NPASS Compound

Structure

NPC236132 OpenBabel07101719152D 35 37 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 -6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 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 3.4641 -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 4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 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 2.5981 -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 3.0000 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 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 2.0000 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 -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 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 -2.5981 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 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 -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 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 2.5981 1.5000 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 -1.7321 3.0000 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 0.0000 3.0000 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 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 15 1 0 0 0 0 2 15 1 0 0 0 0 3 16 1 0 0 0 0 4 16 1 0 0 0 0 5 17 1 0 0 0 0 6 17 1 0 0 0 0 7 34 1 0 0 0 0 8 11 1 0 0 0 0 8 15 2 0 0 0 0 9 12 1 0 0 0 0 9 16 2 0 0 0 0 10 13 1 0 0 0 0 10 17 2 0 0 0 0 11 18 1 0 0 0 0 12 19 1 0 0 0 0 13 20 1 0 0 0 0 14 21 2 0 0 0 0 14 22 1 0 0 0 0 18 21 1 0 0 0 0 18 25 2 0 0 0 0 19 23 2 0 0 0 0 19 29 1 0 0 0 0 20 26 1 0 0 0 0 20 28 2 0 0 0 0 21 30 1 0 0 0 0 22 24 2 0 0 0 0 22 35 1 0 0 0 0 23 27 1 0 0 0 0 23 28 1 0 0 0 0 24 25 1 0 0 0 0 24 27 1 0 0 0 0 25 31 1 0 0 0 0 26 29 2 0 0 0 0 26 32 1 0 0 0 0 27 33 2 0 0 0 0 28 35 1 0 0 0 0 29 34 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	478.24
Volume:	510.847
LogP:	7.525
LogD:	4.145
LogS:	-3.205
# Rotatable Bonds:	7
TPSA:	100.13
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.256
Synthetic Accessibility Score:	3.52
Fsp3:	0.345
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:	-4.866
MDCK Permeability:	1.4341253518068697e-05
Pgp-inhibitor:	0.939
Pgp-substrate:	0.467
Human Intestinal Absorption (HIA):	0.432
20% Bioavailability (F20%):	0.818
30% Bioavailability (F30%):	0.08

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.003
Plasma Protein Binding (PPB):	85.0456314086914%
Volume Distribution (VD):	0.949
Pgp-substrate:	17.506269454956055%

ADMET: Metabolism

CYP1A2-inhibitor:	0.199
CYP1A2-substrate:	0.493
CYP2C19-inhibitor:	0.773
CYP2C19-substrate:	0.168
CYP2C9-inhibitor:	0.87
CYP2C9-substrate:	0.941
CYP2D6-inhibitor:	0.159
CYP2D6-substrate:	0.265
CYP3A4-inhibitor:	0.123
CYP3A4-substrate:	0.104

ADMET: Excretion

Clearance (CL):	6.216
Half-life (T1/2):	0.135

ADMET: Toxicity

hERG Blockers:	0.016
Human Hepatotoxicity (H-HT):	0.967
Drug-inuced Liver Injury (DILI):	0.95
AMES Toxicity:	0.316
Rat Oral Acute Toxicity:	0.636
Maximum Recommended Daily Dose:	0.128
Skin Sensitization:	0.88
Carcinogencity:	0.244
Eye Corrosion:	0.003
Eye Irritation:	0.185
Respiratory Toxicity:	0.359

