NPASS Compound

Structure

NPC472207 OpenBabel07101718332D 38 44 0 0 1 0 0 0 0 0999 V2000 -0.6688 -6.2656 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3136 2.9836 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9905 -2.4659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3704 -3.2395 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9905 -1.4659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5783 -2.2614 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1245 -2.9659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4193 -3.5485 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1245 -0.9659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8352 -1.5922 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0181 1.4013 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2584 -2.4659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6762 -2.8794 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2584 -1.4659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8841 -1.9013 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1045 0.9945 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.3074 -2.7749 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6817 -2.9839 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9006 -3.6884 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0939 -3.7930 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7196 -1.9659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2749 -2.0704 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6180 1.1756 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7226 0.1810 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.7045 1.5823 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.3074 -4.6020 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3018 -4.7711 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9135 -0.4067 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.3074 -1.1568 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.5642 -5.2711 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.0181 -1.4013 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.1226 2.3958 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4271 1.7634 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6361 -0.2257 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2855 -4.8099 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2153 -5.1778 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6000 2.5768 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 30 1 0 0 0 0 2 37 1 0 0 0 0 3 5 2 0 0 0 0 3 7 1 0 0 0 0 4 6 2 0 0 0 0 4 8 1 0 0 0 0 5 9 1 0 0 0 0 6 10 1 0 0 0 0 7 12 2 0 0 0 0 8 13 2 0 0 0 0 9 14 2 0 0 0 0 10 15 2 0 0 0 0 11 32 1 0 0 0 0 12 14 1 0 0 0 0 12 17 1 0 0 0 0 13 15 1 0 0 0 0 13 18 1 0 0 0 0 14 29 1 0 0 0 0 15 31 1 0 0 0 0 16 11 1 6 0 0 0 16 25 1 0 0 0 0 16 38 1 0 0 0 0 17 19 2 0 0 0 0 17 21 1 0 0 0 0 18 20 2 0 0 0 0 18 22 1 0 0 0 0 19 20 1 0 0 0 0 19 26 1 0 0 0 0 20 27 1 0 0 0 0 21 22 2 0 0 0 0 21 29 1 0 0 0 0 22 31 1 0 0 0 0 23 24 1 0 0 0 0 23 25 1 0 0 0 0 23 33 1 6 0 0 0 24 28 1 0 0 0 0 24 34 1 1 0 0 0 25 37 1 1 0 0 0 26 30 1 0 0 0 0 26 35 2 0 0 0 0 27 30 1 0 0 0 0 27 36 2 0 0 0 0 28 31 1 6 0 0 0 28 38 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	354.19
Volume:	370.092
LogP:	3.436
LogD:	3.367
LogS:	-4.041
# Rotatable Bonds:	3
TPSA:	62.4
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.842
Synthetic Accessibility Score:	4.586
Fsp3:	0.524
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.892
MDCK Permeability:	2.074330041068606e-05
Pgp-inhibitor:	0.895
Pgp-substrate:	0.537
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.011
30% Bioavailability (F30%):	0.005

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.948
Plasma Protein Binding (PPB):	56.76127243041992%
Volume Distribution (VD):	1.883
Pgp-substrate:	48.553531646728516%

ADMET: Metabolism

CYP1A2-inhibitor:	0.762
CYP1A2-substrate:	0.656
CYP2C19-inhibitor:	0.401
CYP2C19-substrate:	0.932
CYP2C9-inhibitor:	0.232
CYP2C9-substrate:	0.312
CYP2D6-inhibitor:	0.679
CYP2D6-substrate:	0.878
CYP3A4-inhibitor:	0.819
CYP3A4-substrate:	0.829

ADMET: Excretion

Clearance (CL):	10.878
Half-life (T1/2):	0.359

ADMET: Toxicity

hERG Blockers:	0.599
Human Hepatotoxicity (H-HT):	0.386
Drug-inuced Liver Injury (DILI):	0.555
AMES Toxicity:	0.039
Rat Oral Acute Toxicity:	0.947
Maximum Recommended Daily Dose:	0.924
Skin Sensitization:	0.462
Carcinogencity:	0.48
Eye Corrosion:	0.01
Eye Irritation:	0.03
Respiratory Toxicity:	0.98

