NPASS Compound

Structure

NPC272242 OpenBabel07101718192D 48 53 0 0 1 0 0 0 0 0999 V2000 1.5506 4.5858 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2873 3.4483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3628 -1.9415 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4294 -2.2448 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8500 -1.4722 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8500 -0.4907 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3008 0.8966 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5135 0.9155 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8801 3.0256 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8500 -1.4722 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.9815 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2793 2.1290 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5500 0.4907 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.9630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9367 1.2367 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2090 -0.6021 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2473 3.6524 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9040 2.9230 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8500 1.4722 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8500 1.4722 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.2329 -0.7047 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7000 -0.9815 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.6334 0.3033 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.8967 1.4408 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7000 1.9630 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.8337 -1.6013 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.8576 -1.7039 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.2807 -0.9099 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8500 0.4907 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.6799 -0.0133 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.1269 0.6782 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6334 -1.2848 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8500 0.4907 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 -1.7000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5500 1.4722 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 7.7859 -1.3961 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7000 1.9630 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2000 2.3742 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.4106 -2.3954 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4584 -2.6005 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3046 -1.0125 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7277 -0.2184 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5535 0.7114 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6560 0.0893 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1030 0.7808 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2103 -0.4907 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 18 2 0 0 0 0 2 18 1 0 0 0 0 3 33 1 0 0 0 0 4 33 1 0 0 0 0 5 34 1 0 0 0 0 8 45 1 0 0 0 0 9 12 1 0 0 0 0 9 19 1 0 0 0 0 10 11 1 0 0 0 0 10 23 1 0 0 0 0 11 35 1 0 0 0 0 12 37 1 0 0 0 0 13 14 1 0 0 0 0 13 34 1 0 0 0 0 14 37 1 0 0 0 0 15 20 1 0 0 0 0 15 21 1 0 0 0 0 16 24 1 0 0 0 0 16 25 1 0 0 0 0 17 38 1 0 0 0 0 19 18 1 6 0 0 0 19 26 1 0 0 0 0 20 26 1 0 0 0 0 20 34 1 6 0 0 0 21 30 1 0 0 0 0 21 39 1 6 0 0 0 22 17 1 6 0 0 0 22 27 1 0 0 0 0 22 46 1 0 0 0 0 23 33 1 0 0 0 0 23 36 1 1 0 0 0 24 36 1 6 0 0 0 24 48 1 0 0 0 0 25 40 2 0 0 0 0 25 45 1 0 0 0 0 26 37 1 1 0 0 0 27 28 1 0 0 0 0 27 41 1 1 0 0 0 28 29 1 0 0 0 0 28 42 1 6 0 0 0 29 31 1 0 0 0 0 29 43 1 1 0 0 0 30 35 1 1 0 0 0 30 36 1 0 0 0 0 31 46 1 0 0 0 0 31 47 1 6 0 0 0 32 44 2 0 0 0 0 32 47 1 0 0 0 0 33 48 1 0 0 0 0 34 35 1 1 0 0 0 35 6 1 1 0 0 0 36 7 1 1 0 0 0 37 32 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	678.4
Volume:	685.952
LogP:	3.228
LogD:	3.411
LogS:	-3.867
# Rotatable Bonds:	8
TPSA:	172.21
# H-Bond Aceptor:	11
# H-Bond Donor:	5
# Rings:	6
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.207
Synthetic Accessibility Score:	5.726
Fsp3:	0.892
Lipinski Rule-of-5:	Rejected
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:	-5.363
MDCK Permeability:	4.898020051768981e-05
Pgp-inhibitor:	0.966
Pgp-substrate:	0.145
Human Intestinal Absorption (HIA):	0.034
20% Bioavailability (F20%):	0.01
30% Bioavailability (F30%):	0.571

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.008
Plasma Protein Binding (PPB):	75.8065185546875%
Volume Distribution (VD):	0.523
Pgp-substrate:	11.703227996826172%

