NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	260.07
Volume:	259.083
LogP:	2.273
LogD:	1.702
LogS:	-3.531
# Rotatable Bonds:	2
TPSA:	80.67
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.82
Synthetic Accessibility Score:	2.623
Fsp3:	0.214
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:	-4.761
MDCK Permeability:	2.5463668862357736e-05
Pgp-inhibitor:	0.076
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.027
20% Bioavailability (F20%):	0.072
30% Bioavailability (F30%):	0.141

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.037
Plasma Protein Binding (PPB):	90.22022247314453%
Volume Distribution (VD):	0.736
Pgp-substrate:	3.5235960483551025%

ADMET: Metabolism

CYP1A2-inhibitor:	0.962
CYP1A2-substrate:	0.835
CYP2C19-inhibitor:	0.591
CYP2C19-substrate:	0.134
CYP2C9-inhibitor:	0.641
CYP2C9-substrate:	0.481
CYP2D6-inhibitor:	0.645
CYP2D6-substrate:	0.222
CYP3A4-inhibitor:	0.681
CYP3A4-substrate:	0.173

ADMET: Excretion

Clearance (CL):	2.977
Half-life (T1/2):	0.384

ADMET: Toxicity

hERG Blockers:	0.012
Human Hepatotoxicity (H-HT):	0.575
Drug-inuced Liver Injury (DILI):	0.711
AMES Toxicity:	0.899
Rat Oral Acute Toxicity:	0.845
Maximum Recommended Daily Dose:	0.808
Skin Sensitization:	0.581
Carcinogencity:	0.855
Eye Corrosion:	0.009
Eye Irritation:	0.853
Respiratory Toxicity:	0.867

Download Data

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

Natural Product: NPC254603

Natural Product ID:	NPC254603
*Common Name:**	6-Acetyl-5-Hydroxy-2-Methoxy-7-Methyl-[1,4]Naphthoquinone
IUPAC Name:	6-acetyl-5-hydroxy-2-methoxy-7-methylnaphthalene-1,4-dione
Synonyms:
Standard InCHIKey:	SSHJHOVVYKCJJI-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C14H12O5/c1-6-4-8-12(14(18)11(6)7(2)15)9(16)5-10(19-3)13(8)17/h4-5,18H,1-3H3
SMILES:	Cc1cc2c(C(=O)C=C(C2=O)OC)c(c1C(=O)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL322776
PubChem CID:	158739
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
NPO12079	Dysoxylum cumingianum	Species	Meliaceae	Eukaryota	n.a.	leaf	n.a.	DOI[10.1021/jo00051a050]
NPO11391	Polygonum cuspidatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11076555]
NPO14520	Bassia muricata	Species	Chenopodiaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[11454355]
NPO11391	Polygonum cuspidatum	Species	Polygonaceae	Eukaryota	Roots	n.a.	n.a.	PMID[11459643]
NPO11391	Polygonum cuspidatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1517743]
NPO12477	Dodonaea viscosa	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19719093]
NPO12477	Dodonaea viscosa	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22512738]
NPO13237	Teucrium yemense	Species	n.a.	n.a.	Aerial Parts	n.a.	n.a.	PMID[28581290]
NPO11391	Polygonum cuspidatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8277318]
NPO12477	Dodonaea viscosa	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14014	Eriocheir sinensis	Species	Varunidae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11391	Polygonum cuspidatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25658	Rumex japonicus	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14304	Physalis alkekengi	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25658	Rumex japonicus	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12477	Dodonaea viscosa	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15297	Aconitum seravschanicum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14304	Physalis alkekengi	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14014	Eriocheir sinensis	Species	Varunidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11391	Polygonum cuspidatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12477	Dodonaea viscosa	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14014	Eriocheir sinensis	Species	Varunidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO25658	Rumex japonicus	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11391	Polygonum cuspidatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11391	Polygonum cuspidatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO14304	Physalis alkekengi	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO25658	Rumex japonicus	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO12252	Psychotria stachyoides	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13421	Sphaerella laricina	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO3214	Lavandula vera	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12477	Dodonaea viscosa	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14217	Adansonia grandidieri	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14014	Eriocheir sinensis	Species	Varunidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9752	Miliusa velutina	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO624	Isaria fumosorosea	Species	Cordycipitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7819.1	Epichloe festucae var. lolii	Varieties	Clavicipitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14412	Aphyllocladus denticulatus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8386	Enceliopsis argophylla	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12079	Dysoxylum cumingianum	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10688	Flacourtia jangomas	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11749	Eria mollis	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15297	Aconitum seravschanicum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9448	Dictyopteris australis	Species	Dictyotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO986	Rattus rattus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13716	Aconitum tasiromontanum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13237	Teucrium yemense	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO1501	Senecio subdentatus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14520	Bassia muricata	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22526	Justicia secunda	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11391	Polygonum cuspidatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14104	Dendriopoterium menendezii	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14304	Physalis alkekengi	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4345	Caulocystis cephalornithos	Species	Sargassaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2198	Rivularia firma	Species	Rivulariaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO16590	Cytophaga hutchinsoni	Species	Cytophagaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO13403	Gadus morhua callarias	Species	Gadidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13523	Neobalanocarpus heimii	Species	Dipterocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25658	Rumex japonicus	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2631	Aster sedifolius	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11580	Onobrychis arenaria	Species	Fabaceae	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
IC50	2

