Natural Product: NPC53385

Natural Product ID:  NPC53385
Common Name:   28-Hydroxyisoiguesterin
IUPAC Name:   (6aS,6bS,8aS,12aS,14aR)-3-hydroxy-8a-(hydroxymethyl)-4,6a,6b,14a-tetramethyl-11-methylidene-7,8,9,10,12,12a,13,14-octahydropicen-2-one
Synonyms:   28-Hydroxyisoiguesterin
Molecular Formula:   C28H36O3
Standard InCHIKey:  BWCNPEZRVXBNNU-HKFGFSCZSA-N
Standard InCHI:  InChI=1S/C28H36O3/c1-17-8-9-28(16-29)13-12-26(4)22-7-6-19-18(2)24(31)21(30)15-20(19)25(22,3)10-11-27(26,5)23(28)14-17/h6-7,15,23,29,31H,1,8-14,16H2,2-5H3/t23-,25-,26+,27-,28+/m0/s1
Canonical SMILES:  OC[C@@]12CCC(=C)C[C@H]2[C@]2([C@@](CC1)(C)C1=CC=C3C(=CC(=O)C(=C3C)O)[C@@]1(CC2)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
NPO26085 Salacia kraussii Species Celastraceae Eukaryota PMID[9644053]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT139 Cell Line HT-29 Homo sapiens IC50 = 6.06 ug/ml 25946116
NPT485 Organism Plasmodium falciparum (isolate K1 / Thailand) Plasmodium falciparum K1 IC50 = 0.1144 ug/ml 17938183
NPT6 Organism Plasmodium falciparum Plasmodium falciparum IC50 = 0.1402 ug/ml Open TG-GATES in vivo data: Biochemistry

  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 NPC53385 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
0.9872 High Similarity NPC291999
0.9872 High Similarity NPC309309
0.8974 High Similarity NPC112680
0.8851 High Similarity NPC211230
0.875 High Similarity NPC474882
0.8734 High Similarity NPC292589
0.8675 High Similarity NPC53733
0.8636 High Similarity NPC263780
0.8539 High Similarity NPC23170
0.8539 High Similarity NPC474328
0.8523 High Similarity NPC470036
0.8523 High Similarity NPC174167
0.8506 High Similarity NPC112454
0.8506 High Similarity NPC65615
0.8506 High Similarity NPC68148
0.8471 Intermediate Similarity NPC33881
0.8434 Intermediate Similarity NPC121984
0.8333 Intermediate Similarity NPC310989
0.8313 Intermediate Similarity NPC2482
0.8313 Intermediate Similarity NPC287063
0.8293 Intermediate Similarity NPC72507
0.8242 Intermediate Similarity NPC777
0.8235 Intermediate Similarity NPC82538
0.8235 Intermediate Similarity NPC237795
0.8214 Intermediate Similarity NPC3915
0.8214 Intermediate Similarity NPC225515
0.8214 Intermediate Similarity NPC475863
0.814 Intermediate Similarity NPC180834
0.8118 Intermediate Similarity NPC103486
0.8095 Intermediate Similarity NPC18955
0.8095 Intermediate Similarity NPC108955
0.8077 Intermediate Similarity NPC216460
0.8072 Intermediate Similarity NPC99168
0.8072 Intermediate Similarity NPC470396
0.8072 Intermediate Similarity NPC474989
0.8072 Intermediate Similarity NPC22955
0.8049 Intermediate Similarity NPC106364
0.8046 Intermediate Similarity NPC469993
0.8 Intermediate Similarity NPC6663
0.8 Intermediate Similarity NPC55869
0.8 Intermediate Similarity NPC470034
0.7978 Intermediate Similarity NPC230387
0.7976 Intermediate Similarity NPC27817
0.7976 Intermediate Similarity NPC291379
0.7976 Intermediate Similarity NPC53744
0.7955 Intermediate Similarity NPC94666
0.7952 Intermediate Similarity NPC40394
0.7952 Intermediate Similarity NPC101475
0.7952 Intermediate Similarity NPC34177
0.7952 Intermediate Similarity NPC157996
