NPASS Compound

Structure

CID40491 OpenBabel06191715372D 35 37 0 0 0 0 0 0 0 0999 V2000 -6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 1.0000 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 -1.7321 3.0000 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 -4.3301 2.5000 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 -3.4641 3.0000 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 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 -1.7321 1.0000 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 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 2.5000 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 -2.5981 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -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 0.8660 -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 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 0.0000 -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 3.4641 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 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 -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 34 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 18 1 0 0 0 0 10 12 1 0 0 0 0 10 17 2 0 0 0 0 11 13 1 0 0 0 0 11 18 2 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 24 1 0 0 0 0 15 22 1 0 0 0 0 15 23 2 0 0 0 0 19 21 1 0 0 0 0 19 27 2 0 0 0 0 20 25 2 0 0 0 0 20 29 1 0 0 0 0 21 30 1 0 0 0 0 22 29 2 0 0 0 0 22 31 1 0 0 0 0 23 25 1 0 0 0 0 23 35 1 0 0 0 0 24 26 2 0 0 0 0 24 35 1 0 0 0 0 25 28 1 0 0 0 0 26 27 1 0 0 0 0 26 28 1 0 0 0 0 27 32 1 0 0 0 0 28 33 2 0 0 0 0 29 34 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	478.24
Volume:	510.847
LogP:	7.616
LogD:	4.237
LogS:	-2.568
# Rotatable Bonds:	8
TPSA:	100.13
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.239
Synthetic Accessibility Score:	3.887
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:	-4.925
MDCK Permeability:	1.5036142031021882e-05
Pgp-inhibitor:	0.984
Pgp-substrate:	0.738
Human Intestinal Absorption (HIA):	0.178
20% Bioavailability (F20%):	0.847
30% Bioavailability (F30%):	0.285

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.003
Plasma Protein Binding (PPB):	89.45479583740234%
Volume Distribution (VD):	1.753
Pgp-substrate:	13.420412063598633%

ADMET: Metabolism

CYP1A2-inhibitor:	0.53
CYP1A2-substrate:	0.478
CYP2C19-inhibitor:	0.913
CYP2C19-substrate:	0.102
CYP2C9-inhibitor:	0.897
CYP2C9-substrate:	0.95
CYP2D6-inhibitor:	0.739
CYP2D6-substrate:	0.451
CYP3A4-inhibitor:	0.197
CYP3A4-substrate:	0.113

ADMET: Excretion

Clearance (CL):	7.057
Half-life (T1/2):	0.132

ADMET: Toxicity

hERG Blockers:	0.141
Human Hepatotoxicity (H-HT):	0.953
Drug-inuced Liver Injury (DILI):	0.735
AMES Toxicity:	0.447
Rat Oral Acute Toxicity:	0.201
Maximum Recommended Daily Dose:	0.698
Skin Sensitization:	0.927
Carcinogencity:	0.218
Eye Corrosion:	0.003
Eye Irritation:	0.549
Respiratory Toxicity:	0.521

Download Data

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

Natural Product: NPC40491

Natural Product ID:	NPC40491
*Common Name:**	Cowanin
IUPAC Name:	1-[(2E)-3,7-dimethylocta-2,6-dienyl]-3,6,8-trihydroxy-2-methoxy-7-(3-methylbut-2-enyl)xanthen-9-one
Synonyms:	Cowanin
Standard InCHIKey:	GVDDDYKLKUMEGV-WOJGMQOQSA-N
Standard InCHI:	InChI=1S/C29H34O6/c1-16(2)8-7-9-18(5)11-13-20-25-23(15-22(31)29(20)34-6)35-24-14-21(30)19(12-10-17(3)4)27(32)26(24)28(25)33/h8,10-11,14-15,30-32H,7,9,12-13H2,1-6H3/b18-11+
SMILES:	COc1c(O)cc2c(c1C/C=C(/CCC=C(C)C)C)c(=O)c1c(o2)cc(c(c1O)CC=C(C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL458845
PubChem CID:	11754819
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	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]
NPO22337	Garcinia dulcis	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]
NPO22337	Garcinia dulcis	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
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]
NPO22337	Garcinia dulcis	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	4
Others	8

