Natural Product: NPC147921

Natural Product ID:  NPC147921
Common Name:   Hydroxylindestenolide
IUPAC Name:   (4aS,8aS,9aS)-9a-hydroxy-3,8a-dimethyl-5-methylidene-3,4a,6,9-tetrahydrobenzo[f][1]benzofuran-2-one
Synonyms:   Hydroxylindestenolide
Molecular Formula:   C15H18O3
Standard InCHIKey:  BCKDXTZTXHTKQP-BDHHQKMPSA-N
Standard InCHI:  InChI=1S/C15H18O3/c1-9-5-4-6-14(3)8-15(17)12(7-11(9)14)10(2)13(16)18-15/h4,6-7,10-11,17H,1,5,8H2,2-3H3/t10?,11-,14+,15-/m0/s1
Canonical SMILES:  C=C1CC=C[C@]2([C@H]1C=C1C(C)C(=O)O[C@]1(C2)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
NPO17612 Xanthium sibiricum Species Asteraceae Eukaryota Fruits PMID[26110443]
NPO30415 Lindera aggregate Species Tineidae Eukaryota TCM_Taiwan*

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT65 Cell Line HepG2 Homo sapiens EC50 = 42400 nM 19639966
NPT32 Organism Mus musculus Mus musculus Inhibition = 37.7 % 26110443
NPT2 Others Unspecified IC50 = 3900 nM 26110443
NPT3119 Organism Human coxsackievirus B3 Human coxsackievirus B3 IC50 > 35000 nM 26110443
NPT2 Others Unspecified IC50 > 35000 nM 26110443

