Natural Product: NPC475616

Natural Product ID:  NPC475616
Common Name:   (2,4-Cis And Trans)-Gigantecinone
IUPAC Name:   (5R)-5-[5-[(2R,5S)-5-[(1S,4R)-1,4-dihydroxy-4-[(2R,5R)-5-[(1R)-1-hydroxytridecyl]oxolan-2-yl]butyl]oxolan-2-yl]pentyl]-3-(2-oxopropyl)oxolan-2-one
Synonyms:   (2,4-Cis And Trans)-Gigantecinone
Molecular Formula:   C37H66O8
Standard InCHIKey:  SIKLPUJCNJTZFZ-YUECQCAUSA-N
Standard InCHI:  InChI=1S/C37H66O8/c1-3-4-5-6-7-8-9-10-11-15-18-31(39)35-23-24-36(45-35)33(41)21-20-32(40)34-22-19-29(43-34)16-13-12-14-17-30-26-28(25-27(2)38)37(42)44-30/h28-36,39-41H,3-26H2,1-2H3/t28?,29-,30-,31-,32+,33-,34+,35-,36-/m1/s1
Canonical SMILES:  CCCCCCCCCCCC[C@H]([C@H]1CC[C@@H](O1)[C@@H](CC[C@@H]([C@@H]1CC[C@H](O1)CCCCC[C@H]1OC(=O)C(C1)CC(=O)C)O)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
NPO7202 Goniothalamus giganteus Species Annonaceae Eukaryota PMID[9322367]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT83 Cell Line MCF7 Homo sapiens ED50 > 1 ug/ml 10514324
NPT81 Cell Line A549 Homo sapiens ED50 = 2.14 ug/ml 8691207
NPT139 Cell Line HT-29 Homo sapiens ED50 > 1 ug/ml 19928902
NPT306 Cell Line PC-3 Homo sapiens ED50 = 1.08 ug/ml 18663020
NPT376 Cell Line A498 Homo sapiens ED50 = 2.12 ug/ml 18663020
NPT1381 Organism Aedes aegypti Aedes aegypti LC50 = 0.27 ug/ml 18278870
NPT140 Organism Artemia Artemia LC50 = 3.27 ppm 20058933
NPT783 Cell Line MIA PaCa-2 Homo sapiens ED50 > 1 ug/ml 11421741

