NPASS Compound

Structure

NPC62367 OpenBabel07101719152D 45 49 0 0 1 0 0 0 0 0999 V2000 3.3948 -0.9800 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3859 -2.3659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5461 -0.4900 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1279 -1.9516 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9800 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 4.9000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8487 4.4100 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8487 4.4100 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6974 -2.9400 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0922 1.9600 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5461 -2.4500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8487 3.4300 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8487 3.4300 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2435 1.4700 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8487 -2.4500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0922 2.9400 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1469 0.4739 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4447 1.6424 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3948 2.9400 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8551 0.1108 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5461 -1.4700 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3325 -2.1123 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0935 0.7275 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.9400 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3948 1.9600 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8487 -1.4700 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8932 -0.4727 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.4233 1.5912 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6974 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8487 0.4900 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 1.9600 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5461 1.4700 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6974 -0.9800 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -0.9800 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 4.2435 3.4300 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.0255 -2.8053 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0401 2.3528 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8487 1.4700 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6974 1.9600 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4900 0.8487 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6770 0.6445 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5862 -1.1657 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5461 0.4900 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8487 1.4700 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 21 1 0 0 0 0 2 22 1 0 0 0 0 4 34 1 0 0 0 0 6 7 2 0 0 0 0 6 8 1 0 0 0 0 7 12 1 0 0 0 0 8 13 2 0 0 0 0 9 11 1 0 0 0 0 9 15 1 0 0 0 0 10 14 2 0 0 0 0 10 16 1 0 0 0 0 11 21 2 0 0 0 0 12 24 2 0 0 0 0 13 24 1 0 0 0 0 14 25 1 0 0 0 0 15 26 1 0 0 0 0 16 36 2 0 0 0 0 17 23 1 0 0 0 0 18 23 2 0 0 0 0 18 28 1 0 0 0 0 19 25 2 0 0 0 0 19 36 1 0 0 0 0 20 23 1 0 0 0 0 20 42 1 0 0 0 0 21 33 1 0 0 0 0 22 37 2 0 0 0 0 22 43 1 0 0 0 0 24 31 1 0 0 0 0 25 32 1 0 0 0 0 26 33 1 6 0 0 0 26 34 1 0 0 0 0 27 17 1 1 0 0 0 27 34 1 0 0 0 0 27 43 1 0 0 0 0 28 38 2 0 0 0 0 28 42 1 0 0 0 0 29 30 1 0 0 0 0 29 33 1 6 0 0 0 29 44 1 0 0 0 0 30 35 1 1 0 0 0 30 45 1 0 0 0 0 31 39 2 0 0 0 0 31 45 1 0 0 0 0 32 40 2 0 0 0 0 32 44 1 0 0 0 0 33 3 1 6 0 0 0 34 35 1 6 0 0 0 35 5 1 6 0 0 0 35 41 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	617.26
Volume:	629.605
LogP:	4.284
LogD:	2.779
LogS:	-3.751
# Rotatable Bonds:	11
TPSA:	145.39
# H-Bond Aceptor:	10
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.19
Synthetic Accessibility Score:	5.007
Fsp3:	0.429
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:	-5.337
MDCK Permeability:	2.5826127966865897e-05
Pgp-inhibitor:	0.994
Pgp-substrate:	0.005
Human Intestinal Absorption (HIA):	0.039
20% Bioavailability (F20%):	0.934
30% Bioavailability (F30%):	0.964

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.341
Plasma Protein Binding (PPB):	97.77457427978516%
Volume Distribution (VD):	2.11
Pgp-substrate:	6.850179195404053%

ADMET: Metabolism

CYP1A2-inhibitor:	0.446
CYP1A2-substrate:	0.054
CYP2C19-inhibitor:	0.562
CYP2C19-substrate:	0.06
CYP2C9-inhibitor:	0.596
CYP2C9-substrate:	0.414
CYP2D6-inhibitor:	0.97
CYP2D6-substrate:	0.14
CYP3A4-inhibitor:	0.904
CYP3A4-substrate:	0.266

