NPASS Compound

Structure

NPC219498 OpenBabel07101718242D 42 43 0 0 1 0 0 0 0 0999 V2000 -12.6144 8.8067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2788 -1.7601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -13.2836 8.0636 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.9746 7.1125 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -13.6437 6.3694 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -13.3347 5.4183 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -14.0038 4.6752 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -13.6948 3.7241 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -14.3639 2.9810 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -14.0549 2.0299 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -14.7240 1.2868 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.4472 -0.1771 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.5336 0.2297 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -14.4150 0.3357 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.2562 0.4107 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7930 1.4499 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9840 0.8621 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7246 -0.3581 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7065 1.0431 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0704 1.2688 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -15.0841 -0.4074 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.1697 0.0040 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -13.3902 -2.4800 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.3957 -2.3754 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5388 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3479 1.0878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 -0.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5388 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8111 0.0486 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2614 0.6810 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -14.7751 -1.3585 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -11.2743 -0.9905 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -13.7970 -1.5664 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -12.1878 -1.3973 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0020 -0.5392 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3659 -0.3135 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -15.4443 -2.1016 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.4652 -1.5783 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2788 1.7601 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 -13.0538 -0.8973 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 1 0 0 0 0 3 4 1 0 0 0 0 4 5 1 0 0 0 0 5 6 1 0 0 0 0 6 7 1 0 0 0 0 7 8 1 0 0 0 0 8 9 1 0 0 0 0 9 10 1 0 0 0 0 10 11 1 0 0 0 0 11 14 1 0 0 0 0 12 13 1 0 0 0 0 12 15 1 0 0 0 0 13 18 1 0 0 0 0 14 21 1 0 0 0 0 15 22 1 0 0 0 0 16 17 1 0 0 0 0 16 19 1 0 0 0 0 17 20 1 0 0 0 0 18 29 1 0 0 0 0 19 29 1 0 0 0 0 20 30 1 0 0 0 0 21 31 1 0 0 0 0 22 32 1 0 0 0 0 23 24 1 0 0 0 0 23 33 1 0 0 0 0 24 34 1 0 0 0 0 25 27 1 0 0 0 0 25 28 2 0 0 0 0 26 28 1 0 0 0 0 26 30 1 0 0 0 0 27 2 1 1 0 0 0 27 41 1 0 0 0 0 28 35 1 0 0 0 0 29 36 2 0 0 0 0 30 37 1 6 0 0 0 31 38 1 6 0 0 0 32 39 1 1 0 0 0 33 31 1 6 0 0 0 33 42 1 0 0 0 0 34 32 1 1 0 0 0 34 42 1 0 0 0 0 35 40 2 0 0 0 0 35 41 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	594.45
Volume:	650.425
LogP:	7.517
LogD:	4.582
LogS:	-5.715
# Rotatable Bonds:	26
TPSA:	120.36
# H-Bond Aceptor:	7
# H-Bond Donor:	4
# Rings:	2
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.081
Synthetic Accessibility Score:	4.379
Fsp3:	0.857
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.264
MDCK Permeability:	2.7369887902750634e-05
Pgp-inhibitor:	0.133
Pgp-substrate:	0.995
Human Intestinal Absorption (HIA):	0.016
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	0.973

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.004
Plasma Protein Binding (PPB):	97.19181060791016%
Volume Distribution (VD):	0.843
Pgp-substrate:	2.2249441146850586%

ADMET: Metabolism

CYP1A2-inhibitor:	0.028
CYP1A2-substrate:	0.362
CYP2C19-inhibitor:	0.065
CYP2C19-substrate:	0.048
CYP2C9-inhibitor:	0.086
CYP2C9-substrate:	0.977
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.122
CYP3A4-inhibitor:	0.166
CYP3A4-substrate:	0.018

ADMET: Excretion

Clearance (CL):	6.319
Half-life (T1/2):	0.498

ADMET: Toxicity

hERG Blockers:	0.088
Human Hepatotoxicity (H-HT):	0.531
Drug-inuced Liver Injury (DILI):	0.052
AMES Toxicity:	0.02
Rat Oral Acute Toxicity:	0.192
Maximum Recommended Daily Dose:	0.87
Skin Sensitization:	0.947
Carcinogencity:	0.033
Eye Corrosion:	0.003
Eye Irritation:	0.016
Respiratory Toxicity:	0.793

