NPASS Compound

Structure

NPC83289 OpenBabel07101719132D 39 41 0 0 1 0 0 0 0 0999 V2000 -0.9343 3.0706 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9888 -3.0174 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1152 -1.3306 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3942 1.6388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6915 -0.4507 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2939 0.5022 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2222 2.1374 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9451 -4.1707 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9451 -3.1941 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0994 -4.6590 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0994 -2.7058 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2536 -4.1707 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9852 -3.2172 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3538 -3.6145 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1394 -3.7055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2991 -4.2234 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6808 -1.4446 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3930 -0.5114 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5912 -2.0645 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5651 -2.1375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5579 1.4215 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.5353 -2.4103 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2536 -3.1941 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1655 -3.7785 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1675 -1.1846 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8458 0.4883 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6957 -1.7726 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4078 -2.7058 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.1936 -1.1117 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8196 0.5613 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5501 -0.8069 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7287 0.2045 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.6434 -1.9186 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 4.7176 -0.3777 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.7698 -0.2318 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9652 1.5270 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4592 -0.4501 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2564 -3.4217 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 7 1 0 0 0 0 2 20 1 0 0 0 0 3 20 1 0 0 0 0 5 35 1 0 0 0 0 6 35 1 0 0 0 0 7 21 1 0 0 0 0 8 9 2 0 0 0 0 8 10 1 0 0 0 0 9 11 1 0 0 0 0 10 12 2 0 0 0 0 11 23 2 0 0 0 0 12 23 1 0 0 0 0 13 15 1 0 0 0 0 13 22 2 0 0 0 0 14 16 2 0 0 0 0 14 22 1 0 0 0 0 15 24 2 0 0 0 0 16 24 1 0 0 0 0 17 18 2 0 0 0 0 17 22 1 0 0 0 0 18 32 1 0 0 0 0 19 20 1 0 0 0 0 21 4 1 6 0 0 0 24 39 1 0 0 0 0 25 19 1 1 0 0 0 25 29 1 0 0 0 0 25 35 1 0 0 0 0 26 21 1 6 0 0 0 26 30 1 0 0 0 0 26 33 1 0 0 0 0 27 28 1 0 0 0 0 27 31 1 0 0 0 0 27 34 1 1 0 0 0 28 23 1 6 0 0 0 28 39 1 0 0 0 0 29 34 2 3 0 0 0 29 36 1 0 0 0 0 30 32 2 3 0 0 0 30 37 1 0 0 0 0 31 33 2 3 0 0 0 31 38 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	534.32
Volume:	571.846
LogP:	4.409
LogD:	4.379
LogS:	-3.96
# Rotatable Bonds:	9
TPSA:	100.1
# H-Bond Aceptor:	8
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.534
Synthetic Accessibility Score:	5.51
Fsp3:	0.484
Lipinski Rule-of-5:	Accepted
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:	-5.215
MDCK Permeability:	1.4340702364279423e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.009
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.008
30% Bioavailability (F30%):	0.262

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.288
Plasma Protein Binding (PPB):	94.12550354003906%
Volume Distribution (VD):	1.679
Pgp-substrate:	1.8273661136627197%

ADMET: Metabolism

CYP1A2-inhibitor:	0.046
CYP1A2-substrate:	0.196
CYP2C19-inhibitor:	0.873
CYP2C19-substrate:	0.937
CYP2C9-inhibitor:	0.948
CYP2C9-substrate:	0.772
CYP2D6-inhibitor:	0.412
CYP2D6-substrate:	0.895
CYP3A4-inhibitor:	0.958
CYP3A4-substrate:	0.813

ADMET: Excretion

Clearance (CL):	5.437
Half-life (T1/2):	0.225

ADMET: Toxicity

hERG Blockers:	0.645
Human Hepatotoxicity (H-HT):	0.509
Drug-inuced Liver Injury (DILI):	0.894
AMES Toxicity:	0.135
Rat Oral Acute Toxicity:	0.198
Maximum Recommended Daily Dose:	0.845
Skin Sensitization:	0.033
Carcinogencity:	0.12
Eye Corrosion:	0.003
Eye Irritation:	0.007
Respiratory Toxicity:	0.373