ADMET: Metabolism

CYP1A2-inhibitor:	0.003
CYP1A2-substrate:	0.319
CYP2C19-inhibitor:	0.004
CYP2C19-substrate:	0.76
CYP2C9-inhibitor:	0.012
CYP2C9-substrate:	0.053
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.103
CYP3A4-inhibitor:	0.39
CYP3A4-substrate:	0.159

ADMET: Excretion

Clearance (CL):	1.735
Half-life (T1/2):	0.46

ADMET: Toxicity

hERG Blockers:	0.384
Human Hepatotoxicity (H-HT):	0.364
Drug-inuced Liver Injury (DILI):	0.046
AMES Toxicity:	0.031
Rat Oral Acute Toxicity:	0.072
Maximum Recommended Daily Dose:	0.088
Skin Sensitization:	0.146
Carcinogencity:	0.014
Eye Corrosion:	0.003
Eye Irritation:	0.011
Respiratory Toxicity:	0.204

Download Data

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

Natural Product: NPC272242

Natural Product ID:	NPC272242
*Common Name:**	Acanthosessilioside B
IUPAC Name:	n.a.
Synonyms:	Acanthosessilioside B
Standard InCHIKey:	IXRYSFZKSCQFAA-BYRFBRAMSA-N
Standard InCHI:	InChI=1S/C37H58O11/c1-18(2)19-9-12-37(32(44)47-31-29(43)28(42)27(41)22(17-38)46-31)14-13-34(5)20(26(19)37)15-21(39)30-35(34,6)11-10-23-33(3,4)48-24(36(23,30)7)16-25(40)45-8/h19-24,26-31,38-39,41-43H,1,9-17H2,2-8H3/t19-,20+,21+,22+,23-,24+,26+,27+,28-,29+,30-,31-,34+,35+,36+,37-/m0/s1
SMILES:	OC[C@H]1O[C@@H](OC(=O)[C@@]23CC[C@H]([C@@H]3[C@@H]3[C@](CC2)(C)[C@]2(C)CC[C@@H]4[C@]([C@H]2[C@@H](C3)O)(C)[C@@H](CC(=O)OC)OC4(C)C)C(=C)C)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2063157
PubChem CID:	60155052
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene glycosides [CHEMONTID:0001755] Diterpene glycosides

*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
NPO30633	Acanthopanax sessiliflorus	n.a.	n.a.	n.a.	Fruits	n.a.	n.a.	PMID[22691179]
NPO30633	Acanthopanax sessiliflorus	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[HerDing]
NPO30633	Acanthopanax sessiliflorus	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCM_Taiwan]

☑ 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	8
Others	1

Activity Type	# Activity
Cell Line	9

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	<	10000.0	nM	PMID[486870]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	<	10000.0	nM	PMID[486870]
NPT134	Cell Line	SK-BR-3	Homo sapiens	IC50	<	10000.0	nM	PMID[486870]
NPT146	Cell Line	SK-OV-3	Homo sapiens	IC50	<	10000.0	nM	PMID[486870]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	<	10000.0	nM	PMID[486870]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	<	10000.0	nM	PMID[486870]
NPT373	Cell Line	SK-MEL-5	Homo sapiens	IC50	<	10000.0	nM	PMID[486870]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	20600.0	nM	PMID[486870]
NPT113	Cell Line	RAW264.7	Mus musculus	Activity	=	93.0	%	PMID[486870]

