Natural Product: NPC7464

Natural Product ID:  NPC7464
Common Name:   Garcinialiptone D
IUPAC Name:   (1S,5S,7R)-5-(3,4-dihydroxybenzoyl)-2-hydroxy-6,6-dimethyl-1,3-bis(3-methylbut-2-enyl)-7-[(2R)-5-methyl-2-prop-1-en-2-ylhex-5-enyl]bicyclo[3.3.1]non-2-ene-4,9-dione
Synonyms:   Garcinialiptone D
Molecular Formula:   C38H50O6
Standard InCHIKey:  BZLTYFKCXDZVOR-YPSKTYFSSA-N
Standard InCHI:  InChI=1S/C38H50O6/c1-22(2)11-13-26(25(7)8)19-28-21-37(18-17-24(5)6)33(42)29(15-12-23(3)4)34(43)38(35(37)44,36(28,9)10)32(41)27-14-16-30(39)31(40)20-27/h12,14,16-17,20,26,28,39-40,42H,1,7,11,13,15,18-19,21H2,2-6,8-10H3/t26-,28-,37+,38-/m1/s1
Canonical SMILES:  CC(=CC[C@]12C[C@@H](C[C@H](C(=C)C)CCC(=C)C)C([C@@](C2=O)(C(=O)C(=C1O)CC=C(C)C)C(=O)c1ccc(c(c1)O)O)(C)C)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
NPO7006 Garcinia subelliptica Species Clusiaceae Eukaryota PMID[20232858]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT91 Cell Line KB Homo sapiens IC50 = 3.9 ug/ml 19035792
NPT90 Cell Line DU-145 Homo sapiens IC50 = 3.3 ug/ml 19035792
NPT91 Cell Line KB Homo sapiens IC50 = 4.6 ug/ml 19035792
NPT81 Cell Line A549 Homo sapiens IC50 = 4.4 ug/ml 19035792

  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 NPC7464 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
0.9847 High Similarity NPC5014
0.9847 High Similarity NPC51531
0.9847 High Similarity NPC28592
0.9847 High Similarity NPC297797
0.9847 High Similarity NPC473779
0.9847 High Similarity NPC289358
0.9847 High Similarity NPC46242
0.9847 High Similarity NPC42384
0.9847 High Similarity NPC477849
0.9847 High Similarity NPC50615
0.9847 High Similarity NPC245760
0.9847 High Similarity NPC473479
0.9847 High Similarity NPC149773
0.9847 High Similarity NPC23667
0.9847 High Similarity NPC469857
0.9847 High Similarity NPC91887
0.9847 High Similarity NPC165191
0.9847 High Similarity NPC114333
0.9847 High Similarity NPC157284
0.9773 High Similarity NPC294330
0.9699 High Similarity NPC473527
0.9556 High Similarity NPC471972
0.9556 High Similarity NPC469855
0.9556 High Similarity NPC471971
0.9556 High Similarity NPC30846
0.9416 High Similarity NPC144247
0.9416 High Similarity NPC469856
0.9416 High Similarity NPC8493
0.9416 High Similarity NPC469854
0.9416 High Similarity NPC294679
0.9416 High Similarity NPC145301
0.9416 High Similarity NPC469375
0.9403 High Similarity NPC471974
0.9403 High Similarity NPC469681
0.9403 High Similarity NPC469680
0.9281 High Similarity NPC273798
0.9281 High Similarity NPC471970
0.916 High Similarity NPC25736
0.9149 High Similarity NPC132810
0.9149 High Similarity NPC46549
0.9149 High Similarity NPC264229
0.9085 High Similarity NPC237441
0.903 High Similarity NPC4170
0.903 High Similarity NPC474715
0.903 High Similarity NPC138472
0.8905 High Similarity NPC277559
0.8889 High Similarity NPC111845
0.8889 High Similarity NPC48949
0.8841 High Similarity NPC230811
0.8836 High Similarity NPC305710
0.8806 High Similarity NPC117609
0.8797 High Similarity NPC234175
0.8768 High Similarity NPC49911
0.8759 High Similarity NPC153088
0.8759 High Similarity NPC43353
0.875 High Similarity NPC294226
0.8716 High Similarity NPC471968
0.8714 High Similarity NPC470035
