NPASS Compound

Structure

CID116465 OpenBabel06191715472D 47 53 0 0 1 0 0 0 0 0999 V2000 2.7213 -4.6562 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9890 -1.1900 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8269 -2.7381 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7213 1.2132 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3439 1.1506 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1269 1.4748 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3581 -2.4667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1978 -2.8628 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5740 -5.0884 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0660 -3.3101 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9707 -3.5182 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3153 -4.1623 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5684 -2.2106 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6321 0.4207 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5684 -3.1889 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2117 0.0397 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9763 -1.5127 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5457 -3.7997 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4023 -4.5513 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7213 -0.7433 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0269 -1.7215 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1997 -2.1693 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0367 -4.2709 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7213 -1.7215 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5432 -4.0643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0124 0.1092 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8741 -2.2106 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8741 -3.1889 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5518 -0.9642 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3839 -3.9234 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8741 -0.2541 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2887 -4.6105 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0269 -0.7433 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9723 -0.5832 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7120 0.5203 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3004 -0.4111 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2058 0.4657 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7213 -3.6780 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.1715 -0.6527 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.1074 1.4150 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1207 -2.9812 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8741 0.7241 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3713 1.2555 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9726 -0.1049 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9615 -4.4421 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3910 -0.4664 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 39 1 0 0 0 0 2 40 1 0 0 0 0 3 42 1 0 0 0 0 4 43 1 0 0 0 0 5 44 1 0 0 0 0 6 45 1 0 0 0 0 7 10 1 0 0 0 0 7 22 2 0 0 0 0 8 11 2 0 0 0 0 8 22 1 0 0 0 0 9 12 2 0 0 0 0 9 23 1 0 0 0 0 10 25 2 0 0 0 0 11 25 1 0 0 0 0 12 30 1 0 0 0 0 13 15 1 0 0 0 0 13 24 1 0 0 0 0 14 16 1 0 0 0 0 14 26 1 0 0 0 0 15 39 1 0 0 0 0 16 40 1 0 0 0 0 17 22 1 0 0 0 0 18 23 1 0 0 0 0 19 23 2 0 0 0 0 19 32 1 0 0 0 0 20 24 2 0 0 0 0 20 31 1 0 0 0 0 21 27 2 0 0 0 0 21 33 1 0 0 0 0 24 27 1 0 0 0 0 25 46 1 0 0 0 0 26 34 2 0 0 0 0 26 35 1 0 0 0 0 27 28 1 0 0 0 0 28 18 1 1 0 0 0 28 39 1 0 0 0 0 29 17 1 6 0 0 0 29 34 1 0 0 0 0 29 40 1 0 0 0 0 30 32 2 0 0 0 0 30 42 1 0 0 0 0 31 33 2 0 0 0 0 31 43 1 0 0 0 0 32 46 1 0 0 0 0 33 47 1 0 0 0 0 34 36 1 0 0 0 0 35 37 2 0 0 0 0 35 41 1 0 0 0 0 36 38 2 0 0 0 0 36 47 1 0 0 0 0 37 38 1 0 0 0 0 37 44 1 0 0 0 0 38 45 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	638.3
Volume:	657.796
LogP:	6.021
LogD:	3.798
LogS:	-5.248
# Rotatable Bonds:	4
TPSA:	82.09
# H-Bond Aceptor:	9
# H-Bond Donor:	1
# Rings:	8
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.258
Synthetic Accessibility Score:	5.86
Fsp3:	0.368
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.602
MDCK Permeability:	2.89752733806381e-05
Pgp-inhibitor:	0.998
Pgp-substrate:	0.954
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.137
30% Bioavailability (F30%):	0.809

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.051
Plasma Protein Binding (PPB):	59.72875213623047%
Volume Distribution (VD):	0.933
Pgp-substrate:	32.75148010253906%

ADMET: Metabolism

CYP1A2-inhibitor:	0.054
CYP1A2-substrate:	0.974
CYP2C19-inhibitor:	0.067
CYP2C19-substrate:	0.974
CYP2C9-inhibitor:	0.047
CYP2C9-substrate:	0.79
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.955
CYP3A4-inhibitor:	0.102
CYP3A4-substrate:	0.96

