NPASS Compound

Structure

NPC471570 OpenBabel07101719152D 43 47 0 0 1 0 0 0 0 0999 V2000 -2.8347 -11.9535 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8863 1.3790 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0296 1.8949 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3987 0.0420 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2415 -11.0400 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6537 -10.2310 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0604 -9.3174 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4726 -8.5084 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8794 -7.5949 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2916 -6.7859 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6983 -5.8723 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1106 -5.0633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5173 -4.1498 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9295 -3.3407 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3362 -2.4272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7485 -1.6182 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8712 -0.0230 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0052 -1.5230 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0052 0.4770 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1391 -1.0230 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6457 -0.6811 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0346 0.9716 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0564 1.1795 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2110 -0.1653 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5674 0.1044 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9687 1.1225 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8712 -1.0230 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1552 -0.7046 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.9741 1.0179 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6931 -0.4173 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3918 1.7224 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0112 0.8951 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4010 -0.0258 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.1391 -0.0230 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -3.5564 0.3134 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0149 0.8089 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.7372 -1.5230 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6746 -1.4172 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1960 2.5314 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3864 1.8270 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1497 -0.6001 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 -4.2256 -0.4297 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 5 1 0 0 0 0 2 32 1 0 0 0 0 3 32 1 0 0 0 0 5 6 1 0 0 0 0 6 7 1 0 0 0 0 7 8 1 0 0 0 0 8 9 1 0 0 0 0 9 10 1 0 0 0 0 10 11 1 0 0 0 0 11 12 1 0 0 0 0 12 13 1 0 0 0 0 13 14 1 0 0 0 0 14 15 1 0 0 0 0 15 16 1 0 0 0 0 17 19 2 0 0 0 0 17 27 1 0 0 0 0 18 20 2 0 0 0 0 18 27 1 0 0 0 0 19 34 1 0 0 0 0 20 34 1 0 0 0 0 21 24 1 0 0 0 0 21 33 1 0 0 0 0 22 23 1 0 0 0 0 22 34 1 0 0 0 0 24 36 1 0 0 0 0 25 28 1 0 0 0 0 25 29 1 0 0 0 0 26 29 1 0 0 0 0 26 35 1 0 0 0 0 27 37 2 0 0 0 0 28 16 1 1 0 0 0 28 41 1 0 0 0 0 29 40 1 6 0 0 0 30 33 1 0 0 0 0 30 38 2 0 0 0 0 30 42 1 0 0 0 0 31 39 2 0 0 0 0 31 40 1 0 0 0 0 32 33 1 0 0 0 0 32 36 1 0 0 0 0 33 4 1 6 0 0 0 34 43 1 0 0 0 0 35 23 1 1 0 0 0 35 41 1 0 0 0 0 35 43 1 0 0 0 0 36 31 1 6 0 0 0 36 42 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	598.39
Volume:	636.779
LogP:	7.505
LogD:	4.651
LogS:	-6.853
# Rotatable Bonds:	15
TPSA:	88.13
# H-Bond Aceptor:	7
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.149
Synthetic Accessibility Score:	6.134
Fsp3:	0.806
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.916
MDCK Permeability:	2.9817032555001788e-05
Pgp-inhibitor:	0.965
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.878
30% Bioavailability (F30%):	0.133

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.26
Plasma Protein Binding (PPB):	99.7995376586914%
Volume Distribution (VD):	2.278
Pgp-substrate:	1.0167262554168701%

ADMET: Metabolism

CYP1A2-inhibitor:	0.019
CYP1A2-substrate:	0.234
CYP2C19-inhibitor:	0.678
CYP2C19-substrate:	0.829
CYP2C9-inhibitor:	0.498
CYP2C9-substrate:	0.077
CYP2D6-inhibitor:	0.891
CYP2D6-substrate:	0.017
CYP3A4-inhibitor:	0.953
CYP3A4-substrate:	0.772

