NPASS Compound

Structure

NPC270848 OpenBabel07101718302D 34 37 0 0 0 0 0 0 0 0999 V2000 1.7953 0.3872 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 2.5385 1.0563 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 2.9543 -0.9000 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 -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 -1.3660 -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 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 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 -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 -2.2321 -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 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 -2.4680 -2.2382 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 3 2 0 0 0 0 1 10 1 0 0 0 0 2 4 2 0 0 0 0 2 11 1 0 0 0 0 3 17 1 0 0 0 0 4 18 1 0 0 0 0 5 10 2 0 0 0 0 5 13 1 0 0 0 0 6 10 1 0 0 0 0 6 19 2 0 0 0 0 7 11 2 0 0 0 0 7 14 1 0 0 0 0 8 12 2 0 0 0 0 8 15 1 0 0 0 0 9 12 1 0 0 0 0 9 16 2 0 0 0 0 11 20 1 0 0 0 0 12 22 1 0 0 0 0 13 17 2 0 0 0 0 13 25 1 0 0 0 0 14 18 2 0 0 0 0 14 26 1 0 0 0 0 15 23 2 0 0 0 0 15 27 1 0 0 0 0 16 23 1 0 0 0 0 16 28 1 0 0 0 0 17 29 1 0 0 0 0 18 30 1 0 0 0 0 19 20 1 0 0 0 0 19 34 1 0 0 0 0 20 21 2 0 0 0 0 21 22 1 0 0 0 0 21 24 1 0 0 0 0 22 31 2 0 0 0 0 23 32 1 0 0 0 0 24 33 2 0 0 0 0 24 34 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	711.74
Volume:	485.036
LogP:	5.843
LogD:	2.397
LogS:	-3.996
# Rotatable Bonds:	4
TPSA:	104.06
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.152
Synthetic Accessibility Score:	3.126
Fsp3:	0.0
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.047
MDCK Permeability:	1.2649217751459219e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.866
20% Bioavailability (F20%):	0.709
30% Bioavailability (F30%):	0.808

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.003
Plasma Protein Binding (PPB):	105.59221649169922%
Volume Distribution (VD):	0.414
Pgp-substrate:	1.6987780332565308%

ADMET: Metabolism

CYP1A2-inhibitor:	0.873
CYP1A2-substrate:	0.088
CYP2C19-inhibitor:	0.809
CYP2C19-substrate:	0.051
CYP2C9-inhibitor:	0.564
CYP2C9-substrate:	0.22
CYP2D6-inhibitor:	0.295
CYP2D6-substrate:	0.15
CYP3A4-inhibitor:	0.095
CYP3A4-substrate:	0.055

ADMET: Excretion

Clearance (CL):	-0.126
Half-life (T1/2):	0.473

ADMET: Toxicity

hERG Blockers:	0.046
Human Hepatotoxicity (H-HT):	0.465
Drug-inuced Liver Injury (DILI):	0.959
AMES Toxicity:	0.013
Rat Oral Acute Toxicity:	0.828
Maximum Recommended Daily Dose:	0.849
Skin Sensitization:	0.473
Carcinogencity:	0.192
Eye Corrosion:	0.003
Eye Irritation:	0.822
Respiratory Toxicity:	0.029

