Natural Product: NPC27817

Natural Product ID:  NPC27817
Common Name:   Taxodione
IUPAC Name:   (4bS,8aS)-4-hydroxy-4b,8,8-trimethyl-2-propan-2-yl-5,6,7,8a-tetrahydrophenanthrene-3,9-dione
Synonyms:   taxodione
Molecular Formula:   C20H26O3
Standard InCHIKey:  FNNZMRSRVYUVQT-AZUAARDMSA-N
Standard InCHI:  InChI=1S/C20H26O3/c1-11(2)13-9-12-10-14(21)18-19(3,4)7-6-8-20(18,5)15(12)17(23)16(13)22/h9-11,18,23H,6-8H2,1-5H3/t18-,20+/m0/s1
Canonical SMILES:  CC(C1=CC2=CC(=O)[C@@H]3[C@](C2=C(C1=O)O)(C)CCCC3(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
NPO19278 Taxodium distichum Species Cupressaceae Eukaryota PMID[17869103]
NPO1397 Cylindrocarpon lucidum Species Nectriaceae Eukaryota UNPD*
NPO1809 Delphinium scabriflorum Species Ranunculaceae Eukaryota UNPD*
NPO9555 Aplysilla tango Species Darwinellidae Eukaryota UNPD*

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT518 Protein Complex Tubulin Homo sapiens Inhibition = 45 % 17869103
NPT926 Cell Line SK-MEL-1 Homo sapiens IC50 = 9600 nM 23865778
NPT116 Cell Line HL-60 Homo sapiens IC50 = 4800 nM 23865778
NPT466 Cell Line U-937 Homo sapiens IC50 = 3000 nM 23865778
NPT793 Cell Line MOLT-3 Homo sapiens IC50 = 1800 nM 23865778
NPT83 Cell Line MCF7 Homo sapiens IC50 > 30000 nM 23865778
NPT633 Organism Leishmania donovani Leishmania donovani IC50 = 1600 nM 26905523
NPT139 Cell Line HT-29 Homo sapiens IC50 = 2500 nM 26905523
NPT2 Others Unspecified Ratio IC50 = 1.6 26905523
NPT634 Organism Leishmania amazonensis Leishmania amazonensis IC50 = 14300 nM 26905523
NPT2 Others Unspecified Ratio IC50 = 0.2 26905523

