NPASS Compound

Structure

NPC474186 OpenBabel07101719252D 36 38 0 0 0 0 0 0 0 0999 V2000 -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 3.4641 -3.0000 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 -2.5981 3.5000 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 2.5981 3.5000 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 -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 -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 -3.4641 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 -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 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 18 1 0 0 0 0 7 19 1 0 0 0 0 8 19 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 20 1 0 0 0 0 13 21 1 0 0 0 0 14 22 2 0 0 0 0 14 24 1 0 0 0 0 15 23 2 0 0 0 0 15 25 1 0 0 0 0 18 34 1 0 0 0 0 19 35 1 0 0 0 0 20 22 1 0 0 0 0 20 28 2 0 0 0 0 21 26 2 0 0 0 0 21 30 1 0 0 0 0 22 34 1 0 0 0 0 23 26 1 0 0 0 0 23 36 1 0 0 0 0 24 27 2 0 0 0 0 24 36 1 0 0 0 0 25 30 2 0 0 0 0 25 35 1 0 0 0 0 26 29 1 0 0 0 0 27 28 1 0 0 0 0 27 29 1 0 0 0 0 28 31 1 0 0 0 0 29 32 2 0 0 0 0 30 33 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	494.27
Volume:	530.78
LogP:	7.27
LogD:	5.436
LogS:	-5.135
# 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:	0.246
Synthetic Accessibility Score:	3.324
Fsp3:	0.433
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.754
MDCK Permeability:	1.4053923223400488e-05
Pgp-inhibitor:	0.998
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.014
20% Bioavailability (F20%):	0.014
30% Bioavailability (F30%):	0.148

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.014
Plasma Protein Binding (PPB):	90.94363403320312%
Volume Distribution (VD):	1.117
Pgp-substrate:	13.314059257507324%

ADMET: Metabolism

CYP1A2-inhibitor:	0.092
CYP1A2-substrate:	0.384
CYP2C19-inhibitor:	0.821
CYP2C19-substrate:	0.693
CYP2C9-inhibitor:	0.919
CYP2C9-substrate:	0.962
CYP2D6-inhibitor:	0.095
CYP2D6-substrate:	0.291
CYP3A4-inhibitor:	0.168
CYP3A4-substrate:	0.219

ADMET: Excretion

Clearance (CL):	3.292
Half-life (T1/2):	0.066

ADMET: Toxicity

hERG Blockers:	0.031
Human Hepatotoxicity (H-HT):	0.756
Drug-inuced Liver Injury (DILI):	0.854
AMES Toxicity:	0.268
Rat Oral Acute Toxicity:	0.193
Maximum Recommended Daily Dose:	0.036
Skin Sensitization:	0.272
Carcinogencity:	0.41
Eye Corrosion:	0.003
Eye Irritation:	0.023
Respiratory Toxicity:	0.581

