NPASS Compound

Structure

NPC147137 OpenBabel07101719512D 36 39 0 0 0 0 0 0 0 0999 V2000 2.9543 -0.9000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7953 0.3872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2601 -1.2601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3660 -3.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3660 -3.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7953 0.3872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9543 -0.9000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0032 -0.5909 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 -2.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0032 -0.5909 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6974 -0.2308 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5385 1.0563 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3660 -4.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3660 -4.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5385 1.0563 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6974 -0.2308 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3090 -0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 -1.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3090 -0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2601 -1.2601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4895 0.7473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 -4.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4895 0.7473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6485 -0.5398 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 2.3305 2.0345 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 -2.2321 -4.5388 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 1.2321 -4.5388 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 -3.3305 2.0345 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 -5.6485 -0.5398 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 -2.4680 -2.2382 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2327 1.4164 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 -5.5388 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2327 1.4164 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5878 0.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 8 2 0 0 0 0 1 11 1 0 0 0 0 2 8 1 0 0 0 0 2 12 2 0 0 0 0 3 8 1 0 0 0 0 3 17 2 0 0 0 0 4 9 2 0 0 0 0 4 13 1 0 0 0 0 5 9 1 0 0 0 0 5 14 2 0 0 0 0 6 10 2 0 0 0 0 6 15 1 0 0 0 0 7 10 1 0 0 0 0 7 16 2 0 0 0 0 9 18 1 0 0 0 0 10 20 1 0 0 0 0 11 21 2 0 0 0 0 11 25 1 0 0 0 0 12 21 1 0 0 0 0 12 26 1 0 0 0 0 13 22 2 0 0 0 0 13 27 1 0 0 0 0 14 22 1 0 0 0 0 14 28 1 0 0 0 0 15 23 2 0 0 0 0 15 29 1 0 0 0 0 16 23 1 0 0 0 0 16 30 1 0 0 0 0 17 18 1 0 0 0 0 17 36 1 0 0 0 0 18 19 2 0 0 0 0 19 20 1 0 0 0 0 19 24 1 0 0 0 0 20 31 2 0 0 0 0 21 32 1 0 0 0 0 22 33 1 0 0 0 0 23 34 1 0 0 0 0 24 35 2 0 0 0 0 24 36 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	867.56
Volume:	523.603
LogP:	6.565
LogD:	2.379
LogS:	-3.923
# Rotatable Bonds:	4
TPSA:	104.06
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.138
Synthetic Accessibility Score:	3.312
Fsp3:	0.0
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:	-6.221
MDCK Permeability:	1.423387584509328e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.942
20% Bioavailability (F20%):	0.86
30% Bioavailability (F30%):	0.916

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001
Plasma Protein Binding (PPB):	111.2300033569336%
Volume Distribution (VD):	0.413
Pgp-substrate:	5.204953193664551%

ADMET: Metabolism

CYP1A2-inhibitor:	0.744
CYP1A2-substrate:	0.087
CYP2C19-inhibitor:	0.686
CYP2C19-substrate:	0.054
CYP2C9-inhibitor:	0.545
CYP2C9-substrate:	0.077
CYP2D6-inhibitor:	0.019
CYP2D6-substrate:	0.121
CYP3A4-inhibitor:	0.053
CYP3A4-substrate:	0.024

ADMET: Excretion

Clearance (CL):	-0.471
Half-life (T1/2):	0.351

ADMET: Toxicity

hERG Blockers:	0.272
Human Hepatotoxicity (H-HT):	0.509
Drug-inuced Liver Injury (DILI):	0.899
AMES Toxicity:	0.01
Rat Oral Acute Toxicity:	0.833
Maximum Recommended Daily Dose:	0.927
Skin Sensitization:	0.418
Carcinogencity:	0.096
Eye Corrosion:	0.003
Eye Irritation:	0.645
Respiratory Toxicity:	0.046