☑ 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 NPC272242 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	290
0.1-0.2	2027
0.2-0.3	6409
0.3-0.4	12815
0.4-0.5	8188
0.5-0.6	5719
0.6-0.7	3810
0.7-0.8	2604
0.8-0.85	729
0.85-0.9	90
0.9-0.95	12
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9808	High Similarity	NPC102619
0.9706	High Similarity	NPC224414
0.9519	High Similarity	NPC106760
0.9429	High Similarity	NPC11035
0.934	High Similarity	NPC243572
0.934	High Similarity	NPC470543
0.9327	High Similarity	NPC88744
0.9252	High Similarity	NPC73986
0.9252	High Similarity	NPC146563
0.9238	High Similarity	NPC91583
0.9238	High Similarity	NPC51947
0.9238	High Similarity	NPC473844
0.9238	High Similarity	NPC240125
0.9216	High Similarity	NPC94919
0.9167	High Similarity	NPC54395
0.9083	High Similarity	NPC469823
0.9083	High Similarity	NPC469820
0.9083	High Similarity	NPC137414
0.9065	High Similarity	NPC204392
0.9065	High Similarity	NPC91838
0.9065	High Similarity	NPC1876
0.9065	High Similarity	NPC240734
0.9065	High Similarity	NPC275668
0.9057	High Similarity	NPC8431
0.9	High Similarity	NPC156651
0.8972	High Similarity	NPC101450
0.8919	High Similarity	NPC469822
0.8919	High Similarity	NPC239293
0.8889	High Similarity	NPC263827
0.8889	High Similarity	NPC274833
0.8889	High Similarity	NPC285410
0.8889	High Similarity	NPC250481
0.8868	High Similarity	NPC287269
0.8824	High Similarity	NPC253586
0.8818	High Similarity	NPC469821
0.8818	High Similarity	NPC116024
0.8807	High Similarity	NPC472719
0.8807	High Similarity	NPC207845
0.8796	High Similarity	NPC129340
0.8785	High Similarity	NPC195708
0.8774	High Similarity	NPC473199
0.8725	High Similarity	NPC472989
0.8716	High Similarity	NPC31839
0.8707	High Similarity	NPC273962
0.8704	High Similarity	NPC265655
0.8704	High Similarity	NPC477069
0.8704	High Similarity	NPC218853
0.8704	High Similarity	NPC477070
0.8684	High Similarity	NPC470478
0.8673	High Similarity	NPC477071
0.8661	High Similarity	NPC473304
0.8654	High Similarity	NPC108371
0.8649	High Similarity	NPC473882
0.8636	High Similarity	NPC1046
0.8636	High Similarity	NPC233003
0.8636	High Similarity	NPC48249
0.8636	High Similarity	NPC80843
0.8624	High Similarity	NPC475317
0.8624	High Similarity	NPC52241
0.8624	High Similarity	NPC154856
0.8624	High Similarity	NPC242611
0.8611	High Similarity	NPC258323
0.8611	High Similarity	NPC472988
0.8611	High Similarity	NPC295389
0.8611	High Similarity	NPC38217
0.8611	High Similarity	NPC230888
0.8598	High Similarity	NPC165405
0.8596	High Similarity	NPC37860
0.8596	High Similarity	NPC144644
0.8596	High Similarity	NPC110385
0.8596	High Similarity	NPC267694
0.8596	High Similarity	NPC473645
0.8596	High Similarity	NPC153673
0.8596	High Similarity	NPC142151
0.8596	High Similarity	NPC470312
0.8585	High Similarity	NPC213190
0.8584	High Similarity	NPC105800
0.8584	High Similarity	NPC232237
0.8571	High Similarity	NPC88945
0.8571	High Similarity	NPC472718
0.8571	High Similarity	NPC244127
0.8559	High Similarity	NPC475208
0.8559	High Similarity	NPC238935
0.8559	High Similarity	NPC251309
0.8558	High Similarity	NPC157739
0.8547	High Similarity	NPC174367
0.8547	High Similarity	NPC47113
0.8545	High Similarity	NPC471251
0.8545	High Similarity	NPC477073
0.8545	High Similarity	NPC292196
0.8545	High Similarity	NPC470311
0.8545	High Similarity	NPC270586
0.8534	High Similarity	NPC41129
0.8532	High Similarity	NPC167383
0.8532	High Similarity	NPC125361
0.8532	High Similarity	NPC296761
0.8532	High Similarity	NPC57362
0.8532	High Similarity	NPC137917
0.8532	High Similarity	NPC471250
0.8532	High Similarity	NPC51925
0.8532	High Similarity	NPC204407
0.8532	High Similarity	NPC237503
0.8532	High Similarity	NPC43976
0.8532	High Similarity	NPC306746
0.8532	High Similarity	NPC154085
0.8532	High Similarity	NPC131903
