NPASS Compound

Structure

CID110094 OpenBabel06191715462D 34 37 0 0 1 0 0 0 0 0999 V2000 -3.3729 -0.9737 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5297 -2.4342 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5297 2.4342 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7030 -0.3564 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3301 -2.3038 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8432 1.4605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.9737 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6865 -0.9737 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8432 -1.4605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6865 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8432 -3.1470 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3564 -2.3038 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8432 0.4868 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3729 1.9474 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2162 1.4605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6865 1.9474 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8432 1.4605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3729 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5297 -1.4605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6865 -0.9737 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6865 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5297 0.4868 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -0.9737 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.3564 -3.9902 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1899 0.4868 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5297 1.4605 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.2162 0.4868 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8432 -1.4605 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8432 0.4868 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8432 -4.8335 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6173 -3.9902 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6767 -0.3564 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6767 1.3301 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 19 2 0 0 0 0 2 19 1 0 0 0 0 6 29 1 0 0 0 0 8 9 1 0 0 0 0 8 21 2 0 0 0 0 9 23 1 0 0 0 0 10 13 1 0 0 0 0 10 20 1 0 0 0 0 11 12 1 0 0 0 0 11 24 1 0 0 0 0 12 28 1 0 0 0 0 13 30 1 0 0 0 0 14 15 1 0 0 0 0 14 26 1 0 0 0 0 15 27 1 0 0 0 0 16 17 1 0 0 0 0 16 26 1 0 0 0 0 17 29 1 0 0 0 0 18 22 1 0 0 0 0 18 27 1 0 0 0 0 19 20 1 0 0 0 0 20 28 1 6 0 0 0 21 22 1 0 0 0 0 21 29 1 0 0 0 0 22 26 1 1 0 0 0 23 28 1 6 0 0 0 23 30 1 0 0 0 0 24 31 2 0 0 0 0 24 32 1 0 0 0 0 25 27 1 0 0 0 0 25 33 2 0 0 0 0 25 34 1 0 0 0 0 26 3 1 6 0 0 0 27 4 1 6 0 0 0 28 5 1 6 0 0 0 29 30 1 6 0 0 0 30 7 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	470.34
Volume:	517.825
LogP:	6.214
LogD:	4.222
LogS:	-3.992
# Rotatable Bonds:	5
TPSA:	74.6
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.408
Synthetic Accessibility Score:	4.804
Fsp3:	0.8
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.745
MDCK Permeability:	5.713387054129271e-06
Pgp-inhibitor:	0.006
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.089
30% Bioavailability (F30%):	0.082

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.057
Plasma Protein Binding (PPB):	96.34075164794922%
Volume Distribution (VD):	0.558
Pgp-substrate:	6.0840535163879395%

ADMET: Metabolism

CYP1A2-inhibitor:	0.005
CYP1A2-substrate:	0.334
CYP2C19-inhibitor:	0.008
CYP2C19-substrate:	0.77
CYP2C9-inhibitor:	0.056
CYP2C9-substrate:	0.271
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.103
CYP3A4-inhibitor:	0.123
CYP3A4-substrate:	0.135

ADMET: Excretion

Clearance (CL):	1.428
Half-life (T1/2):	0.277

ADMET: Toxicity

hERG Blockers:	0.018
Human Hepatotoxicity (H-HT):	0.517
Drug-inuced Liver Injury (DILI):	0.014
AMES Toxicity:	0.004
Rat Oral Acute Toxicity:	0.233
Maximum Recommended Daily Dose:	0.406
Skin Sensitization:	0.094
Carcinogencity:	0.377
Eye Corrosion:	0.335
Eye Irritation:	0.047
Respiratory Toxicity:	0.943

