Natural Product: NPC159168

Natural Product ID:  NPC159168
Common Name:   Barringtogenol C
IUPAC Name:   (3R,4R,4aR,5R,6aR,6aS,6bR,8aR,10S,12aR,14bS)-4a-(hydroxymethyl)-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-3,4,5,10-tetrol
Synonyms:   Barringtogenol C
Molecular Formula:   C30H50O5
Standard InCHIKey:  AYDKOFQQBHRXEW-AAUPIIFFSA-N
Standard InCHI:  InChI=1S/C30H50O5/c1-25(2)14-18-17-8-9-20-27(5)12-11-21(32)26(3,4)19(27)10-13-28(20,6)29(17,7)15-22(33)30(18,16-31)24(35)23(25)34/h8,18-24,31-35H,9-16H2,1-7H3/t18-,19-,20+,21-,22+,23-,24-,27-,28+,29+,30-/m0/s1
Canonical SMILES:  OC[C@]12[C@H](O)C[C@@]3(C(=CC[C@H]4[C@@]3(C)CC[C@@H]3[C@]4(C)CC[C@@H](C3(C)C)O)[C@@H]2CC([C@H]([C@@H]1O)O)(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
NPO23044 Aesculus hippocastanum Species Sapindaceae Eukaryota PMID[3783160]
NPO5697 Barringtonia racemosa Species Lecythidaceae Eukaryota PMID[19388709]
NPO2845 Actinomadura atramentaria Species Thermomonosporaceae Bacteria UNPD*
NPO5169 Acetobacter aceti Species Acetobacteraceae Bacteria UNPD*
NPO10667 Thermopsis rhombifolia Species Fabaceae Eukaryota UNPD*
NPO10503 Semen aesculi NA NA NA TCMSP*
NPO8322 Piscidia communis Species Fabaceae Eukaryota UNPD*
NPO16900 Aesculus turbinata Species Hippocastanaceae Eukaryota TCMID*
NPO16900 Aesculus turbinata Species Hippocastanaceae Eukaryota HerDing*

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT165 Cell Line HeLa Homo sapiens IC50 > 50000 nM 19388709
NPT2 Others Unspecified IC50 > 50000 nM 19388709

