NPASS Compound

Structure

CID39091 OpenBabel06191715372D 35 38 0 0 0 0 0 0 0 0999 V2000 9.5263 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3923 5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3660 -0.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 3.0000 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 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -0.0000 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 9.5263 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 4.5000 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 5.1962 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 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 4.3301 0.5000 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 4.3301 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 2.0000 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 6.0622 1.5000 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 6.9282 -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 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 2.0000 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 0.0000 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 29 1 0 0 0 0 5 29 1 0 0 0 0 6 33 1 0 0 0 0 7 8 1 0 0 0 0 7 9 1 0 0 0 0 8 16 2 0 0 0 0 9 17 1 0 0 0 0 10 11 1 0 0 0 0 10 17 2 0 0 0 0 11 19 1 0 0 0 0 12 13 2 0 0 0 0 12 18 1 0 0 0 0 13 29 1 0 0 0 0 14 20 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 18 21 1 0 0 0 0 18 26 2 0 0 0 0 19 24 2 0 0 0 0 19 28 1 0 0 0 0 20 28 2 0 0 0 0 20 30 1 0 0 0 0 21 35 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 27 1 0 0 0 0 25 26 1 0 0 0 0 25 27 1 0 0 0 0 26 31 1 0 0 0 0 27 32 2 0 0 0 0 28 33 1 0 0 0 0 29 35 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	476.22
Volume:	502.291
LogP:	7.503
LogD:	4.781
LogS:	-2.561
# Rotatable Bonds:	6
TPSA:	89.13
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.296
Synthetic Accessibility Score:	3.999
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:	-4.902
MDCK Permeability:	1.4264352103054989e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.046
20% Bioavailability (F20%):	0.012
30% Bioavailability (F30%):	0.018

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.005
Plasma Protein Binding (PPB):	95.60459899902344%
Volume Distribution (VD):	0.807
Pgp-substrate:	8.691019058227539%

ADMET: Metabolism

CYP1A2-inhibitor:	0.51
CYP1A2-substrate:	0.664
CYP2C19-inhibitor:	0.912
CYP2C19-substrate:	0.284
CYP2C9-inhibitor:	0.92
CYP2C9-substrate:	0.945
CYP2D6-inhibitor:	0.877
CYP2D6-substrate:	0.638
CYP3A4-inhibitor:	0.389
CYP3A4-substrate:	0.18

ADMET: Excretion

Clearance (CL):	1.711
Half-life (T1/2):	0.085

ADMET: Toxicity

hERG Blockers:	0.335
Human Hepatotoxicity (H-HT):	0.966
Drug-inuced Liver Injury (DILI):	0.938
AMES Toxicity:	0.367
Rat Oral Acute Toxicity:	0.475
Maximum Recommended Daily Dose:	0.835
Skin Sensitization:	0.841
Carcinogencity:	0.793
Eye Corrosion:	0.003
Eye Irritation:	0.138
Respiratory Toxicity:	0.751

Download Data

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

Natural Product: NPC39091

Natural Product ID:	NPC39091
*Common Name:**	Fuscaxanthone A
IUPAC Name:	7-[(2E)-3,7-dimethylocta-2,6-dienyl]-5,9-dihydroxy-8-methoxy-2,2-dimethylpyrano[3,2-b]xanthen-6-one
Synonyms:
Standard InCHIKey:	XDMFZDJOFFBFDK-LICLKQGHSA-N
Standard InCHI:	InChI=1S/C29H32O6/c1-16(2)8-7-9-17(3)10-11-19-24-22(14-20(30)28(19)33-6)34-23-15-21-18(12-13-29(4,5)35-21)26(31)25(23)27(24)32/h8,10,12-15,30-31H,7,9,11H2,1-6H3/b17-10+
SMILES:	COc1c(O)cc2c(c1C/C=C(/CCC=C(C)C)C)c(=O)c1c(o2)cc2c(c1O)C=CC(O2)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3421661
PubChem CID:	5324264
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]
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	young fruits	Khokkhon, Tha Bo District, Nong Khai Province, Thailand	2011-Aug	PMID[25651042]
NPO25472	Garcinia cowa	Species	Clusiaceae	Eukaryota	flowers	Pakook, Muang District, Chiang Rai Province, Thailand	2013-Feb	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]
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	1

