NPASS Compound

Structure

CID274730 OpenBabel06191716082D 24 26 0 0 0 0 0 0 0 0999 V2000 -1.7321 5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 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 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 4.5000 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 -2.5981 1.5000 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 -1.7321 0.0000 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 1.5000 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 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 3.4641 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 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 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 8 1 0 0 0 0 2 8 1 0 0 0 0 3 4 1 0 0 0 0 3 8 2 0 0 0 0 4 10 1 0 0 0 0 5 9 2 0 0 0 0 5 12 1 0 0 0 0 6 9 1 0 0 0 0 6 14 2 0 0 0 0 7 11 2 0 0 0 0 7 13 1 0 0 0 0 9 19 1 0 0 0 0 10 11 1 0 0 0 0 10 15 2 0 0 0 0 11 20 1 0 0 0 0 12 16 2 0 0 0 0 12 21 1 0 0 0 0 13 18 2 0 0 0 0 13 22 1 0 0 0 0 14 16 1 0 0 0 0 14 24 1 0 0 0 0 15 17 1 0 0 0 0 15 18 1 0 0 0 0 16 17 1 0 0 0 0 17 23 2 0 0 0 0 18 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	500.34
Volume:	536.424
LogP:	4.202
LogD:	4.553
LogS:	-4.007
# Rotatable Bonds:	9
TPSA:	100.1
# H-Bond Aceptor:	8
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.571
Synthetic Accessibility Score:	5.653
Fsp3:	0.643
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-5.095
MDCK Permeability:	1.1334735972923227e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.017
Human Intestinal Absorption (HIA):	0.019
20% Bioavailability (F20%):	0.04
30% Bioavailability (F30%):	0.508

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.299
Plasma Protein Binding (PPB):	89.1731185913086%
Volume Distribution (VD):	1.329
Pgp-substrate:	3.841984748840332%

ADMET: Metabolism

CYP1A2-inhibitor:	0.049
CYP1A2-substrate:	0.105
CYP2C19-inhibitor:	0.651
CYP2C19-substrate:	0.921
CYP2C9-inhibitor:	0.871
CYP2C9-substrate:	0.497
CYP2D6-inhibitor:	0.277
CYP2D6-substrate:	0.858
CYP3A4-inhibitor:	0.943
CYP3A4-substrate:	0.624

ADMET: Excretion

Clearance (CL):	7.466
Half-life (T1/2):	0.331

ADMET: Toxicity

hERG Blockers:	0.511
Human Hepatotoxicity (H-HT):	0.563
Drug-inuced Liver Injury (DILI):	0.762
AMES Toxicity:	0.035
Rat Oral Acute Toxicity:	0.418
Maximum Recommended Daily Dose:	0.431
Skin Sensitization:	0.038
Carcinogencity:	0.117
Eye Corrosion:	0.003
Eye Irritation:	0.007
Respiratory Toxicity:	0.876

Download Data

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

Natural Product: NPC274730

Natural Product ID:	NPC274730
*Common Name:**	1,3,5,7-Tetrahydroxy-8-Isoprenylxanthone
IUPAC Name:	2,4,6,8-tetrahydroxy-1-(3-methylbut-2-enyl)xanthen-9-one
Synonyms:
Standard InCHIKey:	BRERQMIMCLBRCS-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C18H16O6/c1-8(2)3-4-10-11(20)7-13(22)18-15(10)17(23)16-12(21)5-9(19)6-14(16)24-18/h3,5-7,19-22H,4H2,1-2H3
SMILES:	CC(=CCc1c(O)cc(c2c1c(=O)c1c(o2)cc(cc1O)O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3314605
PubChem CID:	5493670
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:0003519] 8-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
NPO19755	Artemisia anomala	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20000780]
NPO32711	garcinia esculenta	Species	Clusiaceae	Eukaryota	twigs	n.a.	n.a.	PMID[24960143]
NPO19755	Artemisia anomala	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17885	Eupatorium sachalinense	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7336	Senecio brasiliensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11057	Artocarpus integra	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18911	Piper umbellatum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11057	Artocarpus integra	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19755	Artemisia anomala	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7336	Senecio brasiliensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18911	Piper umbellatum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17885	Eupatorium sachalinense	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19755	Artemisia anomala	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO19755	Artemisia anomala	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17885	Eupatorium sachalinense	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19563	Gyrophora hyperborea	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO16291	Leptochloa digitata	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18911	Piper umbellatum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18412	Lobophytum microlobulatum	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7336	Senecio brasiliensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18013	Sceletium subvelutinum	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO1755	Pinus heldreichii	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11057	Artocarpus integra	Species	Moraceae	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	5

