NPASS Compound

Structure

NPC472456 OpenBabel07101718202D 26 28 0 0 0 0 0 0 0 0999 V2000 -5.9609 -1.6508 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0904 -3.3780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5139 -3.6235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5299 -2.6265 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9665 -1.8003 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 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 -5.5271 -2.5518 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 2.5139 -1.6235 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 0.7818 -0.6235 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 -1.4088 -1.1235 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 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 -0.9749 -0.2225 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3799 -2.1235 0.0000 O 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 -2.8399 -0.1478 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 1.6479 -3.1235 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 9 1 0 0 0 0 2 9 1 0 0 0 0 3 24 1 0 0 0 0 4 5 1 0 0 0 0 4 9 2 0 0 0 0 5 10 1 0 0 0 0 6 7 2 0 0 0 0 6 11 1 0 0 0 0 7 13 1 0 0 0 0 8 12 2 0 0 0 0 8 14 1 0 0 0 0 10 12 1 0 0 0 0 10 16 2 0 0 0 0 11 17 2 0 0 0 0 11 20 1 0 0 0 0 12 21 1 0 0 0 0 13 18 2 0 0 0 0 13 26 1 0 0 0 0 14 15 2 0 0 0 0 14 25 1 0 0 0 0 15 16 1 0 0 0 0 15 19 1 0 0 0 0 16 22 1 0 0 0 0 17 18 1 0 0 0 0 17 24 1 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:	358.11
Volume:	351.951
LogP:	4.738
LogD:	2.896
LogS:	-3.572
# Rotatable Bonds:	3
TPSA:	105.45
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.437
Synthetic Accessibility Score:	3.111
Fsp3:	0.211
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.045
MDCK Permeability:	1.9486287783365697e-05
Pgp-inhibitor:	0.168
Pgp-substrate:	0.047
Human Intestinal Absorption (HIA):	0.142
20% Bioavailability (F20%):	0.114
30% Bioavailability (F30%):	0.002

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.011
Plasma Protein Binding (PPB):	97.3960952758789%
Volume Distribution (VD):	0.498
Pgp-substrate:	6.772489070892334%

ADMET: Metabolism

CYP1A2-inhibitor:	0.859
CYP1A2-substrate:	0.325
CYP2C19-inhibitor:	0.773
CYP2C19-substrate:	0.068
CYP2C9-inhibitor:	0.727
CYP2C9-substrate:	0.821
CYP2D6-inhibitor:	0.14
CYP2D6-substrate:	0.276
CYP3A4-inhibitor:	0.247
CYP3A4-substrate:	0.149

ADMET: Excretion

Clearance (CL):	12.591
Half-life (T1/2):	0.573

ADMET: Toxicity

hERG Blockers:	0.007
Human Hepatotoxicity (H-HT):	0.034
Drug-inuced Liver Injury (DILI):	0.278
AMES Toxicity:	0.075
Rat Oral Acute Toxicity:	0.986
Maximum Recommended Daily Dose:	0.558
Skin Sensitization:	0.924
Carcinogencity:	0.303
Eye Corrosion:	0.003
Eye Irritation:	0.911
Respiratory Toxicity:	0.659

Download Data

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

Natural Product: NPC472456

Natural Product ID:	NPC472456
*Common Name:**	COQJJLIEGLZUBC-UHFFFAOYSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	COQJJLIEGLZUBC-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C19H18O7/c1-9(2)4-5-10-12(21)8-14-15(16(10)22)19(23)26-13-7-6-11(20)17(24-3)18(13)25-14/h4,6-8,20-22H,5H2,1-3H3
SMILES:	COc1c(O)ccc2c1Oc1cc(O)c(c(c1C(=O)O2)O)CC=C(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3422283
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0001645] Depsides and depsidones

*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
NPO5259	Garcinia buchananii	Species	Clusiaceae	Eukaryota	stem bark	n.a.	n.a.	PMID[25625705]
NPO5259	Garcinia buchananii	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	1
Others	4

