Natural Product: NPC473882

Natural Product ID:  NPC473882
Common Name:   Bryonioside C
IUPAC Name:   [(2S,3R,4S,5R,6S)-6-[(2R,3R,4S,5S,6R)-2-[[(3S,8S,9R,10R,13R,14S,17R)-17-[(2R,5R)-5,6-dihydroxy-6-methylheptan-2-yl]-4,4,9,13,14-pentamethyl-11-oxo-1,2,3,7,8,10,12,15,16,17-decahydrocyclopenta[a]phenanthren-3-yl]oxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]oxy-4,5-dihydroxy-2-methyloxan-3-yl] acetate
Synonyms:   bryonioside C
Molecular Formula:   C44H72O14
Standard InCHIKey:  UMAHJKNVOBUTJL-BBFQHCCVSA-N
Standard InCHI:  InChI=1S/C44H72O14/c1-21(11-15-29(47)41(6,7)53)24-17-18-42(8)28-14-12-25-26(44(28,10)30(48)19-43(24,42)9)13-16-31(40(25,4)5)57-39-37(33(50)32(49)27(20-45)56-39)58-38-35(52)34(51)36(22(2)54-38)55-23(3)46/h12,21-22,24,26-29,31-39,45,47,49-53H,11,13-20H2,1-10H3/t21-,22+,24-,26-,27-,28+,29-,31+,32-,33+,34+,35-,36+,37-,38+,39+,42+,43-,44+/m1/s1
Canonical SMILES:  OC[C@H]1O[C@@H](O[C@H]2CC[C@@H]3C(=CC[C@@H]4[C@@]3(C)C(=O)C[C@]3([C@@]4(C)CC[C@@H]3[C@@H](CC[C@H](C(O)(C)C)O)C)C)C2(C)C)[C@@H]([C@H]([C@@H]1O)O)O[C@@H]1O[C@@H](C)[C@@H]([C@H]([C@H]1O)O)OC(=O)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
NPO33132 bryonia dioica Species Cucurbitaceae Eukaryota Roots PMID[11858752]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT2 Others Unspecified Inhibition = 73.5 % PubChem BioAssay data set
NPT2 Others Unspecified Inhibition = 30.2 % 25729554
NPT2 Others Unspecified Inhibition = 100 % 9599253
NPT32 Organism Mus musculus Mus musculus Activity = 83 % 19785430
NPT32 Organism Mus musculus Mus musculus ID50 = 0.3 ug 2853205
NPT80 Cell Line Raji Homo sapiens Activity = 60 % 21816516
NPT2 Others Unspecified Inhibition = 0 % 22037378

