NPASS Compound

Structure

NPC471609 OpenBabel07101718202D 21 23 0 0 1 0 0 0 0 0999 V2000 -2.7198 -3.8819 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4634 -5.0741 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9622 -1.0405 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0591 -3.3899 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3431 -2.4311 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6092 -2.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4752 -0.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6914 -0.3078 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0518 -1.9770 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7475 -4.1153 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9626 -1.0144 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7431 -1.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4752 -1.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6092 -0.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7431 -0.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4067 0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3412 -2.1691 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 1.4013 0.8090 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.6548 -1.7057 0.0000 N 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 -0.0933 1.7796 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 1 10 1 0 0 0 0 2 10 1 0 0 0 0 4 5 1 0 0 0 0 4 10 2 0 0 0 0 5 19 1 0 0 0 0 6 12 2 0 0 0 0 6 13 1 0 0 0 0 7 13 2 0 0 0 0 7 14 1 0 0 0 0 8 11 1 0 0 0 0 8 20 1 0 0 0 0 9 12 1 0 0 0 0 9 19 1 0 0 0 0 11 3 1 1 0 0 0 11 19 1 0 0 0 0 12 15 1 0 0 0 0 13 17 1 0 0 0 0 14 15 2 0 0 0 0 14 18 1 0 0 0 0 15 20 1 0 0 0 0 16 18 2 0 0 0 0 16 20 1 0 0 0 0 16 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	321.11
Volume:	313.151
LogP:	4.294
LogD:	3.998
LogS:	-3.584
# Rotatable Bonds:	2
TPSA:	23.96
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.649
Synthetic Accessibility Score:	3.575
Fsp3:	0.438
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.805
MDCK Permeability:	1.8775375792756677e-05
Pgp-inhibitor:	0.995
Pgp-substrate:	0.005
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.133
30% Bioavailability (F30%):	0.011

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.938
Plasma Protein Binding (PPB):	95.6411361694336%
Volume Distribution (VD):	1.514
Pgp-substrate:	5.860048294067383%

ADMET: Metabolism

CYP1A2-inhibitor:	0.935
CYP1A2-substrate:	0.651
CYP2C19-inhibitor:	0.948
CYP2C19-substrate:	0.433
CYP2C9-inhibitor:	0.459
CYP2C9-substrate:	0.666
CYP2D6-inhibitor:	0.943
CYP2D6-substrate:	0.89
CYP3A4-inhibitor:	0.627
CYP3A4-substrate:	0.358

ADMET: Excretion

Clearance (CL):	10.626
Half-life (T1/2):	0.378

ADMET: Toxicity

hERG Blockers:	0.017
Human Hepatotoxicity (H-HT):	0.98
Drug-inuced Liver Injury (DILI):	0.853
AMES Toxicity:	0.397
Rat Oral Acute Toxicity:	0.849
Maximum Recommended Daily Dose:	0.953
Skin Sensitization:	0.09
Carcinogencity:	0.93
Eye Corrosion:	0.003
Eye Irritation:	0.012
Respiratory Toxicity:	0.935

Download Data

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

Natural Product: NPC471609

Natural Product ID:	NPC471609
*Common Name:**	RCSLUNOLLUVOOG-NSHDSACASA-N
IUPAC Name:	n.a.
Synonyms:	R-82913
Standard InCHIKey:	RCSLUNOLLUVOOG-NSHDSACASA-N
Standard InCHI:	InChI=1S/C16H20ClN3S/c1-10(2)4-5-19-9-12-6-13(17)7-14-15(12)20(8-11(19)3)16(21)18-14/h4,6-7,11H,5,8-9H2,1-3H3,(H,18,21)/t11-/m0/s1
SMILES:	CC(=CCN1Cc2cc(Cl)cc3c2n(C[C@@H]1C)c(n3)S)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL293498
PubChem CID:	3000237
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000295] Benzodiazepines [CHEMONTID:0004097] 1,4-benzodiazepines

