Natural Product: NPC469509

Natural Product ID:  NPC469509
Common Name:   4-Hydroxyhyperolactone D
IUPAC Name:   (4S)-4-ethenyl-3-hydroxy-3-[(Z)-3-hydroxy-3-phenylprop-2-enoyl]-4-methyloxolan-2-one
Synonyms:   4-Hydroxyhyperolactone D
Molecular Formula:   C16H16O5
Standard InCHIKey:  BHPIIQWXAQWASX-JCWIHFPZSA-N
Standard InCHI:  InChI=1S/C16H16O5/c1-3-15(2)10-21-14(19)16(15,20)13(18)9-12(17)11-7-5-4-6-8-11/h3-9,17,20H,1,10H2,2H3/b12-9-/t15-,16?/m0/s1
Canonical SMILES:  C=C[C@@]1(C)COC(=O)C1(O)C(=O)/C=C(/c1ccccc1)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
NPO8089 Hypericum chinense Species Hypericaceae Eukaryota PMID[19606850]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT111 Cell Line K562 Homo sapiens IC50 > 100 ug/ml 8864236
NPT2 Others Unspecified IC50 > 100 ug/ml 26287401
NPT91 Cell Line KB Homo sapiens IC50 > 100 ug/ml 26091285
NPT407 Cell Line COLO 205 Homo sapiens IC50 = 79 ug/ml 25310730
NPT2 Others Unspecified IC50 = 53.1 ug/ml 10.1039/C4MD00399C
NPT111 Cell Line K562 Homo sapiens IC50 = 33.7 ug/ml 21155589
NPT83 Cell Line MCF7 Homo sapiens IC50 = 62.1 ug/ml 23398362

  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 NPC469509 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
0.9252 High Similarity NPC469511
0.885 High Similarity NPC216387
0.7937 Intermediate Similarity NPC472707
0.7881 Intermediate Similarity NPC474363
0.7823 Intermediate Similarity NPC469927
0.7788 Intermediate Similarity NPC160382
0.7739 Intermediate Similarity NPC136962
0.7669 Intermediate Similarity NPC255428
0.7647 Intermediate Similarity NPC474176
0.7632 Intermediate Similarity NPC91820
0.7632 Intermediate Similarity NPC82426
0.7619 Intermediate Similarity NPC236981
0.7619 Intermediate Similarity NPC471466
0.7619 Intermediate Similarity NPC472704
0.7603 Intermediate Similarity NPC210531
0.7594 Intermediate Similarity NPC217673
0.7594 Intermediate Similarity NPC52523
0.7589 Intermediate Similarity NPC476120
0.7586 Intermediate Similarity NPC472315
0.7586 Intermediate Similarity NPC475203
0.7586 Intermediate Similarity NPC474376
0.7586 Intermediate Similarity NPC472316
0.7578 Intermediate Similarity NPC147192
0.7565 Intermediate Similarity NPC280616
0.7565 Intermediate Similarity NPC242913
0.7565 Intermediate Similarity NPC171831
0.7565 Intermediate Similarity NPC19136
0.7559 Intermediate Similarity NPC246166
0.7541 Intermediate Similarity NPC108532
0.754 Intermediate Similarity NPC472703
0.7522 Intermediate Similarity NPC474308
0.7521 Intermediate Similarity NPC277788
0.7519 Intermediate Similarity NPC472247
0.75 Intermediate Similarity NPC278228
0.75 Intermediate Similarity NPC79608
0.748 Intermediate Similarity NPC14141
0.7477 Intermediate Similarity NPC473347
0.7459 Intermediate Similarity NPC471616
0.7458 Intermediate Similarity NPC281604
0.7442 Intermediate Similarity NPC475695
0.744 Intermediate Similarity NPC474223
0.744 Intermediate Similarity NPC475827
0.7438 Intermediate Similarity NPC87069
0.7436 Intermediate Similarity NPC37115
0.7434 Intermediate Similarity NPC175852
0.7434 Intermediate Similarity NPC210529
0.7434 Intermediate Similarity NPC160548
0.7424 Intermediate Similarity NPC469499
