Structure

Physi-Chem Properties

Molecular Weight:  290.14
Volume:  288.126
LogP:  3.063
LogD:  3.006
LogS:  -4.314
# Rotatable Bonds:  7
TPSA:  88.48
# H-Bond Aceptor:  7
# H-Bond Donor:  2
# Rings:  2
# Heavy Atoms:  7

MedChem Properties

QED Drug-Likeness Score:  0.847
Synthetic Accessibility Score:  2.845
Fsp3:  0.357
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.612
MDCK Permeability:  3.051780731766485e-05
Pgp-inhibitor:  0.006
Pgp-substrate:  0.984
Human Intestinal Absorption (HIA):  0.02
20% Bioavailability (F20%):  0.004
30% Bioavailability (F30%):  0.054

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.999
Plasma Protein Binding (PPB):  64.24415588378906%
Volume Distribution (VD):  0.745
Pgp-substrate:  28.51961326599121%

ADMET: Metabolism

CYP1A2-inhibitor:  0.911
CYP1A2-substrate:  0.955
CYP2C19-inhibitor:  0.539
CYP2C19-substrate:  0.37
CYP2C9-inhibitor:  0.139
CYP2C9-substrate:  0.806
CYP2D6-inhibitor:  0.268
CYP2D6-substrate:  0.257
CYP3A4-inhibitor:  0.323
CYP3A4-substrate:  0.678

ADMET: Excretion

Clearance (CL):  5.45
Half-life (T1/2):  0.86

ADMET: Toxicity

hERG Blockers:  0.026
Human Hepatotoxicity (H-HT):  0.977
Drug-inuced Liver Injury (DILI):  0.951
AMES Toxicity:  0.723
Rat Oral Acute Toxicity:  0.89
Maximum Recommended Daily Dose:  0.906
Skin Sensitization:  0.322
Carcinogencity:  0.9
Eye Corrosion:  0.003
Eye Irritation:  0.017
Respiratory Toxicity:  0.844

Download Data

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

  Natural Product: NPC330923

Natural Product ID:  NPC330923
Common Name*:   RIOXQFHNBCKOKP-UHFFFAOYSA-N
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  RIOXQFHNBCKOKP-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C14H18N4O3/c1-3-4-9-15-13(19)18-11-8-6-5-7-10(11)16-12(18)17-14(20)21-2/h5-8H,3-4,9H2,1-2H3,(H,15,19)(H,16,17,20)
SMILES:  CCCCN=C(n1c2ccccc2nc1N=C(O)OC)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   n.a.
PubChem CID:   28780
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0000294] Benzimidazoles
        • [CHEMONTID:0004711] 2-benzimidazolylcarbamic acid esters

*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
NPO7694 Anasterias minuta Species n.a. n.a. n.a. n.a. n.a. PMID[11858747]
NPO7694 Anasterias minuta Species n.a. n.a. n.a. n.a. n.a. PMID[16124779]
NPO7694 Anasterias minuta Species n.a. n.a. 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

