NPASS Compound

Structure

CID200594 OpenBabel06191715592D 23 26 0 0 0 0 0 0 0 0999 V2000 -2.8399 0.1478 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9693 1.8750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6479 0.1235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5382 2.8507 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4649 0.3145 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4060 1.0488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5139 0.6235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5355 2.7760 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9749 2.0245 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 -1.4088 1.1235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5139 1.6235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6479 2.1235 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 3.4649 1.9325 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9749 0.2225 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0988 3.6022 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6479 3.1235 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.7740 2.8836 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5984 -0.5593 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0527 1.1235 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.2470 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 6 1 0 0 0 0 2 6 2 0 0 0 0 2 8 1 0 0 0 0 3 7 2 0 0 0 0 3 10 1 0 0 0 0 4 8 2 0 0 0 0 4 9 1 0 0 0 0 5 7 1 0 0 0 0 5 21 1 0 0 0 0 6 11 1 0 0 0 0 7 12 1 0 0 0 0 8 17 1 0 0 0 0 9 11 2 0 0 0 0 9 22 1 0 0 0 0 10 14 2 0 0 0 0 10 23 1 0 0 0 0 11 16 1 0 0 0 0 12 13 2 0 0 0 0 12 15 1 0 0 0 0 13 14 1 0 0 0 0 13 18 1 0 0 0 0 14 22 1 0 0 0 0 15 19 2 0 0 0 0 15 21 1 0 0 0 0 16 20 2 0 0 0 0 16 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	314.04
Volume:	291.506
LogP:	3.526
LogD:	2.613
LogS:	-4.215
# Rotatable Bonds:	0
TPSA:	109.36
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.432
Synthetic Accessibility Score:	3.396
Fsp3:	0.062
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:	-5.097
MDCK Permeability:	1.6909836631384678e-05
Pgp-inhibitor:	0.003
Pgp-substrate:	0.023
Human Intestinal Absorption (HIA):	0.077
20% Bioavailability (F20%):	0.028
30% Bioavailability (F30%):	0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.024
Plasma Protein Binding (PPB):	98.20970916748047%
Volume Distribution (VD):	0.452
Pgp-substrate:	4.819476127624512%

ADMET: Metabolism

CYP1A2-inhibitor:	0.943
CYP1A2-substrate:	0.117
CYP2C19-inhibitor:	0.064
CYP2C19-substrate:	0.055
CYP2C9-inhibitor:	0.67
CYP2C9-substrate:	0.412
CYP2D6-inhibitor:	0.078
CYP2D6-substrate:	0.195
CYP3A4-inhibitor:	0.164
CYP3A4-substrate:	0.079

ADMET: Excretion

Clearance (CL):	12.229
Half-life (T1/2):	0.867

ADMET: Toxicity

hERG Blockers:	0.01
Human Hepatotoxicity (H-HT):	0.012
Drug-inuced Liver Injury (DILI):	0.489
AMES Toxicity:	0.015
Rat Oral Acute Toxicity:	0.996
Maximum Recommended Daily Dose:	0.923
Skin Sensitization:	0.847
Carcinogencity:	0.839
Eye Corrosion:	0.004
Eye Irritation:	0.915
Respiratory Toxicity:	0.672

Download Data

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

Natural Product: NPC200594

Natural Product ID:	NPC200594
*Common Name:**	Variolaric Acid
IUPAC Name:	n.a.
Synonyms:	Variolaric Acid
Standard InCHIKey:	LPUOVEFMUOQBFV-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C16H10O7/c1-6-2-8(17)4-9-11(6)16(20)23-10-3-7-5-21-15(19)12(7)13(18)14(10)22-9/h2-4,17-18H,5H2,1H3
SMILES:	Cc1cc(cc2c1C(=O)Oc1cc3COC(=O)c3c(c1O2)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL220486
PubChem CID:	12444681
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000254] Ethers [CHEMONTID:0002463] Diarylethers

*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
NPO10332	Garcinia atroviridis	Species	Clusiaceae	Eukaryota	roots	n.a.	n.a.	PMID[11473441]
NPO16337	Ochrolechia parella	Species	Ochrolechiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17256903]
NPO12221	Acacia saligna	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25183120]
NPO12221	Acacia saligna	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16337	Ochrolechia parella	Species	Ochrolechiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13194	Gentiana purpurea	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27306	Sterculia urens	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10332	Garcinia atroviridis	Species	Clusiaceae	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
EC50	4
IC50	1

Activity Type	# Activity
Cell Line	1
NON-MOLECULAR	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT319	Cell Line	B16	Mus musculus	IC50	=	38700.0	nM	PMID[490718]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	EC50	>	100000.0	nM	PMID[490719]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	EC50	>	50000.0	nM	PMID[490719]

