NPASS Compound

Structure

CID227337 OpenBabel06191716022D 28 30 0 0 0 0 0 0 0 0999 V2000 -6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -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 -6.9282 0.0000 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 1.7321 -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 -4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 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 -6.9282 1.0000 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 -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 1.7321 -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 -0.8660 -0.5000 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 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 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 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 -1.7321 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 1 0 0 0 0 2 13 1 0 0 0 0 3 14 1 0 0 0 0 4 6 1 0 0 0 0 4 7 1 0 0 0 0 5 8 2 0 0 0 0 5 9 1 0 0 0 0 6 13 2 0 0 0 0 7 14 1 0 0 0 0 8 16 1 0 0 0 0 9 17 2 0 0 0 0 10 11 1 0 0 0 0 10 14 2 0 0 0 0 11 15 1 0 0 0 0 12 18 2 0 0 0 0 12 19 1 0 0 0 0 15 18 1 0 0 0 0 15 21 2 0 0 0 0 16 22 1 0 0 0 0 16 23 2 0 0 0 0 17 23 1 0 0 0 0 17 24 1 0 0 0 0 18 25 1 0 0 0 0 19 20 2 0 0 0 0 19 28 1 0 0 0 0 20 21 1 0 0 0 0 20 22 1 0 0 0 0 21 26 1 0 0 0 0 22 27 2 0 0 0 0 23 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	380.16
Volume:	400.918
LogP:	5.67
LogD:	3.464
LogS:	-2.8
# Rotatable Bonds:	5
TPSA:	90.9
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.413
Synthetic Accessibility Score:	2.945
Fsp3:	0.261
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:	-4.895
MDCK Permeability:	1.665966738073621e-05
Pgp-inhibitor:	0.5
Pgp-substrate:	0.229
Human Intestinal Absorption (HIA):	0.019
20% Bioavailability (F20%):	0.652
30% Bioavailability (F30%):	0.565

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.005
Plasma Protein Binding (PPB):	96.05455780029297%
Volume Distribution (VD):	0.435
Pgp-substrate:	3.5307586193084717%

ADMET: Metabolism

CYP1A2-inhibitor:	0.918
CYP1A2-substrate:	0.286
CYP2C19-inhibitor:	0.909
CYP2C19-substrate:	0.063
CYP2C9-inhibitor:	0.867
CYP2C9-substrate:	0.927
CYP2D6-inhibitor:	0.816
CYP2D6-substrate:	0.339
CYP3A4-inhibitor:	0.198
CYP3A4-substrate:	0.067

ADMET: Excretion

Clearance (CL):	4.013
Half-life (T1/2):	0.508

ADMET: Toxicity

hERG Blockers:	0.004
Human Hepatotoxicity (H-HT):	0.829
Drug-inuced Liver Injury (DILI):	0.936
AMES Toxicity:	0.474
Rat Oral Acute Toxicity:	0.104
Maximum Recommended Daily Dose:	0.566
Skin Sensitization:	0.916
Carcinogencity:	0.129
Eye Corrosion:	0.004
Eye Irritation:	0.895
Respiratory Toxicity:	0.271

Download Data

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

Natural Product: NPC227337

Natural Product ID:	NPC227337
*Common Name:**	Mangostinone
IUPAC Name:	2-[(2E)-3,7-dimethylocta-2,6-dienyl]-1,3,5-trihydroxyxanthen-9-one
Synonyms:	Mangostinone
Standard InCHIKey:	RJLWIAOXQDZMTB-GXDHUFHOSA-N
Standard InCHI:	InChI=1S/C23H24O5/c1-13(2)6-4-7-14(3)10-11-15-18(25)12-19-20(21(15)26)22(27)16-8-5-9-17(24)23(16)28-19/h5-6,8-10,12,24-26H,4,7,11H2,1-3H3/b14-10+
SMILES:	CC(=CCC/C(=C/Cc1c(cc2c(c1O)c(=O)c1cccc(c1o2)O)O)/C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL481310
PubChem CID:	6478778
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:0003517] 2-prenylated xanthones