0.8522	High Similarity	NPC68767
0.8522	High Similarity	NPC293031
0.8522	High Similarity	NPC51099
0.8522	High Similarity	NPC275225
0.8519	High Similarity	NPC234160
0.8509	High Similarity	NPC207738
0.8505	High Similarity	NPC85593
0.8505	High Similarity	NPC31430
0.8505	High Similarity	NPC469827
0.8487	Intermediate Similarity	NPC477235
0.8482	Intermediate Similarity	NPC220293
0.8482	Intermediate Similarity	NPC477580
0.8482	Intermediate Similarity	NPC475486
0.8482	Intermediate Similarity	NPC164389
0.8476	Intermediate Similarity	NPC317019
0.8475	Intermediate Similarity	NPC117702
0.8475	Intermediate Similarity	NPC471357
0.8475	Intermediate Similarity	NPC146456
0.8475	Intermediate Similarity	NPC469757
0.8468	Intermediate Similarity	NPC477253
0.8468	Intermediate Similarity	NPC210420
0.8468	Intermediate Similarity	NPC100383
0.8468	Intermediate Similarity	NPC46388
0.8468	Intermediate Similarity	NPC471245
0.8468	Intermediate Similarity	NPC130427
0.8468	Intermediate Similarity	NPC37739
0.8468	Intermediate Similarity	NPC474265
0.8462	Intermediate Similarity	NPC476674
0.8462	Intermediate Similarity	NPC278939
0.8462	Intermediate Similarity	NPC472273
0.8462	Intermediate Similarity	NPC473555
0.8462	Intermediate Similarity	NPC471770
0.8455	Intermediate Similarity	NPC320383
0.8455	Intermediate Similarity	NPC59804
0.8455	Intermediate Similarity	NPC476886
0.8455	Intermediate Similarity	NPC476881
0.8455	Intermediate Similarity	NPC475296
0.8455	Intermediate Similarity	NPC7870
0.8455	Intermediate Similarity	NPC476880
0.8455	Intermediate Similarity	NPC476887
0.8455	Intermediate Similarity	NPC90856
0.8455	Intermediate Similarity	NPC78046
0.8455	Intermediate Similarity	NPC250956
0.8455	Intermediate Similarity	NPC110139
0.8455	Intermediate Similarity	NPC270667
0.8455	Intermediate Similarity	NPC476883
0.8455	Intermediate Similarity	NPC274507
0.8455	Intermediate Similarity	NPC474589
0.8455	Intermediate Similarity	NPC137104
0.8455	Intermediate Similarity	NPC476882
0.8455	Intermediate Similarity	NPC102914
0.8455	Intermediate Similarity	NPC474786
0.8455	Intermediate Similarity	NPC75747
0.8455	Intermediate Similarity	NPC220984
0.8455	Intermediate Similarity	NPC199457
0.8455	Intermediate Similarity	NPC476885
0.8455	Intermediate Similarity	NPC269095
0.8455	Intermediate Similarity	NPC174679
0.8455	Intermediate Similarity	NPC476884
0.8455	Intermediate Similarity	NPC164194
0.8455	Intermediate Similarity	NPC127056
0.8455	Intermediate Similarity	NPC29069
0.8455	Intermediate Similarity	NPC108709
0.8455	Intermediate Similarity	NPC136877
0.8455	Intermediate Similarity	NPC56713
0.8455	Intermediate Similarity	NPC68419
0.8455	Intermediate Similarity	NPC279554
0.844	Intermediate Similarity	NPC177246
0.844	Intermediate Similarity	NPC28198
0.844	Intermediate Similarity	NPC63841
0.844	Intermediate Similarity	NPC476123
0.844	Intermediate Similarity	NPC284807
0.844	Intermediate Similarity	NPC469826
0.8435	Intermediate Similarity	NPC471406
0.8426	Intermediate Similarity	NPC95243
0.8426	Intermediate Similarity	NPC285927
0.8426	Intermediate Similarity	NPC63023
0.8421	Intermediate Similarity	NPC475899
0.8407	Intermediate Similarity	NPC288205
0.8407	Intermediate Similarity	NPC51465
0.8407	Intermediate Similarity	NPC75287
0.8407	Intermediate Similarity	NPC291903
0.8407	Intermediate Similarity	NPC37134
0.8407	Intermediate Similarity	NPC305267
0.8407	Intermediate Similarity	NPC476992
0.8407	Intermediate Similarity	NPC26626
0.8396	Intermediate Similarity	NPC4831
0.8396	Intermediate Similarity	NPC129372
0.8396	Intermediate Similarity	NPC160734
0.8396	Intermediate Similarity	NPC472023
0.8396	Intermediate Similarity	NPC309425
0.8396	Intermediate Similarity	NPC47566
0.8396	Intermediate Similarity	NPC88000
0.8393	Intermediate Similarity	NPC271138

