NPASS Compound

Structure

NPC472842 OpenBabel07101718332D 47 54 0 0 1 0 0 0 0 0999 V2000 6.9282 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3506 4.6778 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1596 4.0900 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6019 -0.8226 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5629 4.2710 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2929 0.1285 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9328 -1.5657 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0551 3.0955 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6674 3.2765 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3147 0.3364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9546 -1.3578 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1416 2.6887 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.4765 2.6887 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8147 1.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4546 2.8966 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1237 2.1535 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1674 1.7377 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6456 -0.4067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8366 0.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.9546 3.7627 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0373 2.5602 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.2855 -2.1009 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 1.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.1674 1.7377 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.9328 3.5547 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5479 4.6762 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9033 2.0602 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 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 35 1 0 0 0 0 2 44 1 0 0 0 0 3 4 2 0 0 0 0 3 6 1 0 0 0 0 4 9 1 0 0 0 0 5 7 2 0 0 0 0 5 8 1 0 0 0 0 6 13 2 0 0 0 0 7 14 1 0 0 0 0 8 15 2 0 0 0 0 9 16 2 0 0 0 0 10 18 1 0 0 0 0 10 20 1 0 0 0 0 11 17 1 0 0 0 0 11 45 1 0 0 0 0 12 46 1 0 0 0 0 13 16 1 0 0 0 0 13 21 1 0 0 0 0 14 22 1 0 0 0 0 14 26 2 0 0 0 0 15 26 1 0 0 0 0 15 34 1 0 0 0 0 16 36 1 0 0 0 0 17 18 1 0 0 0 0 17 35 1 1 0 0 0 18 39 1 6 0 0 0 19 12 1 6 0 0 0 19 30 1 0 0 0 0 19 47 1 0 0 0 0 20 45 1 0 0 0 0 20 46 1 1 0 0 0 21 23 2 0 0 0 0 21 25 1 0 0 0 0 22 24 2 0 0 0 0 22 27 1 0 0 0 0 23 24 1 0 0 0 0 23 31 1 0 0 0 0 24 32 1 0 0 0 0 25 27 2 0 0 0 0 25 36 1 0 0 0 0 26 38 1 0 0 0 0 27 38 1 0 0 0 0 28 29 1 0 0 0 0 28 30 1 0 0 0 0 28 40 1 6 0 0 0 29 33 1 0 0 0 0 29 41 1 1 0 0 0 30 44 1 1 0 0 0 31 37 2 0 0 0 0 31 42 1 0 0 0 0 32 37 1 0 0 0 0 32 43 2 0 0 0 0 33 38 1 6 0 0 0 33 47 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	664.19
Volume:	620.181
LogP:	1.927
LogD:	2.542
LogS:	-6.848
# Rotatable Bonds:	6
TPSA:	176.53
# H-Bond Aceptor:	13
# H-Bond Donor:	6
# Rings:	8
# Heavy Atoms:	14

MedChem Properties

QED Drug-Likeness Score:	0.148
Synthetic Accessibility Score:	4.976
Fsp3:	0.394
Lipinski Rule-of-5:	Rejected
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:	-5.785
MDCK Permeability:	4.50242714578053e-06
Pgp-inhibitor:	0.581
Pgp-substrate:	0.998
Human Intestinal Absorption (HIA):	0.904
20% Bioavailability (F20%):	0.167
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.156
Plasma Protein Binding (PPB):	93.2688217163086%
Volume Distribution (VD):	1.549
Pgp-substrate:	2.391273260116577%

ADMET: Metabolism

CYP1A2-inhibitor:	0.144
CYP1A2-substrate:	0.973
CYP2C19-inhibitor:	0.159
CYP2C19-substrate:	0.292
CYP2C9-inhibitor:	0.442
CYP2C9-substrate:	0.071
CYP2D6-inhibitor:	0.034
CYP2D6-substrate:	0.148
CYP3A4-inhibitor:	0.253
CYP3A4-substrate:	0.537