0.7938 Intermediate Similarity NPC213366
0.7931 Intermediate Similarity NPC237712
0.7931 Intermediate Similarity NPC472265
0.7931 Intermediate Similarity NPC33913
0.7912 Intermediate Similarity NPC301244
0.7901 Intermediate Similarity NPC471799
0.7889 Intermediate Similarity NPC477973
0.7865 Intermediate Similarity NPC93778
0.7865 Intermediate Similarity NPC71507
0.7865 Intermediate Similarity NPC73064
0.7865 Intermediate Similarity NPC470523
0.7857 Intermediate Similarity NPC253807
0.7857 Intermediate Similarity NPC158662
0.7857 Intermediate Similarity NPC189485
0.7857 Intermediate Similarity NPC98386
0.7857 Intermediate Similarity NPC300499
0.7857 Intermediate Similarity NPC196753
0.7857 Intermediate Similarity NPC230295
0.7849 Intermediate Similarity NPC147232
0.7848 Intermediate Similarity NPC32055
0.7841 Intermediate Similarity NPC263997
0.7841 Intermediate Similarity NPC241512
0.7841 Intermediate Similarity NPC32037
0.7841 Intermediate Similarity NPC474537
0.7841 Intermediate Similarity NPC8518
0.7841 Intermediate Similarity NPC133954
0.7841 Intermediate Similarity NPC133652
0.7841 Intermediate Similarity NPC132228
0.7841 Intermediate Similarity NPC274724
0.7841 Intermediate Similarity NPC6185
0.7841 Intermediate Similarity NPC469948
0.7831 Intermediate Similarity NPC92080
0.7831 Intermediate Similarity NPC122418
0.7831 Intermediate Similarity NPC265328
0.7831 Intermediate Similarity NPC290598
0.7831 Intermediate Similarity NPC27765
0.7831 Intermediate Similarity NPC30590
0.7831 Intermediate Similarity NPC120098
0.7816 Intermediate Similarity NPC70834
0.7816 Intermediate Similarity NPC307258
0.7805 Intermediate Similarity NPC100334
0.7805 Intermediate Similarity NPC471797
0.7802 Intermediate Similarity NPC46441
0.7802 Intermediate Similarity NPC129913
0.7802 Intermediate Similarity NPC212369
0.7791 Intermediate Similarity NPC6434
0.7791 Intermediate Similarity NPC471898
0.7778 Intermediate Similarity NPC474511
0.7778 Intermediate Similarity NPC242001
0.7778 Intermediate Similarity NPC472802
0.7778 Intermediate Similarity NPC470524
0.7778 Intermediate Similarity NPC1753
0.7778 Intermediate Similarity NPC206060
0.7765 Intermediate Similarity NPC474113
0.7753 Intermediate Similarity NPC327115
0.7753 Intermediate Similarity NPC213412
0.7753 Intermediate Similarity NPC51014
0.7753 Intermediate Similarity NPC145879
0.7753 Intermediate Similarity NPC158393
0.7753 Intermediate Similarity NPC475862
0.7753 Intermediate Similarity NPC31564
0.7753 Intermediate Similarity NPC474778
0.7753 Intermediate Similarity NPC74363
0.7753 Intermediate Similarity NPC474732
0.7753 Intermediate Similarity NPC474733
0.7742 Intermediate Similarity NPC80365
0.7738 Intermediate Similarity NPC90979
0.7738 Intermediate Similarity NPC472805
0.7727 Intermediate Similarity NPC96095
0.7727 Intermediate Similarity NPC214043
0.7727 Intermediate Similarity NPC85774
0.7727 Intermediate Similarity NPC473246
0.7722 Intermediate Similarity NPC197805
0.7717 Intermediate Similarity NPC474525
0.7717 Intermediate Similarity NPC145067
0.7717 Intermediate Similarity NPC233455
0.7717 Intermediate Similarity NPC4036