☑ 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 NPC200594 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	368
0.1-0.2	1775
0.2-0.3	4462
0.3-0.4	9945
0.4-0.5	7970
0.5-0.6	3483
0.6-0.7	5108
0.7-0.8	6479
0.8-0.85	2403
0.85-0.9	646
0.9-0.95	55
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9545	High Similarity	NPC238381
0.9542	High Similarity	NPC54928
0.9351	High Similarity	NPC471800
0.9342	High Similarity	NPC96501
0.929	High Similarity	NPC150227
0.9281	High Similarity	NPC204350
0.9255	High Similarity	NPC17219
0.9245	High Similarity	NPC8070
0.9231	High Similarity	NPC77679
0.9231	High Similarity	NPC84935
0.9231	High Similarity	NPC190020
0.9226	High Similarity	NPC20541
0.9226	High Similarity	NPC79998
0.9226	High Similarity	NPC199926
0.9182	High Similarity	NPC300984
0.9182	High Similarity	NPC156082
0.9177	High Similarity	NPC303565
0.9172	High Similarity	NPC168616
0.9172	High Similarity	NPC83763
0.9167	High Similarity	NPC227062
0.9125	High Similarity	NPC267153
0.9125	High Similarity	NPC112981
0.9119	High Similarity	NPC144843
0.9119	High Similarity	NPC93739
0.9103	High Similarity	NPC16082
0.9103	High Similarity	NPC82592
0.9097	High Similarity	NPC289968
0.9085	High Similarity	NPC139350
0.9074	High Similarity	NPC26568
0.9068	High Similarity	NPC472452
0.9068	High Similarity	NPC20216
0.9062	High Similarity	NPC475985
0.9062	High Similarity	NPC284007
0.9038	High Similarity	NPC281477
0.9032	High Similarity	NPC473732
0.9018	High Similarity	NPC1827
0.9018	High Similarity	NPC10576
0.9018	High Similarity	NPC20543
0.9018	High Similarity	NPC239440
0.9018	High Similarity	NPC246716
0.9012	High Similarity	NPC272485
0.9012	High Similarity	NPC292788
0.9006	High Similarity	NPC326520
0.8994	High Similarity	NPC47623
0.8987	High Similarity	NPC300727
0.8987	High Similarity	NPC241904
0.8981	High Similarity	NPC38898
0.8974	High Similarity	NPC295646
0.8974	High Similarity	NPC199773
0.8974	High Similarity	NPC475116
0.8968	High Similarity	NPC151473
0.8961	High Similarity	NPC120464
0.8961	High Similarity	NPC107636
0.8957	High Similarity	NPC165979
0.8957	High Similarity	NPC163130
0.8954	High Similarity	NPC138978
0.8954	High Similarity	NPC32058
0.8954	High Similarity	NPC85734
0.8951	High Similarity	NPC170245
0.8947	High Similarity	NPC66404
0.8947	High Similarity	NPC95123
0.8944	High Similarity	NPC474350
0.8944	High Similarity	NPC234004
0.8944	High Similarity	NPC133065
0.894	High Similarity	NPC105648
0.8931	High Similarity	NPC37502
0.8931	High Similarity	NPC476242
0.8931	High Similarity	NPC40702
0.8931	High Similarity	NPC267627
0.8924	High Similarity	NPC472456
0.8924	High Similarity	NPC274730
0.8922	High Similarity	NPC240887
0.8922	High Similarity	NPC113446
0.8922	High Similarity	NPC470091
0.8922	High Similarity	NPC329161
0.891	High Similarity	NPC31363
0.8909	High Similarity	NPC181523
0.8903	High Similarity	NPC223579
0.8903	High Similarity	NPC183950
0.8903	High Similarity	NPC287101
0.8903	High Similarity	NPC48479
0.8903	High Similarity	NPC177298
0.8903	High Similarity	NPC137062
0.8903	High Similarity	NPC52005
0.8902	High Similarity	NPC109827
0.8902	High Similarity	NPC124470
0.8889	High Similarity	NPC39306
0.8889	High Similarity	NPC134621
0.8882	High Similarity	NPC8300
0.8882	High Similarity	NPC258307
0.8875	High Similarity	NPC36217
0.8875	High Similarity	NPC228785
0.8875	High Similarity	NPC14353
0.8875	High Similarity	NPC292415
0.8875	High Similarity	NPC56085
