NPASS Compound

Structure

NPC474350 OpenBabel07101718222D 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 -4.3301 -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 2.5981 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -3.5000 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 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 14 1 0 0 0 0 2 14 1 0 0 0 0 3 15 1 0 0 0 0 4 15 1 0 0 0 0 5 16 1 0 0 0 0 6 17 1 0 0 0 0 7 33 1 0 0 0 0 8 10 1 0 0 0 0 8 14 2 0 0 0 0 9 11 1 0 0 0 0 9 15 2 0 0 0 0 10 18 1 0 0 0 0 11 19 1 0 0 0 0 12 20 2 0 0 0 0 12 22 1 0 0 0 0 13 21 2 0 0 0 0 13 23 1 0 0 0 0 16 29 2 0 0 0 0 16 34 1 0 0 0 0 17 30 2 0 0 0 0 17 35 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 34 1 0 0 0 0 21 24 1 0 0 0 0 21 36 1 0 0 0 0 22 25 2 0 0 0 0 22 36 1 0 0 0 0 23 28 2 0 0 0 0 23 35 1 0 0 0 0 24 27 1 0 0 0 0 25 26 1 0 0 0 0 25 27 1 0 0 0 0 26 31 1 0 0 0 0 27 32 2 0 0 0 0 28 33 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	494.19
Volume:	508.495
LogP:	6.088
LogD:	2.999
LogS:	-3.61
# Rotatable Bonds:	9
TPSA:	112.27
# H-Bond Aceptor:	8
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.193
Synthetic Accessibility Score:	3.333
Fsp3:	0.321
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:	-4.885
MDCK Permeability:	2.060472070297692e-05
Pgp-inhibitor:	0.989
Pgp-substrate:	0.069
Human Intestinal Absorption (HIA):	0.787
20% Bioavailability (F20%):	0.075
30% Bioavailability (F30%):	0.036

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.02
Plasma Protein Binding (PPB):	90.81652069091797%
Volume Distribution (VD):	1.229
Pgp-substrate:	11.21955394744873%

ADMET: Metabolism

CYP1A2-inhibitor:	0.174
CYP1A2-substrate:	0.32
CYP2C19-inhibitor:	0.628
CYP2C19-substrate:	0.269
CYP2C9-inhibitor:	0.894
CYP2C9-substrate:	0.895
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.246
CYP3A4-inhibitor:	0.236
CYP3A4-substrate:	0.164

ADMET: Excretion

Clearance (CL):	1.26
Half-life (T1/2):	0.186

ADMET: Toxicity

hERG Blockers:	0.002
Human Hepatotoxicity (H-HT):	0.05
Drug-inuced Liver Injury (DILI):	0.658
AMES Toxicity:	0.262
Rat Oral Acute Toxicity:	0.842
Maximum Recommended Daily Dose:	0.275
Skin Sensitization:	0.932
Carcinogencity:	0.369
Eye Corrosion:	0.004
Eye Irritation:	0.275
Respiratory Toxicity:	0.395

Download Data

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

Natural Product: NPC474350

Natural Product ID:	NPC474350
*Common Name:**	Di-O-Acetylmangostin
IUPAC Name:	[6-acetyloxy-1-hydroxy-7-methoxy-2,8-bis(3-methylbut-2-enyl)-9-oxoxanthen-3-yl] acetate
Synonyms:	Di-O-Acetylmangostin
Standard InCHIKey:	WBVGQHDFFNOEEI-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C28H30O8/c1-14(2)8-10-18-20(34-16(5)29)12-22-25(26(18)31)27(32)24-19(11-9-15(3)4)28(33-7)23(35-17(6)30)13-21(24)36-22/h8-9,12-13,31H,10-11H2,1-7H3
SMILES:	COc1c(OC(=O)C)cc2c(c1CC=C(C)C)c(=O)c1c(o2)cc(c(c1O)CC=C(C)C)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL465553
PubChem CID:	44566652
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
ED50	1
IC50	7
Others	13

