Natural Product: NPC475108

Natural Product ID:  NPC475108
Common Name:   10-Hydroxy-18-Methoxybetaenone
IUPAC Name:   (2S,3R,4R,4aR,5R,7R,8aR)-3-butan-2-yl-2,7,8a-trihydroxy-4-[(E)-3-methoxyprop-2-enoyl]-2,4,5,7-tetramethyl-4a,5,6,8-tetrahydro-3H-naphthalen-1-one
Synonyms:  
Molecular Formula:   C22H36O6
Standard InCHIKey:  ONZDNBGTAVEQQN-FJXLOMMUSA-N
Standard InCHI:  InChI=1S/C22H36O6/c1-8-13(2)16-20(5,15(23)9-10-28-7)17-14(3)11-19(4,25)12-22(17,27)18(24)21(16,6)26/h9-10,13-14,16-17,25-27H,8,11-12H2,1-7H3/b10-9+/t13?,14-,16-,17-,19-,20-,21+,22-/m1/s1
Canonical SMILES:  CO/C=C/C(=O)[C@]1(C)[C@@H](C(CC)C)[C@](C)(O)C(=O)[C@@]2([C@@H]1[C@H](C)C[C@@](C2)(C)O)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
NPO33476 microsphaeropsis sp. Species NA Eukaryota PMID[10869191]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT6611 Individual Protein Protein kinase C epsilon Mus musculus IC50 = 36000 nM 20598551
NPT2213 Individual Protein Cyclin-dependent kinase 4 Homo sapiens IC50 = 11500 nM 18341287
NPT285 Individual Protein Epidermal growth factor receptor erbB1 Homo sapiens IC50 = 10500 nM Open TG-GATES in vivo data: Organ Weight

  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 NPC475108 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
0.8125 Intermediate Similarity NPC474724
0.7957 Intermediate Similarity NPC46758
0.7895 Intermediate Similarity NPC103527
0.7835 Intermediate Similarity NPC273269
0.7812 Intermediate Similarity NPC476245
0.7778 Intermediate Similarity NPC477051
0.7778 Intermediate Similarity NPC477053
0.7778 Intermediate Similarity NPC477052
0.7766 Intermediate Similarity NPC474209
0.7766 Intermediate Similarity NPC475823
0.7765 Intermediate Similarity NPC162164
0.7765 Intermediate Similarity NPC38426
0.7755 Intermediate Similarity NPC477653
0.7755 Intermediate Similarity NPC191565
0.7701 Intermediate Similarity NPC476811
0.7701 Intermediate Similarity NPC472746
0.77 Intermediate Similarity NPC477054
0.7677 Intermediate Similarity NPC55503
0.7677 Intermediate Similarity NPC46761
0.7677 Intermediate Similarity NPC156324
0.7642 Intermediate Similarity NPC198539
0.764 Intermediate Similarity NPC469637
0.7629 Intermediate Similarity NPC272617
0.7624 Intermediate Similarity NPC247957
0.7624 Intermediate Similarity NPC249187
0.7609 Intermediate Similarity NPC224345
0.7547 Intermediate Similarity NPC90769
0.7526 Intermediate Similarity NPC64006
0.75 Intermediate Similarity NPC26865
0.75 Intermediate Similarity NPC198054
0.75 Intermediate Similarity NPC293890
0.7477 Intermediate Similarity NPC474271
0.7476 Intermediate Similarity NPC257353
0.7451 Intermediate Similarity NPC320294
0.7447 Intermediate Similarity NPC153604
0.7426 Intermediate Similarity NPC118964
0.7419 Intermediate Similarity NPC241512
0.7419 Intermediate Similarity NPC477445
0.7419 Intermediate Similarity NPC6185
0.7412 Intermediate Similarity NPC163020
0.74 Intermediate Similarity NPC98837
0.74 Intermediate Similarity NPC162459
0.74 Intermediate Similarity NPC28864
0.74 Intermediate Similarity NPC20479
0.74 Intermediate Similarity NPC38471
0.74 Intermediate Similarity NPC38296
0.7396 Intermediate Similarity NPC149761