Activity Type	# Activity
Organism	6
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		Inhibition	=	71.7	%	PMID[506751]
NPT2	Others	Unspecified		IC50	=	18600.0	nM	PMID[506751]
NPT314	Organism	Bacillus cereus	Bacillus cereus	MIC	=	64.0	ug.mL-1	PMID[506751]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	64.0	ug.mL-1	PMID[506751]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	128.0	ug.mL-1	PMID[506751]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	64.0	ug.mL-1	PMID[506751]
NPT566	Organism	Salmonella typhimurium	Salmonella enterica subsp. enterica serovar Typhimurium	MIC	=	128.0	ug.mL-1	PMID[506751]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	=	128.0	ug.mL-1	PMID[506751]

☑ 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 NPC39091 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	459
0.1-0.2	1779
0.2-0.3	4088
0.3-0.4	10480
0.4-0.5	7767
0.5-0.6	3569
0.6-0.7	5138
0.7-0.8	5131
0.8-0.85	2535
0.85-0.9	1165
0.9-0.95	515
0.95-1	71

Similarity Score	Similarity Level	Natural Product ID
0.9936	High Similarity	NPC239752
0.9936	High Similarity	NPC275780
0.9936	High Similarity	NPC472450
0.9872	High Similarity	NPC189473
0.9872	High Similarity	NPC23298
0.9808	High Similarity	NPC229632
0.9747	High Similarity	NPC472449
0.9747	High Similarity	NPC37870
0.9745	High Similarity	NPC236521
0.9745	High Similarity	NPC152659
0.9745	High Similarity	NPC248638
0.9744	High Similarity	NPC61010
0.9744	High Similarity	NPC278052
0.9744	High Similarity	NPC40491
0.9682	High Similarity	NPC83922
0.9682	High Similarity	NPC25152
0.9682	High Similarity	NPC472448
0.9682	High Similarity	NPC329760
0.9679	High Similarity	NPC14353
0.9679	High Similarity	NPC56085
0.9679	High Similarity	NPC204290
0.9679	High Similarity	NPC320359
0.9679	High Similarity	NPC139036
0.9679	High Similarity	NPC228785
0.9679	High Similarity	NPC471973
0.962	High Similarity	NPC220313
0.962	High Similarity	NPC207690
0.962	High Similarity	NPC236132
0.962	High Similarity	NPC186686
0.962	High Similarity	NPC7483
0.9618	High Similarity	NPC167678
0.9618	High Similarity	NPC474187
0.9618	High Similarity	NPC29876
0.9615	High Similarity	NPC100123
0.9615	High Similarity	NPC474290
0.9615	High Similarity	NPC476242
0.9563	High Similarity	NPC218226
0.9563	High Similarity	NPC6588
0.9563	High Similarity	NPC117854
0.9563	High Similarity	NPC477154
0.956	High Similarity	NPC293319
0.9557	High Similarity	NPC474150
0.9557	High Similarity	NPC474162
0.9554	High Similarity	NPC476980
0.9554	High Similarity	NPC475886
0.9554	High Similarity	NPC474287
0.9554	High Similarity	NPC200746
0.9551	High Similarity	NPC78225
0.9551	High Similarity	NPC217677
0.9551	High Similarity	NPC241904
0.9551	High Similarity	NPC300727
0.9551	High Similarity	NPC236796
0.9551	High Similarity	NPC165977
0.9551	High Similarity	NPC136674
0.95	High Similarity	NPC170245
0.95	High Similarity	NPC43319
0.9497	High Similarity	NPC270837
0.9497	High Similarity	NPC306321
0.9497	High Similarity	NPC146134
0.9497	High Similarity	NPC303460
0.9494	High Similarity	NPC474351
0.9494	High Similarity	NPC474186
0.9494	High Similarity	NPC475883
0.9494	High Similarity	NPC32694
0.9494	High Similarity	NPC259456
0.949	High Similarity	NPC204879
0.9487	High Similarity	NPC191146
0.9487	High Similarity	NPC68093
0.9487	High Similarity	NPC142339
0.9487	High Similarity	NPC274730
0.9441	High Similarity	NPC126204
0.9437	High Similarity	NPC326520
0.9434	High Similarity	NPC201800
0.9434	High Similarity	NPC261470
0.9434	High Similarity	NPC52204
0.9434	High Similarity	NPC294965
0.943	High Similarity	NPC474960
0.943	High Similarity	NPC235018
0.943	High Similarity	NPC119209
0.943	High Similarity	NPC45146
0.943	High Similarity	NPC36217
0.943	High Similarity	NPC119224
0.943	High Similarity	NPC80375
0.943	High Similarity	NPC118256
0.943	High Similarity	NPC192686
