NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	166.06
Volume:	171.489
LogP:	1.295
LogD:	1.181
LogS:	-1.917
# Rotatable Bonds:	3
TPSA:	35.53
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	1
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.638
Synthetic Accessibility Score:	1.586
Fsp3:	0.222
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.469
MDCK Permeability:	1.7234046026715077e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.051
Human Intestinal Absorption (HIA):	0.015
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.009

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.991
Plasma Protein Binding (PPB):	71.99759674072266%
Volume Distribution (VD):	0.965
Pgp-substrate:	21.315366744995117%

ADMET: Metabolism

CYP1A2-inhibitor:	0.919
CYP1A2-substrate:	0.905
CYP2C19-inhibitor:	0.167
CYP2C19-substrate:	0.829
CYP2C9-inhibitor:	0.022
CYP2C9-substrate:	0.774
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.817
CYP3A4-inhibitor:	0.02
CYP3A4-substrate:	0.343

ADMET: Excretion

Clearance (CL):	8.409
Half-life (T1/2):	0.836

ADMET: Toxicity

hERG Blockers:	0.085
Human Hepatotoxicity (H-HT):	0.033
Drug-inuced Liver Injury (DILI):	0.048
AMES Toxicity:	0.055
Rat Oral Acute Toxicity:	0.025
Maximum Recommended Daily Dose:	0.036
Skin Sensitization:	0.335
Carcinogencity:	0.076
Eye Corrosion:	0.952
Eye Irritation:	0.986
Respiratory Toxicity:	0.612

Download Data

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

Natural Product: NPC295317

Natural Product ID:	NPC295317
*Common Name:**	3,4-Dimethoxybenzaldehyde
IUPAC Name:	3,4-dimethoxybenzaldehyde
Synonyms:	3,4-Dimethoxybenzaldehyde
Standard InCHIKey:	WJUFSDZVCOTFON-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C9H10O3/c1-11-8-4-3-7(6-10)5-9(8)12-2/h3-6H,1-2H3
SMILES:	COc1ccc(cc1OC)C=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1088937
PubChem CID:	8419
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0004113] Methoxybenzenes [CHEMONTID:0004111] Dimethoxybenzenes