  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 NPC475616 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
0.9306 High Similarity NPC475232
0.9306 High Similarity NPC51249
0.9306 High Similarity NPC474100
0.9306 High Similarity NPC473699
0.9306 High Similarity NPC473775
0.9306 High Similarity NPC475260
0.9231 High Similarity NPC473791
0.88 High Similarity NPC228411
0.8214 Intermediate Similarity NPC314364
0.8108 Intermediate Similarity NPC286842
0.8 Intermediate Similarity NPC82315
0.7976 Intermediate Similarity NPC475206
0.7895 Intermediate Similarity NPC28526
0.7791 Intermediate Similarity NPC51662
0.7722 Intermediate Similarity NPC125164
0.7654 Intermediate Similarity NPC474003
0.7632 Intermediate Similarity NPC469925
0.7614 Intermediate Similarity NPC92974
0.7561 Intermediate Similarity NPC470014
0.7527 Intermediate Similarity NPC274695
0.75 Intermediate Similarity NPC215030
0.75 Intermediate Similarity NPC58219
0.75 Intermediate Similarity NPC177629
0.7444 Intermediate Similarity NPC469627
0.7442 Intermediate Similarity NPC3464
0.7442 Intermediate Similarity NPC475963
0.7442 Intermediate Similarity NPC151176
0.7407 Intermediate Similarity NPC217725
0.7397 Intermediate Similarity NPC470363
0.7386 Intermediate Similarity NPC186148
0.7375 Intermediate Similarity NPC291228
0.7375 Intermediate Similarity NPC308096
0.7333 Intermediate Similarity NPC65359
0.7273 Intermediate Similarity NPC476717
0.725 Intermediate Similarity NPC185419
0.725 Intermediate Similarity NPC184550
0.7237 Intermediate Similarity NPC314103
0.7159 Intermediate Similarity NPC476715
0.7143 Intermediate Similarity NPC470114
0.7143 Intermediate Similarity NPC478003
0.7143 Intermediate Similarity NPC478004
0.7143 Intermediate Similarity NPC158388
0.7111 Intermediate Similarity NPC476435
0.7111 Intermediate Similarity NPC470009
0.7105 Intermediate Similarity NPC235788
0.7079 Intermediate Similarity NPC474949
0.7079 Intermediate Similarity NPC475019
0.7079 Intermediate Similarity NPC476015
0.7079 Intermediate Similarity NPC474762
0.7073 Intermediate Similarity NPC138273
0.7071 Intermediate Similarity NPC469441
0.7071 Intermediate Similarity NPC228311
0.7071 Intermediate Similarity NPC41674
0.7071 Intermediate Similarity NPC168890
0.7065 Intermediate Similarity NPC208886
0.7065 Intermediate Similarity NPC12172
0.7053 Intermediate Similarity NPC278028
0.7053 Intermediate Similarity NPC328180
0.7051 Intermediate Similarity NPC135043
0.7051 Intermediate Similarity NPC315525
0.7045 Intermediate Similarity NPC115995
0.7045 Intermediate Similarity NPC474780
0.7024 Intermediate Similarity NPC83108
0.7024 Intermediate Similarity NPC214030
0.7011 Intermediate Similarity NPC311642
0.7011 Intermediate Similarity NPC212340
0.7011 Intermediate Similarity NPC164289
0.7011 Intermediate Similarity NPC242771
0.7011 Intermediate Similarity NPC100366
0.7 Intermediate Similarity NPC290247
0.7 Intermediate Similarity NPC469788
0.7 Intermediate Similarity NPC469787
0.7 Intermediate Similarity NPC176756
0.6989 Remote Similarity NPC81419
0.6989 Remote Similarity NPC179746
0.6988 Remote Similarity NPC179922
0.6966 Remote Similarity NPC329749
0.6966 Remote Similarity NPC149725
0.6966 Remote Similarity NPC51267
0.6966 Remote Similarity NPC478111
0.6966 Remote Similarity NPC47958
0.6966 Remote Similarity NPC304509
0.6947 Remote Similarity NPC158416
0.6947 Remote Similarity NPC475785
0.6947 Remote Similarity NPC475765
0.6947 Remote Similarity NPC39859
0.6947 Remote Similarity NPC470883
0.6947 Remote Similarity NPC76862
0.6939 Remote Similarity NPC292803
0.6932 Remote Similarity NPC157328
0.6931 Remote Similarity NPC167044
0.6931 Remote Similarity NPC278693
0.6931 Remote Similarity NPC329876
