NPASS Compound

Structure

CID121327 OpenBabel06191715472D 42 47 0 0 0 0 0 0 0 0999 V2000 -2.6471 -5.3565 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0484 -4.3385 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5919 5.2952 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9932 4.2772 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0979 -2.5271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9941 3.7530 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6863 -0.8933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6311 0.8320 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2741 -1.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2189 1.6411 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4661 -3.6340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4109 3.5727 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5474 -2.4760 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4922 2.4147 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0539 -4.4430 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9987 4.3817 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6918 -0.9979 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6366 0.9366 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8728 -2.7204 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8176 2.6591 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4037 -2.1670 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4589 2.1057 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1316 -0.5197 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0764 0.4584 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2850 -1.9114 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2299 1.8501 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0826 -0.8287 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0274 0.7674 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9486 -0.3287 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8934 0.2674 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6116 -1.1889 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6668 1.1276 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8673 -2.6159 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.8122 2.5546 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.2905 -1.8069 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.2353 1.7456 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.0532 0.6658 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9980 -0.7271 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5627 -0.8798 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6178 0.8185 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1468 -2.8361 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2020 2.7748 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 15 1 0 0 0 0 2 15 1 0 0 0 0 3 16 1 0 0 0 0 4 16 1 0 0 0 0 5 41 1 0 0 0 0 6 42 1 0 0 0 0 7 9 2 0 0 0 0 7 17 1 0 0 0 0 8 10 2 0 0 0 0 8 18 1 0 0 0 0 9 33 1 0 0 0 0 10 34 1 0 0 0 0 11 15 1 0 0 0 0 11 19 1 0 0 0 0 12 16 1 0 0 0 0 12 20 1 0 0 0 0 13 21 2 0 0 0 0 13 35 1 0 0 0 0 14 22 2 0 0 0 0 14 36 1 0 0 0 0 17 25 2 0 0 0 0 17 29 1 0 0 0 0 18 26 2 0 0 0 0 18 30 1 0 0 0 0 19 25 1 0 0 0 0 19 33 2 0 0 0 0 20 26 1 0 0 0 0 20 34 2 0 0 0 0 21 31 1 0 0 0 0 21 41 1 0 0 0 0 22 32 1 0 0 0 0 22 42 1 0 0 0 0 23 24 1 0 0 0 0 23 27 2 0 0 0 0 23 31 1 0 0 0 0 24 28 2 0 0 0 0 24 32 1 0 0 0 0 25 35 1 0 0 0 0 26 36 1 0 0 0 0 27 29 1 0 0 0 0 27 35 1 0 0 0 0 28 30 1 0 0 0 0 28 36 1 0 0 0 0 29 37 2 0 0 0 0 30 38 2 0 0 0 0 31 39 2 0 0 0 0 32 40 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	566.22
Volume:	570.507
LogP:	4.269
LogD:	2.243
LogS:	-4.636
# Rotatable Bonds:	5
TPSA:	133.46
# H-Bond Aceptor:	10
# H-Bond Donor:	4
# Rings:	6
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.208
Synthetic Accessibility Score:	4.091
Fsp3:	0.188
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:	-5.819
MDCK Permeability:	7.598448064527474e-06
Pgp-inhibitor:	0.994
Pgp-substrate:	0.999
Human Intestinal Absorption (HIA):	0.711
20% Bioavailability (F20%):	0.235
30% Bioavailability (F30%):	0.015

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.044
Plasma Protein Binding (PPB):	81.80266571044922%
Volume Distribution (VD):	0.416
Pgp-substrate:	19.005104064941406%

ADMET: Metabolism

CYP1A2-inhibitor:	0.232
CYP1A2-substrate:	0.983
CYP2C19-inhibitor:	0.763
CYP2C19-substrate:	0.474
CYP2C9-inhibitor:	0.934
CYP2C9-substrate:	0.952
CYP2D6-inhibitor:	0.326
CYP2D6-substrate:	0.893
CYP3A4-inhibitor:	0.359
CYP3A4-substrate:	0.528