0.8671 High Similarity NPC470038
0.8662 High Similarity NPC199936
0.8633 High Similarity NPC118366
0.8623 High Similarity NPC258502
0.8592 High Similarity NPC184935
0.8582 High Similarity NPC471853
0.8582 High Similarity NPC72667
0.8582 High Similarity NPC476534
0.8571 High Similarity NPC416
0.8571 High Similarity NPC61398
0.8552 High Similarity NPC10842
0.8542 High Similarity NPC258856
0.8507 High Similarity NPC254492
0.8507 High Similarity NPC15837
0.85 High Similarity NPC471152
0.8462 Intermediate Similarity NPC229218
0.8462 Intermediate Similarity NPC192597
0.8462 Intermediate Similarity NPC141817
0.8462 Intermediate Similarity NPC176030
0.8462 Intermediate Similarity NPC169214
0.8462 Intermediate Similarity NPC248068
0.8456 Intermediate Similarity NPC171460
0.845 Intermediate Similarity NPC150919
0.8444 Intermediate Similarity NPC176130
0.8444 Intermediate Similarity NPC78364
0.8444 Intermediate Similarity NPC69424
0.8444 Intermediate Similarity NPC84672
0.8444 Intermediate Similarity NPC324209
0.8414 Intermediate Similarity NPC75295
0.8394 Intermediate Similarity NPC108129
0.8382 Intermediate Similarity NPC96024
0.838 Intermediate Similarity NPC472903
0.8378 Intermediate Similarity NPC470037
0.8369 Intermediate Similarity NPC290030
0.8369 Intermediate Similarity NPC147418
0.8369 Intermediate Similarity NPC264022
0.8358 Intermediate Similarity NPC15127
0.8358 Intermediate Similarity NPC199273
0.8346 Intermediate Similarity NPC91478
0.8333 Intermediate Similarity NPC236520
0.8333 Intermediate Similarity NPC294361
0.8322 Intermediate Similarity NPC203063
0.8321 Intermediate Similarity NPC276238
0.8321 Intermediate Similarity NPC117899
0.831 Intermediate Similarity NPC87723
0.8309 Intermediate Similarity NPC471530
0.8298 Intermediate Similarity NPC65005
0.8298 Intermediate Similarity NPC194764
0.8298 Intermediate Similarity NPC264112
0.8286 Intermediate Similarity NPC202225
0.8286 Intermediate Similarity NPC50924
0.8271 Intermediate Similarity NPC120545
0.8264 Intermediate Similarity NPC472904
0.8248 Intermediate Similarity NPC193203
0.8239 Intermediate Similarity NPC53001
0.8235 Intermediate Similarity NPC3224
0.8235 Intermediate Similarity NPC71610
0.8231 Intermediate Similarity NPC299252
0.8231 Intermediate Similarity NPC277394
0.8231 Intermediate Similarity NPC61062
0.8227 Intermediate Similarity NPC72918
0.8219 Intermediate Similarity NPC309169
0.8219 Intermediate Similarity NPC196941
0.8209 Intermediate Similarity NPC86900
0.8209 Intermediate Similarity NPC282577
0.8207 Intermediate Similarity NPC477873
0.8207 Intermediate Similarity NPC469447
0.8207 Intermediate Similarity NPC291078
0.8201 Intermediate Similarity NPC18798
0.8201 Intermediate Similarity NPC471851
0.8201 Intermediate Similarity NPC244699
0.8201 Intermediate Similarity NPC291001
0.82 Intermediate Similarity NPC35
0.82 Intermediate Similarity NPC144283
0.8188 Intermediate Similarity NPC303910
0.8182 Intermediate Similarity NPC206207
0.8176 Intermediate Similarity NPC52692
0.8175 Intermediate Similarity NPC107672
0.8169 Intermediate Similarity NPC474311
0.8163 Intermediate Similarity NPC73416
0.8163 Intermediate Similarity NPC160777