Activity Type	# Activity
Cell Line	5
Individual Protein	1
Others	5
PROTEIN FAMILY	4

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[551915]
NPT80	Cell Line	Raji	Homo sapiens	Activity	>	80.0	%	PMID[551915]
NPT156	Individual Protein	Sphingomyelin phosphodiesterase	Homo sapiens	IC50	=	19200.0	nM	PMID[551916]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	11680.0	nM	PMID[551917]
NPT2	Others	Unspecified		Inhibition	=	0.0	%	PMID[551915]
NPT2	Others	Unspecified		Inhibition	=	33.6	%	PMID[551915]
NPT2	Others	Unspecified		Inhibition	=	71.6	%	PMID[551915]
NPT2	Others	Unspecified		Inhibition	=	95.8	%	PMID[551915]
NPT2	Others	Unspecified		IC50	=	320.0	molar ratio	PMID[551915]
NPT20648	PROTEIN FAMILY	Alpha glucosidase	Homo sapiens	IC50	=	37400.0	nM	PMID[551918]

☑ 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 NPC40491 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	454
0.1-0.2	1784
0.2-0.3	4235
0.3-0.4	10504
0.4-0.5	7733
0.5-0.6	3576
0.6-0.7	4973
0.7-0.8	5229
0.8-0.85	2414
0.85-0.9	1126
0.9-0.95	589
0.95-1	80

