NPASS Compound

Structure

NPC148860 OpenBabel07101719142D 42 47 0 0 1 0 0 0 0 0999 V2000 3.3919 0.9792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5439 0.4896 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1278 1.9500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9792 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -4.8958 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8480 -4.4063 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8480 -4.4063 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6960 2.9375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0879 -1.9583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5439 2.4479 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8480 -3.4271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8480 -3.4271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2399 -1.4687 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8480 2.4479 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0879 -2.9375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2425 -0.4418 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3919 -2.9375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0415 -0.9239 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5439 1.4688 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.9375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3919 -1.9583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2203 -0.3906 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8480 1.4688 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8916 0.4723 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4738 0.5552 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6960 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8480 -0.4896 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -1.9583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5439 -1.4687 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4516 0.6065 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6960 0.9792 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 0.9792 0.0000 C 0 0 2 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 4.2399 -3.4271 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.8480 -1.4688 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6960 -1.9583 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9849 1.4277 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4896 -0.8480 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8025 -0.3077 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6526 1.0885 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5439 -0.4896 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8480 -1.4687 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 19 1 0 0 0 0 3 32 1 0 0 0 0 5 6 2 0 0 0 0 5 7 1 0 0 0 0 6 11 1 0 0 0 0 7 12 2 0 0 0 0 8 10 1 0 0 0 0 8 14 1 0 0 0 0 9 13 2 0 0 0 0 9 15 1 0 0 0 0 10 19 2 0 0 0 0 11 20 2 0 0 0 0 12 20 1 0 0 0 0 13 21 1 0 0 0 0 14 23 1 0 0 0 0 15 34 2 0 0 0 0 16 22 1 0 0 0 0 17 21 2 0 0 0 0 17 34 1 0 0 0 0 18 22 1 0 0 0 0 18 39 1 0 0 0 0 19 31 1 0 0 0 0 20 28 1 0 0 0 0 21 29 1 0 0 0 0 22 25 2 0 0 0 0 23 31 1 1 0 0 0 23 32 1 0 0 0 0 24 16 1 1 0 0 0 24 32 1 0 0 0 0 24 40 1 0 0 0 0 25 30 1 0 0 0 0 25 40 1 0 0 0 0 26 27 1 0 0 0 0 26 31 1 1 0 0 0 26 41 1 0 0 0 0 27 33 1 6 0 0 0 27 42 1 0 0 0 0 28 35 2 0 0 0 0 28 42 1 0 0 0 0 29 36 2 0 0 0 0 29 41 1 0 0 0 0 30 37 2 0 0 0 0 30 39 1 0 0 0 0 31 2 1 1 0 0 0 32 33 1 1 0 0 0 33 4 1 1 0 0 0 33 38 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	573.24
Volume:	580.303
LogP:	4.434
LogD:	3.261
LogS:	-3.795
# Rotatable Bonds:	7
TPSA:	128.32
# H-Bond Aceptor:	9
# H-Bond Donor:	2
# Rings:	6
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.31
Synthetic Accessibility Score:	4.976
Fsp3:	0.424
Lipinski Rule-of-5:	Accepted
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:	-5.422
MDCK Permeability:	1.9667357264552265e-05
Pgp-inhibitor:	0.979
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.619
30% Bioavailability (F30%):	0.601

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.09
Plasma Protein Binding (PPB):	98.24346160888672%
Volume Distribution (VD):	1.985
Pgp-substrate:	6.260000228881836%

ADMET: Metabolism

CYP1A2-inhibitor:	0.352
CYP1A2-substrate:	0.095
CYP2C19-inhibitor:	0.845
CYP2C19-substrate:	0.064
CYP2C9-inhibitor:	0.885
CYP2C9-substrate:	0.833
CYP2D6-inhibitor:	0.974
CYP2D6-substrate:	0.207
CYP3A4-inhibitor:	0.911
CYP3A4-substrate:	0.243

