Structure

Physi-Chem Properties

Molecular Weight:  264.14
Volume:  263.658
LogP:  1.759
LogD:  1.466
LogS:  -4.064
# Rotatable Bonds:  0
TPSA:  63.6
# H-Bond Aceptor:  4
# H-Bond Donor:  1
# Rings:  5
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.665
Synthetic Accessibility Score:  6.588
Fsp3:  0.867
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  1
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.355
MDCK Permeability:  1.85357694135746e-05
Pgp-inhibitor:  0.004
Pgp-substrate:  0.069
Human Intestinal Absorption (HIA):  0.011
20% Bioavailability (F20%):  0.006
30% Bioavailability (F30%):  0.935

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.972
Plasma Protein Binding (PPB):  62.052249908447266%
Volume Distribution (VD):  0.842
Pgp-substrate:  48.12875747680664%

ADMET: Metabolism

CYP1A2-inhibitor:  0.018
CYP1A2-substrate:  0.983
CYP2C19-inhibitor:  0.023
CYP2C19-substrate:  0.848
CYP2C9-inhibitor:  0.018
CYP2C9-substrate:  0.029
CYP2D6-inhibitor:  0.002
CYP2D6-substrate:  0.117
CYP3A4-inhibitor:  0.054
CYP3A4-substrate:  0.919

ADMET: Excretion

Clearance (CL):  6.836
Half-life (T1/2):  0.279

ADMET: Toxicity

hERG Blockers:  0.009
Human Hepatotoxicity (H-HT):  0.368
Drug-inuced Liver Injury (DILI):  0.747
AMES Toxicity:  0.867
Rat Oral Acute Toxicity:  0.973
Maximum Recommended Daily Dose:  0.171
Skin Sensitization:  0.06
Carcinogencity:  0.966
Eye Corrosion:  0.09
Eye Irritation:  0.149
Respiratory Toxicity:  0.976

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

  Natural Product: NPC129938

Natural Product ID:  NPC129938
Common Name*:   JXHZYOVPJZOQIF-NQJPVCRJSA-N
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  JXHZYOVPJZOQIF-NQJPVCRJSA-N
Standard InCHI:  InChI=1S/C15H20O4/c1-8-4-5-14(18)12(3)7-19-15(11(17)9(12)2)10(16)6-13(8,14)15/h8-9,18H,4-7H2,1-3H3/t8-,9?,12-,13+,14?,15?/m1/s1
SMILES:  C[C@@H]1CCC2([C@]3(C)COC4(C(=O)C[C@]124)C(=O)C3C)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   n.a.
PubChem CID:   6852268
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001549] Monoterpenoids
          • [CHEMONTID:0001565] Iridoids 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
NPO1576 Anthriscus sylvestris Species Apiaceae Eukaryota n.a. root n.a. PMID[10230514]
NPO9140 Illicium minwanense Species Schisandraceae Eukaryota n.a. n.a. n.a. PMID[12828465]
NPO1576 Anthriscus sylvestris Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[12956064]
NPO1576 Anthriscus sylvestris Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[25608854]
NPO3925 Bursera microphylla Species Burseraceae Eukaryota Resin Baha de Kino 2013-JAN PMID[25966052]
NPO3925 Bursera microphylla Species Burseraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO20275.1 Juniperus sabina var. tamariscifolia Varieties Cupressaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO9140 Illicium minwanense Species Schisandraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO1576 Anthriscus sylvestris Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO20275 Juniperus sabina Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO19042 Illicium henryi Species Schisandraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO3403 Juniperus silicicola Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO27244 Dysosma pleiantha Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO3925 Bursera microphylla Species Burseraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO1576 Anthriscus sylvestris Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO9140 Illicium minwanense Species Schisandraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO3403 Juniperus silicicola Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO20275.1 Juniperus sabina var. tamariscifolia Varieties Cupressaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7609 Thujopsis dolabrata Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO27244 Dysosma pleiantha Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO19042 Illicium henryi Species Schisandraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO20275 Juniperus sabina Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO20275 Juniperus sabina Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO9140 Illicium minwanense Species Schisandraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO7609 Thujopsis dolabrata Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3925 Bursera microphylla Species Burseraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3403 Juniperus silicicola Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20275 Juniperus sabina Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27244 Dysosma pleiantha Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1576 Anthriscus sylvestris Species Apiaceae 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 NPC129938 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 NPC129938 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