Download Data

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

Natural Product: NPC110094

Natural Product ID:	NPC110094
*Common Name:**	20-Epikoetjapic Acid
IUPAC Name:	(3R,4aR,6aR,7S,8S,10aR,10bS,12aS)-7-(2-carboxyethyl)-3,7,10a,10b,12a-pentamethyl-8-prop-1-en-2-yl-2,4,4a,6,6a,8,9,10,11,12-decahydro-1H-chrysene-3-carboxylic acid
Synonyms:	20-Epikoetjapic Acid
Standard InCHIKey:	ASOUKQDZWGOCBR-TYAUOZCYSA-N
Standard InCHI:	InChI=1S/C30H46O4/c1-19(2)20-10-13-30(7)23(28(20,5)12-11-24(31)32)9-8-21-22-18-27(4,25(33)34)15-14-26(22,3)16-17-29(21,30)6/h8,20,22-23H,1,9-18H2,2-7H3,(H,31,32)(H,33,34)/t20-,22-,23+,26+,27+,28-,29+,30+/m0/s1
SMILES:	C=C(C)[C@@H]1CC[C@]2(C)[C@H](CC=C3[C@@H]4C[C@@](C)(CC[C@]4(C)CC[C@@]23C)C(=O)O)[C@@]1(C)CCC(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL517189
PubChem CID:	10790564
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0003364] Steroid acids

*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
NPO13817	Maytenus undata	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10843569]
NPO26165	Sandoricum indicum	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11575968]
NPO8412	Monanchora arbuscula	Species	Crambeidae	Eukaryota	n.a.	Caribbean	n.a.	PMID[19743809]
NPO631	Osyris lanceolata	Species	Santalaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20499922]
NPO4016	Ligularia fischeri	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24892518]
NPO8412	Monanchora arbuscula	Species	Crambeidae	Eukaryota	n.a.	n.a.	n.a.	PMID[25924111]
NPO4016	Ligularia fischeri	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4016	Ligularia fischeri	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8412	Monanchora arbuscula	Species	Crambeidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13817	Maytenus undata	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26165	Sandoricum indicum	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO631	Osyris lanceolata	Species	Santalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4016	Ligularia fischeri	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8117	Aureolaria virginica	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2871	Canistrocarpus cervicornis	Species	Dictyotaceae	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
IC50	9
MIC	9

Activity Type	# Activity
Cell Line	5
NON-MOLECULAR	2
Organism	8
Others	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2831	Cell Line	P388/S	Mus musculus	IC50	>	25.0	ug.mL-1	PMID[455630]
NPT168	Cell Line	P388	Mus musculus	IC50	>	25.0	ug.mL-1	PMID[455630]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	3.25	ug.mL-1	PMID[455629]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	6.25	ug.mL-1	PMID[455629]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	=	6.25	ug.mL-1	PMID[455629]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	1900.0	nM	PMID[455629]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	500.0	nM	PMID[455629]
NPT27	Others	Unspecified		IC50	>	1000.0	nM	PMID[455629]
NPT2	Others	Unspecified		IC50	>	100.0	ug.mL-1	PMID[455630]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	0.01	ug	PMID[455631]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	0.001	ug	PMID[455631]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	=	0.01	ug	PMID[455631]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	0.01	ug	PMID[455631]
NPT20	Organism	Candida albicans	Candida albicans	MIC	=	0.001	ug	PMID[455631]
NPT1	Others	Radical scavenging activity		MIC	=	10.0	ug	PMID[455631]

☑ 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 NPC110094 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	180
0.1-0.2	1277
0.2-0.3	5892
0.3-0.4	16260
0.4-0.5	7528
0.5-0.6	5846
0.6-0.7	4195
0.7-0.8	1136
0.8-0.85	286
0.85-0.9	57
0.9-0.95	28
0.95-1	12

