Natural Product: NPC475243

Natural Product ID:  NPC475243
Common Name:   Hebelomic Acid B
IUPAC Name:   (3S)-5-[[(2R,3R,5R,10S,12S,13R,14S,17R)-3,12-diacetyloxy-17-[(2S,3R,6R)-2-hydroxy-6-(2-hydroxypropan-2-yl)oxan-3-yl]-4,4,10,13,14-pentamethyl-2,3,5,6,7,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-2-yl]oxy]-3-hydroxy-3-methyl-5-oxopentanoic acid
Synonyms:  
Molecular Formula:   C40H62O12
Standard InCHIKey:  NWNZSOBRAQBTIG-YXLXRQEESA-N
Standard InCHI:  InChI=1S/C40H62O12/c1-21(41)49-30-17-26-25(39(9)16-15-24(40(30,39)10)23-11-14-29(36(5,6)47)52-34(23)46)12-13-28-35(3,4)33(50-22(2)42)27(18-38(26,28)8)51-32(45)20-37(7,48)19-31(43)44/h23-24,27-30,33-34,46-48H,11-20H2,1-10H3,(H,43,44)/t23-,24-,27-,28+,29-,30+,33+,34+,37+,38-,39+,40+/m1/s1
Canonical SMILES:  CC(=O)O[C@H]1CC2=C([C@]3([C@@]1(C)[C@H](CC3)[C@H]1CC[C@@H](O[C@@H]1O)C(O)(C)C)C)CC[C@@H]1[C@]2(C)C[C@@H](OC(=O)C[C@](CC(=O)O)(O)C)[C@@H](C1(C)C)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
NPO26953 Hebeloma senescens Species Cortinariaceae Eukaryota fruiting bodies PMID[7561908]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT176 Organism Artemia salina Artemia salina LD50 = 386 ug/ml 18183025

  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 NPC475243 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
1.0 High Similarity NPC90630
0.9706 High Similarity NPC475364
0.9406 High Similarity NPC218513
0.9406 High Similarity NPC55954
0.9307 High Similarity NPC471119
0.9307 High Similarity NPC296879
0.9143 High Similarity NPC477069
0.9143 High Similarity NPC477070
0.9074 High Similarity NPC116024
0.8972 High Similarity NPC477073
0.8807 High Similarity NPC477074
0.8716 High Similarity NPC233003
0.8704 High Similarity NPC129340
0.8692 High Similarity NPC195708
0.8636 High Similarity NPC251309
0.8624 High Similarity NPC250481
0.8624 High Similarity NPC285410
0.8624 High Similarity NPC263827
0.8611 High Similarity NPC265655
0.8571 High Similarity NPC473788
0.8571 High Similarity NPC475558
0.8455 Intermediate Similarity NPC292196
0.844 Intermediate Similarity NPC218853
0.8435 Intermediate Similarity NPC129434
0.8421 Intermediate Similarity NPC232258
0.8407 Intermediate Similarity NPC477252
0.8393 Intermediate Similarity NPC220293
0.8393 Intermediate Similarity NPC473882
0.8378 Intermediate Similarity NPC477253
0.8376 Intermediate Similarity NPC130229
0.8364 Intermediate Similarity NPC52241
0.8364 Intermediate Similarity NPC475317
0.8364 Intermediate Similarity NPC154856
0.8364 Intermediate Similarity NPC250956
0.8349 Intermediate Similarity NPC295389
0.8349 Intermediate Similarity NPC285576
0.8348 Intermediate Similarity NPC476849
0.8348 Intermediate Similarity NPC471406
0.8333 Intermediate Similarity NPC473199
0.8319 Intermediate Similarity NPC244127
0.8288 Intermediate Similarity NPC272242
0.8276 Intermediate Similarity NPC202051
0.8273 Intermediate Similarity NPC296761
0.8273 Intermediate Similarity NPC118225
0.8273 Intermediate Similarity NPC43976
0.8273 Intermediate Similarity NPC125361
0.8273 Intermediate Similarity NPC51925
0.8273 Intermediate Similarity NPC154085
0.8261 Intermediate Similarity NPC477071
