Structure

Physi-Chem Properties

Molecular Weight:  242.14
Volume:  259.928
LogP:  1.754
LogD:  1.66
LogS:  -2.297
# Rotatable Bonds:  0
TPSA:  58.88
# H-Bond Aceptor:  3
# H-Bond Donor:  3
# Rings:  3
# Heavy Atoms:  3

MedChem Properties

QED Drug-Likeness Score:  0.684
Synthetic Accessibility Score:  4.941
Fsp3:  0.4
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:  -5.529
MDCK Permeability:  1.845571750891395e-05
Pgp-inhibitor:  0.0
Pgp-substrate:  0.88
Human Intestinal Absorption (HIA):  0.008
20% Bioavailability (F20%):  0.005
30% Bioavailability (F30%):  0.001

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.021
Plasma Protein Binding (PPB):  76.19424438476562%
Volume Distribution (VD):  1.718
Pgp-substrate:  28.105863571166992%

ADMET: Metabolism

CYP1A2-inhibitor:  0.172
CYP1A2-substrate:  0.678
CYP2C19-inhibitor:  0.206
CYP2C19-substrate:  0.385
CYP2C9-inhibitor:  0.117
CYP2C9-substrate:  0.194
CYP2D6-inhibitor:  0.044
CYP2D6-substrate:  0.183
CYP3A4-inhibitor:  0.327
CYP3A4-substrate:  0.515

ADMET: Excretion

Clearance (CL):  7.987
Half-life (T1/2):  0.515

ADMET: Toxicity

hERG Blockers:  0.034
Human Hepatotoxicity (H-HT):  0.174
Drug-inuced Liver Injury (DILI):  0.077
AMES Toxicity:  0.686
Rat Oral Acute Toxicity:  0.697
Maximum Recommended Daily Dose:  0.928
Skin Sensitization:  0.222
Carcinogencity:  0.856
Eye Corrosion:  0.003
Eye Irritation:  0.01
Respiratory Toxicity:  0.968

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

  Natural Product: NPC482954

Natural Product ID:  NPC482954
Common Name*:   ZRJBHWIHUMBLCN-HZRLMBICSA-N
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  ZRJBHWIHUMBLCN-HZRLMBICSA-N
Standard InCHI:  InChI=1S/C15H18N2O/c1-3-11-10-6-9(2)8-15(11,16)12-4-5-14(18)17-13(12)7-10/h3-6,10H,7-8,16H2,1-2H3,(H,17,18)/b11-3+/t10-,15-/m0/s1
SMILES:  C/C=C/1[C@H]2C=C(C)C[C@]1(c1ccc(nc1C2)O)N
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   n.a.
PubChem CID:   9794806
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0001253] Quinolines and derivatives
        • [CHEMONTID:0000056] Quinolones and derivatives

*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
NPO14928 Huperzia serrata Species Lycopodiaceae Eukaryota n.a. n.a. n.a. PMID[12141864]
NPO14928 Huperzia serrata Species Lycopodiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO14928 Huperzia serrata Species Lycopodiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14928 Huperzia serrata Species Lycopodiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO14928 Huperzia serrata Species Lycopodiaceae 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

