NPASS Compound

Structure

CID28425 OpenBabel06191715352D 21 24 0 0 0 0 0 0 0 0999 V2000 3.3552 -3.1342 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2403 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0504 -0.4678 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6203 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2401 -1.8708 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0001 -2.8061 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4302 -0.4676 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0503 -1.4032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4301 -1.4030 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.8705 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8099 -0.4676 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8101 -3.2737 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8103 -1.4029 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6202 -1.8705 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6201 -2.8059 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8100 -1.4029 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 4.9026 -1.8954 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8101 -4.2458 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7458 -1.6537 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4302 -3.2736 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 21 1 0 0 0 0 2 3 2 0 0 0 0 2 7 1 0 0 0 0 3 8 1 0 0 0 0 4 7 2 0 0 0 0 4 11 1 0 0 0 0 5 8 2 0 0 0 0 5 9 1 0 0 0 0 6 10 2 0 0 0 0 6 12 1 0 0 0 0 7 9 1 0 0 0 0 8 18 1 0 0 0 0 9 14 2 0 0 0 0 10 13 1 0 0 0 0 10 16 1 0 0 0 0 11 13 2 0 0 0 0 11 17 1 0 0 0 0 12 15 2 0 0 0 0 12 19 1 0 0 0 0 13 14 1 0 0 0 0 14 15 1 0 0 0 0 15 21 1 0 0 0 0 16 17 2 0 0 0 0 16 20 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	281.07
Volume:	276.132
LogP:	3.47
LogD:	2.819
LogS:	-6.061
# Rotatable Bonds:	1
TPSA:	78.79
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.599
Synthetic Accessibility Score:	2.773
Fsp3:	0.062
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.111
MDCK Permeability:	5.463532033900265e-06
Pgp-inhibitor:	0.003
Pgp-substrate:	0.485
Human Intestinal Absorption (HIA):	0.028
20% Bioavailability (F20%):	0.042
30% Bioavailability (F30%):	0.992

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.011
Plasma Protein Binding (PPB):	94.5850601196289%
Volume Distribution (VD):	0.703
Pgp-substrate:	8.704699516296387%

ADMET: Metabolism

CYP1A2-inhibitor:	0.98
CYP1A2-substrate:	0.758
CYP2C19-inhibitor:	0.109
CYP2C19-substrate:	0.065
CYP2C9-inhibitor:	0.54
CYP2C9-substrate:	0.884
CYP2D6-inhibitor:	0.653
CYP2D6-substrate:	0.261
CYP3A4-inhibitor:	0.331
CYP3A4-substrate:	0.071

ADMET: Excretion

Clearance (CL):	5.639
Half-life (T1/2):	0.551

ADMET: Toxicity

hERG Blockers:	0.035
Human Hepatotoxicity (H-HT):	0.164
Drug-inuced Liver Injury (DILI):	0.935
AMES Toxicity:	0.697
Rat Oral Acute Toxicity:	0.029
Maximum Recommended Daily Dose:	0.913
Skin Sensitization:	0.925
Carcinogencity:	0.139
Eye Corrosion:	0.007
Eye Irritation:	0.91
Respiratory Toxicity:	0.664

Download Data

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

Natural Product: NPC28425

Natural Product ID:	NPC28425
*Common Name:**	Aristolactam Aiiia
IUPAC Name:	n.a.
Synonyms:	SCH-546909
Standard InCHIKey:	PFXGXKFPTAJYHV-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C16H11NO4/c1-21-15-12(19)6-10-13-11(17-16(10)20)4-7-2-3-8(18)5-9(7)14(13)15/h2-6,18-19H,1H3,(H,17,20)
SMILES:	COc1c(O)cc2c3c1c1cc(O)ccc1cc3N=C2O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL388956
PubChem CID:	10356352
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0002663] Aristolactams

