NPASS Compound

Structure

NPC226001 OpenBabel07101718312D 52 56 0 0 0 0 0 0 0 0999 V2000 -0.7975 -0.8121 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8902 1.4534 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3546 -0.4494 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8181 2.0212 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6839 0.3952 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8623 -1.2142 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7040 -1.8178 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2107 2.5003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3389 4.0511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4310 4.6684 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4409 3.7665 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3932 1.6442 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9933 0.3952 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0493 2.7292 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3080 -1.0710 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8386 0.8832 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9054 3.9687 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2802 2.2054 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6839 -0.5808 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4205 3.4536 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4344 -1.2348 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5487 -1.8484 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7680 4.0098 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5880 4.6074 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9205 3.4538 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3828 1.0719 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9933 -0.5808 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2889 3.1911 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8386 -1.0689 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6611 2.7014 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9975 -1.1320 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2192 3.8468 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3216 3.0454 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2497 0.5151 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5292 -1.0689 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 1.9027 4.3022 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 -2.5752 -3.1819 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 -3.0059 -2.7107 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 -1.4174 5.9302 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 -1.0402 5.4153 0.0000 Br 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 -4.6255 2.5603 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.5388 4.2090 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.3511 0.9488 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.8386 -2.0449 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8093 1.7366 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0878 3.6500 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1689 0.1868 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1940 5.1222 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9418 1.7259 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5254 -0.9106 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7184 3.5695 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 1 0 0 0 0 1 15 1 0 0 0 0 2 4 1 0 0 0 0 2 16 1 0 0 0 0 3 41 1 0 0 0 0 4 42 1 0 0 0 0 5 16 2 0 0 0 0 5 19 1 0 0 0 0 6 15 2 0 0 0 0 6 21 1 0 0 0 0 7 15 1 0 0 0 0 7 22 2 0 0 0 0 8 18 2 0 0 0 0 8 20 1 0 0 0 0 9 17 2 0 0 0 0 9 23 1 0 0 0 0 10 17 1 0 0 0 0 10 24 2 0 0 0 0 11 17 1 0 0 0 0 11 25 1 0 0 0 0 12 18 1 0 0 0 0 12 26 1 0 0 0 0 13 16 1 0 0 0 0 13 27 2 0 0 0 0 14 18 1 0 0 0 0 14 28 2 0 0 0 0 19 29 2 0 0 0 0 19 35 1 0 0 0 0 20 30 2 0 0 0 0 20 36 1 0 0 0 0 21 31 2 0 0 0 0 21 37 1 0 0 0 0 22 31 1 0 0 0 0 22 38 1 0 0 0 0 23 32 2 0 0 0 0 23 39 1 0 0 0 0 24 32 1 0 0 0 0 24 40 1 0 0 0 0 25 33 1 0 0 0 0 25 43 2 0 0 0 0 26 34 1 0 0 0 0 26 44 2 0 0 0 0 27 29 1 0 0 0 0 27 51 1 0 0 0 0 28 30 1 0 0 0 0 28 52 1 0 0 0 0 29 45 1 0 0 0 0 30 46 1 0 0 0 0 31 51 1 0 0 0 0 32 52 1 0 0 0 0 33 42 2 3 0 0 0 33 47 1 0 0 0 0 34 41 2 3 0 0 0 34 48 1 0 0 0 0 43 49 1 0 0 0 0 44 50 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	1091.69
Volume:	741.665
LogP:	7.181
LogD:	2.93
LogS:	-4.05
# Rotatable Bonds:	0
TPSA:	182.3
# H-Bond Aceptor:	12
# H-Bond Donor:	6
# Rings:	8
# Heavy Atoms:	18

MedChem Properties

QED Drug-Likeness Score:	0.075
Synthetic Accessibility Score:	5.945
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:	-6.073
MDCK Permeability:	1.303034423472127e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.974
20% Bioavailability (F20%):	0.087
30% Bioavailability (F30%):	0.231