Activity Type	# Activity
Others	5

Target ID	Target Type	Target Name	Activity Type	Activity Relation	Value	Unit	Reference
NPT35	Others	n.a.	EC50	<=	45400.0	nM	PMID[557447]
NPT35	Others	n.a.	Activity	=	1.68	mmolequiv/mmol	PMID[557447]
NPT35	Others	n.a.	Activity	=	0.89	mmolequiv/mmol	PMID[557447]
NPT35	Others	n.a.	Activity	=	4.34	mmolequiv/mmol	PMID[557447]
NPT35	Others	n.a.	Activity	=	2.5	mmolequiv/mmol	PMID[557447]

☑ 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 NPC472456 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	374
0.1-0.2	1741
0.2-0.3	4848
0.3-0.4	10989
0.4-0.5	6574
0.5-0.6	3832
0.6-0.7	5400
0.7-0.8	5506
0.8-0.85	2531
0.85-0.9	830
0.9-0.95	69
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9735	High Similarity	NPC168616
0.9735	High Similarity	NPC83763
0.961	High Similarity	NPC234004
0.9545	High Similarity	NPC8300
0.9423	High Similarity	NPC130920
0.9423	High Similarity	NPC85057
0.9351	High Similarity	NPC238381
0.9276	High Similarity	NPC289968
0.9276	High Similarity	NPC199773
0.9236	High Similarity	NPC156082
0.9177	High Similarity	NPC112981
0.9167	High Similarity	NPC292415
0.9161	High Similarity	NPC78225
0.9156	High Similarity	NPC471800
0.9119	High Similarity	NPC20216
0.9108	High Similarity	NPC103201
0.9108	High Similarity	NPC349525
0.9108	High Similarity	NPC473106
0.9097	High Similarity	NPC68093
0.9097	High Similarity	NPC191146
0.9091	High Similarity	NPC475895
0.9091	High Similarity	NPC298802
0.9062	High Similarity	NPC292788
0.9062	High Similarity	NPC272485
0.9057	High Similarity	NPC8070
0.9045	High Similarity	NPC476980
0.9038	High Similarity	NPC223787
0.9038	High Similarity	NPC262286
0.9038	High Similarity	NPC36852
0.9032	High Similarity	NPC286052
0.9026	High Similarity	NPC471982
0.9018	High Similarity	NPC139350
0.8994	High Similarity	NPC300984
0.8994	High Similarity	NPC474350
0.8987	High Similarity	NPC303565
0.8987	High Similarity	NPC258331
0.8987	High Similarity	NPC266314
0.8981	High Similarity	NPC250214
0.8981	High Similarity	NPC95936
0.8974	High Similarity	NPC138243
0.8974	High Similarity	NPC291878
0.8974	High Similarity	NPC35038
0.8974	High Similarity	NPC54928
0.8974	High Similarity	NPC195796
0.8974	High Similarity	NPC278778
0.8968	High Similarity	NPC176775
0.8968	High Similarity	NPC231018
0.8968	High Similarity	NPC145379
0.8968	High Similarity	NPC183878
0.8968	High Similarity	NPC22519
0.8968	High Similarity	NPC47781
0.8968	High Similarity	NPC274327
0.8968	High Similarity	NPC69394
0.8968	High Similarity	NPC255350
0.8968	High Similarity	NPC160951
0.8957	High Similarity	NPC181523
0.8951	High Similarity	NPC239440
0.8951	High Similarity	NPC20543
0.8951	High Similarity	NPC109827
0.8951	High Similarity	NPC124470
0.8951	High Similarity	NPC17219
0.8951	High Similarity	NPC246716
0.8938	High Similarity	NPC267153
0.8931	High Similarity	NPC83922
0.8931	High Similarity	NPC93739
0.8931	High Similarity	NPC472448
0.8924	High Similarity	NPC200594
0.8924	High Similarity	NPC228785
0.8924	High Similarity	NPC246478
0.8924	High Similarity	NPC56085
0.8924	High Similarity	NPC204290
0.8924	High Similarity	NPC14353
0.8917	High Similarity	NPC475267
0.8917	High Similarity	NPC472910
0.8917	High Similarity	NPC472913
0.8917	High Similarity	NPC48208
0.8917	High Similarity	NPC162869
0.8917	High Similarity	NPC27337
0.8917	High Similarity	NPC472598
0.8917	High Similarity	NPC474836
0.8917	High Similarity	NPC476981
0.8917	High Similarity	NPC474208
0.8917	High Similarity	NPC472914
0.8917	High Similarity	NPC472911
0.8917	High Similarity	NPC96167
0.8917	High Similarity	NPC108456
0.8917	High Similarity	NPC222814
0.8917	High Similarity	NPC245758
