NPASS Compound

Structure

NPC475886 OpenBabel07101718182D 34 36 0 0 0 0 0 0 0 0999 V2000 -4.3301 -0.5000 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 -5.1962 1.0000 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 1.7321 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 -4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 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 -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 -4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -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 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 2.5981 -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 -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 -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 -0.0000 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 8 1 0 0 0 0 2 9 1 0 0 0 0 3 16 1 0 0 0 0 4 16 1 0 0 0 0 5 17 1 0 0 0 0 6 17 1 0 0 0 0 7 31 1 0 0 0 0 8 32 1 0 0 0 0 9 33 1 0 0 0 0 10 12 1 0 0 0 0 10 16 2 0 0 0 0 11 13 1 0 0 0 0 11 17 2 0 0 0 0 12 18 1 0 0 0 0 13 19 1 0 0 0 0 14 20 2 0 0 0 0 14 22 1 0 0 0 0 15 21 2 0 0 0 0 15 23 1 0 0 0 0 18 20 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 32 1 0 0 0 0 21 24 1 0 0 0 0 21 34 1 0 0 0 0 22 25 2 0 0 0 0 22 34 1 0 0 0 0 23 28 2 0 0 0 0 23 33 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 29 1 0 0 0 0 27 30 2 0 0 0 0 28 31 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	466.24
Volume:	496.188
LogP:	6.898
LogD:	4.689
LogS:	-5.52
# Rotatable Bonds:	9
TPSA:	78.13
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.281
Synthetic Accessibility Score:	3.184
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:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.858
MDCK Permeability:	1.5593943317071535e-05
Pgp-inhibitor:	0.997
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.046
30% Bioavailability (F30%):	0.008

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.01
Plasma Protein Binding (PPB):	90.4253158569336%
Volume Distribution (VD):	1.395
Pgp-substrate:	12.898977279663086%

ADMET: Metabolism

CYP1A2-inhibitor:	0.173
CYP1A2-substrate:	0.811
CYP2C19-inhibitor:	0.882
CYP2C19-substrate:	0.485
CYP2C9-inhibitor:	0.924
CYP2C9-substrate:	0.935
CYP2D6-inhibitor:	0.241
CYP2D6-substrate:	0.781
CYP3A4-inhibitor:	0.225
CYP3A4-substrate:	0.187

ADMET: Excretion

Clearance (CL):	2.2
Half-life (T1/2):	0.077

ADMET: Toxicity

hERG Blockers:	0.11
Human Hepatotoxicity (H-HT):	0.55
Drug-inuced Liver Injury (DILI):	0.596
AMES Toxicity:	0.415
Rat Oral Acute Toxicity:	0.076
Maximum Recommended Daily Dose:	0.086
Skin Sensitization:	0.43
Carcinogencity:	0.188
Eye Corrosion:	0.003
Eye Irritation:	0.179
Respiratory Toxicity:	0.279

Download Data

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

Natural Product: NPC475886

Natural Product ID:	NPC475886
*Common Name:**	Di-O-Ethylmangostin
IUPAC Name:	3,6-diethoxy-1-hydroxy-7-methoxy-2,8-bis(3-methylbut-2-enyl)xanthen-9-one
Synonyms:	Di-O-Ethylmangostin
Standard InCHIKey:	URKKQYOYBPWWGJ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C28H34O6/c1-8-32-20-14-22-25(26(29)18(20)12-10-16(3)4)27(30)24-19(13-11-17(5)6)28(31-7)23(33-9-2)15-21(24)34-22/h10-11,14-15,29H,8-9,12-13H2,1-7H3
SMILES:	CCOc1cc2oc3cc(OCC)c(c(c3c(=O)c2c(c1CC=C(C)C)O)CC=C(C)C)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL517940
PubChem CID:	10671899
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
NPO6249	Garcinia mangostana	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18464091]
NPO6249	Garcinia mangostana	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18558747]
NPO6249	Garcinia mangostana	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19299148]
NPO6249	Garcinia mangostana	Species	Clusiaceae	Eukaryota	stem bark	Pangradin village, Jasinga, West Java, Indonesia	2005-AUG	PMID[19839614]
NPO6249	Garcinia mangostana	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20817450]
NPO6249	Garcinia mangostana	Species	Clusiaceae	Eukaryota	n.a.	pericarp	n.a.	PMID[24555285]
NPO6249	Garcinia mangostana	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24717154]
NPO6249	Garcinia mangostana	Species	Clusiaceae	Eukaryota	fruit hulls	Madras, Tamil Nadu, India	1993-MAR	PMID[9213587]
NPO6249	Garcinia mangostana	Species	Clusiaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO6249	Garcinia mangostana	Species	Clusiaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO6249	Garcinia mangostana	Species	Clusiaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO6249	Garcinia mangostana	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6249	Garcinia mangostana	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6249	Garcinia mangostana	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
Others	12