ADMET: Excretion

Clearance (CL):	2.217
Half-life (T1/2):	0.427

ADMET: Toxicity

hERG Blockers:	0.015
Human Hepatotoxicity (H-HT):	0.964
Drug-inuced Liver Injury (DILI):	0.975
AMES Toxicity:	0.892
Rat Oral Acute Toxicity:	0.306
Maximum Recommended Daily Dose:	0.993
Skin Sensitization:	0.313
Carcinogencity:	0.811
Eye Corrosion:	0.003
Eye Irritation:	0.151
Respiratory Toxicity:	0.229

Download Data

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

Natural Product: NPC121327

Natural Product ID:	NPC121327
*Common Name:**	Pterocellin E
IUPAC Name:	8-methoxy-6-[8-methoxy-1-(2-methylpropyl)-5,7-dioxopyrido[4,3-b]indolizin-6-yl]-1-(2-methylpropyl)pyrido[4,3-b]indolizine-5,7-dione
Synonyms:	Pterocellin E
Standard InCHIKey:	LYLGSTUCVSNTAR-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C32H30N4O6/c1-15(2)11-19-25-17(7-9-33-19)29(37)27-23(31(39)21(41-5)13-35(25)27)24-28-30(38)18-8-10-34-20(12-16(3)4)26(18)36(28)14-22(42-6)32(24)40/h7-10,13-16H,11-12H2,1-6H3
SMILES:	CC(C)Cc1c2-n3cc(c(=O)c(c4c5C(=O)c6ccnc(CC(C)C)c6-n5cc(c4=O)OC)c3C(=O)c2ccn1)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL403030
PubChem CID:	24770105
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000089] Pyridines and derivatives [CHEMONTID:0000326] Bipyridines and oligopyridines

*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
NPO26327	Chaenomeles sinensis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14600382]
NPO24293	Neorautanenia mitis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16562843]
NPO25419	Pterocella vesiculosa	Species	n.a.	n.a.	n.a.	New Zealand	n.a.	PMID[18052329]
NPO25419	Pterocella vesiculosa	Species	n.a.	n.a.	n.a.	Alderman Islands off the North Island of New Zealand	n.a.	PMID[18052329]
NPO25419	Pterocella vesiculosa	Species	n.a.	n.a.	n.a.	New Zealand	n.a.	PMID[19220033]
NPO25419	Pterocella vesiculosa	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[19220033]
NPO26327	Chaenomeles sinensis	Species	Rosaceae	Eukaryota	Twigs	n.a.	n.a.	PMID[25894905]
NPO26327	Chaenomeles sinensis	Species	Rosaceae	Eukaryota	Twigs	n.a.	n.a.	PMID[28358502]
NPO26327	Chaenomeles sinensis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26327	Chaenomeles sinensis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24293	Neorautanenia mitis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26327	Chaenomeles sinensis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO24293	Neorautanenia mitis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25419	Pterocella vesiculosa	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO26055	Relhania fruticosa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26327	Chaenomeles sinensis	Species	Rosaceae	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
MIC	1

Activity Type	# Activity
Cell Line	1
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	IC50	>	6.25	ug.mL-1	PMID[480688]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	1.0	ug	PMID[480688]

