NPASS Compound

Structure

CID315914 OpenBabel06191716132D 42 48 0 0 1 0 0 0 0 0999 V2000 0.2079 2.5962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3578 -0.6045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7453 7.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2812 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1472 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7453 4.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7453 5.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7431 2.2872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1472 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8793 4.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8793 6.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2812 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0132 4.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1472 3.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0132 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0132 5.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2812 2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1472 4.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0132 2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.6180 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.9511 0.3090 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.9511 1.3090 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.5352 3.2653 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.8793 1.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.1472 6.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 2.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 3.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2812 4.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 2.8090 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 7.8793 7.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.8793 3.3090 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 29 1 0 0 0 0 2 30 1 0 0 0 0 3 40 1 0 0 0 0 4 5 1 0 0 0 0 4 11 1 0 0 0 0 5 13 1 0 0 0 0 6 7 2 0 0 0 0 6 14 1 0 0 0 0 7 15 1 0 0 0 0 8 11 2 0 0 0 0 8 12 1 0 0 0 0 9 12 1 0 0 0 0 9 30 1 0 0 0 0 10 29 1 0 0 0 0 10 32 1 0 0 0 0 11 16 1 0 0 0 0 12 17 2 0 0 0 0 13 18 2 0 0 0 0 13 21 1 0 0 0 0 14 19 2 0 0 0 0 14 41 1 0 0 0 0 15 22 2 0 0 0 0 15 40 1 0 0 0 0 16 18 1 0 0 0 0 16 23 2 0 0 0 0 17 23 1 0 0 0 0 17 27 1 0 0 0 0 18 24 1 0 0 0 0 19 22 1 0 0 0 0 19 25 1 0 0 0 0 20 24 2 0 0 0 0 20 25 1 0 0 0 0 20 26 1 0 0 0 0 21 26 2 0 0 0 0 21 33 1 0 0 0 0 22 34 1 0 0 0 0 23 35 1 0 0 0 0 24 36 1 0 0 0 0 25 37 2 0 0 0 0 26 41 1 0 0 0 0 27 31 1 0 0 0 0 27 38 2 0 0 0 0 28 29 1 0 0 0 0 28 39 2 0 0 0 0 28 42 1 0 0 0 0 29 31 1 0 0 0 0 30 31 1 0 0 0 0 30 42 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	575.14
Volume:	543.593
LogP:	3.511
LogD:	1.469
LogS:	-4.096
# Rotatable Bonds:	2
TPSA:	190.36
# H-Bond Aceptor:	12
# H-Bond Donor:	6
# Rings:	7
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.078
Synthetic Accessibility Score:	4.788
Fsp3:	0.267
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.839
MDCK Permeability:	7.735897270322312e-06
Pgp-inhibitor:	0.648
Pgp-substrate:	0.743
Human Intestinal Absorption (HIA):	0.929
20% Bioavailability (F20%):	0.025
30% Bioavailability (F30%):	0.377

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.009
Plasma Protein Binding (PPB):	82.14157104492188%
Volume Distribution (VD):	0.772
Pgp-substrate:	29.678138732910156%

ADMET: Metabolism

CYP1A2-inhibitor:	0.218
CYP1A2-substrate:	0.438
CYP2C19-inhibitor:	0.028
CYP2C19-substrate:	0.65
CYP2C9-inhibitor:	0.765
CYP2C9-substrate:	0.595
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.136
CYP3A4-inhibitor:	0.092
CYP3A4-substrate:	0.957

ADMET: Excretion

Clearance (CL):	2.629
Half-life (T1/2):	0.785

ADMET: Toxicity

hERG Blockers:	0.0
Human Hepatotoxicity (H-HT):	0.186
Drug-inuced Liver Injury (DILI):	0.979
AMES Toxicity:	0.417
Rat Oral Acute Toxicity:	0.015
Maximum Recommended Daily Dose:	0.765
Skin Sensitization:	0.155
Carcinogencity:	0.05
Eye Corrosion:	0.003
Eye Irritation:	0.006
Respiratory Toxicity:	0.068

