.952
CYP1A2-substrate:	0.89
CYP2C19-inhibitor:	0.921
CYP2C19-substrate:	0.14
CYP2C9-inhibitor:	0.767
CYP2C9-substrate:	0.895
CYP2D6-inhibitor:	0.649
CYP2D6-substrate:	0.66
CYP3A4-inhibitor:	0.767
CYP3A4-substrate:	0.227

ADMET: Excretion

Clearance (CL):	12.523
Half-life (T1/2):	0.85

ADMET: Toxicity

hERG Blockers:	0.01
Human Hepatotoxicity (H-HT):	0.041
Drug-inuced Liver Injury (DILI):	0.455
AMES Toxicity:	0.063
Rat Oral Acute Toxicity:	0.28
Maximum Recommended Daily Dose:	0.768
Skin Sensitization:	0.359
Carcinogencity:	0.014
Eye Corrosion:	0.005
Eye Irritation:	0.773
Respiratory Toxicity:	0.351

Download Data

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

Natural Product: NPC285527

Natural Product ID:	NPC285527
*Common Name:**	Methyl Asterrate
IUPAC Name:	methyl 2-hydroxy-6-(4-hydroxy-2-methoxy-6-methoxycarbonylphenoxy)-4-methylbenzoate
Synonyms:	Methyl Asterrate
Standard InCHIKey:	KYDNOVLBVBYOSW-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C18H18O8/c1-9-5-12(20)15(18(22)25-4)13(6-9)26-16-11(17(21)24-3)7-10(19)8-14(16)23-2/h5-8,19-20H,1-4H3
SMILES:	COc1cc(O)cc(c1Oc1cc(C)cc(c1C(=O)OC)O)C(=O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL451989
PubChem CID:	5249326
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
NPO32471	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11809055]
NPO20214	Ruprechtia tangarana	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12932125]
NPO20214	Ruprechtia tangarana	Species	Polygonaceae	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
Others	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT530	Organism	Caenorhabditis elegans	Caenorhabditis elegans	LD90	=	75.0	ppm	PMID[494186]

