NPASS Compound

Structure

NPC124029 OpenBabel07101719512D 42 47 0 0 1 0 0 0 0 0999 V2000 0.8660 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0570 1.0878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6750 1.0878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3660 2.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.2218 2.8479 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3660 2.0388 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 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 1 20 1 0 0 0 0 3 31 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 20 2 0 0 0 0 11 21 2 0 0 0 0 12 21 1 0 0 0 0 13 22 1 0 0 0 0 14 23 1 0 0 0 0 15 34 2 0 0 0 0 16 24 1 0 0 0 0 17 25 1 0 0 0 0 17 33 1 0 0 0 0 18 22 2 0 0 0 0 18 34 1 0 0 0 0 19 33 1 0 0 0 0 19 39 1 0 0 0 0 20 30 1 0 0 0 0 21 28 1 0 0 0 0 22 29 1 0 0 0 0 23 30 1 6 0 0 0 23 31 1 0 0 0 0 24 31 1 1 0 0 0 24 40 1 0 0 0 0 25 35 2 0 0 0 0 25 39 1 0 0 0 0 26 27 1 0 0 0 0 26 32 1 1 0 0 0 26 36 1 0 0 0 0 27 30 1 6 0 0 0 27 41 1 0 0 0 0 28 37 2 0 0 0 0 28 41 1 0 0 0 0 29 38 2 0 0 0 0 29 40 1 0 0 0 0 30 2 1 6 0 0 0 31 32 1 6 0 0 0 32 4 1 6 0 0 0 32 42 1 0 0 0 0 33 16 1 1 0 0 0 33 42 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	575.25
Volume:	582.939
LogP:	4.142
LogD:	2.897
LogS:	-4.399
# Rotatable Bonds:	6
TPSA:	121.25
# H-Bond Aceptor:	9
# H-Bond Donor:	1
# Rings:	6
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.32
Synthetic Accessibility Score:	5.402
Fsp3:	0.515
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:	-5.383
MDCK Permeability:	2.705423321458511e-05
Pgp-inhibitor:	0.998
Pgp-substrate:	0.108
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.972
30% Bioavailability (F30%):	0.984

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.802
Plasma Protein Binding (PPB):	92.51293182373047%
Volume Distribution (VD):	1.737
Pgp-substrate:	6.73664665222168%

ADMET: Metabolism

CYP1A2-inhibitor:	0.179
CYP1A2-substrate:	0.139
CYP2C19-inhibitor:	0.46
CYP2C19-substrate:	0.12
CYP2C9-inhibitor:	0.424
CYP2C9-substrate:	0.053
CYP2D6-inhibitor:	0.273
CYP2D6-substrate:	0.052
CYP3A4-inhibitor:	0.951
CYP3A4-substrate:	0.415

ADMET: Excretion

Clearance (CL):	12.691
Half-life (T1/2):	0.526

ADMET: Toxicity

hERG Blockers:	0.855
Human Hepatotoxicity (H-HT):	0.191
Drug-inuced Liver Injury (DILI):	0.751
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.315
Maximum Recommended Daily Dose:	0.923
Skin Sensitization:	0.344
Carcinogencity:	0.155
Eye Corrosion:	0.003
Eye Irritation:	0.035
Respiratory Toxicity:	0.878

Download Data

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

Natural Product: NPC124029

Natural Product ID:	NPC124029
*Common Name:**	Scutehenanine B
IUPAC Name:	[(1S,3S,4aR,5S,6R,6aR,10aS,10bS)-6-benzoyloxy-5-hydroxy-4a,6a,7,10b-tetramethyl-2'-oxospiro[2,5,6,9,10,10a-hexahydro-1H-benzo[f]chromene-3,4'-oxolane]-1-yl] pyridine-3-carboxylate
Synonyms:
Standard InCHIKey:	WFFUGMCEOIJHMN-GRTFKUIQSA-N
Standard InCHI:	InChI=1S/C33H37NO8/c1-20-10-8-14-23-30(20,2)27(41-28(37)21-11-6-5-7-12-21)26(36)32(4)31(23,3)24(16-33(42-32)17-25(35)39-19-33)40-29(38)22-13-9-15-34-18-22/h5-7,9-13,15,18,23-24,26-27,36H,8,14,16-17,19H2,1-4H3/t23-,24-,26-,27-,30-,31-,32-,33-/m0/s1
SMILES:	CC1=CCC[C@H]2[C@@]1(C)[C@H]([C@@H]([C@@]1(C)[C@]2(C)[C@H](C[C@@]2(CC(=O)OC2)O1)OC(=O)c1cccnc1)O)OC(=O)c1ccccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1077449
PubChem CID:	44556948
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	=	4700.0	nM	PMID[556202]
NPT139	Cell Line	HT-29	Homo sapiens	IC50	=	5000.0	nM	PMID[556202]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	3500.0	nM	PMID[556202]