ADMET: Excretion

Clearance (CL):	9.717
Half-life (T1/2):	0.676

ADMET: Toxicity

hERG Blockers:	0.756
Human Hepatotoxicity (H-HT):	0.25
Drug-inuced Liver Injury (DILI):	0.773
AMES Toxicity:	0.005
Rat Oral Acute Toxicity:	0.19
Maximum Recommended Daily Dose:	0.165
Skin Sensitization:	0.287
Carcinogencity:	0.15
Eye Corrosion:	0.003
Eye Irritation:	0.035
Respiratory Toxicity:	0.888

Download Data

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

Natural Product: NPC62367

Natural Product ID:	NPC62367
*Common Name:**	Barbatellarines B
IUPAC Name:	[(1R,2S,3R,4S,4aS,8aR)-4-[(1S)-1-acetyloxy-2-(5-oxo-2H-furan-3-yl)ethyl]-2-benzoyloxy-3-hydroxy-3,4,8,8a-tetramethyl-2,4a,5,6-tetrahydro-1H-naphthalen-1-yl] pyridine-3-carboxylate
Synonyms:
Standard InCHIKey:	MCLQCMZKRLWBGH-MJBSQTHJSA-N
Standard InCHI:	InChI=1S/C35H39NO9/c1-21-11-9-15-26-33(21,3)29(44-32(40)25-14-10-16-36-19-25)30(45-31(39)24-12-7-6-8-13-24)35(5,41)34(26,4)27(43-22(2)37)17-23-18-28(38)42-20-23/h6-8,10-14,16,18-19,26-27,29-30,41H,9,15,17,20H2,1-5H3/t26-,27-,29-,30-,33-,34-,35-/m0/s1
SMILES:	CC(=O)O[C@H]([C@]1(C)[C@H]2CCC=C([C@]2(C)[C@H]([C@@H]([C@]1(C)O)OC(=O)c1ccccc1)OC(=O)c1cccnc1)C)CC1=CC(=O)OC1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL595527
PubChem CID:	46225292
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	1
Others	1

Activity Type	# Activity
Cell Line	1
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	41400.0	nM	PMID[472776]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	Inhibition	<	50.0	%	PMID[472777]

☑ 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 NPC62367 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	324
0.1-0.2	1374
0.2-0.3	3292
0.3-0.4	10141
0.4-0.5	17090
0.5-0.6	8402
0.6-0.7	1753
0.7-0.8	141
0.8-0.85	53
0.85-0.9	38
0.9-0.95	72
0.95-1	17