Download Data

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

Natural Product: NPC270848

Natural Product ID:	NPC270848
*Common Name:**	Cadiolide C
IUPAC Name:	(5Z)-4-(3-bromo-4-hydroxyphenyl)-5-[(3-bromo-4-hydroxyphenyl)methylidene]-3-(3,5-dibromo-4-hydroxybenzoyl)furan-2-one
Synonyms:	Cadiolide C
Standard InCHIKey:	KKSJLDNZJFUGNY-SWNXQHNESA-N
Standard InCHI:	InChI=1S/C24H12Br4O6/c25-13-5-10(1-3-17(13)29)6-19-20(11-2-4-18(30)14(26)7-11)21(24(33)34-19)22(31)12-8-15(27)23(32)16(28)9-12/h1-9,29-30,32H/b19-6-
SMILES:	c1cc(c(cc1/C=C1/C(=C(C(=O)c2cc(c(c(c2)Br)O)Br)C(=O)O1)c1ccc(c(c1)Br)O)Br)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2204150
PubChem CID:	71457561
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	=	59000.0	nM	PMID[475495]
NPT1087	Individual Protein	Isocitrate lyase	Candida albicans	IC50	=	17000.0	nM	PMID[475495]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	<	0.13	ug.mL-1	PMID[475493]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	0.5	ug.mL-1	PMID[475493]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	0.25	ug.mL-1	PMID[475493]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	3.1	ug.mL-1	PMID[475493]
NPT3147	Organism	Kocuria rhizophila	Kocuria rhizophila	MIC	=	0.2	ug.mL-1	PMID[475493]
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	MIC	=	0.4	ug.mL-1	PMID[475493]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	0.4	ug.mL-1	PMID[475493]
NPT1242	Organism	Salmonella typhi	Salmonella enterica subsp. enterica serovar Typhi	MIC	=	3.9	ug.mL-1	PMID[475494]
NPT175	Organism	Enterococcus faecalis	Enterococcus faecalis	MIC	=	3.9	ug.mL-1	PMID[475494]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	3.9	ug.mL-1	PMID[475494]
NPT314	Organism	Bacillus cereus	Bacillus cereus	MIC	=	3.9	ug.mL-1	PMID[475494]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	3.9	ug.mL-1	PMID[475494]
NPT1286	Organism	Pectobacterium carotovorum	Pectobacterium carotovorum	MIC	=	125.0	ug.mL-1	PMID[475494]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	125.0	ug.mL-1	PMID[475494]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	125.0	ug.mL-1	PMID[475494]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	32.0	ug.mL-1	PMID[475495]
NPT175	Organism	Enterococcus faecalis	Enterococcus faecalis	MIC	>	128.0	ug.mL-1	PMID[475495]
NPT1531	Organism	Enterococcus faecium	Enterococcus faecium	MIC	>	128.0	ug.mL-1	PMID[475495]
NPT1190	Organism	Salmonella enterica	Salmonella enterica	MIC	=	64.0	ug.mL-1	PMID[475495]
NPT25245	ORGANISM	Proteus hauseri	Proteus hauseri	MIC	>	128.0	ug.mL-1	PMID[475495]
NPT173	Organism	Klebsiella pneumoniae	Klebsiella pneumoniae	MIC	>	128.0	ug.mL-1	PMID[475495]