*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
NPO25701	Amentotaxus yunnanensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12880325]
NPO25779	Vicia sativa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1567426]
NPO25813	Salvia przewalskii	Species	Lamiaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[17217287]
NPO487	Tabebuia avellanedae	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17950604]
NPO487	Tabebuia avellanedae	Species	Bignoniaceae	Eukaryota	n.a.	bark	n.a.	PMID[17950604]
NPO12933	Gymnadenia conopsea	Species	Orchidaceae	Eukaryota	tubers	n.a.	n.a.	PMID[18348533]
NPO487	Tabebuia avellanedae	Species	Bignoniaceae	Eukaryota	n.a.	Brazilian	n.a.	PMID[19674905]
NPO10742	Galium verum	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20209910]
NPO12933	Gymnadenia conopsea	Species	Orchidaceae	Eukaryota	n.a.	tuber	n.a.	PMID[21322946]
NPO487	Tabebuia avellanedae	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32044231]
NPO19935	Evodia rutaecarpa	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7463094]
NPO19935	Evodia rutaecarpa	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8201313]
NPO19935	Evodia rutaecarpa	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8699182]
NPO17752	Mentha X piperita	Strain	Lamiaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO17752	Mentha X piperita	Strain	Lamiaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO17752	Mentha X piperita	Strain	Lamiaceae	Eukaryota	Shoot	n.a.	n.a.	Database[FooDB]
NPO17752	Mentha X piperita	Strain	Lamiaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO17752	Mentha X piperita	Strain	Lamiaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO25701	Amentotaxus yunnanensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO30823	Evodia rutaecarpa	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[HerDing]
NPO12933	Gymnadenia conopsea	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10742	Galium verum	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25813	Salvia przewalskii	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24267	Paeonia veitchii	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25779	Vicia sativa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17752	Mentha X piperita	Strain	Lamiaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO10742	Galium verum	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24740	Uvaria klaineana	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25779	Vicia sativa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12933	Gymnadenia conopsea	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25701	Amentotaxus yunnanensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17752	Mentha X piperita	Strain	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24267	Paeonia veitchii	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28257	Dioscorea communis	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19935	Evodia rutaecarpa	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25813	Salvia przewalskii	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10742	Galium verum	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO30823	Evodia rutaecarpa	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO24267	Paeonia veitchii	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO25779	Vicia sativa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO19935	Evodia rutaecarpa	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO25868	Decachaeta ovatifolia	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO23960	Artemisia siversiana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26087	Euphorbia retusa	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10742	Galium verum	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12933	Gymnadenia conopsea	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26223	Cladonia bellidiflora	Species	Cladoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23417	Rhabdia lycioides	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO27437	Camptothecium lutescens	Species	Brachytheciaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17752	Mentha X piperita	Strain	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6346	Phallusia fumigata	Species	Ascidiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25974	Streptomyces lateritius	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO25212	Ritterella rubra	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO415	Deguelia hatschbachii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10155	Stauntonia obovatifoliola	Species	Lardizabalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28257	Dioscorea communis	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24988	Viburnum sieboldi	Species	Adoxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24267	Paeonia veitchii	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25701	Amentotaxus yunnanensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4009	Allochromatium minutissimum	Species	Chromatiaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO12476	Delphinium cyphoplectrum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22016	0tholaena dealbata	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3751	Orthantha lutea	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO26054	Palmaria palmata	Species	Palmariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26316	Pleurophycus gardneri	Species	Alariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25813	Salvia przewalskii	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19935	Evodia rutaecarpa	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10497	Hydrolithon reinboldii	Species	Corallinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24740	Uvaria klaineana	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25779	Vicia sativa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12083	Hydnellum zonatum	Species	Thelephoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO487	Tabebuia avellanedae	Species	Bignoniaceae	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
NPO17752	NPC295317	Other	Leaf	0.0011	0.0002	0.002	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
EC50	1
Others	4
Potency	14