Download Data

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

Natural Product: NPC147137

Natural Product ID:	NPC147137
*Common Name:**	Cadiolide B
IUPAC Name:	(5Z)-3-(3,5-dibromo-4-hydroxybenzoyl)-4-(3,5-dibromo-4-hydroxyphenyl)-5-[(3,5-dibromo-4-hydroxyphenyl)methylidene]furan-2-one
Synonyms:	Cadiolide B
Standard InCHIKey:	CJOZHMMQXWACBU-YPEHOIGNSA-N
Standard InCHI:	InChI=1S/C24H10Br6O6/c25-11-1-8(2-12(26)21(11)32)3-17-18(9-4-13(27)22(33)14(28)5-9)19(24(35)36-17)20(31)10-6-15(29)23(34)16(30)7-10/h1-7,32-34H/b17-3-
SMILES:	O=C1O/C(=Cc2cc(Br)c(c(c2)Br)O)/C(=C1C(=O)c1cc(Br)c(c(c1)Br)O)c1cc(Br)c(c(c1)Br)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2204154
PubChem CID:	11400288
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000476] Cinnamic acids and derivatives

*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
NPO33352	pseudodistoma antinboja	Species	Pseudodistomidae	Eukaryota	n.a.	Korean	n.a.	PMID[23145884]
NPO40655	Synoicum sp. Ascidian	Strain	Polyclinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[31967465]

☑ 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	2
MIC	26

Activity Type	# Activity
Individual Protein	2
Organism	26

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1821	Individual Protein	Sortase	Staphylococcus aureus	IC50	=	103000.0	nM	PMID[558923]
NPT1087	Individual Protein	Isocitrate lyase	Candida albicans	IC50	=	61000.0	nM	PMID[558923]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	0.5	ug.mL-1	PMID[558921]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	1.0	ug.mL-1	PMID[558921]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	2.0	ug.mL-1	PMID[558921]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	3.1	ug.mL-1	PMID[558921]
NPT3147	Organism	Kocuria rhizophila	Kocuria rhizophila	MIC	=	3.1	ug.mL-1	PMID[558921]
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	MIC	=	3.1	ug.mL-1	PMID[558921]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	3.1	ug.mL-1	PMID[558921]
NPT1242	Organism	Salmonella typhi	Salmonella enterica subsp. enterica serovar Typhi	MIC	=	15.62	ug.mL-1	PMID[558922]
NPT175	Organism	Enterococcus faecalis	Enterococcus faecalis	MIC	=	7.81	ug.mL-1	PMID[558922]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	7.81	ug.mL-1	PMID[558922]
NPT314	Organism	Bacillus cereus	Bacillus cereus	MIC	=	7.81	ug.mL-1	PMID[558922]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	7.81	ug.mL-1	PMID[558922]
NPT1286	Organism	Pectobacterium carotovorum	Pectobacterium carotovorum	MIC	>	125.0	ug.mL-1	PMID[558922]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	>	125.0	ug.mL-1	PMID[558922]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	125.0	ug.mL-1	PMID[558922]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	64.0	ug.mL-1	PMID[558923]
NPT175	Organism	Enterococcus faecalis	Enterococcus faecalis	MIC	>	128.0	ug.mL-1	PMID[558923]
NPT1531	Organism	Enterococcus faecium	Enterococcus faecium	MIC	>	128.0	ug.mL-1	PMID[558923]
NPT1190	Organism	Salmonella enterica	Salmonella enterica	MIC	>	128.0	ug.mL-1	PMID[558923]
NPT25245	ORGANISM	Proteus hauseri	Proteus hauseri	MIC	>	128.0	ug.mL-1	PMID[558923]
NPT173	Organism	Klebsiella pneumoniae	Klebsiella pneumoniae	MIC	>	128.0	ug.mL-1	PMID[558923]