ADMET: Excretion

Clearance (CL):	4.334
Half-life (T1/2):	0.074

ADMET: Toxicity

hERG Blockers:	0.583
Human Hepatotoxicity (H-HT):	0.667
Drug-inuced Liver Injury (DILI):	0.978
AMES Toxicity:	0.913
Rat Oral Acute Toxicity:	0.047
Maximum Recommended Daily Dose:	0.979
Skin Sensitization:	0.8
Carcinogencity:	0.802
Eye Corrosion:	0.003
Eye Irritation:	0.009
Respiratory Toxicity:	0.92

Download Data

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

Natural Product: NPC472842

Natural Product ID:	NPC472842
*Common Name:**	ATEGCFWPRAJCNX-NVCNUFFYSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	ATEGCFWPRAJCNX-NVCNUFFYSA-N
Standard InCHI:	InChI=1S/C33H33ClN4O9/c1-35-17-11-45-20(10-18(17)39)46-12-19-30(44-2)28(40)29(41)33(47-19)38-26-14(7-5-8-15(26)34)22-24-23(31(42)37-32(24)43)21-13-6-3-4-9-16(13)36-25(21)27(22)38/h3-9,17-20,28-30,33,35-36,39-41H,10-12H2,1-2H3,(H,37,42,43)/t17-,18-,19+,20-,28+,29+,30+,33+/m0/s1
SMILES:	CNC1COC(CC1O)OCC2C(C(C(C(O2)N3C4=C(C=CC=C4Cl)C5=C6C(=C7C8=CC=CC=C8NC7=C53)C(=O)NC6=O)O)O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3589059
PubChem CID:	n.a.
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	3
MIC	4
Others	3

Activity Type	# Activity
Cell Line	4
NON-MOLECULAR	2
Organism	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	=	69.6	nM	PMID[486745]
NPT306	Cell Line	PC-3	Homo sapiens	IC50	=	45.8	nM	PMID[486745]
NPT81	Cell Line	A549	Homo sapiens	Activity	=	19.9	%	PMID[486745]
NPT306	Cell Line	PC-3	Homo sapiens	Activity	=	39.0	%	PMID[486745]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	47.3	nM	PMID[486745]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	31.3	%	PMID[486745]
NPT602	Organism	Mycobacterium smegmatis	Mycobacterium smegmatis	MIC	=	7500.0	nM	PMID[486745]
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	MIC	=	1000.0	nM	PMID[486745]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	=	7500.0	nM	PMID[486745]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	7500.0	nM	PMID[486745]