Activity Type	# Activity
Cell Line	4
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT65	Cell Line	HepG2	Homo sapiens	IC50	>	10000.0	nM	PMID[544293]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	10000.0	nM	PMID[544293]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	>	10000.0	nM	PMID[544293]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	6400.0	nM	PMID[544293]
NPT27	Others	Unspecified		IC50	>	10000.0	nM	PMID[544293]

☑ 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 NPC274730 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	454
0.1-0.2	2070
0.2-0.3	4963
0.3-0.4	11350
0.4-0.5	6097
0.5-0.6	3840
0.6-0.7	5044
0.7-0.8	5171
0.8-0.85	1945
0.85-0.9	1014
0.9-0.95	608
0.95-1	141

Similarity Score	Similarity Level	Natural Product ID
0.9933	High Similarity	NPC241904
0.9933	High Similarity	NPC300727
0.9867	High Similarity	NPC100123
0.9867	High Similarity	NPC476242
0.9865	High Similarity	NPC89474
0.9801	High Similarity	NPC14353
0.9801	High Similarity	NPC320359
0.9801	High Similarity	NPC56085
0.9801	High Similarity	NPC200746
0.9801	High Similarity	NPC228785
0.9737	High Similarity	NPC278052
0.9737	High Similarity	NPC40491
0.9737	High Similarity	NPC61010
0.9733	High Similarity	NPC142339
0.973	High Similarity	NPC202157
0.9673	High Similarity	NPC25152
0.9671	High Similarity	NPC139036
0.9669	High Similarity	NPC469584
0.9669	High Similarity	NPC236796
0.9669	High Similarity	NPC165977
0.9669	High Similarity	NPC217677
0.9662	High Similarity	NPC151473
0.961	High Similarity	NPC475985
0.961	High Similarity	NPC189473
0.961	High Similarity	NPC152659
0.961	High Similarity	NPC220313
0.961	High Similarity	NPC236132
0.961	High Similarity	NPC248638
0.961	High Similarity	NPC236521
0.961	High Similarity	NPC23298
0.961	High Similarity	NPC7483
0.9605	High Similarity	NPC474290
0.9605	High Similarity	NPC329091
0.9603	High Similarity	NPC191146
0.9603	High Similarity	NPC68093
0.9603	High Similarity	NPC138243
0.9548	High Similarity	NPC275780
0.9548	High Similarity	NPC326520
0.9548	High Similarity	NPC472450
0.9548	High Similarity	NPC239752
0.9542	High Similarity	NPC474287
0.9542	High Similarity	NPC235018
0.9542	High Similarity	NPC45146
0.9542	High Similarity	NPC475886
0.9542	High Similarity	NPC119224
0.9539	High Similarity	NPC136674
0.9539	High Similarity	NPC48208
0.9539	High Similarity	NPC222814
0.9539	High Similarity	NPC78225
0.9539	High Similarity	NPC36852
0.9539	High Similarity	NPC96167
0.9539	High Similarity	NPC474836
0.9539	High Similarity	NPC475267
0.9539	High Similarity	NPC162869
0.9539	High Similarity	NPC262286
0.9539	High Similarity	NPC474208
0.9539	High Similarity	NPC472913
0.9539	High Similarity	NPC245758
0.9539	High Similarity	NPC472914
0.9539	High Similarity	NPC156057
0.9539	High Similarity	NPC472910
0.9539	High Similarity	NPC472911
0.9533	High Similarity	NPC180234
0.9533	High Similarity	NPC120537
0.9533	High Similarity	NPC101996
0.9533	High Similarity	NPC199100
0.953	High Similarity	NPC61620
0.9487	High Similarity	NPC39091
0.9487	High Similarity	NPC170245
0.9487	High Similarity	NPC37870
0.9487	High Similarity	NPC472449
0.9484	High Similarity	NPC146134
0.9484	High Similarity	NPC270837
0.9481	High Similarity	NPC32694
0.9481	High Similarity	NPC474187
0.9481	High Similarity	NPC474351
0.9481	High Similarity	NPC474186
0.9481	High Similarity	NPC475883
0.9477	High Similarity	NPC235448
0.9474	High Similarity	NPC235165
0.9474	High Similarity	NPC472916
0.9474	High Similarity	NPC255106
0.9474	High Similarity	NPC472907
0.947	High Similarity	NPC75279
0.947	High Similarity	NPC47781
0.947	High Similarity	NPC167091
0.947	High Similarity	NPC183878
0.947	High Similarity	NPC160951