Similarity Score	Similarity Level	Natural Product ID
0.9948	High Similarity	NPC216428
0.9896	High Similarity	NPC477909
0.9896	High Similarity	NPC42678
0.9896	High Similarity	NPC477907
0.9847	High Similarity	NPC477912
0.9745	High Similarity	NPC301368
0.9745	High Similarity	NPC84815
0.9741	High Similarity	NPC472553
0.965	High Similarity	NPC148860
0.9645	High Similarity	NPC472555
0.9643	High Similarity	NPC471016
0.9643	High Similarity	NPC6981
0.96	High Similarity	NPC477902
0.9598	High Similarity	NPC127026
0.9598	High Similarity	NPC127720
0.9594	High Similarity	NPC294579
0.9594	High Similarity	NPC144779
0.9592	High Similarity	NPC470306
0.9585	High Similarity	NPC48042
0.9585	High Similarity	NPC472550
0.9585	High Similarity	NPC304179
0.955	High Similarity	NPC471980
0.9543	High Similarity	NPC475408
0.9543	High Similarity	NPC206343
0.9543	High Similarity	NPC471014
0.9543	High Similarity	NPC477908
0.9541	High Similarity	NPC319128
0.9541	High Similarity	NPC4421
0.9505	High Similarity	NPC124029
0.9502	High Similarity	NPC328154
0.95	High Similarity	NPC477911
0.9492	High Similarity	NPC477910
0.9442	High Similarity	NPC228331
0.9433	High Similarity	NPC63041
0.9409	High Similarity	NPC328186
0.9409	High Similarity	NPC228377
0.9409	High Similarity	NPC87152
0.9409	High Similarity	NPC475631
0.9409	High Similarity	NPC211920
0.9409	High Similarity	NPC476110
0.9409	High Similarity	NPC475600
0.9409	High Similarity	NPC122968
0.9409	High Similarity	NPC477787
0.9397	High Similarity	NPC158020
0.9397	High Similarity	NPC75600
0.9397	High Similarity	NPC473115
0.9397	High Similarity	NPC6576
0.9397	High Similarity	NPC473089
0.9397	High Similarity	NPC212768
0.9363	High Similarity	NPC475644
0.9363	High Similarity	NPC470486
0.9363	High Similarity	NPC471977
0.9363	High Similarity	NPC471190
0.9356	High Similarity	NPC57797
0.9356	High Similarity	NPC76565
0.9356	High Similarity	NPC250807
0.9353	High Similarity	NPC477903
0.9343	High Similarity	NPC264674
0.931	High Similarity	NPC475137
0.931	High Similarity	NPC473850
0.931	High Similarity	NPC475498
0.9272	High Similarity	NPC477906
0.9272	High Similarity	NPC475596
0.9272	High Similarity	NPC292416
0.9272	High Similarity	NPC316841
0.9272	High Similarity	NPC150698
0.9272	High Similarity	NPC473689
0.9272	High Similarity	NPC475303
0.9272	High Similarity	NPC96801
0.9265	High Similarity	NPC473506
0.9227	High Similarity	NPC244839
0.9227	High Similarity	NPC30456
0.9227	High Similarity	NPC320324
0.9227	High Similarity	NPC319880
0.922	High Similarity	NPC475601
0.922	High Similarity	NPC146824
0.9216	High Similarity	NPC477900
0.9216	High Similarity	NPC477899
0.9212	High Similarity	NPC235364
0.9212	High Similarity	NPC477788
0.9183	High Similarity	NPC237702
0.9175	High Similarity	NPC475362
0.9139	High Similarity	NPC475406
0.9139	High Similarity	NPC327769
0.9122	High Similarity	NPC26881
0.9113	High Similarity	NPC477901
0.9095	High Similarity	NPC38959
0.9095	High Similarity	NPC327904
0.9048	High Similarity	NPC170751
0.9043	High Similarity	NPC469748
0.8967	High Similarity	NPC253482
0.8957	High Similarity	NPC35208
0.8957	High Similarity	NPC475426
0.8955	High Similarity	NPC476467
0.8947	High Similarity	NPC91125
0.8852	High Similarity	NPC14116
0.8852	High Similarity	NPC285411
0.8843	High Similarity	NPC475648
0.881	High Similarity	NPC134384
0.881	High Similarity	NPC311196
0.8794	High Similarity	NPC289086
0.8768	High Similarity	NPC280473
0.8768	High Similarity	NPC323551
0.8732	High Similarity	NPC30570
0.8725	High Similarity	NPC51008
0.8725	High Similarity	NPC41724
0.8689	High Similarity	NPC162812
0.8676	High Similarity	NPC292517
0.8645	High Similarity	NPC238278