ADMET: Excretion

Clearance (CL):	9.119
Half-life (T1/2):	0.073

ADMET: Toxicity

hERG Blockers:	0.73
Human Hepatotoxicity (H-HT):	0.782
Drug-inuced Liver Injury (DILI):	0.344
AMES Toxicity:	0.749
Rat Oral Acute Toxicity:	0.056
Maximum Recommended Daily Dose:	0.991
Skin Sensitization:	0.97
Carcinogencity:	0.875
Eye Corrosion:	0.014
Eye Irritation:	0.044
Respiratory Toxicity:	0.961

Download Data

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

Natural Product: NPC471570

Natural Product ID:	NPC471570
*Common Name:**	[(2R,4R,6R)-11-Oxo-4-Tridecyl-5,7-Dioxadispiro[5.1.5^{8}.2^{6}]Pentadeca-9,12-Dien-2-Yl] (1R,4S)-1,7,7-Trimethyl-2-Oxo-3-Oxabicyclo[2.2.1]Heptane-4-Carboxylate
IUPAC Name:	[(2R,4R,6R)-11-oxo-4-tridecyl-5,7-dioxadispiro[5.1.5^{8}.2^{6}]pentadeca-9,12-dien-2-yl] (1R,4S)-1,7,7-trimethyl-2-oxo-3-oxabicyclo[2.2.1]heptane-4-carboxylate
Synonyms:
Standard InCHIKey:	DFSURPSOPLVGMH-WTWDCUJCSA-N
Standard InCHI:	InChI=1S/C36H54O7/c1-5-6-7-8-9-10-11-12-13-14-15-16-28-25-29(26-35(41-28)23-22-34(43-35)19-17-27(37)18-20-34)40-31(39)36-24-21-33(4,30(38)42-36)32(36,2)3/h17-20,28-29H,5-16,21-26H2,1-4H3/t28-,29-,33+,35-,36-/m1/s1
SMILES:	CCCCCCCCCCCCCC1CC(CC2(O1)CCC3(O2)C=CC(=O)C=C3)OC(=O)C45CCC(C4(C)C)(C(=O)O5)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL258417
PubChem CID:	24853677
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000050] Lactones [CHEMONTID:0001244] Delta valerolactones

*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
NPO17710	Amomum aculeatum	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18260638]
NPO17710	Amomum aculeatum	Species	Zingiberaceae	Eukaryota	n.a.	leaf	n.a.	PMID[18260638]
NPO17710	Amomum aculeatum	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17710	Amomum aculeatum	Species	Zingiberaceae	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
ED50	3

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1034	Cell Line	Lu1	Homo sapiens	ED50	=	1.0	uM	PMID[523031]
NPT858	Cell Line	LNCaP	Homo sapiens	ED50	=	3.0	uM	PMID[523031]
NPT83	Cell Line	MCF7	Homo sapiens	ED50	=	3.2	uM	PMID[523031]