☑ 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 NPC285527 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	367
0.1-0.2	1756
0.2-0.3	5140
0.3-0.4	10850
0.4-0.5	6588
0.5-0.6	3755
0.6-0.7	5424
0.7-0.8	7068
0.8-0.85	1513
0.85-0.9	224
0.9-0.95	6
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC106334
0.993	High Similarity	NPC164527
0.993	High Similarity	NPC213382
0.9521	High Similarity	NPC225129
0.9467	High Similarity	NPC287458
0.9404	High Similarity	NPC98892
0.9262	High Similarity	NPC289968
0.9133	High Similarity	NPC75069
0.9054	High Similarity	NPC46941
0.9026	High Similarity	NPC130955
0.9013	High Similarity	NPC208197
0.8987	High Similarity	NPC49487
0.8987	High Similarity	NPC99613
0.8974	High Similarity	NPC300984
0.8968	High Similarity	NPC217950
0.8954	High Similarity	NPC54928
0.8947	High Similarity	NPC250822
0.8947	High Similarity	NPC472915
0.8947	High Similarity	NPC276409
0.8947	High Similarity	NPC75279
0.8947	High Similarity	NPC280937
0.894	High Similarity	NPC208043
0.894	High Similarity	NPC226973
0.894	High Similarity	NPC308451
0.8933	High Similarity	NPC294502
0.8933	High Similarity	NPC200221
0.8933	High Similarity	NPC328119
0.8931	High Similarity	NPC109827
0.8931	High Similarity	NPC124470
0.8931	High Similarity	NPC72696
0.8926	High Similarity	NPC93034
0.8926	High Similarity	NPC119660
0.8889	High Similarity	NPC196439
0.8889	High Similarity	NPC20830
0.8889	High Similarity	NPC256612
0.8889	High Similarity	NPC2476
0.8889	High Similarity	NPC167815
0.8889	High Similarity	NPC138360
0.8889	High Similarity	NPC280339
0.8889	High Similarity	NPC128863
0.8889	High Similarity	NPC183597
0.8889	High Similarity	NPC163780
0.8889	High Similarity	NPC4455
0.8889	High Similarity	NPC146165
0.8889	High Similarity	NPC201136
0.8889	High Similarity	NPC50715
0.8889	High Similarity	NPC471800
0.8889	High Similarity	NPC92659
0.8889	High Similarity	NPC227325
0.8882	High Similarity	NPC199773
0.8875	High Similarity	NPC158226
0.8875	High Similarity	NPC188618
0.8874	High Similarity	NPC306821
0.8874	High Similarity	NPC179183
0.8861	High Similarity	NPC20216
0.8861	High Similarity	NPC29160
0.8854	High Similarity	NPC474350
0.8854	High Similarity	NPC156082
0.8846	High Similarity	NPC303565
0.8844	High Similarity	NPC124467
0.8844	High Similarity	NPC214919
0.8839	High Similarity	NPC238381
0.8839	High Similarity	NPC154304
0.8839	High Similarity	NPC190487
0.8839	High Similarity	NPC83763
0.8839	High Similarity	NPC168616
0.8831	High Similarity	NPC472916
0.8831	High Similarity	NPC474520
0.8831	High Similarity	NPC178854
0.8824	High Similarity	NPC160951
0.8824	High Similarity	NPC183878
0.8824	High Similarity	NPC274327
0.8824	High Similarity	NPC22519
0.8824	High Similarity	NPC298802
0.8824	High Similarity	NPC145379
0.8824	High Similarity	NPC86485
0.8824	High Similarity	NPC471981
0.8824	High Similarity	NPC176775
0.8824	High Similarity	NPC69394
0.8824	High Similarity	NPC231018
0.8824	High Similarity	NPC246204
0.8824	High Similarity	NPC47781
0.8824	High Similarity	NPC475895
0.8824	High Similarity	NPC255350
0.882	High Similarity	NPC181523
0.8816	High Similarity	NPC117579
0.8816	High Similarity	NPC149614
0.8816	High Similarity	NPC474663
0.8812	High Similarity	NPC10576
0.8812	High Similarity	NPC17219
0.8812	High Similarity	NPC246716
0.8808	High Similarity	NPC92722
0.8808	High Similarity	NPC102003
0.8805	High Similarity	NPC234331
0.88	High Similarity	NPC62536
