Structure

Physi-Chem Properties

Molecular Weight:  230.09
Volume:  244.139
LogP:  2.496
LogD:  2.542
LogS:  -3.097
# Rotatable Bonds:  1
TPSA:  27.69
# H-Bond Aceptor:  3
# H-Bond Donor:  0
# Rings:  2
# Heavy Atoms:  3

MedChem Properties

QED Drug-Likeness Score:  0.644
Synthetic Accessibility Score:  5.299
Fsp3:  0.429
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
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:  -4.256
MDCK Permeability:  2.911527371907141e-05
Pgp-inhibitor:  0.014
Pgp-substrate:  0.0
Human Intestinal Absorption (HIA):  0.003
20% Bioavailability (F20%):  0.863
30% Bioavailability (F30%):  0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.044
Plasma Protein Binding (PPB):  100.28417205810547%
Volume Distribution (VD):  2.199
Pgp-substrate:  3.411531925201416%

ADMET: Metabolism

CYP1A2-inhibitor:  0.123
CYP1A2-substrate:  0.733
CYP2C19-inhibitor:  0.894
CYP2C19-substrate:  0.835
CYP2C9-inhibitor:  0.867
CYP2C9-substrate:  0.064
CYP2D6-inhibitor:  0.324
CYP2D6-substrate:  0.159
CYP3A4-inhibitor:  0.924
CYP3A4-substrate:  0.58

ADMET: Excretion

Clearance (CL):  14.685
Half-life (T1/2):  0.233

ADMET: Toxicity

hERG Blockers:  0.001
Human Hepatotoxicity (H-HT):  0.993
Drug-inuced Liver Injury (DILI):  0.981
AMES Toxicity:  0.978
Rat Oral Acute Toxicity:  0.633
Maximum Recommended Daily Dose:  0.924
Skin Sensitization:  0.944
Carcinogencity:  0.898
Eye Corrosion:  0.648
Eye Irritation:  0.76
Respiratory Toxicity:  0.954

Download Data

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

  Natural Product: NPC474711

Natural Product ID:  NPC474711
Common Name*:   Flosculin C
IUPAC Name:   (2Z)-2-hexa-2,4-diynylidene-7-methoxy-1,6-dioxaspiro[4.4]non-3-ene
Synonyms:   flosculin C
Standard InCHIKey:  BACKKBRUFWBBSR-GHXNOFRVSA-N
Standard InCHI:  InChI=1S/C14H14O3/c1-3-4-5-6-7-12-8-10-14(16-12)11-9-13(15-2)17-14/h7-8,10,13H,9,11H2,1-2H3/b12-7-
SMILES:  CC#CC#CC=C1C=CC2(O1)CCC(O2)OC
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL479897
PubChem CID:   11593812
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0004603] Organic oxygen compounds
      • [CHEMONTID:0000323] Organooxygen compounds
        • [CHEMONTID:0000254] Ethers
          • [CHEMONTID:0001656] Acetals
            • [CHEMONTID:0004472] Ketals

*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
NPO3028 Plagius flosculosus Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[16499337]
NPO3028 Plagius flosculosus 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
NPT15 Cell Line Jurkat Homo sapiens IC50 = 10800.0 nM PMID[449472]
NPT15 Cell Line Jurkat Homo sapiens IC50 = 16900.0 nM PMID[449472]
NPT116 Cell Line HL-60 Homo sapiens IC50 = 16700.0 nM PMID[449472]