Download Data

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

Natural Product: NPC83289

Natural Product ID:	NPC83289
*Common Name:**	Erythro-Myrianthine A
IUPAC Name:	(2S)-N-[(2Z,6S,9S,10S)-6-[(2S)-butan-2-yl]-5,8-dioxo-10-phenyl-11-oxa-4,7-diazabicyclo[10.2.2]hexadeca-1(14),2,12,15-tetraen-9-yl]-2-(dimethylamino)-4-methylpentanamide
Synonyms:
Standard InCHIKey:	FMWVLOOFBWURQV-WHRPCMNDSA-N
Standard InCHI:	InChI=1S/C31H42N4O4/c1-7-21(4)26-30(37)32-18-17-22-13-15-24(16-14-22)39-28(23-11-9-8-10-12-23)27(31(38)33-26)34-29(36)25(35(5)6)19-20(2)3/h8-18,20-21,25-28H,7,19H2,1-6H3,(H,32,37)(H,33,38)(H,34,36)/b18-17-/t21-,25-,26-,27-,28-/m0/s1
SMILES:	CC[C@@H]([C@@H]1N=C(O)[C@@H](N=C([C@@H](N(C)C)CC(C)C)O)[C@@H](Oc2ccc(/C=CN=C1O)cc2)c1ccccc1)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2407350
PubChem CID:	73349058
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0000013] Amino acids, peptides, and analogues [CHEMONTID:0000348] Peptides [CHEMONTID:0004831] Oligopeptides

*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
NPO25938	Discaria febrifuga	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23819826]
NPO25938	Discaria febrifuga	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
Others	11

Activity Type	# Activity
NON-MOLECULAR	2
Organism	9

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2580	Organism	Candida dubliniensis	Candida dubliniensis	Activity	>	50.0	ug	PMID[464492]
NPT186	Organism	Candida tropicalis	Candida tropicalis	Activity	>	50.0	ug	PMID[464492]
NPT85	Organism	Filobasidiella neoformans	Cryptococcus neoformans	Activity	>	50.0	ug	PMID[464492]
NPT20	Organism	Candida albicans	Candida albicans	Activity	>	50.0	ug	PMID[464492]
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	Activity	>	50.0	ug	PMID[464492]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	Activity	>	50.0	ug	PMID[464492]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	>	50.0	ug	PMID[464492]
NPT173	Organism	Klebsiella pneumoniae	Klebsiella pneumoniae	Activity	>	50.0	ug	PMID[464492]
NPT19	Organism	Escherichia coli	Escherichia coli	Activity	>	50.0	ug	PMID[464492]
NPT1277	Organism	Staphylococcus epidermidis ATCC 12228	Staphylococcus epidermidis ATCC 12228	Activity	>	50.0	ug	PMID[464492]

