NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	202.06
Volume:	209.547
LogP:	1.951
LogD:	1.782
LogS:	-3.434
# Rotatable Bonds:	1
TPSA:	43.37
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.699
Synthetic Accessibility Score:	2.122
Fsp3:	0.167
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.591
MDCK Permeability:	2.2746771719539538e-05
Pgp-inhibitor:	0.059
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.708

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.178
Plasma Protein Binding (PPB):	89.11145782470703%
Volume Distribution (VD):	0.638
Pgp-substrate:	4.608647346496582%

ADMET: Metabolism

CYP1A2-inhibitor:	0.982
CYP1A2-substrate:	0.879
CYP2C19-inhibitor:	0.849
CYP2C19-substrate:	0.403
CYP2C9-inhibitor:	0.651
CYP2C9-substrate:	0.814
CYP2D6-inhibitor:	0.88
CYP2D6-substrate:	0.453
CYP3A4-inhibitor:	0.624
CYP3A4-substrate:	0.222

ADMET: Excretion

Clearance (CL):	6.771
Half-life (T1/2):	0.473

ADMET: Toxicity

hERG Blockers:	0.021
Human Hepatotoxicity (H-HT):	0.186
Drug-inuced Liver Injury (DILI):	0.474
AMES Toxicity:	0.855
Rat Oral Acute Toxicity:	0.931
Maximum Recommended Daily Dose:	0.86
Skin Sensitization:	0.89
Carcinogencity:	0.84
Eye Corrosion:	0.22
Eye Irritation:	0.99
Respiratory Toxicity:	0.813

Download Data

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

Natural Product: NPC182646

Natural Product ID:	NPC182646
*Common Name:**	Sid22411775
IUPAC Name:	5-methoxy-2-methylnaphthalene-1,4-dione
Synonyms:
Standard InCHIKey:	ITNOIFSYUBMQKB-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C12H10O3/c1-7-6-9(13)11-8(12(7)14)4-3-5-10(11)15-2/h3-6H,1-2H3
SMILES:	CC1=CC(=O)c2c(cccc2OC)C1=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1531003
PubChem CID:	185478
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000023] Naphthalenes [CHEMONTID:0000153] Naphthoquinones

*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
NPO6969	Triphyophyllum peltatum	Species	Dioncophyllaceae	Eukaryota	n.a.	stem	n.a.	DOI[10.1007/s004360050318]
NPO6969	Triphyophyllum peltatum	Species	Dioncophyllaceae	Eukaryota	n.a.	root	n.a.	DOI[10.1007/s004360050318]
NPO6969	Triphyophyllum peltatum	Species	Dioncophyllaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22019229]
NPO32707	burman diospyros burmanica	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[22858297]
NPO6969	Triphyophyllum peltatum	Species	Dioncophyllaceae	Eukaryota	n.a.	root	n.a.	PMID[9371362]
NPO6969	Triphyophyllum peltatum	Species	Dioncophyllaceae	Eukaryota	n.a.	stem	n.a.	PMID[9371362]
NPO6969	Triphyophyllum peltatum	Species	Dioncophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6969	Triphyophyllum peltatum	Species	Dioncophyllaceae	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
AC50	7
EC50	2
IC50	13
Others	2
Potency	45