  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 NPC159168 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 NPC253402
0.9872 High Similarity NPC238992
0.987 High Similarity NPC47763
0.9625 High Similarity NPC237344
0.9351 High Similarity NPC98386
0.9351 High Similarity NPC253807
0.9351 High Similarity NPC196753
0.9351 High Similarity NPC230295
0.9351 High Similarity NPC300499
0.9351 High Similarity NPC158662
0.9277 High Similarity NPC259875
0.9277 High Similarity NPC187785
0.9231 High Similarity NPC53744
0.9221 High Similarity NPC101475
0.9221 High Similarity NPC34177
0.9221 High Similarity NPC40394
0.9221 High Similarity NPC157996
0.9103 High Similarity NPC99168
0.9103 High Similarity NPC22955
0.9103 High Similarity NPC474989
0.9103 High Similarity NPC470396
0.9091 High Similarity NPC120098
0.9091 High Similarity NPC265328
0.9091 High Similarity NPC290598
0.9091 High Similarity NPC122418
0.9091 High Similarity NPC30590
0.9091 High Similarity NPC27765
0.9036 High Similarity NPC470620
0.9 High Similarity NPC242350
0.8987 High Similarity NPC291379
0.8974 High Similarity NPC477924
0.8961 High Similarity NPC34700
0.8961 High Similarity NPC138374
0.8875 High Similarity NPC295131
0.8851 High Similarity NPC88116
0.8851 High Similarity NPC20235
0.8851 High Similarity NPC231063
0.8851 High Similarity NPC299996
0.8851 High Similarity NPC282395
0.8851 High Similarity NPC145667
0.8851 High Similarity NPC32407
0.8851 High Similarity NPC263548
0.8846 High Similarity NPC274079
0.8846 High Similarity NPC106364
0.8846 High Similarity NPC477925
0.8831 High Similarity NPC100334
0.878 High Similarity NPC82538
0.878 High Similarity NPC207013
0.878 High Similarity NPC237795
0.8734 High Similarity NPC130136
0.8734 High Similarity NPC472805
0.8734 High Similarity NPC90979
0.8718 High Similarity NPC477923
0.8718 High Similarity NPC66566
0.8659 High Similarity NPC30166
0.8659 High Similarity NPC304285
0.8652 High Similarity NPC173744
0.8652 High Similarity NPC201657
0.8652 High Similarity NPC204961
0.8652 High Similarity NPC305464
0.8652 High Similarity NPC25848
0.8652 High Similarity NPC19376
0.8652 High Similarity NPC73004
0.8652 High Similarity NPC307282
0.8642 High Similarity NPC236112
0.8642 High Similarity NPC287749
0.8625 High Similarity NPC72507
0.8621 High Similarity NPC25299
0.8621 High Similarity NPC235884
0.8621 High Similarity NPC472149
0.8621 High Similarity NPC300351
0.8621 High Similarity NPC52021
0.8621 High Similarity NPC306541
0.8621 High Similarity NPC84319
0.8621 High Similarity NPC71074
0.8605 High Similarity NPC105495
0.859 High Similarity NPC91858
0.8556 High Similarity NPC9613
0.8556 High Similarity NPC247139
0.8556 High Similarity NPC261935
0.8556 High Similarity NPC106112
0.8539 High Similarity NPC96916
0.8539 High Similarity NPC32118
0.8537 High Similarity NPC474531
0.8537 High Similarity NPC116202
0.8523 High Similarity NPC307335
0.8523 High Similarity NPC275809
0.8523 High Similarity NPC74855
0.8523 High Similarity NPC136313
0.8506 High Similarity NPC49320
0.8506 High Similarity NPC130278
0.8481 Intermediate Similarity NPC291503
0.8471 Intermediate Similarity NPC137306
0.8471 Intermediate Similarity NPC84121
0.8471 Intermediate Similarity NPC213412
0.8462 Intermediate Similarity NPC477876
0.8462 Intermediate Similarity NPC182717
0.8462 Intermediate Similarity NPC29765
0.8462 Intermediate Similarity NPC477875
0.8462 Intermediate Similarity NPC111214
0.8462 Intermediate Similarity NPC211009
0.8462 Intermediate Similarity NPC271614
0.8444 Intermediate Similarity NPC259733
0.8444 Intermediate Similarity NPC158371
0.8444 Intermediate Similarity NPC207922
0.8444 Intermediate Similarity NPC473158
0.8427 Intermediate Similarity NPC215700
0.8415 Intermediate Similarity NPC236237