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.005
Plasma Protein Binding (PPB):	107.88106536865234%
Volume Distribution (VD):	0.396
Pgp-substrate:	1.0203921794891357%

ADMET: Metabolism

CYP1A2-inhibitor:	0.232
CYP1A2-substrate:	0.037
CYP2C19-inhibitor:	0.947
CYP2C19-substrate:	0.048
CYP2C9-inhibitor:	0.979
CYP2C9-substrate:	0.746
CYP2D6-inhibitor:	0.65
CYP2D6-substrate:	0.2
CYP3A4-inhibitor:	0.405
CYP3A4-substrate:	0.254

ADMET: Excretion

Clearance (CL):	-0.82
Half-life (T1/2):	0.11

ADMET: Toxicity

hERG Blockers:	0.079
Human Hepatotoxicity (H-HT):	0.268
Drug-inuced Liver Injury (DILI):	0.484
AMES Toxicity:	0.021
Rat Oral Acute Toxicity:	0.97
Maximum Recommended Daily Dose:	0.969
Skin Sensitization:	0.897
Carcinogencity:	0.094
Eye Corrosion:	0.003
Eye Irritation:	0.008
Respiratory Toxicity:	0.036

Download Data

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

Natural Product: NPC226001

Natural Product ID:	NPC226001
*Common Name:**	Bastadin 6
IUPAC Name:	n.a.
Synonyms:	Bastadin 6; Bastadin-6
Standard InCHIKey:	WSOCBHDTRCSWRH-PJUICVFASA-N
Standard InCHI:	InChI=1S/C34H26Br6N4O8/c35-19-5-16-2-4-42-33(47)25(43-49)11-17-9-23(39)32(24(40)10-17)52-28-14-18(8-20(36)30(28)46)12-26(44-50)34(48)41-3-1-15-6-21(37)31(22(38)7-15)51-27(13-16)29(19)45/h5-10,13-14,45-46,49-50H,1-4,11-12H2,(H,41,48)(H,42,47)/b43-25+,44-26+
SMILES:	C1CN=C(/C(=N/O)/Cc2cc(c(c(c2)Oc2c(cc(cc2Br)C/C(=NO)/C(=NCCc2cc(c(c(c2)Oc2c(cc1cc2Br)Br)O)Br)O)Br)O)Br)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL510730
PubChem CID:	9833337
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]
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
IC50	9
MIC	2
Others	6

Activity Type	# Activity
Cell Line	2
Individual Protein	10
Organism	2
Others	2
Protein Complex	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1432	Individual Protein	Serine/threonine-protein kinase Aurora-A	Homo sapiens	IC50	=	1700.0	nM	PMID[573291]
NPT1433	Individual Protein	Serine/threonine-protein kinase Aurora-B	Homo sapiens	IC50	=	2900.0	nM	PMID[573291]
NPT2571	Individual Protein	Mitogen-activated protein kinase kinase kinase 8	Homo sapiens	IC50	=	4800.0	nM	PMID[573291]
NPT285	Individual Protein	Epidermal growth factor receptor erbB1	Homo sapiens	IC50	=	2000.0	nM	PMID[573291]
NPT286	Individual Protein	Receptor protein-tyrosine kinase erbB-2	Homo sapiens	IC50	=	7000.0	nM	PMID[573291]
NPT1650	Individual Protein	Tyrosine-protein kinase receptor FLT3	Homo sapiens	IC50	=	5300.0	nM	PMID[573291]
NPT1864	Cell Line	L5178Y	Mus musculus	IC50	=	1500.0	nM	PMID[573291]
NPT737	Cell Line	HUVEC	Homo sapiens	IC50	=	52.0	nM	PMID[573292]
NPT2584	Individual Protein	Acyl coenzyme A:cholesterol acyltransferase 2	Homo sapiens	Inhibition	=	89.0	%	PMID[573293]
NPT1214	Individual Protein	Acyl coenzyme A:cholesterol acyltransferase 1	Homo sapiens	Inhibition	=	82.0	%	PMID[573293]
NPT2584	Individual Protein	Acyl coenzyme A:cholesterol acyltransferase 2	Homo sapiens	Inhibition	=	87.0	%	PMID[573293]
NPT1214	Individual Protein	Acyl coenzyme A:cholesterol acyltransferase 1	Homo sapiens	Inhibition	=	86.0	%	PMID[573293]
NPT175	Organism	Enterococcus faecalis	Enterococcus faecalis	MIC	=	12.5	ug	PMID[573289]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	6.25	ug	PMID[573289]
NPT1560	Protein Complex	Cyclin-dependent kinase 4/cyclin D1	Homo sapiens	IC50	=	3600.0	nM	PMID[573291]
NPT2	Others	Unspecified		Ratio IC50	=	41.0	n.a.	PMID[573292]
NPT2	Others	Unspecified		Inhibition	=	96.0	%	PMID[573293]