Activity Type	# Activity
Cell Line	9
Individual Protein	37
NON-MOLECULAR	4
Organism	4
Others	12
PROTEIN COMPLEX	3
Uncleic Acid	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT483	Individual Protein	Prelamin-A/C	Homo sapiens	Potency	=	22387.2	nM	PMID[520489]
NPT1197	Individual Protein	Huntingtin	Homo sapiens	Potency	=	14125.4	nM	PMID[520489]
NPT51	Individual Protein	Microtubule-associated protein tau	Homo sapiens	Potency	=	7079.5	nM	PMID[520489]
NPT531	Individual Protein	Nuclear receptor ROR-gamma	Mus musculus	Potency	=	7079.5	nM	PMID[520489]
NPT3	Individual Protein	Thioredoxin glutathione reductase	Schistosoma mansoni	Potency	=	39810.7	nM	PMID[520489]
NPT54	Individual Protein	Nonstructural protein 1	Influenza A virus	Potency	=	3981.1	nM	PMID[520489]
NPT51	Individual Protein	Microtubule-associated protein tau	Homo sapiens	Potency	=	17782.8	nM	PMID[520489]
NPT55	Individual Protein	Putative fructose-1,6-bisphosphate aldolase	Giardia intestinalis	Potency	=	501.2	nM	PMID[520489]
NPT531	Individual Protein	Nuclear receptor ROR-gamma	Mus musculus	Potency	=	11220.2	nM	PMID[520489]
NPT1282	Individual Protein	Microphthalmia-associated transcription factor	Homo sapiens	AC50	=	7828.0	nM	PMID[520489]
NPT1861	Individual Protein	Mitochondrial import inner membrane translocase subunit TIM10	Saccharomyces cerevisiae S288c	IC50	=	13200.0	nM	PMID[520489]
NPT5055	Individual Protein	Mitochondrial import inner membrane translocase subunit TIM23	Saccharomyces cerevisiae S288c	IC50	=	5320.0	nM	PMID[520489]
NPT1282	Individual Protein	Microphthalmia-associated transcription factor	Homo sapiens	AC50	=	18804.0	nM	PMID[520489]
NPT64	Individual Protein	ATPase family AAA domain-containing protein 5	Homo sapiens	Potency	n.a.	29092.9	nM	PMID[520489]
NPT4674	Individual Protein	Apoptotic protease-activating factor 1	Homo sapiens	IC50	>	100000.0	nM	PMID[520489]
NPT198	Individual Protein	Vitamin D receptor	Homo sapiens	Potency	n.a.	39810.7	nM	PMID[520489]
NPT1083	Cell Line	A-375	Homo sapiens	AC50	=	37758.0	nM	PMID[520489]
NPT65	Cell Line	HepG2	Homo sapiens	Potency	n.a.	25118.9	nM	PMID[520489]
NPT154	Individual Protein	Mothers against decapentaplegic homolog 3	Homo sapiens	Potency	n.a.	35481.3	nM	PMID[520489]
NPT71	Cell Line	HEK293	Homo sapiens	Potency	n.a.	11220.2	nM	PMID[520489]
NPT4674	Individual Protein	Apoptotic protease-activating factor 1	Homo sapiens	IC50	=	14400.0	nM	PMID[520489]
NPT927	Cell Line	PBMC	Homo sapiens	EC50	=	16000.0	nM	PMID[520490]
NPT2971	Individual Protein	DNA dC->dU-editing enzyme APOBEC-3F	Homo sapiens	Potency	n.a.	11220.2	nM	PMID[520489]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	45000.0	nM	PMID[520491]
NPT10	Individual Protein	Geminin	Homo sapiens	Potency	n.a.	23109.3	nM	PMID[520489]
NPT10	Individual Protein	Geminin	Homo sapiens	Potency	n.a.	20596.2	nM	PMID[520489]
NPT478	Individual Protein	Ataxin-2	Homo sapiens	Potency	n.a.	14125.4	nM	PMID[520489]