Download Data

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

Natural Product: NPC236132

Natural Product ID:	NPC236132
*Common Name:**	7-O-Methylgarcinone
IUPAC Name:	3,6,8-trihydroxy-2-methoxy-1,4,7-tris(3-methylbut-2-enyl)xanthen-9-one
Synonyms:	7-O-Methylgarcinone
Standard InCHIKey:	CYZRCBIQIBAFCQ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C29H34O6/c1-15(2)8-11-18-21(30)14-22-24(25(18)31)27(33)23-19(12-9-16(3)4)29(34-7)26(32)20(28(23)35-22)13-10-17(5)6/h8-10,14,30-32H,11-13H2,1-7H3
SMILES:	CC(=CCc1c(cc2c(c1O)c(=O)c1c(CC=C(C)C)c(c(c(CC=C(C)C)c1o2)O)OC)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL463410
PubChem CID:	10435205
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
NPO25472	Garcinia cowa	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1071/CH03175]
NPO18783	Garcinia fusca	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12608849]
NPO25472	Garcinia cowa	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19299148]
NPO25472	Garcinia cowa	Species	Clusiaceae	Eukaryota	twigs	n.a.	n.a.	PMID[20058933]
NPO25472	Garcinia cowa	Species	Clusiaceae	Eukaryota	flowers	Pakook, Muang District, Chiang Rai Province, Thailand	2013-Feb	PMID[25651042]
NPO25472	Garcinia cowa	Species	Clusiaceae	Eukaryota	young fruits	Khokkhon, Tha Bo District, Nong Khai Province, Thailand	2011-Aug	PMID[25651042]
NPO25472	Garcinia cowa	Species	Clusiaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[31860303]
NPO25472	Garcinia cowa	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25472	Garcinia cowa	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18783	Garcinia fusca	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25472	Garcinia cowa	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	6
Others	9

Activity Type	# Activity
Cell Line	4
Organism	6
Others	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT80	Cell Line	Raji	Homo sapiens	Activity	=	70.0	%	PMID[524067]
NPT80	Cell Line	Raji	Homo sapiens	Activity	>	80.0	%	PMID[524067]
NPT2	Others	Unspecified		Inhibition	=	0.0	%	PMID[524067]
NPT2	Others	Unspecified		Inhibition	=	16.3	%	PMID[524067]
NPT2	Others	Unspecified		Inhibition	=	59.2	%	PMID[524067]
NPT2	Others	Unspecified		Inhibition	=	83.8	%	PMID[524067]
NPT2	Others	Unspecified		IC50	=	210.0	molar ratio	PMID[524067]
NPT2	Others	Unspecified		Inhibition	>	100.0	%	PMID[524068]
NPT314	Organism	Bacillus cereus	Bacillus cereus	MIC	=	32.0	ug.mL-1	PMID[524068]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	32.0	ug.mL-1	PMID[524068]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	128.0	ug.mL-1	PMID[524068]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	128.0	ug.mL-1	PMID[524068]
NPT566	Organism	Salmonella typhimurium	Salmonella enterica subsp. enterica serovar Typhimurium	MIC	=	128.0	ug.mL-1	PMID[524068]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	=	128.0	ug.mL-1	PMID[524068]

☑ 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 NPC236132 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	462
0.1-0.2	1820
0.2-0.3	4204
0.3-0.4	10620
0.4-0.5	7683
0.5-0.6	3541
0.6-0.7	5097
0.7-0.8	5385
0.8-0.85	2324
0.85-0.9	1065
0.9-0.95	437
0.95-1	59

