Natural Product: NPC278091

Natural Product ID:  NPC278091
Common Name:   23-Hydroxybetulin
IUPAC Name:   (1R,3aS,5aR,5bR,7aR,8R,9S,11aR,11bR,13aR,13bR)-3a,8-bis(hydroxymethyl)-5a,5b,8,11a-tetramethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysen-9-ol
Synonyms:  
Molecular Formula:   C30H50O3
Standard InCHIKey:  PHMKDBZGQWXPAZ-MZFJGDBOSA-N
Standard InCHI:  InChI=1S/C30H50O3/c1-19(2)20-9-14-30(18-32)16-15-28(5)21(25(20)30)7-8-23-26(3)12-11-24(33)27(4,17-31)22(26)10-13-29(23,28)6/h20-25,31-33H,1,7-18H2,2-6H3/t20-,21+,22+,23+,24-,25+,26-,27-,28+,29+,30+/m0/s1
Canonical SMILES:  OC[C@@]12CC[C@H]([C@@H]2[C@@H]2[C@](CC1)(C)[C@]1(C)CC[C@@H]3[C@]([C@H]1CC2)(C)CC[C@@H]([C@@]3(C)CO)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
NPO26183 Scabiosa pyrenaica Species Caprifoliaceae Eukaryota UNPD*
NPO2201 Orthocaulis attenuatus Species Anastrophyllaceae Eukaryota UNPD*
NPO25532 Blitum virgatum Species Chenopodiaceae Eukaryota UNPD*
NPO23780 Psoroma crassum Species Pannariaceae Eukaryota UNPD*
NPO26828 Barbarea verna Species Brassicaceae Eukaryota UNPD*
NPO25482 Phyllogeiton zeyheri NA NA NA UNPD*

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT6 Organism Plasmodium falciparum Plasmodium falciparum IC50 = 3400 nM 26722868
NPT6 Organism Plasmodium falciparum Plasmodium falciparum IC50 = 5200 nM 26722868
NPT2 Others Unspecified Ratio IC50 = 1.5 26722868
NPT165 Cell Line HeLa Homo sapiens IC50 > 20000 nM 26722868
NPT2 Others Unspecified Ratio IC50 > 5.9 26722868
NPT2 Others Unspecified Ratio IC50 > 3.8 26722868

