Structure

Physi-Chem Properties

Molecular Weight:  242.09
Volume:  252.879
LogP:  3.203
LogD:  2.668
LogS:  -3.769
# Rotatable Bonds:  0
TPSA:  50.44
# H-Bond Aceptor:  3
# H-Bond Donor:  1
# Rings:  3
# Heavy Atoms:  3

MedChem Properties

QED Drug-Likeness Score:  0.749
Synthetic Accessibility Score:  4.028
Fsp3:  0.267
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:  -4.939
MDCK Permeability:  1.9941287973779254e-05
Pgp-inhibitor:  0.001
Pgp-substrate:  0.102
Human Intestinal Absorption (HIA):  0.006
20% Bioavailability (F20%):  0.003
30% Bioavailability (F30%):  0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.004
Plasma Protein Binding (PPB):  93.43379974365234%
Volume Distribution (VD):  1.345
Pgp-substrate:  4.364486217498779%

ADMET: Metabolism

CYP1A2-inhibitor:  0.966
CYP1A2-substrate:  0.553
CYP2C19-inhibitor:  0.161
CYP2C19-substrate:  0.802
CYP2C9-inhibitor:  0.209
CYP2C9-substrate:  0.213
CYP2D6-inhibitor:  0.057
CYP2D6-substrate:  0.193
CYP3A4-inhibitor:  0.047
CYP3A4-substrate:  0.245

ADMET: Excretion

Clearance (CL):  4.751
Half-life (T1/2):  0.856

ADMET: Toxicity

hERG Blockers:  0.001
Human Hepatotoxicity (H-HT):  0.635
Drug-inuced Liver Injury (DILI):  0.979
AMES Toxicity:  0.234
Rat Oral Acute Toxicity:  0.882
Maximum Recommended Daily Dose:  0.346
Skin Sensitization:  0.826
Carcinogencity:  0.894
Eye Corrosion:  0.016
Eye Irritation:  0.095
Respiratory Toxicity:  0.971

Download Data

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

  Natural Product: NPC131174

Natural Product ID:  NPC131174
Common Name*:   Taraxacin
IUPAC Name:   1,5,8-trimethyl-3a,4-dihydroazuleno[6,5-b]furan-2,6-dione
Synonyms:   Taraxacin
Standard InCHIKey:  BAHMQESJBKGPTE-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C15H14O3/c1-7-4-12(16)14-8(2)5-13-11(6-10(7)14)9(3)15(17)18-13/h4,6,13H,5H2,1-3H3
SMILES:  CC1=C2C=C3C(=CC(=O)C3=C(CC2OC1=O)C)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL449951
PubChem CID:   5241825
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0001983] Dihydrofurans
        • [CHEMONTID:0001982] Furanones
          • [CHEMONTID:0002223] Butenolides

*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
NPO26622 Taraxacum officinale Species Asteraceae Eukaryota n.a. n.a. Database[FooDB]
NPO26622 Taraxacum officinale Species Asteraceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO26622 Taraxacum officinale Species Asteraceae Eukaryota Plant n.a. n.a. Database[FooDB]
NPO26622 Taraxacum officinale Species Asteraceae Eukaryota Root n.a. n.a. Database[FooDB]
NPO26622 Taraxacum officinale Species Asteraceae Eukaryota n.a. n.a. Database[FooDB]
NPO26785 Taraxacum mongolicum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO26622 Taraxacum officinale Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO26622 Taraxacum officinale Species Asteraceae Eukaryota n.a. n.a. Database[Phenol-Explorer]
NPO26785 Taraxacum mongolicum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO26622 Taraxacum officinale Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO26622 Taraxacum officinale Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO26785 Taraxacum mongolicum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO26785 Taraxacum mongolicum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO26622 Taraxacum officinale Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO1596 Taraxacum borealisinense Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO13668 Taraxacum platycarpum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO23327 Taraxacum coreanum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO23327 Taraxacum coreanum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26785 Taraxacum mongolicum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13668 Taraxacum platycarpum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26622 Taraxacum officinale 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
NPT2 Others Unspecified IC50 = 57570.0 nM PMID[481332]