☑ 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 NPC270848 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	379
0.1-0.2	2144
0.2-0.3	5534
0.3-0.4	12537
0.4-0.5	5891
0.5-0.6	8729
0.6-0.7	7327
0.7-0.8	125
0.8-0.85	13
0.85-0.9	8
0.9-0.95	5
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC272868
1.0	High Similarity	NPC122599
0.9853	High Similarity	NPC147137
0.9577	High Similarity	NPC470710
0.9275	High Similarity	NPC471236
0.9275	High Similarity	NPC197766
0.9203	High Similarity	NPC177967
0.9203	High Similarity	NPC471237
0.9071	High Similarity	NPC81137
0.8603	High Similarity	NPC213414
0.8533	High Similarity	NPC471235
0.8533	High Similarity	NPC73132
0.8533	High Similarity	NPC235033
0.8529	High Similarity	NPC105999
0.8456	Intermediate Similarity	NPC296202
0.8382	Intermediate Similarity	NPC7830
0.8298	Intermediate Similarity	NPC478071
0.8239	Intermediate Similarity	NPC11449
0.8028	Intermediate Similarity	NPC78061
0.8028	Intermediate Similarity	NPC122359
0.8028	Intermediate Similarity	NPC159987
0.7842	Intermediate Similarity	NPC180207
0.7698	Intermediate Similarity	NPC471033
0.7698	Intermediate Similarity	NPC311091
0.7681	Intermediate Similarity	NPC128249
0.7676	Intermediate Similarity	NPC116562
0.7676	Intermediate Similarity	NPC68167
0.7643	Intermediate Similarity	NPC100395
0.7516	Intermediate Similarity	NPC112789
0.7516	Intermediate Similarity	NPC19622
0.7483	Intermediate Similarity	NPC2596
0.7468	Intermediate Similarity	NPC275903
0.7467	Intermediate Similarity	NPC471328
0.7426	Intermediate Similarity	NPC79543
0.7391	Intermediate Similarity	NPC17693
0.7372	Intermediate Similarity	NPC473358
0.7372	Intermediate Similarity	NPC116842
0.7365	Intermediate Similarity	NPC196034
0.7353	Intermediate Similarity	NPC17525
0.7325	Intermediate Similarity	NPC271451
0.7324	Intermediate Similarity	NPC249435
0.7299	Intermediate Similarity	NPC54543
0.7248	Intermediate Similarity	NPC79332
0.7234	Intermediate Similarity	NPC322197
0.7226	Intermediate Similarity	NPC471495
0.7222	Intermediate Similarity	NPC233282
0.7219	Intermediate Similarity	NPC259017
0.7211	Intermediate Similarity	NPC288945
0.7203	Intermediate Similarity	NPC27633
0.7203	Intermediate Similarity	NPC94298
0.7194	Intermediate Similarity	NPC114682
0.7194	Intermediate Similarity	NPC268388
0.7188	Intermediate Similarity	NPC25844
0.7188	Intermediate Similarity	NPC178097
0.7183	Intermediate Similarity	NPC131192
0.7181	Intermediate Similarity	NPC22783
0.7178	Intermediate Similarity	NPC135103
0.7174	Intermediate Similarity	NPC88141
0.7171	Intermediate Similarity	NPC262359
0.7162	Intermediate Similarity	NPC4164
0.7153	Intermediate Similarity	NPC226699
0.7153	Intermediate Similarity	NPC264976
0.7143	Intermediate Similarity	NPC172262
0.7143	Intermediate Similarity	NPC119767
0.7143	Intermediate Similarity	NPC14141
0.7135	Intermediate Similarity	NPC470566
0.7134	Intermediate Similarity	NPC470986
0.7133	Intermediate Similarity	NPC95537
0.7125	Intermediate Similarity	NPC97188
0.7124	Intermediate Similarity	NPC129132
0.7124	Intermediate Similarity	NPC287533
0.7124	Intermediate Similarity	NPC205468
0.7124	Intermediate Similarity	NPC87231
0.7124	Intermediate Similarity	NPC257756
0.7124	Intermediate Similarity	NPC212631
0.7123	Intermediate Similarity	NPC115159
0.7123	Intermediate Similarity	NPC45438
0.7123	Intermediate Similarity	NPC267552
0.7123	Intermediate Similarity	NPC143427
0.7123	Intermediate Similarity	NPC19174
0.7123	Intermediate Similarity	NPC73532
0.7123	Intermediate Similarity	NPC224273
0.7122	Intermediate Similarity	NPC21162
0.7122	Intermediate Similarity	NPC183700
0.7115	Intermediate Similarity	NPC250266
0.7115	Intermediate Similarity	NPC266597
0.7115	Intermediate Similarity	NPC290291
0.7115	Intermediate Similarity	NPC275055
0.7114	Intermediate Similarity	NPC204579
0.7114	Intermediate Similarity	NPC110211
0.7113	Intermediate Similarity	NPC296526
0.7113	Intermediate Similarity	NPC23402
0.7107	Intermediate Similarity	NPC474692
0.7107	Intermediate Similarity	NPC66593
0.7097	Intermediate Similarity	NPC9985
0.7097	Intermediate Similarity	NPC239495
0.7095	Intermediate Similarity	NPC193805