0.8415 Intermediate Similarity NPC13554
0.8415 Intermediate Similarity NPC102253
0.8415 Intermediate Similarity NPC322313
0.8395 Intermediate Similarity NPC244385
0.8395 Intermediate Similarity NPC138621
0.8395 Intermediate Similarity NPC6978
0.8395 Intermediate Similarity NPC167037
0.8395 Intermediate Similarity NPC102708
0.8391 Intermediate Similarity NPC130520
0.8391 Intermediate Similarity NPC263393
0.8391 Intermediate Similarity NPC61543
0.8391 Intermediate Similarity NPC121798
0.8391 Intermediate Similarity NPC127689
0.8391 Intermediate Similarity NPC234346
0.8391 Intermediate Similarity NPC25906
0.8391 Intermediate Similarity NPC293048
0.8391 Intermediate Similarity NPC225585
0.8391 Intermediate Similarity NPC270768
0.8391 Intermediate Similarity NPC290972
0.8391 Intermediate Similarity NPC64872
0.8391 Intermediate Similarity NPC59263
0.8375 Intermediate Similarity NPC106432
0.8372 Intermediate Similarity NPC474657
0.8372 Intermediate Similarity NPC186145
0.837 Intermediate Similarity NPC476195
0.837 Intermediate Similarity NPC473790
0.837 Intermediate Similarity NPC35239
0.837 Intermediate Similarity NPC474190
0.8354 Intermediate Similarity NPC471797
0.8354 Intermediate Similarity NPC477138
0.8354 Intermediate Similarity NPC243342
0.8353 Intermediate Similarity NPC133954
0.8353 Intermediate Similarity NPC191965
0.8352 Intermediate Similarity NPC255589
0.8352 Intermediate Similarity NPC259788
0.8352 Intermediate Similarity NPC43686
0.8333 Intermediate Similarity NPC198245
0.8333 Intermediate Similarity NPC301226
0.8333 Intermediate Similarity NPC167706
0.8315 Intermediate Similarity NPC133579
0.8315 Intermediate Similarity NPC474806
0.8315 Intermediate Similarity NPC229281
0.8295 Intermediate Similarity NPC126369
0.8295 Intermediate Similarity NPC18872
0.8295 Intermediate Similarity NPC227467
0.8295 Intermediate Similarity NPC210037
0.8295 Intermediate Similarity NPC471432
0.8295 Intermediate Similarity NPC290614
0.8295 Intermediate Similarity NPC273621
0.8295 Intermediate Similarity NPC471433
0.8295 Intermediate Similarity NPC477872
0.8295 Intermediate Similarity NPC7260
0.8295 Intermediate Similarity NPC476226
0.8295 Intermediate Similarity NPC470589
0.8295 Intermediate Similarity NPC92885
0.8295 Intermediate Similarity NPC77796
0.8295 Intermediate Similarity NPC111110
0.8295 Intermediate Similarity NPC120968
0.8293 Intermediate Similarity NPC80530
0.8293 Intermediate Similarity NPC273410
0.828 Intermediate Similarity NPC256247
0.828 Intermediate Similarity NPC96784
0.828 Intermediate Similarity NPC476132
0.828 Intermediate Similarity NPC235920
0.8276 Intermediate Similarity NPC182797
0.8276 Intermediate Similarity NPC52169
0.8276 Intermediate Similarity NPC67872
0.8276 Intermediate Similarity NPC475664
0.8272 Intermediate Similarity NPC470758
0.8272 Intermediate Similarity NPC470711
0.8272 Intermediate Similarity NPC471798
0.8256 Intermediate Similarity NPC269058
0.8256 Intermediate Similarity NPC477579
0.8256 Intermediate Similarity NPC235341
0.8256 Intermediate Similarity NPC475862
0.8256 Intermediate Similarity NPC95594
0.8256 Intermediate Similarity NPC74363
0.8256 Intermediate Similarity NPC24277
0.8256 Intermediate Similarity NPC71520
0.825 Intermediate Similarity NPC144075
0.8242 Intermediate Similarity NPC230151
0.8242 Intermediate Similarity NPC88847
0.8235 Intermediate Similarity NPC185568
0.8228 Intermediate Similarity NPC471799
0.8222 Intermediate Similarity NPC188102
0.8222 Intermediate Similarity NPC6818
0.8222 Intermediate Similarity NPC191412
0.8222 Intermediate Similarity NPC87095
0.8222 Intermediate Similarity NPC114159
0.8214 Intermediate Similarity NPC248886
0.8205 Intermediate Similarity NPC92801
0.8202 Intermediate Similarity NPC155120