☑ 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 NPC472842 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	525
0.1-0.2	2452
0.2-0.3	11577
0.3-0.4	17846
0.4-0.5	6529
0.5-0.6	2788
0.6-0.7	940
0.7-0.8	32
0.8-0.85	2
0.85-0.9	3
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9252	High Similarity	NPC472845
0.9157	High Similarity	NPC1203
0.875	High Similarity	NPC107836
0.8701	High Similarity	NPC472846
0.8622	High Similarity	NPC472843
0.8185	Intermediate Similarity	NPC472844
0.8071	Intermediate Similarity	NPC472207
0.7818	Intermediate Similarity	NPC45048
0.7782	Intermediate Similarity	NPC279589
0.7738	Intermediate Similarity	NPC313884
0.7738	Intermediate Similarity	NPC98371
0.7621	Intermediate Similarity	NPC31700
0.7433	Intermediate Similarity	NPC94428
0.7433	Intermediate Similarity	NPC263937
0.7356	Intermediate Similarity	NPC132329
0.7338	Intermediate Similarity	NPC57453
0.7241	Intermediate Similarity	NPC33949
0.7212	Intermediate Similarity	NPC160898
0.7138	Intermediate Similarity	NPC476514
0.7088	Intermediate Similarity	NPC475271
0.7082	Intermediate Similarity	NPC476114
0.708	Intermediate Similarity	NPC473800
0.7066	Intermediate Similarity	NPC52254
0.7027	Intermediate Similarity	NPC82070
0.7027	Intermediate Similarity	NPC174788
0.6988	Remote Similarity	NPC312645
0.6943	Remote Similarity	NPC476492
0.694	Remote Similarity	NPC323198
0.6935	Remote Similarity	NPC195314
0.6914	Remote Similarity	NPC316411
0.6911	Remote Similarity	NPC274842
0.6911	Remote Similarity	NPC478157
0.6899	Remote Similarity	NPC244856
0.6887	Remote Similarity	NPC9482
0.6877	Remote Similarity	NPC478009
0.6877	Remote Similarity	NPC70155
0.6877	Remote Similarity	NPC478010
0.6873	Remote Similarity	NPC306644
0.6873	Remote Similarity	NPC89508
0.6873	Remote Similarity	NPC236424
0.6866	Remote Similarity	NPC267853
0.6858	Remote Similarity	NPC472285
0.6854	Remote Similarity	NPC56109
0.6854	Remote Similarity	NPC191382
0.6848	Remote Similarity	NPC477548
0.6846	Remote Similarity	NPC131273
0.6846	Remote Similarity	NPC473441
0.684	Remote Similarity	NPC244897
0.6836	Remote Similarity	NPC244741
0.6835	Remote Similarity	NPC476515
0.6809	Remote Similarity	NPC478006
0.6804	Remote Similarity	NPC172355
0.6803	Remote Similarity	NPC315062
0.6777	Remote Similarity	NPC473565
0.6774	Remote Similarity	NPC14812
0.6764	Remote Similarity	NPC94541
0.6764	Remote Similarity	NPC470843
0.6763	Remote Similarity	NPC471564
0.6742	Remote Similarity	NPC476818
0.6728	Remote Similarity	NPC325976
0.6726	Remote Similarity	NPC314882
0.6725	Remote Similarity	NPC315467
0.6719	Remote Similarity	NPC165599
0.6718	Remote Similarity	NPC477979
0.6718	Remote Similarity	NPC478158
0.6705	Remote Similarity	NPC281049
0.6705	Remote Similarity	NPC294620
0.6704	Remote Similarity	NPC326363
0.6704	Remote Similarity	NPC229893
0.6698	Remote Similarity	NPC115282
0.6692	Remote Similarity	NPC471506
0.6691	Remote Similarity	NPC192712
0.6691	Remote Similarity	NPC476491
0.669	Remote Similarity	NPC476493
0.6689	Remote Similarity	NPC116701
0.6667	Remote Similarity	NPC249428
0.6667	Remote Similarity	NPC155444
0.6667	Remote Similarity	NPC39370
0.6667	Remote Similarity	NPC191489
0.6667	Remote Similarity	NPC204303
0.6667	Remote Similarity	NPC470901
0.6655	Remote Similarity	NPC311451
0.6654	Remote Similarity	NPC89987
0.6654	Remote Similarity	NPC79107
0.6654	Remote Similarity	NPC131887
0.6654	Remote Similarity	NPC475424
0.6644	Remote Similarity	NPC471303
0.6642	Remote Similarity	NPC473806
0.6642	Remote Similarity	NPC471634
0.6641	Remote Similarity	NPC75634
0.6632	Remote Similarity	NPC100734
0.6632	Remote Similarity	NPC88923
0.6632	Remote Similarity	NPC315634
0.663	Remote Similarity	NPC475258