0.8156 Intermediate Similarity NPC293454
0.8156 Intermediate Similarity NPC475088
0.8154 Intermediate Similarity NPC322197
0.8151 Intermediate Similarity NPC239608
0.8151 Intermediate Similarity NPC46161
0.8151 Intermediate Similarity NPC238629
0.8143 Intermediate Similarity NPC175738
0.8143 Intermediate Similarity NPC135801
0.8138 Intermediate Similarity NPC472410
0.8138 Intermediate Similarity NPC84273
0.8134 Intermediate Similarity NPC154696
0.8116 Intermediate Similarity NPC3009
0.8116 Intermediate Similarity NPC229894
0.8116 Intermediate Similarity NPC48248
0.8112 Intermediate Similarity NPC36868
0.8112 Intermediate Similarity NPC475957
0.8108 Intermediate Similarity NPC476535
0.8102 Intermediate Similarity NPC306765
0.8101 Intermediate Similarity NPC478059
0.8101 Intermediate Similarity NPC478060
0.8101 Intermediate Similarity NPC471975
0.8101 Intermediate Similarity NPC470374
0.8101 Intermediate Similarity NPC470377
0.8099 Intermediate Similarity NPC283088
0.8099 Intermediate Similarity NPC477596
0.8099 Intermediate Similarity NPC249272
0.8095 Intermediate Similarity NPC53520
0.8085 Intermediate Similarity NPC327410
0.8085 Intermediate Similarity NPC78307
0.8085 Intermediate Similarity NPC53896
0.8085 Intermediate Similarity NPC477139
0.8082 Intermediate Similarity NPC11314
0.8079 Intermediate Similarity NPC124842
0.8074 Intermediate Similarity NPC68167
0.8074 Intermediate Similarity NPC139171
0.8071 Intermediate Similarity NPC243305
0.8071 Intermediate Similarity NPC34070
0.8071 Intermediate Similarity NPC469526
0.8069 Intermediate Similarity NPC169452
0.8069 Intermediate Similarity NPC181560
0.8067 Intermediate Similarity NPC142654
0.806 Intermediate Similarity NPC259703
0.806 Intermediate Similarity NPC32322
0.806 Intermediate Similarity NPC98305
0.8058 Intermediate Similarity NPC34414
0.8058 Intermediate Similarity NPC99731
0.8058 Intermediate Similarity NPC146647
0.8056 Intermediate Similarity NPC141368
0.8056 Intermediate Similarity NPC473622
0.8054 Intermediate Similarity NPC476821
0.8043 Intermediate Similarity NPC473787
0.8042 Intermediate Similarity NPC193358
0.8041 Intermediate Similarity NPC225351
0.8029 Intermediate Similarity NPC123506
0.8028 Intermediate Similarity NPC166480
0.8028 Intermediate Similarity NPC270899
0.8028 Intermediate Similarity NPC12070
0.8028 Intermediate Similarity NPC477594
0.8028 Intermediate Similarity NPC282780
0.8027 Intermediate Similarity NPC224884
0.8027 Intermediate Similarity NPC209085

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC7464 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
0.8392 Intermediate Similarity NPD8166 Discontinued
0.8143 Intermediate Similarity NPD943 Approved
0.812 Intermediate Similarity NPD2932 Approved
0.7985 Intermediate Similarity NPD3019 Approved
0.7899 Intermediate Similarity NPD1470 Approved
0.78 Intermediate Similarity NPD7422 Clinical (unspecified phase)
0.7793 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.7793 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.7737 Intermediate Similarity NPD1201 Approved
0.7692 Intermediate Similarity NPD3022 Approved
0.7692 Intermediate Similarity NPD3021 Approved
0.7687 Intermediate Similarity NPD405 Clinical (unspecified phase)