Download Data

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

Natural Product: NPC474186

Natural Product ID:	NPC474186
*Common Name:**	Di-O-Isopropylmangostin
IUPAC Name:	1-hydroxy-7-methoxy-2,8-bis(3-methylbut-2-enyl)-3,6-di(propan-2-yloxy)xanthen-9-one
Synonyms:	Di-O-Isopropylmangostin
Standard InCHIKey:	ULAWVIJYOOSDRZ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C30H38O6/c1-16(2)10-12-20-22(34-18(5)6)14-24-27(28(20)31)29(32)26-21(13-11-17(3)4)30(33-9)25(35-19(7)8)15-23(26)36-24/h10-11,14-15,18-19,31H,12-13H2,1-9H3
SMILES:	COc1c(OC(C)C)cc2c(c1CC=C(C)C)c(=O)c1c(o2)cc(c(c1O)CC=C(C)C)OC(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL463292
PubChem CID:	10625023
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	=	-10.0	%	PMID[564523]
NPT2646	Organism	Alternaria tenuis	Alternaria tenuis	Inhibition	=	2.0	%	PMID[564523]
NPT2646	Organism	Alternaria tenuis	Alternaria tenuis	Inhibition	=	-1.0	%	PMID[564523]
NPT2646	Organism	Alternaria tenuis	Alternaria tenuis	Inhibition	=	1.0	%	PMID[564523]
NPT2647	Organism	Drechslera	Drechslera	Inhibition	=	-1.0	%	PMID[564523]
NPT2647	Organism	Drechslera	Drechslera	Inhibition	=	4.0	%	PMID[564523]
NPT2647	Organism	Drechslera	Drechslera	Inhibition	=	1.0	%	PMID[564523]
NPT2647	Organism	Drechslera	Drechslera	Inhibition	=	9.0	%	PMID[564523]
NPT2648	Organism	Fusarium oxysporum f. sp. vasinfectum	Fusarium oxysporum f. sp. vasinfectum	Inhibition	=	3.0	%	PMID[564523]
NPT2648	Organism	Fusarium oxysporum f. sp. vasinfectum	Fusarium oxysporum f. sp. vasinfectum	Inhibition	=	1.0	%	PMID[564523]
NPT2648	Organism	Fusarium oxysporum f. sp. vasinfectum	Fusarium oxysporum f. sp. vasinfectum	Inhibition	=	4.0	%	PMID[564523]

☑ 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 NPC474186 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	437
0.1-0.2	1670
0.2-0.3	3873
0.3-0.4	9712
0.4-0.5	8824
0.5-0.6	3491
0.6-0.7	5013
0.7-0.8	5086
0.8-0.85	2707
0.85-0.9	1486
0.9-0.95	360
0.95-1	38

