Structure

Physi-Chem Properties

Molecular Weight:  202.14
Volume:  231.832
LogP:  4.191
LogD:  3.453
LogS:  -3.898
# Rotatable Bonds:  1
TPSA:  20.23
# H-Bond Aceptor:  1
# H-Bond Donor:  1
# Rings:  2
# Heavy Atoms:  1

MedChem Properties

QED Drug-Likeness Score:  0.692
Synthetic Accessibility Score:  3.019
Fsp3:  0.429
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.722
MDCK Permeability:  2.2674310457659885e-05
Pgp-inhibitor:  0.926
Pgp-substrate:  0.005
Human Intestinal Absorption (HIA):  0.003
20% Bioavailability (F20%):  0.913
30% Bioavailability (F30%):  0.023

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.901
Plasma Protein Binding (PPB):  95.08452606201172%
Volume Distribution (VD):  1.714
Pgp-substrate:  5.415775775909424%

ADMET: Metabolism

CYP1A2-inhibitor:  0.899
CYP1A2-substrate:  0.908
CYP2C19-inhibitor:  0.636
CYP2C19-substrate:  0.648
CYP2C9-inhibitor:  0.203
CYP2C9-substrate:  0.88
CYP2D6-inhibitor:  0.726
CYP2D6-substrate:  0.922
CYP3A4-inhibitor:  0.116
CYP3A4-substrate:  0.306

ADMET: Excretion

Clearance (CL):  9.736
Half-life (T1/2):  0.558

ADMET: Toxicity

hERG Blockers:  0.014
Human Hepatotoxicity (H-HT):  0.197
Drug-inuced Liver Injury (DILI):  0.074
AMES Toxicity:  0.052
Rat Oral Acute Toxicity:  0.035
Maximum Recommended Daily Dose:  0.909
Skin Sensitization:  0.574
Carcinogencity:  0.511
Eye Corrosion:  0.834
Eye Irritation:  0.988
Respiratory Toxicity:  0.733

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

  Natural Product: NPC49480

Natural Product ID:  NPC49480
Common Name*:   BVEBOMULMBWPIS-GFCCVEGCSA-N
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  BVEBOMULMBWPIS-GFCCVEGCSA-N
Standard InCHI:  InChI=1S/C14H18O/c1-9(2)12-5-4-11-6-7-14(15)10(3)13(11)8-12/h6-7,12,15H,1,4-5,8H2,2-3H3/t12-/m1/s1
SMILES:  C=C(C)[C@@H]1CCc2ccc(c(C)c2C1)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   n.a.
PubChem CID:   11009001
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0002448] Benzenoids
      • [CHEMONTID:0000048] Tetralins

*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
NPO1315 Sinomenium acutum Species Menispermaceae Eukaryota n.a. n.a. n.a. DOI[10.3987/COM-96-7609.]
NPO403 Gentiana lutea Species Gentianaceae Eukaryota n.a. n.a. n.a. PMID[10705751]
NPO403 Gentiana lutea Species Gentianaceae Eukaryota n.a. seed n.a. PMID[12822897]
NPO1315 Sinomenium acutum Species Menispermaceae Eukaryota n.a. n.a. n.a. PMID[16038566]
NPO1315 Sinomenium acutum Species Menispermaceae Eukaryota n.a. stem n.a. PMID[16964757]
NPO403 Gentiana lutea Species Gentianaceae Eukaryota n.a. root n.a. PMID[18064621]
NPO403 Gentiana lutea Species Gentianaceae Eukaryota n.a. n.a. n.a. PMID[18064621]
NPO1315 Sinomenium acutum Species Menispermaceae Eukaryota n.a. n.a. n.a. PMID[18081254]
NPO1315 Sinomenium acutum Species Menispermaceae Eukaryota n.a. rhizome n.a. PMID[23059629]
NPO403 Gentiana lutea Species Gentianaceae Eukaryota n.a. root n.a. PMID[24257774]
NPO1451 Aspergillus duricaulis Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[26517152]
NPO40189 Ligularia rumicifolia Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[30212198]
NPO403 Gentiana lutea Species Gentianaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO1315 Sinomenium acutum Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO1315 Sinomenium acutum Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO403 Gentiana lutea Species Gentianaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO1315 Sinomenium acutum Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO403 Gentiana lutea Species Gentianaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO403 Gentiana lutea Species Gentianaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO1315 Sinomenium acutum Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO1315 Sinomenium acutum Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3315 Eucalyptus hybr Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2343 Haplopappus arbutoides Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3691 Albizia mollis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10901 Tessaria dodoneaefolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4944 Bactris plumeriana Species Arecaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1380 Phylica rogersii Species Rhamnaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1451 Aspergillus duricaulis Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO403 Gentiana lutea Species Gentianaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18088 Euglena longa Species Euglenaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7529 Viscum multinerve Species Viscaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3817 Chrysosporium queenslandicum Species n.a. Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4851 Penstemon confertus Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4484 Maytenus obtusifolia Species Celastraceae 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

☑ 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 NPC49480 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 NPC49480 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