Natural Product: NPC52449

Natural Product ID:  NPC52449
Common Name:   Labdadienedial
IUPAC Name:   (2Z)-2-[2-[(1S,4aS,8aS)-5,5,8a-trimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]ethylidene]butanedial
Synonyms:  
Molecular Formula:   C20H30O2
Standard InCHIKey:  TZCSIFOYBLPUIF-BNYLVOSESA-N
Standard InCHI:  InChI=1S/C20H30O2/c1-15-6-9-18-19(2,3)11-5-12-20(18,4)17(15)8-7-16(14-22)10-13-21/h7,13-14,17-18H,1,5-6,8-12H2,2-4H3/b16-7-/t17-,18-,20+/m0/s1
Canonical SMILES:  O=CC/C(=C/C[C@H]1C(=C)CC[C@@H]2[C@]1(C)CCCC2(C)C)/C=O
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
NPO24124 Curcuma longa Species Zingiberaceae Eukaryota PMID[9584408]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT165 Cell Line HeLa Homo sapiens IC50 = 19.5 ug/ml Open TG-GATES in vivo data: Biochemistry
NPT788 Cell Line SNU1 Homo sapiens IC50 = 12 ug/ml 10346951
NPT189 Cell Line Vero Chlorocebus aethiops IC50 = 13.1 ug/ml 8984161
NPT319 Cell Line B16 Mus musculus IC50 = 41.2 ug/ml 15387647
NPT168 Cell Line P388 Mus musculus IC50 = 4.1 ug/ml 20361780
NPT91 Cell Line KB Homo sapiens ED50 = 40 ug/ml 22377672
NPT329 Organism Trichophyton rubrum Trichophyton rubrum MIC = 0.62 ug/ml 23398362
NPT1381 Organism Aedes aegypti Aedes aegypti Activity = 100 % 12193011
NPT637 Organism Fusarium oxysporum Fusarium oxysporum MIC = 19.8 ug/ml 18227183
NPT190 Organism Human herpesvirus 1 Human herpesvirus 1 Activity = 100 Open TG-GATES in vivo data: Hematology
NPT330 Organism Trichophyton mentagrophytes Trichophyton mentagrophytes MIC = 1.24 ug/ml Open TG-GATES in vivo data: Hematology
NPT87 Organism Aspergillus fumigatus Aspergillus fumigatus MIC = 79.4 ug/ml 20553004

