Structure

Physi-Chem Properties

Molecular Weight:  354.39
Volume:  432.45
LogP:  10.31
LogD:  4.371
LogS:  -7.2
# Rotatable Bonds:  22
TPSA:  20.23
# H-Bond Aceptor:  1
# H-Bond Donor:  1
# Rings:  0
# Heavy Atoms:  1

MedChem Properties

QED Drug-Likeness Score:  0.193
Synthetic Accessibility Score:  1.478
Fsp3:  1.0
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:  -5.166
MDCK Permeability:  5.843654435011558e-06
Pgp-inhibitor:  0.0
Pgp-substrate:  0.001
Human Intestinal Absorption (HIA):  0.004
20% Bioavailability (F20%):  0.06
30% Bioavailability (F30%):  0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.01
Plasma Protein Binding (PPB):  97.68862915039062%
Volume Distribution (VD):  3.94
Pgp-substrate:  1.2042664289474487%

ADMET: Metabolism

CYP1A2-inhibitor:  0.076
CYP1A2-substrate:  0.151
CYP2C19-inhibitor:  0.15
CYP2C19-substrate:  0.047
CYP2C9-inhibitor:  0.039
CYP2C9-substrate:  0.964
CYP2D6-inhibitor:  0.12
CYP2D6-substrate:  0.021
CYP3A4-inhibitor:  0.152
CYP3A4-substrate:  0.018

ADMET: Excretion

Clearance (CL):  5.003
Half-life (T1/2):  0.035

ADMET: Toxicity

hERG Blockers:  0.409
Human Hepatotoxicity (H-HT):  0.007
Drug-inuced Liver Injury (DILI):  0.161
AMES Toxicity:  0.007
Rat Oral Acute Toxicity:  0.01
Maximum Recommended Daily Dose:  0.016
Skin Sensitization:  0.973
Carcinogencity:  0.024
Eye Corrosion:  0.995
Eye Irritation:  0.917
Respiratory Toxicity:  0.43

Download Data

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

  Natural Product: NPC161917

Natural Product ID:  NPC161917
Common Name*:   TYWMIZZBOVGFOV-UHFFFAOYSA-N
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  TYWMIZZBOVGFOV-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C24H50O/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-24-25/h25H,2-24H2,1H3
SMILES:  CCCCCCCCCCCCCCCCCCCCCCCCO
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   n.a.
PubChem CID:   10472
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0003909] Fatty Acyls
        • [CHEMONTID:0001334] Fatty alcohols

*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
NPO18932 Melia azedarach Species Meliaceae Eukaryota n.a. Brazilian n.a. PMID[15387656]
NPO18932 Melia azedarach Species Meliaceae Eukaryota n.a. ripe fruit n.a. PMID[16205005]
NPO4435 Brunfelsia grandiflora Species Solanaceae Eukaryota n.a. leaf n.a. PMID[18175984]
NPO9585 Oenothera biennis Species Onagraceae Eukaryota Seeds Yichun, Heilongjiang Province, China 2018-Sep PMID[31292343]
NPO18932 Melia azedarach Species Meliaceae Eukaryota Fruits n.a. n.a. PMID[33253570]
NPO18932 Melia azedarach Species Meliaceae Eukaryota Seeds n.a. n.a. PMID[3701342]
NPO9585 Oenothera biennis Species Onagraceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO9585 Oenothera biennis Species Onagraceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO18932 Melia azedarach Species Meliaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO7132 Smilax glabra Species Smilacaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO4789 Adiantum caudatum Species Pteridaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO18641 Radix euphorbiae pekinensis Species Lymnaeidae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO4095 Hedysarum multijugum Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO18932.1 Melia azedarach var. toosendan Varieties Meliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7132 Smilax glabra Species Smilacaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO18932 Melia azedarach Species Meliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO18932 Melia azedarach Species Meliaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO4789 Adiantum caudatum Species Pteridaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO7132 Smilax glabra Species Smilacaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO18932.1 Melia azedarach var. toosendan Varieties Meliaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO18932 Melia azedarach Species Meliaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO7132 Smilax glabra Species Smilacaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO24257 Asphodeline lutea Species Xanthorrhoeaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6815 Streptomyces sclerotialus Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO26126 'prosuberites' laughlini Species Suberitidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18873.1 Salmonella enterica subsp. enterica serovar anatum Subspecies Enterobacteriaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO20177 Verbesina luetzelburgii Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4435 Brunfelsia grandiflora Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3052 Shorea resina-nigra Species Dipterocarpaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7893 Xanthoparmelia camtschadalis Species Parmeliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4789 Adiantum caudatum Species Pteridaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9585 Oenothera biennis Species Onagraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4095 Hedysarum multijugum Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8037 Bryum rutilans Species Bryaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14349 Aconitum turczaninowii Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14496 Eranthis cilicica Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6429 Phlomis regelii Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18932.1 Melia azedarach var. toosendan Varieties Meliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2790 Anthopleura elegantissima Species Actiniidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7132 Smilax glabra Species Smilacaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10952 Camelina sativa Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11238 Ocotea suaveolens Species Lauraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18275 Struthiopteris amabilis Species Blechnaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18932 Melia azedarach Species Meliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12837 Simsia dombeyana Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6988 Diploschistes cretaceus Species Graphidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14099 Ocotea pretiosa Species Lauraceae 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
NPO42044 NPC161917 n.a. Leaves 5 n.a. n.a. mg/g of DW PMID[35056798]
NPO42044 NPC161917 n.a. Roots 3 n.a. n.a. mg/g of DW PMID[35056798]
NPO6473 NPC161917 Cold press Seeds 52.96±0.44 n.a. n.a. mg/kg of oil PMID[34645745]
NPO9585 NPC161917 the AOCS method Seeds 454.7 n.a. n.a. mg/kg of oil PMID[31292343]

☑ 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 NPC161917 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 NPC161917 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