NPASS Compound

Structure

NPC121272 OpenBabel07101719132D 29 33 0 0 1 0 0 0 0 0999 V2000 -3.5254 3.6270 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4824 -1.9319 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5472 3.4190 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4483 -1.6730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2382 2.4680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1906 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9849 0.9482 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5310 0.0572 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7568 -0.4010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7568 1.4010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7071 -0.7071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4403 1.7869 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5323 0.0049 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2601 2.2601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7818 -0.6235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7818 1.6235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4417 1.7346 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9877 0.8436 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 -0.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.9511 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7346 2.4417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 1.0000 1.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 1.8910 3.4294 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2601 -1.2601 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5388 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8436 1.9877 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 1 0 0 0 0 2 4 1 0 0 0 0 3 5 1 0 0 0 0 4 11 1 0 0 0 0 5 14 1 0 0 0 0 6 9 1 0 0 0 0 6 10 1 0 0 0 0 7 8 2 0 0 0 0 7 12 1 0 0 0 0 8 13 1 0 0 0 0 9 15 2 0 0 0 0 10 16 1 0 0 0 0 11 19 1 0 0 0 0 12 17 2 0 0 0 0 13 18 2 0 0 0 0 14 20 2 0 0 0 0 15 23 1 0 0 0 0 16 24 1 0 0 0 0 17 18 1 0 0 0 0 17 21 1 0 0 0 0 18 25 1 0 0 0 0 19 23 1 0 0 0 0 19 25 1 0 0 0 0 20 24 1 0 0 0 0 20 28 1 0 0 0 0 21 26 2 0 0 0 0 21 29 1 0 0 0 0 22 23 1 0 0 0 0 22 27 2 0 0 0 0 22 28 1 0 0 0 0 23 24 1 0 0 0 0 24 25 1 0 0 0 0 25 29 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	392.2
Volume:	414.879
LogP:	5.483
LogD:	5.161
LogS:	-5.433
# Rotatable Bonds:	4
TPSA:	52.6
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.506
Synthetic Accessibility Score:	5.205
Fsp3:	0.52
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.83
MDCK Permeability:	1.857502866187133e-05
Pgp-inhibitor:	0.781
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.258
30% Bioavailability (F30%):	0.256

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.889
Plasma Protein Binding (PPB):	98.49813842773438%
Volume Distribution (VD):	0.959
Pgp-substrate:	1.5669898986816406%

ADMET: Metabolism

CYP1A2-inhibitor:	0.375
CYP1A2-substrate:	0.31
CYP2C19-inhibitor:	0.911
CYP2C19-substrate:	0.821
CYP2C9-inhibitor:	0.877
CYP2C9-substrate:	0.775
CYP2D6-inhibitor:	0.312
CYP2D6-substrate:	0.141
CYP3A4-inhibitor:	0.875
CYP3A4-substrate:	0.693

ADMET: Excretion

Clearance (CL):	8.449
Half-life (T1/2):	0.018

ADMET: Toxicity

hERG Blockers:	0.005
Human Hepatotoxicity (H-HT):	0.719
Drug-inuced Liver Injury (DILI):	0.092
AMES Toxicity:	0.684
Rat Oral Acute Toxicity:	0.968
Maximum Recommended Daily Dose:	0.124
Skin Sensitization:	0.023
Carcinogencity:	0.875
Eye Corrosion:	0.005
Eye Irritation:	0.604
Respiratory Toxicity:	0.95

Download Data

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

Natural Product: NPC121272

Natural Product ID:	NPC121272
*Common Name:**	Sinaspirolide
IUPAC Name:	n.a.
Synonyms:	Sinaspirolide
Standard InCHIKey:	WXOFSAKMVZUYNE-ZHZULCJRSA-N
Standard InCHI:	InChI=1S/C25H28O4/c1-3-5-14-20-24-16-10-6-9-15-23(24,22(27)28-20)19(11-4-2)25(24)18-13-8-7-12-17(18)21(26)29-25/h7-9,12-15,19H,3-6,10-11,16H2,1-2H3/b20-14-
SMILES:	CCC/C=C/1OC(=O)C23C1(CCCC=C2)C1(C3CCC)OC(=O)c2c1cccc2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL519465
PubChem CID:	44575264
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000301] Benzofurans [CHEMONTID:0001578] Benzofuranones