☑ 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 NPC121327 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	630
0.1-0.2	3838
0.2-0.3	13192
0.3-0.4	8871
0.4-0.5	12156
0.5-0.6	2560
0.6-0.7	1337
0.7-0.8	104
0.8-0.85	3
0.85-0.9	4
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9669	High Similarity	NPC143977
0.9101	High Similarity	NPC46895
0.904	High Similarity	NPC61011
0.8927	High Similarity	NPC83774
0.8827	High Similarity	NPC73994
0.829	Intermediate Similarity	NPC81535
0.7624	Intermediate Similarity	NPC472069
0.7624	Intermediate Similarity	NPC472063
0.7624	Intermediate Similarity	NPC472062
0.7598	Intermediate Similarity	NPC472064
0.7598	Intermediate Similarity	NPC472065
0.7576	Intermediate Similarity	NPC326422
0.755	Intermediate Similarity	NPC106824
0.7538	Intermediate Similarity	NPC118084
0.75	Intermediate Similarity	NPC317701
0.75	Intermediate Similarity	NPC472116
0.7475	Intermediate Similarity	NPC284338
0.7435	Intermediate Similarity	NPC469529
0.7423	Intermediate Similarity	NPC191415
0.7404	Intermediate Similarity	NPC472070
0.7389	Intermediate Similarity	NPC74413
0.7347	Intermediate Similarity	NPC258480
0.7343	Intermediate Similarity	NPC238457
0.732	Intermediate Similarity	NPC12649
0.7283	Intermediate Similarity	NPC70406
0.7282	Intermediate Similarity	NPC260900
0.7268	Intermediate Similarity	NPC157583
0.7268	Intermediate Similarity	NPC284775
0.7264	Intermediate Similarity	NPC216550
0.7255	Intermediate Similarity	NPC474916
0.7241	Intermediate Similarity	NPC128244
0.7225	Intermediate Similarity	NPC70949
0.7214	Intermediate Similarity	NPC476460
0.7208	Intermediate Similarity	NPC102755
0.7206	Intermediate Similarity	NPC167710
0.7194	Intermediate Similarity	NPC471997
0.7189	Intermediate Similarity	NPC470679
0.7189	Intermediate Similarity	NPC472260
0.7189	Intermediate Similarity	NPC217021
0.7188	Intermediate Similarity	NPC65080
0.7186	Intermediate Similarity	NPC66210
0.7158	Intermediate Similarity	NPC265100
0.7158	Intermediate Similarity	NPC478182
0.7151	Intermediate Similarity	NPC251391
0.7143	Intermediate Similarity	NPC304203
0.7129	Intermediate Similarity	NPC472259
0.7129	Intermediate Similarity	NPC114974
0.7129	Intermediate Similarity	NPC473763
0.7129	Intermediate Similarity	NPC117244
0.712	Intermediate Similarity	NPC105811
0.7105	Intermediate Similarity	NPC242116
0.7103	Intermediate Similarity	NPC234078
0.7103	Intermediate Similarity	NPC221100
0.7092	Intermediate Similarity	NPC237188
0.7087	Intermediate Similarity	NPC168911
0.7085	Intermediate Similarity	NPC467063
0.7085	Intermediate Similarity	NPC477003
0.7083	Intermediate Similarity	NPC114637
0.7083	Intermediate Similarity	NPC56233
0.7081	Intermediate Similarity	NPC123906
0.7079	Intermediate Similarity	NPC472112
0.7073	Intermediate Similarity	NPC472293
0.7059	Intermediate Similarity	NPC267343
0.7053	Intermediate Similarity	NPC237414
0.7048	Intermediate Similarity	NPC327592
0.7048	Intermediate Similarity	NPC101350
0.7045	Intermediate Similarity	NPC229893
0.7043	Intermediate Similarity	NPC313889
0.7039	Intermediate Similarity	NPC227582
0.7033	Intermediate Similarity	NPC328318
0.7033	Intermediate Similarity	NPC328596
0.703	Intermediate Similarity	NPC255909
0.7028	Intermediate Similarity	NPC266249
0.7024	Intermediate Similarity	NPC135950
0.7019	Intermediate Similarity	NPC252338
0.7014	Intermediate Similarity	NPC317373
0.7011	Intermediate Similarity	NPC467188
0.7005	Intermediate Similarity	NPC212213
0.7005	Intermediate Similarity	NPC27041
0.7004	Intermediate Similarity	NPC235685
0.7	Intermediate Similarity	NPC80681
0.7	Intermediate Similarity	NPC293487
0.6995	Remote Similarity	NPC324091
0.6995	Remote Similarity	NPC154339
0.6995	Remote Similarity	NPC469489
0.699	Remote Similarity	NPC102592
0.699	Remote Similarity	NPC79356
0.6977	Remote Similarity	NPC471194
0.6977	Remote Similarity	NPC318299