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 NPC272242 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	281
0.1-0.2	2410
0.2-0.3	3989
0.3-0.4	1574
0.4-0.5	438
0.5-0.6	272
0.6-0.7	141
0.7-0.8	40
0.8-0.85	4
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8727	High Similarity	NPD8133	Approved
0.8333	Intermediate Similarity	NPD7319	Approved
0.825	Intermediate Similarity	NPD7736	Approved
0.8235	Intermediate Similarity	NPD7507	Approved
0.8036	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.8017	Intermediate Similarity	NPD8293	Discontinued
0.8017	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7966	Intermediate Similarity	NPD8377	Approved
0.7966	Intermediate Similarity	NPD8294	Approved
0.7949	Intermediate Similarity	NPD7327	Approved
0.7949	Intermediate Similarity	NPD7328	Approved
0.7917	Intermediate Similarity	NPD8328	Phase 3
0.7899	Intermediate Similarity	NPD8296	Approved
0.7899	Intermediate Similarity	NPD8033	Approved
0.7899	Intermediate Similarity	NPD8380	Approved
0.7899	Intermediate Similarity	NPD8378	Approved
0.7899	Intermediate Similarity	NPD8379	Approved
0.7899	Intermediate Similarity	NPD8335	Approved
0.7881	Intermediate Similarity	NPD7516	Approved
0.7857	Intermediate Similarity	NPD6412	Phase 2
0.7833	Intermediate Similarity	NPD6370	Approved
0.781	Intermediate Similarity	NPD8035	Phase 2
0.781	Intermediate Similarity	NPD8034	Phase 2
0.7705	Intermediate Similarity	NPD7492	Approved
0.7667	Intermediate Similarity	NPD6059	Approved
0.7667	Intermediate Similarity	NPD6054	Approved
0.7642	Intermediate Similarity	NPD6616	Approved
0.7632	Intermediate Similarity	NPD6686	Approved
0.7581	Intermediate Similarity	NPD7078	Approved
0.7573	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.757	Intermediate Similarity	NPD8171	Discontinued
0.7459	Intermediate Similarity	NPD6016	Approved
0.7459	Intermediate Similarity	NPD6015	Approved
0.7398	Intermediate Similarity	NPD5988	Approved
0.7377	Intermediate Similarity	NPD6319	Approved
0.7328	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD8517	Approved
0.7317	Intermediate Similarity	NPD8513	Phase 3
0.7317	Intermediate Similarity	NPD8516	Approved
0.7317	Intermediate Similarity	NPD8515	Approved
0.7317	Intermediate Similarity	NPD7503	Approved
0.7227	Intermediate Similarity	NPD8297	Approved
0.7227	Intermediate Similarity	NPD6882	Approved
0.7131	Intermediate Similarity	NPD6009	Approved
0.7131	Intermediate Similarity	NPD7115	Discovery
0.7109	Intermediate Similarity	NPD6033	Approved
0.708	Intermediate Similarity	NPD7638	Approved
0.7063	Intermediate Similarity	NPD6067	Discontinued
0.7059	Intermediate Similarity	NPD6697	Approved
0.7059	Intermediate Similarity	NPD6115	Approved
0.7059	Intermediate Similarity	NPD6118	Approved
0.7059	Intermediate Similarity	NPD6114	Approved
0.7049	Intermediate Similarity	NPD6940	Discontinued
0.7034	Intermediate Similarity	NPD7320	Approved
0.7025	Intermediate Similarity	NPD4632	Approved
0.7018	Intermediate Similarity	NPD7640	Approved
0.7018	Intermediate Similarity	NPD7639	Approved
0.7009	Intermediate Similarity	NPD5739	Approved
