Natural Product: NPC175186

Natural Product ID:  NPC175186
Common Name:   23-Hydroxytoonacilide
IUPAC Name:   methyl 2-[(1R,2S)-2-[(1aR,3R,3aR,4R,5R,6R,7aS)-4,5-diacetyloxy-3-(2-hydroxy-5-oxo-2H-furan-4-yl)-3a-methyl-7-methylidene-1a,2,3,4,5,6-hexahydroindeno[1,7a-b]oxiren-6-yl]-2,6,6-trimethyl-5-oxocyclohex-3-en-1-yl]acetate
Synonyms:   23-Hydroxytoonacilide
Molecular Formula:   C31H38O11
Standard InCHIKey:  JMIQCHPADBJCET-VKUOMARPSA-N
Standard InCHI:  InChI=1S/C31H38O11/c1-14-24(29(6)10-9-20(34)28(4,5)19(29)13-22(35)38-8)25(39-15(2)32)26(40-16(3)33)30(7)18(12-21-31(14,30)42-21)17-11-23(36)41-27(17)37/h9-11,18-19,21,23-26,36H,1,12-13H2,2-8H3/t18-,19-,21+,23?,24+,25+,26-,29-,30+,31+/m0/s1
Canonical SMILES:  COC(=O)C[C@@H]1[C@](C)(C=CC(=O)C1(C)C)[C@H]1[C@@H](OC(=O)C)[C@H](OC(=O)C)[C@@]2([C@]3(C1=C)O[C@@H]3C[C@H]2C1=CC(OC1=O)O)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
NPO10033 Turraea pubescens Species Meliaceae Eukaryota Twigs Dongfang, Hainan Province, China 2010-MAR PMID[23734701]
NPO20688 Turraea parvifolia Species Meliaceae Eukaryota TCMID*

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT113 Cell Line RAW264.7 Mus musculus IC50 = 41400 nM 22537362
NPT113 Cell Line RAW264.7 Mus musculus IC50 > 20000 nM 23734701
NPT116 Cell Line HL-60 Homo sapiens IC50 < 10000 nM 23734701