*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
NPO2804	Calophyllum inophyllum	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15678383]
NPO2804	Calophyllum inophyllum	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16045947]
NPO2804	Calophyllum inophyllum	Species	Calophyllaceae	Eukaryota	n.a.	stem	n.a.	PMID[20188156]
NPO2804	Calophyllum inophyllum	Species	Calophyllaceae	Eukaryota	n.a.	Malaysian	n.a.	PMID[7506311]
NPO2804	Calophyllum inophyllum	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2804	Calophyllum inophyllum	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2804	Calophyllum inophyllum	Species	Calophyllaceae	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
EC50	6
ED50	1
IC50	18
Others	17

Activity Type	# Activity
Cell Line	15
Individual Protein	16
NON-MOLECULAR	1
Organism	6
Others	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1452	Cell Line	C8166	Homo sapiens	EC50	=	2.0	nM	PMID[452726]
NPT1452	Cell Line	C8166	Homo sapiens	TC50	=	62.0	uM	PMID[452726]
NPT459	Individual Protein	Human immunodeficiency virus type 1 reverse transcriptase	Human immunodeficiency virus 1	Activity	=	0.05	uM	PMID[452728]
NPT459	Individual Protein	Human immunodeficiency virus type 1 reverse transcriptase	Human immunodeficiency virus 1	Activity	=	0.034	uM	PMID[452729]
NPT459	Individual Protein	Human immunodeficiency virus type 1 reverse transcriptase	Human immunodeficiency virus 1	EC50	=	60.0	nM	PMID[452730]
NPT459	Individual Protein	Human immunodeficiency virus type 1 reverse transcriptase	Human immunodeficiency virus 1	EC50	=	5600.0	nM	PMID[452730]
NPT1452	Cell Line	C8166	Homo sapiens	EC50	=	2.0	nM	PMID[452731]
NPT1452	Cell Line	C8166	Homo sapiens	TC50	=	62.0	uM	PMID[452731]
NPT459	Individual Protein	Human immunodeficiency virus type 1 reverse transcriptase	Human immunodeficiency virus 1	Concentration	=	0.16	uM	PMID[452731]
NPT459	Individual Protein	Human immunodeficiency virus type 1 reverse transcriptase	Human immunodeficiency virus 1	Inhibition	=	50.0	%	PMID[452731]
NPT459	Individual Protein	Human immunodeficiency virus type 1 reverse transcriptase	Human immunodeficiency virus 1	IC50	=	0.005	ug.mL-1	PMID[452732]
NPT315	Cell Line	CEM-SS	Homo sapiens	IC50	=	55.0	nM	PMID[452732]
NPT315	Cell Line	CEM-SS	Homo sapiens	CC50	=	35000.0	nM	PMID[452732]
NPT609	Individual Protein	Human immunodeficiency virus type 1 protease	Human immunodeficiency virus 1	IC50	=	311.0	nM	PMID[452734]
NPT25	Cell Line	MT4	Homo sapiens	IC95	=	400.0	nM	PMID[452734]