0.7717 Intermediate Similarity NPC158030
0.7717 Intermediate Similarity NPC65120
0.7711 Intermediate Similarity NPC471468
0.7711 Intermediate Similarity NPC34700
0.7711 Intermediate Similarity NPC138374
0.7701 Intermediate Similarity NPC48362
0.7701 Intermediate Similarity NPC69101
0.7701 Intermediate Similarity NPC251779
0.7692 Intermediate Similarity NPC95246
0.7692 Intermediate Similarity NPC161751
0.7692 Intermediate Similarity NPC184663
0.7692 Intermediate Similarity NPC474972
0.7692 Intermediate Similarity NPC210216
0.7692 Intermediate Similarity NPC474686
0.7674 Intermediate Similarity NPC295131
0.7667 Intermediate Similarity NPC158141
0.7667 Intermediate Similarity NPC173089
0.7667 Intermediate Similarity NPC475772
0.7667 Intermediate Similarity NPC475740
0.7667 Intermediate Similarity NPC136548
0.7667 Intermediate Similarity NPC58063
0.766 Intermediate Similarity NPC280725
0.7654 Intermediate Similarity NPC145498
0.7647 Intermediate Similarity NPC76931
0.7647 Intermediate Similarity NPC18603
0.7647 Intermediate Similarity NPC30321
0.7647 Intermediate Similarity NPC307965
0.764 Intermediate Similarity NPC191965
0.764 Intermediate Similarity NPC474680
0.7634 Intermediate Similarity NPC250575
0.7634 Intermediate Similarity NPC295643
0.7634 Intermediate Similarity NPC12722
0.7634 Intermediate Similarity NPC214756
0.7634 Intermediate Similarity NPC272075
0.7625 Intermediate Similarity NPC208999
0.7619 Intermediate Similarity NPC250621
0.7619 Intermediate Similarity NPC106432
0.7619 Intermediate Similarity NPC321381
0.7619 Intermediate Similarity NPC321016
0.7619 Intermediate Similarity NPC110725
0.7619 Intermediate Similarity NPC107059
0.7619 Intermediate Similarity NPC470525
0.7614 Intermediate Similarity NPC105803
0.7609 Intermediate Similarity NPC252737
0.7609 Intermediate Similarity NPC38952
0.7609 Intermediate Similarity NPC85173
0.7595 Intermediate Similarity NPC476039
0.7595 Intermediate Similarity NPC286669
0.7595 Intermediate Similarity NPC149680
0.7595 Intermediate Similarity NPC222366
0.759 Intermediate Similarity NPC477138
0.759 Intermediate Similarity NPC243342
0.7586 Intermediate Similarity NPC474085
0.7586 Intermediate Similarity NPC162632
0.7586 Intermediate Similarity NPC274050
0.7586 Intermediate Similarity NPC263272
0.7586 Intermediate Similarity NPC242350
0.7586 Intermediate Similarity NPC116202
0.7586 Intermediate Similarity NPC116797
0.7586 Intermediate Similarity NPC267691
0.7586 Intermediate Similarity NPC142244
0.7582 Intermediate Similarity NPC7280
0.7582 Intermediate Similarity NPC229612
0.7582 Intermediate Similarity NPC181225
0.7582 Intermediate Similarity NPC474512
0.7582 Intermediate Similarity NPC471722
0.7582 Intermediate Similarity NPC470629
0.7582 Intermediate Similarity NPC474474
0.7582 Intermediate Similarity NPC290690
0.7582 Intermediate Similarity NPC473242
0.7582 Intermediate Similarity NPC17733
0.7579 Intermediate Similarity NPC62516
0.7579 Intermediate Similarity NPC157113

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC53385 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
0.8506 High Similarity NPD7285 Clinical (unspecified phase)