ADMET: Excretion

Clearance (CL):	11.59
Half-life (T1/2):	0.51

ADMET: Toxicity

hERG Blockers:	0.482
Human Hepatotoxicity (H-HT):	0.249
Drug-inuced Liver Injury (DILI):	0.574
AMES Toxicity:	0.004
Rat Oral Acute Toxicity:	0.75
Maximum Recommended Daily Dose:	0.288
Skin Sensitization:	0.505
Carcinogencity:	0.15
Eye Corrosion:	0.003
Eye Irritation:	0.043
Respiratory Toxicity:	0.43

Download Data

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

Natural Product: NPC148860

Natural Product ID:	NPC148860
*Common Name:**	Scutehenanine D
IUPAC Name:	[(1R,2S,3R,4S,4aS,8aR)-2-benzoyloxy-3-hydroxy-3,4,8,8a-tetramethyl-4-[(2R)-6-oxo-3,4-dihydro-2H-furo[2,3-c]furan-2-yl]-2,4a,5,6-tetrahydro-1H-naphthalen-1-yl] pyridine-3-carboxylate
Synonyms:	Scutehenanine D
Standard InCHIKey:	NFCXCBLWABDYMW-FWQSJGQVSA-N
Standard InCHI:	InChI=1S/C33H35NO8/c1-19-10-8-14-23-31(19,2)26(41-29(36)21-13-9-15-34-17-21)27(42-28(35)20-11-6-5-7-12-20)33(4,38)32(23,3)24-16-22-18-39-30(37)25(22)40-24/h5-7,9-13,15,17,23-24,26-27,38H,8,14,16,18H2,1-4H3/t23-,24+,26-,27-,31-,32-,33-/m0/s1
SMILES:	CC1=CCC[C@H]2[C@@]1(C)[C@H]([C@@H]([C@@](C)([C@]2(C)[C@H]1CC2=C(C(=O)OC2)O1)O)OC(=O)c1ccccc1)OC(=O)c1cccnc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1077451
PubChem CID:	44556950
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001538] Diterpene lactones

*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
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[16755060]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[17666848]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[18239311]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19785430]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19962306]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20078074]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	whole plants	Nanning District, Guangxi Province, China	2012-Sep	PMID[25647077]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	aerial parts	Seoul, Korea	n.a.	PMID[26331882]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO16039	Scutellaria barbata	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
IC50	3

Activity Type	# Activity
Cell Line	2
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	=	2800.0	nM	PMID[547048]
NPT139	Cell Line	HT-29	Homo sapiens	IC50	=	6400.0	nM	PMID[547048]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	4100.0	nM	PMID[547048]

