NPASS Compound

Structure

NPC229632 OpenBabel07101718282D 31 34 0 0 0 0 0 0 0 0999 V2000 -5.1962 -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 1.8660 -0.5000 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 -6.9282 1.0000 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 -4.3301 -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 -1.7321 0.0000 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 -4.3301 -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 -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 -6.0622 -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 -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 0.0000 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 13 1 0 0 0 0 2 13 1 0 0 0 0 3 25 1 0 0 0 0 4 25 1 0 0 0 0 5 28 1 0 0 0 0 6 29 1 0 0 0 0 7 8 1 0 0 0 0 7 13 2 0 0 0 0 8 15 1 0 0 0 0 9 10 2 0 0 0 0 9 14 1 0 0 0 0 10 25 1 0 0 0 0 11 16 2 0 0 0 0 11 18 1 0 0 0 0 12 17 2 0 0 0 0 12 19 1 0 0 0 0 14 16 1 0 0 0 0 14 22 2 0 0 0 0 15 20 2 0 0 0 0 15 24 1 0 0 0 0 16 31 1 0 0 0 0 17 20 1 0 0 0 0 17 30 1 0 0 0 0 18 21 2 0 0 0 0 18 30 1 0 0 0 0 19 24 2 0 0 0 0 19 28 1 0 0 0 0 20 23 1 0 0 0 0 21 22 1 0 0 0 0 21 23 1 0 0 0 0 22 26 1 0 0 0 0 23 27 2 0 0 0 0 24 29 1 0 0 0 0 25 31 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	422.17
Volume:	435.743
LogP:	6.263
LogD:	3.795
LogS:	-3.361
# Rotatable Bonds:	4
TPSA:	78.13
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.45
Synthetic Accessibility Score:	3.199
Fsp3:	0.32
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.756
MDCK Permeability:	1.6241659977822565e-05
Pgp-inhibitor:	0.997
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.115
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.014

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.013
Plasma Protein Binding (PPB):	80.88256072998047%
Volume Distribution (VD):	0.891
Pgp-substrate:	17.803834915161133%

ADMET: Metabolism

CYP1A2-inhibitor:	0.23
CYP1A2-substrate:	0.916
CYP2C19-inhibitor:	0.895
CYP2C19-substrate:	0.504
CYP2C9-inhibitor:	0.904
CYP2C9-substrate:	0.928
CYP2D6-inhibitor:	0.455
CYP2D6-substrate:	0.558
CYP3A4-inhibitor:	0.453
CYP3A4-substrate:	0.217

ADMET: Excretion

Clearance (CL):	2.332
Half-life (T1/2):	0.124

ADMET: Toxicity

hERG Blockers:	0.021
Human Hepatotoxicity (H-HT):	0.939
Drug-inuced Liver Injury (DILI):	0.87
AMES Toxicity:	0.298
Rat Oral Acute Toxicity:	0.547
Maximum Recommended Daily Dose:	0.482
Skin Sensitization:	0.472
Carcinogencity:	0.558
Eye Corrosion:	0.003
Eye Irritation:	0.051
Respiratory Toxicity:	0.811

Download Data

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

Natural Product: NPC229632

Natural Product ID:	NPC229632
*Common Name:**	XMZHFNRJGBRHGV-UHFFFAOYSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	XMZHFNRJGBRHGV-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C25H26O6/c1-13(2)7-8-15-20-17(12-19(28-5)24(15)29-6)30-18-11-16-14(9-10-25(3,4)31-16)22(26)21(18)23(20)27/h7,9-12,26H,8H2,1-6H3
SMILES:	COc1cc2oc3cc4OC(C)(C)C=Cc4c(c3c(=O)c2c(c1OC)CC=C(C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3421660
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 [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	=	62.2	%	PMID[550403]
NPT2	Others	Unspecified		IC50	=	26200.0	nM	PMID[550403]
NPT314	Organism	Bacillus cereus	Bacillus cereus	MIC	=	128.0	ug.mL-1	PMID[550403]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	128.0	ug.mL-1	PMID[550403]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	128.0	ug.mL-1	PMID[550403]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	128.0	ug.mL-1	PMID[550403]
NPT566	Organism	Salmonella typhimurium	Salmonella enterica subsp. enterica serovar Typhimurium	MIC	=	64.0	ug.mL-1	PMID[550403]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	=	128.0	ug.mL-1	PMID[550403]