*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
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	roots	purchased from Kiu Shun Trading Ltd., Vancouver, Canada	2000	PMID[16643021]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25538068]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27400088]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO15462	Angelica sinensis	Species	Apiaceae	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
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1785	Individual Protein	Serotonin 7 (5-HT7) receptor	Homo sapiens	Inhibition	=	24.0	%	PMID[553334]

☑ 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 NPC121272 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	322
0.1-0.2	1376
0.2-0.3	2594
0.3-0.4	7138
0.4-0.5	12316
0.5-0.6	13177
0.6-0.7	5198
0.7-0.8	571
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.881	High Similarity	NPC51292
0.843	Intermediate Similarity	NPC307651
0.8305	Intermediate Similarity	NPC37622
0.8305	Intermediate Similarity	NPC30594
0.8217	Intermediate Similarity	NPC246166
0.8182	Intermediate Similarity	NPC147561
0.8182	Intermediate Similarity	NPC475508
0.8115	Intermediate Similarity	NPC82899
0.8115	Intermediate Similarity	NPC270699
0.8099	Intermediate Similarity	NPC196246
0.8099	Intermediate Similarity	NPC214067
0.8074	Intermediate Similarity	NPC324898
0.8074	Intermediate Similarity	NPC134937
0.8074	Intermediate Similarity	NPC298547
0.8033	Intermediate Similarity	NPC1082
0.8033	Intermediate Similarity	NPC305912
0.8017	Intermediate Similarity	NPC10251
0.8017	Intermediate Similarity	NPC265407
0.8017	Intermediate Similarity	NPC17417
0.8017	Intermediate Similarity	NPC83628
0.8015	Intermediate Similarity	NPC149401
0.8015	Intermediate Similarity	NPC279637
0.8	Intermediate Similarity	NPC149691
0.7951	Intermediate Similarity	NPC251854
0.7951	Intermediate Similarity	NPC93084
0.7941	Intermediate Similarity	NPC474608
0.7934	Intermediate Similarity	NPC56493
0.7926	Intermediate Similarity	NPC238370
0.7923	Intermediate Similarity	NPC472703
0.792	Intermediate Similarity	NPC210092
0.7917	Intermediate Similarity	NPC209632
0.7914	Intermediate Similarity	NPC251294
0.7907	Intermediate Similarity	NPC50872
0.7899	Intermediate Similarity	NPC205305
0.7899	Intermediate Similarity	NPC327511
0.7886	Intermediate Similarity	NPC474157
0.7883	Intermediate Similarity	NPC66761
0.7883	Intermediate Similarity	NPC472577
0.7883	Intermediate Similarity	NPC17877
0.7883	Intermediate Similarity	NPC200154
0.7883	Intermediate Similarity	NPC195647
0.7883	Intermediate Similarity	NPC291638
0.7869	Intermediate Similarity	NPC469636
0.7863	Intermediate Similarity	NPC472704
0.7857	Intermediate Similarity	NPC187566
0.7851	Intermediate Similarity	NPC119271
0.7842	Intermediate Similarity	NPC121268
0.7842	Intermediate Similarity	NPC53361
0.784	Intermediate Similarity	NPC153053
0.7833	Intermediate Similarity	NPC114594
0.7833	Intermediate Similarity	NPC31786
0.7826	Intermediate Similarity	NPC202729