Similarity Score	Similarity Level	Natural Product ID
0.987	High Similarity	NPC40491
0.987	High Similarity	NPC278052
0.9805	High Similarity	NPC14353
0.9805	High Similarity	NPC228785
0.9805	High Similarity	NPC320359
0.9805	High Similarity	NPC56085
0.9805	High Similarity	NPC119224
0.9744	High Similarity	NPC270837
0.9744	High Similarity	NPC7483
0.9742	High Similarity	NPC61010
0.974	High Similarity	NPC100123
0.9679	High Similarity	NPC294965
0.9677	High Similarity	NPC475886
0.9677	High Similarity	NPC474287
0.9675	High Similarity	NPC241904
0.9675	High Similarity	NPC217677
0.9675	High Similarity	NPC300727
0.9675	High Similarity	NPC236796
0.9675	High Similarity	NPC165977
0.962	High Similarity	NPC37870
0.962	High Similarity	NPC39091
0.9618	High Similarity	NPC220313
0.9618	High Similarity	NPC152659
0.9618	High Similarity	NPC248638
0.9618	High Similarity	NPC236521
0.9618	High Similarity	NPC197168
0.9615	High Similarity	NPC474351
0.9615	High Similarity	NPC475883
0.9615	High Similarity	NPC474187
0.9615	High Similarity	NPC474186
0.9615	High Similarity	NPC66288
0.9613	High Similarity	NPC476242
0.961	High Similarity	NPC274730
0.961	High Similarity	NPC142339
0.9557	High Similarity	NPC326520
0.9557	High Similarity	NPC275780
0.9557	High Similarity	NPC472450
0.9557	High Similarity	NPC25361
0.9557	High Similarity	NPC239752
0.9554	High Similarity	NPC470694
0.9554	High Similarity	NPC25152
0.9548	High Similarity	NPC262286
0.9548	High Similarity	NPC36852
0.9548	High Similarity	NPC78225
0.9497	High Similarity	NPC170245
0.9494	High Similarity	NPC23298
0.9494	High Similarity	NPC189473
0.9494	High Similarity	NPC207690
0.949	High Similarity	NPC32694
0.9487	High Similarity	NPC85121
0.9484	High Similarity	NPC138243
0.9484	High Similarity	NPC191146
0.9484	High Similarity	NPC68093
0.9481	High Similarity	NPC89474
0.9437	High Similarity	NPC117854
0.9437	High Similarity	NPC218226
0.9437	High Similarity	NPC6588
0.9437	High Similarity	NPC477154
0.943	High Similarity	NPC201800
0.943	High Similarity	NPC229632
0.9427	High Similarity	NPC84571
0.9427	High Similarity	NPC235018
0.9427	High Similarity	NPC200746
0.9427	High Similarity	NPC36217
0.9427	High Similarity	NPC45146
0.9423	High Similarity	NPC223787
0.9423	High Similarity	NPC469584
0.9423	High Similarity	NPC136674
0.9419	High Similarity	NPC113906
0.9383	High Similarity	NPC158226
0.9379	High Similarity	NPC163130
0.9379	High Similarity	NPC165979
0.9375	High Similarity	NPC472449
0.9375	High Similarity	NPC43319
0.9371	High Similarity	NPC146134
0.9371	High Similarity	NPC41301
0.9371	High Similarity	NPC474350
0.9371	High Similarity	NPC475985
0.9367	High Similarity	NPC278427
0.9367	High Similarity	NPC311740
0.9367	High Similarity	NPC266314
0.9363	High Similarity	NPC95936
0.9363	High Similarity	NPC250214
0.9363	High Similarity	NPC210459
0.9363	High Similarity	NPC235448
0.9363	High Similarity	NPC329091
0.9359	High Similarity	NPC209614
0.9359	High Similarity	NPC470328
0.9359	High Similarity	NPC472626
0.9351	High Similarity	NPC202157
0.9321	High Similarity	NPC124470
0.9321	High Similarity	NPC109827
0.9317	High Similarity	NPC126204
0.9317	High Similarity	NPC474024
0.9313	High Similarity	NPC293319
0.9313	High Similarity	NPC473286
0.9313	High Similarity	NPC475888
0.9308	High Similarity	NPC211107
0.9308	High Similarity	NPC472448
