NPASS Compound

Structure

NPC473812 OpenBabel07101718222D 34 36 0 0 1 0 0 0 0 0999 V2000 -2.0012 4.1225 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5529 5.7956 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1088 2.7483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7716 1.1481 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1213 2.1213 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0694 3.6049 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3282 4.5708 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8966 3.3461 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0544 1.3741 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4483 1.6730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9239 0.3827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7071 0.7071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -0.5000 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 -0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2941 4.8296 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9783 1.7568 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1554 2.3801 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 -3.4641 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 -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 -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 -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 -0.0000 -0.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -5.1962 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -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 1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 16 1 0 0 0 0 2 16 1 0 0 0 0 3 17 1 0 0 0 0 4 17 1 0 0 0 0 5 18 1 0 0 0 0 6 7 1 0 0 0 0 6 8 1 0 0 0 0 7 16 2 0 0 0 0 8 18 1 0 0 0 0 9 11 1 0 0 0 0 9 17 2 0 0 0 0 10 12 1 0 0 0 0 10 18 2 0 0 0 0 11 28 1 0 0 0 0 12 28 1 0 0 0 0 13 19 2 0 0 0 0 13 20 1 0 0 0 0 14 19 1 0 0 0 0 14 22 2 0 0 0 0 15 21 2 0 0 0 0 15 23 1 0 0 0 0 19 29 1 0 0 0 0 20 24 2 0 0 0 0 20 30 1 0 0 0 0 21 27 1 0 0 0 0 21 31 1 0 0 0 0 22 24 1 0 0 0 0 22 34 1 0 0 0 0 23 25 2 0 0 0 0 23 34 1 0 0 0 0 24 26 1 0 0 0 0 25 26 1 0 0 0 0 25 28 1 0 0 0 0 26 32 2 0 0 0 0 27 28 1 0 0 0 0 27 33 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	464.22
Volume:	493.551
LogP:	6.06
LogD:	4.298
LogS:	-3.249
# Rotatable Bonds:	7
TPSA:	104.81
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.41
Synthetic Accessibility Score:	4.102
Fsp3:	0.393
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.819
MDCK Permeability:	1.8746477508102544e-05
Pgp-inhibitor:	0.425
Pgp-substrate:	0.877
Human Intestinal Absorption (HIA):	0.042
20% Bioavailability (F20%):	0.803
30% Bioavailability (F30%):	0.01

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.004
Plasma Protein Binding (PPB):	93.49849700927734%
Volume Distribution (VD):	0.819
Pgp-substrate:	4.943253517150879%

ADMET: Metabolism

CYP1A2-inhibitor:	0.583
CYP1A2-substrate:	0.221
CYP2C19-inhibitor:	0.943
CYP2C19-substrate:	0.167
CYP2C9-inhibitor:	0.928
CYP2C9-substrate:	0.974
CYP2D6-inhibitor:	0.813
CYP2D6-substrate:	0.093
CYP3A4-inhibitor:	0.738
CYP3A4-substrate:	0.197

ADMET: Excretion

Clearance (CL):	4.831
Half-life (T1/2):	0.222

ADMET: Toxicity

hERG Blockers:	0.006
Human Hepatotoxicity (H-HT):	0.955
Drug-inuced Liver Injury (DILI):	0.86
AMES Toxicity:	0.352
Rat Oral Acute Toxicity:	0.648
Maximum Recommended Daily Dose:	0.092
Skin Sensitization:	0.616
Carcinogencity:	0.327
Eye Corrosion:	0.003
Eye Irritation:	0.127
Respiratory Toxicity:	0.259

Download Data

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

Natural Product: NPC473812

Natural Product ID:	NPC473812
*Common Name:**	Garcinianone A
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	FZFFGBOPCQADGY-VCHYOVAHSA-N
Standard InCHI:	InChI=1S/C28H32O6/c1-16(2)7-6-8-18(5)10-12-28(11-9-17(3)4)25-23(15-21(31)27(28)33)34-22-14-19(29)13-20(30)24(22)26(25)32/h7,9-10,13-15,29-31H,6,8,11-12H2,1-5H3/b18-10+
SMILES:	C/C(=CCC1(CC=C(C)C)C(=O)C(=Cc2c1c(=O)c1c(o2)cc(cc1O)O)O)/CCC=C(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL452501
PubChem CID:	n.a.
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