Activity Type	# Activity
Individual Protein	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT4312	Individual Protein	Human rhinovirus A protease	Human rhinovirus sp.	IC50	=	4600.0	nM	PMID[534195]
NPT201	Individual Protein	Papain	Carica papaya	IC50	=	23000.0	nM	PMID[534195]

☑ 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 NPC254603 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	337
0.1-0.2	1524
0.2-0.3	3506
0.3-0.4	9605
0.4-0.5	10062
0.5-0.6	5835
0.6-0.7	7731
0.7-0.8	3712
0.8-0.85	325
0.85-0.9	48
0.9-0.95	9
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9764	High Similarity	NPC309430
0.9535	High Similarity	NPC193169
0.9453	High Similarity	NPC198305
0.9308	High Similarity	NPC88864
0.9297	High Similarity	NPC165257
0.9147	High Similarity	NPC237225
0.9141	High Similarity	NPC231774
0.9077	High Similarity	NPC278928
0.903	High Similarity	NPC86524
0.8992	High Similarity	NPC51037
0.8939	High Similarity	NPC17083
0.8921	High Similarity	NPC29932
0.8857	High Similarity	NPC474630
0.8841	High Similarity	NPC283292
0.8837	High Similarity	NPC310540
0.8832	High Similarity	NPC26924
0.8828	High Similarity	NPC307174
0.8824	High Similarity	NPC471452
0.8806	High Similarity	NPC171968
0.8768	High Similarity	NPC315578
0.8723	High Similarity	NPC28632
0.8722	High Similarity	NPC475741
0.8712	High Similarity	NPC282923
0.8702	High Similarity	NPC1991
0.8702	High Similarity	NPC3224
0.8696	High Similarity	NPC114620
0.8696	High Similarity	NPC103337
0.8667	High Similarity	NPC115458
0.8662	High Similarity	NPC136878
0.8623	High Similarity	NPC173980
0.8615	High Similarity	NPC135062
0.8613	High Similarity	NPC315275
0.8613	High Similarity	NPC474311
0.8603	High Similarity	NPC288089
0.8594	High Similarity	NPC206778
0.8594	High Similarity	NPC285829
0.8593	High Similarity	NPC70622
0.8593	High Similarity	NPC58685
0.8592	High Similarity	NPC474309
0.8592	High Similarity	NPC475923
0.8582	High Similarity	NPC27659
0.8582	High Similarity	NPC143898
0.8582	High Similarity	NPC469885
0.8571	High Similarity	NPC110810
0.8561	High Similarity	NPC1268
0.855	High Similarity	NPC142956
0.8529	High Similarity	NPC53896
0.8521	High Similarity	NPC477409
0.8519	High Similarity	NPC205360
0.8519	High Similarity	NPC205992
0.8507	High Similarity	NPC99731
0.8507	High Similarity	NPC146647
0.8507	High Similarity	NPC34414
0.8489	Intermediate Similarity	NPC13715
0.8485	Intermediate Similarity	NPC103540
0.8478	Intermediate Similarity	NPC38158
0.8478	Intermediate Similarity	NPC141934
0.8478	Intermediate Similarity	NPC272268
0.8456	Intermediate Similarity	NPC110609
0.8456	Intermediate Similarity	NPC242358
0.8456	Intermediate Similarity	NPC246693
0.8444	Intermediate Similarity	NPC199253
0.8444	Intermediate Similarity	NPC31799
0.8444	Intermediate Similarity	NPC55949