0.7667 Intermediate Similarity NPD3300 Phase 2
0.7647 Intermediate Similarity NPD4196 Clinical (unspecified phase)
0.7536 Intermediate Similarity NPD3026 Approved
0.7536 Intermediate Similarity NPD3023 Approved
0.7518 Intermediate Similarity NPD3025 Approved
0.7518 Intermediate Similarity NPD3024 Approved
0.7429 Intermediate Similarity NPD9269 Phase 2
0.7429 Intermediate Similarity NPD3972 Approved
0.7413 Intermediate Similarity NPD9494 Approved
0.7405 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7386 Intermediate Similarity NPD7390 Discontinued
0.7383 Intermediate Similarity NPD5406 Approved
0.7383 Intermediate Similarity NPD5405 Approved
0.7383 Intermediate Similarity NPD5404 Approved
0.7383 Intermediate Similarity NPD5408 Approved
0.7378 Intermediate Similarity NPD7473 Discontinued
0.7376 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.7329 Intermediate Similarity NPD6663 Approved
0.7315 Intermediate Similarity NPD3299 Clinical (unspecified phase)
0.7296 Intermediate Similarity NPD2801 Approved
0.7292 Intermediate Similarity NPD5736 Approved
0.7273 Intermediate Similarity NPD1511 Approved
0.7261 Intermediate Similarity NPD7458 Discontinued
0.7233 Intermediate Similarity NPD1934 Approved
0.723 Intermediate Similarity NPD230 Phase 1
0.7219 Intermediate Similarity NPD2344 Approved
0.7218 Intermediate Similarity NPD6831 Clinical (unspecified phase)
0.7205 Intermediate Similarity NPD3882 Suspended
0.72 Intermediate Similarity NPD2799 Discontinued
0.7195 Intermediate Similarity NPD6232 Discontinued
0.719 Intermediate Similarity NPD4628 Phase 3
0.7179 Intermediate Similarity NPD1512 Approved
0.7168 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7153 Intermediate Similarity NPD5951 Approved
0.7153 Intermediate Similarity NPD1164 Approved
0.7152 Intermediate Similarity NPD2935 Discontinued
0.7143 Intermediate Similarity NPD3764 Approved
0.7143 Intermediate Similarity NPD9268 Approved
0.7113 Intermediate Similarity NPD3092 Approved
0.7107 Intermediate Similarity NPD7028 Phase 2
0.7105 Intermediate Similarity NPD2346 Discontinued
0.7103 Intermediate Similarity NPD2798 Approved
0.7081 Intermediate Similarity NPD7819 Suspended
0.7078 Intermediate Similarity NPD7003 Approved
0.7071 Intermediate Similarity NPD3091 Approved
0.7034 Intermediate Similarity NPD3094 Phase 2
0.7032 Intermediate Similarity NPD2309 Approved
0.7032 Intermediate Similarity NPD6190 Approved
0.7015 Intermediate Similarity NPD9265 Clinical (unspecified phase)
0.7014 Intermediate Similarity NPD1755 Approved
0.7 Intermediate Similarity NPD3020 Approved
0.6994 Remote Similarity NPD8055 Clinical (unspecified phase)
0.698 Remote Similarity NPD8032 Phase 2
0.6977 Remote Similarity NPD3534 Clinical (unspecified phase)
0.6974 Remote Similarity NPD1510 Phase 2
0.6972 Remote Similarity NPD7163 Clinical (unspecified phase)
0.6972 Remote Similarity NPD3412 Clinical (unspecified phase)
0.6972 Remote Similarity NPD4059 Approved
0.6966 Remote Similarity NPD1876 Approved
0.6962 Remote Similarity NPD6273 Approved
0.6954 Remote Similarity NPD6651 Approved
0.6954 Remote Similarity NPD8434 Phase 2
0.6954 Remote Similarity NPD1607 Approved