  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 NPC52449 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 NPC169275
0.8906 High Similarity NPC4370
0.8906 High Similarity NPC290350
0.8806 High Similarity NPC144947
0.8769 High Similarity NPC155198
0.8676 High Similarity NPC211641
0.8676 High Similarity NPC75485
0.8676 High Similarity NPC219232
0.8676 High Similarity NPC168975
0.8676 High Similarity NPC128346
0.8406 Intermediate Similarity NPC238146
0.8382 Intermediate Similarity NPC474562
0.8308 Intermediate Similarity NPC268039
0.8226 Intermediate Similarity NPC60772
0.8194 Intermediate Similarity NPC115515
0.8169 Intermediate Similarity NPC469793
0.8169 Intermediate Similarity NPC469796
0.8082 Intermediate Similarity NPC283789
0.7945 Intermediate Similarity NPC59436
0.7917 Intermediate Similarity NPC19907
0.7857 Intermediate Similarity NPC304983
0.7808 Intermediate Similarity NPC470428
0.7794 Intermediate Similarity NPC193770
0.7778 Intermediate Similarity NPC208749
0.7778 Intermediate Similarity NPC321568
0.7778 Intermediate Similarity NPC22019
0.7778 Intermediate Similarity NPC281986
0.7761 Intermediate Similarity NPC183422
0.7733 Intermediate Similarity NPC474509
0.7714 Intermediate Similarity NPC251929
0.7714 Intermediate Similarity NPC260040
0.7714 Intermediate Similarity NPC265782
0.7714 Intermediate Similarity NPC2634
0.7703 Intermediate Similarity NPC228911
0.7703 Intermediate Similarity NPC476949
0.7692 Intermediate Similarity NPC127582
0.7681 Intermediate Similarity NPC260474
0.7681 Intermediate Similarity NPC188292
0.7662 Intermediate Similarity NPC307258
0.7647 Intermediate Similarity NPC185587
0.7639 Intermediate Similarity NPC20025
0.7639 Intermediate Similarity NPC309852
0.7632 Intermediate Similarity NPC90055
0.7606 Intermediate Similarity NPC54123
0.76 Intermediate Similarity NPC470429
0.76 Intermediate Similarity NPC90965
0.76 Intermediate Similarity NPC170793
0.7571 Intermediate Similarity NPC139397
0.7532 Intermediate Similarity NPC470813
0.7532 Intermediate Similarity NPC142683
0.75 Intermediate Similarity NPC251118
0.75 Intermediate Similarity NPC474228
0.75 Intermediate Similarity NPC303613
0.75 Intermediate Similarity NPC107258
0.7468 Intermediate Similarity NPC2709
0.7465 Intermediate Similarity NPC307176
0.7463 Intermediate Similarity NPC288253
0.7463 Intermediate Similarity NPC202118
0.7463 Intermediate Similarity NPC197238
0.7432 Intermediate Similarity NPC4509
0.7429 Intermediate Similarity NPC87141
0.7429 Intermediate Similarity NPC310992
0.7419 Intermediate Similarity NPC23117
0.7397 Intermediate Similarity NPC474797
0.7397 Intermediate Similarity NPC78527
0.7397 Intermediate Similarity NPC474796
0.7397 Intermediate Similarity NPC329866
0.7391 Intermediate Similarity NPC92327
0.7385 Intermediate Similarity NPC311852
0.7368 Intermediate Similarity NPC476177
0.7361 Intermediate Similarity NPC21944
0.7361 Intermediate Similarity NPC133253
0.7361 Intermediate Similarity NPC190035
0.7353 Intermediate Similarity NPC469662
0.7353 Intermediate Similarity NPC475124
0.7353 Intermediate Similarity NPC212210
0.7353 Intermediate Similarity NPC285371
0.7333 Intermediate Similarity NPC219809
0.7324 Intermediate Similarity NPC256846
0.7313 Intermediate Similarity NPC60565
0.7302 Intermediate Similarity NPC250539
0.7286 Intermediate Similarity NPC176107
0.7286 Intermediate Similarity NPC475523
0.7273 Intermediate Similarity NPC471514
0.7273 Intermediate Similarity NPC276764
0.7273 Intermediate Similarity NPC472304
0.726 Intermediate Similarity NPC251705
0.7222 Intermediate Similarity NPC159577
0.7222 Intermediate Similarity NPC282593
0.7222 Intermediate Similarity NPC35734
0.7215 Intermediate Similarity NPC470165
0.72 Intermediate Similarity NPC69408
0.72 Intermediate Similarity NPC474463
0.7188 Intermediate Similarity NPC188789
0.7162 Intermediate Similarity NPC159497
0.7162 Intermediate Similarity NPC255021