Activity Type	# Activity
Cell Line	6
Individual Protein	1
NON-MOLECULAR	1
Organism	12
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT139	Cell Line	HT-29	Homo sapiens	ED50	=	1.0	uM	PMID[570144]
NPT139	Cell Line	HT-29	Homo sapiens	IC50	=	1800.0	nM	PMID[570144]
NPT397	Cell Line	NCI-H460	Homo sapiens	IC50	=	12490.0	nM	PMID[570145]
NPT2297	Cell Line	ASPC1	Homo sapiens	IC50	=	14250.0	nM	PMID[570145]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	=	17450.0	nM	PMID[570145]
NPT323	Cell Line	SW-620	Homo sapiens	IC50	=	22730.0	nM	PMID[570145]
NPT2646	Organism	Alternaria tenuis	Alternaria tenuis	Inhibition	=	8.0	%	PMID[570143]
NPT2646	Organism	Alternaria tenuis	Alternaria tenuis	Inhibition	=	6.0	%	PMID[570143]
NPT2646	Organism	Alternaria tenuis	Alternaria tenuis	Inhibition	=	-6.0	%	PMID[570143]
NPT2647	Organism	Drechslera	Drechslera	Inhibition	=	11.0	%	PMID[570143]
NPT2647	Organism	Drechslera	Drechslera	Inhibition	=	51.0	%	PMID[570143]
NPT2647	Organism	Drechslera	Drechslera	Inhibition	=	14.0	%	PMID[570143]
NPT2648	Organism	Fusarium oxysporum f. sp. vasinfectum	Fusarium oxysporum f. sp. vasinfectum	Inhibition	=	6.0	%	PMID[570143]
NPT2648	Organism	Fusarium oxysporum f. sp. vasinfectum	Fusarium oxysporum f. sp. vasinfectum	Inhibition	=	5.0	%	PMID[570143]
NPT2648	Organism	Fusarium oxysporum f. sp. vasinfectum	Fusarium oxysporum f. sp. vasinfectum	Inhibition	=	4.0	%	PMID[570143]
NPT2648	Organism	Fusarium oxysporum f. sp. vasinfectum	Fusarium oxysporum f. sp. vasinfectum	Inhibition	=	3.0	%	PMID[570143]
NPT721	Individual Protein	Nuclear factor NF-kappa-B p65 subunit	Homo sapiens	IC50	>	10000.0	nM	PMID[570144]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	15080.0	nM	PMID[570145]
NPT35	Others	n.a.		Solubility	=	122000.0	nM	PMID[570145]

☑ 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 NPC474350 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	402
0.1-0.2	1796
0.2-0.3	4257
0.3-0.4	9768
0.4-0.5	8403
0.5-0.6	3608
0.6-0.7	5150
0.7-0.8	4876
0.8-0.85	2708
0.85-0.9	1440
0.9-0.95	268
0.95-1	21