0.9308	High Similarity	NPC329760
0.9308	High Similarity	NPC52204
0.9308	High Similarity	NPC83922
0.9304	High Similarity	NPC139036
0.9304	High Similarity	NPC321399
0.9304	High Similarity	NPC471973
0.9304	High Similarity	NPC246478
0.9304	High Similarity	NPC204290
0.9304	High Similarity	NPC299436
0.9304	High Similarity	NPC476980
0.9304	High Similarity	NPC80375
0.9299	High Similarity	NPC475267
0.9299	High Similarity	NPC48208
0.9299	High Similarity	NPC474836
0.9299	High Similarity	NPC199463
0.9299	High Similarity	NPC472910
0.9299	High Similarity	NPC472911
0.9299	High Similarity	NPC245758
0.9299	High Similarity	NPC96167
0.9299	High Similarity	NPC156057
0.9299	High Similarity	NPC472913
0.9299	High Similarity	NPC162869
0.9299	High Similarity	NPC37543
0.9299	High Similarity	NPC222814
0.9299	High Similarity	NPC474208
0.9299	High Similarity	NPC472914
0.9299	High Similarity	NPC472963
0.9295	High Similarity	NPC57674
0.9295	High Similarity	NPC230149
0.9295	High Similarity	NPC168247
0.9295	High Similarity	NPC45849
0.9295	High Similarity	NPC200761
0.9295	High Similarity	NPC470327
0.9295	High Similarity	NPC152951
0.9295	High Similarity	NPC117992
0.9295	High Similarity	NPC477503
0.929	High Similarity	NPC120537
0.929	High Similarity	NPC471982
0.929	High Similarity	NPC249570
0.929	High Similarity	NPC180234
0.929	High Similarity	NPC101996
0.929	High Similarity	NPC199100
0.9286	High Similarity	NPC151473
0.9268	High Similarity	NPC245975
0.9268	High Similarity	NPC227906
0.9259	High Similarity	NPC476637
0.9259	High Similarity	NPC49487
0.9259	High Similarity	NPC99613
0.9255	High Similarity	NPC29160
0.925	High Similarity	NPC474240
0.925	High Similarity	NPC186686
0.9245	High Similarity	NPC29876
0.9245	High Similarity	NPC167678
0.9245	High Similarity	NPC258331
0.9245	High Similarity	NPC472275
0.9241	High Similarity	NPC185258
0.9241	High Similarity	NPC474290
0.9241	High Similarity	NPC172770
0.9236	High Similarity	NPC5379
0.9236	High Similarity	NPC472916
0.9236	High Similarity	NPC291878
0.9236	High Similarity	NPC472907
0.9236	High Similarity	NPC474167
0.9236	High Similarity	NPC235165
0.9236	High Similarity	NPC278778
0.9236	High Similarity	NPC14561
0.9236	High Similarity	NPC77807
0.9236	High Similarity	NPC35038
0.9236	High Similarity	NPC255106
0.9236	High Similarity	NPC470762
0.9236	High Similarity	NPC195796
0.9236	High Similarity	NPC475799
0.9236	High Similarity	NPC13779
0.9231	High Similarity	NPC227337
0.9231	High Similarity	NPC276409
0.9231	High Similarity	NPC231018
0.9231	High Similarity	NPC274327
0.9231	High Similarity	NPC70433
0.9231	High Similarity	NPC33051
0.9231	High Similarity	NPC271779
0.9231	High Similarity	NPC250822
0.9231	High Similarity	NPC167091
0.9231	High Similarity	NPC49402
0.9231	High Similarity	NPC183878
0.9231	High Similarity	NPC273462
0.9231	High Similarity	NPC75279
0.9231	High Similarity	NPC292214
0.9231	High Similarity	NPC160951
0.9231	High Similarity	NPC206238
0.9231	High Similarity	NPC298692
0.9231	High Similarity	NPC255350
0.9231	High Similarity	NPC88645
0.9231	High Similarity	NPC176775
0.9231	High Similarity	NPC69394
0.9231	High Similarity	NPC476631
0.9231	High Similarity	NPC47781
0.9231	High Similarity	NPC145379
0.9231	High Similarity	NPC22519
0.9226	High Similarity	NPC171010
0.9226	High Similarity	NPC117579
0.9217	High Similarity	NPC113446

