Natural Product: NPC14002

Natural Product ID:  NPC14002
Common Name:   Alpha-Ionone
IUPAC Name:   (E)-4-(2,6,6-trimethylcyclohex-2-en-1-yl)but-3-en-2-one
Synonyms:  
Molecular Formula:   C13H20O
Standard InCHIKey:  UZFLPKAIBPNNCA-BQYQJAHWSA-N
Standard InCHI:  InChI=1S/C13H20O/c1-10-6-5-9-13(3,4)12(10)8-7-11(2)14/h6-8,12H,5,9H2,1-4H3/b8-7+
Canonical SMILES:  CC(=O)/C=C/C1C(=CCCC1(C)C)C
First Find Year:  
Max Developmental Stage:  
Synthetic Gene Cluster:   ;

  Species Source

Organism ID Organism Name Taxonomy Level Family SuperKingdom Isolation Part Collection Location Collection Time Reference
NPO1797 Homo sapiens Species Hominidae Eukaryota saliva PMID[20809147]
NPO18176 Ephedra sinica Species Ephedraceae Eukaryota HerDing*
NPO27558 Podocarpus macrophyllus Species Podocarpaceae Eukaryota HerDing*
NPO23548 Leonurus japonicus Species Lamiaceae Eukaryota TM-MC*
NPO13989 Uncaria macrophylla Species Rubiaceae Eukaryota TCMID*
NPO27558 Podocarpus macrophyllus Species Podocarpaceae Eukaryota TCMID*
NPO8108.1 Citrullus lanatus subsp. vulgaris Subspecies Cucurbitaceae Eukaryota TCMID*
NPO18176 Ephedra sinica Species Ephedraceae Eukaryota TCMID*

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT858 Cell Line LNCaP Homo sapiens IC50 = 151000 nM 19138519
NPT1280 Organism Thrips tabaci Thrips tabaci Ratio = 1.3 17602496
NPT1281 Organism Thrips obscuratus Thrips obscuratus Ratio = 0 17602496
NPT1281 Organism Thrips obscuratus Thrips obscuratus Ratio = 1.8 17602496
NPT2 Others Unspecified Potency 436.4 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency 27306 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency 44668.4 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency 275.4 nM PubChem BioAssay data set
NPT603 Individual Protein Olfactory receptor 5K1 Homo sapiens Inhibition >= 75 % Patent: WO2013171535 A3

