Structure

Physi-Chem Properties

Molecular Weight:  602.36
Volume:  663.875
LogP:  8.547
LogD:  5.565
LogS:  -4.173
# Rotatable Bonds:  11
TPSA:  108.74
# H-Bond Aceptor:  6
# H-Bond Donor:  2
# Rings:  3
# Heavy Atoms:  6

MedChem Properties

QED Drug-Likeness Score:  0.114
Synthetic Accessibility Score:  5.756
Fsp3:  0.526
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  2
PAINS Alert:  1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.063
MDCK Permeability:  1.3363604921323713e-05
Pgp-inhibitor:  0.119
Pgp-substrate:  0.963
Human Intestinal Absorption (HIA):  0.079
20% Bioavailability (F20%):  0.994
30% Bioavailability (F30%):  0.892

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.021
Plasma Protein Binding (PPB):  98.24397277832031%
Volume Distribution (VD):  2.047
Pgp-substrate:  4.869913101196289%

ADMET: Metabolism

CYP1A2-inhibitor:  0.026
CYP1A2-substrate:  0.19
CYP2C19-inhibitor:  0.845
CYP2C19-substrate:  0.417
CYP2C9-inhibitor:  0.794
CYP2C9-substrate:  0.965
CYP2D6-inhibitor:  0.813
CYP2D6-substrate:  0.049
CYP3A4-inhibitor:  0.898
CYP3A4-substrate:  0.7

ADMET: Excretion

Clearance (CL):  17.005
Half-life (T1/2):  0.092

ADMET: Toxicity

hERG Blockers:  0.003
Human Hepatotoxicity (H-HT):  0.591
Drug-inuced Liver Injury (DILI):  0.915
AMES Toxicity:  0.013
Rat Oral Acute Toxicity:  0.901
Maximum Recommended Daily Dose:  0.932
Skin Sensitization:  0.034
Carcinogencity:  0.531
Eye Corrosion:  0.043
Eye Irritation:  0.544
Respiratory Toxicity:  0.974

Download Data

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

  Natural Product: NPC93556

Natural Product ID:  NPC93556
Common Name*:   QDKLRKZQSOQWJQ-AKAMJVKKSA-N
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  QDKLRKZQSOQWJQ-AKAMJVKKSA-N
Standard InCHI:  InChI=1S/C38H50O6/c1-22(2)11-13-27(25(7)8)20-37-21-28(15-12-23(3)4)36(9,10)38(35(37)44,18-17-24(5)6)34(43)31(33(37)42)32(41)26-14-16-29(39)30(40)19-26/h11-12,14,16-17,19,27-28,39-40,42H,7,13,15,18,20-21H2,1-6,8-10H3/t27-,28+,37+,38-/m1/s1
SMILES:  CC(=CC[C@H](C[C@]12C[C@H](CC=C(C)C)C(C)(C)[C@](CC=C(C)C)(C(=O)C(=C1O)C(=O)c1ccc(c(c1)O)O)C2=O)C(=C)C)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:0001549] Monoterpenoids
          • [CHEMONTID:0001564] Bicyclic monoterpenoids