  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 NPC27817 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
0.9589 High Similarity NPC110725
0.9342 High Similarity NPC108955
0.9333 High Similarity NPC189485
0.9324 High Similarity NPC1254
0.9221 High Similarity NPC225515
0.9221 High Similarity NPC55869
0.8846 High Similarity NPC287063
0.8816 High Similarity NPC92080
0.8767 High Similarity NPC474060
0.8765 High Similarity NPC132228
0.8765 High Similarity NPC263997
0.8765 High Similarity NPC8518
0.8734 High Similarity NPC470034
0.8734 High Similarity NPC475863
0.8734 High Similarity NPC99308
0.863 High Similarity NPC310992
0.8625 High Similarity NPC103486
0.859 High Similarity NPC30321
0.8537 High Similarity NPC33881
0.8537 High Similarity NPC241512
0.8537 High Similarity NPC6185
0.8537 High Similarity NPC32037
0.8519 High Similarity NPC105803
0.8519 High Similarity NPC53733
0.85 High Similarity NPC474085
0.85 High Similarity NPC121984
0.8378 Intermediate Similarity NPC188292
0.8378 Intermediate Similarity NPC260474
0.8353 Intermediate Similarity NPC112454
0.8353 Intermediate Similarity NPC65615
0.8353 Intermediate Similarity NPC68148
0.8333 Intermediate Similarity NPC112680
0.8333 Intermediate Similarity NPC292589
0.8333 Intermediate Similarity NPC26504
0.8313 Intermediate Similarity NPC474680
0.8313 Intermediate Similarity NPC33663
0.8276 Intermediate Similarity NPC263780
0.8272 Intermediate Similarity NPC116797
0.8205 Intermediate Similarity NPC175079
0.8161 Intermediate Similarity NPC174167
0.8161 Intermediate Similarity NPC470036
0.8148 Intermediate Similarity NPC476809
0.8148 Intermediate Similarity NPC2482
0.814 Intermediate Similarity NPC474918
0.8133 Intermediate Similarity NPC87141
0.8125 Intermediate Similarity NPC476808
0.8125 Intermediate Similarity NPC74410
0.8101 Intermediate Similarity NPC180886
0.8101 Intermediate Similarity NPC309399
0.8101 Intermediate Similarity NPC470525
0.8095 Intermediate Similarity NPC255174
0.8095 Intermediate Similarity NPC469993
0.8095 Intermediate Similarity NPC133652
0.8077 Intermediate Similarity NPC147438
0.8072 Intermediate Similarity NPC102197
0.8068 Intermediate Similarity NPC211230
0.8049 Intermediate Similarity NPC278459
0.8049 Intermediate Similarity NPC6663
0.8049 Intermediate Similarity NPC475833
0.8046 Intermediate Similarity NPC129913
0.8025 Intermediate Similarity NPC192329
0.8025 Intermediate Similarity NPC472490
0.8023 Intermediate Similarity NPC72397
0.8 Intermediate Similarity NPC94666
0.8 Intermediate Similarity NPC165711
0.7978 Intermediate Similarity NPC474328
0.7978 Intermediate Similarity NPC23170
0.7978 Intermediate Similarity NPC474882
0.7976 Intermediate Similarity NPC53385
0.7976 Intermediate Similarity NPC237712
0.7976 Intermediate Similarity NPC87552
0.7976 Intermediate Similarity NPC144258
0.7973 Intermediate Similarity NPC251118
0.7927 Intermediate Similarity NPC26139
0.7927 Intermediate Similarity NPC18955
0.7927 Intermediate Similarity NPC472478
0.7922 Intermediate Similarity NPC2634
0.7922 Intermediate Similarity NPC265782
0.7922 Intermediate Similarity NPC251929
0.7907 Intermediate Similarity NPC136548
0.7901 Intermediate Similarity NPC275494
0.7901 Intermediate Similarity NPC471409
0.7889 Intermediate Similarity NPC147232
0.7889 Intermediate Similarity NPC777
0.7882 Intermediate Similarity NPC474537
0.7865 Intermediate Similarity NPC250575
0.7865 Intermediate Similarity NPC134826
0.7857 Intermediate Similarity NPC470015
0.7857 Intermediate Similarity NPC49019
0.7857 Intermediate Similarity NPC291999
0.7857 Intermediate Similarity NPC168188
0.7857 Intermediate Similarity NPC83569
0.7857 Intermediate Similarity NPC69279
0.7857 Intermediate Similarity NPC309309
0.7848 Intermediate Similarity NPC301065
0.7841 Intermediate Similarity NPC474209
0.7841 Intermediate Similarity NPC475823
0.7831 Intermediate Similarity NPC472684
0.7831 Intermediate Similarity NPC473217
0.7831 Intermediate Similarity NPC189237
0.7831 Intermediate Similarity NPC44963