☑ 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 NPC148860 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	331
0.1-0.2	1441
0.2-0.3	3486
0.3-0.4	10370
0.4-0.5	16124
0.5-0.6	9018
0.6-0.7	1645
0.7-0.8	98
0.8-0.85	59
0.85-0.9	87
0.9-0.95	33
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.98	High Similarity	NPC477912
0.965	High Similarity	NPC62367
0.9602	High Similarity	NPC216428
0.955	High Similarity	NPC42678
0.955	High Similarity	NPC477907
0.955	High Similarity	NPC477909
0.95	High Similarity	NPC319128
0.9461	High Similarity	NPC477911
0.9453	High Similarity	NPC477910
0.9409	High Similarity	NPC301368
0.9409	High Similarity	NPC84815
0.9403	High Similarity	NPC228331
0.94	High Similarity	NPC472553
0.9369	High Similarity	NPC328154
0.9314	High Similarity	NPC472555
0.931	High Similarity	NPC471016
0.931	High Similarity	NPC6981
0.9275	High Similarity	NPC477902
0.9272	High Similarity	NPC127026
0.9272	High Similarity	NPC127720
0.9265	High Similarity	NPC294579
0.9265	High Similarity	NPC144779
0.9261	High Similarity	NPC470306
0.925	High Similarity	NPC472550
0.925	High Similarity	NPC48042
0.925	High Similarity	NPC304179
0.9238	High Similarity	NPC150698
0.9238	High Similarity	NPC96801
0.9227	High Similarity	NPC471980
0.9216	High Similarity	NPC471014
0.9216	High Similarity	NPC477908
0.9216	High Similarity	NPC475408
0.9216	High Similarity	NPC206343
0.9212	High Similarity	NPC4421
0.9194	High Similarity	NPC319880
0.9194	High Similarity	NPC244839
0.9194	High Similarity	NPC320324
0.9187	High Similarity	NPC475601
0.9187	High Similarity	NPC124029
0.9151	High Similarity	NPC237702
0.9147	High Similarity	NPC292416
0.9147	High Similarity	NPC473689
0.9104	High Similarity	NPC63041
0.9095	High Similarity	NPC228377
0.9095	High Similarity	NPC477787
0.9095	High Similarity	NPC87152
0.9095	High Similarity	NPC475631
0.9095	High Similarity	NPC211920
0.9095	High Similarity	NPC328186
0.9095	High Similarity	NPC476110
0.9095	High Similarity	NPC122968
0.9095	High Similarity	NPC146824
0.9095	High Similarity	NPC475600
0.9078	High Similarity	NPC75600
0.9078	High Similarity	NPC212768
0.9078	High Similarity	NPC473115
0.9078	High Similarity	NPC473089
0.9078	High Similarity	NPC158020
0.9078	High Similarity	NPC6576
0.9065	High Similarity	NPC38959
0.9065	High Similarity	NPC327904
0.9052	High Similarity	NPC471190
0.9052	High Similarity	NPC475644
0.9052	High Similarity	NPC471977
0.9052	High Similarity	NPC475362
0.9052	High Similarity	NPC470486
0.9043	High Similarity	NPC250807
0.9043	High Similarity	NPC76565
0.9043	High Similarity	NPC57797
0.9038	High Similarity	NPC477903
0.9024	High Similarity	NPC264674
0.9019	High Similarity	NPC475406
0.9	High Similarity	NPC475137
0.9	High Similarity	NPC473850
0.9	High Similarity	NPC475498
0.8967	High Similarity	NPC475596
0.8967	High Similarity	NPC316841
0.8967	High Similarity	NPC475303
0.8967	High Similarity	NPC477906
0.8957	High Similarity	NPC473506
0.894	High Similarity	NPC253482
0.893	High Similarity	NPC35208
0.8925	High Similarity	NPC469748
0.8925	High Similarity	NPC30456
0.891	High Similarity	NPC477900
0.891	High Similarity	NPC477899
0.8905	High Similarity	NPC235364
0.8905	High Similarity	NPC477788
0.8843	High Similarity	NPC327769
0.8824	High Similarity	NPC475533
0.8821	High Similarity	NPC26881
0.8818	High Similarity	NPC475648
0.881	High Similarity	NPC477901
0.8785	High Similarity	NPC134384
0.8785	High Similarity	NPC311196
0.8784	High Similarity	NPC324619
0.8784	High Similarity	NPC475315
0.8756	High Similarity	NPC170751
0.8738	High Similarity	NPC285411
0.8738	High Similarity	NPC14116
0.871	High Similarity	NPC238278
0.8676	High Similarity	NPC289086
0.867	High Similarity	NPC475426
0.8664	High Similarity	NPC213143
0.8657	High Similarity	NPC91125