  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 NPC278091 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 NPC93662
1.0 High Similarity NPC78067
0.9857 High Similarity NPC104387
0.9857 High Similarity NPC178383
0.9857 High Similarity NPC240235
0.9857 High Similarity NPC212879
0.9857 High Similarity NPC231256
0.9718 High Similarity NPC86305
0.9718 High Similarity NPC14112
0.9714 High Similarity NPC192638
0.9714 High Similarity NPC62657
0.9714 High Similarity NPC25511
0.9589 High Similarity NPC472742
0.9589 High Similarity NPC116119
0.9589 High Similarity NPC475727
0.9589 High Similarity NPC80297
0.9583 High Similarity NPC248830
0.9583 High Similarity NPC212241
0.9583 High Similarity NPC202540
0.9583 High Similarity NPC119355
0.9459 High Similarity NPC475679
0.9452 High Similarity NPC42853
0.9452 High Similarity NPC102708
0.9429 High Similarity NPC111234
0.9324 High Similarity NPC49599
0.9324 High Similarity NPC49627
0.9306 High Similarity NPC70982
0.9306 High Similarity NPC185536
0.9306 High Similarity NPC230704
0.9306 High Similarity NPC3403
0.9286 High Similarity NPC45296
0.9189 High Similarity NPC31828
0.9178 High Similarity NPC91573
0.9167 High Similarity NPC196358
0.9167 High Similarity NPC254509
0.9167 High Similarity NPC472503
0.9167 High Similarity NPC145552
0.9167 High Similarity NPC5046
0.9167 High Similarity NPC308440
0.9167 High Similarity NPC49168
0.9054 High Similarity NPC257191
0.9054 High Similarity NPC260301
0.9054 High Similarity NPC331618
0.9054 High Similarity NPC307336
0.9041 High Similarity NPC200243
0.9028 High Similarity NPC211009
0.9028 High Similarity NPC195489
0.8933 High Similarity NPC472342
0.8933 High Similarity NPC285761
0.8933 High Similarity NPC167037
0.8933 High Similarity NPC301707
0.8933 High Similarity NPC6978
0.8933 High Similarity NPC138621
0.8933 High Similarity NPC244385
0.8933 High Similarity NPC477817
0.8933 High Similarity NPC477819
0.8933 High Similarity NPC472501
0.8919 High Similarity NPC237460
0.8889 High Similarity NPC301226
0.8846 High Similarity NPC246956
0.8846 High Similarity NPC472743
0.8846 High Similarity NPC475726
0.8846 High Similarity NPC5280
0.8846 High Similarity NPC470929
0.8816 High Similarity NPC80530
0.8816 High Similarity NPC476316
0.8816 High Similarity NPC273410
0.88 High Similarity NPC138502
0.8784 High Similarity NPC103822
0.8784 High Similarity NPC144075
0.8734 High Similarity NPC264665
0.8734 High Similarity NPC74595
0.8734 High Similarity NPC474482
0.8734 High Similarity NPC475745
0.8714 High Similarity NPC142712
0.8701 High Similarity NPC13554
0.8701 High Similarity NPC236237
0.8701 High Similarity NPC71535
0.8701 High Similarity NPC322313
0.8701 High Similarity NPC78545
0.8701 High Similarity NPC102253
0.8684 High Similarity NPC98386
0.8684 High Similarity NPC65897
0.8684 High Similarity NPC472499
0.8684 High Similarity NPC158662
0.8684 High Similarity NPC230295
0.8684 High Similarity NPC196753
0.8684 High Similarity NPC302041
0.8684 High Similarity NPC472500
0.8684 High Similarity NPC253807
0.8684 High Similarity NPC85346
0.8667 High Similarity NPC38141
0.8667 High Similarity NPC189883
0.8667 High Similarity NPC73875
0.8649 High Similarity NPC476736
0.8642 High Similarity NPC269360
0.8642 High Similarity NPC264005
0.8625 High Similarity NPC294438
0.8625 High Similarity NPC264317
0.8625 High Similarity NPC292553
0.8608 High Similarity NPC85095
0.8608 High Similarity NPC211135
0.8608 High Similarity NPC216420
0.8608 High Similarity NPC113978
0.8608 High Similarity NPC232023
0.8592 High Similarity NPC48079