0.7424 Intermediate Similarity NPC108553
0.7417 Intermediate Similarity NPC234376
0.7417 Intermediate Similarity NPC474314
0.7405 Intermediate Similarity NPC272946
0.7402 Intermediate Similarity NPC327070
0.7398 Intermediate Similarity NPC242764
0.7398 Intermediate Similarity NPC105141
0.7391 Intermediate Similarity NPC45307
0.7385 Intermediate Similarity NPC268607
0.7373 Intermediate Similarity NPC156648
0.7372 Intermediate Similarity NPC475413
0.7372 Intermediate Similarity NPC474303
0.7372 Intermediate Similarity NPC473497
0.7364 Intermediate Similarity NPC476033
0.736 Intermediate Similarity NPC472708
0.736 Intermediate Similarity NPC160235
0.736 Intermediate Similarity NPC204784
0.7357 Intermediate Similarity NPC170668
0.7355 Intermediate Similarity NPC161611
0.7355 Intermediate Similarity NPC48525
0.7355 Intermediate Similarity NPC265002
0.735 Intermediate Similarity NPC321670
0.7344 Intermediate Similarity NPC477362
0.7328 Intermediate Similarity NPC301943
0.7328 Intermediate Similarity NPC474365
0.7328 Intermediate Similarity NPC234305
0.7317 Intermediate Similarity NPC149691
0.7313 Intermediate Similarity NPC215484
0.7311 Intermediate Similarity NPC474364
0.7308 Intermediate Similarity NPC81135
0.7308 Intermediate Similarity NPC477365
0.7308 Intermediate Similarity NPC472706
0.7295 Intermediate Similarity NPC153053
0.7293 Intermediate Similarity NPC281798
0.7293 Intermediate Similarity NPC233692
0.7288 Intermediate Similarity NPC51174
0.7287 Intermediate Similarity NPC295664
0.7281 Intermediate Similarity NPC154517
0.7281 Intermediate Similarity NPC135951
0.728 Intermediate Similarity NPC104514
0.7273 Intermediate Similarity NPC321852
0.7273 Intermediate Similarity NPC185840
0.7273 Intermediate Similarity NPC477250
0.7273 Intermediate Similarity NPC471832
0.7266 Intermediate Similarity NPC325301
0.7266 Intermediate Similarity NPC474159
0.7266 Intermediate Similarity NPC474254
0.7259 Intermediate Similarity NPC477367
0.7259 Intermediate Similarity NPC232888
0.7258 Intermediate Similarity NPC212891
0.7257 Intermediate Similarity NPC30361
0.7252 Intermediate Similarity NPC477370
0.7246 Intermediate Similarity NPC256162
0.7246 Intermediate Similarity NPC59775
0.7239 Intermediate Similarity NPC477364
0.7236 Intermediate Similarity NPC221870
0.7231 Intermediate Similarity NPC477363
0.7231 Intermediate Similarity NPC477366
0.7231 Intermediate Similarity NPC132921
0.7227 Intermediate Similarity NPC20485
0.7218 Intermediate Similarity NPC329344
0.7218 Intermediate Similarity NPC217052
0.7218 Intermediate Similarity NPC32626
0.7218 Intermediate Similarity NPC237506
0.7217 Intermediate Similarity NPC80115
0.7213 Intermediate Similarity NPC477245
0.7213 Intermediate Similarity NPC477246
0.7203 Intermediate Similarity NPC477101
0.7203 Intermediate Similarity NPC477097
0.7203 Intermediate Similarity NPC472919
0.7203 Intermediate Similarity NPC477099
0.72 Intermediate Similarity NPC94425
0.72 Intermediate Similarity NPC325295
0.72 Intermediate Similarity NPC76308
0.72 Intermediate Similarity NPC471553
0.7197 Intermediate Similarity NPC217431
0.719 Intermediate Similarity NPC260818