0.947	High Similarity	NPC22519
0.947	High Similarity	NPC88645
0.947	High Similarity	NPC292214
0.947	High Similarity	NPC231018
0.947	High Similarity	NPC250822
0.947	High Similarity	NPC206238
0.947	High Similarity	NPC255350
0.947	High Similarity	NPC276409
0.947	High Similarity	NPC472905
0.947	High Similarity	NPC145379
0.947	High Similarity	NPC69394
0.947	High Similarity	NPC271779
0.947	High Similarity	NPC176775
0.947	High Similarity	NPC274327
0.9467	High Similarity	NPC171010
0.9467	High Similarity	NPC117579
0.9467	High Similarity	NPC251110
0.9427	High Similarity	NPC6588
0.9427	High Similarity	NPC477154
0.9427	High Similarity	NPC117854
0.9419	High Similarity	NPC294965
0.9419	High Similarity	NPC329760
0.9419	High Similarity	NPC229632
0.9419	High Similarity	NPC470694
0.9416	High Similarity	NPC36217
0.9416	High Similarity	NPC80375
0.9416	High Similarity	NPC471973
0.9416	High Similarity	NPC204290
0.9412	High Similarity	NPC181960
0.9412	High Similarity	NPC210084
0.9412	High Similarity	NPC129684
0.9412	High Similarity	NPC472963
0.9412	High Similarity	NPC99597
0.9412	High Similarity	NPC299520
0.9412	High Similarity	NPC223787
0.9408	High Similarity	NPC37392
0.9408	High Similarity	NPC4455
0.9408	High Similarity	NPC146165
0.9408	High Similarity	NPC92659
0.9408	High Similarity	NPC213622
0.9408	High Similarity	NPC256612
0.9408	High Similarity	NPC67396
0.9408	High Similarity	NPC20830
0.9408	High Similarity	NPC183597
0.9408	High Similarity	NPC227325
0.9408	High Similarity	NPC2476
0.9408	High Similarity	NPC128863
0.9408	High Similarity	NPC138360
0.9408	High Similarity	NPC280339
0.9408	High Similarity	NPC208197
0.9408	High Similarity	NPC113906
0.9408	High Similarity	NPC196439
0.9408	High Similarity	NPC163780
0.9408	High Similarity	NPC167815
0.9408	High Similarity	NPC50715
0.9408	High Similarity	NPC201136
0.9408	High Similarity	NPC472909
0.9408	High Similarity	NPC2928
0.9404	High Similarity	NPC188203
0.9404	High Similarity	NPC241498
0.9404	High Similarity	NPC100887
0.9404	High Similarity	NPC71334
0.9404	High Similarity	NPC83508
0.9404	High Similarity	NPC198826
0.9404	High Similarity	NPC301323
0.9404	High Similarity	NPC275836
0.9404	High Similarity	NPC275722
0.9404	High Similarity	NPC212678
0.9404	High Similarity	NPC162313
0.9404	High Similarity	NPC39007
0.9404	High Similarity	NPC25270
0.9404	High Similarity	NPC293183
0.9404	High Similarity	NPC156222
0.9404	High Similarity	NPC222830
0.9404	High Similarity	NPC239128
0.9404	High Similarity	NPC131624
0.9404	High Similarity	NPC256283
0.9404	High Similarity	NPC187498
0.9404	High Similarity	NPC161277
0.9404	High Similarity	NPC120163
0.9404	High Similarity	NPC57030
0.94	High Similarity	NPC179183
0.94	High Similarity	NPC248102
0.94	High Similarity	NPC62042
0.9396	High Similarity	NPC276930
0.9396	High Similarity	NPC194856
0.9359	High Similarity	NPC41301
0.9359	High Similarity	NPC474350
0.9359	High Similarity	NPC133065
0.9359	High Similarity	NPC207690
0.9359	High Similarity	NPC197168
0.9355	High Similarity	NPC266314
0.9355	High Similarity	NPC167678
0.9355	High Similarity	NPC29876
0.9355	High Similarity	NPC66288
0.9351	High Similarity	NPC172770
0.9351	High Similarity	NPC250214
0.9351	High Similarity	NPC95936
0.9351	High Similarity	NPC152904
0.9351	High Similarity	NPC185258
0.9346	High Similarity	NPC474520
0.9346	High Similarity	NPC24640
0.9346	High Similarity	NPC49824
0.9342	High Similarity	NPC273462
0.9342	High Similarity	NPC472915
0.9342	High Similarity	NPC33051
0.9342	High Similarity	NPC227337
0.9342	High Similarity	NPC70433
0.9342	High Similarity	NPC18727
0.9342	High Similarity	NPC49402
0.9342	High Similarity	NPC280937
0.9338	High Similarity	NPC149614