Similarity Score	Similarity Level	Natural Product ID
0.9675	High Similarity	NPC217677
0.9675	High Similarity	NPC165977
0.9623	High Similarity	NPC99613
0.9623	High Similarity	NPC49487
0.9551	High Similarity	NPC475886
0.9551	High Similarity	NPC228785
0.9551	High Similarity	NPC474287
0.9551	High Similarity	NPC14353
0.9551	High Similarity	NPC56085
0.9503	High Similarity	NPC158226
0.9497	High Similarity	NPC29160
0.9494	High Similarity	NPC300984
0.949	High Similarity	NPC474351
0.949	High Similarity	NPC278052
0.949	High Similarity	NPC475883
0.949	High Similarity	NPC40491
0.949	High Similarity	NPC474186
0.949	High Similarity	NPC474187
0.949	High Similarity	NPC61010
0.9487	High Similarity	NPC100123
0.9441	High Similarity	NPC124470
0.9441	High Similarity	NPC109827
0.9437	High Similarity	NPC234331
0.9434	High Similarity	NPC267153
0.943	High Similarity	NPC229632
0.943	High Similarity	NPC93739
0.9427	High Similarity	NPC320359
0.9423	High Similarity	NPC300727
0.9423	High Similarity	NPC241904
0.9387	High Similarity	NPC289147
0.9379	High Similarity	NPC163130
0.9379	High Similarity	NPC165979
0.9375	High Similarity	NPC20216
0.9371	High Similarity	NPC236521
0.9371	High Similarity	NPC152659
0.9371	High Similarity	NPC156082
0.9371	High Similarity	NPC284007
0.9371	High Similarity	NPC220313
0.9371	High Similarity	NPC7483
0.9371	High Similarity	NPC248638
0.9371	High Similarity	NPC197168
0.9371	High Similarity	NPC236132
0.9367	High Similarity	NPC66288
0.9367	High Similarity	NPC303565
0.9363	High Similarity	NPC476242
0.9359	High Similarity	NPC274730
0.9359	High Similarity	NPC54928
0.9359	High Similarity	NPC142339
0.9333	High Similarity	NPC113446
0.9321	High Similarity	NPC20543
0.9321	High Similarity	NPC17219
0.9321	High Similarity	NPC246716
0.9321	High Similarity	NPC239440
0.9313	High Similarity	NPC472450
0.9313	High Similarity	NPC275780
0.9313	High Similarity	NPC25361
0.9313	High Similarity	NPC326520
0.9313	High Similarity	NPC8070
0.9313	High Similarity	NPC112981
0.9313	High Similarity	NPC239752
0.9308	High Similarity	NPC52204
0.9308	High Similarity	NPC108767
0.9308	High Similarity	NPC25152
0.9299	High Similarity	NPC36852
0.9299	High Similarity	NPC236796
0.9299	High Similarity	NPC78225
0.9299	High Similarity	NPC262286
0.9295	High Similarity	NPC471800
0.9268	High Similarity	NPC139350
0.9259	High Similarity	NPC26568
0.9255	High Similarity	NPC170245
0.9255	High Similarity	NPC472452
0.9255	High Similarity	NPC39091
0.925	High Similarity	NPC23298
0.925	High Similarity	NPC270837
0.925	High Similarity	NPC41301
0.925	High Similarity	NPC189473
0.9245	High Similarity	NPC266314
0.9245	High Similarity	NPC32694
0.9241	High Similarity	NPC238381
0.9241	High Similarity	NPC83763
0.9241	High Similarity	NPC168616
0.9236	High Similarity	NPC138243
0.9236	High Similarity	NPC191146
0.9236	High Similarity	NPC68093
0.9231	High Similarity	NPC475895
0.9231	High Similarity	NPC89474
0.9226	High Similarity	NPC117579
0.9226	High Similarity	NPC474663
0.9207	High Similarity	NPC181523
0.9202	High Similarity	NPC1827
0.9202	High Similarity	NPC10576
0.9198	High Similarity	NPC117854
0.9198	High Similarity	NPC272485
0.9198	High Similarity	NPC477154
0.9198	High Similarity	NPC6588
0.9198	High Similarity	NPC292788
0.9187	High Similarity	NPC294965
0.9182	High Similarity	NPC45146
0.9182	High Similarity	NPC200746