  Similar Natural Products 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 NPC14002 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
0.98 High Similarity NPC5626
0.96 High Similarity NPC23117
0.9074 High Similarity NPC311852
0.8727 High Similarity NPC60772
0.8491 Intermediate Similarity NPC295777
0.8491 Intermediate Similarity NPC69898
0.8148 Intermediate Similarity NPC37644
0.8136 Intermediate Similarity NPC288253
0.8113 Intermediate Similarity NPC64866
0.8103 Intermediate Similarity NPC127582
0.807 Intermediate Similarity NPC308108
0.807 Intermediate Similarity NPC170799
0.8033 Intermediate Similarity NPC176171
0.8033 Intermediate Similarity NPC92327
0.8 Intermediate Similarity NPC212210
0.7966 Intermediate Similarity NPC213152
0.7925 Intermediate Similarity NPC118788
0.7925 Intermediate Similarity NPC32351
0.7925 Intermediate Similarity NPC163984
0.7925 Intermediate Similarity NPC176819
0.7925 Intermediate Similarity NPC58970
0.7925 Intermediate Similarity NPC228776
0.7903 Intermediate Similarity NPC176107
0.7869 Intermediate Similarity NPC251118
0.7818 Intermediate Similarity NPC268564
0.78 Intermediate Similarity NPC216921
0.7778 Intermediate Similarity NPC188292
0.7778 Intermediate Similarity NPC117804
0.7778 Intermediate Similarity NPC260474
0.7778 Intermediate Similarity NPC87141
0.7705 Intermediate Similarity NPC285371
0.7705 Intermediate Similarity NPC475124
0.7705 Intermediate Similarity NPC6697
0.7656 Intermediate Similarity NPC256846
0.7627 Intermediate Similarity NPC276764
0.7627 Intermediate Similarity NPC472304
0.7619 Intermediate Similarity NPC475523
0.7586 Intermediate Similarity NPC281986
0.7586 Intermediate Similarity NPC22019
0.7586 Intermediate Similarity NPC208749
0.7586 Intermediate Similarity NPC321568
0.7586 Intermediate Similarity NPC115385
0.7541 Intermediate Similarity NPC165695
0.7541 Intermediate Similarity NPC202118
0.7541 Intermediate Similarity NPC197238
0.75 Intermediate Similarity NPC166788
0.75 Intermediate Similarity NPC310992
0.75 Intermediate Similarity NPC155198
0.7458 Intermediate Similarity NPC56905
0.7458 Intermediate Similarity NPC27610
0.7424 Intermediate Similarity NPC54123
0.7424 Intermediate Similarity NPC95863
0.7419 Intermediate Similarity NPC469662
0.7414 Intermediate Similarity NPC473733
0.7385 Intermediate Similarity NPC136473
0.7358 Intermediate Similarity NPC8610
0.7358 Intermediate Similarity NPC262558
0.7347 Intermediate Similarity NPC217923
0.7333 Intermediate Similarity NPC96551
0.7333 Intermediate Similarity NPC285594
0.7313 Intermediate Similarity NPC251705
0.7313 Intermediate Similarity NPC470044
0.7313 Intermediate Similarity NPC470045
0.7313 Intermediate Similarity NPC276336
0.7302 Intermediate Similarity NPC470329
0.7273 Intermediate Similarity NPC265782
0.7273 Intermediate Similarity NPC251929
0.7273 Intermediate Similarity NPC2634
0.7258 Intermediate Similarity NPC32285
0.7241 Intermediate Similarity NPC200258
0.7222 Intermediate Similarity NPC91962
0.7213 Intermediate Similarity NPC25853
0.7206 Intermediate Similarity NPC309852
0.7193 Intermediate Similarity NPC296311
0.717 Intermediate Similarity NPC13991
0.717 Intermediate Similarity NPC114239
0.717 Intermediate Similarity NPC191337
0.717 Intermediate Similarity NPC86683
0.717 Intermediate Similarity NPC241784
0.7167 Intermediate Similarity NPC266295
0.7167 Intermediate Similarity NPC94991
0.7167 Intermediate Similarity NPC30215
0.7164 Intermediate Similarity NPC5701
0.7164 Intermediate Similarity NPC474562
0.7164 Intermediate Similarity NPC225467
0.7164 Intermediate Similarity NPC234707
0.7164 Intermediate Similarity NPC115023
0.7143 Intermediate Similarity NPC52449
0.7143 Intermediate Similarity NPC169275
0.7143 Intermediate Similarity NPC4638
0.7121 Intermediate Similarity NPC139397
0.7101 Intermediate Similarity NPC293803