0.7815	Intermediate Similarity	NPC45613
0.7805	Intermediate Similarity	NPC174099
0.7801	Intermediate Similarity	NPC183540
0.7797	Intermediate Similarity	NPC325497
0.7794	Intermediate Similarity	NPC239358
0.7794	Intermediate Similarity	NPC233692
0.7794	Intermediate Similarity	NPC469499
0.7794	Intermediate Similarity	NPC233860
0.7786	Intermediate Similarity	NPC477904
0.7786	Intermediate Similarity	NPC183270
0.777	Intermediate Similarity	NPC27721
0.777	Intermediate Similarity	NPC183122
0.777	Intermediate Similarity	NPC283375
0.777	Intermediate Similarity	NPC475373
0.7754	Intermediate Similarity	NPC265459
0.7754	Intermediate Similarity	NPC290833
0.7754	Intermediate Similarity	NPC475262
0.7754	Intermediate Similarity	NPC473216
0.7754	Intermediate Similarity	NPC270364
0.7754	Intermediate Similarity	NPC473399
0.775	Intermediate Similarity	NPC89886
0.7746	Intermediate Similarity	NPC153214
0.7746	Intermediate Similarity	NPC131966
0.7746	Intermediate Similarity	NPC191387
0.7744	Intermediate Similarity	NPC476599
0.7737	Intermediate Similarity	NPC472248
0.7724	Intermediate Similarity	NPC269023
0.7724	Intermediate Similarity	NPC99846
0.7714	Intermediate Similarity	NPC210591
0.7714	Intermediate Similarity	NPC475652
0.7714	Intermediate Similarity	NPC214550
0.7714	Intermediate Similarity	NPC9905
0.7708	Intermediate Similarity	NPC469513
0.7698	Intermediate Similarity	NPC285221
0.7698	Intermediate Similarity	NPC194769
0.7692	Intermediate Similarity	NPC232958
0.7692	Intermediate Similarity	NPC473243
0.7687	Intermediate Similarity	NPC472706
0.7681	Intermediate Similarity	NPC153617
0.7681	Intermediate Similarity	NPC28836
0.7681	Intermediate Similarity	NPC472250
0.7681	Intermediate Similarity	NPC311492
0.768	Intermediate Similarity	NPC321852
0.7671	Intermediate Similarity	NPC303429
0.7671	Intermediate Similarity	NPC222102
0.7664	Intermediate Similarity	NPC472394
0.766	Intermediate Similarity	NPC97667
0.766	Intermediate Similarity	NPC87934
0.766	Intermediate Similarity	NPC184747
0.766	Intermediate Similarity	NPC171207
0.766	Intermediate Similarity	NPC275592
0.766	Intermediate Similarity	NPC476094
0.766	Intermediate Similarity	NPC100913
0.766	Intermediate Similarity	NPC473085
0.766	Intermediate Similarity	NPC48017
0.766	Intermediate Similarity	NPC90614
0.766	Intermediate Similarity	NPC473081
0.766	Intermediate Similarity	NPC200592
0.766	Intermediate Similarity	NPC473613
0.766	Intermediate Similarity	NPC162613
0.766	Intermediate Similarity	NPC211137
0.766	Intermediate Similarity	NPC43241
0.766	Intermediate Similarity	NPC473112
0.766	Intermediate Similarity	NPC473109
0.766	Intermediate Similarity	NPC4341
0.766	Intermediate Similarity	NPC473060
0.766	Intermediate Similarity	NPC147880
0.766	Intermediate Similarity	NPC473758
0.7647	Intermediate Similarity	NPC42234
0.7643	Intermediate Similarity	NPC86772
0.7626	Intermediate Similarity	NPC79699
0.7622	Intermediate Similarity	NPC95449
0.7619	Intermediate Similarity	NPC161611
0.7619	Intermediate Similarity	NPC128368