0.6954 Remote Similarity NPD8150 Discontinued
0.6944 Remote Similarity NPD4878 Approved
0.6937 Remote Similarity NPD3226 Approved
0.6933 Remote Similarity NPD8443 Clinical (unspecified phase)
0.6933 Remote Similarity NPD3619 Clinical (unspecified phase)
0.6933 Remote Similarity NPD1240 Approved
0.6933 Remote Similarity NPD3620 Phase 2
0.6928 Remote Similarity NPD6100 Approved
0.6928 Remote Similarity NPD6099 Approved
0.6923 Remote Similarity NPD3818 Discontinued
0.6923 Remote Similarity NPD7910 Clinical (unspecified phase)
0.6905 Remote Similarity NPD6168 Clinical (unspecified phase)
0.6905 Remote Similarity NPD6167 Clinical (unspecified phase)
0.6905 Remote Similarity NPD6166 Phase 2
0.6903 Remote Similarity NPD2800 Approved
0.6899 Remote Similarity NPD4378 Clinical (unspecified phase)
0.6894 Remote Similarity NPD4380 Phase 2
0.689 Remote Similarity NPD4868 Clinical (unspecified phase)
0.6883 Remote Similarity NPD1471 Phase 3
0.6879 Remote Similarity NPD5536 Phase 2
0.6879 Remote Similarity NPD7610 Discontinued
0.6871 Remote Similarity NPD257 Approved
0.6871 Remote Similarity NPD258 Approved
0.6867 Remote Similarity NPD5494 Approved
0.6861 Remote Similarity NPD4141 Clinical (unspecified phase)
0.6859 Remote Similarity NPD6398 Clinical (unspecified phase)
0.6853 Remote Similarity NPD3095 Discontinued
0.6849 Remote Similarity NPD1283 Approved
0.6848 Remote Similarity NPD7075 Discontinued
0.6842 Remote Similarity NPD7074 Phase 3
0.6839 Remote Similarity NPD970 Clinical (unspecified phase)
0.6835 Remote Similarity NPD6143 Clinical (unspecified phase)
0.6832 Remote Similarity NPD3455 Phase 2
0.6831 Remote Similarity NPD9545 Approved
0.6829 Remote Similarity NPD8438 Clinical (unspecified phase)
0.6826 Remote Similarity NPD8127 Discontinued
0.6822 Remote Similarity NPD1432 Clinical (unspecified phase)
0.6812 Remote Similarity NPD1609 Clinical (unspecified phase)
0.68 Remote Similarity NPD2313 Discontinued
0.6795 Remote Similarity NPD7421 Clinical (unspecified phase)
0.6792 Remote Similarity NPD7410 Clinical (unspecified phase)
0.679 Remote Similarity NPD6599 Discontinued
0.6784 Remote Similarity NPD7054 Approved
0.6783 Remote Similarity NPD1651 Approved
0.6776 Remote Similarity NPD447 Suspended
0.6772 Remote Similarity NPD7236 Approved
0.6769 Remote Similarity NPD2859 Approved
0.6769 Remote Similarity NPD2860 Approved
0.6768 Remote Similarity NPD7096 Clinical (unspecified phase)
0.6768 Remote Similarity NPD1465 Phase 2
0.6763 Remote Similarity NPD7635 Approved
0.6763 Remote Similarity NPD5027 Approved
0.6763 Remote Similarity NPD5029 Approved
0.6763 Remote Similarity NPD7685 Pre-registration
0.6763 Remote Similarity NPD5031 Approved
0.6752 Remote Similarity NPD4110 Phase 3
0.6752 Remote Similarity NPD3750 Approved
0.6752 Remote Similarity NPD4109 Clinical (unspecified phase)
0.6748 Remote Similarity NPD6873 Phase 2
0.6744 Remote Similarity NPD7472 Approved
0.6733 Remote Similarity NPD7095 Approved
0.6733 Remote Similarity NPD5952 Clinical (unspecified phase)
0.6731 Remote Similarity NPD1549 Phase 2
0.6727 Remote Similarity NPD5978 Approved
0.6727 Remote Similarity NPD5977 Approved
0.6727 Remote Similarity NPD3817 Phase 2