0.9427	High Similarity	NPC476981
0.9427	High Similarity	NPC218313
0.9427	High Similarity	NPC474681
0.9427	High Similarity	NPC218871
0.9427	High Similarity	NPC36852
0.9427	High Similarity	NPC476630
0.9427	High Similarity	NPC472963
0.9427	High Similarity	NPC262286
0.9383	High Similarity	NPC476637
0.9379	High Similarity	NPC120593
0.9375	High Similarity	NPC41301
0.9375	High Similarity	NPC475985
0.9371	High Similarity	NPC266314
0.9371	High Similarity	NPC258331
0.9371	High Similarity	NPC471210
0.9371	High Similarity	NPC57715
0.9371	High Similarity	NPC66288
0.9371	High Similarity	NPC278427
0.9371	High Similarity	NPC474038
0.9371	High Similarity	NPC234644
0.9367	High Similarity	NPC95936
0.9367	High Similarity	NPC235448
0.9367	High Similarity	NPC250214
0.9367	High Similarity	NPC210459
0.9363	High Similarity	NPC138243
0.9363	High Similarity	NPC472455
0.9363	High Similarity	NPC133970
0.9363	High Similarity	NPC276444
0.9363	High Similarity	NPC5322
0.9363	High Similarity	NPC6633
0.9363	High Similarity	NPC472907
0.9363	High Similarity	NPC471985
0.9359	High Similarity	NPC183878
0.9359	High Similarity	NPC231018
0.9359	High Similarity	NPC280530
0.9359	High Similarity	NPC178964
0.9359	High Similarity	NPC95842
0.9359	High Similarity	NPC176775
0.9359	High Similarity	NPC69394
0.9359	High Similarity	NPC47781
0.9359	High Similarity	NPC160951
0.9359	High Similarity	NPC22519
0.9359	High Similarity	NPC255350
0.9359	High Similarity	NPC89474
0.9359	High Similarity	NPC145379
0.9359	High Similarity	NPC274327
0.9329	High Similarity	NPC310794
0.9325	High Similarity	NPC472276
0.9325	High Similarity	NPC101107
0.9317	High Similarity	NPC50960
0.9317	High Similarity	NPC224280
0.9317	High Similarity	NPC62261
0.9317	High Similarity	NPC156432
0.9317	High Similarity	NPC303174
0.9313	High Similarity	NPC472964
0.9313	High Similarity	NPC472402
0.9308	High Similarity	NPC321399
0.9308	High Similarity	NPC188433
0.9308	High Similarity	NPC246478
0.9308	High Similarity	NPC299436
0.9308	High Similarity	NPC475784
0.9304	High Similarity	NPC472914
0.9304	High Similarity	NPC245758
0.9304	High Similarity	NPC27337
0.9304	High Similarity	NPC156057
0.9304	High Similarity	NPC162869
0.9304	High Similarity	NPC284820
0.9304	High Similarity	NPC222814
0.9304	High Similarity	NPC475267
0.9304	High Similarity	NPC474208
0.9304	High Similarity	NPC472913
0.9304	High Similarity	NPC472910
0.9304	High Similarity	NPC472911
0.9304	High Similarity	NPC273843
0.9304	High Similarity	NPC48208
0.9304	High Similarity	NPC469584
0.9304	High Similarity	NPC473272
0.9304	High Similarity	NPC474836
0.9304	High Similarity	NPC96167
0.9304	High Similarity	NPC52889
0.9304	High Similarity	NPC223787
0.9299	High Similarity	NPC117992
0.9299	High Similarity	NPC57674
0.9299	High Similarity	NPC167815
0.9299	High Similarity	NPC128863
0.9299	High Similarity	NPC4455
0.9299	High Similarity	NPC472280
0.9299	High Similarity	NPC200246
0.9299	High Similarity	NPC92659
0.9299	High Similarity	NPC234255
0.9299	High Similarity	NPC20830
0.9299	High Similarity	NPC227325
0.9299	High Similarity	NPC183597
0.9299	High Similarity	NPC163780
0.9299	High Similarity	NPC2476
0.9299	High Similarity	NPC256612
0.9299	High Similarity	NPC201136
0.9299	High Similarity	NPC138360
0.9299	High Similarity	NPC196439
0.9299	High Similarity	NPC152951
0.9299	High Similarity	NPC113906
0.9299	High Similarity	NPC230149
0.9299	High Similarity	NPC280339
0.9299	High Similarity	NPC213622
0.9299	High Similarity	NPC168247
0.9299	High Similarity	NPC50715
0.9299	High Similarity	NPC146165
0.9299	High Similarity	NPC256925
0.9295	High Similarity	NPC199100
0.9295	High Similarity	NPC256283
0.9295	High Similarity	NPC249570
0.9295	High Similarity	NPC100887
0.9295	High Similarity	NPC241498
0.9295	High Similarity	NPC471982
0.9295	High Similarity	NPC71334