0.859 High Similarity NPC157655
0.8571 High Similarity NPC476737
0.8571 High Similarity NPC53744
0.8571 High Similarity NPC1319
0.8571 High Similarity NPC24504
0.8571 High Similarity NPC5604
0.8571 High Similarity NPC27243
0.8553 High Similarity NPC34177
0.8553 High Similarity NPC101475
0.8553 High Similarity NPC214570
0.8553 High Similarity NPC157996
0.8553 High Similarity NPC40394
0.8537 High Similarity NPC471900
0.8533 High Similarity NPC118508
0.8533 High Similarity NPC141071
0.8533 High Similarity NPC257347
0.8533 High Similarity NPC121744
0.8533 High Similarity NPC471723
0.8533 High Similarity NPC322353
0.8519 High Similarity NPC472738
0.8519 High Similarity NPC2783
0.8519 High Similarity NPC98236
0.8519 High Similarity NPC269396
0.8519 High Similarity NPC168231
0.8519 High Similarity NPC12774
0.8514 High Similarity NPC472506
0.85 High Similarity NPC255882
0.85 High Similarity NPC474233
0.85 High Similarity NPC209802
0.85 High Similarity NPC86238
0.8481 Intermediate Similarity NPC30166
0.8481 Intermediate Similarity NPC477599
0.8481 Intermediate Similarity NPC218616
0.8481 Intermediate Similarity NPC296701
0.8481 Intermediate Similarity NPC248886
0.8472 Intermediate Similarity NPC472741
0.8462 Intermediate Similarity NPC236112
0.8462 Intermediate Similarity NPC206735
0.8462 Intermediate Similarity NPC47149
0.8442 Intermediate Similarity NPC472502
0.8442 Intermediate Similarity NPC275910
0.8442 Intermediate Similarity NPC99168
0.8442 Intermediate Similarity NPC475
0.8442 Intermediate Similarity NPC470396
0.8442 Intermediate Similarity NPC300499
0.8442 Intermediate Similarity NPC312328
0.8442 Intermediate Similarity NPC474989
0.8442 Intermediate Similarity NPC22955
0.8434 Intermediate Similarity NPC213832
0.8434 Intermediate Similarity NPC57954
0.8421 Intermediate Similarity NPC202642
0.8421 Intermediate Similarity NPC46160
0.8421 Intermediate Similarity NPC30590
0.8421 Intermediate Similarity NPC321016
0.8421 Intermediate Similarity NPC27765
0.8421 Intermediate Similarity NPC321381
0.8421 Intermediate Similarity NPC129165
0.8421 Intermediate Similarity NPC122418
0.8421 Intermediate Similarity NPC107059
0.8421 Intermediate Similarity NPC300324
0.8421 Intermediate Similarity NPC290598
0.8421 Intermediate Similarity NPC240604
0.8421 Intermediate Similarity NPC120098
0.8421 Intermediate Similarity NPC265328
0.8421 Intermediate Similarity NPC134330
0.8415 Intermediate Similarity NPC4643
0.8415 Intermediate Similarity NPC57469
0.8415 Intermediate Similarity NPC33768
0.84 Intermediate Similarity NPC100334
0.8378 Intermediate Similarity NPC164045
0.8375 Intermediate Similarity NPC477818
0.8375 Intermediate Similarity NPC110778
0.8375 Intermediate Similarity NPC207013
0.8356 Intermediate Similarity NPC254037
0.8356 Intermediate Similarity NPC210323
0.8356 Intermediate Similarity NPC129829
0.8354 Intermediate Similarity NPC242350
0.8354 Intermediate Similarity NPC470383
0.8354 Intermediate Similarity NPC474531
0.8333 Intermediate Similarity NPC473230
0.8333 Intermediate Similarity NPC30986
0.8333 Intermediate Similarity NPC472463
0.8333 Intermediate Similarity NPC475884
0.8333 Intermediate Similarity NPC305835
0.8333 Intermediate Similarity NPC209430
0.8333 Intermediate Similarity NPC291379
0.8333 Intermediate Similarity NPC201459
0.8333 Intermediate Similarity NPC155924
0.8313 Intermediate Similarity NPC16377
0.8313 Intermediate Similarity NPC472739
0.8313 Intermediate Similarity NPC474719
0.8312 Intermediate Similarity NPC318495
0.8312 Intermediate Similarity NPC155986
0.8312 Intermediate Similarity NPC472805

