Natural Product: NPC130427

Natural Product ID:  NPC130427
Common Name:   Bryonioside F
IUPAC Name:   (3S,8S,9R,10R,13R,14S,17R)-17-[(2R)-6-hydroxy-6-methyl-5-oxoheptan-2-yl]-4,4,9,13,14-pentamethyl-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,2,3,7,8,10,12,15,16,17-decahydrocyclopenta[a]phenanthren-11-one
Synonyms:   bryonioside F
Molecular Formula:   C36H58O9
Standard InCHIKey:  IMFAPKVFQZYYJK-CKPIZJOLSA-N
Standard InCHI:  InChI=1S/C36H58O9/c1-19(9-13-25(38)33(4,5)43)20-15-16-34(6)24-12-10-21-22(36(24,8)26(39)17-35(20,34)7)11-14-27(32(21,2)3)45-31-30(42)29(41)28(40)23(18-37)44-31/h10,19-20,22-24,27-31,37,40-43H,9,11-18H2,1-8H3/t19-,20-,22-,23-,24+,27+,28-,29+,30-,31+,34+,35-,36+/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](CCC(=O)C(O)(C)C)C)C)C2(C)C)[C@@H]([C@H]([C@@H]1O)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
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 = 29.2 % 23586849
NPT80 Cell Line Raji Homo sapiens Activity = 60 % 23398362
NPT2 Others Unspecified Inhibition = 97.6 % DrugMatrix in vivo data: Pathology
NPT2 Others Unspecified Inhibition = 71.4 % 24597894
NPT2 Others Unspecified Inhibition = 0 % 16202590