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 NPC39091 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	399
0.1-0.2	970
0.2-0.3	1780
0.3-0.4	2703
0.4-0.5	1788
0.5-0.6	926
0.6-0.7	407
0.7-0.8	127
0.8-0.85	33
0.85-0.9	16
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9359	High Similarity	NPD2801	Approved
0.9114	High Similarity	NPD2393	Clinical (unspecified phase)
0.9051	High Similarity	NPD1934	Approved
0.8834	High Similarity	NPD5494	Approved
0.8782	High Similarity	NPD1511	Approved
0.8735	High Similarity	NPD6166	Phase 2
0.8735	High Similarity	NPD6167	Clinical (unspecified phase)
0.8735	High Similarity	NPD6168	Clinical (unspecified phase)
0.869	High Similarity	NPD7054	Approved
0.8683	High Similarity	NPD7473	Discontinued
0.8671	High Similarity	NPD1512	Approved
0.865	High Similarity	NPD3882	Suspended
0.8639	High Similarity	NPD7074	Phase 3
0.8639	High Similarity	NPD7472	Approved
0.8614	High Similarity	NPD6232	Discontinued
0.8608	High Similarity	NPD4378	Clinical (unspecified phase)
0.8596	High Similarity	NPD4338	Clinical (unspecified phase)
0.858	High Similarity	NPD5844	Phase 1
0.8571	High Similarity	NPD4380	Phase 2
0.8528	High Similarity	NPD7819	Suspended
0.8521	High Similarity	NPD3818	Discontinued
0.8476	Intermediate Similarity	NPD3817	Phase 2
0.843	Intermediate Similarity	NPD7251	Discontinued
0.8424	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8415	Intermediate Similarity	NPD1465	Phase 2
0.8382	Intermediate Similarity	NPD7808	Phase 3
0.8375	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8373	Intermediate Similarity	NPD7075	Discontinued
0.8372	Intermediate Similarity	NPD6797	Phase 2
0.8364	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD6959	Discontinued
0.8303	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8263	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8256	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8165	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8165	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8118	Intermediate Similarity	NPD1247	Approved
0.8113	Intermediate Similarity	NPD1549	Phase 2
0.8101	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8072	Intermediate Similarity	NPD7411	Suspended
0.8047	Intermediate Similarity	NPD3749	Approved
0.8038	Intermediate Similarity	NPD1510	Phase 2
0.8036	Intermediate Similarity	NPD5402	Approved
0.8024	Intermediate Similarity	NPD6801	Discontinued
0.8012	Intermediate Similarity	NPD3750	Approved
0.8011	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD2796	Approved
0.7955	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7927	Intermediate Similarity	NPD2533	Approved
0.7927	Intermediate Similarity	NPD2532	Approved
0.7927	Intermediate Similarity	NPD2534	Approved
0.7903	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7898	Intermediate Similarity	NPD943	Approved
0.7898	Intermediate Similarity	NPD1240	Approved
0.7882	Intermediate Similarity	NPD7768	Phase 2
0.7875	Intermediate Similarity	NPD2935	Discontinued
0.7874	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7866	Intermediate Similarity	NPD6799	Approved
0.784	Intermediate Similarity	NPD2800	Approved
