Natural Product: NPC309309

Natural Product ID:  NPC309309
Common Name:   20-Epi-Isoiguesterinol
IUPAC Name:   (6aS,6bS,8aR,11S,12aR,14aR)-3-hydroxy-11-(hydroxymethyl)-4,6a,6b,8a,14a-pentamethyl-8,9,10,11,12,12a,13,14-octahydro-7H-picen-2-one
Synonyms:   20-Epi-Isoiguesterinol
Molecular Formula:   C28H38O3
Standard InCHIKey:  RRKSDDREVOXSJD-TXARQUJHSA-N
Standard InCHI:  InChI=1S/C28H38O3/c1-17-19-6-7-22-26(3,20(19)15-21(30)24(17)31)11-13-28(5)23-14-18(16-29)8-9-25(23,2)10-12-27(22,28)4/h6-7,15,18,23,29,31H,8-14,16H2,1-5H3/t18-,23+,25+,26-,27+,28-/m0/s1
Canonical SMILES:  OC[C@H]1CC[C@]2([C@@H](C1)[C@]1(C)CC[C@@]3(C(=CC=C4C3=CC(=O)C(=C4C)O)[C@]1(CC2)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
NPO26927 Salacia madagascariensis Species Celastraceae Eukaryota PMID[15730255]
NPO26927 Salacia madagascariensis Species Celastraceae Eukaryota Root PMID[15730255]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT633 Organism Leishmania donovani Leishmania donovani IC50 = 0.027 ug/ml 15730255
NPT16 Organism Staphylococcus aureus Staphylococcus aureus IC50 = 0.65 ug/ml 15730255
NPT16 Organism Staphylococcus aureus Staphylococcus aureus IC50 = 0.7 ug/ml 15730255
NPT86 Organism Mycobacterium intracellulare Mycobacterium intracellulare IC50 = 15 ug/ml 15730255
NPT6 Organism Plasmodium falciparum Plasmodium falciparum IC50 = 0.068 ug/ml 15730255
NPT189 Cell Line Vero Chlorocebus aethiops IC50 = 2.1 ug/ml 15730255
NPT633 Organism Leishmania donovani Leishmania donovani IC90 = 0.057 ug/ml 15730255

  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 NPC309309 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 NPC291999
0.9872 High Similarity NPC53385
0.8953 High Similarity NPC211230
0.8851 High Similarity NPC474882
0.8846 High Similarity NPC112680
0.8636 High Similarity NPC474328
0.8621 High Similarity NPC174167
0.8621 High Similarity NPC470036
0.8608 High Similarity NPC292589
0.8605 High Similarity NPC112454
0.8605 High Similarity NPC65615
0.8605 High Similarity NPC68148
0.8554 High Similarity NPC53733
0.8523 High Similarity NPC263780
0.8427 Intermediate Similarity NPC23170
0.8415 Intermediate Similarity NPC287063
0.8395 Intermediate Similarity NPC72507
0.8353 Intermediate Similarity NPC33881
0.8333 Intermediate Similarity NPC777
0.8313 Intermediate Similarity NPC475863
0.8313 Intermediate Similarity NPC121984
0.8214 Intermediate Similarity NPC310989
0.8193 Intermediate Similarity NPC18955
0.8193 Intermediate Similarity NPC2482
0.8118 Intermediate Similarity NPC237795
0.8118 Intermediate Similarity NPC82538
0.8095 Intermediate Similarity NPC3915
0.8095 Intermediate Similarity NPC225515
0.8095 Intermediate Similarity NPC470034
0.8068 Intermediate Similarity NPC230387
0.8023 Intermediate Similarity NPC180834
0.8021 Intermediate Similarity NPC213366
0.8 Intermediate Similarity NPC103486
0.7976 Intermediate Similarity NPC108955
0.7952 Intermediate Similarity NPC470396
0.7952 Intermediate Similarity NPC99168
0.7952 Intermediate Similarity NPC474989
0.7952 Intermediate Similarity NPC22955
0.7949 Intermediate Similarity NPC216460
0.7949 Intermediate Similarity NPC32055
0.7931 Intermediate Similarity NPC469993
