Natural Product: NPC208307

Natural Product ID:  NPC208307
Common Name:   Volvaltrate B
IUPAC Name:   [(1S,4aR,6S,7S,7aS)-6-acetyloxy-7-(chloromethyl)-4a,7-dihydroxy-1-(3-methylbutanoyloxy)-1,5,6,7a-tetrahydrocyclopenta[c]pyran-4-yl]methyl (2R)-3-methyl-2-(3-methylbutanoyloxy)butanoate
Synonyms:  
Molecular Formula:   C27H41ClO11
Standard InCHIKey:  OEVPPNBQSYOUCV-PXKJKYEHSA-N
Standard InCHI:  InChI=1S/C27H41ClO11/c1-14(2)8-20(30)38-22(16(5)6)24(32)35-11-18-12-36-25(39-21(31)9-15(3)4)23-26(18,33)10-19(37-17(7)29)27(23,34)13-28/h12,14-16,19,22-23,25,33-34H,8-11,13H2,1-7H3/t19-,22+,23-,25-,26-,27+/m0/s1
Canonical SMILES:  ClC[C@@]1(O)[C@@H](OC(=O)C)C[C@]2([C@@H]1[C@@H](OC=C2COC(=O)[C@@H](C(C)C)OC(=O)CC(C)C)OC(=O)CC(C)C)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
NPO29016 Valeriana jatamansi Species Caprifoliaceae Eukaryota PMID[20853876]
NPO17333 Valeriana officinalis Species Caprifoliaceae Eukaryota PMID[20853876]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT181 Cell Line Bel-7402 Homo sapiens IC50 = 6100 nM 8450319
NPT180 Cell Line HCT-8 Homo sapiens IC50 = 3200 nM 8450319
NPT2 Others Unspecified IC50 = 2000 nM 8450319
NPT81 Cell Line A549 Homo sapiens IC50 = 8500 nM 8450319

