NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	654.47
Volume:	702.598
LogP:	7.036
LogD:	4.173
LogS:	-5.547
# Rotatable Bonds:	28
TPSA:	142.75
# H-Bond Aceptor:	9
# H-Bond Donor:	4
# Rings:	2
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.055
Synthetic Accessibility Score:	4.851
Fsp3:	0.892
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.009
MDCK Permeability:	1.4861997442494612e-05
Pgp-inhibitor:	0.733
Pgp-substrate:	0.995
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.942
30% Bioavailability (F30%):	0.736

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.004
Plasma Protein Binding (PPB):	98.0040054321289%
Volume Distribution (VD):	0.735
Pgp-substrate:	3.3669393062591553%

ADMET: Metabolism

CYP1A2-inhibitor:	0.016
CYP1A2-substrate:	0.153
CYP2C19-inhibitor:	0.145
CYP2C19-substrate:	0.061
CYP2C9-inhibitor:	0.151
CYP2C9-substrate:	0.844
CYP2D6-inhibitor:	0.052
CYP2D6-substrate:	0.009
CYP3A4-inhibitor:	0.799
CYP3A4-substrate:	0.051

ADMET: Excretion

Clearance (CL):	4.077
Half-life (T1/2):	0.21

ADMET: Toxicity

hERG Blockers:	0.438
Human Hepatotoxicity (H-HT):	0.692
Drug-inuced Liver Injury (DILI):	0.464
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.001
Maximum Recommended Daily Dose:	0.926
Skin Sensitization:	0.987
Carcinogencity:	0.074
Eye Corrosion:	0.004
Eye Irritation:	0.132
Respiratory Toxicity:	0.871

Download Data

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

Natural Product: NPC139416

Natural Product ID:	NPC139416
*Common Name:**	1-Methylnaphthalene
IUPAC Name:	1-methylnaphthalene
Synonyms:	1-Methyl-Naphthalene; 1-Methylnaphthalene
Standard InCHIKey:	QPUYECUOLPXSFR-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C11H10/c1-9-5-4-7-10-6-2-3-8-11(9)10/h2-8H,1H3
SMILES:	Cc1cccc2ccccc12
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL383808
PubChem CID:	7002
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000023] Naphthalenes

*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
NPO17823	Lycium chinense	Species	Solanaceae	Eukaryota	fruits	n.a.	n.a.	PMID[12467621]
NPO29276	Juglans nigra	Species	Juglandaceae	Eukaryota	n.a.	root	n.a.	PMID[14727919]
NPO29276	Juglans nigra	Species	Juglandaceae	Eukaryota	n.a.	leaf	n.a.	PMID[14727919]
NPO29276	Juglans nigra	Species	Juglandaceae	Eukaryota	n.a.	bark	n.a.	PMID[14727919]
NPO29276	Juglans nigra	Species	Juglandaceae	Eukaryota	n.a.	xylem	n.a.	PMID[14727919]
NPO17823	Lycium chinense	Species	Solanaceae	Eukaryota	n.a.	root	n.a.	PMID[16212233]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	leaf	n.a.	PMID[18409045]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	flower buds	n.a.	n.a.	PMID[19926279]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	root	n.a.	PMID[2092947]
NPO13989	Uncaria macrophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21070010]
NPO13989	Uncaria macrophylla	Species	Rubiaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[21070010]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	berry	n.a.	n.a.	PMID[21216145]
NPO17823	Lycium chinense	Species	Solanaceae	Eukaryota	root bark	n.a.	n.a.	PMID[23282106]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	leaves	n.a.	n.a.	PMID[24290061]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24968750]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25152999]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	stems-leaves	n.a.	n.a.	PMID[26420067]
NPO17823	Lycium chinense	Species	Solanaceae	Eukaryota	Root Bark	n.a.	n.a.	PMID[26982999]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	stem	n.a.	PMID[27914541]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	Flower Buds	n.a.	n.a.	PMID[28345906]
NPO23429	Lycium barbarum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31397570]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32129622]
NPO17823	Lycium chinense	Species	Solanaceae	Eukaryota	fruits	n.a.	n.a.	PMID[9090870]
NPO29276	Juglans nigra	Species	Juglandaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO29276	Juglans nigra	Species	Juglandaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO29276	Juglans nigra	Species	Juglandaceae	Eukaryota	Pericarp	n.a.	n.a.	Database[FooDB]
NPO29276	Juglans nigra	Species	Juglandaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO29276	Juglans nigra	Species	Juglandaceae	Eukaryota	Shoot	n.a.	n.a.	Database[FooDB]
NPO9822	Typha angustifolia	Species	Typhaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO29276	Juglans nigra	Species	Juglandaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO29276	Juglans nigra	Species	Juglandaceae	Eukaryota	Essential Oil	n.a.	n.a.	Database[FooDB]
NPO17823	Lycium chinense	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13989	Uncaria macrophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23429	Lycium barbarum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9822	Typha angustifolia	Species	Typhaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14650	Lobelia chinensis	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29276	Juglans nigra	Species	Juglandaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[MetaboLights]
NPO13989	Uncaria macrophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17823	Lycium chinense	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14650	Lobelia chinensis	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9822	Typha angustifolia	Species	Typhaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23429	Lycium barbarum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29276	Juglans nigra	Species	Juglandaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13989	Uncaria macrophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29276	Juglans nigra	Species	Juglandaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14650	Lobelia chinensis	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO23429	Lycium barbarum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9822	Typha angustifolia	Species	Typhaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO17823	Lycium chinense	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO17823	Lycium chinense	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO13989	Uncaria macrophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO9822	Typha angustifolia	Species	Typhaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO14650	Lobelia chinensis	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO23429	Lycium barbarum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO17823	Lycium chinense	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23429	Lycium barbarum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14650	Lobelia chinensis	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13989	Uncaria macrophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9822	Typha angustifolia	Species	Typhaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29276	Juglans nigra	Species	Juglandaceae	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
NPO29276	NPC139416	Other (raw)	Essential Oil	1200	1200	1200	mg/100g	Database [DUKE]