  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 NPC130427 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 NPC474557
0.9806 High Similarity NPC475317
0.9806 High Similarity NPC154856
0.9806 High Similarity NPC52241
0.9619 High Similarity NPC474265
0.9619 High Similarity NPC210420
0.9439 High Similarity NPC473882
0.9364 High Similarity NPC471406
0.9352 High Similarity NPC279638
0.9259 High Similarity NPC74727
0.9238 High Similarity NPC295389
0.9167 High Similarity NPC260665
0.9159 High Similarity NPC250481
0.9159 High Similarity NPC285410
0.9159 High Similarity NPC263827
0.9151 High Similarity NPC246205
0.9065 High Similarity NPC129340
0.9048 High Similarity NPC210178
0.9048 High Similarity NPC63023
0.9048 High Similarity NPC95243
0.9018 High Similarity NPC472257
0.9009 High Similarity NPC475632
0.9009 High Similarity NPC86020
0.9009 High Similarity NPC45475
0.8991 High Similarity NPC477944
0.8991 High Similarity NPC251309
0.8981 High Similarity NPC269466
0.8972 High Similarity NPC477069
0.8972 High Similarity NPC265655
0.8972 High Similarity NPC118225
0.8972 High Similarity NPC477070
0.8952 High Similarity NPC100955
0.8952 High Similarity NPC121566
0.8938 High Similarity NPC476545
0.8938 High Similarity NPC476544
0.8938 High Similarity NPC476543
0.8909 High Similarity NPC165439
0.8899 High Similarity NPC233003
0.8889 High Similarity NPC101450
0.8879 High Similarity NPC195708
0.887 High Similarity NPC475194
0.8868 High Similarity NPC162033
0.885 High Similarity NPC475187
0.885 High Similarity NPC472075
0.885 High Similarity NPC472076
0.8829 High Similarity NPC244127
0.8807 High Similarity NPC292196
0.8807 High Similarity NPC477073
0.8803 High Similarity NPC293623
0.8803 High Similarity NPC69273
0.8803 High Similarity NPC168899
0.8796 High Similarity NPC8431
0.8783 High Similarity NPC476542
0.8774 High Similarity NPC223741
0.8774 High Similarity NPC470885
0.8774 High Similarity NPC221562
0.8774 High Similarity NPC187400
0.8762 High Similarity NPC136816
0.8761 High Similarity NPC477071
0.8761 High Similarity NPC161738
0.8739 High Similarity NPC220293
0.8739 High Similarity NPC477580
0.8739 High Similarity NPC116024
0.8738 High Similarity NPC473890
0.8738 High Similarity NPC243728
0.8729 High Similarity NPC471407
0.8727 High Similarity NPC46388
0.8727 High Similarity NPC37739
0.8716 High Similarity NPC114961
0.8716 High Similarity NPC27551
0.8716 High Similarity NPC274507
0.8704 High Similarity NPC258323
0.8696 High Similarity NPC156789
0.8696 High Similarity NPC28532
0.8696 High Similarity NPC475431
0.8692 High Similarity NPC473199
0.8692 High Similarity NPC309448
0.8684 High Similarity NPC129393
0.8673 High Similarity NPC239293
0.8667 High Similarity NPC88000
0.8667 High Similarity NPC4831
0.8667 High Similarity NPC160734
0.8667 High Similarity NPC129372
0.8667 High Similarity NPC472023
0.8667 High Similarity NPC47566
0.8667 High Similarity NPC309425
0.8655 High Similarity NPC241008
0.8654 High Similarity NPC158088
0.8649 High Similarity NPC189884
0.8649 High Similarity NPC62696
0.8649 High Similarity NPC138334
0.8649 High Similarity NPC271138
0.8649 High Similarity NPC73455
0.8649 High Similarity NPC204458
0.8649 High Similarity NPC47063
0.8649 High Similarity NPC200944
0.8649 High Similarity NPC178981
0.8649 High Similarity NPC269315
0.8649 High Similarity NPC477074
0.8649 High Similarity NPC293038
0.8636 High Similarity NPC108748
0.8636 High Similarity NPC211798
0.8636 High Similarity NPC297208
0.8636 High Similarity NPC274833
0.8636 High Similarity NPC235841
0.8636 High Similarity NPC30397
0.8636 High Similarity NPC473481
0.8636 High Similarity NPC191763
0.8624 High Similarity NPC218853
0.8624 High Similarity NPC306746
0.8624 High Similarity NPC137917
0.8624 High Similarity NPC204407
0.8624 High Similarity NPC167383
0.8624 High Similarity NPC237503
0.8624 High Similarity NPC57362
0.8621 High Similarity NPC160084
0.8621 High Similarity NPC472077
0.8621 High Similarity NPC472078
0.8611 High Similarity NPC293512
0.8611 High Similarity NPC190395
0.8611 High Similarity NPC226642
0.8611 High Similarity NPC33053
0.8609 High Similarity NPC202051
0.8609 High Similarity NPC249553
0.8609 High Similarity NPC475182
0.8609 High Similarity NPC42675
0.8609 High Similarity NPC182900
0.8609 High Similarity NPC476672
0.8609 High Similarity NPC476675
0.8598 High Similarity NPC93352
0.8598 High Similarity NPC75608
0.8596 High Similarity NPC190939
0.8596 High Similarity NPC197003
0.8585 High Similarity NPC272015
0.8585 High Similarity NPC154452
0.8585 High Similarity NPC94919
0.8584 High Similarity NPC309433
0.8583 High Similarity NPC471855
0.8583 High Similarity NPC473519
0.8583 High Similarity NPC473805
0.8571 High Similarity NPC7341
0.8571 High Similarity NPC167974
0.8571 High Similarity NPC102088
0.8571 High Similarity NPC473200
0.8571 High Similarity NPC282669
0.8559 High Similarity NPC471967
0.8559 High Similarity NPC256798
0.8559 High Similarity NPC472719
0.8559 High Similarity NPC477253
0.8559 High Similarity NPC128925
0.8559 High Similarity NPC116794
0.8559 High Similarity NPC207845
0.8547 High Similarity NPC473474
0.8547 High Similarity NPC476674
0.8547 High Similarity NPC130229
0.8545 High Similarity NPC270667
0.8545 High Similarity NPC75747
0.8545 High Similarity NPC29069
0.8545 High Similarity NPC476885
0.8545 High Similarity NPC269095
0.8545 High Similarity NPC110139
0.8545 High Similarity NPC136877
0.8545 High Similarity NPC56713
0.8545 High Similarity NPC78046
0.8545 High Similarity NPC68419
0.8545 High Similarity NPC174679
0.8545 High Similarity NPC279554
0.8545 High Similarity NPC474589
0.8545 High Similarity NPC476882
0.8545 High Similarity NPC220984
0.8545 High Similarity NPC476884
0.8545 High Similarity NPC476887
0.8545 High Similarity NPC476881
0.8545 High Similarity NPC59804
0.8545 High Similarity NPC108709
0.8545 High Similarity NPC102914
0.8545 High Similarity NPC7870
0.8545 High Similarity NPC476880
0.8545 High Similarity NPC164194
0.8545 High Similarity NPC90856
0.8545 High Similarity NPC199457
0.8545 High Similarity NPC127056
0.8545 High Similarity NPC476886
0.8545 High Similarity NPC470065
0.8545 High Similarity NPC475296
0.8545 High Similarity NPC476883
0.8534 High Similarity NPC94072
0.8534 High Similarity NPC305771
0.8534 High Similarity NPC169816
0.8534 High Similarity NPC15918
0.8532 High Similarity NPC177246
0.8532 High Similarity NPC295980
0.8532 High Similarity NPC472988
0.8532 High Similarity NPC38217
0.8532 High Similarity NPC28198
0.8532 High Similarity NPC476123
0.8532 High Similarity NPC284807
0.8532 High Similarity NPC88744
0.8522 High Similarity NPC308459
0.8519 High Similarity NPC473476