0.8917	High Similarity	NPC474055
0.8917	High Similarity	NPC156057
0.8917	High Similarity	NPC291508
0.891	High Similarity	NPC92659
0.891	High Similarity	NPC113906
0.891	High Similarity	NPC201136
0.891	High Similarity	NPC183597
0.891	High Similarity	NPC57674
0.891	High Similarity	NPC2476
0.891	High Similarity	NPC200761
0.891	High Similarity	NPC213622
0.891	High Similarity	NPC50715
0.891	High Similarity	NPC117992
0.891	High Similarity	NPC152951
0.891	High Similarity	NPC230149
0.891	High Similarity	NPC146165
0.891	High Similarity	NPC163780
0.891	High Similarity	NPC196439
0.891	High Similarity	NPC256612
0.891	High Similarity	NPC138360
0.891	High Similarity	NPC167815
0.891	High Similarity	NPC234255
0.891	High Similarity	NPC20830
0.891	High Similarity	NPC128863
0.891	High Similarity	NPC45849
0.891	High Similarity	NPC470327
0.891	High Similarity	NPC477503
0.891	High Similarity	NPC280339
0.891	High Similarity	NPC168247
0.891	High Similarity	NPC4455
0.891	High Similarity	NPC227325
0.8903	High Similarity	NPC100887
0.8903	High Similarity	NPC188203
0.8903	High Similarity	NPC162313
0.8903	High Similarity	NPC241498
0.8903	High Similarity	NPC71334
0.8903	High Similarity	NPC156222
0.8903	High Similarity	NPC275836
0.8903	High Similarity	NPC198826
0.8903	High Similarity	NPC83508
0.8903	High Similarity	NPC57030
0.8903	High Similarity	NPC120163
0.8903	High Similarity	NPC301323
0.8903	High Similarity	NPC131624
0.8903	High Similarity	NPC212678
0.8903	High Similarity	NPC222830
0.8903	High Similarity	NPC275722
0.8903	High Similarity	NPC120537
0.8903	High Similarity	NPC199100
0.8903	High Similarity	NPC25270
0.8903	High Similarity	NPC293183
0.8903	High Similarity	NPC256283
0.8903	High Similarity	NPC239128
0.8903	High Similarity	NPC187498
0.8903	High Similarity	NPC180234
0.8903	High Similarity	NPC249570
0.8896	High Similarity	NPC3825
0.8896	High Similarity	NPC158226
0.8896	High Similarity	NPC88804
0.8889	High Similarity	NPC163130
0.8889	High Similarity	NPC26568
0.8889	High Similarity	NPC165979
0.8882	High Similarity	NPC472452
0.8875	High Similarity	NPC220313
0.8875	High Similarity	NPC284007
0.8868	High Similarity	NPC278052
0.8868	High Similarity	NPC259456
0.8868	High Similarity	NPC61010
0.8868	High Similarity	NPC167678
0.8868	High Similarity	NPC29876
0.8868	High Similarity	NPC40491
0.8861	High Similarity	NPC100123
0.8855	High Similarity	NPC113446
0.8854	High Similarity	NPC471985
0.8854	High Similarity	NPC49824
0.8854	High Similarity	NPC472916
0.8854	High Similarity	NPC276444
0.8854	High Similarity	NPC235165
0.8854	High Similarity	NPC470328
0.8854	High Similarity	NPC255106
0.8854	High Similarity	NPC472455
0.8854	High Similarity	NPC472626
0.8854	High Similarity	NPC209614
0.8846	High Similarity	NPC292214
0.8846	High Similarity	NPC271779
0.8846	High Similarity	NPC70433
0.8846	High Similarity	NPC192083
0.8846	High Similarity	NPC18727
0.8846	High Similarity	NPC273462
0.8846	High Similarity	NPC167091
0.8846	High Similarity	NPC213896
0.8846	High Similarity	NPC33051
0.8846	High Similarity	NPC227337
0.8846	High Similarity	NPC88645
0.8846	High Similarity	NPC49402
0.8846	High Similarity	NPC276409
0.8846	High Similarity	NPC476631
0.8846	High Similarity	NPC206238
0.8846	High Similarity	NPC75279
0.8846	High Similarity	NPC250822
0.8839	High Similarity	NPC226973
0.8839	High Similarity	NPC117579
0.8839	High Similarity	NPC208043
0.8839	High Similarity	NPC308451
0.8834	High Similarity	NPC1827
0.8834	High Similarity	NPC10576
0.8831	High Similarity	NPC48479
0.8831	High Similarity	NPC177298
0.8831	High Similarity	NPC102003
0.8831	High Similarity	NPC52005
0.8831	High Similarity	NPC92722
0.8831	High Similarity	NPC287101

