NPASS Compound

Structure

NPC138243 OpenBabel07101719132D 29 31 0 0 0 0 0 0 0 0999 V2000 -5.1962 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -3.0000 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 -3.4641 -2.0000 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 -2.0000 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 -4.3301 -3.5000 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 -2.5981 -1.5000 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 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 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 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 -0.8660 -0.5000 0.0000 C 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 1.7321 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 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 11 1 0 0 0 0 2 11 1 0 0 0 0 3 12 1 0 0 0 0 4 12 1 0 0 0 0 5 7 1 0 0 0 0 5 11 2 0 0 0 0 6 8 1 0 0 0 0 6 12 2 0 0 0 0 7 14 1 0 0 0 0 8 15 1 0 0 0 0 9 13 2 0 0 0 0 9 16 1 0 0 0 0 10 13 1 0 0 0 0 10 17 2 0 0 0 0 13 24 1 0 0 0 0 14 19 2 0 0 0 0 14 20 1 0 0 0 0 15 19 1 0 0 0 0 15 23 2 0 0 0 0 16 21 1 0 0 0 0 16 22 2 0 0 0 0 17 22 1 0 0 0 0 17 25 1 0 0 0 0 18 20 2 0 0 0 0 18 21 1 0 0 0 0 18 23 1 0 0 0 0 19 26 1 0 0 0 0 20 27 1 0 0 0 0 21 28 2 0 0 0 0 22 29 1 0 0 0 0 23 29 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	396.16
Volume:	409.708
LogP:	5.826
LogD:	2.642
LogS:	-2.978
# Rotatable Bonds:	4
TPSA:	111.13
# H-Bond Aceptor:	6
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.373
Synthetic Accessibility Score:	3.219
Fsp3:	0.261
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.056
MDCK Permeability:	1.1207347597519401e-05
Pgp-inhibitor:	0.273
Pgp-substrate:	0.913
Human Intestinal Absorption (HIA):	0.191
20% Bioavailability (F20%):	0.971
30% Bioavailability (F30%):	0.92

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.006
Plasma Protein Binding (PPB):	82.71208953857422%
Volume Distribution (VD):	0.899
Pgp-substrate:	14.65916633605957%

ADMET: Metabolism

CYP1A2-inhibitor:	0.635
CYP1A2-substrate:	0.179
CYP2C19-inhibitor:	0.537
CYP2C19-substrate:	0.056
CYP2C9-inhibitor:	0.758
CYP2C9-substrate:	0.762
CYP2D6-inhibitor:	0.34
CYP2D6-substrate:	0.159
CYP3A4-inhibitor:	0.136
CYP3A4-substrate:	0.035

ADMET: Excretion

Clearance (CL):	8.709
Half-life (T1/2):	0.746

ADMET: Toxicity

hERG Blockers:	0.003
Human Hepatotoxicity (H-HT):	0.961
Drug-inuced Liver Injury (DILI):	0.977
AMES Toxicity:	0.301
Rat Oral Acute Toxicity:	0.395
Maximum Recommended Daily Dose:	0.188
Skin Sensitization:	0.909
Carcinogencity:	0.117
Eye Corrosion:	0.003
Eye Irritation:	0.39
Respiratory Toxicity:	0.278

Download Data

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

Natural Product: NPC138243

Natural Product ID:	NPC138243
*Common Name:**	Staudtiixanthone A
IUPAC Name:	1,3,5,7-tetrahydroxy-2,4-bis(3-methylbut-2-enyl)xanthen-9-one
Synonyms:
Standard InCHIKey:	XFOVRUSXFOUQFT-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C23H24O6/c1-11(2)5-7-14-19(26)15(8-6-12(3)4)23-18(20(14)27)21(28)16-9-13(24)10-17(25)22(16)29-23/h5-6,9-10,24-27H,7-8H2,1-4H3
SMILES:	CC(=CCc1c(c(CC=C(C)C)c2c(c1O)c(=O)c1cc(cc(c1o2)O)O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL563245
PubChem CID:	44517666
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0002817] Dibenzopyrans [CHEMONTID:0000200] Xanthenes [CHEMONTID:0000204] Xanthones [CHEMONTID:0003518] 4-prenylated xanthones