  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 NPC147921 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
0.8132 Intermediate Similarity NPC166346
0.809 Intermediate Similarity NPC477128
0.8068 Intermediate Similarity NPC250981
0.8022 Intermediate Similarity NPC233345
0.8022 Intermediate Similarity NPC186363
0.8 Intermediate Similarity NPC195424
0.7978 Intermediate Similarity NPC171722
0.7955 Intermediate Similarity NPC52628
0.7917 Intermediate Similarity NPC469657
0.7917 Intermediate Similarity NPC244456
0.7912 Intermediate Similarity NPC281942
0.7912 Intermediate Similarity NPC232426
0.7889 Intermediate Similarity NPC277771
0.7865 Intermediate Similarity NPC6979
0.7826 Intermediate Similarity NPC141831
0.7816 Intermediate Similarity NPC186276
0.7802 Intermediate Similarity NPC168131
0.7778 Intermediate Similarity NPC231599
0.7778 Intermediate Similarity NPC312561
0.7766 Intermediate Similarity NPC183012
0.7753 Intermediate Similarity NPC177932
0.7727 Intermediate Similarity NPC22611
0.7727 Intermediate Similarity NPC470948
0.7717 Intermediate Similarity NPC15059
0.7717 Intermediate Similarity NPC469372
0.7701 Intermediate Similarity NPC52861
0.7692 Intermediate Similarity NPC215831
0.7692 Intermediate Similarity NPC24816
0.7692 Intermediate Similarity NPC136879
0.7674 Intermediate Similarity NPC89128
0.766 Intermediate Similarity NPC475572
0.766 Intermediate Similarity NPC250075
0.766 Intermediate Similarity NPC477130
0.766 Intermediate Similarity NPC477129
0.7653 Intermediate Similarity NPC235369
0.764 Intermediate Similarity NPC295799
0.7634 Intermediate Similarity NPC289479
0.7634 Intermediate Similarity NPC65513
0.7614 Intermediate Similarity NPC89555
0.7609 Intermediate Similarity NPC73995
0.7609 Intermediate Similarity NPC173042
0.7609 Intermediate Similarity NPC218927
0.7609 Intermediate Similarity NPC206001
0.7604 Intermediate Similarity NPC70145
0.7604 Intermediate Similarity NPC476253
0.7604 Intermediate Similarity NPC76266
0.7604 Intermediate Similarity NPC91695
0.7582 Intermediate Similarity NPC475678
0.7558 Intermediate Similarity NPC179028
0.7558 Intermediate Similarity NPC267231
0.7558 Intermediate Similarity NPC169095
0.7553 Intermediate Similarity NPC472303
0.7551 Intermediate Similarity NPC63249
0.7529 Intermediate Similarity NPC41017
0.7527 Intermediate Similarity NPC469368
0.7526 Intermediate Similarity NPC216478
0.7526 Intermediate Similarity NPC23364
0.75 Intermediate Similarity NPC258532
0.75 Intermediate Similarity NPC477302
0.7475 Intermediate Similarity NPC134077
0.7475 Intermediate Similarity NPC58329
0.7473 Intermediate Similarity NPC82979
0.7473 Intermediate Similarity NPC85698
0.7473 Intermediate Similarity NPC474062
0.7473 Intermediate Similarity NPC239685
0.7473 Intermediate Similarity NPC473226
0.7473 Intermediate Similarity NPC329692
0.7449 Intermediate Similarity NPC472644
0.7447 Intermediate Similarity NPC252433
0.7447 Intermediate Similarity NPC49420
0.7447 Intermediate Similarity NPC179517
0.7447 Intermediate Similarity NPC165904
0.7444 Intermediate Similarity NPC472326
0.7444 Intermediate Similarity NPC141193
0.7444 Intermediate Similarity NPC476804
0.7444 Intermediate Similarity NPC96259
0.7444 Intermediate Similarity NPC114979
0.7444 Intermediate Similarity NPC191476
0.7442 Intermediate Similarity NPC187568
0.7442 Intermediate Similarity NPC320630
0.7442 Intermediate Similarity NPC41780
0.7442 Intermediate Similarity NPC116177
0.7442 Intermediate Similarity NPC7563
0.7439 Intermediate Similarity NPC199557
0.7426 Intermediate Similarity NPC477125
0.7426 Intermediate Similarity NPC252296
0.7423 Intermediate Similarity NPC208094
0.7419 Intermediate Similarity NPC5509
0.7416 Intermediate Similarity NPC178676
0.7416 Intermediate Similarity NPC474252
0.7412 Intermediate Similarity NPC476795
0.7396 Intermediate Similarity NPC295347
0.7391 Intermediate Similarity NPC181103
0.7391 Intermediate Similarity NPC128644
0.7391 Intermediate Similarity NPC305029
0.7386 Intermediate Similarity NPC10636
0.7374 Intermediate Similarity NPC472643
0.7368 Intermediate Similarity NPC471571
0.7368 Intermediate Similarity NPC242069
