Structure

Physi-Chem Properties

Molecular Weight:  328.17
Volume:  354.069
LogP:  4.196
LogD:  3.473
LogS:  -4.29
# Rotatable Bonds:  7
TPSA:  59.67
# H-Bond Aceptor:  4
# H-Bond Donor:  1
# Rings:  2
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.613
Synthetic Accessibility Score:  2.849
Fsp3:  0.35
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.77
MDCK Permeability:  2.1133999325684272e-05
Pgp-inhibitor:  0.081
Pgp-substrate:  0.092
Human Intestinal Absorption (HIA):  0.018
20% Bioavailability (F20%):  0.402
30% Bioavailability (F30%):  0.99

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.045
Plasma Protein Binding (PPB):  93.78437805175781%
Volume Distribution (VD):  0.509
Pgp-substrate:  3.8078150749206543%

ADMET: Metabolism

CYP1A2-inhibitor:  0.965
CYP1A2-substrate:  0.705
CYP2C19-inhibitor:  0.867
CYP2C19-substrate:  0.116
CYP2C9-inhibitor:  0.774
CYP2C9-substrate:  0.826
CYP2D6-inhibitor:  0.669
CYP2D6-substrate:  0.74
CYP3A4-inhibitor:  0.613
CYP3A4-substrate:  0.214

ADMET: Excretion

Clearance (CL):  11.937
Half-life (T1/2):  0.587

ADMET: Toxicity

hERG Blockers:  0.034
Human Hepatotoxicity (H-HT):  0.904
Drug-inuced Liver Injury (DILI):  0.451
AMES Toxicity:  0.048
Rat Oral Acute Toxicity:  0.01
Maximum Recommended Daily Dose:  0.461
Skin Sensitization:  0.922
Carcinogencity:  0.374
Eye Corrosion:  0.006
Eye Irritation:  0.934
Respiratory Toxicity:  0.178

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

  Natural Product: NPC153171

Natural Product ID:  NPC153171
Common Name*:   HUMPYOCQOJFKOK-MHWRWJLKSA-N
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  HUMPYOCQOJFKOK-MHWRWJLKSA-N
Standard InCHI:  InChI=1S/C20H24O4/c1-14(2)6-4-8-16(13-21)10-11-23-18-12-19(22)24-17-9-5-7-15(3)20(17)18/h5-7,9-10,12,21H,4,8,11,13H2,1-3H3/b16-10+
SMILES:  CC(=CCC/C(=CCOc1cc(=O)oc2cccc(C)c12)/CO)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   n.a.
PubChem CID:   n.a.
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001283] Terpene lactones

*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
NPO11874 Ambrosia hispida Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO14802.1 Lonicera tatarica var. morrowii Varieties Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11874 Ambrosia hispida Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11874 Ambrosia hispida Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10034 Penstemon mucronatus Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14802.1 Lonicera tatarica var. morrowii Varieties Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6008 Cacalia pilgeriana Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1545 Baeckea crenulata Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6402 Sideritis kuegleriana Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10637 Byssochlamys fulva Species Thermoascaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2544 Stemona saxorum Species Stemonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8742 Hamamelistes betulae Species Hormaphididae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12264 Mutisia orbignyana Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12388 Saccharopolyspora hirsuta Species Pseudonocardiaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO3661 Goniothalamus tamirensis Species Annonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12606 Achillea spinulifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7743 Helicoverpa zea Species 0ctuidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9256 Lecanora nipponica Species Lecanoraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12491 Astragalus onobrychis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10302 Sphagnum rubellum Species Sphagnaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12036 Fritillaria raddeana Species Liliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11695 Petasites hybridus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1965 Alnus incana Species Betulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5668 Allium waldsteinii Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7387 Aster batangensis 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 NPC153171 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 NPC153171 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