0.88	High Similarity	NPC33265
0.8797	High Similarity	NPC267153
0.8797	High Similarity	NPC112981
0.879	High Similarity	NPC93739
0.8782	High Similarity	NPC188967
0.8774	High Similarity	NPC78302
0.8774	High Similarity	NPC224137
0.8774	High Similarity	NPC75215
0.8774	High Similarity	NPC29841
0.8774	High Similarity	NPC235215
0.8774	High Similarity	NPC7973
0.8774	High Similarity	NPC93376
0.8774	High Similarity	NPC476981
0.8774	High Similarity	NPC181960
0.8774	High Similarity	NPC227192
0.8774	High Similarity	NPC472438
0.8774	High Similarity	NPC262286
0.8774	High Similarity	NPC36852
0.8774	High Similarity	NPC189179
0.8766	High Similarity	NPC37392
0.8766	High Similarity	NPC286052
0.8766	High Similarity	NPC32557
0.8766	High Similarity	NPC472909
0.8766	High Similarity	NPC189960
0.8766	High Similarity	NPC213622
0.8766	High Similarity	NPC2928
0.8758	High Similarity	NPC241498
0.8758	High Similarity	NPC60972
0.8758	High Similarity	NPC275722
0.8758	High Similarity	NPC256283
0.8758	High Similarity	NPC188203
0.8758	High Similarity	NPC83508
0.8758	High Similarity	NPC275836
0.8758	High Similarity	NPC131624
0.8758	High Similarity	NPC39732
0.8758	High Similarity	NPC57030
0.8758	High Similarity	NPC101996
0.8758	High Similarity	NPC120163
0.8758	High Similarity	NPC198826
0.8758	High Similarity	NPC212678
0.8758	High Similarity	NPC134677
0.8758	High Similarity	NPC142540
0.8758	High Similarity	NPC25270
0.8758	High Similarity	NPC100887
0.8758	High Similarity	NPC156222
0.8758	High Similarity	NPC239128
0.8758	High Similarity	NPC301323
0.8758	High Similarity	NPC222830
0.8758	High Similarity	NPC293183
0.8758	High Similarity	NPC187498
0.8758	High Similarity	NPC162313
0.8758	High Similarity	NPC71334
0.8758	High Similarity	NPC301123
0.875	High Similarity	NPC239363
0.875	High Similarity	NPC219330
0.875	High Similarity	NPC165979
0.875	High Similarity	NPC476279
0.875	High Similarity	NPC163130
0.875	High Similarity	NPC29056
0.875	High Similarity	NPC280493
0.875	High Similarity	NPC26568
0.8742	High Similarity	NPC15329
0.8742	High Similarity	NPC55327
0.8742	High Similarity	NPC107636
0.8742	High Similarity	NPC195202
0.8742	High Similarity	NPC131451
0.8734	High Similarity	NPC477689
0.8734	High Similarity	NPC284007
0.8733	High Similarity	NPC302408
0.8733	High Similarity	NPC209278
0.8733	High Similarity	NPC283002
0.8726	High Similarity	NPC66288
0.8725	High Similarity	NPC23955
0.8718	High Similarity	NPC300943
0.8718	High Similarity	NPC143828
0.8718	High Similarity	NPC115798
0.8718	High Similarity	NPC288669
0.8718	High Similarity	NPC193842
0.8718	High Similarity	NPC19687
0.8718	High Similarity	NPC25495
0.8718	High Similarity	NPC261004
0.8718	High Similarity	NPC18772
0.8718	High Similarity	NPC195832
0.8718	High Similarity	NPC4481
0.8718	High Similarity	NPC152166
0.8718	High Similarity	NPC18607
0.8718	High Similarity	NPC176300
0.8718	High Similarity	NPC253634
0.8718	High Similarity	NPC22472
0.8718	High Similarity	NPC105242
0.8718	High Similarity	NPC45846
0.8718	High Similarity	NPC204854
0.8718	High Similarity	NPC9609
0.8718	High Similarity	NPC191459
0.8718	High Similarity	NPC130894
0.8718	High Similarity	NPC7846
0.871	High Similarity	NPC100916
0.871	High Similarity	NPC55619
0.871	High Similarity	NPC472453
0.871	High Similarity	NPC247017
0.871	High Similarity	NPC98661
0.871	High Similarity	NPC200388
0.871	High Similarity	NPC268161
0.871	High Similarity	NPC138243
0.871	High Similarity	NPC45131