0.6724 Remote Similarity NPD4954 Approved
0.6724 Remote Similarity NPD4955 Approved
0.6724 Remote Similarity NPD36 Approved
0.6724 Remote Similarity NPD5026 Approved
0.6724 Remote Similarity NPD5028 Approved
0.6724 Remote Similarity NPD5034 Approved
0.6716 Remote Similarity NPD1931 Clinical (unspecified phase)
0.6716 Remote Similarity NPD1929 Approved
0.6716 Remote Similarity NPD1930 Approved
0.6715 Remote Similarity NPD74 Approved
0.6715 Remote Similarity NPD9266 Approved
0.6711 Remote Similarity NPD826 Approved
0.6711 Remote Similarity NPD825 Approved
0.6708 Remote Similarity NPD6980 Clinical (unspecified phase)
0.6692 Remote Similarity NPD2934 Approved
0.6692 Remote Similarity NPD2933 Approved
0.669 Remote Similarity NPD9493 Approved
0.6687 Remote Similarity NPD2534 Approved
0.6687 Remote Similarity NPD2532 Approved
0.6687 Remote Similarity NPD2533 Approved
0.6686 Remote Similarity NPD5844 Phase 1
0.6667 Remote Similarity NPD2629 Approved
0.6667 Remote Similarity NPD5030 Phase 2
0.6667 Remote Similarity NPD1552 Clinical (unspecified phase)
0.6667 Remote Similarity NPD1550 Clinical (unspecified phase)
0.6667 Remote Similarity NPD7266 Discontinued
0.6667 Remote Similarity NPD7251 Discontinued
0.6644 Remote Similarity NPD1281 Approved
0.6642 Remote Similarity NPD9264 Approved
0.6642 Remote Similarity NPD9267 Approved
0.6642 Remote Similarity NPD9263 Approved
0.6629 Remote Similarity NPD7808 Phase 3
0.6627 Remote Similarity NPD6959 Discontinued
0.6621 Remote Similarity NPD1751 Approved
0.6617 Remote Similarity NPD2066 Phase 3
0.6611 Remote Similarity NPD7879 Clinical (unspecified phase)
0.6609 Remote Similarity NPD6797 Phase 2
0.6609 Remote Similarity NPD7993 Clinical (unspecified phase)
0.6607 Remote Similarity NPD6234 Discontinued
0.6603 Remote Similarity NPD2796 Approved
0.66 Remote Similarity NPD9569 Approved
0.6599 Remote Similarity NPD1608 Approved
0.6597 Remote Similarity NPD7009 Phase 2
0.6596 Remote Similarity NPD5283 Phase 1
0.6592 Remote Similarity NPD6836 Approved
0.6591 Remote Similarity NPD288 Approved
0.6591 Remote Similarity NPD3495 Discontinued
0.6591 Remote Similarity NPD8312 Approved
0.6591 Remote Similarity NPD8313 Approved
0.659 Remote Similarity NPD1221 Approved
0.6587 Remote Similarity NPD7768 Phase 2
0.6579 Remote Similarity NPD3268 Approved
0.6573 Remote Similarity NPD5037 Approved
0.6573 Remote Similarity NPD5038 Approved
0.6571 Remote Similarity NPD228 Approved
0.6567 Remote Similarity NPD289 Clinical (unspecified phase)
0.6566 Remote Similarity NPD5761 Phase 2
0.6566 Remote Similarity NPD5760 Phase 2
0.6564 Remote Similarity NPD7239 Suspended

Structure

External Identifiers

PubChem CID   46209780
ChEMBL   CHEMBL1098254
ZINC  

Physicochemical Properties

Molecular Weight:  602.36
ALogP:  4.3237
MLogP:  4.98
XLogP:  9.116
# Rotatable Bonds:  23
Polar Surface Area:  111.9
# H-Bond Aceptor:  4
# H-Bond Donor:  3
# Rings:  3
# Heavy Atoms:  44

Download Data

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General Info & Identifiers & Properties  
Structure MOL file  
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Biological Activities  
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