0.7831 Intermediate Similarity NPC471898
0.7821 Intermediate Similarity NPC54123
0.7816 Intermediate Similarity NPC58271
0.7805 Intermediate Similarity NPC170793
0.7805 Intermediate Similarity NPC474113
0.7792 Intermediate Similarity NPC256846
0.7792 Intermediate Similarity NPC139397
0.7791 Intermediate Similarity NPC327115
0.7791 Intermediate Similarity NPC472974
0.7791 Intermediate Similarity NPC475022
0.7791 Intermediate Similarity NPC118648
0.7791 Intermediate Similarity NPC222613
0.7778 Intermediate Similarity NPC283087
0.7778 Intermediate Similarity NPC97377
0.7778 Intermediate Similarity NPC257666
0.7778 Intermediate Similarity NPC266193
0.7765 Intermediate Similarity NPC473246
0.7753 Intermediate Similarity NPC99380
0.7753 Intermediate Similarity NPC204341
0.775 Intermediate Similarity NPC473171
0.775 Intermediate Similarity NPC476346
0.7738 Intermediate Similarity NPC142253
0.7738 Intermediate Similarity NPC3511
0.7738 Intermediate Similarity NPC302661
0.7738 Intermediate Similarity NPC238991
0.7738 Intermediate Similarity NPC260956
0.7738 Intermediate Similarity NPC193347
0.7738 Intermediate Similarity NPC320514
0.7727 Intermediate Similarity NPC210216
0.7722 Intermediate Similarity NPC474228
0.7722 Intermediate Similarity NPC130016
0.7722 Intermediate Similarity NPC470045
0.7722 Intermediate Similarity NPC109576
0.7722 Intermediate Similarity NPC303613
0.7722 Intermediate Similarity NPC470044
0.7722 Intermediate Similarity NPC56747
0.7722 Intermediate Similarity NPC180015
0.7711 Intermediate Similarity NPC74086
0.7711 Intermediate Similarity NPC469637
0.7703 Intermediate Similarity NPC288253
0.7701 Intermediate Similarity NPC220930
0.7701 Intermediate Similarity NPC272039
0.7701 Intermediate Similarity NPC470523
0.7692 Intermediate Similarity NPC295347
0.7692 Intermediate Similarity NPC307176
0.7692 Intermediate Similarity NPC280725
0.7692 Intermediate Similarity NPC260040
0.7683 Intermediate Similarity NPC62336
0.7683 Intermediate Similarity NPC475994
0.7683 Intermediate Similarity NPC207772
0.7674 Intermediate Similarity NPC476426
0.7674 Intermediate Similarity NPC123319
0.7674 Intermediate Similarity NPC311702
0.7674 Intermediate Similarity NPC469948
0.7674 Intermediate Similarity NPC94531
0.7674 Intermediate Similarity NPC29447
0.7674 Intermediate Similarity NPC11711
0.7671 Intermediate Similarity NPC127582
0.7662 Intermediate Similarity NPC155198
0.7654 Intermediate Similarity NPC263582
0.7654 Intermediate Similarity NPC186554
0.7654 Intermediate Similarity NPC69143
0.7654 Intermediate Similarity NPC76966
0.7647 Intermediate Similarity NPC70834
0.7625 Intermediate Similarity NPC241854
0.7625 Intermediate Similarity NPC213223
0.7625 Intermediate Similarity NPC476046
0.7625 Intermediate Similarity NPC474797
0.7625 Intermediate Similarity NPC251970
0.7625 Intermediate Similarity NPC474796
0.7625 Intermediate Similarity NPC329866
0.7619 Intermediate Similarity NPC477372
0.7619 Intermediate Similarity NPC142244
0.7619 Intermediate Similarity NPC201912
0.7619 Intermediate Similarity NPC38350
0.7619 Intermediate Similarity NPC4166
0.7614 Intermediate Similarity NPC470524
0.7614 Intermediate Similarity NPC307298
0.7614 Intermediate Similarity NPC471722
0.76 Intermediate Similarity NPC469662
0.76 Intermediate Similarity NPC285371
0.76 Intermediate Similarity NPC475124
0.7595 Intermediate Similarity NPC181204
0.7595 Intermediate Similarity NPC474539
0.7595 Intermediate Similarity NPC190035
0.7595 Intermediate Similarity NPC84790
0.7595 Intermediate Similarity NPC160817
0.759 Intermediate Similarity NPC476177
0.759 Intermediate Similarity NPC170394
0.759 Intermediate Similarity NPC475681
0.759 Intermediate Similarity NPC19900
0.7586 Intermediate Similarity NPC31564
0.7586 Intermediate Similarity NPC145879
0.7586 Intermediate Similarity NPC474733
0.7586 Intermediate Similarity NPC203795
0.7586 Intermediate Similarity NPC51014
0.7586 Intermediate Similarity NPC474732
0.7586 Intermediate Similarity NPC20688
0.7586 Intermediate Similarity NPC474778

