Structure

Physi-Chem Properties

Molecular Weight:  296.27
Volume:  349.488
LogP:  6.656
LogD:  4.519
LogS:  -4.326
# Rotatable Bonds:  16
TPSA:  26.3
# H-Bond Aceptor:  2
# H-Bond Donor:  0
# Rings:  0
# Heavy Atoms:  2

MedChem Properties

QED Drug-Likeness Score:  0.204
Synthetic Accessibility Score:  2.068
Fsp3:  0.842
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Rejected
BMS Rule:  1
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.824
MDCK Permeability:  2.5359515348100103e-05
Pgp-inhibitor:  0.002
Pgp-substrate:  0.001
Human Intestinal Absorption (HIA):  0.02
20% Bioavailability (F20%):  0.989
30% Bioavailability (F30%):  0.995

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.461
Plasma Protein Binding (PPB):  98.07112884521484%
Volume Distribution (VD):  2.937
Pgp-substrate:  1.5030455589294434%

ADMET: Metabolism

CYP1A2-inhibitor:  0.436
CYP1A2-substrate:  0.245
CYP2C19-inhibitor:  0.42
CYP2C19-substrate:  0.102
CYP2C9-inhibitor:  0.258
CYP2C9-substrate:  0.946
CYP2D6-inhibitor:  0.427
CYP2D6-substrate:  0.314
CYP3A4-inhibitor:  0.609
CYP3A4-substrate:  0.084

ADMET: Excretion

Clearance (CL):  4.635
Half-life (T1/2):  0.765

ADMET: Toxicity

hERG Blockers:  0.324
Human Hepatotoxicity (H-HT):  0.046
Drug-inuced Liver Injury (DILI):  0.058
AMES Toxicity:  0.02
Rat Oral Acute Toxicity:  0.035
Maximum Recommended Daily Dose:  0.034
Skin Sensitization:  0.962
Carcinogencity:  0.085
Eye Corrosion:  0.815
Eye Irritation:  0.881
Respiratory Toxicity:  0.905

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

  Natural Product: NPC163297

Natural Product ID:  NPC163297
Common Name*:   QRTVDKVXAFJVRU-YPKPFQOOSA-N
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  QRTVDKVXAFJVRU-YPKPFQOOSA-N
Standard InCHI:  InChI=1S/C19H36O2/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19(20)21-2/h13-14H,3-12,15-18H2,1-2H3/b14-13-
SMILES:  CCCCCCCCCCC/C=CCCCCC(=O)OC
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   n.a.
PubChem CID:   5362717
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0003909] Fatty Acyls
        • [CHEMONTID:0000324] Fatty acid esters
          • [CHEMONTID:0003417] Fatty acid methyl 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
NPO5954 Petroselinum crispum Species Apiaceae Eukaryota n.a. callus n.a. PMID[10552648]
NPO26919 Sanguisorba officinalis Species Rosaceae Eukaryota n.a. n.a. n.a. PMID[11520216]
NPO12078 Teclea nobilis Species Rutaceae Eukaryota n.a. n.a. n.a. PMID[12350171]
NPO27036 Xenia blumi Species Xeniidae Eukaryota n.a. Green Island, Taiwan 2002-MAY PMID[16180809]
NPO157 Convallaria majalis Species Asparagaceae Eukaryota n.a. rhizome n.a. PMID[17268112]
NPO6365 Pachychalina alcaloidifera Species Niphatidae Eukaryota n.a. Brazilian n.a. PMID[17346073]
NPO5954 Petroselinum crispum Species Apiaceae Eukaryota n.a. leaf n.a. PMID[18214349]
NPO5227 Lawsonia inermis Species Lythraceae Eukaryota leaves n.a. n.a. PMID[20634065]
NPO5954 Petroselinum crispum Species Apiaceae Eukaryota n.a. seed n.a. PMID[21049975]
NPO5954 Petroselinum crispum Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[21800857]
NPO6749 Bergenia crassifolia Species Saxifragaceae Eukaryota n.a. leaf n.a. PMID[24895781]
NPO5227 Lawsonia inermis Species Lythraceae Eukaryota flower buds n.a. n.a. PMID[25987378]
NPO157 Convallaria majalis Species Asparagaceae Eukaryota n.a. aerial part n.a. PMID[6893493]
NPO157 Convallaria majalis Species Asparagaceae Eukaryota n.a. rhizome n.a. PMID[6893493]
NPO5954 Petroselinum crispum Species Apiaceae Eukaryota n.a. n.a. Database[FooDB]
NPO25198 Octopus vulgaris Species Octopodidae Eukaryota n.a. n.a. Database[FooDB]
NPO5954 Petroselinum crispum Species Apiaceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO5954 Petroselinum crispum Species Apiaceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO5954 Petroselinum crispum Species Apiaceae Eukaryota Plant n.a. n.a. Database[FooDB]
NPO5954 Petroselinum crispum Species Apiaceae Eukaryota Root n.a. n.a. Database[FooDB]
NPO5954 Petroselinum crispum Species Apiaceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO5954 Petroselinum crispum Species Apiaceae Eukaryota Shoot n.a. n.a. Database[FooDB]
NPO25198 Octopus vulgaris Species Octopodidae Eukaryota n.a. n.a. Database[FooDB]
NPO5954 Petroselinum crispum Species Apiaceae Eukaryota n.a. n.a. Database[FooDB]
NPO26919 Sanguisorba officinalis Species Rosaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO25198 Octopus vulgaris Species Octopodidae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO5954 Petroselinum crispum Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO6749 Bergenia crassifolia Species Saxifragaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO5227 Lawsonia inermis Species Lythraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO5954 Petroselinum crispum Species Apiaceae Eukaryota n.a. n.a. Database[Phenol-Explorer]
NPO6749 Bergenia crassifolia Species Saxifragaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO12078 Teclea nobilis Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO5954 Petroselinum crispum Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25198 Octopus vulgaris Species Octopodidae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO5227 Lawsonia inermis Species Lythraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO26919 Sanguisorba officinalis Species Rosaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO26919 Sanguisorba officinalis Species Rosaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO5954 Petroselinum crispum Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO26919 Sanguisorba officinalis Species Rosaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO1068 Platytaenia lasiocarpa n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO21533 Smilax bracteata Species Smilacaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2352 Tynanthus panurensis Species Bignoniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO832 Pseudocinchona pachyceras Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25123 Scutellaria sieberi Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27036 Xenia blumi Species Xeniidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO157 Convallaria majalis Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1420 Tenebrio obscurus Species Tenebrionidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26056 Atroxima liberica Species Polygalaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25198 Octopus vulgaris Species Octopodidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26919 Sanguisorba officinalis Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5227 Lawsonia inermis Species Lythraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26387 Linum crispum Species Linaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8830 Crotalaria orixensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12078 Teclea nobilis Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6365 Pachychalina alcaloidifera Species Niphatidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8710 Licaria brasiliensis Species Lauraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25071 Aspergillus albus Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5954 Petroselinum crispum Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25444 Christisonia bicolor Species Orobanchaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6749 Bergenia crassifolia Species Saxifragaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1763 Rabdosia angustifolia Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26501 Palafoxia texana Species Asteraceae 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 NPC163297 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 NPC163297 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