0.7927 Intermediate Similarity NPC106364
0.7927 Intermediate Similarity NPC92080
0.7882 Intermediate Similarity NPC55869
0.7882 Intermediate Similarity NPC6663
0.7857 Intermediate Similarity NPC291379
0.7857 Intermediate Similarity NPC27817
0.7857 Intermediate Similarity NPC474113
0.7857 Intermediate Similarity NPC53744
0.7841 Intermediate Similarity NPC94666
0.7831 Intermediate Similarity NPC40394
0.7831 Intermediate Similarity NPC101475
0.7831 Intermediate Similarity NPC34177
0.7831 Intermediate Similarity NPC157996
0.7816 Intermediate Similarity NPC472265
0.7816 Intermediate Similarity NPC237712
0.7816 Intermediate Similarity NPC33913
0.7805 Intermediate Similarity NPC34700
0.7805 Intermediate Similarity NPC138374
0.7802 Intermediate Similarity NPC301244
0.7778 Intermediate Similarity NPC471799
0.7778 Intermediate Similarity NPC477973
0.7753 Intermediate Similarity NPC470523
0.7753 Intermediate Similarity NPC71507
0.7753 Intermediate Similarity NPC73064
0.7753 Intermediate Similarity NPC93778
0.7742 Intermediate Similarity NPC147232
0.7738 Intermediate Similarity NPC300499
0.7738 Intermediate Similarity NPC158662
0.7738 Intermediate Similarity NPC196753
0.7738 Intermediate Similarity NPC253807
0.7738 Intermediate Similarity NPC98386
0.7738 Intermediate Similarity NPC230295
0.7738 Intermediate Similarity NPC30321
0.7738 Intermediate Similarity NPC189485
0.7727 Intermediate Similarity NPC474680
0.7727 Intermediate Similarity NPC32037
0.7727 Intermediate Similarity NPC132228
0.7727 Intermediate Similarity NPC474537
0.7727 Intermediate Similarity NPC241512
0.7727 Intermediate Similarity NPC6185
0.7727 Intermediate Similarity NPC8518
0.7727 Intermediate Similarity NPC274724
0.7727 Intermediate Similarity NPC469948
0.7727 Intermediate Similarity NPC133652
0.7727 Intermediate Similarity NPC133954
0.7727 Intermediate Similarity NPC263997
0.7711 Intermediate Similarity NPC290598
0.7711 Intermediate Similarity NPC27765
0.7711 Intermediate Similarity NPC265328
0.7711 Intermediate Similarity NPC120098
0.7711 Intermediate Similarity NPC30590
0.7711 Intermediate Similarity NPC106432
0.7711 Intermediate Similarity NPC122418
0.7701 Intermediate Similarity NPC70834
0.7701 Intermediate Similarity NPC307258
0.7701 Intermediate Similarity NPC105803
0.7692 Intermediate Similarity NPC129913
0.7692 Intermediate Similarity NPC212369
0.7692 Intermediate Similarity NPC46441
0.7692 Intermediate Similarity NPC252737
0.7683 Intermediate Similarity NPC100334
0.7683 Intermediate Similarity NPC471797
0.7674 Intermediate Similarity NPC116202
0.7674 Intermediate Similarity NPC471898
0.7674 Intermediate Similarity NPC6434
0.7667 Intermediate Similarity NPC206060
0.7667 Intermediate Similarity NPC472802
0.7667 Intermediate Similarity NPC1753
0.7667 Intermediate Similarity NPC474511
0.7667 Intermediate Similarity NPC470524
0.7654 Intermediate Similarity NPC242001
0.764 Intermediate Similarity NPC474732
0.764 Intermediate Similarity NPC74363
0.764 Intermediate Similarity NPC158393
0.764 Intermediate Similarity NPC474778
0.764 Intermediate Similarity NPC51014
0.764 Intermediate Similarity NPC327115
0.764 Intermediate Similarity NPC213412
0.764 Intermediate Similarity NPC475862