Download Data

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

Natural Product: NPC472207

Natural Product ID:	NPC472207
*Common Name:**	DCJDTHHXEQWNBO-KWHOMZPESA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	DCJDTHHXEQWNBO-KWHOMZPESA-N
Standard InCHI:	InChI=1S/C28H25N3O7/c1-30-26(35)19-17-12-7-3-5-9-14(12)29-21(17)22-18(20(19)27(30)36)13-8-4-6-10-15(13)31(22)28-24(34)23(33)25(37-2)16(11-32)38-28/h3-10,16,23-25,28-29,32-34H,11H2,1-2H3/t16-,23-,24-,25-,28-/m1/s1
SMILES:	CN1C(=O)C2=C3C4=CC=CC=C4NC3=C5C(=C2C1=O)C6=CC=CC=C6N5C7C(C(C(C(O7)CO)OC)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3350560
PubChem CID:	10481621
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles and derivatives [CHEMONTID:0000210] Carbazoles [CHEMONTID:0001865] Pyrrolocarbazoles [CHEMONTID:0001866] Indolocarbazoles

*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
NPO33195	actinomadura melliaura atcc 39691	Species	Thermomonosporaceae	Bacteria	n.a.	n.a.	n.a.	PMID[26091285]

☑ 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	9
MIC	10
Others	7

Activity Type	# Activity
Cell Line	12
Individual Protein	4
NON-MOLECULAR	1
Organism	7
Others	1
Protein Family	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	IC50	=	670.0	nM	PMID[565843]
NPT315	Cell Line	CEM-SS	Homo sapiens	IC50	=	4000.0	nM	PMID[565843]
NPT315	Cell Line	CEM-SS	Homo sapiens	CC50	=	7900.0	nM	PMID[565843]
NPT143	Individual Protein	DNA topoisomerase I	Homo sapiens	MIC	=	580.0	nM	PMID[565843]
NPT315	Cell Line	CEM-SS	Homo sapiens	Selectivity index	=	2.0	n.a.	PMID[565843]
NPT182	Individual Protein	Protein kinase C alpha	Homo sapiens	IC50	>	100000.0	nM	PMID[565844]
NPT319	Cell Line	B16	Mus musculus	IC50	=	1060.0	nM	PMID[565844]
NPT168	Cell Line	P388	Mus musculus	IC50	=	700.0	nM	PMID[565844]
NPT143	Individual Protein	DNA topoisomerase I	Homo sapiens	MIC	=	600.0	nM	PMID[565844]
NPT168	Cell Line	P388	Mus musculus	IC50	=	1060.0	nM	PMID[565845]
NPT313	Cell Line	P388CPT5	Mus musculus	IC50	=	700.0	nM	PMID[565845]
NPT315	Cell Line	CEM-SS	Homo sapiens	IC50	=	4170.0	nM	PMID[565845]
NPT315	Cell Line	CEM-SS	Homo sapiens	CC50	=	7960.0	nM	PMID[565845]
NPT143	Individual Protein	DNA topoisomerase I	Homo sapiens	MIC	=	600.0	nM	PMID[565845]
NPT81	Cell Line	A549	Homo sapiens	Activity	=	96.6	%	PMID[565846]
NPT306	Cell Line	PC-3	Homo sapiens	Activity	=	98.3	%	PMID[565846]
NPT314	Organism	Bacillus cereus	Bacillus cereus	MIC	=	1550.0	nM	PMID[565843]
NPT314	Organism	Bacillus cereus	Bacillus cereus	MIC	=	1550.0	nM	PMID[565844]
NPT316	Protein Family	Protein kinase C (PKC)	Homo sapiens	IC50	>	100000.0	nM	PMID[565845]
NPT314	Organism	Bacillus cereus	Bacillus cereus	MIC	=	1550.0	nM	PMID[565845]
NPT2	Others	Unspecified		Selectivity index	=	1.9	n.a.	PMID[565845]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	61.0	%	PMID[565846]
NPT602	Organism	Mycobacterium smegmatis	Mycobacterium smegmatis	MIC	=	7500.0	nM	PMID[565846]
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	MIC	=	7500.0	nM	PMID[565846]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	=	15000.0	nM	PMID[565846]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	7500.0	nM	PMID[565846]