0.8614	High Similarity	NPC475835
0.8598	High Similarity	NPC213143
0.8591	High Similarity	NPC475533
0.8552	High Similarity	NPC324619
0.8552	High Similarity	NPC475315
0.8545	High Similarity	NPC180668
0.8545	High Similarity	NPC471013
0.8545	High Similarity	NPC148896
0.8529	High Similarity	NPC472752
0.8491	Intermediate Similarity	NPC233727
0.8454	Intermediate Similarity	NPC165837
0.8407	Intermediate Similarity	NPC85879
0.8407	Intermediate Similarity	NPC475301
0.8407	Intermediate Similarity	NPC53255
0.8407	Intermediate Similarity	NPC326930
0.8393	Intermediate Similarity	NPC10904
0.8381	Intermediate Similarity	NPC187494
0.8373	Intermediate Similarity	NPC62844
0.8373	Intermediate Similarity	NPC193361
0.837	Intermediate Similarity	NPC13603
0.8363	Intermediate Similarity	NPC471015
0.8357	Intermediate Similarity	NPC470189
0.8357	Intermediate Similarity	NPC40919
0.8301	Intermediate Similarity	NPC470190
0.8294	Intermediate Similarity	NPC319556
0.8291	Intermediate Similarity	NPC103230
0.8268	Intermediate Similarity	NPC328928
0.8261	Intermediate Similarity	NPC473833
0.8227	Intermediate Similarity	NPC470279
0.8214	Intermediate Similarity	NPC476090
0.8204	Intermediate Similarity	NPC309498
0.8199	Intermediate Similarity	NPC207531
0.819	Intermediate Similarity	NPC471978
0.8085	Intermediate Similarity	NPC471979
0.8009	Intermediate Similarity	NPC253314
0.7928	Intermediate Similarity	NPC471004
0.7887	Intermediate Similarity	NPC111732
0.7864	Intermediate Similarity	NPC324245
0.7864	Intermediate Similarity	NPC320748
0.7837	Intermediate Similarity	NPC32451
0.7837	Intermediate Similarity	NPC328559
0.7788	Intermediate Similarity	NPC79223
0.7729	Intermediate Similarity	NPC329024
0.7653	Intermediate Similarity	NPC156044
0.7647	Intermediate Similarity	NPC44354
0.7609	Intermediate Similarity	NPC37473
0.7608	Intermediate Similarity	NPC317672
0.7608	Intermediate Similarity	NPC59033
0.7562	Intermediate Similarity	NPC471997
0.7559	Intermediate Similarity	NPC12944
0.7559	Intermediate Similarity	NPC25442
0.7475	Intermediate Similarity	NPC317010
0.7466	Intermediate Similarity	NPC141385
0.7429	Intermediate Similarity	NPC109922
0.7418	Intermediate Similarity	NPC155792
0.7406	Intermediate Similarity	NPC123395
0.7384	Intermediate Similarity	NPC476516
0.7381	Intermediate Similarity	NPC135950
0.7364	Intermediate Similarity	NPC317752
0.7358	Intermediate Similarity	NPC107287
0.7348	Intermediate Similarity	NPC70155
0.7333	Intermediate Similarity	NPC106593
0.7331	Intermediate Similarity	NPC107123
0.7324	Intermediate Similarity	NPC160127
0.7324	Intermediate Similarity	NPC103361
0.7324	Intermediate Similarity	NPC50997
0.7321	Intermediate Similarity	NPC140311
0.7318	Intermediate Similarity	NPC318299
0.7306	Intermediate Similarity	NPC314834
0.7301	Intermediate Similarity	NPC473667
0.7299	Intermediate Similarity	NPC146724
0.7294	Intermediate Similarity	NPC470280
0.7282	Intermediate Similarity	NPC207851
0.7264	Intermediate Similarity	NPC249614
0.726	Intermediate Similarity	NPC328798
0.726	Intermediate Similarity	NPC325775
0.7255	Intermediate Similarity	NPC164340
0.7233	Intermediate Similarity	NPC327373
0.7228	Intermediate Similarity	NPC191310
0.7225	Intermediate Similarity	NPC327699
0.7217	Intermediate Similarity	NPC21483
0.7217	Intermediate Similarity	NPC198205
0.7193	Intermediate Similarity	NPC235885
0.7175	Intermediate Similarity	NPC274842
0.7173	Intermediate Similarity	NPC15406
0.7169	Intermediate Similarity	NPC314297
0.7169	Intermediate Similarity	NPC315545
0.7162	Intermediate Similarity	NPC244856
0.7156	Intermediate Similarity	NPC477043
0.7155	Intermediate Similarity	NPC233334
0.715	Intermediate Similarity	NPC112741

