Natural Product: NPC475364

Natural Product ID:  NPC475364
Common Name:   Hebelomic Acid F
IUPAC Name:   (3S)-5-[[(2R,3R,5R,10S,13R,14R,17R)-3-acetyloxy-17-[(2R,3R,6R)-2-acetyloxy-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:   Hebelomic Acid F
Molecular Formula:   C40H62O11
Standard InCHIKey:  JBMORHZTYFJYCP-BVHPACAWSA-N
Standard InCHI:  InChI=1S/C40H62O11/c1-22(41)48-33-28(50-32(45)21-37(7,47)20-31(43)44)19-38(8)26-16-18-39(9)25(15-17-40(39,10)27(26)12-13-29(38)35(33,3)4)24-11-14-30(36(5,6)46)51-34(24)49-23(2)42/h24-25,28-30,33-34,46-47H,11-21H2,1-10H3,(H,43,44)/t24-,25-,28-,29+,30-,33+,34+,37+,38-,39-,40+/m1/s1
Canonical SMILES:  CC(=O)O[C@H]1[C@H](OC(=O)C[C@](CC(=O)O)(O)C)C[C@]2([C@H](C1(C)C)CCC1=C2CC[C@]2([C@@]1(C)CC[C@@H]2[C@H]1CC[C@@H](O[C@@H]1OC(=O)C)C(O)(C)C)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
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 = 19.7 ug/ml 16309305

  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 NPC475364 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
0.9706 High Similarity NPC475243
0.9706 High Similarity NPC90630
0.9159 High Similarity NPC116024
0.9118 High Similarity NPC55954
0.9118 High Similarity NPC218513
0.9048 High Similarity NPC477069
0.9048 High Similarity NPC477070
0.902 High Similarity NPC296879
0.902 High Similarity NPC471119
0.8879 High Similarity NPC477073
0.8785 High Similarity NPC129340
0.8774 High Similarity NPC195708
0.8716 High Similarity NPC477074
0.8704 High Similarity NPC285410
0.8704 High Similarity NPC263827
0.8704 High Similarity NPC250481
0.8692 High Similarity NPC265655
0.8624 High Similarity NPC233003
0.8545 High Similarity NPC251309
0.8532 High Similarity NPC292196
0.8468 Intermediate Similarity NPC220293
0.8455 Intermediate Similarity NPC477253
0.8421 Intermediate Similarity NPC476849
0.8411 Intermediate Similarity NPC473199
0.8393 Intermediate Similarity NPC244127
0.8364 Intermediate Similarity NPC272242
0.8349 Intermediate Similarity NPC51925
0.8349 Intermediate Similarity NPC43976
0.8349 Intermediate Similarity NPC154085
0.8349 Intermediate Similarity NPC296761
0.8349 Intermediate Similarity NPC125361
0.8348 Intermediate Similarity NPC129434
0.8333 Intermediate Similarity NPC232258
0.8319 Intermediate Similarity NPC477252
0.8318 Intermediate Similarity NPC223741
0.8304 Intermediate Similarity NPC473882
0.8302 Intermediate Similarity NPC473788
0.8302 Intermediate Similarity NPC475558
0.8291 Intermediate Similarity NPC130229
0.8288 Intermediate Similarity NPC48249
0.8273 Intermediate Similarity NPC52241
0.8273 Intermediate Similarity NPC114961
0.8273 Intermediate Similarity NPC475317
0.8273 Intermediate Similarity NPC27551
0.8273 Intermediate Similarity NPC154856
0.8273 Intermediate Similarity NPC220984
0.8273 Intermediate Similarity NPC101450
0.8261 Intermediate Similarity NPC471406
0.8257 Intermediate Similarity NPC295389
0.8257 Intermediate Similarity NPC472988
0.8257 Intermediate Similarity NPC285576
0.8257 Intermediate Similarity NPC38217
0.8246 Intermediate Similarity NPC239293
0.8241 Intermediate Similarity NPC162033