Activity Type	# Activity
Cell Line	1
Individual Protein	6
Organism	2
Others	10

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT210	Individual Protein	Thyroid stimulating hormone receptor	Homo sapiens	Potency	=	1995.3	nM	PMID[513213]
NPT3175	Individual Protein	Collagen	Meloidogyne javanica	Activity	=	70.0	%	PMID[513214]
NPT3175	Individual Protein	Collagen	Meloidogyne javanica	Activity	=	65.0	%	PMID[513214]
NPT65	Cell Line	HepG2	Homo sapiens	CC50	>	1500000.0	nM	PMID[513215]
NPT94	Individual Protein	Aldehyde dehydrogenase 1A1	Homo sapiens	Potency	=	11220.2	nM	PMID[513213]
NPT450	Organism	Meloidogyne incognita	Meloidogyne incognita	EC50	>	1000.0	ug.mL-1	PMID[513214]
NPT450	Organism	Meloidogyne incognita	Meloidogyne incognita	EC100	>	1000.0	mg/L	PMID[513214]
NPT2	Others	Unspecified		Potency	n.a.	6859	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	15486.4	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	13802.2	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	62316.7	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	77742.1	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	49052	nM	PubChem BioAssay data set
NPT74	Individual Protein	Proto-oncogene c-JUN	Homo sapiens	Potency	n.a.	49499.9	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	55539.8	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	61752.8	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	27583.9	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 NPC295317 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	410
0.1-0.2	2552
0.2-0.3	6292
0.3-0.4	12207
0.4-0.5	3728
0.5-0.6	6227
0.6-0.7	9363
0.7-0.8	1777
0.8-0.85	101
0.85-0.9	29
0.9-0.95	9
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9576	High Similarity	NPC473626
0.9483	High Similarity	NPC225245
0.9417	High Similarity	NPC117237
0.9417	High Similarity	NPC203719
0.925	High Similarity	NPC120066
0.9244	High Similarity	NPC474691
0.9187	High Similarity	NPC298268
0.918	High Similarity	NPC304747
0.9115	High Similarity	NPC54626
0.9115	High Similarity	NPC57879
0.9027	High Similarity	NPC179309
0.9016	High Similarity	NPC154275
0.9008	High Similarity	NPC30216
0.8943	High Similarity	NPC32163
0.8943	High Similarity	NPC286683
0.8943	High Similarity	NPC16651
0.8879	High Similarity	NPC252004
0.875	High Similarity	NPC144662
0.875	High Similarity	NPC237330
0.874	High Similarity	NPC50763
0.873	High Similarity	NPC285776
0.8696	High Similarity	NPC183648
0.8682	High Similarity	NPC38101
0.8682	High Similarity	NPC274613
0.8651	High Similarity	NPC261759
0.8621	High Similarity	NPC23332
0.8594	High Similarity	NPC153453
0.8594	High Similarity	NPC111888
0.8583	High Similarity	NPC299010
0.8583	High Similarity	NPC66905
0.8571	High Similarity	NPC316062
0.855	High Similarity	NPC474274
0.855	High Similarity	NPC157944
0.8538	High Similarity	NPC139519
0.8527	High Similarity	NPC159418
0.8527	High Similarity	NPC288743
0.8527	High Similarity	NPC283823
0.85	High Similarity	NPC39793
0.8417	Intermediate Similarity	NPC111225
0.8417	Intermediate Similarity	NPC268317
0.8397	Intermediate Similarity	NPC95485
0.8397	Intermediate Similarity	NPC89504
0.8397	Intermediate Similarity	NPC88065
0.8387	Intermediate Similarity	NPC114298