*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]
NPO5049	Garcinia multiflora	Species	Clusiaceae	Eukaryota	stems	n.a.	n.a.	PMID[12932126]
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]
NPO5049	Garcinia multiflora	Species	Clusiaceae	Eukaryota	twigs	n.a.	n.a.	PMID[20681570]
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]
NPO5049	Garcinia multiflora	Species	Clusiaceae	Eukaryota	Twigs and leaves	Taichung, Taiwan	1993-Aug	PMID[9322359]
NPO5049	Garcinia multiflora	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
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]
NPO5049	Garcinia multiflora	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5049	Garcinia multiflora	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5049	Garcinia multiflora	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	2
LD50	1
MIC	6
Others	1

Activity Type	# Activity
Organism	7
Others	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT140	Organism	Artemia	Artemia	LD50	=	7.7	uM	PMID[524766]
NPT1	Others	Radical scavenging activity		IC50	=	107400.0	nM	PMID[524766]
NPT2	Others	Unspecified		IC50	=	34000.0	nM	PMID[524767]
NPT314	Organism	Bacillus cereus	Bacillus cereus	MIC	=	4.0	ug.mL-1	PMID[524767]
NPT2	Others	Unspecified		Inhibition	=	66.7	%	PMID[524767]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	2.0	ug.mL-1	PMID[524767]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	64.0	ug.mL-1	PMID[524767]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	64.0	ug.mL-1	PMID[524767]
NPT566	Organism	Salmonella typhimurium	Salmonella enterica subsp. enterica serovar Typhimurium	MIC	=	64.0	ug.mL-1	PMID[524767]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	=	128.0	ug.mL-1	PMID[524767]