☑ 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	5
Others	2
Potency	12

Activity Type	# Activity
Cell Line	1
Individual Protein	10
Others	8

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT208	Individual Protein	Cytochrome P450 1A2	Homo sapiens	IC50	=	110000.0	nM	PMID[456248]
NPT240	Individual Protein	Cytochrome P450 2A6	Homo sapiens	IC50	=	34000.0	nM	PMID[456249]
NPT1420	Individual Protein	Cytochrome P450 2A5	Mus musculus	IC50	=	24000.0	nM	PMID[456249]
NPT1420	Individual Protein	Cytochrome P450 2A5	Mus musculus	IC50	=	23988.33	nM	PMID[456250]
NPT240	Individual Protein	Cytochrome P450 2A6	Homo sapiens	IC50	=	33962.53	nM	PMID[456250]
NPT347	Cell Line	Lymphoblastoid cells	Homo sapiens	Potency	=	79432.8	nM	PMID[456251]
NPT249	Individual Protein	Glucocorticoid receptor	Homo sapiens	Potency	n.a.	5623.4	nM	PMID[456251]
NPT106	Individual Protein	Peroxisome proliferator-activated receptor delta	Homo sapiens	Potency	n.a.	1122.0	nM	PMID[456251]
NPT103	Individual Protein	Nuclear receptor ROR-gamma	Homo sapiens	Potency	n.a.	5955.7	nM	PMID[456251]
NPT153	Individual Protein	Androgen Receptor	Homo sapiens	Potency	n.a.	22196.6	nM	PubChem BioAssay data set
NPT27	Others	Unspecified		Ratio	=	1.4	n.a.	PMID[456249]
NPT94	Individual Protein	Aldehyde dehydrogenase 1A1	Homo sapiens	Potency	=	39810.7	nM	PMID[456251]
NPT35	Others	n.a.		LogP	=	3.965	n.a.	PMID[456252]
NPT2	Others	Unspecified		Potency	n.a.	153.6	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	55762.1	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	30637.9	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	69567.3	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	55755.4	nM	PubChem BioAssay data set

☑ 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 NPC139416 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	1541
0.1-0.2	3971
0.2-0.3	14085
0.3-0.4	15682
0.4-0.5	6126
0.5-0.6	984
0.6-0.7	207
0.7-0.8	40
0.8-0.85	22
0.85-0.9	21
0.9-0.95	6
0.95-1	12