Similarity Score	Similarity Level	Natural Product ID
0.9934	High Similarity	NPC474287
0.9934	High Similarity	NPC475886
0.9869	High Similarity	NPC475883
0.9869	High Similarity	NPC474187
0.9869	High Similarity	NPC474351
0.9803	High Similarity	NPC165977
0.9803	High Similarity	NPC217677
0.9742	High Similarity	NPC7483
0.9742	High Similarity	NPC197168
0.974	High Similarity	NPC40491
0.974	High Similarity	NPC278052
0.9679	High Similarity	NPC326520
0.9679	High Similarity	NPC25361
0.9675	High Similarity	NPC14353
0.9675	High Similarity	NPC299436
0.9675	High Similarity	NPC228785
0.9675	High Similarity	NPC320359
0.9675	High Similarity	NPC56085
0.9618	High Similarity	NPC170245
0.9615	High Similarity	NPC236132
0.9613	High Similarity	NPC61010
0.961	High Similarity	NPC100123
0.9557	High Similarity	NPC6588
0.9557	High Similarity	NPC477154
0.9557	High Similarity	NPC117854
0.9551	High Similarity	NPC229632
0.9551	High Similarity	NPC201800
0.9548	High Similarity	NPC36217
0.9545	High Similarity	NPC236796
0.9545	High Similarity	NPC300727
0.9545	High Similarity	NPC241904
0.9545	High Similarity	NPC223787
0.9542	High Similarity	NPC226025
0.9542	High Similarity	NPC37392
0.9494	High Similarity	NPC39091
0.949	High Similarity	NPC248638
0.949	High Similarity	NPC273959
0.949	High Similarity	NPC475985
0.949	High Similarity	NPC152659
0.949	High Similarity	NPC220313
0.949	High Similarity	NPC236521
0.949	High Similarity	NPC474350
0.949	High Similarity	NPC474240
0.9487	High Similarity	NPC66288
0.9484	High Similarity	NPC329091
0.9484	High Similarity	NPC250214
0.9484	High Similarity	NPC95936
0.9484	High Similarity	NPC476242
0.9484	High Similarity	NPC210459
0.9481	High Similarity	NPC470328
0.9481	High Similarity	NPC209614
0.9481	High Similarity	NPC142339
0.9481	High Similarity	NPC274730
0.9481	High Similarity	NPC472626
0.943	High Similarity	NPC473286
0.943	High Similarity	NPC472450
0.943	High Similarity	NPC293319
0.943	High Similarity	NPC275780
0.943	High Similarity	NPC239752
0.943	High Similarity	NPC475888
0.9427	High Similarity	NPC211107
0.9427	High Similarity	NPC25152
0.9427	High Similarity	NPC52204
0.9423	High Similarity	NPC321399
0.9423	High Similarity	NPC119224
0.9419	High Similarity	NPC78225
0.9419	High Similarity	NPC181960
0.9419	High Similarity	NPC474836
0.9419	High Similarity	NPC48208
0.9419	High Similarity	NPC469584
0.9419	High Similarity	NPC262286
0.9419	High Similarity	NPC156057
0.9419	High Similarity	NPC162869
0.9419	High Similarity	NPC474208
0.9419	High Similarity	NPC475267
0.9419	High Similarity	NPC36852
0.9416	High Similarity	NPC472909
0.9416	High Similarity	NPC45849
0.9416	High Similarity	NPC200761
0.9416	High Similarity	NPC470327
0.9416	High Similarity	NPC477503
0.9408	High Similarity	NPC338131
0.9371	High Similarity	NPC120593
0.9367	High Similarity	NPC23298
0.9367	High Similarity	NPC186686
0.9367	High Similarity	NPC189473
0.9367	High Similarity	NPC270837
0.9367	High Similarity	NPC41301
0.9363	High Similarity	NPC474239
0.9363	High Similarity	NPC266314
0.9363	High Similarity	NPC32694
0.9359	High Similarity	NPC85121
0.9355	High Similarity	NPC278778
0.9355	High Similarity	NPC191146
0.9355	High Similarity	NPC138243
0.9355	High Similarity	NPC291878
0.9355	High Similarity	NPC255106
0.9355	High Similarity	NPC195796
0.9355	High Similarity	NPC235165