Download Data

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

Natural Product: NPC315914

Natural Product ID:	NPC315914
*Common Name:**	Citreamicin Epsilon
IUPAC Name:	n.a.
Synonyms:	Citreamicin Epsilon
Standard InCHIKey:	FJAZFAHKUIAABK-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C30H25NO11/c1-29(10-32)28(39)42-30(2)9-12-8-11-4-5-13-18(16(11)23(35)17(12)27(38)31(29)30)24(36)20-25(37)19-14(41-26(20)21(13)33)6-7-15(40-3)22(19)34/h6-8,32-36H,4-5,9-10H2,1-3H3
SMILES:	COc1ccc2c(c1O)c(=O)c1c(o2)c(O)c2c(c1O)c1c(CC2)cc2c(c1O)C(=O)N1C(C2)(C)OC(=O)C1(C)CO
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL507445
PubChem CID:	25147606
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0002817] Dibenzopyrans [CHEMONTID:0000200] Xanthenes [CHEMONTID:0000204] Xanthones

*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
NPO19824	Streptomyces vinaceus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[19053507]
NPO19824	Streptomyces vinaceus	Species	Streptomycetaceae	Bacteria	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
MIC	20
Others	2

Activity Type	# Activity
Cell Line	1
NON-MOLECULAR	1
Organism	20

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT3190	Cell Line	NHDF	Homo sapiens	CC90	=	0.1	ug ml-1	PMID[528814]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	0.13	ug.mL-1	PMID[528814]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	0.12	ug.mL-1	PMID[528814]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	0.25	ug.mL-1	PMID[528814]
NPT1531	Organism	Enterococcus faecium	Enterococcus faecium	MIC	=	0.5	ug.mL-1	PMID[528814]
NPT1118	Organism	Streptococcus pneumoniae	Streptococcus pneumoniae	MIC	=	0.25	ug.mL-1	PMID[528814]
NPT1118	Organism	Streptococcus pneumoniae	Streptococcus pneumoniae	MIC	=	0.12	ug.mL-1	PMID[528814]
NPT1122	Organism	Haemophilus influenzae	Haemophilus influenzae	MIC	>	32.0	ug.mL-1	PMID[528814]
NPT3189	Organism	Haemophilus parainfluenzae	Haemophilus parainfluenzae	MIC	>	32.0	ug.mL-1	PMID[528814]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	64.0	ug.mL-1	PMID[528814]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	32.0	ug.mL-1	PMID[528814]
NPT173	Organism	Klebsiella pneumoniae	Klebsiella pneumoniae	MIC	>	32.0	ug.mL-1	PMID[528814]
NPT1121	Organism	Moraxella catarrhalis	Moraxella catarrhalis	MIC	=	0.5	ug.mL-1	PMID[528814]
NPT1248	Organism	Serratia marcescens	Serratia marcescens	MIC	>	32.0	ug.mL-1	PMID[528814]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	>	32.0	ug.mL-1	PMID[528814]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	CC90	=	1.0	ug ml-1	PMID[528814]