0.7143 Intermediate Similarity NPC242945
0.7143 Intermediate Similarity NPC176171
0.7143 Intermediate Similarity NPC14002
0.7143 Intermediate Similarity NPC259156
0.7125 Intermediate Similarity NPC470812
0.7123 Intermediate Similarity NPC234707
0.7123 Intermediate Similarity NPC474539
0.7123 Intermediate Similarity NPC305501
0.7123 Intermediate Similarity NPC225467
0.7123 Intermediate Similarity NPC115023
0.7121 Intermediate Similarity NPC56905
0.7121 Intermediate Similarity NPC27610
0.7108 Intermediate Similarity NPC469546
0.7108 Intermediate Similarity NPC184663
0.7105 Intermediate Similarity NPC472300
0.7101 Intermediate Similarity NPC329698
0.7089 Intermediate Similarity NPC200513
0.7089 Intermediate Similarity NPC94200
0.7083 Intermediate Similarity NPC61702
0.7083 Intermediate Similarity NPC286814
0.7083 Intermediate Similarity NPC162867
0.7067 Intermediate Similarity NPC255650
0.7067 Intermediate Similarity NPC473171
0.7067 Intermediate Similarity NPC65650
0.7067 Intermediate Similarity NPC476346
0.7067 Intermediate Similarity NPC293803
0.7059 Intermediate Similarity NPC213152
0.7051 Intermediate Similarity NPC472478
0.7051 Intermediate Similarity NPC2482
0.7049 Intermediate Similarity NPC22765
0.7037 Intermediate Similarity NPC70685
0.7037 Intermediate Similarity NPC33881
0.7031 Intermediate Similarity NPC5626
0.7031 Intermediate Similarity NPC100809
0.7031 Intermediate Similarity NPC209431
0.7027 Intermediate Similarity NPC470044
0.7027 Intermediate Similarity NPC470045
0.7027 Intermediate Similarity NPC130016
0.7027 Intermediate Similarity NPC56747
0.7027 Intermediate Similarity NPC109576
0.7027 Intermediate Similarity NPC180015
0.7024 Intermediate Similarity NPC101651
0.7024 Intermediate Similarity NPC159748
0.7015 Intermediate Similarity NPC259261
0.7013 Intermediate Similarity NPC253561
0.7013 Intermediate Similarity NPC62336
0.7013 Intermediate Similarity NPC80088
0.7013 Intermediate Similarity NPC198240
0.7 Intermediate Similarity NPC470329
0.7 Intermediate Similarity NPC469
0.6988 Remote Similarity NPC206060
0.6986 Remote Similarity NPC40574
0.6984 Remote Similarity NPC22182
0.6974 Remote Similarity NPC26504
0.6974 Remote Similarity NPC263582
0.6974 Remote Similarity NPC1254
0.6974 Remote Similarity NPC250621
0.6974 Remote Similarity NPC470525
0.697 Remote Similarity NPC11130
0.697 Remote Similarity NPC192427
0.697 Remote Similarity NPC115385
0.6962 Remote Similarity NPC6663
0.6962 Remote Similarity NPC149237
0.6962 Remote Similarity NPC121984
0.6962 Remote Similarity NPC116797
0.6951 Remote Similarity NPC168248
0.6944 Remote Similarity NPC20610
0.6944 Remote Similarity NPC39157
0.6944 Remote Similarity NPC296697
0.6944 Remote Similarity NPC82477
0.6944 Remote Similarity NPC142754
0.6941 Remote Similarity NPC230064
0.6935 Remote Similarity NPC228776
0.6933 Remote Similarity NPC147438
0.6933 Remote Similarity NPC166797
0.6923 Remote Similarity NPC152061
0.6923 Remote Similarity NPC170394
0.6923 Remote Similarity NPC190211
0.6914 Remote Similarity NPC472265
0.6914 Remote Similarity NPC476412
0.6912 Remote Similarity NPC25853
0.6901 Remote Similarity NPC323005
0.6892 Remote Similarity NPC72343
0.6892 Remote Similarity NPC5701
0.6883 Remote Similarity NPC203403
0.6883 Remote Similarity NPC165711
0.6883 Remote Similarity NPC61952
0.6875 Remote Similarity NPC296311
0.6875 Remote Similarity NPC103486
0.6867 Remote Similarity NPC89747
0.6866 Remote Similarity NPC30215
0.6866 Remote Similarity NPC94991
0.6866 Remote Similarity NPC266295
0.6866 Remote Similarity NPC170799
0.6866 Remote Similarity NPC308108
0.686 Remote Similarity NPC151722
0.6857 Remote Similarity NPC4638
0.6857 Remote Similarity NPC473902
0.6857 Remote Similarity NPC6697
0.6849 Remote Similarity NPC182815
0.6835 Remote Similarity NPC474956
0.6835 Remote Similarity NPC476809
0.6835 Remote Similarity NPC472301
0.6833 Remote Similarity NPC86683

