Natural Product: NPC478263

Natural Product ID:  NPC478263
Common Name:   Vulgarisin C
IUPAC Name:  
Synonyms:  
Molecular Formula:   C31H44O6
Standard InCHIKey:  WOLXYSLWYBGXMV-WOIKJDTKSA-N
Standard InCHI:  InChI=1S/C31H44O6/c1-17(2)21-14-15-31(35)24-23-19(5)12-13-22(23)29(24,6)25(32)26(37-27(33)18(3)4)30(21,31)16-36-28(34)20-10-8-7-9-11-20/h7-11,17-19,21-26,32,35H,12-16H2,1-6H3/t19-,21-,22+,23-,24+,25+,26+,29-,30+,31+/m0/s1
Canonical SMILES:  CC(C(=O)O[C@@H]1[C@@H](O)[C@@]2(C)[C@@H]3CC[C@@H]([C@@H]3[C@H]2[C@]2([C@]1(COC(=O)c1ccccc1)[C@@H](CC2)C(C)C)O)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
NPO17494 Prunella vulgaris Species Lamiaceae Eukaryota whole plant DOI[10.1016/j.tetlet.2016.12.029]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT81 Cell Line A549 Homo sapiens IC50 = 25.7 µM 10.1016/j.tetlet.2016.12.029