0.7368 Intermediate Similarity NPC115021
0.7363 Intermediate Similarity NPC329738
0.7363 Intermediate Similarity NPC269638
0.7363 Intermediate Similarity NPC255307
0.7363 Intermediate Similarity NPC165162
0.7356 Intermediate Similarity NPC471465
0.7356 Intermediate Similarity NPC196653
0.7356 Intermediate Similarity NPC35574
0.7356 Intermediate Similarity NPC93763
0.7356 Intermediate Similarity NPC108816
0.7353 Intermediate Similarity NPC301666
0.7353 Intermediate Similarity NPC184512
0.7347 Intermediate Similarity NPC124703
0.7347 Intermediate Similarity NPC316598
0.7347 Intermediate Similarity NPC234617
0.734 Intermediate Similarity NPC152467
0.734 Intermediate Similarity NPC220454
0.734 Intermediate Similarity NPC212679
0.734 Intermediate Similarity NPC477782
0.734 Intermediate Similarity NPC469595
0.734 Intermediate Similarity NPC472307
0.734 Intermediate Similarity NPC214844
0.734 Intermediate Similarity NPC76286
0.734 Intermediate Similarity NPC158488
0.7333 Intermediate Similarity NPC310470
0.7333 Intermediate Similarity NPC250315
0.7333 Intermediate Similarity NPC193198
0.7333 Intermediate Similarity NPC49019
0.7327 Intermediate Similarity NPC296950
0.7327 Intermediate Similarity NPC146731
0.7326 Intermediate Similarity NPC40353
0.7326 Intermediate Similarity NPC69143
0.732 Intermediate Similarity NPC112654
0.732 Intermediate Similarity NPC311166
0.7312 Intermediate Similarity NPC226863
0.7308 Intermediate Similarity NPC235014
0.7308 Intermediate Similarity NPC5103
0.7303 Intermediate Similarity NPC229584
0.7303 Intermediate Similarity NPC14203
0.7303 Intermediate Similarity NPC470241
0.7303 Intermediate Similarity NPC325031
0.7303 Intermediate Similarity NPC209318
0.7303 Intermediate Similarity NPC24417
0.7303 Intermediate Similarity NPC223330
0.7303 Intermediate Similarity NPC38642
0.73 Intermediate Similarity NPC238397
0.73 Intermediate Similarity NPC31058
0.73 Intermediate Similarity NPC471363
0.73 Intermediate Similarity NPC469606
0.73 Intermediate Similarity NPC273005
0.7294 Intermediate Similarity NPC241854
0.7294 Intermediate Similarity NPC476046
0.7294 Intermediate Similarity NPC301065
0.7294 Intermediate Similarity NPC213223
0.7294 Intermediate Similarity NPC251970
0.7292 Intermediate Similarity NPC474554
0.7292 Intermediate Similarity NPC53685
0.7292 Intermediate Similarity NPC474555
0.7292 Intermediate Similarity NPC167219
0.7292 Intermediate Similarity NPC471720
0.7283 Intermediate Similarity NPC475461
0.7283 Intermediate Similarity NPC305475
0.7283 Intermediate Similarity NPC198314
0.7283 Intermediate Similarity NPC9231
0.7273 Intermediate Similarity NPC470244
0.7273 Intermediate Similarity NPC477720
0.7273 Intermediate Similarity NPC98557
0.7273 Intermediate Similarity NPC167881
0.7273 Intermediate Similarity NPC17550
0.7273 Intermediate Similarity NPC475210
0.7273 Intermediate Similarity NPC469617
0.7273 Intermediate Similarity NPC470239
0.7263 Intermediate Similarity NPC477783
0.7263 Intermediate Similarity NPC303697
0.7263 Intermediate Similarity NPC324157
0.7262 Intermediate Similarity NPC160817
0.7262 Intermediate Similarity NPC129665
0.7255 Intermediate Similarity NPC469607
0.7255 Intermediate Similarity NPC472645
0.7253 Intermediate Similarity NPC159635
0.7245 Intermediate Similarity NPC53844
0.7245 Intermediate Similarity NPC474343
0.7245 Intermediate Similarity NPC98112
0.7245 Intermediate Similarity NPC257726
0.7245 Intermediate Similarity NPC204054
0.7245 Intermediate Similarity NPC254496
0.7241 Intermediate Similarity NPC122264
0.7241 Intermediate Similarity NPC137547
0.7241 Intermediate Similarity NPC107668
0.7241 Intermediate Similarity NPC97377
0.7238 Intermediate Similarity NPC304180
0.7238 Intermediate Similarity NPC179798
0.7234 Intermediate Similarity NPC50488
0.7234 Intermediate Similarity NPC118011
0.7234 Intermediate Similarity NPC284561
0.7234 Intermediate Similarity NPC174765
0.7234 Intermediate Similarity NPC251528
0.7234 Intermediate Similarity NPC474396
0.7234 Intermediate Similarity NPC36668
0.7228 Intermediate Similarity NPC36688
0.7228 Intermediate Similarity NPC475889