Activity Type	# Activity
Organism	12

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2646	Organism	Alternaria tenuis	Alternaria tenuis	Inhibition	=	-4.0	%	PMID[496871]
NPT2646	Organism	Alternaria tenuis	Alternaria tenuis	Inhibition	=	4.0	%	PMID[496871]
NPT2646	Organism	Alternaria tenuis	Alternaria tenuis	Inhibition	=	-11.0	%	PMID[496871]
NPT2646	Organism	Alternaria tenuis	Alternaria tenuis	Inhibition	=	-1.0	%	PMID[496871]
NPT2647	Organism	Drechslera	Drechslera	Inhibition	=	-72.0	%	PMID[496871]
NPT2647	Organism	Drechslera	Drechslera	Inhibition	=	-34.0	%	PMID[496871]
NPT2647	Organism	Drechslera	Drechslera	Inhibition	=	-31.0	%	PMID[496871]
NPT2647	Organism	Drechslera	Drechslera	Inhibition	=	-57.0	%	PMID[496871]
NPT2648	Organism	Fusarium oxysporum f. sp. vasinfectum	Fusarium oxysporum f. sp. vasinfectum	Inhibition	=	-3.0	%	PMID[496871]
NPT2648	Organism	Fusarium oxysporum f. sp. vasinfectum	Fusarium oxysporum f. sp. vasinfectum	Inhibition	=	-2.0	%	PMID[496871]
NPT2648	Organism	Fusarium oxysporum f. sp. vasinfectum	Fusarium oxysporum f. sp. vasinfectum	Inhibition	=	-1.0	%	PMID[496871]

☑ 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 NPC475886 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	429
0.1-0.2	1761
0.2-0.3	4195
0.3-0.4	10463
0.4-0.5	7781
0.5-0.6	3465
0.6-0.7	4920
0.7-0.8	5081
0.8-0.85	2560
0.85-0.9	1423
0.9-0.95	560
0.95-1	59