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 NPC62367 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	215
0.1-0.2	534
0.2-0.3	676
0.3-0.4	1541
0.4-0.5	3296
0.5-0.6	2285
0.6-0.7	569
0.7-0.8	32
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8341	Intermediate Similarity	NPD8468	Phase 2
0.8238	Intermediate Similarity	NPD8304	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD7396	Approved
0.7805	Intermediate Similarity	NPD5975	Clinical (unspecified phase)
0.7604	Intermediate Similarity	NPD3795	Approved
0.7604	Intermediate Similarity	NPD3794	Approved
0.7593	Intermediate Similarity	NPD7927	Clinical (unspecified phase)
0.7513	Intermediate Similarity	NPD820	Phase 3
0.7449	Intermediate Similarity	NPD6635	Approved
0.7442	Intermediate Similarity	NPD7010	Phase 3
0.7359	Intermediate Similarity	NPD5891	Approved
0.7318	Intermediate Similarity	NPD7069	Discontinued
0.7302	Intermediate Similarity	NPD5721	Clinical (unspecified phase)
0.7277	Intermediate Similarity	NPD1483	Discontinued
0.7265	Intermediate Similarity	NPD8327	Clinical (unspecified phase)
0.7265	Intermediate Similarity	NPD8326	Phase 3
0.7265	Intermediate Similarity	NPD8325	Phase 3
0.726	Intermediate Similarity	NPD6529	Discontinued
0.7244	Intermediate Similarity	NPD3280	Approved
0.7206	Intermediate Similarity	NPD5751	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD4417	Approved
0.7191	Intermediate Similarity	NPD7885	Phase 2
0.7191	Intermediate Similarity	NPD7886	Phase 2
0.7178	Intermediate Similarity	NPD485	Clinical (unspecified phase)
0.7156	Intermediate Similarity	NPD3947	Discontinued
0.715	Intermediate Similarity	NPD9271	Approved
0.7143	Intermediate Similarity	NPD7234	Approved
0.7143	Intermediate Similarity	NPD3393	Approved
0.7143	Intermediate Similarity	NPD7233	Approved
0.7143	Intermediate Similarity	NPD3389	Approved
0.7143	Intermediate Similarity	NPD3394	Approved
0.7136	Intermediate Similarity	NPD2510	Approved
0.7136	Intermediate Similarity	NPD2509	Approved
0.7107	Intermediate Similarity	NPD6026	Approved
0.71	Intermediate Similarity	NPD5088	Discontinued
0.7083	Intermediate Similarity	NPD6661	Clinical (unspecified phase)
0.7064	Intermediate Similarity	NPD6477	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.7028	Intermediate Similarity	NPD8063	Discontinued
0.7027	Intermediate Similarity	NPD4506	Discontinued
0.7018	Intermediate Similarity	NPD8479	Phase 2
0.7009	Intermediate Similarity	NPD6657	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD2831	Approved
0.7	Intermediate Similarity	NPD6987	Phase 1
0.6995	Remote Similarity	NPD2336	Approved
0.6991	Remote Similarity	NPD8485	Approved
0.6987	Remote Similarity	NPD4301	Approved
0.6974	Remote Similarity	NPD6770	Approved
0.6964	Remote Similarity	NPD5475	Discontinued
0.6963	Remote Similarity	NPD4376	Phase 3
0.6959	Remote Similarity	NPD9075	Approved
0.6959	Remote Similarity	NPD4987	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD9074	Approved
0.6935	Remote Similarity	NPD7708	Approved
0.693	Remote Similarity	NPD6361	Phase 2
0.6898	Remote Similarity	NPD4427	Phase 2
0.6895	Remote Similarity	NPD8486	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD7803	Approved
0.6886	Remote Similarity	NPD4989	Phase 2
0.6885	Remote Similarity	NPD6525	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD53	Approved