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC278091 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
0.8701 High Similarity NPD7525 Registered
0.8625 High Similarity NPD7520 Clinical (unspecified phase)
0.8571 High Similarity NPD7645 Phase 2
0.8289 Intermediate Similarity NPD6942 Approved
0.8289 Intermediate Similarity NPD7339 Approved
0.8108 Intermediate Similarity NPD4267 Clinical (unspecified phase)
0.7949 Intermediate Similarity NPD3701 Clinical (unspecified phase)
0.7816 Intermediate Similarity NPD8034 Phase 2
0.7816 Intermediate Similarity NPD8035 Phase 2
0.7692 Intermediate Similarity NPD6924 Approved
0.7692 Intermediate Similarity NPD6926 Approved
0.7619 Intermediate Similarity NPD4786 Approved
0.7586 Intermediate Similarity NPD5328 Approved
0.7532 Intermediate Similarity NPD4787 Phase 1
0.75 Intermediate Similarity NPD4788 Approved
0.75 Intermediate Similarity NPD6933 Approved
0.7442 Intermediate Similarity NPD3618 Phase 1
0.7439 Intermediate Similarity NPD6929 Approved
0.7436 Intermediate Similarity NPD7150 Approved
0.7436 Intermediate Similarity NPD4243 Approved
0.7436 Intermediate Similarity NPD7151 Approved
0.7436 Intermediate Similarity NPD4809 Clinical (unspecified phase)
0.7436 Intermediate Similarity NPD7152 Approved
0.7436 Intermediate Similarity NPD4808 Clinical (unspecified phase)
0.7416 Intermediate Similarity NPD6079 Approved
0.7403 Intermediate Similarity NPD6923 Approved
0.7403 Intermediate Similarity NPD6922 Approved
0.7381 Intermediate Similarity NPD3667 Approved
0.7349 Intermediate Similarity NPD6931 Approved
0.7349 Intermediate Similarity NPD4748 Discontinued
0.7349 Intermediate Similarity NPD6930 Phase 2
0.7308 Intermediate Similarity NPD7143 Approved
0.7308 Intermediate Similarity NPD7144 Approved
0.7284 Intermediate Similarity NPD6117 Approved
0.725 Intermediate Similarity NPD6113 Clinical (unspecified phase)
0.725 Intermediate Similarity NPD4785 Approved
0.725 Intermediate Similarity NPD4784 Approved
0.7222 Intermediate Similarity NPD7515 Phase 2
0.7195 Intermediate Similarity NPD6932 Approved
0.7195 Intermediate Similarity NPD5776 Phase 2
0.7195 Intermediate Similarity NPD6925 Approved
0.7195 Intermediate Similarity NPD6116 Phase 1
0.7179 Intermediate Similarity NPD3700 Clinical (unspecified phase)
0.7179 Intermediate Similarity NPD3699 Clinical (unspecified phase)
0.7159 Intermediate Similarity NPD4751 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD4202 Approved
0.7143 Intermediate Similarity NPD7509 Discontinued
0.7108 Intermediate Similarity NPD6114 Approved
0.7108 Intermediate Similarity NPD6118 Approved
0.7108 Intermediate Similarity NPD6697 Approved
0.7108 Intermediate Similarity NPD6115 Approved
0.7108 Intermediate Similarity NPD7145 Approved
0.7093 Intermediate Similarity NPD6695 Phase 3
0.7024 Intermediate Similarity NPD6683 Phase 2
0.7021 Intermediate Similarity NPD4755 Approved
0.7011 Intermediate Similarity NPD3666 Approved
0.7011 Intermediate Similarity NPD3133 Approved
0.7011 Intermediate Similarity NPD7338 Clinical (unspecified phase)
0.7011 Intermediate Similarity NPD3665 Phase 1
0.6951 Remote Similarity NPD5275 Approved
0.6951 Remote Similarity NPD3703 Phase 2