☑ 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 NPC124029 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	347
0.1-0.2	1421
0.2-0.3	3016
0.3-0.4	9384
0.4-0.5	16786
0.5-0.6	9527
0.6-0.7	1894
0.7-0.8	129
0.8-0.85	47
0.85-0.9	43
0.9-0.95	81
0.95-1	22

Similarity Score	Similarity Level	Natural Product ID
0.9901	High Similarity	NPC211920
0.99	High Similarity	NPC477902
0.9756	High Similarity	NPC477906
0.9565	High Similarity	NPC96801
0.9565	High Similarity	NPC150698
0.9557	High Similarity	NPC477903
0.9512	High Similarity	NPC26881
0.9505	High Similarity	NPC62367
0.9463	High Similarity	NPC471980
0.9458	High Similarity	NPC216428
0.9458	High Similarity	NPC301368
0.9458	High Similarity	NPC84815
0.9453	High Similarity	NPC264674
0.942	High Similarity	NPC475601
0.9417	High Similarity	NPC477900
0.9417	High Similarity	NPC477899
0.9417	High Similarity	NPC328154
0.9415	High Similarity	NPC127026
0.9415	High Similarity	NPC127720
0.9415	High Similarity	NPC235364
0.9409	High Similarity	NPC144779
0.9409	High Similarity	NPC294579
0.9406	High Similarity	NPC477907
0.9406	High Similarity	NPC42678
0.9406	High Similarity	NPC477909
0.9366	High Similarity	NPC477912
0.936	High Similarity	NPC471016
0.936	High Similarity	NPC471014
0.936	High Similarity	NPC475408
0.936	High Similarity	NPC6981
0.9333	High Similarity	NPC469748
0.933	High Similarity	NPC91125
0.9317	High Similarity	NPC477901
0.931	High Similarity	NPC470306
0.9268	High Similarity	NPC472555
0.9261	High Similarity	NPC4421
0.9257	High Similarity	NPC472553
0.922	High Similarity	NPC473089
0.922	High Similarity	NPC6576
0.922	High Similarity	NPC158020
0.922	High Similarity	NPC75600
0.922	High Similarity	NPC212768
0.922	High Similarity	NPC473115
0.919	High Similarity	NPC470486
0.919	High Similarity	NPC471190
0.919	High Similarity	NPC471977
0.919	High Similarity	NPC475644
0.9187	High Similarity	NPC148860
0.9171	High Similarity	NPC206343
0.9171	High Similarity	NPC477908
0.9163	High Similarity	NPC253482
0.9155	High Similarity	NPC35208
0.9151	High Similarity	NPC30456
0.9143	High Similarity	NPC122968
0.9143	High Similarity	NPC475600
0.9143	High Similarity	NPC477787
0.9143	High Similarity	NPC328186
0.9143	High Similarity	NPC475631
0.9143	High Similarity	NPC87152
0.9143	High Similarity	NPC228377
0.9143	High Similarity	NPC476110
0.9139	High Similarity	NPC475137
0.9139	High Similarity	NPC475498
0.9139	High Similarity	NPC473850
0.9135	High Similarity	NPC477911
0.9124	High Similarity	NPC475648
0.9122	High Similarity	NPC477910
0.9109	High Similarity	NPC48042
0.9109	High Similarity	NPC472550
0.9109	High Similarity	NPC304179
0.9104	High Similarity	NPC475303
0.9104	High Similarity	NPC475596
0.9104	High Similarity	NPC316841
0.9095	High Similarity	NPC473506
0.9091	High Similarity	NPC57797
0.9091	High Similarity	NPC76565
0.9091	High Similarity	NPC250807
0.9073	High Similarity	NPC319128
0.9065	High Similarity	NPC475426
0.9065	High Similarity	NPC327769
0.9059	High Similarity	NPC63041
0.9029	High Similarity	NPC30570
0.9019	High Similarity	NPC237702
0.9014	High Similarity	NPC473689
0.9014	High Similarity	NPC292416
0.9009	High Similarity	NPC475362
0.8981	High Similarity	NPC228331
0.8977	High Similarity	NPC475406
0.8972	High Similarity	NPC319880
0.8972	High Similarity	NPC244839
0.8972	High Similarity	NPC320324
0.8962	High Similarity	NPC146824
0.8952	High Similarity	NPC477788
0.8935	High Similarity	NPC38959
0.8935	High Similarity	NPC327904
0.8889	High Similarity	NPC170751
0.8883	High Similarity	NPC292517
0.8843	High Similarity	NPC238278
0.8804	High Similarity	NPC162812
0.8796	High Similarity	NPC213143
0.8785	High Similarity	NPC285411
0.8785	High Similarity	NPC14116
0.8744	High Similarity	NPC311196
0.8744	High Similarity	NPC134384
0.8702	High Similarity	NPC476467
0.8692	High Similarity	NPC233727