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 NPC274730 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	436
0.1-0.2	1029
0.2-0.3	1880
0.3-0.4	2707
0.4-0.5	1678
0.5-0.6	940
0.6-0.7	316
0.7-0.8	120
0.8-0.85	27
0.85-0.9	11
0.9-0.95	6
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.947	High Similarity	NPD2801	Approved
0.9276	High Similarity	NPD1934	Approved
0.9091	High Similarity	NPD2393	Clinical (unspecified phase)
0.9	High Similarity	NPD1511	Approved
0.8882	High Similarity	NPD1512	Approved
0.8854	High Similarity	NPD3882	Suspended
0.882	High Similarity	NPD6167	Clinical (unspecified phase)
0.882	High Similarity	NPD6166	Phase 2
0.882	High Similarity	NPD6168	Clinical (unspecified phase)
0.8726	High Similarity	NPD1465	Phase 2
0.8688	High Similarity	NPD5494	Approved
0.8616	High Similarity	NPD4868	Clinical (unspecified phase)
0.8606	High Similarity	NPD7074	Phase 3
0.8598	High Similarity	NPD3818	Discontinued
0.858	High Similarity	NPD6232	Discontinued
0.8563	High Similarity	NPD4338	Clinical (unspecified phase)
0.8553	High Similarity	NPD3817	Phase 2
0.8545	High Similarity	NPD7054	Approved
0.8537	High Similarity	NPD7473	Discontinued
0.8494	Intermediate Similarity	NPD7472	Approved
0.8452	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8434	Intermediate Similarity	NPD5844	Phase 1
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	NPD6797	Phase 2
0.8302	Intermediate Similarity	NPD4380	Phase 2
0.8301	Intermediate Similarity	NPD1549	Phase 2
0.8293	Intermediate Similarity	NPD6959	Discontinued
0.8284	Intermediate Similarity	NPD7251	Discontinued
0.8235	Intermediate Similarity	NPD7808	Phase 3
0.8221	Intermediate Similarity	NPD7075	Discontinued
0.8221	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.82	Intermediate Similarity	NPD943	Approved
0.8182	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8148	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8118	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.811	Intermediate Similarity	NPD3749	Approved
0.8108	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8105	Intermediate Similarity	NPD1510	Phase 2
0.8101	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8098	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8079	Intermediate Similarity	NPD1240	Approved
0.8077	Intermediate Similarity	NPD3750	Approved
0.8054	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8052	Intermediate Similarity	NPD2796	Approved
0.8038	Intermediate Similarity	NPD6799	Approved
0.8013	Intermediate Similarity	NPD2800	Approved
0.7988	Intermediate Similarity	NPD5402	Approved
0.7987	Intermediate Similarity	NPD2533	Approved
0.7987	Intermediate Similarity	NPD2534	Approved
0.7987	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD2532	Approved
0.7976	Intermediate Similarity	NPD3926	Phase 2
0.7974	Intermediate Similarity	NPD1607	Approved
0.7964	Intermediate Similarity	NPD1247	Approved
0.7963	Intermediate Similarity	NPD6599	Discontinued
0.7935	Intermediate Similarity	NPD6100	Approved
0.7935	Intermediate Similarity	NPD6099	Approved
0.7914	Intermediate Similarity	NPD7411	Suspended