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC246822
1.0	High Similarity	NPC213570
0.9697	High Similarity	NPC226999
0.9697	High Similarity	NPC158028
0.9697	High Similarity	NPC280135
0.9697	High Similarity	NPC193578
0.9697	High Similarity	NPC39799
0.9697	High Similarity	NPC135433
0.9697	High Similarity	NPC1008
0.9697	High Similarity	NPC87099
0.9545	High Similarity	NPC251490
0.9375	High Similarity	NPC291066
0.9275	High Similarity	NPC307195
0.9265	High Similarity	NPC1901
0.9254	High Similarity	NPC72670
0.9219	High Similarity	NPC113670
0.913	High Similarity	NPC258492
0.913	High Similarity	NPC96835
0.9091	High Similarity	NPC267443
0.9091	High Similarity	NPC6107
0.9062	High Similarity	NPC71009
0.8986	High Similarity	NPC54269
0.8971	High Similarity	NPC263385
0.8939	High Similarity	NPC289915
0.8939	High Similarity	NPC113837
0.8906	High Similarity	NPC246588
0.8906	High Similarity	NPC238023
0.8906	High Similarity	NPC310758
0.8906	High Similarity	NPC150196
0.8788	High Similarity	NPC32312
0.8788	High Similarity	NPC155172
0.8767	High Similarity	NPC159661
0.875	High Similarity	NPC147062
0.8649	High Similarity	NPC315216
0.8636	High Similarity	NPC45756
0.863	High Similarity	NPC255345
0.863	High Similarity	NPC245896
0.863	High Similarity	NPC66270
0.8615	High Similarity	NPC135924
0.8594	High Similarity	NPC114327
0.8594	High Similarity	NPC36357
0.8594	High Similarity	NPC64270
0.8551	High Similarity	NPC473206
0.8493	Intermediate Similarity	NPC3190
0.8493	Intermediate Similarity	NPC249018
0.8485	Intermediate Similarity	NPC29680
0.8485	Intermediate Similarity	NPC22786
0.8485	Intermediate Similarity	NPC66517
0.8438	Intermediate Similarity	NPC212114
0.8438	Intermediate Similarity	NPC65873
0.8438	Intermediate Similarity	NPC120441
0.8438	Intermediate Similarity	NPC300345
0.84	Intermediate Similarity	NPC50063
0.8358	Intermediate Similarity	NPC88566
0.8358	Intermediate Similarity	NPC21211
0.8333	Intermediate Similarity	NPC210849
0.8333	Intermediate Similarity	NPC54368
0.8333	Intermediate Similarity	NPC248705
0.8281	Intermediate Similarity	NPC269586
0.8281	Intermediate Similarity	NPC198841
0.8235	Intermediate Similarity	NPC198023
0.8209	Intermediate Similarity	NPC200745
0.8125	Intermediate Similarity	NPC277704
0.8125	Intermediate Similarity	NPC149436
0.8116	Intermediate Similarity	NPC178527
0.8108	Intermediate Similarity	NPC110264
0.803	Intermediate Similarity	NPC8235
0.7971	Intermediate Similarity	NPC264470
0.791	Intermediate Similarity	NPC169110
0.7887	Intermediate Similarity	NPC22760
0.7857	Intermediate Similarity	NPC36440
0.7778	Intermediate Similarity	NPC297358
0.7778	Intermediate Similarity	NPC200936
0.7619	Intermediate Similarity	NPC277277
0.7595	Intermediate Similarity	NPC242628
0.7534	Intermediate Similarity	NPC5324
0.7531	Intermediate Similarity	NPC133162
0.75	Intermediate Similarity	NPC418308
0.75	Intermediate Similarity	NPC199567
0.75	Intermediate Similarity	NPC325709
0.747	Intermediate Similarity	NPC60408
0.7467	Intermediate Similarity	NPC212463
0.7326	Intermediate Similarity	NPC103346
0.7324	Intermediate Similarity	NPC50266
0.7317	Intermediate Similarity	NPC267704
0.7308	Intermediate Similarity	NPC9796
0.7294	Intermediate Similarity	NPC298115
0.7286	Intermediate Similarity	NPC45255
0.7241	Intermediate Similarity	NPC128645
0.7209	Intermediate Similarity	NPC26224
0.7176	Intermediate Similarity	NPC267262
0.7162	Intermediate Similarity	NPC311343
0.7159	Intermediate Similarity	NPC289883
0.7143	Intermediate Similarity	NPC307
0.7143	Intermediate Similarity	NPC147578
0.7143	Intermediate Similarity	NPC160339
0.7126	Intermediate Similarity	NPC220596
0.7126	Intermediate Similarity	NPC125226
