NPASS Compound

Structure

CID69279 OpenBabel06191715402D 34 37 0 0 1 0 0 0 0 0999 V2000 -0.0790 -6.5842 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4631 -5.8971 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8724 -4.8036 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3803 2.9616 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2557 2.4560 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5349 -0.5240 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0006 -1.9862 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0003 1.0111 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6697 -4.1165 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2730 -3.2261 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8454 1.4633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6906 1.9509 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6891 -0.9746 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6897 -0.9756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2240 0.4866 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3795 -0.0010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6888 0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8446 -1.4632 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4937 -5.7955 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0970 -4.9052 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8457 -2.4374 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.8454 -1.4627 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6900 -0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8452 0.4876 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5355 1.4628 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.2243 1.4623 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8151 -2.5390 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3800 1.9504 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5352 0.4871 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0003 -0.9751 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.0905 1.9621 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2118 -3.4293 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3878 -1.7503 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 19 1 0 0 0 0 2 19 1 0 0 0 0 3 20 2 0 0 0 0 4 28 1 0 0 0 0 5 28 1 0 0 0 0 7 30 1 0 0 0 0 9 10 1 0 0 0 0 9 20 1 0 0 0 0 10 21 1 0 0 0 0 11 12 1 0 0 0 0 11 24 2 0 0 0 0 12 25 1 0 0 0 0 13 17 1 0 0 0 0 13 22 1 0 0 0 0 14 18 1 0 0 0 0 14 23 2 0 0 0 0 15 16 1 0 0 0 0 15 26 1 0 0 0 0 16 29 1 0 0 0 0 17 31 1 0 0 0 0 18 30 1 0 0 0 0 19 20 1 0 0 0 0 21 22 1 0 0 0 0 21 27 1 0 0 0 0 22 30 1 6 0 0 0 23 24 1 0 0 0 0 23 29 1 0 0 0 0 24 31 1 0 0 0 0 25 28 1 0 0 0 0 25 29 1 6 0 0 0 26 28 1 0 0 0 0 26 32 2 0 0 0 0 27 33 2 0 0 0 0 27 34 1 0 0 0 0 29 6 1 6 0 0 0 30 31 1 6 0 0 0 31 8 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	466.34
Volume:	523.695
LogP:	6.092
LogD:	4.86
LogS:	-5.466
# Rotatable Bonds:	6
TPSA:	54.37
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.407
Synthetic Accessibility Score:	4.873
Fsp3:	0.742
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:	-5.273
MDCK Permeability:	1.7772546925698407e-05
Pgp-inhibitor:	0.563
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.022
30% Bioavailability (F30%):	0.918

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.069
Plasma Protein Binding (PPB):	93.70238494873047%
Volume Distribution (VD):	0.948
Pgp-substrate:	3.0468039512634277%

ADMET: Metabolism

CYP1A2-inhibitor:	0.015
CYP1A2-substrate:	0.582
CYP2C19-inhibitor:	0.044
CYP2C19-substrate:	0.963
CYP2C9-inhibitor:	0.219
CYP2C9-substrate:	0.962
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.762
CYP3A4-inhibitor:	0.167
CYP3A4-substrate:	0.703

ADMET: Excretion

Clearance (CL):	2.839
Half-life (T1/2):	0.302

ADMET: Toxicity

hERG Blockers:	0.049
Human Hepatotoxicity (H-HT):	0.721
Drug-inuced Liver Injury (DILI):	0.017
AMES Toxicity:	0.007
Rat Oral Acute Toxicity:	0.084
Maximum Recommended Daily Dose:	0.853
Skin Sensitization:	0.625
Carcinogencity:	0.662
Eye Corrosion:	0.004
Eye Irritation:	0.029
Respiratory Toxicity:	0.976