0.8214 Intermediate Similarity NPC102619
0.8214 Intermediate Similarity NPC238935
0.8214 Intermediate Similarity NPC475208
0.8198 Intermediate Similarity NPC65167
0.8198 Intermediate Similarity NPC11035
0.8198 Intermediate Similarity NPC31839
0.819 Intermediate Similarity NPC187950
0.819 Intermediate Similarity NPC278163
0.819 Intermediate Similarity NPC202051
0.8182 Intermediate Similarity NPC91583
0.8182 Intermediate Similarity NPC240125
0.8182 Intermediate Similarity NPC218853
0.8182 Intermediate Similarity NPC118225
0.8182 Intermediate Similarity NPC137917
0.8174 Intermediate Similarity NPC51564
0.8174 Intermediate Similarity NPC135849
0.8174 Intermediate Similarity NPC477071
0.8174 Intermediate Similarity NPC25663
0.8165 Intermediate Similarity NPC234160
0.8148 Intermediate Similarity NPC31430
0.8148 Intermediate Similarity NPC85593
0.8136 Intermediate Similarity NPC248202
0.8125 Intermediate Similarity NPC64106
0.8125 Intermediate Similarity NPC80843
0.8125 Intermediate Similarity NPC470543
0.8125 Intermediate Similarity NPC1046
0.8125 Intermediate Similarity NPC474265
0.8125 Intermediate Similarity NPC65590
0.8125 Intermediate Similarity NPC212968
0.8125 Intermediate Similarity NPC130427
0.8125 Intermediate Similarity NPC243572
0.8125 Intermediate Similarity NPC125923
0.8125 Intermediate Similarity NPC210420
0.8108 Intermediate Similarity NPC242611
0.8108 Intermediate Similarity NPC68419
0.8108 Intermediate Similarity NPC102914
0.8108 Intermediate Similarity NPC110139
0.8108 Intermediate Similarity NPC78046
0.8108 Intermediate Similarity NPC108709
0.8108 Intermediate Similarity NPC75747
0.8108 Intermediate Similarity NPC199457
0.8108 Intermediate Similarity NPC250956
0.8108 Intermediate Similarity NPC269095
0.8108 Intermediate Similarity NPC7870
0.8103 Intermediate Similarity NPC476991
0.8103 Intermediate Similarity NPC473645
0.8103 Intermediate Similarity NPC142151
0.8103 Intermediate Similarity NPC144644
0.8103 Intermediate Similarity NPC153673
0.8103 Intermediate Similarity NPC110385
0.8103 Intermediate Similarity NPC267694
0.8103 Intermediate Similarity NPC37860
0.8091 Intermediate Similarity NPC258323
0.8091 Intermediate Similarity NPC88744
0.8091 Intermediate Similarity NPC224414
0.8087 Intermediate Similarity NPC291564
0.8083 Intermediate Similarity NPC245094
0.8067 Intermediate Similarity NPC47113
0.8067 Intermediate Similarity NPC104427
0.8067 Intermediate Similarity NPC174367
0.8053 Intermediate Similarity NPC73455
0.8053 Intermediate Similarity NPC271138
0.8053 Intermediate Similarity NPC320118
0.8053 Intermediate Similarity NPC260665
0.8053 Intermediate Similarity NPC73986
0.8053 Intermediate Similarity NPC200944
0.8053 Intermediate Similarity NPC269315
0.8053 Intermediate Similarity NPC146563
0.8053 Intermediate Similarity NPC144068
0.8037 Intermediate Similarity NPC472023
0.8037 Intermediate Similarity NPC47566
0.8037 Intermediate Similarity NPC88000
0.8037 Intermediate Similarity NPC129372
0.8037 Intermediate Similarity NPC309425
0.8037 Intermediate Similarity NPC160734
0.8037 Intermediate Similarity NPC4831