NPT101	Individual Protein	Glucagon-like peptide 1 receptor	Homo sapiens	Potency	n.a.	28183.8	nM	PMID[520489]
NPT159	Individual Protein	Aberrant vpr protein	Human immunodeficiency virus 1	Potency	n.a.	14125.4	nM	PMID[520489]
NPT1043	Individual Protein	Glycoprotein hormones alpha chain	Homo sapiens	Potency	n.a.	10000.0	nM	PMID[520489]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	4610.9	nM	PMID[520489]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	2909.3	nM	PMID[520489]
NPT444	Individual Protein	Ubiquitin carboxyl-terminal hydrolase 1	Homo sapiens	Potency	n.a.	35481.3	nM	PMID[520489]
NPT535	Individual Protein	Parathyroid hormone receptor	Homo sapiens	Potency	n.a.	44668.4	nM	PMID[520489]
NPT105	Individual Protein	Muscleblind-like protein 1	Homo sapiens	Potency	n.a.	891.3	nM	PMID[520489]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	4000.0	nM	PMID[520492]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	5000.0	nM	PMID[520492]
NPT170	Cell Line	SK-MEL-28	Homo sapiens	IC50	=	5000.0	nM	PMID[520492]
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	Potency	=	11220.2	nM	PMID[520489]
NPT536	Uncleic Acid	microRNA 21	Homo sapiens	Potency	=	23280.9	nM	PMID[520489]
NPT94	Individual Protein	Aldehyde dehydrogenase 1A1	Homo sapiens	Potency	=	39810.7	nM	PMID[520489]
NPT2	Others	Unspecified		Potency	=	29092.9	nM	PMID[520489]
NPT2	Others	Unspecified		Potency	n.a.	29092.9	nM	PMID[520489]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	14715.7	nM	PMID[520489]
NPT20798	PROTEIN COMPLEX	GTP-binding nuclear protein Ran/Importin subunit beta-1/Snurportin-1	Homo sapiens	Potency	n.a.	29092.9	nM	PMID[520489]
NPT8	Individual Protein	DNA polymerase iota	Homo sapiens	Potency	n.a.	100000.0	nM	PMID[520489]
NPT9	Individual Protein	DNA polymerase eta	Homo sapiens	Potency	n.a.	89125.1	nM	PMID[520489]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	4653.5	nM	PMID[520489]
NPT2	Others	Unspecified		Potency	n.a.	11220.2	nM	PMID[520489]
NPT2	Others	Unspecified		IC50	=	16600.0	nM	PMID[520489]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	EC50	=	4000.0	nM	PMID[520490]
NPT841	Organism	Leishmania major	Leishmania major	IC50	=	3300.0	nM	PMID[520491]
NPT2	Others	Unspecified		Ratio IC50	=	13.6	n.a.	PMID[520491]
NPT2	Others	Unspecified		Potency	n.a.	2818.4	nM	PMID[520489]
NPT2	Others	Unspecified		Potency	n.a.	22387.2	nM	PMID[520489]
NPT2	Others	Unspecified		Potency	n.a.	20596.2	nM	PMID[520489]
NPT861	Individual Protein	Isocitrate dehydrogenase [NADP] cytoplasmic	Homo sapiens	Potency	n.a.	18356.4	nM	PMID[520489]
NPT2	Others	Unspecified		AC50	=	15250.0	nM	PMID[520489]
NPT2	Others	Unspecified		AbsAC35_uM	=	6.68	uM	PMID[520489]
NPT2	Others	Unspecified		Potency	n.a.	39810.7	nM	PMID[520489]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	3000.0	nM	PMID[520492]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	2000.0	nM	PMID[520492]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	5000.0	nM	PMID[520492]