Download Data

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

Natural Product: NPC69279

Natural Product ID:	NPC69279
*Common Name:**	Dehydroeburiconic Acid
IUPAC Name:	6-methyl-5-methylidene-2-[(5R,10S,13R,14R,17R)-4,4,10,13,14-pentamethyl-3-oxo-1,2,5,6,12,15,16,17-octahydrocyclopenta[a]phenanthren-17-yl]heptanoic acid
Synonyms:	Dehydroeburiconic Acid
Standard InCHIKey:	DVXFDXIVWQWLIU-IZARGIBGSA-N
Standard InCHI:	InChI=1S/C31H46O3/c1-19(2)20(3)9-10-21(27(33)34)22-13-17-31(8)24-11-12-25-28(4,5)26(32)15-16-29(25,6)23(24)14-18-30(22,31)7/h11,14,19,21-22,25H,3,9-10,12-13,15-18H2,1-2,4-8H3,(H,33,34)/t21?,22-,25+,29-,30-,31+/m1/s1
SMILES:	CC(C)C(=C)CCC([C@H]1CC[C@@]2(C)C3=CC[C@H]4C(C)(C)C(=O)CC[C@]4(C)C3=CC[C@]12C)C(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL449350
PubChem CID:	12133302
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0003567] Ergostane steroids [CHEMONTID:0001403] Ergosterols and derivatives

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO23577	Wolfiporia cocos	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11975480]
NPO33546	Poria coco	Species		Eukaryota	n.a.	Yunnan, Kunming, China	n.a.	PMID[17488130]
NPO23577	Wolfiporia cocos	Species	Coriolaceae	Eukaryota	epidermis of the sclerotia	n.a.	n.a.	PMID[19746919]
NPO23577	Wolfiporia cocos	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27808511]
NPO23577	Wolfiporia cocos	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8984162]
NPO3354	Fomes officinalis	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23577	Wolfiporia cocos	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3354	Fomes officinalis	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23577	Wolfiporia cocos	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO23577	Wolfiporia cocos	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3354	Fomes officinalis	Species	Coriolaceae	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	10
Others	5

Activity Type	# Activity
Cell Line	8
Individual Protein	1
NON-MOLECULAR	2
Organism	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT80	Cell Line	Raji	Homo sapiens	Activity	=	70.0	%	PMID[549434]
NPT461	Cell Line	PANC-1	Homo sapiens	IC50	=	5500.0	nM	PMID[549435]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	10000.0	nM	PMID[549435]
NPT134	Cell Line	SK-BR-3	Homo sapiens	IC50	=	12200.0	nM	PMID[549435]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	29200.0	nM	PMID[549435]
NPT377	Cell Line	OVCAR-3	Homo sapiens	IC50	=	37700.0	nM	PMID[549435]
NPT90	Cell Line	DU-145	Homo sapiens	IC50	>	100000.0	nM	PMID[549435]
NPT2477	Cell Line	NUGC-3	Homo sapiens	IC50	=	38400.0	nM	PMID[549436]
NPT1044	Individual Protein	DNA topoisomerase II alpha	Homo sapiens	IC50	=	4600.0	nM	PMID[549436]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	Inhibition	=	9.5	%	PMID[549434]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	Inhibition	=	43.9	%	PMID[549434]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	Inhibition	=	79.5	%	PMID[549434]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	Inhibition	=	100.0	%	PMID[549434]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	89700.0	nM	PMID[549435]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	100000.0	nM	PMID[549435]