Download Data

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

Natural Product: NPC219498

Natural Product ID:	NPC219498
*Common Name:**	Annoreticuin-9-One
IUPAC Name:	(2S)-4-[(2R,13R)-2,13-dihydroxy-13-[(2R,5R)-5-[(1R)-1-hydroxytridecyl]oxolan-2-yl]-7-oxotridecyl]-2-methyl-2H-furan-5-one
Synonyms:	Annoreticuin-9-One
Standard InCHIKey:	QCICHLFBIUXRKT-DOXWYWRGSA-N
Standard InCHI:	InChI=1S/C35H62O7/c1-3-4-5-6-7-8-9-10-11-14-21-31(38)33-23-24-34(42-33)32(39)22-15-12-13-18-29(36)19-16-17-20-30(37)26-28-25-27(2)41-35(28)40/h25,27,30-34,37-39H,3-24,26H2,1-2H3/t27-,30+,31+,32+,33+,34+/m0/s1
SMILES:	CCCCCCCCCCCC[C@H]([C@H]1CC[C@@H](O1)[C@@H](CCCCCC(=O)CCCC[C@H](CC1=C[C@@H](OC1=O)C)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL503350
PubChem CID:	10054216
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0001334] Fatty alcohols [CHEMONTID:0002518] Annonaceous acetogenins

*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
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	seeds	n.a.	n.a.	PMID[11141125]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12398544]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18419154]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19296389]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21910504]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	seed	n.a.	PMID[22011319]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	seeds	n.a.	n.a.	PMID[22011319]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	Barks	n.a.	n.a.	PMID[2348205]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	fruit	n.a.	PMID[8786370]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	bark	n.a.	n.a.	PMID[9214729]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2884	Annona squamosa	Species	Annonaceae	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	6
Others	1

Activity Type	# Activity
Cell Line	6
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	ED50	=	2.7	10'-1 ug/ml	PMID[489689]
NPT83	Cell Line	MCF7	Homo sapiens	ED50	>	1.0	ug ml-1	PMID[489689]
NPT139	Cell Line	HT-29	Homo sapiens	ED50	>	1.0	ug ml-1	PMID[489689]
NPT376	Cell Line	A498	Homo sapiens	ED50	>	1.0	ug ml-1	PMID[489689]
NPT306	Cell Line	PC-3	Homo sapiens	ED50	=	9.6	10'-3 ug/ml	PMID[489689]
NPT783	Cell Line	MIA PaCa-2	Homo sapiens	ED50	=	2.4	10'-4 ug/ml	PMID[489689]
NPT140	Organism	Artemia	Artemia	LC50	=	0.41	ug.mL-1	PMID[489689]

☑ 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 NPC219498 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	179
0.1-0.2	1377
0.2-0.3	5555
0.3-0.4	13255
0.4-0.5	11794
0.5-0.6	6732
0.6-0.7	2945
0.7-0.8	654
0.8-0.85	28
0.85-0.9	50
0.9-0.95	67
0.95-1	61