  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 NPC175186 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
0.9916 High Similarity NPC471170
0.9832 High Similarity NPC104382
0.9187 High Similarity NPC470851
0.9083 High Similarity NPC310511
0.8952 High Similarity NPC470850
0.8889 High Similarity NPC472769
0.888 High Similarity NPC472770
0.8699 High Similarity NPC470419
0.8678 High Similarity NPC470420
0.8629 High Similarity NPC473979
0.8629 High Similarity NPC472768
0.8607 High Similarity NPC472667
0.8605 High Similarity NPC478072
0.8605 High Similarity NPC471234
0.8583 High Similarity NPC231529
0.8571 High Similarity NPC287423
0.8571 High Similarity NPC42399
0.8537 High Similarity NPC143755
0.8537 High Similarity NPC4548
0.8512 High Similarity NPC470793
0.8504 High Similarity NPC473620
0.8504 High Similarity NPC311534
0.8468 Intermediate Similarity NPC204731
0.8468 Intermediate Similarity NPC470418
0.845 Intermediate Similarity NPC471855
0.8372 Intermediate Similarity NPC476852
0.8361 Intermediate Similarity NPC471816
0.8359 Intermediate Similarity NPC476859
0.8346 Intermediate Similarity NPC293112
0.8333 Intermediate Similarity NPC27363
0.8333 Intermediate Similarity NPC469382
0.8295 Intermediate Similarity NPC476851
0.8295 Intermediate Similarity NPC473593
0.8295 Intermediate Similarity NPC471407
0.8281 Intermediate Similarity NPC117702
0.8281 Intermediate Similarity NPC471356
0.8281 Intermediate Similarity NPC469757
0.8281 Intermediate Similarity NPC471357
0.8281 Intermediate Similarity NPC298841
0.8281 Intermediate Similarity NPC146456
0.8281 Intermediate Similarity NPC179412
0.8268 Intermediate Similarity NPC469379
0.8268 Intermediate Similarity NPC86346
0.8268 Intermediate Similarity NPC172154
0.8268 Intermediate Similarity NPC81736
0.8268 Intermediate Similarity NPC75856
0.8254 Intermediate Similarity NPC222688
0.824 Intermediate Similarity NPC241192
0.824 Intermediate Similarity NPC472004
0.824 Intermediate Similarity NPC48692
0.8231 Intermediate Similarity NPC476855
0.8231 Intermediate Similarity NPC476863
0.8231 Intermediate Similarity NPC476862
0.8217 Intermediate Similarity NPC270109
0.8211 Intermediate Similarity NPC106228
0.8211 Intermediate Similarity NPC138372
0.8203 Intermediate Similarity NPC473635
0.8203 Intermediate Similarity NPC469750
0.8203 Intermediate Similarity NPC250556
0.8189 Intermediate Similarity NPC11895
0.8189 Intermediate Similarity NPC469789
0.8175 Intermediate Similarity NPC46570
0.8175 Intermediate Similarity NPC202051
0.8168 Intermediate Similarity NPC93416
0.8168 Intermediate Similarity NPC231240
0.8162 Intermediate Similarity NPC48414
0.8162 Intermediate Similarity NPC5153
0.816 Intermediate Similarity NPC19028
0.816 Intermediate Similarity NPC475041
0.816 Intermediate Similarity NPC161065
0.816 Intermediate Similarity NPC5292
0.816 Intermediate Similarity NPC9674
0.8154 Intermediate Similarity NPC10823
0.8154 Intermediate Similarity NPC6108
0.8154 Intermediate Similarity NPC251866
0.8154 Intermediate Similarity NPC471352
0.8154 Intermediate Similarity NPC219085
0.8154 Intermediate Similarity NPC17896
0.8154 Intermediate Similarity NPC469751
0.8154 Intermediate Similarity NPC284406
0.8154 Intermediate Similarity NPC469754
0.8154 Intermediate Similarity NPC471361
0.8154 Intermediate Similarity NPC197707
0.8154 Intermediate Similarity NPC469753
0.8154 Intermediate Similarity NPC471359
0.8154 Intermediate Similarity NPC180079
0.8154 Intermediate Similarity NPC86159
0.8154 Intermediate Similarity NPC70542
0.8154 Intermediate Similarity NPC89514
0.8154 Intermediate Similarity NPC476854
0.8154 Intermediate Similarity NPC9499
0.8154 Intermediate Similarity NPC471360
0.8154 Intermediate Similarity NPC471358
0.8154 Intermediate Similarity NPC469752
0.8154 Intermediate Similarity NPC469755
0.814 Intermediate Similarity NPC240070
0.814 Intermediate Similarity NPC329784
0.813 Intermediate Similarity NPC178289
0.8125 Intermediate Similarity NPC8369
0.811 Intermediate Similarity NPC23786