☑ 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 NPC69279 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	146
0.1-0.2	906
0.2-0.3	5228
0.3-0.4	15850
0.4-0.5	8119
0.5-0.6	7162
0.6-0.7	3892
0.7-0.8	1138
0.8-0.85	190
0.85-0.9	51
0.9-0.95	10
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC83569
0.974	High Similarity	NPC38350
0.974	High Similarity	NPC201912
0.9615	High Similarity	NPC260956
0.9487	High Similarity	NPC147066
0.9481	High Similarity	NPC477371
0.9241	High Similarity	NPC477372
0.9231	High Similarity	NPC196827
0.9231	High Similarity	NPC274996
0.9125	High Similarity	NPC133391
0.9125	High Similarity	NPC320514
0.9091	High Similarity	NPC309399
0.9059	High Similarity	NPC204341
0.9048	High Similarity	NPC84271
0.9048	High Similarity	NPC102414
0.9048	High Similarity	NPC77168
0.9024	High Similarity	NPC29447
0.9012	High Similarity	NPC470015
0.9012	High Similarity	NPC477373
0.9012	High Similarity	NPC168188
0.9012	High Similarity	NPC310470
0.8953	High Similarity	NPC152897
0.8953	High Similarity	NPC66429
0.8889	High Similarity	NPC296367
0.8831	High Similarity	NPC301065
0.881	High Similarity	NPC233836
0.881	High Similarity	NPC187376
0.881	High Similarity	NPC136948
0.881	High Similarity	NPC96496
0.881	High Similarity	NPC159046
0.8795	High Similarity	NPC123319
0.8795	High Similarity	NPC311702
0.8795	High Similarity	NPC94531
0.878	High Similarity	NPC70834
0.8765	High Similarity	NPC142244
0.875	High Similarity	NPC158846
0.875	High Similarity	NPC263347
0.875	High Similarity	NPC215843
0.875	High Similarity	NPC171395
0.869	High Similarity	NPC89077
0.869	High Similarity	NPC155011
0.869	High Similarity	NPC55309
0.869	High Similarity	NPC28252
0.8675	High Similarity	NPC165064
0.8675	High Similarity	NPC87552
0.8675	High Similarity	NPC473246
0.8652	High Similarity	NPC155676
0.8636	High Similarity	NPC469406
0.8608	High Similarity	NPC899
0.8605	High Similarity	NPC262043
0.8605	High Similarity	NPC54689
0.8605	High Similarity	NPC474570
0.8588	High Similarity	NPC474684
0.8588	High Similarity	NPC142361
0.8588	High Similarity	NPC136548
0.8571	High Similarity	NPC474083
0.8571	High Similarity	NPC11711
0.8571	High Similarity	NPC160817
0.8571	High Similarity	NPC473038
0.8554	High Similarity	NPC477852
0.8554	High Similarity	NPC167103
0.8539	High Similarity	NPC45324
0.8539	High Similarity	NPC162001
0.8539	High Similarity	NPC222845
0.8537	High Similarity	NPC267691
0.8537	High Similarity	NPC471898
0.8537	High Similarity	NPC278459
0.8537	High Similarity	NPC263272
0.8537	High Similarity	NPC274050
0.8537	High Similarity	NPC162632
0.8519	High Similarity	NPC192744
0.8519	High Similarity	NPC231431
0.8506	High Similarity	NPC148414
0.8506	High Similarity	NPC111585
0.8506	High Similarity	NPC69622
0.8506	High Similarity	NPC46281
0.8506	High Similarity	NPC175628
0.85	High Similarity	NPC471897
0.85	High Similarity	NPC107039
0.85	High Similarity	NPC165711
0.85	High Similarity	NPC66105
0.85	High Similarity	NPC471899
0.8488	Intermediate Similarity	NPC44181
0.8488	Intermediate Similarity	NPC242864
0.8488	Intermediate Similarity	NPC48866
0.8488	Intermediate Similarity	NPC247406
0.8481	Intermediate Similarity	NPC476844
0.8481	Intermediate Similarity	NPC279666
0.8481	Intermediate Similarity	NPC192540
0.8471	Intermediate Similarity	NPC473168
0.8471	Intermediate Similarity	NPC6247
0.8462	Intermediate Similarity	NPC166745
0.8462	Intermediate Similarity	NPC235464
0.8452	Intermediate Similarity	NPC221758
0.8452	Intermediate Similarity	NPC214043
0.8452	Intermediate Similarity	NPC164577
0.8452	Intermediate Similarity	NPC82902
0.8452	Intermediate Similarity	NPC209882
0.8452	Intermediate Similarity	NPC85774
0.8452	Intermediate Similarity	NPC59453
0.8434	Intermediate Similarity	NPC327969
0.8434	Intermediate Similarity	NPC251779
0.8434	Intermediate Similarity	NPC3511
0.8434	Intermediate Similarity	NPC321289
0.8434	Intermediate Similarity	NPC240302