0.663	Remote Similarity	NPC471782
0.663	Remote Similarity	NPC471583
0.6629	Remote Similarity	NPC204491
0.6628	Remote Similarity	NPC234999
0.6628	Remote Similarity	NPC314648
0.6615	Remote Similarity	NPC476073
0.6615	Remote Similarity	NPC193761
0.6608	Remote Similarity	NPC89549
0.6606	Remote Similarity	NPC475844
0.6599	Remote Similarity	NPC237901
0.6599	Remote Similarity	NPC195788
0.6594	Remote Similarity	NPC278540
0.6593	Remote Similarity	NPC473186
0.6593	Remote Similarity	NPC472762
0.6593	Remote Similarity	NPC475338
0.6593	Remote Similarity	NPC909
0.659	Remote Similarity	NPC162860
0.6589	Remote Similarity	NPC476115
0.6587	Remote Similarity	NPC478011
0.6587	Remote Similarity	NPC478012
0.6585	Remote Similarity	NPC478080
0.6579	Remote Similarity	NPC473310
0.6578	Remote Similarity	NPC151976
0.6578	Remote Similarity	NPC475778
0.6577	Remote Similarity	NPC477065
0.6577	Remote Similarity	NPC474905
0.6573	Remote Similarity	NPC472436
0.6573	Remote Similarity	NPC284685
0.6571	Remote Similarity	NPC310618
0.6569	Remote Similarity	NPC323752
0.6568	Remote Similarity	NPC57690
0.6566	Remote Similarity	NPC260909
0.6565	Remote Similarity	NPC314834
0.6565	Remote Similarity	NPC314176
0.6565	Remote Similarity	NPC475422
0.6562	Remote Similarity	NPC32200
0.6559	Remote Similarity	NPC291609
0.6558	Remote Similarity	NPC28945
0.6558	Remote Similarity	NPC285343
0.6557	Remote Similarity	NPC282033
0.6556	Remote Similarity	NPC141428
0.655	Remote Similarity	NPC476874
0.6547	Remote Similarity	NPC81175
0.654	Remote Similarity	NPC82370
0.6537	Remote Similarity	NPC67401
0.6536	Remote Similarity	NPC472434
0.6533	Remote Similarity	NPC321592
0.6533	Remote Similarity	NPC54803
0.6531	Remote Similarity	NPC24370
0.6531	Remote Similarity	NPC319232
0.6528	Remote Similarity	NPC313640
0.6523	Remote Similarity	NPC124300
0.6517	Remote Similarity	NPC477714
0.6517	Remote Similarity	NPC264285
0.6517	Remote Similarity	NPC314056
0.6513	Remote Similarity	NPC314297
0.6513	Remote Similarity	NPC315545
0.6513	Remote Similarity	NPC54420
0.6512	Remote Similarity	NPC469734
0.6511	Remote Similarity	NPC216507
0.6507	Remote Similarity	NPC183426
0.6506	Remote Similarity	NPC474896
0.6504	Remote Similarity	NPC36405
0.6504	Remote Similarity	NPC203614
0.6503	Remote Similarity	NPC478083
0.6502	Remote Similarity	NPC476516
0.6498	Remote Similarity	NPC184680
0.6498	Remote Similarity	NPC104712
0.6496	Remote Similarity	NPC474701
0.6495	Remote Similarity	NPC227824
0.6494	Remote Similarity	NPC235885
0.6491	Remote Similarity	NPC229348
0.6491	Remote Similarity	NPC329982
0.6489	Remote Similarity	NPC127677
0.6489	Remote Similarity	NPC87755
0.6489	Remote Similarity	NPC473389
0.6486	Remote Similarity	NPC327769
0.6484	Remote Similarity	NPC253580
0.6484	Remote Similarity	NPC141454
0.6483	Remote Similarity	NPC152620
0.6481	Remote Similarity	NPC469312
0.6481	Remote Similarity	NPC41318
0.6481	Remote Similarity	NPC16352
0.6481	Remote Similarity	NPC31097
0.6479	Remote Similarity	NPC477715
0.6477	Remote Similarity	NPC78609
0.6475	Remote Similarity	NPC470785
0.6475	Remote Similarity	NPC313345
0.6475	Remote Similarity	NPC470784
0.6475	Remote Similarity	NPC313796
0.6475	Remote Similarity	NPC314855
0.6475	Remote Similarity	NPC315638
0.6475	Remote Similarity	NPC41679
0.6473	Remote Similarity	NPC313985
0.6473	Remote Similarity	NPC195461
0.6473	Remote Similarity	NPC79129
0.6473	Remote Similarity	NPC249150
0.6473	Remote Similarity	NPC81654
0.6473	Remote Similarity	NPC49196
0.6471	Remote Similarity	NPC112547
0.6469	Remote Similarity	NPC472435
0.6468	Remote Similarity	NPC272174
0.6464	Remote Similarity	NPC469743
0.6464	Remote Similarity	NPC478081
0.646	Remote Similarity	NPC95240
0.646	Remote Similarity	NPC223409