0.7396 Intermediate Similarity NPC470378
0.7396 Intermediate Similarity NPC472325
0.7396 Intermediate Similarity NPC261994
0.7386 Intermediate Similarity NPC104806
0.7379 Intermediate Similarity NPC72255
0.7374 Intermediate Similarity NPC260223
0.7374 Intermediate Similarity NPC140242
0.7374 Intermediate Similarity NPC165616
0.7374 Intermediate Similarity NPC219353
0.7374 Intermediate Similarity NPC223169
0.7374 Intermediate Similarity NPC473964
0.7364 Intermediate Similarity NPC146786
0.7363 Intermediate Similarity NPC473217
0.7347 Intermediate Similarity NPC91772
0.7347 Intermediate Similarity NPC169751
0.7347 Intermediate Similarity NPC153775
0.7347 Intermediate Similarity NPC245972
0.7347 Intermediate Similarity NPC292374
0.7347 Intermediate Similarity NPC196485
0.7347 Intermediate Similarity NPC29247
0.7347 Intermediate Similarity NPC261333
0.7347 Intermediate Similarity NPC215271
0.7347 Intermediate Similarity NPC289539
0.7347 Intermediate Similarity NPC272635
0.7347 Intermediate Similarity NPC23170
0.7347 Intermediate Similarity NPC129004
0.7347 Intermediate Similarity NPC101233
0.7347 Intermediate Similarity NPC258674
0.7347 Intermediate Similarity NPC104371
0.7347 Intermediate Similarity NPC209662
0.7347 Intermediate Similarity NPC111524
0.734 Intermediate Similarity NPC203795
0.734 Intermediate Similarity NPC94666
0.734 Intermediate Similarity NPC34190
0.7333 Intermediate Similarity NPC289702
0.7333 Intermediate Similarity NPC208461
0.7333 Intermediate Similarity NPC476812
0.7327 Intermediate Similarity NPC293866
0.732 Intermediate Similarity NPC299185
0.7312 Intermediate Similarity NPC251170
0.7308 Intermediate Similarity NPC85529
0.7308 Intermediate Similarity NPC32006
0.7308 Intermediate Similarity NPC34768
0.73 Intermediate Similarity NPC190080
0.73 Intermediate Similarity NPC10864
0.73 Intermediate Similarity NPC111187
0.73 Intermediate Similarity NPC473963
0.7283 Intermediate Similarity NPC48362
0.7282 Intermediate Similarity NPC239716
0.7282 Intermediate Similarity NPC179208
0.7282 Intermediate Similarity NPC275583
0.7282 Intermediate Similarity NPC478057
0.7273 Intermediate Similarity NPC157686
0.7273 Intermediate Similarity NPC217329
0.7273 Intermediate Similarity NPC472824
0.7273 Intermediate Similarity NPC259042
0.7273 Intermediate Similarity NPC98639
0.7273 Intermediate Similarity NPC180950
0.7264 Intermediate Similarity NPC300026
0.7264 Intermediate Similarity NPC27814
0.7263 Intermediate Similarity NPC259009
0.7263 Intermediate Similarity NPC174619
0.7255 Intermediate Similarity NPC71706
0.7255 Intermediate Similarity NPC46848
0.7253 Intermediate Similarity NPC476809
0.7245 Intermediate Similarity NPC233118
0.7245 Intermediate Similarity NPC294263
0.7245 Intermediate Similarity NPC144739
0.7245 Intermediate Similarity NPC181594
0.7241 Intermediate Similarity NPC177826
0.7238 Intermediate Similarity NPC302788
0.7238 Intermediate Similarity NPC185
0.7238 Intermediate Similarity NPC165873
0.7238 Intermediate Similarity NPC179380
0.7238 Intermediate Similarity NPC176949
0.7238 Intermediate Similarity NPC201908
0.7234 Intermediate Similarity NPC474680