0.8874	High Similarity	NPC220106
0.8874	High Similarity	NPC90411
0.8868	High Similarity	NPC299520
0.8868	High Similarity	NPC108456
0.8868	High Similarity	NPC129684
0.8868	High Similarity	NPC469584
0.8868	High Similarity	NPC111969
0.8868	High Similarity	NPC247713
0.8861	High Similarity	NPC213622
0.8861	High Similarity	NPC2928
0.8861	High Similarity	NPC67396
0.8855	High Similarity	NPC289147
0.8854	High Similarity	NPC236637
0.8854	High Similarity	NPC120163
0.8854	High Similarity	NPC198826
0.8854	High Similarity	NPC83508
0.8854	High Similarity	NPC304954
0.8854	High Similarity	NPC100887
0.8854	High Similarity	NPC301323
0.8854	High Similarity	NPC212678
0.8854	High Similarity	NPC39732
0.8854	High Similarity	NPC131624
0.8854	High Similarity	NPC302950
0.8854	High Similarity	NPC25270
0.8854	High Similarity	NPC260979
0.8854	High Similarity	NPC477231
0.8854	High Similarity	NPC239128
0.8854	High Similarity	NPC293183
0.8854	High Similarity	NPC275836
0.8854	High Similarity	NPC219582
0.8854	High Similarity	NPC187498
0.8854	High Similarity	NPC57030
0.8854	High Similarity	NPC71334
0.8854	High Similarity	NPC188203
0.8854	High Similarity	NPC162313
0.8854	High Similarity	NPC60972
0.8854	High Similarity	NPC222830
0.8854	High Similarity	NPC257648
0.8854	High Similarity	NPC156222
0.8854	High Similarity	NPC256283
0.8854	High Similarity	NPC241498
0.8854	High Similarity	NPC275722
0.8848	High Similarity	NPC158226
0.8841	High Similarity	NPC247136
0.8834	High Similarity	NPC29160
0.8831	High Similarity	NPC237208
0.8827	High Similarity	NPC18100
0.8827	High Similarity	NPC7483
0.8824	High Similarity	NPC27106
0.882	High Similarity	NPC61010
0.882	High Similarity	NPC278052
0.882	High Similarity	NPC473106
0.882	High Similarity	NPC103201
0.882	High Similarity	NPC188486
0.882	High Similarity	NPC349525
0.882	High Similarity	NPC40491
0.8812	High Similarity	NPC55738
0.8812	High Similarity	NPC195832
0.8812	High Similarity	NPC196879
0.8812	High Similarity	NPC100123
0.8812	High Similarity	NPC329091
0.8805	High Similarity	NPC255106
0.8805	High Similarity	NPC235165
0.8805	High Similarity	NPC24640
0.8805	High Similarity	NPC472916
0.8797	High Similarity	NPC47781
0.8797	High Similarity	NPC176775
0.8797	High Similarity	NPC89474
0.8797	High Similarity	NPC22519
0.8797	High Similarity	NPC250822
0.8797	High Similarity	NPC75279
0.8797	High Similarity	NPC18727
0.8797	High Similarity	NPC255350
0.8797	High Similarity	NPC160951
0.8797	High Similarity	NPC231018
0.8797	High Similarity	NPC69394
0.8797	High Similarity	NPC469550
0.8797	High Similarity	NPC298802
0.8797	High Similarity	NPC274327
0.8797	High Similarity	NPC183878
0.8797	High Similarity	NPC145379
0.8797	High Similarity	NPC276409
0.879	High Similarity	NPC202157
0.879	High Similarity	NPC200740
0.879	High Similarity	NPC200773
0.879	High Similarity	NPC252933
0.879	High Similarity	NPC133953
0.879	High Similarity	NPC125062
0.879	High Similarity	NPC54394
0.879	High Similarity	NPC50403
0.879	High Similarity	NPC240768
0.879	High Similarity	NPC28274
0.879	High Similarity	NPC75695
0.878	High Similarity	NPC234331
0.878	High Similarity	NPC86477
0.8774	High Similarity	NPC30647
0.8774	High Similarity	NPC33265
0.8774	High Similarity	NPC62536
0.8774	High Similarity	NPC108406
0.8774	High Similarity	NPC55557
0.8774	High Similarity	NPC12200
0.8774	High Similarity	NPC61871
0.8773	High Similarity	NPC473286
0.8773	High Similarity	NPC130920
0.8773	High Similarity	NPC472277