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO25472	Garcinia cowa	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1071/CH03175]
NPO7811	Scleronephthya pallida	Species	Nephtheidae	Eukaryota	n.a.	n.a.	n.a.	PMID[10075773]
NPO10376	Arcyria denudata	Species	Trichiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[16933891]
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]
NPO25472	Garcinia cowa	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19299148]
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]
NPO25472	Garcinia cowa	Species	Clusiaceae	Eukaryota	twigs	n.a.	n.a.	PMID[20058933]
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]
NPO25472	Garcinia cowa	Species	Clusiaceae	Eukaryota	flowers	Pakook, Muang District, Chiang Rai Province, Thailand	2013-Feb	PMID[25651042]
NPO25472	Garcinia cowa	Species	Clusiaceae	Eukaryota	young fruits	Khokkhon, Tha Bo District, Nong Khai Province, Thailand	2011-Aug	PMID[25651042]
NPO25472	Garcinia cowa	Species	Clusiaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[31860303]
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]
NPO10849	Eucalyptus camaldulensis	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6249	Garcinia mangostana	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25472	Garcinia cowa	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10849	Eucalyptus camaldulensis	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6249	Garcinia mangostana	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25472	Garcinia cowa	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10391	Dolomiaea souliei	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10391	Dolomiaea souliei	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO10221	Streptomyces alboniger	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO10056	Nicotiana sylvestris	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7534	Leptogorgia sarmentosa	Species	Gorgoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24931	Myelochroa aurulenta	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8560	Aplidium tabascum	Species	Polyclinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25472	Garcinia cowa	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9741	Actinopyga agassizi	Species	Holothuriidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10849	Eucalyptus camaldulensis	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3707	Chromatium okenii	Species	Chromatiaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO8927	Poria selecta	Species	Coccinellidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6249	Garcinia mangostana	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7811	Scleronephthya pallida	Species	Nephtheidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27924	Serpocaulon triseriale	Species	Polypodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10391	Dolomiaea souliei	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4064	Halimodendron halodendron	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25216	Senecio vellereus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10376	Arcyria denudata	Species	Trichiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9717	Wibelia divaricata	Species	Davalliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8354	Aster bellidiastrum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12600	Trametes cinnabarina	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3449	Lonicera hypoleuca	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	1
Others	1

Activity Type	# Activity
Cell Line	1
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	19000.0	nM	PMID[547879]
NPT441	Individual Protein	Cytochrome P450 19A1	Homo sapiens	Activity	=	78.8	%	PMID[547880]

☑ 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 NPC227337 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	444
0.1-0.2	1874
0.2-0.3	4719
0.3-0.4	11266
0.4-0.5	6368
0.5-0.6	3723
0.6-0.7	5076
0.7-0.8	4704
0.8-0.85	2349
0.85-0.9	1386
0.9-0.95	658
0.95-1	130