0.8647	High Similarity	NPC472752
0.8634	High Similarity	NPC471015
0.8578	High Similarity	NPC193361
0.8578	High Similarity	NPC62844
0.8571	High Similarity	NPC180668
0.8571	High Similarity	NPC148896
0.8571	High Similarity	NPC471013
0.8524	High Similarity	NPC323551
0.8524	High Similarity	NPC280473
0.8498	Intermediate Similarity	NPC187494
0.8496	Intermediate Similarity	NPC324619
0.8496	Intermediate Similarity	NPC475315
0.8483	Intermediate Similarity	NPC51008
0.8483	Intermediate Similarity	NPC41724
0.8462	Intermediate Similarity	NPC475835
0.8454	Intermediate Similarity	NPC289086
0.8451	Intermediate Similarity	NPC475533
0.8448	Intermediate Similarity	NPC473833
0.8421	Intermediate Similarity	NPC10904
0.8326	Intermediate Similarity	NPC319556
0.831	Intermediate Similarity	NPC165837
0.8302	Intermediate Similarity	NPC470189
0.8302	Intermediate Similarity	NPC40919
0.8298	Intermediate Similarity	NPC471978
0.8276	Intermediate Similarity	NPC475301
0.8276	Intermediate Similarity	NPC85879
0.8276	Intermediate Similarity	NPC326930
0.8276	Intermediate Similarity	NPC53255
0.8246	Intermediate Similarity	NPC470190
0.824	Intermediate Similarity	NPC13603
0.8233	Intermediate Similarity	NPC207531
0.822	Intermediate Similarity	NPC328928
0.8166	Intermediate Similarity	NPC476090
0.8128	Intermediate Similarity	NPC253314
0.8117	Intermediate Similarity	NPC471979
0.8086	Intermediate Similarity	NPC470279
0.8066	Intermediate Similarity	NPC309498
0.8058	Intermediate Similarity	NPC103230
0.7965	Intermediate Similarity	NPC471004
0.7844	Intermediate Similarity	NPC111732
0.782	Intermediate Similarity	NPC324245
0.782	Intermediate Similarity	NPC320748
0.7793	Intermediate Similarity	NPC32451
0.7793	Intermediate Similarity	NPC328559
0.7746	Intermediate Similarity	NPC79223
0.7689	Intermediate Similarity	NPC329024
0.7615	Intermediate Similarity	NPC156044
0.757	Intermediate Similarity	NPC59033
0.757	Intermediate Similarity	NPC317672
0.7546	Intermediate Similarity	NPC155792
0.7523	Intermediate Similarity	NPC25442
0.7523	Intermediate Similarity	NPC12944
0.7521	Intermediate Similarity	NPC107123
0.75	Intermediate Similarity	NPC476516
0.7441	Intermediate Similarity	NPC44354
0.744	Intermediate Similarity	NPC471997
0.7426	Intermediate Similarity	NPC37473
0.7377	Intermediate Similarity	NPC478045
0.7357	Intermediate Similarity	NPC141385
0.7356	Intermediate Similarity	NPC317010
0.7316	Intermediate Similarity	NPC141428
0.7315	Intermediate Similarity	NPC191193
0.7315	Intermediate Similarity	NPC321072
0.7315	Intermediate Similarity	NPC242662
0.7315	Intermediate Similarity	NPC109922
0.7315	Intermediate Similarity	NPC215892
0.7294	Intermediate Similarity	NPC50997
0.7294	Intermediate Similarity	NPC160127
0.729	Intermediate Similarity	NPC324251
0.729	Intermediate Similarity	NPC473400
0.729	Intermediate Similarity	NPC306001
0.729	Intermediate Similarity	NPC206211
0.729	Intermediate Similarity	NPC475336
0.729	Intermediate Similarity	NPC471629
0.729	Intermediate Similarity	NPC453583
0.729	Intermediate Similarity	NPC317882
0.729	Intermediate Similarity	NPC471754
0.729	Intermediate Similarity	NPC275170
0.729	Intermediate Similarity	NPC473300
0.7281	Intermediate Similarity	NPC471606
0.7281	Intermediate Similarity	NPC208553
0.7281	Intermediate Similarity	NPC181964
0.7277	Intermediate Similarity	NPC314834
0.7269	Intermediate Similarity	NPC135950
0.7261	Intermediate Similarity	NPC476517
0.7258	Intermediate Similarity	NPC191489
0.7256	Intermediate Similarity	NPC33372
0.7256	Intermediate Similarity	NPC67246
0.7253	Intermediate Similarity	NPC57690
0.7248	Intermediate Similarity	NPC473558
0.7241	Intermediate Similarity	NPC235885
0.723	Intermediate Similarity	NPC328798
0.723	Intermediate Similarity	NPC325775
0.7229	Intermediate Similarity	NPC106593