*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
NPO6871	Garcinia staudtii	Species	Clusiaceae	Eukaryota	twigs	n.a.	n.a.	PMID[19604701]
NPO6871	Garcinia staudtii	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
IC50	1
MIC	1
Others	11

Activity Type	# Activity
Cell Line	9
Organism	1
Others	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT927	Cell Line	PBMC	Homo sapiens	IC50	=	6.2	ug.mL-1	PMID[473249]
NPT927	Cell Line	PBMC	Homo sapiens	Inhibition	=	94.3	%	PMID[473249]
NPT927	Cell Line	PBMC	Homo sapiens	Inhibition	=	68.2	%	PMID[473249]
NPT927	Cell Line	PBMC	Homo sapiens	Inhibition	=	62.5	%	PMID[473249]
NPT927	Cell Line	PBMC	Homo sapiens	Inhibition	=	88.1	%	PMID[473249]
NPT927	Cell Line	PBMC	Homo sapiens	Inhibition	=	40.6	%	PMID[473249]
NPT927	Cell Line	PBMC	Homo sapiens	Activity	=	528.5	pg/ml	PMID[473249]
NPT927	Cell Line	PBMC	Homo sapiens	Activity	=	120.5	pg/ml	PMID[473249]
NPT927	Cell Line	PBMC	Homo sapiens	Activity	=	4033.7	pg/ml	PMID[473249]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	16.0	ug.mL-1	PMID[473249]
NPT2	Others	Unspecified		Activity	=	73.0	%	PMID[473249]
NPT2	Others	Unspecified		Inhibition	=	27.0	%	PMID[473249]

☑ 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 NPC138243 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	453
0.1-0.2	1974
0.2-0.3	4969
0.3-0.4	11316
0.4-0.5	6193
0.5-0.6	3920
0.6-0.7	5003
0.7-0.8	4801
0.8-0.85	2100
0.85-0.9	1154
0.9-0.95	621
0.95-1	193