0.6977	Remote Similarity	NPC471193
0.6977	Remote Similarity	NPC153980
0.6977	Remote Similarity	NPC6865
0.6971	Remote Similarity	NPC472297
0.6971	Remote Similarity	NPC103361
0.6971	Remote Similarity	NPC472296
0.6968	Remote Similarity	NPC281094
0.6965	Remote Similarity	NPC282103
0.6963	Remote Similarity	NPC100104
0.6963	Remote Similarity	NPC470680
0.6963	Remote Similarity	NPC123839
0.6952	Remote Similarity	NPC57398
0.6952	Remote Similarity	NPC473878
0.6951	Remote Similarity	NPC476491
0.695	Remote Similarity	NPC143533
0.6948	Remote Similarity	NPC116555
0.6947	Remote Similarity	NPC141053
0.6944	Remote Similarity	NPC317752
0.6935	Remote Similarity	NPC15840
0.6931	Remote Similarity	NPC209362
0.693	Remote Similarity	NPC72956
0.6927	Remote Similarity	NPC472292
0.6927	Remote Similarity	NPC47190
0.6927	Remote Similarity	NPC472113
0.6923	Remote Similarity	NPC239954
0.6923	Remote Similarity	NPC34837
0.6923	Remote Similarity	NPC471943
0.6919	Remote Similarity	NPC234987
0.6915	Remote Similarity	NPC472119
0.6907	Remote Similarity	NPC478183
0.6903	Remote Similarity	NPC207686
0.6898	Remote Similarity	NPC477413
0.6897	Remote Similarity	NPC472323
0.6895	Remote Similarity	NPC473310
0.6893	Remote Similarity	NPC198673
0.6891	Remote Similarity	NPC478184
0.689	Remote Similarity	NPC123395
0.6888	Remote Similarity	NPC152620
0.6887	Remote Similarity	NPC289086
0.6887	Remote Similarity	NPC88115
0.6881	Remote Similarity	NPC471192
0.6881	Remote Similarity	NPC472107
0.6881	Remote Similarity	NPC79062
0.6881	Remote Similarity	NPC207531
0.6872	Remote Similarity	NPC106757
0.6869	Remote Similarity	NPC151635
0.6863	Remote Similarity	NPC103119
0.686	Remote Similarity	NPC202812
0.6859	Remote Similarity	NPC213914
0.6856	Remote Similarity	NPC233380
0.6849	Remote Similarity	NPC53534
0.6847	Remote Similarity	NPC155444
0.6847	Remote Similarity	NPC311858
0.6845	Remote Similarity	NPC100726
0.6845	Remote Similarity	NPC272458
0.6844	Remote Similarity	NPC191382
0.6844	Remote Similarity	NPC56109
0.6842	Remote Similarity	NPC229055
0.6839	Remote Similarity	NPC478185
0.6837	Remote Similarity	NPC32534
0.6835	Remote Similarity	NPC474412
0.6827	Remote Similarity	NPC109922
0.6823	Remote Similarity	NPC474492
0.6818	Remote Similarity	NPC319556
0.6818	Remote Similarity	NPC469938
0.6816	Remote Similarity	NPC122436
0.6812	Remote Similarity	NPC247735
0.6812	Remote Similarity	NPC472210
0.6812	Remote Similarity	NPC269886
0.6812	Remote Similarity	NPC472295
0.6812	Remote Similarity	NPC81802
0.681	Remote Similarity	NPC474767
0.6806	Remote Similarity	NPC74357
0.6804	Remote Similarity	NPC21174
0.6804	Remote Similarity	NPC271797
0.6802	Remote Similarity	NPC262338
0.68	Remote Similarity	NPC475258
0.6798	Remote Similarity	NPC308931
0.6798	Remote Similarity	NPC99939
0.6798	Remote Similarity	NPC133003
0.6796	Remote Similarity	NPC472097
0.6796	Remote Similarity	NPC138370
0.6782	Remote Similarity	NPC159125
0.6782	Remote Similarity	NPC470205
0.6782	Remote Similarity	NPC117027
0.678	Remote Similarity	NPC473666
0.6779	Remote Similarity	NPC220151
0.6779	Remote Similarity	NPC19692
0.6769	Remote Similarity	NPC42372
0.6768	Remote Similarity	NPC161861
0.6768	Remote Similarity	NPC252572
0.6766	Remote Similarity	NPC477042
0.6766	Remote Similarity	NPC24864
0.6765	Remote Similarity	NPC141612
0.6765	Remote Similarity	NPC17273
0.6765	Remote Similarity	NPC135601
0.6759	Remote Similarity	NPC472752
0.6756	Remote Similarity	NPC909
0.6756	Remote Similarity	NPC475338
0.6751	Remote Similarity	NPC91895
0.675	Remote Similarity	NPC28848
0.675	Remote Similarity	NPC64436
0.675	Remote Similarity	NPC14325
0.6749	Remote Similarity	NPC228835
0.6746	Remote Similarity	NPC245916
0.6744	Remote Similarity	NPC225821
0.6743	Remote Similarity	NPC118940
0.6739	Remote Similarity	NPC477549
0.6739	Remote Similarity	NPC471574
0.6735	Remote Similarity	NPC41717
0.6734	Remote Similarity	NPC293216