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT1418 Individual Protein Anandamide amidohydrolase Homo sapiens Inhibition = 34.0 % PMID[19850474]
NPT1173 Organism Candida albicans SC5314 Candida albicans SC5314 MIC = 20.0 ug.mL-1 PMID[17325226]
NPT20 Organism Candida albicans Candida albicans MIC = 20.0 ug.mL-1 PMID[17325226]
NPT985 Organism Cladosporium cucumerinum Cladosporium cucumerinum IZ = 20.0 mm PMID[11858747]
NPT1198 Organism Magnaporthe grisea Magnaporthe grisea MIC = 200.0 ug.mL-1 PMID[14738379]
NPT1198 Organism Magnaporthe grisea Magnaporthe grisea EC50 = 0.06 ug.mL-1 PMID[14738379]
NPT1780 Organism Davidiella tassiana Davidiella tassiana MIC < 25.0 ug PMID[14738379]
NPT985 Organism Cladosporium cucumerinum Cladosporium cucumerinum IZ = 15.0 mm PMID[16124779]
NPT185 Organism Aspergillus flavus Aspergillus flavus IZ = 14.0 mm PMID[16124779]
NPT985 Organism Cladosporium cucumerinum Cladosporium cucumerinum IZ = 20.0 mm PMID[15165137]
NPT3821 Organism Alternaria citri Alternaria citri EC50 > 200.0 ug.mL-1 PMID[12088422]
NPT3660 Organism Fusarium avenaceum Fusarium avenaceum EC50 = 0.02 ug.mL-1 PMID[12088422]
NPT1198 Organism Magnaporthe grisea Magnaporthe grisea EC50 = 0.06 ug.mL-1 PMID[12088422]
NPT3821 Organism Alternaria citri Alternaria citri EC90 > 200.0 ug ml-1 PMID[12088422]
NPT3660 Organism Fusarium avenaceum Fusarium avenaceum EC90 > 200.0 ug ml-1 PMID[12088422]
NPT1198 Organism Magnaporthe grisea Magnaporthe grisea EC90 = 84.0 ug ml-1 PMID[12088422]
NPT3821 Organism Alternaria citri Alternaria citri MIC > 200.0 ug.mL-1 PMID[12088422]
NPT3660 Organism Fusarium avenaceum Fusarium avenaceum MIC = 100.0 ug.mL-1 PMID[12088422]
NPT1198 Organism Magnaporthe grisea Magnaporthe grisea MIC = 200.0 ug.mL-1 PMID[12088422]
NPT635 Organism Botryotinia fuckeliana Botryotinia fuckeliana MIC > 200.0 ug.mL-1 PMID[12088422]
NPT1780 Organism Davidiella tassiana Davidiella tassiana MIC > 200.0 ug.mL-1 PMID[12088422]
NPT635 Organism Botryotinia fuckeliana Botryotinia fuckeliana Inhibition = 85.0 % PMID[12088422]
NPT1780 Organism Davidiella tassiana Davidiella tassiana Inhibition = 85.0 % PMID[12088422]
NPT312 Organism Saccharomyces cerevisiae Saccharomyces cerevisiae IZ = 9.0 mm PMID[20739103]
NPT312 Organism Saccharomyces cerevisiae Saccharomyces cerevisiae IZ = 4.0 mm PMID[20739103]
NPT3594 Organism Galactomyces geotrichum Galactomyces geotrichum IZ = 0.0 mm PMID[23062823]
NPT2793 Organism Phytophthora citrophthora Phytophthora citrophthora IZ = 44.33 mm PMID[23062823]
NPT2567 Organism Trichoderma viride Hypocrea rufa IZ = 29.33 mm PMID[23062823]
NPT1262 Organism Aspergillus parasiticus Aspergillus parasiticus IZ = 29.33 mm PMID[23062823]
NPT1278 Organism Fusarium culmorum Fusarium culmorum IZ = 27.66 mm PMID[23062823]
NPT3519 Organism Blumeria graminis f. sp. hordei Blumeria graminis f. sp. hordei Activity = 75.0 % PMID[21910504]
NPT3519 Organism Blumeria graminis f. sp. hordei Blumeria graminis f. sp. hordei Activity = 100.0 % PMID[21910504]