0.8241 Intermediate Similarity NPC223741
0.8224 Intermediate Similarity NPC470053
0.822 Intermediate Similarity NPC248202
0.8214 Intermediate Similarity NPC65590
0.8214 Intermediate Similarity NPC48249
0.8214 Intermediate Similarity NPC130427
0.8214 Intermediate Similarity NPC474265
0.8214 Intermediate Similarity NPC125923
0.8214 Intermediate Similarity NPC210420
0.8214 Intermediate Similarity NPC212968
0.8214 Intermediate Similarity NPC64106
0.8198 Intermediate Similarity NPC220984
0.8198 Intermediate Similarity NPC114961
0.8198 Intermediate Similarity NPC27551
0.8198 Intermediate Similarity NPC101450
0.8182 Intermediate Similarity NPC38217
0.8182 Intermediate Similarity NPC472988
0.8174 Intermediate Similarity NPC291564
0.8174 Intermediate Similarity NPC239293
0.8174 Intermediate Similarity NPC471118
0.8174 Intermediate Similarity NPC471121
0.8167 Intermediate Similarity NPC245094
0.8165 Intermediate Similarity NPC162033
0.8151 Intermediate Similarity NPC174367
0.8151 Intermediate Similarity NPC47113
0.8142 Intermediate Similarity NPC475208
0.8142 Intermediate Similarity NPC269315
0.8142 Intermediate Similarity NPC194273
0.8142 Intermediate Similarity NPC238935
0.8142 Intermediate Similarity NPC271138
0.8142 Intermediate Similarity NPC102619
0.8142 Intermediate Similarity NPC320118
0.8142 Intermediate Similarity NPC144068
0.8131 Intermediate Similarity NPC470054
0.8125 Intermediate Similarity NPC11035
0.8125 Intermediate Similarity NPC31839
0.8125 Intermediate Similarity NPC190837
0.8125 Intermediate Similarity NPC114188
0.8125 Intermediate Similarity NPC65167
0.8125 Intermediate Similarity NPC472003
0.812 Intermediate Similarity NPC187950
0.812 Intermediate Similarity NPC278163
0.812 Intermediate Similarity NPC475182
0.8108 Intermediate Similarity NPC91583
0.8108 Intermediate Similarity NPC240125
0.8108 Intermediate Similarity NPC137917
0.8103 Intermediate Similarity NPC25663
0.8103 Intermediate Similarity NPC51564
0.8103 Intermediate Similarity NPC135849
0.8099 Intermediate Similarity NPC476966
0.8091 Intermediate Similarity NPC234160
0.8091 Intermediate Similarity NPC293512
0.8087 Intermediate Similarity NPC471120
0.8087 Intermediate Similarity NPC471117
0.8087 Intermediate Similarity NPC470171
0.8073 Intermediate Similarity NPC470885
0.8073 Intermediate Similarity NPC85593
0.8073 Intermediate Similarity NPC221562
0.8073 Intermediate Similarity NPC31430
0.8073 Intermediate Similarity NPC187400
0.807 Intermediate Similarity NPC475633
0.807 Intermediate Similarity NPC474557
0.807 Intermediate Similarity NPC243354
0.8056 Intermediate Similarity NPC136816
0.8056 Intermediate Similarity NPC154452
0.8053 Intermediate Similarity NPC161434
0.8053 Intermediate Similarity NPC80843
0.8053 Intermediate Similarity NPC195132
0.8053 Intermediate Similarity NPC46388
0.8053 Intermediate Similarity NPC1046
0.8053 Intermediate Similarity NPC116794
0.8053 Intermediate Similarity NPC470543
0.8053 Intermediate Similarity NPC37739
0.8053 Intermediate Similarity NPC243572
0.8051 Intermediate Similarity NPC156789
0.8036 Intermediate Similarity NPC199457
0.8036 Intermediate Similarity NPC269095