0.8444	Intermediate Similarity	NPC136588
0.8429	Intermediate Similarity	NPC477408
0.8421	Intermediate Similarity	NPC306765
0.8409	Intermediate Similarity	NPC173978
0.8409	Intermediate Similarity	NPC68756
0.8409	Intermediate Similarity	NPC152525
0.8406	Intermediate Similarity	NPC80035
0.8406	Intermediate Similarity	NPC283088
0.8369	Intermediate Similarity	NPC156872
0.8357	Intermediate Similarity	NPC61590
0.8356	Intermediate Similarity	NPC226578
0.8346	Intermediate Similarity	NPC123506
0.8345	Intermediate Similarity	NPC254847
0.8345	Intermediate Similarity	NPC476821
0.8333	Intermediate Similarity	NPC474519
0.8333	Intermediate Similarity	NPC50924
0.8333	Intermediate Similarity	NPC375356
0.8333	Intermediate Similarity	NPC474637
0.831	Intermediate Similarity	NPC124365
0.8298	Intermediate Similarity	NPC256463
0.8298	Intermediate Similarity	NPC216312
0.8298	Intermediate Similarity	NPC471602
0.8298	Intermediate Similarity	NPC29771
0.8298	Intermediate Similarity	NPC299405
0.8298	Intermediate Similarity	NPC111422
0.8298	Intermediate Similarity	NPC306835
0.8298	Intermediate Similarity	NPC476477
0.8298	Intermediate Similarity	NPC295339
0.8296	Intermediate Similarity	NPC179898
0.8296	Intermediate Similarity	NPC48248
0.8288	Intermediate Similarity	NPC470479
0.8288	Intermediate Similarity	NPC112816
0.8286	Intermediate Similarity	NPC53414
0.8286	Intermediate Similarity	NPC53206
0.8286	Intermediate Similarity	NPC305060
0.8286	Intermediate Similarity	NPC471905
0.8284	Intermediate Similarity	NPC15837
0.8281	Intermediate Similarity	NPC108288
0.8273	Intermediate Similarity	NPC22222
0.8273	Intermediate Similarity	NPC161632
0.8273	Intermediate Similarity	NPC281513
0.8264	Intermediate Similarity	NPC469385
0.8264	Intermediate Similarity	NPC471906
0.8264	Intermediate Similarity	NPC79627
0.8261	Intermediate Similarity	NPC225051
0.8261	Intermediate Similarity	NPC52407
0.8261	Intermediate Similarity	NPC114183
0.8261	Intermediate Similarity	NPC48036
0.8261	Intermediate Similarity	NPC314048
0.8258	Intermediate Similarity	NPC300274
0.8258	Intermediate Similarity	NPC282577
0.8258	Intermediate Similarity	NPC164947
0.8252	Intermediate Similarity	NPC193555
0.8252	Intermediate Similarity	NPC291078
0.8252	Intermediate Similarity	NPC73061
0.8252	Intermediate Similarity	NPC308572
0.8248	Intermediate Similarity	NPC244699
0.8244	Intermediate Similarity	NPC472046
0.8239	Intermediate Similarity	NPC32749
0.8239	Intermediate Similarity	NPC147542
0.8239	Intermediate Similarity	NPC96421
0.8239	Intermediate Similarity	NPC220496
0.8239	Intermediate Similarity	NPC42262
0.8239	Intermediate Similarity	NPC37992
0.8239	Intermediate Similarity	NPC241349
0.8239	Intermediate Similarity	NPC183345
0.8239	Intermediate Similarity	NPC327916
0.8231	Intermediate Similarity	NPC474310