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC33051
1.0	High Similarity	NPC70433
1.0	High Similarity	NPC273462
1.0	High Similarity	NPC49402
0.9932	High Similarity	NPC57674
0.9932	High Similarity	NPC117992
0.9932	High Similarity	NPC168247
0.9932	High Similarity	NPC230149
0.9932	High Similarity	NPC152951
0.9799	High Similarity	NPC161960
0.9799	High Similarity	NPC474681
0.9799	High Similarity	NPC187745
0.9799	High Similarity	NPC304008
0.9799	High Similarity	NPC218313
0.9797	High Similarity	NPC472280
0.9797	High Similarity	NPC256925
0.9733	High Similarity	NPC204879
0.9732	High Similarity	NPC115853
0.9732	High Similarity	NPC191146
0.9732	High Similarity	NPC5322
0.9732	High Similarity	NPC68093
0.9732	High Similarity	NPC133970
0.9732	High Similarity	NPC470600
0.9732	High Similarity	NPC6633
0.9732	High Similarity	NPC472455
0.9732	High Similarity	NPC138243
0.9667	High Similarity	NPC180011
0.9667	High Similarity	NPC136674
0.9667	High Similarity	NPC291508
0.9667	High Similarity	NPC262286
0.9667	High Similarity	NPC219867
0.9667	High Similarity	NPC78225
0.9667	High Similarity	NPC36852
0.9664	High Similarity	NPC234255
0.9664	High Similarity	NPC200246
0.9662	High Similarity	NPC237994
0.9662	High Similarity	NPC257648
0.9662	High Similarity	NPC477231
0.966	High Similarity	NPC29231
0.9658	High Similarity	NPC272721
0.9658	High Similarity	NPC196277
0.9658	High Similarity	NPC43669
0.9605	High Similarity	NPC29876
0.9605	High Similarity	NPC234644
0.9605	High Similarity	NPC167678
0.9603	High Similarity	NPC235448
0.96	High Similarity	NPC35038
0.96	High Similarity	NPC291878
0.96	High Similarity	NPC195796
0.96	High Similarity	NPC278778
0.9595	High Similarity	NPC154345
0.9595	High Similarity	NPC31363
0.9589	High Similarity	NPC77378
0.9542	High Similarity	NPC472448
0.9542	High Similarity	NPC83922
0.9539	High Similarity	NPC471973
0.9539	High Similarity	NPC476980
0.9539	High Similarity	NPC204290
0.9539	High Similarity	NPC188433
0.9536	High Similarity	NPC27337
0.9536	High Similarity	NPC299520
0.9536	High Similarity	NPC472598
0.9536	High Similarity	NPC129684
0.9536	High Similarity	NPC474055
0.9536	High Similarity	NPC52889
0.9533	High Similarity	NPC113906
0.9533	High Similarity	NPC477503
0.9533	High Similarity	NPC470327
0.9533	High Similarity	NPC45849
0.9533	High Similarity	NPC200761
0.953	High Similarity	NPC39732
0.953	High Similarity	NPC472912
0.953	High Similarity	NPC471982
0.953	High Similarity	NPC60972
0.9527	High Similarity	NPC88804
0.9527	High Similarity	NPC3825
0.9527	High Similarity	NPC472279
0.9481	High Similarity	NPC124038
0.9481	High Similarity	NPC319200
0.9481	High Similarity	NPC187491
0.9477	High Similarity	NPC258331
0.9477	High Similarity	NPC266314
0.9477	High Similarity	NPC57715
0.9477	High Similarity	NPC134783
0.9477	High Similarity	NPC259456
0.9474	High Similarity	NPC185258
0.9474	High Similarity	NPC95936
0.9474	High Similarity	NPC100123
0.9474	High Similarity	NPC184755
0.9474	High Similarity	NPC250214
0.9474	High Similarity	NPC74178
0.9474	High Similarity	NPC172770
0.947	High Similarity	NPC471985
0.947	High Similarity	NPC472916
0.947	High Similarity	NPC470328
0.947	High Similarity	NPC209614
0.947	High Similarity	NPC472907
0.947	High Similarity	NPC472626
0.9467	High Similarity	NPC18727
0.9467	High Similarity	NPC213896