0.8036 Intermediate Similarity NPC190837
0.8036 Intermediate Similarity NPC114188
0.8036 Intermediate Similarity NPC179434
0.8036 Intermediate Similarity NPC269466
0.8034 Intermediate Similarity NPC275225
0.8034 Intermediate Similarity NPC68767
0.8034 Intermediate Similarity NPC293031
0.8034 Intermediate Similarity NPC51099
0.8034 Intermediate Similarity NPC475182
0.8018 Intermediate Similarity NPC473844
0.8018 Intermediate Similarity NPC167383
0.8018 Intermediate Similarity NPC51947
0.8018 Intermediate Similarity NPC57362
0.8018 Intermediate Similarity NPC306746
0.8018 Intermediate Similarity NPC127853
0.8018 Intermediate Similarity NPC204407
0.8018 Intermediate Similarity NPC237503
0.8017 Intermediate Similarity NPC258592
0.8017 Intermediate Similarity NPC476966
0.8017 Intermediate Similarity NPC471577
0.8017 Intermediate Similarity NPC178548
0.8 Intermediate Similarity NPC292290
0.8 Intermediate Similarity NPC300419
0.8 Intermediate Similarity NPC224121
0.8 Intermediate Similarity NPC2757
0.8 Intermediate Similarity NPC293512
0.7983 Intermediate Similarity NPC6615
0.7983 Intermediate Similarity NPC7850
0.7982 Intermediate Similarity NPC475486
0.7982 Intermediate Similarity NPC475633
0.7982 Intermediate Similarity NPC187400
0.7982 Intermediate Similarity NPC474557
0.7982 Intermediate Similarity NPC54395
0.7982 Intermediate Similarity NPC470885
0.7982 Intermediate Similarity NPC273879
0.7982 Intermediate Similarity NPC221562
0.7982 Intermediate Similarity NPC164389
0.7982 Intermediate Similarity NPC165033
0.7966 Intermediate Similarity NPC156789
0.7966 Intermediate Similarity NPC28532
0.7966 Intermediate Similarity NPC131824
0.7965 Intermediate Similarity NPC139894
0.7965 Intermediate Similarity NPC116794
0.7965 Intermediate Similarity NPC161434
0.7965 Intermediate Similarity NPC100383
0.7965 Intermediate Similarity NPC37739
0.7965 Intermediate Similarity NPC195132
0.7965 Intermediate Similarity NPC473383
0.7965 Intermediate Similarity NPC46388
0.7963 Intermediate Similarity NPC470053
0.7963 Intermediate Similarity NPC154452
0.7963 Intermediate Similarity NPC136816
0.7963 Intermediate Similarity NPC94919
0.7951 Intermediate Similarity NPC173347
0.7949 Intermediate Similarity NPC472076
0.7949 Intermediate Similarity NPC472075
0.7946 Intermediate Similarity NPC476884
0.7946 Intermediate Similarity NPC270667
0.7946 Intermediate Similarity NPC476886
0.7946 Intermediate Similarity NPC476883
0.7946 Intermediate Similarity NPC279554
0.7946 Intermediate Similarity NPC127056
0.7946 Intermediate Similarity NPC29069
0.7946 Intermediate Similarity NPC475296
0.7946 Intermediate Similarity NPC56713
0.7946 Intermediate Similarity NPC136877
0.7946 Intermediate Similarity NPC274507
0.7946 Intermediate Similarity NPC474589
0.7946 Intermediate Similarity NPC476880
0.7946 Intermediate Similarity NPC59804

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC475364 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
0.8349 Intermediate Similarity NPD8132 Clinical (unspecified phase)
0.8 Intermediate Similarity NPD8295 Clinical (unspecified phase)