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC27817 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
0.8846 High Similarity NPD4695 Discontinued
0.8434 Intermediate Similarity NPD5280 Approved
0.8434 Intermediate Similarity NPD4694 Approved
0.8353 Intermediate Similarity NPD7285 Clinical (unspecified phase)
0.8214 Intermediate Similarity NPD5690 Phase 2
0.8214 Intermediate Similarity NPD5279 Phase 3
0.8125 Intermediate Similarity NPD3617 Approved
0.8077 Intermediate Similarity NPD4058 Approved
0.8077 Intermediate Similarity NPD5733 Approved
0.8077 Intermediate Similarity NPD4687 Approved
0.8052 Intermediate Similarity NPD5276 Approved
0.7976 Intermediate Similarity NPD4197 Approved
0.7922 Intermediate Similarity NPD4691 Approved
0.7882 Intermediate Similarity NPD5329 Approved
0.7792 Intermediate Similarity NPD4137 Phase 3
0.7738 Intermediate Similarity NPD4223 Phase 3
0.7738 Intermediate Similarity NPD4221 Approved
0.7711 Intermediate Similarity NPD8259 Clinical (unspecified phase)
0.7692 Intermediate Similarity NPD4747 Approved
0.7667 Intermediate Similarity NPD5133 Approved
0.7558 Intermediate Similarity NPD3666 Approved
0.7558 Intermediate Similarity NPD3665 Phase 1
0.7558 Intermediate Similarity NPD3133 Approved
0.7556 Intermediate Similarity NPD5284 Approved
0.7556 Intermediate Similarity NPD5281 Approved
0.7529 Intermediate Similarity NPD3667 Approved
0.7528 Intermediate Similarity NPD4753 Phase 2
0.7444 Intermediate Similarity NPD5692 Phase 3
0.7444 Intermediate Similarity NPD4096 Approved
0.7442 Intermediate Similarity NPD3527 Clinical (unspecified phase)
0.7416 Intermediate Similarity NPD4518 Approved
0.7386 Intermediate Similarity NPD5205 Approved
0.7386 Intermediate Similarity NPD4688 Approved
0.7386 Intermediate Similarity NPD4690 Approved
0.7386 Intermediate Similarity NPD4623 Approved
0.7386 Intermediate Similarity NPD4693 Phase 3
0.7386 Intermediate Similarity NPD4689 Approved
0.7386 Intermediate Similarity NPD3618 Phase 1
0.7386 Intermediate Similarity NPD4138 Approved
0.7386 Intermediate Similarity NPD4519 Discontinued
0.7386 Intermediate Similarity NPD3574 Clinical (unspecified phase)
0.7363 Intermediate Similarity NPD5694 Approved
0.7363 Intermediate Similarity NPD6050 Approved
0.7356 Intermediate Similarity NPD4786 Approved
0.7312 Intermediate Similarity NPD5210 Approved
0.7312 Intermediate Similarity NPD5695 Phase 3
0.7312 Intermediate Similarity NPD4629 Approved
0.7237 Intermediate Similarity NPD2664 Clinical (unspecified phase)
0.7234 Intermediate Similarity NPD5221 Approved
0.7234 Intermediate Similarity NPD5222 Approved
0.7234 Intermediate Similarity NPD5220 Clinical (unspecified phase)
0.7215 Intermediate Similarity NPD3621 Clinical (unspecified phase)
0.7176 Intermediate Similarity NPD4195 Approved
0.7174 Intermediate Similarity NPD6079 Approved
0.7158 Intermediate Similarity NPD5173 Approved
0.7143 Intermediate Similarity NPD5328 Approved
0.7079 Intermediate Similarity NPD1696 Phase 3
0.7065 Intermediate Similarity NPD5207 Approved
0.7053 Intermediate Similarity NPD4697 Phase 3
0.7033 Intermediate Similarity NPD6672 Approved
0.7033 Intermediate Similarity NPD5737 Approved
0.7011 Intermediate Similarity NPD4692 Approved