NPT851 Organism Colletotrichum fragariae Colletotrichum fragariae GI = 21.3 % PMID[19113871]
NPT15775 ORGANISM Fusarium oxysporum f. sp. cubense race 4 Fusarium oxysporum f. sp. cubense race 4 Activity = 72.2 % DOI[10.1016/j.cropro.2006.06.008]
NPT15775 ORGANISM Fusarium oxysporum f. sp. cubense race 4 Fusarium oxysporum f. sp. cubense race 4 Activity = 22.2 % DOI[10.1016/j.cropro.2006.06.008]
NPT15775 ORGANISM Fusarium oxysporum f. sp. cubense race 4 Fusarium oxysporum f. sp. cubense race 4 Activity = 66.7 % DOI[10.1016/j.cropro.2006.06.008]
NPT1525 Organism Rhizoctonia solani AG-1 IA Rhizoctonia solani AG-1 IA EC90 = 17.43 mg/L DOI[10.1016/j.cropro.2005.11.008]
NPT1525 Organism Rhizoctonia solani AG-1 IA Rhizoctonia solani AG-1 IA EC50 = 0.352 ug.mL-1 DOI[10.1016/j.cropro.2005.11.008]
NPT1525 Organism Rhizoctonia solani AG-1 IA Rhizoctonia solani AG-1 IA Activity = 0.0 mm DOI[10.1016/j.cropro.2005.11.008]
NPT1525 Organism Rhizoctonia solani AG-1 IA Rhizoctonia solani AG-1 IA Activity = 9.6 mm DOI[10.1016/j.cropro.2005.11.008]
NPT1525 Organism Rhizoctonia solani AG-1 IA Rhizoctonia solani AG-1 IA Activity = 38.8 mm DOI[10.1016/j.cropro.2005.11.008]
NPT6220 Organism Monilinia laxa Monilinia laxa Activity = 100.0 % DOI[10.1016/j.cropro.2012.04.001]
NPT6220 Organism Monilinia laxa Monilinia laxa Activity = 80.01 % DOI[10.1016/j.cropro.2012.04.001]
NPT6220 Organism Monilinia laxa Monilinia laxa Activity = 0.0 % DOI[10.1016/j.cropro.2012.04.001]
NPT4814 Organism Penicillium italicum Penicillium italicum IZ = 16.67 mm PMID[17628075]
NPT1262 Organism Aspergillus parasiticus Aspergillus parasiticus IZ = 8.33 mm PMID[17628075]
NPT2567 Organism Trichoderma viride Hypocrea rufa IZ = 12.33 mm PMID[17628075]
NPT6882 Organism Trichothecium roseum Trichothecium roseum IZ = 29.67 mm PMID[17628075]
NPT562 Organism Colletotrichum gloeosporioides Colletotrichum gloeosporioides IZ = 26.67 mm PMID[17628075]
NPT2793 Organism Phytophthora citrophthora Phytophthora citrophthora IZ = 17.13 mm PMID[17628075]
NPT1503 Organism Verticillium dahliae Verticillium dahliae IZ = 14.32 mm PMID[17628075]
NPT6887 Organism Fusarium oxysporum f. sp. gladioli Fusarium oxysporum f. sp. gladioli IZ = 9.33 mm PMID[17628075]
NPT5164 Organism Fusarium oxysporum f. sp. niveum Fusarium oxysporum f. sp. niveum IZ = 17.33 mm PMID[17628075]
NPT1278 Organism Fusarium culmorum Fusarium culmorum IZ = 19.0 mm PMID[17628075]
NPT851 Organism Colletotrichum fragariae Colletotrichum fragariae Activity = 21.3 mm PMID[17894463]
NPT562 Organism Colletotrichum gloeosporioides Colletotrichum gloeosporioides IZ = 19.33 mm PMID[16939314]
NPT851 Organism Colletotrichum fragariae Colletotrichum fragariae IZ = 18.33 mm PMID[16939314]
NPT1096 Organism Colletotrichum acutatum Colletotrichum acutatum IZ = 18.0 mm PMID[16939314]
NPT1276 Organism Gibberella zeae Gibberella zeae EC50 = 3.93 ug.mL-1 PMID[21077124]
NPT1276 Organism Gibberella zeae Gibberella zeae EC50 = 3.19 ug.mL-1 PMID[21077124]
NPT1276 Organism Gibberella zeae Gibberella zeae EC50 = 4.46 ug.mL-1 PMID[21077124]