☑ 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 NPC83289 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	183
0.1-0.2	1171
0.2-0.3	7003
0.3-0.4	10592
0.4-0.5	7606
0.5-0.6	12614
0.6-0.7	3256
0.7-0.8	255
0.8-0.85	6
0.85-0.9	1
0.9-0.95	4
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC189724
1.0	High Similarity	NPC212850
0.9704	High Similarity	NPC247298
0.9562	High Similarity	NPC245974
0.9466	High Similarity	NPC274732
0.9173	High Similarity	NPC471953
0.8733	High Similarity	NPC254700
0.8271	Intermediate Similarity	NPC263835
0.8195	Intermediate Similarity	NPC256369
0.8162	Intermediate Similarity	NPC211218
0.8102	Intermediate Similarity	NPC95733
0.8102	Intermediate Similarity	NPC62101
0.806	Intermediate Similarity	NPC43275
0.8043	Intermediate Similarity	NPC29477
0.7987	Intermediate Similarity	NPC132771
0.7974	Intermediate Similarity	NPC233926
0.7974	Intermediate Similarity	NPC56635
0.7958	Intermediate Similarity	NPC307123
0.7958	Intermediate Similarity	NPC470392
0.7958	Intermediate Similarity	NPC97870
0.7958	Intermediate Similarity	NPC247018
0.7895	Intermediate Similarity	NPC317254
0.7895	Intermediate Similarity	NPC47672
0.7895	Intermediate Similarity	NPC303370
0.7868	Intermediate Similarity	NPC321133
0.7834	Intermediate Similarity	NPC472923
0.7829	Intermediate Similarity	NPC258222
0.7806	Intermediate Similarity	NPC319320
0.7806	Intermediate Similarity	NPC287757
0.7742	Intermediate Similarity	NPC212699
0.7742	Intermediate Similarity	NPC207675
0.7698	Intermediate Similarity	NPC471314
0.7698	Intermediate Similarity	NPC471315
0.7697	Intermediate Similarity	NPC115144
0.7697	Intermediate Similarity	NPC277857
0.7682	Intermediate Similarity	NPC313414
0.7681	Intermediate Similarity	NPC83279
0.7667	Intermediate Similarity	NPC63628
0.7667	Intermediate Similarity	NPC178466
0.7665	Intermediate Similarity	NPC315542
0.7664	Intermediate Similarity	NPC283760
0.7651	Intermediate Similarity	NPC195814
0.7647	Intermediate Similarity	NPC38458
0.7647	Intermediate Similarity	NPC311737
0.7647	Intermediate Similarity	NPC323948
0.764	Intermediate Similarity	NPC196091
0.7639	Intermediate Similarity	NPC114102
0.7635	Intermediate Similarity	NPC299583
0.7625	Intermediate Similarity	NPC473502
0.7609	Intermediate Similarity	NPC160120
0.7609	Intermediate Similarity	NPC41801
0.7609	Intermediate Similarity	NPC289330
0.7609	Intermediate Similarity	NPC53596
0.7609	Intermediate Similarity	NPC17388
0.7609	Intermediate Similarity	NPC471308
0.76	Intermediate Similarity	NPC266741
0.7594	Intermediate Similarity	NPC166837
0.7584	Intermediate Similarity	NPC168861
0.7582	Intermediate Similarity	NPC324081
0.7574	Intermediate Similarity	NPC258992
0.7574	Intermediate Similarity	NPC82963
0.7568	Intermediate Similarity	NPC41473
0.7568	Intermediate Similarity	NPC160607
0.7568	Intermediate Similarity	NPC312770
0.7568	Intermediate Similarity	NPC14600
0.7568	Intermediate Similarity	NPC204848
0.7566	Intermediate Similarity	NPC9373
0.7556	Intermediate Similarity	NPC118202
0.7552	Intermediate Similarity	NPC251571
0.7551	Intermediate Similarity	NPC6570
0.755	Intermediate Similarity	NPC135349
0.755	Intermediate Similarity	NPC81026
0.7535	Intermediate Similarity	NPC320242
0.7518	Intermediate Similarity	NPC255253
0.7518	Intermediate Similarity	NPC307020
0.7518	Intermediate Similarity	NPC328267
0.7517	Intermediate Similarity	NPC197921
0.7517	Intermediate Similarity	NPC476989
0.7516	Intermediate Similarity	NPC156311
0.75	Intermediate Similarity	NPC164608
0.7483	Intermediate Similarity	NPC301713
0.7481	Intermediate Similarity	NPC26524
0.7469	Intermediate Similarity	NPC186617
0.7467	Intermediate Similarity	NPC469360
0.7467	Intermediate Similarity	NPC91953
0.7466	Intermediate Similarity	NPC214869
0.745	Intermediate Similarity	NPC214988
0.7448	Intermediate Similarity	NPC52029
0.7448	Intermediate Similarity	NPC195749
0.7448	Intermediate Similarity	NPC35961
0.7444	Intermediate Similarity	NPC474272
0.7439	Intermediate Similarity	NPC248670
0.7438	Intermediate Similarity	NPC22014
0.7423	Intermediate Similarity	NPC471568
0.7423	Intermediate Similarity	NPC473693
0.7419	Intermediate Similarity	NPC471032
0.7419	Intermediate Similarity	NPC470935