0.7724 Intermediate Similarity NPD7319 Approved
0.7642 Intermediate Similarity NPD7736 Approved
0.7623 Intermediate Similarity NPD7507 Approved
0.7603 Intermediate Similarity NPD8328 Phase 3
0.7586 Intermediate Similarity NPD8133 Approved
0.7563 Intermediate Similarity NPD7516 Approved
0.7561 Intermediate Similarity NPD8293 Discontinued
0.7522 Intermediate Similarity NPD6412 Phase 2
0.75 Intermediate Similarity NPD8294 Approved
0.75 Intermediate Similarity NPD8377 Approved
0.7479 Intermediate Similarity NPD7328 Approved
0.7479 Intermediate Similarity NPD7327 Approved
0.7438 Intermediate Similarity NPD8335 Approved
0.7438 Intermediate Similarity NPD8379 Approved
0.7438 Intermediate Similarity NPD8378 Approved
0.7438 Intermediate Similarity NPD8033 Approved
0.7438 Intermediate Similarity NPD8296 Approved
0.7438 Intermediate Similarity NPD8380 Approved
0.7377 Intermediate Similarity NPD6370 Approved
0.7295 Intermediate Similarity NPD7503 Approved
0.7258 Intermediate Similarity NPD7492 Approved
0.7213 Intermediate Similarity NPD6059 Approved
0.7213 Intermediate Similarity NPD6319 Approved
0.7213 Intermediate Similarity NPD6054 Approved
0.72 Intermediate Similarity NPD6616 Approved
0.7155 Intermediate Similarity NPD6686 Approved
0.7154 Intermediate Similarity NPD8517 Approved
0.7154 Intermediate Similarity NPD8515 Approved
0.7154 Intermediate Similarity NPD8513 Phase 3
0.7154 Intermediate Similarity NPD8516 Approved
0.7143 Intermediate Similarity NPD7078 Approved
0.7059 Intermediate Similarity NPD6882 Approved
0.7059 Intermediate Similarity NPD8297 Approved
0.7043 Intermediate Similarity NPD8170 Clinical (unspecified phase)
0.7016 Intermediate Similarity NPD6016 Approved
0.7016 Intermediate Similarity NPD6015 Approved
0.6967 Remote Similarity NPD6009 Approved
0.6967 Remote Similarity NPD7115 Discovery
0.696 Remote Similarity NPD5988 Approved
0.6949 Remote Similarity NPD4061 Clinical (unspecified phase)
0.6903 Remote Similarity NPD7638 Approved
0.6891 Remote Similarity NPD5955 Clinical (unspecified phase)
0.6864 Remote Similarity NPD5345 Clinical (unspecified phase)
0.686 Remote Similarity NPD4632 Approved
0.6842 Remote Similarity NPD7639 Approved
0.6842 Remote Similarity NPD7640 Approved
0.6838 Remote Similarity NPD6675 Approved
0.6838 Remote Similarity NPD7128 Approved
0.6838 Remote Similarity NPD5739 Approved
0.6838 Remote Similarity NPD6402 Approved
0.6818 Remote Similarity NPD8034 Phase 2
0.6818 Remote Similarity NPD8035 Phase 2
0.6807 Remote Similarity NPD6372 Approved
0.6807 Remote Similarity NPD6373 Approved
0.6757 Remote Similarity NPD8171 Discontinued
0.6757 Remote Similarity NPD6399 Phase 3
0.6724 Remote Similarity NPD7632 Discontinued
0.6723 Remote Similarity NPD6881 Approved
0.6723 Remote Similarity NPD6899 Approved
0.6723 Remote Similarity NPD7320 Approved
0.6696 Remote Similarity NPD7748 Approved
0.6694 Remote Similarity NPD6649 Approved
0.6694 Remote Similarity NPD6650 Approved
0.6694 Remote Similarity NPD8130 Phase 1
0.6692 Remote Similarity NPD6033 Approved
0.6667 Remote Similarity NPD6411 Approved
0.6639 Remote Similarity NPD5954 Clinical (unspecified phase)