☑ 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 NPC226001 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	451
0.1-0.2	3085
0.2-0.3	14437
0.3-0.4	5133
0.4-0.5	10511
0.5-0.6	7957
0.6-0.7	1047
0.7-0.8	47
0.8-0.85	0
0.85-0.9	5
0.9-0.95	10
0.95-1	14

Similarity Score	Similarity Level	Natural Product ID
0.9937	High Similarity	NPC473462
0.9937	High Similarity	NPC207819
0.9937	High Similarity	NPC126128
0.9937	High Similarity	NPC298981
0.9937	High Similarity	NPC110454
0.9874	High Similarity	NPC469979
0.9811	High Similarity	NPC225130
0.9753	High Similarity	NPC301941
0.9753	High Similarity	NPC214188
0.9753	High Similarity	NPC74618
0.963	High Similarity	NPC290534
0.9518	High Similarity	NPC471591
0.9518	High Similarity	NPC144823
0.9461	High Similarity	NPC141405
0.9461	High Similarity	NPC473409
0.9461	High Similarity	NPC82741
0.9341	High Similarity	NPC49172
0.9333	High Similarity	NPC475396
0.9186	High Similarity	NPC469721
0.9172	High Similarity	NPC475658
0.9172	High Similarity	NPC473892
0.9118	High Similarity	NPC470951
0.908	High Similarity	NPC469731
0.9048	High Similarity	NPC152205
0.9048	High Similarity	NPC475283
0.8982	High Similarity	NPC475615
0.8876	High Similarity	NPC156055
0.8012	Intermediate Similarity	NPC474128
0.7952	Intermediate Similarity	NPC258222
0.7904	Intermediate Similarity	NPC475432
0.7765	Intermediate Similarity	NPC156311
0.7744	Intermediate Similarity	NPC222039
0.7744	Intermediate Similarity	NPC100478
0.7719	Intermediate Similarity	NPC473738
0.7673	Intermediate Similarity	NPC475735
0.761	Intermediate Similarity	NPC474091
0.7529	Intermediate Similarity	NPC109968
0.75	Intermediate Similarity	NPC50380
0.75	Intermediate Similarity	NPC5462
0.75	Intermediate Similarity	NPC179250
0.7453	Intermediate Similarity	NPC114102
0.7414	Intermediate Similarity	NPC107602
0.7407	Intermediate Similarity	NPC214869
0.7394	Intermediate Similarity	NPC213471
0.7384	Intermediate Similarity	NPC47672
0.7381	Intermediate Similarity	NPC78530
0.7381	Intermediate Similarity	NPC135349
0.7374	Intermediate Similarity	NPC90984
0.7368	Intermediate Similarity	NPC470935
0.7368	Intermediate Similarity	NPC471032
0.7333	Intermediate Similarity	NPC309667
0.733	Intermediate Similarity	NPC123848
0.731	Intermediate Similarity	NPC277857
0.731	Intermediate Similarity	NPC115144
0.7284	Intermediate Similarity	NPC195749
0.7284	Intermediate Similarity	NPC52029
0.7284	Intermediate Similarity	NPC35961
0.7257	Intermediate Similarity	NPC233926
0.7241	Intermediate Similarity	NPC127402
0.7239	Intermediate Similarity	NPC473724