0.7125	Intermediate Similarity	NPC272260
0.7108	Intermediate Similarity	NPC95429
0.7105	Intermediate Similarity	NPC74458
0.7093	Intermediate Similarity	NPC113307
0.7089	Intermediate Similarity	NPC298023
0.7079	Intermediate Similarity	NPC172925
0.7079	Intermediate Similarity	NPC472880
0.7067	Intermediate Similarity	NPC98880
0.7051	Intermediate Similarity	NPC189371
0.7051	Intermediate Similarity	NPC276699
0.7042	Intermediate Similarity	NPC200624
0.7037	Intermediate Similarity	NPC95868
0.7037	Intermediate Similarity	NPC184030
0.7037	Intermediate Similarity	NPC164449
0.7033	Intermediate Similarity	NPC49994
0.7013	Intermediate Similarity	NPC285679
0.7011	Intermediate Similarity	NPC173413
0.7011	Intermediate Similarity	NPC19256
0.7	Intermediate Similarity	NPC224544
0.7	Intermediate Similarity	NPC103488
0.6988	Remote Similarity	NPC104070
0.6977	Remote Similarity	NPC153308
0.6977	Remote Similarity	NPC157778
0.6974	Remote Similarity	NPC95289
0.6974	Remote Similarity	NPC229235
0.6951	Remote Similarity	NPC273033
0.6951	Remote Similarity	NPC12936
0.6941	Remote Similarity	NPC164526
0.6941	Remote Similarity	NPC148231
0.6933	Remote Similarity	NPC239931
0.6933	Remote Similarity	NPC82770
0.6933	Remote Similarity	NPC78954
0.6932	Remote Similarity	NPC470926
0.6932	Remote Similarity	NPC133461
0.6923	Remote Similarity	NPC112609
0.6923	Remote Similarity	NPC122327
0.6923	Remote Similarity	NPC113000
0.6914	Remote Similarity	NPC139901
0.6914	Remote Similarity	NPC151405
0.6883	Remote Similarity	NPC208302
0.6883	Remote Similarity	NPC326200
0.6875	Remote Similarity	NPC290638
0.6875	Remote Similarity	NPC179726
0.6867	Remote Similarity	NPC121478
0.6867	Remote Similarity	NPC73637
0.686	Remote Similarity	NPC43945
0.6854	Remote Similarity	NPC59677
0.6854	Remote Similarity	NPC153885
0.6854	Remote Similarity	NPC323420
0.6854	Remote Similarity	NPC155232
0.6842	Remote Similarity	NPC235059
0.6842	Remote Similarity	NPC169222
0.6842	Remote Similarity	NPC16190
0.6829	Remote Similarity	NPC285716
0.6829	Remote Similarity	NPC71664
0.6829	Remote Similarity	NPC328178
0.6829	Remote Similarity	NPC17408
0.6829	Remote Similarity	NPC157055
0.6829	Remote Similarity	NPC477703
0.6824	Remote Similarity	NPC475710
0.6813	Remote Similarity	NPC185208
0.6813	Remote Similarity	NPC219573
0.6809	Remote Similarity	NPC239854
0.68	Remote Similarity	NPC52330
0.6795	Remote Similarity	NPC271437
0.6795	Remote Similarity	NPC244738
0.6786	Remote Similarity	NPC172984
0.6786	Remote Similarity	NPC119677
0.6786	Remote Similarity	NPC39600
0.6786	Remote Similarity	NPC273758
0.6778	Remote Similarity	NPC238219
0.675	Remote Similarity	NPC139658
0.6747	Remote Similarity	NPC133050
0.6742	Remote Similarity	NPC284475
0.6739	Remote Similarity	NPC239185
0.6739	Remote Similarity	NPC324602
0.6739	Remote Similarity	NPC226041
0.6719	Remote Similarity	NPC11150
0.6709	Remote Similarity	NPC108218
0.6709	Remote Similarity	NPC208075
0.6705	Remote Similarity	NPC176858
0.6703	Remote Similarity	NPC260233
0.6702	Remote Similarity	NPC472879
0.6667	Remote Similarity	NPC283012
0.6667	Remote Similarity	NPC108800
0.6667	Remote Similarity	NPC134882
0.6667	Remote Similarity	NPC188844
0.6667	Remote Similarity	NPC475199
0.6667	Remote Similarity	NPC69057
0.6667	Remote Similarity	NPC155429
0.6667	Remote Similarity	NPC238696
0.6667	Remote Similarity	NPC98269
0.6667	Remote Similarity	NPC1682
0.6667	Remote Similarity	NPC230068
0.6667	Remote Similarity	NPC325662
0.6667	Remote Similarity	NPC314690
0.663	Remote Similarity	NPC21959
0.6629	Remote Similarity	NPC191444
0.6628	Remote Similarity	NPC99482
0.6627	Remote Similarity	NPC190567
0.6625	Remote Similarity	NPC98976
0.6596	Remote Similarity	NPC221825