☑ 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 NPC471570 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	281
0.1-0.2	1804
0.2-0.3	6424
0.3-0.4	11884
0.4-0.5	10949
0.5-0.6	7453
0.6-0.7	3639
0.7-0.8	257
0.8-0.85	5
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8362	Intermediate Similarity	NPC147635
0.8362	Intermediate Similarity	NPC163693
0.8304	Intermediate Similarity	NPC474750
0.8091	Intermediate Similarity	NPC169843
0.8049	Intermediate Similarity	NPC469351
0.8036	Intermediate Similarity	NPC10150
0.7965	Intermediate Similarity	NPC187876
0.7951	Intermediate Similarity	NPC11732
0.7946	Intermediate Similarity	NPC470192
0.7909	Intermediate Similarity	NPC471757
0.7909	Intermediate Similarity	NPC78127
0.7903	Intermediate Similarity	NPC213634
0.7886	Intermediate Similarity	NPC172823
0.7857	Intermediate Similarity	NPC291643
0.7778	Intermediate Similarity	NPC224623
0.7769	Intermediate Similarity	NPC192309
0.7768	Intermediate Similarity	NPC164835
0.7768	Intermediate Similarity	NPC228669
0.7759	Intermediate Similarity	NPC473522
0.7759	Intermediate Similarity	NPC477093
0.7759	Intermediate Similarity	NPC475277
0.7748	Intermediate Similarity	NPC49393
0.7748	Intermediate Similarity	NPC105725
0.7742	Intermediate Similarity	NPC473888
0.7739	Intermediate Similarity	NPC41551
0.7705	Intermediate Similarity	NPC1538
0.7705	Intermediate Similarity	NPC42747
0.7698	Intermediate Similarity	NPC471855
0.768	Intermediate Similarity	NPC13071
0.7679	Intermediate Similarity	NPC472747
0.7679	Intermediate Similarity	NPC472750
0.7672	Intermediate Similarity	NPC475495
0.7642	Intermediate Similarity	NPC144625
0.7636	Intermediate Similarity	NPC470188
0.7627	Intermediate Similarity	NPC471398
0.7611	Intermediate Similarity	NPC472748
0.7586	Intermediate Similarity	NPC50223
0.7578	Intermediate Similarity	NPC471234
0.757	Intermediate Similarity	NPC221282
0.7563	Intermediate Similarity	NPC277583
0.7561	Intermediate Similarity	NPC186339
0.7544	Intermediate Similarity	NPC472751
0.7544	Intermediate Similarity	NPC472749
0.7544	Intermediate Similarity	NPC469401
0.7541	Intermediate Similarity	NPC204731
0.7541	Intermediate Similarity	NPC472001
0.754	Intermediate Similarity	NPC471407
0.7521	Intermediate Similarity	NPC9674
0.7521	Intermediate Similarity	NPC19028
0.752	Intermediate Similarity	NPC287423
0.752	Intermediate Similarity	NPC152091
0.75	Intermediate Similarity	NPC475305
0.7477	Intermediate Similarity	NPC471569
0.7459	Intermediate Similarity	NPC474585
0.744	Intermediate Similarity	NPC93368
0.7438	Intermediate Similarity	NPC473720
0.7438	Intermediate Similarity	NPC475401
0.7438	Intermediate Similarity	NPC13710
0.7436	Intermediate Similarity	NPC206595
0.7417	Intermediate Similarity	NPC106228
0.7417	Intermediate Similarity	NPC138372
0.7417	Intermediate Similarity	NPC148458
0.7414	Intermediate Similarity	NPC470269
0.7414	Intermediate Similarity	NPC475960
0.7407	Intermediate Similarity	NPC290651
0.7398	Intermediate Similarity	NPC42675
0.7398	Intermediate Similarity	NPC470829
0.7398	Intermediate Similarity	NPC471999
0.7398	Intermediate Similarity	NPC473228
0.7398	Intermediate Similarity	NPC472000
0.7387	Intermediate Similarity	NPC266842
0.7377	Intermediate Similarity	NPC477092
0.7377	Intermediate Similarity	NPC475834
0.7377	Intermediate Similarity	NPC474179
0.7368	Intermediate Similarity	NPC123505
0.736	Intermediate Similarity	NPC190846
0.736	Intermediate Similarity	NPC277191
0.7355	Intermediate Similarity	NPC239273
0.7355	Intermediate Similarity	NPC23046
0.735	Intermediate Similarity	NPC471934
0.735	Intermediate Similarity	NPC77089
0.7344	Intermediate Similarity	NPC471170
0.7333	Intermediate Similarity	NPC474181
0.7333	Intermediate Similarity	NPC473353
0.7328	Intermediate Similarity	NPC471601
0.7323	Intermediate Similarity	NPC473620
0.7317	Intermediate Similarity	NPC4548
0.7311	Intermediate Similarity	NPC475524
0.7311	Intermediate Similarity	NPC98038
0.7311	Intermediate Similarity	NPC221144
0.7311	Intermediate Similarity	NPC313921
0.7311	Intermediate Similarity	NPC100267
0.7311	Intermediate Similarity	NPC471933
0.7304	Intermediate Similarity	NPC307846
0.7304	Intermediate Similarity	NPC305157
0.7297	Intermediate Similarity	NPC113433