NPT609	Individual Protein	Human immunodeficiency virus type 1 protease	Human immunodeficiency virus 1	IC50	=	7320.0	nM	PMID[452734]
NPT609	Individual Protein	Human immunodeficiency virus type 1 protease	Human immunodeficiency virus 1	IC50	=	39500.0	nM	PMID[452734]
NPT459	Individual Protein	Human immunodeficiency virus type 1 reverse transcriptase	Human immunodeficiency virus 1	IC50	=	200.0	nM	PMID[452736]
NPT459	Individual Protein	Human immunodeficiency virus type 1 reverse transcriptase	Human immunodeficiency virus 1	ED50	=	0.25	uM	PMID[452736]
NPT459	Individual Protein	Human immunodeficiency virus type 1 reverse transcriptase	Human immunodeficiency virus 1	CD50	=	93.0	uM	PMID[452736]
NPT459	Individual Protein	Human immunodeficiency virus type 1 reverse transcriptase	Human immunodeficiency virus 1	IC50	=	34000.0	nM	PMID[452737]
NPT315	Cell Line	CEM-SS	Homo sapiens	CC50	>	10000.0	nM	PMID[452738]
NPT25	Cell Line	MT4	Homo sapiens	IC50	=	39.0	nM	PMID[452739]
NPT25	Cell Line	MT4	Homo sapiens	IC50	=	42.0	nM	PMID[452740]
NPT1452	Cell Line	C8166	Homo sapiens	IC50	=	1.5	nM	PMID[452741]
NPT1452	Cell Line	C8166	Homo sapiens	CC50	=	34000.0	nM	PMID[452741]
NPT1452	Cell Line	C8166	Homo sapiens	Selectivity index	=	22600.0	n.a.	PMID[452741]
NPT459	Individual Protein	Human immunodeficiency virus type 1 reverse transcriptase	Human immunodeficiency virus 1	IC50	=	700.0	nM	PMID[452742]
NPT112	Cell Line	MOLT-4	Homo sapiens	IC50	=	19000.0	nM	PMID[452742]
NPT459	Individual Protein	Human immunodeficiency virus type 1 reverse transcriptase	Human immunodeficiency virus 1	EC50	=	33.0	nM	PMID[452743]
NPT25	Cell Line	MT4	Homo sapiens	EC50	=	33.0	nM	PMID[452744]
NPT2	Others	Unspecified		Ratio	=	31000.0	n.a.	PMID[452726]
NPT2	Others	Unspecified		FR	=	93.3	n.a.	PMID[452730]
NPT2	Others	Unspecified		Ratio	=	31000.0	n.a.	PMID[452731]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	IC50	>	10000.0	nM	PMID[452733]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	CC50	>	10000.0	nM	PMID[452733]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	IC50	=	34.0	nM	PMID[452735]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	IC50	>	10000.0	nM	PMID[452738]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	IC50	=	190.0	nM	PMID[452742]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Selectivity index	=	100.0	n.a.	PMID[452742]
NPT2	Others	Unspecified		IC50	=	42.66	nM	PMID[452745]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	IC50	=	33.88	nM	PMID[452746]