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 NPC236132 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	403
0.1-0.2	989
0.2-0.3	1853
0.3-0.4	2684
0.4-0.5	1774
0.5-0.6	887
0.6-0.7	388
0.7-0.8	131
0.8-0.85	27
0.85-0.9	13
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9231	High Similarity	NPD2801	Approved
0.9108	High Similarity	NPD2393	Clinical (unspecified phase)
0.9045	High Similarity	NPD1934	Approved
0.8902	High Similarity	NPD7473	Discontinued
0.8834	High Similarity	NPD6232	Discontinued
0.8712	High Similarity	NPD5494	Approved
0.8683	High Similarity	NPD5844	Phase 1
0.8654	High Similarity	NPD1511	Approved
0.8642	High Similarity	NPD3882	Suspended
0.8614	High Similarity	NPD6166	Phase 2
0.8614	High Similarity	NPD6168	Clinical (unspecified phase)
0.8614	High Similarity	NPD6167	Clinical (unspecified phase)
0.8545	High Similarity	NPD6959	Discontinued
0.8544	High Similarity	NPD1512	Approved
0.8521	High Similarity	NPD7074	Phase 3
0.8519	High Similarity	NPD7819	Suspended
0.8481	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8462	Intermediate Similarity	NPD7054	Approved
0.8415	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8412	Intermediate Similarity	NPD7472	Approved
0.8405	Intermediate Similarity	NPD1465	Phase 2
0.8402	Intermediate Similarity	NPD3818	Discontinued
0.8372	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8364	Intermediate Similarity	NPD7075	Discontinued
0.8354	Intermediate Similarity	NPD3817	Phase 2
0.8333	Intermediate Similarity	NPD4380	Phase 2
0.8293	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.825	Intermediate Similarity	NPD2532	Approved
0.825	Intermediate Similarity	NPD2534	Approved
0.825	Intermediate Similarity	NPD2533	Approved
0.8242	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8208	Intermediate Similarity	NPD7251	Discontinued
0.8192	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8161	Intermediate Similarity	NPD7808	Phase 3
0.8153	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8153	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.815	Intermediate Similarity	NPD6797	Phase 2
0.8101	Intermediate Similarity	NPD1549	Phase 2
0.8036	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8035	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8025	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8025	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8013	Intermediate Similarity	NPD1607	Approved
0.8	Intermediate Similarity	NPD6599	Discontinued
0.8	Intermediate Similarity	NPD6559	Discontinued
0.8	Intermediate Similarity	NPD1247	Approved
0.8	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD6100	Approved
0.7975	Intermediate Similarity	NPD6099	Approved
0.7952	Intermediate Similarity	NPD7411	Suspended
0.7943	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7939	Intermediate Similarity	NPD3226	Approved
0.7937	Intermediate Similarity	NPD2800	Approved
0.7925	Intermediate Similarity	NPD2346	Discontinued
0.7911	Intermediate Similarity	NPD1510	Phase 2
0.7904	Intermediate Similarity	NPD6801	Discontinued
0.7892	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7885	Intermediate Similarity	NPD943	Approved
0.7885	Intermediate Similarity	NPD1240	Approved
0.7882	Intermediate Similarity	NPD6234	Discontinued
0.7862	Intermediate Similarity	NPD2796	Approved
0.7862	Intermediate Similarity	NPD2935	Discontinued
0.7853	Intermediate Similarity	NPD7390	Discontinued
0.7853	Intermediate Similarity	NPD6799	Approved
0.7824	Intermediate Similarity	NPD3749	Approved
0.7811	Intermediate Similarity	NPD5402	Approved
0.7803	Intermediate Similarity	NPD3926	Phase 2
0.7792	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD3750	Approved
0.7771	Intermediate Similarity	NPD7228	Approved
0.7765	Intermediate Similarity	NPD7768	Phase 2
0.7759	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7746	Intermediate Similarity	NPD5711	Approved
0.7746	Intermediate Similarity	NPD5710	Approved
0.7742	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7722	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7709	Intermediate Similarity	NPD8313	Approved
0.7709	Intermediate Similarity	NPD8312	Approved
0.7697	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD37	Approved
0.7688	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7674	Intermediate Similarity	NPD919	Approved
0.7669	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7661	Intermediate Similarity	NPD4967	Phase 2
0.7661	Intermediate Similarity	NPD4965	Approved
0.7661	Intermediate Similarity	NPD4966	Approved
0.7658	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7658	Intermediate Similarity	NPD1613	Approved
0.761	Intermediate Similarity	NPD230	Phase 1
0.7606	Intermediate Similarity	NPD6777	Approved
0.7606	Intermediate Similarity	NPD6778	Approved
0.7606	Intermediate Similarity	NPD6779	Approved