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 NPC139416 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	1052
0.1-0.2	666
0.2-0.3	2589
0.3-0.4	3129
0.4-0.5	1223
0.5-0.6	352
0.6-0.7	107
0.7-0.8	31
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9219	High Similarity	NPD675	Discontinued
0.7922	Intermediate Similarity	NPD3903	Approved
0.7922	Intermediate Similarity	NPD3981	Approved
0.7922	Intermediate Similarity	NPD3979	Approved
0.7922	Intermediate Similarity	NPD3904	Approved
0.7778	Intermediate Similarity	NPD9497	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD1673	Approved
0.775	Intermediate Similarity	NPD4544	Approved
0.7625	Intermediate Similarity	NPD4635	Approved
0.7531	Intermediate Similarity	NPD3427	Approved
0.7531	Intermediate Similarity	NPD3429	Approved
0.7465	Intermediate Similarity	NPD173	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD4405	Approved
0.7442	Intermediate Similarity	NPD4408	Approved
0.7442	Intermediate Similarity	NPD4407	Approved
0.7375	Intermediate Similarity	NPD3035	Approved
0.7356	Intermediate Similarity	NPD4542	Approved
0.7356	Intermediate Similarity	NPD4545	Approved
0.7349	Intermediate Similarity	NPD4406	Approved
0.7349	Intermediate Similarity	NPD4409	Approved
0.7342	Intermediate Similarity	NPD1475	Approved
0.7333	Intermediate Similarity	NPD292	Approved
0.7333	Intermediate Similarity	NPD294	Approved
0.7308	Intermediate Similarity	NPD4144	Approved
0.7308	Intermediate Similarity	NPD4147	Approved
0.7284	Intermediate Similarity	NPD4701	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD4169	Approved
0.7284	Intermediate Similarity	NPD4170	Approved
0.7262	Intermediate Similarity	NPD3428	Approved
0.7262	Intermediate Similarity	NPD3426	Approved
0.725	Intermediate Similarity	NPD914	Suspended
0.725	Intermediate Similarity	NPD1617	Discontinued
0.7195	Intermediate Similarity	NPD3971	Phase 1
0.7195	Intermediate Similarity	NPD2001	Discontinued
0.7195	Intermediate Similarity	NPD423	Phase 3
0.7191	Intermediate Similarity	NPD3093	Approved
0.7176	Intermediate Similarity	NPD3345	Approved
0.716	Intermediate Similarity	NPD4027	Approved
0.716	Intermediate Similarity	NPD4026	Approved
0.7143	Intermediate Similarity	NPD3099	Discontinued
0.7111	Intermediate Similarity	NPD5598	Approved
0.7111	Intermediate Similarity	NPD5597	Approved
0.7079	Intermediate Similarity	NPD688	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD1507	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD260	Discontinued
0.7011	Intermediate Similarity	NPD3346	Approved
0.7011	Intermediate Similarity	NPD3344	Approved
0.6988	Remote Similarity	NPD1185	Approved
0.6966	Remote Similarity	NPD3980	Approved
0.6966	Remote Similarity	NPD2878	Approved
0.6966	Remote Similarity	NPD3982	Approved
0.6951	Remote Similarity	NPD942	Approved
0.6941	Remote Similarity	NPD4636	Approved
0.6923	Remote Similarity	NPD80	Approved
0.6923	Remote Similarity	NPD9594	Approved
0.6923	Remote Similarity	NPD2487	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD9591	Approved
0.6923	Remote Similarity	NPD9588	Approved
0.6923	Remote Similarity	NPD9592	Approved
0.6923	Remote Similarity	NPD9590	Approved