0.7009	Intermediate Similarity	NPD6675	Approved
0.7009	Intermediate Similarity	NPD6402	Approved
0.7009	Intermediate Similarity	NPD7128	Approved
0.6975	Remote Similarity	NPD6373	Approved
0.6975	Remote Similarity	NPD6372	Approved
0.6961	Remote Similarity	NPD6116	Phase 1
0.6937	Remote Similarity	NPD6399	Phase 3
0.6923	Remote Similarity	NPD6928	Phase 2
0.6891	Remote Similarity	NPD6881	Approved
0.6891	Remote Similarity	NPD6899	Approved
0.6875	Remote Similarity	NPD7748	Approved
0.6864	Remote Similarity	NPD6008	Approved
0.6863	Remote Similarity	NPD6117	Approved
0.686	Remote Similarity	NPD6650	Approved
0.686	Remote Similarity	NPD8130	Phase 1
0.686	Remote Similarity	NPD6649	Approved
0.6842	Remote Similarity	NPD7902	Approved
0.6833	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD5701	Approved
0.6807	Remote Similarity	NPD5697	Approved
0.6777	Remote Similarity	NPD7102	Approved
0.6777	Remote Similarity	NPD4634	Approved
0.6777	Remote Similarity	NPD6883	Approved
0.6777	Remote Similarity	NPD7290	Approved
0.6772	Remote Similarity	NPD6921	Approved
0.6721	Remote Similarity	NPD6869	Approved
0.6721	Remote Similarity	NPD6847	Approved
0.6721	Remote Similarity	NPD6617	Approved
0.6721	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD7515	Phase 2
0.6696	Remote Similarity	NPD6083	Phase 2
0.6696	Remote Similarity	NPD6084	Phase 2
0.6694	Remote Similarity	NPD6013	Approved
0.6694	Remote Similarity	NPD6014	Approved
0.6694	Remote Similarity	NPD6012	Approved
0.6667	Remote Similarity	NPD7604	Phase 2
0.6667	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6641	Remote Similarity	NPD8074	Phase 3
0.6641	Remote Similarity	NPD5983	Phase 2
0.6639	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6638	Remote Similarity	NPD4225	Approved
0.6617	Remote Similarity	NPD5956	Approved
0.6612	Remote Similarity	NPD6011	Approved
0.661	Remote Similarity	NPD7632	Discontinued
0.6604	Remote Similarity	NPD7525	Registered
0.6585	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD7900	Approved
0.6579	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6574	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6574	Remote Similarity	NPD4788	Approved
0.6574	Remote Similarity	NPD3669	Approved
0.6565	Remote Similarity	NPD6336	Discontinued
0.6552	Remote Similarity	NPD4755	Approved
0.6525	Remote Similarity	NPD1700	Approved
0.6522	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6518	Remote Similarity	NPD5328	Approved
0.6514	Remote Similarity	NPD4786	Approved
0.65	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.65	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.6491	Remote Similarity	NPD4202	Approved
0.6466	Remote Similarity	NPD8337	Approved
0.6466	Remote Similarity	NPD8336	Approved
0.6441	Remote Similarity	NPD4696	Approved
0.6441	Remote Similarity	NPD5286	Approved
0.6441	Remote Similarity	NPD4700	Approved
0.6441	Remote Similarity	NPD5285	Approved
0.6429	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD7637	Suspended
0.6404	Remote Similarity	NPD6079	Approved
0.6404	Remote Similarity	NPD6411	Approved