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 NPC472842 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	254
0.1-0.2	604
0.2-0.3	1050
0.3-0.4	2383
0.4-0.5	2883
0.5-0.6	1654
0.6-0.7	309
0.7-0.8	9
0.8-0.85	3
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8549	High Similarity	NPD7772	Phase 3
0.8106	Intermediate Similarity	NPD6456	Discontinued
0.8086	Intermediate Similarity	NPD7921	Approved
0.8015	Intermediate Similarity	NPD7181	Phase 3
0.7817	Intermediate Similarity	NPD6977	Clinical (unspecified phase)
0.7817	Intermediate Similarity	NPD6978	Phase 2
0.7738	Intermediate Similarity	NPD6976	Clinical (unspecified phase)
0.7441	Intermediate Similarity	NPD6717	Clinical (unspecified phase)
0.7402	Intermediate Similarity	NPD6455	Phase 3
0.7385	Intermediate Similarity	NPD7688	Phase 1
0.7383	Intermediate Similarity	NPD6995	Phase 1
0.7381	Intermediate Similarity	NPD7073	Clinical (unspecified phase)
0.7249	Intermediate Similarity	NPD5807	Phase 2
0.7232	Intermediate Similarity	NPD7769	Phase 3
0.7159	Intermediate Similarity	NPD3746	Discontinued
0.71	Intermediate Similarity	NPD7576	Discontinued
0.7074	Intermediate Similarity	NPD7770	Phase 3
0.7068	Intermediate Similarity	NPD7790	Approved
0.7068	Intermediate Similarity	NPD7950	Approved
0.7068	Intermediate Similarity	NPD7951	Approved
0.7068	Intermediate Similarity	NPD7791	Approved
0.7068	Intermediate Similarity	NPD7789	Approved
0.7068	Intermediate Similarity	NPD7952	Approved
0.7068	Intermediate Similarity	NPD7953	Approved
0.6968	Remote Similarity	NPD8463	Approved
0.6929	Remote Similarity	NPD7001	Phase 3
0.6929	Remote Similarity	NPD6732	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD8093	Discontinued
0.688	Remote Similarity	NPD7731	Approved
0.688	Remote Similarity	NPD7730	Approved
0.6866	Remote Similarity	NPD5450	Discontinued
0.6854	Remote Similarity	NPD7780	Approved
0.6854	Remote Similarity	NPD7781	Approved
0.6828	Remote Similarity	NPD7824	Approved
0.6805	Remote Similarity	NPD7271	Approved
0.6768	Remote Similarity	NPD7878	Phase 2
0.6763	Remote Similarity	NPD7398	Approved
0.6763	Remote Similarity	NPD7397	Approved
0.6758	Remote Similarity	NPD5426	Phase 3
0.6744	Remote Similarity	NPD7666	Phase 3
0.6744	Remote Similarity	NPD7665	Phase 2
0.6731	Remote Similarity	NPD8279	Clinical (unspecified phase)
0.673	Remote Similarity	NPD8000	Clinical (unspecified phase)
0.6728	Remote Similarity	NPD6142	Phase 3
0.6691	Remote Similarity	NPD5040	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD8046	Discontinued
0.6667	Remote Similarity	NPD7708	Approved
0.6667	Remote Similarity	NPD7767	Approved
0.6655	Remote Similarity	NPD7776	Approved
0.6643	Remote Similarity	NPD7860	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD7803	Approved
0.6631	Remote Similarity	NPD5488	Discontinued
0.6629	Remote Similarity	NPD6615	Clinical (unspecified phase)
0.6628	Remote Similarity	NPD7998	Clinical (unspecified phase)
0.662	Remote Similarity	NPD8244	Phase 2
0.6619	Remote Similarity	NPD7787	Discontinued
0.6616	Remote Similarity	NPD8094	Discontinued
0.6599	Remote Similarity	NPD8467	Approved
0.6599	Remote Similarity	NPD8466	Approved
0.6599	Remote Similarity	NPD8465	Approved
0.6593	Remote Similarity	NPD8289	Discontinued
0.6579	Remote Similarity	NPD8524	Approved
0.6578	Remote Similarity	NPD7455	Approved