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC280654
1.0	High Similarity	NPC260385
0.9863	High Similarity	NPC199595
0.9861	High Similarity	NPC471899
0.9861	High Similarity	NPC107039
0.9861	High Similarity	NPC471897
0.973	High Similarity	NPC104545
0.973	High Similarity	NPC37038
0.9722	High Similarity	NPC89294
0.96	High Similarity	NPC221647
0.9595	High Similarity	NPC231431
0.9595	High Similarity	NPC16394
0.9467	High Similarity	NPC477057
0.9351	High Similarity	NPC200752
0.9342	High Similarity	NPC142244
0.9342	High Similarity	NPC471898
0.9342	High Similarity	NPC162632
0.9342	High Similarity	NPC267691
0.9342	High Similarity	NPC274050
0.9342	High Similarity	NPC263272
0.9315	High Similarity	NPC279666
0.9315	High Similarity	NPC192540
0.9231	High Similarity	NPC156981
0.9231	High Similarity	NPC96095
0.9221	High Similarity	NPC69101
0.9221	High Similarity	NPC251779
0.9189	High Similarity	NPC69143
0.9178	High Similarity	NPC241854
0.9178	High Similarity	NPC103958
0.9178	High Similarity	NPC283908
0.9178	High Similarity	NPC161923
0.9178	High Similarity	NPC183503
0.9178	High Similarity	NPC251970
0.9178	High Similarity	NPC476046
0.9167	High Similarity	NPC160817
0.9103	High Similarity	NPC70834
0.9091	High Similarity	NPC278459
0.9041	High Similarity	NPC36310
0.9	High Similarity	NPC324063
0.8987	High Similarity	NPC477289
0.8947	High Similarity	NPC321514
0.8933	High Similarity	NPC309399
0.8919	High Similarity	NPC255168
0.8889	High Similarity	NPC158141
0.8889	High Similarity	NPC173089
0.8875	High Similarity	NPC474537
0.8861	High Similarity	NPC167103
0.8846	High Similarity	NPC147066
0.8831	High Similarity	NPC327674
0.8816	High Similarity	NPC165711
0.88	High Similarity	NPC476844
0.88	High Similarity	NPC201027
0.878	High Similarity	NPC474511
0.878	High Similarity	NPC52169
0.878	High Similarity	NPC182797
0.878	High Similarity	NPC1753
0.878	High Similarity	NPC474474
0.875	High Similarity	NPC290445
0.875	High Similarity	NPC36616
0.8718	High Similarity	NPC267517
0.8701	High Similarity	NPC179028
0.8684	High Similarity	NPC246445
0.8684	High Similarity	NPC180886
0.8675	High Similarity	NPC293048
0.8675	High Similarity	NPC274330
0.8675	High Similarity	NPC270768
0.8675	High Similarity	NPC234346
0.8675	High Similarity	NPC59263
0.8675	High Similarity	NPC25906
0.8675	High Similarity	NPC290972
0.8675	High Similarity	NPC143232
0.8675	High Similarity	NPC198664
0.8675	High Similarity	NPC474700
0.8675	High Similarity	NPC64872
0.8675	High Similarity	NPC477973
0.8675	High Similarity	NPC130520
0.8675	High Similarity	NPC61543
0.8675	High Similarity	NPC281524
0.8675	High Similarity	NPC127689
0.8675	High Similarity	NPC121798
0.8675	High Similarity	NPC263393
0.8675	High Similarity	NPC225585
0.8667	High Similarity	NPC166797
0.8667	High Similarity	NPC301065
0.8667	High Similarity	NPC237591
0.8667	High Similarity	NPC3753
0.8659	High Similarity	NPC102683
0.8659	High Similarity	NPC130577
0.8659	High Similarity	NPC18064
0.8659	High Similarity	NPC71507
0.8659	High Similarity	NPC88716
0.8659	High Similarity	NPC51700
0.8659	High Similarity	NPC98442
0.8659	High Similarity	NPC171203
0.8659	High Similarity	NPC142415
0.8659	High Similarity	NPC293564
0.8659	High Similarity	NPC68160
0.8659	High Similarity	NPC307426
0.8659	High Similarity	NPC242468
0.8608	High Similarity	NPC38350
0.8608	High Similarity	NPC201912
0.8608	High Similarity	NPC327002
0.8608	High Similarity	NPC3915
0.859	High Similarity	NPC158846
0.859	High Similarity	NPC477371
0.8571	High Similarity	NPC113989