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC159168 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
0.9231 High Similarity NPD7645 Phase 2
0.8415 Intermediate Similarity NPD7525 Registered
0.8 Intermediate Similarity NPD7515 Phase 2
0.7805 Intermediate Similarity NPD6942 Approved
0.7805 Intermediate Similarity NPD7339 Approved
0.7711 Intermediate Similarity NPD3701 Clinical (unspecified phase)
0.7634 Intermediate Similarity NPD7748 Approved
0.7579 Intermediate Similarity NPD7902 Approved
0.7294 Intermediate Similarity NPD6933 Approved
0.7263 Intermediate Similarity NPD7900 Approved
0.7263 Intermediate Similarity NPD7901 Clinical (unspecified phase)
0.7253 Intermediate Similarity NPD3618 Phase 1
0.7222 Intermediate Similarity NPD4786 Approved
0.7204 Intermediate Similarity NPD5328 Approved
0.7195 Intermediate Similarity NPD4267 Clinical (unspecified phase)
0.7191 Intermediate Similarity NPD3667 Approved
0.7143 Intermediate Similarity NPD7520 Clinical (unspecified phase)
0.7059 Intermediate Similarity NPD6926 Approved
0.7059 Intermediate Similarity NPD6924 Approved
0.7053 Intermediate Similarity NPD6079 Approved
0.7041 Intermediate Similarity NPD4755 Approved
0.7024 Intermediate Similarity NPD4243 Approved
0.6989 Remote Similarity NPD7524 Approved
0.6979 Remote Similarity NPD4202 Approved
0.6977 Remote Similarity NPD8264 Approved
0.6966 Remote Similarity NPD7509 Discontinued
0.69 Remote Similarity NPD5286 Approved
0.69 Remote Similarity NPD5285 Approved
0.69 Remote Similarity NPD4696 Approved
0.69 Remote Similarity NPD4700 Approved
0.6875 Remote Similarity NPD8035 Phase 2
0.6875 Remote Similarity NPD8034 Phase 2
0.686 Remote Similarity NPD4785 Approved
0.686 Remote Similarity NPD4784 Approved
0.6857 Remote Similarity NPD8132 Clinical (unspecified phase)
0.6854 Remote Similarity NPD6929 Approved
0.6848 Remote Similarity NPD3133 Approved
0.6848 Remote Similarity NPD7338 Clinical (unspecified phase)
0.6848 Remote Similarity NPD3665 Phase 1
0.6848 Remote Similarity NPD3666 Approved
0.6824 Remote Similarity NPD7152 Approved
0.6824 Remote Similarity NPD7151 Approved
0.6824 Remote Similarity NPD7150 Approved
0.6809 Remote Similarity NPD4751 Clinical (unspecified phase)
0.6804 Remote Similarity NPD6399 Phase 3
0.68 Remote Similarity NPD7638 Approved
0.6786 Remote Similarity NPD6923 Approved
0.6786 Remote Similarity NPD6922 Approved
0.6778 Remote Similarity NPD4748 Discontinued
0.6778 Remote Similarity NPD6930 Phase 2
0.6778 Remote Similarity NPD6931 Approved
0.6768 Remote Similarity NPD5220 Clinical (unspecified phase)
0.6768 Remote Similarity NPD4697 Phase 3
0.6768 Remote Similarity NPD5221 Approved
0.6768 Remote Similarity NPD5222 Approved
0.6765 Remote Similarity NPD5211 Phase 2
0.6765 Remote Similarity NPD5224 Approved
0.6765 Remote Similarity NPD5225 Approved
0.6765 Remote Similarity NPD5226 Approved
0.6765 Remote Similarity NPD4633 Approved
0.6739 Remote Similarity NPD6695 Phase 3
0.6733 Remote Similarity NPD7640 Approved
0.6733 Remote Similarity NPD7639 Approved
0.6731 Remote Similarity NPD6402 Approved
0.6731 Remote Similarity NPD7128 Approved
0.6731 Remote Similarity NPD5739 Approved