0.7222	Intermediate Similarity	NPC155838
0.7212	Intermediate Similarity	NPC303993
0.7212	Intermediate Similarity	NPC71888
0.7212	Intermediate Similarity	NPC120114
0.7168	Intermediate Similarity	NPC76412
0.716	Intermediate Similarity	NPC153990
0.716	Intermediate Similarity	NPC251571
0.716	Intermediate Similarity	NPC186898
0.7099	Intermediate Similarity	NPC304630
0.7099	Intermediate Similarity	NPC134431
0.7099	Intermediate Similarity	NPC301713
0.7099	Intermediate Similarity	NPC156854
0.7099	Intermediate Similarity	NPC17837
0.7097	Intermediate Similarity	NPC32064
0.7091	Intermediate Similarity	NPC130595
0.7091	Intermediate Similarity	NPC93882
0.7083	Intermediate Similarity	NPC312770
0.7083	Intermediate Similarity	NPC160607
0.7083	Intermediate Similarity	NPC41473
0.7083	Intermediate Similarity	NPC14600
0.7083	Intermediate Similarity	NPC204848
0.7048	Intermediate Similarity	NPC6854
0.7048	Intermediate Similarity	NPC313737
0.7048	Intermediate Similarity	NPC285078
0.7041	Intermediate Similarity	NPC299583
0.7024	Intermediate Similarity	NPC474587
0.7024	Intermediate Similarity	NPC475132
0.7006	Intermediate Similarity	NPC218530
0.6995	Remote Similarity	NPC42549
0.6995	Remote Similarity	NPC317272
0.6995	Remote Similarity	NPC268503
0.6995	Remote Similarity	NPC240841
0.6995	Remote Similarity	NPC250846
0.6995	Remote Similarity	NPC256012
0.6989	Remote Similarity	NPC7398
0.6985	Remote Similarity	NPC254581
0.6982	Remote Similarity	NPC475293
0.6977	Remote Similarity	NPC470472
0.697	Remote Similarity	NPC99280
0.697	Remote Similarity	NPC210655
0.6966	Remote Similarity	NPC56635
0.6947	Remote Similarity	NPC138083
0.6941	Remote Similarity	NPC296898
0.6928	Remote Similarity	NPC308885
0.6928	Remote Similarity	NPC255550
0.6918	Remote Similarity	NPC268572
0.6918	Remote Similarity	NPC38483
0.6911	Remote Similarity	NPC276120
0.691	Remote Similarity	NPC275027
0.6907	Remote Similarity	NPC318805
0.6907	Remote Similarity	NPC41122
0.6882	Remote Similarity	NPC164608
0.6872	Remote Similarity	NPC227953
0.6868	Remote Similarity	NPC38980
0.6854	Remote Similarity	NPC52475
0.6845	Remote Similarity	NPC131128
0.6845	Remote Similarity	NPC475215
0.6845	Remote Similarity	NPC73656
0.6845	Remote Similarity	NPC108434
0.6845	Remote Similarity	NPC474134
0.6839	Remote Similarity	NPC234069
0.6837	Remote Similarity	NPC202866
0.6837	Remote Similarity	NPC85381
0.6823	Remote Similarity	NPC77435
0.6823	Remote Similarity	NPC259071
0.6816	Remote Similarity	NPC18614
0.6804	Remote Similarity	NPC29531