0.7417	Intermediate Similarity	NPC474128
0.7397	Intermediate Similarity	NPC326966
0.7388	Intermediate Similarity	NPC474149
0.7379	Intermediate Similarity	NPC155838
0.7372	Intermediate Similarity	NPC109968
0.7372	Intermediate Similarity	NPC114659
0.7372	Intermediate Similarity	NPC139699
0.7368	Intermediate Similarity	NPC146530
0.7365	Intermediate Similarity	NPC475421
0.7361	Intermediate Similarity	NPC218323
0.7355	Intermediate Similarity	NPC473491
0.7351	Intermediate Similarity	NPC477837
0.7351	Intermediate Similarity	NPC477838
0.7321	Intermediate Similarity	NPC32064
0.7315	Intermediate Similarity	NPC237227
0.7313	Intermediate Similarity	NPC258056
0.731	Intermediate Similarity	NPC186898
0.7308	Intermediate Similarity	NPC76412
0.7303	Intermediate Similarity	NPC204546
0.7301	Intermediate Similarity	NPC107938
0.7301	Intermediate Similarity	NPC294516
0.7297	Intermediate Similarity	NPC267237
0.7292	Intermediate Similarity	NPC141739
0.7292	Intermediate Similarity	NPC136112
0.7289	Intermediate Similarity	NPC279871
0.7289	Intermediate Similarity	NPC158277
0.7273	Intermediate Similarity	NPC470393
0.7273	Intermediate Similarity	NPC16188
0.7254	Intermediate Similarity	NPC474862
0.7246	Intermediate Similarity	NPC37302
0.7241	Intermediate Similarity	NPC473378
0.7241	Intermediate Similarity	NPC473407
0.7239	Intermediate Similarity	NPC24101
0.7239	Intermediate Similarity	NPC179250
0.7239	Intermediate Similarity	NPC50380
0.7239	Intermediate Similarity	NPC96224
0.7235	Intermediate Similarity	NPC470903
0.7235	Intermediate Similarity	NPC167763
0.7235	Intermediate Similarity	NPC470112
0.7226	Intermediate Similarity	NPC5462
0.7219	Intermediate Similarity	NPC193528
0.7219	Intermediate Similarity	NPC231163
0.7219	Intermediate Similarity	NPC318591
0.7218	Intermediate Similarity	NPC231705
0.7215	Intermediate Similarity	NPC39431
0.7212	Intermediate Similarity	NPC90984
0.7212	Intermediate Similarity	NPC40234
0.7212	Intermediate Similarity	NPC151030
0.7212	Intermediate Similarity	NPC269383
0.7209	Intermediate Similarity	NPC276120
0.7208	Intermediate Similarity	NPC78530
0.72	Intermediate Similarity	NPC138365
0.72	Intermediate Similarity	NPC64205
0.7197	Intermediate Similarity	NPC38079
0.7197	Intermediate Similarity	NPC108875
0.7192	Intermediate Similarity	NPC153990
0.7192	Intermediate Similarity	NPC296712
0.7188	Intermediate Similarity	NPC140915
0.7188	Intermediate Similarity	NPC18249
0.7188	Intermediate Similarity	NPC305700
0.7188	Intermediate Similarity	NPC197741
0.7188	Intermediate Similarity	NPC10221
0.7188	Intermediate Similarity	NPC187028
0.7181	Intermediate Similarity	NPC313737
0.7181	Intermediate Similarity	NPC6854
0.7181	Intermediate Similarity	NPC169766
0.7181	Intermediate Similarity	NPC285078
0.7171	Intermediate Similarity	NPC296898
0.7169	Intermediate Similarity	NPC230611
0.7164	Intermediate Similarity	NPC142297
0.716	Intermediate Similarity	NPC194671
0.716	Intermediate Similarity	NPC269750
0.7152	Intermediate Similarity	NPC167944
0.7152	Intermediate Similarity	NPC231884
0.7152	Intermediate Similarity	NPC42793
0.7152	Intermediate Similarity	NPC182119
0.7151	Intermediate Similarity	NPC138083
0.7151	Intermediate Similarity	NPC299806
0.7143	Intermediate Similarity	NPC222039
0.7143	Intermediate Similarity	NPC283079
0.7143	Intermediate Similarity	NPC100478
0.7133	Intermediate Similarity	NPC29650
0.7133	Intermediate Similarity	NPC218530
0.7127	Intermediate Similarity	NPC311357
0.7126	Intermediate Similarity	NPC306804
0.7126	Intermediate Similarity	NPC137627
0.7126	Intermediate Similarity	NPC273755
0.7125	Intermediate Similarity	NPC206372
0.7125	Intermediate Similarity	NPC203424
0.7124	Intermediate Similarity	NPC314113
0.7114	Intermediate Similarity	NPC118419
0.7114	Intermediate Similarity	NPC93882
0.7114	Intermediate Similarity	NPC130595
0.7114	Intermediate Similarity	NPC244866
0.7111	Intermediate Similarity	NPC153690
0.7111	Intermediate Similarity	NPC97811
0.709	Intermediate Similarity	NPC113457
0.7089	Intermediate Similarity	NPC233702
0.7086	Intermediate Similarity	NPC29531
0.7086	Intermediate Similarity	NPC11147
0.7083	Intermediate Similarity	NPC473354
0.7083	Intermediate Similarity	NPC159767
0.7083	Intermediate Similarity	NPC471165