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 NPC472456 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	351
0.1-0.2	964
0.2-0.3	1858
0.3-0.4	2663
0.4-0.5	1676
0.5-0.6	1060
0.6-0.7	413
0.7-0.8	122
0.8-0.85	37
0.85-0.9	6
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8968	High Similarity	NPD2801	Approved
0.8846	High Similarity	NPD2393	Clinical (unspecified phase)
0.8782	High Similarity	NPD1934	Approved
0.8571	High Similarity	NPD4378	Clinical (unspecified phase)
0.8562	High Similarity	NPD7075	Discontinued
0.8553	High Similarity	NPD3817	Phase 2
0.8506	High Similarity	NPD1511	Approved
0.8506	High Similarity	NPD6799	Approved
0.85	High Similarity	NPD3882	Suspended
0.8491	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8466	Intermediate Similarity	NPD6232	Discontinued
0.8434	Intermediate Similarity	NPD5844	Phase 1
0.8428	Intermediate Similarity	NPD6801	Discontinued
0.8397	Intermediate Similarity	NPD1512	Approved
0.8385	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8365	Intermediate Similarity	NPD7411	Suspended
0.8364	Intermediate Similarity	NPD6166	Phase 2
0.8364	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8364	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8343	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8313	Intermediate Similarity	NPD7473	Discontinued
0.8302	Intermediate Similarity	NPD4380	Phase 2
0.8302	Intermediate Similarity	NPD6599	Discontinued
0.8289	Intermediate Similarity	NPD2935	Discontinued
0.8274	Intermediate Similarity	NPD7074	Phase 3
0.8263	Intermediate Similarity	NPD3818	Discontinued
0.8235	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8235	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8232	Intermediate Similarity	NPD5494	Approved
0.8217	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8214	Intermediate Similarity	NPD7054	Approved
0.82	Intermediate Similarity	NPD1240	Approved
0.8182	Intermediate Similarity	NPD1549	Phase 2
0.8166	Intermediate Similarity	NPD7472	Approved
0.8148	Intermediate Similarity	NPD1465	Phase 2
0.8148	Intermediate Similarity	NPD7819	Suspended
0.811	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8092	Intermediate Similarity	NPD1607	Approved
0.8067	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8061	Intermediate Similarity	NPD919	Approved
0.8049	Intermediate Similarity	NPD7768	Phase 2
0.8013	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD6797	Phase 2
0.8	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7988	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD2799	Discontinued
0.7987	Intermediate Similarity	NPD1510	Phase 2
0.7965	Intermediate Similarity	NPD7251	Discontinued
0.7949	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7935	Intermediate Similarity	NPD2796	Approved
0.7935	Intermediate Similarity	NPD1551	Phase 2
0.7929	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7919	Intermediate Similarity	NPD7808	Phase 3
0.7908	Intermediate Similarity	NPD447	Suspended
0.7907	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7898	Intermediate Similarity	NPD1243	Approved
0.7888	Intermediate Similarity	NPD920	Approved
