NPASS Compound

Structure

CID223384 OpenBabel06191716022D 25 27 0 0 1 0 0 0 0 0999 V2000 -4.4152 4.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8666 0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 4.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 3.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 2.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 1.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 1.1910 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 -2.6831 -1.3090 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 -0.9511 -1.3090 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 2.1266 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1756 -1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1266 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5878 -0.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.9356 -1.8968 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 0.8666 -2.5691 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 1.1756 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 0.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3090 -2.5691 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9356 0.2788 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 1 0 0 0 0 2 21 1 0 0 0 0 3 4 1 0 0 0 0 4 5 1 0 0 0 0 5 6 1 0 0 0 0 6 7 1 0 0 0 0 7 10 1 0 0 0 0 8 9 2 0 0 0 0 8 11 1 0 0 0 0 9 12 1 0 0 0 0 10 12 2 0 0 0 0 10 14 1 0 0 0 0 11 14 2 0 0 0 0 11 16 1 0 0 0 0 12 22 1 0 0 0 0 13 15 2 0 0 0 0 13 17 1 0 0 0 0 13 19 1 0 0 0 0 14 25 1 0 0 0 0 15 20 1 0 0 0 0 16 18 1 0 0 0 0 16 23 2 0 0 0 0 17 21 1 0 0 0 0 17 24 2 0 0 0 0 18 15 1 1 0 0 0 18 21 1 0 0 0 0 18 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	244.07
Volume:	250.293
LogP:	2.693
LogD:	2.918
LogS:	-2.489
# Rotatable Bonds:	2
TPSA:	80.92
# H-Bond Aceptor:	4
# H-Bond Donor:	4
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.483
Synthetic Accessibility Score:	2.11
Fsp3:	0.0
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.031
MDCK Permeability:	1.3639996723213699e-05
Pgp-inhibitor:	0.023
Pgp-substrate:	0.021
Human Intestinal Absorption (HIA):	0.016
20% Bioavailability (F20%):	0.583
30% Bioavailability (F30%):	0.164

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.021
Plasma Protein Binding (PPB):	98.2811050415039%
Volume Distribution (VD):	0.579
Pgp-substrate:	1.4254989624023438%

ADMET: Metabolism

CYP1A2-inhibitor:	0.746
CYP1A2-substrate:	0.132
CYP2C19-inhibitor:	0.051
CYP2C19-substrate:	0.052
CYP2C9-inhibitor:	0.363
CYP2C9-substrate:	0.702
CYP2D6-inhibitor:	0.103
CYP2D6-substrate:	0.881
CYP3A4-inhibitor:	0.231
CYP3A4-substrate:	0.13

ADMET: Excretion

Clearance (CL):	19.96
Half-life (T1/2):	0.927

ADMET: Toxicity

hERG Blockers:	0.024
Human Hepatotoxicity (H-HT):	0.388
Drug-inuced Liver Injury (DILI):	0.144
AMES Toxicity:	0.677
Rat Oral Acute Toxicity:	0.637
Maximum Recommended Daily Dose:	0.256
Skin Sensitization:	0.966
Carcinogencity:	0.56
Eye Corrosion:	0.016
Eye Irritation:	0.954
Respiratory Toxicity:	0.761

Download Data

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

Natural Product: NPC223384

Natural Product ID:	NPC223384
*Common Name:**	Armeniaspirole A
IUPAC Name:	(2R)-3',4'-dichloro-7-hexyl-6-hydroxy-1'-methylspiro[1-benzofuran-2,5'-pyrrole]-2',3-dione
Synonyms:	Armeniaspirole A
Standard InCHIKey:	ZSUZJBBHPTXKIV-SFHVURJKSA-N
Standard InCHI:	InChI=1S/C18H19Cl2NO4/c1-3-4-5-6-7-10-12(22)9-8-11-14(10)25-18(16(11)23)15(20)13(19)17(24)21(18)2/h8-9,22H,3-7H2,1-2H3/t18-/m0/s1
SMILES:	CCCCCCc1c(ccc2c1O[C@@]1(C(=C(C(=O)N1C)Cl)Cl)C2=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2087639
PubChem CID:	58534983
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000301] Benzofurans