  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 NPC473882 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
0.981 High Similarity NPC474265
0.981 High Similarity NPC210420
0.9626 High Similarity NPC474557
0.9619 High Similarity NPC52241
0.9619 High Similarity NPC154856
0.9619 High Similarity NPC475317
0.9537 High Similarity NPC279638
0.9533 High Similarity NPC251309
0.9439 High Similarity NPC233003
0.9439 High Similarity NPC130427
0.9429 High Similarity NPC295389
0.9346 High Similarity NPC250481
0.9346 High Similarity NPC477073
0.9346 High Similarity NPC285410
0.9346 High Similarity NPC263827
0.9252 High Similarity NPC129340
0.9204 High Similarity NPC156789
0.9196 High Similarity NPC471406
0.9189 High Similarity NPC475632
0.9189 High Similarity NPC86020
0.9174 High Similarity NPC204458
0.9174 High Similarity NPC477074
0.9174 High Similarity NPC47063
0.9174 High Similarity NPC189884
0.9174 High Similarity NPC138334
0.9167 High Similarity NPC211798
0.9167 High Similarity NPC30397
0.9167 High Similarity NPC235841
0.9167 High Similarity NPC473481
0.9167 High Similarity NPC108748
0.9167 High Similarity NPC297208
0.9159 High Similarity NPC265655
0.9159 High Similarity NPC118225
0.9159 High Similarity NPC477069
0.9159 High Similarity NPC477070
0.9123 High Similarity NPC160084
0.9115 High Similarity NPC475182
0.9091 High Similarity NPC165439
0.9091 High Similarity NPC74727
0.9083 High Similarity NPC37739
0.9083 High Similarity NPC46388
0.9083 High Similarity NPC128925
0.9083 High Similarity NPC256798
0.9074 High Similarity NPC269095
0.9074 High Similarity NPC164194
0.9074 High Similarity NPC279554
0.9074 High Similarity NPC270667
0.9074 High Similarity NPC59804
0.9074 High Similarity NPC127056
0.9074 High Similarity NPC174679
0.9074 High Similarity NPC56713
0.9074 High Similarity NPC136877
0.9074 High Similarity NPC29069
0.9074 High Similarity NPC101450
0.9074 High Similarity NPC475296
0.9074 High Similarity NPC274507
0.9074 High Similarity NPC474589
0.9074 High Similarity NPC78046
0.9074 High Similarity NPC90856
0.9065 High Similarity NPC195708
0.9065 High Similarity NPC295980
0.9065 High Similarity NPC472988
0.9065 High Similarity NPC38217
0.9057 High Similarity NPC162033
0.9043 High Similarity NPC473474
0.9027 High Similarity NPC475187
0.9009 High Similarity NPC58448
0.9009 High Similarity NPC244127
0.9009 High Similarity NPC160415
0.9 High Similarity NPC124296
0.9 High Similarity NPC258885
0.9 High Similarity NPC269315
0.9 High Similarity NPC271138
0.9 High Similarity NPC260665
0.8991 High Similarity NPC292196
0.8991 High Similarity NPC191763
0.8991 High Similarity NPC179434
0.8991 High Similarity NPC164419
0.8991 High Similarity NPC114188
0.8981 High Similarity NPC57362
0.8981 High Similarity NPC296761
0.8981 High Similarity NPC137917
0.8981 High Similarity NPC246205
0.8981 High Similarity NPC125361
0.8981 High Similarity NPC51947
0.8981 High Similarity NPC204407
0.8981 High Similarity NPC154085
0.8981 High Similarity NPC43976
0.8981 High Similarity NPC237503
0.8981 High Similarity NPC473844
0.8981 High Similarity NPC51925
0.8981 High Similarity NPC167383
0.8981 High Similarity NPC306746
0.8972 High Similarity NPC234160
0.8962 High Similarity NPC187400
0.8962 High Similarity NPC221562
0.8962 High Similarity NPC470885
0.8962 High Similarity NPC223741