*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
NPO23507	Fissistigma balansae	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10978218]
NPO18509	Fissistigma oldhamii	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10978218]
NPO4865	Piper kadsura	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11040054]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	seeds	n.a.	n.a.	PMID[11141125]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12398544]
NPO18443	Aristolochia manshuriensis	Species	Aristolochiaceae	Eukaryota	Stems	n.a.	n.a.	PMID[12880323]
NPO4865	Piper kadsura	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16724856]
NPO18509	Fissistigma oldhamii	Species	Annonaceae	Eukaryota	stem	n.a.	n.a.	PMID[17081761]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18419154]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19296389]
NPO4865	Piper kadsura	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19900811]
NPO18443	Aristolochia manshuriensis	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20097074]
NPO18443	Aristolochia manshuriensis	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21353775]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21910504]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	seeds	n.a.	n.a.	PMID[22011319]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	seed	n.a.	PMID[22011319]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	Barks	n.a.	n.a.	PMID[2348205]
NPO4865	Piper kadsura	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8237383]
NPO4865	Piper kadsura	Species	Piperaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[8237383]
NPO4865	Piper kadsura	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8368081]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	fruit	n.a.	PMID[8786370]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	bark	n.a.	n.a.	PMID[9214729]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO18443	Aristolochia manshuriensis	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4865	Piper kadsura	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18443	Aristolochia manshuriensis	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4865	Piper kadsura	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18443	Aristolochia manshuriensis	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4865	Piper kadsura	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4865	Piper kadsura	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23507	Fissistigma balansae	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9769	Mortonia palmeri	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11236	Mycale mytilorum	Species	Mycalidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18509	Fissistigma oldhamii	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10517	Aconitum vilmorini	Species	Ranunculaceae	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	14
Others	7

Activity Type	# Activity
Cell Line	3
CELL-LINE	4
Individual Protein	8
Others	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1076	Cell Line	B-cells		IC50	=	19200.0	nM	PMID[514927]
NPT1371	Individual Protein	Cyclin-dependent kinase 2	Homo sapiens	IC50	=	140.0	nM	PMID[514929]
NPT1423	Individual Protein	Cyclin-dependent kinase 1	Homo sapiens	IC50	=	200.0	nM	PMID[514929]
NPT2213	Individual Protein	Cyclin-dependent kinase 4	Homo sapiens	IC50	=	2000.0	nM	PMID[514929]
NPT1432	Individual Protein	Serine/threonine-protein kinase Aurora-A	Homo sapiens	IC50	=	5000.0	nM	PMID[514929]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	10.0	nM	PMID[514929]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	3000.0	nM	PMID[514929]
NPT1371	Individual Protein	Cyclin-dependent kinase 2	Homo sapiens	IC50	=	140.0	nM	PMID[514930]
NPT1423	Individual Protein	Cyclin-dependent kinase 1	Homo sapiens	IC50	=	214.0	nM	PMID[514930]
NPT2213	Individual Protein	Cyclin-dependent kinase 4	Homo sapiens	IC50	=	1420.0	nM	PMID[514930]
NPT1433	Individual Protein	Serine/threonine-protein kinase Aurora-B	Homo sapiens	IC50	=	2140.0	nM	PMID[514930]
NPT27	Others	Unspecified		CC50	>	100000.0	nM	PMID[514927]
NPT2	Others	Unspecified		IC50	=	18500.0	nM	PMID[514927]
NPT2	Others	Unspecified		Ratio CC50/IC50	>	5.0	n.a.	PMID[514927]
NPT20967	CELL-LINE	Platelet	n.a.	Inhibition	=	90.6	%	PMID[514928]
NPT20967	CELL-LINE	Platelet	n.a.	Inhibition	=	56.9	%	PMID[514928]
NPT20967	CELL-LINE	Platelet	n.a.	Inhibition	=	39.6	%	PMID[514928]
NPT20967	CELL-LINE	Platelet	n.a.	Inhibition	=	80.7	%	PMID[514928]
NPT2	Others	Unspecified		IC50	>	50000.0	nM	PMID[514929]
NPT2	Others	Unspecified		IC50	=	35335.0	nM	PMID[514930]

☑ 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 NPC28425 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	511
0.1-0.2	2190
0.2-0.3	9660
0.3-0.4	7872
0.4-0.5	6579
0.5-0.6	12145
0.6-0.7	3239
0.7-0.8	467
0.8-0.85	12
0.85-0.9	3
0.9-0.95	10
0.95-1	9