0.6923	Remote Similarity	NPD9593	Approved
0.6923	Remote Similarity	NPD9589	Approved
0.6905	Remote Similarity	NPD5178	Approved
0.6889	Remote Similarity	NPD6048	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD6049	Phase 2
0.686	Remote Similarity	NPD4146	Approved
0.686	Remote Similarity	NPD4145	Approved
0.686	Remote Similarity	NPD2002	Discontinued
0.686	Remote Similarity	NPD650	Approved
0.6848	Remote Similarity	NPD5832	Phase 3
0.6824	Remote Similarity	NPD5734	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD5916	Discontinued
0.6813	Remote Similarity	NPD2895	Discontinued
0.6795	Remote Similarity	NPD9728	Phase 1
0.679	Remote Similarity	NPD9563	Approved
0.679	Remote Similarity	NPD79	Approved
0.679	Remote Similarity	NPD9564	Approved
0.6786	Remote Similarity	NPD4000	Phase 3
0.6786	Remote Similarity	NPD5288	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD5675	Discontinued
0.6742	Remote Similarity	NPD7609	Phase 3
0.6739	Remote Similarity	NPD3495	Discontinued
0.6737	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.6709	Remote Similarity	NPD505	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD589	Approved
0.6707	Remote Similarity	NPD590	Approved
0.6706	Remote Similarity	NPD2538	Approved
0.6706	Remote Similarity	NPD2539	Approved
0.6705	Remote Similarity	NPD5656	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD6354	Discontinued
0.6667	Remote Similarity	NPD4936	Approved
0.6667	Remote Similarity	NPD7631	Approved
0.6667	Remote Similarity	NPD4937	Approved
0.6667	Remote Similarity	NPD1508	Approved
0.6632	Remote Similarity	NPD4321	Approved
0.663	Remote Similarity	NPD3458	Approved
0.663	Remote Similarity	NPD2005	Discontinued
0.663	Remote Similarity	NPD3457	Approved
0.663	Remote Similarity	NPD6472	Discontinued
0.663	Remote Similarity	NPD3456	Approved
0.6629	Remote Similarity	NPD5915	Approved
0.6593	Remote Similarity	NPD1563	Approved
0.6585	Remote Similarity	NPD293	Approved
0.6585	Remote Similarity	NPD295	Approved
0.6585	Remote Similarity	NPD296	Approved
0.6556	Remote Similarity	NPD4543	Discontinued
0.6556	Remote Similarity	NPD1239	Approved
0.6556	Remote Similarity	NPD517	Discontinued
0.6552	Remote Similarity	NPD5252	Clinical (unspecified phase)
0.6506	Remote Similarity	NPD1052	Approved
0.6506	Remote Similarity	NPD1051	Approved
0.6506	Remote Similarity	NPD1053	Approved
0.6477	Remote Similarity	NPD781	Approved
0.6477	Remote Similarity	NPD780	Approved
0.6477	Remote Similarity	NPD783	Approved
0.6477	Remote Similarity	NPD782	Approved
0.6463	Remote Similarity	NPD603	Approved
0.6452	Remote Similarity	NPD1843	Approved
0.6452	Remote Similarity	NPD1989	Approved
0.6444	Remote Similarity	NPD2811	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD4728	Approved
0.6437	Remote Similarity	NPD2205	Approved
0.6437	Remote Similarity	NPD2208	Approved
0.6437	Remote Similarity	NPD9505	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD1269	Approved
0.6429	Remote Similarity	NPD5372	Approved
0.6429	Remote Similarity	NPD5371	Approved
0.6429	Remote Similarity	NPD1268	Approved
0.6421	Remote Similarity	NPD1946	Clinical (unspecified phase)
0.642	Remote Similarity	NPD9716	Approved
