NPASS Compound

Structure

NPC473478 OpenBabel07101719512D 44 45 0 0 1 0 0 0 0 0999 V2000 23.5799 -3.7969 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0933 -1.7796 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 23.2709 -2.8459 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 22.2928 -2.6380 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 21.6236 -3.3811 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 20.6455 -3.1732 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 19.9764 -3.9163 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 18.9982 -3.7084 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 18.3291 -4.4516 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 17.3509 -4.2437 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7769 -0.3740 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9678 0.2138 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6904 0.0327 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 16.6818 -4.9868 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0543 -0.1930 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4994 -0.5551 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 15.7037 -4.7789 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 14.1075 -2.6689 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 13.1293 -2.4610 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2453 0.3948 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.4130 -0.1483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 15.0345 -5.5220 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 14.4165 -3.6199 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.4602 -3.2041 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.1730 -0.4271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.7608 -1.2361 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4013 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5227 0.5759 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4067 -0.9135 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6092 0.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3317 -0.0119 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 10.2220 -0.7361 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 14.0564 -5.3141 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 13.7474 -4.3631 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 11.4821 -2.9962 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 11.1730 -2.0451 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.7431 0.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2272 -1.0064 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 13.3873 -6.0573 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 12.7692 -4.1552 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 10.8129 -3.7393 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6386 1.6637 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 10.2220 -1.7361 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 14 1 0 0 0 0 11 12 1 0 0 0 0 11 13 1 0 0 0 0 12 15 1 0 0 0 0 13 16 1 0 0 0 0 14 17 1 0 0 0 0 15 20 1 0 0 0 0 16 21 1 0 0 0 0 17 22 1 0 0 0 0 18 19 1 0 0 0 0 18 23 1 0 0 0 0 19 24 1 0 0 0 0 20 31 1 0 0 0 0 22 33 1 0 0 0 0 23 34 1 0 0 0 0 24 35 1 0 0 0 0 25 26 1 0 0 0 0 25 32 1 0 0 0 0 26 36 1 0 0 0 0 27 29 1 0 0 0 0 27 30 2 0 0 0 0 28 30 1 0 0 0 0 28 31 1 0 0 0 0 29 2 1 6 0 0 0 29 43 1 0 0 0 0 30 37 1 0 0 0 0 31 38 1 0 0 0 0 32 21 1 1 0 0 0 32 44 1 0 0 0 0 33 34 1 0 0 0 0 33 39 1 6 0 0 0 34 40 1 1 0 0 0 35 41 1 1 0 0 0 36 35 1 6 0 0 0 36 44 1 0 0 0 0 37 42 2 0 0 0 0 37 43 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	624.5
Volume:	687.654
LogP:	8.852
LogD:	4.876
LogS:	-4.507
# Rotatable Bonds:	28
TPSA:	123.52
# H-Bond Aceptor:	7
# H-Bond Donor:	5
# Rings:	2
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.059
Synthetic Accessibility Score:	4.511
Fsp3:	0.892
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:	-5.243
MDCK Permeability:	1.0839075002877507e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.624
Human Intestinal Absorption (HIA):	0.03
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	0.937

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.006
Plasma Protein Binding (PPB):	96.79378509521484%
Volume Distribution (VD):	1.162
Pgp-substrate:	2.6294498443603516%

ADMET: Metabolism

CYP1A2-inhibitor:	0.034
CYP1A2-substrate:	0.212
CYP2C19-inhibitor:	0.048
CYP2C19-substrate:	0.05
CYP2C9-inhibitor:	0.067
CYP2C9-substrate:	0.973
CYP2D6-inhibitor:	0.009
CYP2D6-substrate:	0.071
CYP3A4-inhibitor:	0.137
CYP3A4-substrate:	0.012

ADMET: Excretion

Clearance (CL):	6.901
Half-life (T1/2):	0.091

ADMET: Toxicity

hERG Blockers:	0.22
Human Hepatotoxicity (H-HT):	0.277
Drug-inuced Liver Injury (DILI):	0.019
AMES Toxicity:	0.015
Rat Oral Acute Toxicity:	0.011
Maximum Recommended Daily Dose:	0.837
Skin Sensitization:	0.964
Carcinogencity:	0.038
Eye Corrosion:	0.003
Eye Irritation:	0.02
Respiratory Toxicity:	0.847