0.6951 Remote Similarity NPD4190 Phase 3
0.6947 Remote Similarity NPD7638 Approved
0.6941 Remote Similarity NPD6928 Phase 2
0.6941 Remote Similarity NPD7514 Phase 3
0.6932 Remote Similarity NPD6893 Approved
0.6915 Remote Similarity NPD5222 Approved
0.6915 Remote Similarity NPD5220 Clinical (unspecified phase)
0.6915 Remote Similarity NPD4697 Phase 3
0.6915 Remote Similarity NPD5221 Approved
0.6882 Remote Similarity NPD7748 Approved
0.6875 Remote Similarity NPD4700 Approved
0.6875 Remote Similarity NPD5286 Approved
0.6875 Remote Similarity NPD4245 Approved
0.6875 Remote Similarity NPD5285 Approved
0.6875 Remote Similarity NPD4789 Approved
0.6875 Remote Similarity NPD7639 Approved
0.6875 Remote Similarity NPD4696 Approved
0.6875 Remote Similarity NPD7640 Approved
0.6875 Remote Similarity NPD4244 Approved
0.686 Remote Similarity NPD6902 Approved
0.6842 Remote Similarity NPD5173 Approved
0.6835 Remote Similarity NPD5360 Phase 3
0.6835 Remote Similarity NPD5361 Clinical (unspecified phase)
0.6824 Remote Similarity NPD4195 Approved
0.6813 Remote Similarity NPD4753 Phase 2
0.6778 Remote Similarity NPD7750 Discontinued
0.6778 Remote Similarity NPD7524 Approved
0.6774 Remote Similarity NPD6399 Phase 3
0.675 Remote Similarity NPD3698 Phase 2
0.6744 Remote Similarity NPD7332 Phase 2
0.6735 Remote Similarity NPD5226 Approved
0.6735 Remote Similarity NPD5224 Approved
0.6735 Remote Similarity NPD5225 Approved
0.6735 Remote Similarity NPD4633 Approved
0.6735 Remote Similarity NPD5211 Phase 2
0.6706 Remote Similarity NPD7322 Clinical (unspecified phase)
0.67 Remote Similarity NPD5739 Approved
0.67 Remote Similarity NPD6402 Approved
0.67 Remote Similarity NPD7128 Approved
0.67 Remote Similarity NPD6675 Approved
0.6667 Remote Similarity NPD5279 Phase 3
0.6667 Remote Similarity NPD7902 Approved
0.6667 Remote Similarity NPD3171 Clinical (unspecified phase)
0.6667 Remote Similarity NPD5175 Approved
0.6667 Remote Similarity NPD6898 Phase 1
0.6667 Remote Similarity NPD5174 Approved
0.6633 Remote Similarity NPD5223 Approved
0.6629 Remote Similarity NPD3668 Phase 3
0.66 Remote Similarity NPD5141 Approved
0.6598 Remote Similarity NPD5290 Discontinued
0.6591 Remote Similarity NPD4223 Phase 3
0.6591 Remote Similarity NPD4221 Approved
0.6569 Remote Similarity NPD7320 Approved
0.6569 Remote Similarity NPD6881 Approved
0.6569 Remote Similarity NPD6899 Approved
0.6556 Remote Similarity NPD5329 Approved
0.6548 Remote Similarity NPD8264 Approved
0.6535 Remote Similarity NPD4768 Approved
0.6535 Remote Similarity NPD4767 Approved
0.6522 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6512 Remote Similarity NPD3671 Phase 1
0.6505 Remote Similarity NPD6372 Approved
0.6505 Remote Similarity NPD6373 Approved
0.65 Remote Similarity NPD4754 Approved
0.6495 Remote Similarity NPD6084 Phase 2
0.6495 Remote Similarity NPD6083 Phase 2
0.6489 Remote Similarity NPD7087 Discontinued
0.6471 Remote Similarity NPD5697 Approved
0.6471 Remote Similarity NPD5701 Approved
0.6458 Remote Similarity NPD5210 Approved
0.6458 Remote Similarity NPD4629 Approved
0.6444 Remote Similarity NPD4197 Approved
0.6442 Remote Similarity NPD7290 Approved
0.6442 Remote Similarity NPD6883 Approved