0.837	Intermediate Similarity	NPC299154
0.8347	Intermediate Similarity	NPC185738
0.8346	Intermediate Similarity	NPC325625
0.8333	Intermediate Similarity	NPC278102
0.8333	Intermediate Similarity	NPC220540
0.8321	Intermediate Similarity	NPC155098
0.832	Intermediate Similarity	NPC242372
0.832	Intermediate Similarity	NPC257976
0.832	Intermediate Similarity	NPC4181
0.832	Intermediate Similarity	NPC164778
0.8319	Intermediate Similarity	NPC12714
0.8319	Intermediate Similarity	NPC53953
0.8319	Intermediate Similarity	NPC310905
0.8279	Intermediate Similarity	NPC205502
0.8258	Intermediate Similarity	NPC208760
0.8254	Intermediate Similarity	NPC312404
0.8254	Intermediate Similarity	NPC273686
0.825	Intermediate Similarity	NPC294941
0.8235	Intermediate Similarity	NPC27220
0.823	Intermediate Similarity	NPC13755
0.8226	Intermediate Similarity	NPC471877
0.8226	Intermediate Similarity	NPC158949
0.8222	Intermediate Similarity	NPC250597
0.8211	Intermediate Similarity	NPC299406
0.8209	Intermediate Similarity	NPC470962
0.8197	Intermediate Similarity	NPC240664
0.8197	Intermediate Similarity	NPC469954
0.8188	Intermediate Similarity	NPC9370
0.8188	Intermediate Similarity	NPC287495
0.8182	Intermediate Similarity	NPC45404
0.8174	Intermediate Similarity	NPC292792
0.8148	Intermediate Similarity	NPC223336
0.8148	Intermediate Similarity	NPC4796
0.8134	Intermediate Similarity	NPC25305
0.8134	Intermediate Similarity	NPC125417
0.8134	Intermediate Similarity	NPC110899
0.8134	Intermediate Similarity	NPC95679
0.8134	Intermediate Similarity	NPC112068
0.813	Intermediate Similarity	NPC212743
0.813	Intermediate Similarity	NPC277460
0.8125	Intermediate Similarity	NPC177925
0.8125	Intermediate Similarity	NPC179777
0.812	Intermediate Similarity	NPC143649
0.812	Intermediate Similarity	NPC227894
0.812	Intermediate Similarity	NPC258171
0.8116	Intermediate Similarity	NPC275278
0.8115	Intermediate Similarity	NPC470860
0.811	Intermediate Similarity	NPC255073
0.811	Intermediate Similarity	NPC4012
0.8102	Intermediate Similarity	NPC28326
0.8088	Intermediate Similarity	NPC138438
0.8088	Intermediate Similarity	NPC908
0.8088	Intermediate Similarity	NPC326065
0.8077	Intermediate Similarity	NPC226855
0.8074	Intermediate Similarity	NPC44573
0.8065	Intermediate Similarity	NPC37858
0.8065	Intermediate Similarity	NPC61779
0.8062	Intermediate Similarity	NPC123228
0.8062	Intermediate Similarity	NPC158654
0.8062	Intermediate Similarity	NPC5018
0.8062	Intermediate Similarity	NPC276466
0.8062	Intermediate Similarity	NPC123722
0.8062	Intermediate Similarity	NPC151167
0.8062	Intermediate Similarity	NPC281020
0.8049	Intermediate Similarity	NPC212643
0.8049	Intermediate Similarity	NPC280001
0.8049	Intermediate Similarity	NPC199209
0.8049	Intermediate Similarity	NPC150919
0.8045	Intermediate Similarity	NPC311339
0.8043	Intermediate Similarity	NPC469615
0.8043	Intermediate Similarity	NPC239608
0.8043	Intermediate Similarity	NPC46161
0.8043	Intermediate Similarity	NPC473090
0.8031	Intermediate Similarity	NPC108545
0.8031	Intermediate Similarity	NPC141252
0.8031	Intermediate Similarity	NPC11799
0.8031	Intermediate Similarity	NPC244876
0.8029	Intermediate Similarity	NPC84273