☑ 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 NPC147137 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	378
0.1-0.2	2036
0.2-0.3	5614
0.3-0.4	12631
0.4-0.5	6266
0.5-0.6	9178
0.6-0.7	6515
0.7-0.8	48
0.8-0.85	16
0.85-0.9	5
0.9-0.95	6
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9853	High Similarity	NPC270848
0.9853	High Similarity	NPC272868
0.9853	High Similarity	NPC122599
0.9437	High Similarity	NPC470710
0.9338	High Similarity	NPC177967
0.9338	High Similarity	NPC471237
0.9203	High Similarity	NPC81137
0.913	High Similarity	NPC197766
0.913	High Similarity	NPC471236
0.8657	High Similarity	NPC105999
0.8456	Intermediate Similarity	NPC213414
0.84	Intermediate Similarity	NPC471235
0.84	Intermediate Similarity	NPC73132
0.84	Intermediate Similarity	NPC235033
0.8309	Intermediate Similarity	NPC296202
0.8235	Intermediate Similarity	NPC7830
0.8156	Intermediate Similarity	NPC478071
0.8099	Intermediate Similarity	NPC11449
0.7956	Intermediate Similarity	NPC180207
0.7887	Intermediate Similarity	NPC78061
0.7887	Intermediate Similarity	NPC122359
0.7887	Intermediate Similarity	NPC159987
0.7786	Intermediate Similarity	NPC116562
0.7754	Intermediate Similarity	NPC100395
0.7554	Intermediate Similarity	NPC311091
0.7554	Intermediate Similarity	NPC471033
0.7536	Intermediate Similarity	NPC128249
0.7535	Intermediate Similarity	NPC68167
0.745	Intermediate Similarity	NPC471328
0.7407	Intermediate Similarity	NPC54543
0.7386	Intermediate Similarity	NPC19622
0.7386	Intermediate Similarity	NPC112789
0.7347	Intermediate Similarity	NPC2596
0.7338	Intermediate Similarity	NPC275903
0.7315	Intermediate Similarity	NPC259017
0.7279	Intermediate Similarity	NPC79543
0.7246	Intermediate Similarity	NPC17693
0.723	Intermediate Similarity	NPC196034
0.7226	Intermediate Similarity	NPC116842
0.7226	Intermediate Similarity	NPC473358
0.7206	Intermediate Similarity	NPC17525
0.7197	Intermediate Similarity	NPC271451
0.7183	Intermediate Similarity	NPC249435
0.717	Intermediate Similarity	NPC178097
0.716	Intermediate Similarity	NPC135103
0.7118	Intermediate Similarity	NPC470566
0.7115	Intermediate Similarity	NPC470986
0.7114	Intermediate Similarity	NPC79332
0.7092	Intermediate Similarity	NPC322197
0.7083	Intermediate Similarity	NPC233282
0.708	Intermediate Similarity	NPC471495
0.7076	Intermediate Similarity	NPC470567
0.7075	Intermediate Similarity	NPC288945
0.707	Intermediate Similarity	NPC184632
0.7063	Intermediate Similarity	NPC94298
0.7063	Intermediate Similarity	NPC25844
0.7063	Intermediate Similarity	NPC27633