Download Data

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

Natural Product: NPC473478

Natural Product ID:	NPC473478
*Common Name:**	Squadiolin C
IUPAC Name:	(2S)-4-[2-hydroxy-9-[(2S,5R)-5-[(1R,6S,7S)-1,6,7-trihydroxynonadecyl]oxolan-2-yl]nonyl]-2-methyl-2H-furan-5-one
Synonyms:	squadiolin C
Standard InCHIKey:	NMFDDBWJYTYLTB-FSIHDYJCSA-N
Standard InCHI:	InChI=1S/C37H68O7/c1-3-4-5-6-7-8-9-10-14-17-22-33(39)34(40)23-18-19-24-35(41)36-26-25-32(44-36)21-16-13-11-12-15-20-31(38)28-30-27-29(2)43-37(30)42/h27,29,31-36,38-41H,3-26,28H2,1-2H3/t29-,31?,32-,33-,34-,35+,36+/m0/s1
SMILES:	CCCCCCCCCCCCC(C(CCCCC(C1CCC(O1)CCCCCCCC(CC2=CC(OC2=O)C)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL442941
PubChem CID:	44577076
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	seeds	n.a.	n.a.	PMID[22011319]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	seed	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
IC50	4

Activity Type	# Activity
Cell Line	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	=	14450.0	nM	PMID[558133]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	3620.0	nM	PMID[558133]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	8110.0	nM	PMID[558133]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	3480.0	nM	PMID[558133]

☑ 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 NPC473478 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	1359
0.2-0.3	5551
0.3-0.4	13882
0.4-0.5	11207
0.5-0.6	6800
0.6-0.7	2850
0.7-0.8	649
0.8-0.85	46
0.85-0.9	30
0.9-0.95	69
0.95-1	75