☑ 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 NPC315914 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	401
0.1-0.2	1798
0.2-0.3	5219
0.3-0.4	11355
0.4-0.5	6475
0.5-0.6	7568
0.6-0.7	7563
0.7-0.8	2303
0.8-0.85	6
0.85-0.9	1
0.9-0.95	4
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9429	High Similarity	NPC316292
0.8287	Intermediate Similarity	NPC82056
0.8133	Intermediate Similarity	NPC185031
0.8111	Intermediate Similarity	NPC38964
0.8044	Intermediate Similarity	NPC211215
0.7952	Intermediate Similarity	NPC83019
0.7905	Intermediate Similarity	NPC204580
0.7887	Intermediate Similarity	NPC286135
0.7883	Intermediate Similarity	NPC170101
0.7864	Intermediate Similarity	NPC478048
0.786	Intermediate Similarity	NPC314946
0.7828	Intermediate Similarity	NPC321226
0.7828	Intermediate Similarity	NPC478046
0.7828	Intermediate Similarity	NPC180210
0.7828	Intermediate Similarity	NPC314914
0.7828	Intermediate Similarity	NPC328856
0.7828	Intermediate Similarity	NPC478047
0.7804	Intermediate Similarity	NPC119818
0.7804	Intermediate Similarity	NPC202771
0.7804	Intermediate Similarity	NPC328700
0.7804	Intermediate Similarity	NPC2173
0.7793	Intermediate Similarity	NPC284236
0.7793	Intermediate Similarity	NPC316368
0.7773	Intermediate Similarity	NPC315253
0.7745	Intermediate Similarity	NPC81332
0.7745	Intermediate Similarity	NPC212038
0.7745	Intermediate Similarity	NPC271848
0.7745	Intermediate Similarity	NPC289396
0.7745	Intermediate Similarity	NPC262580
0.774	Intermediate Similarity	NPC150977
0.7729	Intermediate Similarity	NPC324742
0.7729	Intermediate Similarity	NPC473785
0.7714	Intermediate Similarity	NPC105591
0.7703	Intermediate Similarity	NPC208890
0.7696	Intermediate Similarity	NPC80472
0.7689	Intermediate Similarity	NPC131258
0.7681	Intermediate Similarity	NPC207467
0.7674	Intermediate Similarity	NPC316164
0.7671	Intermediate Similarity	NPC46990
0.7659	Intermediate Similarity	NPC4200
0.7659	Intermediate Similarity	NPC158226
0.7653	Intermediate Similarity	NPC24228
0.7644	Intermediate Similarity	NPC185275
0.7635	Intermediate Similarity	NPC272560
0.7633	Intermediate Similarity	NPC324220
0.7633	Intermediate Similarity	NPC216307
0.7633	Intermediate Similarity	NPC312630
0.7619	Intermediate Similarity	NPC469437
0.7617	Intermediate Similarity	NPC124302
0.7617	Intermediate Similarity	NPC70290
0.7617	Intermediate Similarity	NPC73020
0.7617	Intermediate Similarity	NPC14622
0.7617	Intermediate Similarity	NPC215098
0.7617	Intermediate Similarity	NPC46744
0.7611	Intermediate Similarity	NPC44040
0.761	Intermediate Similarity	NPC17219
0.7606	Intermediate Similarity	NPC264302
0.7598	Intermediate Similarity	NPC474024
0.7598	Intermediate Similarity	NPC6588
0.7598	Intermediate Similarity	NPC14662
0.7598	Intermediate Similarity	NPC477154
0.7598	Intermediate Similarity	NPC117854