0.7888	Intermediate Similarity	NPD5403	Approved
0.7879	Intermediate Similarity	NPD5402	Approved
0.7875	Intermediate Similarity	NPD2532	Approved
0.7875	Intermediate Similarity	NPD2534	Approved
0.7875	Intermediate Similarity	NPD2533	Approved
0.7857	Intermediate Similarity	NPD1247	Approved
0.7852	Intermediate Similarity	NPD1203	Approved
0.7848	Intermediate Similarity	NPD4628	Phase 3
0.7848	Intermediate Similarity	NPD3750	Approved
0.7792	Intermediate Similarity	NPD1933	Approved
0.7792	Intermediate Similarity	NPD230	Phase 1
0.7791	Intermediate Similarity	NPD7286	Phase 2
0.7785	Intermediate Similarity	NPD2800	Approved
0.7784	Intermediate Similarity	NPD3749	Approved
0.7764	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7764	Intermediate Similarity	NPD5401	Approved
0.7759	Intermediate Similarity	NPD6559	Discontinued
0.7753	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.775	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD943	Approved
0.7701	Intermediate Similarity	NPD5953	Discontinued
0.7697	Intermediate Similarity	NPD6832	Phase 2
0.7669	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD9717	Approved
0.7647	Intermediate Similarity	NPD6959	Discontinued
0.7628	Intermediate Similarity	NPD6651	Approved
0.7625	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD1653	Approved
0.7597	Intermediate Similarity	NPD2313	Discontinued
0.7593	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7584	Intermediate Similarity	NPD422	Phase 1
0.7582	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD3226	Approved
0.7558	Intermediate Similarity	NPD3926	Phase 2
0.7544	Intermediate Similarity	NPD7199	Phase 2
0.7532	Intermediate Similarity	NPD3748	Approved
0.7532	Intermediate Similarity	NPD3027	Phase 3
0.7529	Intermediate Similarity	NPD6234	Discontinued
0.7516	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2797	Approved
0.75	Intermediate Similarity	NPD1613	Approved
0.7484	Intermediate Similarity	NPD3268	Approved
0.7457	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD6233	Phase 2
0.7421	Intermediate Similarity	NPD7033	Discontinued
0.7405	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7377	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD1296	Phase 2
0.7372	Intermediate Similarity	NPD6798	Discontinued
0.7362	Intermediate Similarity	NPD6190	Approved
0.7342	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD5124	Phase 1
0.7337	Intermediate Similarity	NPD37	Approved
0.7329	Intermediate Similarity	NPD2346	Discontinued
0.7329	Intermediate Similarity	NPD2344	Approved
0.732	Intermediate Similarity	NPD3225	Approved
0.7318	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD4308	Phase 3
0.731	Intermediate Similarity	NPD4967	Phase 2
0.731	Intermediate Similarity	NPD4966	Approved
0.731	Intermediate Similarity	NPD4965	Approved
0.7303	Intermediate Similarity	NPD1481	Phase 2
0.7301	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD5710	Approved
0.7299	Intermediate Similarity	NPD5711	Approved
0.7261	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD5242	Approved
0.7239	Intermediate Similarity	NPD1652	Phase 2
0.7237	Intermediate Similarity	NPD1535	Discovery