0.8434	Intermediate Similarity	NPC193347
0.8434	Intermediate Similarity	NPC69101
0.8434	Intermediate Similarity	NPC142253
0.8427	Intermediate Similarity	NPC49670
0.8415	Intermediate Similarity	NPC37038
0.8409	Intermediate Similarity	NPC26888
0.8409	Intermediate Similarity	NPC297265
0.8409	Intermediate Similarity	NPC154101
0.8395	Intermediate Similarity	NPC280654
0.8395	Intermediate Similarity	NPC321514
0.8395	Intermediate Similarity	NPC189485
0.8395	Intermediate Similarity	NPC4827
0.8395	Intermediate Similarity	NPC110094
0.8395	Intermediate Similarity	NPC74410
0.8395	Intermediate Similarity	NPC179028
0.8395	Intermediate Similarity	NPC260385
0.8391	Intermediate Similarity	NPC475921
0.8391	Intermediate Similarity	NPC474704
0.8391	Intermediate Similarity	NPC474889
0.8375	Intermediate Similarity	NPC20466
0.8375	Intermediate Similarity	NPC69143
0.8375	Intermediate Similarity	NPC246445
0.8375	Intermediate Similarity	NPC89294
0.8375	Intermediate Similarity	NPC180886
0.8372	Intermediate Similarity	NPC167877
0.8372	Intermediate Similarity	NPC312215
0.8354	Intermediate Similarity	NPC241854
0.8354	Intermediate Similarity	NPC103958
0.8354	Intermediate Similarity	NPC306928
0.8354	Intermediate Similarity	NPC237591
0.8354	Intermediate Similarity	NPC3753
0.8354	Intermediate Similarity	NPC283908
0.8354	Intermediate Similarity	NPC476046
0.8354	Intermediate Similarity	NPC183503
0.8354	Intermediate Similarity	NPC161923
0.8354	Intermediate Similarity	NPC251970
0.8353	Intermediate Similarity	NPC470223
0.8353	Intermediate Similarity	NPC471224
0.8353	Intermediate Similarity	NPC470048
0.8353	Intermediate Similarity	NPC269638
0.8353	Intermediate Similarity	NPC474537
0.8353	Intermediate Similarity	NPC469948
0.8353	Intermediate Similarity	NPC474218
0.8333	Intermediate Similarity	NPC102197
0.8333	Intermediate Similarity	NPC97913
0.8315	Intermediate Similarity	NPC472942
0.8315	Intermediate Similarity	NPC206810
0.8315	Intermediate Similarity	NPC243866
0.8315	Intermediate Similarity	NPC250575
0.8313	Intermediate Similarity	NPC4166
0.8295	Intermediate Similarity	NPC471896
0.8295	Intermediate Similarity	NPC123854
0.8295	Intermediate Similarity	NPC469400
0.8295	Intermediate Similarity	NPC129913
0.8293	Intermediate Similarity	NPC472490
0.8293	Intermediate Similarity	NPC16394
0.8293	Intermediate Similarity	NPC199595
0.828	Intermediate Similarity	NPC99411
0.8276	Intermediate Similarity	NPC72397
0.8276	Intermediate Similarity	NPC294480
0.8276	Intermediate Similarity	NPC472220
0.8276	Intermediate Similarity	NPC97884
0.8276	Intermediate Similarity	NPC24816
0.8276	Intermediate Similarity	NPC471722
0.8272	Intermediate Similarity	NPC68828
0.8272	Intermediate Similarity	NPC212661
0.8272	Intermediate Similarity	NPC471035
0.8261	Intermediate Similarity	NPC471717
0.8261	Intermediate Similarity	NPC477813
0.8261	Intermediate Similarity	NPC48647
0.8261	Intermediate Similarity	NPC186810
0.8256	Intermediate Similarity	NPC31564
0.8256	Intermediate Similarity	NPC145879
0.8256	Intermediate Similarity	NPC475022
0.8256	Intermediate Similarity	NPC51014
0.8256	Intermediate Similarity	NPC212843
0.8256	Intermediate Similarity	NPC72133
0.8256	Intermediate Similarity	NPC474732
0.8256	Intermediate Similarity	NPC222613
0.8256	Intermediate Similarity	NPC474733
0.8256	Intermediate Similarity	NPC474778
0.8256	Intermediate Similarity	NPC94755
0.8256	Intermediate Similarity	NPC469994
0.8256	Intermediate Similarity	NPC118648
0.8242	Intermediate Similarity	NPC472941
0.8242	Intermediate Similarity	NPC456
0.8235	Intermediate Similarity	NPC320801
0.8235	Intermediate Similarity	NPC237712
0.8235	Intermediate Similarity	NPC476038
0.8235	Intermediate Similarity	NPC472865
0.8235	Intermediate Similarity	NPC194937
0.8235	Intermediate Similarity	NPC96095
0.8235	Intermediate Similarity	NPC144258
0.8228	Intermediate Similarity	NPC330659
0.8228	Intermediate Similarity	NPC244708