☑ 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 NPC471609 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	2660
0.1-0.2	18233
0.2-0.3	14539
0.3-0.4	3582
0.4-0.5	2516
0.5-0.6	1045
0.6-0.7	120
0.7-0.8	1
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.7207	Intermediate Similarity	NPC477591
0.7135	Intermediate Similarity	NPC476297
0.7111	Intermediate Similarity	NPC300238
0.6949	Remote Similarity	NPC114209
0.6851	Remote Similarity	NPC476219
0.6804	Remote Similarity	NPC476341
0.6763	Remote Similarity	NPC216159
0.6737	Remote Similarity	NPC317054
0.663	Remote Similarity	NPC476464
0.6529	Remote Similarity	NPC75999
0.6517	Remote Similarity	NPC316018
0.6517	Remote Similarity	NPC314058
0.648	Remote Similarity	NPC473868
0.648	Remote Similarity	NPC63157
0.6464	Remote Similarity	NPC204141
0.6444	Remote Similarity	NPC20144
0.6444	Remote Similarity	NPC42483
0.6436	Remote Similarity	NPC316359
0.6436	Remote Similarity	NPC315617
0.6429	Remote Similarity	NPC314919
0.6421	Remote Similarity	NPC2165
0.6421	Remote Similarity	NPC195507
0.6413	Remote Similarity	NPC40070
0.6402	Remote Similarity	NPC470203
0.6369	Remote Similarity	NPC315348
0.6369	Remote Similarity	NPC32002
0.6349	Remote Similarity	NPC470204
0.6348	Remote Similarity	NPC150259
0.6304	Remote Similarity	NPC21605
0.6298	Remote Similarity	NPC88121
0.6278	Remote Similarity	NPC104483
0.6243	Remote Similarity	NPC115611
0.6236	Remote Similarity	NPC198988
0.6216	Remote Similarity	NPC470111
0.6203	Remote Similarity	NPC469975
0.6201	Remote Similarity	NPC218268
0.6201	Remote Similarity	NPC325252
0.6196	Remote Similarity	NPC285731
0.619	Remote Similarity	NPC469308
0.6188	Remote Similarity	NPC88097
0.6183	Remote Similarity	NPC282531
0.6167	Remote Similarity	NPC125746
0.6154	Remote Similarity	NPC59084
0.6145	Remote Similarity	NPC325599
0.6129	Remote Similarity	NPC201380
0.6129	Remote Similarity	NPC179787
0.6119	Remote Similarity	NPC83381
0.6114	Remote Similarity	NPC478182
0.61	Remote Similarity	NPC16659
0.6099	Remote Similarity	NPC73767
0.6099	Remote Similarity	NPC110126
0.6096	Remote Similarity	NPC321911
0.6094	Remote Similarity	NPC122141
0.6075	Remote Similarity	NPC63545
0.6066	Remote Similarity	NPC469767
0.6066	Remote Similarity	NPC469768
0.6066	Remote Similarity	NPC2949
0.6066	Remote Similarity	NPC469761
0.6066	Remote Similarity	NPC469779
0.6066	Remote Similarity	NPC469783
0.6066	Remote Similarity	NPC469780
0.6066	Remote Similarity	NPC469784
0.6064	Remote Similarity	NPC33421
0.6062	Remote Similarity	NPC225018
0.605	Remote Similarity	NPC265710
0.6043	Remote Similarity	NPC469811
0.6033	Remote Similarity	NPC469766
0.6033	Remote Similarity	NPC476454
0.6031	Remote Similarity	NPC247987
0.6021	Remote Similarity	NPC51054
0.6012	Remote Similarity	NPC41174
0.6011	Remote Similarity	NPC22079
0.601	Remote Similarity	NPC255229
0.601	Remote Similarity	NPC81229
0.6	Remote Similarity	NPC325903
0.6	Remote Similarity	NPC81561
0.599	Remote Similarity	NPC91895
0.599	Remote Similarity	NPC307191
0.599	Remote Similarity	NPC47596
0.5989	Remote Similarity	NPC314102
0.5989	Remote Similarity	NPC478186
0.5989	Remote Similarity	NPC251722
0.5989	Remote Similarity	NPC105127
0.5989	Remote Similarity	NPC84911
0.5989	Remote Similarity	NPC143872
0.5978	Remote Similarity	NPC284635
0.5969	Remote Similarity	NPC49217
0.5966	Remote Similarity	NPC476140
0.596	Remote Similarity	NPC105758
0.596	Remote Similarity	NPC476688
0.596	Remote Similarity	NPC476686
0.5959	Remote Similarity	NPC318065
0.5959	Remote Similarity	NPC56765
0.5959	Remote Similarity	NPC293487
0.5959	Remote Similarity	NPC206819
0.5957	Remote Similarity	NPC471957