0.7295	Intermediate Similarity	NPC474286
0.7295	Intermediate Similarity	NPC475913
0.7295	Intermediate Similarity	NPC475372
0.7295	Intermediate Similarity	NPC475130
0.7295	Intermediate Similarity	NPC153440
0.7295	Intermediate Similarity	NPC470420
0.7288	Intermediate Similarity	NPC5103
0.7287	Intermediate Similarity	NPC472769
0.7282	Intermediate Similarity	NPC471552
0.7282	Intermediate Similarity	NPC473339
0.728	Intermediate Similarity	NPC471392
0.728	Intermediate Similarity	NPC238005
0.728	Intermediate Similarity	NPC141196
0.728	Intermediate Similarity	NPC1980
0.7273	Intermediate Similarity	NPC243981
0.7273	Intermediate Similarity	NPC190286
0.7273	Intermediate Similarity	NPC281775
0.7266	Intermediate Similarity	NPC175186
0.7266	Intermediate Similarity	NPC472770
0.7265	Intermediate Similarity	NPC61411
0.7258	Intermediate Similarity	NPC310511
0.7257	Intermediate Similarity	NPC469402
0.725	Intermediate Similarity	NPC9848
0.725	Intermediate Similarity	NPC469496
0.725	Intermediate Similarity	NPC469454
0.725	Intermediate Similarity	NPC469463
0.725	Intermediate Similarity	NPC101400
0.725	Intermediate Similarity	NPC101965
0.725	Intermediate Similarity	NPC209058
0.725	Intermediate Similarity	NPC312017
0.7244	Intermediate Similarity	NPC473253
0.7244	Intermediate Similarity	NPC42399
0.7244	Intermediate Similarity	NPC470882
0.7244	Intermediate Similarity	NPC473265
0.7236	Intermediate Similarity	NPC475520
0.7236	Intermediate Similarity	NPC312536
0.7236	Intermediate Similarity	NPC319570
0.7236	Intermediate Similarity	NPC5292
0.7231	Intermediate Similarity	NPC88668
0.7231	Intermediate Similarity	NPC168879
0.7227	Intermediate Similarity	NPC304180
0.7227	Intermediate Similarity	NPC179798
0.7227	Intermediate Similarity	NPC118860
0.7227	Intermediate Similarity	NPC214797
0.7227	Intermediate Similarity	NPC231589
0.7222	Intermediate Similarity	NPC241456
0.7222	Intermediate Similarity	NPC32868
0.7209	Intermediate Similarity	NPC475389
0.7209	Intermediate Similarity	NPC473838
0.7203	Intermediate Similarity	NPC304495
0.7203	Intermediate Similarity	NPC474242
0.72	Intermediate Similarity	NPC313528
0.7197	Intermediate Similarity	NPC245017
0.7193	Intermediate Similarity	NPC472753
0.7193	Intermediate Similarity	NPC471767
0.7193	Intermediate Similarity	NPC473384
0.719	Intermediate Similarity	NPC178289
0.719	Intermediate Similarity	NPC123117
0.7188	Intermediate Similarity	NPC311534
0.7185	Intermediate Similarity	NPC470426
0.7182	Intermediate Similarity	NPC477361
0.7182	Intermediate Similarity	NPC202824
0.7179	Intermediate Similarity	NPC26617
0.7177	Intermediate Similarity	NPC107338
0.7177	Intermediate Similarity	NPC79579
0.7177	Intermediate Similarity	NPC151616
0.7177	Intermediate Similarity	NPC48692
0.7177	Intermediate Similarity	NPC109973
0.7177	Intermediate Similarity	NPC109607
0.7168	Intermediate Similarity	NPC54843
0.7167	Intermediate Similarity	NPC147180
0.7167	Intermediate Similarity	NPC170487
0.7165	Intermediate Similarity	NPC198714
0.7155	Intermediate Similarity	NPC119493
0.7155	Intermediate Similarity	NPC474917
0.7155	Intermediate Similarity	NPC472756
0.7154	Intermediate Similarity	NPC311554
0.7154	Intermediate Similarity	NPC180902
0.7154	Intermediate Similarity	NPC257457
0.7154	Intermediate Similarity	NPC102316
0.7154	Intermediate Similarity	NPC475139
0.7153	Intermediate Similarity	NPC194854
0.7153	Intermediate Similarity	NPC48813
0.7143	Intermediate Similarity	NPC477354
0.7143	Intermediate Similarity	NPC472768
0.7143	Intermediate Similarity	NPC27363
0.7143	Intermediate Similarity	NPC204812
0.7143	Intermediate Similarity	NPC471884
0.7132	Intermediate Similarity	NPC471171
0.7132	Intermediate Similarity	NPC470880
0.7132	Intermediate Similarity	NPC104382
0.7132	Intermediate Similarity	NPC470851
0.7131	Intermediate Similarity	NPC268213
0.713	Intermediate Similarity	NPC250594
0.713	Intermediate Similarity	NPC118405
0.713	Intermediate Similarity	NPC271266
0.713	Intermediate Similarity	NPC308351
0.713	Intermediate Similarity	NPC472754
0.7121	Intermediate Similarity	NPC171619
0.712	Intermediate Similarity	NPC473250
0.712	Intermediate Similarity	NPC46570
0.7111	Intermediate Similarity	NPC25887
0.7109	Intermediate Similarity	NPC240070
0.7109	Intermediate Similarity	NPC329784