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC147921 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
0.7753 Intermediate Similarity NPD1694 Approved
0.7041 Intermediate Similarity NPD1698 Clinical (unspecified phase)
0.7011 Intermediate Similarity NPD8039 Approved
0.701 Intermediate Similarity NPD6399 Phase 3
0.6979 Remote Similarity NPD5785 Approved
0.6907 Remote Similarity NPD5284 Approved
0.6907 Remote Similarity NPD5281 Approved
0.6848 Remote Similarity NPD4752 Clinical (unspecified phase)
0.6837 Remote Similarity NPD5779 Approved
0.6837 Remote Similarity NPD5778 Approved
0.6832 Remote Similarity NPD4225 Approved
0.6804 Remote Similarity NPD5207 Approved
0.6778 Remote Similarity NPD5784 Clinical (unspecified phase)
0.6774 Remote Similarity NPD7154 Phase 3
0.6774 Remote Similarity NPD5362 Discontinued
0.6737 Remote Similarity NPD4623 Approved
0.6737 Remote Similarity NPD4519 Discontinued
0.6735 Remote Similarity NPD6411 Approved
0.6702 Remote Similarity NPD6400 Clinical (unspecified phase)
0.6667 Remote Similarity NPD8513 Phase 3
0.6667 Remote Similarity NPD4270 Approved
0.6667 Remote Similarity NPD8516 Approved
0.6667 Remote Similarity NPD8517 Approved
0.6667 Remote Similarity NPD4269 Approved
0.6667 Remote Similarity NPD8515 Approved
0.663 Remote Similarity NPD5790 Clinical (unspecified phase)
0.6607 Remote Similarity NPD7115 Discovery
0.6606 Remote Similarity NPD8413 Clinical (unspecified phase)
0.6602 Remote Similarity NPD7639 Approved
0.6602 Remote Similarity NPD7640 Approved
0.6569 Remote Similarity NPD7902 Approved
0.6566 Remote Similarity NPD5693 Phase 1
0.6562 Remote Similarity NPD5786 Approved
0.6535 Remote Similarity NPD5695 Phase 3
0.6531 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6531 Remote Similarity NPD6101 Approved
0.6505 Remote Similarity NPD7638 Approved
0.6505 Remote Similarity NPD8029 Clinical (unspecified phase)
0.6495 Remote Similarity NPD3573 Approved
0.6489 Remote Similarity NPD3667 Approved
0.6481 Remote Similarity NPD6686 Approved
0.6465 Remote Similarity NPD6698 Approved
0.6465 Remote Similarity NPD46 Approved
0.6458 Remote Similarity NPD5363 Approved
0.6458 Remote Similarity NPD6082 Clinical (unspecified phase)
0.6452 Remote Similarity NPD4822 Approved
0.6452 Remote Similarity NPD4820 Approved
0.6452 Remote Similarity NPD4821 Approved
0.6452 Remote Similarity NPD4252 Approved
0.6452 Remote Similarity NPD4819 Approved
0.6436 Remote Similarity NPD7748 Approved
0.6436 Remote Similarity NPD6001 Approved
0.6413 Remote Similarity NPD4268 Approved
0.6413 Remote Similarity NPD4271 Approved
0.64 Remote Similarity NPD7637 Suspended
0.64 Remote Similarity NPD5694 Approved
0.6392 Remote Similarity NPD7146 Approved
0.6392 Remote Similarity NPD5690 Phase 2
0.6392 Remote Similarity NPD4249 Approved
0.6392 Remote Similarity NPD7521 Approved
0.6392 Remote Similarity NPD7334 Approved
0.6392 Remote Similarity NPD6684 Approved
0.6392 Remote Similarity NPD5330 Approved
0.6392 Remote Similarity NPD3618 Phase 1
0.6392 Remote Similarity NPD6409 Approved
0.6392 Remote Similarity NPD6098 Approved
0.6387 Remote Similarity NPD8074 Phase 3
0.6383 Remote Similarity NPD5369 Approved