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC278052
0.9934	High Similarity	NPC228785
0.9934	High Similarity	NPC320359
0.9934	High Similarity	NPC14353
0.9934	High Similarity	NPC56085
0.987	High Similarity	NPC236132
0.987	High Similarity	NPC7483
0.9869	High Similarity	NPC61010
0.9868	High Similarity	NPC100123
0.9804	High Similarity	NPC475886
0.9804	High Similarity	NPC474287
0.9803	High Similarity	NPC165977
0.9803	High Similarity	NPC236796
0.9803	High Similarity	NPC241904
0.9803	High Similarity	NPC300727
0.9803	High Similarity	NPC217677
0.9744	High Similarity	NPC39091
0.9742	High Similarity	NPC236521
0.9742	High Similarity	NPC152659
0.9742	High Similarity	NPC220313
0.9742	High Similarity	NPC248638
0.974	High Similarity	NPC474186
0.974	High Similarity	NPC474187
0.974	High Similarity	NPC474351
0.974	High Similarity	NPC475883
0.9739	High Similarity	NPC476242
0.9737	High Similarity	NPC142339
0.9737	High Similarity	NPC274730
0.9679	High Similarity	NPC326520
0.9679	High Similarity	NPC472450
0.9679	High Similarity	NPC239752
0.9679	High Similarity	NPC275780
0.9677	High Similarity	NPC25152
0.9675	High Similarity	NPC119224
0.9673	High Similarity	NPC78225
0.9673	High Similarity	NPC36852
0.9673	High Similarity	NPC262286
0.9618	High Similarity	NPC170245
0.9615	High Similarity	NPC23298
0.9615	High Similarity	NPC189473
0.9615	High Similarity	NPC270837
0.9613	High Similarity	NPC32694
0.9608	High Similarity	NPC191146
0.9608	High Similarity	NPC68093
0.9608	High Similarity	NPC138243
0.9605	High Similarity	NPC89474
0.9557	High Similarity	NPC6588
0.9557	High Similarity	NPC477154
0.9557	High Similarity	NPC117854
0.9551	High Similarity	NPC229632
0.9551	High Similarity	NPC294965
0.9551	High Similarity	NPC201800
0.9548	High Similarity	NPC235018
0.9548	High Similarity	NPC45146
0.9548	High Similarity	NPC200746
0.9548	High Similarity	NPC36217
0.9545	High Similarity	NPC136674
0.9545	High Similarity	NPC223787
0.9545	High Similarity	NPC469584
0.9542	High Similarity	NPC113906
0.9494	High Similarity	NPC472449
0.9494	High Similarity	NPC37870
0.949	High Similarity	NPC475985
0.949	High Similarity	NPC41301
0.949	High Similarity	NPC197168
0.949	High Similarity	NPC146134
0.949	High Similarity	NPC474350
0.9487	High Similarity	NPC66288
0.9487	High Similarity	NPC266314
0.9484	High Similarity	NPC329091
0.9484	High Similarity	NPC250214
0.9484	High Similarity	NPC235448
0.9484	High Similarity	NPC95936
0.9484	High Similarity	NPC210459
0.9481	High Similarity	NPC470328
0.9481	High Similarity	NPC209614
0.9481	High Similarity	NPC472626
0.9474	High Similarity	NPC202157
0.943	High Similarity	NPC473286
0.943	High Similarity	NPC25361
0.943	High Similarity	NPC293319
0.943	High Similarity	NPC475888
0.9427	High Similarity	NPC211107
0.9427	High Similarity	NPC470694
0.9427	High Similarity	NPC83922
0.9427	High Similarity	NPC472448
0.9427	High Similarity	NPC329760
0.9427	High Similarity	NPC52204
0.9423	High Similarity	NPC321399
0.9423	High Similarity	NPC299436
0.9423	High Similarity	NPC471973
0.9423	High Similarity	NPC139036
0.9423	High Similarity	NPC476980
0.9423	High Similarity	NPC246478
0.9423	High Similarity	NPC80375
0.9423	High Similarity	NPC204290
0.9419	High Similarity	NPC474836
0.9419	High Similarity	NPC472910
0.9419	High Similarity	NPC472914
0.9419	High Similarity	NPC48208