0.7596	Intermediate Similarity	NPC265380
0.7594	Intermediate Similarity	NPC473618
0.7591	Intermediate Similarity	NPC153365
0.7586	Intermediate Similarity	NPC326520
0.7581	Intermediate Similarity	NPC207239
0.7561	Intermediate Similarity	NPC300307
0.7561	Intermediate Similarity	NPC188079
0.7561	Intermediate Similarity	NPC49487
0.7561	Intermediate Similarity	NPC99613
0.7561	Intermediate Similarity	NPC163130
0.7561	Intermediate Similarity	NPC165979
0.756	Intermediate Similarity	NPC113446
0.7559	Intermediate Similarity	NPC295436
0.7549	Intermediate Similarity	NPC37870
0.7549	Intermediate Similarity	NPC472449
0.7549	Intermediate Similarity	NPC472452
0.7549	Intermediate Similarity	NPC170245
0.7548	Intermediate Similarity	NPC196771
0.7547	Intermediate Similarity	NPC179947
0.7547	Intermediate Similarity	NPC174486
0.7546	Intermediate Similarity	NPC226652
0.7546	Intermediate Similarity	NPC120671
0.7546	Intermediate Similarity	NPC314100
0.7546	Intermediate Similarity	NPC72788
0.7545	Intermediate Similarity	NPC257728
0.7537	Intermediate Similarity	NPC236521
0.7537	Intermediate Similarity	NPC152659
0.7537	Intermediate Similarity	NPC474350
0.7537	Intermediate Similarity	NPC197168
0.7537	Intermediate Similarity	NPC248638
0.7537	Intermediate Similarity	NPC270837
0.7537	Intermediate Similarity	NPC7483
0.7537	Intermediate Similarity	NPC236132
0.7536	Intermediate Similarity	NPC154527
0.7536	Intermediate Similarity	NPC310794
0.7536	Intermediate Similarity	NPC327005
0.7535	Intermediate Similarity	NPC314020
0.7535	Intermediate Similarity	NPC477082
0.7524	Intermediate Similarity	NPC102277
0.7524	Intermediate Similarity	NPC124470
0.7524	Intermediate Similarity	NPC53680
0.7524	Intermediate Similarity	NPC208797
0.7524	Intermediate Similarity	NPC313304
0.7524	Intermediate Similarity	NPC279209
0.7524	Intermediate Similarity	NPC265795
0.7524	Intermediate Similarity	NPC109827
0.7524	Intermediate Similarity	NPC47883
0.7523	Intermediate Similarity	NPC477258
0.7512	Intermediate Similarity	NPC477081
0.7512	Intermediate Similarity	NPC243877
0.7512	Intermediate Similarity	NPC472387
0.7512	Intermediate Similarity	NPC476619
0.7512	Intermediate Similarity	NPC234331
0.7512	Intermediate Similarity	NPC247973
0.7512	Intermediate Similarity	NPC476621
0.7512	Intermediate Similarity	NPC477083
0.7512	Intermediate Similarity	NPC476622
0.7512	Intermediate Similarity	NPC297807
0.7512	Intermediate Similarity	NPC476618
0.7512	Intermediate Similarity	NPC205721
0.7512	Intermediate Similarity	NPC476623
0.7512	Intermediate Similarity	NPC476620
0.75	Intermediate Similarity	NPC239752
0.75	Intermediate Similarity	NPC472450
0.75	Intermediate Similarity	NPC25361
0.75	Intermediate Similarity	NPC314596
0.75	Intermediate Similarity	NPC226725
0.75	Intermediate Similarity	NPC261623
0.75	Intermediate Similarity	NPC139350