Similarity Score	Similarity Level	Natural Product ID
0.9939	High Similarity	NPC119579
0.9878	High Similarity	NPC311936
0.9878	High Similarity	NPC215747
0.9878	High Similarity	NPC192939
0.9817	High Similarity	NPC260118
0.9756	High Similarity	NPC265383
0.9586	High Similarity	NPC22928
0.9527	High Similarity	NPC219170
0.9527	High Similarity	NPC180253
0.9419	High Similarity	NPC294244
0.9415	High Similarity	NPC296742
0.9415	High Similarity	NPC112676
0.9408	High Similarity	NPC276060
0.9357	High Similarity	NPC224293
0.9298	High Similarity	NPC69213
0.9091	High Similarity	NPC29472
0.8798	High Similarity	NPC159101
0.8492	Intermediate Similarity	NPC320088
0.8402	Intermediate Similarity	NPC235628
0.8383	Intermediate Similarity	NPC18614
0.838	Intermediate Similarity	NPC276674
0.838	Intermediate Similarity	NPC33902
0.8323	Intermediate Similarity	NPC52475
0.8156	Intermediate Similarity	NPC190461
0.8136	Intermediate Similarity	NPC231371
0.8108	Intermediate Similarity	NPC78284
0.8034	Intermediate Similarity	NPC168153
0.7989	Intermediate Similarity	NPC285941
0.7966	Intermediate Similarity	NPC158376
0.7966	Intermediate Similarity	NPC474931
0.7966	Intermediate Similarity	NPC306555
0.7966	Intermediate Similarity	NPC81218
0.7966	Intermediate Similarity	NPC117188
0.7966	Intermediate Similarity	NPC205421
0.7966	Intermediate Similarity	NPC145832
0.7966	Intermediate Similarity	NPC12053
0.7946	Intermediate Similarity	NPC312531
0.7946	Intermediate Similarity	NPC474904
0.791	Intermediate Similarity	NPC68328
0.7853	Intermediate Similarity	NPC136508
0.7853	Intermediate Similarity	NPC96603
0.7853	Intermediate Similarity	NPC253043
0.7853	Intermediate Similarity	NPC212794
0.7853	Intermediate Similarity	NPC13504
0.7853	Intermediate Similarity	NPC78222
0.7853	Intermediate Similarity	NPC477563
0.7853	Intermediate Similarity	NPC196447
0.7853	Intermediate Similarity	NPC306843
0.7849	Intermediate Similarity	NPC275027
0.7826	Intermediate Similarity	NPC249405
0.7797	Intermediate Similarity	NPC324144
0.7797	Intermediate Similarity	NPC1229
0.779	Intermediate Similarity	NPC192135
0.779	Intermediate Similarity	NPC66341
0.779	Intermediate Similarity	NPC477020
0.7778	Intermediate Similarity	NPC91234
0.776	Intermediate Similarity	NPC320223
0.776	Intermediate Similarity	NPC114364
0.7755	Intermediate Similarity	NPC90185
0.774	Intermediate Similarity	NPC60186
0.7716	Intermediate Similarity	NPC85661
0.7716	Intermediate Similarity	NPC171882
0.7716	Intermediate Similarity	NPC121510
0.7701	Intermediate Similarity	NPC10875
0.7701	Intermediate Similarity	NPC10730
0.7684	Intermediate Similarity	NPC27410
0.7684	Intermediate Similarity	NPC166014
0.768	Intermediate Similarity	NPC26240
0.768	Intermediate Similarity	NPC477562
0.768	Intermediate Similarity	NPC69712
0.7674	Intermediate Similarity	NPC77359
0.7665	Intermediate Similarity	NPC100573
0.7665	Intermediate Similarity	NPC207873
0.7665	Intermediate Similarity	NPC46679
0.7656	Intermediate Similarity	NPC17677
0.765	Intermediate Similarity	NPC128560
0.765	Intermediate Similarity	NPC229166
0.765	Intermediate Similarity	NPC199465
0.7644	Intermediate Similarity	NPC162653
0.7637	Intermediate Similarity	NPC239775
0.7627	Intermediate Similarity	NPC329837
0.7594	Intermediate Similarity	NPC135772
0.7585	Intermediate Similarity	NPC200888
0.7582	Intermediate Similarity	NPC168753
0.7582	Intermediate Similarity	NPC118274
0.7581	Intermediate Similarity	NPC179704
0.7577	Intermediate Similarity	NPC25897
0.7571	Intermediate Similarity	NPC476572
0.7558	Intermediate Similarity	NPC16436
0.7527	Intermediate Similarity	NPC474507
0.7524	Intermediate Similarity	NPC122463
0.7515	Intermediate Similarity	NPC228843
0.7514	Intermediate Similarity	NPC476573
0.7514	Intermediate Similarity	NPC287588
0.7514	Intermediate Similarity	NPC81247
0.7514	Intermediate Similarity	NPC35627
0.7513	Intermediate Similarity	NPC38961
0.75	Intermediate Similarity	NPC228040
0.75	Intermediate Similarity	NPC474051
0.75	Intermediate Similarity	NPC19555
0.7488	Intermediate Similarity	NPC240684