0.6804	Remote Similarity	NPC64140
0.6804	Remote Similarity	NPC174122
0.6802	Remote Similarity	NPC477838
0.6802	Remote Similarity	NPC477837
0.6798	Remote Similarity	NPC152947
0.6792	Remote Similarity	NPC86947
0.6788	Remote Similarity	NPC249113
0.6784	Remote Similarity	NPC474673
0.6768	Remote Similarity	NPC234318
0.6765	Remote Similarity	NPC66840
0.6765	Remote Similarity	NPC245386
0.6765	Remote Similarity	NPC256307
0.6765	Remote Similarity	NPC141023
0.675	Remote Similarity	NPC471337
0.675	Remote Similarity	NPC122009
0.675	Remote Similarity	NPC104124
0.6746	Remote Similarity	NPC163810
0.6744	Remote Similarity	NPC271942
0.6742	Remote Similarity	NPC182119
0.6738	Remote Similarity	NPC66573
0.6736	Remote Similarity	NPC121571
0.6736	Remote Similarity	NPC8093
0.6728	Remote Similarity	NPC170824
0.6727	Remote Similarity	NPC110131
0.6727	Remote Similarity	NPC220311
0.6724	Remote Similarity	NPC8577
0.6724	Remote Similarity	NPC470372
0.6723	Remote Similarity	NPC88896
0.6708	Remote Similarity	NPC86007
0.6708	Remote Similarity	NPC44270
0.6701	Remote Similarity	NPC474678
0.6701	Remote Similarity	NPC471338
0.6701	Remote Similarity	NPC174607
0.6687	Remote Similarity	NPC283468
0.6686	Remote Similarity	NPC470470
0.6686	Remote Similarity	NPC474753
0.6684	Remote Similarity	NPC30779
0.6667	Remote Similarity	NPC475843
0.6667	Remote Similarity	NPC245974
0.6667	Remote Similarity	NPC272463
0.6667	Remote Similarity	NPC147847
0.6667	Remote Similarity	NPC41232
0.6667	Remote Similarity	NPC63317
0.6667	Remote Similarity	NPC262189
0.6667	Remote Similarity	NPC470471
0.6648	Remote Similarity	NPC247298
0.6647	Remote Similarity	NPC474390
0.6647	Remote Similarity	NPC13004
0.6647	Remote Similarity	NPC202776
0.6647	Remote Similarity	NPC156356
0.6647	Remote Similarity	NPC189482
0.6632	Remote Similarity	NPC286119
0.6629	Remote Similarity	NPC89341
0.6626	Remote Similarity	NPC196371
0.6626	Remote Similarity	NPC47769
0.6626	Remote Similarity	NPC226737
0.6626	Remote Similarity	NPC299939
0.6626	Remote Similarity	NPC153580
0.6614	Remote Similarity	NPC288747
0.6612	Remote Similarity	NPC247639
0.6612	Remote Similarity	NPC25084
0.6611	Remote Similarity	NPC478189
0.6611	Remote Similarity	NPC88249
0.6611	Remote Similarity	NPC151895
0.6611	Remote Similarity	NPC97221
0.6611	Remote Similarity	NPC192768
0.6611	Remote Similarity	NPC220858
0.6609	Remote Similarity	NPC55947
0.6609	Remote Similarity	NPC260842
0.6606	Remote Similarity	NPC13020
0.6606	Remote Similarity	NPC473572
0.6606	Remote Similarity	NPC140359
0.6606	Remote Similarity	NPC474169