0.6931 Remote Similarity NPC220773
0.6923 Remote Similarity NPC471221
0.6915 Remote Similarity NPC190294
0.6915 Remote Similarity NPC470424
0.6914 Remote Similarity NPC470268
0.69 Remote Similarity NPC166079
0.69 Remote Similarity NPC306776
0.6889 Remote Similarity NPC470657
0.6889 Remote Similarity NPC469626
0.6889 Remote Similarity NPC475491
0.6889 Remote Similarity NPC228593
0.6889 Remote Similarity NPC235196
0.6882 Remote Similarity NPC30515
0.6882 Remote Similarity NPC184463
0.6875 Remote Similarity NPC319007
0.6875 Remote Similarity NPC328562
0.6875 Remote Similarity NPC323421
0.6863 Remote Similarity NPC217041
0.6848 Remote Similarity NPC173926
0.6848 Remote Similarity NPC474951
0.6848 Remote Similarity NPC67653
0.6848 Remote Similarity NPC307411
0.6848 Remote Similarity NPC471459
0.6842 Remote Similarity NPC470191
0.6842 Remote Similarity NPC36954
0.6837 Remote Similarity NPC478181
0.6813 Remote Similarity NPC239938
0.6813 Remote Similarity NPC31349
0.6813 Remote Similarity NPC179659
0.6809 Remote Similarity NPC476300
0.68 Remote Similarity NPC132304
0.68 Remote Similarity NPC123070
0.68 Remote Similarity NPC169089
0.68 Remote Similarity NPC88890
0.68 Remote Similarity NPC154962
0.68 Remote Similarity NPC18044
0.68 Remote Similarity NPC114365
0.68 Remote Similarity NPC473701
0.68 Remote Similarity NPC18433
0.68 Remote Similarity NPC100078
0.68 Remote Similarity NPC473526
0.68 Remote Similarity NPC177518
0.6796 Remote Similarity NPC182185
0.6795 Remote Similarity NPC476702
0.679 Remote Similarity NPC475062
0.6786 Remote Similarity NPC81052
0.6782 Remote Similarity NPC200446
0.6774 Remote Similarity NPC51004
0.6774 Remote Similarity NPC206614
0.6774 Remote Similarity NPC474323
0.6771 Remote Similarity NPC476009
0.6771 Remote Similarity NPC31645
0.6768 Remote Similarity NPC213528
0.6768 Remote Similarity NPC244969
0.6753 Remote Similarity NPC469923
0.675 Remote Similarity NPC206601
0.6744 Remote Similarity NPC191345
0.6744 Remote Similarity NPC3852
0.6744 Remote Similarity NPC252483
0.6742 Remote Similarity NPC320936
0.6739 Remote Similarity NPC202672
0.6737 Remote Similarity NPC470423
0.6712 Remote Similarity NPC320588
0.6712 Remote Similarity NPC469937
0.6712 Remote Similarity NPC53463
0.6712 Remote Similarity NPC23155
0.6709 Remote Similarity NPC476330
0.6709 Remote Similarity NPC469926
0.6705 Remote Similarity NPC211049
0.6705 Remote Similarity NPC119922
0.6705 Remote Similarity NPC116320
0.6702 Remote Similarity NPC475878
0.6702 Remote Similarity NPC329952
0.6701 Remote Similarity NPC472145
0.6667 Remote Similarity NPC200580
0.6667 Remote Similarity NPC322188
0.6667 Remote Similarity NPC91067
0.6667 Remote Similarity NPC146992
0.6667 Remote Similarity NPC477434
0.6667 Remote Similarity NPC93794
0.6667 Remote Similarity NPC473504
0.6667 Remote Similarity NPC42598
0.6667 Remote Similarity NPC477440
0.6667 Remote Similarity NPC85759
0.6667 Remote Similarity NPC98870
0.6667 Remote Similarity NPC477011
0.6667 Remote Similarity NPC20621
0.6667 Remote Similarity NPC477867
0.6667 Remote Similarity NPC477443
0.6667 Remote Similarity NPC477016
0.6667 Remote Similarity NPC318963
0.6667 Remote Similarity NPC22742
0.6667 Remote Similarity NPC280612
0.6667 Remote Similarity NPC209995
0.6667 Remote Similarity NPC477017
0.6667 Remote Similarity NPC291310
0.6667 Remote Similarity NPC477346
0.6667 Remote Similarity NPC477344
0.6667 Remote Similarity NPC294748
0.6667 Remote Similarity NPC475900
0.6667 Remote Similarity NPC40066
0.6667 Remote Similarity NPC158302
0.6667 Remote Similarity NPC81778
0.6635 Remote Similarity NPC475463
0.6633 Remote Similarity NPC472144
0.6633 Remote Similarity NPC211087
0.6632 Remote Similarity NPC475912