0.7234 Intermediate Similarity NPC471034
0.7234 Intermediate Similarity NPC263997
0.7234 Intermediate Similarity NPC8518
0.7234 Intermediate Similarity NPC132228
0.7234 Intermediate Similarity NPC190704
0.7228 Intermediate Similarity NPC78427
0.7228 Intermediate Similarity NPC89099
0.7228 Intermediate Similarity NPC16911
0.7228 Intermediate Similarity NPC109059
0.7228 Intermediate Similarity NPC17183
0.7228 Intermediate Similarity NPC288
0.7222 Intermediate Similarity NPC476810
0.7222 Intermediate Similarity NPC476808
0.7216 Intermediate Similarity NPC263977
0.7216 Intermediate Similarity NPC80401
0.7212 Intermediate Similarity NPC84928
0.7212 Intermediate Similarity NPC98603
0.72 Intermediate Similarity NPC470387
0.72 Intermediate Similarity NPC264979
0.72 Intermediate Similarity NPC29410
0.72 Intermediate Similarity NPC49371
0.72 Intermediate Similarity NPC200054
0.72 Intermediate Similarity NPC135548
0.72 Intermediate Similarity NPC469545
0.72 Intermediate Similarity NPC61369
0.72 Intermediate Similarity NPC93245
0.72 Intermediate Similarity NPC284518
0.72 Intermediate Similarity NPC5532
0.7196 Intermediate Similarity NPC100908
0.7191 Intermediate Similarity NPC198473
0.7191 Intermediate Similarity NPC63958
0.7188 Intermediate Similarity NPC471791
0.7188 Intermediate Similarity NPC292491
0.7188 Intermediate Similarity NPC471793
0.7188 Intermediate Similarity NPC193360
0.7188 Intermediate Similarity NPC310752
0.7184 Intermediate Similarity NPC476081
0.7184 Intermediate Similarity NPC304832
0.7184 Intermediate Similarity NPC88203
0.7184 Intermediate Similarity NPC148628
0.7184 Intermediate Similarity NPC275990
0.7184 Intermediate Similarity NPC76866
0.7184 Intermediate Similarity NPC214946
0.7184 Intermediate Similarity NPC272472
0.7184 Intermediate Similarity NPC246736
0.7184 Intermediate Similarity NPC286519
0.7182 Intermediate Similarity NPC270478
0.7174 Intermediate Similarity NPC48673
0.7174 Intermediate Similarity NPC20096
0.7174 Intermediate Similarity NPC328264
0.7172 Intermediate Similarity NPC24861
0.7172 Intermediate Similarity NPC299100
0.7172 Intermediate Similarity NPC148000
0.7172 Intermediate Similarity NPC469596
0.7172 Intermediate Similarity NPC293086
0.7172 Intermediate Similarity NPC225474
0.7172 Intermediate Similarity NPC47853
0.7172 Intermediate Similarity NPC471207
0.7172 Intermediate Similarity NPC474328
0.717 Intermediate Similarity NPC168883
0.7158 Intermediate Similarity NPC158393
0.7158 Intermediate Similarity NPC73038
0.7157 Intermediate Similarity NPC474720
0.7157 Intermediate Similarity NPC287676
0.7157 Intermediate Similarity NPC144956
0.7157 Intermediate Similarity NPC477655
0.7157 Intermediate Similarity NPC47024
0.7157 Intermediate Similarity NPC471727
0.7157 Intermediate Similarity NPC477656
0.7143 Intermediate Similarity NPC252433
0.7143 Intermediate Similarity NPC473167
0.7143 Intermediate Similarity NPC472978
0.7143 Intermediate Similarity NPC475708
0.7143 Intermediate Similarity NPC279143
0.7143 Intermediate Similarity NPC248913
0.7143 Intermediate Similarity NPC131872

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC475108 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