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 NPC69279 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	145
0.1-0.2	1242
0.2-0.3	4041
0.3-0.4	2499
0.4-0.5	703
0.5-0.6	228
0.6-0.7	181
0.7-0.8	87
0.8-0.85	19
0.85-0.9	5
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8837	High Similarity	NPD5281	Approved
0.8837	High Similarity	NPD5284	Approved
0.869	High Similarity	NPD5280	Approved
0.869	High Similarity	NPD4694	Approved
0.8471	Intermediate Similarity	NPD5279	Phase 3
0.8452	Intermediate Similarity	NPD4786	Approved
0.8434	Intermediate Similarity	NPD4221	Approved
0.8434	Intermediate Similarity	NPD4223	Phase 3
0.8409	Intermediate Similarity	NPD6050	Approved
0.8354	Intermediate Similarity	NPD5733	Approved
0.8353	Intermediate Similarity	NPD5329	Approved
0.8315	Intermediate Similarity	NPD6399	Phase 3
0.8295	Intermediate Similarity	NPD5207	Approved
0.8295	Intermediate Similarity	NPD5692	Phase 3
0.8256	Intermediate Similarity	NPD5690	Phase 2
0.8256	Intermediate Similarity	NPD6098	Approved
0.8235	Intermediate Similarity	NPD4197	Approved
0.8214	Intermediate Similarity	NPD3667	Approved
0.8202	Intermediate Similarity	NPD5694	Approved
0.8182	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.8132	Intermediate Similarity	NPD5695	Phase 3
0.8125	Intermediate Similarity	NPD4687	Approved
0.8101	Intermediate Similarity	NPD5276	Approved
0.8095	Intermediate Similarity	NPD4692	Approved
0.8095	Intermediate Similarity	NPD4139	Approved
0.809	Intermediate Similarity	NPD4096	Approved
0.8068	Intermediate Similarity	NPD6672	Approved
0.8068	Intermediate Similarity	NPD5737	Approved
0.8046	Intermediate Similarity	NPD4689	Approved
0.8046	Intermediate Similarity	NPD7146	Approved
0.8046	Intermediate Similarity	NPD4138	Approved
0.8046	Intermediate Similarity	NPD5330	Approved
0.8046	Intermediate Similarity	NPD7334	Approved
0.8046	Intermediate Similarity	NPD4688	Approved
0.8046	Intermediate Similarity	NPD4693	Phase 3
0.8046	Intermediate Similarity	NPD6684	Approved
0.8046	Intermediate Similarity	NPD4690	Approved
0.8046	Intermediate Similarity	NPD5205	Approved
0.8046	Intermediate Similarity	NPD7521	Approved
0.8046	Intermediate Similarity	NPD6409	Approved
0.8023	Intermediate Similarity	NPD3133	Approved
0.8023	Intermediate Similarity	NPD3665	Phase 1
0.8023	Intermediate Similarity	NPD3666	Approved
0.7979	Intermediate Similarity	NPD6404	Discontinued
0.7978	Intermediate Similarity	NPD6904	Approved
0.7978	Intermediate Similarity	NPD6673	Approved
0.7978	Intermediate Similarity	NPD5328	Approved
0.7978	Intermediate Similarity	NPD6080	Approved
0.7957	Intermediate Similarity	NPD6084	Phase 2
0.7957	Intermediate Similarity	NPD6083	Phase 2
0.7952	Intermediate Similarity	NPD3617	Approved
0.7912	Intermediate Similarity	NPD5133	Approved
0.7865	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7865	Intermediate Similarity	NPD6903	Approved
0.7865	Intermediate Similarity	NPD4518	Approved
0.7865	Intermediate Similarity	NPD5208	Approved
0.7841	Intermediate Similarity	NPD3618	Phase 1
0.7802	Intermediate Similarity	NPD6079	Approved
0.7778	Intermediate Similarity	NPD4753	Phase 2
0.775	Intermediate Similarity	NPD4747	Approved