0.7487	Intermediate Similarity	NPC155442
0.7487	Intermediate Similarity	NPC312918
0.7487	Intermediate Similarity	NPC476574
0.7487	Intermediate Similarity	NPC477561
0.7475	Intermediate Similarity	NPC304183
0.7472	Intermediate Similarity	NPC195766
0.7472	Intermediate Similarity	NPC206736
0.7458	Intermediate Similarity	NPC325871
0.7458	Intermediate Similarity	NPC99659
0.7456	Intermediate Similarity	NPC243759
0.7456	Intermediate Similarity	NPC218131
0.7456	Intermediate Similarity	NPC105847
0.7449	Intermediate Similarity	NPC471489
0.7447	Intermediate Similarity	NPC116284
0.7442	Intermediate Similarity	NPC5462
0.744	Intermediate Similarity	NPC118121
0.7438	Intermediate Similarity	NPC298449
0.7438	Intermediate Similarity	NPC290227
0.7419	Intermediate Similarity	NPC148709
0.7419	Intermediate Similarity	NPC173416
0.7419	Intermediate Similarity	NPC476577
0.7416	Intermediate Similarity	NPC291359
0.7415	Intermediate Similarity	NPC204446
0.7412	Intermediate Similarity	NPC12668
0.7412	Intermediate Similarity	NPC308768
0.7396	Intermediate Similarity	NPC230919
0.7396	Intermediate Similarity	NPC266453
0.7396	Intermediate Similarity	NPC200935
0.7396	Intermediate Similarity	NPC151656
0.7387	Intermediate Similarity	NPC261388
0.7377	Intermediate Similarity	NPC298979
0.7377	Intermediate Similarity	NPC310894
0.7377	Intermediate Similarity	NPC247389
0.7366	Intermediate Similarity	NPC477558
0.7358	Intermediate Similarity	NPC302001
0.7354	Intermediate Similarity	NPC248642
0.7353	Intermediate Similarity	NPC132804
0.7353	Intermediate Similarity	NPC220344
0.7353	Intermediate Similarity	NPC275061
0.7353	Intermediate Similarity	NPC243996
0.7337	Intermediate Similarity	NPC156728
0.7337	Intermediate Similarity	NPC244606
0.733	Intermediate Similarity	NPC477186
0.7326	Intermediate Similarity	NPC175838
0.7322	Intermediate Similarity	NPC257354
0.7322	Intermediate Similarity	NPC476432
0.7322	Intermediate Similarity	NPC90984
0.7322	Intermediate Similarity	NPC24264
0.7322	Intermediate Similarity	NPC219341
0.7318	Intermediate Similarity	NPC186063
0.7316	Intermediate Similarity	NPC156576
0.731	Intermediate Similarity	NPC470090
0.7294	Intermediate Similarity	NPC22902
0.7294	Intermediate Similarity	NPC242715
0.7294	Intermediate Similarity	NPC56329
0.7294	Intermediate Similarity	NPC266006
0.7292	Intermediate Similarity	NPC476576
0.7292	Intermediate Similarity	NPC186546
0.7291	Intermediate Similarity	NPC61731
0.7291	Intermediate Similarity	NPC186569
0.7288	Intermediate Similarity	NPC81733
0.7288	Intermediate Similarity	NPC326316
0.7288	Intermediate Similarity	NPC127402
0.7283	Intermediate Similarity	NPC150879
0.7283	Intermediate Similarity	NPC210140
0.7278	Intermediate Similarity	NPC126637
0.7268	Intermediate Similarity	NPC225774
0.7268	Intermediate Similarity	NPC16805
0.7268	Intermediate Similarity	NPC302527
0.7268	Intermediate Similarity	NPC167546
0.7268	Intermediate Similarity	NPC478093
0.7263	Intermediate Similarity	NPC244112
0.7259	Intermediate Similarity	NPC212163
0.7254	Intermediate Similarity	NPC82763
0.7249	Intermediate Similarity	NPC126284
0.7247	Intermediate Similarity	NPC26601
0.724	Intermediate Similarity	NPC57036
0.7235	Intermediate Similarity	NPC30632
0.7235	Intermediate Similarity	NPC202846
0.7235	Intermediate Similarity	NPC143139
0.7232	Intermediate Similarity	NPC184161
0.7232	Intermediate Similarity	NPC219383
0.7231	Intermediate Similarity	NPC473589
0.7231	Intermediate Similarity	NPC30182
0.7231	Intermediate Similarity	NPC478092
0.7231	Intermediate Similarity	NPC478091
0.7225	Intermediate Similarity	NPC183709
0.722	Intermediate Similarity	NPC124658
0.722	Intermediate Similarity	NPC227361
0.7219	Intermediate Similarity	NPC160697
0.7216	Intermediate Similarity	NPC428
0.7216	Intermediate Similarity	NPC476571
0.7216	Intermediate Similarity	NPC246587
0.7216	Intermediate Similarity	NPC135538
0.7216	Intermediate Similarity	NPC79213
0.7216	Intermediate Similarity	NPC147390
0.7216	Intermediate Similarity	NPC24233
0.7212	Intermediate Similarity	NPC21563
0.7209	Intermediate Similarity	NPC165026