0.7955 Intermediate Similarity NPD5279 Phase 3
0.7882 Intermediate Similarity NPD4695 Discontinued
0.7765 Intermediate Similarity NPD7645 Phase 2
0.7717 Intermediate Similarity NPD7515 Phase 2
0.7556 Intermediate Similarity NPD5280 Approved
0.7556 Intermediate Similarity NPD4694 Approved
0.7528 Intermediate Similarity NPD4786 Approved
0.7528 Intermediate Similarity NPD3666 Approved
0.7528 Intermediate Similarity NPD3665 Phase 1
0.7528 Intermediate Similarity NPD3133 Approved
0.75 Intermediate Similarity NPD3667 Approved
0.75 Intermediate Similarity NPD4753 Phase 2
0.75 Intermediate Similarity NPD6942 Approved
0.75 Intermediate Similarity NPD7339 Approved
0.7444 Intermediate Similarity NPD5329 Approved
0.7442 Intermediate Similarity NPD3617 Approved
0.7412 Intermediate Similarity NPD3701 Clinical (unspecified phase)
0.7381 Intermediate Similarity NPD6924 Approved
0.7381 Intermediate Similarity NPD6926 Approved
0.7368 Intermediate Similarity NPD7748 Approved
0.7363 Intermediate Similarity NPD3618 Phase 1
0.7356 Intermediate Similarity NPD4195 Approved
0.7333 Intermediate Similarity NPD4197 Approved
0.7312 Intermediate Similarity NPD5328 Approved
0.7273 Intermediate Similarity NPD8259 Clinical (unspecified phase)
0.7209 Intermediate Similarity NPD6933 Approved
0.7174 Intermediate Similarity NPD5690 Phase 2
0.7158 Intermediate Similarity NPD6079 Approved
0.7143 Intermediate Similarity NPD6083 Phase 2
0.7143 Intermediate Similarity NPD7902 Approved
0.7143 Intermediate Similarity NPD6084 Phase 2
0.7113 Intermediate Similarity NPD4629 Approved
0.7113 Intermediate Similarity NPD5210 Approved
0.7111 Intermediate Similarity NPD4221 Approved
0.7111 Intermediate Similarity NPD4223 Phase 3
0.7108 Intermediate Similarity NPD6922 Approved
0.7108 Intermediate Similarity NPD6923 Approved
0.7093 Intermediate Similarity NPD8264 Approved
0.7079 Intermediate Similarity NPD7525 Registered
0.7041 Intermediate Similarity NPD4697 Phase 3
0.7041 Intermediate Similarity NPD5220 Clinical (unspecified phase)
0.7041 Intermediate Similarity NPD5222 Approved
0.7041 Intermediate Similarity NPD5221 Approved
0.7033 Intermediate Similarity NPD4788 Approved
0.7024 Intermediate Similarity NPD7144 Approved
0.7024 Intermediate Similarity NPD7143 Approved
0.7021 Intermediate Similarity NPD7513 Clinical (unspecified phase)
0.7021 Intermediate Similarity NPD6672 Approved
0.7021 Intermediate Similarity NPD5737 Approved
0.6977 Remote Similarity NPD4785 Approved
0.6977 Remote Similarity NPD4784 Approved
0.697 Remote Similarity NPD4755 Approved
0.697 Remote Similarity NPD5173 Approved
0.6966 Remote Similarity NPD6929 Approved
0.6941 Remote Similarity NPD7152 Approved
0.6941 Remote Similarity NPD4243 Approved
0.6941 Remote Similarity NPD7151 Approved
0.6941 Remote Similarity NPD7150 Approved
0.6939 Remote Similarity NPD5695 Phase 3
0.6907 Remote Similarity NPD4202 Approved
0.6907 Remote Similarity NPD5133 Approved
0.6889 Remote Similarity NPD6931 Approved
0.6889 Remote Similarity NPD6930 Phase 2
0.6889 Remote Similarity NPD7509 Discontinued
0.6882 Remote Similarity NPD1696 Phase 3
0.6869 Remote Similarity NPD7614 Phase 1