0.7742	Intermediate Similarity	NPD5654	Approved
0.7727	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7684	Intermediate Similarity	NPD5696	Approved
0.7683	Intermediate Similarity	NPD4058	Approved
0.7654	Intermediate Similarity	NPD4243	Approved
0.7647	Intermediate Similarity	NPD4195	Approved
0.764	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7625	Intermediate Similarity	NPD4137	Phase 3
0.7614	Intermediate Similarity	NPD3668	Phase 3
0.7609	Intermediate Similarity	NPD5693	Phase 1
0.7609	Intermediate Similarity	NPD7515	Phase 2
0.7579	Intermediate Similarity	NPD5959	Approved
0.7558	Intermediate Similarity	NPD4695	Discontinued
0.7553	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD4691	Approved
0.7527	Intermediate Similarity	NPD4202	Approved
0.75	Intermediate Similarity	NPD3621	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4788	Approved
0.747	Intermediate Similarity	NPD4784	Approved
0.747	Intermediate Similarity	NPD4785	Approved
0.7468	Intermediate Similarity	NPD4224	Phase 2
0.7447	Intermediate Similarity	NPD7748	Approved
0.7447	Intermediate Similarity	NPD6001	Approved
0.7444	Intermediate Similarity	NPD4623	Approved
0.7444	Intermediate Similarity	NPD4519	Discontinued
0.7439	Intermediate Similarity	NPD6081	Approved
0.7419	Intermediate Similarity	NPD6411	Approved
0.74	Intermediate Similarity	NPD5739	Approved
0.74	Intermediate Similarity	NPD7128	Approved
0.74	Intermediate Similarity	NPD6675	Approved
0.74	Intermediate Similarity	NPD6402	Approved
0.7381	Intermediate Similarity	NPD7339	Approved
0.7381	Intermediate Similarity	NPD6942	Approved
0.7368	Intermediate Similarity	NPD4629	Approved
0.7368	Intermediate Similarity	NPD5210	Approved
0.7326	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD7614	Phase 1
0.7292	Intermediate Similarity	NPD5222	Approved
0.7292	Intermediate Similarity	NPD5221	Approved
0.7292	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD4697	Phase 3
0.7262	Intermediate Similarity	NPD6926	Approved
0.7262	Intermediate Similarity	NPD6924	Approved
0.7255	Intermediate Similarity	NPD7320	Approved
0.7255	Intermediate Similarity	NPD6899	Approved
0.7255	Intermediate Similarity	NPD6881	Approved
0.7234	Intermediate Similarity	NPD8035	Phase 2
0.7234	Intermediate Similarity	NPD8034	Phase 2
0.7216	Intermediate Similarity	NPD4755	Approved
0.7216	Intermediate Similarity	NPD5173	Approved
0.7216	Intermediate Similarity	NPD7902	Approved
0.7204	Intermediate Similarity	NPD6101	Approved
0.7204	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD6372	Approved
0.7184	Intermediate Similarity	NPD6373	Approved
0.7176	Intermediate Similarity	NPD4190	Phase 3
0.7176	Intermediate Similarity	NPD5275	Approved
0.7174	Intermediate Similarity	NPD3573	Approved
0.7157	Intermediate Similarity	NPD5701	Approved
0.7157	Intermediate Similarity	NPD5697	Approved
0.7115	Intermediate Similarity	NPD7290	Approved
0.7115	Intermediate Similarity	NPD6883	Approved
0.7115	Intermediate Similarity	NPD7102	Approved
0.7111	Intermediate Similarity	NPD3527	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD6933	Approved
0.7093	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD6011	Approved