0.9419	High Similarity	NPC222814
0.9419	High Similarity	NPC472963
0.9419	High Similarity	NPC472913
0.9419	High Similarity	NPC156057
0.9419	High Similarity	NPC245758
0.9419	High Similarity	NPC96167
0.9419	High Similarity	NPC474208
0.9419	High Similarity	NPC162869
0.9419	High Similarity	NPC472911
0.9419	High Similarity	NPC475267
0.9416	High Similarity	NPC117992
0.9416	High Similarity	NPC230149
0.9416	High Similarity	NPC45849
0.9416	High Similarity	NPC200761
0.9416	High Similarity	NPC470327
0.9416	High Similarity	NPC57674
0.9416	High Similarity	NPC168247
0.9416	High Similarity	NPC152951
0.9416	High Similarity	NPC477503
0.9412	High Similarity	NPC101996
0.9412	High Similarity	NPC249570
0.9412	High Similarity	NPC471982
0.9412	High Similarity	NPC120537
0.9412	High Similarity	NPC199100
0.9412	High Similarity	NPC180234
0.9408	High Similarity	NPC151473
0.9367	High Similarity	NPC207690
0.9367	High Similarity	NPC186686
0.9367	High Similarity	NPC474240
0.9363	High Similarity	NPC278427
0.9363	High Similarity	NPC29876
0.9363	High Similarity	NPC167678
0.9363	High Similarity	NPC258331
0.9363	High Similarity	NPC472275
0.9359	High Similarity	NPC474290
0.9359	High Similarity	NPC172770
0.9359	High Similarity	NPC85121
0.9359	High Similarity	NPC185258
0.9355	High Similarity	NPC278778
0.9355	High Similarity	NPC472916
0.9355	High Similarity	NPC472907
0.9355	High Similarity	NPC291878
0.9355	High Similarity	NPC255106
0.9355	High Similarity	NPC195796
0.9355	High Similarity	NPC235165
0.9355	High Similarity	NPC13779
0.9355	High Similarity	NPC35038
0.9355	High Similarity	NPC475799
0.9351	High Similarity	NPC33051
0.9351	High Similarity	NPC271779
0.9351	High Similarity	NPC227337
0.9351	High Similarity	NPC88645
0.9351	High Similarity	NPC276409
0.9351	High Similarity	NPC70433
0.9351	High Similarity	NPC231018
0.9351	High Similarity	NPC49402
0.9351	High Similarity	NPC250822
0.9351	High Similarity	NPC298692
0.9351	High Similarity	NPC255350
0.9351	High Similarity	NPC206238
0.9351	High Similarity	NPC176775
0.9351	High Similarity	NPC476631
0.9351	High Similarity	NPC292214
0.9351	High Similarity	NPC183878
0.9351	High Similarity	NPC75279
0.9351	High Similarity	NPC69394
0.9351	High Similarity	NPC47781
0.9351	High Similarity	NPC273462
0.9351	High Similarity	NPC160951
0.9351	High Similarity	NPC22519
0.9351	High Similarity	NPC145379
0.9351	High Similarity	NPC167091
0.9351	High Similarity	NPC274327
0.9346	High Similarity	NPC117579
0.9346	High Similarity	NPC171010
0.9313	High Similarity	NPC126204
0.9313	High Similarity	NPC218226
0.9308	High Similarity	NPC39306
0.9304	High Similarity	NPC81679
0.9304	High Similarity	NPC474150
0.9304	High Similarity	NPC472964
0.9304	High Similarity	NPC474162
0.9299	High Similarity	NPC472630
0.9299	High Similarity	NPC472631
0.9299	High Similarity	NPC84571
0.9295	High Similarity	NPC79053
0.9295	High Similarity	NPC299520
0.9295	High Similarity	NPC291508
0.9295	High Similarity	NPC129684
0.9295	High Similarity	NPC474055
0.9295	High Similarity	NPC476981
0.9295	High Similarity	NPC99597
0.9295	High Similarity	NPC27337
0.9295	High Similarity	NPC181960
0.9295	High Similarity	NPC187745
0.9295	High Similarity	NPC273843
0.9295	High Similarity	NPC180011
0.9295	High Similarity	NPC219867
0.9295	High Similarity	NPC161960
0.9295	High Similarity	NPC304008