0.9355	High Similarity	NPC68093
0.9355	High Similarity	NPC35038
0.9351	High Similarity	NPC280937
0.9351	High Similarity	NPC298692
0.9351	High Similarity	NPC472915
0.9351	High Similarity	NPC89474
0.9346	High Similarity	NPC117579
0.9313	High Similarity	NPC218226
0.9304	High Similarity	NPC294965
0.9304	High Similarity	NPC472964
0.9304	High Similarity	NPC81679
0.9299	High Similarity	NPC472631
0.9299	High Similarity	NPC45146
0.9299	High Similarity	NPC200746
0.9299	High Similarity	NPC472630
0.9299	High Similarity	NPC235018
0.9295	High Similarity	NPC99597
0.9295	High Similarity	NPC476981
0.9295	High Similarity	NPC291508
0.9295	High Similarity	NPC472910
0.9295	High Similarity	NPC472911
0.9295	High Similarity	NPC245758
0.9295	High Similarity	NPC474055
0.9295	High Similarity	NPC96167
0.9295	High Similarity	NPC284820
0.9295	High Similarity	NPC27337
0.9295	High Similarity	NPC472913
0.9295	High Similarity	NPC473272
0.9295	High Similarity	NPC222814
0.9295	High Similarity	NPC136674
0.9295	High Similarity	NPC472598
0.9295	High Similarity	NPC472914
0.9295	High Similarity	NPC210084
0.929	High Similarity	NPC255807
0.929	High Similarity	NPC113906
0.929	High Similarity	NPC67396
0.929	High Similarity	NPC31018
0.9286	High Similarity	NPC106976
0.9286	High Similarity	NPC474843
0.9281	High Similarity	NPC227122
0.9281	High Similarity	NPC179183
0.925	High Similarity	NPC128293
0.925	High Similarity	NPC472452
0.925	High Similarity	NPC272502
0.925	High Similarity	NPC472449
0.925	High Similarity	NPC43319
0.925	High Similarity	NPC37870
0.9245	High Similarity	NPC329669
0.9245	High Similarity	NPC473313
0.9245	High Similarity	NPC472278
0.9245	High Similarity	NPC146134
0.9245	High Similarity	NPC18100
0.9241	High Similarity	NPC471211
0.9241	High Similarity	NPC134783
0.9241	High Similarity	NPC472634
0.9241	High Similarity	NPC471210
0.9241	High Similarity	NPC471212
0.9236	High Similarity	NPC473990
0.9236	High Similarity	NPC469658
0.9236	High Similarity	NPC235448
0.9236	High Similarity	NPC152904
0.9231	High Similarity	NPC24640
0.9231	High Similarity	NPC472916
0.9226	High Similarity	NPC74924
0.9226	High Similarity	NPC213896
0.9226	High Similarity	NPC18727
0.9226	High Similarity	NPC192083
0.9221	High Similarity	NPC208043
0.9221	High Similarity	NPC226973
0.9221	High Similarity	NPC202157
0.9221	High Similarity	NPC149614
0.9216	High Similarity	NPC328119
0.9193	High Similarity	NPC470456
0.9193	High Similarity	NPC158761
0.9193	High Similarity	NPC474024
0.9187	High Similarity	NPC234052
0.9187	High Similarity	NPC224280
0.9187	High Similarity	NPC62261
0.9187	High Similarity	NPC472277
0.9187	High Similarity	NPC470457
0.9182	High Similarity	NPC474150
0.9182	High Similarity	NPC83922
0.9182	High Similarity	NPC329760
0.9182	High Similarity	NPC472448
0.9182	High Similarity	NPC474162
0.9182	High Similarity	NPC220912
0.9182	High Similarity	NPC470694
0.9182	High Similarity	NPC472402
0.9177	High Similarity	NPC118256
0.9177	High Similarity	NPC472902
0.9177	High Similarity	NPC287328
0.9177	High Similarity	NPC470326
0.9177	High Similarity	NPC282009
0.9177	High Similarity	NPC204290
0.9177	High Similarity	NPC475784
0.9177	High Similarity	NPC139036
0.9177	High Similarity	NPC246478
0.9177	High Similarity	NPC476980
0.9177	High Similarity	NPC472624
0.9177	High Similarity	NPC192686
0.9177	High Similarity	NPC174953