0.7619	Intermediate Similarity	NPC469415
0.7606	Intermediate Similarity	NPC87448
0.7606	Intermediate Similarity	NPC97947
0.7606	Intermediate Similarity	NPC16912
0.7606	Intermediate Similarity	NPC118080
0.7606	Intermediate Similarity	NPC41481
0.7606	Intermediate Similarity	NPC266374
0.7606	Intermediate Similarity	NPC472576
0.7606	Intermediate Similarity	NPC27377
0.7606	Intermediate Similarity	NPC291599
0.7603	Intermediate Similarity	NPC301943
0.7603	Intermediate Similarity	NPC474365
0.76	Intermediate Similarity	NPC260818
0.7591	Intermediate Similarity	NPC470278
0.7589	Intermediate Similarity	NPC276652
0.7589	Intermediate Similarity	NPC272523
0.7589	Intermediate Similarity	NPC170718
0.7589	Intermediate Similarity	NPC325805
0.7586	Intermediate Similarity	NPC478263
0.7586	Intermediate Similarity	NPC240115
0.7581	Intermediate Similarity	NPC85493
0.7581	Intermediate Similarity	NPC474364
0.7578	Intermediate Similarity	NPC226093
0.7571	Intermediate Similarity	NPC472545
0.7571	Intermediate Similarity	NPC472551
0.7559	Intermediate Similarity	NPC308744
0.7559	Intermediate Similarity	NPC196075
0.7557	Intermediate Similarity	NPC238861
0.7557	Intermediate Similarity	NPC77000
0.7556	Intermediate Similarity	NPC169913
0.7554	Intermediate Similarity	NPC48929
0.7552	Intermediate Similarity	NPC51181
0.7552	Intermediate Similarity	NPC192658
0.754	Intermediate Similarity	NPC212415
0.7536	Intermediate Similarity	NPC477360
0.7535	Intermediate Similarity	NPC475400
0.7535	Intermediate Similarity	NPC475660
0.7535	Intermediate Similarity	NPC472547
0.7534	Intermediate Similarity	NPC132652
0.7518	Intermediate Similarity	NPC194979
0.7518	Intermediate Similarity	NPC39549
0.7518	Intermediate Similarity	NPC471832
0.7518	Intermediate Similarity	NPC272946
0.7517	Intermediate Similarity	NPC134131
0.7517	Intermediate Similarity	NPC25043
0.7517	Intermediate Similarity	NPC471100
0.7517	Intermediate Similarity	NPC471107
0.7517	Intermediate Similarity	NPC478264
0.7517	Intermediate Similarity	NPC311825
0.7517	Intermediate Similarity	NPC92867
0.7517	Intermediate Similarity	NPC125882
0.75	Intermediate Similarity	NPC246480
0.75	Intermediate Similarity	NPC146351
0.75	Intermediate Similarity	NPC477893
0.75	Intermediate Similarity	NPC475429
0.75	Intermediate Similarity	NPC163087
0.75	Intermediate Similarity	NPC139067
0.75	Intermediate Similarity	NPC270498
0.75	Intermediate Similarity	NPC147217
0.75	Intermediate Similarity	NPC473673
0.75	Intermediate Similarity	NPC191082
0.75	Intermediate Similarity	NPC177340
0.75	Intermediate Similarity	NPC311339
0.7483	Intermediate Similarity	NPC473654
0.7483	Intermediate Similarity	NPC473497
0.7481	Intermediate Similarity	NPC275576
0.7481	Intermediate Similarity	NPC476033
0.748	Intermediate Similarity	NPC272524
0.7467	Intermediate Similarity	NPC469422
0.7467	Intermediate Similarity	NPC34066
0.7467	Intermediate Similarity	NPC469398
0.7466	Intermediate Similarity	NPC209592
0.7466	Intermediate Similarity	NPC48599
0.7466	Intermediate Similarity	NPC20255