0.705	Intermediate Similarity	NPC114682
0.705	Intermediate Similarity	NPC268388
0.7047	Intermediate Similarity	NPC22783
0.7042	Intermediate Similarity	NPC131192
0.7039	Intermediate Similarity	NPC262359
0.703	Intermediate Similarity	NPC474535
0.7029	Intermediate Similarity	NPC88141
0.7027	Intermediate Similarity	NPC4164
0.702	Intermediate Similarity	NPC470987
0.702	Intermediate Similarity	NPC21378
0.7019	Intermediate Similarity	NPC119767
0.7014	Intermediate Similarity	NPC264976
0.7013	Intermediate Similarity	NPC172262
0.7007	Intermediate Similarity	NPC14141
0.7007	Intermediate Similarity	NPC226699
0.7	Intermediate Similarity	NPC469953
0.7	Intermediate Similarity	NPC95537
0.7	Intermediate Similarity	NPC97188
0.6994	Remote Similarity	NPC151973
0.6993	Remote Similarity	NPC212631
0.6993	Remote Similarity	NPC287533
0.6993	Remote Similarity	NPC87231
0.6993	Remote Similarity	NPC257756
0.6993	Remote Similarity	NPC129132
0.6993	Remote Similarity	NPC205468
0.6988	Remote Similarity	NPC475697
0.6987	Remote Similarity	NPC275055
0.6987	Remote Similarity	NPC290291
0.6987	Remote Similarity	NPC250266
0.6987	Remote Similarity	NPC266597
0.6986	Remote Similarity	NPC115159
0.6986	Remote Similarity	NPC45438
0.6986	Remote Similarity	NPC224273
0.6986	Remote Similarity	NPC73532
0.6986	Remote Similarity	NPC267552
0.6986	Remote Similarity	NPC19174
0.6986	Remote Similarity	NPC143427
0.6981	Remote Similarity	NPC66593
0.6981	Remote Similarity	NPC36181
0.6981	Remote Similarity	NPC474692
0.698	Remote Similarity	NPC110211
0.698	Remote Similarity	NPC204579
0.6978	Remote Similarity	NPC21162
0.6978	Remote Similarity	NPC183700
0.6972	Remote Similarity	NPC23402
0.6972	Remote Similarity	NPC296526
0.6968	Remote Similarity	NPC9985
0.6968	Remote Similarity	NPC239495
0.6959	Remote Similarity	NPC293312
0.6959	Remote Similarity	NPC193805
0.6957	Remote Similarity	NPC469498
0.6957	Remote Similarity	NPC147250
0.6954	Remote Similarity	NPC94810
0.6954	Remote Similarity	NPC214246
0.695	Remote Similarity	NPC471488
0.6948	Remote Similarity	NPC274121
0.6948	Remote Similarity	NPC56031
0.6948	Remote Similarity	NPC78540
0.6948	Remote Similarity	NPC50898
0.6948	Remote Similarity	NPC472365
0.6948	Remote Similarity	NPC337373
0.6948	Remote Similarity	NPC242294
0.6948	Remote Similarity	NPC213216
0.6948	Remote Similarity	NPC188646
0.6948	Remote Similarity	NPC139813
0.6948	Remote Similarity	NPC263670
0.6948	Remote Similarity	NPC175098
0.6948	Remote Similarity	NPC192304
0.6948	Remote Similarity	NPC57601
0.6948	Remote Similarity	NPC312318