0.5954	Remote Similarity	NPC265605
0.5954	Remote Similarity	NPC48564
0.5954	Remote Similarity	NPC182570
0.595	Remote Similarity	NPC121903
0.5949	Remote Similarity	NPC478184
0.5949	Remote Similarity	NPC162799
0.5947	Remote Similarity	NPC470823
0.5945	Remote Similarity	NPC71238
0.5941	Remote Similarity	NPC476566
0.5941	Remote Similarity	NPC148140
0.5939	Remote Similarity	NPC278874
0.5936	Remote Similarity	NPC470440
0.5934	Remote Similarity	NPC96102
0.5934	Remote Similarity	NPC29886
0.5934	Remote Similarity	NPC261195
0.5931	Remote Similarity	NPC108011
0.593	Remote Similarity	NPC314557
0.5924	Remote Similarity	NPC134657
0.592	Remote Similarity	NPC240088
0.592	Remote Similarity	NPC473380
0.592	Remote Similarity	NPC234987
0.5916	Remote Similarity	NPC200214
0.5909	Remote Similarity	NPC164664
0.5909	Remote Similarity	NPC116961
0.5907	Remote Similarity	NPC236711
0.5897	Remote Similarity	NPC194881
0.5895	Remote Similarity	NPC148592
0.5894	Remote Similarity	NPC472289
0.5892	Remote Similarity	NPC238499
0.5889	Remote Similarity	NPC82295
0.5889	Remote Similarity	NPC475450
0.5888	Remote Similarity	NPC478183
0.5886	Remote Similarity	NPC46358
0.5885	Remote Similarity	NPC120070
0.5879	Remote Similarity	NPC82331
0.5876	Remote Similarity	NPC475990
0.5876	Remote Similarity	NPC474880
0.5876	Remote Similarity	NPC221786
0.5876	Remote Similarity	NPC41257
0.5876	Remote Similarity	NPC6436
0.5872	Remote Similarity	NPC116555
0.5871	Remote Similarity	NPC280852
0.5871	Remote Similarity	NPC315715
0.5871	Remote Similarity	NPC474958
0.5867	Remote Similarity	NPC317105
0.5864	Remote Similarity	NPC54981
0.5851	Remote Similarity	NPC469525
0.5851	Remote Similarity	NPC314372
0.5846	Remote Similarity	NPC229173
0.5833	Remote Similarity	NPC113626
0.5833	Remote Similarity	NPC281094
0.5829	Remote Similarity	NPC190296
0.5825	Remote Similarity	NPC286427
0.5824	Remote Similarity	NPC143156
0.5816	Remote Similarity	NPC224632
0.5816	Remote Similarity	NPC478185
0.5815	Remote Similarity	NPC471312
0.5812	Remote Similarity	NPC53947
0.5812	Remote Similarity	NPC24678
0.5812	Remote Similarity	NPC105818
0.5808	Remote Similarity	NPC56233
0.5806	Remote Similarity	NPC279081
0.5805	Remote Similarity	NPC215519
0.5787	Remote Similarity	NPC476950
0.5787	Remote Similarity	NPC250361
0.5787	Remote Similarity	NPC271797
0.5787	Remote Similarity	NPC90723
0.5787	Remote Similarity	NPC21174
0.5781	Remote Similarity	NPC216713
0.578	Remote Similarity	NPC54102
0.578	Remote Similarity	NPC162689
0.5778	Remote Similarity	NPC473587
0.5771	Remote Similarity	NPC208060
0.5763	Remote Similarity	NPC122718
0.5759	Remote Similarity	NPC37548
0.5759	Remote Similarity	NPC288445
0.5759	Remote Similarity	NPC2272
0.5756	Remote Similarity	NPC477891
0.5756	Remote Similarity	NPC39092
0.5751	Remote Similarity	NPC73952
0.5751	Remote Similarity	NPC25008
0.5751	Remote Similarity	NPC469760
0.5751	Remote Similarity	NPC469786
0.5751	Remote Similarity	NPC232798
0.5751	Remote Similarity	NPC259644
0.5751	Remote Similarity	NPC469763
0.5751	Remote Similarity	NPC469765
0.575	Remote Similarity	NPC32534
0.575	Remote Similarity	NPC194411
0.5746	Remote Similarity	NPC475428
0.5744	Remote Similarity	NPC129721
0.5743	Remote Similarity	NPC189812
0.5743	Remote Similarity	NPC297034
0.5743	Remote Similarity	NPC329688
0.5743	Remote Similarity	NPC469938
0.574	Remote Similarity	NPC282247
0.5737	Remote Similarity	NPC288838
0.5733	Remote Similarity	NPC267811
0.5733	Remote Similarity	NPC69843
0.5722	Remote Similarity	NPC473762
0.5722	Remote Similarity	NPC80597
0.5722	Remote Similarity	NPC70922
0.5722	Remote Similarity	NPC230002
0.5722	Remote Similarity	NPC211572