ADMET: Excretion

Clearance (CL):	11.113
Half-life (T1/2):	0.237

ADMET: Toxicity

hERG Blockers:	0.971
Human Hepatotoxicity (H-HT):	0.026
Drug-inuced Liver Injury (DILI):	0.714
AMES Toxicity:	0.07
Rat Oral Acute Toxicity:	0.782
Maximum Recommended Daily Dose:	0.992
Skin Sensitization:	0.799
Carcinogencity:	0.033
Eye Corrosion:	0.003
Eye Irritation:	0.005
Respiratory Toxicity:	0.468

Download Data

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

Natural Product: NPC116465

Natural Product ID:	NPC116465
*Common Name:**	Thaligosine
IUPAC Name:	n.a.
Synonyms:	Thaligosine
Standard InCHIKey:	QAFGBLDGRLFICB-VMPREFPWSA-N
Standard InCHI:	InChI=1S/C38H42N2O7/c1-39-15-13-24-20-31(43-4)33-21-27(24)28(39)18-23-9-12-30(42-3)32(19-23)46-25-10-7-22(8-11-25)17-29-34-26(14-16-40(29)2)35(41)37(44-5)38(45-6)36(34)47-33/h7-12,19-21,28-29,41H,13-18H2,1-6H3/t28-,29-/m0/s1
SMILES:	CN1CCc2cc(c3cc2[C@@H]1Cc1ccc(c(c1)Oc1ccc(cc1)C[C@H]1c2c(CCN1C)c(c(c(c2O3)OC)OC)O)OC)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL443881
PubChem CID:	179390
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds

*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
NPO20891	Coleonema pulchellum	Species	Rutaceae	Eukaryota	n.a.	Costa Rica; Bartica, Guyana	n.a.	PMID[16124770]
NPO22044	Tamarix chinensis	Species	Tamaricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22044	Tamarix chinensis	Species	Tamaricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20891	Coleonema pulchellum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22044	Tamarix chinensis	Species	Tamaricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22044	Tamarix chinensis	Species	Tamaricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO20891	Coleonema pulchellum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22625	Copris tripartitus	Species	Scarabaeidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22044	Tamarix chinensis	Species	Tamaricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20320	Cryptostegia madagascariensis	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21985	Koenigia coriaria	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20451	Vitex scabra	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

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

NP Quantity Composition/Concentration

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

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

Biological Activity

Activity Type	# Activity
Others	3

Activity Type	# Activity
Organism	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	Activity	=	100.0	ug ml-1	PMID[481646]
NPT602	Organism	Mycobacterium smegmatis	Mycobacterium smegmatis	Activity	=	100.0	ug ml-1	PMID[481646]
NPT20	Organism	Candida albicans	Candida albicans	Activity	=	1000.0	ug ml-1	PMID[481646]

☑ 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 NPC116465 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	385
0.1-0.2	1848
0.2-0.3	9058
0.3-0.4	9420
0.4-0.5	5532
0.5-0.6	8662
0.6-0.7	6280
0.7-0.8	1252
0.8-0.85	120
0.85-0.9	45
0.9-0.95	49
0.95-1	46