0.8017	Intermediate Similarity	NPC38209
0.8016	Intermediate Similarity	NPC194416
0.8016	Intermediate Similarity	NPC177291
0.8016	Intermediate Similarity	NPC201777
0.8	Intermediate Similarity	NPC245552
0.8	Intermediate Similarity	NPC202474
0.7986	Intermediate Similarity	NPC469683
0.7985	Intermediate Similarity	NPC204592
0.7984	Intermediate Similarity	NPC84076
0.7984	Intermediate Similarity	NPC90128
0.7984	Intermediate Similarity	NPC272471
0.7984	Intermediate Similarity	NPC166591
0.7984	Intermediate Similarity	NPC171023
0.7984	Intermediate Similarity	NPC70744
0.7984	Intermediate Similarity	NPC159916
0.7984	Intermediate Similarity	NPC124916
0.7984	Intermediate Similarity	NPC303680
0.7984	Intermediate Similarity	NPC276014
0.7984	Intermediate Similarity	NPC164706
0.7984	Intermediate Similarity	NPC137537
0.7984	Intermediate Similarity	NPC107588
0.7971	Intermediate Similarity	NPC176030
0.7971	Intermediate Similarity	NPC192597
0.7971	Intermediate Similarity	NPC229218
0.7971	Intermediate Similarity	NPC125134
0.7971	Intermediate Similarity	NPC185607
0.7971	Intermediate Similarity	NPC141817
0.7971	Intermediate Similarity	NPC312256
0.7971	Intermediate Similarity	NPC169214
0.7971	Intermediate Similarity	NPC137920
0.7971	Intermediate Similarity	NPC86455
0.7958	Intermediate Similarity	NPC227980
0.7956	Intermediate Similarity	NPC28398
0.7956	Intermediate Similarity	NPC50823
0.7953	Intermediate Similarity	NPC286573
0.7953	Intermediate Similarity	NPC256167
0.7953	Intermediate Similarity	NPC291189
0.7953	Intermediate Similarity	NPC69403
0.7941	Intermediate Similarity	NPC207516
0.7941	Intermediate Similarity	NPC46947
0.7941	Intermediate Similarity	NPC233780
0.7941	Intermediate Similarity	NPC284409
0.7939	Intermediate Similarity	NPC304622
0.7939	Intermediate Similarity	NPC150809
0.7937	Intermediate Similarity	NPC204466
0.7931	Intermediate Similarity	NPC298224
0.7929	Intermediate Similarity	NPC30890
0.7926	Intermediate Similarity	NPC77955
0.7926	Intermediate Similarity	NPC324929
0.7923	Intermediate Similarity	NPC223807
0.792	Intermediate Similarity	NPC69670
0.7917	Intermediate Similarity	NPC137685
0.7914	Intermediate Similarity	NPC46880
0.7907	Intermediate Similarity	NPC280767
0.7907	Intermediate Similarity	NPC470858
0.7907	Intermediate Similarity	NPC271985
0.7899	Intermediate Similarity	NPC58229
0.7899	Intermediate Similarity	NPC110419
0.7895	Intermediate Similarity	NPC175298
0.7891	Intermediate Similarity	NPC160900
0.7891	Intermediate Similarity	NPC18984
0.7891	Intermediate Similarity	NPC21238
0.7891	Intermediate Similarity	NPC229084
0.7891	Intermediate Similarity	NPC106659
0.7891	Intermediate Similarity	NPC163083
0.7881	Intermediate Similarity	NPC1065
0.7879	Intermediate Similarity	NPC172673
0.7879	Intermediate Similarity	NPC245395
0.7874	Intermediate Similarity	NPC114845
0.7874	Intermediate Similarity	NPC70752
0.7872	Intermediate Similarity	NPC216314
0.7872	Intermediate Similarity	NPC195919
0.7872	Intermediate Similarity	NPC120924
0.7872	Intermediate Similarity	NPC24257
0.7872	Intermediate Similarity	NPC153620
0.7869	Intermediate Similarity	NPC303522
0.7857	Intermediate Similarity	NPC300603
0.7857	Intermediate Similarity	NPC293201