Similarity Score	Similarity Level	Natural Product ID
0.9933	High Similarity	NPC262286
0.9933	High Similarity	NPC36852
0.9866	High Similarity	NPC191146
0.9866	High Similarity	NPC68093
0.98	High Similarity	NPC78225
0.9799	High Similarity	NPC113906
0.9737	High Similarity	NPC167678
0.9737	High Similarity	NPC29876
0.9735	High Similarity	NPC100123
0.9732	High Similarity	NPC273462
0.9732	High Similarity	NPC33051
0.9732	High Similarity	NPC227337
0.9732	High Similarity	NPC49402
0.9732	High Similarity	NPC70433
0.9673	High Similarity	NPC472448
0.9673	High Similarity	NPC83922
0.9671	High Similarity	NPC14353
0.9671	High Similarity	NPC56085
0.9671	High Similarity	NPC204290
0.9671	High Similarity	NPC228785
0.9671	High Similarity	NPC320359
0.9671	High Similarity	NPC476980
0.9669	High Similarity	NPC223787
0.9667	High Similarity	NPC230149
0.9667	High Similarity	NPC57674
0.9667	High Similarity	NPC168247
0.9667	High Similarity	NPC117992
0.9667	High Similarity	NPC152951
0.9664	High Similarity	NPC101996
0.9608	High Similarity	NPC61010
0.9608	High Similarity	NPC258331
0.9608	High Similarity	NPC278052
0.9608	High Similarity	NPC259456
0.9608	High Similarity	NPC40491
0.9608	High Similarity	NPC266314
0.9605	High Similarity	NPC185258
0.9605	High Similarity	NPC95936
0.9605	High Similarity	NPC250214
0.9605	High Similarity	NPC172770
0.9603	High Similarity	NPC274730
0.9603	High Similarity	NPC472916
0.9603	High Similarity	NPC142339
0.96	High Similarity	NPC292214
0.96	High Similarity	NPC271779
0.96	High Similarity	NPC88645
0.96	High Similarity	NPC167091
0.96	High Similarity	NPC206238
0.9597	High Similarity	NPC251110
0.9597	High Similarity	NPC171010
0.9545	High Similarity	NPC25152
0.9545	High Similarity	NPC81679
0.9542	High Similarity	NPC246478
0.9539	High Similarity	NPC48208
0.9539	High Similarity	NPC222814
0.9539	High Similarity	NPC217677
0.9539	High Similarity	NPC291508
0.9539	High Similarity	NPC96167
0.9539	High Similarity	NPC474836
0.9539	High Similarity	NPC241904
0.9539	High Similarity	NPC161960
0.9539	High Similarity	NPC162869
0.9539	High Similarity	NPC304008
0.9539	High Similarity	NPC476981
0.9539	High Similarity	NPC469584
0.9539	High Similarity	NPC165977
0.9539	High Similarity	NPC472913
0.9539	High Similarity	NPC245758
0.9539	High Similarity	NPC236796
0.9539	High Similarity	NPC187745
0.9539	High Similarity	NPC79053
0.9539	High Similarity	NPC472914
0.9539	High Similarity	NPC474681
0.9539	High Similarity	NPC210084
0.9539	High Similarity	NPC475267
0.9539	High Similarity	NPC474208
0.9539	High Similarity	NPC300727
0.9539	High Similarity	NPC156057
0.9539	High Similarity	NPC472910
0.9539	High Similarity	NPC99597
0.9539	High Similarity	NPC472911
0.9539	High Similarity	NPC218313
0.9536	High Similarity	NPC208197
0.9536	High Similarity	NPC20830
0.9536	High Similarity	NPC477503
0.9536	High Similarity	NPC2928
0.9536	High Similarity	NPC472280
0.9536	High Similarity	NPC134287
0.9536	High Similarity	NPC256612
0.9536	High Similarity	NPC470327
0.9536	High Similarity	NPC256925
0.9536	High Similarity	NPC45849
0.9536	High Similarity	NPC200761
0.9536	High Similarity	NPC130589
0.9533	High Similarity	NPC39007
0.9533	High Similarity	NPC180234
0.9533	High Similarity	NPC120537
0.9533	High Similarity	NPC249570
0.9533	High Similarity	NPC161277
0.9533	High Similarity	NPC199100