0.6881	Remote Similarity	NPD7778	Approved
0.6881	Remote Similarity	NPD7777	Approved
0.6875	Remote Similarity	NPD6641	Approved
0.6875	Remote Similarity	NPD6642	Approved
0.6872	Remote Similarity	NPD7707	Approved
0.6869	Remote Similarity	NPD8361	Approved
0.6869	Remote Similarity	NPD8435	Approved
0.6869	Remote Similarity	NPD8360	Approved
0.6866	Remote Similarity	NPD2307	Discontinued
0.6866	Remote Similarity	NPD7061	Clinical (unspecified phase)
0.6856	Remote Similarity	NPD7878	Phase 2
0.6854	Remote Similarity	NPD6791	Phase 2
0.6854	Remote Similarity	NPD6257	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.6851	Remote Similarity	NPD8052	Clinical (unspecified phase)
0.6851	Remote Similarity	NPD5801	Clinical (unspecified phase)
0.6847	Remote Similarity	NPD6323	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD107	Approved
0.6833	Remote Similarity	NPD7187	Phase 2
0.6832	Remote Similarity	NPD2511	Approved
0.6827	Remote Similarity	NPD7955	Approved
0.6827	Remote Similarity	NPD7956	Approved
0.682	Remote Similarity	NPD8409	Suspended
0.6816	Remote Similarity	NPD6732	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD8289	Discontinued
0.6794	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD7562	Approved
0.6776	Remote Similarity	NPD4948	Discontinued
0.6771	Remote Similarity	NPD5901	Discontinued
0.6761	Remote Similarity	NPD4889	Approved
0.6753	Remote Similarity	NPD7404	Approved
0.6742	Remote Similarity	NPD4396	Clinical (unspecified phase)
0.6741	Remote Similarity	NPD4862	Clinical (unspecified phase)
0.674	Remote Similarity	NPD7470	Discontinued
0.6739	Remote Similarity	NPD3326	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD2896	Discontinued
0.6736	Remote Similarity	NPD7417	Discontinued
0.672	Remote Similarity	NPD8091	Phase 3
0.6712	Remote Similarity	NPD6226	Phase 3
0.6711	Remote Similarity	NPD5866	Approved
0.671	Remote Similarity	NPD7395	Discontinued
0.6709	Remote Similarity	NPD5022	Discontinued
0.6708	Remote Similarity	NPD8412	Phase 1
0.6698	Remote Similarity	NPD8021	Approved
0.6698	Remote Similarity	NPD8020	Approved
0.6698	Remote Similarity	NPD7414	Clinical (unspecified phase)
0.6697	Remote Similarity	NPD4528	Approved
0.6697	Remote Similarity	NPD4529	Approved
0.6697	Remote Similarity	NPD4526	Approved
0.6696	Remote Similarity	NPD6262	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD5490	Discontinued
0.6695	Remote Similarity	NPD6298	Discontinued
0.6681	Remote Similarity	NPD3925	Approved
0.6681	Remote Similarity	NPD7947	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD8000	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD8356	Approved
0.6667	Remote Similarity	NPD6790	Phase 1
0.6667	Remote Similarity	NPD4901	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6479	Discontinued
0.6653	Remote Similarity	NPD5640	Discontinued
0.6653	Remote Similarity	NPD7967	Discontinued
0.6652	Remote Similarity	NPD8112	Clinical (unspecified phase)
0.6651	Remote Similarity	NPD3921	Approved
0.6651	Remote Similarity	NPD3923	Approved
0.6651	Remote Similarity	NPD3922	Approved
0.6651	Remote Similarity	NPD3924	Approved
0.665	Remote Similarity	NPD2581	Approved
0.665	Remote Similarity	NPD2582	Approved
0.664	Remote Similarity	NPD8350	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD3006	Discontinued
0.6638	Remote Similarity	NPD1926	Approved