0.6639 Remote Similarity NPD5697 Approved
0.6639 Remote Similarity NPD5701 Approved
0.6637 Remote Similarity NPD5695 Phase 3
0.6617 Remote Similarity NPD8338 Approved
0.6612 Remote Similarity NPD7290 Approved
0.6612 Remote Similarity NPD6883 Approved
0.6612 Remote Similarity NPD4634 Approved
0.6612 Remote Similarity NPD7102 Approved
0.6574 Remote Similarity NPD7520 Clinical (unspecified phase)
0.6565 Remote Similarity NPD8336 Approved
0.6565 Remote Similarity NPD8337 Approved
0.6557 Remote Similarity NPD6617 Approved
0.6557 Remote Similarity NPD6869 Approved
0.6557 Remote Similarity NPD6847 Approved
0.6555 Remote Similarity NPD6008 Approved
0.6542 Remote Similarity NPD3669 Approved
0.6542 Remote Similarity NPD3670 Clinical (unspecified phase)
0.6529 Remote Similarity NPD6014 Approved
0.6529 Remote Similarity NPD6012 Approved
0.6529 Remote Similarity NPD6013 Approved
0.6522 Remote Similarity NPD7902 Approved
0.6522 Remote Similarity NPD6083 Phase 2
0.6522 Remote Similarity NPD6084 Phase 2
0.6512 Remote Similarity NPD7604 Phase 2
0.6512 Remote Similarity NPD6067 Discontinued
0.6489 Remote Similarity NPD8074 Phase 3
0.6486 Remote Similarity NPD6101 Approved
0.6486 Remote Similarity NPD5328 Approved
0.6486 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6484 Remote Similarity NPD5983 Phase 2
0.6466 Remote Similarity NPD5696 Approved
0.6466 Remote Similarity NPD4225 Approved
0.6446 Remote Similarity NPD6011 Approved
0.6429 Remote Similarity NPD8137 Clinical (unspecified phase)
0.6423 Remote Similarity NPD6401 Clinical (unspecified phase)
0.6412 Remote Similarity NPD6336 Discontinued
0.6381 Remote Similarity NPD6114 Approved
0.6381 Remote Similarity NPD6118 Approved
0.6381 Remote Similarity NPD6697 Approved
0.6381 Remote Similarity NPD6115 Approved
0.6379 Remote Similarity NPD4755 Approved
0.6372 Remote Similarity NPD7515 Phase 2
0.6372 Remote Similarity NPD6079 Approved
0.6372 Remote Similarity NPD7637 Suspended
0.6357 Remote Similarity NPD6921 Approved
0.6349 Remote Similarity NPD6940 Discontinued
0.633 Remote Similarity NPD4786 Approved
0.6316 Remote Similarity NPD5778 Approved
0.6316 Remote Similarity NPD5779 Approved
0.6306 Remote Similarity NPD7524 Approved
0.629 Remote Similarity NPD8413 Clinical (unspecified phase)
0.6271 Remote Similarity NPD5286 Approved
0.6271 Remote Similarity NPD4700 Approved
0.6271 Remote Similarity NPD4696 Approved
0.6271 Remote Similarity NPD5285 Approved
0.6262 Remote Similarity NPD7525 Registered
0.6261 Remote Similarity NPD7900 Approved
0.6261 Remote Similarity NPD7901 Clinical (unspecified phase)
0.625 Remote Similarity NPD5737 Approved
0.625 Remote Similarity NPD6672 Approved
0.625 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6231 Remote Similarity NPD8274 Clinical (unspecified phase)
0.622 Remote Similarity NPD6274 Approved
0.6218 Remote Similarity NPD1700 Approved
0.6216 Remote Similarity NPD7334 Approved
0.6216 Remote Similarity NPD5330 Approved
0.6216 Remote Similarity NPD7146 Approved
0.6216 Remote Similarity NPD6684 Approved
0.6216 Remote Similarity NPD6409 Approved