0.8571	High Similarity	NPC477872
0.8571	High Similarity	NPC130278
0.8571	High Similarity	NPC68828
0.8571	High Similarity	NPC7260
0.8571	High Similarity	NPC46441
0.8571	High Similarity	NPC120968
0.8571	High Similarity	NPC126369
0.8571	High Similarity	NPC193750
0.8571	High Similarity	NPC227467
0.8571	High Similarity	NPC198818
0.8571	High Similarity	NPC273621
0.8571	High Similarity	NPC474728
0.8571	High Similarity	NPC111110
0.8571	High Similarity	NPC120840
0.8571	High Similarity	NPC61952
0.8571	High Similarity	NPC210037
0.8571	High Similarity	NPC18872
0.8571	High Similarity	NPC290614
0.8571	High Similarity	NPC291028
0.8571	High Similarity	NPC470589
0.8554	High Similarity	NPC473242
0.8554	High Similarity	NPC40552
0.8554	High Similarity	NPC181225
0.8554	High Similarity	NPC290690
0.8554	High Similarity	NPC470629
0.8554	High Similarity	NPC17733
0.8554	High Similarity	NPC246708
0.8554	High Similarity	NPC474512
0.8553	High Similarity	NPC476795
0.8537	High Similarity	NPC73038
0.8537	High Similarity	NPC72638
0.8533	High Similarity	NPC330659
0.8533	High Similarity	NPC244708
0.8533	High Similarity	NPC161187
0.8519	High Similarity	NPC248758
0.85	High Similarity	NPC320514
0.85	High Similarity	NPC260956
0.85	High Similarity	NPC133391
0.85	High Similarity	NPC310989
0.8471	Intermediate Similarity	NPC71074
0.8471	Intermediate Similarity	NPC187722
0.8471	Intermediate Similarity	NPC306541
0.8471	Intermediate Similarity	NPC4036
0.8471	Intermediate Similarity	NPC60755
0.8471	Intermediate Similarity	NPC472149
0.8471	Intermediate Similarity	NPC230064
0.8471	Intermediate Similarity	NPC285184
0.8471	Intermediate Similarity	NPC474525
0.8471	Intermediate Similarity	NPC38754
0.8471	Intermediate Similarity	NPC235884
0.8471	Intermediate Similarity	NPC228784
0.8471	Intermediate Similarity	NPC65120
0.8471	Intermediate Similarity	NPC155120
0.8471	Intermediate Similarity	NPC324341
0.8471	Intermediate Similarity	NPC158030
0.8471	Intermediate Similarity	NPC966
0.8471	Intermediate Similarity	NPC288833
0.8471	Intermediate Similarity	NPC84319
0.8471	Intermediate Similarity	NPC145067
0.8471	Intermediate Similarity	NPC105189
0.8471	Intermediate Similarity	NPC282616
0.8471	Intermediate Similarity	NPC6255
0.8471	Intermediate Similarity	NPC471588
0.8471	Intermediate Similarity	NPC233455
0.8471	Intermediate Similarity	NPC52021
0.8471	Intermediate Similarity	NPC25299
0.8471	Intermediate Similarity	NPC470590
0.8471	Intermediate Similarity	NPC300351
0.8471	Intermediate Similarity	NPC77099
0.8462	Intermediate Similarity	NPC198240
0.8462	Intermediate Similarity	NPC239098
0.8462	Intermediate Similarity	NPC74410
0.8452	Intermediate Similarity	NPC161751
0.8452	Intermediate Similarity	NPC470588
0.8452	Intermediate Similarity	NPC95246
0.8452	Intermediate Similarity	NPC30522
0.8452	Intermediate Similarity	NPC474972
0.8452	Intermediate Similarity	NPC112454
0.8442	Intermediate Similarity	NPC899
0.8434	Intermediate Similarity	NPC96496
0.8434	Intermediate Similarity	NPC136948
0.8415	Intermediate Similarity	NPC76333
0.8415	Intermediate Similarity	NPC29447
0.8395	Intermediate Similarity	NPC83569
0.8395	Intermediate Similarity	NPC53733
0.8395	Intermediate Similarity	NPC69279
0.8395	Intermediate Similarity	NPC215893
0.8395	Intermediate Similarity	NPC477373
0.8395	Intermediate Similarity	NPC307258
0.8395	Intermediate Similarity	NPC97913
0.8395	Intermediate Similarity	NPC105803
0.8375	Intermediate Similarity	NPC40228
0.8375	Intermediate Similarity	NPC229584
0.8375	Intermediate Similarity	NPC14203