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 NPC471570 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	244
0.1-0.2	2249
0.2-0.3	4091
0.3-0.4	1731
0.4-0.5	495
0.5-0.6	208
0.6-0.7	120
0.7-0.8	12
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
0.752	Intermediate Similarity	NPD7078	Approved
0.75	Intermediate Similarity	NPD7492	Approved
0.746	Intermediate Similarity	NPD7736	Approved
0.7459	Intermediate Similarity	NPD6054	Approved
0.744	Intermediate Similarity	NPD6616	Approved
0.7339	Intermediate Similarity	NPD6370	Approved
0.7258	Intermediate Similarity	NPD6016	Approved
0.7258	Intermediate Similarity	NPD6015	Approved
0.7244	Intermediate Similarity	NPD8293	Discontinued
0.7213	Intermediate Similarity	NPD6009	Approved
0.72	Intermediate Similarity	NPD5988	Approved
0.7179	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7177	Intermediate Similarity	NPD6059	Approved
0.7167	Intermediate Similarity	NPD6882	Approved
0.7167	Intermediate Similarity	NPD8297	Approved
0.7031	Intermediate Similarity	NPD7507	Approved
0.6975	Remote Similarity	NPD6881	Approved
0.6975	Remote Similarity	NPD6899	Approved
0.6949	Remote Similarity	NPD6008	Approved
0.6942	Remote Similarity	NPD8130	Phase 1
0.6942	Remote Similarity	NPD6650	Approved
0.6942	Remote Similarity	NPD6649	Approved
0.6905	Remote Similarity	NPD6319	Approved
0.6891	Remote Similarity	NPD5697	Approved
0.687	Remote Similarity	NPD7319	Approved
0.686	Remote Similarity	NPD6883	Approved
0.686	Remote Similarity	NPD7290	Approved
0.686	Remote Similarity	NPD7102	Approved
0.6833	Remote Similarity	NPD6686	Approved
0.6833	Remote Similarity	NPD7320	Approved
0.6829	Remote Similarity	NPD4632	Approved
0.6807	Remote Similarity	NPD5739	Approved
0.6807	Remote Similarity	NPD6402	Approved
0.6807	Remote Similarity	NPD6675	Approved
0.6807	Remote Similarity	NPD7128	Approved
0.6803	Remote Similarity	NPD6617	Approved
0.6803	Remote Similarity	NPD6869	Approved
0.6803	Remote Similarity	NPD6847	Approved
0.6803	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD5693	Phase 1
0.6777	Remote Similarity	NPD6013	Approved
0.6777	Remote Similarity	NPD6372	Approved
0.6777	Remote Similarity	NPD6373	Approved
0.6777	Remote Similarity	NPD6014	Approved
0.6777	Remote Similarity	NPD6012	Approved
0.675	Remote Similarity	NPD6412	Phase 2
0.6748	Remote Similarity	NPD6053	Discontinued
0.6744	Remote Similarity	NPD7604	Phase 2
0.6724	Remote Similarity	NPD5696	Approved
0.6721	Remote Similarity	NPD6371	Approved
0.6719	Remote Similarity	NPD5983	Phase 2
0.6697	Remote Similarity	NPD1694	Approved
0.6694	Remote Similarity	NPD6011	Approved
0.6667	Remote Similarity	NPD6033	Approved
0.6642	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6642	Remote Similarity	NPD7260	Phase 2
0.6641	Remote Similarity	NPD6336	Discontinued
0.6638	Remote Similarity	NPD6084	Phase 2
0.6638	Remote Similarity	NPD6083	Phase 2
0.6612	Remote Similarity	NPD5701	Approved
0.6609	Remote Similarity	NPD5695	Phase 3
0.6607	Remote Similarity	NPD6673	Approved
0.6607	Remote Similarity	NPD1695	Approved
0.6607	Remote Similarity	NPD6080	Approved