0.764 Intermediate Similarity NPC56588
0.764 Intermediate Similarity NPC474733
0.764 Intermediate Similarity NPC145879
0.764 Intermediate Similarity NPC31564
0.7634 Intermediate Similarity NPC80365
0.7634 Intermediate Similarity NPC160413
0.7619 Intermediate Similarity NPC476811
0.7619 Intermediate Similarity NPC90979
0.7619 Intermediate Similarity NPC472805
0.7614 Intermediate Similarity NPC96095
0.7614 Intermediate Similarity NPC473246
0.7614 Intermediate Similarity NPC85774
0.7614 Intermediate Similarity NPC214043
0.7609 Intermediate Similarity NPC65120
0.7609 Intermediate Similarity NPC4036
0.7609 Intermediate Similarity NPC474525
0.7609 Intermediate Similarity NPC158030
0.7609 Intermediate Similarity NPC145067
0.7609 Intermediate Similarity NPC233455
0.7595 Intermediate Similarity NPC197805
0.759 Intermediate Similarity NPC471468
0.7586 Intermediate Similarity NPC48362
0.7586 Intermediate Similarity NPC69101
0.7586 Intermediate Similarity NPC20853
0.7586 Intermediate Similarity NPC251779
0.7582 Intermediate Similarity NPC474686
0.7582 Intermediate Similarity NPC95246
0.7582 Intermediate Similarity NPC184663
0.7582 Intermediate Similarity NPC210216
0.7582 Intermediate Similarity NPC474972
0.7582 Intermediate Similarity NPC161751
0.7564 Intermediate Similarity NPC163678
0.7558 Intermediate Similarity NPC295131
0.7556 Intermediate Similarity NPC475740
0.7556 Intermediate Similarity NPC136548
0.7556 Intermediate Similarity NPC173089
0.7556 Intermediate Similarity NPC475772
0.7556 Intermediate Similarity NPC158141
0.7556 Intermediate Similarity NPC220930
0.7556 Intermediate Similarity NPC272039
0.7556 Intermediate Similarity NPC58063
0.7553 Intermediate Similarity NPC280725
0.7531 Intermediate Similarity NPC145498
0.7529 Intermediate Similarity NPC18603
0.7529 Intermediate Similarity NPC476808
0.7529 Intermediate Similarity NPC307965
0.7529 Intermediate Similarity NPC76931
0.7528 Intermediate Similarity NPC191965
0.7527 Intermediate Similarity NPC250575
0.7527 Intermediate Similarity NPC242637
0.7527 Intermediate Similarity NPC295643
0.7527 Intermediate Similarity NPC214756
0.7527 Intermediate Similarity NPC12722
0.7527 Intermediate Similarity NPC272075
0.75 Intermediate Similarity NPC208999
0.75 Intermediate Similarity NPC321016
0.75 Intermediate Similarity NPC474789
0.75 Intermediate Similarity NPC52108
0.75 Intermediate Similarity NPC107059
0.75 Intermediate Similarity NPC250621
0.75 Intermediate Similarity NPC475823
0.75 Intermediate Similarity NPC38952
0.75 Intermediate Similarity NPC85173
0.75 Intermediate Similarity NPC470525
0.75 Intermediate Similarity NPC321381
0.75 Intermediate Similarity NPC110725
0.75 Intermediate Similarity NPC474209
0.7474 Intermediate Similarity NPC62516
0.7474 Intermediate Similarity NPC473158
0.7474 Intermediate Similarity NPC157113
0.7474 Intermediate Similarity NPC88847
0.7473 Intermediate Similarity NPC471722
0.7473 Intermediate Similarity NPC473242
0.7473 Intermediate Similarity NPC229612
0.7473 Intermediate Similarity NPC17733
0.7473 Intermediate Similarity NPC474474
0.7473 Intermediate Similarity NPC474512
0.7473 Intermediate Similarity NPC7280
0.7473 Intermediate Similarity NPC290690