*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
NPO16310	Streptomyces armeniacus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[22921279]
NPO16310	Streptomyces armeniacus	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
IC50	2
MIC	5
Others	25

Activity Type	# Activity
Individual Protein	3
Organism	26
Others	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT109	Individual Protein	Cytochrome P450 3A4	Homo sapiens	IC50	>	10000.0	nM	PMID[551857]
NPT110	Individual Protein	Cytochrome P450 2D6	Homo sapiens	IC50	>	10000.0	nM	PMID[551857]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IC80	=	0.125	uM	PMID[551857]
NPT1118	Organism	Streptococcus pneumoniae	Streptococcus pneumoniae	IC80	=	2.3	uM	PMID[551857]
NPT1531	Organism	Enterococcus faecium	Enterococcus faecium	IC80	=	8.2	uM	PMID[551857]
NPT19	Organism	Escherichia coli	Escherichia coli	IC80	>	30.0	uM	PMID[551857]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	IC80	>	30.0	uM	PMID[551857]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	Survival	=	0.0	%	PMID[551857]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	Survival	=	50.0	%	PMID[551857]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	Survival	=	33.0	%	PMID[551857]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	Survival	=	67.0	%	PMID[551857]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	FC	=	0.2	n.a.	PMID[551857]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	FC	=	0.8	n.a.	PMID[551857]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	FC	=	1.7	n.a.	PMID[551857]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	FC	=	0.05	n.a.	PMID[551857]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	FC	=	0.9	n.a.	PMID[551857]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	FC	=	2.8	n.a.	PMID[551857]
NPT35	Others	n.a.		Solubility	=	25.0	ug.mL-1	PMID[551857]
NPT35	Others	n.a.		Drug degradation	=	30.0	%	PMID[551857]
NPT35	Others	n.a.		Drug degradation	<	10.0	%	PMID[551857]
NPT98	Individual Protein	HERG	Homo sapiens	Inhibition	<	35.0	%	PMID[551857]
NPT32	Organism	Mus musculus	Mus musculus	CL	=	20.0	mL.min-1.kg-1	PMID[551857]
NPT32	Organism	Mus musculus	Mus musculus	Vdss	=	2.4	L.kg-1	PMID[551857]
NPT32	Organism	Mus musculus	Mus musculus	Cmax	=	27.4	ug.mL-1	PMID[551857]
NPT32	Organism	Mus musculus	Mus musculus	T1/2	=	3.0	hr	PMID[551857]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	0.5	ug.mL-1	PMID[551858]
NPT1531	Organism	Enterococcus faecium	Enterococcus faecium	MIC	>	32.0	ug.mL-1	PMID[551858]
NPT175	Organism	Enterococcus faecalis	Enterococcus faecalis	MIC	=	16.0	ug.mL-1	PMID[551858]
NPT4151	Organism	Bacillus subtilis subsp. subtilis	Bacillus subtilis subsp. subtilis	MIC	=	2.0	ug.mL-1	PMID[551858]