0.719 Intermediate Similarity NPC476003
0.719 Intermediate Similarity NPC477247
0.7185 Intermediate Similarity NPC477359
0.7185 Intermediate Similarity NPC88255
0.7185 Intermediate Similarity NPC28836
0.7185 Intermediate Similarity NPC311492
0.7185 Intermediate Similarity NPC136994
0.7185 Intermediate Similarity NPC477368
0.7183 Intermediate Similarity NPC205389
0.7182 Intermediate Similarity NPC173443
0.7182 Intermediate Similarity NPC220893
0.7176 Intermediate Similarity NPC477357
0.7176 Intermediate Similarity NPC251407
0.7176 Intermediate Similarity NPC168653
0.7167 Intermediate Similarity NPC469636
0.7167 Intermediate Similarity NPC475282
0.7167 Intermediate Similarity NPC31274
0.7164 Intermediate Similarity NPC239358
0.7164 Intermediate Similarity NPC233860
0.7163 Intermediate Similarity NPC25043
0.7163 Intermediate Similarity NPC134131
0.7163 Intermediate Similarity NPC127857
0.7156 Intermediate Similarity NPC89377
0.7155 Intermediate Similarity NPC158623
0.7155 Intermediate Similarity NPC469481
0.7154 Intermediate Similarity NPC172525
0.7154 Intermediate Similarity NPC307651
0.7154 Intermediate Similarity NPC244454
0.7153 Intermediate Similarity NPC51602
0.7153 Intermediate Similarity NPC27721
0.7153 Intermediate Similarity NPC86772
0.7153 Intermediate Similarity NPC471103
0.7143 Intermediate Similarity NPC254233
0.7143 Intermediate Similarity NPC329705
0.7143 Intermediate Similarity NPC477251
0.7143 Intermediate Similarity NPC474111
0.7132 Intermediate Similarity NPC79699
0.7132 Intermediate Similarity NPC474895
0.7132 Intermediate Similarity NPC200154
0.7131 Intermediate Similarity NPC139946
0.7131 Intermediate Similarity NPC158282
0.7131 Intermediate Similarity NPC470355
0.713 Intermediate Similarity NPC179411
0.7123 Intermediate Similarity NPC21410
0.7123 Intermediate Similarity NPC473670
0.7122 Intermediate Similarity NPC77493
0.7122 Intermediate Similarity NPC242355
0.7121 Intermediate Similarity NPC51448
0.7121 Intermediate Similarity NPC115797
0.712 Intermediate Similarity NPC190298
0.7113 Intermediate Similarity NPC469513
0.7111 Intermediate Similarity NPC472248
0.7109 Intermediate Similarity NPC229600
0.7107 Intermediate Similarity NPC174099
0.7107 Intermediate Similarity NPC326187
0.7101 Intermediate Similarity NPC67349
0.7101 Intermediate Similarity NPC272523
0.7101 Intermediate Similarity NPC325805
0.7101 Intermediate Similarity NPC279676
0.7099 Intermediate Similarity NPC476599
0.7099 Intermediate Similarity NPC328997
0.7099 Intermediate Similarity NPC236405
0.7099 Intermediate Similarity NPC294050
0.7094 Intermediate Similarity NPC60373
0.7094 Intermediate Similarity NPC154905
0.7092 Intermediate Similarity NPC80895
0.7092 Intermediate Similarity NPC471912
0.7087 Intermediate Similarity NPC328459
0.7087 Intermediate Similarity NPC241634
0.7087 Intermediate Similarity NPC90522
0.7083 Intermediate Similarity NPC249811
0.7083 Intermediate Similarity NPC232583
0.7083 Intermediate Similarity NPC25484
0.708 Intermediate Similarity NPC233350
0.708 Intermediate Similarity NPC202729

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC469509 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