☑ 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 NPC473812 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	418
0.1-0.2	1615
0.2-0.3	3964
0.3-0.4	9857
0.4-0.5	8920
0.5-0.6	4080
0.6-0.7	5989
0.7-0.8	4595
0.8-0.85	2264
0.85-0.9	960
0.9-0.95	29
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC473813
0.9928	High Similarity	NPC472447
0.9928	High Similarity	NPC472446
0.9315	High Similarity	NPC470353
0.9247	High Similarity	NPC81474
0.9225	High Similarity	NPC204469
0.9214	High Similarity	NPC25427
0.9197	High Similarity	NPC10971
0.9161	High Similarity	NPC190637
0.9161	High Similarity	NPC212932
0.9161	High Similarity	NPC24821
0.9161	High Similarity	NPC11700
0.9161	High Similarity	NPC9117
0.9161	High Similarity	NPC293053
0.9149	High Similarity	NPC49242
0.9143	High Similarity	NPC228661
0.9128	High Similarity	NPC470354
0.9128	High Similarity	NPC470352
0.9097	High Similarity	NPC273538
0.9097	High Similarity	NPC216538
0.9097	High Similarity	NPC326500
0.9091	High Similarity	NPC473042
0.9091	High Similarity	NPC200694
0.9091	High Similarity	NPC325346
0.9085	High Similarity	NPC172986
0.9085	High Similarity	NPC281207
0.9085	High Similarity	NPC269652
0.9085	High Similarity	NPC261227
0.9085	High Similarity	NPC270883
0.9078	High Similarity	NPC131130
0.9071	High Similarity	NPC13408
0.9071	High Similarity	NPC174999
0.9051	High Similarity	NPC270369
0.9051	High Similarity	NPC5515
0.9048	High Similarity	NPC188403
0.9034	High Similarity	NPC178343
0.9034	High Similarity	NPC5820
0.9034	High Similarity	NPC306488
0.9034	High Similarity	NPC124729
0.9034	High Similarity	NPC329678
0.9028	High Similarity	NPC158874
0.9021	High Similarity	NPC205006
0.9021	High Similarity	NPC110969
0.9021	High Similarity	NPC316911
0.9021	High Similarity	NPC136840
0.9021	High Similarity	NPC147688
0.9021	High Similarity	NPC64908
0.9021	High Similarity	NPC316560
0.9021	High Similarity	NPC156590
0.9021	High Similarity	NPC118840
0.9021	High Similarity	NPC90582
0.9021	High Similarity	NPC262094
0.9014	High Similarity	NPC143799
0.9014	High Similarity	NPC220062
0.9014	High Similarity	NPC152042
0.9014	High Similarity	NPC301217
0.9014	High Similarity	NPC303633
0.9014	High Similarity	NPC55018
0.9014	High Similarity	NPC96565
0.9014	High Similarity	NPC241838
0.9014	High Similarity	NPC216978
0.9013	High Similarity	NPC103816
0.9013	High Similarity	NPC61382
0.9007	High Similarity	NPC250266
0.9007	High Similarity	NPC266597
0.9007	High Similarity	NPC299379
0.8993	High Similarity	NPC108113
0.8993	High Similarity	NPC93756
0.8986	High Similarity	NPC475589
0.8986	High Similarity	NPC31872
0.8986	High Similarity	NPC473584
0.898	High Similarity	NPC269420
0.8973	High Similarity	NPC166757
0.8973	High Similarity	NPC14001
0.8966	High Similarity	NPC234629
0.8966	High Similarity	NPC311741
0.8958	High Similarity	NPC323884
0.8958	High Similarity	NPC11561
0.8958	High Similarity	NPC321629
0.8958	High Similarity	NPC321148
0.8958	High Similarity	NPC226636
0.8958	High Similarity	NPC144499
0.8958	High Similarity	NPC326193
0.8951	High Similarity	NPC475680
0.8951	High Similarity	NPC146679
0.8951	High Similarity	NPC184536
0.8951	High Similarity	NPC235239
0.8951	High Similarity	NPC159275
0.8951	High Similarity	NPC305355
0.8951	High Similarity	NPC471587
0.8951	High Similarity	NPC103342
0.8951	High Similarity	NPC230285
0.8951	High Similarity	NPC477272
0.8951	High Similarity	NPC103904
0.8951	High Similarity	NPC69769
0.8951	High Similarity	NPC59951