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 NPC121272 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	288
0.1-0.2	817
0.2-0.3	1509
0.3-0.4	2886
0.4-0.5	2439
0.5-0.6	989
0.6-0.7	213
0.7-0.8	9
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8182	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.8017	Intermediate Similarity	NPD2182	Approved
0.7833	Intermediate Similarity	NPD164	Approved
0.7591	Intermediate Similarity	NPD3764	Approved
0.7557	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7556	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.754	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7364	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD2067	Discontinued
0.7185	Intermediate Similarity	NPD6287	Discontinued
0.7165	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD5951	Approved
0.7073	Intermediate Similarity	NPD1238	Approved
0.7034	Intermediate Similarity	NPD3748	Approved
0.6985	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD5909	Discontinued
0.6933	Remote Similarity	NPD7236	Approved
0.6918	Remote Similarity	NPD2799	Discontinued
0.6913	Remote Similarity	NPD4628	Phase 3
0.6912	Remote Similarity	NPD17	Approved
0.6906	Remote Similarity	NPD1876	Approved
0.6901	Remote Similarity	NPD7008	Discontinued
0.6889	Remote Similarity	NPD9545	Approved
0.6883	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD2532	Approved
0.6842	Remote Similarity	NPD2534	Approved
0.6842	Remote Similarity	NPD2533	Approved
0.6824	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD6005	Phase 3
0.6824	Remote Similarity	NPD6002	Phase 3
0.6824	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD2346	Discontinued
0.6824	Remote Similarity	NPD6004	Phase 3
0.6803	Remote Similarity	NPD1202	Approved
0.68	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.68	Remote Similarity	NPD3750	Approved
0.6788	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.678	Remote Similarity	NPD9259	Approved
0.678	Remote Similarity	NPD9257	Approved
0.6772	Remote Similarity	NPD1929	Approved
0.6772	Remote Similarity	NPD1930	Approved
0.6772	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD1608	Approved
0.6763	Remote Similarity	NPD3972	Approved
0.6763	Remote Similarity	NPD6637	Approved
0.6759	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD4307	Phase 2
0.6736	Remote Similarity	NPD2313	Discontinued
0.6713	Remote Similarity	NPD6832	Phase 2
0.671	Remote Similarity	NPD7239	Suspended
0.669	Remote Similarity	NPD2798	Approved
0.669	Remote Similarity	NPD8032	Phase 2
0.6689	Remote Similarity	NPD7003	Approved
0.6688	Remote Similarity	NPD6273	Approved
0.6667	Remote Similarity	NPD3226	Approved
0.6667	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2066	Phase 3
0.6644	Remote Similarity	NPD2979	Phase 3
0.6643	Remote Similarity	NPD9717	Approved
0.6622	Remote Similarity	NPD2569	Approved
0.6622	Remote Similarity	NPD2567	Approved
0.662	Remote Similarity	NPD2797	Approved
0.662	Remote Similarity	NPD3267	Approved
0.662	Remote Similarity	NPD3266	Approved
0.6618	Remote Similarity	NPD9493	Approved
0.6599	Remote Similarity	NPD230	Phase 1
0.6594	Remote Similarity	NPD5585	Approved
0.6593	Remote Similarity	NPD2629	Approved
0.6585	Remote Similarity	NPD1088	Approved
0.6584	Remote Similarity	NPD3749	Approved
0.6583	Remote Similarity	NPD1087	Approved
0.6579	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD4308	Phase 3
0.6573	Remote Similarity	NPD1019	Discontinued
0.6571	Remote Similarity	NPD1281	Approved
0.6571	Remote Similarity	NPD518	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD7799	Discontinued
0.6557	Remote Similarity	NPD9256	Approved
0.6557	Remote Similarity	NPD9258	Approved
0.6544	Remote Similarity	NPD4198	Discontinued
0.6538	Remote Similarity	NPD920	Approved
0.6538	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6533	Remote Similarity	NPD2935	Discontinued
0.6532	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6525	Remote Similarity	NPD1877	Discontinued
0.6522	Remote Similarity	NPD7741	Discontinued
0.6519	Remote Similarity	NPD6599	Discontinued
0.6513	Remote Similarity	NPD1243	Approved
0.6513	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6513	Remote Similarity	NPD2800	Approved
0.6512	Remote Similarity	NPD6647	Phase 2
0.6512	Remote Similarity	NPD8434	Phase 2
0.6507	Remote Similarity	NPD1296	Phase 2
0.6507	Remote Similarity	NPD3268	Approved
0.65	Remote Similarity	NPD7819	Suspended
0.649	Remote Similarity	NPD1471	Phase 3
0.6489	Remote Similarity	NPD6685	Approved