0.6397	Remote Similarity	NPD8338	Approved
0.6397	Remote Similarity	NPD8449	Approved
0.6396	Remote Similarity	NPD3618	Phase 1
0.6393	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6393	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD1779	Approved
0.6389	Remote Similarity	NPD1780	Approved
0.6389	Remote Similarity	NPD7625	Phase 1
0.6379	Remote Similarity	NPD5695	Phase 3
0.6378	Remote Similarity	NPD6274	Approved
0.6357	Remote Similarity	NPD7101	Approved
0.6357	Remote Similarity	NPD7100	Approved
0.6356	Remote Similarity	NPD5696	Approved
0.635	Remote Similarity	NPD8450	Suspended
0.6333	Remote Similarity	NPD5226	Approved
0.6333	Remote Similarity	NPD4633	Approved
0.6333	Remote Similarity	NPD5225	Approved
0.6333	Remote Similarity	NPD5224	Approved
0.6333	Remote Similarity	NPD5211	Phase 2
0.633	Remote Similarity	NPD3667	Approved
0.6328	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD4767	Approved
0.6311	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD4768	Approved
0.6289	Remote Similarity	NPD7799	Discontinued
0.6286	Remote Similarity	NPD3703	Phase 2
0.6286	Remote Similarity	NPD3702	Approved
0.6283	Remote Similarity	NPD6672	Approved
0.6283	Remote Similarity	NPD6903	Approved
0.6283	Remote Similarity	NPD5737	Approved
0.6281	Remote Similarity	NPD5175	Approved
0.6281	Remote Similarity	NPD5174	Approved
0.6279	Remote Similarity	NPD6335	Approved
0.6275	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.627	Remote Similarity	NPD6053	Discontinued
0.6261	Remote Similarity	NPD7983	Approved
0.626	Remote Similarity	NPD6909	Approved
0.626	Remote Similarity	NPD6908	Approved
0.626	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.625	Remote Similarity	NPD7334	Approved
0.625	Remote Similarity	NPD5223	Approved
0.625	Remote Similarity	NPD5330	Approved
0.625	Remote Similarity	NPD7146	Approved
0.625	Remote Similarity	NPD6409	Approved
0.625	Remote Similarity	NPD6684	Approved
0.625	Remote Similarity	NPD7521	Approved
0.6239	Remote Similarity	NPD7991	Discontinued
0.623	Remote Similarity	NPD5141	Approved
0.6228	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6228	Remote Similarity	NPD6101	Approved
0.6228	Remote Similarity	NPD4753	Phase 2
0.621	Remote Similarity	NPD4730	Approved
0.621	Remote Similarity	NPD4729	Approved
0.6202	Remote Similarity	NPD6317	Approved
0.6195	Remote Similarity	NPD7524	Approved
0.6186	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6186	Remote Similarity	NPD4697	Phase 3
0.6186	Remote Similarity	NPD5221	Approved
0.6186	Remote Similarity	NPD5222	Approved
0.6174	Remote Similarity	NPD6698	Approved
0.6174	Remote Similarity	NPD46	Approved
0.6154	Remote Similarity	NPD5282	Discontinued
0.6154	Remote Similarity	NPD6314	Approved
0.6154	Remote Similarity	NPD6001	Approved
0.6154	Remote Similarity	NPD6313	Approved
0.6148	Remote Similarity	NPD4754	Approved
0.6136	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.6134	Remote Similarity	NPD5173	Approved
0.6124	Remote Similarity	NPD6868	Approved
0.6117	Remote Similarity	NPD3700	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