0.8951	High Similarity	NPC241100
0.8944	High Similarity	NPC474487
0.8944	High Similarity	NPC470671
0.8944	High Similarity	NPC477055
0.8944	High Similarity	NPC470672
0.8944	High Similarity	NPC201395
0.8944	High Similarity	NPC124269
0.8944	High Similarity	NPC470669
0.8944	High Similarity	NPC474504
0.8944	High Similarity	NPC276905
0.8944	High Similarity	NPC477056
0.8944	High Similarity	NPC470668
0.8936	High Similarity	NPC473887
0.8936	High Similarity	NPC47815
0.8936	High Similarity	NPC281917
0.8936	High Similarity	NPC29353
0.8936	High Similarity	NPC256042
0.8936	High Similarity	NPC231772
0.8936	High Similarity	NPC216361
0.8936	High Similarity	NPC194281
0.8936	High Similarity	NPC234133
0.8936	High Similarity	NPC127447
0.8936	High Similarity	NPC121243
0.8936	High Similarity	NPC240147
0.8936	High Similarity	NPC124784
0.8936	High Similarity	NPC116775
0.8936	High Similarity	NPC187432
0.8929	High Similarity	NPC144027
0.8929	High Similarity	NPC125920
0.8929	High Similarity	NPC236974
0.8929	High Similarity	NPC172262
0.8921	High Similarity	NPC25937
0.8921	High Similarity	NPC203817
0.8919	High Similarity	NPC61258
0.8912	High Similarity	NPC244407
0.8912	High Similarity	NPC296869
0.8912	High Similarity	NPC470460
0.8904	High Similarity	NPC220418
0.8904	High Similarity	NPC470458
0.8897	High Similarity	NPC166138
0.8897	High Similarity	NPC38219
0.8897	High Similarity	NPC106985
0.8897	High Similarity	NPC219915
0.8897	High Similarity	NPC18585
0.8889	High Similarity	NPC282300
0.8889	High Similarity	NPC103362
0.8881	High Similarity	NPC23257
0.8881	High Similarity	NPC217186
0.8881	High Similarity	NPC230902
0.8881	High Similarity	NPC18260
0.8881	High Similarity	NPC140890
0.8881	High Similarity	NPC78913
0.8881	High Similarity	NPC139554
0.8881	High Similarity	NPC53181
0.8874	High Similarity	NPC192587
0.8873	High Similarity	NPC160972
0.8873	High Similarity	NPC181124
0.8873	High Similarity	NPC7013
0.8873	High Similarity	NPC116632
0.8873	High Similarity	NPC209560
0.8873	High Similarity	NPC294409
0.8873	High Similarity	NPC162680
0.8873	High Similarity	NPC303644
0.8873	High Similarity	NPC188879
0.8865	High Similarity	NPC60667
0.8865	High Similarity	NPC9985
0.8865	High Similarity	NPC239495
0.8865	High Similarity	NPC151113
0.8857	High Similarity	NPC57601
0.8857	High Similarity	NPC223457
0.8857	High Similarity	NPC78540
0.8857	High Similarity	NPC50898
0.8857	High Similarity	NPC274121
0.8857	High Similarity	NPC213216
0.8851	High Similarity	NPC470461
0.8844	High Similarity	NPC79469
0.8844	High Similarity	NPC10990
0.8844	High Similarity	NPC97716
0.8844	High Similarity	NPC104406
0.8844	High Similarity	NPC24673
0.8844	High Similarity	NPC201731
0.8844	High Similarity	NPC259632
0.8844	High Similarity	NPC300988
0.8844	High Similarity	NPC237635
0.8836	High Similarity	NPC476055
0.8836	High Similarity	NPC236766
0.8836	High Similarity	NPC470673
0.8836	High Similarity	NPC470674
0.8836	High Similarity	NPC197252
0.8836	High Similarity	NPC224714
0.8836	High Similarity	NPC117716
0.8831	High Similarity	NPC475106
0.8828	High Similarity	NPC202981
0.8828	High Similarity	NPC78803
0.8828	High Similarity	NPC62840
0.8828	High Similarity	NPC293852
0.8828	High Similarity	NPC59739
0.8828	High Similarity	NPC1534
0.8828	High Similarity	NPC214236
0.8828	High Similarity	NPC162476
0.8828	High Similarity	NPC299080
0.8828	High Similarity	NPC217083
0.8819	High Similarity	NPC172250
0.8819	High Similarity	NPC219917