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT204 Individual Protein Acetylcholinesterase Homo sapiens IC50 = 5.0 nM DOI[10.1016/0960-894X(96)00337-X]
NPT2749 Individual Protein Acetylcholinesterase Rattus norvegicus IC50 = 80.0 nM PMID[9873409]
NPT2749 Individual Protein Acetylcholinesterase Rattus norvegicus IC50 = 114.0 nM PMID[10476864]
NPT2748 Individual Protein Butyrylcholinesterase Rattus norvegicus IC50 = 135000.0 nM PMID[10476864]
NPT2749 Individual Protein Acetylcholinesterase Rattus norvegicus IC50 = 44.5 nM PMID[1766006]
NPT2749 Individual Protein Acetylcholinesterase Rattus norvegicus IC50 = 80.0 nM PMID[7658452]
NPT2748 Individual Protein Butyrylcholinesterase Rattus norvegicus IC50 > 1000000.0 nM PMID[7658452]
NPT2749 Individual Protein Acetylcholinesterase Rattus norvegicus IC50 = 71.5 nM PMID[1766006]
NPT204 Individual Protein Acetylcholinesterase Homo sapiens IC50 = 47.0 nM PMID[12166941]
NPT439 Individual Protein Butyrylcholinesterase Homo sapiens IC50 > 10000.0 nM PMID[12166941]
NPT439 Individual Protein Butyrylcholinesterase Homo sapiens IC50 > 100000.0 nM PMID[10464010]
NPT2749 Individual Protein Acetylcholinesterase Rattus norvegicus Ki = 24.0 nM PMID[11551765]
NPT204 Individual Protein Acetylcholinesterase Homo sapiens IC50 = 260.0 nM PMID[11101357]
NPT439 Individual Protein Butyrylcholinesterase Homo sapiens IC50 > 10000.0 nM PMID[11101357]
NPT204 Individual Protein Acetylcholinesterase Homo sapiens IC50 = 260.0 nM PMID[11741490]
NPT439 Individual Protein Butyrylcholinesterase Homo sapiens IC50 > 10000.0 nM PMID[11741490]
NPT204 Individual Protein Acetylcholinesterase Homo sapiens Ratio = 0.28 n.a. PMID[11741490]
NPT2749 Individual Protein Acetylcholinesterase Rattus norvegicus IC50 = 94.0 nM DOI[10.1016/0960-894X(96)00102-3]
NPT204 Individual Protein Acetylcholinesterase Homo sapiens IC50 = 150.0 nM DOI[10.1016/0960-894X(96)00102-3]
NPT2749 Individual Protein Acetylcholinesterase Rattus norvegicus IC50 = 72.4 nM PMID[15689148]
NPT2748 Individual Protein Butyrylcholinesterase Rattus norvegicus IC50 = 702000.0 nM PMID[15689148]
NPT204 Individual Protein Acetylcholinesterase Homo sapiens IC50 = 47.0 nM PMID[15715468]
NPT439 Individual Protein Butyrylcholinesterase Homo sapiens IC50 > 10000.0 nM PMID[15715468]
NPT2749 Individual Protein Acetylcholinesterase Rattus norvegicus IC50 = 53.0 nM PMID[15993600]
NPT2748 Individual Protein Butyrylcholinesterase Rattus norvegicus IC50 = 56200.0 nM PMID[15993600]
NPT204 Individual Protein Acetylcholinesterase Homo sapiens IC50 = 260.0 nM PMID[15771413]
NPT439 Individual Protein Butyrylcholinesterase Homo sapiens IC50 > 10000.0 nM PMID[15771413]
NPT204 Individual Protein Acetylcholinesterase Homo sapiens IC50 = 47.0 nM PMID[16570913]
NPT439 Individual Protein Butyrylcholinesterase Homo sapiens IC50 > 10000.0 nM PMID[16570913]
NPT204 Individual Protein Acetylcholinesterase Homo sapiens Ki = 47.0 nM PMID[16722663]
NPT439 Individual Protein Butyrylcholinesterase Homo sapiens Ki > 1000.0 nM PMID[16722663]
NPT204 Individual Protein Acetylcholinesterase Homo sapiens IC50 = 260.0 nM PMID[17154513]
NPT439 Individual Protein Butyrylcholinesterase Homo sapiens IC50 > 10000.0 nM PMID[17154513]
NPT2749 Individual Protein Acetylcholinesterase Rattus norvegicus IC50 = 72.4 nM PMID[17126020]
NPT2748 Individual Protein Butyrylcholinesterase Rattus norvegicus IC50 = 70200.0 nM PMID[17126020]
NPT204 Individual Protein Acetylcholinesterase Homo sapiens Inhibition = 50.0 % PMID[12141864]
NPT2749 Individual Protein Acetylcholinesterase Rattus norvegicus IC50 = 114.0 nM PMID[18479118]
NPT2668 Individual Protein Acetylcholinesterase Torpedo californica Ki = 175.0 nM PMID[18479118]
NPT2668 Individual Protein Acetylcholinesterase Torpedo californica IC50 = 11.4 nM PMID[19726199]
NPT204 Individual Protein Acetylcholinesterase Homo sapiens IC50 = 21.0 nM PMID[19726199]
NPT2668 Individual Protein Acetylcholinesterase Torpedo californica Inhibition = 99.67 % PMID[19726199]
NPT2668 Individual Protein Acetylcholinesterase Torpedo californica Inhibition = 85.7 % PMID[19726199]
NPT2668 Individual Protein Acetylcholinesterase Torpedo californica Inhibition = 81.93 % PMID[19726199]
NPT2668 Individual Protein Acetylcholinesterase Torpedo californica Inhibition = 70.24 % PMID[19726199]
NPT2668 Individual Protein Acetylcholinesterase Torpedo californica Inhibition = 53.35 % PMID[19726199]