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC52449 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
0.7714 Intermediate Similarity NPD4691 Approved
0.7571 Intermediate Similarity NPD4137 Phase 3
0.7465 Intermediate Similarity NPD4747 Approved
0.7397 Intermediate Similarity NPD4058 Approved
0.7123 Intermediate Similarity NPD5276 Approved
0.7089 Intermediate Similarity NPD4752 Clinical (unspecified phase)
0.6944 Remote Similarity NPD3621 Clinical (unspecified phase)
0.6933 Remote Similarity NPD4687 Approved
0.6933 Remote Similarity NPD5733 Approved
0.6866 Remote Similarity NPD287 Approved
0.6835 Remote Similarity NPD4695 Discontinued
0.6707 Remote Similarity NPD3665 Phase 1
0.6707 Remote Similarity NPD3133 Approved
0.6707 Remote Similarity NPD3666 Approved
0.6548 Remote Similarity NPD7521 Approved
0.6548 Remote Similarity NPD3618 Phase 1
0.6548 Remote Similarity NPD7334 Approved
0.6548 Remote Similarity NPD7146 Approved
0.6548 Remote Similarity NPD6684 Approved
0.6548 Remote Similarity NPD5330 Approved
0.6548 Remote Similarity NPD6409 Approved
0.6543 Remote Similarity NPD8028 Phase 2
0.65 Remote Similarity NPD4195 Approved
0.6463 Remote Similarity NPD4223 Phase 3
0.6463 Remote Similarity NPD4221 Approved
0.6463 Remote Similarity NPD3667 Approved
0.6444 Remote Similarity NPD4697 Phase 3
0.6395 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6395 Remote Similarity NPD6903 Approved
0.6395 Remote Similarity NPD5737 Approved
0.6395 Remote Similarity NPD6672 Approved
0.6386 Remote Similarity NPD3527 Clinical (unspecified phase)
0.6364 Remote Similarity NPD6079 Approved
0.6353 Remote Similarity NPD5279 Phase 3
0.6338 Remote Similarity NPD4192 Approved
0.6338 Remote Similarity NPD4191 Approved
0.6338 Remote Similarity NPD4194 Approved
0.6338 Remote Similarity NPD4193 Approved
0.6322 Remote Similarity NPD5328 Approved
0.6322 Remote Similarity NPD4753 Phase 2
0.631 Remote Similarity NPD4786 Approved
0.631 Remote Similarity NPD3668 Phase 3
0.631 Remote Similarity NPD4197 Approved
0.6279 Remote Similarity NPD3573 Approved
0.6235 Remote Similarity NPD5329 Approved
0.6222 Remote Similarity NPD7900 Approved
0.6222 Remote Similarity NPD7901 Clinical (unspecified phase)
0.6184 Remote Similarity NPD6922 Approved
0.6184 Remote Similarity NPD6923 Approved
0.618 Remote Similarity NPD7515 Phase 2
0.6173 Remote Similarity NPD3617 Approved
0.6164 Remote Similarity NPD5325 Clinical (unspecified phase)
0.6163 Remote Similarity NPD4688 Approved
0.6163 Remote Similarity NPD5205 Approved
0.6163 Remote Similarity NPD4138 Approved
0.6163 Remote Similarity NPD4690 Approved
0.6163 Remote Similarity NPD4693 Phase 3
0.6163 Remote Similarity NPD3574 Clinical (unspecified phase)
0.6163 Remote Similarity NPD5690 Phase 2
0.6163 Remote Similarity NPD4623 Approved
0.6163 Remote Similarity NPD4689 Approved
0.6163 Remote Similarity NPD4519 Discontinued
0.6154 Remote Similarity NPD4629 Approved
0.6154 Remote Similarity NPD5210 Approved
0.6125 Remote Similarity NPD3701 Clinical (unspecified phase)
0.6111 Remote Similarity NPD4202 Approved
0.6104 Remote Similarity NPD7144 Approved
0.6104 Remote Similarity NPD7143 Approved
0.6087 Remote Similarity NPD5222 Approved
0.6087 Remote Similarity NPD5220 Clinical (unspecified phase)
0.6087 Remote Similarity NPD5221 Approved
0.6087 Remote Similarity NPD4219 Approved
0.6076 Remote Similarity NPD6924 Approved
0.6076 Remote Similarity NPD6926 Approved
0.6066 Remote Similarity NPD1799 Clinical (unspecified phase)
0.6044 Remote Similarity NPD7748 Approved
0.6026 Remote Similarity NPD7152 Approved
0.6026 Remote Similarity NPD7150 Approved
0.6026 Remote Similarity NPD7151 Approved
0.6024 Remote Similarity NPD8259 Clinical (unspecified phase)