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC212237
0.982	High Similarity	NPC182052
0.982	High Similarity	NPC54654
0.982	High Similarity	NPC8836
0.982	High Similarity	NPC49075
0.982	High Similarity	NPC217748
0.982	High Similarity	NPC7715
0.982	High Similarity	NPC42663
0.982	High Similarity	NPC223690
0.982	High Similarity	NPC290582
0.982	High Similarity	NPC239824
0.982	High Similarity	NPC285931
0.982	High Similarity	NPC222661
0.982	High Similarity	NPC279228
0.982	High Similarity	NPC271013
0.982	High Similarity	NPC229373
0.982	High Similarity	NPC258657
0.982	High Similarity	NPC181796
0.982	High Similarity	NPC90998
0.982	High Similarity	NPC311973
0.982	High Similarity	NPC104196
0.982	High Similarity	NPC15414
0.982	High Similarity	NPC251735
0.982	High Similarity	NPC290005
0.982	High Similarity	NPC328155
0.982	High Similarity	NPC185639
0.9762	High Similarity	NPC167116
0.9762	High Similarity	NPC274716
0.9762	High Similarity	NPC254441
0.976	High Similarity	NPC286119
0.9706	High Similarity	NPC275680
0.9706	High Similarity	NPC22115
0.9702	High Similarity	NPC30779
0.9588	High Similarity	NPC95426
0.9588	High Similarity	NPC16357
0.9588	High Similarity	NPC302245
0.9581	High Similarity	NPC293093
0.9535	High Similarity	NPC206900
0.9535	High Similarity	NPC274661
0.9535	High Similarity	NPC48490
0.9535	High Similarity	NPC175890
0.9535	High Similarity	NPC82457
0.9535	High Similarity	NPC11296
0.9532	High Similarity	NPC139783
0.9532	High Similarity	NPC65312
0.948	High Similarity	NPC60295
0.948	High Similarity	NPC191132
0.9425	High Similarity	NPC24260
0.9401	High Similarity	NPC198498
0.9401	High Similarity	NPC317439
0.9401	High Similarity	NPC317145
0.9401	High Similarity	NPC63646
0.9401	High Similarity	NPC227060
0.9401	High Similarity	NPC276890
0.9401	High Similarity	NPC10908
0.9401	High Similarity	NPC115284
0.9401	High Similarity	NPC76682
0.9345	High Similarity	NPC41376
0.9345	High Similarity	NPC251580
0.9345	High Similarity	NPC12424
0.9345	High Similarity	NPC129518
0.9314	High Similarity	NPC478093
0.9261	High Similarity	NPC478092
0.9261	High Similarity	NPC30182
0.9261	High Similarity	NPC478091
0.9261	High Similarity	NPC256124
0.9261	High Similarity	NPC473589
0.9231	High Similarity	NPC190783
0.9231	High Similarity	NPC232386
0.9231	High Similarity	NPC152680
0.9162	High Similarity	NPC42549
0.9162	High Similarity	NPC317272
0.9162	High Similarity	NPC240841
0.9162	High Similarity	NPC13916
0.9162	High Similarity	NPC256012
0.9162	High Similarity	NPC268503
0.9162	High Similarity	NPC264850
0.9162	High Similarity	NPC250846
0.9153	High Similarity	NPC85381
0.9148	High Similarity	NPC41122
0.9148	High Similarity	NPC318805
0.9128	High Similarity	NPC475479
0.9128	High Similarity	NPC243454
0.9111	High Similarity	NPC475654
0.9102	High Similarity	NPC24465
0.9075	High Similarity	NPC239584
0.9053	High Similarity	NPC204908
0.9053	High Similarity	NPC83198
0.905	High Similarity	NPC234318
0.9023	High Similarity	NPC73492
0.9023	High Similarity	NPC299990
0.8977	High Similarity	NPC14507
0.8977	High Similarity	NPC47077
0.8864	High Similarity	NPC302275
0.8859	High Similarity	NPC254581
0.8837	High Similarity	NPC475215
0.8837	High Similarity	NPC108434
0.8814	High Similarity	NPC249996
0.8771	High Similarity	NPC281581
0.875	High Similarity	NPC195538
0.8743	High Similarity	NPC247639
0.8743	High Similarity	NPC25084
0.8722	High Similarity	NPC473716
0.8722	High Similarity	NPC475597
0.8701	High Similarity	NPC476202
0.8683	High Similarity	NPC172765
0.8683	High Similarity	NPC204828
0.8683	High Similarity	NPC127674
0.8683	High Similarity	NPC39701