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC130427 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
0.8785 High Similarity NPD6412 Phase 2
0.8288 Intermediate Similarity NPD8132 Clinical (unspecified phase)
0.822 Intermediate Similarity NPD6370 Approved
0.8182 Intermediate Similarity NPD7736 Approved
0.8151 Intermediate Similarity NPD8328 Phase 3
0.8103 Intermediate Similarity NPD8295 Clinical (unspecified phase)
0.8099 Intermediate Similarity NPD8293 Discontinued
0.8051 Intermediate Similarity NPD6059 Approved
0.8051 Intermediate Similarity NPD6054 Approved
0.8017 Intermediate Similarity NPD7507 Approved
0.8 Intermediate Similarity NPD8133 Approved
0.7913 Intermediate Similarity NPD6882 Approved
0.7913 Intermediate Similarity NPD8297 Approved
0.7876 Intermediate Similarity NPD6686 Approved
0.7833 Intermediate Similarity NPD6015 Approved
0.7833 Intermediate Similarity NPD8033 Approved
0.7833 Intermediate Similarity NPD6016 Approved
0.7823 Intermediate Similarity NPD7319 Approved
0.7797 Intermediate Similarity NPD6009 Approved
0.7787 Intermediate Similarity NPD7492 Approved
0.7769 Intermediate Similarity NPD5988 Approved
0.775 Intermediate Similarity NPD8294 Approved
0.775 Intermediate Similarity NPD8377 Approved
0.775 Intermediate Similarity NPD6319 Approved
0.7731 Intermediate Similarity NPD7327 Approved
0.7731 Intermediate Similarity NPD7328 Approved
0.7724 Intermediate Similarity NPD6616 Approved
0.7699 Intermediate Similarity NPD6675 Approved
0.7699 Intermediate Similarity NPD6402 Approved
0.7699 Intermediate Similarity NPD7128 Approved
0.7699 Intermediate Similarity NPD5739 Approved
0.7692 Intermediate Similarity NPD4632 Approved
0.7686 Intermediate Similarity NPD8296 Approved
0.7686 Intermediate Similarity NPD8380 Approved
0.7686 Intermediate Similarity NPD8379 Approved
0.7686 Intermediate Similarity NPD8335 Approved
0.7686 Intermediate Similarity NPD8378 Approved
0.7667 Intermediate Similarity NPD7516 Approved
0.7664 Intermediate Similarity NPD6399 Phase 3
0.7661 Intermediate Similarity NPD7078 Approved
0.7652 Intermediate Similarity NPD6373 Approved
0.7652 Intermediate Similarity NPD6372 Approved
0.7573 Intermediate Similarity NPD4786 Approved
0.7565 Intermediate Similarity NPD7320 Approved
0.7565 Intermediate Similarity NPD6899 Approved
0.7565 Intermediate Similarity NPD6881 Approved
0.7545 Intermediate Similarity NPD6083 Phase 2
0.7545 Intermediate Similarity NPD4755 Approved
0.7545 Intermediate Similarity NPD6084 Phase 2
0.7541 Intermediate Similarity NPD7503 Approved
0.7521 Intermediate Similarity NPD8130 Phase 1
0.7521 Intermediate Similarity NPD6649 Approved
0.7521 Intermediate Similarity NPD6650 Approved
0.7478 Intermediate Similarity NPD5701 Approved
0.7478 Intermediate Similarity NPD5697 Approved
0.746 Intermediate Similarity NPD6033 Approved
0.7456 Intermediate Similarity NPD8170 Clinical (unspecified phase)
0.7436 Intermediate Similarity NPD6883 Approved
0.7436 Intermediate Similarity NPD7290 Approved
0.7436 Intermediate Similarity NPD4634 Approved
0.7436 Intermediate Similarity NPD7102 Approved
0.7419 Intermediate Similarity NPD6067 Discontinued
0.7411 Intermediate Similarity NPD5285 Approved
0.7411 Intermediate Similarity NPD5286 Approved
0.7411 Intermediate Similarity NPD4700 Approved
0.7411 Intermediate Similarity NPD4696 Approved