☑ 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 NPC182646 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	394
0.1-0.2	1911
0.2-0.3	4812
0.3-0.4	11678
0.4-0.5	6005
0.5-0.6	5423
0.6-0.7	8801
0.7-0.8	3459
0.8-0.85	169
0.85-0.9	35
0.9-0.95	8
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9667	High Similarity	NPC45537
0.9355	High Similarity	NPC205360
0.9194	High Similarity	NPC57552
0.9153	High Similarity	NPC171023
0.9062	High Similarity	NPC22222
0.9062	High Similarity	NPC281513
0.8992	High Similarity	NPC232996
0.8984	High Similarity	NPC1249
0.8923	High Similarity	NPC284184
0.8923	High Similarity	NPC301341
0.8898	High Similarity	NPC477412
0.888	High Similarity	NPC470841
0.8846	High Similarity	NPC141934
0.8843	High Similarity	NPC206778
0.8843	High Similarity	NPC285829
0.88	High Similarity	NPC177925
0.879	High Similarity	NPC56332
0.8788	High Similarity	NPC477408
0.8729	High Similarity	NPC279916
0.872	High Similarity	NPC224657
0.8661	High Similarity	NPC237225
0.8657	High Similarity	NPC84273
0.8651	High Similarity	NPC474737
0.8651	High Similarity	NPC474264
0.8647	High Similarity	NPC1268
0.8647	High Similarity	NPC223336
0.864	High Similarity	NPC470163
0.864	High Similarity	NPC470162
0.8629	High Similarity	NPC307174
0.8607	High Similarity	NPC201284
0.8583	High Similarity	NPC298884
0.8582	High Similarity	NPC109007
0.8571	High Similarity	NPC53953
0.8538	High Similarity	NPC183103
0.8519	High Similarity	NPC124365
0.8512	High Similarity	NPC108288
0.8504	High Similarity	NPC51037
0.8492	Intermediate Similarity	NPC310540
0.8485	Intermediate Similarity	NPC217914
0.8473	Intermediate Similarity	NPC470406
0.8467	Intermediate Similarity	NPC274085
0.8467	Intermediate Similarity	NPC89664
0.8467	Intermediate Similarity	NPC475201
0.8462	Intermediate Similarity	NPC279596
0.8462	Intermediate Similarity	NPC239134
0.8456	Intermediate Similarity	NPC69755
0.843	Intermediate Similarity	NPC188907
0.8403	Intermediate Similarity	NPC54626
0.8397	Intermediate Similarity	NPC474340
0.8397	Intermediate Similarity	NPC477406
0.8394	Intermediate Similarity	NPC215451
0.8394	Intermediate Similarity	NPC53016
0.8394	Intermediate Similarity	NPC277369
0.8387	Intermediate Similarity	NPC470092
0.8385	Intermediate Similarity	NPC198305
0.8385	Intermediate Similarity	NPC473271
0.8374	Intermediate Similarity	NPC32298
0.8372	Intermediate Similarity	NPC165257
0.837	Intermediate Similarity	NPC470407
0.8359	Intermediate Similarity	NPC306765
0.8359	Intermediate Similarity	NPC3224
0.8359	Intermediate Similarity	NPC231774
0.8358	Intermediate Similarity	NPC471542
0.8346	Intermediate Similarity	NPC30216
0.8346	Intermediate Similarity	NPC4012
0.8333	Intermediate Similarity	NPC300274