0.7093	Intermediate Similarity	NPC470567
0.7089	Intermediate Similarity	NPC184632
0.7086	Intermediate Similarity	NPC214246
0.7086	Intermediate Similarity	NPC94810
0.7081	Intermediate Similarity	NPC147250
0.7081	Intermediate Similarity	NPC469498
0.708	Intermediate Similarity	NPC69332
0.708	Intermediate Similarity	NPC29989
0.708	Intermediate Similarity	NPC6984
0.708	Intermediate Similarity	NPC70843
0.708	Intermediate Similarity	NPC95178
0.7078	Intermediate Similarity	NPC213216
0.7078	Intermediate Similarity	NPC78540
0.7078	Intermediate Similarity	NPC56031
0.7078	Intermediate Similarity	NPC139813
0.7078	Intermediate Similarity	NPC274121
0.7078	Intermediate Similarity	NPC175098
0.7078	Intermediate Similarity	NPC192304
0.7078	Intermediate Similarity	NPC263670
0.7078	Intermediate Similarity	NPC242294
0.7078	Intermediate Similarity	NPC337373
0.7078	Intermediate Similarity	NPC188646
0.7078	Intermediate Similarity	NPC312318
0.7078	Intermediate Similarity	NPC57601
0.7078	Intermediate Similarity	NPC472365
0.7078	Intermediate Similarity	NPC50898
0.7075	Intermediate Similarity	NPC32032
0.7075	Intermediate Similarity	NPC91478
0.7075	Intermediate Similarity	NPC133909
0.707	Intermediate Similarity	NPC243528
0.707	Intermediate Similarity	NPC251681
0.707	Intermediate Similarity	NPC188947
0.707	Intermediate Similarity	NPC99333
0.707	Intermediate Similarity	NPC280284
0.7063	Intermediate Similarity	NPC19290
0.7063	Intermediate Similarity	NPC470216
0.7059	Intermediate Similarity	NPC64359
0.7059	Intermediate Similarity	NPC308037
0.7055	Intermediate Similarity	NPC297186
0.7055	Intermediate Similarity	NPC52931
0.7051	Intermediate Similarity	NPC194281
0.7051	Intermediate Similarity	NPC29353
0.7051	Intermediate Similarity	NPC234133
0.7051	Intermediate Similarity	NPC301915
0.7051	Intermediate Similarity	NPC47815
0.7051	Intermediate Similarity	NPC261292
0.7051	Intermediate Similarity	NPC231772
0.7051	Intermediate Similarity	NPC473887
0.7051	Intermediate Similarity	NPC124784
0.7051	Intermediate Similarity	NPC127447
0.7051	Intermediate Similarity	NPC13408
0.705	Intermediate Similarity	NPC95172
0.7048	Intermediate Similarity	NPC474535
0.7047	Intermediate Similarity	NPC137416
0.7044	Intermediate Similarity	NPC14871
0.7042	Intermediate Similarity	NPC285350
0.7039	Intermediate Similarity	NPC247779
0.7034	Intermediate Similarity	NPC61779
0.7034	Intermediate Similarity	NPC158222
0.7032	Intermediate Similarity	NPC311742
0.7032	Intermediate Similarity	NPC286336
0.703	Intermediate Similarity	NPC41326
0.7029	Intermediate Similarity	NPC29883
0.7029	Intermediate Similarity	NPC141523
0.7027	Intermediate Similarity	NPC473942
0.7025	Intermediate Similarity	NPC290664
0.7025	Intermediate Similarity	NPC261234
0.702	Intermediate Similarity	NPC221777
0.7019	Intermediate Similarity	NPC469953
0.7014	Intermediate Similarity	NPC469954
0.7012	Intermediate Similarity	NPC474620
0.7012	Intermediate Similarity	NPC151973
0.7007	Intermediate Similarity	NPC198336
0.7007	Intermediate Similarity	NPC120545
0.7007	Intermediate Similarity	NPC242895
0.7007	Intermediate Similarity	NPC156139
0.7006	Intermediate Similarity	NPC254841
0.7006	Intermediate Similarity	NPC162680
0.7006	Intermediate Similarity	NPC294409
0.7006	Intermediate Similarity	NPC116632
0.7006	Intermediate Similarity	NPC475697
0.7006	Intermediate Similarity	NPC188879
0.7006	Intermediate Similarity	NPC7013
0.7006	Intermediate Similarity	NPC4214
0.7006	Intermediate Similarity	NPC299379
0.7006	Intermediate Similarity	NPC303644
0.7006	Intermediate Similarity	NPC209560
0.7006	Intermediate Similarity	NPC228661
0.7006	Intermediate Similarity	NPC181124
0.7	Intermediate Similarity	NPC36181
0.7	Intermediate Similarity	NPC95309
0.7	Intermediate Similarity	NPC473751
0.6994	Remote Similarity	NPC17600
0.6993	Remote Similarity	NPC51345
0.6987	Remote Similarity	NPC474726
0.6987	Remote Similarity	NPC234560
0.6987	Remote Similarity	NPC131039
0.6987	Remote Similarity	NPC39426
0.6987	Remote Similarity	NPC163029
0.6987	Remote Similarity	NPC475955
0.6987	Remote Similarity	NPC324929
0.6986	Remote Similarity	NPC159525
0.6981	Remote Similarity	NPC235239