0.6731 Remote Similarity NPD6675 Approved
0.6706 Remote Similarity NPD7144 Approved
0.6706 Remote Similarity NPD7143 Approved
0.67 Remote Similarity NPD5173 Approved
0.6699 Remote Similarity NPD5174 Approved
0.6699 Remote Similarity NPD5175 Approved
0.6667 Remote Similarity NPD4753 Phase 2
0.6667 Remote Similarity NPD3668 Phase 3
0.6667 Remote Similarity NPD5223 Approved
0.6667 Remote Similarity NPD8328 Phase 3
0.6667 Remote Similarity NPD6412 Phase 2
0.6636 Remote Similarity NPD4634 Approved
0.6635 Remote Similarity NPD5141 Approved
0.6634 Remote Similarity NPD4225 Approved
0.6629 Remote Similarity NPD6925 Approved
0.6629 Remote Similarity NPD6932 Approved
0.6629 Remote Similarity NPD5776 Phase 2
0.6607 Remote Similarity NPD7516 Approved
0.6604 Remote Similarity NPD7320 Approved
0.6604 Remote Similarity NPD6899 Approved
0.6604 Remote Similarity NPD6881 Approved
0.6591 Remote Similarity NPD4190 Phase 3
0.6591 Remote Similarity NPD5275 Approved
0.6577 Remote Similarity NPD8295 Clinical (unspecified phase)
0.6571 Remote Similarity NPD4767 Approved
0.6571 Remote Similarity NPD4768 Approved
0.6556 Remote Similarity NPD7145 Approved
0.6549 Remote Similarity NPD8294 Approved
0.6549 Remote Similarity NPD8377 Approved
0.6543 Remote Similarity NPD368 Approved
0.6542 Remote Similarity NPD6372 Approved
0.6542 Remote Similarity NPD6373 Approved
0.6538 Remote Similarity NPD4754 Approved
0.6518 Remote Similarity NPD7328 Approved
0.6518 Remote Similarity NPD7327 Approved
0.6514 Remote Similarity NPD8297 Approved
0.6509 Remote Similarity NPD5697 Approved
0.6509 Remote Similarity NPD5701 Approved
0.6505 Remote Similarity NPD4159 Approved
0.6495 Remote Similarity NPD7285 Clinical (unspecified phase)
0.6491 Remote Similarity NPD8335 Approved
0.6491 Remote Similarity NPD8380 Approved
0.6491 Remote Similarity NPD8033 Approved
0.6491 Remote Similarity NPD8296 Approved
0.6491 Remote Similarity NPD8379 Approved
0.6491 Remote Similarity NPD8378 Approved
0.6484 Remote Similarity NPD6683 Phase 2
0.6484 Remote Similarity NPD4195 Approved
0.6481 Remote Similarity NPD7102 Approved
0.6481 Remote Similarity NPD7290 Approved
0.6481 Remote Similarity NPD6883 Approved
0.6471 Remote Similarity NPD5290 Discontinued
0.6458 Remote Similarity NPD7750 Discontinued
0.6449 Remote Similarity NPD4730 Approved
0.6449 Remote Similarity NPD4729 Approved
0.6449 Remote Similarity NPD5128 Approved
0.6429 Remote Similarity NPD7115 Discovery
0.6422 Remote Similarity NPD6650 Approved
0.6422 Remote Similarity NPD6617 Approved
0.6422 Remote Similarity NPD8130 Phase 1
0.6422 Remote Similarity NPD6869 Approved
0.6422 Remote Similarity NPD6649 Approved
0.6422 Remote Similarity NPD6847 Approved
0.6421 Remote Similarity NPD6893 Approved
0.6413 Remote Similarity NPD7332 Phase 2
0.6413 Remote Similarity NPD4695 Discontinued
0.6413 Remote Similarity NPD7514 Phase 3
0.6392 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6389 Remote Similarity NPD6012 Approved
0.6389 Remote Similarity NPD6013 Approved
0.6389 Remote Similarity NPD6014 Approved
0.6389 Remote Similarity NPD4061 Clinical (unspecified phase)