0.8231	Intermediate Similarity	NPC80370
0.8227	Intermediate Similarity	NPC61398
0.8227	Intermediate Similarity	NPC4214
0.8227	Intermediate Similarity	NPC416
0.8219	Intermediate Similarity	NPC126767
0.8219	Intermediate Similarity	NPC245584
0.8219	Intermediate Similarity	NPC289042
0.8219	Intermediate Similarity	NPC190648
0.8219	Intermediate Similarity	NPC56433
0.8219	Intermediate Similarity	NPC5568
0.8219	Intermediate Similarity	NPC312929
0.8219	Intermediate Similarity	NPC118027
0.8214	Intermediate Similarity	NPC474813
0.8212	Intermediate Similarity	NPC201127
0.8209	Intermediate Similarity	NPC287473
0.8203	Intermediate Similarity	NPC161304
0.8201	Intermediate Similarity	NPC12070
0.8201	Intermediate Similarity	NPC270899
0.8201	Intermediate Similarity	NPC1249
0.82	Intermediate Similarity	NPC471456
0.8194	Intermediate Similarity	NPC66593
0.8188	Intermediate Similarity	NPC477406
0.8182	Intermediate Similarity	NPC305845
0.8182	Intermediate Similarity	NPC204045
0.8182	Intermediate Similarity	NPC471444
0.8182	Intermediate Similarity	NPC257003
0.8182	Intermediate Similarity	NPC290550
0.8176	Intermediate Similarity	NPC315520
0.8175	Intermediate Similarity	NPC117609
0.8169	Intermediate Similarity	NPC143438
0.8169	Intermediate Similarity	NPC242994
0.8169	Intermediate Similarity	NPC138099
0.8169	Intermediate Similarity	NPC190457
0.8169	Intermediate Similarity	NPC162939
0.8156	Intermediate Similarity	NPC245923
0.8156	Intermediate Similarity	NPC264022
0.8156	Intermediate Similarity	NPC475957
0.8151	Intermediate Similarity	NPC300540
0.8148	Intermediate Similarity	NPC96915
0.8148	Intermediate Similarity	NPC160499
0.8143	Intermediate Similarity	NPC249272
0.8143	Intermediate Similarity	NPC22644
0.8143	Intermediate Similarity	NPC258502
0.8138	Intermediate Similarity	NPC274085
0.8138	Intermediate Similarity	NPC48762
0.8138	Intermediate Similarity	NPC89664
0.8138	Intermediate Similarity	NPC475813
0.8138	Intermediate Similarity	NPC475201
0.8138	Intermediate Similarity	NPC19896
0.8138	Intermediate Similarity	NPC21599
0.8138	Intermediate Similarity	NPC193703
0.8134	Intermediate Similarity	NPC234890
0.8134	Intermediate Similarity	NPC74507
0.8133	Intermediate Similarity	NPC208806
0.8129	Intermediate Similarity	NPC267205
0.8129	Intermediate Similarity	NPC59459
0.8125	Intermediate Similarity	NPC201297
0.8125	Intermediate Similarity	NPC474300
0.8125	Intermediate Similarity	NPC69755
0.8125	Intermediate Similarity	NPC94076
0.8125	Intermediate Similarity	NPC182255
0.8125	Intermediate Similarity	NPC135524
0.8121	Intermediate Similarity	NPC230848
0.8116	Intermediate Similarity	NPC41847
0.8112	Intermediate Similarity	NPC181560
0.8112	Intermediate Similarity	NPC169452
0.8108	Intermediate Similarity	NPC120171
0.8105	Intermediate Similarity	NPC313368