0.8036 Intermediate Similarity NPC108709
0.8036 Intermediate Similarity NPC75747
0.8036 Intermediate Similarity NPC102914
0.8036 Intermediate Similarity NPC7870
0.8036 Intermediate Similarity NPC242611
0.8036 Intermediate Similarity NPC110139
0.8036 Intermediate Similarity NPC78046
0.8036 Intermediate Similarity NPC68419
0.8036 Intermediate Similarity NPC274507
0.8034 Intermediate Similarity NPC472076
0.8034 Intermediate Similarity NPC142151
0.8034 Intermediate Similarity NPC110385
0.8034 Intermediate Similarity NPC267694
0.8034 Intermediate Similarity NPC473645
0.8034 Intermediate Similarity NPC472075
0.8034 Intermediate Similarity NPC144644
0.8034 Intermediate Similarity NPC476991
0.8034 Intermediate Similarity NPC37860
0.8034 Intermediate Similarity NPC153673
0.8033 Intermediate Similarity NPC173347
0.8018 Intermediate Similarity NPC258323
0.8018 Intermediate Similarity NPC88744
0.8018 Intermediate Similarity NPC295980
0.8018 Intermediate Similarity NPC224414
0.8017 Intermediate Similarity NPC276758
0.8017 Intermediate Similarity NPC297179
0.8017 Intermediate Similarity NPC86020
0.8017 Intermediate Similarity NPC311534
0.8017 Intermediate Similarity NPC475632
0.8017 Intermediate Similarity NPC18233
0.8 Intermediate Similarity NPC104427
0.8 Intermediate Similarity NPC146652
0.8 Intermediate Similarity NPC279638
0.8 Intermediate Similarity NPC88945
0.8 Intermediate Similarity NPC470767
0.8 Intermediate Similarity NPC475494
0.8 Intermediate Similarity NPC470763
0.8 Intermediate Similarity NPC210178
0.7983 Intermediate Similarity NPC160084
0.7983 Intermediate Similarity NPC478066
0.7982 Intermediate Similarity NPC47063
0.7982 Intermediate Similarity NPC204458
0.7982 Intermediate Similarity NPC260665
0.7982 Intermediate Similarity NPC200944
0.7982 Intermediate Similarity NPC189884
0.7982 Intermediate Similarity NPC146563
0.7982 Intermediate Similarity NPC255017
0.7982 Intermediate Similarity NPC132668
0.7982 Intermediate Similarity NPC138334
0.7982 Intermediate Similarity NPC73986
0.7982 Intermediate Similarity NPC73455
0.7981 Intermediate Similarity NPC27918
0.7966 Intermediate Similarity NPC275225
0.7966 Intermediate Similarity NPC75417
0.7966 Intermediate Similarity NPC293031
0.7966 Intermediate Similarity NPC68767
0.7966 Intermediate Similarity NPC51099
0.7965 Intermediate Similarity NPC108748
0.7965 Intermediate Similarity NPC297208
0.7965 Intermediate Similarity NPC30397
0.7965 Intermediate Similarity NPC471243
0.7965 Intermediate Similarity NPC179434
0.7965 Intermediate Similarity NPC191763
0.7965 Intermediate Similarity NPC269466
0.7965 Intermediate Similarity NPC235841
0.7965 Intermediate Similarity NPC211798
0.7965 Intermediate Similarity NPC473481
0.7963 Intermediate Similarity NPC121072
0.7963 Intermediate Similarity NPC88000
0.7963 Intermediate Similarity NPC47566
0.7963 Intermediate Similarity NPC309425
0.7963 Intermediate Similarity NPC472023
0.7963 Intermediate Similarity NPC21064
0.7963 Intermediate Similarity NPC129372

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC475243 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
