NPASS Compound

Structure

CID110454 OpenBabel06191715462D 51 55 0 0 0 0 0 0 0 0999 V2000 2.4754 -3.0843 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4754 -1.9472 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1582 -4.1546 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1490 0.1884 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7555 -4.5797 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5642 0.1567 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4449 -3.0843 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0311 1.1893 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6415 -1.2880 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5174 -4.7572 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8143 -5.3223 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5642 -5.1881 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3181 -1.1196 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2708 -0.1231 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6898 -2.2229 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4601 -3.6528 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7268 0.0936 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -5.0315 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5640 -1.6510 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4449 -1.9472 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9228 1.0927 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7452 -1.2560 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9637 -4.3781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4733 -4.7625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1490 -5.2198 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9637 -0.6534 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4601 -1.3786 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7555 -0.4517 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6898 -2.8085 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2850 0.2722 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2693 -2.0163 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3181 -3.9119 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7268 -5.1251 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5174 -0.2743 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4296 -1.3786 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 3.5940 2.0106 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 -1.2121 -0.2516 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 -1.7892 -5.1601 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 -2.5442 -5.1450 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 2.2708 -4.9084 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.2105 -6.3553 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.7892 0.1286 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 4.4155 0.1498 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1330 -1.9758 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0311 -6.2207 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1555 0.6669 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2580 -6.9763 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8792 -0.1954 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1582 -0.8769 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5640 -3.3804 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 0 0 0 1 16 1 0 0 0 0 2 27 1 0 0 0 0 3 5 1 0 0 0 0 3 16 1 0 0 0 0 4 6 1 0 0 0 0 4 17 1 0 0 0 0 5 40 1 0 0 0 0 6 41 1 0 0 0 0 7 16 2 0 0 0 0 7 20 1 0 0 0 0 8 17 2 0 0 0 0 8 21 1 0 0 0 0 9 19 2 0 0 0 0 9 22 1 0 0 0 0 10 18 2 0 0 0 0 10 23 1 0 0 0 0 11 18 1 0 0 0 0 11 24 2 0 0 0 0 12 18 1 0 0 0 0 12 25 1 0 0 0 0 13 19 1 0 0 0 0 13 26 1 0 0 0 0 14 17 1 0 0 0 0 14 28 2 0 0 0 0 15 19 1 0 0 0 0 15 29 2 0 0 0 0 20 27 2 0 0 0 0 20 35 1 0 0 0 0 21 30 2 0 0 0 0 21 36 1 0 0 0 0 22 31 2 0 0 0 0 22 37 1 0 0 0 0 23 32 2 0 0 0 0 23 38 1 0 0 0 0 24 32 1 0 0 0 0 24 39 1 0 0 0 0 25 33 1 0 0 0 0 25 42 2 0 0 0 0 26 34 1 0 0 0 0 26 43 2 0 0 0 0 27 50 1 0 0 0 0 28 30 1 0 0 0 0 28 50 1 0 0 0 0 29 31 1 0 0 0 0 29 51 1 0 0 0 0 30 44 1 0 0 0 0 31 45 1 0 0 0 0 32 51 1 0 0 0 0 33 40 2 3 0 0 0 33 46 1 0 0 0 0 34 41 2 3 0 0 0 34 47 1 0 0 0 0 42 48 1 0 0 0 0 43 49 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	1013.77
Volume:	722.381
LogP:	6.744
LogD:	2.925
LogS:	-4.018
# Rotatable Bonds:	0
TPSA:	182.3
# H-Bond Aceptor:	12
# H-Bond Donor:	6
# Rings:	7
# Heavy Atoms:	17

MedChem Properties

QED Drug-Likeness Score:	0.075
Synthetic Accessibility Score:	5.984
Fsp3:	0.176
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:	-6.043
MDCK Permeability:	1.348930618405575e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.954
20% Bioavailability (F20%):	0.08
30% Bioavailability (F30%):	0.09

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.005
Plasma Protein Binding (PPB):	105.56787109375%
Volume Distribution (VD):	0.366
Pgp-substrate:	0.6760635375976562%

ADMET: Metabolism

CYP1A2-inhibitor:	0.317
CYP1A2-substrate:	0.032
CYP2C19-inhibitor:	0.951
CYP2C19-substrate:	0.048
CYP2C9-inhibitor:	0.981
CYP2C9-substrate:	0.838
CYP2D6-inhibitor:	0.776
CYP2D6-substrate:	0.241
CYP3A4-inhibitor:	0.567
CYP3A4-substrate:	0.347