☑ 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 NPC472207 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	385
0.1-0.2	2123
0.2-0.3	12538
0.3-0.4	19342
0.4-0.5	4110
0.5-0.6	2597
0.6-0.7	1515
0.7-0.8	78
0.8-0.85	3
0.85-0.9	2
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9378	High Similarity	NPC472843
0.9295	High Similarity	NPC472846
0.9107	High Similarity	NPC107836
0.8755	High Similarity	NPC472845
0.841	Intermediate Similarity	NPC1203
0.8071	Intermediate Similarity	NPC472842
0.7857	Intermediate Similarity	NPC31700
0.7765	Intermediate Similarity	NPC45048
0.7749	Intermediate Similarity	NPC313884
0.7749	Intermediate Similarity	NPC98371
0.7725	Intermediate Similarity	NPC279589
0.7637	Intermediate Similarity	NPC263937
0.7637	Intermediate Similarity	NPC94428
0.7553	Intermediate Similarity	NPC132329
0.7445	Intermediate Similarity	NPC162860
0.7426	Intermediate Similarity	NPC191382
0.7426	Intermediate Similarity	NPC56109
0.7395	Intermediate Similarity	NPC472844
0.7388	Intermediate Similarity	NPC160898
0.7359	Intermediate Similarity	NPC478157
0.7357	Intermediate Similarity	NPC54420
0.7349	Intermediate Similarity	NPC470205
0.7309	Intermediate Similarity	NPC149708
0.7293	Intermediate Similarity	NPC478158
0.7288	Intermediate Similarity	NPC155444
0.7265	Intermediate Similarity	NPC174788
0.7256	Intermediate Similarity	NPC91179
0.7222	Intermediate Similarity	NPC472285
0.7222	Intermediate Similarity	NPC312645
0.7198	Intermediate Similarity	NPC75634
0.7191	Intermediate Similarity	NPC477714
0.7191	Intermediate Similarity	NPC281049
0.7175	Intermediate Similarity	NPC195314
0.7167	Intermediate Similarity	NPC476491
0.7149	Intermediate Similarity	NPC324091
0.7149	Intermediate Similarity	NPC475969
0.7149	Intermediate Similarity	NPC475859
0.7149	Intermediate Similarity	NPC477715
0.7143	Intermediate Similarity	NPC477548
0.7137	Intermediate Similarity	NPC33949
0.713	Intermediate Similarity	NPC244741
0.7112	Intermediate Similarity	NPC234999
0.7107	Intermediate Similarity	NPC470730
0.7107	Intermediate Similarity	NPC477175
0.7102	Intermediate Similarity	NPC57453
0.7095	Intermediate Similarity	NPC476492
0.7094	Intermediate Similarity	NPC89508
0.7093	Intermediate Similarity	NPC79129
0.7093	Intermediate Similarity	NPC249150
0.7093	Intermediate Similarity	NPC49196
0.7093	Intermediate Similarity	NPC313985
0.7093	Intermediate Similarity	NPC195461
0.7093	Intermediate Similarity	NPC81654
0.709	Intermediate Similarity	NPC70155
0.7089	Intermediate Similarity	NPC52254
0.7078	Intermediate Similarity	NPC474877
0.7074	Intermediate Similarity	NPC317701
0.7064	Intermediate Similarity	NPC477979
0.7051	Intermediate Similarity	NPC475778
0.7049	Intermediate Similarity	NPC165743
0.7037	Intermediate Similarity	NPC470729
0.7037	Intermediate Similarity	NPC477176
0.7036	Intermediate Similarity	NPC14812
0.7035	Intermediate Similarity	NPC227582
0.7031	Intermediate Similarity	NPC476073
0.7025	Intermediate Similarity	NPC475258
0.7024	Intermediate Similarity	NPC471564
0.7022	Intermediate Similarity	NPC181502
0.7022	Intermediate Similarity	NPC85066
0.702	Intermediate Similarity	NPC63279
0.7013	Intermediate Similarity	NPC277350
0.7012	Intermediate Similarity	NPC476818
0.7008	Intermediate Similarity	NPC477177
0.7004	Intermediate Similarity	NPC131887
0.7004	Intermediate Similarity	NPC50503
0.7	Intermediate Similarity	NPC165599
0.6996	Remote Similarity	NPC107077
0.6996	Remote Similarity	NPC223791
0.6992	Remote Similarity	NPC325976
0.6992	Remote Similarity	NPC297642
0.6983	Remote Similarity	NPC477065
0.6982	Remote Similarity	NPC17059
0.698	Remote Similarity	NPC89987
0.6976	Remote Similarity	NPC478029
0.6975	Remote Similarity	NPC82070
0.6974	Remote Similarity	NPC474767
0.6974	Remote Similarity	NPC74413
0.6972	Remote Similarity	NPC475094
0.6971	Remote Similarity	NPC475271
0.6968	Remote Similarity	NPC133003