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 NPC285527 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	324
0.1-0.2	982
0.2-0.3	1982
0.3-0.4	2600
0.4-0.5	1692
0.5-0.6	1042
0.6-0.7	367
0.7-0.8	132
0.8-0.85	27
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8824	High Similarity	NPD2801	Approved
0.863	High Similarity	NPD1551	Phase 2
0.8611	High Similarity	NPD447	Suspended
0.8553	High Similarity	NPD6232	Discontinued
0.8526	High Similarity	NPD3817	Phase 2
0.8526	High Similarity	NPD5402	Approved
0.8471	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8471	Intermediate Similarity	NPD3882	Suspended
0.8397	Intermediate Similarity	NPD1934	Approved
0.8395	Intermediate Similarity	NPD7473	Discontinued
0.8313	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8293	Intermediate Similarity	NPD5844	Phase 1
0.8255	Intermediate Similarity	NPD2935	Discontinued
0.8235	Intermediate Similarity	NPD1511	Approved
0.8232	Intermediate Similarity	NPD3818	Discontinued
0.8228	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8129	Intermediate Similarity	NPD1512	Approved
0.8117	Intermediate Similarity	NPD6799	Approved
0.8113	Intermediate Similarity	NPD1465	Phase 2
0.811	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.811	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.811	Intermediate Similarity	NPD6166	Phase 2
0.8108	Intermediate Similarity	NPD1933	Approved
0.8086	Intermediate Similarity	NPD5494	Approved
0.8077	Intermediate Similarity	NPD5403	Approved
0.8075	Intermediate Similarity	NPD7075	Discontinued
0.8072	Intermediate Similarity	NPD7054	Approved
0.8056	Intermediate Similarity	NPD1203	Approved
0.8038	Intermediate Similarity	NPD6599	Discontinued
0.8026	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8024	Intermediate Similarity	NPD7074	Phase 3
0.8024	Intermediate Similarity	NPD7472	Approved
0.8	Intermediate Similarity	NPD7819	Suspended
0.7987	Intermediate Similarity	NPD230	Phase 1
0.7975	Intermediate Similarity	NPD3226	Approved
0.7949	Intermediate Similarity	NPD2534	Approved
0.7949	Intermediate Similarity	NPD2532	Approved
0.7949	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7949	Intermediate Similarity	NPD5401	Approved
0.7949	Intermediate Similarity	NPD2533	Approved
0.7933	Intermediate Similarity	NPD1607	Approved
0.7929	Intermediate Similarity	NPD6559	Discontinued
0.7922	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7922	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7905	Intermediate Similarity	NPD411	Approved
0.7891	Intermediate Similarity	NPD6832	Phase 2
0.7888	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7882	Intermediate Similarity	NPD7808	Phase 3
0.7875	Intermediate Similarity	NPD7411	Suspended
0.787	Intermediate Similarity	NPD6797	Phase 2
0.787	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7867	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7853	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7847	Intermediate Similarity	NPD9717	Approved
0.7843	Intermediate Similarity	NPD2346	Discontinued
0.7826	Intermediate Similarity	NPD6801	Discontinued
0.7824	Intermediate Similarity	NPD7251	Discontinued
0.7812	Intermediate Similarity	NPD4380	Phase 2
0.7806	Intermediate Similarity	NPD3750	Approved
0.78	Intermediate Similarity	NPD1240	Approved
0.7799	Intermediate Similarity	NPD1653	Approved
0.7792	Intermediate Similarity	NPD1549	Phase 2
0.7791	Intermediate Similarity	NPD7768	Phase 2
0.7736	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7725	Intermediate Similarity	NPD3926	Phase 2
0.7722	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7716	Intermediate Similarity	NPD37	Approved
0.7714	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7712	Intermediate Similarity	NPD1510	Phase 2
0.7711	Intermediate Similarity	NPD1247	Approved
0.7711	Intermediate Similarity	NPD6959	Discontinued
0.7697	Intermediate Similarity	NPD919	Approved
0.7697	Intermediate Similarity	NPD6234	Discontinued
0.7692	Intermediate Similarity	NPD4628	Phase 3
0.7683	Intermediate Similarity	NPD4965	Approved
0.7683	Intermediate Similarity	NPD4967	Phase 2
0.7683	Intermediate Similarity	NPD4966	Approved
0.7667	Intermediate Similarity	NPD2313	Discontinued
0.7667	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7662	Intermediate Similarity	NPD2796	Approved
0.7597	Intermediate Similarity	NPD2799	Discontinued
0.7597	Intermediate Similarity	NPD4308	Phase 3
0.7574	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7566	Intermediate Similarity	NPD943	Approved
0.7532	Intermediate Similarity	NPD6190	Approved
0.753	Intermediate Similarity	NPD3749	Approved
0.7529	Intermediate Similarity	NPD8313	Approved
0.7529	Intermediate Similarity	NPD8312	Approved