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 NPC28425 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	331
0.1-0.2	791
0.2-0.3	965
0.3-0.4	2018
0.4-0.5	2592
0.5-0.6	1974
0.6-0.7	451
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
0.7644	Intermediate Similarity	NPD5617	Suspended
0.7486	Intermediate Similarity	NPD5602	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD2883	Discontinued
0.7401	Intermediate Similarity	NPD3778	Approved
0.7386	Intermediate Similarity	NPD5811	Approved
0.7377	Intermediate Similarity	NPD4083	Discontinued
0.7308	Intermediate Similarity	NPD1850	Phase 3
0.7293	Intermediate Similarity	NPD3453	Discontinued
0.7278	Intermediate Similarity	NPD2358	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD6184	Discontinued
0.7202	Intermediate Similarity	NPD2843	Phase 2
0.7202	Intermediate Similarity	NPD2845	Phase 2
0.7181	Intermediate Similarity	NPD3920	Phase 2
0.7151	Intermediate Similarity	NPD3296	Phase 1
0.7143	Intermediate Similarity	NPD2674	Phase 3
0.7143	Intermediate Similarity	NPD6996	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD2789	Approved
0.7104	Intermediate Similarity	NPD4055	Discovery
0.7098	Intermediate Similarity	NPD4951	Discontinued
0.7095	Intermediate Similarity	NPD4005	Discontinued
0.7077	Intermediate Similarity	NPD5641	Discontinued
0.7072	Intermediate Similarity	NPD3812	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD7906	Approved
0.7062	Intermediate Similarity	NPD4123	Phase 3
0.7059	Intermediate Similarity	NPD2489	Approved
0.7059	Intermediate Similarity	NPD6607	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD27	Approved
0.7043	Intermediate Similarity	NPD4606	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD3051	Approved
0.7039	Intermediate Similarity	NPD4003	Phase 3
0.7039	Intermediate Similarity	NPD950	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD5917	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.7026	Intermediate Similarity	NPD3408	Clinical (unspecified phase)
0.7017	Intermediate Similarity	NPD3237	Clinical (unspecified phase)
0.7017	Intermediate Similarity	NPD3236	Phase 3
0.7006	Intermediate Similarity	NPD2420	Approved
0.7006	Intermediate Similarity	NPD2421	Approved
0.7005	Intermediate Similarity	NPD2970	Approved
0.7005	Intermediate Similarity	NPD2969	Approved
0.7	Intermediate Similarity	NPD7479	Phase 2
0.6995	Remote Similarity	NPD5599	Discontinued
0.6989	Remote Similarity	NPD2821	Approved
0.6982	Remote Similarity	NPD3144	Approved
0.6982	Remote Similarity	NPD3145	Approved
0.6968	Remote Similarity	NPD677	Clinical (unspecified phase)
0.6967	Remote Similarity	NPD3763	Approved
0.6963	Remote Similarity	NPD6496	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD5810	Discontinued
0.6943	Remote Similarity	NPD7311	Approved
0.6943	Remote Similarity	NPD7312	Approved
0.6943	Remote Similarity	NPD4577	Approved
0.6943	Remote Similarity	NPD7310	Approved
0.6943	Remote Similarity	NPD4578	Approved
0.6943	Remote Similarity	NPD7313	Approved
0.6931	Remote Similarity	NPD5966	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD5261	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD7263	Phase 2
0.6923	Remote Similarity	NPD4663	Approved
0.6919	Remote Similarity	NPD7262	Phase 1
0.6907	Remote Similarity	NPD7309	Approved