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 NPC200594 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	334
0.1-0.2	962
0.2-0.3	1969
0.3-0.4	2582
0.4-0.5	1739
0.5-0.6	959
0.6-0.7	438
0.7-0.8	132
0.8-0.85	30
0.85-0.9	5
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8924	High Similarity	NPD3882	Suspended
0.8854	High Similarity	NPD1934	Approved
0.8797	High Similarity	NPD2801	Approved
0.8679	High Similarity	NPD1465	Phase 2
0.8625	High Similarity	NPD3817	Phase 2
0.8581	High Similarity	NPD1511	Approved
0.8571	High Similarity	NPD4868	Clinical (unspecified phase)
0.8562	High Similarity	NPD2393	Clinical (unspecified phase)
0.8554	High Similarity	NPD3818	Discontinued
0.8537	High Similarity	NPD6232	Discontinued
0.8497	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8471	Intermediate Similarity	NPD1512	Approved
0.8408	Intermediate Similarity	NPD2532	Approved
0.8408	Intermediate Similarity	NPD2534	Approved
0.8408	Intermediate Similarity	NPD2533	Approved
0.8383	Intermediate Similarity	NPD7473	Discontinued
0.8323	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8323	Intermediate Similarity	NPD6166	Phase 2
0.8323	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8304	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8284	Intermediate Similarity	NPD5844	Phase 1
0.8284	Intermediate Similarity	NPD7054	Approved
0.8235	Intermediate Similarity	NPD7472	Approved
0.8235	Intermediate Similarity	NPD7074	Phase 3
0.8228	Intermediate Similarity	NPD6799	Approved
0.8224	Intermediate Similarity	NPD230	Phase 1
0.8221	Intermediate Similarity	NPD7819	Suspended
0.8193	Intermediate Similarity	NPD5494	Approved
0.8182	Intermediate Similarity	NPD3749	Approved
0.8133	Intermediate Similarity	NPD919	Approved
0.8133	Intermediate Similarity	NPD6234	Discontinued
0.8105	Intermediate Similarity	NPD447	Suspended
0.8081	Intermediate Similarity	NPD6797	Phase 2
0.8081	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8072	Intermediate Similarity	NPD7075	Discontinued
0.8037	Intermediate Similarity	NPD6599	Discontinued
0.8036	Intermediate Similarity	NPD7199	Phase 2
0.8035	Intermediate Similarity	NPD7251	Discontinued
0.8	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7989	Intermediate Similarity	NPD7808	Phase 3
0.7962	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7962	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.795	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7941	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7939	Intermediate Similarity	NPD37	Approved
0.7925	Intermediate Similarity	NPD3750	Approved
0.7911	Intermediate Similarity	NPD1549	Phase 2
0.7904	Intermediate Similarity	NPD4965	Approved
0.7904	Intermediate Similarity	NPD4967	Phase 2
0.7904	Intermediate Similarity	NPD4966	Approved
0.7898	Intermediate Similarity	NPD1551	Phase 2
0.7862	Intermediate Similarity	NPD2800	Approved
0.7857	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7853	Intermediate Similarity	NPD920	Approved
0.7844	Intermediate Similarity	NPD5402	Approved
0.7836	Intermediate Similarity	NPD3926	Phase 2
0.7834	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7834	Intermediate Similarity	NPD1510	Phase 2
0.7831	Intermediate Similarity	NPD6801	Discontinued
0.7824	Intermediate Similarity	NPD1247	Approved
0.7824	Intermediate Similarity	NPD6959	Discontinued
0.7818	Intermediate Similarity	NPD4380	Phase 2
0.7806	Intermediate Similarity	NPD943	Approved
0.7806	Intermediate Similarity	NPD1240	Approved
0.7803	Intermediate Similarity	NPD7228	Approved
0.7792	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD5710	Approved
0.7778	Intermediate Similarity	NPD5711	Approved
0.7771	Intermediate Similarity	NPD7411	Suspended
0.7758	Intermediate Similarity	NPD3226	Approved
0.775	Intermediate Similarity	NPD1243	Approved
0.7744	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD6559	Discontinued
0.7722	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7707	Intermediate Similarity	NPD1607	Approved
0.7702	Intermediate Similarity	NPD4628	Phase 3
0.7702	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD7768	Phase 2
0.7673	Intermediate Similarity	NPD2796	Approved
0.7673	Intermediate Similarity	NPD2935	Discontinued
0.7669	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7636	Intermediate Similarity	NPD5403	Approved
0.7633	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD5401	Approved
0.761	Intermediate Similarity	NPD3748	Approved
0.761	Intermediate Similarity	NPD2799	Discontinued
0.7607	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7597	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD1203	Approved
0.758	Intermediate Similarity	NPD1613	Approved
