NPASS Compound

Structure

NPC475883 OpenBabel07101718182D 38 40 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 2.5981 -4.5000 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 -5.1962 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -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 3.4641 -3.0000 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 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 -3.5000 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 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 18 1 0 0 0 0 2 18 1 0 0 0 0 3 19 1 0 0 0 0 4 19 1 0 0 0 0 5 20 2 0 0 0 0 6 20 1 0 0 0 0 7 21 2 0 0 0 0 8 21 1 0 0 0 0 9 35 1 0 0 0 0 10 12 1 0 0 0 0 10 18 2 0 0 0 0 11 13 1 0 0 0 0 11 19 2 0 0 0 0 12 22 1 0 0 0 0 13 23 1 0 0 0 0 14 24 2 0 0 0 0 14 26 1 0 0 0 0 15 25 2 0 0 0 0 15 27 1 0 0 0 0 16 20 1 0 0 0 0 16 36 1 0 0 0 0 17 21 1 0 0 0 0 17 37 1 0 0 0 0 22 24 1 0 0 0 0 22 30 2 0 0 0 0 23 28 2 0 0 0 0 23 32 1 0 0 0 0 24 36 1 0 0 0 0 25 28 1 0 0 0 0 25 38 1 0 0 0 0 26 29 2 0 0 0 0 26 38 1 0 0 0 0 27 32 2 0 0 0 0 27 37 1 0 0 0 0 28 31 1 0 0 0 0 29 30 1 0 0 0 0 29 31 1 0 0 0 0 30 33 1 0 0 0 0 31 34 2 0 0 0 0 32 35 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	518.27
Volume:	560.099
LogP:	7.992
LogD:	4.436
LogS:	-5.361
# Rotatable Bonds:	11
TPSA:	78.13
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.207
Synthetic Accessibility Score:	3.468
Fsp3:	0.344
Lipinski Rule-of-5:	Rejected
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:	-4.72
MDCK Permeability:	1.5348019587690942e-05
Pgp-inhibitor:	0.998
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.021
20% Bioavailability (F20%):	0.953
30% Bioavailability (F30%):	0.145

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.002
Plasma Protein Binding (PPB):	86.09790802001953%
Volume Distribution (VD):	0.82
Pgp-substrate:	11.306851387023926%

ADMET: Metabolism

CYP1A2-inhibitor:	0.138
CYP1A2-substrate:	0.887
CYP2C19-inhibitor:	0.56
CYP2C19-substrate:	0.478
CYP2C9-inhibitor:	0.817
CYP2C9-substrate:	0.826
CYP2D6-inhibitor:	0.054
CYP2D6-substrate:	0.72
CYP3A4-inhibitor:	0.242
CYP3A4-substrate:	0.179

ADMET: Excretion

Clearance (CL):	7.397
Half-life (T1/2):	0.069

ADMET: Toxicity

hERG Blockers:	0.037
Human Hepatotoxicity (H-HT):	0.979
Drug-inuced Liver Injury (DILI):	0.932
AMES Toxicity:	0.615
Rat Oral Acute Toxicity:	0.118
Maximum Recommended Daily Dose:	0.194
Skin Sensitization:	0.681
Carcinogencity:	0.924
Eye Corrosion:	0.003
Eye Irritation:	0.172
Respiratory Toxicity:	0.753