0.6023 Remote Similarity NPD5208 Approved
0.6022 Remote Similarity NPD7902 Approved
0.6022 Remote Similarity NPD5173 Approved
0.6 Remote Similarity NPD4788 Approved
0.6 Remote Similarity NPD6942 Approved
0.6 Remote Similarity NPD7339 Approved
0.5977 Remote Similarity NPD4694 Approved
0.5977 Remote Similarity NPD5280 Approved
0.5957 Remote Similarity NPD4225 Approved
0.5955 Remote Similarity NPD6080 Approved
0.5955 Remote Similarity NPD6904 Approved
0.5955 Remote Similarity NPD6673 Approved
0.5934 Remote Similarity NPD6399 Phase 3
0.5926 Remote Similarity NPD6933 Approved
0.5904 Remote Similarity NPD7645 Phase 2
0.5895 Remote Similarity NPD5285 Approved
0.5895 Remote Similarity NPD4696 Approved
0.5895 Remote Similarity NPD5286 Approved
0.5862 Remote Similarity NPD1694 Approved
0.5854 Remote Similarity NPD6925 Approved
0.5854 Remote Similarity NPD5776 Phase 2
0.5854 Remote Similarity NPD6932 Approved
0.5851 Remote Similarity NPD4755 Approved
0.5851 Remote Similarity NPD6084 Phase 2
0.5851 Remote Similarity NPD6083 Phase 2
0.5833 Remote Similarity NPD7525 Registered
0.5833 Remote Similarity NPD5223 Approved
0.5824 Remote Similarity NPD5693 Phase 1
0.5823 Remote Similarity NPD4243 Approved
0.5806 Remote Similarity NPD6356 Clinical (unspecified phase)
0.5806 Remote Similarity NPD5695 Phase 3
0.5802 Remote Similarity NPD8264 Approved
0.5802 Remote Similarity NPD8039 Approved
0.5795 Remote Similarity NPD6098 Approved
0.5789 Remote Similarity NPD7638 Approved
0.5789 Remote Similarity NPD7331 Phase 2
0.5789 Remote Similarity NPD5696 Approved
0.5783 Remote Similarity NPD7145 Approved
0.5783 Remote Similarity NPD7322 Clinical (unspecified phase)
0.5778 Remote Similarity NPD7285 Clinical (unspecified phase)
0.5773 Remote Similarity NPD5225 Approved
0.5773 Remote Similarity NPD4633 Approved
0.5773 Remote Similarity NPD5211 Phase 2
0.5773 Remote Similarity NPD5224 Approved
0.5773 Remote Similarity NPD5226 Approved
0.5758 Remote Similarity NPD8262 Approved
0.5745 Remote Similarity NPD7732 Phase 3
0.5729 Remote Similarity NPD7639 Approved
0.5729 Remote Similarity NPD4700 Approved
0.5729 Remote Similarity NPD7640 Approved
0.5714 Remote Similarity NPD5692 Phase 3
0.5714 Remote Similarity NPD5175 Approved
0.5714 Remote Similarity NPD5207 Approved
0.5714 Remote Similarity NPD5174 Approved
0.5714 Remote Similarity NPD4096 Approved
0.5714 Remote Similarity NPD6683 Phase 2
0.5714 Remote Similarity NPD6929 Approved
0.5699 Remote Similarity NPD6001 Approved
0.5698 Remote Similarity NPD5209 Approved
0.5684 Remote Similarity NPD3495 Discontinued
0.5682 Remote Similarity NPD1696 Phase 3
0.5679 Remote Similarity NPD4784 Approved
0.5679 Remote Similarity NPD4785 Approved
0.5658 Remote Similarity NPD2685 Clinical (unspecified phase)
0.5657 Remote Similarity NPD5141 Approved
0.5652 Remote Similarity NPD5281 Approved
0.5652 Remote Similarity NPD6050 Approved
0.5652 Remote Similarity NPD5694 Approved
0.5652 Remote Similarity NPD5284 Approved
0.5652 Remote Similarity NPD7637 Suspended
0.5647 Remote Similarity NPD6931 Approved
0.5647 Remote Similarity NPD7509 Discontinued
0.5647 Remote Similarity NPD7514 Phase 3
0.5647 Remote Similarity NPD6930 Phase 2
0.5647 Remote Similarity NPD7332 Phase 2
0.5625 Remote Similarity NPD5290 Discontinued
0.561 Remote Similarity NPD4190 Phase 3
0.561 Remote Similarity NPD5275 Approved
0.5604 Remote Similarity NPD6051 Approved

Structure

External Identifiers

PubChem CID   9796432
ChEMBL   CHEMBL491531
ZINC  

Physicochemical Properties

Molecular Weight:  302.22
ALogP:  1.5759
MLogP:  3.44
XLogP:  6.642
# Rotatable Bonds:  8
Polar Surface Area:  34.14
# H-Bond Aceptor:  2
# H-Bond Donor:  0
# Rings:  2
# Heavy Atoms:  22

Download Data

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