Structure

Physi-Chem Properties

Molecular Weight:  282.13
Volume:  302.13
LogP:  3.452
LogD:  3.231
LogS:  -3.109
# Rotatable Bonds:  2
TPSA:  49.69
# H-Bond Aceptor:  3
# H-Bond Donor:  2
# Rings:  3
# Heavy Atoms:  3

MedChem Properties

QED Drug-Likeness Score:  0.81
Synthetic Accessibility Score:  3.283
Fsp3:  0.222
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:  -4.679
MDCK Permeability:  7.352322882070439e-06
Pgp-inhibitor:  0.001
Pgp-substrate:  0.975
Human Intestinal Absorption (HIA):  0.007
20% Bioavailability (F20%):  0.048
30% Bioavailability (F30%):  0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.048
Plasma Protein Binding (PPB):  95.8097915649414%
Volume Distribution (VD):  1.8
Pgp-substrate:  1.9772887229919434%

ADMET: Metabolism

CYP1A2-inhibitor:  0.249
CYP1A2-substrate:  0.19
CYP2C19-inhibitor:  0.917
CYP2C19-substrate:  0.244
CYP2C9-inhibitor:  0.758
CYP2C9-substrate:  0.955
CYP2D6-inhibitor:  0.768
CYP2D6-substrate:  0.757
CYP3A4-inhibitor:  0.667
CYP3A4-substrate:  0.288

ADMET: Excretion

Clearance (CL):  7.921
Half-life (T1/2):  0.383

ADMET: Toxicity

hERG Blockers:  0.082
Human Hepatotoxicity (H-HT):  0.759
Drug-inuced Liver Injury (DILI):  0.272
AMES Toxicity:  0.009
Rat Oral Acute Toxicity:  0.127
Maximum Recommended Daily Dose:  0.076
Skin Sensitization:  0.627
Carcinogencity:  0.016
Eye Corrosion:  0.02
Eye Irritation:  0.824
Respiratory Toxicity:  0.164

Download Data

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

  Natural Product: NPC136531

Natural Product ID:  NPC136531
Common Name*:   QLSUUELDMMCCEI-ROUUACIJSA-N
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  QLSUUELDMMCCEI-ROUUACIJSA-N
Standard InCHI:  InChI=1S/C18H18O3/c1-11-12(2)18(14-5-9-16(20)10-6-14)21-17(11)13-3-7-15(19)8-4-13/h3-10,17-20H,1-2H3/t17-,18-/m0/s1
SMILES:  CC1=C(C)[C@@H](c2ccc(cc2)O)O[C@@H]1c1ccc(cc1)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   n.a.
PubChem CID:   25775479
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0002448] Benzenoids
      • [CHEMONTID:0000134] Phenols
        • [CHEMONTID:0004646] 1-hydroxy-2-unsubstituted benzenoids

*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
NPO1751 Ribes nigrum Species n.a. n.a. Fruit n.a. n.a. DOI[10.1016/S0963-9969(99)00095-2]
NPO14178 Leonurus persicus Species Lamiaceae Eukaryota Aerial parts n.a. n.a. PMID[10395493]
NPO15442 Magnolia sieboldii Species Magnoliaceae Eukaryota n.a. n.a. n.a. PMID[11534769]
NPO1751 Ribes nigrum Species n.a. n.a. n.a. fruit n.a. PMID[16417304]
NPO14284 Delphinium shawurense Species Ranunculaceae Eukaryota n.a. n.a. n.a. PMID[20351801]
NPO15442 Magnolia sieboldii Species Magnoliaceae Eukaryota stem bark n.a. n.a. PMID[8988596]
NPO1751 Ribes nigrum Species n.a. n.a. n.a. n.a. Database[FooDB]
NPO1751 Ribes nigrum Species n.a. n.a. Bulb n.a. n.a. Database[FooDB]
NPO1751 Ribes nigrum Species n.a. n.a. Fruit n.a. n.a. Database[FooDB]
NPO1751 Ribes nigrum Species n.a. n.a. Fruit Juice n.a. n.a. Database[FooDB]
NPO1751 Ribes nigrum Species n.a. n.a. Leaf n.a. n.a. Database[FooDB]
NPO1751 Ribes nigrum Species n.a. n.a. Seed n.a. n.a. Database[FooDB]
NPO1751 Ribes nigrum Species n.a. n.a. Seed Essent. Oil n.a. n.a. Database[FooDB]
NPO1751 Ribes nigrum Species n.a. n.a. Fruits n.a. Database[FooDB]
NPO16741 Codonopsis pilosula Species Campanulaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO14178 Leonurus persicus Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO15442 Magnolia sieboldii Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO1751 Ribes nigrum Species n.a. n.a. n.a. n.a. n.a. Database[TCMID]
NPO2458 Aconitum violaceum Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14673 Lathyrus nissolia Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14178 Leonurus persicus Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO16741 Codonopsis pilosula Species Campanulaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15442 Magnolia sieboldii Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO16741 Codonopsis pilosula Species Campanulaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO16741 Codonopsis pilosula Species Campanulaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO14673 Lathyrus nissolia Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14178 Leonurus persicus Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11912 Peltogyne porphyrocardia Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14284 Delphinium shawurense Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11128 Ratibida mexicana Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9860.1 Pinus brutia var. eldarica Varieties Pinaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13311 Agelas linnaei Species Agelasidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28601 Aspergillus falconensis Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10191 Ormosia balansae Species Limoniidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12982 Dysidea amblia Species Dysideidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15626 Alternaria japonica Species Pleosporaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1751 Ribes nigrum Species n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO3949 Ceramium rubrum Species Ceramiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7713 Euplotes raikovi Species Euplotidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13477 Cyberlindnera jadinii Species Phaffomycetaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO965 Bleekeria vitiensis Species Plesiopidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3244 Ascidia ahodori Species Ascidiidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2458 Aconitum violaceum Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4512 Fagraea gracilipes Species Gentianaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15160 Gutierrezia lucida Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15442 Magnolia sieboldii Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13160 Garcinia xipshuanbannaensis Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14043 Caulerpa serrulata Species Caulerpaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10887 Pseudeurotium zonatum Species Pseudeurotiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6347 Iryanthera paraensis Species Myristicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16741 Codonopsis pilosula Species Campanulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12756 Roboastra tigris Species Polyceridae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15253 Helichrysum graveolens 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 NPC136531 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 NPC136531 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