0.7473 Intermediate Similarity NPC470629

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC309309 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
0.8605 High Similarity NPD7285 Clinical (unspecified phase)
0.7841 Intermediate Similarity NPD5279 Phase 3
0.7765 Intermediate Similarity NPD4695 Discontinued
0.7647 Intermediate Similarity NPD7645 Phase 2
0.7609 Intermediate Similarity NPD7515 Phase 2
0.7529 Intermediate Similarity NPD3617 Approved
0.7444 Intermediate Similarity NPD5280 Approved
0.7444 Intermediate Similarity NPD4694 Approved
0.7416 Intermediate Similarity NPD3133 Approved
0.7416 Intermediate Similarity NPD3665 Phase 1
0.7416 Intermediate Similarity NPD3666 Approved
0.7416 Intermediate Similarity NPD4786 Approved
0.7391 Intermediate Similarity NPD4753 Phase 2
0.7386 Intermediate Similarity NPD3667 Approved
0.7381 Intermediate Similarity NPD7339 Approved
0.7381 Intermediate Similarity NPD6942 Approved
0.7333 Intermediate Similarity NPD5329 Approved
0.7294 Intermediate Similarity NPD3701 Clinical (unspecified phase)
0.7263 Intermediate Similarity NPD7748 Approved
0.7262 Intermediate Similarity NPD6924 Approved
0.7262 Intermediate Similarity NPD6926 Approved
0.7253 Intermediate Similarity NPD3618 Phase 1
0.7241 Intermediate Similarity NPD4195 Approved
0.7222 Intermediate Similarity NPD4197 Approved
0.7204 Intermediate Similarity NPD5328 Approved
0.7159 Intermediate Similarity NPD8259 Clinical (unspecified phase)
0.7093 Intermediate Similarity NPD6933 Approved
0.7065 Intermediate Similarity NPD5690 Phase 2
0.7053 Intermediate Similarity NPD6079 Approved
0.7041 Intermediate Similarity NPD6084 Phase 2
0.7041 Intermediate Similarity NPD7902 Approved
0.7041 Intermediate Similarity NPD6083 Phase 2
0.701 Intermediate Similarity NPD5210 Approved
0.701 Intermediate Similarity NPD4629 Approved
0.7 Intermediate Similarity NPD4221 Approved
0.7 Intermediate Similarity NPD4223 Phase 3
0.6988 Remote Similarity NPD6922 Approved
0.6988 Remote Similarity NPD6923 Approved
0.6979 Remote Similarity NPD5133 Approved
0.6977 Remote Similarity NPD8264 Approved
0.6966 Remote Similarity NPD7525 Registered
0.6957 Remote Similarity NPD1696 Phase 3
0.6939 Remote Similarity NPD7614 Phase 1
0.6939 Remote Similarity NPD5220 Clinical (unspecified phase)
0.6939 Remote Similarity NPD5221 Approved
0.6939 Remote Similarity NPD5222 Approved
0.6939 Remote Similarity NPD4697 Phase 3
0.6923 Remote Similarity NPD4788 Approved
0.6915 Remote Similarity NPD5737 Approved
0.6915 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6915 Remote Similarity NPD6672 Approved
0.6905 Remote Similarity NPD7144 Approved
0.6905 Remote Similarity NPD7143 Approved
0.6869 Remote Similarity NPD4755 Approved
0.6869 Remote Similarity NPD5173 Approved
0.686 Remote Similarity NPD4785 Approved
0.686 Remote Similarity NPD4784 Approved
0.6854 Remote Similarity NPD6929 Approved
0.6837 Remote Similarity NPD5695 Phase 3
0.6824 Remote Similarity NPD7152 Approved
0.6824 Remote Similarity NPD4243 Approved
0.6824 Remote Similarity NPD7151 Approved
0.6824 Remote Similarity NPD7150 Approved
0.6804 Remote Similarity NPD4202 Approved
0.6778 Remote Similarity NPD6930 Phase 2