☑ 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 NPC229632 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	453
0.1-0.2	1836
0.2-0.3	4222
0.3-0.4	10730
0.4-0.5	7360
0.5-0.6	3487
0.6-0.7	5095
0.7-0.8	5002
0.8-0.85	2582
0.85-0.9	1387
0.9-0.95	481
0.95-1	62

Similarity Score	Similarity Level	Natural Product ID
0.9871	High Similarity	NPC239752
0.9871	High Similarity	NPC275780
0.9871	High Similarity	NPC472450
0.9808	High Similarity	NPC39091
0.9806	High Similarity	NPC189473
0.9806	High Similarity	NPC23298
0.9739	High Similarity	NPC165977
0.9739	High Similarity	NPC217677
0.9682	High Similarity	NPC472449
0.9682	High Similarity	NPC37870
0.9679	High Similarity	NPC152659
0.9679	High Similarity	NPC248638
0.9679	High Similarity	NPC236521
0.9677	High Similarity	NPC61010
0.9677	High Similarity	NPC474187
0.9615	High Similarity	NPC329760
0.9615	High Similarity	NPC25152
0.9615	High Similarity	NPC472448
0.9615	High Similarity	NPC83922
0.9615	High Similarity	NPC52204
0.9613	High Similarity	NPC204290
0.9613	High Similarity	NPC475886
0.9613	High Similarity	NPC139036
0.9613	High Similarity	NPC228785
0.9613	High Similarity	NPC474287
0.9613	High Similarity	NPC471973
0.9613	High Similarity	NPC56085
0.9613	High Similarity	NPC14353
0.961	High Similarity	NPC476981
0.9557	High Similarity	NPC120593
0.9554	High Similarity	NPC186686
0.9554	High Similarity	NPC220313
0.9554	High Similarity	NPC207690
0.9551	High Similarity	NPC278052
0.9551	High Similarity	NPC29876
0.9551	High Similarity	NPC167678
0.9551	High Similarity	NPC66288
0.9551	High Similarity	NPC474186
0.9551	High Similarity	NPC40491
0.9551	High Similarity	NPC474351
0.9551	High Similarity	NPC475883
0.9548	High Similarity	NPC100123
0.9548	High Similarity	NPC474290
0.9548	High Similarity	NPC476242
0.9542	High Similarity	NPC280530
0.9542	High Similarity	NPC178964
0.9542	High Similarity	NPC95842
0.9497	High Similarity	NPC477154
0.9497	High Similarity	NPC6588
0.9497	High Similarity	NPC117854
0.949	High Similarity	NPC474162
0.949	High Similarity	NPC474150
0.9487	High Similarity	NPC476980
0.9487	High Similarity	NPC320359
0.9487	High Similarity	NPC200746
0.9484	High Similarity	NPC284820
0.9484	High Similarity	NPC241904
0.9484	High Similarity	NPC300727
0.9484	High Similarity	NPC78225
0.9484	High Similarity	NPC136674
0.9484	High Similarity	NPC473272
0.9434	High Similarity	NPC43319
0.9434	High Similarity	NPC170245
0.9434	High Similarity	NPC272502
0.943	High Similarity	NPC306321
0.943	High Similarity	NPC303460
0.943	High Similarity	NPC197168
0.943	High Similarity	NPC236132
0.943	High Similarity	NPC146134
0.943	High Similarity	NPC7483
0.943	High Similarity	NPC474350
0.943	High Similarity	NPC270837
0.9427	High Similarity	NPC32694
0.9427	High Similarity	NPC40037
0.9427	High Similarity	NPC259456
0.9423	High Similarity	NPC204879
0.9419	High Similarity	NPC191146
0.9419	High Similarity	NPC274730
0.9419	High Similarity	NPC68093
0.9419	High Similarity	NPC142339
0.9412	High Similarity	NPC226973
0.9412	High Similarity	NPC208043
0.9412	High Similarity	NPC117579
0.9375	High Similarity	NPC218226
0.9371	High Similarity	NPC25361
0.9371	High Similarity	NPC293319
0.9371	High Similarity	NPC326520
0.9367	High Similarity	NPC472402
0.9367	High Similarity	NPC294965
0.9367	High Similarity	NPC261470
0.9363	High Similarity	NPC235018
0.9363	High Similarity	NPC192686
0.9363	High Similarity	NPC45146
0.9363	High Similarity	NPC299436
0.9363	High Similarity	NPC80375