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 NPC471609 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	554
0.1-0.2	1074
0.2-0.3	1389
0.3-0.4	2281
0.4-0.5	2256
0.5-0.6	1269
0.6-0.7	293
0.7-0.8	32
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
1.0	High Similarity	NPD2111	Clinical (unspecified phase)
0.9018	High Similarity	NPD2149	Clinical (unspecified phase)
0.8092	Intermediate Similarity	NPD3361	Phase 1
0.7978	Intermediate Similarity	NPD2729	Approved
0.7978	Intermediate Similarity	NPD2728	Approved
0.7978	Intermediate Similarity	NPD2730	Approved
0.779	Intermediate Similarity	NPD3310	Approved
0.7772	Intermediate Similarity	NPD5012	Phase 2
0.768	Intermediate Similarity	NPD5013	Approved
0.768	Intermediate Similarity	NPD2315	Approved
0.7627	Intermediate Similarity	NPD509	Phase 3
0.7568	Intermediate Similarity	NPD1860	Approved
0.7554	Intermediate Similarity	NPD2301	Approved
0.7539	Intermediate Similarity	NPD2316	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD2927	Phase 3
0.7486	Intermediate Similarity	NPD4213	Clinical (unspecified phase)
0.743	Intermediate Similarity	NPD3889	Approved
0.7414	Intermediate Similarity	NPD2660	Approved
0.7414	Intermediate Similarity	NPD2662	Approved
0.7391	Intermediate Similarity	NPD2731	Phase 2
0.7389	Intermediate Similarity	NPD6794	Approved
0.7322	Intermediate Similarity	NPD5996	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD1313	Approved
0.7234	Intermediate Similarity	NPD3512	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD2128	Phase 1
0.7196	Intermediate Similarity	NPD1887	Clinical (unspecified phase)
0.7189	Intermediate Similarity	NPD7006	Approved
0.7179	Intermediate Similarity	NPD3362	Clinical (unspecified phase)
0.7166	Intermediate Similarity	NPD40	Phase 2
0.7166	Intermediate Similarity	NPD5730	Phase 2
0.7151	Intermediate Similarity	NPD5943	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD4892	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD2793	Discontinued
0.7027	Intermediate Similarity	NPD2875	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD1248	Discontinued
0.7011	Intermediate Similarity	NPD4047	Discontinued
0.7006	Intermediate Similarity	NPD5538	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD4447	Phase 2
0.7	Intermediate Similarity	NPD4649	Clinical (unspecified phase)
0.699	Remote Similarity	NPD3403	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD1288	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD2774	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD2406	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD2373	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD2110	Approved
0.6947	Remote Similarity	NPD1873	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD4902	Discontinued
0.6923	Remote Similarity	NPD2318	Discontinued
0.6919	Remote Similarity	NPD2392	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD1215	Discontinued
0.6908	Remote Similarity	NPD7164	Discontinued
0.6906	Remote Similarity	NPD473	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD2150	Discontinued
0.6897	Remote Similarity	NPD4446	Approved
0.6897	Remote Similarity	NPD6714	Phase 3
0.6895	Remote Similarity	NPD3341	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD6192	Phase 3
0.6891	Remote Similarity	NPD2868	Clinical (unspecified phase)
0.6888	Remote Similarity	NPD6761	Discontinued
0.6882	Remote Similarity	NPD2333	Discontinued