0.9533	High Similarity	NPC471982
0.953	High Similarity	NPC61620
0.953	High Similarity	NPC179183
0.953	High Similarity	NPC248102
0.9527	High Similarity	NPC194856
0.9484	High Similarity	NPC189473
0.9484	High Similarity	NPC152659
0.9484	High Similarity	NPC236521
0.9484	High Similarity	NPC303460
0.9484	High Similarity	NPC7483
0.9484	High Similarity	NPC41301
0.9484	High Similarity	NPC23298
0.9484	High Similarity	NPC248638
0.9484	High Similarity	NPC306321
0.9484	High Similarity	NPC236132
0.9484	High Similarity	NPC220313
0.9481	High Similarity	NPC134783
0.9481	High Similarity	NPC472275
0.9477	High Similarity	NPC204879
0.9477	High Similarity	NPC476242
0.9474	High Similarity	NPC278778
0.9474	High Similarity	NPC133970
0.9474	High Similarity	NPC235165
0.9474	High Similarity	NPC470600
0.9474	High Similarity	NPC6633
0.9474	High Similarity	NPC472626
0.9474	High Similarity	NPC195796
0.9474	High Similarity	NPC5322
0.9474	High Similarity	NPC470328
0.9474	High Similarity	NPC291878
0.9474	High Similarity	NPC35038
0.9474	High Similarity	NPC472455
0.9474	High Similarity	NPC115853
0.9474	High Similarity	NPC209614
0.9474	High Similarity	NPC255106
0.947	High Similarity	NPC75279
0.947	High Similarity	NPC47781
0.947	High Similarity	NPC183878
0.947	High Similarity	NPC280937
0.947	High Similarity	NPC160951
0.947	High Similarity	NPC472915
0.947	High Similarity	NPC22519
0.947	High Similarity	NPC231018
0.947	High Similarity	NPC250822
0.947	High Similarity	NPC255350
0.947	High Similarity	NPC274327
0.947	High Similarity	NPC276409
0.947	High Similarity	NPC145379
0.947	High Similarity	NPC69394
0.947	High Similarity	NPC176775
0.947	High Similarity	NPC89474
0.947	High Similarity	NPC476631
0.9467	High Similarity	NPC117579
0.9467	High Similarity	NPC149614
0.9459	High Similarity	NPC207729
0.9423	High Similarity	NPC326520
0.9423	High Similarity	NPC239752
0.9423	High Similarity	NPC472450
0.9423	High Similarity	NPC275780
0.9419	High Similarity	NPC329760
0.9419	High Similarity	NPC261470
0.9419	High Similarity	NPC220912
0.9419	High Similarity	NPC470694
0.9416	High Similarity	NPC45146
0.9416	High Similarity	NPC474287
0.9416	High Similarity	NPC119224
0.9416	High Similarity	NPC475886
0.9416	High Similarity	NPC235018
0.9416	High Similarity	NPC200746
0.9412	High Similarity	NPC181960
0.9412	High Similarity	NPC474055
0.9412	High Similarity	NPC136674
0.9412	High Similarity	NPC78103
0.9412	High Similarity	NPC129684
0.9412	High Similarity	NPC219867
0.9412	High Similarity	NPC299520
0.9412	High Similarity	NPC472598
0.9412	High Similarity	NPC52889
0.9412	High Similarity	NPC27337
0.9412	High Similarity	NPC180011
0.9408	High Similarity	NPC37392
0.9408	High Similarity	NPC4455
0.9408	High Similarity	NPC200246
0.9408	High Similarity	NPC146165
0.9408	High Similarity	NPC92659
0.9408	High Similarity	NPC213622
0.9408	High Similarity	NPC183597
0.9408	High Similarity	NPC2476
0.9408	High Similarity	NPC128863
0.9408	High Similarity	NPC138360
0.9408	High Similarity	NPC280339
0.9408	High Similarity	NPC227325
0.9408	High Similarity	NPC196439
0.9408	High Similarity	NPC163780
0.9408	High Similarity	NPC167815
0.9408	High Similarity	NPC50715
0.9408	High Similarity	NPC234255
0.9408	High Similarity	NPC472909
0.9408	High Similarity	NPC201136
0.9408	High Similarity	NPC39184
0.9404	High Similarity	NPC83508