0.75	Intermediate Similarity	NPC471788
0.75	Intermediate Similarity	NPC275780
0.75	Intermediate Similarity	NPC469650
0.75	Intermediate Similarity	NPC257266
0.75	Intermediate Similarity	NPC227906
0.75	Intermediate Similarity	NPC111490
0.749	Intermediate Similarity	NPC133864
0.7488	Intermediate Similarity	NPC174700
0.7488	Intermediate Similarity	NPC260263
0.7488	Intermediate Similarity	NPC25152
0.7488	Intermediate Similarity	NPC257667
0.7488	Intermediate Similarity	NPC162694
0.7488	Intermediate Similarity	NPC186847
0.7488	Intermediate Similarity	NPC294965
0.7488	Intermediate Similarity	NPC472454
0.7488	Intermediate Similarity	NPC121333
0.7477	Intermediate Similarity	NPC160543
0.7477	Intermediate Similarity	NPC174140
0.7477	Intermediate Similarity	NPC472720
0.7477	Intermediate Similarity	NPC93065
0.7477	Intermediate Similarity	NPC472724
0.7477	Intermediate Similarity	NPC469652
0.7477	Intermediate Similarity	NPC472721
0.7477	Intermediate Similarity	NPC31208
0.7476	Intermediate Similarity	NPC475212
0.7476	Intermediate Similarity	NPC153578
0.7476	Intermediate Similarity	NPC299149
0.7476	Intermediate Similarity	NPC114257
0.7476	Intermediate Similarity	NPC183843
0.7476	Intermediate Similarity	NPC212290
0.7476	Intermediate Similarity	NPC84494
0.7476	Intermediate Similarity	NPC245059
0.7476	Intermediate Similarity	NPC476279
0.7476	Intermediate Similarity	NPC244903
0.7476	Intermediate Similarity	NPC277710
0.7475	Intermediate Similarity	NPC228785
0.7475	Intermediate Similarity	NPC14353
0.7475	Intermediate Similarity	NPC56085
0.7465	Intermediate Similarity	NPC475654
0.7465	Intermediate Similarity	NPC226708
0.7464	Intermediate Similarity	NPC49667
0.7464	Intermediate Similarity	NPC8127
0.7464	Intermediate Similarity	NPC473562
0.7463	Intermediate Similarity	NPC39091
0.7463	Intermediate Similarity	NPC224851
0.7463	Intermediate Similarity	NPC20216
0.7463	Intermediate Similarity	NPC277480
0.7463	Intermediate Similarity	NPC30027
0.7463	Intermediate Similarity	NPC29160
0.7463	Intermediate Similarity	NPC43319
0.7463	Intermediate Similarity	NPC128293
0.7453	Intermediate Similarity	NPC49690
0.7453	Intermediate Similarity	NPC22115
0.7453	Intermediate Similarity	NPC275680
0.7453	Intermediate Similarity	NPC231254
0.7452	Intermediate Similarity	NPC261471
0.7451	Intermediate Similarity	NPC220313
0.7451	Intermediate Similarity	NPC475985
0.7451	Intermediate Similarity	NPC67959
0.7451	Intermediate Similarity	NPC189473
0.7451	Intermediate Similarity	NPC146134
0.7451	Intermediate Similarity	NPC23298
0.7451	Intermediate Similarity	NPC207690
0.7451	Intermediate Similarity	NPC273959
0.7441	Intermediate Similarity	NPC470453
0.7441	Intermediate Similarity	NPC470448
0.7441	Intermediate Similarity	NPC470452
0.7441	Intermediate Similarity	NPC18306
0.7441	Intermediate Similarity	NPC477860