0.9363	High Similarity	NPC118256
0.9363	High Similarity	NPC475784
0.9363	High Similarity	NPC119209
0.9363	High Similarity	NPC36217
0.9363	High Similarity	NPC474960
0.9359	High Similarity	NPC218313
0.9359	High Similarity	NPC181960
0.9359	High Similarity	NPC262286
0.9359	High Similarity	NPC36852
0.9359	High Similarity	NPC236796
0.9359	High Similarity	NPC474681
0.9355	High Similarity	NPC37392
0.9355	High Similarity	NPC166054
0.9355	High Similarity	NPC472909
0.9355	High Similarity	NPC55662
0.9351	High Similarity	NPC166201
0.9346	High Similarity	NPC227122
0.9346	High Similarity	NPC306821
0.9321	High Similarity	NPC223375
0.9321	High Similarity	NPC475825
0.9317	High Similarity	NPC476637
0.9317	High Similarity	NPC177480
0.9308	High Similarity	NPC273959
0.9308	High Similarity	NPC475985
0.9308	High Similarity	NPC41301
0.9304	High Similarity	NPC57715
0.9304	High Similarity	NPC234644
0.9304	High Similarity	NPC266314
0.9304	High Similarity	NPC258331
0.9304	High Similarity	NPC474038
0.9299	High Similarity	NPC152904
0.9299	High Similarity	NPC250214
0.9299	High Similarity	NPC95936
0.9299	High Similarity	NPC235448
0.9295	High Similarity	NPC471985
0.9295	High Similarity	NPC6633
0.9295	High Similarity	NPC276444
0.9295	High Similarity	NPC472455
0.9295	High Similarity	NPC133970
0.9295	High Similarity	NPC138243
0.9295	High Similarity	NPC5322
0.929	High Similarity	NPC86485
0.929	High Similarity	NPC280937
0.929	High Similarity	NPC47781
0.929	High Similarity	NPC183878
0.929	High Similarity	NPC89474
0.929	High Similarity	NPC22519
0.929	High Similarity	NPC472915
0.929	High Similarity	NPC160951
0.929	High Similarity	NPC231018
0.929	High Similarity	NPC255350
0.929	High Similarity	NPC472408
0.929	High Similarity	NPC145379
0.929	High Similarity	NPC69394
0.929	High Similarity	NPC274327
0.929	High Similarity	NPC176775
0.9286	High Similarity	NPC308451
0.9286	High Similarity	NPC149614
0.9281	High Similarity	NPC328119
0.9264	High Similarity	NPC310794
0.9259	High Similarity	NPC472276
0.9259	High Similarity	NPC101107
0.9255	High Similarity	NPC126204
0.9255	High Similarity	NPC8965
0.925	High Similarity	NPC156432
0.925	High Similarity	NPC234052
0.925	High Similarity	NPC224280
0.925	High Similarity	NPC62261
0.925	High Similarity	NPC303174
0.925	High Similarity	NPC50960
0.9245	High Similarity	NPC201800
0.9241	High Similarity	NPC188433
0.9241	High Similarity	NPC246478
0.9241	High Similarity	NPC119224
0.9236	High Similarity	NPC475267
0.9236	High Similarity	NPC222814
0.9236	High Similarity	NPC156057
0.9236	High Similarity	NPC218871
0.9236	High Similarity	NPC472910
0.9236	High Similarity	NPC245758
0.9236	High Similarity	NPC474836
0.9236	High Similarity	NPC469584
0.9236	High Similarity	NPC27337
0.9236	High Similarity	NPC48208
0.9236	High Similarity	NPC474208
0.9236	High Similarity	NPC52889
0.9236	High Similarity	NPC472911
0.9236	High Similarity	NPC96167
0.9236	High Similarity	NPC162869
0.9236	High Similarity	NPC476630
0.9236	High Similarity	NPC472963
0.9236	High Similarity	NPC472914
0.9236	High Similarity	NPC472913
0.9236	High Similarity	NPC223787
0.9231	High Similarity	NPC230149
0.9231	High Similarity	NPC256612
0.9231	High Similarity	NPC168247
0.9231	High Similarity	NPC256925
0.9231	High Similarity	NPC92659
0.9231	High Similarity	NPC128863
0.9231	High Similarity	NPC200246
0.9231	High Similarity	NPC31018
0.9231	High Similarity	NPC20830
0.9231	High Similarity	NPC183597
0.9231	High Similarity	NPC50715