0.6964	Remote Similarity	NPC478028
0.6962	Remote Similarity	NPC476114
0.6958	Remote Similarity	NPC471506
0.6957	Remote Similarity	NPC155143
0.6951	Remote Similarity	NPC175474
0.6949	Remote Similarity	NPC221100
0.6949	Remote Similarity	NPC234078
0.6949	Remote Similarity	NPC54744
0.6943	Remote Similarity	NPC252338
0.6941	Remote Similarity	NPC476493
0.6933	Remote Similarity	NPC472113
0.693	Remote Similarity	NPC171317
0.6923	Remote Similarity	NPC39370
0.6917	Remote Similarity	NPC272174
0.6914	Remote Similarity	NPC79107
0.6914	Remote Similarity	NPC475338
0.6914	Remote Similarity	NPC475424
0.6914	Remote Similarity	NPC909
0.6913	Remote Similarity	NPC475506
0.6911	Remote Similarity	NPC63031
0.6911	Remote Similarity	NPC473186
0.6907	Remote Similarity	NPC294620
0.6904	Remote Similarity	NPC473310
0.6901	Remote Similarity	NPC229893
0.6897	Remote Similarity	NPC314648
0.6894	Remote Similarity	NPC314834
0.6894	Remote Similarity	NPC475422
0.6891	Remote Similarity	NPC471192
0.6891	Remote Similarity	NPC322064
0.6891	Remote Similarity	NPC470731
0.6889	Remote Similarity	NPC476460
0.6888	Remote Similarity	NPC474896
0.6883	Remote Similarity	NPC162730
0.6883	Remote Similarity	NPC193761
0.6883	Remote Similarity	NPC260900
0.6883	Remote Similarity	NPC476874
0.688	Remote Similarity	NPC87755
0.6878	Remote Similarity	NPC19679
0.6878	Remote Similarity	NPC472108
0.6878	Remote Similarity	NPC472291
0.6878	Remote Similarity	NPC139291
0.6867	Remote Similarity	NPC315638
0.6867	Remote Similarity	NPC314855
0.6867	Remote Similarity	NPC313345
0.6867	Remote Similarity	NPC313796
0.6866	Remote Similarity	NPC161861
0.6864	Remote Similarity	NPC320968
0.6864	Remote Similarity	NPC82370
0.6862	Remote Similarity	NPC249428
0.6861	Remote Similarity	NPC478077
0.6861	Remote Similarity	NPC62749
0.686	Remote Similarity	NPC31097
0.6856	Remote Similarity	NPC52557
0.6851	Remote Similarity	NPC469743
0.6846	Remote Similarity	NPC89549
0.6844	Remote Similarity	NPC472112
0.6842	Remote Similarity	NPC231342
0.6842	Remote Similarity	NPC102592
0.6842	Remote Similarity	NPC292361
0.6842	Remote Similarity	NPC79356
0.684	Remote Similarity	NPC300183
0.6838	Remote Similarity	NPC314297
0.6838	Remote Similarity	NPC315545
0.6836	Remote Similarity	NPC473800
0.6835	Remote Similarity	NPC153980
0.6835	Remote Similarity	NPC6865
0.6829	Remote Similarity	NPC326363
0.6828	Remote Similarity	NPC304203
0.6826	Remote Similarity	NPC32200
0.6826	Remote Similarity	NPC293917
0.6826	Remote Similarity	NPC100321
0.682	Remote Similarity	NPC470732
0.682	Remote Similarity	NPC36405
0.6818	Remote Similarity	NPC478009
0.6818	Remote Similarity	NPC478010
0.6816	Remote Similarity	NPC99939
0.6816	Remote Similarity	NPC62510
0.6816	Remote Similarity	NPC308931
0.681	Remote Similarity	NPC474116
0.6809	Remote Similarity	NPC314957
0.6808	Remote Similarity	NPC478006
0.6807	Remote Similarity	NPC229348
0.6802	Remote Similarity	NPC472109
0.6802	Remote Similarity	NPC472110
0.68	Remote Similarity	NPC184680
0.68	Remote Similarity	NPC213629
0.6797	Remote Similarity	NPC254240
0.6797	Remote Similarity	NPC128265
0.6797	Remote Similarity	NPC312870
0.6797	Remote Similarity	NPC199851
0.6797	Remote Similarity	NPC294909
0.6795	Remote Similarity	NPC18661
0.6795	Remote Similarity	NPC471191
0.6793	Remote Similarity	NPC72956
0.6792	Remote Similarity	NPC79386
0.6789	Remote Similarity	NPC194740
0.6787	Remote Similarity	NPC15840
0.6786	Remote Similarity	NPC475844
0.6783	Remote Similarity	NPC473640
0.6783	Remote Similarity	NPC67288
0.6781	Remote Similarity	NPC476115
0.6778	Remote Similarity	NPC313640
0.6777	Remote Similarity	NPC61813
0.6773	Remote Similarity	NPC470785
0.6773	Remote Similarity	NPC470784
0.6771	Remote Similarity	NPC472119
0.6771	Remote Similarity	NPC228835
0.677	Remote Similarity	NPC95783
0.6767	Remote Similarity	NPC471944
0.6766	Remote Similarity	NPC474905