☑ 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 NPC223384 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	337
0.1-0.2	2010
0.2-0.3	7930
0.3-0.4	10574
0.4-0.5	5742
0.5-0.6	9177
0.6-0.7	6334
0.7-0.8	592
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.75	Intermediate Similarity	NPC327005
0.7473	Intermediate Similarity	NPC129578
0.7444	Intermediate Similarity	NPC189130
0.7443	Intermediate Similarity	NPC210826
0.7443	Intermediate Similarity	NPC5820
0.7443	Intermediate Similarity	NPC178343
0.7443	Intermediate Similarity	NPC306488
0.7436	Intermediate Similarity	NPC264938
0.7429	Intermediate Similarity	NPC212932
0.7429	Intermediate Similarity	NPC293053
0.7429	Intermediate Similarity	NPC9117
0.7429	Intermediate Similarity	NPC24821
0.7429	Intermediate Similarity	NPC190637
0.7414	Intermediate Similarity	NPC171870
0.7407	Intermediate Similarity	NPC309692
0.7401	Intermediate Similarity	NPC12148
0.7401	Intermediate Similarity	NPC130581
0.7399	Intermediate Similarity	NPC137009
0.7399	Intermediate Similarity	NPC37206
0.7386	Intermediate Similarity	NPC273538
0.7386	Intermediate Similarity	NPC216538
0.7386	Intermediate Similarity	NPC326500
0.7384	Intermediate Similarity	NPC254841
0.7371	Intermediate Similarity	NPC144499
0.7371	Intermediate Similarity	NPC473042
0.7371	Intermediate Similarity	NPC162476
0.7371	Intermediate Similarity	NPC200694
0.736	Intermediate Similarity	NPC135325
0.736	Intermediate Similarity	NPC168085
0.7356	Intermediate Similarity	NPC261227
0.7356	Intermediate Similarity	NPC270883
0.7356	Intermediate Similarity	NPC69769
0.7356	Intermediate Similarity	NPC172986
0.7345	Intermediate Similarity	NPC124729
0.7345	Intermediate Similarity	NPC300267
0.7345	Intermediate Similarity	NPC51641
0.7345	Intermediate Similarity	NPC329678
0.7341	Intermediate Similarity	NPC470672
0.7341	Intermediate Similarity	NPC470669
0.7341	Intermediate Similarity	NPC474504
0.7341	Intermediate Similarity	NPC470668
0.7341	Intermediate Similarity	NPC474487
0.7341	Intermediate Similarity	NPC131130
0.7341	Intermediate Similarity	NPC470671
0.733	Intermediate Similarity	NPC225884
0.733	Intermediate Similarity	NPC106985
0.733	Intermediate Similarity	NPC166138
0.733	Intermediate Similarity	NPC158874
0.733	Intermediate Similarity	NPC18585
0.7326	Intermediate Similarity	NPC156910
0.7326	Intermediate Similarity	NPC174999
0.732	Intermediate Similarity	NPC469437
0.7318	Intermediate Similarity	NPC39929
0.7318	Intermediate Similarity	NPC470461
0.7318	Intermediate Similarity	NPC226644
0.7318	Intermediate Similarity	NPC37208
0.7318	Intermediate Similarity	NPC317492
0.7318	Intermediate Similarity	NPC37226
0.7318	Intermediate Similarity	NPC221868
0.7318	Intermediate Similarity	NPC296030
0.7314	Intermediate Similarity	NPC110969
0.7314	Intermediate Similarity	NPC64908
0.7314	Intermediate Similarity	NPC156590
0.7314	Intermediate Similarity	NPC205006
0.7314	Intermediate Similarity	NPC147688
0.7314	Intermediate Similarity	NPC118840
0.7303	Intermediate Similarity	NPC166757
0.7303	Intermediate Similarity	NPC14001
0.7299	Intermediate Similarity	NPC303633
0.7299	Intermediate Similarity	NPC96565
0.7299	Intermediate Similarity	NPC301217
0.7299	Intermediate Similarity	NPC220062
0.7299	Intermediate Similarity	NPC216978
0.7299	Intermediate Similarity	NPC55018
0.7299	Intermediate Similarity	NPC23257
0.7288	Intermediate Similarity	NPC71210
0.7288	Intermediate Similarity	NPC470857
0.7288	Intermediate Similarity	NPC311741
0.7288	Intermediate Similarity	NPC234629
0.7278	Intermediate Similarity	NPC78335
0.7278	Intermediate Similarity	NPC472421
0.7278	Intermediate Similarity	NPC61258
0.7278	Intermediate Similarity	NPC230713
0.7277	Intermediate Similarity	NPC99723
0.7273	Intermediate Similarity	NPC204469
0.7273	Intermediate Similarity	NPC471520
0.7273	Intermediate Similarity	NPC11561
0.7273	Intermediate Similarity	NPC226636
0.7267	Intermediate Similarity	NPC151113
0.7263	Intermediate Similarity	NPC211811
0.7263	Intermediate Similarity	NPC470460
0.7263	Intermediate Similarity	NPC296869
0.7263	Intermediate Similarity	NPC272194
0.7263	Intermediate Similarity	NPC244407
0.7258	Intermediate Similarity	NPC473196
0.7257	Intermediate Similarity	NPC28337
0.7257	Intermediate Similarity	NPC471587
