Structure

Physi-Chem Properties

Molecular Weight:  273.22
Volume:  302.0
LogP:  3.345
LogD:  3.504
LogS:  -3.22
# Rotatable Bonds:  4
TPSA:  50.74
# H-Bond Aceptor:  3
# H-Bond Donor:  2
# Rings:  3
# Heavy Atoms:  3

MedChem Properties

QED Drug-Likeness Score:  0.782
Synthetic Accessibility Score:  4.749
Fsp3:  0.765
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
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:  -4.752
MDCK Permeability:  1.9037574020330794e-05
Pgp-inhibitor:  0.093
Pgp-substrate:  0.891
Human Intestinal Absorption (HIA):  0.02
20% Bioavailability (F20%):  0.967
30% Bioavailability (F30%):  0.274

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.818
Plasma Protein Binding (PPB):  61.17013931274414%
Volume Distribution (VD):  1.859
Pgp-substrate:  24.728471755981445%

ADMET: Metabolism

CYP1A2-inhibitor:  0.092
CYP1A2-substrate:  0.16
CYP2C19-inhibitor:  0.021
CYP2C19-substrate:  0.82
CYP2C9-inhibitor:  0.017
CYP2C9-substrate:  0.099
CYP2D6-inhibitor:  0.279
CYP2D6-substrate:  0.882
CYP3A4-inhibitor:  0.464
CYP3A4-substrate:  0.285

ADMET: Excretion

Clearance (CL):  8.902
Half-life (T1/2):  0.592

ADMET: Toxicity

hERG Blockers:  0.364
Human Hepatotoxicity (H-HT):  0.773
Drug-inuced Liver Injury (DILI):  0.655
AMES Toxicity:  0.083
Rat Oral Acute Toxicity:  0.933
Maximum Recommended Daily Dose:  0.373
Skin Sensitization:  0.782
Carcinogencity:  0.729
Eye Corrosion:  0.004
Eye Irritation:  0.042
Respiratory Toxicity:  0.933

Download Data

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

  Natural Product: NPC471867

Natural Product ID:  NPC471867
Common Name*:   CBLDAFLGMLRBJJ-BEKUSENUSA-N
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  CBLDAFLGMLRBJJ-BEKUSENUSA-N
Standard InCHI:  InChI=1S/C17H27N3/c1-3-4-5-6-7-13-11(2)10-12-8-9-14-15(12)16(13)20-17(18)19-14/h5-6,11-12,14-15H,3-4,7-10H2,1-2H3,(H3,18,19,20)/b6-5-/t11-,12+,14+,15-/m1/s1
SMILES:  CCCC=CCC1=C2C3C(CCC3N=C(N2)N)CC1C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL3261946
PubChem CID:   90676179
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0004788] Diazanaphthalenes
        • [CHEMONTID:0004789] Benzodiazines
          • [CHEMONTID:0000485] Quinazolines

*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
NPO21865 Biemna laboutei Species Biemnidae Eukaryota n.a. n.a. n.a. PMID[24601655]
NPO21865 Biemna laboutei Species Biemnidae 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
NPT91 Cell Line KB Homo sapiens IC50 = 1000.0 nM PMID[558781]

☑ 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 NPC471867 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
0.9359 High Similarity NPC57599
0.7303 Intermediate Similarity NPC471868
0.7079 Intermediate Similarity NPC12035
0.7011 Intermediate Similarity NPC174803
0.7011 Intermediate Similarity NPC259989
0.679 Remote Similarity NPC472544
0.6707 Remote Similarity NPC325268
0.663 Remote Similarity NPC329782
0.663 Remote Similarity NPC474122
0.663 Remote Similarity NPC118329
0.663 Remote Similarity NPC152039
0.6559 Remote Similarity NPC472312
0.6526 Remote Similarity NPC24733
0.6413 Remote Similarity NPC211322
0.6364 Remote Similarity NPC21773
0.6316 Remote Similarity NPC171639
0.625 Remote Similarity NPC472543
0.6222 Remote Similarity NPC476904
0.6211 Remote Similarity NPC283277
0.618 Remote Similarity NPC265789
0.6154 Remote Similarity NPC125828
0.6146 Remote Similarity NPC161344
0.6087 Remote Similarity NPC7214
0.596 Remote Similarity NPC56107
0.5904 Remote Similarity NPC231129
0.5849 Remote Similarity NPC474164
0.5833 Remote Similarity NPC82919
0.5823 Remote Similarity NPC153280
0.5747 Remote Similarity NPC476559
0.5728 Remote Similarity NPC84171
0.5714 Remote Similarity NPC215474
0.5714 Remote Similarity NPC472830
0.5714 Remote Similarity NPC472735
0.5701 Remote Similarity NPC167419
0.5698 Remote Similarity NPC219621
0.5657 Remote Similarity NPC21667
0.5636 Remote Similarity NPC176012
0.5636 Remote Similarity NPC58200
0.5631 Remote Similarity NPC304455
0.5618 Remote Similarity NPC37792
0.5614 Remote Similarity NPC175585

  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 NPC471867 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
0.6022 Remote Similarity NPD1426 Clinical (unspecified phase)
0.602 Remote Similarity NPD1353 Suspended
0.6 Remote Similarity NPD5365 Phase 2

  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