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 NPC110094 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	174
0.1-0.2	1624
0.2-0.3	3974
0.3-0.4	2268
0.4-0.5	637
0.5-0.6	236
0.6-0.7	171
0.7-0.8	63
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
0.8471	Intermediate Similarity	NPD7515	Phase 2
0.8452	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.8276	Intermediate Similarity	NPD7748	Approved
0.8025	Intermediate Similarity	NPD4695	Discontinued
0.8	Intermediate Similarity	NPD7902	Approved
0.7955	Intermediate Similarity	NPD6399	Phase 3
0.7907	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7889	Intermediate Similarity	NPD7614	Phase 1
0.7857	Intermediate Similarity	NPD4786	Approved
0.7831	Intermediate Similarity	NPD4221	Approved
0.7831	Intermediate Similarity	NPD4223	Phase 3
0.7831	Intermediate Similarity	NPD3667	Approved
0.7765	Intermediate Similarity	NPD5329	Approved
0.7765	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7701	Intermediate Similarity	NPD6672	Approved
0.7701	Intermediate Similarity	NPD5737	Approved
0.7674	Intermediate Similarity	NPD6409	Approved
0.7674	Intermediate Similarity	NPD7334	Approved
0.7674	Intermediate Similarity	NPD5330	Approved
0.7674	Intermediate Similarity	NPD7146	Approved
0.7674	Intermediate Similarity	NPD6098	Approved
0.7674	Intermediate Similarity	NPD7521	Approved
0.7674	Intermediate Similarity	NPD6684	Approved
0.7667	Intermediate Similarity	NPD7900	Approved
0.7667	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD3133	Approved
0.7647	Intermediate Similarity	NPD4197	Approved
0.7647	Intermediate Similarity	NPD3666	Approved
0.7647	Intermediate Similarity	NPD3665	Phase 1
0.764	Intermediate Similarity	NPD5281	Approved
0.764	Intermediate Similarity	NPD5284	Approved
0.7614	Intermediate Similarity	NPD6673	Approved
0.7614	Intermediate Similarity	NPD6904	Approved
0.7614	Intermediate Similarity	NPD6080	Approved
0.7609	Intermediate Similarity	NPD6083	Phase 2
0.7609	Intermediate Similarity	NPD6084	Phase 2
0.7586	Intermediate Similarity	NPD3573	Approved
0.7561	Intermediate Similarity	NPD3617	Approved
0.75	Intermediate Similarity	NPD6903	Approved
0.7471	Intermediate Similarity	NPD4688	Approved
0.7471	Intermediate Similarity	NPD4138	Approved
0.7471	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD4623	Approved
0.7471	Intermediate Similarity	NPD4693	Phase 3
0.7471	Intermediate Similarity	NPD5205	Approved
0.7471	Intermediate Similarity	NPD4690	Approved
0.7471	Intermediate Similarity	NPD4519	Discontinued
0.7471	Intermediate Similarity	NPD4689	Approved
0.7471	Intermediate Similarity	NPD3618	Phase 1
0.7444	Intermediate Similarity	NPD8034	Phase 2
0.7444	Intermediate Similarity	NPD8035	Phase 2
0.7442	Intermediate Similarity	NPD3668	Phase 3
0.7416	Intermediate Similarity	NPD5328	Approved
0.7416	Intermediate Similarity	NPD4753	Phase 2
0.7412	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD5695	Phase 3
0.734	Intermediate Similarity	NPD5696	Approved
0.7312	Intermediate Similarity	NPD7732	Phase 3
0.7303	Intermediate Similarity	NPD5208	Approved