0.7257	Intermediate Similarity	NPC241100
0.7257	Intermediate Similarity	NPC235239
0.7257	Intermediate Similarity	NPC475680
0.7257	Intermediate Similarity	NPC305355
0.7257	Intermediate Similarity	NPC477272
0.7257	Intermediate Similarity	NPC159275
0.7251	Intermediate Similarity	NPC93756
0.7251	Intermediate Similarity	NPC108113
0.7247	Intermediate Similarity	NPC477955
0.7247	Intermediate Similarity	NPC220418
0.7247	Intermediate Similarity	NPC470458
0.7241	Intermediate Similarity	NPC124269
0.7241	Intermediate Similarity	NPC21350
0.7241	Intermediate Similarity	NPC201395
0.7238	Intermediate Similarity	NPC472580
0.7238	Intermediate Similarity	NPC318424
0.7238	Intermediate Similarity	NPC474744
0.7238	Intermediate Similarity	NPC472423
0.7238	Intermediate Similarity	NPC170169
0.7238	Intermediate Similarity	NPC474772
0.7235	Intermediate Similarity	NPC27490
0.7232	Intermediate Similarity	NPC39329
0.7232	Intermediate Similarity	NPC150408
0.7232	Intermediate Similarity	NPC175504
0.7232	Intermediate Similarity	NPC91560
0.7232	Intermediate Similarity	NPC221432
0.7232	Intermediate Similarity	NPC75049
0.7232	Intermediate Similarity	NPC301751
0.7232	Intermediate Similarity	NPC143896
0.7232	Intermediate Similarity	NPC169591
0.7232	Intermediate Similarity	NPC219915
0.7232	Intermediate Similarity	NPC11700
0.7232	Intermediate Similarity	NPC302181
0.7232	Intermediate Similarity	NPC310130
0.7232	Intermediate Similarity	NPC38219
0.7232	Intermediate Similarity	NPC473813
0.7232	Intermediate Similarity	NPC164980
0.7232	Intermediate Similarity	NPC473812
0.7232	Intermediate Similarity	NPC68104
0.7232	Intermediate Similarity	NPC245482
0.7232	Intermediate Similarity	NPC149026
0.7232	Intermediate Similarity	NPC257097
0.7228	Intermediate Similarity	NPC161650
0.7228	Intermediate Similarity	NPC210048
0.7225	Intermediate Similarity	NPC168105
0.7225	Intermediate Similarity	NPC187826
0.7225	Intermediate Similarity	NPC186838
0.7225	Intermediate Similarity	NPC477244
0.7225	Intermediate Similarity	NPC150399
0.7225	Intermediate Similarity	NPC274109
0.7225	Intermediate Similarity	NPC1486
0.7225	Intermediate Similarity	NPC240147
0.7225	Intermediate Similarity	NPC121243
0.7225	Intermediate Similarity	NPC98115
0.7225	Intermediate Similarity	NPC477243
0.7225	Intermediate Similarity	NPC249606
0.7225	Intermediate Similarity	NPC12165
0.7225	Intermediate Similarity	NPC66349
0.7225	Intermediate Similarity	NPC41461
0.7225	Intermediate Similarity	NPC477242
0.7225	Intermediate Similarity	NPC25287
0.7222	Intermediate Similarity	NPC178202
0.7222	Intermediate Similarity	NPC269420
0.7219	Intermediate Similarity	NPC84772
0.7219	Intermediate Similarity	NPC472582
0.7216	Intermediate Similarity	NPC136840
0.7216	Intermediate Similarity	NPC90582
0.7216	Intermediate Similarity	NPC262094
0.7216	Intermediate Similarity	NPC310128
0.7216	Intermediate Similarity	NPC282300
0.7216	Intermediate Similarity	NPC103362
0.7216	Intermediate Similarity	NPC3188
0.7209	Intermediate Similarity	NPC125920
0.7209	Intermediate Similarity	NPC144027
0.7209	Intermediate Similarity	NPC236974
0.7209	Intermediate Similarity	NPC164136
0.7207	Intermediate Similarity	NPC201731
0.7207	Intermediate Similarity	NPC104406
0.7207	Intermediate Similarity	NPC237635
0.7207	Intermediate Similarity	NPC471285
0.7207	Intermediate Similarity	NPC97716
0.7207	Intermediate Similarity	NPC24673
0.7207	Intermediate Similarity	NPC79469
0.7204	Intermediate Similarity	NPC469505
0.72	Intermediate Similarity	NPC78913
0.72	Intermediate Similarity	NPC270913
0.72	Intermediate Similarity	NPC18260
0.72	Intermediate Similarity	NPC217186
0.72	Intermediate Similarity	NPC473076
0.72	Intermediate Similarity	NPC53181
0.72	Intermediate Similarity	NPC139554
0.72	Intermediate Similarity	NPC477956
0.7198	Intermediate Similarity	NPC327269
0.7198	Intermediate Similarity	NPC476238
0.7198	Intermediate Similarity	NPC171651
0.7198	Intermediate Similarity	NPC31627
0.7198	Intermediate Similarity	NPC477957
0.7198	Intermediate Similarity	NPC473996
0.7198	Intermediate Similarity	NPC243171
0.7198	Intermediate Similarity	NPC285623
0.7198	Intermediate Similarity	NPC35567
0.7193	Intermediate Similarity	NPC203817
0.7193	Intermediate Similarity	NPC10971