0.6943	Remote Similarity	NPC251681
0.6943	Remote Similarity	NPC188947
0.6943	Remote Similarity	NPC280284
0.6943	Remote Similarity	NPC243528
0.6943	Remote Similarity	NPC99333
0.6939	Remote Similarity	NPC133909
0.6939	Remote Similarity	NPC32032
0.6939	Remote Similarity	NPC91478
0.6937	Remote Similarity	NPC87609
0.6937	Remote Similarity	NPC112791
0.6937	Remote Similarity	NPC188632
0.6937	Remote Similarity	NPC94794
0.6937	Remote Similarity	NPC196459
0.6937	Remote Similarity	NPC470216
0.6937	Remote Similarity	NPC470296
0.6934	Remote Similarity	NPC6984
0.6934	Remote Similarity	NPC70843
0.6934	Remote Similarity	NPC95178
0.6934	Remote Similarity	NPC69332
0.6934	Remote Similarity	NPC29989
0.6933	Remote Similarity	NPC52931
0.6928	Remote Similarity	NPC185624
0.6928	Remote Similarity	NPC308037
0.6928	Remote Similarity	NPC64359
0.6923	Remote Similarity	NPC124784
0.6923	Remote Similarity	NPC301915
0.6923	Remote Similarity	NPC194281
0.6923	Remote Similarity	NPC29353
0.6923	Remote Similarity	NPC19290
0.6923	Remote Similarity	NPC261292
0.6923	Remote Similarity	NPC47815
0.6923	Remote Similarity	NPC231772
0.6923	Remote Similarity	NPC234133
0.6923	Remote Similarity	NPC473887
0.6923	Remote Similarity	NPC13408
0.6923	Remote Similarity	NPC83718
0.6923	Remote Similarity	NPC127447
0.6918	Remote Similarity	NPC297186
0.6918	Remote Similarity	NPC14871
0.6918	Remote Similarity	NPC471486
0.6914	Remote Similarity	NPC180477
0.6914	Remote Similarity	NPC12305
0.6913	Remote Similarity	NPC137416
0.6909	Remote Similarity	NPC41326
0.6908	Remote Similarity	NPC247779
0.6906	Remote Similarity	NPC95172
0.6903	Remote Similarity	NPC311742
0.6903	Remote Similarity	NPC286336
0.6901	Remote Similarity	NPC285350
0.6899	Remote Similarity	NPC290664
0.6899	Remote Similarity	NPC261234
0.6899	Remote Similarity	NPC250597
0.6897	Remote Similarity	NPC158222
0.6897	Remote Similarity	NPC61779
0.6894	Remote Similarity	NPC469935
0.6894	Remote Similarity	NPC178627
0.6894	Remote Similarity	NPC257236
0.6894	Remote Similarity	NPC278175
0.6894	Remote Similarity	NPC1886
0.6894	Remote Similarity	NPC196137
0.6892	Remote Similarity	NPC473942
0.689	Remote Similarity	NPC474620
0.6887	Remote Similarity	NPC221777
0.6887	Remote Similarity	NPC214553
0.6884	Remote Similarity	NPC156648
0.6884	Remote Similarity	NPC29883
0.6884	Remote Similarity	NPC141523
0.6883	Remote Similarity	NPC470988
0.6879	Remote Similarity	NPC209560
0.6879	Remote Similarity	NPC4214
0.6879	Remote Similarity	NPC228661
0.6879	Remote Similarity	NPC299379
0.6879	Remote Similarity	NPC7013