0.7528	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD3748	Approved
0.7483	Intermediate Similarity	NPD9493	Approved
0.7467	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7457	Intermediate Similarity	NPD5953	Discontinued
0.7442	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD6100	Approved
0.7436	Intermediate Similarity	NPD6099	Approved
0.7417	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD5353	Approved
0.7407	Intermediate Similarity	NPD920	Approved
0.7405	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD1243	Approved
0.7405	Intermediate Similarity	NPD2800	Approved
0.74	Intermediate Similarity	NPD1019	Discontinued
0.7396	Intermediate Similarity	NPD7199	Phase 2
0.7384	Intermediate Similarity	NPD7228	Approved
0.7368	Intermediate Similarity	NPD3027	Phase 3
0.7365	Intermediate Similarity	NPD9269	Phase 2
0.7353	Intermediate Similarity	NPD5711	Approved
0.7353	Intermediate Similarity	NPD5710	Approved
0.7341	Intermediate Similarity	NPD7286	Phase 2
0.7338	Intermediate Similarity	NPD4307	Phase 2
0.7338	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD1613	Approved
0.7333	Intermediate Similarity	NPD2797	Approved
0.7329	Intermediate Similarity	NPD9268	Approved
0.7317	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD5242	Approved
0.7297	Intermediate Similarity	NPD422	Phase 1
0.7284	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD1778	Approved
0.7267	Intermediate Similarity	NPD3225	Approved
0.7261	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD1608	Approved
0.7247	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD3018	Phase 2
0.7237	Intermediate Similarity	NPD9494	Approved
0.723	Intermediate Similarity	NPD3496	Discontinued
0.7229	Intermediate Similarity	NPD6385	Approved
0.7229	Intermediate Similarity	NPD6386	Approved
0.7222	Intermediate Similarity	NPD4357	Discontinued
0.7216	Intermediate Similarity	NPD7039	Approved
0.7216	Intermediate Similarity	NPD7685	Pre-registration
0.7216	Intermediate Similarity	NPD7038	Approved
0.7208	Intermediate Similarity	NPD3268	Approved
0.7208	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD8150	Discontinued
0.7207	Intermediate Similarity	NPD8434	Phase 2
0.72	Intermediate Similarity	NPD4749	Approved
0.7186	Intermediate Similarity	NPD6844	Discontinued
0.7184	Intermediate Similarity	NPD3751	Discontinued
0.7171	Intermediate Similarity	NPD2798	Approved
0.717	Intermediate Similarity	NPD2344	Approved
0.7168	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD6233	Phase 2
0.716	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD7033	Discontinued
0.7152	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4625	Phase 3
0.7134	Intermediate Similarity	NPD6651	Approved
0.7134	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD1481	Phase 2
0.7128	Intermediate Similarity	NPD7435	Discontinued
0.7117	Intermediate Similarity	NPD7390	Discontinued
0.7107	Intermediate Similarity	NPD5408	Approved
0.7107	Intermediate Similarity	NPD5405	Approved
0.7107	Intermediate Similarity	NPD5404	Approved
0.7107	Intermediate Similarity	NPD5406	Approved
0.7093	Intermediate Similarity	NPD8127	Discontinued
0.7086	Intermediate Similarity	NPD2983	Phase 2
0.7086	Intermediate Similarity	NPD2982	Phase 2
0.7079	Intermediate Similarity	NPD7549	Discontinued
0.7075	Intermediate Similarity	NPD5536	Phase 2
0.7073	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD1535	Discovery
0.7063	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD6778	Approved
0.7059	Intermediate Similarity	NPD6779	Approved
0.7059	Intermediate Similarity	NPD6777	Approved
0.7059	Intermediate Similarity	NPD6780	Approved
0.7059	Intermediate Similarity	NPD6782	Approved
0.7059	Intermediate Similarity	NPD6781	Approved
0.7059	Intermediate Similarity	NPD6776	Approved
0.7052	Intermediate Similarity	NPD3787	Discontinued
0.7047	Intermediate Similarity	NPD17	Approved
0.7037	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD4110	Phase 3
0.7031	Intermediate Similarity	NPD8151	Discontinued
0.7027	Intermediate Similarity	NPD9545	Approved
0.7024	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7022	Intermediate Similarity	NPD7240	Approved
0.702	Intermediate Similarity	NPD2981	Phase 2
0.7018	Intermediate Similarity	NPD6971	Discontinued
0.7	Intermediate Similarity	NPD4288	Approved
0.6994	Remote Similarity	NPD2309	Approved
0.6993	Remote Similarity	NPD1470	Approved
0.6987	Remote Similarity	NPD6798	Discontinued
0.6987	Remote Similarity	NPD3764	Approved
0.6987	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD6823	Phase 2
0.6968	Remote Similarity	NPD4908	Phase 1
0.6962	Remote Similarity	NPD6355	Discontinued

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