0.6374 Remote Similarity NPD7322 Clinical (unspecified phase)
0.6373 Remote Similarity NPD6083 Phase 2
0.6373 Remote Similarity NPD6084 Phase 2
0.6364 Remote Similarity NPD6411 Approved
0.6364 Remote Similarity NPD6882 Approved
0.6354 Remote Similarity NPD3574 Clinical (unspecified phase)
0.6354 Remote Similarity NPD5279 Phase 3
0.6348 Remote Similarity NPD7503 Approved
0.6344 Remote Similarity NPD6902 Approved
0.6344 Remote Similarity NPD6898 Phase 1
0.6337 Remote Similarity NPD5210 Approved
0.6337 Remote Similarity NPD4629 Approved
0.633 Remote Similarity NPD5250 Approved
0.633 Remote Similarity NPD5251 Approved
0.633 Remote Similarity NPD5249 Phase 3
0.633 Remote Similarity NPD5247 Approved
0.633 Remote Similarity NPD5248 Approved
0.6306 Remote Similarity NPD4632 Approved
0.6296 Remote Similarity NPD6011 Approved
0.6277 Remote Similarity NPD4223 Phase 3
0.6277 Remote Similarity NPD4221 Approved
0.6273 Remote Similarity NPD6401 Clinical (unspecified phase)
0.6273 Remote Similarity NPD5217 Approved
0.6273 Remote Similarity NPD5215 Approved
0.6273 Remote Similarity NPD5216 Approved
0.6264 Remote Similarity NPD6116 Phase 1
0.625 Remote Similarity NPD5329 Approved
0.625 Remote Similarity NPD4869 Clinical (unspecified phase)
0.6211 Remote Similarity NPD4788 Approved
0.62 Remote Similarity NPD7087 Discontinued
0.619 Remote Similarity NPD5344 Discontinued
0.6186 Remote Similarity NPD7334 Approved
0.6186 Remote Similarity NPD6684 Approved
0.6186 Remote Similarity NPD7146 Approved
0.6186 Remote Similarity NPD6409 Approved
0.6186 Remote Similarity NPD5330 Approved
0.6186 Remote Similarity NPD7521 Approved
0.6182 Remote Similarity NPD5134 Clinical (unspecified phase)
0.6182 Remote Similarity NPD5169 Approved
0.6182 Remote Similarity NPD5135 Approved
0.6162 Remote Similarity NPD6101 Approved
0.6162 Remote Similarity NPD6051 Approved
0.6162 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6161 Remote Similarity NPD8133 Approved
0.6154 Remote Similarity NPD6117 Approved
0.6147 Remote Similarity NPD5345 Clinical (unspecified phase)
0.6147 Remote Similarity NPD5168 Approved
0.6147 Remote Similarity NPD6686 Approved
0.6146 Remote Similarity NPD4197 Approved
0.6136 Remote Similarity NPD4787 Phase 1
0.6134 Remote Similarity NPD7507 Approved
0.6132 Remote Similarity NPD7632 Discontinued
0.6126 Remote Similarity NPD5127 Approved
0.6122 Remote Similarity NPD3573 Approved
0.6121 Remote Similarity NPD6054 Approved
0.6121 Remote Similarity NPD6319 Approved
0.6121 Remote Similarity NPD6059 Approved
0.6117 Remote Similarity NPD7614 Phase 1
0.61 Remote Similarity NPD3168 Discontinued
0.6067 Remote Similarity NPD4809 Clinical (unspecified phase)
0.6067 Remote Similarity NPD4808 Clinical (unspecified phase)
0.6064 Remote Similarity NPD8259 Clinical (unspecified phase)

Structure

External Identifiers

PubChem CID   185465
ChEMBL   CHEMBL487606
ZINC  

Physicochemical Properties

Molecular Weight:  490.37
ALogP:  0.2016
MLogP:  4.21
XLogP:  6.079
# Rotatable Bonds:  13
Polar Surface Area:  101.15
# H-Bond Aceptor:  5
# H-Bond Donor:  5
# Rings:  5
# Heavy Atoms:  35

Download Data

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