0.7011 Intermediate Similarity NPD8028 Phase 2
0.7011 Intermediate Similarity NPD4139 Approved
0.701 Intermediate Similarity NPD4696 Approved
0.701 Intermediate Similarity NPD5286 Approved
0.701 Intermediate Similarity NPD5285 Approved
0.6989 Remote Similarity NPD7515 Phase 2
0.6979 Remote Similarity NPD4755 Approved
0.6979 Remote Similarity NPD6083 Phase 2
0.6979 Remote Similarity NPD6084 Phase 2
0.6966 Remote Similarity NPD3668 Phase 3
0.6962 Remote Similarity NPD7331 Phase 2
0.6957 Remote Similarity NPD6673 Approved
0.6957 Remote Similarity NPD6904 Approved
0.6957 Remote Similarity NPD6080 Approved
0.6947 Remote Similarity NPD5654 Approved
0.6939 Remote Similarity NPD5223 Approved
0.6933 Remote Similarity NPD287 Approved
0.6923 Remote Similarity NPD3573 Approved
0.6915 Remote Similarity NPD4202 Approved
0.6907 Remote Similarity NPD5696 Approved
0.6875 Remote Similarity NPD7614 Phase 1
0.6869 Remote Similarity NPD5211 Phase 2
0.6869 Remote Similarity NPD4633 Approved
0.6869 Remote Similarity NPD5225 Approved
0.6869 Remote Similarity NPD5224 Approved
0.6869 Remote Similarity NPD5226 Approved
0.6869 Remote Similarity NPD5091 Approved
0.6854 Remote Similarity NPD4788 Approved
0.6842 Remote Similarity NPD7748 Approved
0.6837 Remote Similarity NPD6404 Discontinued
0.6837 Remote Similarity NPD4700 Approved
0.6813 Remote Similarity NPD6684 Approved
0.6813 Remote Similarity NPD6409 Approved
0.6813 Remote Similarity NPD7521 Approved
0.6813 Remote Similarity NPD7334 Approved
0.6813 Remote Similarity NPD5330 Approved
0.6813 Remote Similarity NPD6098 Approved
0.6813 Remote Similarity NPD7146 Approved
0.6809 Remote Similarity NPD5693 Phase 1
0.6804 Remote Similarity NPD5959 Approved
0.68 Remote Similarity NPD5174 Approved
0.68 Remote Similarity NPD5175 Approved
0.6744 Remote Similarity NPD4756 Discovery
0.6737 Remote Similarity NPD6399 Phase 3
0.6733 Remote Similarity NPD5141 Approved
0.6667 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6667 Remote Similarity NPD6903 Approved
0.6667 Remote Similarity NPD5208 Approved
0.6634 Remote Similarity NPD4754 Approved
0.6633 Remote Similarity NPD7902 Approved
0.6632 Remote Similarity NPD6411 Approved
0.6625 Remote Similarity NPD7341 Phase 2
0.6602 Remote Similarity NPD5697 Approved
0.6543 Remote Similarity NPD6108 Clinical (unspecified phase)
0.6538 Remote Similarity NPD4729 Approved
0.6538 Remote Similarity NPD4730 Approved
0.6538 Remote Similarity NPD6899 Approved
0.6538 Remote Similarity NPD6011 Approved
0.6538 Remote Similarity NPD5168 Approved
0.6538 Remote Similarity NPD5128 Approved
0.6538 Remote Similarity NPD6881 Approved
0.6512 Remote Similarity NPD8264 Approved
0.6505 Remote Similarity NPD6675 Approved
0.6505 Remote Similarity NPD6402 Approved
0.6505 Remote Similarity NPD7128 Approved
0.6505 Remote Similarity NPD4767 Approved
0.6505 Remote Similarity NPD5739 Approved
0.6505 Remote Similarity NPD4768 Approved
0.6476 Remote Similarity NPD6013 Approved
0.6476 Remote Similarity NPD6014 Approved
0.6476 Remote Similarity NPD6012 Approved
0.6442 Remote Similarity NPD5701 Approved
0.6437 Remote Similarity NPD3701 Clinical (unspecified phase)