0.7815 Intermediate Similarity NPD690 Clinical (unspecified phase)
0.775 Intermediate Similarity NPD4198 Discontinued
0.7712 Intermediate Similarity NPD969 Suspended
0.7667 Intermediate Similarity NPD2629 Approved
0.7632 Intermediate Similarity NPD6647 Phase 2
0.7542 Intermediate Similarity NPD2067 Discontinued
0.7434 Intermediate Similarity NPD9495 Approved
0.7302 Intermediate Similarity NPD5306 Approved
0.7302 Intermediate Similarity NPD5305 Approved
0.7258 Intermediate Similarity NPD694 Clinical (unspecified phase)
0.7244 Intermediate Similarity NPD4135 Approved
0.7244 Intermediate Similarity NPD4106 Approved
0.7244 Intermediate Similarity NPD4136 Approved
0.719 Intermediate Similarity NPD2181 Clinical (unspecified phase)
0.7188 Intermediate Similarity NPD4807 Approved
0.7188 Intermediate Similarity NPD4806 Approved
0.7143 Intermediate Similarity NPD5952 Clinical (unspecified phase)
0.7121 Intermediate Similarity NPD3664 Approved
0.7121 Intermediate Similarity NPD3662 Phase 3
0.7121 Intermediate Similarity NPD3661 Approved
0.7121 Intermediate Similarity NPD3663 Approved
0.7121 Intermediate Similarity NPD5204 Approved
0.7111 Intermediate Similarity NPD7966 Clinical (unspecified phase)
0.7087 Intermediate Similarity NPD4102 Approved
0.7087 Intermediate Similarity NPD4105 Approved
0.7045 Intermediate Similarity NPD5647 Approved
0.7034 Intermediate Similarity NPD5738 Clinical (unspecified phase)
0.7025 Intermediate Similarity NPD6831 Clinical (unspecified phase)
0.7025 Intermediate Similarity NPD2182 Approved
0.697 Remote Similarity NPD2627 Approved
0.697 Remote Similarity NPD2160 Approved
0.697 Remote Similarity NPD2626 Approved
0.697 Remote Similarity NPD2159 Approved
0.697 Remote Similarity NPD2628 Approved
0.697 Remote Similarity NPD2625 Approved
0.6963 Remote Similarity NPD4621 Approved
0.6963 Remote Similarity NPD4619 Approved
0.693 Remote Similarity NPD5122 Clinical (unspecified phase)
0.6917 Remote Similarity NPD6007 Clinical (unspecified phase)
0.6917 Remote Similarity NPD5048 Discontinued
0.6901 Remote Similarity NPD2575 Approved
0.6889 Remote Similarity NPD7095 Approved
0.688 Remote Similarity NPD2652 Approved
0.688 Remote Similarity NPD2650 Approved
0.685 Remote Similarity NPD9493 Approved
0.6833 Remote Similarity NPD5909 Discontinued
0.6833 Remote Similarity NPD1237 Approved
0.6815 Remote Similarity NPD4620 Approved
0.6815 Remote Similarity NPD5203 Approved
0.6815 Remote Similarity NPD4617 Approved
0.6815 Remote Similarity NPD5202 Clinical (unspecified phase)
0.6815 Remote Similarity NPD5201 Approved
0.6814 Remote Similarity NPD9256 Approved
0.6814 Remote Similarity NPD9258 Approved
0.6803 Remote Similarity NPD1358 Approved
0.6791 Remote Similarity NPD6085 Phase 2
0.6791 Remote Similarity NPD5740 Clinical (unspecified phase)
0.678 Remote Similarity NPD2066 Phase 3
0.6739 Remote Similarity NPD6311 Approved
0.6739 Remote Similarity NPD6310 Approved
0.6739 Remote Similarity NPD6309 Approved
0.6724 Remote Similarity NPD1693 Approved
0.6721 Remote Similarity NPD6685 Approved
0.6696 Remote Similarity NPD1282 Approved
0.6696 Remote Similarity NPD1088 Approved