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 NPC121327 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	341
0.1-0.2	655
0.2-0.3	1044
0.3-0.4	1971
0.4-0.5	2764
0.5-0.6	1802
0.6-0.7	537
0.7-0.8	36
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
0.7333	Intermediate Similarity	NPD4011	Clinical (unspecified phase)
0.7323	Intermediate Similarity	NPD4988	Discontinued
0.7316	Intermediate Similarity	NPD1343	Approved
0.7308	Intermediate Similarity	NPD1270	Approved
0.7277	Intermediate Similarity	NPD3389	Approved
0.7277	Intermediate Similarity	NPD3394	Approved
0.7277	Intermediate Similarity	NPD3393	Approved
0.7225	Intermediate Similarity	NPD3905	Phase 3
0.7194	Intermediate Similarity	NPD1291	Clinical (unspecified phase)
0.7194	Intermediate Similarity	NPD2481	Approved
0.7194	Intermediate Similarity	NPD2479	Phase 3
0.719	Intermediate Similarity	NPD2509	Approved
0.719	Intermediate Similarity	NPD2510	Approved
0.719	Intermediate Similarity	NPD7665	Phase 2
0.719	Intermediate Similarity	NPD7666	Phase 3
0.7163	Intermediate Similarity	NPD8000	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD5088	Discontinued
0.7121	Intermediate Similarity	NPD7401	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD2879	Approved
0.7115	Intermediate Similarity	NPD2881	Approved
0.7098	Intermediate Similarity	NPD1573	Approved
0.7098	Intermediate Similarity	NPD1575	Approved
0.7073	Intermediate Similarity	NPD7061	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD5017	Discontinued
0.7059	Intermediate Similarity	NPD5887	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD6454	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD6999	Discontinued
0.7053	Intermediate Similarity	NPD6137	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD7000	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD1292	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD6173	Approved
0.7019	Intermediate Similarity	NPD8248	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD7568	Phase 1
0.7	Intermediate Similarity	NPD7482	Phase 2
0.7	Intermediate Similarity	NPD7483	Phase 2
0.699	Remote Similarity	NPD4848	Phase 1
0.6977	Remote Similarity	NPD6954	Phase 2
0.6976	Remote Similarity	NPD460	Discontinued
0.6967	Remote Similarity	NPD6987	Phase 1
0.6967	Remote Similarity	NPD3947	Discontinued
0.6967	Remote Similarity	NPD6288	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD2336	Approved
0.6961	Remote Similarity	NPD6180	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD1568	Clinical (unspecified phase)
0.6934	Remote Similarity	NPD2008	Discontinued
0.6931	Remote Similarity	NPD5820	Clinical (unspecified phase)
0.693	Remote Similarity	NPD7927	Clinical (unspecified phase)
0.693	Remote Similarity	NPD4614	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD2121	Clinical (unspecified phase)
0.6916	Remote Similarity	NPD1600	Suspended
0.6915	Remote Similarity	NPD6178	Phase 3
0.6915	Remote Similarity	NPD5965	Clinical (unspecified phase)
0.6912	Remote Similarity	NPD5685	Approved
0.6912	Remote Similarity	NPD5686	Approved
0.6911	Remote Similarity	NPD1630	Approved
0.6907	Remote Similarity	NPD4643	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD3839	Phase 2
0.6901	Remote Similarity	NPD3840	Phase 2
0.6898	Remote Similarity	NPD2411	Approved
0.6892	Remote Similarity	NPD7661	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD7712	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD4051	Discontinued