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 NPC124029 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	534
0.2-0.3	680
0.3-0.4	1791
0.4-0.5	3345
0.5-0.6	2052
0.6-0.7	494
0.7-0.8	28
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
0.821	Intermediate Similarity	NPD8468	Phase 2
0.791	Intermediate Similarity	NPD8304	Clinical (unspecified phase)
0.7767	Intermediate Similarity	NPD7396	Approved
0.7557	Intermediate Similarity	NPD7927	Clinical (unspecified phase)
0.7512	Intermediate Similarity	NPD5975	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD1483	Discontinued
0.7467	Intermediate Similarity	NPD8325	Phase 3
0.7467	Intermediate Similarity	NPD8327	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD8326	Phase 3
0.7411	Intermediate Similarity	NPD3794	Approved
0.7411	Intermediate Similarity	NPD3795	Approved
0.7281	Intermediate Similarity	NPD8485	Approved
0.7258	Intermediate Similarity	NPD7708	Approved
0.7257	Intermediate Similarity	NPD5891	Approved
0.7238	Intermediate Similarity	NPD7886	Phase 2
0.7238	Intermediate Similarity	NPD7885	Phase 2
0.7214	Intermediate Similarity	NPD820	Phase 3
0.7211	Intermediate Similarity	NPD7803	Approved
0.7195	Intermediate Similarity	NPD5721	Clinical (unspecified phase)
0.7182	Intermediate Similarity	NPD8486	Clinical (unspecified phase)
0.7175	Intermediate Similarity	NPD7010	Phase 3
0.7157	Intermediate Similarity	NPD6635	Approved
0.7143	Intermediate Similarity	NPD6525	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD53	Approved
0.7091	Intermediate Similarity	NPD7778	Approved
0.7091	Intermediate Similarity	NPD7777	Approved
0.7083	Intermediate Similarity	NPD8435	Approved
0.7083	Intermediate Similarity	NPD8360	Approved
0.7083	Intermediate Similarity	NPD8361	Approved
0.708	Intermediate Similarity	NPD6529	Discontinued
0.7069	Intermediate Similarity	NPD3280	Approved
0.7061	Intermediate Similarity	NPD7069	Discontinued
0.7056	Intermediate Similarity	NPD7878	Phase 2
0.7043	Intermediate Similarity	NPD3389	Approved
0.7043	Intermediate Similarity	NPD3394	Approved
0.7043	Intermediate Similarity	NPD3393	Approved
0.7037	Intermediate Similarity	NPD7233	Approved
0.7037	Intermediate Similarity	NPD7234	Approved
0.7018	Intermediate Similarity	NPD4417	Approved
0.7014	Intermediate Similarity	NPD6641	Approved
0.7014	Intermediate Similarity	NPD6642	Approved
0.7012	Intermediate Similarity	NPD7956	Approved
0.7012	Intermediate Similarity	NPD7955	Approved
0.7012	Intermediate Similarity	NPD8409	Suspended
0.6996	Remote Similarity	NPD8479	Phase 2
0.6986	Remote Similarity	NPD485	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD3947	Discontinued
0.696	Remote Similarity	NPD2510	Approved
0.696	Remote Similarity	NPD2509	Approved
0.6946	Remote Similarity	NPD8372	Clinical (unspecified phase)
0.6934	Remote Similarity	NPD5751	Clinical (unspecified phase)
0.693	Remote Similarity	NPD4506	Discontinued
0.6927	Remote Similarity	NPD8063	Discontinued
0.6926	Remote Similarity	NPD7707	Approved
0.6912	Remote Similarity	NPD6026	Approved
0.6912	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD6661	Clinical (unspecified phase)
0.6895	Remote Similarity	NPD2336	Approved
0.6894	Remote Similarity	NPD4301	Approved
0.688	Remote Similarity	NPD6770	Approved
0.6867	Remote Similarity	NPD4989	Phase 2
0.6866	Remote Similarity	NPD9271	Approved