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC283085
1.0	High Similarity	NPC286338
1.0	High Similarity	NPC82795
1.0	High Similarity	NPC107986
1.0	High Similarity	NPC473669
1.0	High Similarity	NPC473651
1.0	High Similarity	NPC231009
1.0	High Similarity	NPC66346
1.0	High Similarity	NPC223871
1.0	High Similarity	NPC110710
1.0	High Similarity	NPC1083
1.0	High Similarity	NPC132496
1.0	High Similarity	NPC103284
0.9875	High Similarity	NPC171174
0.9875	High Similarity	NPC210218
0.9875	High Similarity	NPC142117
0.9875	High Similarity	NPC231096
0.9875	High Similarity	NPC219498
0.9875	High Similarity	NPC62118
0.9875	High Similarity	NPC204686
0.9875	High Similarity	NPC308412
0.9875	High Similarity	NPC279267
0.9875	High Similarity	NPC134865
0.9875	High Similarity	NPC240695
0.9875	High Similarity	NPC69082
0.9875	High Similarity	NPC475581
0.9875	High Similarity	NPC232555
0.9875	High Similarity	NPC103523
0.9875	High Similarity	NPC134807
0.9875	High Similarity	NPC473687
0.9875	High Similarity	NPC134885
0.9875	High Similarity	NPC107717
0.9875	High Similarity	NPC114694
0.9753	High Similarity	NPC178215
0.9634	High Similarity	NPC81045
0.9634	High Similarity	NPC169511
0.9634	High Similarity	NPC171135
0.9634	High Similarity	NPC172821
0.9634	High Similarity	NPC48338
0.9634	High Similarity	NPC39754
0.9634	High Similarity	NPC151403
0.9634	High Similarity	NPC21208
0.9634	High Similarity	NPC40376
0.9634	High Similarity	NPC242364
0.9634	High Similarity	NPC320569
0.9634	High Similarity	NPC287164
0.9634	High Similarity	NPC280621
0.9634	High Similarity	NPC261952
0.9634	High Similarity	NPC100454
0.9634	High Similarity	NPC233551
0.9634	High Similarity	NPC191929
0.9634	High Similarity	NPC234077
0.9634	High Similarity	NPC274446
0.9634	High Similarity	NPC20339
0.9634	High Similarity	NPC133730
0.9634	High Similarity	NPC61257
0.963	High Similarity	NPC112685
0.9625	High Similarity	NPC163093
0.9625	High Similarity	NPC156804
0.962	High Similarity	NPC131002
0.962	High Similarity	NPC329829
0.962	High Similarity	NPC11332
0.962	High Similarity	NPC65930
0.962	High Similarity	NPC473712
0.962	High Similarity	NPC73310
0.962	High Similarity	NPC475159
0.962	High Similarity	NPC145914
0.962	High Similarity	NPC473780
0.962	High Similarity	NPC180363
0.962	High Similarity	NPC94875
0.962	High Similarity	NPC473529
0.9518	High Similarity	NPC20621
0.9518	High Similarity	NPC473504
0.9518	High Similarity	NPC81778
0.9518	High Similarity	NPC93794
0.9518	High Similarity	NPC477011
0.9518	High Similarity	NPC91067
0.9518	High Similarity	NPC130359
0.9518	High Similarity	NPC139418
0.9518	High Similarity	NPC40066
0.9518	High Similarity	NPC14901
0.9518	High Similarity	NPC42598
0.9518	High Similarity	NPC318963
0.9506	High Similarity	NPC471567
0.9506	High Similarity	NPC120398
0.9506	High Similarity	NPC329838
0.9506	High Similarity	NPC182383
0.9506	High Similarity	NPC329615
0.9506	High Similarity	NPC477014
0.9506	High Similarity	NPC477013
0.9506	High Similarity	NPC322529
0.95	High Similarity	NPC253801
0.95	High Similarity	NPC144415
0.9405	High Similarity	NPC239517
0.9405	High Similarity	NPC473904
0.939	High Similarity	NPC477015
0.939	High Similarity	NPC132940
0.939	High Similarity	NPC293136
0.939	High Similarity	NPC241360
0.939	High Similarity	NPC47937
0.9286	High Similarity	NPC280612
0.9277	High Similarity	NPC20533
0.9277	High Similarity	NPC476583
0.9277	High Similarity	NPC258068
0.9268	High Similarity	NPC202055
0.9268	High Similarity	NPC39279
0.9268	High Similarity	NPC235809