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC474287
0.9934	High Similarity	NPC475883
0.9934	High Similarity	NPC474351
0.9934	High Similarity	NPC474186
0.9934	High Similarity	NPC474187
0.9868	High Similarity	NPC217677
0.9868	High Similarity	NPC165977
0.9805	High Similarity	NPC7483
0.9804	High Similarity	NPC278052
0.9804	High Similarity	NPC40491
0.9739	High Similarity	NPC320359
0.9739	High Similarity	NPC56085
0.9739	High Similarity	NPC14353
0.9739	High Similarity	NPC228785
0.9677	High Similarity	NPC197168
0.9677	High Similarity	NPC236132
0.9675	High Similarity	NPC61010
0.9673	High Similarity	NPC100123
0.9615	High Similarity	NPC25361
0.9615	High Similarity	NPC326520
0.9613	High Similarity	NPC229632
0.961	High Similarity	NPC299436
0.9608	High Similarity	NPC236796
0.9608	High Similarity	NPC300727
0.9608	High Similarity	NPC241904
0.9554	High Similarity	NPC39091
0.9554	High Similarity	NPC170245
0.9551	High Similarity	NPC236521
0.9551	High Similarity	NPC220313
0.9551	High Similarity	NPC474350
0.9551	High Similarity	NPC152659
0.9551	High Similarity	NPC248638
0.9548	High Similarity	NPC66288
0.9545	High Similarity	NPC476242
0.9542	High Similarity	NPC274730
0.9542	High Similarity	NPC142339
0.9494	High Similarity	NPC477154
0.9494	High Similarity	NPC6588
0.9494	High Similarity	NPC117854
0.949	High Similarity	NPC239752
0.949	High Similarity	NPC472450
0.949	High Similarity	NPC275780
0.9487	High Similarity	NPC52204
0.9487	High Similarity	NPC25152
0.9487	High Similarity	NPC201800
0.9484	High Similarity	NPC36217
0.9484	High Similarity	NPC119224
0.9481	High Similarity	NPC223787
0.9481	High Similarity	NPC78225
0.9481	High Similarity	NPC469584
0.9481	High Similarity	NPC181960
0.9481	High Similarity	NPC36852
0.9481	High Similarity	NPC262286
0.9477	High Similarity	NPC472909
0.9477	High Similarity	NPC37392
0.9477	High Similarity	NPC226025
0.9427	High Similarity	NPC270837
0.9427	High Similarity	NPC41301
0.9427	High Similarity	NPC474240
0.9427	High Similarity	NPC23298
0.9427	High Similarity	NPC475985
0.9427	High Similarity	NPC273959
0.9427	High Similarity	NPC189473
0.9423	High Similarity	NPC32694
0.9423	High Similarity	NPC266314
0.9419	High Similarity	NPC210459
0.9419	High Similarity	NPC95936
0.9419	High Similarity	NPC250214
0.9419	High Similarity	NPC329091
0.9416	High Similarity	NPC209614
0.9416	High Similarity	NPC191146
0.9416	High Similarity	NPC138243
0.9416	High Similarity	NPC472626
0.9416	High Similarity	NPC470328
0.9416	High Similarity	NPC68093
0.9412	High Similarity	NPC472915
0.9412	High Similarity	NPC89474
0.9412	High Similarity	NPC280937
0.9408	High Similarity	NPC117579
0.9367	High Similarity	NPC293319
0.9367	High Similarity	NPC473286
0.9367	High Similarity	NPC475888
0.9363	High Similarity	NPC211107
0.9363	High Similarity	NPC294965
0.9359	High Similarity	NPC200746
0.9359	High Similarity	NPC235018
0.9359	High Similarity	NPC321399
0.9359	High Similarity	NPC45146
0.9355	High Similarity	NPC136674
0.9355	High Similarity	NPC475267
0.9355	High Similarity	NPC472911
0.9355	High Similarity	NPC472910
0.9355	High Similarity	NPC96167
0.9355	High Similarity	NPC476981
0.9355	High Similarity	NPC474836
0.9355	High Similarity	NPC472914
0.9355	High Similarity	NPC156057
0.9355	High Similarity	NPC245758
0.9355	High Similarity	NPC162869
0.9355	High Similarity	NPC472913