0.7383 Intermediate Similarity NPD4753 Phase 2
0.7379 Intermediate Similarity NPD3667 Approved
0.7373 Intermediate Similarity NPD6869 Approved
0.7373 Intermediate Similarity NPD6847 Approved
0.7373 Intermediate Similarity NPD6617 Approved
0.7355 Intermediate Similarity NPD7115 Discovery
0.735 Intermediate Similarity NPD6013 Approved
0.735 Intermediate Similarity NPD6012 Approved
0.735 Intermediate Similarity NPD6014 Approved
0.7281 Intermediate Similarity NPD5225 Approved
0.7281 Intermediate Similarity NPD5211 Phase 2
0.7281 Intermediate Similarity NPD4633 Approved
0.7281 Intermediate Similarity NPD5224 Approved
0.7281 Intermediate Similarity NPD5226 Approved
0.728 Intermediate Similarity NPD7604 Phase 2
0.7265 Intermediate Similarity NPD6011 Approved
0.7258 Intermediate Similarity NPD8517 Approved
0.7258 Intermediate Similarity NPD8516 Approved
0.7258 Intermediate Similarity NPD5983 Phase 2
0.7258 Intermediate Similarity NPD8513 Phase 3
0.7258 Intermediate Similarity NPD8515 Approved
0.7241 Intermediate Similarity NPD4768 Approved
0.7241 Intermediate Similarity NPD4767 Approved
0.7227 Intermediate Similarity NPD6401 Clinical (unspecified phase)
0.7227 Intermediate Similarity NPD8413 Clinical (unspecified phase)
0.7222 Intermediate Similarity NPD5328 Approved
0.7217 Intermediate Similarity NPD5175 Approved
0.7217 Intermediate Similarity NPD5174 Approved
0.7207 Intermediate Similarity NPD5695 Phase 3
0.7193 Intermediate Similarity NPD5223 Approved
0.7182 Intermediate Similarity NPD4202 Approved
0.7168 Intermediate Similarity NPD5696 Approved
0.7165 Intermediate Similarity NPD6336 Discontinued
0.7155 Intermediate Similarity NPD5141 Approved
0.7143 Intermediate Similarity NPD5222 Approved
0.7143 Intermediate Similarity NPD5221 Approved
0.7143 Intermediate Similarity NPD4697 Phase 3
0.7143 Intermediate Similarity NPD5220 Clinical (unspecified phase)
0.713 Intermediate Similarity NPD6672 Approved
0.713 Intermediate Similarity NPD5737 Approved
0.7119 Intermediate Similarity NPD5345 Clinical (unspecified phase)
0.7119 Intermediate Similarity NPD4729 Approved
0.7119 Intermediate Similarity NPD4730 Approved
0.7117 Intermediate Similarity NPD7748 Approved
0.7103 Intermediate Similarity NPD3618 Phase 1
0.7094 Intermediate Similarity NPD6008 Approved
0.7091 Intermediate Similarity NPD8034 Phase 2
0.7091 Intermediate Similarity NPD8035 Phase 2
0.7091 Intermediate Similarity NPD6079 Approved
0.708 Intermediate Similarity NPD7902 Approved
0.708 Intermediate Similarity NPD5173 Approved
0.7077 Intermediate Similarity NPD5956 Approved
0.7069 Intermediate Similarity NPD4754 Approved
0.7054 Intermediate Similarity NPD5210 Approved
0.7054 Intermediate Similarity NPD4629 Approved
0.7018 Intermediate Similarity NPD7638 Approved
0.7009 Intermediate Similarity NPD5329 Approved
0.7 Intermediate Similarity NPD5250 Approved
0.7 Intermediate Similarity NPD5248 Approved
0.7 Intermediate Similarity NPD5249 Phase 3
0.7 Intermediate Similarity NPD5251 Approved
0.7 Intermediate Similarity NPD5247 Approved
0.6992 Remote Similarity NPD6274 Approved
0.6975 Remote Similarity NPD5128 Approved
0.696 Remote Similarity NPD7101 Approved
0.696 Remote Similarity NPD7100 Approved
0.6957 Remote Similarity NPD7640 Approved
0.6957 Remote Similarity NPD7639 Approved