☑ 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 NPC474711 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
1.0 High Similarity NPC474588
0.9636 High Similarity NPC223804
0.8421 Intermediate Similarity NPC151923
0.8421 Intermediate Similarity NPC9611
0.7385 Intermediate Similarity NPC474729
0.7385 Intermediate Similarity NPC474723
0.7273 Intermediate Similarity NPC90463
0.7143 Intermediate Similarity NPC474869
0.6765 Remote Similarity NPC471460
0.6622 Remote Similarity NPC472173
0.6562 Remote Similarity NPC474913
0.6418 Remote Similarity NPC133600
0.6349 Remote Similarity NPC106531
0.6324 Remote Similarity NPC476585
0.6286 Remote Similarity NPC475618
0.6212 Remote Similarity NPC86948
0.6212 Remote Similarity NPC245002
0.6197 Remote Similarity NPC220766
0.6184 Remote Similarity NPC472174
0.6176 Remote Similarity NPC222852
0.6173 Remote Similarity NPC474439
0.6173 Remote Similarity NPC474028
0.6154 Remote Similarity NPC269615
0.6154 Remote Similarity NPC159535
0.6154 Remote Similarity NPC151761
0.6143 Remote Similarity NPC476584
0.6111 Remote Similarity NPC191233
0.6098 Remote Similarity NPC475714
0.6087 Remote Similarity NPC299730
0.6024 Remote Similarity NPC30915
0.5972 Remote Similarity NPC182794
0.5972 Remote Similarity NPC476586
0.5968 Remote Similarity NPC90490
0.5946 Remote Similarity NPC287705
0.5942 Remote Similarity NPC474267
0.5932 Remote Similarity NPC57923
0.5915 Remote Similarity NPC473737
0.5882 Remote Similarity NPC44542
0.5882 Remote Similarity NPC472445
0.5873 Remote Similarity NPC98284
0.5873 Remote Similarity NPC82446
0.5867 Remote Similarity NPC470693
0.5857 Remote Similarity NPC130953
0.5833 Remote Similarity NPC477457
0.5833 Remote Similarity NPC475706
0.5833 Remote Similarity NPC477456
0.5811 Remote Similarity NPC225272
0.5781 Remote Similarity NPC328784
0.5781 Remote Similarity NPC291437
0.5775 Remote Similarity NPC15193
0.5769 Remote Similarity NPC470686
0.5765 Remote Similarity NPC474424
0.5753 Remote Similarity NPC131174
0.5738 Remote Similarity NPC12907
0.5733 Remote Similarity NPC474823
0.5696 Remote Similarity NPC478193
0.5696 Remote Similarity NPC478195
0.5696 Remote Similarity NPC478192
0.5696 Remote Similarity NPC478194
0.5696 Remote Similarity NPC478196
0.5696 Remote Similarity NPC478191
0.5694 Remote Similarity NPC210303
0.5694 Remote Similarity NPC132243
0.5694 Remote Similarity NPC475073
0.5694 Remote Similarity NPC44343
0.5694 Remote Similarity NPC179087
0.5692 Remote Similarity NPC71053
0.5692 Remote Similarity NPC59408
0.5682 Remote Similarity NPC242877
0.5682 Remote Similarity NPC64913
0.5676 Remote Similarity NPC276299
0.5676 Remote Similarity NPC37382
0.5672 Remote Similarity NPC110732
0.5667 Remote Similarity NPC206906
0.5658 Remote Similarity NPC232812
0.5658 Remote Similarity NPC475004
0.5652 Remote Similarity NPC471279
0.5652 Remote Similarity NPC474825
0.5652 Remote Similarity NPC265551
0.5652 Remote Similarity NPC212730
0.5652 Remote Similarity NPC471277
0.5645 Remote Similarity NPC47946
0.5645 Remote Similarity NPC26600
0.5641 Remote Similarity NPC476489
0.5641 Remote Similarity NPC132938
0.5641 Remote Similarity NPC476490
0.5634 Remote Similarity NPC98519
0.5634 Remote Similarity NPC309408
0.5625 Remote Similarity NPC135698
0.5625 Remote Similarity NPC91765
0.5625 Remote Similarity NPC229655
0.5618 Remote Similarity NPC475995
0.5618 Remote Similarity NPC474098
0.5616 Remote Similarity NPC471611

  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 NPC474711 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
NPD

  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