0.9467	High Similarity	NPC472905
0.9467	High Similarity	NPC292214
0.9467	High Similarity	NPC271779
0.9467	High Similarity	NPC167091
0.9467	High Similarity	NPC469550
0.9467	High Similarity	NPC88645
0.9467	High Similarity	NPC192083
0.9467	High Similarity	NPC206238
0.9463	High Similarity	NPC251110
0.9463	High Similarity	NPC256406
0.9456	High Similarity	NPC168803
0.9419	High Similarity	NPC472277
0.9419	High Similarity	NPC108433
0.9419	High Similarity	NPC300053
0.9416	High Similarity	NPC474162
0.9416	High Similarity	NPC474150
0.9416	High Similarity	NPC474033
0.9416	High Similarity	NPC474034
0.9416	High Similarity	NPC476247
0.9412	High Similarity	NPC282009
0.9412	High Similarity	NPC228785
0.9412	High Similarity	NPC192686
0.9412	High Similarity	NPC36217
0.9412	High Similarity	NPC119209
0.9412	High Similarity	NPC14353
0.9412	High Similarity	NPC287328
0.9412	High Similarity	NPC320359
0.9412	High Similarity	NPC118256
0.9412	High Similarity	NPC56085
0.9412	High Similarity	NPC472624
0.9408	High Similarity	NPC156057
0.9408	High Similarity	NPC475267
0.9408	High Similarity	NPC476981
0.9408	High Similarity	NPC223787
0.9408	High Similarity	NPC162869
0.9408	High Similarity	NPC472911
0.9408	High Similarity	NPC79053
0.9408	High Similarity	NPC245758
0.9408	High Similarity	NPC474208
0.9408	High Similarity	NPC210084
0.9408	High Similarity	NPC474836
0.9408	High Similarity	NPC472910
0.9408	High Similarity	NPC67876
0.9408	High Similarity	NPC222814
0.9408	High Similarity	NPC472963
0.9408	High Similarity	NPC472913
0.9408	High Similarity	NPC48208
0.9408	High Similarity	NPC472914
0.9408	High Similarity	NPC99597
0.9408	High Similarity	NPC96167
0.9404	High Similarity	NPC255807
0.9404	High Similarity	NPC20830
0.9404	High Similarity	NPC226025
0.9404	High Similarity	NPC31018
0.9404	High Similarity	NPC256612
0.9404	High Similarity	NPC321779
0.9404	High Similarity	NPC2928
0.94	High Similarity	NPC157784
0.94	High Similarity	NPC37684
0.94	High Similarity	NPC219582
0.94	High Similarity	NPC106976
0.94	High Similarity	NPC302950
0.94	High Similarity	NPC120537
0.94	High Similarity	NPC39007
0.94	High Similarity	NPC161277
0.94	High Similarity	NPC236637
0.94	High Similarity	NPC101996
0.94	High Similarity	NPC180234
0.94	High Similarity	NPC260979
0.94	High Similarity	NPC63187
0.94	High Similarity	NPC199100
0.9396	High Similarity	NPC248102
0.9396	High Similarity	NPC151473
0.9396	High Similarity	NPC61620
0.9388	High Similarity	NPC209278
0.9384	High Similarity	NPC59551
0.9359	High Similarity	NPC235610
0.9355	High Similarity	NPC472281
0.9355	High Similarity	NPC205265
0.9355	High Similarity	NPC303460
0.9355	High Similarity	NPC306321
0.9355	High Similarity	NPC23298
0.9355	High Similarity	NPC189473
0.9355	High Similarity	NPC18100
0.9355	High Similarity	NPC220313
0.9351	High Similarity	NPC472632
0.9351	High Similarity	NPC472634
0.9351	High Similarity	NPC471499
0.9351	High Similarity	NPC471210
0.9351	High Similarity	NPC40491
0.9351	High Similarity	NPC61010
0.9351	High Similarity	NPC26326
0.9351	High Similarity	NPC278052
0.9351	High Similarity	NPC474038
0.9351	High Similarity	NPC472275
0.9346	High Similarity	NPC22192
0.9346	High Similarity	NPC55738
0.9342	High Similarity	NPC274730
0.9342	High Similarity	NPC282307
0.9342	High Similarity	NPC235165