0.6881	Remote Similarity	NPD2807	Discontinued
0.6875	Remote Similarity	NPD4441	Phase 2
0.6856	Remote Similarity	NPD2591	Phase 2
0.6839	Remote Similarity	NPD5892	Approved
0.6825	Remote Similarity	NPD5129	Phase 3
0.6818	Remote Similarity	NPD3460	Discontinued
0.6811	Remote Similarity	NPD2738	Approved
0.6806	Remote Similarity	NPD676	Discontinued
0.6802	Remote Similarity	NPD3419	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD4853	Approved
0.6793	Remote Similarity	NPD6074	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD2864	Phase 1
0.6786	Remote Similarity	NPD5016	Approved
0.6778	Remote Similarity	NPD9709	Approved
0.6778	Remote Similarity	NPD9708	Approved
0.6774	Remote Similarity	NPD1580	Clinical (unspecified phase)
0.6769	Remote Similarity	NPD3378	Clinical (unspecified phase)
0.6743	Remote Similarity	NPD2400	Phase 2
0.6743	Remote Similarity	NPD174	Discontinued
0.674	Remote Similarity	NPD1257	Approved
0.674	Remote Similarity	NPD2524	Discontinued
0.6736	Remote Similarity	NPD1895	Discontinued
0.6734	Remote Similarity	NPD3485	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD2866	Approved
0.672	Remote Similarity	NPD1567	Clinical (unspecified phase)
0.6716	Remote Similarity	NPD1952	Discontinued
0.6716	Remote Similarity	NPD3497	Clinical (unspecified phase)
0.6706	Remote Similarity	NPD3654	Approved
0.67	Remote Similarity	NPD6816	Phase 3
0.6684	Remote Similarity	NPD4940	Approved
0.6684	Remote Similarity	NPD966	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD5962	Phase 2
0.6683	Remote Similarity	NPD6469	Phase 3
0.6683	Remote Similarity	NPD6468	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1043	Phase 3
0.6667	Remote Similarity	NPD1272	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2818	Discontinued
0.665	Remote Similarity	NPD6265	Discontinued
0.6648	Remote Similarity	NPD3630	Approved
0.6648	Remote Similarity	NPD3629	Approved
0.6634	Remote Similarity	NPD5462	Discontinued
0.6634	Remote Similarity	NPD691	Discontinued
0.663	Remote Similarity	NPD3115	Approved
0.663	Remote Similarity	NPD3113	Approved
0.663	Remote Similarity	NPD3114	Approved
0.663	Remote Similarity	NPD939	Clinical (unspecified phase)
0.663	Remote Similarity	NPD3112	Approved
0.6621	Remote Similarity	NPD1579	Discontinued
0.6616	Remote Similarity	NPD7884	Discontinued
0.6615	Remote Similarity	NPD2137	Approved
0.6615	Remote Similarity	NPD2138	Approved
0.6601	Remote Similarity	NPD5885	Approved
0.6597	Remote Similarity	NPD409	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD1333	Phase 3
0.6595	Remote Similarity	NPD2865	Clinical (unspecified phase)
0.6583	Remote Similarity	NPD2352	Approved
0.6578	Remote Similarity	NPD1015	Phase 2
0.6578	Remote Similarity	NPD1016	Phase 2
0.6576	Remote Similarity	NPD2165	Phase 1
0.6566	Remote Similarity	NPD3002	Clinical (unspecified phase)
0.6564	Remote Similarity	NPD1637	Clinical (unspecified phase)
0.6559	Remote Similarity	NPD1042	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD3385	Approved
0.655	Remote Similarity	NPD1658	Discontinued
0.6546	Remote Similarity	NPD2084	Discontinued
0.6546	Remote Similarity	NPD1327	Discontinued
0.6546	Remote Similarity	NPD2930	Clinical (unspecified phase)
0.654	Remote Similarity	NPD1468	Clinical (unspecified phase)
0.6537	Remote Similarity	NPD2536	Discontinued
0.6536	Remote Similarity	NPD4637	Clinical (unspecified phase)
0.6526	Remote Similarity	NPD2390	Clinical (unspecified phase)