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 NPC270848 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	358
0.1-0.2	1000
0.2-0.3	1604
0.3-0.4	3037
0.4-0.5	2094
0.5-0.6	844
0.6-0.7	200
0.7-0.8	12
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
0.8258	Intermediate Similarity	NPD2296	Approved
0.7778	Intermediate Similarity	NPD4287	Approved
0.75	Intermediate Similarity	NPD3764	Approved
0.7469	Intermediate Similarity	NPD4288	Approved
0.7288	Intermediate Similarity	NPD3269	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD2344	Approved
0.7203	Intermediate Similarity	NPD9545	Approved
0.7162	Intermediate Similarity	NPD1203	Approved
0.7044	Intermediate Similarity	NPD2309	Approved
0.7039	Intermediate Similarity	NPD2313	Discontinued
0.7029	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD1510	Phase 2
0.6987	Remote Similarity	NPD2799	Discontinued
0.6974	Remote Similarity	NPD9718	Approved
0.697	Remote Similarity	NPD7411	Suspended
0.6964	Remote Similarity	NPD3749	Approved
0.6962	Remote Similarity	NPD1549	Phase 2
0.6948	Remote Similarity	NPD1240	Approved
0.6944	Remote Similarity	NPD9493	Approved
0.6943	Remote Similarity	NPD2935	Discontinued
0.6914	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD3750	Approved
0.6859	Remote Similarity	NPD1607	Approved
0.6852	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD3972	Approved
0.6846	Remote Similarity	NPD1481	Phase 2
0.6846	Remote Similarity	NPD9717	Approved
0.6821	Remote Similarity	NPD1164	Approved
0.679	Remote Similarity	NPD7440	Discontinued
0.6779	Remote Similarity	NPD1535	Discovery
0.6776	Remote Similarity	NPD2798	Approved
0.677	Remote Similarity	NPD4628	Phase 3
0.6748	Remote Similarity	NPD6799	Approved
0.6738	Remote Similarity	NPD9266	Approved
0.6738	Remote Similarity	NPD74	Approved
0.673	Remote Similarity	NPD5406	Approved
0.673	Remote Similarity	NPD5405	Approved
0.673	Remote Similarity	NPD5408	Approved
0.673	Remote Similarity	NPD5404	Approved
0.6728	Remote Similarity	NPD2354	Approved
0.6727	Remote Similarity	NPD5586	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD1470	Approved
0.671	Remote Similarity	NPD3268	Approved
0.6707	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6688	Remote Similarity	NPD6832	Phase 2
0.6687	Remote Similarity	NPD2346	Discontinued
0.6667	Remote Similarity	NPD9267	Approved
0.6667	Remote Similarity	NPD9264	Approved
0.6667	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD9263	Approved
0.6667	Remote Similarity	NPD7003	Approved
0.6667	Remote Similarity	NPD7075	Discontinued
0.6667	Remote Similarity	NPD4308	Phase 3
0.6667	Remote Similarity	NPD1201	Approved
0.6647	Remote Similarity	NPD3226	Approved
0.6647	Remote Similarity	NPD7458	Discontinued
0.6646	Remote Similarity	NPD1511	Approved
0.6646	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD1876	Approved
0.6629	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6625	Remote Similarity	NPD1551	Phase 2
0.6624	Remote Similarity	NPD943	Approved
0.6622	Remote Similarity	NPD1894	Discontinued
0.6608	Remote Similarity	NPD7768	Phase 2
0.6607	Remote Similarity	NPD4380	Phase 2
0.6603	Remote Similarity	NPD6798	Discontinued
0.6601	Remote Similarity	NPD2797	Approved
0.6588	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD7819	Suspended
0.6584	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6584	Remote Similarity	NPD2353	Approved
0.6566	Remote Similarity	NPD1512	Approved
0.6562	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD3748	Approved
0.6561	Remote Similarity	NPD6233	Phase 2
0.655	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6536	Remote Similarity	NPD3225	Approved
0.6529	Remote Similarity	NPD6801	Discontinued
0.6527	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6524	Remote Similarity	NPD6190	Approved
0.6522	Remote Similarity	NPD2796	Approved
0.6513	Remote Similarity	NPD1608	Approved
0.6512	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD6599	Discontinued
0.6507	Remote Similarity	NPD1241	Discontinued
0.6497	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6494	Remote Similarity	NPD3266	Approved
0.6494	Remote Similarity	NPD3267	Approved
0.6486	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6478	Remote Similarity	NPD1933	Approved
0.6478	Remote Similarity	NPD230	Phase 1
0.6474	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6467	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6467	Remote Similarity	NPD6273	Approved
0.6463	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6463	Remote Similarity	NPD8166	Discontinued