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 NPC227337 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	398
0.1-0.2	993
0.2-0.3	1735
0.3-0.4	2694
0.4-0.5	1771
0.5-0.6	1006
0.6-0.7	376
0.7-0.8	115
0.8-0.85	40
0.85-0.9	14
0.9-0.95	6
0.95-1	2

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9467	High Similarity	NPD2393	Clinical (unspecified phase)
0.94	High Similarity	NPD1934	Approved
0.9338	High Similarity	NPD2801	Approved
0.9216	High Similarity	NPD3882	Suspended
0.9122	High Similarity	NPD1511	Approved
0.9	High Similarity	NPD1512	Approved
0.8931	High Similarity	NPD6166	Phase 2
0.8931	High Similarity	NPD6167	Clinical (unspecified phase)
0.8931	High Similarity	NPD6168	Clinical (unspecified phase)
0.882	High Similarity	NPD3818	Discontinued
0.8808	High Similarity	NPD4378	Clinical (unspecified phase)
0.8797	High Similarity	NPD5494	Approved
0.879	High Similarity	NPD7075	Discontinued
0.8766	High Similarity	NPD4380	Phase 2
0.8726	High Similarity	NPD4868	Clinical (unspecified phase)
0.8718	High Similarity	NPD7096	Clinical (unspecified phase)
0.8712	High Similarity	NPD7074	Phase 3
0.8684	High Similarity	NPD7410	Clinical (unspecified phase)
0.8662	High Similarity	NPD3817	Phase 2
0.8658	High Similarity	NPD1549	Phase 2
0.865	High Similarity	NPD7054	Approved
0.8599	High Similarity	NPD7819	Suspended
0.8598	High Similarity	NPD7472	Approved
0.8591	High Similarity	NPD1552	Clinical (unspecified phase)
0.8591	High Similarity	NPD1550	Clinical (unspecified phase)
0.8571	High Similarity	NPD6232	Discontinued
0.8562	High Similarity	NPD943	Approved
0.8528	High Similarity	NPD7473	Discontinued
0.8481	Intermediate Similarity	NPD1465	Phase 2
0.8471	Intermediate Similarity	NPD7411	Suspended
0.8456	Intermediate Similarity	NPD1510	Phase 2
0.8443	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8438	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8435	Intermediate Similarity	NPD1240	Approved
0.8434	Intermediate Similarity	NPD6797	Phase 2
0.8428	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8418	Intermediate Similarity	NPD6801	Discontinued
0.84	Intermediate Similarity	NPD2796	Approved
0.8383	Intermediate Similarity	NPD7251	Discontinued
0.8377	Intermediate Similarity	NPD6799	Approved
0.8333	Intermediate Similarity	NPD7808	Phase 3
0.8322	Intermediate Similarity	NPD1607	Approved
0.8313	Intermediate Similarity	NPD5844	Phase 1
0.8214	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8204	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD3926	Phase 2
0.8176	Intermediate Similarity	NPD6599	Discontinued
0.8171	Intermediate Similarity	NPD6959	Discontinued
0.8171	Intermediate Similarity	NPD1247	Approved
0.8166	Intermediate Similarity	NPD6559	Discontinued
0.8163	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.816	Intermediate Similarity	NPD919	Approved
0.8133	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8117	Intermediate Similarity	NPD2800	Approved
0.8098	Intermediate Similarity	NPD3749	Approved
0.8095	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8065	Intermediate Similarity	NPD3750	Approved
0.8039	Intermediate Similarity	NPD2935	Discontinued
0.8037	Intermediate Similarity	NPD7768	Phase 2
0.8013	Intermediate Similarity	NPD447	Suspended
0.8	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD5402	Approved
0.7974	Intermediate Similarity	NPD2799	Discontinued
0.7974	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7947	Intermediate Similarity	NPD1613	Approved
0.7947	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7944	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7935	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD230	Phase 1
0.7888	Intermediate Similarity	NPD3226	Approved
0.7885	Intermediate Similarity	NPD1243	Approved
0.7875	Intermediate Similarity	NPD5403	Approved
0.7871	Intermediate Similarity	NPD2346	Discontinued
0.7871	Intermediate Similarity	NPD2344	Approved
0.7862	Intermediate Similarity	NPD2532	Approved
0.7862	Intermediate Similarity	NPD2534	Approved
0.7862	Intermediate Similarity	NPD2533	Approved
0.7857	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7815	Intermediate Similarity	NPD2313	Discontinued
0.7806	Intermediate Similarity	NPD6100	Approved
0.7806	Intermediate Similarity	NPD1551	Phase 2
0.7806	Intermediate Similarity	NPD6099	Approved
0.7791	Intermediate Similarity	NPD5953	Discontinued
0.7778	Intermediate Similarity	NPD1933	Approved
0.7764	Intermediate Similarity	NPD920	Approved
0.775	Intermediate Similarity	NPD5401	Approved
0.7748	Intermediate Similarity	NPD3027	Phase 3
0.7742	Intermediate Similarity	NPD3748	Approved
0.774	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD9494	Approved
0.7727	Intermediate Similarity	NPD6651	Approved
0.7722	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7722	Intermediate Similarity	NPD4628	Phase 3