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC475616 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
0.7467 Intermediate Similarity NPD7909 Approved
0.68 Remote Similarity NPD4057 Clinical (unspecified phase)
0.68 Remote Similarity NPD4056 Clinical (unspecified phase)
0.6712 Remote Similarity NPD3730 Approved
0.6712 Remote Similarity NPD3728 Approved
0.6702 Remote Similarity NPD7983 Approved
0.65 Remote Similarity NPD9496 Clinical (unspecified phase)
0.6494 Remote Similarity NPD3198 Approved
0.6486 Remote Similarity NPD3729 Clinical (unspecified phase)
0.6463 Remote Similarity NPD229 Approved
0.6436 Remote Similarity NPD8085 Approved
0.6436 Remote Similarity NPD8086 Approved
0.6436 Remote Similarity NPD8084 Approved
0.6436 Remote Similarity NPD8138 Approved
0.6436 Remote Similarity NPD8082 Approved
0.6436 Remote Similarity NPD8139 Approved
0.6436 Remote Similarity NPD8083 Approved
0.6408 Remote Similarity NPD8393 Approved
0.6373 Remote Similarity NPD8276 Approved
0.6373 Remote Similarity NPD8275 Approved
0.6364 Remote Similarity NPD4238 Approved
0.6364 Remote Similarity NPD4802 Phase 2
0.6311 Remote Similarity NPD8170 Clinical (unspecified phase)
0.6311 Remote Similarity NPD8081 Approved
0.6264 Remote Similarity NPD6435 Approved
0.625 Remote Similarity NPD6698 Approved
0.625 Remote Similarity NPD46 Approved
0.6176 Remote Similarity NPD1700 Approved
0.6118 Remote Similarity NPD7532 Clinical (unspecified phase)
0.6104 Remote Similarity NPD73 Approved
0.6087 Remote Similarity NPD7345 Approved
0.6053 Remote Similarity NPD615 Clinical (unspecified phase)
0.6044 Remote Similarity NPD5368 Approved
0.6038 Remote Similarity NPD7899 Clinical (unspecified phase)
0.6 Remote Similarity NPD5786 Approved
0.5952 Remote Similarity NPD897 Approved
0.5952 Remote Similarity NPD896 Approved
0.5952 Remote Similarity NPD898 Approved
0.5926 Remote Similarity NPD8132 Clinical (unspecified phase)
0.5913 Remote Similarity NPD8267 Approved
0.5913 Remote Similarity NPD8269 Approved
0.5913 Remote Similarity NPD8266 Approved
0.5913 Remote Similarity NPD8268 Approved
0.5897 Remote Similarity NPD2267 Suspended
0.589 Remote Similarity NPD6125 Clinical (unspecified phase)
0.5888 Remote Similarity NPD8140 Approved
0.5888 Remote Similarity NPD8307 Discontinued
0.5851 Remote Similarity NPD3670 Clinical (unspecified phase)
0.5851 Remote Similarity NPD3669 Approved
0.5833 Remote Similarity NPD634 Phase 3
0.5833 Remote Similarity NPD5345 Clinical (unspecified phase)
0.5824 Remote Similarity NPD6115 Approved
0.5824 Remote Similarity NPD6118 Approved
0.5824 Remote Similarity NPD6697 Approved
0.5824 Remote Similarity NPD6114 Approved
0.5823 Remote Similarity NPD8959 Approved
0.5818 Remote Similarity NPD8413 Clinical (unspecified phase)
0.5806 Remote Similarity NPD5369 Approved
0.5789 Remote Similarity NPD3186 Phase 1
0.578 Remote Similarity NPD8306 Approved
0.578 Remote Similarity NPD8305 Approved
0.5773 Remote Similarity NPD4250 Approved
0.5773 Remote Similarity NPD4251 Approved
0.5761 Remote Similarity NPD7329 Approved
0.5758 Remote Similarity NPD7838 Discovery
0.5729 Remote Similarity NPD1733 Clinical (unspecified phase)
0.5727 Remote Similarity NPD8087 Discontinued
0.5714 Remote Similarity NPD6116 Phase 1
0.5694 Remote Similarity NPD2699 Approved
0.5686 Remote Similarity NPD1698 Clinical (unspecified phase)
0.5673 Remote Similarity NPD8029 Clinical (unspecified phase)
0.567 Remote Similarity NPD4249 Approved
0.5667 Remote Similarity NPD11 Approved
0.5667 Remote Similarity NPD3703 Phase 2
0.5667 Remote Similarity NPD376 Approved
0.5641 Remote Similarity NPD8513 Phase 3
0.5641 Remote Similarity NPD8517 Approved
0.5641 Remote Similarity NPD8515 Approved
0.5641 Remote Similarity NPD8516 Approved
0.5638 Remote Similarity NPD1780 Approved
0.5638 Remote Similarity NPD1779 Approved
0.5631 Remote Similarity NPD7839 Suspended
0.5618 Remote Similarity NPD3181 Approved
0.5604 Remote Similarity NPD6117 Approved

Structure

External Identifiers

PubChem CID   10627889
ChEMBL   CHEMBL509358
ZINC  

Physicochemical Properties

Molecular Weight:  638.48
ALogP:  -8.5763
MLogP:  4.65
XLogP:  7.883
# Rotatable Bonds:  30
Polar Surface Area:  122.52
# H-Bond Aceptor:  8
# H-Bond Donor:  3
# Rings:  3
# Heavy Atoms:  45

Download Data

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