0.9355	High Similarity	NPC48208
0.9355	High Similarity	NPC222814
0.9355	High Similarity	NPC474208
0.9351	High Similarity	NPC477503
0.9351	High Similarity	NPC255807
0.9351	High Similarity	NPC45849
0.9351	High Similarity	NPC200761
0.9351	High Similarity	NPC470327
0.9351	High Similarity	NPC31018
0.9351	High Similarity	NPC113906
0.9342	High Similarity	NPC179183
0.9342	High Similarity	NPC227122
0.9342	High Similarity	NPC338131
0.9308	High Similarity	NPC472449
0.9308	High Similarity	NPC120593
0.9308	High Similarity	NPC37870
0.9304	High Similarity	NPC186686
0.9304	High Similarity	NPC146134
0.9299	High Similarity	NPC474239
0.9295	High Similarity	NPC85121
0.9295	High Similarity	NPC152904
0.9295	High Similarity	NPC235448
0.929	High Similarity	NPC278778
0.929	High Similarity	NPC235165
0.929	High Similarity	NPC291878
0.929	High Similarity	NPC255106
0.929	High Similarity	NPC35038
0.929	High Similarity	NPC472916
0.929	High Similarity	NPC195796
0.9286	High Similarity	NPC298692
0.9281	High Similarity	NPC226973
0.9281	High Similarity	NPC208043
0.9281	High Similarity	NPC149614
0.9281	High Similarity	NPC202157
0.9276	High Similarity	NPC328119
0.925	High Similarity	NPC218226
0.9241	High Similarity	NPC470694
0.9241	High Similarity	NPC81679
0.9241	High Similarity	NPC472964
0.9241	High Similarity	NPC83922
0.9241	High Similarity	NPC329760
0.9241	High Similarity	NPC474150
0.9241	High Similarity	NPC472448
0.9241	High Similarity	NPC474162
0.9236	High Similarity	NPC204290
0.9236	High Similarity	NPC471973
0.9236	High Similarity	NPC472631
0.9236	High Similarity	NPC246478
0.9236	High Similarity	NPC80375
0.9236	High Similarity	NPC472630
0.9236	High Similarity	NPC139036
0.9236	High Similarity	NPC476980
0.9231	High Similarity	NPC472598
0.9231	High Similarity	NPC210084
0.9231	High Similarity	NPC472963
0.9231	High Similarity	NPC299520
0.9231	High Similarity	NPC27337
0.9231	High Similarity	NPC129684
0.9231	High Similarity	NPC473272
0.9231	High Similarity	NPC291508
0.9231	High Similarity	NPC474055
0.9231	High Similarity	NPC284820
0.9231	High Similarity	NPC99597
0.9226	High Similarity	NPC117992
0.9226	High Similarity	NPC213622
0.9226	High Similarity	NPC152951
0.9226	High Similarity	NPC130589
0.9226	High Similarity	NPC57674
0.9226	High Similarity	NPC67396
0.9226	High Similarity	NPC2928
0.9226	High Similarity	NPC230149
0.9226	High Similarity	NPC168247
0.9226	High Similarity	NPC134287
0.9221	High Similarity	NPC199100
0.9221	High Similarity	NPC120537
0.9221	High Similarity	NPC474843
0.9221	High Similarity	NPC101996
0.9221	High Similarity	NPC180234
0.9221	High Similarity	NPC249570
0.9221	High Similarity	NPC106976
0.9221	High Similarity	NPC471982
0.9216	High Similarity	NPC151473
0.9216	High Similarity	NPC239363
0.9216	High Similarity	NPC306821
0.9202	High Similarity	NPC289147
0.9198	High Similarity	NPC260263
0.9193	High Similarity	NPC99613
0.9193	High Similarity	NPC49487
0.9187	High Similarity	NPC29160
0.9187	High Similarity	NPC43319
0.9187	High Similarity	NPC470462
0.9187	High Similarity	NPC472452
0.9187	High Similarity	NPC272502
0.9187	High Similarity	NPC128293
0.9182	High Similarity	NPC207690
0.9182	High Similarity	NPC473313
0.9182	High Similarity	NPC470459
0.9182	High Similarity	NPC18100
0.9182	High Similarity	NPC472278
0.9182	High Similarity	NPC329669