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC308412
1.0	High Similarity	NPC204686
1.0	High Similarity	NPC210218
1.0	High Similarity	NPC134885
1.0	High Similarity	NPC473687
1.0	High Similarity	NPC134807
0.9875	High Similarity	NPC82795
0.9875	High Similarity	NPC473669
0.9875	High Similarity	NPC473478
0.9875	High Similarity	NPC103284
0.9875	High Similarity	NPC231009
0.9875	High Similarity	NPC110710
0.9875	High Similarity	NPC107986
0.9875	High Similarity	NPC473651
0.9875	High Similarity	NPC286338
0.9875	High Similarity	NPC66346
0.9875	High Similarity	NPC132496
0.9875	High Similarity	NPC283085
0.9875	High Similarity	NPC1083
0.9875	High Similarity	NPC223871
0.9753	High Similarity	NPC142117
0.9753	High Similarity	NPC232555
0.9753	High Similarity	NPC107717
0.9753	High Similarity	NPC171174
0.9753	High Similarity	NPC231096
0.9753	High Similarity	NPC134865
0.9753	High Similarity	NPC475581
0.9753	High Similarity	NPC279267
0.9753	High Similarity	NPC240695
0.9753	High Similarity	NPC114694
0.9753	High Similarity	NPC69082
0.9753	High Similarity	NPC103523
0.9753	High Similarity	NPC62118
0.9639	High Similarity	NPC14901
0.9639	High Similarity	NPC130359
0.9634	High Similarity	NPC178215
0.9625	High Similarity	NPC144415
0.9518	High Similarity	NPC40376
0.9518	High Similarity	NPC20339
0.9518	High Similarity	NPC133730
0.9518	High Similarity	NPC100454
0.9518	High Similarity	NPC61257
0.9518	High Similarity	NPC39754
0.9518	High Similarity	NPC191929
0.9518	High Similarity	NPC274446
0.9518	High Similarity	NPC287164
0.9518	High Similarity	NPC233551
0.9518	High Similarity	NPC81045
0.9518	High Similarity	NPC169511
0.9518	High Similarity	NPC21208
0.9518	High Similarity	NPC242364
0.9518	High Similarity	NPC320569
0.9518	High Similarity	NPC172821
0.9518	High Similarity	NPC280621
0.9518	High Similarity	NPC171135
0.9518	High Similarity	NPC261952
0.9518	High Similarity	NPC48338
0.9518	High Similarity	NPC151403
0.9518	High Similarity	NPC234077
0.9512	High Similarity	NPC112685
0.9512	High Similarity	NPC477015
0.9506	High Similarity	NPC156804
0.9506	High Similarity	NPC163093
0.95	High Similarity	NPC475159
0.95	High Similarity	NPC473529
0.95	High Similarity	NPC473712
0.95	High Similarity	NPC131002
0.95	High Similarity	NPC180363
0.95	High Similarity	NPC473780
0.95	High Similarity	NPC65930
0.95	High Similarity	NPC73310
0.95	High Similarity	NPC329829
0.95	High Similarity	NPC11332
0.95	High Similarity	NPC94875
0.95	High Similarity	NPC145914
0.9405	High Similarity	NPC81778
0.9405	High Similarity	NPC477011
0.9405	High Similarity	NPC42598
0.9405	High Similarity	NPC91067
0.9405	High Similarity	NPC318963
0.9405	High Similarity	NPC280612
0.9405	High Similarity	NPC40066
0.9405	High Similarity	NPC20621
0.9405	High Similarity	NPC139418
0.9405	High Similarity	NPC473504
0.9405	High Similarity	NPC93794
0.939	High Similarity	NPC329615
0.939	High Similarity	NPC471567
0.939	High Similarity	NPC322529
0.939	High Similarity	NPC477013
0.939	High Similarity	NPC477014
0.939	High Similarity	NPC182383
0.939	High Similarity	NPC120398
0.939	High Similarity	NPC329838
0.9383	High Similarity	NPC253801
0.9302	High Similarity	NPC11456
0.9294	High Similarity	NPC239517
0.9294	High Similarity	NPC473904
0.9277	High Similarity	NPC241360
0.9277	High Similarity	NPC293136
0.9277	High Similarity	NPC477010
0.9277	High Similarity	NPC132940
0.9277	High Similarity	NPC47937
0.9176	High Similarity	NPC477016
0.9176	High Similarity	NPC477017
0.9167	High Similarity	NPC20533
0.9167	High Similarity	NPC258068