0.8654	High Similarity	NPC476467
0.8634	High Similarity	NPC475301
0.8634	High Similarity	NPC326930
0.8634	High Similarity	NPC53255
0.8634	High Similarity	NPC85879
0.8619	High Similarity	NPC30570
0.8596	High Similarity	NPC13603
0.8578	High Similarity	NPC162812
0.8565	High Similarity	NPC292517
0.8565	High Similarity	NPC280473
0.8565	High Similarity	NPC323551
0.8558	High Similarity	NPC233727
0.8527	High Similarity	NPC180668
0.8527	High Similarity	NPC471013
0.8527	High Similarity	NPC148896
0.8524	High Similarity	NPC41724
0.8524	High Similarity	NPC51008
0.851	High Similarity	NPC472752
0.8509	High Similarity	NPC471015
0.8502	High Similarity	NPC475835
0.8491	Intermediate Similarity	NPC328928
0.8485	Intermediate Similarity	NPC473833
0.8412	Intermediate Similarity	NPC471978
0.8377	Intermediate Similarity	NPC10904
0.8364	Intermediate Similarity	NPC187494
0.8341	Intermediate Similarity	NPC470189
0.8341	Intermediate Similarity	NPC40919
0.8305	Intermediate Similarity	NPC471979
0.8286	Intermediate Similarity	NPC470190
0.8279	Intermediate Similarity	NPC319556
0.8263	Intermediate Similarity	NPC165837
0.8186	Intermediate Similarity	NPC103230
0.8186	Intermediate Similarity	NPC193361
0.8186	Intermediate Similarity	NPC207531
0.8186	Intermediate Similarity	NPC62844
0.8038	Intermediate Similarity	NPC470279
0.7965	Intermediate Similarity	NPC476090
0.7934	Intermediate Similarity	NPC309498
0.792	Intermediate Similarity	NPC471004
0.7838	Intermediate Similarity	NPC253314
0.7798	Intermediate Similarity	NPC111732
0.7773	Intermediate Similarity	NPC320748
0.7773	Intermediate Similarity	NPC324245
0.7746	Intermediate Similarity	NPC32451
0.7746	Intermediate Similarity	NPC328559
0.77	Intermediate Similarity	NPC79223
0.7642	Intermediate Similarity	NPC329024
0.7569	Intermediate Similarity	NPC156044
0.7561	Intermediate Similarity	NPC471997
0.7523	Intermediate Similarity	NPC59033
0.7523	Intermediate Similarity	NPC317672
0.7477	Intermediate Similarity	NPC12944
0.7477	Intermediate Similarity	NPC25442
0.7476	Intermediate Similarity	NPC44354
0.7458	Intermediate Similarity	NPC37473
0.743	Intermediate Similarity	NPC109922
0.7314	Intermediate Similarity	NPC476516
0.7313	Intermediate Similarity	NPC141385
0.7273	Intermediate Similarity	NPC235885
0.7261	Intermediate Similarity	NPC107123
0.726	Intermediate Similarity	NPC155792
0.7248	Intermediate Similarity	NPC50997
0.7248	Intermediate Similarity	NPC160127
0.7225	Intermediate Similarity	NPC317010
0.7203	Intermediate Similarity	NPC70155
0.7186	Intermediate Similarity	NPC106593
0.7183	Intermediate Similarity	NPC328798
0.7183	Intermediate Similarity	NPC325775
0.7174	Intermediate Similarity	NPC140311
0.7169	Intermediate Similarity	NPC123395
0.7163	Intermediate Similarity	NPC114974
0.7162	Intermediate Similarity	NPC477043
0.7156	Intermediate Similarity	NPC327373
0.7155	Intermediate Similarity	NPC473667
0.715	Intermediate Similarity	NPC327699
0.7143	Intermediate Similarity	NPC2395
0.7143	Intermediate Similarity	NPC470280
0.7143	Intermediate Similarity	NPC146724
0.7143	Intermediate Similarity	NPC135950
0.7137	Intermediate Similarity	NPC317752
0.7124	Intermediate Similarity	NPC141428
0.7107	Intermediate Similarity	NPC15406
0.71	Intermediate Similarity	NPC107287
0.7095	Intermediate Similarity	NPC164340
0.7093	Intermediate Similarity	NPC318299
0.7091	Intermediate Similarity	NPC103361
0.7089	Intermediate Similarity	NPC233334
0.7083	Intermediate Similarity	NPC306001
0.7083	Intermediate Similarity	NPC471629
0.7083	Intermediate Similarity	NPC324251
0.7083	Intermediate Similarity	NPC473400
0.7083	Intermediate Similarity	NPC206211
0.7083	Intermediate Similarity	NPC275170
0.708	Intermediate Similarity	NPC314834
0.7078	Intermediate Similarity	NPC476517

