Structure

Physi-Chem Properties

Molecular Weight:  244.07
Volume:  250.293
LogP:  3.682
LogD:  3.366
LogS:  -3.111
# Rotatable Bonds:  4
TPSA:  66.76
# H-Bond Aceptor:  4
# H-Bond Donor:  2
# Rings:  2
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.814
Synthetic Accessibility Score:  1.763
Fsp3:  0.071
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:  -4.744
MDCK Permeability:  2.811887679854408e-05
Pgp-inhibitor:  0.004
Pgp-substrate:  0.0
Human Intestinal Absorption (HIA):  0.017
20% Bioavailability (F20%):  0.655
30% Bioavailability (F30%):  0.957

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.593
Plasma Protein Binding (PPB):  97.89193725585938%
Volume Distribution (VD):  0.693
Pgp-substrate:  2.5147926807403564%

ADMET: Metabolism

CYP1A2-inhibitor:  0.984
CYP1A2-substrate:  0.127
CYP2C19-inhibitor:  0.905
CYP2C19-substrate:  0.068
CYP2C9-inhibitor:  0.75
CYP2C9-substrate:  0.555
CYP2D6-inhibitor:  0.934
CYP2D6-substrate:  0.375
CYP3A4-inhibitor:  0.4
CYP3A4-substrate:  0.182

ADMET: Excretion

Clearance (CL):  13.572
Half-life (T1/2):  0.853

ADMET: Toxicity

hERG Blockers:  0.025
Human Hepatotoxicity (H-HT):  0.029
Drug-inuced Liver Injury (DILI):  0.789
AMES Toxicity:  0.259
Rat Oral Acute Toxicity:  0.026
Maximum Recommended Daily Dose:  0.009
Skin Sensitization:  0.82
Carcinogencity:  0.512
Eye Corrosion:  0.235
Eye Irritation:  0.988
Respiratory Toxicity:  0.072

Download Data

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

  Natural Product: NPC16737

Natural Product ID:  NPC16737
Common Name*:   UONCJNZKQVIGHS-UHFFFAOYSA-N
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  UONCJNZKQVIGHS-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C14H12O4/c15-11-7-4-8-12(16)13(11)14(17)18-9-10-5-2-1-3-6-10/h1-8,15-16H,9H2
SMILES:  c1ccc(cc1)COC(=O)c1c(cccc1O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   n.a.
PubChem CID:   10586364
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0002448] Benzenoids
      • [CHEMONTID:0002279] Benzene and substituted derivatives
        • [CHEMONTID:0000176] Benzoic acids and derivatives
          • [CHEMONTID:0001350] Benzoic acid esters
            • [CHEMONTID:0004700] o-Hydroxybenzoic acid esters

*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
NPO14260 Euphorbia kansui Species Euphorbiaceae Eukaryota roots n.a. n.a. PMID[12350140]
NPO14260 Euphorbia kansui Species Euphorbiaceae Eukaryota Roots n.a. n.a. PMID[12762796]
NPO12181 Albizia julibrissin Species Fabaceae Eukaryota n.a. bark n.a. PMID[15283458]
NPO14260 Euphorbia kansui Species Euphorbiaceae Eukaryota n.a. n.a. n.a. PMID[15387657]
NPO12181 Albizia julibrissin Species Fabaceae Eukaryota n.a. stem n.a. PMID[15577257]
NPO14260 Euphorbia kansui Species Euphorbiaceae Eukaryota n.a. root n.a. PMID[1955882]
NPO8896 Anacardium occidentale Species Anacardiaceae Eukaryota Fruits n.a. n.a. PMID[8021657]
NPO12181 Albizia julibrissin Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[9051910]
NPO13274 Illicium verum Species Schisandraceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO13274 Illicium verum Species Schisandraceae Eukaryota n.a. n.a. Database[FooDB]
NPO8896 Anacardium occidentale Species Anacardiaceae Eukaryota n.a. n.a. Database[FooDB]
NPO8896 Anacardium occidentale Species Anacardiaceae Eukaryota n.a. n.a. Database[FooDB]
NPO8896 Anacardium occidentale Species Anacardiaceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO13274 Illicium verum Species Schisandraceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO8896 Anacardium occidentale Species Anacardiaceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO13274 Illicium verum Species Schisandraceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO8896 Anacardium occidentale Species Anacardiaceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO5911 Anchusa officinalis Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO12693 Mesembryanthemum tortuosum Species Aizoaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO8896 Anacardium occidentale Species Anacardiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO13274 Illicium verum Species Schisandraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO14260 Euphorbia kansui Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO13274 Illicium verum Species Schisandraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO12693 Mesembryanthemum tortuosum Species Aizoaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO5911 Anchusa officinalis Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14260 Euphorbia kansui Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO8896 Anacardium occidentale Species Anacardiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO12181 Albizia julibrissin Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO12181 Albizia julibrissin Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO14260 Euphorbia kansui Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO8896 Anacardium occidentale Species Anacardiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO13274 Illicium verum Species Schisandraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO12181 Albizia julibrissin Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO14260 Euphorbia kansui Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO13274 Illicium verum Species Schisandraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO13970 Caryopteris mongholica Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14260 Euphorbia kansui Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10551 Acanthopanax ricinifolius n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO14465 Ramalina terebrata Species Ramalinaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12693 Mesembryanthemum tortuosum Species Aizoaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18379 Satureja atropatana Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16137 Mappia foetida Species Icacinaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8896 Anacardium occidentale Species Anacardiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16626 Leucetta microrhaphis Species Leucettidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7027 Metapenaeus macleayi Species Penaeidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6519 Calocera viscosa Species Dacrymycetaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12181 Albizia julibrissin Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20056 Pinus monophylla Species Pinaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13368 Monomorium delagoense Species Formicidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10773 Dalbergia rubiginosa Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13274 Illicium verum Species Schisandraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5911 Anchusa officinalis Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20274 Cynanchum formosanum Species Apocynaceae 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 NPC16737 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 NPC16737 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