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 NPC472207 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	214
0.1-0.2	594
0.2-0.3	902
0.3-0.4	2230
0.4-0.5	2774
0.5-0.6	1863
0.6-0.7	534
0.7-0.8	33
0.8-0.85	4
0.85-0.9	1
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9039	High Similarity	NPD7772	Phase 3
0.8566	High Similarity	NPD7181	Phase 3
0.8299	Intermediate Similarity	NPD6456	Discontinued
0.8205	Intermediate Similarity	NPD7921	Approved
0.7974	Intermediate Similarity	NPD6995	Phase 1
0.7835	Intermediate Similarity	NPD6977	Clinical (unspecified phase)
0.7835	Intermediate Similarity	NPD6978	Phase 2
0.7763	Intermediate Similarity	NPD6455	Phase 3
0.7749	Intermediate Similarity	NPD6976	Clinical (unspecified phase)
0.7729	Intermediate Similarity	NPD6717	Clinical (unspecified phase)
0.7675	Intermediate Similarity	NPD8000	Clinical (unspecified phase)
0.766	Intermediate Similarity	NPD7688	Phase 1
0.7448	Intermediate Similarity	NPD7952	Approved
0.7448	Intermediate Similarity	NPD7791	Approved
0.7448	Intermediate Similarity	NPD7950	Approved
0.7448	Intermediate Similarity	NPD7953	Approved
0.7448	Intermediate Similarity	NPD7790	Approved
0.7448	Intermediate Similarity	NPD7951	Approved
0.7448	Intermediate Similarity	NPD7789	Approved
0.7426	Intermediate Similarity	NPD7781	Approved
0.7426	Intermediate Similarity	NPD7780	Approved
0.7389	Intermediate Similarity	NPD6732	Clinical (unspecified phase)
0.7357	Intermediate Similarity	NPD8322	Phase 2
0.7336	Intermediate Similarity	NPD7998	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD3746	Discontinued
0.7311	Intermediate Similarity	NPD7730	Approved
0.7311	Intermediate Similarity	NPD7731	Approved
0.73	Intermediate Similarity	NPD7271	Approved
0.7284	Intermediate Similarity	NPD7073	Clinical (unspecified phase)
0.7269	Intermediate Similarity	NPD7769	Phase 3
0.725	Intermediate Similarity	NPD7824	Approved
0.7237	Intermediate Similarity	NPD7001	Phase 3
0.7198	Intermediate Similarity	NPD7454	Approved
0.7198	Intermediate Similarity	NPD7455	Approved
0.7193	Intermediate Similarity	NPD5426	Phase 3
0.7185	Intermediate Similarity	NPD7716	Approved
0.7185	Intermediate Similarity	NPD7717	Approved
0.7124	Intermediate Similarity	NPD8093	Discontinued
0.7118	Intermediate Similarity	NPD8114	Approved
0.7118	Intermediate Similarity	NPD8115	Approved
0.7105	Intermediate Similarity	NPD5721	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD7770	Phase 3
0.7093	Intermediate Similarity	NPD4601	Approved
0.7093	Intermediate Similarity	NPD4600	Approved
0.7046	Intermediate Similarity	NPD7878	Phase 2
0.7042	Intermediate Similarity	NPD5021	Discontinued
0.7039	Intermediate Similarity	NPD6204	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD3318	Approved
0.7032	Intermediate Similarity	NPD3320	Approved
0.7032	Intermediate Similarity	NPD3319	Phase 1
0.7022	Intermediate Similarity	NPD7944	Discontinued
0.702	Intermediate Similarity	NPD5040	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD6180	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD6630	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD5809	Phase 3
0.6926	Remote Similarity	NPD7767	Approved
0.6923	Remote Similarity	NPD6142	Phase 3
0.6923	Remote Similarity	NPD3607	Clinical (unspecified phase)
0.6913	Remote Similarity	NPD7817	Phase 1
0.6913	Remote Similarity	NPD7727	Phase 2
0.69	Remote Similarity	NPD7000	Clinical (unspecified phase)