NPT1276 Organism Gibberella zeae Gibberella zeae EC50 = 5.81 ug.mL-1 PMID[21077124]
NPT1276 Organism Gibberella zeae Gibberella zeae EC50 = 6.05 ug.mL-1 PMID[21077124]
NPT1276 Organism Gibberella zeae Gibberella zeae EC50 = 8.83 ug.mL-1 PMID[21077124]
NPT1276 Organism Gibberella zeae Gibberella zeae EC50 = 14.99 ug.mL-1 PMID[21077124]
NPT1276 Organism Gibberella zeae Gibberella zeae EC50 = 17.68 ug.mL-1 PMID[21077124]
NPT1262 Organism Aspergillus parasiticus Aspergillus parasiticus GI = 100.0 % PMID[10956170]
NPT4814 Organism Penicillium italicum Penicillium italicum GI = 100.0 % PMID[10956170]
NPT2567 Organism Trichoderma viride Hypocrea rufa GI = 100.0 % PMID[10956170]
NPT2793 Organism Phytophthora citrophthora Phytophthora citrophthora GI = 100.0 % PMID[10956170]
NPT1503 Organism Verticillium dahliae Verticillium dahliae GI = 100.0 % PMID[10956170]
NPT2646 Organism Alternaria tenuis Alternaria tenuis GI = 0.0 % PMID[10956170]
NPT6882 Organism Trichothecium roseum Trichothecium roseum GI = 100.0 % PMID[10956170]
NPT3518 Organism Colletotrichum coccodes Colletotrichum coccodes GI = 100.0 % PMID[10956170]
NPT562 Organism Colletotrichum gloeosporioides Colletotrichum gloeosporioides GI = 100.0 % PMID[10956170]
NPT3594 Organism Galactomyces geotrichum Galactomyces geotrichum GI = 0.0 % PMID[10956170]
NPT5164 Organism Fusarium oxysporum f. sp. niveum Fusarium oxysporum f. sp. niveum GI = 100.0 % PMID[10956170]
NPT6887 Organism Fusarium oxysporum f. sp. gladioli Fusarium oxysporum f. sp. gladioli GI = 11.1 % PMID[10956170]
NPT1278 Organism Fusarium culmorum Fusarium culmorum GI = 87.0 % PMID[10956170]
NPT1276 Organism Gibberella zeae Gibberella zeae EC50 = 3.02 ug.mL-1 PMID[21077124]
NPT1276 Organism Gibberella zeae Gibberella zeae EC50 = 0.61 ug.mL-1 PMID[21077124]
NPT2241 Organism Glomerella acutata Glomerella acutata GI = 33.0 % PMID[12568545]
NPT637 Organism Fusarium oxysporum Fusarium oxysporum GI = 77.0 % PMID[12568545]
NPT851 Organism Colletotrichum fragariae Colletotrichum fragariae GI = 76.0 % PMID[12568545]
NPT562 Organism Colletotrichum gloeosporioides Colletotrichum gloeosporioides GI = 66.0 % PMID[12568545]
NPT850 Organism Diaporthe ampelina Diaporthe ampelina GI = 57.0 % PMID[12568545]
NPT827 Organism Mycosphaerella graminicola Mycosphaerella graminicola MIC = 0.6 ug.mL-1 PMID[12568568]
NPT529 Organism Rhizoctonia solani Rhizoctonia solani MIC = 6.2 ug.mL-1 PMID[12568568]
NPT1276 Organism Gibberella zeae Gibberella zeae MIC = 0.6 ug.mL-1 PMID[12568568]
NPT1279 Organism Fusarium oxysporum f. sp. lycopersici Fusarium oxysporum f. sp. lycopersici MIC = 1.5 ug.mL-1 PMID[12568568]
NPT852 Organism Phomopsis obscurans Phomopsis obscurans GI = 100.0 % PMID[18085331]
NPT637 Organism Fusarium oxysporum Fusarium oxysporum GI = 77.0 % PMID[18085331]
NPT851 Organism Colletotrichum fragariae Colletotrichum fragariae GI = 76.0 % PMID[18085331]
NPT2241 Organism Glomerella acutata Glomerella acutata GI = 33.0 % PMID[18085331]