ADMET: Excretion

Clearance (CL):	-0.35
Half-life (T1/2):	0.134

ADMET: Toxicity

hERG Blockers:	0.067
Human Hepatotoxicity (H-HT):	0.282
Drug-inuced Liver Injury (DILI):	0.627
AMES Toxicity:	0.023
Rat Oral Acute Toxicity:	0.935
Maximum Recommended Daily Dose:	0.963
Skin Sensitization:	0.896
Carcinogencity:	0.102
Eye Corrosion:	0.003
Eye Irritation:	0.007
Respiratory Toxicity:	0.023

Download Data

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

Natural Product: NPC110454

Natural Product ID:	NPC110454
*Common Name:**	Bastadin 19
IUPAC Name:	n.a.
Synonyms:	(E,E)-Bastadin-19; Bastadin 19
Standard InCHIKey:	AHBBQQLIUBAPCY-DCRHPOARSA-N
Standard InCHI:	InChI=1S/C34H27Br5N4O8/c35-20-7-16-1-2-27(20)50-28-14-17(8-21(36)30(28)44)4-6-41-34(47)26(43-49)13-19-9-22(37)31(45)29(15-19)51-32-23(38)10-18(11-24(32)39)12-25(42-48)33(46)40-5-3-16/h1-2,7-11,14-15,44-45,48-49H,3-6,12-13H2,(H,40,46)(H,41,47)/b42-25+,43-26+
SMILES:	c1cc2c(cc1CCN=C(/C(=N/O)/Cc1cc(c(c(c1)Br)Oc1cc(cc(c1O)Br)C/C(=NO)/C(=NCCc1cc(c(c(c1)O2)O)Br)O)Br)O)Br
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL506286
PubChem CID:	6413514
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds

*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
NPO33031	ianthella cf. reticulata	Species	Ianthellidae	Eukaryota	n.a.	n.a.	n.a.	PMID[20102170]
NPO16920	Ianthella basta	Species	Ianthellidae	Eukaryota	n.a.	Papua New Guinea	n.a.	PMID[2089117]
NPO29858	Ianthella	Genus	Ianthellidae	Eukaryota	n.a.	n.a.	n.a.	PMID[21214221]
NPO16920	Ianthella basta	Species	Ianthellidae	Eukaryota	n.a.	n.a.	n.a.	PMID[23249297]
NPO16920	Ianthella basta	Species	Ianthellidae	Eukaryota	n.a.	Bismarck archipelago	n.a.	PMID[7623047]
NPO16920	Ianthella basta	Species	Ianthellidae	Eukaryota	n.a.	Papua New Guinea	n.a.	PMID[8904842]
NPO16920	Ianthella basta	Species	Ianthellidae	Eukaryota	n.a.	n.a.	n.a.	PMID[8988595]
NPO16920	Ianthella basta	Species	Ianthellidae	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
EC50	2
IC50	2
Others	1

Activity Type	# Activity
Cell Line	1
Individual Protein	2
Organism	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT4277	Individual Protein	Ryanodine receptor 1	Homo sapiens	EC50	>	100000.0	nM	PMID[515081]
NPT2699	Individual Protein	Ryanodine receptor 1	Oryctolagus cuniculus	EC50	>	100000.0	nM	PMID[515082]
NPT737	Cell Line	HUVEC	Homo sapiens	IC50	=	120.0	nM	PMID[515084]
NPT471	Organism	Trypanosoma brucei brucei	Trypanosoma brucei brucei	IC50	=	1310.0	nM	PMID[515083]
NPT2	Others	Unspecified		Ratio IC50	=	19.0	n.a.	PMID[515084]

☑ 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 NPC110454 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	432
0.1-0.2	2786
0.2-0.3	14161
0.3-0.4	5053
0.4-0.5	9739
0.5-0.6	8841
0.6-0.7	1573
0.7-0.8	80
0.8-0.85	3
0.85-0.9	3
0.9-0.95	15
0.95-1	11