0.6442 Remote Similarity NPD7102 Approved
0.642 Remote Similarity NPD6705 Phase 1
0.6408 Remote Similarity NPD4729 Approved
0.6408 Remote Similarity NPD5128 Approved
0.6408 Remote Similarity NPD4730 Approved
0.64 Remote Similarity NPD7632 Discontinued
0.6386 Remote Similarity NPD4758 Discontinued
0.6381 Remote Similarity NPD6650 Approved
0.6381 Remote Similarity NPD8130 Phase 1
0.6381 Remote Similarity NPD6649 Approved
0.6381 Remote Similarity NPD6847 Approved
0.6381 Remote Similarity NPD6869 Approved
0.6381 Remote Similarity NPD6617 Approved
0.6354 Remote Similarity NPD7900 Approved
0.6354 Remote Similarity NPD7901 Clinical (unspecified phase)
0.6346 Remote Similarity NPD6013 Approved
0.6346 Remote Similarity NPD6014 Approved
0.6346 Remote Similarity NPD6012 Approved
0.633 Remote Similarity NPD7328 Approved
0.633 Remote Similarity NPD7327 Approved
0.6322 Remote Similarity NPD3617 Approved
0.6321 Remote Similarity NPD8297 Approved
0.6321 Remote Similarity NPD6882 Approved
0.6304 Remote Similarity NPD4689 Approved
0.6304 Remote Similarity NPD4688 Approved
0.6304 Remote Similarity NPD4693 Phase 3
0.6304 Remote Similarity NPD6684 Approved
0.6304 Remote Similarity NPD5205 Approved
0.6304 Remote Similarity NPD4690 Approved
0.6304 Remote Similarity NPD7521 Approved
0.6304 Remote Similarity NPD7334 Approved
0.6304 Remote Similarity NPD7146 Approved
0.6304 Remote Similarity NPD5330 Approved
0.6304 Remote Similarity NPD6409 Approved
0.6304 Remote Similarity NPD4138 Approved
0.6304 Remote Similarity NPD3574 Clinical (unspecified phase)
0.63 Remote Similarity NPD4159 Approved
0.6286 Remote Similarity NPD5247 Approved
0.6286 Remote Similarity NPD5249 Phase 3
0.6286 Remote Similarity NPD5248 Approved
0.6286 Remote Similarity NPD4634 Approved
0.6286 Remote Similarity NPD5251 Approved
0.6286 Remote Similarity NPD5250 Approved
0.6277 Remote Similarity NPD6051 Approved
0.6273 Remote Similarity NPD7516 Approved
0.6262 Remote Similarity NPD8133 Approved
0.625 Remote Similarity NPD6011 Approved
0.625 Remote Similarity NPD8171 Discontinued
0.625 Remote Similarity NPD5168 Approved
0.6239 Remote Similarity NPD7115 Discovery
0.6226 Remote Similarity NPD5217 Approved
0.6226 Remote Similarity NPD6401 Clinical (unspecified phase)
0.6226 Remote Similarity NPD5215 Approved
0.6226 Remote Similarity NPD5216 Approved
0.6216 Remote Similarity NPD8377 Approved
0.6216 Remote Similarity NPD8294 Approved
0.6211 Remote Similarity NPD6701 Clinical (unspecified phase)
0.6211 Remote Similarity NPD6700 Approved
0.619 Remote Similarity NPD6081 Approved
0.6173 Remote Similarity NPD4224 Phase 2
0.617 Remote Similarity NPD6903 Approved
0.617 Remote Similarity NPD5737 Approved
0.617 Remote Similarity NPD4723 Approved
0.617 Remote Similarity NPD6672 Approved
0.617 Remote Similarity NPD4722 Approved

Structure

External Identifiers

PubChem CID   14605681
ChEMBL   CHEMBL3815071
ZINC  

Physicochemical Properties

Molecular Weight:  458.38
ALogP:  1.0499
MLogP:  4.43
XLogP:  9.011
# Rotatable Bonds:  11
Polar Surface Area:  60.69
# H-Bond Aceptor:  3
# H-Bond Donor:  3
# Rings:  5
# Heavy Atoms:  33

Download Data

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