Download Data

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

Natural Product: NPC475883

Natural Product ID:	NPC475883
*Common Name:**	Di-O-Methallylmangostin
IUPAC Name:	1-hydroxy-7-methoxy-2,8-bis(3-methylbut-2-enyl)-3,6-bis(2-methylprop-2-enoxy)xanthen-9-one
Synonyms:	Di-O-Methallylmangostin
Standard InCHIKey:	QPUAIXLSMPFNKZ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C32H38O6/c1-18(2)10-12-22-24(36-16-20(5)6)14-26-29(30(22)33)31(34)28-23(13-11-19(3)4)32(35-9)27(15-25(28)38-26)37-17-21(7)8/h10-11,14-15,33H,5,7,12-13,16-17H2,1-4,6,8-9H3
SMILES:	COc1c(OCC(=C)C)cc2c(c1CC=C(C)C)c(=O)c1c(o2)cc(c(c1O)CC=C(C)C)OCC(=C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL517920
PubChem CID:	10792038
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	=	-8.0	%	PMID[480075]
NPT2646	Organism	Alternaria tenuis	Alternaria tenuis	Inhibition	=	-2.0	%	PMID[480075]
NPT2646	Organism	Alternaria tenuis	Alternaria tenuis	Inhibition	=	4.0	%	PMID[480075]
NPT2646	Organism	Alternaria tenuis	Alternaria tenuis	Inhibition	=	-1.0	%	PMID[480075]
NPT2647	Organism	Drechslera	Drechslera	Inhibition	=	-1.0	%	PMID[480075]
NPT2647	Organism	Drechslera	Drechslera	Inhibition	=	17.0	%	PMID[480075]
NPT2648	Organism	Fusarium oxysporum f. sp. vasinfectum	Fusarium oxysporum f. sp. vasinfectum	Inhibition	=	1.0	%	PMID[480075]
NPT2648	Organism	Fusarium oxysporum f. sp. vasinfectum	Fusarium oxysporum f. sp. vasinfectum	Inhibition	=	2.0	%	PMID[480075]
NPT2648	Organism	Fusarium oxysporum f. sp. vasinfectum	Fusarium oxysporum f. sp. vasinfectum	Inhibition	=	3.0	%	PMID[480075]
NPT2648	Organism	Fusarium oxysporum f. sp. vasinfectum	Fusarium oxysporum f. sp. vasinfectum	Inhibition	=	9.0	%	PMID[480075]

☑ 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 NPC475883 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	434
0.1-0.2	1705
0.2-0.3	4028
0.3-0.4	10034
0.4-0.5	8367
0.5-0.6	3527
0.6-0.7	5004
0.7-0.8	5116
0.8-0.85	2649
0.85-0.9	1375
0.9-0.95	407
0.95-1	51