0.6637	Remote Similarity	NPD3371	Approved
0.6636	Remote Similarity	NPD6281	Approved
0.6633	Remote Similarity	NPD1270	Approved
0.6623	Remote Similarity	NPD4900	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD7998	Clinical (unspecified phase)
0.6618	Remote Similarity	NPD6446	Discontinued
0.6613	Remote Similarity	NPD5482	Discontinued
0.6612	Remote Similarity	NPD5805	Approved
0.6611	Remote Similarity	NPD8372	Clinical (unspecified phase)
0.6611	Remote Similarity	NPD6962	Phase 2
0.6609	Remote Similarity	NPD6955	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD7571	Clinical (unspecified phase)
0.6608	Remote Similarity	NPD7191	Phase 2
0.6608	Remote Similarity	NPD7467	Discontinued
0.6606	Remote Similarity	NPD5003	Discontinued
0.6598	Remote Similarity	NPD7807	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD7958	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD7001	Phase 3
0.6593	Remote Similarity	NPD7957	Phase 1
0.6592	Remote Similarity	NPD8248	Clinical (unspecified phase)
0.6592	Remote Similarity	NPD4601	Approved
0.6592	Remote Similarity	NPD4600	Approved
0.6582	Remote Similarity	NPD7426	Phase 1
0.6578	Remote Similarity	NPD6176	Phase 1
0.6575	Remote Similarity	NPD6665	Discontinued
0.6575	Remote Similarity	NPD7862	Clinical (unspecified phase)
0.6574	Remote Similarity	NPD4375	Approved
0.6566	Remote Similarity	NPD3813	Approved
0.6564	Remote Similarity	NPD5429	Discontinued
0.6556	Remote Similarity	NPD4373	Phase 2
0.6555	Remote Similarity	NPD8430	Approved
0.6553	Remote Similarity	NPD5147	Discontinued
0.6547	Remote Similarity	NPD6999	Discontinued
0.6547	Remote Similarity	NPD7000	Clinical (unspecified phase)
0.6547	Remote Similarity	NPD6874	Approved
0.6545	Remote Similarity	NPD4551	Phase 2
0.6542	Remote Similarity	NPD7688	Phase 1
0.6542	Remote Similarity	NPD3386	Phase 2
0.6542	Remote Similarity	NPD3178	Discontinued
0.654	Remote Similarity	NPD7269	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD5965	Clinical (unspecified phase)
0.6532	Remote Similarity	NPD6276	Discontinued
0.6528	Remote Similarity	NPD6241	Phase 1
0.6528	Remote Similarity	NPD8407	Phase 2
0.6527	Remote Similarity	NPD8467	Approved
0.6527	Remote Similarity	NPD8466	Approved
0.6527	Remote Similarity	NPD8465	Approved
0.6526	Remote Similarity	NPD1620	Clinical (unspecified phase)
0.6526	Remote Similarity	NPD5398	Clinical (unspecified phase)
0.6525	Remote Similarity	NPD6995	Phase 1
0.6524	Remote Similarity	NPD6739	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD7703	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD1631	Approved
0.6518	Remote Similarity	NPD5483	Clinical (unspecified phase)
0.6518	Remote Similarity	NPD6219	Discontinued
0.6511	Remote Similarity	NPD1996	Discontinued
0.6509	Remote Similarity	NPD5417	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD3238	Discontinued
0.6509	Remote Similarity	NPD5100	Phase 3
0.6507	Remote Similarity	NPD6872	Clinical (unspecified phase)
0.6504	Remote Similarity	NPD5513	Phase 2
0.6504	Remote Similarity	NPD6716	Phase 1
0.65	Remote Similarity	NPD6569	Phase 2
0.6496	Remote Similarity	NPD4429	Discontinued
0.6496	Remote Similarity	NPD3354	Phase 2
0.6494	Remote Similarity	NPD3816	Phase 1
0.6494	Remote Similarity	NPD3815	Phase 1
0.6488	Remote Similarity	NPD6494	Phase 2

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