*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
NPO5638 Garcinia livingstonei Species Clusiaceae Eukaryota n.a. fruit n.a. DOI[10.1016/S0040-4020(01)89039-6]
NPO22214 Theonella swinhoei Species Theonellidae Eukaryota n.a. n.a. n.a. PMID[11421754]
NPO22214 Theonella swinhoei Species Theonellidae Eukaryota n.a. n.a. n.a. PMID[12193024]
NPO22214 Theonella swinhoei Species Theonellidae Eukaryota n.a. Papua New Guinea n.a. PMID[15679329]
NPO22214 Theonella swinhoei Species Theonellidae Eukaryota n.a. Red Sea n.a. PMID[16441091]
NPO5638 Garcinia livingstonei Species Clusiaceae Eukaryota root bark n.a. n.a. PMID[16562837]
NPO22214 Theonella swinhoei Species Theonellidae Eukaryota n.a. n.a. n.a. PMID[17125225]
NPO22214 Theonella swinhoei Species Theonellidae Eukaryota n.a. n.a. n.a. PMID[18318032]
NPO22214 Theonella swinhoei Species Theonellidae Eukaryota n.a. Indonesian n.a. PMID[19961178]
NPO22214 Theonella swinhoei Species Theonellidae Eukaryota n.a. n.a. n.a. PMID[20078073]
NPO22214 Theonella swinhoei Species Theonellidae Eukaryota n.a. palau n.a. PMID[20078073]
NPO30436 Rheedia edulis Species Clusiaceae Eukaryota n.a. exocarp n.a. PMID[21028890]
NPO30436 Rheedia edulis Species Clusiaceae Eukaryota seeds and rinds n.a. n.a. PMID[21028890]
NPO30436 Rheedia edulis Species Clusiaceae Eukaryota n.a. seed n.a. PMID[21028890]
NPO5638 Garcinia livingstonei Species Clusiaceae Eukaryota n.a. fruit n.a. PMID[21028890]
NPO22214 Theonella swinhoei Species Theonellidae Eukaryota n.a. n.a. n.a. PMID[21428459]
NPO22214 Theonella swinhoei Species Theonellidae Eukaryota n.a. n.a. n.a. PMID[23830699]
NPO22214 Theonella swinhoei Species Theonellidae Eukaryota n.a. n.a. n.a. PMID[27213234]
NPO22214 Theonella swinhoei Species Theonellidae Eukaryota n.a. n.a. n.a. PMID[27548648]
NPO22214 Theonella swinhoei Species Theonellidae Eukaryota n.a. n.a. n.a. PMID[29989811]
NPO22214 Theonella swinhoei Species Theonellidae Eukaryota n.a. n.a. n.a. PMID[30346758]
NPO22214 Theonella swinhoei Species Theonellidae Eukaryota n.a. n.a. n.a. PMID[32191460]
NPO3858 Pimpinella magna Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO6556 Garcinia intermedia Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1970 Rubus palmatus Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5638 Garcinia livingstonei Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22214 Theonella swinhoei Species Theonellidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO104 Hymenodictyon floribundum Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4768 Lunaria annua Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3858 Pimpinella magna Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10493 Casearia thwaitesii Species Salicaceae 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
NPT1079 Individual Protein Histone acetyltransferase p300 Homo sapiens IC50 = 500.0 nM PMID[29989811]
NPT1079 Individual Protein Histone acetyltransferase p300 Homo sapiens IC50 = 7000.0 nM PMID[28505447]
NPT1079 Individual Protein Histone acetyltransferase p300 Homo sapiens IC50 = 7000.0 nM PMID[30297119]
NPT1080 Individual Protein Histone acetyltransferase PCAF Homo sapiens IC50 = 5000.0 nM PMID[30297119]
NPT1079 Individual Protein Histone acetyltransferase p300 Homo sapiens IC50 = 7000.0 nM PMID[31910017]
NPT1044 Individual Protein DNA topoisomerase II alpha Homo sapiens IC50 = 101200.0 nM PMID[31618025]
NPT322 Individual Protein DNA topoisomerase II beta Homo sapiens IC50 = 101200.0 nM PMID[31618025]
NPT306 Cell Line PC-3 Homo sapiens IC50 = 3460.0 nM PMID[33325699]
NPT90 Cell Line DU-145 Homo sapiens IC50 = 2870.0 nM PMID[33325699]
NPT306 Cell Line PC-3 Homo sapiens IC50 = 2860.0 nM PMID[33325699]
NPT82 Cell Line MDA-MB-231 Homo sapiens IC50 = 2130.0 nM PMID[33325699]
NPT82 Cell Line MDA-MB-231 Homo sapiens IC50 = 2430.0 nM PMID[33325699]
NPT20 Organism Candida albicans Candida albicans EC50 = 30000.0 nM PMID[28051303]
NPT956 Individual Protein Prostaglandin E synthase Homo sapiens IC50 = 300.0 nM PMID[29329790]
NPT486 Organism Toxoplasma gondii Toxoplasma gondii EC50 = 1800.0 nM PMID[31585276]
NPT2 Others Unspecified IC50 = 0.04305 ug.mL-1 PMID[31255927]

☑ 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 NPC93556 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 NPC93556 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