0.6694 Remote Similarity NPD164 Approved
0.6693 Remote Similarity NPD5951 Approved
0.6691 Remote Similarity NPD6355 Discontinued
0.6667 Remote Similarity NPD9267 Approved
0.6667 Remote Similarity NPD5734 Clinical (unspecified phase)
0.6667 Remote Similarity NPD9263 Approved
0.6667 Remote Similarity NPD6233 Phase 2
0.6667 Remote Similarity NPD4248 Discontinued
0.6667 Remote Similarity NPD9264 Approved
0.6643 Remote Similarity NPD6653 Approved
0.6639 Remote Similarity NPD1238 Approved
0.6621 Remote Similarity NPD6190 Approved
0.6619 Remote Similarity NPD5119 Approved
0.6619 Remote Similarity NPD5121 Approved
0.6619 Remote Similarity NPD5120 Approved
0.6618 Remote Similarity NPD5736 Approved
0.6617 Remote Similarity NPD9717 Approved
0.6615 Remote Similarity NPD9545 Approved
0.6614 Remote Similarity NPD6010 Discontinued
0.6613 Remote Similarity NPD74 Approved
0.6613 Remote Similarity NPD9266 Approved
0.66 Remote Similarity NPD6599 Discontinued
0.6594 Remote Similarity NPD6798 Discontinued
0.6591 Remote Similarity NPD3496 Discontinued
0.6589 Remote Similarity NPD5291 Approved
0.6589 Remote Similarity NPD5292 Approved
0.6585 Remote Similarity NPD3134 Approved
0.6579 Remote Similarity NPD689 Discontinued
0.6575 Remote Similarity NPD7236 Approved
0.6567 Remote Similarity NPD4379 Clinical (unspecified phase)
0.656 Remote Similarity NPD4233 Approved
0.656 Remote Similarity NPD4234 Approved
0.6552 Remote Similarity NPD8166 Discontinued
0.6552 Remote Similarity NPD4628 Phase 3
0.6547 Remote Similarity NPD4062 Phase 3
0.6542 Remote Similarity NPD9294 Approved
0.6531 Remote Similarity NPD6799 Approved
0.6525 Remote Similarity NPD1989 Approved
0.6522 Remote Similarity NPD3673 Approved
0.6522 Remote Similarity NPD1090 Approved
0.6522 Remote Similarity NPD3672 Approved
0.6522 Remote Similarity NPD1086 Approved
0.6522 Remote Similarity NPD1089 Approved
0.6515 Remote Similarity NPD5125 Phase 3
0.6515 Remote Similarity NPD5126 Approved
0.6515 Remote Similarity NPD3412 Clinical (unspecified phase)
0.6515 Remote Similarity NPD1778 Approved
0.6512 Remote Similarity NPD7157 Approved
0.65 Remote Similarity NPD4060 Phase 1
0.65 Remote Similarity NPD7798 Approved
0.6496 Remote Similarity NPD1202 Approved
0.6489 Remote Similarity NPD7741 Discontinued
0.6486 Remote Similarity NPD9491 Approved
0.6486 Remote Similarity NPD3971 Phase 1
0.6475 Remote Similarity NPD1930 Approved
0.6475 Remote Similarity NPD1929 Approved
0.6475 Remote Similarity NPD1931 Clinical (unspecified phase)
0.6475 Remote Similarity NPD5765 Approved
0.6475 Remote Similarity NPD3764 Approved
0.6475 Remote Similarity NPD3268 Approved
0.6471 Remote Similarity NPD2797 Approved
0.646 Remote Similarity NPD9259 Approved
0.646 Remote Similarity NPD9257 Approved
0.6454 Remote Similarity NPD447 Suspended
0.6441 Remote Similarity NPD1432 Clinical (unspecified phase)
0.6439 Remote Similarity NPD5585 Approved
0.6435 Remote Similarity NPD800 Approved
0.6434 Remote Similarity NPD9281 Approved
0.6434 Remote Similarity NPD7033 Discontinued
0.6434 Remote Similarity NPD7305 Phase 1
0.6429 Remote Similarity NPD7961 Discontinued
0.6429 Remote Similarity NPD6663 Approved