  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 NPC478263 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
0.9927 High Similarity NPC478264
0.9231 High Similarity NPC327031
0.9161 High Similarity NPC312393
0.9143 High Similarity NPC275592
0.9143 High Similarity NPC100913
0.9103 High Similarity NPC476173
0.9091 High Similarity NPC92867
0.9091 High Similarity NPC311825
0.9078 High Similarity NPC291599
0.9078 High Similarity NPC87448
0.9078 High Similarity NPC27377
0.9078 High Similarity NPC118080
0.9078 High Similarity NPC41481
0.9078 High Similarity NPC97947
0.9078 High Similarity NPC472576
0.9054 High Similarity NPC70344
0.9028 High Similarity NPC20255
0.9028 High Similarity NPC240115
0.9021 High Similarity NPC34943
0.9007 High Similarity NPC472547
0.9007 High Similarity NPC97667
0.9007 High Similarity NPC171207
0.9007 High Similarity NPC90614
0.9 High Similarity NPC39549
0.8958 High Similarity NPC125882
0.8944 High Similarity NPC16912
0.8929 High Similarity NPC472551
0.8929 High Similarity NPC472545
0.8919 High Similarity NPC471135
0.8904 High Similarity NPC76103
0.8889 High Similarity NPC475122
0.8889 High Similarity NPC475759
0.8889 High Similarity NPC470152
0.8889 High Similarity NPC241951
0.8889 High Similarity NPC38696
0.8881 High Similarity NPC192658
0.8881 High Similarity NPC34012
0.8836 High Similarity NPC473760
0.8828 High Similarity NPC472575
0.8828 High Similarity NPC200471
0.8828 High Similarity NPC470159
0.8828 High Similarity NPC471104
0.8828 High Similarity NPC469349
0.8828 High Similarity NPC174982
0.8828 High Similarity NPC177940
0.8828 High Similarity NPC472572
0.8828 High Similarity NPC473088
0.8828 High Similarity NPC472568
0.8828 High Similarity NPC70403
0.8828 High Similarity NPC184817
0.8828 High Similarity NPC470157
0.8828 High Similarity NPC96903
0.8828 High Similarity NPC171525
0.8828 High Similarity NPC472571
0.8828 High Similarity NPC29704
0.8828 High Similarity NPC476973
0.8828 High Similarity NPC158663
0.8819 High Similarity NPC163087
0.8803 High Similarity NPC9905
0.88 High Similarity NPC290683
0.88 High Similarity NPC475548
0.88 High Similarity NPC475638
0.8786 High Similarity NPC474608
0.8784 High Similarity NPC96308
0.8784 High Similarity NPC469415
0.8777 High Similarity NPC233692
0.8777 High Similarity NPC239358
0.8767 High Similarity NPC209592
0.8767 High Similarity NPC48599
0.8767 High Similarity NPC473602
0.8759 High Similarity NPC57628
0.8759 High Similarity NPC11685
0.8759 High Similarity NPC95265
0.8759 High Similarity NPC70716
0.8759 High Similarity NPC125106
0.8759 High Similarity NPC472569
0.8759 High Similarity NPC472573
0.8759 High Similarity NPC25768
0.8759 High Similarity NPC95810
0.8759 High Similarity NPC188865
0.8759 High Similarity NPC476974
0.8759 High Similarity NPC472570
0.8759 High Similarity NPC163719
0.8742 High Similarity NPC318447
0.8742 High Similarity NPC322048
0.8741 High Similarity NPC87934
0.8741 High Similarity NPC162613
0.8733 High Similarity NPC132599
0.8733 High Similarity NPC469730
0.8733 High Similarity NPC469422
0.8733 High Similarity NPC473632
0.8733 High Similarity NPC469456
0.8733 High Similarity NPC34066
0.8723 High Similarity NPC66761
0.8723 High Similarity NPC200154
0.8723 High Similarity NPC291638
0.8723 High Similarity NPC472577
0.8723 High Similarity NPC195647
0.8723 High Similarity NPC17877
0.8716 High Similarity NPC303429
0.8716 High Similarity NPC222102
0.8714 High Similarity NPC472248
0.8707 High Similarity NPC132652
0.8707 High Similarity NPC217918
0.8705 High Similarity NPC72915
0.8699 High Similarity NPC472556
0.869 High Similarity NPC91703
0.869 High Similarity NPC191387
0.869 High Similarity NPC131966
0.8681 High Similarity NPC224491
0.8675 High Similarity NPC323001
0.8675 High Similarity NPC326235
0.8671 High Similarity NPC473301
0.8652 High Similarity NPC311492
0.8652 High Similarity NPC28836
0.8652 High Similarity NPC48929
0.8649 High Similarity NPC301556
0.8649 High Similarity NPC471101
0.8649 High Similarity NPC270590
0.8649 High Similarity NPC92293
0.8649 High Similarity NPC473215
0.8649 High Similarity NPC476975
0.8649 High Similarity NPC266265
0.8643 High Similarity NPC233860
0.8639 High Similarity NPC474935
0.8636 High Similarity NPC478124
0.8627 High Similarity NPC309991
0.8627 High Similarity NPC326328
0.8627 High Similarity NPC323356
0.8627 High Similarity NPC471138
0.8621 High Similarity NPC472546
0.8609 High Similarity NPC469398
0.8609 High Similarity NPC473611
0.8601 High Similarity NPC183122
0.8601 High Similarity NPC283375
0.86 High Similarity NPC469648
0.86 High Similarity NPC469647
0.86 High Similarity NPC138641
0.86 High Similarity NPC22571
0.86 High Similarity NPC145649
0.86 High Similarity NPC233581
0.86 High Similarity NPC283875
0.8591 High Similarity NPC31829
0.8591 High Similarity NPC469448
0.8591 High Similarity NPC470245
0.8591 High Similarity NPC473214
0.8591 High Similarity NPC91730
0.8581 High Similarity NPC281717
0.8562 High Similarity NPC476784
0.8562 High Similarity NPC477894
0.8562 High Similarity NPC319404
0.8553 High Similarity NPC11410
0.8552 High Similarity NPC266374
0.8543 High Similarity NPC472658
0.8543 High Similarity NPC133430
0.8543 High Similarity NPC469477
0.8543 High Similarity NPC472657
0.8542 High Similarity NPC475652
0.8542 High Similarity NPC214550
0.8542 High Similarity NPC210591
0.8533 High Similarity NPC470153
0.8533 High Similarity NPC197037
0.8533 High Similarity NPC471103
0.8516 High Similarity NPC55744
0.8506 High Similarity NPC477623
0.85 High Similarity NPC147561
0.8493 Intermediate Similarity NPC475135
0.8483 Intermediate Similarity NPC473085
0.8483 Intermediate Similarity NPC4341
0.8483 Intermediate Similarity NPC473613
0.8483 Intermediate Similarity NPC473081
0.8483 Intermediate Similarity NPC476094
0.8483 Intermediate Similarity NPC211137
0.8483 Intermediate Similarity NPC200592
0.8483 Intermediate Similarity NPC43241
0.8483 Intermediate Similarity NPC473758
0.8483 Intermediate Similarity NPC473060
0.8483 Intermediate Similarity NPC48017
0.8483 Intermediate Similarity NPC184747
0.8483 Intermediate Similarity NPC147880
0.8483 Intermediate Similarity NPC473109
0.8483 Intermediate Similarity NPC473112
0.8472 Intermediate Similarity NPC27721
0.8471 Intermediate Similarity NPC475567
0.8471 Intermediate Similarity NPC473557
0.8471 Intermediate Similarity NPC473468
0.8471 Intermediate Similarity NPC477491
0.8462 Intermediate Similarity NPC477893
0.8462 Intermediate Similarity NPC477896
0.8446 Intermediate Similarity NPC127857
0.8442 Intermediate Similarity NPC469399
0.8435 Intermediate Similarity NPC95449
0.8425 Intermediate Similarity NPC242355
0.8421 Intermediate Similarity NPC248265
0.8421 Intermediate Similarity NPC134685
0.8421 Intermediate Similarity NPC229545
0.8421 Intermediate Similarity NPC219419
0.8421 Intermediate Similarity NPC11588
0.8418 Intermediate Similarity NPC475531
0.8418 Intermediate Similarity NPC475198