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 NPC148860 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	226
0.1-0.2	545
0.2-0.3	717
0.3-0.4	1620
0.4-0.5	3278
0.5-0.6	2260
0.6-0.7	484
0.7-0.8	20
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
0.8246	Intermediate Similarity	NPD8468	Phase 2
0.795	Intermediate Similarity	NPD8304	Clinical (unspecified phase)
0.7639	Intermediate Similarity	NPD7396	Approved
0.7547	Intermediate Similarity	NPD5975	Clinical (unspecified phase)
0.7366	Intermediate Similarity	NPD3795	Approved
0.7366	Intermediate Similarity	NPD3794	Approved
0.7354	Intermediate Similarity	NPD7927	Clinical (unspecified phase)
0.7277	Intermediate Similarity	NPD5088	Discontinued
0.725	Intermediate Similarity	NPD820	Phase 3
0.7244	Intermediate Similarity	NPD7069	Discontinued
0.7227	Intermediate Similarity	NPD6477	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD1483	Discontinued
0.7207	Intermediate Similarity	NPD7010	Phase 3
0.7192	Intermediate Similarity	NPD6635	Approved
0.7162	Intermediate Similarity	NPD2831	Approved
0.7143	Intermediate Similarity	NPD5891	Approved
0.7125	Intermediate Similarity	NPD7886	Phase 2
0.7125	Intermediate Similarity	NPD7885	Phase 2
0.7072	Intermediate Similarity	NPD5721	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD5751	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD8325	Phase 3
0.7043	Intermediate Similarity	NPD8327	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD8326	Phase 3
0.7035	Intermediate Similarity	NPD6529	Discontinued
0.7026	Intermediate Similarity	NPD3280	Approved
0.7	Intermediate Similarity	NPD8485	Approved
0.6991	Remote Similarity	NPD2510	Approved
0.6991	Remote Similarity	NPD2509	Approved
0.6974	Remote Similarity	NPD4417	Approved
0.697	Remote Similarity	NPD4989	Phase 2
0.6957	Remote Similarity	NPD7707	Approved
0.6953	Remote Similarity	NPD8479	Phase 2
0.6938	Remote Similarity	NPD485	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD5801	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD6987	Phase 1
0.6933	Remote Similarity	NPD3947	Discontinued
0.6926	Remote Similarity	NPD3394	Approved
0.6926	Remote Similarity	NPD3393	Approved
0.6926	Remote Similarity	NPD3389	Approved
0.6912	Remote Similarity	NPD7233	Approved
0.6912	Remote Similarity	NPD7234	Approved
0.6906	Remote Similarity	NPD8486	Clinical (unspecified phase)
0.69	Remote Similarity	NPD9271	Approved
0.6897	Remote Similarity	NPD3326	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD8435	Approved
0.6877	Remote Similarity	NPD7708	Approved
0.6866	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD6361	Phase 2
0.6863	Remote Similarity	NPD6026	Approved
0.6861	Remote Similarity	NPD6661	Clinical (unspecified phase)
0.6856	Remote Similarity	NPD6262	Clinical (unspecified phase)
0.6836	Remote Similarity	NPD7803	Approved
0.6835	Remote Similarity	NPD3925	Approved
0.6827	Remote Similarity	NPD6525	Clinical (unspecified phase)
0.6814	Remote Similarity	NPD2121	Clinical (unspecified phase)
0.6812	Remote Similarity	NPD4506	Discontinued
0.6807	Remote Similarity	NPD5640	Discontinued
0.6804	Remote Similarity	NPD8360	Approved
0.6804	Remote Similarity	NPD8063	Discontinued
0.6804	Remote Similarity	NPD8361	Approved