0.6578	Remote Similarity	NPD7454	Approved
0.6578	Remote Similarity	NPD8097	Phase 3
0.6578	Remote Similarity	NPD8096	Phase 3
0.6577	Remote Similarity	NPD6838	Clinical (unspecified phase)
0.6573	Remote Similarity	NPD7956	Approved
0.6573	Remote Similarity	NPD7955	Approved
0.6571	Remote Similarity	NPD8468	Phase 2
0.6566	Remote Similarity	NPD8459	Approved
0.6566	Remote Similarity	NPD8460	Approved
0.6564	Remote Similarity	NPD8114	Approved
0.6564	Remote Similarity	NPD8364	Approved
0.6564	Remote Similarity	NPD8115	Approved
0.6564	Remote Similarity	NPD8363	Approved
0.6564	Remote Similarity	NPD5901	Discontinued
0.6562	Remote Similarity	NPD7000	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD6999	Discontinued
0.656	Remote Similarity	NPD5482	Discontinued
0.6557	Remote Similarity	NPD8238	Clinical (unspecified phase)
0.6551	Remote Similarity	NPD6531	Approved
0.6551	Remote Similarity	NPD6530	Approved
0.6542	Remote Similarity	NPD8428	Approved
0.6542	Remote Similarity	NPD8427	Approved
0.6542	Remote Similarity	NPD8429	Approved
0.654	Remote Similarity	NPD7470	Discontinued
0.6523	Remote Similarity	NPD6716	Phase 1
0.6519	Remote Similarity	NPD7717	Approved
0.6519	Remote Similarity	NPD8365	Clinical (unspecified phase)
0.6519	Remote Similarity	NPD7716	Approved
0.6513	Remote Similarity	NPD8322	Phase 2
0.651	Remote Similarity	NPD8426	Approved
0.651	Remote Similarity	NPD8425	Approved
0.6496	Remote Similarity	NPD8372	Clinical (unspecified phase)
0.6494	Remote Similarity	NPD8421	Discontinued
0.6486	Remote Similarity	NPD5721	Clinical (unspecified phase)
0.6477	Remote Similarity	NPD5483	Clinical (unspecified phase)
0.6473	Remote Similarity	NPD4600	Approved
0.6473	Remote Similarity	NPD4601	Approved
0.6466	Remote Similarity	NPD8102	Discontinued
0.6466	Remote Similarity	NPD3757	Clinical (unspecified phase)
0.6464	Remote Similarity	NPD5821	Approved
0.646	Remote Similarity	NPD8374	Phase 3
0.6456	Remote Similarity	NPD6724	Clinical (unspecified phase)
0.6437	Remote Similarity	NPD8098	Approved
0.6431	Remote Similarity	NPD6770	Approved
0.6429	Remote Similarity	NPD3243	Approved
0.6426	Remote Similarity	NPD8329	Phase 3
0.6426	Remote Similarity	NPD7947	Clinical (unspecified phase)
0.6418	Remote Similarity	NPD8325	Phase 3
0.6418	Remote Similarity	NPD8326	Phase 3
0.6418	Remote Similarity	NPD8327	Clinical (unspecified phase)
0.6414	Remote Similarity	NPD8349	Phase 1
0.6413	Remote Similarity	NPD4885	Approved
0.6412	Remote Similarity	NPD7958	Clinical (unspecified phase)
0.6412	Remote Similarity	NPD7957	Phase 1
0.6403	Remote Similarity	NPD1534	Approved
0.6395	Remote Similarity	NPD53	Approved
0.6395	Remote Similarity	NPD7777	Approved
0.6395	Remote Similarity	NPD7778	Approved
0.6394	Remote Similarity	NPD8109	Clinical (unspecified phase)
0.6394	Remote Similarity	NPD8405	Clinical (unspecified phase)
0.6387	Remote Similarity	NPD6164	Phase 2
0.6387	Remote Similarity	NPD6165	Phase 2
0.6387	Remote Similarity	NPD6292	Clinical (unspecified phase)
0.6387	Remote Similarity	NPD7268	Clinical (unspecified phase)
0.6385	Remote Similarity	NPD7727	Phase 2
0.6376	Remote Similarity	NPD8370	Discontinued
0.6373	Remote Similarity	NPD8358	Approved
0.637	Remote Similarity	NPD7417	Discontinued
0.6364	Remote Similarity	NPD2510	Approved
0.6364	Remote Similarity	NPD8423	Phase 2
0.6364	Remote Similarity	NPD2509	Approved