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC126128
1.0	High Similarity	NPC207819
1.0	High Similarity	NPC298981
1.0	High Similarity	NPC473462
0.9937	High Similarity	NPC226001
0.9937	High Similarity	NPC469979
0.9874	High Similarity	NPC225130
0.9815	High Similarity	NPC214188
0.9815	High Similarity	NPC74618
0.9815	High Similarity	NPC301941
0.9691	High Similarity	NPC290534
0.9578	High Similarity	NPC144823
0.9521	High Similarity	NPC82741
0.9521	High Similarity	NPC141405
0.9521	High Similarity	NPC473409
0.9461	High Similarity	NPC471591
0.9401	High Similarity	NPC49172
0.9394	High Similarity	NPC475396
0.9244	High Similarity	NPC469721
0.9231	High Similarity	NPC473892
0.9231	High Similarity	NPC475658
0.9176	High Similarity	NPC470951
0.9138	High Similarity	NPC469731
0.9107	High Similarity	NPC475283
0.9107	High Similarity	NPC152205
0.9042	High Similarity	NPC475615
0.8827	High Similarity	NPC156055
0.8075	Intermediate Similarity	NPC474128
0.8012	Intermediate Similarity	NPC258222
0.7964	Intermediate Similarity	NPC475432
0.7824	Intermediate Similarity	NPC156311
0.7805	Intermediate Similarity	NPC222039
0.7805	Intermediate Similarity	NPC100478
0.7778	Intermediate Similarity	NPC473738
0.7736	Intermediate Similarity	NPC475735
0.7673	Intermediate Similarity	NPC474091
0.7588	Intermediate Similarity	NPC109968
0.756	Intermediate Similarity	NPC5462
0.7557	Intermediate Similarity	NPC50380
0.7557	Intermediate Similarity	NPC179250
0.7516	Intermediate Similarity	NPC114102
0.7471	Intermediate Similarity	NPC107602
0.7469	Intermediate Similarity	NPC214869
0.7455	Intermediate Similarity	NPC213471
0.7442	Intermediate Similarity	NPC47672
0.744	Intermediate Similarity	NPC135349
0.744	Intermediate Similarity	NPC78530
0.743	Intermediate Similarity	NPC90984
0.7427	Intermediate Similarity	NPC471032
0.7427	Intermediate Similarity	NPC470935
0.7394	Intermediate Similarity	NPC309667
0.7386	Intermediate Similarity	NPC123848
0.7368	Intermediate Similarity	NPC115144
0.7368	Intermediate Similarity	NPC277857
0.7346	Intermediate Similarity	NPC52029
0.7346	Intermediate Similarity	NPC35961
0.7346	Intermediate Similarity	NPC195749
0.7314	Intermediate Similarity	NPC233926
0.7301	Intermediate Similarity	NPC473724
0.7299	Intermediate Similarity	NPC127402
0.7284	Intermediate Similarity	NPC155838
0.7273	Intermediate Similarity	NPC120114
0.7273	Intermediate Similarity	NPC71888
0.7273	Intermediate Similarity	NPC303993
0.7225	Intermediate Similarity	NPC76412
0.7222	Intermediate Similarity	NPC251571
0.7222	Intermediate Similarity	NPC153990
0.7222	Intermediate Similarity	NPC186898
0.716	Intermediate Similarity	NPC156854
0.716	Intermediate Similarity	NPC17837
0.716	Intermediate Similarity	NPC304630
0.716	Intermediate Similarity	NPC301713
0.716	Intermediate Similarity	NPC134431
0.7152	Intermediate Similarity	NPC93882
0.7152	Intermediate Similarity	NPC130595
0.7151	Intermediate Similarity	NPC32064
0.7143	Intermediate Similarity	NPC14600
0.7143	Intermediate Similarity	NPC204848
0.7143	Intermediate Similarity	NPC312770
0.7143	Intermediate Similarity	NPC160607
0.7143	Intermediate Similarity	NPC41473
0.7108	Intermediate Similarity	NPC285078
0.7108	Intermediate Similarity	NPC6854
0.7108	Intermediate Similarity	NPC313737
0.7101	Intermediate Similarity	NPC299583
0.7083	Intermediate Similarity	NPC474587
0.7083	Intermediate Similarity	NPC475132
0.7066	Intermediate Similarity	NPC218530
0.7049	Intermediate Similarity	NPC240841
0.7049	Intermediate Similarity	NPC250846
0.7049	Intermediate Similarity	NPC42549
0.7049	Intermediate Similarity	NPC317272
0.7049	Intermediate Similarity	NPC256012
0.7049	Intermediate Similarity	NPC268503
0.7045	Intermediate Similarity	NPC7398