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 NPC295317 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	1094
0.2-0.3	1718
0.3-0.4	2799
0.4-0.5	1679
0.5-0.6	1049
0.6-0.7	362
0.7-0.8	63
0.8-0.85	1
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9417	High Similarity	NPD9494	Approved
0.8347	Intermediate Similarity	NPD5536	Phase 2
0.8017	Intermediate Similarity	NPD1241	Discontinued
0.7891	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7836	Intermediate Similarity	NPD447	Suspended
0.7815	Intermediate Similarity	NPD1358	Approved
0.7812	Intermediate Similarity	NPD3972	Approved
0.7705	Intermediate Similarity	NPD228	Approved
0.7704	Intermediate Similarity	NPD230	Phase 1
0.7698	Intermediate Similarity	NPD9545	Approved
0.7603	Intermediate Similarity	NPD6386	Approved
0.7603	Intermediate Similarity	NPD6385	Approved
0.7586	Intermediate Similarity	NPD824	Approved
0.7583	Intermediate Similarity	NPD3134	Approved
0.7581	Intermediate Similarity	NPD5283	Phase 1
0.7569	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7557	Intermediate Similarity	NPD1876	Approved
0.7534	Intermediate Similarity	NPD1337	Clinical (unspecified phase)
0.7445	Intermediate Similarity	NPD1933	Approved
0.7434	Intermediate Similarity	NPD1247	Approved
0.7417	Intermediate Similarity	NPD919	Approved
0.74	Intermediate Similarity	NPD3882	Suspended
0.7372	Intermediate Similarity	NPD3140	Approved
0.7372	Intermediate Similarity	NPD3142	Approved
0.7364	Intermediate Similarity	NPD1651	Approved
0.7364	Intermediate Similarity	NPD1357	Approved
0.7361	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD5977	Approved
0.7333	Intermediate Similarity	NPD5353	Approved
0.7333	Intermediate Similarity	NPD5978	Approved
0.7328	Intermediate Similarity	NPD1281	Approved
0.7328	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD1934	Approved
0.7308	Intermediate Similarity	NPD17	Approved
0.7273	Intermediate Similarity	NPD4628	Phase 3
0.7267	Intermediate Similarity	NPD2801	Approved
0.7255	Intermediate Similarity	NPD5494	Approved
0.7246	Intermediate Similarity	NPD1240	Approved
0.7234	Intermediate Similarity	NPD2796	Approved
0.7231	Intermediate Similarity	NPD9268	Approved
0.7219	Intermediate Similarity	NPD3817	Phase 2
0.7194	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD3688	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD3146	Approved
0.7185	Intermediate Similarity	NPD1019	Discontinued
0.7164	Intermediate Similarity	NPD1283	Approved
0.7163	Intermediate Similarity	NPD1510	Phase 2
0.7143	Intermediate Similarity	NPD1608	Approved
0.7143	Intermediate Similarity	NPD1607	Approved
0.7143	Intermediate Similarity	NPD9717	Approved
0.7143	Intermediate Similarity	NPD9269	Phase 2
0.7133	Intermediate Similarity	NPD6873	Phase 2
0.7132	Intermediate Similarity	NPD9493	Approved
0.7123	Intermediate Similarity	NPD1511	Approved
0.7115	Intermediate Similarity	NPD5242	Approved
0.7113	Intermediate Similarity	NPD2935	Discontinued
0.7103	Intermediate Similarity	NPD3887	Approved
0.7099	Intermediate Similarity	NPD5691	Approved
0.7097	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD743	Approved
0.708	Intermediate Similarity	NPD6832	Phase 2
0.7068	Intermediate Similarity	NPD3705	Approved
0.7063	Intermediate Similarity	NPD2353	Approved
0.7063	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD2344	Approved
0.7059	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD2798	Approved
0.7045	Intermediate Similarity	NPD1778	Approved
0.704	Intermediate Similarity	NPD2684	Approved
0.7039	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD1006	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD4110	Phase 3
0.7034	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD1512	Approved
0.7015	Intermediate Similarity	NPD2981	Phase 2
0.7014	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7008	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD6799	Approved
0.7006	Intermediate Similarity	NPD3926	Phase 2
0.7	Intermediate Similarity	NPD943	Approved
0.6981	Remote Similarity	NPD2822	Clinical (unspecified phase)
0.698	Remote Similarity	NPD6662	Clinical (unspecified phase)
0.698	Remote Similarity	NPD920	Approved
0.6978	Remote Similarity	NPD411	Approved
0.697	Remote Similarity	NPD5585	Approved
0.6966	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD2983	Phase 2
0.6963	Remote Similarity	NPD2982	Phase 2
0.6959	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD1471	Phase 3
0.6943	Remote Similarity	NPD6232	Discontinued
0.6942	Remote Similarity	NPD1238	Approved