  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 NPC208307 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
0.92 High Similarity NPC476320
0.92 High Similarity NPC476211
0.9109 High Similarity NPC476230
0.9109 High Similarity NPC216911
0.9109 High Similarity NPC27474
0.8932 High Similarity NPC329704
0.8932 High Similarity NPC329834
0.8922 High Similarity NPC476228
0.87 High Similarity NPC274588
0.8627 High Similarity NPC86843
0.8614 High Similarity NPC93869
0.8614 High Similarity NPC6765
0.8544 High Similarity NPC469918
0.8544 High Similarity NPC469919
0.8544 High Similarity NPC117066
0.8544 High Similarity NPC96399
0.8529 High Similarity NPC284063
0.8529 High Similarity NPC170527
0.8365 Intermediate Similarity NPC223700
0.8137 Intermediate Similarity NPC235051
0.8137 Intermediate Similarity NPC66504
0.7727 Intermediate Similarity NPC37240
0.7679 Intermediate Similarity NPC148270
0.7679 Intermediate Similarity NPC80338
0.7679 Intermediate Similarity NPC197813
0.7636 Intermediate Similarity NPC35185
0.7636 Intermediate Similarity NPC474730
0.7636 Intermediate Similarity NPC4899
0.7636 Intermediate Similarity NPC177013
0.7632 Intermediate Similarity NPC193741
0.7611 Intermediate Similarity NPC110701
0.7611 Intermediate Similarity NPC68248
0.7589 Intermediate Similarity NPC127235
0.7589 Intermediate Similarity NPC170432
0.7568 Intermediate Similarity NPC475928
0.7545 Intermediate Similarity NPC3488
0.7545 Intermediate Similarity NPC287539
0.7545 Intermediate Similarity NPC20673
0.7523 Intermediate Similarity NPC151093
0.75 Intermediate Similarity NPC475924
0.75 Intermediate Similarity NPC475851
0.7455 Intermediate Similarity NPC244878
0.7453 Intermediate Similarity NPC294643
0.7453 Intermediate Similarity NPC473150
0.7453 Intermediate Similarity NPC274274
0.7429 Intermediate Similarity NPC93190
0.7387 Intermediate Similarity NPC219038
0.7387 Intermediate Similarity NPC4637
0.7387 Intermediate Similarity NPC98859
0.7383 Intermediate Similarity NPC470187
0.7373 Intermediate Similarity NPC121816
0.7321 Intermediate Similarity NPC471599
0.7321 Intermediate Similarity NPC106668
0.7288 Intermediate Similarity NPC273242
0.7264 Intermediate Similarity NPC50464
0.7257 Intermediate Similarity NPC27687
0.7257 Intermediate Similarity NPC473148
0.7168 Intermediate Similarity NPC304163
0.7167 Intermediate Similarity NPC255450
0.7167 Intermediate Similarity NPC170692
0.7117 Intermediate Similarity NPC261372
0.7117 Intermediate Similarity NPC304445
0.7117 Intermediate Similarity NPC236580
0.7117 Intermediate Similarity NPC263674
0.7117 Intermediate Similarity NPC58267
0.7094 Intermediate Similarity NPC115352
0.708 Intermediate Similarity NPC67296
0.7027 Intermediate Similarity NPC161293
0.7027 Intermediate Similarity NPC474297
0.6992 Remote Similarity NPC219656
0.6981 Remote Similarity NPC149018
0.6981 Remote Similarity NPC171484
0.6944 Remote Similarity NPC22918
0.6937 Remote Similarity NPC291709
0.6937 Remote Similarity NPC241407
0.6929 Remote Similarity NPC470973
0.6917 Remote Similarity NPC95290
0.6917 Remote Similarity NPC189338
0.6903 Remote Similarity NPC49833
0.6903 Remote Similarity NPC124181
0.6903 Remote Similarity NPC90819
0.6903 Remote Similarity NPC249171
0.688 Remote Similarity NPC233500
0.687 Remote Similarity NPC214714
0.687 Remote Similarity NPC200672
0.687 Remote Similarity NPC80144
0.6852 Remote Similarity NPC148534
0.6847 Remote Similarity NPC63897
0.6825 Remote Similarity NPC196130
0.6818 Remote Similarity NPC276298
0.6814 Remote Similarity NPC472290
0.6814 Remote Similarity NPC470683
0.6814 Remote Similarity NPC153559
0.6814 Remote Similarity NPC470684
0.6792 Remote Similarity NPC98276