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 NPC83289 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	121
0.1-0.2	528
0.2-0.3	968
0.3-0.4	1595
0.4-0.5	2688
0.5-0.6	2141
0.6-0.7	918
0.7-0.8	188
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8321	Intermediate Similarity	NPD4993	Discontinued
0.8296	Intermediate Similarity	NPD3676	Clinical (unspecified phase)
0.8273	Intermediate Similarity	NPD3056	Clinical (unspecified phase)
0.8188	Intermediate Similarity	NPD7131	Phase 3
0.8169	Intermediate Similarity	NPD3052	Approved
0.8169	Intermediate Similarity	NPD3054	Approved
0.8085	Intermediate Similarity	NPD7477	Discontinued
0.8082	Intermediate Similarity	NPD2458	Approved
0.8082	Intermediate Similarity	NPD2460	Phase 3
0.8082	Intermediate Similarity	NPD2459	Approved
0.8029	Intermediate Similarity	NPD6583	Phase 3
0.8029	Intermediate Similarity	NPD6582	Phase 2
0.7974	Intermediate Similarity	NPD6072	Discontinued
0.797	Intermediate Similarity	NPD3596	Phase 2
0.7958	Intermediate Similarity	NPD1423	Approved
0.7958	Intermediate Similarity	NPD5745	Approved
0.7926	Intermediate Similarity	NPD6830	Clinical (unspecified phase)
0.7911	Intermediate Similarity	NPD7485	Phase 3
0.7911	Intermediate Similarity	NPD7484	Phase 3
0.7899	Intermediate Similarity	NPD3685	Discontinued
0.7891	Intermediate Similarity	NPD7596	Clinical (unspecified phase)
0.7868	Intermediate Similarity	NPD2668	Approved
0.7868	Intermediate Similarity	NPD2667	Approved
0.7857	Intermediate Similarity	NPD6584	Phase 3
0.7852	Intermediate Similarity	NPD6580	Approved
0.7852	Intermediate Similarity	NPD3692	Discontinued
0.7852	Intermediate Similarity	NPD6581	Approved
0.7834	Intermediate Similarity	NPD8070	Approved
0.7834	Intermediate Similarity	NPD8031	Discontinued
0.7817	Intermediate Similarity	NPD5746	Approved
0.7815	Intermediate Similarity	NPD4123	Phase 3
0.7815	Intermediate Similarity	NPD2874	Phase 2
0.7794	Intermediate Similarity	NPD2595	Approved
0.7794	Intermediate Similarity	NPD2594	Approved
0.7763	Intermediate Similarity	NPD7526	Approved
0.7763	Intermediate Similarity	NPD52	Approved
0.7763	Intermediate Similarity	NPD7527	Clinical (unspecified phase)
0.7761	Intermediate Similarity	NPD2557	Approved
0.7756	Intermediate Similarity	NPD5773	Approved
0.7756	Intermediate Similarity	NPD5772	Approved
0.775	Intermediate Similarity	NPD7608	Discontinued
0.7718	Intermediate Similarity	NPD6364	Approved
0.7718	Intermediate Similarity	NPD44	Approved
0.7714	Intermediate Similarity	NPD7258	Clinical (unspecified phase)
0.7708	Intermediate Similarity	NPD7265	Discontinued
0.7677	Intermediate Similarity	NPD4678	Approved
0.7677	Intermediate Similarity	NPD4675	Approved
0.7669	Intermediate Similarity	NPD821	Approved
0.7667	Intermediate Similarity	NPD6331	Phase 2
0.7651	Intermediate Similarity	NPD4149	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD7153	Discontinued
0.7639	Intermediate Similarity	NPD3374	Clinical (unspecified phase)
0.7635	Intermediate Similarity	NPD1725	Approved
0.7635	Intermediate Similarity	NPD3175	Clinical (unspecified phase)
0.7632	Intermediate Similarity	NPD7213	Phase 3
0.7632	Intermediate Similarity	NPD7212	Phase 2
0.7622	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7606	Intermediate Similarity	NPD2990	Approved
0.7606	Intermediate Similarity	NPD7018	Phase 2
0.7606	Intermediate Similarity	NPD2987	Approved
0.76	Intermediate Similarity	NPD2976	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD4237	Approved
0.76	Intermediate Similarity	NPD4236	Phase 3