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 NPC475886 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	380
0.1-0.2	979
0.2-0.3	1776
0.3-0.4	2654
0.4-0.5	1816
0.5-0.6	931
0.6-0.7	425
0.7-0.8	130
0.8-0.85	39
0.85-0.9	19
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9161	High Similarity	NPD2393	Clinical (unspecified phase)
0.9161	High Similarity	NPD2801	Approved
0.9097	High Similarity	NPD1934	Approved
0.8994	High Similarity	NPD5494	Approved
0.8834	High Similarity	NPD7473	Discontinued
0.8797	High Similarity	NPD7819	Suspended
0.8765	High Similarity	NPD6232	Discontinued
0.8727	High Similarity	NPD5844	Phase 1
0.8688	High Similarity	NPD3882	Suspended
0.8659	High Similarity	NPD6168	Clinical (unspecified phase)
0.8659	High Similarity	NPD6167	Clinical (unspecified phase)
0.8659	High Similarity	NPD6166	Phase 2
0.8645	High Similarity	NPD4378	Clinical (unspecified phase)
0.8589	High Similarity	NPD6959	Discontinued
0.8581	High Similarity	NPD1511	Approved
0.8563	High Similarity	NPD7074	Phase 3
0.8519	High Similarity	NPD7075	Discontinued
0.8509	High Similarity	NPD8443	Clinical (unspecified phase)
0.8509	High Similarity	NPD3817	Phase 2
0.8503	High Similarity	NPD7054	Approved
0.8491	Intermediate Similarity	NPD4380	Phase 2
0.8471	Intermediate Similarity	NPD1512	Approved
0.8457	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8452	Intermediate Similarity	NPD7472	Approved
0.8447	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8443	Intermediate Similarity	NPD3818	Discontinued
0.8431	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8431	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8412	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8377	Intermediate Similarity	NPD1549	Phase 2
0.8333	Intermediate Similarity	NPD1465	Phase 2
0.8304	Intermediate Similarity	NPD7808	Phase 3
0.8291	Intermediate Similarity	NPD2532	Approved
0.8291	Intermediate Similarity	NPD2534	Approved
0.8291	Intermediate Similarity	NPD2533	Approved
0.8253	Intermediate Similarity	NPD1247	Approved
0.8246	Intermediate Similarity	NPD7251	Discontinued
0.821	Intermediate Similarity	NPD7411	Suspended
0.8187	Intermediate Similarity	NPD6797	Phase 2
0.8182	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD1510	Phase 2
0.8176	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8176	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8141	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8129	Intermediate Similarity	NPD2796	Approved
0.8122	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.8089	Intermediate Similarity	NPD2800	Approved
0.8049	Intermediate Similarity	NPD6801	Discontinued
0.8039	Intermediate Similarity	NPD1240	Approved
0.8023	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8013	Intermediate Similarity	NPD2935	Discontinued
0.8012	Intermediate Similarity	NPD7768	Phase 2
0.8	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD6799	Approved
0.7977	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7964	Intermediate Similarity	NPD3749	Approved
0.7952	Intermediate Similarity	NPD5402	Approved
0.7949	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7941	Intermediate Similarity	NPD3926	Phase 2
0.7935	Intermediate Similarity	NPD1607	Approved
0.7933	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7931	Intermediate Similarity	NPD6559	Discontinued
0.7927	Intermediate Similarity	NPD6599	Discontinued
0.7925	Intermediate Similarity	NPD3750	Approved
0.7917	Intermediate Similarity	NPD919	Approved
0.7898	Intermediate Similarity	NPD6100	Approved
0.7898	Intermediate Similarity	NPD6099	Approved
0.7866	Intermediate Similarity	NPD3226	Approved
0.7848	Intermediate Similarity	NPD2346	Discontinued
0.7831	Intermediate Similarity	NPD37	Approved
0.7811	Intermediate Similarity	NPD6234	Discontinued
0.7806	Intermediate Similarity	NPD943	Approved
0.7798	Intermediate Similarity	NPD4965	Approved
0.7798	Intermediate Similarity	NPD4966	Approved
0.7798	Intermediate Similarity	NPD4967	Phase 2
0.7778	Intermediate Similarity	NPD5710	Approved
0.7778	Intermediate Similarity	NPD5711	Approved
0.7778	Intermediate Similarity	NPD7390	Discontinued
0.775	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7719	Intermediate Similarity	NPD7199	Phase 2
0.7712	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7707	Intermediate Similarity	NPD6651	Approved
0.7701	Intermediate Similarity	NPD3751	Discontinued
0.7701	Intermediate Similarity	NPD7228	Approved
0.7692	Intermediate Similarity	NPD1613	Approved
0.7692	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7674	Intermediate Similarity	NPD3787	Discontinued
0.7662	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7657	Intermediate Similarity	NPD7286	Phase 2
0.7654	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD447	Suspended
0.7643	Intermediate Similarity	NPD230	Phase 1