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 NPC315914 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	278
0.1-0.2	706
0.2-0.3	1478
0.3-0.4	2465
0.4-0.5	2462
0.5-0.6	1260
0.6-0.7	407
0.7-0.8	94
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
0.7962	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7804	Intermediate Similarity	NPD5005	Approved
0.7804	Intermediate Similarity	NPD5006	Approved
0.7773	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7689	Intermediate Similarity	NPD8153	Approved
0.7689	Intermediate Similarity	NPD8152	Approved
0.7639	Intermediate Similarity	NPD7048	Phase 3
0.7626	Intermediate Similarity	NPD7701	Phase 2
0.7617	Intermediate Similarity	NPD4420	Approved
0.7611	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7577	Intermediate Similarity	NPD6997	Phase 2
0.7561	Intermediate Similarity	NPD5844	Phase 1
0.7545	Intermediate Similarity	NPD7585	Approved
0.7533	Intermediate Similarity	NPD7907	Approved
0.7523	Intermediate Similarity	NPD7783	Phase 2
0.7523	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7584	Approved
0.75	Intermediate Similarity	NPD7583	Approved
0.7488	Intermediate Similarity	NPD6232	Discontinued
0.7463	Intermediate Similarity	NPD7473	Discontinued
0.7445	Intermediate Similarity	NPD4665	Approved
0.7445	Intermediate Similarity	NPD4111	Phase 1
0.7432	Intermediate Similarity	NPD8151	Discontinued
0.7431	Intermediate Similarity	NPD3452	Approved
0.7431	Intermediate Similarity	NPD2494	Approved
0.7431	Intermediate Similarity	NPD3450	Approved
0.7431	Intermediate Similarity	NPD2493	Approved
0.7416	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7415	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7415	Intermediate Similarity	NPD6166	Phase 2
0.7415	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.7366	Intermediate Similarity	NPD5242	Approved
0.7353	Intermediate Similarity	NPD6959	Discontinued
0.7342	Intermediate Similarity	NPD6973	Clinical (unspecified phase)
0.7339	Intermediate Similarity	NPD8285	Discontinued
0.733	Intermediate Similarity	NPD4583	Approved
0.733	Intermediate Similarity	NPD4582	Approved
0.7317	Intermediate Similarity	NPD5711	Approved
0.7317	Intermediate Similarity	NPD5710	Approved
0.729	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD4004	Approved
0.7285	Intermediate Similarity	NPD4002	Approved
0.7264	Intermediate Similarity	NPD8053	Approved
0.7264	Intermediate Similarity	NPD8054	Approved
0.726	Intermediate Similarity	NPD7177	Discontinued
0.7252	Intermediate Similarity	NPD8320	Phase 1
0.7252	Intermediate Similarity	NPD8319	Approved
0.7248	Intermediate Similarity	NPD2974	Approved
0.7248	Intermediate Similarity	NPD2975	Approved
0.7248	Intermediate Similarity	NPD2973	Approved
0.7227	Intermediate Similarity	NPD6779	Approved
0.7227	Intermediate Similarity	NPD6781	Approved
0.7227	Intermediate Similarity	NPD6776	Approved
0.7227	Intermediate Similarity	NPD6778	Approved
0.7227	Intermediate Similarity	NPD6777	Approved
0.7227	Intermediate Similarity	NPD6780	Approved
0.7227	Intermediate Similarity	NPD6782	Approved
0.7222	Intermediate Similarity	NPD8058	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD8059	Phase 3
0.722	Intermediate Similarity	NPD5494	Approved
0.7217	Intermediate Similarity	NPD2899	Discontinued
0.7207	Intermediate Similarity	NPD7697	Approved
0.7207	Intermediate Similarity	NPD7698	Approved
0.7207	Intermediate Similarity	NPD7696	Phase 3
0.719	Intermediate Similarity	NPD7074	Phase 3
0.7189	Intermediate Similarity	NPD6212	Phase 3
0.7189	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7189	Intermediate Similarity	NPD6213	Phase 3
0.7182	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD3808	Clinical (unspecified phase)
0.7175	Intermediate Similarity	NPD7871	Phase 2
0.7175	Intermediate Similarity	NPD7870	Phase 2
0.717	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD7874	Approved
0.7168	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD7047	Phase 3
0.7157	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7156	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7149	Intermediate Similarity	NPD4580	Approved
0.7143	Intermediate Similarity	NPD7054	Approved
0.7143	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD2801	Approved
0.7137	Intermediate Similarity	NPD5676	Approved
0.7109	Intermediate Similarity	NPD7472	Approved
0.7097	Intermediate Similarity	NPD2488	Approved
0.7097	Intermediate Similarity	NPD2490	Approved
0.7095	Intermediate Similarity	NPD3818	Discontinued
0.7094	Intermediate Similarity	NPD1934	Approved
0.7064	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD6020	Phase 2
0.7059	Intermediate Similarity	NPD1465	Phase 2
0.7059	Intermediate Similarity	NPD8067	Phase 3
0.7056	Intermediate Similarity	NPD8404	Phase 2
0.7054	Intermediate Similarity	NPD4846	Phase 2