0.7582	Intermediate Similarity	NPD6419	Discontinued
0.7582	Intermediate Similarity	NPD7447	Phase 1
0.7582	Intermediate Similarity	NPD3536	Discontinued
0.7582	Intermediate Similarity	NPD3985	Discontinued
0.7569	Intermediate Similarity	NPD3167	Approved
0.7569	Intermediate Similarity	NPD3166	Approved
0.7569	Intermediate Similarity	NPD3164	Approved
0.7569	Intermediate Similarity	NPD3165	Approved
0.7568	Intermediate Similarity	NPD6380	Phase 1
0.755	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.7536	Intermediate Similarity	NPD6382	Discontinued
0.7535	Intermediate Similarity	NPD1817	Approved
0.7535	Intermediate Similarity	NPD1819	Approved
0.7535	Intermediate Similarity	NPD1818	Approved
0.7535	Intermediate Similarity	NPD1820	Approved
0.7534	Intermediate Similarity	NPD5837	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD6390	Discontinued
0.7532	Intermediate Similarity	NPD6060	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD7046	Clinical (unspecified phase)
0.7518	Intermediate Similarity	NPD6540	Phase 3
0.7518	Intermediate Similarity	NPD2429	Approved
0.7518	Intermediate Similarity	NPD6542	Approved
0.7518	Intermediate Similarity	NPD4659	Approved
0.7518	Intermediate Similarity	NPD6539	Approved
0.7518	Intermediate Similarity	NPD6543	Approved
0.7518	Intermediate Similarity	NPD2428	Approved
0.7518	Intermediate Similarity	NPD1669	Approved
0.7517	Intermediate Similarity	NPD2161	Phase 2
0.7516	Intermediate Similarity	NPD7438	Suspended
0.75	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2200	Suspended
0.7483	Intermediate Similarity	NPD7451	Discontinued
0.7483	Intermediate Similarity	NPD4162	Approved
0.7482	Intermediate Similarity	NPD2554	Approved
0.7482	Intermediate Similarity	NPD2556	Approved
0.7468	Intermediate Similarity	NPD7019	Approved
0.7468	Intermediate Similarity	NPD7020	Approved
0.7468	Intermediate Similarity	NPD5348	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD5865	Clinical (unspecified phase)
0.7465	Intermediate Similarity	NPD6538	Approved
0.7465	Intermediate Similarity	NPD6541	Approved
0.7464	Intermediate Similarity	NPD2486	Discontinued
0.7451	Intermediate Similarity	NPD6667	Approved
0.7451	Intermediate Similarity	NPD6666	Approved
0.7448	Intermediate Similarity	NPD3179	Approved
0.7448	Intermediate Similarity	NPD3180	Approved
0.7432	Intermediate Similarity	NPD2157	Approved
0.7431	Intermediate Similarity	NPD1712	Approved
0.7424	Intermediate Similarity	NPD5373	Approved
0.7424	Intermediate Similarity	NPD5374	Approved
0.7419	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD4186	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD7037	Approved
0.7413	Intermediate Similarity	NPD4098	Discontinued
0.7403	Intermediate Similarity	NPD6087	Phase 1
0.74	Intermediate Similarity	NPD6032	Approved
0.7386	Intermediate Similarity	NPD5241	Discontinued
0.7375	Intermediate Similarity	NPD3556	Approved
0.7375	Intermediate Similarity	NPD3560	Approved
0.7375	Intermediate Similarity	NPD3559	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD3557	Approved
0.7375	Intermediate Similarity	NPD3558	Approved
0.7375	Intermediate Similarity	NPD6063	Approved
0.7368	Intermediate Similarity	NPD5289	Phase 2
0.7351	Intermediate Similarity	NPD7030	Discontinued
0.7347	Intermediate Similarity	NPD3530	Approved
0.7347	Intermediate Similarity	NPD3532	Approved
0.7347	Intermediate Similarity	NPD839	Approved
0.7347	Intermediate Similarity	NPD3531	Approved
0.7347	Intermediate Similarity	NPD840	Approved