0.6944 Remote Similarity NPD5279 Phase 3
0.6944 Remote Similarity NPD6098 Approved
0.6937 Remote Similarity NPD7515 Phase 2
0.6917 Remote Similarity NPD4061 Clinical (unspecified phase)
0.6916 Remote Similarity NPD3665 Phase 1
0.6916 Remote Similarity NPD4197 Approved
0.6916 Remote Similarity NPD3133 Approved
0.6916 Remote Similarity NPD3668 Phase 3
0.6916 Remote Similarity NPD3666 Approved
0.6909 Remote Similarity NPD6673 Approved
0.6909 Remote Similarity NPD6080 Approved
0.6909 Remote Similarity NPD6904 Approved
0.6881 Remote Similarity NPD7524 Approved
0.688 Remote Similarity NPD6335 Approved
0.6875 Remote Similarity NPD8171 Discontinued
0.6857 Remote Similarity NPD7525 Registered
0.6852 Remote Similarity NPD7520 Clinical (unspecified phase)
0.685 Remote Similarity NPD6908 Approved
0.685 Remote Similarity NPD6909 Approved
0.6842 Remote Similarity NPD8449 Approved
0.6818 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6814 Remote Similarity NPD7901 Clinical (unspecified phase)
0.6814 Remote Similarity NPD7900 Approved
0.6803 Remote Similarity NPD5215 Approved
0.6803 Remote Similarity NPD5216 Approved
0.6803 Remote Similarity NPD5217 Approved
0.68 Remote Similarity NPD6317 Approved
0.6791 Remote Similarity NPD8450 Suspended
0.6789 Remote Similarity NPD6684 Approved
0.6789 Remote Similarity NPD6409 Approved
0.6789 Remote Similarity NPD7334 Approved
0.6789 Remote Similarity NPD5330 Approved
0.6789 Remote Similarity NPD7521 Approved
0.6789 Remote Similarity NPD7146 Approved
0.6759 Remote Similarity NPD7338 Clinical (unspecified phase)
0.6746 Remote Similarity NPD6314 Approved
0.6746 Remote Similarity NPD6313 Approved
0.6729 Remote Similarity NPD4221 Approved
0.6729 Remote Similarity NPD4223 Phase 3
0.6721 Remote Similarity NPD5134 Clinical (unspecified phase)
0.6721 Remote Similarity NPD5955 Clinical (unspecified phase)
0.6721 Remote Similarity NPD5135 Approved
0.6721 Remote Similarity NPD5169 Approved
0.672 Remote Similarity NPD6868 Approved
0.6699 Remote Similarity NPD7339 Approved
0.6699 Remote Similarity NPD6942 Approved
0.6693 Remote Similarity NPD4522 Approved
0.6667 Remote Similarity NPD5127 Approved
0.6667 Remote Similarity NPD5282 Discontinued
0.6667 Remote Similarity NPD6903 Approved
0.6667 Remote Similarity NPD6695 Phase 3
0.6637 Remote Similarity NPD5693 Phase 1
0.6637 Remote Similarity NPD6050 Approved
0.6636 Remote Similarity NPD5280 Approved
0.6636 Remote Similarity NPD4694 Approved
0.6636 Remote Similarity NPD5690 Phase 2
0.6613 Remote Similarity NPD6053 Discontinued
0.6609 Remote Similarity NPD6356 Clinical (unspecified phase)
0.6591 Remote Similarity NPD8074 Phase 3
0.6589 Remote Similarity NPD6291 Clinical (unspecified phase)
0.6589 Remote Similarity NPD6921 Approved
0.6577 Remote Similarity NPD7750 Discontinued
0.6557 Remote Similarity NPD5168 Approved
0.6549 Remote Similarity NPD5692 Phase 3
0.6549 Remote Similarity NPD46 Approved
0.6549 Remote Similarity NPD6698 Approved

Structure

External Identifiers

PubChem CID   10985073
ChEMBL   CHEMBL451089
ZINC  

Physicochemical Properties

Molecular Weight:  634.41
ALogP:  -0.1379
MLogP:  4.43
XLogP:  3.934
# Rotatable Bonds:  21
Polar Surface Area:  153.75
# H-Bond Aceptor:  9
# H-Bond Donor:  5
# Rings:  5
# Heavy Atoms:  45

Download Data

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