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 NPC40491 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	969
0.2-0.3	1827
0.3-0.4	2723
0.4-0.5	1751
0.5-0.6	911
0.6-0.7	402
0.7-0.8	123
0.8-0.85	28
0.85-0.9	15
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9351	High Similarity	NPD2801	Approved
0.9226	High Similarity	NPD2393	Clinical (unspecified phase)
0.9161	High Similarity	NPD1934	Approved
0.882	High Similarity	NPD5494	Approved
0.878	High Similarity	NPD7473	Discontinued
0.8766	High Similarity	NPD1511	Approved
0.875	High Similarity	NPD3882	Suspended
0.872	High Similarity	NPD6167	Clinical (unspecified phase)
0.872	High Similarity	NPD6166	Phase 2
0.872	High Similarity	NPD6168	Clinical (unspecified phase)
0.8712	High Similarity	NPD6232	Discontinued
0.8654	High Similarity	NPD1512	Approved
0.8625	High Similarity	NPD7819	Suspended
0.8623	High Similarity	NPD7074	Phase 3
0.859	High Similarity	NPD4378	Clinical (unspecified phase)
0.8563	High Similarity	NPD7054	Approved
0.8563	High Similarity	NPD5844	Phase 1
0.8519	High Similarity	NPD4868	Clinical (unspecified phase)
0.8512	High Similarity	NPD7472	Approved
0.8509	High Similarity	NPD1465	Phase 2
0.8503	High Similarity	NPD3818	Discontinued
0.8471	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8466	Intermediate Similarity	NPD7075	Discontinued
0.8457	Intermediate Similarity	NPD3817	Phase 2
0.8438	Intermediate Similarity	NPD4380	Phase 2
0.8424	Intermediate Similarity	NPD6959	Discontinued
0.8395	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8344	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8304	Intermediate Similarity	NPD7251	Discontinued
0.8258	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8258	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8256	Intermediate Similarity	NPD7808	Phase 3
0.8246	Intermediate Similarity	NPD6797	Phase 2
0.8205	Intermediate Similarity	NPD1549	Phase 2
0.8133	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8129	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD2533	Approved
0.8125	Intermediate Similarity	NPD2532	Approved
0.8125	Intermediate Similarity	NPD2534	Approved
0.8095	Intermediate Similarity	NPD1247	Approved
0.8089	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8079	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8049	Intermediate Similarity	NPD7411	Suspended
0.8038	Intermediate Similarity	NPD2800	Approved
0.8035	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8013	Intermediate Similarity	NPD1510	Phase 2
0.8	Intermediate Similarity	NPD6801	Discontinued
0.7987	Intermediate Similarity	NPD1240	Approved
0.7987	Intermediate Similarity	NPD943	Approved
0.7978	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7962	Intermediate Similarity	NPD2796	Approved
0.7962	Intermediate Similarity	NPD2935	Discontinued
0.795	Intermediate Similarity	NPD6799	Approved
0.7917	Intermediate Similarity	NPD3749	Approved
0.7904	Intermediate Similarity	NPD5402	Approved
0.7898	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD3926	Phase 2
0.7889	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7886	Intermediate Similarity	NPD6559	Discontinued
0.7885	Intermediate Similarity	NPD1607	Approved
0.7879	Intermediate Similarity	NPD6599	Discontinued
0.7875	Intermediate Similarity	NPD3750	Approved
0.787	Intermediate Similarity	NPD6234	Discontinued
0.7857	Intermediate Similarity	NPD7768	Phase 2
0.7849	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7848	Intermediate Similarity	NPD6100	Approved
0.7848	Intermediate Similarity	NPD6099	Approved
0.7843	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7818	Intermediate Similarity	NPD3226	Approved
0.7799	Intermediate Similarity	NPD2346	Discontinued
0.7785	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7765	Intermediate Similarity	NPD919	Approved
0.7759	Intermediate Similarity	NPD7228	Approved
0.7756	Intermediate Similarity	NPD1613	Approved
0.7756	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD7390	Discontinued
0.7709	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7707	Intermediate Similarity	NPD230	Phase 1
0.7679	Intermediate Similarity	NPD37	Approved
0.7674	Intermediate Similarity	NPD7199	Phase 2
0.7658	Intermediate Similarity	NPD6651	Approved
0.7657	Intermediate Similarity	NPD3751	Discontinued
0.7647	Intermediate Similarity	NPD4966	Approved
0.7647	Intermediate Similarity	NPD4965	Approved
0.7647	Intermediate Similarity	NPD4967	Phase 2
0.763	Intermediate Similarity	NPD5711	Approved
0.763	Intermediate Similarity	NPD5710	Approved
0.763	Intermediate Similarity	NPD3787	Discontinued
0.7598	Intermediate Similarity	NPD8312	Approved
0.7598	Intermediate Similarity	NPD8313	Approved
0.7595	Intermediate Similarity	NPD447	Suspended