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 NPC147137 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	352
0.1-0.2	1015
0.2-0.3	1655
0.3-0.4	3125
0.4-0.5	2064
0.5-0.6	760
0.6-0.7	172
0.7-0.8	6
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8129	Intermediate Similarity	NPD2296	Approved
0.7765	Intermediate Similarity	NPD4287	Approved
0.7365	Intermediate Similarity	NPD3764	Approved
0.7346	Intermediate Similarity	NPD4288	Approved
0.7175	Intermediate Similarity	NPD3269	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD2344	Approved
0.7067	Intermediate Similarity	NPD9718	Approved
0.7063	Intermediate Similarity	NPD9545	Approved
0.7027	Intermediate Similarity	NPD1203	Approved
0.702	Intermediate Similarity	NPD2313	Discontinued
0.6918	Remote Similarity	NPD2309	Approved
0.6894	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD2799	Discontinued
0.6859	Remote Similarity	NPD1510	Phase 2
0.6848	Remote Similarity	NPD7411	Suspended
0.6845	Remote Similarity	NPD3749	Approved
0.6835	Remote Similarity	NPD1549	Phase 2
0.6818	Remote Similarity	NPD1240	Approved
0.6815	Remote Similarity	NPD2935	Discontinued
0.6806	Remote Similarity	NPD9493	Approved
0.6772	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.675	Remote Similarity	NPD3750	Approved
0.6731	Remote Similarity	NPD1607	Approved
0.6728	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD3972	Approved
0.6711	Remote Similarity	NPD9717	Approved
0.6711	Remote Similarity	NPD1481	Phase 2
0.6709	Remote Similarity	NPD5406	Approved
0.6709	Remote Similarity	NPD5405	Approved
0.6709	Remote Similarity	NPD5408	Approved
0.6709	Remote Similarity	NPD5404	Approved
0.6689	Remote Similarity	NPD1164	Approved
0.6667	Remote Similarity	NPD2346	Discontinued
0.6667	Remote Similarity	NPD7440	Discontinued
0.6646	Remote Similarity	NPD4628	Phase 3
0.6645	Remote Similarity	NPD2798	Approved
0.6644	Remote Similarity	NPD1535	Discovery
0.6626	Remote Similarity	NPD6799	Approved
0.6625	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD5586	Clinical (unspecified phase)
0.6605	Remote Similarity	NPD2354	Approved
0.6599	Remote Similarity	NPD1894	Discontinued
0.6596	Remote Similarity	NPD74	Approved
0.6596	Remote Similarity	NPD9266	Approved
0.6585	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6581	Remote Similarity	NPD3268	Approved
0.6579	Remote Similarity	NPD1470	Approved
0.6558	Remote Similarity	NPD6832	Phase 2
0.6554	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.655	Remote Similarity	NPD7075	Discontinued
0.6543	Remote Similarity	NPD7003	Approved
0.6541	Remote Similarity	NPD4308	Phase 3
0.6541	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6533	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6533	Remote Similarity	NPD1201	Approved
0.6527	Remote Similarity	NPD3226	Approved
0.6527	Remote Similarity	NPD7458	Discontinued
0.6525	Remote Similarity	NPD9263	Approved
0.6525	Remote Similarity	NPD9264	Approved
0.6525	Remote Similarity	NPD9267	Approved
0.6524	Remote Similarity	NPD1511	Approved
0.6514	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6513	Remote Similarity	NPD1876	Approved
0.65	Remote Similarity	NPD1551	Phase 2
0.6497	Remote Similarity	NPD943	Approved
0.6491	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6491	Remote Similarity	NPD7768	Phase 2
0.6488	Remote Similarity	NPD4380	Phase 2
0.6474	Remote Similarity	NPD6798	Discontinued
0.6471	Remote Similarity	NPD2797	Approved
0.6471	Remote Similarity	NPD7819	Suspended
0.6471	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.646	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.646	Remote Similarity	NPD2353	Approved
0.646	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6456	Remote Similarity	NPD230	Phase 1
0.6446	Remote Similarity	NPD1512	Approved
0.6438	Remote Similarity	NPD3748	Approved
0.6438	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6433	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6433	Remote Similarity	NPD6233	Phase 2
0.6412	Remote Similarity	NPD6801	Discontinued
0.6407	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6405	Remote Similarity	NPD3225	Approved
0.6402	Remote Similarity	NPD6190	Approved
0.6398	Remote Similarity	NPD2796	Approved
0.6391	Remote Similarity	NPD6599	Discontinued
0.6382	Remote Similarity	NPD1608	Approved
0.638	Remote Similarity	NPD2800	Approved
0.638	Remote Similarity	NPD1243	Approved
0.6377	Remote Similarity	NPD1238	Approved
0.637	Remote Similarity	NPD1241	Discontinued
0.6369	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD3267	Approved
0.6364	Remote Similarity	NPD3266	Approved
0.6358	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6352	Remote Similarity	NPD1933	Approved