0.8333	Intermediate Similarity	NPC477409
0.8333	Intermediate Similarity	NPC217756
0.8321	Intermediate Similarity	NPC164295
0.8321	Intermediate Similarity	NPC301717
0.8306	Intermediate Similarity	NPC54243
0.8306	Intermediate Similarity	NPC35744
0.8295	Intermediate Similarity	NPC428300
0.8293	Intermediate Similarity	NPC217423
0.8273	Intermediate Similarity	NPC49282
0.8273	Intermediate Similarity	NPC73416
0.8273	Intermediate Similarity	NPC478019
0.8273	Intermediate Similarity	NPC160777
0.8271	Intermediate Similarity	NPC274876
0.8268	Intermediate Similarity	NPC375356
0.8261	Intermediate Similarity	NPC167663
0.8258	Intermediate Similarity	NPC472882
0.8258	Intermediate Similarity	NPC309430
0.8254	Intermediate Similarity	NPC314329
0.825	Intermediate Similarity	NPC23332
0.8248	Intermediate Similarity	NPC149780
0.8244	Intermediate Similarity	NPC475741
0.8226	Intermediate Similarity	NPC166591
0.8222	Intermediate Similarity	NPC186647
0.8217	Intermediate Similarity	NPC237868
0.8214	Intermediate Similarity	NPC300540
0.8209	Intermediate Similarity	NPC22644
0.8209	Intermediate Similarity	NPC470844
0.8203	Intermediate Similarity	NPC74507
0.8203	Intermediate Similarity	NPC234890
0.8203	Intermediate Similarity	NPC75432
0.8203	Intermediate Similarity	NPC265910
0.8203	Intermediate Similarity	NPC142956
0.8203	Intermediate Similarity	NPC91475
0.8201	Intermediate Similarity	NPC19896
0.8201	Intermediate Similarity	NPC229787
0.8195	Intermediate Similarity	NPC171968
0.8189	Intermediate Similarity	NPC46634
0.8175	Intermediate Similarity	NPC225245
0.8168	Intermediate Similarity	NPC34414
0.8168	Intermediate Similarity	NPC146647
0.8167	Intermediate Similarity	NPC183648
0.8162	Intermediate Similarity	NPC265181
0.8162	Intermediate Similarity	NPC233707
0.8162	Intermediate Similarity	NPC61590
0.816	Intermediate Similarity	NPC232178
0.8154	Intermediate Similarity	NPC71525
0.8148	Intermediate Similarity	NPC471670
0.8145	Intermediate Similarity	NPC240664
0.8143	Intermediate Similarity	NPC28632
0.814	Intermediate Similarity	NPC103540
0.814	Intermediate Similarity	NPC2771
0.813	Intermediate Similarity	NPC161304
0.8129	Intermediate Similarity	NPC117674
0.8125	Intermediate Similarity	NPC135062
0.8125	Intermediate Similarity	NPC472888
0.812	Intermediate Similarity	NPC246693
0.812	Intermediate Similarity	NPC118253
0.812	Intermediate Similarity	NPC470160
0.812	Intermediate Similarity	NPC110609
0.812	Intermediate Similarity	NPC242358
0.8106	Intermediate Similarity	NPC7569
0.8106	Intermediate Similarity	NPC117609
0.8106	Intermediate Similarity	NPC278787
0.8102	Intermediate Similarity	NPC476477
0.8102	Intermediate Similarity	NPC471602
0.8102	Intermediate Similarity	NPC306835
0.8102	Intermediate Similarity	NPC256463