0.6607	Remote Similarity	NPD6904	Approved
0.6593	Remote Similarity	NPD6845	Suspended
0.6589	Remote Similarity	NPD7503	Approved
0.6581	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6567	Remote Similarity	NPD5956	Approved
0.6549	Remote Similarity	NPD5785	Approved
0.6522	Remote Similarity	NPD5282	Discontinued
0.6518	Remote Similarity	NPD6672	Approved
0.6518	Remote Similarity	NPD5737	Approved
0.6512	Remote Similarity	NPD8377	Approved
0.6512	Remote Similarity	NPD8294	Approved
0.6491	Remote Similarity	NPD6050	Approved
0.6491	Remote Similarity	NPD5694	Approved
0.6489	Remote Similarity	NPD8328	Phase 3
0.6484	Remote Similarity	NPD7327	Approved
0.6484	Remote Similarity	NPD7328	Approved
0.6466	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6466	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6462	Remote Similarity	NPD8033	Approved
0.6462	Remote Similarity	NPD8380	Approved
0.6462	Remote Similarity	NPD8515	Approved
0.6462	Remote Similarity	NPD8296	Approved
0.6462	Remote Similarity	NPD8335	Approved
0.6462	Remote Similarity	NPD8513	Phase 3
0.6462	Remote Similarity	NPD8517	Approved
0.6462	Remote Similarity	NPD8378	Approved
0.6462	Remote Similarity	NPD8516	Approved
0.6462	Remote Similarity	NPD8379	Approved
0.6446	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.6446	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.6434	Remote Similarity	NPD7100	Approved
0.6434	Remote Similarity	NPD7101	Approved
0.6434	Remote Similarity	NPD7516	Approved
0.6423	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6418	Remote Similarity	NPD8337	Approved
0.6418	Remote Similarity	NPD8336	Approved
0.6417	Remote Similarity	NPD5211	Phase 2
0.6406	Remote Similarity	NPD7115	Discovery
0.6404	Remote Similarity	NPD5207	Approved
0.6404	Remote Similarity	NPD5692	Phase 3
0.64	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6396	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6387	Remote Similarity	NPD5285	Approved
0.6387	Remote Similarity	NPD5286	Approved
0.6387	Remote Similarity	NPD4696	Approved
0.6372	Remote Similarity	NPD6903	Approved
0.6357	Remote Similarity	NPD6335	Approved
0.635	Remote Similarity	NPD8338	Approved
0.6341	Remote Similarity	NPD6614	Approved
0.6339	Remote Similarity	NPD7521	Approved
0.6339	Remote Similarity	NPD5330	Approved
0.6339	Remote Similarity	NPD6098	Approved
0.6339	Remote Similarity	NPD6684	Approved
0.6339	Remote Similarity	NPD7334	Approved
0.6339	Remote Similarity	NPD6409	Approved
0.6339	Remote Similarity	NPD7146	Approved
0.6336	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6328	Remote Similarity	NPD6274	Approved
0.6325	Remote Similarity	NPD4629	Approved
0.6325	Remote Similarity	NPD5210	Approved
0.632	Remote Similarity	NPD4634	Approved
0.6311	Remote Similarity	NPD5141	Approved
0.6281	Remote Similarity	NPD5225	Approved
0.6281	Remote Similarity	NPD5226	Approved
0.6281	Remote Similarity	NPD4633	Approved
0.6281	Remote Similarity	NPD5224	Approved
0.6279	Remote Similarity	NPD6317	Approved
0.6273	Remote Similarity	NPD6435	Approved