0.764	Intermediate Similarity	NPD8313	Approved
0.764	Intermediate Similarity	NPD8312	Approved
0.7636	Intermediate Similarity	NPD920	Approved
0.7636	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.763	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.761	Intermediate Similarity	NPD3748	Approved
0.761	Intermediate Similarity	NPD2799	Discontinued
0.761	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7584	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7572	Intermediate Similarity	NPD7229	Phase 3
0.7571	Intermediate Similarity	NPD5953	Discontinued
0.7564	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7562	Intermediate Similarity	NPD1551	Phase 2
0.754	Intermediate Similarity	NPD6782	Approved
0.754	Intermediate Similarity	NPD6777	Approved
0.754	Intermediate Similarity	NPD6780	Approved
0.754	Intermediate Similarity	NPD6776	Approved
0.754	Intermediate Similarity	NPD6779	Approved
0.754	Intermediate Similarity	NPD6781	Approved
0.754	Intermediate Similarity	NPD6778	Approved
0.7531	Intermediate Similarity	NPD1243	Approved
0.753	Intermediate Similarity	NPD5403	Approved
0.7516	Intermediate Similarity	NPD2344	Approved
0.7515	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD8150	Discontinued
0.7513	Intermediate Similarity	NPD7697	Approved
0.7513	Intermediate Similarity	NPD7698	Approved
0.7513	Intermediate Similarity	NPD7696	Phase 3
0.7513	Intermediate Similarity	NPD7435	Discontinued
0.75	Intermediate Similarity	NPD4625	Phase 3
0.75	Intermediate Similarity	NPD8151	Discontinued
0.75	Intermediate Similarity	NPD3027	Phase 3
0.7485	Intermediate Similarity	NPD4628	Phase 3
0.7474	Intermediate Similarity	NPD7871	Phase 2
0.7474	Intermediate Similarity	NPD7870	Phase 2
0.7455	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD2313	Discontinued
0.7436	Intermediate Similarity	NPD4908	Phase 1
0.7423	Intermediate Similarity	NPD7783	Phase 2
0.7423	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD1933	Approved
0.7418	Intermediate Similarity	NPD8434	Phase 2
0.741	Intermediate Similarity	NPD5401	Approved
0.7394	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD1653	Approved
0.7378	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD6823	Phase 2
0.7366	Intermediate Similarity	NPD4363	Phase 3
0.7366	Intermediate Similarity	NPD4360	Phase 2
0.7358	Intermediate Similarity	NPD7701	Phase 2
0.7353	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD7240	Approved
0.7333	Intermediate Similarity	NPD2309	Approved
0.733	Intermediate Similarity	NPD5242	Approved
0.7326	Intermediate Similarity	NPD5353	Approved
0.732	Intermediate Similarity	NPD1610	Phase 2
0.731	Intermediate Similarity	NPD6844	Discontinued
0.7282	Intermediate Similarity	NPD7874	Approved
0.7282	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD6535	Approved
0.7273	Intermediate Similarity	NPD6534	Approved
0.7261	Intermediate Similarity	NPD2861	Phase 2
0.7261	Intermediate Similarity	NPD9494	Approved
0.725	Intermediate Similarity	NPD4060	Phase 1
0.7249	Intermediate Similarity	NPD7699	Phase 2
0.7249	Intermediate Similarity	NPD7700	Phase 2
0.7245	Intermediate Similarity	NPD7801	Approved
0.7244	Intermediate Similarity	NPD1470	Approved
0.7238	Intermediate Similarity	NPD7685	Pre-registration
0.7235	Intermediate Similarity	NPD7458	Discontinued
0.7233	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD6190	Approved
0.7215	Intermediate Similarity	NPD6832	Phase 2
0.7212	Intermediate Similarity	NPD6674	Discontinued
0.7208	Intermediate Similarity	NPD1201	Approved
0.7208	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7196	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7191	Intermediate Similarity	NPD2403	Approved
0.7151	Intermediate Similarity	NPD6385	Approved
0.7151	Intermediate Similarity	NPD6386	Approved
0.7143	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4361	Phase 2
0.7134	Intermediate Similarity	NPD5408	Approved
0.7134	Intermediate Similarity	NPD1203	Approved
0.7134	Intermediate Similarity	NPD5406	Approved
0.7134	Intermediate Similarity	NPD5404	Approved
0.7134	Intermediate Similarity	NPD5405	Approved
0.7128	Intermediate Similarity	NPD7584	Approved
0.7125	Intermediate Similarity	NPD3268	Approved
0.7125	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD8127	Discontinued
0.7115	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD4749	Approved
0.7108	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7104	Intermediate Similarity	NPD7549	Discontinued
0.7099	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD1471	Phase 3
0.7089	Intermediate Similarity	NPD2798	Approved
0.7073	Intermediate Similarity	NPD7033	Discontinued
0.7069	Intermediate Similarity	NPD5760	Phase 2
0.7069	Intermediate Similarity	NPD8455	Phase 2
0.7069	Intermediate Similarity	NPD5761	Phase 2

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