0.6489	Remote Similarity	NPD3134	Approved
0.6486	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD447	Suspended
0.648	Remote Similarity	NPD1693	Approved
0.6475	Remote Similarity	NPD5691	Approved
0.6471	Remote Similarity	NPD4766	Approved
0.6466	Remote Similarity	NPD5239	Approved
0.6466	Remote Similarity	NPD5235	Approved
0.6466	Remote Similarity	NPD5240	Approved
0.6466	Remote Similarity	NPD5236	Approved
0.6466	Remote Similarity	NPD5237	Approved
0.6463	Remote Similarity	NPD7961	Discontinued
0.6452	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD6858	Approved
0.6444	Remote Similarity	NPD7094	Approved
0.6442	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6434	Remote Similarity	NPD1283	Approved
0.6434	Remote Similarity	NPD1932	Approved
0.6429	Remote Similarity	NPD5126	Approved
0.6429	Remote Similarity	NPD5125	Phase 3
0.6429	Remote Similarity	NPD1989	Approved
0.6424	Remote Similarity	NPD2796	Approved
0.6424	Remote Similarity	NPD2438	Suspended
0.6423	Remote Similarity	NPD1086	Approved
0.6423	Remote Similarity	NPD3672	Approved
0.6423	Remote Similarity	NPD1089	Approved
0.6423	Remote Similarity	NPD3673	Approved
0.6423	Remote Similarity	NPD1090	Approved
0.642	Remote Similarity	NPD4967	Phase 2
0.642	Remote Similarity	NPD7058	Phase 2
0.642	Remote Similarity	NPD4965	Approved
0.642	Remote Similarity	NPD4966	Approved
0.642	Remote Similarity	NPD7057	Phase 3
0.6418	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6418	Remote Similarity	NPD2201	Approved
0.641	Remote Similarity	NPD642	Clinical (unspecified phase)
0.641	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6398	Remote Similarity	NPD5760	Phase 2
0.6398	Remote Similarity	NPD5761	Phase 2
0.6397	Remote Similarity	NPD1241	Discontinued
0.6395	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6395	Remote Similarity	NPD8407	Phase 2
0.6391	Remote Similarity	NPD2329	Discontinued
0.6389	Remote Similarity	NPD1203	Approved
0.6385	Remote Similarity	NPD9261	Approved
0.6383	Remote Similarity	NPD3496	Discontinued
0.6382	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6378	Remote Similarity	NPD3495	Discontinued
0.637	Remote Similarity	NPD969	Suspended
0.6364	Remote Similarity	NPD4359	Approved
0.6358	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6357	Remote Similarity	NPD3025	Approved
0.6357	Remote Similarity	NPD3024	Approved
0.6352	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6351	Remote Similarity	NPD6663	Approved
0.6349	Remote Similarity	NPD9260	Approved
0.6346	Remote Similarity	NPD6799	Approved
0.6345	Remote Similarity	NPD6085	Phase 2
0.6345	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6345	Remote Similarity	NPD2788	Approved
0.6343	Remote Similarity	NPD1317	Discontinued
0.6341	Remote Similarity	NPD800	Approved
0.6341	Remote Similarity	NPD6234	Discontinued
0.6331	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.632	Remote Similarity	NPD7631	Approved
0.6319	Remote Similarity	NPD2198	Approved
0.6319	Remote Similarity	NPD2199	Approved
0.6316	Remote Similarity	NPD5404	Approved
0.6316	Remote Similarity	NPD6100	Approved
0.6316	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD8368	Discontinued
0.6316	Remote Similarity	NPD1551	Phase 2
0.6316	Remote Similarity	NPD1358	Approved
0.6316	Remote Similarity	NPD5405	Approved
0.6316	Remote Similarity	NPD5408	Approved
0.6316	Remote Similarity	NPD2531	Phase 2
0.6316	Remote Similarity	NPD5406	Approved
0.6316	Remote Similarity	NPD6099	Approved
0.6312	Remote Similarity	NPD1778	Approved
0.6312	Remote Similarity	NPD4626	Approved
0.6303	Remote Similarity	NPD5494	Approved
0.6294	Remote Similarity	NPD4878	Approved
0.6284	Remote Similarity	NPD411	Approved
0.6284	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6282	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6277	Remote Similarity	NPD2652	Approved
0.6277	Remote Similarity	NPD2650	Approved
0.6276	Remote Similarity	NPD1470	Approved
0.6275	Remote Similarity	NPD2344	Approved
0.6275	Remote Similarity	NPD2353	Approved
0.6275	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6273	Remote Similarity	NPD6385	Approved
0.6273	Remote Similarity	NPD6386	Approved
0.6268	Remote Similarity	NPD3023	Approved
0.6268	Remote Similarity	NPD3026	Approved
0.6267	Remote Similarity	NPD4618	Approved
0.6267	Remote Similarity	NPD4622	Approved
0.6267	Remote Similarity	NPD6355	Discontinued
0.6267	Remote Similarity	NPD1933	Approved
0.626	Remote Similarity	NPD5765	Approved
0.6258	Remote Similarity	NPD4288	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