0.6216 Remote Similarity NPD7521 Approved
0.6216 Remote Similarity NPD3618 Phase 1
0.6216 Remote Similarity NPD3574 Clinical (unspecified phase)
0.6207 Remote Similarity NPD6356 Clinical (unspecified phase)
0.6204 Remote Similarity NPD1779 Approved
0.6204 Remote Similarity NPD1780 Approved
0.6202 Remote Similarity NPD7101 Approved
0.6202 Remote Similarity NPD7100 Approved
0.619 Remote Similarity NPD6117 Approved
0.6183 Remote Similarity NPD8080 Discontinued
0.6174 Remote Similarity NPD4202 Approved
0.6167 Remote Similarity NPD5211 Phase 2
0.6167 Remote Similarity NPD5226 Approved
0.6167 Remote Similarity NPD5225 Approved
0.6167 Remote Similarity NPD4633 Approved
0.6167 Remote Similarity NPD5224 Approved
0.6161 Remote Similarity NPD3573 Approved
0.6154 Remote Similarity NPD5222 Approved
0.6154 Remote Similarity NPD5221 Approved
0.6154 Remote Similarity NPD5220 Clinical (unspecified phase)
0.6154 Remote Similarity NPD4697 Phase 3
0.6148 Remote Similarity NPD4768 Approved
0.6148 Remote Similarity NPD4767 Approved
0.6147 Remote Similarity NPD3667 Approved
0.6138 Remote Similarity NPD7625 Phase 1
0.6132 Remote Similarity NPD6116 Phase 1
0.6131 Remote Similarity NPD8449 Approved
0.6124 Remote Similarity NPD6335 Approved
0.6116 Remote Similarity NPD5175 Approved
0.6116 Remote Similarity NPD5174 Approved
0.6111 Remote Similarity NPD4748 Discontinued
0.6111 Remote Similarity NPD6053 Discontinued
0.6111 Remote Similarity NPD6928 Phase 2
0.6107 Remote Similarity NPD6909 Approved
0.6107 Remote Similarity NPD6908 Approved
0.6106 Remote Similarity NPD6903 Approved
0.6103 Remote Similarity NPD5956 Approved
0.6102 Remote Similarity NPD5173 Approved
0.6095 Remote Similarity NPD3702 Approved
0.6094 Remote Similarity NPD6868 Approved
0.6087 Remote Similarity NPD7983 Approved
0.6087 Remote Similarity NPD5284 Approved
0.6087 Remote Similarity NPD5281 Approved
0.6087 Remote Similarity NPD8450 Suspended
0.6087 Remote Similarity NPD6050 Approved
0.6083 Remote Similarity NPD5223 Approved
0.6071 Remote Similarity NPD6098 Approved
0.6066 Remote Similarity NPD4057 Clinical (unspecified phase)
0.6066 Remote Similarity NPD4056 Clinical (unspecified phase)
0.6066 Remote Similarity NPD5141 Approved
0.6058 Remote Similarity NPD7260 Phase 2
0.6055 Remote Similarity NPD4692 Approved
0.6055 Remote Similarity NPD4139 Approved
0.6053 Remote Similarity NPD6673 Approved
0.6053 Remote Similarity NPD6051 Approved
0.6053 Remote Similarity NPD6080 Approved
0.6053 Remote Similarity NPD4753 Phase 2
0.6053 Remote Similarity NPD6904 Approved
0.6048 Remote Similarity NPD4729 Approved
0.6048 Remote Similarity NPD4730 Approved
0.6047 Remote Similarity NPD6317 Approved
0.6019 Remote Similarity NPD7645 Phase 2

Structure

External Identifiers

PubChem CID   44584161
ChEMBL   CHEMBL504371
ZINC  

Physicochemical Properties

Molecular Weight:  718.43
ALogP:  1.3582
MLogP:  4.65
XLogP:  6.673
# Rotatable Bonds:  25
Polar Surface Area:  165.89
# H-Bond Aceptor:  11
# H-Bond Donor:  3
# Rings:  5
# Heavy Atoms:  51

Download Data

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