0.7703	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7674	Intermediate Similarity	NPD7286	Phase 2
0.7673	Intermediate Similarity	NPD2309	Approved
0.764	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7633	Intermediate Similarity	NPD7199	Phase 2
0.7625	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD6234	Discontinued
0.761	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD1203	Approved
0.76	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD7390	Discontinued
0.7571	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7556	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7544	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD4625	Phase 3
0.7514	Intermediate Similarity	NPD3751	Discontinued
0.75	Intermediate Similarity	NPD1653	Approved
0.7458	Intermediate Similarity	NPD8312	Approved
0.7458	Intermediate Similarity	NPD8313	Approved
0.7453	Intermediate Similarity	NPD6190	Approved
0.7451	Intermediate Similarity	NPD4908	Phase 1
0.745	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7434	Intermediate Similarity	NPD2798	Approved
0.7425	Intermediate Similarity	NPD37	Approved
0.7414	Intermediate Similarity	NPD7228	Approved
0.74	Intermediate Similarity	NPD9717	Approved
0.74	Intermediate Similarity	NPD9269	Phase 2
0.7396	Intermediate Similarity	NPD4966	Approved
0.7396	Intermediate Similarity	NPD4965	Approved
0.7396	Intermediate Similarity	NPD4967	Phase 2
0.7391	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7384	Intermediate Similarity	NPD3787	Discontinued
0.7384	Intermediate Similarity	NPD5711	Approved
0.7384	Intermediate Similarity	NPD5710	Approved
0.7368	Intermediate Similarity	NPD1470	Approved
0.7355	Intermediate Similarity	NPD3268	Approved
0.7345	Intermediate Similarity	NPD7685	Pre-registration
0.7341	Intermediate Similarity	NPD5242	Approved
0.7338	Intermediate Similarity	NPD6832	Phase 2
0.7333	Intermediate Similarity	NPD1610	Phase 2
0.7317	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD4308	Phase 3
0.7285	Intermediate Similarity	NPD1608	Approved
0.7283	Intermediate Similarity	NPD4363	Phase 3
0.7283	Intermediate Similarity	NPD4360	Phase 2
0.7273	Intermediate Similarity	NPD6778	Approved
0.7273	Intermediate Similarity	NPD6779	Approved
0.7273	Intermediate Similarity	NPD6780	Approved
0.7273	Intermediate Similarity	NPD6782	Approved
0.7273	Intermediate Similarity	NPD6781	Approved
0.7273	Intermediate Similarity	NPD6776	Approved
0.7273	Intermediate Similarity	NPD6777	Approved
0.7262	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD4357	Discontinued
0.7255	Intermediate Similarity	NPD2797	Approved
0.725	Intermediate Similarity	NPD5408	Approved
0.725	Intermediate Similarity	NPD5405	Approved
0.725	Intermediate Similarity	NPD5404	Approved
0.725	Intermediate Similarity	NPD5406	Approved
0.7246	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD7458	Discontinued
0.7244	Intermediate Similarity	NPD411	Approved
0.724	Intermediate Similarity	NPD8151	Discontinued
0.7238	Intermediate Similarity	NPD8434	Phase 2
0.7238	Intermediate Similarity	NPD8150	Discontinued
0.7237	Intermediate Similarity	NPD4749	Approved
0.7235	Intermediate Similarity	NPD5353	Approved
0.723	Intermediate Similarity	NPD5536	Phase 2
0.7225	Intermediate Similarity	NPD7584	Approved
0.7219	Intermediate Similarity	NPD422	Phase 1
0.7219	Intermediate Similarity	NPD1201	Approved
0.7215	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD1471	Phase 3
0.7188	Intermediate Similarity	NPD7033	Discontinued
0.7184	Intermediate Similarity	NPD7229	Phase 3
0.7181	Intermediate Similarity	NPD1548	Phase 1
0.7169	Intermediate Similarity	NPD5049	Phase 3
0.7161	Intermediate Similarity	NPD3018	Phase 2
0.716	Intermediate Similarity	NPD2424	Discontinued
0.716	Intermediate Similarity	NPD6386	Approved
0.716	Intermediate Similarity	NPD6385	Approved
0.7158	Intermediate Similarity	NPD7435	Discontinued
0.7158	Intermediate Similarity	NPD4287	Approved
0.7152	Intermediate Similarity	NPD4060	Phase 1
0.7151	Intermediate Similarity	NPD4361	Phase 2
0.7151	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD2296	Approved
0.7135	Intermediate Similarity	NPD1729	Discontinued
0.7135	Intermediate Similarity	NPD4288	Approved
0.7134	Intermediate Similarity	NPD2354	Approved
0.7134	Intermediate Similarity	NPD6798	Discontinued
0.7134	Intermediate Similarity	NPD3764	Approved
0.7133	Intermediate Similarity	NPD9268	Approved
0.7118	Intermediate Similarity	NPD6844	Discontinued
0.7117	Intermediate Similarity	NPD2654	Approved
0.7107	Intermediate Similarity	NPD5124	Phase 1
0.7107	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7102	Intermediate Similarity	NPD2403	Approved
0.7093	Intermediate Similarity	NPD5019	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD17	Approved
0.7078	Intermediate Similarity	NPD3225	Approved
0.7068	Intermediate Similarity	NPD7697	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