☑ 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 NPC131174 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
0.9032 High Similarity NPC132243
0.8281 Intermediate Similarity NPC151648
0.8182 Intermediate Similarity NPC133904
0.7969 Intermediate Similarity NPC286189
0.7941 Intermediate Similarity NPC203335
0.791 Intermediate Similarity NPC182794
0.7879 Intermediate Similarity NPC473737
0.7879 Intermediate Similarity NPC210303
0.7879 Intermediate Similarity NPC44343
0.7879 Intermediate Similarity NPC179087
0.7838 Intermediate Similarity NPC299235
0.7794 Intermediate Similarity NPC248125
0.7619 Intermediate Similarity NPC478117
0.7571 Intermediate Similarity NPC474823
0.7571 Intermediate Similarity NPC470256
0.7465 Intermediate Similarity NPC475004
0.7429 Intermediate Similarity NPC225272
0.7424 Intermediate Similarity NPC133600
0.7397 Intermediate Similarity NPC287878
0.7353 Intermediate Similarity NPC474658
0.7324 Intermediate Similarity NPC218477
0.7324 Intermediate Similarity NPC287705
0.7313 Intermediate Similarity NPC309408
0.7286 Intermediate Similarity NPC37382
0.7273 Intermediate Similarity NPC472965
0.7273 Intermediate Similarity NPC264227
0.7273 Intermediate Similarity NPC63649
0.726 Intermediate Similarity NPC84038
0.726 Intermediate Similarity NPC133098
0.7237 Intermediate Similarity NPC68156
0.7222 Intermediate Similarity NPC88877
0.7222 Intermediate Similarity NPC476591
0.7213 Intermediate Similarity NPC135698
0.72 Intermediate Similarity NPC469414
0.72 Intermediate Similarity NPC478193
0.72 Intermediate Similarity NPC478195
0.72 Intermediate Similarity NPC478192
0.72 Intermediate Similarity NPC478196
0.72 Intermediate Similarity NPC329826
0.72 Intermediate Similarity NPC478194
0.72 Intermediate Similarity NPC478191
0.7188 Intermediate Similarity NPC478120
0.7183 Intermediate Similarity NPC194871
0.7179 Intermediate Similarity NPC302426
0.7162 Intermediate Similarity NPC474705
0.7143 Intermediate Similarity NPC476589
0.7105 Intermediate Similarity NPC123360
0.7101 Intermediate Similarity NPC474774
0.7101 Intermediate Similarity NPC68110
0.7097 Intermediate Similarity NPC236338
0.7067 Intermediate Similarity NPC15499
0.7067 Intermediate Similarity NPC294434
0.7067 Intermediate Similarity NPC259599
0.7067 Intermediate Similarity NPC117746
0.7059 Intermediate Similarity NPC79756
0.7059 Intermediate Similarity NPC130953
0.7027 Intermediate Similarity NPC186531
0.7027 Intermediate Similarity NPC112983
0.7027 Intermediate Similarity NPC162571
0.7013 Intermediate Similarity NPC65603
0.7013 Intermediate Similarity NPC10572
0.7 Intermediate Similarity NPC53136
0.7 Intermediate Similarity NPC173409
0.6986 Remote Similarity NPC473603
0.6986 Remote Similarity NPC236208
0.6986 Remote Similarity NPC476059
0.6986 Remote Similarity NPC494
0.6974 Remote Similarity NPC138408
0.6974 Remote Similarity NPC226669
0.6974 Remote Similarity NPC193351
0.6957 Remote Similarity NPC217537
0.6957 Remote Similarity NPC15193
0.6951 Remote Similarity NPC78089
0.6944 Remote Similarity NPC21998
0.6933 Remote Similarity NPC146583
0.6912 Remote Similarity NPC478095
0.6901 Remote Similarity NPC470123
0.6901 Remote Similarity NPC220766
0.6901 Remote Similarity NPC470688
0.6901 Remote Similarity NPC282760
0.6875 Remote Similarity NPC42470
0.6875 Remote Similarity NPC10276
0.6875 Remote Similarity NPC35089
0.6867 Remote Similarity NPC107787
0.6857 Remote Similarity NPC2328
0.6857 Remote Similarity NPC155849
0.6849 Remote Similarity NPC276290
0.6849 Remote Similarity NPC477117
0.6842 Remote Similarity NPC476355
0.6842 Remote Similarity NPC474758
0.6842 Remote Similarity NPC114727
0.6842 Remote Similarity NPC476590
0.6835 Remote Similarity NPC178277
0.6835 Remote Similarity NPC471299
0.6829 Remote Similarity NPC115786
0.6825 Remote Similarity NPC15789
0.6818 Remote Similarity NPC173157
0.6812 Remote Similarity NPC98519
0.6806 Remote Similarity NPC191233
0.68 Remote Similarity NPC163003
0.6795 Remote Similarity NPC15975
0.6795 Remote Similarity NPC57744
0.6795 Remote Similarity NPC195785
0.679 Remote Similarity NPC173609
0.6765 Remote Similarity NPC478096
0.6765 Remote Similarity NPC189700
0.6761 Remote Similarity NPC475618
0.6757 Remote Similarity NPC470693
0.6757 Remote Similarity NPC475982
0.6753 Remote Similarity NPC161038
0.6753 Remote Similarity NPC260396
0.6753 Remote Similarity NPC329852
0.675 Remote Similarity NPC74673
0.675 Remote Similarity NPC69271
0.6721 Remote Similarity NPC47946
0.6721 Remote Similarity NPC26600
0.6721 Remote Similarity NPC270706
0.6716 Remote Similarity NPC245002
0.6716 Remote Similarity NPC150717
0.6716 Remote Similarity NPC221763
0.6712 Remote Similarity NPC472266
0.6711 Remote Similarity NPC269206
0.6711 Remote Similarity NPC12815
0.6711 Remote Similarity NPC58956
0.6711 Remote Similarity NPC295633
0.6711 Remote Similarity NPC215745
0.6711 Remote Similarity NPC238948
0.6709 Remote Similarity NPC472960
0.6709 Remote Similarity NPC253749
0.6709 Remote Similarity NPC128276
0.6707 Remote Similarity NPC39588
0.6667 Remote Similarity NPC25684
0.6667 Remote Similarity NPC281949
0.6667 Remote Similarity NPC238554
0.6667 Remote Similarity NPC471325
0.6667 Remote Similarity NPC471556
0.6667 Remote Similarity NPC159650
0.6667 Remote Similarity NPC22897
0.6667 Remote Similarity NPC301477
0.6667 Remote Similarity NPC202011
0.6667 Remote Similarity NPC27205
0.6667 Remote Similarity NPC472967
0.6667 Remote Similarity NPC225022
0.6667 Remote Similarity NPC266159
0.6628 Remote Similarity NPC268298
0.6625 Remote Similarity NPC270126
0.6625 Remote Similarity NPC182550
0.6625 Remote Similarity NPC99651
0.6623 Remote Similarity NPC177030
0.6623 Remote Similarity NPC227396
0.6623 Remote Similarity NPC140287
0.6623 Remote Similarity NPC470686
0.6622 Remote Similarity NPC238223
0.6622 Remote Similarity NPC309466
0.662 Remote Similarity NPC217940
0.6615 Remote Similarity NPC191643
0.6613 Remote Similarity NPC128280
0.6613 Remote Similarity NPC197467
0.6585 Remote Similarity NPC94200
0.6585 Remote Similarity NPC268122
0.6582 Remote Similarity NPC476794
0.6582 Remote Similarity NPC228902
0.6582 Remote Similarity NPC471225
0.6582 Remote Similarity NPC470240
0.6582 Remote Similarity NPC187568
0.6582 Remote Similarity NPC24827
0.6582 Remote Similarity NPC41780
0.6582 Remote Similarity NPC275530
0.6579 Remote Similarity NPC257618
0.6579 Remote Similarity NPC316185
0.6575 Remote Similarity NPC146811
0.6575 Remote Similarity NPC276299
0.6575 Remote Similarity NPC469446
0.6571 Remote Similarity NPC26223
0.6567 Remote Similarity NPC474913
0.6562 Remote Similarity NPC275316
0.6552 Remote Similarity NPC129419
0.6548 Remote Similarity NPC33570
0.6548 Remote Similarity NPC161957
0.6548 Remote Similarity NPC21471
0.6548 Remote Similarity NPC281172
0.6548 Remote Similarity NPC130030
0.6543 Remote Similarity NPC223904
0.6543 Remote Similarity NPC276356
0.6538 Remote Similarity NPC155587
0.6533 Remote Similarity NPC232812
0.6506 Remote Similarity NPC215294
0.6506 Remote Similarity NPC118423
0.6506 Remote Similarity NPC318468
0.6506 Remote Similarity NPC193198
0.6506 Remote Similarity NPC144415
0.6506 Remote Similarity NPC16488
0.65 Remote Similarity NPC108816
0.65 Remote Similarity NPC182292
0.65 Remote Similarity NPC471220
0.65 Remote Similarity NPC99182
0.65 Remote Similarity NPC93763
0.6494 Remote Similarity NPC16349
0.6494 Remote Similarity NPC222244
0.6494 Remote Similarity NPC284006