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 NPC474186 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	383
0.1-0.2	962
0.2-0.3	1795
0.3-0.4	2646
0.4-0.5	1833
0.5-0.6	904
0.6-0.7	449
0.7-0.8	123
0.8-0.85	37
0.85-0.9	17
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9226	High Similarity	NPD2393	Clinical (unspecified phase)
0.9161	High Similarity	NPD1934	Approved
0.9103	High Similarity	NPD2801	Approved
0.9057	High Similarity	NPD5494	Approved
0.8788	High Similarity	NPD5844	Phase 1
0.878	High Similarity	NPD7473	Discontinued
0.8742	High Similarity	NPD7819	Suspended
0.872	High Similarity	NPD6168	Clinical (unspecified phase)
0.872	High Similarity	NPD6167	Clinical (unspecified phase)
0.872	High Similarity	NPD6166	Phase 2
0.8712	High Similarity	NPD6232	Discontinued
0.865	High Similarity	NPD6959	Discontinued
0.8634	High Similarity	NPD3882	Suspended
0.8623	High Similarity	NPD7074	Phase 3
0.859	High Similarity	NPD4378	Clinical (unspecified phase)
0.858	High Similarity	NPD7075	Discontinued
0.8571	High Similarity	NPD8443	Clinical (unspecified phase)
0.8563	High Similarity	NPD7054	Approved
0.8553	High Similarity	NPD4380	Phase 2
0.8526	High Similarity	NPD1511	Approved
0.8519	High Similarity	NPD4868	Clinical (unspecified phase)
0.8512	High Similarity	NPD7472	Approved
0.8509	High Similarity	NPD7096	Clinical (unspecified phase)
0.8503	High Similarity	NPD3818	Discontinued
0.8497	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8497	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8471	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8457	Intermediate Similarity	NPD3817	Phase 2
0.8442	Intermediate Similarity	NPD1549	Phase 2
0.8418	Intermediate Similarity	NPD1512	Approved
0.8363	Intermediate Similarity	NPD7808	Phase 3
0.8304	Intermediate Similarity	NPD7251	Discontinued
0.8282	Intermediate Similarity	NPD1465	Phase 2
0.8246	Intermediate Similarity	NPD6797	Phase 2
0.8242	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8239	Intermediate Similarity	NPD2532	Approved
0.8239	Intermediate Similarity	NPD2533	Approved
0.8239	Intermediate Similarity	NPD2534	Approved
0.8235	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8204	Intermediate Similarity	NPD1247	Approved
0.8194	Intermediate Similarity	NPD2796	Approved
0.816	Intermediate Similarity	NPD7411	Suspended
0.8129	Intermediate Similarity	NPD1510	Phase 2
0.8125	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.811	Intermediate Similarity	NPD6801	Discontinued
0.8089	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8079	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8077	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.8038	Intermediate Similarity	NPD2800	Approved
0.8035	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD5402	Approved
0.7989	Intermediate Similarity	NPD6559	Discontinued
0.7989	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD1240	Approved
0.7964	Intermediate Similarity	NPD7768	Phase 2
0.7962	Intermediate Similarity	NPD2935	Discontinued
0.7953	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.795	Intermediate Similarity	NPD6799	Approved
0.7917	Intermediate Similarity	NPD3749	Approved
0.7898	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD3926	Phase 2
0.7892	Intermediate Similarity	NPD37	Approved
0.7885	Intermediate Similarity	NPD1607	Approved
0.7879	Intermediate Similarity	NPD6599	Discontinued
0.7875	Intermediate Similarity	NPD3750	Approved
0.787	Intermediate Similarity	NPD919	Approved
0.787	Intermediate Similarity	NPD6234	Discontinued
0.7857	Intermediate Similarity	NPD4965	Approved
0.7857	Intermediate Similarity	NPD4966	Approved
0.7857	Intermediate Similarity	NPD4967	Phase 2
0.7848	Intermediate Similarity	NPD6100	Approved
0.7848	Intermediate Similarity	NPD6099	Approved
0.7818	Intermediate Similarity	NPD3226	Approved
0.7799	Intermediate Similarity	NPD2346	Discontinued
0.7759	Intermediate Similarity	NPD3751	Discontinued
0.7759	Intermediate Similarity	NPD7228	Approved
0.7756	Intermediate Similarity	NPD1613	Approved
0.7756	Intermediate Similarity	NPD943	Approved
0.7756	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD5711	Approved
0.7733	Intermediate Similarity	NPD5710	Approved
0.7733	Intermediate Similarity	NPD3787	Discontinued
0.773	Intermediate Similarity	NPD7390	Discontinued
0.7709	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7702	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD8312	Approved
0.7697	Intermediate Similarity	NPD8313	Approved
0.7674	Intermediate Similarity	NPD7199	Phase 2
0.7662	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7658	Intermediate Similarity	NPD6651	Approved
0.7628	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7614	Intermediate Similarity	NPD7286	Phase 2
0.7613	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD230	Phase 1