0.6939	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD2799	Discontinued
0.6917	Remote Similarity	NPD4626	Approved
0.6901	Remote Similarity	NPD2492	Phase 1
0.6897	Remote Similarity	NPD1549	Phase 2
0.6894	Remote Similarity	NPD1894	Discontinued
0.6892	Remote Similarity	NPD4357	Discontinued
0.6887	Remote Similarity	NPD7458	Discontinued
0.6879	Remote Similarity	NPD2979	Phase 3
0.6875	Remote Similarity	NPD2438	Suspended
0.6875	Remote Similarity	NPD3818	Discontinued
0.6875	Remote Similarity	NPD1551	Phase 2
0.6871	Remote Similarity	NPD2309	Approved
0.6871	Remote Similarity	NPD6190	Approved
0.6871	Remote Similarity	NPD2354	Approved
0.6861	Remote Similarity	NPD1203	Approved
0.6855	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD6166	Phase 2
0.6855	Remote Similarity	NPD164	Approved
0.6855	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD5844	Phase 1
0.6828	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6825	Remote Similarity	NPD290	Approved
0.6822	Remote Similarity	NPD7843	Approved
0.6821	Remote Similarity	NPD957	Approved
0.6818	Remote Similarity	NPD1465	Phase 2
0.6813	Remote Similarity	NPD7473	Discontinued
0.681	Remote Similarity	NPD7685	Pre-registration
0.6806	Remote Similarity	NPD651	Clinical (unspecified phase)
0.68	Remote Similarity	NPD6273	Approved
0.68	Remote Similarity	NPD9697	Approved
0.6797	Remote Similarity	NPD7110	Phase 1
0.6797	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD7109	Clinical (unspecified phase)
0.6794	Remote Similarity	NPD7157	Approved
0.679	Remote Similarity	NPD2325	Approved
0.6786	Remote Similarity	NPD3027	Phase 3
0.6776	Remote Similarity	NPD3455	Phase 2
0.6776	Remote Similarity	NPD2649	Approved
0.6776	Remote Similarity	NPD2651	Approved
0.6774	Remote Similarity	NPD9261	Approved
0.6772	Remote Similarity	NPD2182	Approved
0.6772	Remote Similarity	NPD2821	Approved
0.6763	Remote Similarity	NPD3018	Phase 2
0.6761	Remote Similarity	NPD4307	Phase 2
0.675	Remote Similarity	NPD9296	Approved
0.6742	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6741	Remote Similarity	NPD3496	Discontinued
0.6738	Remote Similarity	NPD6798	Discontinued
0.6738	Remote Similarity	NPD2313	Discontinued
0.6738	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD1243	Approved
0.6732	Remote Similarity	NPD6599	Discontinued
0.6732	Remote Similarity	NPD7028	Phase 2
0.6732	Remote Similarity	NPD6875	Approved
0.6732	Remote Similarity	NPD4380	Phase 2
0.6732	Remote Similarity	NPD6876	Approved
0.6728	Remote Similarity	NPD7054	Approved
0.6715	Remote Similarity	NPD4359	Approved
0.6713	Remote Similarity	NPD6355	Discontinued
0.6712	Remote Similarity	NPD2346	Discontinued
0.671	Remote Similarity	NPD7819	Suspended
0.671	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD291	Approved
0.669	Remote Similarity	NPD3748	Approved
0.669	Remote Similarity	NPD1726	Clinical (unspecified phase)
0.669	Remote Similarity	NPD6233	Phase 2
0.669	Remote Similarity	NPD4062	Phase 3
0.6689	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD7003	Approved
0.6689	Remote Similarity	NPD2186	Approved
0.6688	Remote Similarity	NPD958	Approved
0.6687	Remote Similarity	NPD7074	Phase 3
0.6687	Remote Similarity	NPD7472	Approved
0.6667	Remote Similarity	NPD2653	Approved
0.6667	Remote Similarity	NPD2163	Approved
0.6667	Remote Similarity	NPD2922	Phase 1
0.6645	Remote Similarity	NPD6279	Approved
0.6645	Remote Similarity	NPD6280	Approved
0.6645	Remote Similarity	NPD5586	Clinical (unspecified phase)
0.6644	Remote Similarity	NPD2531	Phase 2
0.6643	Remote Similarity	NPD454	Approved
0.6642	Remote Similarity	NPD1481	Phase 2
0.6623	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD2532	Approved
0.6623	Remote Similarity	NPD2534	Approved
0.6623	Remote Similarity	NPD2533	Approved
0.6622	Remote Similarity	NPD2654	Approved
0.662	Remote Similarity	NPD5110	Phase 2
0.662	Remote Similarity	NPD5718	Phase 2
0.662	Remote Similarity	NPD3145	Approved
0.662	Remote Similarity	NPD5111	Phase 2
0.662	Remote Similarity	NPD5109	Approved
0.662	Remote Similarity	NPD3144	Approved
0.662	Remote Similarity	NPD3764	Approved
0.6619	Remote Similarity	NPD3267	Approved
0.6619	Remote Similarity	NPD3266	Approved
0.6619	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.6618	Remote Similarity	NPD3847	Discontinued
0.6593	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6589	Remote Similarity	NPD5451	Approved
0.6582	Remote Similarity	NPD7075	Discontinued
0.6577	Remote Similarity	NPD8166	Discontinued
0.6575	Remote Similarity	NPD4308	Phase 3
0.6573	Remote Similarity	NPD2674	Phase 3

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data