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 NPC229632 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	400
0.1-0.2	992
0.2-0.3	1719
0.3-0.4	2685
0.4-0.5	1803
0.5-0.6	937
0.6-0.7	432
0.7-0.8	130
0.8-0.85	34
0.85-0.9	17
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.929	High Similarity	NPD2801	Approved
0.9045	High Similarity	NPD2393	Clinical (unspecified phase)
0.9	High Similarity	NPD5494	Approved
0.8981	High Similarity	NPD1934	Approved
0.8774	High Similarity	NPD4378	Clinical (unspecified phase)
0.8773	High Similarity	NPD6232	Discontinued
0.8735	High Similarity	NPD5844	Phase 1
0.8727	High Similarity	NPD7473	Discontinued
0.871	High Similarity	NPD1511	Approved
0.8667	High Similarity	NPD6166	Phase 2
0.8667	High Similarity	NPD6167	Clinical (unspecified phase)
0.8667	High Similarity	NPD6168	Clinical (unspecified phase)
0.8616	High Similarity	NPD4380	Phase 2
0.8599	High Similarity	NPD1512	Approved
0.858	High Similarity	NPD3882	Suspended
0.8571	High Similarity	NPD7819	Suspended
0.8535	High Similarity	NPD7410	Clinical (unspecified phase)
0.8529	High Similarity	NPD4338	Clinical (unspecified phase)
0.8519	High Similarity	NPD3817	Phase 2
0.8512	High Similarity	NPD7054	Approved
0.8485	Intermediate Similarity	NPD6959	Discontinued
0.8462	Intermediate Similarity	NPD7472	Approved
0.8462	Intermediate Similarity	NPD7074	Phase 3
0.8452	Intermediate Similarity	NPD3818	Discontinued
0.8405	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8354	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8344	Intermediate Similarity	NPD1465	Phase 2
0.8323	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8323	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8314	Intermediate Similarity	NPD7808	Phase 3
0.8304	Intermediate Similarity	NPD6797	Phase 2
0.8303	Intermediate Similarity	NPD7075	Discontinued
0.8303	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8269	Intermediate Similarity	NPD1549	Phase 2
0.8263	Intermediate Similarity	NPD1247	Approved
0.8256	Intermediate Similarity	NPD7251	Discontinued
0.8232	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8221	Intermediate Similarity	NPD7411	Suspended
0.8194	Intermediate Similarity	NPD1510	Phase 2
0.8193	Intermediate Similarity	NPD3749	Approved
0.8187	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8165	Intermediate Similarity	NPD3750	Approved
0.8153	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8141	Intermediate Similarity	NPD2796	Approved
0.8075	Intermediate Similarity	NPD2534	Approved
0.8075	Intermediate Similarity	NPD2533	Approved
0.8075	Intermediate Similarity	NPD2532	Approved
0.8072	Intermediate Similarity	NPD5402	Approved
0.8061	Intermediate Similarity	NPD6801	Discontinued
0.8052	Intermediate Similarity	NPD1240	Approved
0.8025	Intermediate Similarity	NPD2935	Discontinued
0.8012	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD2800	Approved
0.7953	Intermediate Similarity	NPD3926	Phase 2
0.7949	Intermediate Similarity	NPD1607	Approved
0.7944	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7935	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7933	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7929	Intermediate Similarity	NPD919	Approved