0.8102	Intermediate Similarity	NPC111422
0.8102	Intermediate Similarity	NPC216312
0.8102	Intermediate Similarity	NPC295339
0.8102	Intermediate Similarity	NPC29771
0.8102	Intermediate Similarity	NPC299405
0.8095	Intermediate Similarity	NPC216297
0.8095	Intermediate Similarity	NPC7151
0.8095	Intermediate Similarity	NPC473662
0.8095	Intermediate Similarity	NPC230951
0.8092	Intermediate Similarity	NPC125887
0.8092	Intermediate Similarity	NPC282923
0.8077	Intermediate Similarity	NPC1991
0.8077	Intermediate Similarity	NPC96915
0.8074	Intermediate Similarity	NPC88065
0.8074	Intermediate Similarity	NPC298900
0.8074	Intermediate Similarity	NPC95485
0.8074	Intermediate Similarity	NPC89504
0.8065	Intermediate Similarity	NPC477453
0.8065	Intermediate Similarity	NPC316062
0.8062	Intermediate Similarity	NPC68756
0.8062	Intermediate Similarity	NPC152525
0.806	Intermediate Similarity	NPC254603
0.806	Intermediate Similarity	NPC477536
0.8058	Intermediate Similarity	NPC329493
0.8058	Intermediate Similarity	NPC11314
0.8058	Intermediate Similarity	NPC49108
0.8056	Intermediate Similarity	NPC144283
0.8049	Intermediate Similarity	NPC114144
0.8045	Intermediate Similarity	NPC244699
0.8045	Intermediate Similarity	NPC324488
0.8045	Intermediate Similarity	NPC141549
0.8043	Intermediate Similarity	NPC220496
0.8043	Intermediate Similarity	NPC147542
0.8043	Intermediate Similarity	NPC327916
0.8043	Intermediate Similarity	NPC37992
0.8043	Intermediate Similarity	NPC42262
0.8043	Intermediate Similarity	NPC32749
0.8043	Intermediate Similarity	NPC241349
0.8043	Intermediate Similarity	NPC156872
0.803	Intermediate Similarity	NPC99731
0.803	Intermediate Similarity	NPC261759
0.803	Intermediate Similarity	NPC473019
0.8029	Intermediate Similarity	NPC173980
0.8028	Intermediate Similarity	NPC289042
0.8028	Intermediate Similarity	NPC56433
0.8028	Intermediate Similarity	NPC252208
0.8028	Intermediate Similarity	NPC478018
0.8028	Intermediate Similarity	NPC312929
0.8028	Intermediate Similarity	NPC190648
0.8028	Intermediate Similarity	NPC126767
0.8028	Intermediate Similarity	NPC118027
0.8028	Intermediate Similarity	NPC245584
0.8015	Intermediate Similarity	NPC293387
0.8015	Intermediate Similarity	NPC181715
0.8	Intermediate Similarity	NPC476473
0.8	Intermediate Similarity	NPC469954
0.8	Intermediate Similarity	NPC65041
0.8	Intermediate Similarity	NPC209858
0.8	Intermediate Similarity	NPC45104
0.7986	Intermediate Similarity	NPC471444
0.7986	Intermediate Similarity	NPC255641
0.7986	Intermediate Similarity	NPC290954
0.7986	Intermediate Similarity	NPC257003
0.7985	Intermediate Similarity	NPC312560
0.7984	Intermediate Similarity	NPC141252
0.7984	Intermediate Similarity	NPC474691
0.7984	Intermediate Similarity	NPC93730