0.6907	Remote Similarity	NPD8054	Approved
0.6907	Remote Similarity	NPD8053	Approved
0.6904	Remote Similarity	NPD6656	Clinical (unspecified phase)
0.69	Remote Similarity	NPD7034	Discontinued
0.6897	Remote Similarity	NPD5848	Clinical (unspecified phase)
0.6888	Remote Similarity	NPD3398	Discontinued
0.6869	Remote Similarity	NPD3924	Approved
0.6869	Remote Similarity	NPD3921	Approved
0.6869	Remote Similarity	NPD3923	Approved
0.6869	Remote Similarity	NPD3922	Approved
0.6868	Remote Similarity	NPD4675	Approved
0.6868	Remote Similarity	NPD4678	Approved
0.6842	Remote Similarity	NPD6503	Clinical (unspecified phase)
0.6836	Remote Similarity	NPD6331	Phase 2
0.6836	Remote Similarity	NPD6658	Clinical (unspecified phase)
0.6831	Remote Similarity	NPD980	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD4097	Suspended
0.6818	Remote Similarity	NPD6494	Phase 2
0.6818	Remote Similarity	NPD4664	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD7238	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD4986	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD7493	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD3349	Phase 2
0.6802	Remote Similarity	NPD5800	Discontinued
0.6798	Remote Similarity	NPD6612	Phase 2
0.6798	Remote Similarity	NPD3301	Approved
0.6798	Remote Similarity	NPD5241	Discontinued
0.6796	Remote Similarity	NPD5530	Phase 1
0.6789	Remote Similarity	NPD2898	Approved
0.6784	Remote Similarity	NPD3963	Phase 1
0.6778	Remote Similarity	NPD4584	Approved
0.6774	Remote Similarity	NPD4581	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD5929	Approved
0.675	Remote Similarity	NPD7125	Discontinued
0.6738	Remote Similarity	NPD7831	Phase 2
0.6738	Remote Similarity	NPD7832	Clinical (unspecified phase)
0.6738	Remote Similarity	NPD7833	Phase 2
0.6733	Remote Similarity	NPD6527	Approved
0.6733	Remote Similarity	NPD4605	Approved
0.6733	Remote Similarity	NPD4604	Approved
0.6727	Remote Similarity	NPD8067	Phase 3
0.6722	Remote Similarity	NPD2752	Clinical (unspecified phase)
0.6722	Remote Similarity	NPD4357	Discontinued
0.6716	Remote Similarity	NPD7686	Clinical (unspecified phase)
0.6714	Remote Similarity	NPD5164	Discontinued
0.6714	Remote Similarity	NPD4502	Phase 2
0.6705	Remote Similarity	NPD2161	Phase 2
0.6705	Remote Similarity	NPD1558	Phase 1
0.6684	Remote Similarity	NPD7546	Discontinued
0.6667	Remote Similarity	NPD1375	Discontinued
0.6667	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6818	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6037	Discontinued
0.6667	Remote Similarity	NPD1669	Approved
0.6667	Remote Similarity	NPD7922	Phase 1
0.665	Remote Similarity	NPD3515	Approved
0.665	Remote Similarity	NPD2488	Approved
0.665	Remote Similarity	NPD3516	Approved
0.665	Remote Similarity	NPD2490	Approved
0.6649	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD5819	Phase 2
0.6631	Remote Similarity	NPD6063	Approved
0.6631	Remote Similarity	NPD3556	Approved
0.6631	Remote Similarity	NPD3557	Approved
0.6631	Remote Similarity	NPD3559	Clinical (unspecified phase)
0.6631	Remote Similarity	NPD3560	Approved
0.6631	Remote Similarity	NPD2563	Approved
0.6631	Remote Similarity	NPD3558	Approved
0.6631	Remote Similarity	NPD2560	Approved
0.6616	Remote Similarity	NPD6340	Approved
0.6616	Remote Similarity	NPD6339	Approved