0.6418 Remote Similarity NPD2611 Approved
0.6418 Remote Similarity NPD4218 Approved
0.6418 Remote Similarity NPD4217 Approved
0.6418 Remote Similarity NPD3131 Approved
0.6418 Remote Similarity NPD2612 Approved
0.6418 Remote Similarity NPD2609 Approved
0.6418 Remote Similarity NPD4216 Approved
0.6418 Remote Similarity NPD2608 Approved
0.6418 Remote Similarity NPD4215 Approved
0.6418 Remote Similarity NPD2610 Approved
0.6418 Remote Similarity NPD3132 Approved
0.6418 Remote Similarity NPD6287 Discontinued
0.6414 Remote Similarity NPD2424 Discontinued
0.6414 Remote Similarity NPD4534 Discontinued
0.6406 Remote Similarity NPD7094 Approved
0.6406 Remote Similarity NPD5277 Phase 2
0.6406 Remote Similarity NPD6858 Approved
0.6403 Remote Similarity NPD7008 Discontinued
0.64 Remote Similarity NPD290 Approved
0.64 Remote Similarity NPD5403 Approved
0.6397 Remote Similarity NPD5667 Approved
0.6391 Remote Similarity NPD7163 Clinical (unspecified phase)
0.6389 Remote Similarity NPD4173 Approved
0.6389 Remote Similarity NPD4172 Approved
0.6378 Remote Similarity NPD4141 Clinical (unspecified phase)
0.6358 Remote Similarity NPD7239 Suspended
0.6357 Remote Similarity NPD1048 Approved
0.6355 Remote Similarity NPD9716 Approved
0.635 Remote Similarity NPD6362 Approved
0.635 Remote Similarity NPD1203 Approved
0.635 Remote Similarity NPD987 Approved
0.6349 Remote Similarity NPD2684 Approved
0.6341 Remote Similarity NPD9261 Approved
0.6338 Remote Similarity NPD230 Phase 1
0.6338 Remote Similarity NPD4340 Discontinued
0.6331 Remote Similarity NPD6832 Phase 2
0.6328 Remote Similarity NPD1609 Clinical (unspecified phase)
0.6328 Remote Similarity NPD6912 Phase 3
0.6319 Remote Similarity NPD2799 Discontinued
0.6316 Remote Similarity NPD4196 Clinical (unspecified phase)
0.6316 Remote Similarity NPD446 Clinical (unspecified phase)
0.6312 Remote Similarity NPD520 Approved
0.6306 Remote Similarity NPD226 Approved
0.6303 Remote Similarity NPD2934 Approved
0.6303 Remote Similarity NPD2933 Approved
0.6299 Remote Similarity NPD5236 Approved
0.6299 Remote Similarity NPD5237 Approved
0.6299 Remote Similarity NPD5239 Approved
0.6299 Remote Similarity NPD5235 Approved
0.6299 Remote Similarity NPD5240 Approved
0.6293 Remote Similarity NPD5347 Phase 2
0.6293 Remote Similarity NPD5346 Phase 2
0.6288 Remote Similarity NPD5536 Phase 2
0.6287 Remote Similarity NPD8434 Phase 2
0.6286 Remote Similarity NPD2598 Clinical (unspecified phase)
0.6282 Remote Similarity NPD3882 Suspended
0.6281 Remote Similarity NPD5926 Approved
0.6279 Remote Similarity NPD7843 Approved
0.6277 Remote Similarity NPD3225 Approved
0.627 Remote Similarity NPD9265 Clinical (unspecified phase)
0.6269 Remote Similarity NPD3019 Approved
0.6269 Remote Similarity NPD2932 Approved
0.6269 Remote Similarity NPD4626 Approved

Structure

External Identifiers

PubChem CID   46883483
ChEMBL   CHEMBL1081689
ZINC  

Physicochemical Properties

Molecular Weight:  288.10
ALogP:  -0.3108
MLogP:  2.67
XLogP:  3.015
# Rotatable Bonds:  7
Polar Surface Area:  83.83
# H-Bond Aceptor:  5
# H-Bond Donor:  2
# Rings:  2
# Heavy Atoms:  21

Download Data

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