0.811 Intermediate Similarity NPC170538
0.811 Intermediate Similarity NPC28532
0.811 Intermediate Similarity NPC269642
0.811 Intermediate Similarity NPC470265
0.811 Intermediate Similarity NPC107493
0.8106 Intermediate Similarity NPC298783
0.8106 Intermediate Similarity NPC316915
0.8106 Intermediate Similarity NPC157817
0.8106 Intermediate Similarity NPC104585
0.8106 Intermediate Similarity NPC225385
0.8095 Intermediate Similarity NPC474585
0.8095 Intermediate Similarity NPC151616
0.8095 Intermediate Similarity NPC109973
0.8095 Intermediate Similarity NPC79579
0.8095 Intermediate Similarity NPC157252
0.8095 Intermediate Similarity NPC471128
0.8095 Intermediate Similarity NPC145182
0.8095 Intermediate Similarity NPC471126
0.8092 Intermediate Similarity NPC16569
0.8092 Intermediate Similarity NPC253456
0.8092 Intermediate Similarity NPC475389
0.8092 Intermediate Similarity NPC473838
0.8092 Intermediate Similarity NPC159338
0.8092 Intermediate Similarity NPC173347
0.808 Intermediate Similarity NPC234522
0.808 Intermediate Similarity NPC153440
0.808 Intermediate Similarity NPC475913
0.8077 Intermediate Similarity NPC477490
0.8077 Intermediate Similarity NPC114306
0.8077 Intermediate Similarity NPC245094
0.8074 Intermediate Similarity NPC290746
0.8074 Intermediate Similarity NPC79250
0.8069 Intermediate Similarity NPC471176
0.8065 Intermediate Similarity NPC154363
0.8065 Intermediate Similarity NPC49492
0.8065 Intermediate Similarity NPC471127
0.8065 Intermediate Similarity NPC234858
0.8065 Intermediate Similarity NPC190286
0.8065 Intermediate Similarity NPC266728
0.8065 Intermediate Similarity NPC302471
0.8065 Intermediate Similarity NPC243981
0.8062 Intermediate Similarity NPC222307
0.8049 Intermediate Similarity NPC250109
0.8049 Intermediate Similarity NPC471173
0.8049 Intermediate Similarity NPC962
0.8049 Intermediate Similarity NPC471627
0.8049 Intermediate Similarity NPC317210
0.8047 Intermediate Similarity NPC471392
0.8047 Intermediate Similarity NPC472399
0.8047 Intermediate Similarity NPC204812
0.8043 Intermediate Similarity NPC471172
0.8031 Intermediate Similarity NPC472000
0.8031 Intermediate Similarity NPC471999
0.8031 Intermediate Similarity NPC470878
0.8031 Intermediate Similarity NPC472001
0.8031 Intermediate Similarity NPC67569
0.8031 Intermediate Similarity NPC52839
0.8031 Intermediate Similarity NPC473256
0.803 Intermediate Similarity NPC180902
0.803 Intermediate Similarity NPC42670
0.803 Intermediate Similarity NPC19124
0.803 Intermediate Similarity NPC475139
0.8017 Intermediate Similarity NPC471934
0.8016 Intermediate Similarity NPC475834
0.8016 Intermediate Similarity NPC474179
0.8016 Intermediate Similarity NPC469380
0.8016 Intermediate Similarity NPC475520
0.8016 Intermediate Similarity NPC156745
0.8016 Intermediate Similarity NPC236918
0.8015 Intermediate Similarity NPC140092
0.8015 Intermediate Similarity NPC232785
0.8015 Intermediate Similarity NPC188234
0.8015 Intermediate Similarity NPC125077
0.8015 Intermediate Similarity NPC329986
0.8015 Intermediate Similarity NPC476966
0.8015 Intermediate Similarity NPC276838
0.8015 Intermediate Similarity NPC91
0.8015 Intermediate Similarity NPC470880
0.8 Intermediate Similarity NPC470882
0.8 Intermediate Similarity NPC203862
0.8 Intermediate Similarity NPC473253
0.8 Intermediate Similarity NPC10721
0.8 Intermediate Similarity NPC13713
0.8 Intermediate Similarity NPC305496
0.8 Intermediate Similarity NPC469684
0.8 Intermediate Similarity NPC473968
0.7986 Intermediate Similarity NPC48813
0.7986 Intermediate Similarity NPC194854
0.7984 Intermediate Similarity NPC473709
0.7984 Intermediate Similarity NPC473919
0.7984 Intermediate Similarity NPC241456
0.7984 Intermediate Similarity NPC8374
0.7984 Intermediate Similarity NPC32868
0.7984 Intermediate Similarity NPC238667
0.7984 Intermediate Similarity NPC181145
0.7984 Intermediate Similarity NPC145238
0.797 Intermediate Similarity NPC247190
0.797 Intermediate Similarity NPC477709
0.797 Intermediate Similarity NPC146857
0.797 Intermediate Similarity NPC32793