0.7273	Intermediate Similarity	NPD5280	Approved
0.7273	Intermediate Similarity	NPD4694	Approved
0.7273	Intermediate Similarity	NPD4224	Phase 2
0.7273	Intermediate Similarity	NPD5690	Phase 2
0.7262	Intermediate Similarity	NPD7645	Phase 2
0.7253	Intermediate Similarity	NPD6050	Approved
0.7253	Intermediate Similarity	NPD6411	Approved
0.7253	Intermediate Similarity	NPD6079	Approved
0.7253	Intermediate Similarity	NPD5693	Phase 1
0.725	Intermediate Similarity	NPD6081	Approved
0.725	Intermediate Similarity	NPD4243	Approved
0.7215	Intermediate Similarity	NPD4137	Phase 3
0.7204	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD7638	Approved
0.7143	Intermediate Similarity	NPD5692	Phase 3
0.7126	Intermediate Similarity	NPD4788	Approved
0.7125	Intermediate Similarity	NPD4691	Approved
0.7125	Intermediate Similarity	NPD4747	Approved
0.7093	Intermediate Similarity	NPD4692	Approved
0.7093	Intermediate Similarity	NPD4139	Approved
0.7089	Intermediate Similarity	NPD3621	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD6404	Discontinued
0.7083	Intermediate Similarity	NPD7639	Approved
0.7083	Intermediate Similarity	NPD7640	Approved
0.7079	Intermediate Similarity	NPD5279	Phase 3
0.7073	Intermediate Similarity	NPD4784	Approved
0.7073	Intermediate Similarity	NPD4785	Approved
0.7071	Intermediate Similarity	NPD6675	Approved
0.7071	Intermediate Similarity	NPD6402	Approved
0.7071	Intermediate Similarity	NPD7128	Approved
0.7071	Intermediate Similarity	NPD5739	Approved
0.7065	Intermediate Similarity	NPD5694	Approved
0.7059	Intermediate Similarity	NPD4195	Approved
0.7033	Intermediate Similarity	NPD6101	Approved
0.7033	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD5210	Approved
0.7021	Intermediate Similarity	NPD4629	Approved
0.6989	Remote Similarity	NPD4202	Approved
0.6988	Remote Similarity	NPD6942	Approved
0.6988	Remote Similarity	NPD7339	Approved
0.6977	Remote Similarity	NPD7525	Registered
0.6957	Remote Similarity	NPD5207	Approved
0.6947	Remote Similarity	NPD4697	Phase 3
0.6947	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD5221	Approved
0.6947	Remote Similarity	NPD5222	Approved
0.6931	Remote Similarity	NPD6899	Approved
0.6931	Remote Similarity	NPD7320	Approved
0.6931	Remote Similarity	NPD6881	Approved
0.6915	Remote Similarity	NPD6001	Approved
0.6905	Remote Similarity	NPD6117	Approved
0.6905	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD4755	Approved
0.6875	Remote Similarity	NPD5173	Approved
0.6867	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD5733	Approved
0.6867	Remote Similarity	NPD4058	Approved
0.6863	Remote Similarity	NPD6373	Approved
0.6863	Remote Similarity	NPD6372	Approved
0.6835	Remote Similarity	NPD7331	Phase 2
0.6832	Remote Similarity	NPD5701	Approved
0.6832	Remote Similarity	NPD5697	Approved
0.6832	Remote Similarity	NPD6412	Phase 2
0.6824	Remote Similarity	NPD6116	Phase 1
0.6796	Remote Similarity	NPD7102	Approved
0.6796	Remote Similarity	NPD6883	Approved
0.6796	Remote Similarity	NPD7290	Approved
0.6786	Remote Similarity	NPD5275	Approved