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 NPC473812 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	375
0.1-0.2	969
0.2-0.3	1636
0.3-0.4	2683
0.4-0.5	1969
0.5-0.6	1020
0.6-0.7	340
0.7-0.8	111
0.8-0.85	39
0.85-0.9	8
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9097	High Similarity	NPD4378	Clinical (unspecified phase)
0.8732	High Similarity	NPD1510	Phase 2
0.8707	High Similarity	NPD7410	Clinical (unspecified phase)
0.8681	High Similarity	NPD1549	Phase 2
0.8671	High Similarity	NPD2796	Approved
0.8621	High Similarity	NPD2800	Approved
0.8611	High Similarity	NPD1550	Clinical (unspecified phase)
0.8611	High Similarity	NPD1552	Clinical (unspecified phase)
0.8582	High Similarity	NPD1240	Approved
0.8571	High Similarity	NPD7075	Discontinued
0.8523	High Similarity	NPD1512	Approved
0.8497	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8462	Intermediate Similarity	NPD1607	Approved
0.8462	Intermediate Similarity	NPD6651	Approved
0.8435	Intermediate Similarity	NPD3750	Approved
0.8421	Intermediate Similarity	NPD6599	Discontinued
0.8389	Intermediate Similarity	NPD1511	Approved
0.8389	Intermediate Similarity	NPD6799	Approved
0.8323	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8312	Intermediate Similarity	NPD6801	Discontinued
0.8301	Intermediate Similarity	NPD4380	Phase 2
0.8299	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8269	Intermediate Similarity	NPD3882	Suspended
0.8258	Intermediate Similarity	NPD7819	Suspended
0.8258	Intermediate Similarity	NPD2801	Approved
0.8258	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8247	Intermediate Similarity	NPD7411	Suspended
0.8217	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8194	Intermediate Similarity	NPD1934	Approved
0.8188	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.8163	Intermediate Similarity	NPD6100	Approved
0.8163	Intermediate Similarity	NPD6099	Approved
0.8121	Intermediate Similarity	NPD1243	Approved
0.8098	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8095	Intermediate Similarity	NPD3748	Approved
0.8089	Intermediate Similarity	NPD3817	Phase 2
0.8067	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8038	Intermediate Similarity	NPD7768	Phase 2
0.8025	Intermediate Similarity	NPD6166	Phase 2
0.8025	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8025	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD3749	Approved
0.7987	Intermediate Similarity	NPD2344	Approved
0.7987	Intermediate Similarity	NPD5403	Approved
0.7931	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7919	Intermediate Similarity	NPD1551	Phase 2
0.7914	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7881	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD5401	Approved
0.7844	Intermediate Similarity	NPD7251	Discontinued
0.784	Intermediate Similarity	NPD6959	Discontinued
0.7818	Intermediate Similarity	NPD3818	Discontinued
0.7798	Intermediate Similarity	NPD7808	Phase 3
0.7784	Intermediate Similarity	NPD6797	Phase 2
0.7778	Intermediate Similarity	NPD2309	Approved
0.7771	Intermediate Similarity	NPD7054	Approved
0.7756	Intermediate Similarity	NPD920	Approved
0.775	Intermediate Similarity	NPD5402	Approved
0.7746	Intermediate Similarity	NPD9717	Approved
0.7742	Intermediate Similarity	NPD2533	Approved
0.7742	Intermediate Similarity	NPD2532	Approved
0.7742	Intermediate Similarity	NPD2534	Approved
0.7733	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD2799	Discontinued
0.7727	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7725	Intermediate Similarity	NPD7074	Phase 3
0.7725	Intermediate Similarity	NPD7472	Approved
0.7712	Intermediate Similarity	NPD4628	Phase 3
0.7708	Intermediate Similarity	NPD1203	Approved
0.7702	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7687	Intermediate Similarity	NPD2313	Discontinued
0.7682	Intermediate Similarity	NPD2935	Discontinued
0.7679	Intermediate Similarity	NPD5953	Discontinued
0.7676	Intermediate Similarity	NPD422	Phase 1
0.7655	Intermediate Similarity	NPD2798	Approved
0.7651	Intermediate Similarity	NPD7473	Discontinued
0.7636	Intermediate Similarity	NPD3926	Phase 2
0.7628	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7607	Intermediate Similarity	NPD919	Approved
0.7588	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7588	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7584	Intermediate Similarity	NPD943	Approved
0.7576	Intermediate Similarity	NPD6232	Discontinued
0.7568	Intermediate Similarity	NPD3268	Approved
0.7561	Intermediate Similarity	NPD5494	Approved
0.756	Intermediate Similarity	NPD7286	Phase 2
0.7551	Intermediate Similarity	NPD6832	Phase 2
0.7547	Intermediate Similarity	NPD3226	Approved
0.7532	Intermediate Similarity	NPD2654	Approved