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 NPC223384 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	218
0.1-0.2	813
0.2-0.3	1435
0.3-0.4	2506
0.4-0.5	2459
0.5-0.6	1411
0.6-0.7	297
0.7-0.8	11
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
0.776	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.776	Intermediate Similarity	NPD4361	Phase 2
0.7742	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD4363	Phase 3
0.7436	Intermediate Similarity	NPD4360	Phase 2
0.7399	Intermediate Similarity	NPD2654	Approved
0.7386	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7164	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD7075	Discontinued
0.7122	Intermediate Similarity	NPD7584	Approved
0.7102	Intermediate Similarity	NPD2800	Approved
0.7095	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD3882	Suspended
0.7065	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7016	Intermediate Similarity	NPD5940	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD6801	Discontinued
0.6979	Remote Similarity	NPD6020	Phase 2
0.6949	Remote Similarity	NPD1549	Phase 2
0.6944	Remote Similarity	NPD6799	Approved
0.6936	Remote Similarity	NPD1240	Approved
0.6927	Remote Similarity	NPD7177	Discontinued
0.6895	Remote Similarity	NPD5711	Approved
0.6895	Remote Similarity	NPD5710	Approved
0.6893	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD1510	Phase 2
0.6865	Remote Similarity	NPD7411	Suspended
0.6857	Remote Similarity	NPD1607	Approved
0.6856	Remote Similarity	NPD1729	Discontinued
0.6845	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6836	Remote Similarity	NPD2796	Approved
0.6831	Remote Similarity	NPD1670	Discontinued
0.6823	Remote Similarity	NPD2403	Approved
0.6816	Remote Similarity	NPD1243	Approved
0.6811	Remote Similarity	NPD6599	Discontinued
0.6811	Remote Similarity	NPD4380	Phase 2
0.6791	Remote Similarity	NPD7819	Suspended
0.6788	Remote Similarity	NPD3446	Phase 1
0.6786	Remote Similarity	NPD6104	Discontinued
0.6776	Remote Similarity	NPD1512	Approved
0.6761	Remote Similarity	NPD4377	Discontinued
0.6739	Remote Similarity	NPD920	Approved
0.6736	Remote Similarity	NPD3451	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD2533	Approved
0.6721	Remote Similarity	NPD2534	Approved
0.6721	Remote Similarity	NPD2532	Approved
0.6718	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD3366	Approved
0.6697	Remote Similarity	NPD8469	Approved
0.6684	Remote Similarity	NPD3749	Approved
0.6682	Remote Similarity	NPD7585	Approved
0.6681	Remote Similarity	NPD7048	Phase 3
0.6667	Remote Similarity	NPD6651	Approved
0.6667	Remote Similarity	NPD1511	Approved
0.6649	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD1934	Approved
0.6649	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD919	Approved
0.6648	Remote Similarity	NPD3140	Approved
0.6648	Remote Similarity	NPD3142	Approved
0.6635	Remote Similarity	NPD7583	Approved
0.6632	Remote Similarity	NPD7768	Phase 2
0.6631	Remote Similarity	NPD6585	Discontinued
0.6618	Remote Similarity	NPD4466	Phase 1
0.6617	Remote Similarity	NPD3863	Clinical (unspecified phase)