  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 NPC131174 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
0.6984 Remote Similarity NPD6927 Phase 3
0.679 Remote Similarity NPD5209 Approved
0.6438 Remote Similarity NPD2685 Clinical (unspecified phase)
0.6111 Remote Similarity NPD4246 Clinical (unspecified phase)
0.6 Remote Similarity NPD5343 Approved
0.5976 Remote Similarity NPD4756 Discovery
0.5926 Remote Similarity NPD8039 Approved
0.5914 Remote Similarity NPD1698 Clinical (unspecified phase)
0.5909 Remote Similarity NPD4220 Pre-registration
0.5889 Remote Similarity NPD1695 Approved
0.5867 Remote Similarity NPD5325 Clinical (unspecified phase)
0.5844 Remote Similarity NPD4247 Clinical (unspecified phase)
0.5814 Remote Similarity NPD4752 Clinical (unspecified phase)
0.5795 Remote Similarity NPD1694 Approved
0.5781 Remote Similarity NPD6097 Approved
0.5781 Remote Similarity NPD6096 Approved
0.5732 Remote Similarity NPD1452 Discontinued
0.5682 Remote Similarity NPD6400 Clinical (unspecified phase)
0.5618 Remote Similarity NPD1733 Clinical (unspecified phase)
0.5616 Remote Similarity NPD69 Approved
0.5616 Remote Similarity NPD9119 Approved

  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