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC478263 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
0.8322 Intermediate Similarity NPD7236 Approved
0.8052 Intermediate Similarity NPD7239 Suspended
0.7927 Intermediate Similarity NPD7799 Discontinued
0.7902 Intermediate Similarity NPD6007 Clinical (unspecified phase)
0.7665 Intermediate Similarity NPD8470 Clinical (unspecified phase)
0.7593 Intermediate Similarity NPD7058 Phase 2
0.7593 Intermediate Similarity NPD7057 Phase 3
0.7529 Intermediate Similarity NPD8368 Discontinued
0.75 Intermediate Similarity NPD8407 Phase 2
0.75 Intermediate Similarity NPD5952 Clinical (unspecified phase)
0.7414 Intermediate Similarity NPD8434 Phase 2
0.7394 Intermediate Similarity NPD7741 Discontinued
0.7372 Intermediate Similarity NPD4628 Phase 3
0.7361 Intermediate Similarity NPD7457 Clinical (unspecified phase)
0.7358 Intermediate Similarity NPD6273 Approved
0.7357 Intermediate Similarity NPD2629 Approved
0.7322 Intermediate Similarity NPD7497 Discontinued
0.7305 Intermediate Similarity NPD8127 Discontinued
0.7285 Intermediate Similarity NPD6663 Approved
0.7256 Intermediate Similarity NPD5760 Phase 2
0.7256 Intermediate Similarity NPD5761 Phase 2
0.7232 Intermediate Similarity NPD8360 Approved
0.7232 Intermediate Similarity NPD8435 Approved
0.7232 Intermediate Similarity NPD8361 Approved
0.7225 Intermediate Similarity NPD6765 Approved
0.7225 Intermediate Similarity NPD6764 Approved
0.7179 Intermediate Similarity NPD5763 Approved
0.7179 Intermediate Similarity NPD5762 Approved
0.7171 Intermediate Similarity NPD7961 Discontinued
0.7159 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7119 Intermediate Similarity NPD8424 Clinical (unspecified phase)
0.7071 Intermediate Similarity NPD2181 Clinical (unspecified phase)
0.707 Intermediate Similarity NPD6005 Phase 3
0.707 Intermediate Similarity NPD6006 Clinical (unspecified phase)
0.707 Intermediate Similarity NPD6002 Phase 3
0.707 Intermediate Similarity NPD6004 Phase 3
0.707 Intermediate Similarity NPD6003 Clinical (unspecified phase)
0.7063 Intermediate Similarity NPD4198 Discontinued
0.7062 Intermediate Similarity NPD6784 Approved
0.7062 Intermediate Similarity NPD6785 Approved
0.7039 Intermediate Similarity NPD7008 Discontinued
0.7029 Intermediate Similarity NPD7685 Pre-registration
0.7029 Intermediate Similarity NPD6685 Approved
0.702 Intermediate Similarity NPD5736 Approved
0.7013 Intermediate Similarity NPD7966 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD7274 Clinical (unspecified phase)
0.6995 Remote Similarity NPD8485 Approved
0.6972 Remote Similarity NPD6858 Approved
0.6972 Remote Similarity NPD7094 Approved
0.6954 Remote Similarity NPD5844 Phase 1
0.6939 Remote Similarity NPD5125 Phase 3
0.6939 Remote Similarity NPD5126 Approved
0.6937 Remote Similarity NPD8166 Discontinued
0.6929 Remote Similarity NPD6831 Clinical (unspecified phase)
0.6929 Remote Similarity NPD2182 Approved
0.6894 Remote Similarity NPD6190 Approved
0.6883 Remote Similarity NPD3764 Approved
0.6882 Remote Similarity NPD8486 Clinical (unspecified phase)
0.6875 Remote Similarity NPD5951 Approved
0.6867 Remote Similarity NPD6599 Discontinued
0.6867 Remote Similarity NPD7028 Phase 2
0.6864 Remote Similarity NPD4965 Approved
0.6864 Remote Similarity NPD4966 Approved
0.6864 Remote Similarity NPD4967 Phase 2
0.6859 Remote Similarity NPD5735 Approved