0.9167	High Similarity	NPC477012
0.9167	High Similarity	NPC476583
0.9157	High Similarity	NPC319036
0.9157	High Similarity	NPC477018
0.9157	High Similarity	NPC9678
0.9157	High Similarity	NPC100921
0.9157	High Similarity	NPC292809
0.9157	High Similarity	NPC25764
0.9157	High Similarity	NPC39167
0.9157	High Similarity	NPC202055
0.9157	High Similarity	NPC235809
0.9157	High Similarity	NPC473156
0.9157	High Similarity	NPC470400
0.9157	High Similarity	NPC39279
0.9157	High Similarity	NPC475268
0.9157	High Similarity	NPC473671
0.9157	High Similarity	NPC77871
0.908	High Similarity	NPC473663
0.908	High Similarity	NPC475173
0.908	High Similarity	NPC473723
0.908	High Similarity	NPC473561
0.9059	High Similarity	NPC320458
0.9059	High Similarity	NPC89001
0.9059	High Similarity	NPC473905
0.9048	High Similarity	NPC473840
0.9048	High Similarity	NPC219652
0.9048	High Similarity	NPC282815
0.9048	High Similarity	NPC25703
0.9048	High Similarity	NPC309211
0.8966	High Similarity	NPC473707
0.8941	High Similarity	NPC159750
0.8941	High Similarity	NPC473995
0.8941	High Similarity	NPC470401
0.8941	High Similarity	NPC473649
0.8941	High Similarity	NPC154097
0.8652	High Similarity	NPC473520
0.8444	Intermediate Similarity	NPC162205
0.8444	Intermediate Similarity	NPC288240
0.8444	Intermediate Similarity	NPC273579
0.8444	Intermediate Similarity	NPC295204
0.8333	Intermediate Similarity	NPC30515
0.8276	Intermediate Similarity	NPC21469
0.8242	Intermediate Similarity	NPC81419
0.8242	Intermediate Similarity	NPC179746
0.8222	Intermediate Similarity	NPC51004
0.8222	Intermediate Similarity	NPC473619
0.8132	Intermediate Similarity	NPC12172
0.8132	Intermediate Similarity	NPC473321
0.8132	Intermediate Similarity	NPC208886
0.8132	Intermediate Similarity	NPC184463
0.8118	Intermediate Similarity	NPC47653
0.8111	Intermediate Similarity	NPC307411
0.8111	Intermediate Similarity	NPC295312
0.8065	Intermediate Similarity	NPC36954
0.8046	Intermediate Similarity	NPC284472
0.8046	Intermediate Similarity	NPC229799
0.8046	Intermediate Similarity	NPC286770
0.8043	Intermediate Similarity	NPC476300
0.8043	Intermediate Similarity	NPC475912
0.8025	Intermediate Similarity	NPC84038
0.8022	Intermediate Similarity	NPC473448
0.8022	Intermediate Similarity	NPC476004
0.8022	Intermediate Similarity	NPC474761
0.8	Intermediate Similarity	NPC187268
0.8	Intermediate Similarity	NPC202672
0.8	Intermediate Similarity	NPC473326
0.7978	Intermediate Similarity	NPC469483
0.7976	Intermediate Similarity	NPC475711
0.7957	Intermediate Similarity	NPC474035
0.7957	Intermediate Similarity	NPC81386
0.7955	Intermediate Similarity	NPC474251
0.7931	Intermediate Similarity	NPC474959
0.7931	Intermediate Similarity	NPC475046
0.7931	Intermediate Similarity	NPC310450
0.7931	Intermediate Similarity	NPC11383
0.7927	Intermediate Similarity	NPC474705
0.7912	Intermediate Similarity	NPC474032
0.7889	Intermediate Similarity	NPC179659
0.7889	Intermediate Similarity	NPC160138
0.7882	Intermediate Similarity	NPC93763
0.7882	Intermediate Similarity	NPC279214
0.7882	Intermediate Similarity	NPC221095
0.7882	Intermediate Similarity	NPC108816
0.7872	Intermediate Similarity	NPC270013
0.7872	Intermediate Similarity	NPC14961
0.7857	Intermediate Similarity	NPC123360
0.7849	Intermediate Similarity	NPC469692
0.7849	Intermediate Similarity	NPC212486
0.7849	Intermediate Similarity	NPC469645
0.7841	Intermediate Similarity	NPC475947
0.7841	Intermediate Similarity	NPC169575
0.7841	Intermediate Similarity	NPC116543
0.7841	Intermediate Similarity	NPC40746