0.7833	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7816	Intermediate Similarity	NPD3926	Phase 2
0.7809	Intermediate Similarity	NPD6559	Discontinued
0.7799	Intermediate Similarity	NPD1607	Approved
0.7798	Intermediate Similarity	NPD6599	Discontinued
0.7791	Intermediate Similarity	NPD919	Approved
0.7784	Intermediate Similarity	NPD3751	Discontinued
0.7764	Intermediate Similarity	NPD6099	Approved
0.7764	Intermediate Similarity	NPD6100	Approved
0.7759	Intermediate Similarity	NPD3787	Discontinued
0.7756	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7738	Intermediate Similarity	NPD3226	Approved
0.7716	Intermediate Similarity	NPD2346	Discontinued
0.7702	Intermediate Similarity	NPD3748	Approved
0.7702	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7702	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD6234	Discontinued
0.7684	Intermediate Similarity	NPD7228	Approved
0.7673	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7673	Intermediate Similarity	NPD1613	Approved
0.7651	Intermediate Similarity	NPD7390	Discontinued
0.7624	Intermediate Similarity	NPD8312	Approved
0.7624	Intermediate Similarity	NPD8313	Approved
0.7619	Intermediate Similarity	NPD5403	Approved
0.7619	Intermediate Similarity	NPD6781	Approved
0.7619	Intermediate Similarity	NPD6780	Approved
0.7619	Intermediate Similarity	NPD6782	Approved
0.7619	Intermediate Similarity	NPD6776	Approved
0.7619	Intermediate Similarity	NPD6779	Approved
0.7619	Intermediate Similarity	NPD6778	Approved
0.7619	Intermediate Similarity	NPD6777	Approved
0.76	Intermediate Similarity	NPD7199	Phase 2
0.7596	Intermediate Similarity	NPD8150	Discontinued
0.7592	Intermediate Similarity	NPD7435	Discontinued
0.7516	Intermediate Similarity	NPD447	Suspended
0.7516	Intermediate Similarity	NPD230	Phase 1
0.7515	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD920	Approved
0.7514	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD7685	Pre-registration
0.75	Intermediate Similarity	NPD7698	Approved
0.75	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7783	Phase 2
0.75	Intermediate Similarity	NPD37	Approved
0.75	Intermediate Similarity	NPD5401	Approved
0.75	Intermediate Similarity	NPD7696	Phase 3
0.75	Intermediate Similarity	NPD7697	Approved
0.7485	Intermediate Similarity	NPD2799	Discontinued
0.7484	Intermediate Similarity	NPD4625	Phase 3
0.7484	Intermediate Similarity	NPD3027	Phase 3
0.7473	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD1653	Approved
0.7471	Intermediate Similarity	NPD4965	Approved
0.7471	Intermediate Similarity	NPD4967	Phase 2
0.7471	Intermediate Similarity	NPD4966	Approved
0.747	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7469	Intermediate Similarity	NPD6651	Approved
0.7461	Intermediate Similarity	NPD7870	Phase 2
0.7461	Intermediate Similarity	NPD7871	Phase 2
0.7458	Intermediate Similarity	NPD5710	Approved
0.7458	Intermediate Similarity	NPD5711	Approved
0.7448	Intermediate Similarity	NPD6823	Phase 2
0.7444	Intermediate Similarity	NPD7286	Phase 2
0.7438	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD2313	Discontinued
0.7436	Intermediate Similarity	NPD7701	Phase 2
0.741	Intermediate Similarity	NPD1243	Approved