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 NPC254603 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	307
0.1-0.2	980
0.2-0.3	1564
0.3-0.4	2786
0.4-0.5	2089
0.5-0.6	1020
0.6-0.7	351
0.7-0.8	48
0.8-0.85	5
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8485	Intermediate Similarity	NPD1470	Approved
0.8345	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8281	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD1201	Approved
0.8108	Intermediate Similarity	NPD3226	Approved
0.7724	Intermediate Similarity	NPD2346	Discontinued
0.7655	Intermediate Similarity	NPD5406	Approved
0.7655	Intermediate Similarity	NPD5404	Approved
0.7655	Intermediate Similarity	NPD5405	Approved
0.7655	Intermediate Similarity	NPD5408	Approved
0.7603	Intermediate Similarity	NPD1471	Phase 3
0.76	Intermediate Similarity	NPD2534	Approved
0.76	Intermediate Similarity	NPD2532	Approved
0.76	Intermediate Similarity	NPD2533	Approved
0.7586	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7569	Intermediate Similarity	NPD1607	Approved
0.7551	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7533	Intermediate Similarity	NPD7390	Discontinued
0.7483	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD3300	Phase 2
0.7431	Intermediate Similarity	NPD1240	Approved
0.7431	Intermediate Similarity	NPD943	Approved
0.7368	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD1510	Phase 2
0.7329	Intermediate Similarity	NPD6232	Discontinued
0.7301	Intermediate Similarity	NPD7473	Discontinued
0.7299	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD2935	Discontinued
0.7267	Intermediate Similarity	NPD2800	Approved
0.723	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD7819	Suspended
0.7206	Intermediate Similarity	NPD9493	Approved
0.7183	Intermediate Similarity	NPD1164	Approved
0.7172	Intermediate Similarity	NPD2313	Discontinued
0.716	Intermediate Similarity	NPD6959	Discontinued
0.7152	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD2344	Approved
0.7125	Intermediate Similarity	NPD3882	Suspended
0.7114	Intermediate Similarity	NPD2799	Discontinued
0.711	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD6651	Approved
0.7086	Intermediate Similarity	NPD1549	Phase 2
0.7081	Intermediate Similarity	NPD7075	Discontinued
0.7076	Intermediate Similarity	NPD8150	Discontinued
0.7067	Intermediate Similarity	NPD1551	Phase 2
0.7063	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD3764	Approved
0.7032	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD6599	Discontinued
0.702	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD2798	Approved
0.7012	Intermediate Similarity	NPD5710	Approved
0.7012	Intermediate Similarity	NPD5711	Approved
0.7	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD2932	Approved
0.6993	Remote Similarity	NPD3750	Approved
0.6993	Remote Similarity	NPD1283	Approved
0.6993	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD74	Approved
0.6992	Remote Similarity	NPD9266	Approved
0.6987	Remote Similarity	NPD1512	Approved
0.6981	Remote Similarity	NPD7411	Suspended
0.6978	Remote Similarity	NPD9545	Approved
0.6963	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD1247	Approved
0.6948	Remote Similarity	NPD2309	Approved
0.6939	Remote Similarity	NPD411	Approved
0.6929	Remote Similarity	NPD1651	Approved
0.6918	Remote Similarity	NPD4380	Phase 2
0.6917	Remote Similarity	NPD9264	Approved
0.6917	Remote Similarity	NPD9263	Approved
0.6917	Remote Similarity	NPD9267	Approved
0.6897	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6883	Remote Similarity	NPD7003	Approved
0.6879	Remote Similarity	NPD3019	Approved
0.6879	Remote Similarity	NPD4626	Approved
0.6879	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD1511	Approved
0.6859	Remote Similarity	NPD6799	Approved
0.6853	Remote Similarity	NPD9717	Approved
0.6842	Remote Similarity	NPD6099	Approved
0.6842	Remote Similarity	NPD6100	Approved
0.6836	Remote Similarity	NPD6535	Approved
0.6836	Remote Similarity	NPD6534	Approved
0.6832	Remote Similarity	NPD1934	Approved
0.6832	Remote Similarity	NPD6801	Discontinued
0.6828	Remote Similarity	NPD1203	Approved
0.6826	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD1237	Approved
0.6815	Remote Similarity	NPD4750	Phase 3
0.6812	Remote Similarity	NPD5951	Approved
0.6802	Remote Similarity	NPD8312	Approved
0.6802	Remote Similarity	NPD8313	Approved
0.68	Remote Similarity	NPD447	Suspended