0.69	Remote Similarity	NPD6999	Discontinued
0.69	Remote Similarity	NPD6661	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD7712	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD7809	Clinical (unspecified phase)
0.688	Remote Similarity	NPD7665	Phase 2
0.688	Remote Similarity	NPD7666	Phase 3
0.6877	Remote Similarity	NPD5807	Phase 2
0.687	Remote Similarity	NPD8316	Phase 2
0.687	Remote Similarity	NPD8317	Phase 2
0.6857	Remote Similarity	NPD7888	Approved
0.6857	Remote Similarity	NPD7887	Approved
0.6855	Remote Similarity	NPD7502	Clinical (unspecified phase)
0.684	Remote Similarity	NPD5017	Discontinued
0.6838	Remote Similarity	NPD8493	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD7594	Clinical (unspecified phase)
0.6827	Remote Similarity	NPD6986	Phase 1
0.6826	Remote Similarity	NPD7621	Clinical (unspecified phase)
0.6825	Remote Similarity	NPD6716	Phase 1
0.6824	Remote Similarity	NPD6987	Phase 1
0.6811	Remote Similarity	NPD5488	Discontinued
0.6807	Remote Similarity	NPD8094	Discontinued
0.6797	Remote Similarity	NPD8248	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD4500	Approved
0.6797	Remote Similarity	NPD4501	Approved
0.6793	Remote Similarity	NPD7470	Discontinued
0.679	Remote Similarity	NPD5001	Clinical (unspecified phase)
0.6787	Remote Similarity	NPD8464	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD6531	Approved
0.6782	Remote Similarity	NPD6530	Approved
0.678	Remote Similarity	NPD5834	Phase 3
0.678	Remote Similarity	NPD5835	Phase 3
0.6776	Remote Similarity	NPD8289	Discontinued
0.6773	Remote Similarity	NPD6203	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD6838	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD7656	Approved
0.6765	Remote Similarity	NPD7657	Approved
0.6759	Remote Similarity	NPD5821	Approved
0.6758	Remote Similarity	NPD7397	Approved
0.6758	Remote Similarity	NPD7398	Approved
0.6758	Remote Similarity	NPD4736	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD5901	Discontinued
0.6751	Remote Similarity	NPD4900	Clinical (unspecified phase)
0.6741	Remote Similarity	NPD6610	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD6664	Approved
0.6738	Remote Similarity	NPD7187	Phase 2
0.6737	Remote Similarity	NPD2442	Approved
0.6737	Remote Similarity	NPD2443	Approved
0.6725	Remote Similarity	NPD4602	Approved
0.6723	Remote Similarity	NPD7070	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD8013	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD4614	Clinical (unspecified phase)
0.6722	Remote Similarity	NPD8406	Clinical (unspecified phase)
0.6712	Remote Similarity	NPD5473	Discontinued
0.6709	Remote Similarity	NPD6176	Phase 1
0.6696	Remote Similarity	NPD6449	Clinical (unspecified phase)
0.6695	Remote Similarity	NPD2411	Approved
0.6695	Remote Similarity	NPD6328	Clinical (unspecified phase)
0.6681	Remote Similarity	NPD6248	Phase 2
0.6681	Remote Similarity	NPD4051	Discontinued
0.6681	Remote Similarity	NPD8431	Approved
0.6681	Remote Similarity	NPD6249	Phase 2
0.668	Remote Similarity	NPD6615	Clinical (unspecified phase)
0.668	Remote Similarity	NPD6724	Clinical (unspecified phase)
0.6679	Remote Similarity	NPD8524	Approved
0.6667	Remote Similarity	NPD6770	Approved
0.6667	Remote Similarity	NPD7557	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD8459	Approved
0.6667	Remote Similarity	NPD2510	Approved
0.6667	Remote Similarity	NPD2509	Approved