0.8273 Intermediate Similarity NPD8132 Clinical (unspecified phase)
0.8087 Intermediate Similarity NPD8295 Clinical (unspecified phase)
0.7661 Intermediate Similarity NPD7319 Approved
0.7581 Intermediate Similarity NPD7736 Approved
0.7561 Intermediate Similarity NPD7507 Approved
0.7541 Intermediate Similarity NPD8328 Phase 3
0.7521 Intermediate Similarity NPD8033 Approved
0.7521 Intermediate Similarity NPD8133 Approved
0.75 Intermediate Similarity NPD7516 Approved
0.75 Intermediate Similarity NPD8293 Discontinued
0.7456 Intermediate Similarity NPD6412 Phase 2
0.7438 Intermediate Similarity NPD8377 Approved
0.7438 Intermediate Similarity NPD8294 Approved
0.7417 Intermediate Similarity NPD7328 Approved
0.7417 Intermediate Similarity NPD7327 Approved
0.7377 Intermediate Similarity NPD8378 Approved
0.7377 Intermediate Similarity NPD8380 Approved
0.7377 Intermediate Similarity NPD8335 Approved
0.7377 Intermediate Similarity NPD8379 Approved
0.7377 Intermediate Similarity NPD8296 Approved
0.7317 Intermediate Similarity NPD6370 Approved
0.7295 Intermediate Similarity NPD6319 Approved
0.7236 Intermediate Similarity NPD8515 Approved
0.7236 Intermediate Similarity NPD7503 Approved
0.7236 Intermediate Similarity NPD8517 Approved
0.7236 Intermediate Similarity NPD8516 Approved
0.7236 Intermediate Similarity NPD8513 Phase 3
0.72 Intermediate Similarity NPD7492 Approved
0.719 Intermediate Similarity NPD7115 Discovery
0.7154 Intermediate Similarity NPD6059 Approved
0.7154 Intermediate Similarity NPD6054 Approved
0.7143 Intermediate Similarity NPD8297 Approved
0.7143 Intermediate Similarity NPD6616 Approved
0.7094 Intermediate Similarity NPD6686 Approved
0.7087 Intermediate Similarity NPD7078 Approved
0.7034 Intermediate Similarity NPD4061 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD6882 Approved
0.6991 Remote Similarity NPD7638 Approved
0.6983 Remote Similarity NPD8170 Clinical (unspecified phase)
0.696 Remote Similarity NPD6015 Approved
0.696 Remote Similarity NPD6016 Approved
0.6949 Remote Similarity NPD5345 Clinical (unspecified phase)
0.6942 Remote Similarity NPD4632 Approved
0.693 Remote Similarity NPD7639 Approved
0.693 Remote Similarity NPD7640 Approved
0.6923 Remote Similarity NPD6402 Approved
0.6923 Remote Similarity NPD7128 Approved
0.6923 Remote Similarity NPD6675 Approved
0.6923 Remote Similarity NPD5739 Approved
0.6911 Remote Similarity NPD6009 Approved
0.6909 Remote Similarity NPD6411 Approved
0.6905 Remote Similarity NPD5988 Approved
0.6891 Remote Similarity NPD6373 Approved
0.6891 Remote Similarity NPD6372 Approved
0.6847 Remote Similarity NPD6399 Phase 3
0.6833 Remote Similarity NPD5955 Clinical (unspecified phase)
0.681 Remote Similarity NPD7632 Discontinued
0.6807 Remote Similarity NPD6899 Approved
0.6807 Remote Similarity NPD6881 Approved
0.6807 Remote Similarity NPD7320 Approved
0.6777 Remote Similarity NPD8130 Phase 1
0.6777 Remote Similarity NPD6650 Approved
0.6777 Remote Similarity NPD6649 Approved
0.6757 Remote Similarity NPD8035 Phase 2
0.6757 Remote Similarity NPD8034 Phase 2
0.6727 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6727 Remote Similarity NPD6101 Approved