0.8938 High Similarity NPC477071
0.8938 High Similarity NPC161738
0.8929 High Similarity NPC68175
0.8929 High Similarity NPC477252
0.8919 High Similarity NPC116024
0.8919 High Similarity NPC220293
0.8909 High Similarity NPC139894
0.8909 High Similarity NPC475516
0.8909 High Similarity NPC161434
0.8909 High Similarity NPC104071
0.8909 High Similarity NPC80843
0.8909 High Similarity NPC116794
0.8909 High Similarity NPC473373
0.8909 High Similarity NPC477253
0.8909 High Similarity NPC1046
0.8909 High Similarity NPC257468
0.8909 High Similarity NPC324875
0.8909 High Similarity NPC471383
0.8909 High Similarity NPC276093
0.8909 High Similarity NPC139044
0.8909 High Similarity NPC104400
0.8909 High Similarity NPC195132
0.8909 High Similarity NPC79718
0.8909 High Similarity NPC471967
0.8909 High Similarity NPC469946
0.8909 High Similarity NPC473383
0.8909 High Similarity NPC292677
0.8909 High Similarity NPC109079
0.8909 High Similarity NPC10320
0.8909 High Similarity NPC475504
0.8909 High Similarity NPC102439
0.8909 High Similarity NPC101744
0.8899 High Similarity NPC27551
0.8899 High Similarity NPC108709
0.8899 High Similarity NPC114961
0.8899 High Similarity NPC476881
0.8899 High Similarity NPC476882
0.8899 High Similarity NPC476886
0.8899 High Similarity NPC199457
0.8899 High Similarity NPC75747
0.8899 High Similarity NPC476883
0.8899 High Similarity NPC476880
0.8899 High Similarity NPC476884
0.8899 High Similarity NPC476885
0.8899 High Similarity NPC7870
0.8899 High Similarity NPC68419
0.8899 High Similarity NPC102914
0.8899 High Similarity NPC220984
0.8899 High Similarity NPC476887
0.8899 High Similarity NPC110139
0.8889 High Similarity NPC28198
0.8889 High Similarity NPC177246
0.8889 High Similarity NPC258323
0.8889 High Similarity NPC88744
0.8889 High Similarity NPC476123
0.8889 High Similarity NPC284807
0.8879 High Similarity NPC210178
0.8879 High Similarity NPC473199
0.8879 High Similarity NPC309448
0.8879 High Similarity NPC95243
0.8879 High Similarity NPC248202
0.8879 High Similarity NPC63023
0.887 High Similarity NPC475431
0.886 High Similarity NPC129393
0.885 High Similarity NPC36831
0.885 High Similarity NPC475899
0.885 High Similarity NPC45475
0.885 High Similarity NPC239293
0.8839 High Similarity NPC471384
0.8839 High Similarity NPC161674
0.8839 High Similarity NPC146652
0.8829 High Similarity NPC251263
0.8829 High Similarity NPC155410
0.8829 High Similarity NPC473826
0.8829 High Similarity NPC150400
0.8829 High Similarity NPC114287
0.8829 High Similarity NPC241909
0.8829 High Similarity NPC73455
0.8829 High Similarity NPC295823
0.8829 High Similarity NPC133818
0.8829 High Similarity NPC114304
0.8829 High Similarity NPC73318
0.8829 High Similarity NPC166422
0.8829 High Similarity NPC238935
0.8829 High Similarity NPC163183
0.8829 High Similarity NPC477944
0.8829 High Similarity NPC96641
0.8829 High Similarity NPC475208
0.8829 High Similarity NPC475287
0.8829 High Similarity NPC475467
0.8829 High Similarity NPC46665
0.8829 High Similarity NPC200944
0.8829 High Similarity NPC309714
0.8829 High Similarity NPC473343
0.8829 High Similarity NPC134835
0.8829 High Similarity NPC323341
0.8829 High Similarity NPC174720
0.8829 High Similarity NPC219180
0.8829 High Similarity NPC192600
0.8829 High Similarity NPC151543
0.8818 High Similarity NPC190837
0.8818 High Similarity NPC240734