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC175186 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
0.8203 Intermediate Similarity NPD7507 Approved
0.8154 Intermediate Similarity NPD7319 Approved
0.8016 Intermediate Similarity NPD7516 Approved
0.7937 Intermediate Similarity NPD7327 Approved
0.7937 Intermediate Similarity NPD7328 Approved
0.7829 Intermediate Similarity NPD6370 Approved
0.7803 Intermediate Similarity NPD7736 Approved
0.7717 Intermediate Similarity NPD7115 Discovery
0.771 Intermediate Similarity NPD7492 Approved
0.768 Intermediate Similarity NPD6882 Approved
0.768 Intermediate Similarity NPD8297 Approved
0.7674 Intermediate Similarity NPD6054 Approved
0.7652 Intermediate Similarity NPD6616 Approved
0.7623 Intermediate Similarity NPD6008 Approved
0.7615 Intermediate Similarity NPD8378 Approved
0.7615 Intermediate Similarity NPD8033 Approved
0.7615 Intermediate Similarity NPD8296 Approved
0.7615 Intermediate Similarity NPD8335 Approved
0.7615 Intermediate Similarity NPD8380 Approved
0.7615 Intermediate Similarity NPD8379 Approved
0.7594 Intermediate Similarity NPD8293 Discontinued
0.7594 Intermediate Similarity NPD7078 Approved
0.7581 Intermediate Similarity NPD4061 Clinical (unspecified phase)
0.7578 Intermediate Similarity NPD6009 Approved
0.7538 Intermediate Similarity NPD8377 Approved
0.7538 Intermediate Similarity NPD8294 Approved
0.7538 Intermediate Similarity NPD6319 Approved
0.752 Intermediate Similarity NPD5955 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD6881 Approved
0.75 Intermediate Similarity NPD6686 Approved
0.75 Intermediate Similarity NPD6899 Approved
0.7481 Intermediate Similarity NPD6016 Approved
0.7481 Intermediate Similarity NPD7503 Approved
0.7481 Intermediate Similarity NPD6015 Approved
0.748 Intermediate Similarity NPD4632 Approved
0.746 Intermediate Similarity NPD6649 Approved
0.746 Intermediate Similarity NPD6650 Approved
0.7424 Intermediate Similarity NPD5988 Approved
0.7419 Intermediate Similarity NPD5697 Approved
0.7419 Intermediate Similarity NPD5954 Clinical (unspecified phase)
0.7405 Intermediate Similarity NPD6059 Approved
0.7381 Intermediate Similarity NPD7102 Approved
0.7381 Intermediate Similarity NPD7290 Approved
0.7381 Intermediate Similarity NPD6883 Approved
0.7368 Intermediate Similarity NPD7604 Phase 2
0.736 Intermediate Similarity NPD7320 Approved
0.7339 Intermediate Similarity NPD6402 Approved
0.7339 Intermediate Similarity NPD5739 Approved
0.7339 Intermediate Similarity NPD6675 Approved
0.7339 Intermediate Similarity NPD7128 Approved
0.7323 Intermediate Similarity NPD6617 Approved
0.7323 Intermediate Similarity NPD8130 Phase 1
0.7323 Intermediate Similarity NPD6847 Approved
0.7323 Intermediate Similarity NPD6869 Approved
0.7302 Intermediate Similarity NPD6012 Approved
0.7302 Intermediate Similarity NPD6013 Approved
0.7302 Intermediate Similarity NPD6372 Approved
0.7302 Intermediate Similarity NPD6373 Approved
0.7302 Intermediate Similarity NPD6014 Approved
0.7295 Intermediate Similarity NPD5344 Discontinued
0.728 Intermediate Similarity NPD6412 Phase 2
0.7266 Intermediate Similarity NPD6053 Discontinued
0.7236 Intermediate Similarity NPD5211 Phase 2
0.7222 Intermediate Similarity NPD6011 Approved