0.6723 Remote Similarity NPD5701 Approved
0.6723 Remote Similarity NPD5697 Approved
0.6696 Remote Similarity NPD8171 Discontinued
0.6696 Remote Similarity NPD4225 Approved
0.6694 Remote Similarity NPD6883 Approved
0.6694 Remote Similarity NPD4634 Approved
0.6694 Remote Similarity NPD7290 Approved
0.6694 Remote Similarity NPD7102 Approved
0.6667 Remote Similarity NPD7520 Clinical (unspecified phase)
0.6641 Remote Similarity NPD6033 Approved
0.6639 Remote Similarity NPD6617 Approved
0.6639 Remote Similarity NPD6008 Approved
0.6639 Remote Similarity NPD6869 Approved
0.6639 Remote Similarity NPD6847 Approved
0.6637 Remote Similarity NPD7748 Approved
0.6612 Remote Similarity NPD6014 Approved
0.6612 Remote Similarity NPD6013 Approved
0.6612 Remote Similarity NPD6012 Approved
0.6609 Remote Similarity NPD6083 Phase 2
0.6609 Remote Similarity NPD6084 Phase 2
0.6607 Remote Similarity NPD7637 Suspended
0.6589 Remote Similarity NPD7604 Phase 2
0.6583 Remote Similarity NPD5954 Clinical (unspecified phase)
0.6579 Remote Similarity NPD5695 Phase 3
0.6577 Remote Similarity NPD5328 Approved
0.6574 Remote Similarity NPD4786 Approved
0.6565 Remote Similarity NPD8074 Phase 3
0.6562 Remote Similarity NPD5983 Phase 2
0.6549 Remote Similarity NPD5779 Approved
0.6549 Remote Similarity NPD5778 Approved
0.6545 Remote Similarity NPD7524 Approved
0.6529 Remote Similarity NPD6011 Approved
0.6508 Remote Similarity NPD8137 Clinical (unspecified phase)
0.6504 Remote Similarity NPD6401 Clinical (unspecified phase)
0.6489 Remote Similarity NPD6336 Discontinued
0.6476 Remote Similarity NPD6697 Approved
0.6476 Remote Similarity NPD6115 Approved
0.6476 Remote Similarity NPD6114 Approved
0.6476 Remote Similarity NPD6118 Approved
0.6466 Remote Similarity NPD7902 Approved
0.6466 Remote Similarity NPD4755 Approved
0.6462 Remote Similarity NPD6067 Discontinued
0.646 Remote Similarity NPD7515 Phase 2
0.646 Remote Similarity NPD6079 Approved
0.6444 Remote Similarity NPD8338 Approved
0.6434 Remote Similarity NPD6921 Approved
0.641 Remote Similarity NPD5696 Approved
0.6391 Remote Similarity NPD8337 Approved
0.6391 Remote Similarity NPD8336 Approved
0.6389 Remote Similarity NPD3667 Approved
0.6371 Remote Similarity NPD8413 Clinical (unspecified phase)
0.6356 Remote Similarity NPD5285 Approved
0.6356 Remote Similarity NPD5286 Approved
0.6356 Remote Similarity NPD4700 Approved
0.6356 Remote Similarity NPD4696 Approved
0.6355 Remote Similarity NPD4748 Discontinued
0.6355 Remote Similarity NPD7525 Registered
0.633 Remote Similarity NPD3670 Clinical (unspecified phase)
0.633 Remote Similarity NPD3669 Approved
0.632 Remote Similarity NPD6053 Discontinued
0.6316 Remote Similarity NPD7983 Approved
0.6308 Remote Similarity NPD8274 Clinical (unspecified phase)
0.6306 Remote Similarity NPD3618 Phase 1
0.6299 Remote Similarity NPD6274 Approved
0.6299 Remote Similarity NPD6940 Discontinued
0.6286 Remote Similarity NPD6117 Approved
0.6279 Remote Similarity NPD7100 Approved
0.6279 Remote Similarity NPD7101 Approved
0.6261 Remote Similarity NPD4202 Approved
0.626 Remote Similarity NPD8080 Discontinued