0.7405	Intermediate Similarity	NPD8434	Phase 2
0.7398	Intermediate Similarity	NPD8151	Discontinued
0.7396	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD2344	Approved
0.7365	Intermediate Similarity	NPD4628	Phase 3
0.7363	Intermediate Similarity	NPD5953	Discontinued
0.736	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD7874	Approved
0.736	Intermediate Similarity	NPD7229	Phase 3
0.7354	Intermediate Similarity	NPD6535	Approved
0.7354	Intermediate Similarity	NPD4360	Phase 2
0.7354	Intermediate Similarity	NPD4363	Phase 3
0.7354	Intermediate Similarity	NPD6534	Approved
0.7337	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD1551	Phase 2
0.733	Intermediate Similarity	NPD7699	Phase 2
0.733	Intermediate Similarity	NPD7700	Phase 2
0.7323	Intermediate Similarity	NPD7801	Approved
0.7321	Intermediate Similarity	NPD6190	Approved
0.7312	Intermediate Similarity	NPD4908	Phase 1
0.7301	Intermediate Similarity	NPD1933	Approved
0.7299	Intermediate Similarity	NPD6844	Discontinued
0.7296	Intermediate Similarity	NPD7584	Approved
0.7278	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7277	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD9494	Approved
0.7228	Intermediate Similarity	NPD7240	Approved
0.7225	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD2309	Approved
0.7215	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7189	Intermediate Similarity	NPD7549	Discontinued
0.7171	Intermediate Similarity	NPD7907	Approved
0.7143	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4287	Approved
0.7134	Intermediate Similarity	NPD4060	Phase 1
0.7128	Intermediate Similarity	NPD2493	Approved
0.7128	Intermediate Similarity	NPD2494	Approved
0.7127	Intermediate Similarity	NPD5242	Approved
0.7126	Intermediate Similarity	NPD5405	Approved
0.7126	Intermediate Similarity	NPD5406	Approved
0.7126	Intermediate Similarity	NPD5404	Approved
0.7126	Intermediate Similarity	NPD7458	Discontinued
0.7126	Intermediate Similarity	NPD5408	Approved
0.7125	Intermediate Similarity	NPD1470	Approved
0.7119	Intermediate Similarity	NPD4288	Approved
0.7117	Intermediate Similarity	NPD3268	Approved
0.7101	Intermediate Similarity	NPD6674	Discontinued
0.7093	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD5124	Phase 1
0.7091	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD1201	Approved
0.7089	Intermediate Similarity	NPD1610	Phase 2
0.7088	Intermediate Similarity	NPD2403	Approved
0.7081	Intermediate Similarity	NPD2798	Approved
0.7076	Intermediate Similarity	NPD3300	Phase 2
0.7073	Intermediate Similarity	NPD4111	Phase 1
0.7073	Intermediate Similarity	NPD4665	Approved
0.7066	Intermediate Similarity	NPD7033	Discontinued
0.7062	Intermediate Similarity	NPD8455	Phase 2
0.7047	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD4361	Phase 2
0.7041	Intermediate Similarity	NPD2424	Discontinued
0.7041	Intermediate Similarity	NPD3450	Approved
0.7041	Intermediate Similarity	NPD3452	Approved
0.7037	Intermediate Similarity	NPD2861	Phase 2
0.7031	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD6213	Phase 3
0.7031	Intermediate Similarity	NPD6212	Phase 3

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