0.6792 Remote Similarity NPC259296
0.6786 Remote Similarity NPC167893
0.6786 Remote Similarity NPC472873
0.6783 Remote Similarity NPC26557
0.6783 Remote Similarity NPC471767
0.6777 Remote Similarity NPC35069
0.6777 Remote Similarity NPC258711
0.6774 Remote Similarity NPC109603
0.6774 Remote Similarity NPC93688
0.6772 Remote Similarity NPC219804
0.6759 Remote Similarity NPC258501
0.6754 Remote Similarity NPC473307
0.6754 Remote Similarity NPC37866
0.6752 Remote Similarity NPC86095
0.6727 Remote Similarity NPC246173
0.6724 Remote Similarity NPC78127
0.6724 Remote Similarity NPC250594
0.6724 Remote Similarity NPC252242
0.6724 Remote Similarity NPC471757
0.6724 Remote Similarity NPC475956
0.6724 Remote Similarity NPC49393
0.6718 Remote Similarity NPC213634
0.6696 Remote Similarity NPC130792
0.6696 Remote Similarity NPC255677
0.6696 Remote Similarity NPC306344
0.6696 Remote Similarity NPC22149
0.6696 Remote Similarity NPC186861
0.6696 Remote Similarity NPC473146
0.6695 Remote Similarity NPC470980
0.6695 Remote Similarity NPC44004
0.6667 Remote Similarity NPC234304
0.6667 Remote Similarity NPC471150
0.6667 Remote Similarity NPC474313
0.6667 Remote Similarity NPC260809
0.6667 Remote Similarity NPC118761
0.6667 Remote Similarity NPC232515
0.6667 Remote Similarity NPC474182
0.6667 Remote Similarity NPC474783
0.6667 Remote Similarity NPC267869
0.6667 Remote Similarity NPC106446
0.6667 Remote Similarity NPC284929
0.6667 Remote Similarity NPC321812
0.6667 Remote Similarity NPC181151
0.6667 Remote Similarity NPC322922
0.6667 Remote Similarity NPC197541
0.6639 Remote Similarity NPC470170
0.6639 Remote Similarity NPC470169
0.6639 Remote Similarity NPC313921
0.6639 Remote Similarity NPC98038
0.6638 Remote Similarity NPC28304
0.6638 Remote Similarity NPC298255
0.6613 Remote Similarity NPC277583
0.6612 Remote Similarity NPC106760
0.6609 Remote Similarity NPC45125
0.6609 Remote Similarity NPC274458
0.6609 Remote Similarity NPC474957
0.6609 Remote Similarity NPC472015
0.6609 Remote Similarity NPC79449
0.6607 Remote Similarity NPC472196
0.6607 Remote Similarity NPC472195
0.6607 Remote Similarity NPC238090
0.6607 Remote Similarity NPC320089
0.6607 Remote Similarity NPC474835
0.6607 Remote Similarity NPC475788
0.6606 Remote Similarity NPC31349
0.6587 Remote Similarity NPC477092
0.6585 Remote Similarity NPC101965
0.6585 Remote Similarity NPC89018
0.6585 Remote Similarity NPC287075
0.6585 Remote Similarity NPC101400
0.6583 Remote Similarity NPC117604
0.6581 Remote Similarity NPC105725
0.6581 Remote Similarity NPC94919
0.6581 Remote Similarity NPC222062
0.6581 Remote Similarity NPC195510
0.6581 Remote Similarity NPC13171
0.6581 Remote Similarity NPC475986
0.6579 Remote Similarity NPC98165
0.6579 Remote Similarity NPC54731
0.6577 Remote Similarity NPC120021
0.6577 Remote Similarity NPC117596
0.6577 Remote Similarity NPC216826
0.6577 Remote Similarity NPC471184
0.6577 Remote Similarity NPC270908
0.6577 Remote Similarity NPC65665
0.6577 Remote Similarity NPC231710
0.6577 Remote Similarity NPC470573
0.6555 Remote Similarity NPC41681
0.6555 Remote Similarity NPC85670
0.6555 Remote Similarity NPC166115
0.6555 Remote Similarity NPC475290
0.6552 Remote Similarity NPC471381
0.6549 Remote Similarity NPC281775
0.6549 Remote Similarity NPC159698
0.6549 Remote Similarity NPC472198
0.6545 Remote Similarity NPC233997
0.6532 Remote Similarity NPC88867
0.6532 Remote Similarity NPC226608
0.6529 Remote Similarity NPC471400
0.6529 Remote Similarity NPC473570
0.6522 Remote Similarity NPC182811
0.6522 Remote Similarity NPC347923
0.6522 Remote Similarity NPC476057
0.6518 Remote Similarity NPC472124
0.6518 Remote Similarity NPC472125