0.6373 Remote Similarity NPD6356 Clinical (unspecified phase)
0.6364 Remote Similarity NPD1695 Approved
0.6364 Remote Similarity NPD7285 Clinical (unspecified phase)
0.6354 Remote Similarity NPD4786 Approved
0.6346 Remote Similarity NPD5696 Approved
0.6327 Remote Similarity NPD4251 Approved
0.6327 Remote Similarity NPD4250 Approved
0.6316 Remote Similarity NPD4221 Approved
0.6316 Remote Similarity NPD6435 Approved
0.6316 Remote Similarity NPD4223 Phase 3
0.6311 Remote Similarity NPD7839 Suspended
0.63 Remote Similarity NPD5692 Phase 3
0.6289 Remote Similarity NPD1733 Clinical (unspecified phase)
0.6286 Remote Similarity NPD6404 Discontinued
0.6277 Remote Similarity NPD4695 Discontinued
0.6275 Remote Similarity NPD7901 Clinical (unspecified phase)
0.6275 Remote Similarity NPD5282 Discontinued
0.6275 Remote Similarity NPD7900 Approved
0.6263 Remote Similarity NPD6672 Approved
0.6263 Remote Similarity NPD6903 Approved
0.6263 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6263 Remote Similarity NPD5208 Approved
0.6263 Remote Similarity NPD5737 Approved
0.6263 Remote Similarity NPD4518 Approved
0.625 Remote Similarity NPD5332 Approved
0.625 Remote Similarity NPD6083 Phase 2
0.625 Remote Similarity NPD5331 Approved
0.625 Remote Similarity NPD6882 Approved
0.625 Remote Similarity NPD6084 Phase 2
0.6239 Remote Similarity NPD5697 Approved
0.6238 Remote Similarity NPD7983 Approved
0.6238 Remote Similarity NPD7515 Phase 2
0.6238 Remote Similarity NPD8035 Phase 2
0.6238 Remote Similarity NPD6050 Approved
0.6238 Remote Similarity NPD8034 Phase 2
0.6224 Remote Similarity NPD4694 Approved
0.6224 Remote Similarity NPD5280 Approved
0.6224 Remote Similarity NPD3574 Clinical (unspecified phase)
0.6216 Remote Similarity NPD5955 Clinical (unspecified phase)
0.6216 Remote Similarity NPD6371 Approved
0.6211 Remote Similarity NPD4790 Discontinued
0.62 Remote Similarity NPD6673 Approved
0.62 Remote Similarity NPD6904 Approved
0.62 Remote Similarity NPD6080 Approved
0.619 Remote Similarity NPD368 Approved
0.6186 Remote Similarity NPD3133 Approved
0.6186 Remote Similarity NPD3666 Approved
0.6186 Remote Similarity NPD4197 Approved
0.6186 Remote Similarity NPD3665 Phase 1
0.6182 Remote Similarity NPD6011 Approved
0.6182 Remote Similarity NPD6899 Approved
0.6182 Remote Similarity NPD6881 Approved
0.6161 Remote Similarity NPD6650 Approved
0.6161 Remote Similarity NPD6649 Approved
0.6147 Remote Similarity NPD6402 Approved
0.6147 Remote Similarity NPD5739 Approved
0.6147 Remote Similarity NPD7128 Approved
0.6147 Remote Similarity NPD6675 Approved
0.6147 Remote Similarity NPD6008 Approved
0.6146 Remote Similarity NPD5209 Approved
0.6129 Remote Similarity NPD4756 Discovery
0.6126 Remote Similarity NPD6373 Approved
0.6126 Remote Similarity NPD6014 Approved
0.6126 Remote Similarity NPD6372 Approved
0.6126 Remote Similarity NPD6013 Approved
0.6126 Remote Similarity NPD4061 Clinical (unspecified phase)
0.6126 Remote Similarity NPD6012 Approved
0.6122 Remote Similarity NPD5329 Approved
0.6106 Remote Similarity NPD6053 Discontinued
0.6105 Remote Similarity NPD5368 Approved
0.6092 Remote Similarity NPD7331 Phase 2
0.6091 Remote Similarity NPD5701 Approved