0.6667	Remote Similarity	NPD5592	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5482	Discontinued
0.6667	Remote Similarity	NPD8460	Approved
0.6654	Remote Similarity	NPD8250	Phase 2
0.6653	Remote Similarity	NPD4901	Clinical (unspecified phase)
0.6641	Remote Similarity	NPD5483	Clinical (unspecified phase)
0.664	Remote Similarity	NPD8119	Discontinued
0.6639	Remote Similarity	NPD6210	Phase 3
0.6637	Remote Similarity	NPD4426	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD5744	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD7860	Clinical (unspecified phase)
0.6625	Remote Similarity	NPD4852	Phase 2
0.6608	Remote Similarity	NPD6141	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD8363	Approved
0.6604	Remote Similarity	NPD8364	Approved
0.6597	Remote Similarity	NPD6376	Discontinued
0.6595	Remote Similarity	NPD2880	Discontinued
0.6595	Remote Similarity	NPD5003	Discontinued
0.6592	Remote Similarity	NPD4076	Approved
0.6592	Remote Similarity	NPD4079	Approved
0.6587	Remote Similarity	NPD6840	Approved
0.6582	Remote Similarity	NPD7958	Clinical (unspecified phase)
0.6582	Remote Similarity	NPD7957	Phase 1
0.6581	Remote Similarity	NPD8465	Approved
0.6581	Remote Similarity	NPD8466	Approved
0.6581	Remote Similarity	NPD8467	Approved
0.658	Remote Similarity	NPD7618	Phase 3
0.658	Remote Similarity	NPD7024	Clinical (unspecified phase)
0.658	Remote Similarity	NPD7619	Phase 3
0.6579	Remote Similarity	NPD6965	Clinical (unspecified phase)
0.6578	Remote Similarity	NPD7776	Approved
0.6569	Remote Similarity	NPD2408	Discontinued
0.6568	Remote Similarity	NPD5487	Phase 1
0.6568	Remote Similarity	NPD2920	Discontinued
0.6567	Remote Similarity	NPD7777	Approved
0.6567	Remote Similarity	NPD4987	Clinical (unspecified phase)
0.6567	Remote Similarity	NPD7778	Approved
0.6567	Remote Similarity	NPD53	Approved
0.6565	Remote Similarity	NPD1896	Approved
0.6562	Remote Similarity	NPD6595	Phase 3
0.6557	Remote Similarity	NPD8405	Clinical (unspecified phase)
0.6557	Remote Similarity	NPD6578	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD7195	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD8365	Clinical (unspecified phase)
0.6553	Remote Similarity	NPD7903	Clinical (unspecified phase)
0.6549	Remote Similarity	NPD2091	Phase 2
0.6549	Remote Similarity	NPD2096	Phase 2
0.6549	Remote Similarity	NPD7564	Discontinued
0.6547	Remote Similarity	NPD3505	Approved
0.6547	Remote Similarity	NPD3506	Approved
0.6546	Remote Similarity	NPD6164	Phase 2
0.6546	Remote Similarity	NPD6165	Phase 2
0.6543	Remote Similarity	NPD6733	Discontinued
0.654	Remote Similarity	NPD8272	Phase 2
0.654	Remote Similarity	NPD3947	Discontinued
0.6538	Remote Similarity	NPD3800	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD3486	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD3961	Discontinued
0.6529	Remote Similarity	NPD5888	Phase 2
0.6529	Remote Similarity	NPD3795	Approved
0.6529	Remote Similarity	NPD3794	Approved
0.6527	Remote Similarity	NPD2916	Discontinued
0.6527	Remote Similarity	NPD7191	Phase 2
0.6523	Remote Similarity	NPD7576	Discontinued
0.6522	Remote Similarity	NPD3785	Clinical (unspecified phase)
0.652	Remote Similarity	NPD8429	Approved
0.652	Remote Similarity	NPD8428	Approved
0.652	Remote Similarity	NPD8427	Approved
0.6516	Remote Similarity	NPD2812	Clinical (unspecified phase)
0.6516	Remote Similarity	NPD2813	Phase 3

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