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC474351
0.9934	High Similarity	NPC474287
0.9934	High Similarity	NPC475886
0.9869	High Similarity	NPC474187
0.9869	High Similarity	NPC474186
0.9803	High Similarity	NPC165977
0.9803	High Similarity	NPC217677
0.9742	High Similarity	NPC7483
0.974	High Similarity	NPC40491
0.974	High Similarity	NPC278052
0.9675	High Similarity	NPC14353
0.9675	High Similarity	NPC228785
0.9675	High Similarity	NPC320359
0.9675	High Similarity	NPC299436
0.9675	High Similarity	NPC56085
0.9615	High Similarity	NPC236132
0.9615	High Similarity	NPC197168
0.9613	High Similarity	NPC61010
0.961	High Similarity	NPC100123
0.9554	High Similarity	NPC326520
0.9554	High Similarity	NPC25361
0.9551	High Similarity	NPC229632
0.9551	High Similarity	NPC201800
0.9545	High Similarity	NPC236796
0.9545	High Similarity	NPC300727
0.9545	High Similarity	NPC241904
0.9494	High Similarity	NPC39091
0.9494	High Similarity	NPC170245
0.949	High Similarity	NPC248638
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	NPC476242
0.9481	High Similarity	NPC142339
0.9481	High Similarity	NPC274730
0.9434	High Similarity	NPC6588
0.9434	High Similarity	NPC117854
0.9434	High Similarity	NPC477154
0.943	High Similarity	NPC472450
0.943	High Similarity	NPC275780
0.943	High Similarity	NPC239752
0.943	High Similarity	NPC475888
0.9427	High Similarity	NPC25152
0.9427	High Similarity	NPC52204
0.9423	High Similarity	NPC36217
0.9423	High Similarity	NPC119224
0.9419	High Similarity	NPC78225
0.9419	High Similarity	NPC181960
0.9419	High Similarity	NPC469584
0.9419	High Similarity	NPC262286
0.9419	High Similarity	NPC223787
0.9419	High Similarity	NPC36852
0.9416	High Similarity	NPC472909
0.9416	High Similarity	NPC37392
0.9416	High Similarity	NPC226025
0.9367	High Similarity	NPC189473
0.9367	High Similarity	NPC23298
0.9367	High Similarity	NPC475985
0.9367	High Similarity	NPC273959
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	NPC250214
0.9359	High Similarity	NPC95936
0.9359	High Similarity	NPC329091
0.9359	High Similarity	NPC210459
0.9355	High Similarity	NPC209614
0.9355	High Similarity	NPC470328
0.9355	High Similarity	NPC191146
0.9355	High Similarity	NPC472626
0.9355	High Similarity	NPC138243
0.9355	High Similarity	NPC68093
0.9351	High Similarity	NPC280937
0.9351	High Similarity	NPC472915
0.9351	High Similarity	NPC89474
0.9346	High Similarity	NPC117579
0.9308	High Similarity	NPC293319
0.9308	High Similarity	NPC473286
0.9304	High Similarity	NPC211107
0.9304	High Similarity	NPC294965
0.9299	High Similarity	NPC45146
0.9299	High Similarity	NPC200746
0.9299	High Similarity	NPC235018
0.9299	High Similarity	NPC321399
0.9295	High Similarity	NPC476981
0.9295	High Similarity	NPC475267
0.9295	High Similarity	NPC474208
0.9295	High Similarity	NPC48208
0.9295	High Similarity	NPC474836
0.9295	High Similarity	NPC472910
0.9295	High Similarity	NPC472911
0.9295	High Similarity	NPC245758
0.9295	High Similarity	NPC96167
0.9295	High Similarity	NPC156057
0.9295	High Similarity	NPC472913
0.9295	High Similarity	NPC162869
0.9295	High Similarity	NPC222814
0.9295	High Similarity	NPC136674
0.9295	High Similarity	NPC472914
0.929	High Similarity	NPC31018
0.929	High Similarity	NPC255807
0.929	High Similarity	NPC477503
0.929	High Similarity	NPC200761
0.929	High Similarity	NPC470327
0.929	High Similarity	NPC45849
0.929	High Similarity	NPC113906
0.9281	High Similarity	NPC338131
0.9281	High Similarity	NPC227122
0.9281	High Similarity	NPC179183
0.925	High Similarity	NPC120593
0.925	High Similarity	NPC472449
0.925	High Similarity	NPC37870
0.9245	High Similarity	NPC186686
0.9245	High Similarity	NPC146134
0.9236	High Similarity	NPC152904
0.9236	High Similarity	NPC85121
0.9236	High Similarity	NPC235448
0.9231	High Similarity	NPC472916
0.9231	High Similarity	NPC195796
0.9231	High Similarity	NPC235165
0.9231	High Similarity	NPC278778
0.9231	High Similarity	NPC35038
0.9231	High Similarity	NPC255106
0.9231	High Similarity	NPC291878
0.9226	High Similarity	NPC476631
0.9226	High Similarity	NPC298692
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	NPC218226
0.9182	High Similarity	NPC474150
0.9182	High Similarity	NPC83922
0.9182	High Similarity	NPC329760
0.9182	High Similarity	NPC472448
0.9182	High Similarity	NPC81679
0.9182	High Similarity	NPC474162
0.9182	High Similarity	NPC472964
0.9182	High Similarity	NPC470694
0.9177	High Similarity	NPC204290
0.9177	High Similarity	NPC472631
0.9177	High Similarity	NPC139036
0.9177	High Similarity	NPC246478
0.9177	High Similarity	NPC471973
0.9177	High Similarity	NPC472630
0.9177	High Similarity	NPC476980
0.9177	High Similarity	NPC80375
0.9172	High Similarity	NPC474055
0.9172	High Similarity	NPC473272
0.9172	High Similarity	NPC129684
0.9172	High Similarity	NPC99597
0.9172	High Similarity	NPC27337
0.9172	High Similarity	NPC210084
0.9172	High Similarity	NPC472963
0.9172	High Similarity	NPC472598
0.9172	High Similarity	NPC299520
0.9172	High Similarity	NPC284820
0.9172	High Similarity	NPC291508
0.9167	High Similarity	NPC2928
0.9167	High Similarity	NPC152951
0.9167	High Similarity	NPC117992
0.9167	High Similarity	NPC230149
0.9167	High Similarity	NPC168247
0.9167	High Similarity	NPC134287
0.9167	High Similarity	NPC130589
0.9167	High Similarity	NPC57674
0.9167	High Similarity	NPC67396
0.9167	High Similarity	NPC213622
0.9161	High Similarity	NPC249570
0.9161	High Similarity	NPC199100
0.9161	High Similarity	NPC180234
0.9161	High Similarity	NPC106976
0.9161	High Similarity	NPC120537
0.9161	High Similarity	NPC474843
0.9161	High Similarity	NPC101996
0.9161	High Similarity	NPC471982
0.9156	High Similarity	NPC151473
0.9156	High Similarity	NPC239363
0.9156	High Similarity	NPC306821
0.9146	High Similarity	NPC289147
0.9141	High Similarity	NPC260263
0.9136	High Similarity	NPC99613
0.9136	High Similarity	NPC49487
0.913	High Similarity	NPC272502
0.913	High Similarity	NPC43319
0.913	High Similarity	NPC470462
0.913	High Similarity	NPC128293
0.913	High Similarity	NPC472452
0.913	High Similarity	NPC29160
0.9125	High Similarity	NPC207690
0.9125	High Similarity	NPC473313
0.9125	High Similarity	NPC470459
0.9125	High Similarity	NPC329669
0.9125	High Similarity	NPC472278