0.6091 Remote Similarity NPD7899 Clinical (unspecified phase)
0.6087 Remote Similarity NPD8264 Approved
0.6078 Remote Similarity NPD6079 Approved
0.6071 Remote Similarity NPD7102 Approved
0.6071 Remote Similarity NPD7290 Approved
0.6071 Remote Similarity NPD6883 Approved
0.6064 Remote Similarity NPD3617 Approved
0.6061 Remote Similarity NPD4689 Approved
0.6061 Remote Similarity NPD5279 Phase 3
0.6061 Remote Similarity NPD4690 Approved
0.6061 Remote Similarity NPD5205 Approved
0.6061 Remote Similarity NPD4688 Approved
0.6061 Remote Similarity NPD4693 Phase 3
0.6061 Remote Similarity NPD4138 Approved
0.6048 Remote Similarity NPD7260 Phase 2
0.6047 Remote Similarity NPD5325 Clinical (unspecified phase)
0.6042 Remote Similarity NPD857 Phase 3
0.6042 Remote Similarity NPD4139 Approved
0.6042 Remote Similarity NPD4692 Approved
0.604 Remote Similarity NPD6051 Approved
0.604 Remote Similarity NPD5328 Approved
0.6036 Remote Similarity NPD7320 Approved
0.602 Remote Similarity NPD3668 Phase 3
0.6019 Remote Similarity NPD4202 Approved
0.6019 Remote Similarity NPD5211 Phase 2
0.6019 Remote Similarity NPD7632 Discontinued
0.6018 Remote Similarity NPD6617 Approved
0.6018 Remote Similarity NPD6847 Approved
0.6018 Remote Similarity NPD8130 Phase 1
0.6018 Remote Similarity NPD6869 Approved
0.6 Remote Similarity NPD3172 Approved
0.6 Remote Similarity NPD4194 Approved
0.6 Remote Similarity NPD4192 Approved
0.6 Remote Similarity NPD4193 Approved
0.6 Remote Similarity NPD4191 Approved
0.5982 Remote Similarity NPD8132 Clinical (unspecified phase)
0.5978 Remote Similarity NPD4687 Approved
0.5965 Remote Similarity NPD8297 Approved
0.596 Remote Similarity NPD7520 Clinical (unspecified phase)
0.596 Remote Similarity NPD1696 Phase 3
0.5946 Remote Similarity NPD5954 Clinical (unspecified phase)
0.5946 Remote Similarity NPD6412 Phase 2
0.5926 Remote Similarity NPD3196 Approved
0.5926 Remote Similarity NPD4266 Approved
0.5926 Remote Similarity NPD3194 Approved
0.5926 Remote Similarity NPD3195 Phase 2
0.5922 Remote Similarity NPD4810 Clinical (unspecified phase)
0.5909 Remote Similarity NPD5909 Discontinued
0.5909 Remote Similarity NPD5141 Approved
0.5905 Remote Similarity NPD4629 Approved
0.5905 Remote Similarity NPD5210 Approved
0.5905 Remote Similarity NPD5654 Approved
0.5902 Remote Similarity NPD7507 Approved
0.59 Remote Similarity NPD6422 Discontinued
0.5897 Remote Similarity NPD6009 Approved
0.5889 Remote Similarity NPD4137 Phase 3
0.5882 Remote Similarity NPD5370 Suspended
0.5882 Remote Similarity NPD4753 Phase 2
0.5877 Remote Similarity NPD6401 Clinical (unspecified phase)
0.5865 Remote Similarity NPD1088 Approved

Structure

External Identifiers

PubChem CID   46883415
ChEMBL   CHEMBL1079724
ZINC  

Physicochemical Properties

Molecular Weight:  246.13
ALogP:  1.6696
MLogP:  2.78
XLogP:  1.872
# Rotatable Bonds:  3
Polar Surface Area:  46.53
# H-Bond Aceptor:  3
# H-Bond Donor:  1
# Rings:  3
# Heavy Atoms:  18

Download Data

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General Info & Identifiers & Properties  
Structure MOL file  
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Biological Activities  
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