0.7054	Intermediate Similarity	NPD7435	Discontinued
0.7046	Intermediate Similarity	NPD7654	Discontinued
0.7045	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD4361	Phase 2
0.7042	Intermediate Similarity	NPD7039	Approved
0.7042	Intermediate Similarity	NPD6559	Discontinued
0.7042	Intermediate Similarity	NPD7038	Approved
0.7009	Intermediate Similarity	NPD3448	Approved
0.7009	Intermediate Similarity	NPD6823	Phase 2
0.7009	Intermediate Similarity	NPD3057	Approved
0.7009	Intermediate Similarity	NPD2491	Approved
0.7005	Intermediate Similarity	NPD7906	Approved
0.7	Intermediate Similarity	NPD4363	Phase 3
0.7	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6625	Approved
0.7	Intermediate Similarity	NPD6534	Approved
0.7	Intermediate Similarity	NPD4360	Phase 2
0.7	Intermediate Similarity	NPD6535	Approved
0.6995	Remote Similarity	NPD6797	Phase 2
0.699	Remote Similarity	NPD3882	Suspended
0.6987	Remote Similarity	NPD7801	Approved
0.6982	Remote Similarity	NPD7699	Phase 2
0.6982	Remote Similarity	NPD7700	Phase 2
0.6981	Remote Similarity	NPD8156	Discontinued
0.6978	Remote Similarity	NPD7597	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD8313	Approved
0.6977	Remote Similarity	NPD8312	Approved
0.6976	Remote Similarity	NPD7819	Suspended
0.6963	Remote Similarity	NPD7251	Discontinued
0.6951	Remote Similarity	NPD7811	Phase 3
0.6951	Remote Similarity	NPD7810	Phase 3
0.6944	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6942	Remote Similarity	NPD3817	Phase 2
0.6934	Remote Similarity	NPD7228	Approved
0.6934	Remote Similarity	NPD8252	Approved
0.6934	Remote Similarity	NPD8099	Discontinued
0.6934	Remote Similarity	NPD8251	Approved
0.6933	Remote Similarity	NPD3533	Approved
0.6933	Remote Similarity	NPD2972	Approved
0.693	Remote Similarity	NPD7549	Discontinued
0.693	Remote Similarity	NPD7808	Phase 3
0.692	Remote Similarity	NPD4107	Approved
0.6916	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD4663	Approved
0.6881	Remote Similarity	NPD3863	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD8150	Discontinued
0.6878	Remote Similarity	NPD7411	Suspended
0.6877	Remote Similarity	NPD8461	Discontinued
0.6875	Remote Similarity	NPD3749	Approved
0.6875	Remote Similarity	NPD7075	Discontinued
0.6866	Remote Similarity	NPD6851	Approved
0.6866	Remote Similarity	NPD6853	Approved
0.686	Remote Similarity	NPD7942	Clinical (unspecified phase)
0.6847	Remote Similarity	NPD4413	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD2534	Approved
0.6832	Remote Similarity	NPD2532	Approved
0.6832	Remote Similarity	NPD2533	Approved
0.6829	Remote Similarity	NPD4380	Phase 2
0.6828	Remote Similarity	NPD7497	Discontinued
0.6824	Remote Similarity	NPD7930	Approved
0.6822	Remote Similarity	NPD3050	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.682	Remote Similarity	NPD2971	Approved
0.682	Remote Similarity	NPD2968	Approved
0.682	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.6814	Remote Similarity	NPD4482	Phase 3
0.681	Remote Similarity	NPD5677	Discontinued
0.681	Remote Similarity	NPD7827	Phase 1
0.6802	Remote Similarity	NPD6181	Discontinued
0.6798	Remote Similarity	NPD4040	Phase 1
0.6791	Remote Similarity	NPD5441	Clinical (unspecified phase)
0.6779	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6777	Remote Similarity	NPD7199	Phase 2
0.6774	Remote Similarity	NPD8453	Clinical (unspecified phase)
0.6773	Remote Similarity	NPD8367	Approved
0.6762	Remote Similarity	NPD6234	Discontinued
0.6761	Remote Similarity	NPD3451	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD6297	Approved
0.6758	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD7768	Phase 2
0.6744	Remote Similarity	NPD5313	Approved
0.6744	Remote Similarity	NPD5312	Approved
0.6743	Remote Similarity	NPD4577	Approved
0.6743	Remote Similarity	NPD4578	Approved
0.6734	Remote Similarity	NPD1483	Discontinued
0.6732	Remote Similarity	NPD8492	Approved
0.6731	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6722	Remote Similarity	NPD8469	Approved
0.6721	Remote Similarity	NPD7922	Phase 1
0.6714	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6714	Remote Similarity	NPD8005	Clinical (unspecified phase)
0.6712	Remote Similarity	NPD5525	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD7238	Clinical (unspecified phase)
0.67	Remote Similarity	NPD1511	Approved
0.6699	Remote Similarity	NPD5353	Approved
0.6699	Remote Similarity	NPD5402	Approved
0.6698	Remote Similarity	NPD5940	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6697	Remote Similarity	NPD7291	Discontinued
0.6696	Remote Similarity	NPD5457	Discontinued
0.6696	Remote Similarity	NPD8161	Suspended
0.6683	Remote Similarity	NPD6801	Discontinued
0.6683	Remote Similarity	NPD37	Approved
0.6681	Remote Similarity	NPD7064	Clinical (unspecified phase)
0.668	Remote Similarity	NPD7223	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