0.7073	Intermediate Similarity	NPD5361	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD5360	Phase 3
0.7071	Intermediate Similarity	NPD4696	Approved
0.7071	Intermediate Similarity	NPD4700	Approved
0.7071	Intermediate Similarity	NPD5286	Approved
0.7071	Intermediate Similarity	NPD5285	Approved
0.7059	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD6869	Approved
0.7048	Intermediate Similarity	NPD6650	Approved
0.7048	Intermediate Similarity	NPD6847	Approved
0.7048	Intermediate Similarity	NPD6649	Approved
0.7048	Intermediate Similarity	NPD8130	Phase 1
0.7048	Intermediate Similarity	NPD6617	Approved
0.703	Intermediate Similarity	NPD6052	Approved
0.7019	Intermediate Similarity	NPD6012	Approved
0.7019	Intermediate Similarity	NPD6013	Approved
0.7019	Intermediate Similarity	NPD6014	Approved
0.7	Intermediate Similarity	NPD5223	Approved
0.6988	Remote Similarity	NPD6922	Approved
0.6988	Remote Similarity	NPD6923	Approved
0.6981	Remote Similarity	NPD8297	Approved
0.6981	Remote Similarity	NPD6882	Approved
0.697	Remote Similarity	NPD7638	Approved
0.6966	Remote Similarity	NPD7525	Registered
0.6931	Remote Similarity	NPD5226	Approved
0.6931	Remote Similarity	NPD5091	Approved
0.6931	Remote Similarity	NPD4633	Approved
0.6931	Remote Similarity	NPD5211	Phase 2
0.6931	Remote Similarity	NPD5224	Approved
0.6931	Remote Similarity	NPD5225	Approved
0.6914	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6907	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6907	Remote Similarity	NPD7900	Approved
0.6905	Remote Similarity	NPD4789	Approved
0.6905	Remote Similarity	NPD7144	Approved
0.6905	Remote Similarity	NPD7143	Approved
0.69	Remote Similarity	NPD7640	Approved
0.69	Remote Similarity	NPD7639	Approved
0.6897	Remote Similarity	NPD6117	Approved
0.6875	Remote Similarity	NPD7637	Suspended
0.6863	Remote Similarity	NPD5175	Approved
0.6863	Remote Similarity	NPD5174	Approved
0.6863	Remote Similarity	NPD4754	Approved
0.6854	Remote Similarity	NPD6929	Approved
0.6842	Remote Similarity	NPD6051	Approved
0.6829	Remote Similarity	NPD7331	Phase 2
0.6827	Remote Similarity	NPD6412	Phase 2
0.6827	Remote Similarity	NPD6614	Approved
0.6824	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD7152	Approved
0.6824	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD7151	Approved
0.6824	Remote Similarity	NPD7150	Approved
0.6818	Remote Similarity	NPD6116	Phase 1
0.6813	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6804	Remote Similarity	NPD5778	Approved
0.6804	Remote Similarity	NPD5779	Approved
0.6796	Remote Similarity	NPD5141	Approved
0.6789	Remote Similarity	NPD6868	Approved
0.6782	Remote Similarity	NPD3702	Approved
0.6782	Remote Similarity	NPD8039	Approved
0.6778	Remote Similarity	NPD6931	Approved
0.6778	Remote Similarity	NPD5368	Approved
0.6778	Remote Similarity	NPD6930	Phase 2
0.6768	Remote Similarity	NPD7732	Phase 3
0.6759	Remote Similarity	NPD4632	Approved
0.6742	Remote Similarity	NPD6115	Approved
0.6742	Remote Similarity	NPD6697	Approved
0.6742	Remote Similarity	NPD6118	Approved
0.6742	Remote Similarity	NPD6114	Approved
0.6739	Remote Similarity	NPD5362	Discontinued
0.6731	Remote Similarity	NPD6008	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