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 NPC182646 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	384
0.1-0.2	1007
0.2-0.3	1395
0.3-0.4	2644
0.4-0.5	1938
0.5-0.6	1172
0.6-0.7	495
0.7-0.8	106
0.8-0.85	7
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8512	High Similarity	NPD405	Clinical (unspecified phase)
0.8296	Intermediate Similarity	NPD2346	Discontinued
0.8254	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.8217	Intermediate Similarity	NPD2798	Approved
0.8203	Intermediate Similarity	NPD1876	Approved
0.8162	Intermediate Similarity	NPD1471	Phase 3
0.816	Intermediate Similarity	NPD1651	Approved
0.814	Intermediate Similarity	NPD1470	Approved
0.8115	Intermediate Similarity	NPD1241	Discontinued
0.7969	Intermediate Similarity	NPD1281	Approved
0.7969	Intermediate Similarity	NPD1201	Approved
0.7917	Intermediate Similarity	NPD3226	Approved
0.7907	Intermediate Similarity	NPD3972	Approved
0.7883	Intermediate Similarity	NPD2799	Discontinued
0.7836	Intermediate Similarity	NPD2313	Discontinued
0.7826	Intermediate Similarity	NPD2935	Discontinued
0.782	Intermediate Similarity	NPD6832	Phase 2
0.7805	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7794	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7786	Intermediate Similarity	NPD1283	Approved
0.7778	Intermediate Similarity	NPD9493	Approved
0.777	Intermediate Similarity	NPD2344	Approved
0.7769	Intermediate Similarity	NPD9717	Approved
0.7737	Intermediate Similarity	NPD1607	Approved
0.7734	Intermediate Similarity	NPD5691	Approved
0.7721	Intermediate Similarity	NPD1240	Approved
0.7714	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7704	Intermediate Similarity	NPD411	Approved
0.7674	Intermediate Similarity	NPD4626	Approved
0.7669	Intermediate Similarity	NPD1019	Discontinued
0.7664	Intermediate Similarity	NPD447	Suspended
0.7606	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7594	Intermediate Similarity	NPD1203	Approved
0.7571	Intermediate Similarity	NPD2796	Approved
0.7552	Intermediate Similarity	NPD2309	Approved
0.7521	Intermediate Similarity	NPD164	Approved
0.7518	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1510	Phase 2
0.75	Intermediate Similarity	NPD3748	Approved
0.75	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD7003	Approved
0.7467	Intermediate Similarity	NPD7819	Suspended
0.7438	Intermediate Similarity	NPD9261	Approved
0.741	Intermediate Similarity	NPD1933	Approved
0.7405	Intermediate Similarity	NPD17	Approved
0.7405	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD9494	Approved
0.7338	Intermediate Similarity	NPD4307	Phase 2
0.7338	Intermediate Similarity	NPD2979	Phase 3
0.7324	Intermediate Similarity	NPD1551	Phase 2
0.7315	Intermediate Similarity	NPD2651	Approved
0.7315	Intermediate Similarity	NPD2649	Approved
0.7308	Intermediate Similarity	NPD5536	Phase 2
0.7293	Intermediate Similarity	NPD1611	Approved
0.7292	Intermediate Similarity	NPD1243	Approved
0.728	Intermediate Similarity	NPD2182	Approved
0.7279	Intermediate Similarity	NPD2534	Approved
0.7279	Intermediate Similarity	NPD2533	Approved
0.7279	Intermediate Similarity	NPD2532	Approved
0.7266	Intermediate Similarity	NPD8032	Phase 2
0.7244	Intermediate Similarity	NPD6232	Discontinued
0.7241	Intermediate Similarity	NPD3750	Approved
0.7239	Intermediate Similarity	NPD1608	Approved
0.723	Intermediate Similarity	NPD6273	Approved
0.7222	Intermediate Similarity	NPD1549	Phase 2
0.7215	Intermediate Similarity	NPD7473	Discontinued
0.7206	Intermediate Similarity	NPD3267	Approved
0.7206	Intermediate Similarity	NPD3266	Approved
0.72	Intermediate Similarity	NPD9263	Approved
0.72	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD9264	Approved
0.72	Intermediate Similarity	NPD9267	Approved
0.7192	Intermediate Similarity	NPD3295	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD5616	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD920	Approved
0.7177	Intermediate Similarity	NPD9697	Approved
0.7171	Intermediate Similarity	NPD6279	Approved
0.7171	Intermediate Similarity	NPD6844	Discontinued
0.7171	Intermediate Similarity	NPD6280	Approved
0.7165	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7154	Intermediate Similarity	NPD709	Approved
0.7153	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD74	Approved
0.7143	Intermediate Similarity	NPD9266	Approved
0.7143	Intermediate Similarity	NPD1778	Approved
0.7133	Intermediate Similarity	NPD4308	Phase 3
0.7115	Intermediate Similarity	NPD5494	Approved
0.7095	Intermediate Similarity	NPD6799	Approved
0.7095	Intermediate Similarity	NPD1511	Approved