0.6797	Remote Similarity	NPD6657	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD8052	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD6257	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD4900	Clinical (unspecified phase)
0.678	Remote Similarity	NPD4301	Approved
0.6773	Remote Similarity	NPD2336	Approved
0.6772	Remote Similarity	NPD7955	Approved
0.6772	Remote Similarity	NPD7956	Approved
0.6766	Remote Similarity	NPD6770	Approved
0.6763	Remote Similarity	NPD6962	Phase 2
0.6757	Remote Similarity	NPD4427	Phase 2
0.6753	Remote Similarity	NPD5475	Discontinued
0.6742	Remote Similarity	NPD4376	Phase 3
0.6741	Remote Similarity	NPD4987	Clinical (unspecified phase)
0.6729	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6716	Remote Similarity	NPD9075	Approved
0.6716	Remote Similarity	NPD9074	Approved
0.6708	Remote Similarity	NPD4373	Phase 2
0.6697	Remote Similarity	NPD4889	Approved
0.6681	Remote Similarity	NPD4396	Clinical (unspecified phase)
0.6681	Remote Similarity	NPD6732	Clinical (unspecified phase)
0.668	Remote Similarity	NPD7807	Clinical (unspecified phase)
0.668	Remote Similarity	NPD7417	Discontinued
0.6667	Remote Similarity	NPD53	Approved
0.6667	Remote Similarity	NPD8465	Approved
0.6667	Remote Similarity	NPD8467	Approved
0.6667	Remote Similarity	NPD8466	Approved
0.6667	Remote Similarity	NPD8091	Phase 3
0.6667	Remote Similarity	NPD7778	Approved
0.6667	Remote Similarity	NPD7777	Approved
0.6653	Remote Similarity	NPD7395	Discontinued
0.6653	Remote Similarity	NPD7878	Phase 2
0.6653	Remote Similarity	NPD3006	Discontinued
0.6653	Remote Similarity	NPD5022	Discontinued
0.6652	Remote Similarity	NPD7562	Approved
0.6652	Remote Similarity	NPD5866	Approved
0.6652	Remote Similarity	NPD2307	Discontinued
0.6652	Remote Similarity	NPD7061	Clinical (unspecified phase)
0.6651	Remote Similarity	NPD6641	Approved
0.6651	Remote Similarity	NPD6642	Approved
0.6639	Remote Similarity	NPD6298	Discontinued
0.6638	Remote Similarity	NPD6323	Clinical (unspecified phase)
0.6638	Remote Similarity	NPD3946	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD7414	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD6791	Phase 2
0.6626	Remote Similarity	NPD8409	Suspended
0.6624	Remote Similarity	NPD7571	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD7187	Phase 2
0.6613	Remote Similarity	NPD6790	Phase 1
0.6609	Remote Similarity	NPD4901	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD7470	Discontinued
0.6603	Remote Similarity	NPD2511	Approved
0.66	Remote Similarity	NPD7967	Discontinued
0.66	Remote Similarity	NPD107	Approved
0.6598	Remote Similarity	NPD8289	Discontinued
0.6592	Remote Similarity	NPD3924	Approved
0.6592	Remote Similarity	NPD3923	Approved
0.6592	Remote Similarity	NPD3921	Approved
0.6592	Remote Similarity	NPD3922	Approved
0.6589	Remote Similarity	NPD7862	Clinical (unspecified phase)
0.6587	Remote Similarity	NPD8350	Clinical (unspecified phase)
0.6584	Remote Similarity	NPD4952	Phase 3
0.6582	Remote Similarity	NPD1926	Approved
0.6567	Remote Similarity	NPD8426	Approved
0.6567	Remote Similarity	NPD8460	Approved
0.6567	Remote Similarity	NPD8459	Approved
0.6567	Remote Similarity	NPD8425	Approved
0.6565	Remote Similarity	NPD5901	Discontinued
0.6561	Remote Similarity	NPD4948	Discontinued
0.6561	Remote Similarity	NPD5482	Discontinued
0.6559	Remote Similarity	NPD5805	Approved