0.758	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7557	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7548	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD1933	Approved
0.7516	Intermediate Similarity	NPD2344	Approved
0.7516	Intermediate Similarity	NPD2346	Discontinued
0.7515	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3027	Phase 3
0.75	Intermediate Similarity	NPD3751	Discontinued
0.75	Intermediate Similarity	NPD9269	Phase 2
0.7485	Intermediate Similarity	NPD1653	Approved
0.7484	Intermediate Similarity	NPD9494	Approved
0.7471	Intermediate Similarity	NPD7229	Phase 3
0.7439	Intermediate Similarity	NPD6190	Approved
0.7436	Intermediate Similarity	NPD6832	Phase 2
0.743	Intermediate Similarity	NPD7685	Pre-registration
0.7429	Intermediate Similarity	NPD5242	Approved
0.7423	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD9717	Approved
0.7374	Intermediate Similarity	NPD5953	Discontinued
0.7371	Intermediate Similarity	NPD3787	Discontinued
0.736	Intermediate Similarity	NPD7286	Phase 2
0.7354	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD3764	Approved
0.7333	Intermediate Similarity	NPD2309	Approved
0.7333	Intermediate Similarity	NPD7240	Approved
0.7326	Intermediate Similarity	NPD5353	Approved
0.7322	Intermediate Similarity	NPD8434	Phase 2
0.732	Intermediate Similarity	NPD422	Phase 1
0.7308	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD1608	Approved
0.7262	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7253	Intermediate Similarity	NPD8312	Approved
0.7253	Intermediate Similarity	NPD8313	Approved
0.7251	Intermediate Similarity	NPD6386	Approved
0.7251	Intermediate Similarity	NPD6385	Approved
0.725	Intermediate Similarity	NPD4060	Phase 1
0.7243	Intermediate Similarity	NPD4287	Approved
0.7239	Intermediate Similarity	NPD6099	Approved
0.7239	Intermediate Similarity	NPD6100	Approved
0.7237	Intermediate Similarity	NPD9268	Approved
0.7233	Intermediate Similarity	NPD411	Approved
0.7233	Intermediate Similarity	NPD2313	Discontinued
0.7205	Intermediate Similarity	NPD6355	Discontinued
0.7202	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7198	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD7033	Discontinued
0.7143	Intermediate Similarity	NPD7390	Discontinued
0.7143	Intermediate Similarity	NPD8151	Discontinued
0.7134	Intermediate Similarity	NPD2797	Approved
0.7126	Intermediate Similarity	NPD4288	Approved
0.7125	Intermediate Similarity	NPD3268	Approved
0.7125	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD8127	Discontinued
0.7115	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7098	Intermediate Similarity	NPD5006	Approved
0.7098	Intermediate Similarity	NPD5005	Approved
0.7095	Intermediate Similarity	NPD2403	Approved
0.7091	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD1019	Discontinued
0.7078	Intermediate Similarity	NPD17	Approved
0.7073	Intermediate Similarity	NPD4308	Phase 3
0.7071	Intermediate Similarity	NPD7783	Phase 2
0.7071	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD3225	Approved
0.7066	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD4110	Phase 3
0.7059	Intermediate Similarity	NPD6273	Approved
0.7059	Intermediate Similarity	NPD9545	Approved
0.7055	Intermediate Similarity	NPD6651	Approved
0.7043	Intermediate Similarity	NPD8150	Discontinued
0.7035	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD4477	Approved
0.703	Intermediate Similarity	NPD4476	Approved
0.7019	Intermediate Similarity	NPD1296	Phase 2
0.7019	Intermediate Similarity	NPD6798	Discontinued
0.7006	Intermediate Similarity	NPD1652	Phase 2
0.7006	Intermediate Similarity	NPD2654	Approved
0.7	Intermediate Similarity	NPD4908	Phase 1
0.6988	Remote Similarity	NPD1471	Phase 3
0.6987	Remote Similarity	NPD3705	Approved
0.6987	Remote Similarity	NPD1610	Phase 2
0.6979	Remote Similarity	NPD4420	Approved
0.6975	Remote Similarity	NPD6233	Phase 2
0.6974	Remote Similarity	NPD7435	Discontinued
0.6971	Remote Similarity	NPD1006	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD3658	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD7039	Approved
0.6957	Remote Similarity	NPD7038	Approved
0.6954	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD1548	Phase 1
0.6941	Remote Similarity	NPD4357	Discontinued
0.6928	Remote Similarity	NPD5408	Approved
0.6928	Remote Similarity	NPD9493	Approved
0.6928	Remote Similarity	NPD5404	Approved
0.6928	Remote Similarity	NPD5405	Approved
0.6928	Remote Similarity	NPD5406	Approved
0.6927	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD7549	Discontinued
0.6918	Remote Similarity	NPD3267	Approved
0.6918	Remote Similarity	NPD3266	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