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 NPC219498 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	166
0.1-0.2	2115
0.2-0.3	3832
0.3-0.4	2114
0.4-0.5	611
0.5-0.6	260
0.6-0.7	46
0.7-0.8	6
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7826	Intermediate Similarity	NPD46	Approved
0.7826	Intermediate Similarity	NPD6698	Approved
0.7624	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD7838	Discovery
0.7238	Intermediate Similarity	NPD6371	Approved
0.7188	Intermediate Similarity	NPD7983	Approved
0.7143	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.71	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD5785	Approved
0.7048	Intermediate Similarity	NPD6686	Approved
0.6915	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD5363	Approved
0.6852	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD4756	Discovery
0.6771	Remote Similarity	NPD4250	Approved
0.6771	Remote Similarity	NPD4251	Approved
0.6765	Remote Similarity	NPD4225	Approved
0.6747	Remote Similarity	NPD3197	Phase 1
0.6737	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD7154	Phase 3
0.6702	Remote Similarity	NPD5362	Discontinued
0.6667	Remote Similarity	NPD4249	Approved
0.6633	Remote Similarity	NPD1695	Approved
0.6596	Remote Similarity	NPD4269	Approved
0.6596	Remote Similarity	NPD4270	Approved
0.6559	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6559	Remote Similarity	NPD4252	Approved
0.6512	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6495	Remote Similarity	NPD5786	Approved
0.6489	Remote Similarity	NPD5369	Approved
0.6476	Remote Similarity	NPD5344	Discontinued
0.6421	Remote Similarity	NPD6435	Approved
0.6421	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD7115	Discovery
0.6392	Remote Similarity	NPD1694	Approved
0.6373	Remote Similarity	NPD5282	Discontinued
0.6354	Remote Similarity	NPD6110	Phase 1
0.6344	Remote Similarity	NPD4268	Approved
0.6344	Remote Similarity	NPD4271	Approved
0.6344	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6339	Remote Similarity	NPD6053	Discontinued
0.6325	Remote Similarity	NPD8516	Approved
0.6325	Remote Similarity	NPD8517	Approved
0.6325	Remote Similarity	NPD8515	Approved
0.6325	Remote Similarity	NPD8513	Phase 3
0.6289	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6286	Remote Similarity	NPD7638	Approved
0.6275	Remote Similarity	NPD5778	Approved
0.6275	Remote Similarity	NPD5779	Approved
0.625	Remote Similarity	NPD5209	Approved
0.625	Remote Similarity	NPD7839	Suspended
0.6235	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.6226	Remote Similarity	NPD7640	Approved
0.6226	Remote Similarity	NPD7639	Approved
0.6216	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6211	Remote Similarity	NPD4821	Approved
0.6211	Remote Similarity	NPD4819	Approved
0.6211	Remote Similarity	NPD4822	Approved
0.6211	Remote Similarity	NPD4820	Approved
0.6211	Remote Similarity	NPD5368	Approved
0.6207	Remote Similarity	NPD3704	Approved
0.6196	Remote Similarity	NPD8039	Approved
0.619	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6186	Remote Similarity	NPD5332	Approved
0.6186	Remote Similarity	NPD5331	Approved
0.6146	Remote Similarity	NPD4790	Discontinued
0.6139	Remote Similarity	NPD5370	Suspended
0.6117	Remote Similarity	NPD6399	Phase 3
0.6116	Remote Similarity	NPD7507	Approved
0.6092	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6083	Remote Similarity	NPD7642	Approved
0.6083	Remote Similarity	NPD7829	Approved
0.6083	Remote Similarity	NPD7830	Approved
0.6075	Remote Similarity	NPD6648	Approved
0.6068	Remote Similarity	NPD7641	Discontinued
0.6066	Remote Similarity	NPD8074	Phase 3
0.6049	Remote Similarity	NPD4266	Approved
0.6049	Remote Similarity	NPD3194	Approved
0.6049	Remote Similarity	NPD3728	Approved
0.6049	Remote Similarity	NPD3195	Phase 2
0.6049	Remote Similarity	NPD3730	Approved
0.6049	Remote Similarity	NPD3196	Approved
0.6038	Remote Similarity	NPD7902	Approved
0.6036	Remote Similarity	NPD6412	Phase 2