0.625 Remote Similarity NPD5225 Approved
0.625 Remote Similarity NPD5226 Approved
0.625 Remote Similarity NPD5211 Phase 2
0.625 Remote Similarity NPD5224 Approved
0.625 Remote Similarity NPD4633 Approved
0.6239 Remote Similarity NPD5222 Approved
0.6239 Remote Similarity NPD5220 Clinical (unspecified phase)
0.6239 Remote Similarity NPD4697 Phase 3
0.6239 Remote Similarity NPD5221 Approved
0.623 Remote Similarity NPD4767 Approved
0.623 Remote Similarity NPD4768 Approved
0.6226 Remote Similarity NPD6116 Phase 1
0.6207 Remote Similarity NPD7900 Approved
0.6207 Remote Similarity NPD7901 Clinical (unspecified phase)
0.6204 Remote Similarity NPD8449 Approved
0.6202 Remote Similarity NPD6335 Approved
0.6198 Remote Similarity NPD5174 Approved
0.6198 Remote Similarity NPD5175 Approved
0.6195 Remote Similarity NPD6672 Approved
0.6195 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6195 Remote Similarity NPD5737 Approved
0.619 Remote Similarity NPD7339 Approved
0.619 Remote Similarity NPD6942 Approved
0.6186 Remote Similarity NPD5173 Approved
0.6183 Remote Similarity NPD6908 Approved
0.6183 Remote Similarity NPD6909 Approved
0.6182 Remote Similarity NPD6695 Phase 3
0.6172 Remote Similarity NPD6868 Approved
0.6167 Remote Similarity NPD5223 Approved
0.6167 Remote Similarity NPD1700 Approved
0.6167 Remote Similarity NPD4159 Approved
0.6167 Remote Similarity NPD5344 Discontinued
0.6161 Remote Similarity NPD6684 Approved
0.6161 Remote Similarity NPD7334 Approved
0.6161 Remote Similarity NPD5330 Approved
0.6161 Remote Similarity NPD7521 Approved
0.6161 Remote Similarity NPD6409 Approved
0.6161 Remote Similarity NPD3574 Clinical (unspecified phase)
0.6161 Remote Similarity NPD7146 Approved
0.6159 Remote Similarity NPD8450 Suspended
0.6154 Remote Similarity NPD6356 Clinical (unspecified phase)
0.6148 Remote Similarity NPD5141 Approved
0.614 Remote Similarity NPD4753 Phase 2
0.6131 Remote Similarity NPD7260 Phase 2
0.6129 Remote Similarity NPD4729 Approved
0.6129 Remote Similarity NPD4730 Approved
0.6126 Remote Similarity NPD7338 Clinical (unspecified phase)
0.6124 Remote Similarity NPD6317 Approved
0.6111 Remote Similarity NPD7645 Phase 2
0.6106 Remote Similarity NPD3573 Approved
0.6106 Remote Similarity NPD7750 Discontinued
0.6102 Remote Similarity NPD7839 Suspended
0.6096 Remote Similarity NPD7625 Phase 1
0.6095 Remote Similarity NPD6113 Clinical (unspecified phase)
0.6087 Remote Similarity NPD6845 Suspended
0.6087 Remote Similarity NPD46 Approved
0.6087 Remote Similarity NPD6698 Approved
0.6077 Remote Similarity NPD6313 Approved
0.6077 Remote Similarity NPD6314 Approved
0.6066 Remote Similarity NPD4754 Approved
0.6058 Remote Similarity NPD5956 Approved
0.6055 Remote Similarity NPD6928 Phase 2
0.6053 Remote Similarity NPD6903 Approved

Structure

External Identifiers

PubChem CID   44584160
ChEMBL   CHEMBL501855
ZINC  

Physicochemical Properties

Molecular Weight:  734.42
ALogP:  0.7851
MLogP:  4.54
XLogP:  4.377
# Rotatable Bonds:  26
Polar Surface Area:  186.12
# H-Bond Aceptor:  12
# H-Bond Donor:  4
# Rings:  5
# Heavy Atoms:  52

Download Data

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