0.7449 Intermediate Similarity NPD4629 Approved
0.7449 Intermediate Similarity NPD5210 Approved
0.7333 Intermediate Similarity NPD5345 Clinical (unspecified phase)
0.7157 Intermediate Similarity NPD5286 Approved
0.7157 Intermediate Similarity NPD5285 Approved
0.7157 Intermediate Similarity NPD4696 Approved
0.7065 Intermediate Similarity NPD4695 Discontinued
0.7059 Intermediate Similarity NPD5696 Approved
0.703 Intermediate Similarity NPD5221 Approved
0.703 Intermediate Similarity NPD5222 Approved
0.703 Intermediate Similarity NPD5220 Clinical (unspecified phase)
0.7021 Intermediate Similarity NPD4788 Approved
0.7019 Intermediate Similarity NPD5225 Approved
0.7019 Intermediate Similarity NPD5226 Approved
0.7019 Intermediate Similarity NPD4633 Approved
0.7019 Intermediate Similarity NPD5224 Approved
0.7019 Intermediate Similarity NPD5211 Phase 2
0.7009 Intermediate Similarity NPD6899 Approved
0.7009 Intermediate Similarity NPD6881 Approved
0.6979 Remote Similarity NPD3618 Phase 1
0.6979 Remote Similarity NPD3574 Clinical (unspecified phase)
0.6972 Remote Similarity NPD6649 Approved
0.6972 Remote Similarity NPD6650 Approved
0.697 Remote Similarity NPD6079 Approved
0.6961 Remote Similarity NPD4755 Approved
0.6961 Remote Similarity NPD5173 Approved
0.6952 Remote Similarity NPD5174 Approved
0.6952 Remote Similarity NPD5175 Approved
0.6939 Remote Similarity NPD4753 Phase 2
0.6923 Remote Similarity NPD5223 Approved
0.6916 Remote Similarity NPD5697 Approved
0.6887 Remote Similarity NPD5141 Approved
0.6881 Remote Similarity NPD4634 Approved
0.6881 Remote Similarity NPD7102 Approved
0.6881 Remote Similarity NPD6883 Approved
0.6881 Remote Similarity NPD7290 Approved
0.6863 Remote Similarity NPD4697 Phase 3
0.6832 Remote Similarity NPD5282 Discontinued
0.6832 Remote Similarity NPD7748 Approved
0.6827 Remote Similarity NPD4700 Approved
0.6822 Remote Similarity NPD6675 Approved
0.6822 Remote Similarity NPD7128 Approved
0.6822 Remote Similarity NPD5739 Approved
0.6822 Remote Similarity NPD6402 Approved
0.6818 Remote Similarity NPD6869 Approved
0.6818 Remote Similarity NPD8130 Phase 1
0.6818 Remote Similarity NPD6847 Approved
0.6818 Remote Similarity NPD6617 Approved
0.68 Remote Similarity NPD7515 Phase 2
0.6796 Remote Similarity NPD6084 Phase 2
0.6796 Remote Similarity NPD6083 Phase 2
0.6796 Remote Similarity NPD7902 Approved
0.6789 Remote Similarity NPD6373 Approved
0.6789 Remote Similarity NPD6012 Approved
0.6789 Remote Similarity NPD6372 Approved
0.6789 Remote Similarity NPD6013 Approved
0.6789 Remote Similarity NPD6014 Approved
0.6768 Remote Similarity NPD5328 Approved
0.6757 Remote Similarity NPD6882 Approved
0.6757 Remote Similarity NPD8297 Approved
0.6701 Remote Similarity NPD5329 Approved
0.6697 Remote Similarity NPD7320 Approved
0.6697 Remote Similarity NPD4730 Approved
0.6697 Remote Similarity NPD4729 Approved
0.6697 Remote Similarity NPD6011 Approved
0.6696 Remote Similarity NPD4632 Approved
0.6667 Remote Similarity NPD3617 Approved
0.6638 Remote Similarity NPD6054 Approved
0.6634 Remote Similarity NPD8034 Phase 2
0.6634 Remote Similarity NPD8035 Phase 2
0.6633 Remote Similarity NPD5690 Phase 2