0.6526	Remote Similarity	NPD3848	Phase 2
0.6526	Remote Similarity	NPD5648	Clinical (unspecified phase)
0.6517	Remote Similarity	NPD6577	Clinical (unspecified phase)
0.6517	Remote Similarity	NPD3431	Approved
0.6517	Remote Similarity	NPD3430	Approved
0.6515	Remote Similarity	NPD6721	Phase 1
0.6514	Remote Similarity	NPD2141	Approved
0.6514	Remote Similarity	NPD2142	Approved
0.6514	Remote Similarity	NPD2140	Approved
0.6514	Remote Similarity	NPD2867	Approved
0.6509	Remote Similarity	NPD1937	Approved
0.6503	Remote Similarity	NPD2462	Phase 3
0.6503	Remote Similarity	NPD2466	Phase 3
0.6503	Remote Similarity	NPD2465	Approved
0.6495	Remote Similarity	NPD7111	Discontinued
0.6488	Remote Similarity	NPD6264	Discontinued
0.6488	Remote Similarity	NPD7005	Clinical (unspecified phase)
0.6474	Remote Similarity	NPD2478	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD6828	Phase 2
0.6458	Remote Similarity	NPD3347	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD6827	Clinical (unspecified phase)
0.6447	Remote Similarity	NPD1332	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD9724	Phase 1
0.6441	Remote Similarity	NPD6554	Approved
0.6441	Remote Similarity	NPD45	Approved
0.6438	Remote Similarity	NPD5094	Approved
0.6436	Remote Similarity	NPD6619	Phase 3
0.6429	Remote Similarity	NPD1683	Approved
0.6429	Remote Similarity	NPD702	Clinical (unspecified phase)
0.6425	Remote Similarity	NPD4112	Clinical (unspecified phase)
0.6422	Remote Similarity	NPD7023	Clinical (unspecified phase)
0.6422	Remote Similarity	NPD4854	Phase 3
0.642	Remote Similarity	NPD2399	Clinical (unspecified phase)
0.6415	Remote Similarity	NPD5540	Phase 2
0.6409	Remote Similarity	NPD5671	Approved
0.6402	Remote Similarity	NPD418	Approved
0.6402	Remote Similarity	NPD7264	Clinical (unspecified phase)
0.64	Remote Similarity	NPD2009	Clinical (unspecified phase)
0.6398	Remote Similarity	NPD6285	Phase 2
0.6392	Remote Similarity	NPD3799	Suspended
0.6392	Remote Similarity	NPD7297	Phase 2
0.6392	Remote Similarity	NPD2829	Clinical (unspecified phase)
0.639	Remote Similarity	NPD2880	Discontinued
0.6381	Remote Similarity	NPD6271	Approved
0.6381	Remote Similarity	NPD6403	Clinical (unspecified phase)
0.6378	Remote Similarity	NPD1893	Phase 2
0.6378	Remote Similarity	NPD1892	Phase 2
0.6373	Remote Similarity	NPD3418	Clinical (unspecified phase)
0.6369	Remote Similarity	NPD1902	Approved
0.6369	Remote Similarity	NPD2073	Approved
0.6369	Remote Similarity	NPD2072	Approved
0.6369	Remote Similarity	NPD1904	Approved
0.6369	Remote Similarity	NPD2075	Approved
0.6369	Remote Similarity	NPD2074	Approved
0.6364	Remote Similarity	NPD2767	Approved
0.6364	Remote Similarity	NPD2768	Approved
0.6359	Remote Similarity	NPD5843	Discontinued
0.6355	Remote Similarity	NPD2839	Phase 2
0.6354	Remote Similarity	NPD4864	Approved
0.6351	Remote Similarity	NPD6328	Clinical (unspecified phase)
0.635	Remote Similarity	NPD2963	Phase 1
0.635	Remote Similarity	NPD3913	Clinical (unspecified phase)
0.6345	Remote Similarity	NPD5508	Phase 1
0.6343	Remote Similarity	NPD1556	Clinical (unspecified phase)
0.6335	Remote Similarity	NPD4550	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD5425	Phase 1
0.6332	Remote Similarity	NPD5463	Clinical (unspecified phase)
0.633	Remote Similarity	NPD5300	Clinical (unspecified phase)
0.6321	Remote Similarity	NPD6520	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