0.6261	Remote Similarity	NPD46	Approved
0.6261	Remote Similarity	NPD6698	Approved
0.6231	Remote Similarity	NPD6313	Approved
0.6231	Remote Similarity	NPD6314	Approved
0.623	Remote Similarity	NPD5175	Approved
0.623	Remote Similarity	NPD5174	Approved
0.6228	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6222	Remote Similarity	NPD8074	Phase 3
0.6218	Remote Similarity	NPD4755	Approved
0.621	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6198	Remote Similarity	NPD5223	Approved
0.6186	Remote Similarity	NPD5654	Approved
0.6172	Remote Similarity	NPD8133	Approved
0.6167	Remote Similarity	NPD7638	Approved
0.6154	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.614	Remote Similarity	NPD4250	Approved
0.614	Remote Similarity	NPD4251	Approved
0.6126	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6119	Remote Similarity	NPD7642	Approved
0.6116	Remote Similarity	NPD4700	Approved
0.6116	Remote Similarity	NPD7639	Approved
0.6116	Remote Similarity	NPD7640	Approved
0.6106	Remote Similarity	NPD5363	Approved
0.6102	Remote Similarity	NPD6001	Approved
0.6091	Remote Similarity	NPD5368	Approved
0.609	Remote Similarity	NPD6908	Approved
0.609	Remote Similarity	NPD6909	Approved
0.6083	Remote Similarity	NPD5959	Approved
0.6068	Remote Similarity	NPD5284	Approved
0.6068	Remote Similarity	NPD5281	Approved
0.6066	Remote Similarity	NPD1700	Approved
0.6063	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6053	Remote Similarity	NPD5786	Approved
0.6053	Remote Similarity	NPD4249	Approved
0.6049	Remote Similarity	NPD7799	Discontinued
0.6034	Remote Similarity	NPD6051	Approved
0.6034	Remote Similarity	NPD4753	Phase 2
0.6032	Remote Similarity	NPD4729	Approved
0.6032	Remote Similarity	NPD4730	Approved
0.6017	Remote Similarity	NPD6399	Phase 3
0.6	Remote Similarity	NPD6067	Discontinued
0.6	Remote Similarity	NPD7829	Approved
0.6	Remote Similarity	NPD7830	Approved
0.5984	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.5984	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5983	Remote Similarity	NPD7838	Discovery
0.5968	Remote Similarity	NPD6052	Approved
0.5965	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.5954	Remote Similarity	NPD6868	Approved
0.5948	Remote Similarity	NPD5208	Approved
0.5938	Remote Similarity	NPD5249	Phase 3
0.5938	Remote Similarity	NPD5247	Approved
0.5938	Remote Similarity	NPD5251	Approved
0.5938	Remote Similarity	NPD5248	Approved
0.5938	Remote Similarity	NPD5250	Approved
0.5932	Remote Similarity	NPD7983	Approved
0.5929	Remote Similarity	NPD5362	Discontinued
0.5926	Remote Similarity	NPD8039	Approved
0.5926	Remote Similarity	NPD8080	Discontinued
0.592	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.5913	Remote Similarity	NPD5690	Phase 2
0.5912	Remote Similarity	NPD8451	Approved
0.5909	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5906	Remote Similarity	NPD5128	Approved
0.5902	Remote Similarity	NPD4225	Approved
0.5893	Remote Similarity	NPD5369	Approved
0.5891	Remote Similarity	NPD5217	Approved
0.5891	Remote Similarity	NPD5215	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