NPT3821 Organism Alternaria citri Alternaria citri MIC > 200.0 ug.mL-1 PMID[10775404]
NPT3821 Organism Alternaria citri Alternaria citri EC90 > 200.0 ug ml-1 PMID[10775404]
NPT3660 Organism Fusarium avenaceum Fusarium avenaceum MIC = 100.0 ug.mL-1 PMID[10775404]
NPT3660 Organism Fusarium avenaceum Fusarium avenaceum EC90 > 200.0 ug ml-1 PMID[10775404]
NPT1198 Organism Magnaporthe grisea Magnaporthe grisea MIC = 200.0 ug.mL-1 PMID[10775404]
NPT1198 Organism Magnaporthe grisea Magnaporthe grisea EC90 = 84.0 ug ml-1 PMID[10775404]
NPT3821 Organism Alternaria citri Alternaria citri EC50 > 200.0 ug.mL-1 PMID[10775404]
NPT3660 Organism Fusarium avenaceum Fusarium avenaceum EC50 = 0.02 ug.mL-1 PMID[10775404]
NPT1198 Organism Magnaporthe grisea Magnaporthe grisea EC50 = 0.06 ug.mL-1 PMID[10775404]
NPT5960 Organism Penicillium brevicompactum Penicillium brevicompactum MIC > 25.0 ug.mL-1 PMID[15137845]
NPT1262 Organism Aspergillus parasiticus Aspergillus parasiticus MIC > 25.0 ug.mL-1 PMID[15137845]
NPT635 Organism Botryotinia fuckeliana Botryotinia fuckeliana MIC = 0.19 ug.mL-1 PMID[15137845]
NPT15793 ORGANISM Leptosphaeria biglobosa Leptosphaeria biglobosa Activity = 81.6 % PMID[20013877]
NPT15793 ORGANISM Leptosphaeria biglobosa Leptosphaeria biglobosa Activity = 85.5 % PMID[20013877]
NPT15793 ORGANISM Leptosphaeria biglobosa Leptosphaeria biglobosa Activity = 4.5 % PMID[20013877]
NPT4113 Organism Leptosphaeria maculans Leptosphaeria maculans Activity = 65.8 % PMID[20013877]
NPT4113 Organism Leptosphaeria maculans Leptosphaeria maculans Activity = 68.3 % PMID[20013877]
NPT4113 Organism Leptosphaeria maculans Leptosphaeria maculans Activity = 46.8 % PMID[20013877]
NPT15793 ORGANISM Leptosphaeria biglobosa Leptosphaeria biglobosa Inhibition = 15.0 % PMID[20013877]
NPT4113 Organism Leptosphaeria maculans Leptosphaeria maculans Inhibition > 80.0 % PMID[20013877]
NPT15793 ORGANISM Leptosphaeria biglobosa Leptosphaeria biglobosa Activity = 94.0 % PMID[20013877]
NPT4113 Organism Leptosphaeria maculans Leptosphaeria maculans Activity = 96.0 % PMID[20013877]
NPT3594 Organism Galactomyces geotrichum Galactomyces geotrichum IZ = 0.0 mm PMID[23601815]
NPT1262 Organism Aspergillus parasiticus Aspergillus parasiticus IZ = 18.0 mm PMID[23601815]
NPT2793 Organism Phytophthora citrophthora Phytophthora citrophthora IZ = 24.5 mm PMID[23601815]
NPT2567 Organism Trichoderma viride Hypocrea rufa IZ = 22.0 mm PMID[23601815]
NPT1278 Organism Fusarium culmorum Fusarium culmorum IZ = 18.0 mm PMID[23601815]

☑ 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 NPC330923 and all remaining natural products in the NPASS database.
●  The right table: Most similar natural products (Tc>=0.56 or Top200).

Similarity Score Similarity Level Natural Product ID

  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 NPC330923 and all drugs/candidates.
●  The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

Similarity Score Similarity Level Drug ID Developmental Stage

  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