0.7593	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7564	Intermediate Similarity	NPD3027	Phase 3
0.7562	Intermediate Similarity	NPD3748	Approved
0.7562	Intermediate Similarity	NPD2799	Discontinued
0.7546	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD7286	Phase 2
0.75	Intermediate Similarity	NPD6781	Approved
0.75	Intermediate Similarity	NPD6777	Approved
0.75	Intermediate Similarity	NPD6776	Approved
0.75	Intermediate Similarity	NPD6782	Approved
0.75	Intermediate Similarity	NPD6780	Approved
0.75	Intermediate Similarity	NPD6778	Approved
0.75	Intermediate Similarity	NPD6779	Approved
0.7485	Intermediate Similarity	NPD1243	Approved
0.7485	Intermediate Similarity	NPD5403	Approved
0.7485	Intermediate Similarity	NPD920	Approved
0.7474	Intermediate Similarity	NPD7435	Discontinued
0.7473	Intermediate Similarity	NPD8150	Discontinued
0.7469	Intermediate Similarity	NPD2344	Approved
0.7461	Intermediate Similarity	NPD8151	Discontinued
0.7452	Intermediate Similarity	NPD4625	Phase 3
0.7444	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD1653	Approved
0.7439	Intermediate Similarity	NPD4628	Phase 3
0.743	Intermediate Similarity	NPD5953	Discontinued
0.7429	Intermediate Similarity	NPD7229	Phase 3
0.741	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD1551	Phase 2
0.7405	Intermediate Similarity	NPD2313	Discontinued
0.7405	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7385	Intermediate Similarity	NPD7783	Phase 2
0.7385	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7382	Intermediate Similarity	NPD7697	Approved
0.7382	Intermediate Similarity	NPD7698	Approved
0.7382	Intermediate Similarity	NPD7696	Phase 3
0.7377	Intermediate Similarity	NPD8434	Phase 2
0.7375	Intermediate Similarity	NPD1933	Approved
0.7365	Intermediate Similarity	NPD5401	Approved
0.7365	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7344	Intermediate Similarity	NPD7871	Phase 2
0.7344	Intermediate Similarity	NPD7870	Phase 2
0.733	Intermediate Similarity	NPD6823	Phase 2
0.7325	Intermediate Similarity	NPD9494	Approved
0.732	Intermediate Similarity	NPD7701	Phase 2
0.7293	Intermediate Similarity	NPD7685	Pre-registration
0.7293	Intermediate Similarity	NPD7240	Approved
0.729	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD6190	Approved
0.7289	Intermediate Similarity	NPD2309	Approved
0.7278	Intermediate Similarity	NPD4908	Phase 1
0.7246	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7245	Intermediate Similarity	NPD7874	Approved
0.7245	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD6535	Approved
0.7234	Intermediate Similarity	NPD6534	Approved
0.7234	Intermediate Similarity	NPD4360	Phase 2
0.7234	Intermediate Similarity	NPD4363	Phase 3
0.7229	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD7700	Phase 2
0.7211	Intermediate Similarity	NPD7699	Phase 2
0.7209	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD7801	Approved
0.7205	Intermediate Similarity	NPD4060	Phase 1
0.7197	Intermediate Similarity	NPD1470	Approved
0.7193	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7191	Intermediate Similarity	NPD5242	Approved
0.7184	Intermediate Similarity	NPD5353	Approved
0.7174	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD6674	Discontinued
0.7168	Intermediate Similarity	NPD6844	Discontinued
0.7161	Intermediate Similarity	NPD1610	Phase 2
0.7161	Intermediate Similarity	NPD1201	Approved
0.7158	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD2403	Approved
0.7115	Intermediate Similarity	NPD9269	Phase 2
0.7107	Intermediate Similarity	NPD2861	Phase 2
0.7093	Intermediate Similarity	NPD7458	Discontinued
0.7092	Intermediate Similarity	NPD7584	Approved
0.7091	Intermediate Similarity	NPD5405	Approved
0.7091	Intermediate Similarity	NPD5404	Approved
0.7091	Intermediate Similarity	NPD5408	Approved
0.7091	Intermediate Similarity	NPD5406	Approved
0.7089	Intermediate Similarity	NPD1203	Approved
0.7081	Intermediate Similarity	NPD3268	Approved
0.7081	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD4749	Approved
0.7066	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD6832	Phase 2
0.7059	Intermediate Similarity	NPD7907	Approved
0.7059	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD1471	Phase 3
0.7044	Intermediate Similarity	NPD2798	Approved
0.7029	Intermediate Similarity	NPD8455	Phase 2
0.7021	Intermediate Similarity	NPD4287	Approved
0.7018	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7016	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7016	Intermediate Similarity	NPD4361	Phase 2
0.7011	Intermediate Similarity	NPD6385	Approved
0.7011	Intermediate Similarity	NPD6386	Approved
0.701	Intermediate Similarity	NPD2493	Approved
0.701	Intermediate Similarity	NPD2494	Approved
0.7006	Intermediate Similarity	NPD2424	Discontinued

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