0.8683	High Similarity	NPC469817
0.8683	High Similarity	NPC189266
0.8683	High Similarity	NPC276588
0.8683	High Similarity	NPC2413
0.8683	High Similarity	NPC249797
0.8683	High Similarity	NPC193949
0.8683	High Similarity	NPC184026
0.8683	High Similarity	NPC207757
0.8683	High Similarity	NPC295691
0.8683	High Similarity	NPC278799
0.8683	High Similarity	NPC110416
0.8683	High Similarity	NPC54379
0.8683	High Similarity	NPC5238
0.8621	High Similarity	NPC239775
0.8563	High Similarity	NPC168753
0.8563	High Similarity	NPC118274
0.8514	High Similarity	NPC10871
0.8488	Intermediate Similarity	NPC475393
0.8462	Intermediate Similarity	NPC82056
0.8448	Intermediate Similarity	NPC158376
0.8448	Intermediate Similarity	NPC117188
0.8448	Intermediate Similarity	NPC81218
0.8448	Intermediate Similarity	NPC205421
0.8448	Intermediate Similarity	NPC12053
0.8448	Intermediate Similarity	NPC306555
0.8448	Intermediate Similarity	NPC474931
0.8448	Intermediate Similarity	NPC145832
0.8443	Intermediate Similarity	NPC151895
0.8443	Intermediate Similarity	NPC192768
0.8443	Intermediate Similarity	NPC88249
0.8443	Intermediate Similarity	NPC220858
0.8443	Intermediate Similarity	NPC97221
0.8436	Intermediate Similarity	NPC230276
0.8436	Intermediate Similarity	NPC257269
0.843	Intermediate Similarity	NPC60186
0.843	Intermediate Similarity	NPC79402
0.843	Intermediate Similarity	NPC80759
0.8402	Intermediate Similarity	NPC475557
0.8383	Intermediate Similarity	NPC477565
0.8383	Intermediate Similarity	NPC103379
0.838	Intermediate Similarity	NPC119068
0.838	Intermediate Similarity	NPC474507
0.838	Intermediate Similarity	NPC40496
0.8372	Intermediate Similarity	NPC235143
0.8372	Intermediate Similarity	NPC119649
0.8372	Intermediate Similarity	NPC205255
0.8372	Intermediate Similarity	NPC230956
0.8372	Intermediate Similarity	NPC271388
0.8359	Intermediate Similarity	NPC38964
0.8352	Intermediate Similarity	NPC109925
0.8333	Intermediate Similarity	NPC306843
0.8333	Intermediate Similarity	NPC253043
0.8333	Intermediate Similarity	NPC196447
0.8333	Intermediate Similarity	NPC232514
0.8333	Intermediate Similarity	NPC96603
0.8333	Intermediate Similarity	NPC276944
0.8333	Intermediate Similarity	NPC477563
0.8333	Intermediate Similarity	NPC238530
0.8333	Intermediate Similarity	NPC13504
0.8333	Intermediate Similarity	NPC212794
0.8333	Intermediate Similarity	NPC78222
0.8333	Intermediate Similarity	NPC136508
0.8323	Intermediate Similarity	NPC24233
0.8323	Intermediate Similarity	NPC476571
0.8323	Intermediate Similarity	NPC135538
0.8323	Intermediate Similarity	NPC147390
0.8323	Intermediate Similarity	NPC428
0.8323	Intermediate Similarity	NPC246587
0.8314	Intermediate Similarity	NPC221864
0.8278	Intermediate Similarity	NPC32154
0.8276	Intermediate Similarity	NPC1229
0.8276	Intermediate Similarity	NPC324144
0.8268	Intermediate Similarity	NPC148709
0.8268	Intermediate Similarity	NPC173416
0.8268	Intermediate Similarity	NPC476577
0.8263	Intermediate Similarity	NPC179825
0.8263	Intermediate Similarity	NPC51957
0.8263	Intermediate Similarity	NPC210437
0.8263	Intermediate Similarity	NPC476151
0.8263	Intermediate Similarity	NPC476144
0.8263	Intermediate Similarity	NPC106295
0.8263	Intermediate Similarity	NPC191376
0.8263	Intermediate Similarity	NPC16107
0.8263	Intermediate Similarity	NPC321505
0.8229	Intermediate Similarity	NPC284183
0.8229	Intermediate Similarity	NPC4138
0.8229	Intermediate Similarity	NPC121275
0.8225	Intermediate Similarity	NPC476969
0.8214	Intermediate Similarity	NPC7467
0.8167	Intermediate Similarity	NPC241704
0.8161	Intermediate Similarity	NPC27410