0.7515	Intermediate Similarity	NPD1247	Approved
0.75	Intermediate Similarity	NPD4308	Phase 3
0.7471	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7466	Intermediate Similarity	NPD2797	Approved
0.745	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7448	Intermediate Similarity	NPD4749	Approved
0.7432	Intermediate Similarity	NPD4908	Phase 1
0.7431	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7427	Intermediate Similarity	NPD6559	Discontinued
0.7427	Intermediate Similarity	NPD6104	Discontinued
0.7423	Intermediate Similarity	NPD4288	Approved
0.7394	Intermediate Similarity	NPD1548	Phase 1
0.7386	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD7033	Discontinued
0.7381	Intermediate Similarity	NPD2403	Approved
0.7379	Intermediate Similarity	NPD3972	Approved
0.7374	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD1465	Phase 2
0.7342	Intermediate Similarity	NPD7390	Discontinued
0.7333	Intermediate Similarity	NPD411	Approved
0.7333	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD1296	Phase 2
0.7314	Intermediate Similarity	NPD8434	Phase 2
0.731	Intermediate Similarity	NPD1610	Phase 2
0.7303	Intermediate Similarity	NPD230	Phase 1
0.7303	Intermediate Similarity	NPD447	Suspended
0.729	Intermediate Similarity	NPD1471	Phase 3
0.729	Intermediate Similarity	NPD2346	Discontinued
0.7286	Intermediate Similarity	NPD1241	Discontinued
0.7279	Intermediate Similarity	NPD3225	Approved
0.7273	Intermediate Similarity	NPD9545	Approved
0.7254	Intermediate Similarity	NPD9493	Approved
0.7251	Intermediate Similarity	NPD5844	Phase 1
0.7237	Intermediate Similarity	NPD4307	Phase 2
0.723	Intermediate Similarity	NPD3267	Approved
0.723	Intermediate Similarity	NPD3266	Approved
0.7222	Intermediate Similarity	NPD7458	Discontinued
0.7222	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD2296	Approved
0.7205	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD3751	Discontinued
0.719	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD5124	Phase 1
0.7188	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD4360	Phase 2
0.7167	Intermediate Similarity	NPD4363	Phase 3
0.716	Intermediate Similarity	NPD5710	Approved
0.716	Intermediate Similarity	NPD5711	Approved
0.7151	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1608	Approved
0.7133	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7127	Intermediate Similarity	NPD4361	Phase 2
0.7127	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD1470	Approved
0.711	Intermediate Similarity	NPD1729	Discontinued
0.7107	Intermediate Similarity	NPD2354	Approved
0.7105	Intermediate Similarity	NPD6798	Discontinued
0.7105	Intermediate Similarity	NPD3764	Approved
0.7086	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD6355	Discontinued
0.7078	Intermediate Similarity	NPD1933	Approved
0.7067	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD1019	Discontinued
0.7048	Intermediate Similarity	NPD5761	Phase 2
0.7048	Intermediate Similarity	NPD5760	Phase 2
0.7044	Intermediate Similarity	NPD7003	Approved
0.7039	Intermediate Similarity	NPD4287	Approved
0.7039	Intermediate Similarity	NPD4625	Phase 3
0.7039	Intermediate Similarity	NPD7095	Approved
0.703	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD3658	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD6844	Discontinued
0.6982	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD1008	Clinical (unspecified phase)
0.6973	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD2353	Approved
0.6962	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD1201	Approved
0.6939	Remote Similarity	NPD17	Approved
0.6939	Remote Similarity	NPD1778	Approved
0.6933	Remote Similarity	NPD5049	Phase 3
0.6933	Remote Similarity	NPD1876	Approved
0.6933	Remote Similarity	NPD8651	Approved
0.6931	Remote Similarity	NPD7584	Approved
0.6919	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD3140	Approved
0.6903	Remote Similarity	NPD3142	Approved
0.6903	Remote Similarity	NPD1613	Approved
0.6899	Remote Similarity	NPD5406	Approved
0.6899	Remote Similarity	NPD5404	Approved
0.6899	Remote Similarity	NPD5405	Approved
0.6899	Remote Similarity	NPD5408	Approved
0.6897	Remote Similarity	NPD5940	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD3887	Approved
0.6887	Remote Similarity	NPD1164	Approved
0.6886	Remote Similarity	NPD6279	Approved
0.6886	Remote Similarity	NPD6280	Approved
0.6875	Remote Similarity	NPD1652	Phase 2
0.6871	Remote Similarity	NPD7447	Phase 1
0.6867	Remote Similarity	NPD6585	Discontinued
0.686	Remote Similarity	NPD7229	Phase 3
0.686	Remote Similarity	NPD3787	Discontinued
0.6855	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD6233	Phase 2
0.6829	Remote Similarity	NPD6273	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