0.7595	Intermediate Similarity	NPD447	Suspended
0.7594	Intermediate Similarity	NPD6781	Approved
0.7594	Intermediate Similarity	NPD6776	Approved
0.7594	Intermediate Similarity	NPD6777	Approved
0.7594	Intermediate Similarity	NPD6778	Approved
0.7594	Intermediate Similarity	NPD6779	Approved
0.7594	Intermediate Similarity	NPD6782	Approved
0.7594	Intermediate Similarity	NPD6780	Approved
0.759	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD5403	Approved
0.759	Intermediate Similarity	NPD920	Approved
0.7586	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7569	Intermediate Similarity	NPD8150	Discontinued
0.7566	Intermediate Similarity	NPD7435	Discontinued
0.7566	Intermediate Similarity	NPD7698	Approved
0.7566	Intermediate Similarity	NPD7697	Approved
0.7566	Intermediate Similarity	NPD7696	Phase 3
0.7564	Intermediate Similarity	NPD3027	Phase 3
0.7562	Intermediate Similarity	NPD3748	Approved
0.7562	Intermediate Similarity	NPD2799	Discontinued
0.7562	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7552	Intermediate Similarity	NPD8151	Discontinued
0.7546	Intermediate Similarity	NPD4628	Phase 3
0.7546	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7542	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD7229	Phase 3
0.7528	Intermediate Similarity	NPD5953	Discontinued
0.7526	Intermediate Similarity	NPD7871	Phase 2
0.7526	Intermediate Similarity	NPD7870	Phase 2
0.7516	Intermediate Similarity	NPD1551	Phase 2
0.7516	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD1243	Approved
0.7474	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7474	Intermediate Similarity	NPD7783	Phase 2
0.7473	Intermediate Similarity	NPD8434	Phase 2
0.747	Intermediate Similarity	NPD5401	Approved
0.747	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7469	Intermediate Similarity	NPD2344	Approved
0.7452	Intermediate Similarity	NPD4625	Phase 3
0.744	Intermediate Similarity	NPD1653	Approved
0.7421	Intermediate Similarity	NPD6823	Phase 2
0.7419	Intermediate Similarity	NPD4363	Phase 3
0.7419	Intermediate Similarity	NPD4360	Phase 2
0.7412	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7409	Intermediate Similarity	NPD7701	Phase 2
0.7405	Intermediate Similarity	NPD2313	Discontinued
0.7396	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD4908	Phase 1
0.7389	Intermediate Similarity	NPD7240	Approved
0.7384	Intermediate Similarity	NPD5353	Approved
0.7375	Intermediate Similarity	NPD1933	Approved
0.7368	Intermediate Similarity	NPD6844	Discontinued
0.7349	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD7874	Approved
0.7333	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD6534	Approved
0.7326	Intermediate Similarity	NPD6535	Approved
0.7325	Intermediate Similarity	NPD2861	Phase 2
0.7302	Intermediate Similarity	NPD7700	Phase 2
0.7302	Intermediate Similarity	NPD7699	Phase 2
0.7296	Intermediate Similarity	NPD7801	Approved
0.7293	Intermediate Similarity	NPD7685	Pre-registration
0.7289	Intermediate Similarity	NPD6190	Approved
0.7289	Intermediate Similarity	NPD2309	Approved
0.7288	Intermediate Similarity	NPD5242	Approved
0.7273	Intermediate Similarity	NPD6674	Discontinued
0.7273	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD1610	Phase 2
0.7262	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7249	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD9494	Approved
0.7205	Intermediate Similarity	NPD4060	Phase 1
0.7197	Intermediate Similarity	NPD1470	Approved
0.7193	Intermediate Similarity	NPD7458	Discontinued
0.7188	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD7584	Approved
0.7175	Intermediate Similarity	NPD8127	Discontinued
0.717	Intermediate Similarity	NPD6832	Phase 2
0.7169	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD1201	Approved
0.7151	Intermediate Similarity	NPD2403	Approved
0.7134	Intermediate Similarity	NPD7033	Discontinued
0.7126	Intermediate Similarity	NPD5761	Phase 2
0.7126	Intermediate Similarity	NPD5760	Phase 2
0.7126	Intermediate Similarity	NPD8455	Phase 2
0.711	Intermediate Similarity	NPD6386	Approved
0.711	Intermediate Similarity	NPD6385	Approved
0.7108	Intermediate Similarity	NPD2424	Discontinued
0.7105	Intermediate Similarity	NPD4361	Phase 2
0.7105	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD5405	Approved
0.7091	Intermediate Similarity	NPD5404	Approved
0.7091	Intermediate Similarity	NPD5406	Approved
0.7091	Intermediate Similarity	NPD5408	Approved
0.709	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.709	Intermediate Similarity	NPD6213	Phase 3
0.709	Intermediate Similarity	NPD6212	Phase 3
0.7089	Intermediate Similarity	NPD1203	Approved
0.7081	Intermediate Similarity	NPD3268	Approved
0.7081	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD4749	Approved
0.707	Intermediate Similarity	NPD4379	Clinical (unspecified phase)

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