0.6837 Remote Similarity NPD7901 Clinical (unspecified phase)
0.6837 Remote Similarity NPD7900 Approved
0.6832 Remote Similarity NPD4696 Approved
0.6832 Remote Similarity NPD5285 Approved
0.6832 Remote Similarity NPD5286 Approved
0.6832 Remote Similarity NPD4700 Approved
0.6809 Remote Similarity NPD7146 Approved
0.6809 Remote Similarity NPD4138 Approved
0.6809 Remote Similarity NPD4689 Approved
0.6809 Remote Similarity NPD7521 Approved
0.6809 Remote Similarity NPD4519 Discontinued
0.6809 Remote Similarity NPD4693 Phase 3
0.6809 Remote Similarity NPD6409 Approved
0.6809 Remote Similarity NPD7334 Approved
0.6809 Remote Similarity NPD5330 Approved
0.6809 Remote Similarity NPD4688 Approved
0.6809 Remote Similarity NPD4623 Approved
0.6809 Remote Similarity NPD6684 Approved
0.6809 Remote Similarity NPD5205 Approved
0.6809 Remote Similarity NPD4690 Approved
0.6804 Remote Similarity NPD5284 Approved
0.6804 Remote Similarity NPD5281 Approved
0.6804 Remote Similarity NPD6050 Approved
0.6782 Remote Similarity NPD5733 Approved
0.6774 Remote Similarity NPD3668 Phase 3
0.6765 Remote Similarity NPD5223 Approved
0.6742 Remote Similarity NPD6925 Approved
0.6742 Remote Similarity NPD5776 Phase 2
0.6742 Remote Similarity NPD6932 Approved
0.6735 Remote Similarity NPD6399 Phase 3
0.6733 Remote Similarity NPD5696 Approved
0.6701 Remote Similarity NPD4096 Approved
0.6701 Remote Similarity NPD5692 Phase 3
0.6699 Remote Similarity NPD5225 Approved
0.6699 Remote Similarity NPD5211 Phase 2
0.6699 Remote Similarity NPD5224 Approved
0.6699 Remote Similarity NPD5226 Approved
0.6699 Remote Similarity NPD4633 Approved
0.6667 Remote Similarity NPD7145 Approved
0.6667 Remote Similarity NPD6402 Approved
0.6667 Remote Similarity NPD6903 Approved
0.6667 Remote Similarity NPD6675 Approved
0.6667 Remote Similarity NPD7128 Approved
0.6667 Remote Similarity NPD5739 Approved
0.6667 Remote Similarity NPD7322 Clinical (unspecified phase)
0.6667 Remote Similarity NPD6695 Phase 3
0.6667 Remote Similarity NPD4518 Approved
0.6635 Remote Similarity NPD5175 Approved
0.6635 Remote Similarity NPD5174 Approved
0.6635 Remote Similarity NPD4754 Approved
0.6633 Remote Similarity NPD5694 Approved
0.6633 Remote Similarity NPD6411 Approved
0.6632 Remote Similarity NPD3574 Clinical (unspecified phase)
0.6598 Remote Similarity NPD6673 Approved
0.6598 Remote Similarity NPD6080 Approved
0.6598 Remote Similarity NPD6904 Approved
0.6596 Remote Similarity NPD7338 Clinical (unspecified phase)
0.6593 Remote Similarity NPD6683 Phase 2
0.6591 Remote Similarity NPD4058 Approved
0.6591 Remote Similarity NPD4687 Approved
0.6571 Remote Similarity NPD5141 Approved
0.6569 Remote Similarity NPD7638 Approved
0.6569 Remote Similarity NPD5290 Discontinued
0.6562 Remote Similarity NPD4751 Clinical (unspecified phase)
0.6552 Remote Similarity NPD5276 Approved
0.6542 Remote Similarity NPD6899 Approved
0.6542 Remote Similarity NPD7320 Approved
0.6542 Remote Similarity NPD6881 Approved
0.6535 Remote Similarity NPD7732 Phase 3
0.6526 Remote Similarity NPD7520 Clinical (unspecified phase)
0.6526 Remote Similarity NPD6893 Approved
0.6522 Remote Similarity NPD7332 Phase 2
0.6522 Remote Similarity NPD7514 Phase 3