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 NPC226001 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	241
0.1-0.2	950
0.2-0.3	1540
0.3-0.4	2947
0.4-0.5	2345
0.5-0.6	1029
0.6-0.7	97
0.7-0.8	1
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
0.7091	Intermediate Similarity	NPD2674	Phase 3
0.7088	Intermediate Similarity	NPD4010	Discontinued
0.6977	Remote Similarity	NPD6331	Phase 2
0.6977	Remote Similarity	NPD6658	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD3144	Approved
0.6928	Remote Similarity	NPD3145	Approved
0.6869	Remote Similarity	NPD8095	Phase 1
0.6818	Remote Similarity	NPD4123	Phase 3
0.6763	Remote Similarity	NPD7153	Discontinued
0.6744	Remote Similarity	NPD2161	Phase 2
0.6648	Remote Similarity	NPD7945	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD5837	Clinical (unspecified phase)
0.663	Remote Similarity	NPD4675	Approved
0.663	Remote Similarity	NPD4678	Approved
0.6612	Remote Similarity	NPD5773	Approved
0.6612	Remote Similarity	NPD5772	Approved
0.6607	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD3676	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD8054	Approved
0.6598	Remote Similarity	NPD8053	Approved
0.6592	Remote Similarity	NPD7527	Clinical (unspecified phase)
0.6592	Remote Similarity	NPD52	Approved
0.6592	Remote Similarity	NPD7526	Approved
0.6592	Remote Similarity	NPD5261	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD1726	Clinical (unspecified phase)
0.6575	Remote Similarity	NPD4005	Discontinued
0.6556	Remote Similarity	NPD2122	Discontinued
0.655	Remote Similarity	NPD1558	Phase 1
0.6536	Remote Similarity	NPD4739	Approved
0.6534	Remote Similarity	NPD4162	Approved
0.6524	Remote Similarity	NPD7201	Clinical (unspecified phase)
0.6505	Remote Similarity	NPD7833	Phase 2
0.6505	Remote Similarity	NPD7831	Phase 2
0.6505	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6505	Remote Similarity	NPD7832	Clinical (unspecified phase)
0.6495	Remote Similarity	NPD2802	Phase 3
0.6491	Remote Similarity	NPD7477	Discontinued
0.6488	Remote Similarity	NPD6584	Phase 3
0.6477	Remote Similarity	NPD7596	Clinical (unspecified phase)
0.6461	Remote Similarity	NPD5241	Discontinued
0.6441	Remote Similarity	NPD3060	Approved
0.6433	Remote Similarity	NPD5718	Phase 2
0.6417	Remote Similarity	NPD8070	Approved
0.6413	Remote Similarity	NPD3778	Approved
0.64	Remote Similarity	NPD6029	Clinical (unspecified phase)
0.64	Remote Similarity	NPD6028	Clinical (unspecified phase)
0.6369	Remote Similarity	NPD2922	Phase 1
0.6364	Remote Similarity	NPD7773	Phase 2
0.6354	Remote Similarity	NPD1754	Clinical (unspecified phase)
0.6354	Remote Similarity	NPD7446	Clinical (unspecified phase)
0.6347	Remote Similarity	NPD2337	Clinical (unspecified phase)
0.6344	Remote Similarity	NPD6818	Clinical (unspecified phase)
0.6337	Remote Similarity	NPD5109	Approved
0.6337	Remote Similarity	NPD5110	Phase 2
0.6337	Remote Similarity	NPD5111	Phase 2
0.6335	Remote Similarity	NPD6688	Approved
0.6335	Remote Similarity	NPD6687	Approved
0.6328	Remote Similarity	NPD1375	Discontinued
0.631	Remote Similarity	NPD6582	Phase 2
0.631	Remote Similarity	NPD6583	Phase 3
0.631	Remote Similarity	NPD1669	Approved
0.6294	Remote Similarity	NPD7451	Discontinued