0.6859 Remote Similarity NPD6355 Discontinued
0.6849 Remote Similarity NPD7610 Discontinued
0.6845 Remote Similarity NPD7096 Clinical (unspecified phase)
0.6842 Remote Similarity NPD5740 Clinical (unspecified phase)
0.6842 Remote Similarity NPD6085 Phase 2
0.6833 Remote Similarity NPD8150 Discontinued
0.6832 Remote Similarity NPD6398 Clinical (unspecified phase)
0.6831 Remote Similarity NPD4141 Clinical (unspecified phase)
0.6824 Remote Similarity NPD3412 Clinical (unspecified phase)
0.6815 Remote Similarity NPD6653 Approved
0.6812 Remote Similarity NPD5765 Approved
0.6807 Remote Similarity NPD6591 Clinical (unspecified phase)
0.6802 Remote Similarity NPD7199 Phase 2
0.6795 Remote Similarity NPD4140 Approved
0.6786 Remote Similarity NPD37 Approved
0.6784 Remote Similarity NPD6234 Discontinued
0.6768 Remote Similarity NPD7004 Clinical (unspecified phase)
0.6759 Remote Similarity NPD690 Clinical (unspecified phase)
0.6753 Remote Similarity NPD8462 Phase 1
0.6752 Remote Similarity NPD230 Phase 1
0.6746 Remote Similarity NPD7819 Suspended
0.6733 Remote Similarity NPD6287 Discontinued
0.673 Remote Similarity NPD7305 Phase 1
0.6728 Remote Similarity NPD4109 Clinical (unspecified phase)
0.6728 Remote Similarity NPD4110 Phase 3
0.6725 Remote Similarity NPD7075 Discontinued
0.6707 Remote Similarity NPD7458 Discontinued
0.6705 Remote Similarity NPD7228 Approved
0.6691 Remote Similarity NPD5738 Clinical (unspecified phase)
0.6689 Remote Similarity NPD7009 Phase 2
0.6687 Remote Similarity NPD2935 Discontinued
0.6685 Remote Similarity NPD7879 Clinical (unspecified phase)
0.6667 Remote Similarity NPD4868 Clinical (unspecified phase)
0.6667 Remote Similarity NPD2532 Approved
0.6667 Remote Similarity NPD6912 Phase 3
0.6667 Remote Similarity NPD2533 Approved
0.6667 Remote Similarity NPD2534 Approved
0.6667 Remote Similarity NPD3094 Phase 2
0.6667 Remote Similarity NPD4380 Phase 2
0.6648 Remote Similarity NPD7473 Discontinued
0.6646 Remote Similarity NPD7702 Clinical (unspecified phase)
0.6643 Remote Similarity NPD164 Approved
0.6629 Remote Similarity NPD7184 Clinical (unspecified phase)
0.6627 Remote Similarity NPD7314 Clinical (unspecified phase)
0.6626 Remote Similarity NPD7003 Approved
0.6622 Remote Similarity NPD7516 Approved
0.6608 Remote Similarity NPD5402 Approved
0.6607 Remote Similarity NPD5808 Clinical (unspecified phase)
0.6606 Remote Similarity NPD6799 Approved
0.6604 Remote Similarity NPD6353 Approved
0.66 Remote Similarity NPD7163 Clinical (unspecified phase)
0.6594 Remote Similarity NPD1238 Approved
0.659 Remote Similarity NPD5537 Clinical (unspecified phase)
0.6588 Remote Similarity NPD6801 Discontinued
0.6584 Remote Similarity NPD7137 Phase 2
0.6579 Remote Similarity NPD7507 Approved
0.6577 Remote Similarity NPD9545 Approved
0.6575 Remote Similarity NPD8312 Approved
0.6575 Remote Similarity NPD8313 Approved
0.6571 Remote Similarity NPD1929 Approved
0.6571 Remote Similarity NPD1931 Clinical (unspecified phase)
0.6571 Remote Similarity NPD6232 Discontinued
0.6571 Remote Similarity NPD1930 Approved
0.6571 Remote Similarity NPD6647 Phase 2
0.6564 Remote Similarity NPD7421 Clinical (unspecified phase)
0.6558 Remote Similarity NPD7319 Approved
0.6556 Remote Similarity NPD6559 Discontinued
0.6556 Remote Similarity NPD7240 Approved
0.6554 Remote Similarity NPD4230 Clinical (unspecified phase)