0.6778 Remote Similarity NPD6931 Approved
0.6778 Remote Similarity NPD7509 Discontinued
0.6735 Remote Similarity NPD7900 Approved
0.6735 Remote Similarity NPD7901 Clinical (unspecified phase)
0.6733 Remote Similarity NPD5286 Approved
0.6733 Remote Similarity NPD4700 Approved
0.6733 Remote Similarity NPD4696 Approved
0.6733 Remote Similarity NPD5285 Approved
0.6702 Remote Similarity NPD4688 Approved
0.6702 Remote Similarity NPD4623 Approved
0.6702 Remote Similarity NPD4138 Approved
0.6702 Remote Similarity NPD5205 Approved
0.6702 Remote Similarity NPD4693 Phase 3
0.6702 Remote Similarity NPD7521 Approved
0.6702 Remote Similarity NPD4519 Discontinued
0.6702 Remote Similarity NPD4689 Approved
0.6702 Remote Similarity NPD4690 Approved
0.6702 Remote Similarity NPD7334 Approved
0.6702 Remote Similarity NPD6409 Approved
0.6702 Remote Similarity NPD3574 Clinical (unspecified phase)
0.6702 Remote Similarity NPD6684 Approved
0.6702 Remote Similarity NPD7146 Approved
0.6702 Remote Similarity NPD5330 Approved
0.6701 Remote Similarity NPD5284 Approved
0.6701 Remote Similarity NPD5281 Approved
0.6701 Remote Similarity NPD6050 Approved
0.6667 Remote Similarity NPD5733 Approved
0.6667 Remote Similarity NPD3668 Phase 3
0.6667 Remote Similarity NPD5223 Approved
0.6634 Remote Similarity NPD5696 Approved
0.6633 Remote Similarity NPD6399 Phase 3
0.6629 Remote Similarity NPD6932 Approved
0.6629 Remote Similarity NPD5776 Phase 2
0.6629 Remote Similarity NPD6925 Approved
0.6602 Remote Similarity NPD5211 Phase 2
0.6602 Remote Similarity NPD5225 Approved
0.6602 Remote Similarity NPD5226 Approved
0.6602 Remote Similarity NPD5224 Approved
0.6602 Remote Similarity NPD4633 Approved
0.66 Remote Similarity NPD7732 Phase 3
0.6598 Remote Similarity NPD4096 Approved
0.6598 Remote Similarity NPD5692 Phase 3
0.6593 Remote Similarity NPD4748 Discontinued
0.6571 Remote Similarity NPD5739 Approved
0.6571 Remote Similarity NPD7128 Approved
0.6571 Remote Similarity NPD6675 Approved
0.6571 Remote Similarity NPD6402 Approved
0.6562 Remote Similarity NPD4518 Approved
0.6562 Remote Similarity NPD6903 Approved
0.6559 Remote Similarity NPD6695 Phase 3
0.6556 Remote Similarity NPD7322 Clinical (unspecified phase)
0.6556 Remote Similarity NPD7145 Approved
0.6538 Remote Similarity NPD4754 Approved
0.6538 Remote Similarity NPD5175 Approved
0.6538 Remote Similarity NPD5174 Approved
0.6531 Remote Similarity NPD5694 Approved
0.6531 Remote Similarity NPD6411 Approved
0.6522 Remote Similarity NPD8028 Phase 2
0.6512 Remote Similarity NPD4789 Approved
0.6495 Remote Similarity NPD6673 Approved
0.6495 Remote Similarity NPD6080 Approved
0.6495 Remote Similarity NPD6904 Approved
0.6489 Remote Similarity NPD7338 Clinical (unspecified phase)
0.6484 Remote Similarity NPD6683 Phase 2
0.6477 Remote Similarity NPD4687 Approved
0.6477 Remote Similarity NPD4058 Approved
0.6476 Remote Similarity NPD5141 Approved
0.6471 Remote Similarity NPD7638 Approved
0.6471 Remote Similarity NPD5290 Discontinued
0.6458 Remote Similarity NPD4751 Clinical (unspecified phase)
0.6449 Remote Similarity NPD6881 Approved
0.6449 Remote Similarity NPD7320 Approved
0.6449 Remote Similarity NPD6899 Approved