0.7041	Intermediate Similarity	NPC475293
0.7035	Intermediate Similarity	NPC254581
0.7035	Intermediate Similarity	NPC470472
0.703	Intermediate Similarity	NPC210655
0.703	Intermediate Similarity	NPC99280
0.7022	Intermediate Similarity	NPC56635
0.7	Intermediate Similarity	NPC296898
0.7	Intermediate Similarity	NPC138083
0.6988	Remote Similarity	NPC255550
0.6988	Remote Similarity	NPC308885
0.6981	Remote Similarity	NPC268572
0.6966	Remote Similarity	NPC275027
0.6963	Remote Similarity	NPC276120
0.6959	Remote Similarity	NPC41122
0.6959	Remote Similarity	NPC318805
0.6935	Remote Similarity	NPC164608
0.691	Remote Similarity	NPC52475
0.6905	Remote Similarity	NPC474134
0.6905	Remote Similarity	NPC73656
0.6905	Remote Similarity	NPC131128
0.6898	Remote Similarity	NPC108434
0.6898	Remote Similarity	NPC475215
0.6891	Remote Similarity	NPC234069
0.6888	Remote Similarity	NPC85381
0.6875	Remote Similarity	NPC38483
0.6872	Remote Similarity	NPC18614
0.686	Remote Similarity	NPC477838
0.686	Remote Similarity	NPC477837
0.6856	Remote Similarity	NPC174122
0.6856	Remote Similarity	NPC64140
0.6856	Remote Similarity	NPC29531
0.6855	Remote Similarity	NPC86947
0.6837	Remote Similarity	NPC227953
0.6831	Remote Similarity	NPC38980
0.6824	Remote Similarity	NPC66840
0.6824	Remote Similarity	NPC256307
0.6824	Remote Similarity	NPC141023
0.6818	Remote Similarity	NPC234318
0.6813	Remote Similarity	NPC122009
0.6805	Remote Similarity	NPC163810
0.6802	Remote Similarity	NPC202866
0.6798	Remote Similarity	NPC182119
0.6788	Remote Similarity	NPC77435
0.6788	Remote Similarity	NPC259071
0.6782	Remote Similarity	NPC470372
0.6782	Remote Similarity	NPC8577
0.678	Remote Similarity	NPC88896
0.677	Remote Similarity	NPC44270
0.677	Remote Similarity	NPC86007
0.676	Remote Similarity	NPC152947
0.6753	Remote Similarity	NPC249113
0.675	Remote Similarity	NPC283468
0.6746	Remote Similarity	NPC474753
0.6744	Remote Similarity	NPC474673
0.6744	Remote Similarity	NPC470470
0.6736	Remote Similarity	NPC30779
0.6725	Remote Similarity	NPC470471
0.6725	Remote Similarity	NPC245386
0.6724	Remote Similarity	NPC262189
0.6723	Remote Similarity	NPC245974
0.6716	Remote Similarity	NPC471337
0.6708	Remote Similarity	NPC104124
0.6707	Remote Similarity	NPC202776
0.6706	Remote Similarity	NPC189482
0.6705	Remote Similarity	NPC271942
0.6705	Remote Similarity	NPC247298
0.6705	Remote Similarity	NPC474390
0.6702	Remote Similarity	NPC66573
0.6701	Remote Similarity	NPC8093
0.6701	Remote Similarity	NPC121571
0.6687	Remote Similarity	NPC47769
0.6687	Remote Similarity	NPC153580
0.6687	Remote Similarity	NPC299939
0.6687	Remote Similarity	NPC226737
0.6687	Remote Similarity	NPC220311
0.6687	Remote Similarity	NPC110131
0.6687	Remote Similarity	NPC170824
0.6687	Remote Similarity	NPC196371
0.6684	Remote Similarity	NPC286119
0.6667	Remote Similarity	NPC174607
0.6667	Remote Similarity	NPC478189
0.6667	Remote Similarity	NPC25084
0.6667	Remote Similarity	NPC55947
0.6667	Remote Similarity	NPC13020
0.6667	Remote Similarity	NPC140359
0.6667	Remote Similarity	NPC474678
0.6667	Remote Similarity	NPC260842
0.6667	Remote Similarity	NPC247639
0.6667	Remote Similarity	NPC471338
0.6649	Remote Similarity	NPC49075
0.6649	Remote Similarity	NPC104196
0.6649	Remote Similarity	NPC42663
0.6649	Remote Similarity	NPC7715
0.6649	Remote Similarity	NPC279228
0.6649	Remote Similarity	NPC258657
0.6649	Remote Similarity	NPC185639
0.6649	Remote Similarity	NPC222661
0.6649	Remote Similarity	NPC182052
0.6649	Remote Similarity	NPC90998
0.6649	Remote Similarity	NPC251735
0.6649	Remote Similarity	NPC311973
0.6649	Remote Similarity	NPC290005
0.6649	Remote Similarity	NPC54654
0.6649	Remote Similarity	NPC239824
0.6649	Remote Similarity	NPC290582