0.6858	Remote Similarity	NPD2121	Clinical (unspecified phase)
0.684	Remote Similarity	NPD6657	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD8091	Phase 3
0.6828	Remote Similarity	NPD6987	Phase 1
0.6827	Remote Similarity	NPD5088	Discontinued
0.682	Remote Similarity	NPD8407	Phase 2
0.6814	Remote Similarity	NPD6477	Clinical (unspecified phase)
0.6812	Remote Similarity	NPD2511	Approved
0.6797	Remote Similarity	NPD5475	Discontinued
0.6786	Remote Similarity	NPD4987	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD8289	Discontinued
0.6771	Remote Similarity	NPD2307	Discontinued
0.676	Remote Similarity	NPD8350	Clinical (unspecified phase)
0.6754	Remote Similarity	NPD2831	Approved
0.6745	Remote Similarity	NPD6739	Clinical (unspecified phase)
0.6732	Remote Similarity	NPD8373	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD4601	Approved
0.6726	Remote Similarity	NPD4427	Phase 2
0.6726	Remote Similarity	NPD4600	Approved
0.6725	Remote Similarity	NPD4901	Clinical (unspecified phase)
0.6719	Remote Similarity	NPD8370	Discontinued
0.6712	Remote Similarity	NPD4376	Phase 3
0.6696	Remote Similarity	NPD7061	Clinical (unspecified phase)
0.6695	Remote Similarity	NPD1926	Approved
0.6694	Remote Similarity	NPD8052	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD8412	Phase 1
0.6694	Remote Similarity	NPD5801	Clinical (unspecified phase)
0.6683	Remote Similarity	NPD9075	Approved
0.6683	Remote Similarity	NPD9074	Approved
0.6682	Remote Similarity	NPD6361	Phase 2
0.6682	Remote Similarity	NPD8368	Discontinued
0.6682	Remote Similarity	NPD6791	Phase 2
0.6681	Remote Similarity	NPD6323	Clinical (unspecified phase)
0.668	Remote Similarity	NPD4086	Phase 1
0.6667	Remote Similarity	NPD7404	Approved
0.6667	Remote Similarity	NPD7187	Phase 2
0.6653	Remote Similarity	NPD8356	Approved
0.6653	Remote Similarity	NPD6790	Phase 1
0.6653	Remote Similarity	NPD8404	Phase 2
0.6652	Remote Similarity	NPD6732	Clinical (unspecified phase)
0.6642	Remote Similarity	NPD8467	Approved
0.6642	Remote Similarity	NPD8465	Approved
0.6642	Remote Similarity	NPD8466	Approved
0.6628	Remote Similarity	NPD7862	Clinical (unspecified phase)
0.6626	Remote Similarity	NPD3006	Discontinued
0.6624	Remote Similarity	NPD8462	Phase 1
0.662	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6612	Remote Similarity	NPD4373	Phase 2
0.6609	Remote Similarity	NPD5901	Discontinued
0.6606	Remote Similarity	NPD8021	Approved
0.6606	Remote Similarity	NPD6257	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD8020	Approved
0.6606	Remote Similarity	NPD4948	Discontinued
0.6598	Remote Similarity	NPD3925	Approved
0.6598	Remote Similarity	NPD6962	Phase 2
0.6595	Remote Similarity	NPD7947	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD5003	Discontinued
0.6586	Remote Similarity	NPD7417	Discontinued
0.6582	Remote Similarity	NPD8000	Clinical (unspecified phase)
0.6581	Remote Similarity	NPD7470	Discontinued
0.658	Remote Similarity	NPD4862	Clinical (unspecified phase)
0.658	Remote Similarity	NPD7958	Clinical (unspecified phase)
0.658	Remote Similarity	NPD7957	Phase 1
0.6579	Remote Similarity	NPD4396	Clinical (unspecified phase)
0.657	Remote Similarity	NPD7426	Phase 1
0.6568	Remote Similarity	NPD8112	Clinical (unspecified phase)
0.6567	Remote Similarity	NPD107	Approved
0.6557	Remote Similarity	NPD5022	Discontinued