0.9182	High Similarity	NPC36217
0.9182	High Similarity	NPC119224
0.9182	High Similarity	NPC299436
0.9182	High Similarity	NPC235018
0.9177	High Similarity	NPC476981
0.9177	High Similarity	NPC223787
0.9177	High Similarity	NPC136674
0.9177	High Similarity	NPC108456
0.9177	High Similarity	NPC469584
0.9177	High Similarity	NPC181960
0.9172	High Similarity	NPC20541
0.9172	High Similarity	NPC37392
0.9172	High Similarity	NPC113906
0.9172	High Similarity	NPC472909
0.9167	High Similarity	NPC289968
0.9161	High Similarity	NPC29056
0.9161	High Similarity	NPC227122
0.9161	High Similarity	NPC179183
0.9136	High Similarity	NPC37870
0.9136	High Similarity	NPC472449
0.913	High Similarity	NPC146134
0.913	High Similarity	NPC273959
0.913	High Similarity	NPC475985
0.913	High Similarity	NPC234004
0.9119	High Similarity	NPC95936
0.9119	High Similarity	NPC329091
0.9119	High Similarity	NPC235448
0.9119	High Similarity	NPC250214
0.9114	High Similarity	NPC146211
0.9108	High Similarity	NPC250822
0.9108	High Similarity	NPC75279
0.9108	High Similarity	NPC280937
0.9108	High Similarity	NPC472915
0.9108	High Similarity	NPC276409
0.9103	High Similarity	NPC149614
0.9103	High Similarity	NPC202157
0.9103	High Similarity	NPC226973
0.9103	High Similarity	NPC208043
0.9103	High Similarity	NPC198615
0.9097	High Similarity	NPC328119
0.9074	High Similarity	NPC473286
0.9068	High Similarity	NPC329760
0.9068	High Similarity	NPC472448
0.9068	High Similarity	NPC201800
0.9068	High Similarity	NPC8300
0.9068	High Similarity	NPC470694
0.9068	High Similarity	NPC83922
0.9062	High Similarity	NPC80375
0.9062	High Similarity	NPC471973
0.9062	High Similarity	NPC143050
0.9062	High Similarity	NPC246478
0.9062	High Similarity	NPC47623
0.9062	High Similarity	NPC204290
0.9062	High Similarity	NPC476980
0.9062	High Similarity	NPC139036
0.9057	High Similarity	NPC472911
0.9057	High Similarity	NPC48208
0.9057	High Similarity	NPC162869
0.9057	High Similarity	NPC472913
0.9057	High Similarity	NPC472914
0.9057	High Similarity	NPC474208
0.9057	High Similarity	NPC245758
0.9057	High Similarity	NPC222814
0.9057	High Similarity	NPC474836
0.9057	High Similarity	NPC96167
0.9057	High Similarity	NPC475267
0.9057	High Similarity	NPC472910
0.9057	High Similarity	NPC156057
0.9051	High Similarity	NPC230149
0.9051	High Similarity	NPC92659
0.9051	High Similarity	NPC152951
0.9051	High Similarity	NPC227325
0.9051	High Similarity	NPC226025
0.9051	High Similarity	NPC167815
0.9051	High Similarity	NPC201136
0.9051	High Similarity	NPC146165
0.9051	High Similarity	NPC2476
0.9051	High Similarity	NPC57674
0.9051	High Similarity	NPC128863
0.9051	High Similarity	NPC477503
0.9051	High Similarity	NPC138360
0.9051	High Similarity	NPC280339
0.9051	High Similarity	NPC183597
0.9051	High Similarity	NPC255807
0.9051	High Similarity	NPC45849
0.9051	High Similarity	NPC50715
0.9051	High Similarity	NPC200761
0.9051	High Similarity	NPC31018
0.9051	High Similarity	NPC4455
0.9051	High Similarity	NPC168247
0.9051	High Similarity	NPC196439
0.9051	High Similarity	NPC208197
0.9051	High Similarity	NPC163780
0.9051	High Similarity	NPC117992
0.9051	High Similarity	NPC470327
0.9045	High Similarity	NPC101996
0.9045	High Similarity	NPC120537
0.9045	High Similarity	NPC180234
0.9045	High Similarity	NPC199100
0.9045	High Similarity	NPC471982