0.6292	Remote Similarity	NPD7037	Approved
0.6272	Remote Similarity	NPD5310	Approved
0.6272	Remote Similarity	NPD5311	Approved
0.6257	Remote Similarity	NPD2977	Approved
0.6257	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6257	Remote Similarity	NPD2978	Approved
0.625	Remote Similarity	NPD6896	Approved
0.625	Remote Similarity	NPD6895	Approved
0.625	Remote Similarity	NPD4083	Discontinued
0.6243	Remote Similarity	NPD6783	Clinical (unspecified phase)
0.6237	Remote Similarity	NPD6072	Discontinued
0.6237	Remote Similarity	NPD8252	Approved
0.6237	Remote Similarity	NPD8251	Approved
0.6237	Remote Similarity	NPD8099	Discontinued
0.6235	Remote Similarity	NPD3053	Approved
0.6235	Remote Similarity	NPD3055	Approved
0.6221	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6218	Remote Similarity	NPD27	Approved
0.6218	Remote Similarity	NPD2489	Approved
0.6211	Remote Similarity	NPD228	Approved
0.6205	Remote Similarity	NPD8156	Discontinued
0.6203	Remote Similarity	NPD5722	Discontinued
0.6201	Remote Similarity	NPD4664	Clinical (unspecified phase)
0.6196	Remote Similarity	NPD6030	Approved
0.6196	Remote Similarity	NPD6031	Approved
0.6193	Remote Similarity	NPD2653	Approved
0.6186	Remote Similarity	NPD5602	Clinical (unspecified phase)
0.6183	Remote Similarity	NPD3296	Phase 1
0.6175	Remote Similarity	NPD3985	Discontinued
0.6175	Remote Similarity	NPD7020	Approved
0.6175	Remote Similarity	NPD1771	Clinical (unspecified phase)
0.6175	Remote Similarity	NPD7019	Approved
0.6173	Remote Similarity	NPD821	Approved
0.6169	Remote Similarity	NPD7906	Approved
0.6167	Remote Similarity	NPD4236	Phase 3
0.6167	Remote Similarity	NPD4237	Approved
0.6158	Remote Similarity	NPD4055	Discovery
0.6154	Remote Similarity	NPD7493	Clinical (unspecified phase)
0.615	Remote Similarity	NPD7438	Suspended
0.6149	Remote Similarity	NPD6812	Clinical (unspecified phase)
0.6145	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6145	Remote Similarity	NPD3656	Approved
0.6141	Remote Similarity	NPD2183	Approved
0.6141	Remote Similarity	NPD2184	Approved
0.6129	Remote Similarity	NPD3866	Clinical (unspecified phase)
0.6129	Remote Similarity	NPD6523	Clinical (unspecified phase)
0.6118	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6114	Remote Similarity	NPD7608	Discontinued
0.6114	Remote Similarity	NPD3051	Approved
0.6102	Remote Similarity	NPD2157	Approved
0.6099	Remote Similarity	NPD3692	Discontinued
0.6096	Remote Similarity	NPD6502	Phase 2
0.6092	Remote Similarity	NPD3027	Phase 3
0.6092	Remote Similarity	NPD2669	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD4584	Approved
0.6085	Remote Similarity	NPD5563	Clinical (unspecified phase)
0.6082	Remote Similarity	NPD2969	Approved
0.6082	Remote Similarity	NPD2970	Approved
0.608	Remote Similarity	NPD7132	Clinical (unspecified phase)
0.608	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.608	Remote Similarity	NPD1613	Approved
0.6077	Remote Similarity	NPD2459	Approved
0.6077	Remote Similarity	NPD2458	Approved
0.6077	Remote Similarity	NPD2460	Phase 3
0.6077	Remote Similarity	NPD5177	Phase 3
0.6075	Remote Similarity	NPD3686	Approved
0.6075	Remote Similarity	NPD3687	Approved
0.6074	Remote Similarity	NPD9379	Approved