0.6555	Remote Similarity	NPD7395	Discontinued
0.6553	Remote Similarity	NPD5866	Approved
0.6552	Remote Similarity	NPD7562	Approved
0.6543	Remote Similarity	NPD8430	Approved
0.6543	Remote Similarity	NPD8460	Approved
0.6543	Remote Similarity	NPD8459	Approved
0.6543	Remote Similarity	NPD8425	Approved
0.6543	Remote Similarity	NPD8426	Approved
0.6542	Remote Similarity	NPD6298	Discontinued
0.6542	Remote Similarity	NPD5147	Discontinued
0.654	Remote Similarity	NPD8363	Approved
0.654	Remote Similarity	NPD8364	Approved
0.654	Remote Similarity	NPD5490	Discontinued
0.6538	Remote Similarity	NPD4900	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD5482	Discontinued
0.6533	Remote Similarity	NPD4529	Approved
0.6533	Remote Similarity	NPD4526	Approved
0.6533	Remote Similarity	NPD4528	Approved
0.6526	Remote Similarity	NPD6446	Discontinued
0.6522	Remote Similarity	NPD6276	Discontinued
0.6518	Remote Similarity	NPD7807	Clinical (unspecified phase)
0.6517	Remote Similarity	NPD8427	Approved
0.6517	Remote Similarity	NPD8429	Approved
0.6517	Remote Similarity	NPD8428	Approved
0.6516	Remote Similarity	NPD4889	Approved
0.6508	Remote Similarity	NPD7967	Discontinued
0.6507	Remote Similarity	NPD4500	Approved
0.6507	Remote Similarity	NPD4501	Approved
0.6502	Remote Similarity	NPD5640	Discontinued
0.6494	Remote Similarity	NPD6716	Phase 1
0.6491	Remote Similarity	NPD8365	Clinical (unspecified phase)
0.649	Remote Similarity	NPD4952	Phase 3
0.6489	Remote Similarity	NPD6665	Discontinued
0.6484	Remote Similarity	NPD5897	Approved
0.6484	Remote Similarity	NPD5898	Approved
0.6484	Remote Similarity	NPD5899	Approved
0.6481	Remote Similarity	NPD3371	Approved
0.6476	Remote Similarity	NPD6226	Phase 3
0.6473	Remote Similarity	NPD6281	Approved
0.6468	Remote Similarity	NPD6262	Clinical (unspecified phase)
0.6468	Remote Similarity	NPD2896	Discontinued
0.6468	Remote Similarity	NPD7998	Clinical (unspecified phase)
0.6466	Remote Similarity	NPD5805	Approved
0.6463	Remote Similarity	NPD6874	Approved
0.6461	Remote Similarity	NPD7269	Clinical (unspecified phase)
0.6459	Remote Similarity	NPD4926	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD6955	Clinical (unspecified phase)
0.6456	Remote Similarity	NPD1270	Approved
0.6456	Remote Similarity	NPD7571	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD7414	Clinical (unspecified phase)
0.6454	Remote Similarity	NPD7576	Discontinued
0.6453	Remote Similarity	NPD7191	Phase 2
0.6447	Remote Similarity	NPD6206	Phase 1
0.6446	Remote Similarity	NPD6995	Phase 1
0.6444	Remote Similarity	NPD3326	Clinical (unspecified phase)
0.6443	Remote Similarity	NPD5483	Clinical (unspecified phase)
0.6435	Remote Similarity	NPD6479	Discontinued
0.6435	Remote Similarity	NPD8248	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD4897	Phase 2
0.6422	Remote Similarity	NPD6176	Phase 1
0.6422	Remote Similarity	NPD5513	Phase 2
0.6417	Remote Similarity	NPD8375	Approved
0.6416	Remote Similarity	NPD3923	Approved
0.6416	Remote Similarity	NPD3921	Approved
0.6416	Remote Similarity	NPD3922	Approved
0.6416	Remote Similarity	NPD3924	Approved
0.6414	Remote Similarity	NPD3815	Phase 1
0.6414	Remote Similarity	NPD3816	Phase 1
0.6413	Remote Similarity	NPD4375	Approved
0.6411	Remote Similarity	NPD6741	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