0.6555	Remote Similarity	NPD6955	Clinical (unspecified phase)
0.6555	Remote Similarity	NPD7404	Approved
0.6552	Remote Similarity	NPD7467	Discontinued
0.6545	Remote Similarity	NPD8407	Phase 2
0.6542	Remote Similarity	NPD8356	Approved
0.6541	Remote Similarity	NPD8429	Approved
0.6541	Remote Similarity	NPD8428	Approved
0.6541	Remote Similarity	NPD8427	Approved
0.654	Remote Similarity	NPD8000	Clinical (unspecified phase)
0.6537	Remote Similarity	NPD4862	Clinical (unspecified phase)
0.6532	Remote Similarity	NPD6825	Phase 1
0.6529	Remote Similarity	NPD7426	Phase 1
0.6525	Remote Similarity	NPD4667	Clinical (unspecified phase)
0.652	Remote Similarity	NPD8412	Phase 1
0.6516	Remote Similarity	NPD4375	Approved
0.6509	Remote Similarity	NPD5429	Discontinued
0.6504	Remote Similarity	NPD6226	Phase 3
0.6502	Remote Similarity	NPD8364	Approved
0.6502	Remote Similarity	NPD8363	Approved
0.65	Remote Similarity	NPD2896	Discontinued
0.65	Remote Similarity	NPD5147	Discontinued
0.6498	Remote Similarity	NPD5490	Discontinued
0.6491	Remote Similarity	NPD6874	Approved
0.6489	Remote Similarity	NPD4529	Approved
0.6489	Remote Similarity	NPD4526	Approved
0.6489	Remote Similarity	NPD4528	Approved
0.6489	Remote Similarity	NPD4551	Phase 2
0.6486	Remote Similarity	NPD8020	Approved
0.6486	Remote Similarity	NPD8021	Approved
0.6484	Remote Similarity	NPD3386	Phase 2
0.6484	Remote Similarity	NPD8368	Discontinued
0.6482	Remote Similarity	NPD6276	Discontinued
0.6481	Remote Similarity	NPD7947	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD8404	Phase 2
0.6468	Remote Similarity	NPD7703	Clinical (unspecified phase)
0.6468	Remote Similarity	NPD5483	Clinical (unspecified phase)
0.6468	Remote Similarity	NPD1620	Clinical (unspecified phase)
0.6466	Remote Similarity	NPD7001	Phase 3
0.6463	Remote Similarity	NPD5497	Clinical (unspecified phase)
0.6463	Remote Similarity	NPD6479	Discontinued
0.6463	Remote Similarity	NPD6219	Discontinued
0.6456	Remote Similarity	NPD8112	Clinical (unspecified phase)
0.6456	Remote Similarity	NPD4897	Phase 2
0.6456	Remote Similarity	NPD5417	Clinical (unspecified phase)
0.6454	Remote Similarity	NPD6716	Phase 1
0.6453	Remote Similarity	NPD8365	Clinical (unspecified phase)
0.645	Remote Similarity	NPD5513	Phase 2
0.6449	Remote Similarity	NPD6872	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD6569	Phase 2
0.6444	Remote Similarity	NPD3354	Phase 2
0.6444	Remote Similarity	NPD4429	Discontinued
0.6441	Remote Similarity	NPD3815	Phase 1
0.6441	Remote Similarity	NPD3816	Phase 1
0.6441	Remote Similarity	NPD8462	Phase 1
0.6438	Remote Similarity	NPD3371	Approved
0.6437	Remote Similarity	NPD6494	Phase 2
0.6434	Remote Similarity	NPD6553	Clinical (unspecified phase)
0.6434	Remote Similarity	NPD4328	Approved
0.6434	Remote Similarity	NPD7268	Clinical (unspecified phase)
0.6434	Remote Similarity	NPD8430	Approved
0.6432	Remote Similarity	NPD5506	Approved
0.6432	Remote Similarity	NPD4923	Phase 1
0.6432	Remote Similarity	NPD5507	Approved
0.6432	Remote Similarity	NPD5512	Phase 3
0.6431	Remote Similarity	NPD8101	Phase 3
0.6429	Remote Similarity	NPD6281	Approved
0.6429	Remote Similarity	NPD2582	Approved
0.6429	Remote Similarity	NPD2581	Approved
0.6426	Remote Similarity	NPD7998	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