0.6364	Remote Similarity	NPD8399	Phase 1
0.636	Remote Similarity	NPD6160	Clinical (unspecified phase)
0.6357	Remote Similarity	NPD6710	Phase 3
0.6357	Remote Similarity	NPD5003	Discontinued
0.6357	Remote Similarity	NPD8406	Clinical (unspecified phase)
0.6347	Remote Similarity	NPD3280	Approved
0.6343	Remote Similarity	NPD6745	Discontinued
0.6336	Remote Similarity	NPD2920	Discontinued
0.6332	Remote Similarity	NPD7889	Clinical (unspecified phase)
0.6332	Remote Similarity	NPD7946	Pre-registration
0.633	Remote Similarity	NPD7594	Clinical (unspecified phase)
0.633	Remote Similarity	NPD4852	Phase 2
0.6327	Remote Similarity	NPD4328	Approved
0.6324	Remote Similarity	NPD7726	Phase 1
0.6323	Remote Similarity	NPD7690	Clinical (unspecified phase)
0.632	Remote Similarity	NPD6733	Discontinued
0.632	Remote Similarity	NPD8160	Phase 2
0.6316	Remote Similarity	NPD4900	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD7809	Clinical (unspecified phase)
0.6312	Remote Similarity	NPD2721	Clinical (unspecified phase)
0.6312	Remote Similarity	NPD7712	Clinical (unspecified phase)
0.6308	Remote Similarity	NPD6661	Clinical (unspecified phase)
0.6302	Remote Similarity	NPD2916	Discontinued
0.63	Remote Similarity	NPD7219	Approved
0.63	Remote Similarity	NPD7221	Approved
0.6296	Remote Similarity	NPD6218	Discontinued
0.6291	Remote Similarity	NPD7603	Discontinued
0.6291	Remote Similarity	NPD7766	Phase 2
0.6289	Remote Similarity	NPD6058	Phase 2
0.6288	Remote Similarity	NPD2715	Clinical (unspecified phase)
0.6286	Remote Similarity	NPD5891	Approved
0.6284	Remote Similarity	NPD4500	Approved
0.6284	Remote Similarity	NPD4501	Approved
0.6283	Remote Similarity	NPD8112	Clinical (unspecified phase)
0.6281	Remote Similarity	NPD8375	Approved
0.6279	Remote Similarity	NPD7944	Discontinued
0.6278	Remote Similarity	NPD8489	Phase 1
0.6277	Remote Similarity	NPD8017	Clinical (unspecified phase)
0.6277	Remote Similarity	NPD3222	Phase 2
0.6277	Remote Similarity	NPD7548	Discontinued
0.6277	Remote Similarity	NPD8016	Phase 3
0.6277	Remote Similarity	NPD2921	Clinical (unspecified phase)
0.6273	Remote Similarity	NPD6578	Clinical (unspecified phase)
0.6272	Remote Similarity	NPD7558	Phase 2
0.6268	Remote Similarity	NPD7694	Discontinued
0.6255	Remote Similarity	NPD6449	Clinical (unspecified phase)
0.625	Remote Similarity	NPD7924	Phase 2
0.625	Remote Similarity	NPD7925	Phase 2
0.625	Remote Similarity	NPD6503	Clinical (unspecified phase)
0.625	Remote Similarity	NPD3258	Approved
0.6241	Remote Similarity	NPD8246	Approved
0.6241	Remote Similarity	NPD8247	Approved
0.6241	Remote Similarity	NPD4938	Phase 2
0.624	Remote Similarity	NPD7429	Clinical (unspecified phase)
0.6237	Remote Similarity	NPD7658	Phase 2
0.6237	Remote Similarity	NPD8119	Discontinued
0.6237	Remote Similarity	NPD8371	Clinical (unspecified phase)
0.6236	Remote Similarity	NPD7185	Discontinued
0.6232	Remote Similarity	NPD6517	Phase 3
0.623	Remote Similarity	NPD7867	Phase 1
0.6226	Remote Similarity	NPD4862	Clinical (unspecified phase)
0.6226	Remote Similarity	NPD4901	Clinical (unspecified phase)
0.6219	Remote Similarity	NPD4561	Discontinued
0.6217	Remote Similarity	NPD5835	Phase 3
0.6217	Remote Similarity	NPD5834	Phase 3
0.6214	Remote Similarity	NPD7415	Suspended

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