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 NPC138243 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	410
0.1-0.2	1017
0.2-0.3	1896
0.3-0.4	2700
0.4-0.5	1699
0.5-0.6	954
0.6-0.7	311
0.7-0.8	116
0.8-0.85	28
0.85-0.9	13
0.9-0.95	6
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.947	High Similarity	NPD2801	Approved
0.9342	High Similarity	NPD2393	Clinical (unspecified phase)
0.9276	High Similarity	NPD1934	Approved
0.9	High Similarity	NPD1511	Approved
0.8974	High Similarity	NPD3882	Suspended
0.8924	High Similarity	NPD5494	Approved
0.8882	High Similarity	NPD1512	Approved
0.882	High Similarity	NPD6168	Clinical (unspecified phase)
0.882	High Similarity	NPD6167	Clinical (unspecified phase)
0.882	High Similarity	NPD6166	Phase 2
0.8734	High Similarity	NPD4868	Clinical (unspecified phase)
0.8712	High Similarity	NPD3818	Discontinued
0.8693	High Similarity	NPD4378	Clinical (unspecified phase)
0.8654	High Similarity	NPD4380	Phase 2
0.8606	High Similarity	NPD7074	Phase 3
0.8563	High Similarity	NPD4338	Clinical (unspecified phase)
0.8562	High Similarity	NPD7075	Discontinued
0.8553	High Similarity	NPD3817	Phase 2
0.8545	High Similarity	NPD7054	Approved
0.8494	Intermediate Similarity	NPD7472	Approved
0.8491	Intermediate Similarity	NPD1465	Phase 2
0.8491	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8466	Intermediate Similarity	NPD6232	Discontinued
0.8452	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8434	Intermediate Similarity	NPD5844	Phase 1
0.8424	Intermediate Similarity	NPD7473	Discontinued
0.8421	Intermediate Similarity	NPD1549	Phase 2
0.8375	Intermediate Similarity	NPD7819	Suspended
0.8355	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8355	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD6797	Phase 2
0.8322	Intermediate Similarity	NPD943	Approved
0.8293	Intermediate Similarity	NPD1247	Approved
0.8284	Intermediate Similarity	NPD7251	Discontinued
0.825	Intermediate Similarity	NPD7411	Suspended
0.8235	Intermediate Similarity	NPD7808	Phase 3
0.8225	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8224	Intermediate Similarity	NPD1510	Phase 2
0.821	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.82	Intermediate Similarity	NPD1240	Approved
0.8199	Intermediate Similarity	NPD6801	Discontinued
0.8182	Intermediate Similarity	NPD6959	Discontinued
0.817	Intermediate Similarity	NPD2796	Approved
0.817	Intermediate Similarity	NPD2935	Discontinued
0.8153	Intermediate Similarity	NPD6799	Approved
0.8129	Intermediate Similarity	NPD2800	Approved
0.8108	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8107	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8098	Intermediate Similarity	NPD5402	Approved
0.8092	Intermediate Similarity	NPD1607	Approved
0.807	Intermediate Similarity	NPD6559	Discontinued
0.8054	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7976	Intermediate Similarity	NPD3926	Phase 2
0.7963	Intermediate Similarity	NPD6599	Discontinued
0.7952	Intermediate Similarity	NPD919	Approved
0.7929	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7908	Intermediate Similarity	NPD230	Phase 1
0.7908	Intermediate Similarity	NPD447	Suspended
0.7892	Intermediate Similarity	NPD3749	Approved
0.7875	Intermediate Similarity	NPD2533	Approved
0.7875	Intermediate Similarity	NPD2532	Approved
0.7875	Intermediate Similarity	NPD2534	Approved
0.7871	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7853	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7848	Intermediate Similarity	NPD3750	Approved
0.7843	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7843	Intermediate Similarity	NPD1613	Approved
0.7834	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7831	Intermediate Similarity	NPD7768	Phase 2
0.7791	Intermediate Similarity	NPD3226	Approved
0.7785	Intermediate Similarity	NPD1243	Approved
0.7785	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD2346	Discontinued
0.776	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7756	Intermediate Similarity	NPD2799	Discontinued
0.7756	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7712	Intermediate Similarity	NPD2313	Discontinued
0.7707	Intermediate Similarity	NPD6099	Approved
0.7707	Intermediate Similarity	NPD6100	Approved
0.7669	Intermediate Similarity	NPD5403	Approved
0.7669	Intermediate Similarity	NPD920	Approved
0.7667	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7658	Intermediate Similarity	NPD2344	Approved
0.7647	Intermediate Similarity	NPD3027	Phase 3
0.7633	Intermediate Similarity	NPD6234	Discontinued
0.7628	Intermediate Similarity	NPD6651	Approved
0.7625	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD1653	Approved
0.76	Intermediate Similarity	NPD5953	Discontinued
0.7595	Intermediate Similarity	NPD1551	Phase 2
0.7593	Intermediate Similarity	NPD7390	Discontinued
0.7586	Intermediate Similarity	NPD7286	Phase 2