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 NPC116465 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	216
0.1-0.2	800
0.2-0.3	1200
0.3-0.4	2317
0.4-0.5	2374
0.5-0.6	1522
0.6-0.7	602
0.7-0.8	109
0.8-0.85	4
0.85-0.9	0
0.9-0.95	4
0.95-1	2

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.982	High Similarity	NPD8053	Approved
0.982	High Similarity	NPD8054	Approved
0.9401	High Similarity	NPD8252	Approved
0.9401	High Similarity	NPD8251	Approved
0.9401	High Similarity	NPD8099	Discontinued
0.9345	High Similarity	NPD8156	Discontinued
0.8441	Intermediate Similarity	NPD8095	Phase 1
0.838	Intermediate Similarity	NPD8453	Clinical (unspecified phase)
0.8263	Intermediate Similarity	NPD4584	Approved
0.8251	Intermediate Similarity	NPD7906	Approved
0.8208	Intermediate Similarity	NPD6788	Approved
0.7989	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7977	Intermediate Similarity	NPD4773	Phase 2
0.7977	Intermediate Similarity	NPD4772	Phase 2
0.7935	Intermediate Similarity	NPD7312	Approved
0.7935	Intermediate Similarity	NPD7313	Approved
0.7935	Intermediate Similarity	NPD7311	Approved
0.7935	Intermediate Similarity	NPD7310	Approved
0.7904	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.7903	Intermediate Similarity	NPD4663	Approved
0.7895	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7892	Intermediate Similarity	NPD7309	Approved
0.788	Intermediate Similarity	NPD7549	Discontinued
0.7877	Intermediate Similarity	NPD6071	Discontinued
0.7853	Intermediate Similarity	NPD7831	Phase 2
0.7853	Intermediate Similarity	NPD7833	Phase 2
0.7853	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7838	Intermediate Similarity	NPD4577	Approved
0.7838	Intermediate Similarity	NPD4578	Approved
0.7829	Intermediate Similarity	NPD7298	Approved
0.779	Intermediate Similarity	NPD27	Approved
0.779	Intermediate Similarity	NPD2489	Approved
0.7778	Intermediate Similarity	NPD3051	Approved
0.7759	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7735	Intermediate Similarity	NPD2970	Approved
0.7735	Intermediate Similarity	NPD2969	Approved
0.7733	Intermediate Similarity	NPD7447	Phase 1
0.7733	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD5677	Discontinued
0.7667	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD2563	Approved
0.764	Intermediate Similarity	NPD2560	Approved
0.7582	Intermediate Similarity	NPD4010	Discontinued
0.7572	Intermediate Similarity	NPD7213	Phase 3
0.7572	Intermediate Similarity	NPD7212	Phase 2
0.7558	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD1424	Approved
0.7515	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD4675	Approved
0.7514	Intermediate Similarity	NPD4678	Approved
0.75	Intermediate Similarity	NPD2898	Approved
0.7471	Intermediate Similarity	NPD2420	Approved
0.7471	Intermediate Similarity	NPD2421	Approved
0.7459	Intermediate Similarity	NPD4055	Discovery
0.7443	Intermediate Similarity	NPD6031	Approved
0.7443	Intermediate Similarity	NPD6030	Approved
0.7424	Intermediate Similarity	NPD3450	Approved
0.7424	Intermediate Similarity	NPD2494	Approved
0.7424	Intermediate Similarity	NPD2493	Approved
0.7424	Intermediate Similarity	NPD3452	Approved
0.7414	Intermediate Similarity	NPD7124	Phase 2
0.7387	Intermediate Similarity	NPD8152	Approved
0.7387	Intermediate Similarity	NPD8153	Approved
0.7386	Intermediate Similarity	NPD6090	Discontinued
0.736	Intermediate Similarity	NPD4017	Approved
0.7356	Intermediate Similarity	NPD5241	Discontinued
0.7345	Intermediate Similarity	NPD3640	Phase 3
0.7345	Intermediate Similarity	NPD3639	Approved
0.7345	Intermediate Similarity	NPD3641	Approved
0.7337	Intermediate Similarity	NPD7802	Discontinued
0.7337	Intermediate Similarity	NPD6107	Approved
0.7333	Intermediate Similarity	NPD6997	Phase 2
0.732	Intermediate Similarity	NPD2490	Approved
0.732	Intermediate Similarity	NPD2488	Approved
0.7314	Intermediate Similarity	NPD3845	Phase 1
0.7313	Intermediate Similarity	NPD4582	Approved
0.7313	Intermediate Similarity	NPD4583	Approved
0.7312	Intermediate Similarity	NPD4481	Phase 3
0.7308	Intermediate Similarity	NPD4581	Clinical (unspecified phase)
0.7295	Intermediate Similarity	NPD7047	Phase 3
0.7293	Intermediate Similarity	NPD5772	Approved
0.7293	Intermediate Similarity	NPD5773	Approved
0.7268	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7264	Intermediate Similarity	NPD4002	Approved
0.7264	Intermediate Similarity	NPD4004	Approved
0.7263	Intermediate Similarity	NPD4005	Discontinued
0.7247	Intermediate Similarity	NPD2122	Discontinued
0.7246	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD5177	Phase 3
0.724	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD4123	Phase 3
0.7222	Intermediate Similarity	NPD2975	Approved
0.7222	Intermediate Similarity	NPD2974	Approved
0.7222	Intermediate Similarity	NPD6621	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD2973	Approved
0.7219	Intermediate Similarity	NPD4475	Approved