0.6606 Remote Similarity NPD5701 Approved
0.6602 Remote Similarity NPD5695 Phase 3
0.66 Remote Similarity NPD7285 Clinical (unspecified phase)
0.6598 Remote Similarity NPD4197 Approved
0.6598 Remote Similarity NPD4786 Approved
0.6581 Remote Similarity NPD6921 Approved
0.6577 Remote Similarity NPD5250 Approved
0.6577 Remote Similarity NPD5251 Approved
0.6577 Remote Similarity NPD5247 Approved
0.6577 Remote Similarity NPD5248 Approved
0.6577 Remote Similarity NPD5249 Phase 3
0.6569 Remote Similarity NPD6399 Phase 3
0.6569 Remote Similarity NPD4202 Approved
0.6566 Remote Similarity NPD3573 Approved
0.6562 Remote Similarity NPD3667 Approved
0.6545 Remote Similarity NPD5128 Approved
0.6542 Remote Similarity NPD5091 Approved
0.6531 Remote Similarity NPD7520 Clinical (unspecified phase)
0.6525 Remote Similarity NPD6370 Approved
0.6522 Remote Similarity NPD3703 Phase 2
0.6522 Remote Similarity NPD6009 Approved
0.6518 Remote Similarity NPD5215 Approved
0.6518 Remote Similarity NPD5216 Approved
0.6518 Remote Similarity NPD5217 Approved
0.6514 Remote Similarity NPD4767 Approved
0.6514 Remote Similarity NPD4768 Approved
0.6505 Remote Similarity NPD7900 Approved
0.6505 Remote Similarity NPD7901 Clinical (unspecified phase)
0.65 Remote Similarity NPD5737 Approved
0.65 Remote Similarity NPD6672 Approved
0.6496 Remote Similarity NPD6319 Approved
0.6489 Remote Similarity NPD6115 Approved
0.6489 Remote Similarity NPD6697 Approved
0.6489 Remote Similarity NPD6118 Approved
0.6489 Remote Similarity NPD6114 Approved
0.6481 Remote Similarity NPD4754 Approved
0.6444 Remote Similarity NPD4789 Approved
0.6441 Remote Similarity NPD6016 Approved
0.6441 Remote Similarity NPD6015 Approved
0.6429 Remote Similarity NPD3665 Phase 1
0.6429 Remote Similarity NPD3666 Approved
0.6429 Remote Similarity NPD5135 Approved
0.6429 Remote Similarity NPD5169 Approved
0.6429 Remote Similarity NPD5134 Clinical (unspecified phase)
0.6429 Remote Similarity NPD3133 Approved
0.6417 Remote Similarity NPD7492 Approved
0.6415 Remote Similarity NPD7638 Approved
0.641 Remote Similarity NPD7100 Approved
0.641 Remote Similarity NPD7101 Approved
0.6404 Remote Similarity NPD5360 Phase 3
0.6404 Remote Similarity NPD5361 Clinical (unspecified phase)
0.6396 Remote Similarity NPD5168 Approved
0.6392 Remote Similarity NPD4223 Phase 3
0.6392 Remote Similarity NPD4221 Approved
0.6387 Remote Similarity NPD5988 Approved
0.6379 Remote Similarity NPD7115 Discovery
0.6374 Remote Similarity NPD4809 Clinical (unspecified phase)
0.6374 Remote Similarity NPD4808 Clinical (unspecified phase)
0.6372 Remote Similarity NPD6401 Clinical (unspecified phase)
0.6372 Remote Similarity NPD5127 Approved
0.6364 Remote Similarity NPD6616 Approved
0.6356 Remote Similarity NPD6059 Approved
0.6355 Remote Similarity NPD7639 Approved
0.6355 Remote Similarity NPD7640 Approved
0.6333 Remote Similarity NPD3700 Clinical (unspecified phase)
0.6333 Remote Similarity NPD7604 Phase 2
0.6333 Remote Similarity NPD3699 Clinical (unspecified phase)
0.6325 Remote Similarity NPD6335 Approved
0.6311 Remote Similarity NPD7078 Approved
0.6303 Remote Similarity NPD5983 Phase 2