0.6786	Remote Similarity	NPD4190	Phase 3
0.6786	Remote Similarity	NPD8039	Approved
0.6774	Remote Similarity	NPD4096	Approved
0.6765	Remote Similarity	NPD6011	Approved
0.6744	Remote Similarity	NPD6697	Approved
0.6744	Remote Similarity	NPD6118	Approved
0.6744	Remote Similarity	NPD6114	Approved
0.6744	Remote Similarity	NPD6115	Approved
0.6744	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD5285	Approved
0.6735	Remote Similarity	NPD4700	Approved
0.6735	Remote Similarity	NPD5286	Approved
0.6735	Remote Similarity	NPD4696	Approved
0.6731	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD6650	Approved
0.6731	Remote Similarity	NPD8130	Phase 1
0.6731	Remote Similarity	NPD6617	Approved
0.6731	Remote Similarity	NPD6649	Approved
0.6731	Remote Similarity	NPD6869	Approved
0.6731	Remote Similarity	NPD6847	Approved
0.6712	Remote Similarity	NPD4266	Approved
0.6712	Remote Similarity	NPD3196	Approved
0.6712	Remote Similarity	NPD3194	Approved
0.6712	Remote Similarity	NPD3195	Phase 2
0.6709	Remote Similarity	NPD7341	Phase 2
0.6705	Remote Similarity	NPD8028	Phase 2
0.67	Remote Similarity	NPD6052	Approved
0.6699	Remote Similarity	NPD6013	Approved
0.6699	Remote Similarity	NPD6014	Approved
0.6699	Remote Similarity	NPD6012	Approved
0.6667	Remote Similarity	NPD5223	Approved
0.6667	Remote Similarity	NPD5360	Phase 3
0.6667	Remote Similarity	NPD8297	Approved
0.6667	Remote Similarity	NPD6882	Approved
0.6667	Remote Similarity	NPD4687	Approved
0.6667	Remote Similarity	NPD6051	Approved
0.6667	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5654	Approved
0.6632	Remote Similarity	NPD5779	Approved
0.6632	Remote Similarity	NPD5133	Approved
0.6632	Remote Similarity	NPD5778	Approved
0.6627	Remote Similarity	NPD5276	Approved
0.6602	Remote Similarity	NPD6686	Approved
0.66	Remote Similarity	NPD5091	Approved
0.66	Remote Similarity	NPD5225	Approved
0.66	Remote Similarity	NPD5226	Approved
0.66	Remote Similarity	NPD5211	Phase 2
0.66	Remote Similarity	NPD5224	Approved
0.66	Remote Similarity	NPD4633	Approved
0.6575	Remote Similarity	NPD3172	Approved
0.6574	Remote Similarity	NPD7115	Discovery
0.6559	Remote Similarity	NPD4518	Approved
0.6538	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD4754	Approved
0.6535	Remote Similarity	NPD5174	Approved
0.6535	Remote Similarity	NPD5175	Approved
0.6531	Remote Similarity	NPD5959	Approved
0.6517	Remote Similarity	NPD857	Phase 3
0.6506	Remote Similarity	NPD4244	Approved
0.6506	Remote Similarity	NPD4789	Approved
0.6506	Remote Similarity	NPD4245	Approved
0.6505	Remote Similarity	NPD6614	Approved
0.6481	Remote Similarity	NPD6868	Approved
0.6471	Remote Similarity	NPD6924	Approved
0.6471	Remote Similarity	NPD5141	Approved
0.6471	Remote Similarity	NPD6926	Approved
0.6449	Remote Similarity	NPD4632	Approved
0.6436	Remote Similarity	NPD7632	Discontinued
0.6429	Remote Similarity	NPD5777	Approved
0.6429	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6413	Remote Similarity	NPD1694	Approved
0.6408	Remote Similarity	NPD4767	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