0.6881	Remote Similarity	NPD2412	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD4851	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD180	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD6787	Phase 2
0.6866	Remote Similarity	NPD5888	Phase 2
0.6856	Remote Similarity	NPD4958	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD4524	Discontinued
0.6852	Remote Similarity	NPD6567	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD4989	Phase 2
0.6847	Remote Similarity	NPD5444	Phase 1
0.6845	Remote Similarity	NPD5505	Discontinued
0.6844	Remote Similarity	NPD7780	Approved
0.6844	Remote Similarity	NPD7781	Approved
0.6842	Remote Similarity	NPD4987	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD7204	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD5400	Approved
0.683	Remote Similarity	NPD8289	Discontinued
0.6827	Remote Similarity	NPD2307	Discontinued
0.6821	Remote Similarity	NPD6446	Discontinued
0.6808	Remote Similarity	NPD3247	Clinical (unspecified phase)
0.6804	Remote Similarity	NPD1631	Approved
0.6792	Remote Similarity	NPD7187	Phase 2
0.6792	Remote Similarity	NPD4924	Clinical (unspecified phase)
0.6779	Remote Similarity	NPD7944	Discontinued
0.6778	Remote Similarity	NPD1627	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD7001	Phase 3
0.6776	Remote Similarity	NPD3967	Approved
0.6774	Remote Similarity	NPD6152	Phase 1
0.6765	Remote Similarity	NPD4426	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD3315	Phase 3
0.6763	Remote Similarity	NPD7098	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD7704	Clinical (unspecified phase)
0.6758	Remote Similarity	NPD8242	Clinical (unspecified phase)
0.6749	Remote Similarity	NPD7564	Discontinued
0.6748	Remote Similarity	NPD3321	Discontinued
0.6746	Remote Similarity	NPD7818	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD7023	Clinical (unspecified phase)
0.6745	Remote Similarity	NPD7903	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD6470	Phase 3
0.6739	Remote Similarity	NPD569	Clinical (unspecified phase)
0.6734	Remote Similarity	NPD4736	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD1783	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD8408	Discontinued
0.6732	Remote Similarity	NPD2770	Discontinued
0.673	Remote Similarity	NPD6239	Discontinued
0.6728	Remote Similarity	NPD5072	Discontinued
0.6728	Remote Similarity	NPD6204	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD7730	Approved
0.6726	Remote Similarity	NPD7731	Approved
0.6725	Remote Similarity	NPD7789	Approved
0.6725	Remote Similarity	NPD7790	Approved
0.6725	Remote Similarity	NPD7953	Approved
0.6725	Remote Similarity	NPD7791	Approved
0.6725	Remote Similarity	NPD7951	Approved
0.6725	Remote Similarity	NPD7952	Approved
0.6725	Remote Similarity	NPD7950	Approved
0.6716	Remote Similarity	NPD8304	Clinical (unspecified phase)
0.6714	Remote Similarity	NPD1952	Discontinued
0.6713	Remote Similarity	NPD2442	Approved
0.6713	Remote Similarity	NPD2443	Approved
0.6713	Remote Similarity	NPD7191	Phase 2
0.6712	Remote Similarity	NPD7404	Approved
0.6702	Remote Similarity	NPD7469	Discontinued
0.6701	Remote Similarity	NPD2511	Approved
0.67	Remote Similarity	NPD5104	Approved
0.67	Remote Similarity	NPD5728	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD7234	Approved
0.6699	Remote Similarity	NPD7233	Approved
0.6699	Remote Similarity	NPD4602	Approved