0.68	Remote Similarity	NPD230	Phase 1
0.6797	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6791	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6791	Remote Similarity	NPD2342	Discontinued
0.679	Remote Similarity	NPD2801	Approved
0.6788	Remote Similarity	NPD7635	Approved
0.6783	Remote Similarity	NPD1281	Approved
0.6783	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD4628	Phase 3
0.6768	Remote Similarity	NPD3749	Approved
0.6765	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD1876	Approved
0.675	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD5402	Approved
0.6744	Remote Similarity	NPD288	Approved
0.6741	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.674	Remote Similarity	NPD6780	Approved
0.674	Remote Similarity	NPD6776	Approved
0.674	Remote Similarity	NPD6779	Approved
0.674	Remote Similarity	NPD6777	Approved
0.674	Remote Similarity	NPD6782	Approved
0.674	Remote Similarity	NPD6781	Approved
0.674	Remote Similarity	NPD6778	Approved
0.6736	Remote Similarity	NPD3972	Approved
0.6736	Remote Similarity	NPD1608	Approved
0.6732	Remote Similarity	NPD2796	Approved
0.6727	Remote Similarity	NPD919	Approved
0.6722	Remote Similarity	NPD7700	Phase 2
0.6722	Remote Similarity	NPD7699	Phase 2
0.6721	Remote Similarity	NPD7435	Discontinued
0.671	Remote Similarity	NPD1243	Approved
0.6707	Remote Similarity	NPD7768	Phase 2
0.6691	Remote Similarity	NPD9281	Approved
0.6686	Remote Similarity	NPD5027	Approved
0.6686	Remote Similarity	NPD5029	Approved
0.6686	Remote Similarity	NPD5031	Approved
0.6667	Remote Similarity	NPD3748	Approved
0.6667	Remote Similarity	NPD844	Approved
0.6647	Remote Similarity	NPD3751	Discontinued
0.6647	Remote Similarity	NPD5034	Approved
0.6647	Remote Similarity	NPD4954	Approved
0.6647	Remote Similarity	NPD5026	Approved
0.6647	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD5028	Approved
0.6647	Remote Similarity	NPD7177	Discontinued
0.6647	Remote Similarity	NPD36	Approved
0.6647	Remote Similarity	NPD4955	Approved
0.6646	Remote Similarity	NPD3817	Phase 2
0.6646	Remote Similarity	NPD7458	Discontinued
0.6643	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.663	Remote Similarity	NPD7698	Approved
0.663	Remote Similarity	NPD7697	Approved
0.663	Remote Similarity	NPD7696	Phase 3
0.6627	Remote Similarity	NPD6166	Phase 2
0.6627	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6625	Remote Similarity	NPD5403	Approved
0.6625	Remote Similarity	NPD920	Approved
0.6623	Remote Similarity	NPD4060	Phase 1
0.6622	Remote Similarity	NPD9494	Approved
0.6621	Remote Similarity	NPD9269	Phase 2
0.6617	Remote Similarity	NPD9261	Approved
0.6608	Remote Similarity	NPD5844	Phase 1
0.6608	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD5401	Approved
0.66	Remote Similarity	NPD3268	Approved
0.6595	Remote Similarity	NPD8320	Phase 1
0.6595	Remote Similarity	NPD7870	Phase 2
0.6595	Remote Similarity	NPD7871	Phase 2
0.6595	Remote Similarity	NPD8319	Approved
0.6592	Remote Similarity	NPD6212	Phase 3
0.6592	Remote Similarity	NPD6213	Phase 3
0.6592	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD8434	Phase 2
0.6591	Remote Similarity	NPD5037	Approved
0.6591	Remote Similarity	NPD5038	Approved
0.659	Remote Similarity	NPD5030	Phase 2
0.659	Remote Similarity	NPD6559	Discontinued
0.6587	Remote Similarity	NPD5494	Approved
0.6573	Remote Similarity	NPD9268	Approved
0.6573	Remote Similarity	NPD5691	Approved
0.6571	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6568	Remote Similarity	NPD3926	Phase 2
0.6567	Remote Similarity	NPD164	Approved
0.6561	Remote Similarity	NPD8166	Discontinued
0.6558	Remote Similarity	NPD4308	Phase 3
0.6556	Remote Similarity	NPD520	Approved
0.6554	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6554	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6534	Remote Similarity	NPD5036	Approved
0.6533	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6533	Remote Similarity	NPD4625	Phase 3
0.6532	Remote Similarity	NPD5953	Discontinued
0.6531	Remote Similarity	NPD6696	Suspended
0.6528	Remote Similarity	NPD17	Approved
0.6528	Remote Similarity	NPD1778	Approved
0.6514	Remote Similarity	NPD5035	Approved
0.6512	Remote Similarity	NPD845	Approved
0.6508	Remote Similarity	NPD7874	Approved
0.6508	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6507	Remote Similarity	NPD4878	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