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 NPC474350 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	359
0.1-0.2	998
0.2-0.3	1834
0.3-0.4	2617
0.4-0.5	1835
0.5-0.6	923
0.6-0.7	398
0.7-0.8	135
0.8-0.85	35
0.85-0.9	13
0.9-0.95	3
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9068	High Similarity	NPD6232	Discontinued
0.9018	High Similarity	NPD7473	Discontinued
0.8987	High Similarity	NPD2801	Approved
0.8909	High Similarity	NPD5844	Phase 1
0.8868	High Similarity	NPD7819	Suspended
0.8868	High Similarity	NPD2393	Clinical (unspecified phase)
0.8805	High Similarity	NPD1934	Approved
0.875	High Similarity	NPD1465	Phase 2
0.8712	High Similarity	NPD5494	Approved
0.8696	High Similarity	NPD3817	Phase 2
0.8642	High Similarity	NPD4868	Clinical (unspecified phase)
0.8589	High Similarity	NPD7075	Discontinued
0.8588	High Similarity	NPD4338	Clinical (unspecified phase)
0.8503	High Similarity	NPD6166	Phase 2
0.8503	High Similarity	NPD6167	Clinical (unspecified phase)
0.8503	High Similarity	NPD6168	Clinical (unspecified phase)
0.8481	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8434	Intermediate Similarity	NPD6959	Discontinued
0.8418	Intermediate Similarity	NPD1511	Approved
0.8415	Intermediate Similarity	NPD3882	Suspended
0.8412	Intermediate Similarity	NPD7074	Phase 3
0.8405	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8402	Intermediate Similarity	NPD3818	Discontinued
0.8395	Intermediate Similarity	NPD7411	Suspended
0.8365	Intermediate Similarity	NPD2533	Approved
0.8365	Intermediate Similarity	NPD2532	Approved
0.8365	Intermediate Similarity	NPD2534	Approved
0.8353	Intermediate Similarity	NPD7054	Approved
0.8333	Intermediate Similarity	NPD4380	Phase 2
0.8333	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8313	Intermediate Similarity	NPD1512	Approved
0.8304	Intermediate Similarity	NPD7472	Approved
0.8272	Intermediate Similarity	NPD3226	Approved
0.8253	Intermediate Similarity	NPD3749	Approved
0.8242	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8232	Intermediate Similarity	NPD6801	Discontinued
0.8205	Intermediate Similarity	NPD2935	Discontinued
0.8192	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8176	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8161	Intermediate Similarity	NPD7808	Phase 3
0.8153	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8153	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.815	Intermediate Similarity	NPD6797	Phase 2
0.815	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8144	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8137	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8133	Intermediate Similarity	NPD5402	Approved
0.8113	Intermediate Similarity	NPD3750	Approved
0.8103	Intermediate Similarity	NPD7251	Discontinued
0.8101	Intermediate Similarity	NPD1549	Phase 2
0.8095	Intermediate Similarity	NPD919	Approved
0.8075	Intermediate Similarity	NPD6799	Approved
0.8038	Intermediate Similarity	NPD2346	Discontinued
0.8035	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD37	Approved
0.8	Intermediate Similarity	NPD6559	Discontinued
0.8	Intermediate Similarity	NPD6599	Discontinued
0.8	Intermediate Similarity	NPD1247	Approved
0.8	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7988	Intermediate Similarity	NPD6234	Discontinued
0.7976	Intermediate Similarity	NPD4965	Approved
0.7976	Intermediate Similarity	NPD4967	Phase 2
0.7976	Intermediate Similarity	NPD4966	Approved
0.7976	Intermediate Similarity	NPD7768	Phase 2
0.7949	Intermediate Similarity	NPD447	Suspended
0.7937	Intermediate Similarity	NPD2800	Approved
0.7927	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7911	Intermediate Similarity	NPD1510	Phase 2
0.7907	Intermediate Similarity	NPD3926	Phase 2
0.7895	Intermediate Similarity	NPD7199	Phase 2
0.7892	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7885	Intermediate Similarity	NPD1240	Approved
0.7862	Intermediate Similarity	NPD2796	Approved
0.7849	Intermediate Similarity	NPD5710	Approved
0.7849	Intermediate Similarity	NPD5711	Approved
0.7826	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7826	Intermediate Similarity	NPD1243	Approved
0.7818	Intermediate Similarity	NPD920	Approved
0.7803	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7799	Intermediate Similarity	NPD3748	Approved
0.7799	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7799	Intermediate Similarity	NPD2799	Discontinued
0.7785	Intermediate Similarity	NPD1607	Approved
0.7771	Intermediate Similarity	NPD7228	Approved
0.7744	Intermediate Similarity	NPD7390	Discontinued
0.774	Intermediate Similarity	NPD5953	Discontinued
0.7722	Intermediate Similarity	NPD230	Phase 1
0.7722	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7711	Intermediate Similarity	NPD5403	Approved
0.7709	Intermediate Similarity	NPD8313	Approved
0.7709	Intermediate Similarity	NPD8312	Approved