0.6023	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6018	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5968	Remote Similarity	NPD7319	Approved
0.5965	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.5952	Remote Similarity	NPD69	Approved
0.5952	Remote Similarity	NPD9119	Approved
0.5952	Remote Similarity	NPD6109	Phase 1
0.5926	Remote Similarity	NPD3172	Approved
0.5917	Remote Similarity	NPD8033	Approved
0.5917	Remote Similarity	NPD8444	Approved
0.5913	Remote Similarity	NPD8297	Approved
0.5905	Remote Similarity	NPD7748	Approved
0.5891	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.5877	Remote Similarity	NPD2067	Discontinued
0.5875	Remote Similarity	NPD6927	Phase 3
0.5873	Remote Similarity	NPD7260	Phase 2
0.5865	Remote Similarity	NPD7637	Suspended
0.5862	Remote Similarity	NPD4632	Approved
0.5847	Remote Similarity	NPD7500	Approved
0.5843	Remote Similarity	NPD7331	Phase 2
0.5833	Remote Similarity	NPD9118	Approved
0.5833	Remote Similarity	NPD8377	Approved
0.5833	Remote Similarity	NPD8294	Approved
0.5827	Remote Similarity	NPD6845	Suspended
0.5826	Remote Similarity	NPD2204	Approved
0.5825	Remote Similarity	NPD6101	Approved
0.5825	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5804	Remote Similarity	NPD6008	Approved
0.5798	Remote Similarity	NPD7328	Approved
0.5798	Remote Similarity	NPD7327	Approved
0.5794	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.5785	Remote Similarity	NPD8379	Approved
0.5785	Remote Similarity	NPD8296	Approved
0.5785	Remote Similarity	NPD8380	Approved
0.5785	Remote Similarity	NPD8335	Approved
0.5785	Remote Similarity	NPD8378	Approved
0.5772	Remote Similarity	NPD7492	Approved
0.5766	Remote Similarity	NPD6647	Phase 2
0.576	Remote Similarity	NPD7736	Approved
0.5755	Remote Similarity	NPD7900	Approved
0.5755	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5752	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.575	Remote Similarity	NPD7516	Approved
0.5741	Remote Similarity	NPD6084	Phase 2
0.5741	Remote Similarity	NPD6083	Phase 2
0.5739	Remote Similarity	NPD6421	Discontinued
0.5728	Remote Similarity	NPD6903	Approved
0.5726	Remote Similarity	NPD8451	Approved
0.5726	Remote Similarity	NPD6616	Approved
0.5726	Remote Similarity	NPD8273	Phase 1
0.5714	Remote Similarity	NPD7505	Discontinued
0.5714	Remote Similarity	NPD6411	Approved
0.5714	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD7515	Phase 2
0.5702	Remote Similarity	NPD7320	Approved
0.5702	Remote Similarity	NPD6881	Approved
0.5702	Remote Similarity	NPD6899	Approved
0.5702	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5702	Remote Similarity	NPD6319	Approved
0.5702	Remote Similarity	NPD6054	Approved
0.5691	Remote Similarity	NPD8328	Phase 3
0.569	Remote Similarity	NPD8130	Phase 1
0.569	Remote Similarity	NPD6650	Approved
0.569	Remote Similarity	NPD6649	Approved
0.5686	Remote Similarity	NPD5330	Approved
0.5686	Remote Similarity	NPD6422	Discontinued
0.5686	Remote Similarity	NPD6684	Approved
0.5686	Remote Similarity	NPD7146	Approved
0.5686	Remote Similarity	NPD7521	Approved
0.5686	Remote Similarity	NPD6409	Approved
0.5686	Remote Similarity	NPD7334	Approved
0.568	Remote Similarity	NPD8293	Discontinued
0.568	Remote Similarity	NPD8448	Approved
0.568	Remote Similarity	NPD7078	Approved
0.5679	Remote Similarity	NPD29	Approved
0.5679	Remote Similarity	NPD28	Approved
0.5676	Remote Similarity	NPD7632	Discontinued
0.5664	Remote Similarity	NPD6402	Approved
0.5664	Remote Similarity	NPD6675	Approved
0.5664	Remote Similarity	NPD5739	Approved
0.5664	Remote Similarity	NPD7128	Approved
0.5652	Remote Similarity	NPD6373	Approved
0.5652	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.5652	Remote Similarity	NPD6372	Approved
0.5614	Remote Similarity	NPD5697	Approved
0.561	Remote Similarity	NPD8080	Discontinued
0.561	Remote Similarity	NPD6370	Approved
0.5603	Remote Similarity	NPD6883	Approved
0.5603	Remote Similarity	NPD7102	Approved
0.5603	Remote Similarity	NPD7290	Approved
0.56	Remote Similarity	NPD4800	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