0.7917	Intermediate Similarity	NPD7768	Phase 2
0.7901	Intermediate Similarity	NPD6799	Approved
0.7886	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7879	Intermediate Similarity	NPD3226	Approved
0.7862	Intermediate Similarity	NPD2346	Discontinued
0.7848	Intermediate Similarity	NPD3748	Approved
0.7848	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7841	Intermediate Similarity	NPD6559	Discontinued
0.7831	Intermediate Similarity	NPD6599	Discontinued
0.7821	Intermediate Similarity	NPD943	Approved
0.7816	Intermediate Similarity	NPD3751	Discontinued
0.7799	Intermediate Similarity	NPD6100	Approved
0.7799	Intermediate Similarity	NPD6099	Approved
0.7791	Intermediate Similarity	NPD3787	Discontinued
0.7791	Intermediate Similarity	NPD7390	Discontinued
0.7677	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7658	Intermediate Similarity	NPD447	Suspended
0.7654	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD920	Approved
0.7651	Intermediate Similarity	NPD5403	Approved
0.7647	Intermediate Similarity	NPD6777	Approved
0.7647	Intermediate Similarity	NPD6778	Approved
0.7647	Intermediate Similarity	NPD6779	Approved
0.7647	Intermediate Similarity	NPD6776	Approved
0.7647	Intermediate Similarity	NPD6782	Approved
0.7647	Intermediate Similarity	NPD6780	Approved
0.7647	Intermediate Similarity	NPD6781	Approved
0.7633	Intermediate Similarity	NPD37	Approved
0.763	Intermediate Similarity	NPD7199	Phase 2
0.7628	Intermediate Similarity	NPD4625	Phase 3
0.7625	Intermediate Similarity	NPD2799	Discontinued
0.7625	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD6234	Discontinued
0.7613	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7602	Intermediate Similarity	NPD4965	Approved
0.7602	Intermediate Similarity	NPD4967	Phase 2
0.7602	Intermediate Similarity	NPD4966	Approved
0.7598	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD1613	Approved
0.7595	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD5711	Approved
0.7586	Intermediate Similarity	NPD5710	Approved
0.758	Intermediate Similarity	NPD2313	Discontinued
0.758	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7556	Intermediate Similarity	NPD8312	Approved
0.7556	Intermediate Similarity	NPD8313	Approved
0.7546	Intermediate Similarity	NPD1243	Approved
0.7543	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD2344	Approved
0.753	Intermediate Similarity	NPD5401	Approved
0.753	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7527	Intermediate Similarity	NPD8150	Discontinued
0.7526	Intermediate Similarity	NPD7696	Phase 3
0.7526	Intermediate Similarity	NPD7697	Approved
0.7526	Intermediate Similarity	NPD7698	Approved
0.7526	Intermediate Similarity	NPD7435	Discontinued
0.7514	Intermediate Similarity	NPD7228	Approved
0.75	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6651	Approved
0.7487	Intermediate Similarity	NPD7870	Phase 2
0.7487	Intermediate Similarity	NPD7871	Phase 2
0.7486	Intermediate Similarity	NPD5953	Discontinued
0.7473	Intermediate Similarity	NPD4363	Phase 3
0.7473	Intermediate Similarity	NPD4360	Phase 2
0.7472	Intermediate Similarity	NPD7286	Phase 2
0.747	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7469	Intermediate Similarity	NPD1551	Phase 2