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC473882 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
0.8636 High Similarity NPD8132 Clinical (unspecified phase)
0.8624 High Similarity NPD6412 Phase 2
0.8496 Intermediate Similarity NPD8133 Approved
0.8319 Intermediate Similarity NPD8328 Phase 3
0.8305 Intermediate Similarity NPD8033 Approved
0.8276 Intermediate Similarity NPD8295 Clinical (unspecified phase)
0.822 Intermediate Similarity NPD8377 Approved
0.822 Intermediate Similarity NPD8294 Approved
0.8182 Intermediate Similarity NPD7507 Approved
0.8151 Intermediate Similarity NPD8296 Approved
0.8151 Intermediate Similarity NPD8379 Approved
0.8151 Intermediate Similarity NPD8378 Approved
0.8151 Intermediate Similarity NPD8335 Approved
0.8151 Intermediate Similarity NPD8380 Approved
0.8053 Intermediate Similarity NPD6686 Approved
0.8049 Intermediate Similarity NPD7736 Approved
0.7984 Intermediate Similarity NPD7319 Approved
0.7967 Intermediate Similarity NPD8293 Discontinued
0.7899 Intermediate Similarity NPD7327 Approved
0.7899 Intermediate Similarity NPD7328 Approved
0.7851 Intermediate Similarity NPD7503 Approved
0.785 Intermediate Similarity NPD6399 Phase 3
0.7833 Intermediate Similarity NPD7516 Approved
0.7787 Intermediate Similarity NPD6370 Approved
0.7778 Intermediate Similarity NPD6882 Approved
0.7778 Intermediate Similarity NPD8297 Approved
0.7705 Intermediate Similarity NPD8517 Approved
0.7705 Intermediate Similarity NPD8515 Approved
0.7705 Intermediate Similarity NPD8516 Approved
0.7705 Intermediate Similarity NPD8513 Phase 3
0.7667 Intermediate Similarity NPD6009 Approved
0.7661 Intermediate Similarity NPD7492 Approved
0.7632 Intermediate Similarity NPD8170 Clinical (unspecified phase)
0.7623 Intermediate Similarity NPD6319 Approved
0.7623 Intermediate Similarity NPD6054 Approved
0.7623 Intermediate Similarity NPD6059 Approved
0.76 Intermediate Similarity NPD6616 Approved
0.7565 Intermediate Similarity NPD6402 Approved
0.7565 Intermediate Similarity NPD7128 Approved
0.7565 Intermediate Similarity NPD5739 Approved
0.7565 Intermediate Similarity NPD6675 Approved
0.7563 Intermediate Similarity NPD4632 Approved
0.754 Intermediate Similarity NPD7078 Approved
0.7521 Intermediate Similarity NPD6373 Approved
0.7521 Intermediate Similarity NPD6372 Approved
0.7521 Intermediate Similarity NPD7115 Discovery
0.7455 Intermediate Similarity NPD7748 Approved
0.7436 Intermediate Similarity NPD6881 Approved
0.7436 Intermediate Similarity NPD6899 Approved
0.7436 Intermediate Similarity NPD7320 Approved
0.7429 Intermediate Similarity NPD4786 Approved
0.7419 Intermediate Similarity NPD6016 Approved
0.7419 Intermediate Similarity NPD6015 Approved
0.7411 Intermediate Similarity NPD6083 Phase 2
0.7411 Intermediate Similarity NPD6084 Phase 2
0.7411 Intermediate Similarity NPD7902 Approved
0.7395 Intermediate Similarity NPD8130 Phase 1
0.7395 Intermediate Similarity NPD8413 Clinical (unspecified phase)
0.7395 Intermediate Similarity NPD6650 Approved
0.7395 Intermediate Similarity NPD6649 Approved
0.736 Intermediate Similarity NPD5988 Approved
0.735 Intermediate Similarity NPD5697 Approved
0.735 Intermediate Similarity NPD5701 Approved
0.7311 Intermediate Similarity NPD6883 Approved
0.7311 Intermediate Similarity NPD7102 Approved
0.7311 Intermediate Similarity NPD7290 Approved
0.7302 Intermediate Similarity NPD6067 Discontinued
0.7273 Intermediate Similarity NPD8035 Phase 2
0.7273 Intermediate Similarity NPD7515 Phase 2
0.7273 Intermediate Similarity NPD8034 Phase 2
0.7265 Intermediate Similarity NPD6008 Approved
0.725 Intermediate Similarity NPD6869 Approved
0.725 Intermediate Similarity NPD6617 Approved
0.725 Intermediate Similarity NPD6847 Approved
0.7238 Intermediate Similarity NPD3667 Approved
0.7227 Intermediate Similarity NPD6012 Approved
0.7227 Intermediate Similarity NPD6014 Approved
0.7227 Intermediate Similarity NPD6013 Approved
0.7193 Intermediate Similarity NPD7638 Approved
0.7165 Intermediate Similarity NPD7604 Phase 2
0.7143 Intermediate Similarity NPD6011 Approved
0.7143 Intermediate Similarity NPD7900 Approved
0.7143 Intermediate Similarity NPD7901 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD5983 Phase 2
0.713 Intermediate Similarity NPD7640 Approved
0.713 Intermediate Similarity NPD7639 Approved
0.7107 Intermediate Similarity NPD6401 Clinical (unspecified phase)
0.7105 Intermediate Similarity NPD4755 Approved
0.7091 Intermediate Similarity NPD5328 Approved
0.7083 Intermediate Similarity NPD4061 Clinical (unspecified phase)
0.708 Intermediate Similarity NPD5695 Phase 3
0.7077 Intermediate Similarity NPD6033 Approved
0.7054 Intermediate Similarity NPD8171 Discontinued
0.7054 Intermediate Similarity NPD4202 Approved
0.7054 Intermediate Similarity NPD6336 Discontinued
0.7043 Intermediate Similarity NPD5696 Approved
0.7037 Intermediate Similarity NPD7520 Clinical (unspecified phase)