0.7101 Intermediate Similarity NPC476346
0.7097 Intermediate Similarity NPC60565
0.7077 Intermediate Similarity NPC290350
0.7077 Intermediate Similarity NPC4370
0.7059 Intermediate Similarity NPC153660
0.7059 Intermediate Similarity NPC474228
0.7059 Intermediate Similarity NPC303613
0.7059 Intermediate Similarity NPC186042
0.7049 Intermediate Similarity NPC259261
0.7037 Intermediate Similarity NPC14917
0.7037 Intermediate Similarity NPC236355
0.7037 Intermediate Similarity NPC4079
0.7015 Intermediate Similarity NPC260040
0.7015 Intermediate Similarity NPC159577
0.7015 Intermediate Similarity NPC35734
0.7015 Intermediate Similarity NPC282593
0.7015 Intermediate Similarity NPC307176
0.7 Intermediate Similarity NPC69408
0.7 Intermediate Similarity NPC474463
0.7 Intermediate Similarity NPC192427
0.7 Intermediate Similarity NPC1254
0.6981 Remote Similarity NPC25771
0.6981 Remote Similarity NPC477686
0.6964 Remote Similarity NPC116906
0.6964 Remote Similarity NPC15325
0.6957 Remote Similarity NPC474796
0.6957 Remote Similarity NPC329866
0.6957 Remote Similarity NPC474797
0.6923 Remote Similarity NPC242945
0.6923 Remote Similarity NPC323005
0.6923 Remote Similarity NPC259156
0.6912 Remote Similarity NPC21944
0.6912 Remote Similarity NPC181204
0.6912 Remote Similarity NPC305501
0.6912 Remote Similarity NPC190035
0.6909 Remote Similarity NPC124851
0.6866 Remote Similarity NPC182815
0.6863 Remote Similarity NPC183670
0.6863 Remote Similarity NPC111474
0.6857 Remote Similarity NPC473171
0.6852 Remote Similarity NPC296337
0.6842 Remote Similarity NPC27438
0.6842 Remote Similarity NPC236623
0.6825 Remote Similarity NPC228574
0.6825 Remote Similarity NPC294304
0.6825 Remote Similarity NPC469728
0.6825 Remote Similarity NPC317025
0.6825 Remote Similarity NPC329416
0.6825 Remote Similarity NPC475795
0.6825 Remote Similarity NPC326645
0.6825 Remote Similarity NPC97322
0.6825 Remote Similarity NPC317177
0.6812 Remote Similarity NPC29542
0.6812 Remote Similarity NPC130016
0.6812 Remote Similarity NPC323437
0.6812 Remote Similarity NPC201562
0.6812 Remote Similarity NPC180015
0.6812 Remote Similarity NPC56747
0.6812 Remote Similarity NPC109576
0.6806 Remote Similarity NPC105197
0.6792 Remote Similarity NPC301972
0.6792 Remote Similarity NPC292463
0.6786 Remote Similarity NPC17518
0.678 Remote Similarity NPC100809
0.678 Remote Similarity NPC209431
0.6769 Remote Similarity NPC107258
0.6765 Remote Similarity NPC246722
0.6765 Remote Similarity NPC151045
0.6761 Remote Similarity NPC469793
0.6761 Remote Similarity NPC26504
0.6761 Remote Similarity NPC470525
0.6761 Remote Similarity NPC469796
0.6731 Remote Similarity NPC144023
0.6727 Remote Similarity NPC100380
0.6724 Remote Similarity NPC471751
0.6721 Remote Similarity NPC267626
0.6721 Remote Similarity NPC49575
0.6721 Remote Similarity NPC55004
0.6721 Remote Similarity NPC230823
0.6721 Remote Similarity NPC193695
0.6719 Remote Similarity NPC472306
0.6719 Remote Similarity NPC167256
0.6716 Remote Similarity NPC142754
0.6716 Remote Similarity NPC82477
0.6716 Remote Similarity NPC296697
0.6716 Remote Similarity NPC39157
0.6716 Remote Similarity NPC20610
0.6714 Remote Similarity NPC215050
0.6714 Remote Similarity NPC255021
0.6714 Remote Similarity NPC22134
0.6714 Remote Similarity NPC20025
0.6712 Remote Similarity NPC19900
0.6712 Remote Similarity NPC190211
0.6667 Remote Similarity NPC176621
0.6667 Remote Similarity NPC202189
0.6667 Remote Similarity NPC185587
0.6667 Remote Similarity NPC470078
0.6667 Remote Similarity NPC275472
0.6667 Remote Similarity NPC248411
0.6667 Remote Similarity NPC97377
0.6667 Remote Similarity NPC135648
0.6667 Remote Similarity NPC267514
0.6667 Remote Similarity NPC133253
0.6667 Remote Similarity NPC145755
0.6667 Remote Similarity NPC255781
0.6667 Remote Similarity NPC304983
0.6667 Remote Similarity NPC474539
0.6667 Remote Similarity NPC181587

  Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

●  The left chart: Distribution of similarity level between NPC14002 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
0.807 Intermediate Similarity NPD287 Approved
0.7273 Intermediate Similarity NPD4691 Approved
0.7206 Intermediate Similarity NPD4058 Approved
0.7121 Intermediate Similarity NPD4137 Phase 3
0.7015 Intermediate Similarity NPD4747 Approved
0.6957 Remote Similarity NPD4687 Approved
0.6912 Remote Similarity NPD5276 Approved
0.6825 Remote Similarity NPD4193 Approved
0.6825 Remote Similarity NPD4194 Approved
0.6825 Remote Similarity NPD4192 Approved
0.6825 Remote Similarity NPD4191 Approved
0.6716 Remote Similarity NPD3621 Clinical (unspecified phase)
0.6714 Remote Similarity NPD5733 Approved
0.6712 Remote Similarity NPD4195 Approved
0.6604 Remote Similarity NPD1799 Clinical (unspecified phase)
0.66 Remote Similarity NPD319 Phase 1
0.64 Remote Similarity NPD4695 Discontinued
0.6364 Remote Similarity NPD3527 Clinical (unspecified phase)
0.629 Remote Similarity NPD4219 Approved
0.6207 Remote Similarity NPD8262 Approved
0.6125 Remote Similarity NPD5690 Phase 2
0.6119 Remote Similarity NPD5325 Clinical (unspecified phase)
0.6104 Remote Similarity NPD8028 Phase 2
0.6049 Remote Similarity NPD3573 Approved
0.6038 Remote Similarity NPD5783 Phase 3
0.6026 Remote Similarity NPD4221 Approved
0.6026 Remote Similarity NPD4223 Phase 3
0.5942 Remote Similarity NPD7331 Phase 2
0.5926 Remote Similarity NPD4623 Approved
0.5926 Remote Similarity NPD4519 Discontinued
0.5875 Remote Similarity NPD3665 Phase 1
0.5875 Remote Similarity NPD4197 Approved
0.5875 Remote Similarity NPD3666 Approved
0.5875 Remote Similarity NPD3133 Approved
0.5811 Remote Similarity NPD4784 Approved
0.5811 Remote Similarity NPD4785 Approved
0.5802 Remote Similarity NPD5329 Approved
0.5769 Remote Similarity NPD8259 Clinical (unspecified phase)
0.5765 Remote Similarity NPD6079 Approved
0.5753 Remote Similarity NPD4243 Approved
0.5733 Remote Similarity NPD8264 Approved
0.5732 Remote Similarity NPD4688 Approved
0.5732 Remote Similarity NPD3618 Phase 1
0.5732 Remote Similarity NPD4693 Phase 3
0.5732 Remote Similarity NPD7146 Approved
0.5732 Remote Similarity NPD4690 Approved
0.5732 Remote Similarity NPD5205 Approved
0.5732 Remote Similarity NPD5280 Approved
0.5732 Remote Similarity NPD3574 Clinical (unspecified phase)
0.5732 Remote Similarity NPD4689 Approved
0.5732 Remote Similarity NPD7521 Approved
0.5732 Remote Similarity NPD7334 Approved
0.5732 Remote Similarity NPD4138 Approved
0.5732 Remote Similarity NPD6684 Approved
0.5732 Remote Similarity NPD5330 Approved
0.5732 Remote Similarity NPD4694 Approved
0.5732 Remote Similarity NPD6409 Approved
0.5732 Remote Similarity NPD5279 Phase 3
0.5714 Remote Similarity NPD6108 Clinical (unspecified phase)
0.5714 Remote Similarity NPD3617 Approved
0.5647 Remote Similarity NPD5207 Approved
0.5634 Remote Similarity NPD3709 Clinical (unspecified phase)
0.5625 Remote Similarity NPD5209 Approved
0.5625 Remote Similarity NPD342 Phase 1
0.5625 Remote Similarity NPD3667 Approved
0.5625 Remote Similarity NPD4752 Clinical (unspecified phase)
0.5616 Remote Similarity NPD7144 Approved
0.5616 Remote Similarity NPD7143 Approved
0.561 Remote Similarity NPD1694 Approved
0.561 Remote Similarity NPD1696 Phase 3

Structure

External Identifiers

PubChem CID   5282108
ChEMBL   CHEMBL472877
ZINC  

Physicochemical Properties

Molecular Weight:  192.15
ALogP:  2.2521
MLogP:  2.78
XLogP:  4.103
# Rotatable Bonds:  6
Polar Surface Area:  17.07
# H-Bond Aceptor:  1
# H-Bond Donor:  0
# Rings:  1
# Heavy Atoms:  14

Download Data

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Structure MOL file  
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Biological Activities  
Similar NPs/Drugs