0.6614	Remote Similarity	NPD6668	Clinical (unspecified phase)
0.6614	Remote Similarity	NPD2801	Approved
0.6612	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6611	Remote Similarity	NPD2344	Approved
0.6597	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD5890	Approved
0.6596	Remote Similarity	NPD5889	Approved
0.6593	Remote Similarity	NPD3750	Approved
0.658	Remote Similarity	NPD1247	Approved
0.658	Remote Similarity	NPD6959	Discontinued
0.6579	Remote Similarity	NPD3817	Phase 2
0.6578	Remote Similarity	NPD824	Approved
0.6575	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6564	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6564	Remote Similarity	NPD6166	Phase 2
0.6564	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD7907	Approved
0.6545	Remote Similarity	NPD4947	Clinical (unspecified phase)
0.6541	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6536	Remote Similarity	NPD743	Approved
0.6528	Remote Similarity	NPD5494	Approved
0.652	Remote Similarity	NPD3808	Clinical (unspecified phase)
0.6513	Remote Similarity	NPD5242	Approved
0.6502	Remote Similarity	NPD8491	Approved
0.65	Remote Similarity	NPD2799	Discontinued
0.6497	Remote Similarity	NPD3818	Discontinued
0.6493	Remote Similarity	NPD7064	Clinical (unspecified phase)
0.6492	Remote Similarity	NPD7318	Phase 3
0.6482	Remote Similarity	NPD5953	Discontinued
0.648	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6474	Remote Similarity	NPD6844	Discontinued
0.6474	Remote Similarity	NPD6280	Approved
0.6474	Remote Similarity	NPD6279	Approved
0.6474	Remote Similarity	NPD7577	Discontinued
0.6471	Remote Similarity	NPD5403	Approved
0.6471	Remote Similarity	NPD8366	Approved
0.6467	Remote Similarity	NPD2309	Approved
0.6465	Remote Similarity	NPD7286	Phase 2
0.6464	Remote Similarity	NPD1551	Phase 2
0.6464	Remote Similarity	NPD2935	Discontinued
0.6459	Remote Similarity	NPD7811	Phase 3
0.6459	Remote Similarity	NPD7810	Phase 3
0.6452	Remote Similarity	NPD3146	Approved
0.6452	Remote Similarity	NPD3688	Clinical (unspecified phase)
0.645	Remote Similarity	NPD6559	Discontinued
0.6445	Remote Similarity	NPD3057	Approved
0.6432	Remote Similarity	NPD5441	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD3926	Phase 2
0.6421	Remote Similarity	NPD6386	Approved
0.6421	Remote Similarity	NPD6385	Approved
0.6414	Remote Similarity	NPD2163	Approved
0.6413	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD3819	Phase 2
0.6402	Remote Similarity	NPD6973	Clinical (unspecified phase)
0.64	Remote Similarity	NPD8058	Clinical (unspecified phase)
0.64	Remote Similarity	NPD8059	Phase 3
0.64	Remote Similarity	NPD6797	Phase 2
0.6398	Remote Similarity	NPD3450	Approved
0.6398	Remote Similarity	NPD3452	Approved
0.6398	Remote Similarity	NPD2494	Approved
0.6398	Remote Similarity	NPD2493	Approved
0.6398	Remote Similarity	NPD5297	Approved
0.639	Remote Similarity	NPD6377	Clinical (unspecified phase)
0.6387	Remote Similarity	NPD7317	Phase 3
0.638	Remote Similarity	NPD4111	Phase 1
0.638	Remote Similarity	NPD4665	Approved
0.6378	Remote Similarity	NPD2354	Approved
0.6378	Remote Similarity	NPD6808	Phase 2