NPT2668 Individual Protein Acetylcholinesterase Torpedo californica Inhibition = 34.56 % PMID[19726199]
NPT2668 Individual Protein Acetylcholinesterase Torpedo californica Inhibition = 20.43 % PMID[19726199]
NPT2668 Individual Protein Acetylcholinesterase Torpedo californica Inhibition = 92.97 % PMID[19726199]
NPT204 Individual Protein Acetylcholinesterase Homo sapiens Inhibition = 98.0 % PMID[20797856]
NPT204 Individual Protein Acetylcholinesterase Homo sapiens IC50 = 1700.0 nM PMID[20954721]
NPT204 Individual Protein Acetylcholinesterase Homo sapiens IC50 = 5.0 nM PMID[21216144]
NPT439 Individual Protein Butyrylcholinesterase Homo sapiens IC50 = 100.0 nM PMID[21216144]
NPT66 Individual Protein Acetylcholinesterase Electrophorus electricus IC50 = 120.0 nM PMID[21510637]
NPT204 Individual Protein Acetylcholinesterase Homo sapiens IC50 = 12.0 nM PMID[22775474]
NPT66 Individual Protein Acetylcholinesterase Electrophorus electricus Inhibition = 97.29 % PMID[23062825]
NPT2749 Individual Protein Acetylcholinesterase Rattus norvegicus IC50 = 65.0 nM PMID[23273608]
NPT204 Individual Protein Acetylcholinesterase Homo sapiens IC50 = 45.0 nM PMID[23395652]
NPT204 Individual Protein Acetylcholinesterase Homo sapiens IC50 = 125.0 nM PMID[23941108]
NPT3902 Individual Protein Acetylcholinesterase Mus musculus IC50 = 82.0 nM PMID[23984975]
NPT204 Individual Protein Acetylcholinesterase Homo sapiens Inhibition = 100.0 % PMID[24844448]
NPT204 Individual Protein Acetylcholinesterase Homo sapiens IC50 = 0.54 nM PMID[25222040]
NPT204 Individual Protein Acetylcholinesterase Homo sapiens IC50 = 5.0 nM PMID[26159481]
NPT914 Individual Protein Acetylcholinesterase Bos taurus IC50 = 74.0 nM PMID[10464010]
NPT2 Others Unspecified Ratio > 1000.0 n.a. PMID[10464010]
NPT914 Individual Protein Acetylcholinesterase Bos taurus Ki = 24.0 nM PMID[12031333]
NPT914 Individual Protein Acetylcholinesterase Bos taurus Ki = 5.9 nM DOI[10.1016/0960-894X(96)00012-1]
NPT914 Individual Protein Acetylcholinesterase Bos taurus Ki = 23.6 nM DOI[10.1016/0960-894X(96)00012-1]
NPT914 Individual Protein Acetylcholinesterase Bos taurus Ki = 5.9 nM PMID[11078202]
NPT914 Individual Protein Acetylcholinesterase Bos taurus IC50 = 74.0 nM PMID[11101357]
NPT2 Others Unspecified Ratio = 0.28 n.a. PMID[11101357]
NPT2 Others Unspecified Ratio > 38.0 n.a. PMID[11101357]
NPT914 Individual Protein Acetylcholinesterase Bos taurus IC50 = 74.0 nM PMID[11741490]
NPT3768 Others Cholinesterases; ACHE & BCHE Homo sapiens Ratio > 38.0 n.a. PMID[11741490]
NPT914 Individual Protein Acetylcholinesterase Bos taurus IC50 = 74.0 nM PMID[15771413]
NPT3768 Others Cholinesterases; ACHE & BCHE Homo sapiens Ratio IC50 > 212.0 n.a. PMID[16570913]
NPT914 Individual Protein Acetylcholinesterase Bos taurus IC50 = 74.0 nM PMID[17154513]
NPT2 Others Unspecified Ratio IC50 = 970.0 n.a. PMID[17126020]
NPT914 Individual Protein Acetylcholinesterase Bos taurus IC50 = 53.0 nM PMID[17904850]
NPT914 Individual Protein Acetylcholinesterase Bos taurus IC50 = 74.0 nM PMID[18585045]
NPT67 Individual Protein Cholinesterase Equus caballus Inhibition = 11.85 % PMID[23062825]
NPT19099 ORGANISM Anthrenocerus australis Anthrenocerus australis Activity = 1.5 mg/ml PMID[11804518]
NPT19099 ORGANISM Anthrenocerus australis Anthrenocerus australis Activity = 3.0 % PMID[11804518]
NPT19099 ORGANISM Anthrenocerus australis Anthrenocerus australis LD50 = 110.0 ppm PMID[11804518]
NPT21294 ORGANISM Tineola bisselliella Tineola bisselliella LD50 = 630.0 ppm PMID[11804518]
NPT21294 ORGANISM Tineola bisselliella Tineola bisselliella Activity = 3.0 % PMID[11804518]
NPT5732 Organism Lucilia cuprina Lucilia cuprina Activity = 8.0 % PMID[11804518]
NPT5732 Organism Lucilia cuprina Lucilia cuprina LD50 = 2.38 mg/ml PMID[11804518]
NPT2 Others Unspecified Ratio IC50 = 1138.0 n.a. PMID[23273608]
NPT2 Others Unspecified IC50 = 74000.0 nM PMID[23273608]
NPT73 Individual Protein Solute carrier organic anion transporter family member 1B1 Homo sapiens Inhibition = 93.86 % PMID[23571415]
NPT72 Individual Protein Solute carrier organic anion transporter family member 1B3 Homo sapiens Inhibition = 101.26 % PMID[23571415]

☑ 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 NPC482954 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 NPC482954 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