0.7092	Intermediate Similarity	NPD3142	Approved
0.7092	Intermediate Similarity	NPD3140	Approved
0.7083	Intermediate Similarity	NPD2438	Suspended
0.7083	Intermediate Similarity	NPD2531	Phase 2
0.708	Intermediate Similarity	NPD1164	Approved
0.708	Intermediate Similarity	NPD2797	Approved
0.7068	Intermediate Similarity	NPD5585	Approved
0.7055	Intermediate Similarity	NPD2800	Approved
0.7055	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD4661	Approved
0.7047	Intermediate Similarity	NPD4662	Approved
0.7039	Intermediate Similarity	NPD6599	Discontinued
0.7032	Intermediate Similarity	NPD3882	Suspended
0.7015	Intermediate Similarity	NPD2932	Approved
0.7014	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD2801	Approved
0.7013	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD1512	Approved
0.6992	Remote Similarity	NPD9545	Approved
0.6984	Remote Similarity	NPD3134	Approved
0.6983	Remote Similarity	NPD650	Approved
0.6981	Remote Similarity	NPD3926	Phase 2
0.6974	Remote Similarity	NPD7458	Discontinued
0.6972	Remote Similarity	NPD943	Approved
0.6968	Remote Similarity	NPD2296	Approved
0.6968	Remote Similarity	NPD5402	Approved
0.6966	Remote Similarity	NPD4476	Approved
0.6966	Remote Similarity	NPD5408	Approved
0.6966	Remote Similarity	NPD4477	Approved
0.6966	Remote Similarity	NPD5404	Approved
0.6966	Remote Similarity	NPD5406	Approved
0.6966	Remote Similarity	NPD5405	Approved
0.6963	Remote Similarity	NPD3496	Discontinued
0.6962	Remote Similarity	NPD1247	Approved
0.6962	Remote Similarity	NPD6959	Discontinued
0.695	Remote Similarity	NPD3268	Approved
0.695	Remote Similarity	NPD3764	Approved
0.6948	Remote Similarity	NPD1934	Approved
0.6943	Remote Similarity	NPD919	Approved
0.694	Remote Similarity	NPD3025	Approved
0.694	Remote Similarity	NPD3024	Approved
0.6939	Remote Similarity	NPD2654	Approved
0.6934	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6934	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD5401	Approved
0.6929	Remote Similarity	NPD1358	Approved
0.6928	Remote Similarity	NPD4380	Phase 2
0.6913	Remote Similarity	NPD3300	Phase 2
0.6911	Remote Similarity	NPD1238	Approved
0.6903	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD4628	Phase 3
0.6889	Remote Similarity	NPD3019	Approved
0.6883	Remote Similarity	NPD7411	Suspended
0.6879	Remote Similarity	NPD3749	Approved
0.6875	Remote Similarity	NPD6651	Approved
0.687	Remote Similarity	NPD5283	Phase 1
0.6859	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD5977	Approved
0.6859	Remote Similarity	NPD3817	Phase 2
0.6859	Remote Similarity	NPD5978	Approved
0.6852	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD6099	Approved
0.6849	Remote Similarity	NPD6100	Approved
0.6842	Remote Similarity	NPD5403	Approved
0.6838	Remote Similarity	NPD3023	Approved
0.6838	Remote Similarity	NPD3026	Approved
0.6831	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD9281	Approved
0.6815	Remote Similarity	NPD7768	Phase 2
0.6815	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD6808	Phase 2
0.6812	Remote Similarity	NPD4359	Approved
0.6812	Remote Similarity	NPD5327	Phase 3
0.6807	Remote Similarity	NPD8312	Approved
0.6807	Remote Similarity	NPD8313	Approved
0.6806	Remote Similarity	NPD4618	Approved
0.6806	Remote Similarity	NPD4622	Approved
0.6805	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.68	Remote Similarity	NPD160	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD710	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD5890	Approved
0.6774	Remote Similarity	NPD5889	Approved
0.6772	Remote Similarity	NPD7075	Discontinued
0.6767	Remote Similarity	NPD6671	Approved
0.6757	Remote Similarity	NPD2897	Discontinued
0.6755	Remote Similarity	NPD7390	Discontinued
0.675	Remote Similarity	NPD7609	Phase 3
0.6741	Remote Similarity	NPD1894	Discontinued
0.6736	Remote Similarity	NPD4060	Phase 1
0.6732	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD7317	Phase 3
0.6731	Remote Similarity	NPD7248	Discontinued
0.6731	Remote Similarity	NPD6801	Discontinued
0.6725	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6718	Remote Similarity	NPD228	Approved
0.6718	Remote Similarity	NPD1139	Approved
0.6718	Remote Similarity	NPD1137	Approved
0.6712	Remote Similarity	NPD5688	Approved
0.6712	Remote Similarity	NPD5689	Approved
0.6711	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.671	Remote Similarity	NPD7028	Phase 2
0.671	Remote Similarity	NPD6585	Discontinued
0.6708	Remote Similarity	NPD5710	Approved
0.6708	Remote Similarity	NPD5711	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