0.7468	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD4908	Phase 1
0.7438	Intermediate Similarity	NPD230	Phase 1
0.7438	Intermediate Similarity	NPD1933	Approved
0.7436	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD7783	Phase 2
0.7425	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD3027	Phase 3
0.7396	Intermediate Similarity	NPD1653	Approved
0.7394	Intermediate Similarity	NPD4628	Phase 3
0.7394	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD7229	Phase 3
0.7382	Intermediate Similarity	NPD6823	Phase 2
0.738	Intermediate Similarity	NPD6534	Approved
0.738	Intermediate Similarity	NPD6535	Approved
0.7371	Intermediate Similarity	NPD7701	Phase 2
0.7353	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD2309	Approved
0.7348	Intermediate Similarity	NPD7685	Pre-registration
0.7337	Intermediate Similarity	NPD8434	Phase 2
0.7333	Intermediate Similarity	NPD8151	Discontinued
0.7326	Intermediate Similarity	NPD6844	Discontinued
0.7308	Intermediate Similarity	NPD7549	Discontinued
0.7296	Intermediate Similarity	NPD7874	Approved
0.7296	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD7699	Phase 2
0.7263	Intermediate Similarity	NPD7700	Phase 2
0.7261	Intermediate Similarity	NPD1470	Approved
0.7259	Intermediate Similarity	NPD7801	Approved
0.7258	Intermediate Similarity	NPD4287	Approved
0.7256	Intermediate Similarity	NPD5404	Approved
0.7256	Intermediate Similarity	NPD5406	Approved
0.7256	Intermediate Similarity	NPD5405	Approved
0.7256	Intermediate Similarity	NPD5408	Approved
0.725	Intermediate Similarity	NPD3268	Approved
0.7247	Intermediate Similarity	NPD5242	Approved
0.7246	Intermediate Similarity	NPD6190	Approved
0.7241	Intermediate Similarity	NPD4288	Approved
0.7231	Intermediate Similarity	NPD7584	Approved
0.7226	Intermediate Similarity	NPD1610	Phase 2
0.7226	Intermediate Similarity	NPD1201	Approved
0.7222	Intermediate Similarity	NPD5124	Phase 1
0.7222	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD2798	Approved
0.7211	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD2403	Approved
0.7195	Intermediate Similarity	NPD7033	Discontinued
0.717	Intermediate Similarity	NPD9494	Approved
0.717	Intermediate Similarity	NPD2861	Phase 2
0.7168	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD4060	Phase 1
0.7158	Intermediate Similarity	NPD4361	Phase 2
0.7158	Intermediate Similarity	NPD7240	Approved
0.7158	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD1203	Approved
0.7152	Intermediate Similarity	NPD2797	Approved
0.7151	Intermediate Similarity	NPD7458	Discontinued
0.7143	Intermediate Similarity	NPD3764	Approved
0.7134	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD4749	Approved
0.7115	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD1471	Phase 3
0.7101	Intermediate Similarity	NPD3300	Phase 2
0.7091	Intermediate Similarity	NPD4308	Phase 3
0.7083	Intermediate Similarity	NPD7003	Approved
0.7078	Intermediate Similarity	NPD1548	Phase 1
0.7076	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD1608	Approved
0.7066	Intermediate Similarity	NPD2424	Discontinued
0.7062	Intermediate Similarity	NPD2493	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