0.6615	Remote Similarity	NPD4481	Phase 3
0.6612	Remote Similarity	NPD6030	Approved
0.6612	Remote Similarity	NPD6031	Approved
0.661	Remote Similarity	NPD6522	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD3815	Phase 1
0.6604	Remote Similarity	NPD3816	Phase 1
0.6602	Remote Similarity	NPD3450	Approved
0.6602	Remote Similarity	NPD2493	Approved
0.6602	Remote Similarity	NPD2494	Approved
0.6602	Remote Similarity	NPD3452	Approved
0.6601	Remote Similarity	NPD5582	Discontinued
0.66	Remote Similarity	NPD3342	Phase 2
0.6597	Remote Similarity	NPD4010	Discontinued
0.6596	Remote Similarity	NPD7773	Phase 2
0.6592	Remote Similarity	NPD6723	Discontinued
0.659	Remote Similarity	NPD5111	Phase 2
0.659	Remote Similarity	NPD5110	Phase 2
0.659	Remote Similarity	NPD5109	Approved
0.6589	Remote Similarity	NPD8149	Discontinued
0.6585	Remote Similarity	NPD3837	Clinical (unspecified phase)
0.6584	Remote Similarity	NPD6526	Approved
0.6575	Remote Similarity	NPD3845	Phase 1
0.6569	Remote Similarity	NPD6773	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD2216	Approved
0.6562	Remote Similarity	NPD2215	Approved
0.6561	Remote Similarity	NPD5604	Discontinued
0.6559	Remote Similarity	NPD3796	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD6491	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD7477	Discontinued
0.655	Remote Similarity	NPD7243	Clinical (unspecified phase)
0.6548	Remote Similarity	NPD8453	Clinical (unspecified phase)
0.6546	Remote Similarity	NPD8099	Discontinued
0.6546	Remote Similarity	NPD8252	Approved
0.6546	Remote Similarity	NPD8251	Approved
0.6541	Remote Similarity	NPD6523	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD3633	Approved
0.6535	Remote Similarity	NPD3634	Approved
0.6532	Remote Similarity	NPD3027	Phase 3
0.6526	Remote Similarity	NPD7827	Phase 1
0.6524	Remote Similarity	NPD7453	Approved
0.6524	Remote Similarity	NPD5429	Discontinued
0.6524	Remote Similarity	NPD7222	Phase 2
0.6524	Remote Similarity	NPD7452	Approved
0.652	Remote Similarity	NPD8249	Clinical (unspecified phase)
0.6519	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.6515	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.6515	Remote Similarity	NPD5083	Clinical (unspecified phase)
0.6514	Remote Similarity	NPD3620	Phase 2
0.6514	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6513	Remote Similarity	NPD8156	Discontinued
0.651	Remote Similarity	NPD6071	Discontinued
0.6507	Remote Similarity	NPD4583	Approved
0.6507	Remote Similarity	NPD4582	Approved
0.6505	Remote Similarity	NPD6502	Phase 2
0.6503	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6495	Remote Similarity	NPD5938	Phase 3
0.6495	Remote Similarity	NPD7571	Clinical (unspecified phase)
0.6493	Remote Similarity	NPD5658	Approved
0.6493	Remote Similarity	NPD4859	Phase 1
0.6492	Remote Similarity	NPD6746	Phase 2
0.6489	Remote Similarity	NPD2977	Approved
0.6489	Remote Similarity	NPD2978	Approved
0.6489	Remote Similarity	NPD5773	Approved
0.6489	Remote Similarity	NPD5772	Approved
0.6484	Remote Similarity	NPD1305	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD2422	Clinical (unspecified phase)
0.648	Remote Similarity	NPD5557	Phase 1
0.6479	Remote Similarity	NPD5936	Approved

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