0.7338	Intermediate Similarity	NPD5756	Phase 2
0.7333	Intermediate Similarity	NPD4108	Discontinued
0.7329	Intermediate Similarity	NPD5163	Phase 2
0.7329	Intermediate Similarity	NPD6179	Discontinued
0.7324	Intermediate Similarity	NPD2561	Approved
0.7324	Intermediate Similarity	NPD2562	Approved
0.7324	Intermediate Similarity	NPD2235	Phase 2
0.7324	Intermediate Similarity	NPD2230	Approved
0.7324	Intermediate Similarity	NPD2233	Approved
0.7324	Intermediate Similarity	NPD2232	Approved
0.7324	Intermediate Similarity	NPD2231	Phase 2
0.732	Intermediate Similarity	NPD7466	Approved
0.732	Intermediate Similarity	NPD5481	Discontinued
0.7312	Intermediate Similarity	NPD7972	Discontinued
0.7308	Intermediate Similarity	NPD1975	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD6090	Discontinued
0.7305	Intermediate Similarity	NPD3294	Phase 2
0.7305	Intermediate Similarity	NPD3421	Phase 3
0.7297	Intermediate Similarity	NPD2238	Phase 2
0.7297	Intermediate Similarity	NPD3597	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD2541	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD4103	Phase 2
0.7292	Intermediate Similarity	NPD1770	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD4104	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD1794	Approved
0.7286	Intermediate Similarity	NPD3445	Approved
0.7286	Intermediate Similarity	NPD3443	Approved
0.7286	Intermediate Similarity	NPD3444	Approved
0.7286	Intermediate Similarity	NPD3049	Approved
0.7279	Intermediate Similarity	NPD6812	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD7294	Phase 1
0.7279	Intermediate Similarity	NPD1048	Approved
0.7278	Intermediate Similarity	NPD6523	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD4129	Approved
0.7267	Intermediate Similarity	NPD3554	Approved
0.7267	Intermediate Similarity	NPD3552	Approved
0.7267	Intermediate Similarity	NPD3555	Approved
0.7267	Intermediate Similarity	NPD3553	Approved
0.7261	Intermediate Similarity	NPD2122	Discontinued
0.7256	Intermediate Similarity	NPD4986	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD3060	Approved
0.725	Intermediate Similarity	NPD4227	Discontinued
0.725	Intermediate Similarity	NPD4018	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD7493	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD3656	Approved
0.723	Intermediate Similarity	NPD5729	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD3058	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD4475	Approved
0.723	Intermediate Similarity	NPD4474	Approved
0.7219	Intermediate Similarity	NPD2156	Approved
0.7219	Intermediate Similarity	NPD2154	Approved
0.7219	Intermediate Similarity	NPD2155	Approved
0.7219	Intermediate Similarity	NPD1753	Discontinued
0.7211	Intermediate Similarity	NPD3136	Phase 2
0.7205	Intermediate Similarity	NPD3465	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD3965	Phase 1
0.72	Intermediate Similarity	NPD4579	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD1772	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD5266	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD2752	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD3568	Approved
0.7172	Intermediate Similarity	NPD3567	Approved
0.7171	Intermediate Similarity	NPD2240	Approved
0.7171	Intermediate Similarity	NPD2239	Approved
0.717	Intermediate Similarity	NPD8158	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD5718	Phase 2
0.7161	Intermediate Similarity	NPD5307	Clinical (unspecified phase)

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