0.6554 Remote Similarity NPD7327 Approved
0.6554 Remote Similarity NPD7328 Approved
0.6552 Remote Similarity NPD5494 Approved
0.655 Remote Similarity NPD2393 Clinical (unspecified phase)
0.6543 Remote Similarity NPD2346 Discontinued
0.6543 Remote Similarity NPD2343 Clinical (unspecified phase)
0.6543 Remote Similarity NPD7266 Discontinued
0.6538 Remote Similarity NPD7055 Discontinued
0.6528 Remote Similarity NPD2067 Discontinued
0.6524 Remote Similarity NPD3750 Approved
0.6522 Remote Similarity NPD2799 Discontinued
0.6519 Remote Similarity NPD8032 Phase 2
0.6516 Remote Similarity NPD5647 Approved
0.6513 Remote Similarity NPD3092 Approved
0.6513 Remote Similarity NPD4807 Approved
0.6513 Remote Similarity NPD4806 Approved
0.6512 Remote Similarity NPD3817 Phase 2
0.6506 Remote Similarity NPD6143 Clinical (unspecified phase)
0.6503 Remote Similarity NPD970 Clinical (unspecified phase)
0.6494 Remote Similarity NPD1876 Approved
0.6491 Remote Similarity NPD1934 Approved
0.649 Remote Similarity NPD5305 Approved
0.649 Remote Similarity NPD5306 Approved
0.6488 Remote Similarity NPD5403 Approved
0.6486 Remote Similarity NPD8397 Clinical (unspecified phase)
0.6486 Remote Similarity NPD7115 Discovery
0.6481 Remote Similarity NPD2438 Suspended
0.6478 Remote Similarity NPD3620 Phase 2
0.6478 Remote Similarity NPD3619 Clinical (unspecified phase)
0.6477 Remote Similarity NPD7315 Approved
0.6475 Remote Similarity NPD2066 Phase 3
0.6474 Remote Similarity NPD7768 Phase 2
0.6467 Remote Similarity NPD5401 Approved
0.6467 Remote Similarity NPD8389 Clinical (unspecified phase)
0.6458 Remote Similarity NPD4061 Clinical (unspecified phase)
0.6456 Remote Similarity NPD6859 Clinical (unspecified phase)
0.6453 Remote Similarity NPD8455 Phase 2
0.6452 Remote Similarity NPD6362 Approved
0.645 Remote Similarity NPD8404 Phase 2
0.6437 Remote Similarity NPD4381 Clinical (unspecified phase)
0.6425 Remote Similarity NPD3818 Discontinued
0.6424 Remote Similarity NPD7503 Approved
0.642 Remote Similarity NPD3748 Approved
0.642 Remote Similarity NPD7033 Discontinued
0.6419 Remote Similarity NPD4766 Approved
0.6415 Remote Similarity NPD6233 Phase 2
0.6412 Remote Similarity NPD3226 Approved
0.641 Remote Similarity NPD6917 Clinical (unspecified phase)
0.6408 Remote Similarity NPD1237 Approved
0.6403 Remote Similarity NPD7638 Approved
0.6398 Remote Similarity NPD3528 Clinical (unspecified phase)
0.6395 Remote Similarity NPD4632 Approved
0.6392 Remote Similarity NPD7095 Approved
0.6391 Remote Similarity NPD6980 Clinical (unspecified phase)
0.6387 Remote Similarity NPD1283 Approved
0.6382 Remote Similarity NPD2932 Approved
0.6382 Remote Similarity NPD3095 Discontinued
0.6382 Remote Similarity NPD3019 Approved
0.638 Remote Similarity NPD5405 Approved
0.638 Remote Similarity NPD5404 Approved
0.638 Remote Similarity NPD1551 Phase 2
0.638 Remote Similarity NPD5406 Approved
0.638 Remote Similarity NPD6099 Approved
0.638 Remote Similarity NPD6100 Approved
0.638 Remote Similarity NPD5408 Approved
0.6379 Remote Similarity NPD3882 Suspended

Structure

External Identifiers

PubChem CID  
ChEMBL  
ZINC  

Physicochemical Properties

Molecular Weight:  512.31
ALogP:  0.6547
MLogP:  4.21
XLogP:  7.812
# Rotatable Bonds:  16
Polar Surface Area:  93.06
# H-Bond Aceptor:  6
# H-Bond Donor:  2
# Rings:  5
# Heavy Atoms:  37

Download Data

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