0.7233	Intermediate Similarity	NPD6355	Discontinued
0.7232	Intermediate Similarity	NPD7228	Approved
0.7226	Intermediate Similarity	NPD1019	Discontinued
0.72	Intermediate Similarity	NPD9545	Approved
0.7196	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD9269	Phase 2
0.719	Intermediate Similarity	NPD1608	Approved
0.7186	Intermediate Similarity	NPD5049	Phase 3
0.7181	Intermediate Similarity	NPD9493	Approved
0.7179	Intermediate Similarity	NPD9494	Approved
0.717	Intermediate Similarity	NPD4060	Phase 1
0.7161	Intermediate Similarity	NPD3266	Approved
0.7161	Intermediate Similarity	NPD3267	Approved
0.716	Intermediate Similarity	NPD4476	Approved
0.716	Intermediate Similarity	NPD4477	Approved
0.716	Intermediate Similarity	NPD7458	Discontinued
0.7158	Intermediate Similarity	NPD8434	Phase 2
0.7152	Intermediate Similarity	NPD2354	Approved
0.7152	Intermediate Similarity	NPD2309	Approved
0.7152	Intermediate Similarity	NPD411	Approved
0.7143	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD4908	Phase 1
0.7102	Intermediate Similarity	NPD7229	Phase 3
0.7099	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD8455	Phase 2
0.7092	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD7783	Phase 2
0.7088	Intermediate Similarity	NPD8312	Approved
0.7088	Intermediate Similarity	NPD8313	Approved
0.7086	Intermediate Similarity	NPD1548	Phase 1
0.7083	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7076	Intermediate Similarity	NPD6386	Approved
0.7076	Intermediate Similarity	NPD6385	Approved
0.7072	Intermediate Similarity	NPD7685	Pre-registration
0.7066	Intermediate Similarity	NPD7390	Discontinued
0.7063	Intermediate Similarity	NPD4307	Phase 2
0.7055	Intermediate Similarity	NPD6100	Approved
0.7055	Intermediate Similarity	NPD6099	Approved
0.7052	Intermediate Similarity	NPD4288	Approved
0.7052	Intermediate Similarity	NPD5353	Approved
0.7051	Intermediate Similarity	NPD1164	Approved
0.7039	Intermediate Similarity	NPD3751	Discontinued
0.7033	Intermediate Similarity	NPD7549	Discontinued
0.703	Intermediate Similarity	NPD2654	Approved
0.7024	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD4360	Phase 2
0.7021	Intermediate Similarity	NPD4363	Phase 3
0.7013	Intermediate Similarity	NPD1610	Phase 2
0.7013	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD3787	Discontinued
0.7006	Intermediate Similarity	NPD2798	Approved
0.7	Intermediate Similarity	NPD4062	Phase 3
0.6995	Remote Similarity	NPD7435	Discontinued
0.6993	Remote Similarity	NPD17	Approved
0.6988	Remote Similarity	NPD7003	Approved
0.6974	Remote Similarity	NPD7584	Approved
0.6973	Remote Similarity	NPD8150	Discontinued
0.6961	Remote Similarity	NPD1729	Discontinued
0.6959	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD5405	Approved
0.6951	Remote Similarity	NPD5408	Approved
0.6951	Remote Similarity	NPD5404	Approved
0.6951	Remote Similarity	NPD5406	Approved
0.6949	Remote Similarity	NPD8127	Discontinued
0.6948	Remote Similarity	NPD3496	Discontinued
0.6946	Remote Similarity	NPD3887	Approved
0.6939	Remote Similarity	NPD7585	Approved
0.6937	Remote Similarity	NPD3764	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