0.6074	Remote Similarity	NPD9377	Approved
0.6073	Remote Similarity	NPD5604	Discontinued
0.6069	Remote Similarity	NPD4993	Discontinued
0.6069	Remote Similarity	NPD1712	Approved
0.6064	Remote Similarity	NPD4773	Phase 2
0.6064	Remote Similarity	NPD4772	Phase 2
0.6059	Remote Similarity	NPD2235	Phase 2
0.6059	Remote Similarity	NPD2231	Phase 2
0.6054	Remote Similarity	NPD3647	Clinical (unspecified phase)
0.6052	Remote Similarity	NPD8398	Clinical (unspecified phase)
0.605	Remote Similarity	NPD3337	Discontinued
0.605	Remote Similarity	NPD4577	Approved
0.605	Remote Similarity	NPD4578	Approved
0.6041	Remote Similarity	NPD4873	Discontinued
0.604	Remote Similarity	NPD4663	Approved
0.6037	Remote Similarity	NPD5283	Phase 1
0.6034	Remote Similarity	NPD7425	Clinical (unspecified phase)
0.6034	Remote Similarity	NPD4108	Discontinued
0.6034	Remote Similarity	NPD1169	Approved
0.6033	Remote Similarity	NPD6087	Phase 1
0.603	Remote Similarity	NPD7038	Approved
0.603	Remote Similarity	NPD7039	Approved
0.6029	Remote Similarity	NPD5641	Discontinued
0.6023	Remote Similarity	NPD839	Approved
0.6023	Remote Similarity	NPD840	Approved
0.6023	Remote Similarity	NPD1423	Approved
0.6021	Remote Similarity	NPD4581	Clinical (unspecified phase)
0.6011	Remote Similarity	NPD1772	Clinical (unspecified phase)
0.6011	Remote Similarity	NPD3052	Approved
0.6011	Remote Similarity	NPD2219	Phase 1
0.6011	Remote Similarity	NPD3054	Approved
0.6011	Remote Similarity	NPD5084	Clinical (unspecified phase)
0.6011	Remote Similarity	NPD5314	Approved
0.6	Remote Similarity	NPD9718	Approved
0.6	Remote Similarity	NPD7447	Phase 1
0.6	Remote Similarity	NPD3536	Discontinued
0.6	Remote Similarity	NPD7089	Clinical (unspecified phase)
0.6	Remote Similarity	NPD2874	Phase 2
0.599	Remote Similarity	NPD2804	Phase 1
0.5989	Remote Similarity	NPD4003	Phase 3
0.5989	Remote Similarity	NPD3059	Approved
0.5989	Remote Similarity	NPD3061	Approved
0.5989	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.5989	Remote Similarity	NPD3620	Phase 2
0.5989	Remote Similarity	NPD3062	Approved
0.598	Remote Similarity	NPD6377	Clinical (unspecified phase)
0.5978	Remote Similarity	NPD7124	Phase 2
0.5978	Remote Similarity	NPD3845	Phase 1
0.5977	Remote Similarity	NPD2407	Clinical (unspecified phase)
0.5976	Remote Similarity	NPD2667	Approved
0.5976	Remote Similarity	NPD2668	Approved
0.597	Remote Similarity	NPD7313	Approved
0.597	Remote Similarity	NPD7311	Approved
0.597	Remote Similarity	NPD7310	Approved
0.597	Remote Similarity	NPD7312	Approved
0.5969	Remote Similarity	NPD6063	Approved
0.5969	Remote Similarity	NPD2296	Approved
0.5966	Remote Similarity	NPD2028	Clinical (unspecified phase)
0.5957	Remote Similarity	NPD3111	Phase 1
0.5957	Remote Similarity	NPD5811	Approved
0.5957	Remote Similarity	NPD3455	Phase 2
0.5952	Remote Similarity	NPD6581	Approved
0.5952	Remote Similarity	NPD6580	Approved
0.5949	Remote Similarity	NPD4606	Clinical (unspecified phase)
0.5947	Remote Similarity	NPD4433	Discontinued
0.5947	Remote Similarity	NPD7298	Approved
0.5947	Remote Similarity	NPD5720	Discontinued
0.5946	Remote Similarity	NPD7212	Phase 2
0.5946	Remote Similarity	NPD4357	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