0.7606	Intermediate Similarity	NPD6780	Approved
0.7606	Intermediate Similarity	NPD6776	Approved
0.7606	Intermediate Similarity	NPD6782	Approved
0.7606	Intermediate Similarity	NPD6781	Approved
0.7586	Intermediate Similarity	NPD7199	Phase 2
0.7582	Intermediate Similarity	NPD8150	Discontinued
0.758	Intermediate Similarity	NPD4625	Phase 3
0.7579	Intermediate Similarity	NPD7435	Discontinued
0.7571	Intermediate Similarity	NPD3751	Discontinued
0.7565	Intermediate Similarity	NPD8151	Discontinued
0.7562	Intermediate Similarity	NPD6651	Approved
0.7561	Intermediate Similarity	NPD4628	Phase 3
0.7543	Intermediate Similarity	NPD3787	Discontinued
0.7531	Intermediate Similarity	NPD1551	Phase 2
0.75	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD447	Suspended
0.75	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7487	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7487	Intermediate Similarity	NPD7696	Phase 3
0.7487	Intermediate Similarity	NPD7697	Approved
0.7487	Intermediate Similarity	NPD7783	Phase 2
0.7487	Intermediate Similarity	NPD7698	Approved
0.7469	Intermediate Similarity	NPD2799	Discontinued
0.7469	Intermediate Similarity	NPD3748	Approved
0.7468	Intermediate Similarity	NPD3027	Phase 3
0.7448	Intermediate Similarity	NPD7870	Phase 2
0.7448	Intermediate Similarity	NPD7871	Phase 2
0.7435	Intermediate Similarity	NPD6823	Phase 2
0.743	Intermediate Similarity	NPD7286	Phase 2
0.7423	Intermediate Similarity	NPD7701	Phase 2
0.7421	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD5403	Approved
0.7396	Intermediate Similarity	NPD920	Approved
0.7394	Intermediate Similarity	NPD1243	Approved
0.7391	Intermediate Similarity	NPD8434	Phase 2
0.7378	Intermediate Similarity	NPD2344	Approved
0.7363	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD1653	Approved
0.7348	Intermediate Similarity	NPD5953	Discontinued
0.7347	Intermediate Similarity	NPD7874	Approved
0.7347	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7345	Intermediate Similarity	NPD7229	Phase 3
0.734	Intermediate Similarity	NPD6534	Approved
0.734	Intermediate Similarity	NPD6535	Approved
0.7321	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7316	Intermediate Similarity	NPD7699	Phase 2
0.7316	Intermediate Similarity	NPD7700	Phase 2
0.7312	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD2313	Discontinued
0.731	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD7801	Approved
0.7308	Intermediate Similarity	NPD7240	Approved
0.7289	Intermediate Similarity	NPD6674	Discontinued
0.7284	Intermediate Similarity	NPD1933	Approved
0.7278	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD5401	Approved
0.7233	Intermediate Similarity	NPD9494	Approved
0.7215	Intermediate Similarity	NPD1470	Approved
0.7213	Intermediate Similarity	NPD7685	Pre-registration
0.7212	Intermediate Similarity	NPD5408	Approved
0.7212	Intermediate Similarity	NPD5404	Approved
0.7212	Intermediate Similarity	NPD5405	Approved
0.7212	Intermediate Similarity	NPD5406	Approved
0.7209	Intermediate Similarity	NPD7458	Discontinued
0.7205	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD2309	Approved
0.7202	Intermediate Similarity	NPD6190	Approved
0.7197	Intermediate Similarity	NPD4749	Approved
0.7197	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7189	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD4908	Phase 1
0.7186	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD1201	Approved
0.7176	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD4360	Phase 2
0.7158	Intermediate Similarity	NPD4363	Phase 3
0.7143	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD4060	Phase 1
0.7111	Intermediate Similarity	NPD5242	Approved
0.7105	Intermediate Similarity	NPD6212	Phase 3
0.7105	Intermediate Similarity	NPD6213	Phase 3
0.7105	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7102	Intermediate Similarity	NPD5353	Approved
0.7099	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD6844	Discontinued
0.7083	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD7907	Approved
0.7072	Intermediate Similarity	NPD2403	Approved
0.707	Intermediate Similarity	NPD1610	Phase 2
0.7066	Intermediate Similarity	NPD1471	Phase 3
0.7044	Intermediate Similarity	NPD6696	Suspended
0.7041	Intermediate Similarity	NPD7003	Approved
0.7026	Intermediate Similarity	NPD2494	Approved
0.7026	Intermediate Similarity	NPD2493	Approved
0.7025	Intermediate Similarity	NPD9269	Phase 2
0.702	Intermediate Similarity	NPD7584	Approved
0.7019	Intermediate Similarity	NPD2861	Phase 2
0.701	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD8319	Approved
0.7005	Intermediate Similarity	NPD8320	Phase 1
0.7	Intermediate Similarity	NPD1203	Approved
0.7	Intermediate Similarity	NPD8127	Discontinued
0.6995	Remote Similarity	NPD7177	Discontinued
0.6994	Remote Similarity	NPD3268	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