0.7697	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7669	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7665	Intermediate Similarity	NPD1653	Approved
0.7658	Intermediate Similarity	NPD943	Approved
0.7643	Intermediate Similarity	NPD2313	Discontinued
0.7643	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD6099	Approved
0.764	Intermediate Similarity	NPD6100	Approved
0.764	Intermediate Similarity	NPD1551	Phase 2
0.7636	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7627	Intermediate Similarity	NPD7286	Phase 2
0.761	Intermediate Similarity	NPD1933	Approved
0.759	Intermediate Similarity	NPD5401	Approved
0.7582	Intermediate Similarity	NPD8150	Discontinued
0.7579	Intermediate Similarity	NPD7435	Discontinued
0.7577	Intermediate Similarity	NPD7783	Phase 2
0.7577	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7571	Intermediate Similarity	NPD3751	Discontinued
0.7565	Intermediate Similarity	NPD8151	Discontinued
0.7564	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7562	Intermediate Similarity	NPD6651	Approved
0.7561	Intermediate Similarity	NPD4628	Phase 3
0.7543	Intermediate Similarity	NPD3787	Discontinued
0.7543	Intermediate Similarity	NPD7229	Phase 3
0.7516	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7513	Intermediate Similarity	NPD6782	Approved
0.7513	Intermediate Similarity	NPD6777	Approved
0.7513	Intermediate Similarity	NPD6779	Approved
0.7513	Intermediate Similarity	NPD6778	Approved
0.7513	Intermediate Similarity	NPD6776	Approved
0.7513	Intermediate Similarity	NPD6780	Approved
0.7513	Intermediate Similarity	NPD6781	Approved
0.7486	Intermediate Similarity	NPD8434	Phase 2
0.7469	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD1613	Approved
0.7438	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD1203	Approved
0.7421	Intermediate Similarity	NPD3268	Approved
0.7412	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD6190	Approved
0.7405	Intermediate Similarity	NPD6832	Phase 2
0.7403	Intermediate Similarity	NPD7240	Approved
0.7401	Intermediate Similarity	NPD5242	Approved
0.7396	Intermediate Similarity	NPD7696	Phase 3
0.7396	Intermediate Similarity	NPD7698	Approved
0.7396	Intermediate Similarity	NPD7697	Approved
0.7381	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD2344	Approved
0.7363	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD7870	Phase 2
0.7358	Intermediate Similarity	NPD4625	Phase 3
0.7358	Intermediate Similarity	NPD7871	Phase 2
0.7347	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD7874	Approved
0.7337	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD4060	Phase 1
0.7326	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD2797	Approved
0.7317	Intermediate Similarity	NPD5405	Approved
0.7317	Intermediate Similarity	NPD5404	Approved
0.7317	Intermediate Similarity	NPD5406	Approved
0.7317	Intermediate Similarity	NPD5408	Approved
0.7312	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD4287	Approved
0.7312	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD7685	Pre-registration
0.7299	Intermediate Similarity	NPD5353	Approved
0.7288	Intermediate Similarity	NPD8127	Discontinued
0.7284	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD7549	Discontinued
0.7263	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD6823	Phase 2
0.725	Intermediate Similarity	NPD3027	Phase 3
0.7249	Intermediate Similarity	NPD6534	Approved
0.7249	Intermediate Similarity	NPD6535	Approved
0.7245	Intermediate Similarity	NPD7701	Phase 2
0.7244	Intermediate Similarity	NPD1608	Approved
0.7244	Intermediate Similarity	NPD9717	Approved
0.7209	Intermediate Similarity	NPD7458	Discontinued
0.7205	Intermediate Similarity	NPD3764	Approved
0.7202	Intermediate Similarity	NPD2309	Approved
0.72	Intermediate Similarity	NPD4288	Approved
0.7188	Intermediate Similarity	NPD4908	Phase 1
0.7179	Intermediate Similarity	NPD422	Phase 1
0.7178	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD5124	Phase 1
0.7158	Intermediate Similarity	NPD4360	Phase 2
0.7158	Intermediate Similarity	NPD4363	Phase 3
0.7152	Intermediate Similarity	NPD4308	Phase 3
0.7152	Intermediate Similarity	NPD7033	Discontinued
0.7143	Intermediate Similarity	NPD8455	Phase 2
0.7143	Intermediate Similarity	NPD7003	Approved
0.7136	Intermediate Similarity	NPD7801	Approved
0.7135	Intermediate Similarity	NPD6273	Approved
0.7135	Intermediate Similarity	NPD7699	Phase 2
0.7135	Intermediate Similarity	NPD7700	Phase 2
0.7134	Intermediate Similarity	NPD9269	Phase 2
0.7126	Intermediate Similarity	NPD6386	Approved
0.7126	Intermediate Similarity	NPD6385	Approved
0.7107	Intermediate Similarity	NPD1470	Approved
0.7107	Intermediate Similarity	NPD3267	Approved
0.7107	Intermediate Similarity	NPD3266	Approved
0.7099	Intermediate Similarity	NPD411	Approved
0.7098	Intermediate Similarity	NPD8285	Discontinued
0.7097	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD9268	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