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 NPC475883 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	967
0.2-0.3	1789
0.3-0.4	2652
0.4-0.5	1830
0.5-0.6	913
0.6-0.7	437
0.7-0.8	125
0.8-0.85	39
0.85-0.9	14
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9103	High Similarity	NPD2393	Clinical (unspecified phase)
0.9103	High Similarity	NPD2801	Approved
0.9038	High Similarity	NPD1934	Approved
0.8938	High Similarity	NPD5494	Approved
0.8861	High Similarity	NPD7819	Suspended
0.878	High Similarity	NPD7473	Discontinued
0.8712	High Similarity	NPD6232	Discontinued
0.8675	High Similarity	NPD5844	Phase 1
0.8634	High Similarity	NPD3882	Suspended
0.8606	High Similarity	NPD6168	Clinical (unspecified phase)
0.8606	High Similarity	NPD6167	Clinical (unspecified phase)
0.8606	High Similarity	NPD6166	Phase 2
0.859	High Similarity	NPD4378	Clinical (unspecified phase)
0.8571	High Similarity	NPD8443	Clinical (unspecified phase)
0.8537	High Similarity	NPD6959	Discontinued
0.8526	High Similarity	NPD1511	Approved
0.8512	High Similarity	NPD7074	Phase 3
0.8466	Intermediate Similarity	NPD7075	Discontinued
0.8457	Intermediate Similarity	NPD3817	Phase 2
0.8452	Intermediate Similarity	NPD7054	Approved
0.8438	Intermediate Similarity	NPD4380	Phase 2
0.8418	Intermediate Similarity	NPD1512	Approved
0.8405	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8402	Intermediate Similarity	NPD7472	Approved
0.8395	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8393	Intermediate Similarity	NPD3818	Discontinued
0.8377	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8377	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8363	Intermediate Similarity	NPD7808	Phase 3
0.8363	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8323	Intermediate Similarity	NPD1549	Phase 2
0.8282	Intermediate Similarity	NPD1465	Phase 2
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
0.8198	Intermediate Similarity	NPD7251	Discontinued
0.816	Intermediate Similarity	NPD7411	Suspended
0.814	Intermediate Similarity	NPD6797	Phase 2
0.8133	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8129	Intermediate Similarity	NPD1510	Phase 2
0.8125	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8089	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8079	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8077	Intermediate Similarity	NPD2796	Approved
0.8077	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.8072	Intermediate Similarity	NPD7768	Phase 2
0.8059	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8038	Intermediate Similarity	NPD2800	Approved
0.8035	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD6801	Discontinued
0.7989	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD1240	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	NPD3926	Phase 2
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	NPD919	Approved
0.7848	Intermediate Similarity	NPD6100	Approved
0.7848	Intermediate Similarity	NPD6099	Approved
0.7818	Intermediate Similarity	NPD3226	Approved
0.7799	Intermediate Similarity	NPD2346	Discontinued
0.7784	Intermediate Similarity	NPD37	Approved
0.7765	Intermediate Similarity	NPD6234	Discontinued
0.7756	Intermediate Similarity	NPD943	Approved
0.7751	Intermediate Similarity	NPD4965	Approved
0.7751	Intermediate Similarity	NPD4967	Phase 2
0.7751	Intermediate Similarity	NPD4966	Approved
0.7733	Intermediate Similarity	NPD5711	Approved
0.7733	Intermediate Similarity	NPD5710	Approved
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
0.7657	Intermediate Similarity	NPD7228	Approved
0.7657	Intermediate Similarity	NPD3751	Discontinued
0.7643	Intermediate Similarity	NPD1613	Approved
0.7643	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.763	Intermediate Similarity	NPD3787	Discontinued
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
0.759	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD920	Approved
0.7586	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7569	Intermediate Similarity	NPD8150	Discontinued
0.7566	Intermediate Similarity	NPD7697	Approved