0.9268	High Similarity	NPC477018
0.9268	High Similarity	NPC475268
0.9268	High Similarity	NPC100921
0.9268	High Similarity	NPC39167
0.9268	High Similarity	NPC470400
0.9268	High Similarity	NPC473156
0.9268	High Similarity	NPC77871
0.9268	High Similarity	NPC473671
0.9268	High Similarity	NPC292809
0.9268	High Similarity	NPC319036
0.9268	High Similarity	NPC25764
0.9268	High Similarity	NPC9678
0.9186	High Similarity	NPC475173
0.9186	High Similarity	NPC11456
0.9186	High Similarity	NPC473723
0.9186	High Similarity	NPC473663
0.9186	High Similarity	NPC473561
0.9167	High Similarity	NPC89001
0.9167	High Similarity	NPC473905
0.9167	High Similarity	NPC320458
0.9157	High Similarity	NPC219652
0.9157	High Similarity	NPC25703
0.9157	High Similarity	NPC473840
0.9157	High Similarity	NPC477010
0.9157	High Similarity	NPC282815
0.9157	High Similarity	NPC309211
0.907	High Similarity	NPC473707
0.9059	High Similarity	NPC477016
0.9059	High Similarity	NPC477017
0.9048	High Similarity	NPC154097
0.9048	High Similarity	NPC473649
0.9048	High Similarity	NPC159750
0.9048	High Similarity	NPC470401
0.9048	High Similarity	NPC477012
0.9048	High Similarity	NPC473995
0.875	High Similarity	NPC473520
0.8427	Intermediate Similarity	NPC30515
0.8372	Intermediate Similarity	NPC21469
0.8333	Intermediate Similarity	NPC179746
0.8333	Intermediate Similarity	NPC162205
0.8333	Intermediate Similarity	NPC288240
0.8333	Intermediate Similarity	NPC295204
0.8333	Intermediate Similarity	NPC273579
0.8333	Intermediate Similarity	NPC81419
0.8315	Intermediate Similarity	NPC51004
0.8315	Intermediate Similarity	NPC473619
0.8222	Intermediate Similarity	NPC184463
0.8222	Intermediate Similarity	NPC473321
0.8222	Intermediate Similarity	NPC12172
0.8222	Intermediate Similarity	NPC208886
0.8202	Intermediate Similarity	NPC307411
0.8202	Intermediate Similarity	NPC295312
0.8152	Intermediate Similarity	NPC36954
0.814	Intermediate Similarity	NPC286770
0.814	Intermediate Similarity	NPC229799
0.814	Intermediate Similarity	NPC284472
0.8132	Intermediate Similarity	NPC475912
0.8132	Intermediate Similarity	NPC476300
0.8125	Intermediate Similarity	NPC84038
0.8111	Intermediate Similarity	NPC476004
0.8111	Intermediate Similarity	NPC473448
0.8111	Intermediate Similarity	NPC474761
0.809	Intermediate Similarity	NPC202672
0.8085	Intermediate Similarity	NPC187268
0.8085	Intermediate Similarity	NPC473326
0.8072	Intermediate Similarity	NPC475711
0.8068	Intermediate Similarity	NPC469483
0.8043	Intermediate Similarity	NPC81386
0.8043	Intermediate Similarity	NPC474035
0.8025	Intermediate Similarity	NPC474705
0.8023	Intermediate Similarity	NPC310450
0.8023	Intermediate Similarity	NPC475046
0.8023	Intermediate Similarity	NPC474959
0.8023	Intermediate Similarity	NPC11383
0.8	Intermediate Similarity	NPC474032
0.8	Intermediate Similarity	NPC47653
0.7978	Intermediate Similarity	NPC160138
0.7976	Intermediate Similarity	NPC108816
0.7976	Intermediate Similarity	NPC221095
0.7976	Intermediate Similarity	NPC279214
0.7976	Intermediate Similarity	NPC93763
0.7957	Intermediate Similarity	NPC14961
0.7957	Intermediate Similarity	NPC270013
0.7952	Intermediate Similarity	NPC123360
0.7935	Intermediate Similarity	NPC212486
0.7931	Intermediate Similarity	NPC475947
0.7931	Intermediate Similarity	NPC169575
0.7931	Intermediate Similarity	NPC40746
0.7931	Intermediate Similarity	NPC116543
0.7912	Intermediate Similarity	NPC474232
0.7889	Intermediate Similarity	NPC177629
0.7889	Intermediate Similarity	NPC58219
0.7889	Intermediate Similarity	NPC473715