0.7218 Intermediate Similarity NPD5983 Phase 2
0.7213 Intermediate Similarity NPD7639 Approved
0.7213 Intermediate Similarity NPD6648 Approved
0.7213 Intermediate Similarity NPD7640 Approved
0.7143 Intermediate Similarity NPD5701 Approved
0.7132 Intermediate Similarity NPD6336 Discontinued
0.7131 Intermediate Similarity NPD7638 Approved
0.712 Intermediate Similarity NPD5141 Approved
0.7073 Intermediate Similarity NPD4696 Approved
0.7073 Intermediate Similarity NPD5286 Approved
0.7073 Intermediate Similarity NPD5285 Approved
0.6977 Remote Similarity NPD6371 Approved
0.6977 Remote Similarity NPD4634 Approved
0.6963 Remote Similarity NPD8516 Approved
0.6963 Remote Similarity NPD8513 Phase 3
0.6963 Remote Similarity NPD8517 Approved
0.6963 Remote Similarity NPD8515 Approved
0.696 Remote Similarity NPD5224 Approved
0.696 Remote Similarity NPD5225 Approved
0.696 Remote Similarity NPD4633 Approved
0.696 Remote Similarity NPD5226 Approved
0.6953 Remote Similarity NPD5345 Clinical (unspecified phase)
0.695 Remote Similarity NPD8338 Approved
0.6947 Remote Similarity NPD8133 Approved
0.694 Remote Similarity NPD7101 Approved
0.694 Remote Similarity NPD7100 Approved
0.6923 Remote Similarity NPD6401 Clinical (unspecified phase)
0.6911 Remote Similarity NPD4755 Approved
0.6906 Remote Similarity NPD6033 Approved
0.6905 Remote Similarity NPD5175 Approved
0.6905 Remote Similarity NPD5174 Approved
0.688 Remote Similarity NPD5223 Approved
0.6879 Remote Similarity NPD7260 Phase 2
0.6866 Remote Similarity NPD6335 Approved
0.6861 Remote Similarity NPD6067 Discontinued
0.6861 Remote Similarity NPD8328 Phase 3
0.6842 Remote Similarity NPD6274 Approved
0.6822 Remote Similarity NPD4730 Approved
0.6822 Remote Similarity NPD4729 Approved
0.68 Remote Similarity NPD4700 Approved
0.6791 Remote Similarity NPD6317 Approved
0.6777 Remote Similarity NPD6079 Approved
0.6774 Remote Similarity NPD6084 Phase 2
0.6774 Remote Similarity NPD6083 Phase 2
0.6769 Remote Similarity NPD8132 Clinical (unspecified phase)
0.6748 Remote Similarity NPD6356 Clinical (unspecified phase)
0.6741 Remote Similarity NPD6314 Approved
0.6741 Remote Similarity NPD6313 Approved
0.672 Remote Similarity NPD5696 Approved
0.672 Remote Similarity NPD4225 Approved
0.6718 Remote Similarity NPD5251 Approved
0.6718 Remote Similarity NPD5250 Approved
0.6718 Remote Similarity NPD5248 Approved
0.6718 Remote Similarity NPD5249 Phase 3
0.6718 Remote Similarity NPD5247 Approved
0.6715 Remote Similarity NPD6291 Clinical (unspecified phase)
0.6694 Remote Similarity NPD46 Approved
0.6694 Remote Similarity NPD6698 Approved
0.6693 Remote Similarity NPD7632 Discontinued
0.6667 Remote Similarity NPD4767 Approved
0.6667 Remote Similarity NPD4768 Approved
0.6615 Remote Similarity NPD7899 Clinical (unspecified phase)
0.6613 Remote Similarity NPD5210 Approved
0.6613 Remote Similarity NPD5695 Phase 3
0.6613 Remote Similarity NPD4629 Approved
0.6612 Remote Similarity NPD5328 Approved
0.6597 Remote Similarity NPD6845 Suspended
0.6594 Remote Similarity NPD6909 Approved
0.6594 Remote Similarity NPD6908 Approved
0.6585 Remote Similarity NPD4202 Approved
0.6585 Remote Similarity NPD6399 Phase 3
0.6566 Remote Similarity NPD7799 Discontinued