0.7566	Intermediate Similarity	NPD7698	Approved
0.7566	Intermediate Similarity	NPD7696	Phase 3
0.7562	Intermediate Similarity	NPD3748	Approved
0.7562	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7562	Intermediate Similarity	NPD2799	Discontinued
0.7552	Intermediate Similarity	NPD8151	Discontinued
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)
0.75	Intermediate Similarity	NPD6781	Approved
0.75	Intermediate Similarity	NPD6777	Approved
0.75	Intermediate Similarity	NPD6776	Approved
0.75	Intermediate Similarity	NPD6780	Approved
0.75	Intermediate Similarity	NPD6778	Approved
0.75	Intermediate Similarity	NPD6782	Approved
0.75	Intermediate Similarity	NPD6779	Approved
0.7485	Intermediate Similarity	NPD1243	Approved
0.7485	Intermediate Similarity	NPD5403	Approved
0.7474	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7474	Intermediate Similarity	NPD7783	Phase 2
0.7474	Intermediate Similarity	NPD7435	Discontinued
0.7473	Intermediate Similarity	NPD8434	Phase 2
0.747	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7469	Intermediate Similarity	NPD2344	Approved
0.7452	Intermediate Similarity	NPD3027	Phase 3
0.7452	Intermediate Similarity	NPD4625	Phase 3
0.7439	Intermediate Similarity	NPD4628	Phase 3
0.741	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7409	Intermediate Similarity	NPD7701	Phase 2
0.7405	Intermediate Similarity	NPD2313	Discontinued
0.7389	Intermediate Similarity	NPD4908	Phase 1
0.7375	Intermediate Similarity	NPD1933	Approved
0.7365	Intermediate Similarity	NPD5401	Approved
0.7349	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD1653	Approved
0.7333	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD7874	Approved
0.7333	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD6823	Phase 2
0.7326	Intermediate Similarity	NPD4363	Phase 3
0.7326	Intermediate Similarity	NPD4360	Phase 2
0.731	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7302	Intermediate Similarity	NPD7700	Phase 2
0.7302	Intermediate Similarity	NPD7699	Phase 2
0.7296	Intermediate Similarity	NPD7801	Approved
0.7294	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD7685	Pre-registration
0.7293	Intermediate Similarity	NPD7240	Approved
0.7289	Intermediate Similarity	NPD2309	Approved
0.7288	Intermediate Similarity	NPD5242	Approved
0.7283	Intermediate Similarity	NPD5353	Approved
0.7273	Intermediate Similarity	NPD1610	Phase 2
0.7267	Intermediate Similarity	NPD6844	Discontinued
0.7249	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD6535	Approved
0.7234	Intermediate Similarity	NPD6534	Approved
0.7215	Intermediate Similarity	NPD9494	Approved
0.7215	Intermediate Similarity	NPD2861	Phase 2
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)
0.7186	Intermediate Similarity	NPD6190	Approved
0.7175	Intermediate Similarity	NPD8127	Discontinued
0.717	Intermediate Similarity	NPD6832	Phase 2
0.7169	Intermediate Similarity	NPD6674	Discontinued
0.7161	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD1201	Approved
0.716	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD2403	Approved
0.7126	Intermediate Similarity	NPD8455	Phase 2
0.711	Intermediate Similarity	NPD6386	Approved
0.711	Intermediate Similarity	NPD6385	Approved
0.7105	Intermediate Similarity	NPD4361	Phase 2
0.7105	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD7584	Approved
0.7091	Intermediate Similarity	NPD5405	Approved
0.7091	Intermediate Similarity	NPD5404	Approved
0.7091	Intermediate Similarity	NPD5406	Approved
0.7091	Intermediate Similarity	NPD5408	Approved
0.7089	Intermediate Similarity	NPD1203	Approved
0.7081	Intermediate Similarity	NPD3268	Approved
0.7081	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD4749	Approved
0.707	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD7549	Discontinued
0.7059	Intermediate Similarity	NPD7907	Approved
0.7055	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD1471	Phase 3
0.7044	Intermediate Similarity	NPD2798	Approved
0.703	Intermediate Similarity	NPD7033	Discontinued
0.7029	Intermediate Similarity	NPD5760	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