0.6395	Remote Similarity	NPD263	Approved
0.6395	Remote Similarity	NPD262	Approved
0.6386	Remote Similarity	NPD9393	Approved
0.6386	Remote Similarity	NPD9397	Approved
0.6386	Remote Similarity	NPD225	Approved
0.6386	Remote Similarity	NPD227	Approved
0.6383	Remote Similarity	NPD1566	Phase 3
0.6383	Remote Similarity	NPD713	Clinical (unspecified phase)
0.6383	Remote Similarity	NPD1564	Approved
0.6383	Remote Similarity	NPD1565	Approved
0.6374	Remote Similarity	NPD3000	Approved
0.6374	Remote Similarity	NPD2997	Approved
0.6374	Remote Similarity	NPD2998	Approved
0.6364	Remote Similarity	NPD1697	Approved
0.6364	Remote Similarity	NPD7170	Discontinued
0.6354	Remote Similarity	NPD5630	Phase 1
0.6353	Remote Similarity	NPD472	Approved
0.6344	Remote Similarity	NPD4094	Approved
0.6344	Remote Similarity	NPD5554	Approved
0.6333	Remote Similarity	NPD1628	Approved
0.6333	Remote Similarity	NPD1629	Approved
0.631	Remote Similarity	NPD507	Approved
0.631	Remote Similarity	NPD508	Approved
0.63	Remote Similarity	NPD2342	Discontinued
0.6292	Remote Similarity	NPD1087	Approved
0.6289	Remote Similarity	NPD2841	Approved
0.6277	Remote Similarity	NPD5963	Phase 2
0.6277	Remote Similarity	NPD5964	Phase 2
0.6277	Remote Similarity	NPD2507	Clinical (unspecified phase)
0.6275	Remote Similarity	NPD2384	Clinical (unspecified phase)
0.625	Remote Similarity	NPD4737	Phase 2
0.6237	Remote Similarity	NPD845	Approved
0.6224	Remote Similarity	NPD1929	Approved
0.6224	Remote Similarity	NPD1930	Approved
0.6224	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6222	Remote Similarity	NPD1101	Approved
0.6211	Remote Similarity	NPD4655	Approved
0.6211	Remote Similarity	NPD4657	Approved
0.6207	Remote Similarity	NPD1800	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD830	Approved
0.6207	Remote Similarity	NPD831	Approved
0.6186	Remote Similarity	NPD1616	Discontinued
0.6186	Remote Similarity	NPD1916	Discontinued
0.617	Remote Similarity	NPD3772	Phase 3
0.6163	Remote Similarity	NPD226	Approved
0.6162	Remote Similarity	NPD179	Clinical (unspecified phase)
0.6162	Remote Similarity	NPD3048	Approved
0.6162	Remote Similarity	NPD3046	Approved
0.6162	Remote Similarity	NPD3047	Approved
0.6154	Remote Similarity	NPD7635	Approved
0.6154	Remote Similarity	NPD771	Phase 3
0.6146	Remote Similarity	NPD4117	Approved
0.6136	Remote Similarity	NPD9395	Approved
0.6136	Remote Similarity	NPD785	Approved
0.6129	Remote Similarity	NPD752	Approved
0.6129	Remote Similarity	NPD9361	Approved
0.6118	Remote Similarity	NPD9490	Approved
0.6105	Remote Similarity	NPD3832	Clinical (unspecified phase)
0.6105	Remote Similarity	NPD1738	Approved
0.6105	Remote Similarity	NPD2860	Approved
0.6105	Remote Similarity	NPD2859	Approved
0.6095	Remote Similarity	NPD498	Approved
0.6095	Remote Similarity	NPD495	Approved
0.6095	Remote Similarity	NPD496	Approved
0.6087	Remote Similarity	NPD3673	Approved
0.6087	Remote Similarity	NPD1086	Approved
0.6087	Remote Similarity	NPD1090	Approved
0.6087	Remote Similarity	NPD3672	Approved
0.6087	Remote Similarity	NPD1089	Approved
0.6082	Remote Similarity	NPD3020	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