0.63 Remote Similarity NPD5280 Approved
0.63 Remote Similarity NPD4694 Approved
0.63 Remote Similarity NPD5279 Phase 3
0.63 Remote Similarity NPD4623 Approved
0.63 Remote Similarity NPD4519 Discontinued
0.6293 Remote Similarity NPD6274 Approved
0.6293 Remote Similarity NPD6868 Approved
0.6286 Remote Similarity NPD6356 Clinical (unspecified phase)
0.6283 Remote Similarity NPD5955 Clinical (unspecified phase)
0.6277 Remote Similarity NPD6117 Approved
0.6275 Remote Similarity NPD6080 Approved
0.6275 Remote Similarity NPD6904 Approved
0.6275 Remote Similarity NPD6673 Approved
0.6263 Remote Similarity NPD3668 Phase 3
0.626 Remote Similarity NPD7736 Approved
0.625 Remote Similarity NPD7645 Phase 2
0.625 Remote Similarity NPD3171 Clinical (unspecified phase)
0.6239 Remote Similarity NPD6317 Approved
0.623 Remote Similarity NPD6336 Discontinued
0.6226 Remote Similarity NPD7614 Phase 1
0.6216 Remote Similarity NPD6008 Approved
0.6211 Remote Similarity NPD6116 Phase 1
0.6207 Remote Similarity NPD5167 Approved
0.62 Remote Similarity NPD1694 Approved
0.6198 Remote Similarity NPD8328 Phase 3
0.6196 Remote Similarity NPD6081 Approved
0.6195 Remote Similarity NPD8132 Clinical (unspecified phase)
0.6195 Remote Similarity NPD4061 Clinical (unspecified phase)
0.6186 Remote Similarity NPD6314 Approved
0.6186 Remote Similarity NPD8259 Clinical (unspecified phase)
0.6186 Remote Similarity NPD7525 Registered
0.6186 Remote Similarity NPD6313 Approved
0.6167 Remote Similarity NPD6291 Clinical (unspecified phase)
0.6161 Remote Similarity NPD6412 Phase 2
0.6161 Remote Similarity NPD6614 Approved
0.6154 Remote Similarity NPD5281 Approved
0.6154 Remote Similarity NPD5284 Approved
0.6139 Remote Similarity NPD4138 Approved
0.6139 Remote Similarity NPD7521 Approved
0.6139 Remote Similarity NPD5330 Approved
0.6139 Remote Similarity NPD6098 Approved
0.6139 Remote Similarity NPD4689 Approved
0.6139 Remote Similarity NPD4693 Phase 3
0.6139 Remote Similarity NPD6684 Approved
0.6139 Remote Similarity NPD7334 Approved
0.6139 Remote Similarity NPD7146 Approved
0.6139 Remote Similarity NPD4690 Approved
0.6139 Remote Similarity NPD6409 Approved
0.6139 Remote Similarity NPD5205 Approved
0.6139 Remote Similarity NPD4688 Approved
0.6111 Remote Similarity NPD4225 Approved
0.6087 Remote Similarity NPD4244 Approved
0.6087 Remote Similarity NPD4245 Approved
0.6082 Remote Similarity NPD4195 Approved
0.6075 Remote Similarity NPD7732 Phase 3
0.6064 Remote Similarity NPD6113 Clinical (unspecified phase)
0.6061 Remote Similarity NPD4752 Clinical (unspecified phase)
0.6048 Remote Similarity NPD8293 Discontinued
0.604 Remote Similarity NPD1696 Phase 3

Structure

External Identifiers

PubChem CID   10644450
ChEMBL   CHEMBL498247
ZINC  

Physicochemical Properties

Molecular Weight:  396.25
ALogP:  -1.9306
MLogP:  3.22
XLogP:  2.561
# Rotatable Bonds:  15
Polar Surface Area:  104.06
# H-Bond Aceptor:  6
# H-Bond Donor:  3
# Rings:  2
# Heavy Atoms:  28

Download Data

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General Info & Identifiers & Properties  
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Biological Activities  
Similar NPs/Drugs