Structure

Physi-Chem Properties

Molecular Weight:  301.17
Volume:  312.48
LogP:  2.8
LogD:  2.76
LogS:  -2.143
# Rotatable Bonds:  2
TPSA:  41.93
# H-Bond Aceptor:  4
# H-Bond Donor:  1
# Rings:  4
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.853
Synthetic Accessibility Score:  4.371
Fsp3:  0.556
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:  -4.677
MDCK Permeability:  1.3596903954748996e-05
Pgp-inhibitor:  0.035
Pgp-substrate:  0.985
Human Intestinal Absorption (HIA):  0.004
20% Bioavailability (F20%):  0.891
30% Bioavailability (F30%):  0.029

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.995
Plasma Protein Binding (PPB):  57.029136657714844%
Volume Distribution (VD):  3.183
Pgp-substrate:  35.3118896484375%

ADMET: Metabolism

CYP1A2-inhibitor:  0.033
CYP1A2-substrate:  0.607
CYP2C19-inhibitor:  0.048
CYP2C19-substrate:  0.918
CYP2C9-inhibitor:  0.052
CYP2C9-substrate:  0.549
CYP2D6-inhibitor:  0.29
CYP2D6-substrate:  0.81
CYP3A4-inhibitor:  0.327
CYP3A4-substrate:  0.908

ADMET: Excretion

Clearance (CL):  14.655
Half-life (T1/2):  0.568

ADMET: Toxicity

hERG Blockers:  0.039
Human Hepatotoxicity (H-HT):  0.312
Drug-inuced Liver Injury (DILI):  0.058
AMES Toxicity:  0.584
Rat Oral Acute Toxicity:  0.431
Maximum Recommended Daily Dose:  0.947
Skin Sensitization:  0.066
Carcinogencity:  0.943
Eye Corrosion:  0.004
Eye Irritation:  0.017
Respiratory Toxicity:  0.952

Download Data

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

  Natural Product: NPC179597

Natural Product ID:  NPC179597
Common Name*:   RDXIEGVPUDECJS-KSSFIOAISA-N
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  RDXIEGVPUDECJS-KSSFIOAISA-N
Standard InCHI:  InChI=1S/C18H23NO3/c1-21-14-4-3-12-5-7-19-8-6-15-16(18(12,19)11-14)9-13(20)10-17(15)22-2/h3,9-10,14,20H,4-8,11H2,1-2H3/t14-,18-/m0/s1
SMILES:  CO[C@H]1CC=C2CCN3CCc4c(cc(cc4OC)O)[C@]23C1
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   n.a.
PubChem CID:   n.a.
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000279] Alkaloids and derivatives
      • [CHEMONTID:0001782] Erythrina alkaloids
        • [CHEMONTID:0002780] Erythrinanes

*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
NPO1698 Glycyrrhiza inflata Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[21123068]
NPO1698 Glycyrrhiza inflata Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[28522265]
NPO1698 Glycyrrhiza inflata Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[29641206]
NPO4824 Cocculus trilobus Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO96 Rhododendron capitatum Species Ericaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO1698 Glycyrrhiza inflata Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO23450 Chionographis japonica Species Melanthiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO23450 Chionographis japonica Species Melanthiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO5156 Hypoestes rosea Species Acanthaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7389 Rhodiola atuntsuensis Species Crassulaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO1698 Glycyrrhiza inflata Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO4824 Cocculus trilobus Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO96 Rhododendron capitatum Species Ericaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO4824 Cocculus trilobus Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO96 Rhododendron capitatum Species Ericaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO1698 Glycyrrhiza inflata Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO1698 Glycyrrhiza inflata Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO6730 Crossopteryx febrifuga Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4824 Cocculus trilobus Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23450 Chionographis japonica Species Melanthiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24372 Artemisia palustris Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19931 Pyrus x nivalis Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1516 Passiflora suberosa Species Passifloraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5156 Hypoestes rosea Species Acanthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1698 Glycyrrhiza inflata Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7389 Rhodiola atuntsuensis Species Crassulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO96 Rhododendron capitatum Species Ericaceae 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 NPC179597 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 NPC179597 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