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 NPC110454 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	235
0.1-0.2	915
0.2-0.3	1446
0.3-0.4	2847
0.4-0.5	2381
0.5-0.6	1168
0.6-0.7	155
0.7-0.8	3
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
0.7152	Intermediate Similarity	NPD2674	Phase 3
0.7049	Intermediate Similarity	NPD4010	Discontinued
0.7035	Intermediate Similarity	NPD6331	Phase 2
0.7035	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD3144	Approved
0.6988	Remote Similarity	NPD3145	Approved
0.6919	Remote Similarity	NPD8095	Phase 1
0.6875	Remote Similarity	NPD4123	Phase 3
0.6821	Remote Similarity	NPD7153	Discontinued
0.6802	Remote Similarity	NPD2161	Phase 2
0.6706	Remote Similarity	NPD5837	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD7945	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD4675	Approved
0.6685	Remote Similarity	NPD4678	Approved
0.6667	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3676	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5772	Approved
0.6667	Remote Similarity	NPD5773	Approved
0.6649	Remote Similarity	NPD8053	Approved
0.6649	Remote Similarity	NPD8054	Approved
0.6648	Remote Similarity	NPD52	Approved
0.6648	Remote Similarity	NPD7527	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD7526	Approved
0.6648	Remote Similarity	NPD5261	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD1726	Clinical (unspecified phase)
0.6611	Remote Similarity	NPD2122	Discontinued
0.6608	Remote Similarity	NPD1558	Phase 1
0.6592	Remote Similarity	NPD4739	Approved
0.6591	Remote Similarity	NPD4162	Approved
0.6578	Remote Similarity	NPD7201	Clinical (unspecified phase)
0.6559	Remote Similarity	NPD7832	Clinical (unspecified phase)
0.6559	Remote Similarity	NPD7831	Phase 2
0.6559	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6559	Remote Similarity	NPD7833	Phase 2
0.655	Remote Similarity	NPD7477	Discontinued
0.6548	Remote Similarity	NPD6584	Phase 3
0.6546	Remote Similarity	NPD2802	Phase 3
0.6538	Remote Similarity	NPD4005	Discontinued
0.6534	Remote Similarity	NPD7596	Clinical (unspecified phase)
0.6517	Remote Similarity	NPD5241	Discontinued
0.6497	Remote Similarity	NPD3060	Approved
0.6491	Remote Similarity	NPD5718	Phase 2
0.6471	Remote Similarity	NPD8070	Approved
0.6467	Remote Similarity	NPD3778	Approved
0.6457	Remote Similarity	NPD6029	Clinical (unspecified phase)
0.6457	Remote Similarity	NPD6028	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD2922	Phase 1
0.6417	Remote Similarity	NPD7773	Phase 2
0.6409	Remote Similarity	NPD7446	Clinical (unspecified phase)
0.6409	Remote Similarity	NPD1754	Clinical (unspecified phase)
0.6407	Remote Similarity	NPD2337	Clinical (unspecified phase)
0.6398	Remote Similarity	NPD6818	Clinical (unspecified phase)
0.6395	Remote Similarity	NPD5109	Approved
0.6395	Remote Similarity	NPD5110	Phase 2
0.6395	Remote Similarity	NPD5111	Phase 2
0.6384	Remote Similarity	NPD1375	Discontinued
0.6369	Remote Similarity	NPD1669	Approved
0.6369	Remote Similarity	NPD6582	Phase 2
0.6369	Remote Similarity	NPD6583	Phase 3
0.6353	Remote Similarity	NPD7451	Discontinued
0.6348	Remote Similarity	NPD7037	Approved
0.6331	Remote Similarity	NPD5311	Approved