0.7219	Intermediate Similarity	NPD4474	Approved
0.7214	Intermediate Similarity	NPD5005	Approved
0.7214	Intermediate Similarity	NPD5006	Approved
0.72	Intermediate Similarity	NPD6748	Discontinued
0.7186	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7182	Intermediate Similarity	NPD6072	Discontinued
0.7176	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD1613	Approved
0.7175	Intermediate Similarity	NPD7598	Phase 2
0.7168	Intermediate Similarity	NPD1632	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD5718	Phase 2
0.7151	Intermediate Similarity	NPD2200	Suspended
0.715	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD6996	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD2422	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD4580	Approved
0.7114	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD42	Phase 2
0.7105	Intermediate Similarity	NPD6042	Phase 2
0.7105	Intermediate Similarity	NPD5312	Approved
0.7105	Intermediate Similarity	NPD5313	Approved
0.7104	Intermediate Similarity	NPD7046	Clinical (unspecified phase)
0.7102	Intermediate Similarity	NPD7466	Approved
0.7086	Intermediate Similarity	NPD7045	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD3124	Discontinued
0.7072	Intermediate Similarity	NPD8158	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD7827	Phase 1
0.7062	Intermediate Similarity	NPD3692	Discontinued
0.7062	Intermediate Similarity	NPD6853	Approved
0.7062	Intermediate Similarity	NPD6851	Approved
0.7049	Intermediate Similarity	NPD7945	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD7132	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD4908	Phase 1
0.7039	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD6297	Approved
0.7029	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7015	Intermediate Similarity	NPD4420	Approved
0.7011	Intermediate Similarity	NPD2978	Approved
0.7011	Intermediate Similarity	NPD2977	Approved
0.701	Intermediate Similarity	NPD2971	Approved
0.701	Intermediate Similarity	NPD2968	Approved
0.701	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD3027	Phase 3
0.7	Intermediate Similarity	NPD5602	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD6523	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD2238	Phase 2
0.6976	Remote Similarity	NPD4040	Phase 1
0.697	Remote Similarity	NPD3808	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD2677	Approved
0.6963	Remote Similarity	NPD7907	Approved
0.6959	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD3383	Approved
0.6957	Remote Similarity	NPD3384	Approved
0.6957	Remote Similarity	NPD3382	Approved
0.6954	Remote Similarity	NPD6111	Discontinued
0.6954	Remote Similarity	NPD6896	Approved
0.6954	Remote Similarity	NPD6895	Approved
0.6949	Remote Similarity	NPD4236	Phase 3
0.6949	Remote Similarity	NPD4237	Approved
0.6949	Remote Similarity	NPD4162	Approved
0.6949	Remote Similarity	NPD3060	Approved
0.6931	Remote Similarity	NPD4166	Phase 2
0.6927	Remote Similarity	NPD6666	Approved
0.6927	Remote Similarity	NPD4873	Discontinued
0.6927	Remote Similarity	NPD6783	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD6667	Approved
0.6919	Remote Similarity	NPD2674	Phase 3
0.6919	Remote Similarity	NPD4585	Approved
0.6914	Remote Similarity	NPD1753	Discontinued
0.6911	Remote Similarity	NPD5938	Phase 3
0.691	Remote Similarity	NPD3977	Clinical (unspecified phase)
0.6902	Remote Similarity	NPD5090	Approved
0.6902	Remote Similarity	NPD5089	Approved
0.6901	Remote Similarity	NPD2669	Clinical (unspecified phase)
0.6898	Remote Similarity	NPD8005	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD3837	Clinical (unspecified phase)
0.6895	Remote Similarity	NPD8051	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD7037	Approved
0.6891	Remote Similarity	NPD7479	Phase 2
0.6875	Remote Similarity	NPD7701	Phase 2
0.6872	Remote Similarity	NPD5084	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD5160	Discontinued
0.6869	Remote Similarity	NPD2899	Discontinued
0.6869	Remote Similarity	NPD6842	Approved
0.6869	Remote Similarity	NPD6841	Approved
0.6869	Remote Similarity	NPD7291	Discontinued
0.6869	Remote Similarity	NPD6843	Phase 3
0.6864	Remote Similarity	NPD4098	Discontinued
0.6859	Remote Similarity	NPD6166	Phase 2
0.6859	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD7718	Clinical (unspecified phase)
0.6834	Remote Similarity	NPD6377	Clinical (unspecified phase)
0.6825	Remote Similarity	NPD4666	Phase 3
0.6821	Remote Similarity	NPD7477	Discontinued
0.6816	Remote Similarity	NPD6658	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD7125	Discontinued
0.6813	Remote Similarity	NPD7526	Approved
0.6813	Remote Similarity	NPD52	Approved
0.6813	Remote Similarity	NPD3647	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD7527	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD5604	Discontinued

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