0.6421 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6421 Remote Similarity NPD6101 Approved
0.6415 Remote Similarity NPD5251 Approved
0.6415 Remote Similarity NPD5134 Clinical (unspecified phase)
0.6415 Remote Similarity NPD4634 Approved
0.6415 Remote Similarity NPD7102 Approved
0.6415 Remote Similarity NPD5169 Approved
0.6415 Remote Similarity NPD5247 Approved
0.6415 Remote Similarity NPD5248 Approved
0.6415 Remote Similarity NPD5135 Approved
0.6415 Remote Similarity NPD5249 Phase 3
0.6415 Remote Similarity NPD7290 Approved
0.6415 Remote Similarity NPD5250 Approved
0.6415 Remote Similarity NPD6883 Approved
0.6395 Remote Similarity NPD4784 Approved
0.6395 Remote Similarity NPD4785 Approved
0.6381 Remote Similarity NPD7320 Approved
0.6374 Remote Similarity NPD4752 Clinical (unspecified phase)
0.6364 Remote Similarity NPD7732 Phase 3
0.6355 Remote Similarity NPD6847 Approved
0.6355 Remote Similarity NPD5215 Approved
0.6355 Remote Similarity NPD6649 Approved
0.6355 Remote Similarity NPD6869 Approved
0.6355 Remote Similarity NPD5216 Approved
0.6355 Remote Similarity NPD6617 Approved
0.6355 Remote Similarity NPD8130 Phase 1
0.6355 Remote Similarity NPD6650 Approved
0.6355 Remote Similarity NPD5217 Approved
0.6355 Remote Similarity NPD5127 Approved
0.6353 Remote Similarity NPD4243 Approved
0.6341 Remote Similarity NPD3704 Approved
0.6327 Remote Similarity NPD6001 Approved
0.6327 Remote Similarity NPD7901 Clinical (unspecified phase)
0.6327 Remote Similarity NPD5282 Discontinued
0.6327 Remote Similarity NPD7900 Approved
0.6322 Remote Similarity NPD6942 Approved
0.6322 Remote Similarity NPD7339 Approved
0.6321 Remote Similarity NPD6373 Approved
0.6321 Remote Similarity NPD6372 Approved
0.631 Remote Similarity NPD6923 Approved
0.631 Remote Similarity NPD6922 Approved
0.63 Remote Similarity NPD3495 Discontinued
0.6296 Remote Similarity NPD6882 Approved
0.6296 Remote Similarity NPD8297 Approved
0.6263 Remote Similarity NPD6356 Clinical (unspecified phase)
0.625 Remote Similarity NPD4194 Approved
0.625 Remote Similarity NPD4193 Approved
0.625 Remote Similarity NPD4191 Approved
0.625 Remote Similarity NPD4192 Approved
0.6239 Remote Similarity NPD4632 Approved
0.6235 Remote Similarity NPD7143 Approved
0.6235 Remote Similarity NPD7144 Approved
0.6207 Remote Similarity NPD6924 Approved
0.6207 Remote Similarity NPD6926 Approved
0.6204 Remote Similarity NPD6401 Clinical (unspecified phase)
0.6182 Remote Similarity NPD5167 Approved
0.6176 Remote Similarity NPD2066 Phase 3
0.617 Remote Similarity NPD1694 Approved
0.6163 Remote Similarity NPD7150 Approved
0.6163 Remote Similarity NPD7151 Approved
0.6163 Remote Similarity NPD7152 Approved
0.6162 Remote Similarity NPD5122 Clinical (unspecified phase)
0.6136 Remote Similarity NPD4190 Phase 3
0.6136 Remote Similarity NPD5275 Approved
0.6132 Remote Similarity NPD6614 Approved

Structure

External Identifiers

PubChem CID   73588
ChEMBL   CHEMBL235195
ZINC  

Physicochemical Properties

Molecular Weight:  314.19
ALogP:  1.0706
MLogP:  3.33
XLogP:  4.474
# Rotatable Bonds:  7
Polar Surface Area:  54.37
# H-Bond Aceptor:  3
# H-Bond Donor:  1
# Rings:  3
# Heavy Atoms:  23

Download Data

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