0.6331	Remote Similarity	NPD5310	Approved
0.631	Remote Similarity	NPD2977	Approved
0.631	Remote Similarity	NPD2978	Approved
0.6307	Remote Similarity	NPD6895	Approved
0.6307	Remote Similarity	NPD6896	Approved
0.6302	Remote Similarity	NPD6687	Approved
0.6302	Remote Similarity	NPD4083	Discontinued
0.6302	Remote Similarity	NPD6688	Approved
0.6298	Remote Similarity	NPD6783	Clinical (unspecified phase)
0.6294	Remote Similarity	NPD3053	Approved
0.6294	Remote Similarity	NPD3055	Approved
0.629	Remote Similarity	NPD6072	Discontinued
0.6289	Remote Similarity	NPD8252	Approved
0.6289	Remote Similarity	NPD8251	Approved
0.6289	Remote Similarity	NPD8099	Discontinued
0.6279	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6273	Remote Similarity	NPD228	Approved
0.6269	Remote Similarity	NPD27	Approved
0.6269	Remote Similarity	NPD2489	Approved
0.6257	Remote Similarity	NPD5722	Discontinued
0.6257	Remote Similarity	NPD4664	Clinical (unspecified phase)
0.6256	Remote Similarity	NPD8156	Discontinued
0.625	Remote Similarity	NPD2653	Approved
0.625	Remote Similarity	NPD6030	Approved
0.625	Remote Similarity	NPD6031	Approved
0.6237	Remote Similarity	NPD5602	Clinical (unspecified phase)
0.6237	Remote Similarity	NPD3296	Phase 1
0.6235	Remote Similarity	NPD821	Approved
0.623	Remote Similarity	NPD3985	Discontinued
0.623	Remote Similarity	NPD7019	Approved
0.623	Remote Similarity	NPD7020	Approved
0.623	Remote Similarity	NPD1771	Clinical (unspecified phase)
0.6222	Remote Similarity	NPD4236	Phase 3
0.6222	Remote Similarity	NPD4237	Approved
0.6221	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6219	Remote Similarity	NPD7906	Approved
0.6211	Remote Similarity	NPD4055	Discovery
0.6207	Remote Similarity	NPD6812	Clinical (unspecified phase)
0.6205	Remote Similarity	NPD7493	Clinical (unspecified phase)
0.6203	Remote Similarity	NPD7438	Suspended
0.6201	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6201	Remote Similarity	NPD3656	Approved
0.6196	Remote Similarity	NPD2183	Approved
0.6196	Remote Similarity	NPD2184	Approved
0.6183	Remote Similarity	NPD6523	Clinical (unspecified phase)
0.6183	Remote Similarity	NPD3866	Clinical (unspecified phase)
0.6176	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6166	Remote Similarity	NPD7608	Discontinued
0.6166	Remote Similarity	NPD3051	Approved
0.6158	Remote Similarity	NPD2157	Approved
0.6154	Remote Similarity	NPD3692	Discontinued
0.615	Remote Similarity	NPD6502	Phase 2
0.6149	Remote Similarity	NPD3027	Phase 3
0.6141	Remote Similarity	NPD4584	Approved
0.6141	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6138	Remote Similarity	NPD5563	Clinical (unspecified phase)
0.6136	Remote Similarity	NPD1613	Approved
0.6136	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6135	Remote Similarity	NPD9379	Approved
0.6135	Remote Similarity	NPD9377	Approved
0.6134	Remote Similarity	NPD2969	Approved
0.6134	Remote Similarity	NPD2970	Approved
0.6133	Remote Similarity	NPD2460	Phase 3
0.6133	Remote Similarity	NPD5177	Phase 3
0.6133	Remote Similarity	NPD2458	Approved
0.6133	Remote Similarity	NPD2459	Approved
0.6131	Remote Similarity	NPD7132	Clinical (unspecified phase)
0.6129	Remote Similarity	NPD3686	Approved
0.6129	Remote Similarity	NPD3687	Approved