0.6522 Remote Similarity NPD4748 Discontinued
0.6517 Remote Similarity NPD4190 Phase 3
0.6517 Remote Similarity NPD5275 Approved
0.6512 Remote Similarity NPD4137 Phase 3
0.6509 Remote Similarity NPD4768 Approved
0.6509 Remote Similarity NPD4767 Approved
0.6505 Remote Similarity NPD7639 Approved
0.6505 Remote Similarity NPD7640 Approved
0.6481 Remote Similarity NPD6373 Approved
0.6481 Remote Similarity NPD6372 Approved
0.6458 Remote Similarity NPD6098 Approved
0.6452 Remote Similarity NPD6902 Approved
0.6452 Remote Similarity NPD8028 Phase 2
0.6452 Remote Similarity NPD6898 Phase 1
0.6449 Remote Similarity NPD5697 Approved
0.6449 Remote Similarity NPD5701 Approved
0.6449 Remote Similarity NPD6412 Phase 2
0.6437 Remote Similarity NPD4691 Approved
0.6437 Remote Similarity NPD4789 Approved
0.6437 Remote Similarity NPD4747 Approved
0.6429 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6429 Remote Similarity NPD6101 Approved
0.6422 Remote Similarity NPD6883 Approved
0.6422 Remote Similarity NPD7290 Approved
0.6422 Remote Similarity NPD7102 Approved
0.6392 Remote Similarity NPD7750 Discontinued
0.6392 Remote Similarity NPD7524 Approved
0.6392 Remote Similarity NPD3573 Approved
0.6389 Remote Similarity NPD5128 Approved
0.6389 Remote Similarity NPD5168 Approved
0.6389 Remote Similarity NPD6011 Approved
0.6389 Remote Similarity NPD4730 Approved
0.6389 Remote Similarity NPD4729 Approved
0.6364 Remote Similarity NPD5207 Approved
0.6364 Remote Similarity NPD6650 Approved
0.6364 Remote Similarity NPD6649 Approved
0.6364 Remote Similarity NPD6869 Approved
0.6364 Remote Similarity NPD6847 Approved
0.6364 Remote Similarity NPD6617 Approved
0.6364 Remote Similarity NPD8130 Phase 1
0.6364 Remote Similarity NPD6401 Clinical (unspecified phase)
0.633 Remote Similarity NPD6012 Approved
0.633 Remote Similarity NPD6014 Approved
0.633 Remote Similarity NPD6013 Approved
0.6306 Remote Similarity NPD8297 Approved
0.6306 Remote Similarity NPD6882 Approved
0.63 Remote Similarity NPD5693 Phase 1
0.6277 Remote Similarity NPD4139 Approved
0.6277 Remote Similarity NPD4692 Approved
0.6275 Remote Similarity NPD5654 Approved
0.6273 Remote Similarity NPD5248 Approved
0.6273 Remote Similarity NPD5169 Approved
0.6273 Remote Similarity NPD5247 Approved
0.6273 Remote Similarity NPD5250 Approved
0.6273 Remote Similarity NPD4634 Approved
0.6273 Remote Similarity NPD5134 Clinical (unspecified phase)
0.6273 Remote Similarity NPD5251 Approved
0.6273 Remote Similarity NPD5249 Phase 3
0.6273 Remote Similarity NPD5135 Approved
0.6226 Remote Similarity NPD5091 Approved

Structure

External Identifiers

PubChem CID   10622044
ChEMBL   CHEMBL515947
ZINC  

Physicochemical Properties

Molecular Weight:  420.27
ALogP:  1.8719
MLogP:  4.21
XLogP:  6.764
# Rotatable Bonds:  7
Polar Surface Area:  57.53
# H-Bond Aceptor:  3
# H-Bond Donor:  2
# Rings:  5
# Heavy Atoms:  31

Download Data

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General Info & Identifiers & Properties  
Structure MOL file  
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Biological Activities  
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