0.6351	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6347	Remote Similarity	NPD6273	Approved
0.6341	Remote Similarity	NPD8166	Discontinued
0.6341	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6335	Remote Similarity	NPD7033	Discontinued
0.6327	Remote Similarity	NPD9281	Approved
0.6325	Remote Similarity	NPD7390	Discontinued
0.6316	Remote Similarity	NPD1934	Approved
0.6312	Remote Similarity	NPD5909	Discontinued
0.631	Remote Similarity	NPD5403	Approved
0.6307	Remote Similarity	NPD1161	Approved
0.6307	Remote Similarity	NPD6232	Discontinued
0.6306	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6303	Remote Similarity	NPD3887	Approved
0.6301	Remote Similarity	NPD5535	Approved
0.6301	Remote Similarity	NPD3882	Suspended
0.6292	Remote Similarity	NPD7473	Discontinued
0.6289	Remote Similarity	NPD4307	Phase 2
0.6287	Remote Similarity	NPD5401	Approved
0.6287	Remote Similarity	NPD2534	Approved
0.6287	Remote Similarity	NPD2533	Approved
0.6287	Remote Similarity	NPD2532	Approved
0.6279	Remote Similarity	NPD2801	Approved
0.6279	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6275	Remote Similarity	NPD9269	Phase 2
0.6266	Remote Similarity	NPD411	Approved
0.6258	Remote Similarity	NPD1471	Phase 3
0.625	Remote Similarity	NPD447	Suspended
0.625	Remote Similarity	NPD1202	Approved
0.625	Remote Similarity	NPD3847	Discontinued
0.625	Remote Similarity	NPD5049	Phase 3
0.625	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6243	Remote Similarity	NPD3817	Phase 2
0.6241	Remote Similarity	NPD9261	Approved
0.6235	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6234	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6233	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6226	Remote Similarity	NPD520	Approved
0.6225	Remote Similarity	NPD9268	Approved
0.6221	Remote Similarity	NPD7577	Discontinued
0.6216	Remote Similarity	NPD5951	Approved
0.6211	Remote Similarity	NPD6651	Approved
0.6197	Remote Similarity	NPD1237	Approved
0.6194	Remote Similarity	NPD1283	Approved
0.619	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6188	Remote Similarity	NPD4445	Approved
0.6184	Remote Similarity	NPD3019	Approved
0.6184	Remote Similarity	NPD17	Approved
0.6178	Remote Similarity	NPD9494	Approved
0.6168	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6167	Remote Similarity	NPD3818	Discontinued
0.6158	Remote Similarity	NPD6959	Discontinued
0.6154	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6149	Remote Similarity	NPD6355	Discontinued
0.6148	Remote Similarity	NPD9258	Approved
0.6148	Remote Similarity	NPD9256	Approved
0.6145	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6145	Remote Similarity	NPD6166	Phase 2
0.6145	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.614	Remote Similarity	NPD3455	Phase 2
0.6139	Remote Similarity	NPD2614	Approved
0.6138	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6127	Remote Similarity	NPD1929	Approved
0.6127	Remote Similarity	NPD1930	Approved
0.6127	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6125	Remote Similarity	NPD4062	Phase 3
0.6125	Remote Similarity	NPD6663	Approved
0.6124	Remote Similarity	NPD6808	Phase 2
0.6121	Remote Similarity	NPD7596	Clinical (unspecified phase)
0.6118	Remote Similarity	NPD920	Approved
0.6115	Remote Similarity	NPD1019	Discontinued
0.6115	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6101	Remote Similarity	NPD7008	Discontinued
0.6101	Remote Similarity	NPD7095	Approved
0.6095	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6092	Remote Similarity	NPD1465	Phase 2
0.6087	Remote Similarity	NPD2933	Approved
0.6087	Remote Similarity	NPD3142	Approved
0.6087	Remote Similarity	NPD3140	Approved
0.6087	Remote Similarity	NPD2934	Approved
0.608	Remote Similarity	NPD6971	Discontinued
0.6078	Remote Similarity	NPD2932	Approved
0.6078	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6076	Remote Similarity	NPD5736	Approved
0.6066	Remote Similarity	NPD5953	Discontinued
0.6057	Remote Similarity	NPD5402	Approved
0.6057	Remote Similarity	NPD8438	Clinical (unspecified phase)
0.6054	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6045	Remote Similarity	NPD1168	Approved
0.6044	Remote Similarity	NPD7286	Phase 2
0.6044	Remote Similarity	NPD5844	Phase 1
0.6043	Remote Similarity	NPD2859	Approved
0.6043	Remote Similarity	NPD2860	Approved
0.6037	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6034	Remote Similarity	NPD6280	Approved
0.6034	Remote Similarity	NPD6279	Approved
0.6033	Remote Similarity	NPD6559	Discontinued
0.6027	Remote Similarity	NPD2182	Approved
0.6025	Remote Similarity	NPD8032	Phase 2
0.6013	Remote Similarity	NPD5647	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