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 NPC473478 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	162
0.1-0.2	2109
0.2-0.3	3819
0.3-0.4	2150
0.4-0.5	610
0.5-0.6	245
0.6-0.7	51
0.7-0.8	4
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
0.7912	Intermediate Similarity	NPD46	Approved
0.7912	Intermediate Similarity	NPD6698	Approved
0.77	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7527	Intermediate Similarity	NPD7838	Discovery
0.7263	Intermediate Similarity	NPD7983	Approved
0.7172	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6371	Approved
0.7115	Intermediate Similarity	NPD6686	Approved
0.7041	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6979	Remote Similarity	NPD5785	Approved
0.6916	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD4250	Approved
0.6842	Remote Similarity	NPD4251	Approved
0.6832	Remote Similarity	NPD4225	Approved
0.6829	Remote Similarity	NPD3197	Phase 1
0.6809	Remote Similarity	NPD5363	Approved
0.6809	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD7154	Phase 3
0.6774	Remote Similarity	NPD5362	Discontinued
0.6737	Remote Similarity	NPD4249	Approved
0.6701	Remote Similarity	NPD1695	Approved
0.6667	Remote Similarity	NPD4756	Discovery
0.663	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD5344	Discontinued
0.6489	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD4270	Approved
0.6489	Remote Similarity	NPD4269	Approved
0.6452	Remote Similarity	NPD4252	Approved
0.6413	Remote Similarity	NPD4271	Approved
0.6413	Remote Similarity	NPD4268	Approved
0.6396	Remote Similarity	NPD6053	Discontinued
0.6392	Remote Similarity	NPD5786	Approved
0.6383	Remote Similarity	NPD5369	Approved
0.6379	Remote Similarity	NPD8513	Phase 3
0.6379	Remote Similarity	NPD8517	Approved
0.6379	Remote Similarity	NPD8515	Approved
0.6379	Remote Similarity	NPD8516	Approved
0.6354	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD7638	Approved
0.6337	Remote Similarity	NPD5779	Approved
0.6337	Remote Similarity	NPD5778	Approved
0.6316	Remote Similarity	NPD6435	Approved
0.6316	Remote Similarity	NPD7115	Discovery
0.6311	Remote Similarity	NPD7839	Suspended
0.6289	Remote Similarity	NPD1694	Approved
0.6286	Remote Similarity	NPD7639	Approved
0.6286	Remote Similarity	NPD7640	Approved
0.6277	Remote Similarity	NPD4819	Approved
0.6277	Remote Similarity	NPD4821	Approved
0.6277	Remote Similarity	NPD4822	Approved
0.6277	Remote Similarity	NPD4820	Approved
0.6275	Remote Similarity	NPD5282	Discontinued
0.6273	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6265	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6264	Remote Similarity	NPD8039	Approved
0.625	Remote Similarity	NPD6110	Phase 1
0.625	Remote Similarity	NPD5332	Approved
0.625	Remote Similarity	NPD5331	Approved
0.6237	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6211	Remote Similarity	NPD4790	Discontinued
0.6167	Remote Similarity	NPD7507	Approved
0.6163	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6146	Remote Similarity	NPD5209	Approved
0.6134	Remote Similarity	NPD7829	Approved
0.6134	Remote Similarity	NPD7830	Approved
0.6132	Remote Similarity	NPD6648	Approved
0.6125	Remote Similarity	NPD4266	Approved
0.6125	Remote Similarity	NPD3728	Approved
0.6125	Remote Similarity	NPD3730	Approved
0.6125	Remote Similarity	NPD3194	Approved
0.6125	Remote Similarity	NPD3195	Phase 2
0.6125	Remote Similarity	NPD3196	Approved
0.6118	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.6116	Remote Similarity	NPD8074	Phase 3
0.6105	Remote Similarity	NPD5368	Approved
0.6092	Remote Similarity	NPD3704	Approved
0.6071	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.604	Remote Similarity	NPD5370	Suspended
0.6024	Remote Similarity	NPD69	Approved
0.6024	Remote Similarity	NPD6109	Phase 1
0.6024	Remote Similarity	NPD9119	Approved
0.6019	Remote Similarity	NPD6399	Phase 3
0.6016	Remote Similarity	NPD7319	Approved
0.6	Remote Similarity	NPD3172	Approved
0.6	Remote Similarity	NPD7642	Approved
0.5983	Remote Similarity	NPD7641	Discontinued
0.5966	Remote Similarity	NPD8033	Approved
0.5949	Remote Similarity	NPD6927	Phase 3
0.5946	Remote Similarity	NPD6412	Phase 2
0.5943	Remote Similarity	NPD7902	Approved
0.5938	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.5929	Remote Similarity	NPD2067	Discontinued
0.5922	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.5922	Remote Similarity	NPD7637	Suspended
0.5909	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.5904	Remote Similarity	NPD9118	Approved
0.5882	Remote Similarity	NPD6101	Approved
0.5882	Remote Similarity	NPD8294	Approved
0.5882	Remote Similarity	NPD8377	Approved
0.5882	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5877	Remote Similarity	NPD2204	Approved
0.5877	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.5849	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.5847	Remote Similarity	NPD7328	Approved
0.5847	Remote Similarity	NPD7327	Approved
0.5833	Remote Similarity	NPD8380	Approved
0.5833	Remote Similarity	NPD8378	Approved
0.5833	Remote Similarity	NPD8379	Approved
0.5833	Remote Similarity	NPD8296	Approved
0.5833	Remote Similarity	NPD8444	Approved
0.5833	Remote Similarity	NPD8335	Approved
0.5826	Remote Similarity	NPD8297	Approved
0.581	Remote Similarity	NPD7748	Approved
0.5804	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5798	Remote Similarity	NPD7516	Approved
0.5794	Remote Similarity	NPD7260	Phase 2
0.5789	Remote Similarity	NPD6421	Discontinued
0.5776	Remote Similarity	NPD4632	Approved
0.5772	Remote Similarity	NPD8273	Phase 1
0.5772	Remote Similarity	NPD8451	Approved
0.5769	Remote Similarity	NPD6411	Approved
0.5763	Remote Similarity	NPD7505	Discontinued
0.5763	Remote Similarity	NPD7500	Approved
0.575	Remote Similarity	NPD29	Approved
0.575	Remote Similarity	NPD28	Approved
0.5748	Remote Similarity	NPD6845	Suspended
0.5743	Remote Similarity	NPD6422	Discontinued
0.573	Remote Similarity	NPD7331	Phase 2
0.5727	Remote Similarity	NPD7632	Discontinued
0.5726	Remote Similarity	NPD8448	Approved
0.5714	Remote Similarity	NPD6008	Approved
0.5691	Remote Similarity	NPD7492	Approved
0.568	Remote Similarity	NPD7736	Approved
0.5676	Remote Similarity	NPD6647	Phase 2
0.566	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.566	Remote Similarity	NPD7900	Approved
0.5648	Remote Similarity	NPD6083	Phase 2
0.5648	Remote Similarity	NPD6084	Phase 2
0.5645	Remote Similarity	NPD6616	Approved
0.5641	Remote Similarity	NPD8133	Approved
0.5631	Remote Similarity	NPD6903	Approved
0.562	Remote Similarity	NPD6054	Approved
0.562	Remote Similarity	NPD6319	Approved
0.5619	Remote Similarity	NPD7515	Phase 2
0.5614	Remote Similarity	NPD7320	Approved
0.5614	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5614	Remote Similarity	NPD6899	Approved
0.5614	Remote Similarity	NPD6881	Approved
0.5612	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.561	Remote Similarity	NPD8328	Phase 3
0.5603	Remote Similarity	NPD6649	Approved
0.5603	Remote Similarity	NPD6650	Approved
0.5603	Remote Similarity	NPD8130	Phase 1
0.56	Remote Similarity	NPD8293	Discontinued
0.56	Remote Similarity	NPD7078	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