0.6373	Remote Similarity	NPD5019	Clinical (unspecified phase)
0.6372	Remote Similarity	NPD7701	Phase 2
0.6368	Remote Similarity	NPD2972	Approved
0.6368	Remote Similarity	NPD7251	Discontinued
0.6368	Remote Similarity	NPD3533	Approved
0.6364	Remote Similarity	NPD7447	Phase 1
0.6364	Remote Similarity	NPD2973	Approved
0.6364	Remote Similarity	NPD2974	Approved
0.6364	Remote Similarity	NPD2975	Approved
0.6364	Remote Similarity	NPD5401	Approved
0.6359	Remote Similarity	NPD2490	Approved
0.6359	Remote Similarity	NPD2488	Approved
0.6358	Remote Similarity	NPD9717	Approved
0.6351	Remote Similarity	NPD5457	Discontinued
0.6348	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD4413	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD6312	Discontinued
0.6345	Remote Similarity	NPD8051	Clinical (unspecified phase)
0.6344	Remote Similarity	NPD3281	Clinical (unspecified phase)
0.6344	Remote Similarity	NPD6667	Approved
0.6344	Remote Similarity	NPD160	Clinical (unspecified phase)
0.6344	Remote Similarity	NPD6666	Approved
0.634	Remote Similarity	NPD8005	Clinical (unspecified phase)
0.6337	Remote Similarity	NPD7808	Phase 3
0.6335	Remote Similarity	NPD6198	Phase 1
0.6321	Remote Similarity	NPD5967	Approved
0.6321	Remote Similarity	NPD5402	Approved
0.6321	Remote Similarity	NPD2379	Clinical (unspecified phase)
0.6319	Remote Similarity	NPD3748	Approved
0.6318	Remote Similarity	NPD3823	Discontinued
0.6316	Remote Similarity	NPD7667	Clinical (unspecified phase)
0.6313	Remote Similarity	NPD5726	Clinical (unspecified phase)
0.6313	Remote Similarity	NPD6894	Phase 1
0.631	Remote Similarity	NPD7212	Phase 2
0.631	Remote Similarity	NPD7213	Phase 3
0.631	Remote Similarity	NPD4357	Discontinued
0.6308	Remote Similarity	NPD4582	Approved
0.6308	Remote Similarity	NPD3298	Approved
0.6308	Remote Similarity	NPD4583	Approved
0.6303	Remote Similarity	NPD1880	Phase 3
0.6296	Remote Similarity	NPD7131	Phase 3
0.6296	Remote Similarity	NPD5586	Clinical (unspecified phase)
0.6294	Remote Similarity	NPD6232	Discontinued
0.6291	Remote Similarity	NPD3448	Approved
0.6291	Remote Similarity	NPD5006	Approved
0.6291	Remote Similarity	NPD5005	Approved
0.6291	Remote Similarity	NPD2491	Approved
0.6287	Remote Similarity	NPD3658	Clinical (unspecified phase)
0.6287	Remote Similarity	NPD5192	Clinical (unspecified phase)
0.6284	Remote Similarity	NPD4476	Approved
0.6284	Remote Similarity	NPD4477	Approved
0.6283	Remote Similarity	NPD1337	Clinical (unspecified phase)
0.6281	Remote Similarity	NPD7473	Discontinued
0.628	Remote Similarity	NPD5525	Clinical (unspecified phase)
0.6277	Remote Similarity	NPD4661	Approved
0.6277	Remote Similarity	NPD4662	Approved
0.6276	Remote Similarity	NPD2042	Clinical (unspecified phase)
0.6276	Remote Similarity	NPD2041	Clinical (unspecified phase)
0.6274	Remote Similarity	NPD4580	Approved
0.6274	Remote Similarity	NPD4107	Approved
0.6269	Remote Similarity	NPD7074	Phase 3
0.6268	Remote Similarity	NPD3473	Clinical (unspecified phase)
0.6262	Remote Similarity	NPD4004	Approved
0.6262	Remote Similarity	NPD1898	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