0.6127	Remote Similarity	NPD1712	Approved
0.6127	Remote Similarity	NPD4993	Discontinued
0.6126	Remote Similarity	NPD5604	Discontinued
0.6118	Remote Similarity	NPD2231	Phase 2
0.6118	Remote Similarity	NPD2235	Phase 2
0.6108	Remote Similarity	NPD3647	Clinical (unspecified phase)
0.61	Remote Similarity	NPD4577	Approved
0.61	Remote Similarity	NPD4578	Approved
0.6098	Remote Similarity	NPD5283	Phase 1
0.6094	Remote Similarity	NPD8398	Clinical (unspecified phase)
0.6091	Remote Similarity	NPD4873	Discontinued
0.6089	Remote Similarity	NPD4663	Approved
0.6089	Remote Similarity	NPD1169	Approved
0.6089	Remote Similarity	NPD7425	Clinical (unspecified phase)
0.6089	Remote Similarity	NPD4108	Discontinued
0.6087	Remote Similarity	NPD6087	Phase 1
0.608	Remote Similarity	NPD7038	Approved
0.608	Remote Similarity	NPD1423	Approved
0.608	Remote Similarity	NPD7039	Approved
0.608	Remote Similarity	NPD839	Approved
0.608	Remote Similarity	NPD840	Approved
0.6078	Remote Similarity	NPD5641	Discontinued
0.6073	Remote Similarity	NPD4581	Clinical (unspecified phase)
0.6067	Remote Similarity	NPD3052	Approved
0.6067	Remote Similarity	NPD1772	Clinical (unspecified phase)
0.6067	Remote Similarity	NPD5314	Approved
0.6067	Remote Similarity	NPD3054	Approved
0.6066	Remote Similarity	NPD5084	Clinical (unspecified phase)
0.6057	Remote Similarity	NPD2669	Clinical (unspecified phase)
0.6054	Remote Similarity	NPD2874	Phase 2
0.6054	Remote Similarity	NPD3536	Discontinued
0.6054	Remote Similarity	NPD7447	Phase 1
0.6053	Remote Similarity	NPD7089	Clinical (unspecified phase)
0.6045	Remote Similarity	NPD3061	Approved
0.6045	Remote Similarity	NPD3059	Approved
0.6045	Remote Similarity	NPD3062	Approved
0.6043	Remote Similarity	NPD4003	Phase 3
0.6039	Remote Similarity	NPD2804	Phase 1
0.6036	Remote Similarity	NPD2667	Approved
0.6036	Remote Similarity	NPD2668	Approved
0.6034	Remote Similarity	NPD2407	Clinical (unspecified phase)
0.6033	Remote Similarity	NPD3845	Phase 1
0.6033	Remote Similarity	NPD7124	Phase 2
0.6032	Remote Similarity	NPD4773	Phase 2
0.6032	Remote Similarity	NPD4772	Phase 2
0.6029	Remote Similarity	NPD6377	Clinical (unspecified phase)
0.6023	Remote Similarity	NPD2028	Clinical (unspecified phase)
0.6021	Remote Similarity	NPD2296	Approved
0.6021	Remote Similarity	NPD6063	Approved
0.602	Remote Similarity	NPD7312	Approved
0.602	Remote Similarity	NPD7313	Approved
0.602	Remote Similarity	NPD3337	Discontinued
0.602	Remote Similarity	NPD7311	Approved
0.602	Remote Similarity	NPD7310	Approved
0.6012	Remote Similarity	NPD6580	Approved
0.6012	Remote Similarity	NPD6581	Approved
0.6011	Remote Similarity	NPD3455	Phase 2
0.6011	Remote Similarity	NPD3111	Phase 1
0.6011	Remote Similarity	NPD5811	Approved
0.6	Remote Similarity	NPD4357	Discontinued
0.6	Remote Similarity	NPD5720	Discontinued
0.6	Remote Similarity	NPD4606	Clinical (unspecified phase)
0.6	Remote Similarity	NPD4433	Discontinued
0.6	Remote Similarity	NPD7212	Phase 2
0.6	Remote Similarity	NPD7213	Phase 3
0.599	Remote Similarity	NPD7309	Approved
0.599	Remote Similarity	NPD6788	Approved
0.5989	Remote Similarity	NPD1044	Clinical (unspecified phase)
0.5989	Remote Similarity	NPD2808	Discontinued

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