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC208307 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
0.6726 Remote Similarity NPD4792 Clinical (unspecified phase)
0.6614 Remote Similarity NPD7503 Approved
0.6585 Remote Similarity NPD8133 Approved
0.6423 Remote Similarity NPD8413 Clinical (unspecified phase)
0.6378 Remote Similarity NPD7328 Approved
0.6378 Remote Similarity NPD7327 Approved
0.6364 Remote Similarity NPD7899 Clinical (unspecified phase)
0.6357 Remote Similarity NPD8033 Approved
0.6328 Remote Similarity NPD7516 Approved
0.6316 Remote Similarity NPD6033 Approved
0.6311 Remote Similarity NPD6686 Approved
0.6306 Remote Similarity NPD4251 Approved
0.6306 Remote Similarity NPD4250 Approved
0.6288 Remote Similarity NPD7507 Approved
0.6279 Remote Similarity NPD8294 Approved
0.6279 Remote Similarity NPD8377 Approved
0.624 Remote Similarity NPD6053 Discontinued
0.6231 Remote Similarity NPD8378 Approved
0.6231 Remote Similarity NPD8296 Approved
0.6231 Remote Similarity NPD8380 Approved
0.6231 Remote Similarity NPD8335 Approved
0.6231 Remote Similarity NPD8379 Approved
0.6222 Remote Similarity NPD5956 Approved
0.6216 Remote Similarity NPD4249 Approved
0.6198 Remote Similarity NPD4057 Clinical (unspecified phase)
0.6198 Remote Similarity NPD4056 Clinical (unspecified phase)
0.6172 Remote Similarity NPD6009 Approved
0.6148 Remote Similarity NPD7319 Approved
0.6119 Remote Similarity NPD8293 Discontinued
0.6107 Remote Similarity NPD5983 Phase 2
0.6098 Remote Similarity NPD6412 Phase 2
0.6074 Remote Similarity NPD7736 Approved
0.6061 Remote Similarity NPD6370 Approved
0.605 Remote Similarity NPD8029 Clinical (unspecified phase)
0.6045 Remote Similarity NPD6336 Discontinued
0.6 Remote Similarity NPD6698 Approved
0.6 Remote Similarity NPD46 Approved
0.5985 Remote Similarity NPD8513 Phase 3
0.5982 Remote Similarity NPD6082 Clinical (unspecified phase)
0.597 Remote Similarity NPD7492 Approved
0.5963 Remote Similarity NPD4821 Approved
0.5963 Remote Similarity NPD4820 Approved
0.5963 Remote Similarity NPD4822 Approved
0.5963 Remote Similarity NPD4819 Approved
0.5963 Remote Similarity NPD5790 Clinical (unspecified phase)
0.5954 Remote Similarity NPD7100 Approved
0.5952 Remote Similarity NPD6371 Approved
0.5938 Remote Similarity NPD4632 Approved
0.5926 Remote Similarity NPD6616 Approved
0.5909 Remote Similarity NPD6054 Approved
0.5909 Remote Similarity NPD6319 Approved
0.5909 Remote Similarity NPD6059 Approved
0.5882 Remote Similarity NPD7078 Approved
0.5878 Remote Similarity NPD6335 Approved
0.5865 Remote Similarity NPD8515 Approved
0.5865 Remote Similarity NPD8517 Approved
0.5865 Remote Similarity NPD8516 Approved
0.5862 Remote Similarity NPD7838 Discovery
0.5859 Remote Similarity NPD6882 Approved
0.5833 Remote Similarity NPD7101 Approved
0.5804 Remote Similarity NPD7154 Phase 3
0.578 Remote Similarity NPD4268 Approved
0.578 Remote Similarity NPD4271 Approved
0.5758 Remote Similarity NPD6313 Approved
0.5758 Remote Similarity NPD6314 Approved
0.5746 Remote Similarity NPD6016 Approved
0.5746 Remote Similarity NPD6015 Approved
0.5746 Remote Similarity NPD8274 Clinical (unspecified phase)
0.5738 Remote Similarity NPD7639 Approved
0.5738 Remote Similarity NPD7640 Approved
0.5736 Remote Similarity NPD8297 Approved
0.5714 Remote Similarity NPD4522 Approved
0.5714 Remote Similarity NPD6435 Approved
0.5704 Remote Similarity NPD5988 Approved
0.5704 Remote Similarity NPD8080 Discontinued
0.5702 Remote Similarity NPD6083 Phase 2
0.5702 Remote Similarity NPD6084 Phase 2
0.5691 Remote Similarity NPD5344 Discontinued
0.5678 Remote Similarity NPD7983 Approved
0.5667 Remote Similarity NPD5695 Phase 3
0.5664 Remote Similarity NPD5362 Discontinued
0.5656 Remote Similarity NPD7638 Approved
0.5635 Remote Similarity NPD6675 Approved
0.5635 Remote Similarity NPD5739 Approved
0.5635 Remote Similarity NPD7128 Approved
0.5635 Remote Similarity NPD6402 Approved
0.5625 Remote Similarity NPD6372 Approved
0.5625 Remote Similarity NPD6373 Approved
0.5603 Remote Similarity NPD7524 Approved

Structure

External Identifiers

PubChem CID   49831716
ChEMBL   CHEMBL1270648
ZINC  

Physicochemical Properties

Molecular Weight:  576.23
ALogP:  0.1822
MLogP:  3.11
XLogP:  3.518
# Rotatable Bonds:  26
Polar Surface Area:  154.89
# H-Bond Aceptor:  11
# H-Bond Donor:  2
# Rings:  2
# Heavy Atoms:  39

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