0.7584	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7564	Intermediate Similarity	NPD1933	Approved
0.7546	Intermediate Similarity	NPD5401	Approved
0.7546	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD3748	Approved
0.7529	Intermediate Similarity	NPD3751	Discontinued
0.7516	Intermediate Similarity	NPD4628	Phase 3
0.7516	Intermediate Similarity	NPD9494	Approved
0.7485	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7469	Intermediate Similarity	NPD2309	Approved
0.7469	Intermediate Similarity	NPD6190	Approved
0.7442	Intermediate Similarity	NPD7199	Phase 2
0.744	Intermediate Similarity	NPD37	Approved
0.7429	Intermediate Similarity	NPD7228	Approved
0.7423	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD9269	Phase 2
0.7416	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7412	Intermediate Similarity	NPD4967	Phase 2
0.7412	Intermediate Similarity	NPD4965	Approved
0.7412	Intermediate Similarity	NPD4966	Approved
0.7407	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7399	Intermediate Similarity	NPD5711	Approved
0.7399	Intermediate Similarity	NPD3787	Discontinued
0.7399	Intermediate Similarity	NPD5710	Approved
0.7386	Intermediate Similarity	NPD1203	Approved
0.738	Intermediate Similarity	NPD6776	Approved
0.738	Intermediate Similarity	NPD6780	Approved
0.738	Intermediate Similarity	NPD6781	Approved
0.738	Intermediate Similarity	NPD6779	Approved
0.738	Intermediate Similarity	NPD6778	Approved
0.738	Intermediate Similarity	NPD6782	Approved
0.738	Intermediate Similarity	NPD6777	Approved
0.7374	Intermediate Similarity	NPD8313	Approved
0.7374	Intermediate Similarity	NPD8312	Approved
0.7372	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD4625	Phase 3
0.7263	Intermediate Similarity	NPD7685	Pre-registration
0.7263	Intermediate Similarity	NPD7435	Discontinued
0.7257	Intermediate Similarity	NPD5242	Approved
0.7254	Intermediate Similarity	NPD8151	Discontinued
0.7253	Intermediate Similarity	NPD8150	Discontinued
0.7253	Intermediate Similarity	NPD8434	Phase 2
0.7251	Intermediate Similarity	NPD5353	Approved
0.7244	Intermediate Similarity	NPD4908	Phase 1
0.7237	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD6844	Discontinued
0.7226	Intermediate Similarity	NPD2798	Approved
0.7219	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7204	Intermediate Similarity	NPD4363	Phase 3
0.7204	Intermediate Similarity	NPD4360	Phase 2
0.719	Intermediate Similarity	NPD9717	Approved
0.7176	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7173	Intermediate Similarity	NPD7697	Approved
0.7173	Intermediate Similarity	NPD7696	Phase 3
0.7173	Intermediate Similarity	NPD7698	Approved
0.7161	Intermediate Similarity	NPD1470	Approved
0.7152	Intermediate Similarity	NPD3268	Approved
0.7152	Intermediate Similarity	NPD9268	Approved
0.715	Intermediate Similarity	NPD7584	Approved
0.7143	Intermediate Similarity	NPD4749	Approved
0.7135	Intermediate Similarity	NPD7871	Phase 2
0.7135	Intermediate Similarity	NPD7870	Phase 2
0.7134	Intermediate Similarity	NPD6832	Phase 2
0.7125	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD1610	Phase 2
0.712	Intermediate Similarity	NPD6823	Phase 2
0.7119	Intermediate Similarity	NPD2403	Approved
0.7113	Intermediate Similarity	NPD7701	Phase 2
0.7112	Intermediate Similarity	NPD6534	Approved
0.7112	Intermediate Similarity	NPD6535	Approved
0.7102	Intermediate Similarity	NPD7229	Phase 3
0.71	Intermediate Similarity	NPD2899	Discontinued
0.7099	Intermediate Similarity	NPD4308	Phase 3
0.7092	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD7783	Phase 2
0.7078	Intermediate Similarity	NPD1608	Approved
0.7076	Intermediate Similarity	NPD6386	Approved
0.7076	Intermediate Similarity	NPD6385	Approved
0.7073	Intermediate Similarity	NPD2424	Discontinued
0.707	Intermediate Similarity	NPD2861	Phase 2
0.7066	Intermediate Similarity	NPD4357	Discontinued
0.7059	Intermediate Similarity	NPD7458	Discontinued
0.7059	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD5406	Approved
0.7055	Intermediate Similarity	NPD5404	Approved
0.7055	Intermediate Similarity	NPD5408	Approved
0.7055	Intermediate Similarity	NPD5405	Approved
0.7051	Intermediate Similarity	NPD2797	Approved
0.7044	Intermediate Similarity	NPD411	Approved
0.7041	Intermediate Similarity	NPD7874	Approved
0.7041	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD7549	Discontinued
0.703	Intermediate Similarity	NPD2654	Approved
0.7024	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD5536	Phase 2
0.7013	Intermediate Similarity	NPD1201	Approved
0.7013	Intermediate Similarity	NPD422	Phase 1
0.7012	Intermediate Similarity	NPD1471	Phase 3
0.7005	Intermediate Similarity	NPD7801	Approved
0.7	Intermediate Similarity	NPD7699	Phase 2
0.7	Intermediate Similarity	NPD7700	Phase 2
0.7	Intermediate Similarity	NPD6233	Phase 2

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