0.6437 Remote Similarity NPD5276 Approved
0.6421 Remote Similarity NPD7520 Clinical (unspecified phase)
0.6421 Remote Similarity NPD6893 Approved
0.6415 Remote Similarity NPD4767 Approved
0.6415 Remote Similarity NPD4768 Approved
0.6413 Remote Similarity NPD7332 Phase 2
0.6413 Remote Similarity NPD7514 Phase 3
0.6408 Remote Similarity NPD7640 Approved
0.6408 Remote Similarity NPD7639 Approved
0.6404 Remote Similarity NPD5275 Approved
0.6404 Remote Similarity NPD4190 Phase 3
0.6395 Remote Similarity NPD4137 Phase 3
0.6389 Remote Similarity NPD6373 Approved
0.6389 Remote Similarity NPD6372 Approved
0.6355 Remote Similarity NPD5701 Approved
0.6355 Remote Similarity NPD6412 Phase 2
0.6355 Remote Similarity NPD5697 Approved
0.6354 Remote Similarity NPD6098 Approved
0.6344 Remote Similarity NPD4692 Approved
0.6344 Remote Similarity NPD6902 Approved
0.6344 Remote Similarity NPD4139 Approved
0.6344 Remote Similarity NPD6898 Phase 1
0.6337 Remote Similarity NPD5654 Approved
0.633 Remote Similarity NPD7290 Approved
0.633 Remote Similarity NPD6883 Approved
0.633 Remote Similarity NPD7102 Approved
0.6327 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6327 Remote Similarity NPD6101 Approved
0.6322 Remote Similarity NPD4691 Approved
0.6322 Remote Similarity NPD4747 Approved
0.6296 Remote Similarity NPD4729 Approved
0.6296 Remote Similarity NPD4730 Approved
0.6296 Remote Similarity NPD5168 Approved
0.6296 Remote Similarity NPD6011 Approved
0.6296 Remote Similarity NPD5128 Approved
0.6289 Remote Similarity NPD3573 Approved
0.6289 Remote Similarity NPD7750 Discontinued
0.6289 Remote Similarity NPD7524 Approved
0.6273 Remote Similarity NPD6401 Clinical (unspecified phase)
0.6273 Remote Similarity NPD6617 Approved
0.6273 Remote Similarity NPD6650 Approved
0.6273 Remote Similarity NPD6847 Approved
0.6273 Remote Similarity NPD6649 Approved
0.6273 Remote Similarity NPD6869 Approved
0.6273 Remote Similarity NPD8130 Phase 1
0.6263 Remote Similarity NPD5207 Approved
0.6239 Remote Similarity NPD6012 Approved
0.6239 Remote Similarity NPD6014 Approved
0.6239 Remote Similarity NPD6013 Approved
0.6216 Remote Similarity NPD6882 Approved
0.6216 Remote Similarity NPD8297 Approved
0.6214 Remote Similarity NPD5959 Approved
0.62 Remote Similarity NPD5693 Phase 1
0.6182 Remote Similarity NPD5249 Phase 3
0.6182 Remote Similarity NPD5248 Approved
0.6182 Remote Similarity NPD5247 Approved
0.6182 Remote Similarity NPD5250 Approved
0.6182 Remote Similarity NPD4634 Approved
0.6182 Remote Similarity NPD5251 Approved
0.6182 Remote Similarity NPD5134 Clinical (unspecified phase)
0.6182 Remote Similarity NPD5169 Approved
0.6182 Remote Similarity NPD5135 Approved

Structure

External Identifiers

PubChem CID   21575471
ChEMBL   CHEMBL495863
ZINC  

Physicochemical Properties

Molecular Weight:  422.28
ALogP:  1.6303
MLogP:  4.21
XLogP:  7.892
# Rotatable Bonds:  8
Polar Surface Area:  57.53
# H-Bond Aceptor:  3
# H-Bond Donor:  2
# Rings:  5
# Heavy Atoms:  31

Download Data

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Structure MOL file  
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Biological Activities  
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