0.6565 Remote Similarity NPD5128 Approved
0.656 Remote Similarity NPD5220 Clinical (unspecified phase)
0.656 Remote Similarity NPD5221 Approved
0.656 Remote Similarity NPD5222 Approved
0.6557 Remote Similarity NPD5785 Approved
0.6549 Remote Similarity NPD8336 Approved
0.6549 Remote Similarity NPD8337 Approved
0.6544 Remote Similarity NPD8295 Clinical (unspecified phase)
0.6541 Remote Similarity NPD5215 Approved
0.6541 Remote Similarity NPD5217 Approved
0.6541 Remote Similarity NPD5216 Approved
0.6529 Remote Similarity NPD6903 Approved
0.6512 Remote Similarity NPD4754 Approved
0.6508 Remote Similarity NPD5173 Approved
0.6504 Remote Similarity NPD5693 Phase 1
0.65 Remote Similarity NPD7146 Approved
0.65 Remote Similarity NPD6409 Approved
0.65 Remote Similarity NPD7334 Approved
0.65 Remote Similarity NPD7521 Approved
0.65 Remote Similarity NPD6684 Approved
0.65 Remote Similarity NPD5330 Approved
0.6479 Remote Similarity NPD8074 Phase 3
0.6475 Remote Similarity NPD6921 Approved
0.6471 Remote Similarity NPD6868 Approved
0.6466 Remote Similarity NPD5169 Approved
0.6466 Remote Similarity NPD5134 Clinical (unspecified phase)
0.6466 Remote Similarity NPD5135 Approved
0.6458 Remote Similarity NPD5956 Approved
0.6457 Remote Similarity NPD8029 Clinical (unspecified phase)
0.6452 Remote Similarity NPD5778 Approved
0.6452 Remote Similarity NPD5779 Approved
0.6423 Remote Similarity NPD7838 Discovery
0.6418 Remote Similarity NPD5127 Approved
0.6417 Remote Similarity NPD1694 Approved
0.64 Remote Similarity NPD6001 Approved
0.6393 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6376 Remote Similarity NPD6334 Approved
0.6376 Remote Similarity NPD6333 Approved
0.6371 Remote Similarity NPD5284 Approved
0.6371 Remote Similarity NPD7637 Suspended
0.6371 Remote Similarity NPD5281 Approved
0.6364 Remote Similarity NPD7625 Phase 1
0.6357 Remote Similarity NPD1700 Approved
0.6349 Remote Similarity NPD1698 Clinical (unspecified phase)
0.6341 Remote Similarity NPD6904 Approved
0.6341 Remote Similarity NPD6080 Approved
0.6341 Remote Similarity NPD6673 Approved
0.6341 Remote Similarity NPD4753 Phase 2
0.6341 Remote Similarity NPD1695 Approved
0.6336 Remote Similarity NPD8170 Clinical (unspecified phase)
0.6333 Remote Similarity NPD6400 Clinical (unspecified phase)
0.6311 Remote Similarity NPD3573 Approved
0.6303 Remote Similarity NPD4752 Clinical (unspecified phase)
0.6299 Remote Similarity NPD4697 Phase 3
0.6296 Remote Similarity NPD8413 Clinical (unspecified phase)
0.629 Remote Similarity NPD5207 Approved
0.6282 Remote Similarity NPD7236 Approved
0.6277 Remote Similarity NPD5167 Approved
0.627 Remote Similarity NPD7748 Approved
0.6268 Remote Similarity NPD7829 Approved
0.6268 Remote Similarity NPD7830 Approved
0.6268 Remote Similarity NPD7642 Approved
0.626 Remote Similarity NPD6672 Approved
0.626 Remote Similarity NPD5737 Approved

Structure

External Identifiers

PubChem CID   5318363
ChEMBL   CHEMBL2035089
ZINC  

Physicochemical Properties

Molecular Weight:  586.24
ALogP:  1.0771
MLogP:  3.66
XLogP:  0.91
# Rotatable Bonds:  17
Polar Surface Area:  155.03
# H-Bond Aceptor:  11
# H-Bond Donor:  1
# Rings:  5
# Heavy Atoms:  42

Download Data

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