0.7025 Intermediate Similarity NPD4634 Approved
0.7 Intermediate Similarity NPD5737 Approved
0.7 Intermediate Similarity NPD5345 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD6672 Approved
0.7 Intermediate Similarity NPD7513 Clinical (unspecified phase)
0.6992 Remote Similarity NPD8449 Approved
0.6983 Remote Similarity NPD5286 Approved
0.6983 Remote Similarity NPD5285 Approved
0.6983 Remote Similarity NPD4700 Approved
0.6983 Remote Similarity NPD4696 Approved
0.6972 Remote Similarity NPD6684 Approved
0.6972 Remote Similarity NPD3618 Phase 1
0.6972 Remote Similarity NPD7334 Approved
0.6972 Remote Similarity NPD6409 Approved
0.6972 Remote Similarity NPD7146 Approved
0.6972 Remote Similarity NPD5330 Approved
0.6972 Remote Similarity NPD7521 Approved
0.6964 Remote Similarity NPD6079 Approved
0.694 Remote Similarity NPD8450 Suspended
0.6937 Remote Similarity NPD4753 Phase 2
0.6885 Remote Similarity NPD5955 Clinical (unspecified phase)
0.688 Remote Similarity NPD6274 Approved
0.687 Remote Similarity NPD8074 Phase 3
0.6864 Remote Similarity NPD5211 Phase 2
0.6864 Remote Similarity NPD5224 Approved
0.6864 Remote Similarity NPD5225 Approved
0.6864 Remote Similarity NPD4633 Approved
0.6864 Remote Similarity NPD5226 Approved
0.685 Remote Similarity NPD7101 Approved
0.685 Remote Similarity NPD7100 Approved
0.6847 Remote Similarity NPD6903 Approved
0.6833 Remote Similarity NPD4768 Approved
0.6833 Remote Similarity NPD4767 Approved
0.6818 Remote Similarity NPD8336 Approved
0.6818 Remote Similarity NPD8337 Approved
0.6818 Remote Similarity NPD6098 Approved
0.6807 Remote Similarity NPD5175 Approved
0.6807 Remote Similarity NPD5174 Approved
0.6789 Remote Similarity NPD3666 Approved
0.6789 Remote Similarity NPD3133 Approved
0.6789 Remote Similarity NPD3668 Phase 3
0.6789 Remote Similarity NPD3665 Phase 1
0.6786 Remote Similarity NPD6673 Approved
0.6786 Remote Similarity NPD6080 Approved
0.6786 Remote Similarity NPD6904 Approved
0.6783 Remote Similarity NPD6356 Clinical (unspecified phase)
0.678 Remote Similarity NPD5223 Approved
0.6774 Remote Similarity NPD6053 Discontinued
0.6772 Remote Similarity NPD6335 Approved
0.6757 Remote Similarity NPD7524 Approved
0.675 Remote Similarity NPD5141 Approved
0.6744 Remote Similarity NPD6908 Approved
0.6744 Remote Similarity NPD6909 Approved
0.6729 Remote Similarity NPD7525 Registered
0.6726 Remote Similarity NPD46 Approved
0.6726 Remote Similarity NPD6698 Approved
0.6724 Remote Similarity NPD5221 Approved
0.6724 Remote Similarity NPD5220 Clinical (unspecified phase)
0.6724 Remote Similarity NPD5222 Approved
0.6724 Remote Similarity NPD4697 Phase 3
0.6721 Remote Similarity NPD4730 Approved
0.6721 Remote Similarity NPD4729 Approved
0.6716 Remote Similarity NPD5956 Approved
0.6693 Remote Similarity NPD6317 Approved
0.6667 Remote Similarity NPD4754 Approved
0.6667 Remote Similarity NPD5173 Approved
0.6667 Remote Similarity NPD5284 Approved
0.6667 Remote Similarity NPD6411 Approved
0.6667 Remote Similarity NPD5281 Approved
0.6667 Remote Similarity NPD7637 Suspended
0.6641 Remote Similarity NPD6313 Approved
0.6641 Remote Similarity NPD6314 Approved
0.6639 Remote Similarity NPD5954 Clinical (unspecified phase)
0.6638 Remote Similarity NPD4629 Approved
0.6638 Remote Similarity NPD5210 Approved
0.6636 Remote Similarity NPD7338 Clinical (unspecified phase)
0.6614 Remote Similarity NPD6940 Discontinued
0.6614 Remote Similarity NPD6868 Approved
0.6613 Remote Similarity NPD5249 Phase 3
0.6613 Remote Similarity NPD5247 Approved
0.6613 Remote Similarity NPD5251 Approved
0.6613 Remote Similarity NPD5250 Approved
0.6613 Remote Similarity NPD5248 Approved
0.661 Remote Similarity NPD4225 Approved
0.661 Remote Similarity NPD8029 Clinical (unspecified phase)
0.6607 Remote Similarity NPD3573 Approved
0.6606 Remote Similarity NPD4223 Phase 3
0.6606 Remote Similarity NPD4221 Approved
0.6597 Remote Similarity NPD7625 Phase 1
0.6585 Remote Similarity NPD5128 Approved
0.6583 Remote Similarity NPD7632 Discontinued
0.6577 Remote Similarity NPD5329 Approved
0.6571 Remote Similarity NPD7339 Approved
0.6571 Remote Similarity NPD6942 Approved
0.6562 Remote Similarity NPD8137 Clinical (unspecified phase)
0.6549 Remote Similarity NPD5208 Approved
0.6545 Remote Similarity NPD6695 Phase 3
0.6542 Remote Similarity NPD6697 Approved
0.6542 Remote Similarity NPD6115 Approved
0.6542 Remote Similarity NPD6118 Approved
0.6542 Remote Similarity NPD6114 Approved
0.6522 Remote Similarity NPD6050 Approved
0.6522 Remote Similarity NPD5693 Phase 1

Structure

External Identifiers

PubChem CID   10996447
ChEMBL   CHEMBL454236
ZINC  

Physicochemical Properties

Molecular Weight:  824.49
ALogP:  -1.5754
MLogP:  4.76
XLogP:  3.861
# Rotatable Bonds:  29
Polar Surface Area:  221.9
# H-Bond Aceptor:  14
# H-Bond Donor:  7
# Rings:  6
# Heavy Atoms:  58

Download Data

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