0.6463	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6463	Remote Similarity	NPD9281	Approved
0.646	Remote Similarity	NPD7033	Discontinued
0.6438	Remote Similarity	NPD5535	Approved
0.6433	Remote Similarity	NPD1934	Approved
0.6429	Remote Similarity	NPD5403	Approved
0.6424	Remote Similarity	NPD3887	Approved
0.642	Remote Similarity	NPD6232	Discontinued
0.6416	Remote Similarity	NPD3882	Suspended
0.6415	Remote Similarity	NPD4307	Phase 2
0.6407	Remote Similarity	NPD5401	Approved
0.6404	Remote Similarity	NPD7473	Discontinued
0.6403	Remote Similarity	NPD1238	Approved
0.6402	Remote Similarity	NPD1243	Approved
0.6395	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6395	Remote Similarity	NPD2801	Approved
0.6392	Remote Similarity	NPD411	Approved
0.6383	Remote Similarity	NPD9261	Approved
0.6382	Remote Similarity	NPD3847	Discontinued
0.638	Remote Similarity	NPD1471	Phase 3
0.6375	Remote Similarity	NPD447	Suspended
0.6375	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6358	Remote Similarity	NPD3817	Phase 2
0.6353	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6352	Remote Similarity	NPD520	Approved
0.6347	Remote Similarity	NPD7390	Discontinued
0.6338	Remote Similarity	NPD5909	Discontinued
0.6337	Remote Similarity	NPD7577	Discontinued
0.6329	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6328	Remote Similarity	NPD1161	Approved
0.6323	Remote Similarity	NPD1283	Approved
0.6316	Remote Similarity	NPD3019	Approved
0.6316	Remote Similarity	NPD17	Approved
0.631	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6306	Remote Similarity	NPD9494	Approved
0.6303	Remote Similarity	NPD2800	Approved
0.6299	Remote Similarity	NPD9269	Phase 2
0.6287	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6278	Remote Similarity	NPD3818	Discontinued
0.6277	Remote Similarity	NPD1202	Approved
0.6273	Remote Similarity	NPD6355	Discontinued
0.6272	Remote Similarity	NPD5049	Phase 3
0.6266	Remote Similarity	NPD2614	Approved
0.6259	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6257	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6257	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6257	Remote Similarity	NPD6166	Phase 2
0.6257	Remote Similarity	NPD3455	Phase 2
0.625	Remote Similarity	NPD6663	Approved
0.625	Remote Similarity	NPD4062	Phase 3
0.625	Remote Similarity	NPD9268	Approved
0.6242	Remote Similarity	NPD1019	Discontinued
0.6242	Remote Similarity	NPD5951	Approved
0.6242	Remote Similarity	NPD7596	Clinical (unspecified phase)
0.6236	Remote Similarity	NPD6808	Phase 2
0.6235	Remote Similarity	NPD920	Approved
0.6232	Remote Similarity	NPD2934	Approved
0.6232	Remote Similarity	NPD2933	Approved
0.6226	Remote Similarity	NPD7095	Approved
0.6224	Remote Similarity	NPD1237	Approved
0.6213	Remote Similarity	NPD2533	Approved
0.6213	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6213	Remote Similarity	NPD2534	Approved
0.6213	Remote Similarity	NPD2532	Approved
0.6211	Remote Similarity	NPD4445	Approved
0.6211	Remote Similarity	NPD3140	Approved
0.6211	Remote Similarity	NPD3142	Approved
0.6209	Remote Similarity	NPD2932	Approved
0.6203	Remote Similarity	NPD5736	Approved
0.6193	Remote Similarity	NPD6971	Discontinued
0.6187	Remote Similarity	NPD2859	Approved
0.6187	Remote Similarity	NPD2860	Approved
0.618	Remote Similarity	NPD6959	Discontinued
0.6176	Remote Similarity	NPD9258	Approved
0.6176	Remote Similarity	NPD9256	Approved
0.6175	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6175	Remote Similarity	NPD5953	Discontinued
0.6171	Remote Similarity	NPD5402	Approved
0.6164	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6159	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6158	Remote Similarity	NPD1168	Approved
0.6154	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD1929	Approved
0.6154	Remote Similarity	NPD5844	Phase 1
0.6154	Remote Similarity	NPD7286	Phase 2
0.6154	Remote Similarity	NPD1930	Approved
0.6149	Remote Similarity	NPD8032	Phase 2
0.6149	Remote Similarity	NPD6280	Approved
0.6149	Remote Similarity	NPD6279	Approved
0.6141	Remote Similarity	NPD6559	Discontinued
0.6139	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6139	Remote Similarity	NPD5647	Approved
0.6138	Remote Similarity	NPD3134	Approved
0.6135	Remote Similarity	NPD6651	Approved
0.6129	Remote Similarity	NPD1281	Approved
0.6129	Remote Similarity	NPD422	Phase 1
0.6125	Remote Similarity	NPD7008	Discontinued
0.6121	Remote Similarity	NPD1519	Approved
0.6121	Remote Similarity	NPD1537	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