0.7895	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7871	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7866	Intermediate Similarity	NPD6801	Discontinued
0.7853	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7844	Intermediate Similarity	NPD6234	Discontinued
0.7843	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7843	Intermediate Similarity	NPD1613	Approved
0.7821	Intermediate Similarity	NPD2935	Discontinued
0.7792	Intermediate Similarity	NPD447	Suspended
0.7792	Intermediate Similarity	NPD230	Phase 1
0.7791	Intermediate Similarity	NPD3226	Approved
0.7771	Intermediate Similarity	NPD2346	Discontinued
0.776	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7759	Intermediate Similarity	NPD6559	Discontinued
0.7756	Intermediate Similarity	NPD3748	Approved
0.7751	Intermediate Similarity	NPD7199	Phase 2
0.7733	Intermediate Similarity	NPD3751	Discontinued
0.7719	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7706	Intermediate Similarity	NPD3787	Discontinued
0.7702	Intermediate Similarity	NPD7390	Discontinued
0.7669	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7661	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7658	Intermediate Similarity	NPD2344	Approved
0.7651	Intermediate Similarity	NPD37	Approved
0.7647	Intermediate Similarity	NPD3027	Phase 3
0.7633	Intermediate Similarity	NPD919	Approved
0.763	Intermediate Similarity	NPD7228	Approved
0.7619	Intermediate Similarity	NPD4967	Phase 2
0.7619	Intermediate Similarity	NPD4966	Approved
0.7619	Intermediate Similarity	NPD7768	Phase 2
0.7619	Intermediate Similarity	NPD4965	Approved
0.7584	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD5403	Approved
0.7532	Intermediate Similarity	NPD2799	Discontinued
0.7516	Intermediate Similarity	NPD4628	Phase 3
0.7516	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD1653	Approved
0.75	Intermediate Similarity	NPD5710	Approved
0.75	Intermediate Similarity	NPD5711	Approved
0.7485	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD1551	Phase 2
0.7484	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7469	Intermediate Similarity	NPD2309	Approved
0.7453	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD1243	Approved
0.7452	Intermediate Similarity	NPD1933	Approved
0.7439	Intermediate Similarity	NPD5401	Approved
0.7439	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD4625	Phase 3
0.7405	Intermediate Similarity	NPD6651	Approved
0.7403	Intermediate Similarity	NPD9494	Approved
0.738	Intermediate Similarity	NPD6776	Approved
0.738	Intermediate Similarity	NPD6781	Approved
0.738	Intermediate Similarity	NPD6780	Approved
0.738	Intermediate Similarity	NPD6779	Approved
0.738	Intermediate Similarity	NPD6782	Approved
0.738	Intermediate Similarity	NPD6778	Approved
0.738	Intermediate Similarity	NPD6777	Approved
0.7374	Intermediate Similarity	NPD8312	Approved
0.7374	Intermediate Similarity	NPD8313	Approved
0.7372	Intermediate Similarity	NPD2313	Discontinued
0.7368	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD6190	Approved
0.7355	Intermediate Similarity	NPD4908	Phase 1
0.7349	Intermediate Similarity	NPD920	Approved
0.7318	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD5953	Discontinued