0.6698	Remote Similarity	NPD6732	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD4501	Approved
0.6698	Remote Similarity	NPD4500	Approved
0.6697	Remote Similarity	NPD3326	Clinical (unspecified phase)
0.6697	Remote Similarity	NPD2787	Clinical (unspecified phase)
0.6697	Remote Similarity	NPD5475	Discontinued
0.6697	Remote Similarity	NPD3805	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD8356	Approved
0.6684	Remote Similarity	NPD2915	Discontinued
0.6683	Remote Similarity	NPD3927	Phase 2
0.6683	Remote Similarity	NPD4922	Phase 2
0.6682	Remote Similarity	NPD3968	Approved
0.6667	Remote Similarity	NPD6771	Discontinued
0.6667	Remote Similarity	NPD7824	Approved
0.6667	Remote Similarity	NPD7594	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6838	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1096	Discontinued
0.6667	Remote Similarity	NPD1506	Discontinued
0.6667	Remote Similarity	NPD7195	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3607	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD715	Phase 3
0.6667	Remote Similarity	NPD2753	Discontinued
0.6652	Remote Similarity	NPD8430	Approved
0.6651	Remote Similarity	NPD5854	Approved
0.6651	Remote Similarity	NPD6661	Clinical (unspecified phase)
0.6651	Remote Similarity	NPD8114	Approved
0.6651	Remote Similarity	NPD8115	Approved
0.665	Remote Similarity	NPD4174	Clinical (unspecified phase)
0.665	Remote Similarity	NPD4883	Approved
0.6637	Remote Similarity	NPD7271	Approved
0.6635	Remote Similarity	NPD6206	Phase 1
0.6635	Remote Similarity	NPD3785	Clinical (unspecified phase)
0.6634	Remote Similarity	NPD4336	Clinical (unspecified phase)
0.6634	Remote Similarity	NPD5555	Phase 1
0.663	Remote Similarity	NPD200	Phase 2
0.663	Remote Similarity	NPD201	Phase 2
0.6626	Remote Similarity	NPD5867	Clinical (unspecified phase)
0.6624	Remote Similarity	NPD6790	Phase 1
0.6623	Remote Similarity	NPD7887	Approved
0.6623	Remote Similarity	NPD8159	Discontinued
0.6623	Remote Similarity	NPD7888	Approved
0.662	Remote Similarity	NPD7289	Clinical (unspecified phase)
0.662	Remote Similarity	NPD6479	Discontinued
0.6619	Remote Similarity	NPD7024	Clinical (unspecified phase)
0.6619	Remote Similarity	NPD5975	Clinical (unspecified phase)
0.6617	Remote Similarity	NPD3238	Discontinued
0.6616	Remote Similarity	NPD2390	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD7660	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD6242	Discontinued
0.6607	Remote Similarity	NPD8479	Phase 2
0.6607	Remote Similarity	NPD5827	Discontinued
0.6606	Remote Similarity	NPD5510	Approved
0.6606	Remote Similarity	NPD2295	Clinical (unspecified phase)
0.6605	Remote Similarity	NPD5513	Phase 2
0.6603	Remote Similarity	NPD4376	Phase 3
0.6603	Remote Similarity	NPD3430	Approved
0.6603	Remote Similarity	NPD3431	Approved
0.6601	Remote Similarity	NPD5473	Discontinued
0.6595	Remote Similarity	NPD2896	Discontinued
0.6592	Remote Similarity	NPD6578	Clinical (unspecified phase)
0.659	Remote Similarity	NPD3411	Phase 2
0.659	Remote Similarity	NPD3410	Approved
0.659	Remote Similarity	NPD6135	Phase 1
0.6588	Remote Similarity	NPD6226	Phase 3
0.6584	Remote Similarity	NPD5755	Clinical (unspecified phase)
0.6575	Remote Similarity	NPD3476	Approved
0.6575	Remote Similarity	NPD3475	Approved
0.6574	Remote Similarity	NPD5426	Phase 3
0.6574	Remote Similarity	NPD4299	Phase 1

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