0.7303	Intermediate Similarity	NPD9269	Phase 2
0.7301	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7288	Intermediate Similarity	NPD7286	Phase 2
0.7273	Intermediate Similarity	NPD1470	Approved
0.7273	Intermediate Similarity	NPD1203	Approved
0.7263	Intermediate Similarity	NPD7685	Pre-registration
0.7263	Intermediate Similarity	NPD7435	Discontinued
0.7261	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD3268	Approved
0.7257	Intermediate Similarity	NPD5242	Approved
0.7255	Intermediate Similarity	NPD4749	Approved
0.7254	Intermediate Similarity	NPD8151	Discontinued
0.7253	Intermediate Similarity	NPD8150	Discontinued
0.7253	Intermediate Similarity	NPD8434	Phase 2
0.7237	Intermediate Similarity	NPD1201	Approved
0.7237	Intermediate Similarity	NPD1610	Phase 2
0.7229	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD2798	Approved
0.7216	Intermediate Similarity	NPD2403	Approved
0.72	Intermediate Similarity	NPD7229	Phase 3
0.719	Intermediate Similarity	NPD1608	Approved
0.7179	Intermediate Similarity	NPD2861	Phase 2
0.7179	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD7783	Phase 2
0.7174	Intermediate Similarity	NPD4287	Approved
0.7173	Intermediate Similarity	NPD7697	Approved
0.7173	Intermediate Similarity	NPD7696	Phase 3
0.7173	Intermediate Similarity	NPD7698	Approved
0.7167	Intermediate Similarity	NPD7240	Approved
0.7161	Intermediate Similarity	NPD2797	Approved
0.7152	Intermediate Similarity	NPD3764	Approved
0.7151	Intermediate Similarity	NPD5353	Approved
0.7151	Intermediate Similarity	NPD4288	Approved
0.7135	Intermediate Similarity	NPD7870	Phase 2
0.7135	Intermediate Similarity	NPD6844	Discontinued
0.7135	Intermediate Similarity	NPD7871	Phase 2
0.7126	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD6823	Phase 2
0.7117	Intermediate Similarity	NPD1471	Phase 3
0.7113	Intermediate Similarity	NPD7701	Phase 2
0.7112	Intermediate Similarity	NPD6534	Approved
0.7112	Intermediate Similarity	NPD4360	Phase 2
0.7112	Intermediate Similarity	NPD6535	Approved
0.7112	Intermediate Similarity	NPD4363	Phase 3
0.7108	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD9717	Approved
0.7063	Intermediate Similarity	NPD4060	Phase 1
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
0.7049	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD7874	Approved
0.7041	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD9268	Approved
0.7033	Intermediate Similarity	NPD7549	Discontinued
0.703	Intermediate Similarity	NPD2654	Approved
0.7025	Intermediate Similarity	NPD6832	Phase 2
0.7019	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7015	Intermediate Similarity	NPD2899	Discontinued
0.7013	Intermediate Similarity	NPD422	Phase 1
0.7006	Intermediate Similarity	NPD3300	Phase 2
0.7005	Intermediate Similarity	NPD7801	Approved
0.7	Intermediate Similarity	NPD7699	Phase 2
0.7	Intermediate Similarity	NPD6233	Phase 2
0.7	Intermediate Similarity	NPD7700	Phase 2
0.6994	Remote Similarity	NPD7033	Discontinued
0.6994	Remote Similarity	NPD4308	Phase 3
0.6993	Remote Similarity	NPD17	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