Natural Product: NPC471815

Natural Product ID:  NPC471815
Common Name:   Cercosporene F
IUPAC Name:   (3aR,5aR,7R)-9-[2-[(3R,3aR,5aR,7R)-1,7-dihydroxy-3a,5a-dimethyl-2,8-dioxo-3-propan-2-yl-3,4,5,6,7,10-hexahydrobenzo[f]azulen-9-yl]ethyl]-2,7-dihydroxy-3a,5a-dimethyl-3-propan-2-yl-4,5,6,7-tetrahydrobenzo[g]azulene-1,8-dione
Synonyms:  
Molecular Formula:   C40H52O8
Standard InCHIKey:  VOGUQGKZIRVTPC-DXUFHKGRSA-N
Standard InCHI:  InChI=1S/C40H52O8/c1-19(2)29-35(47)33(45)25-15-23-21(31(43)27(41)17-37(23,5)11-13-39(25,29)7)9-10-22-24-16-26-34(46)36(48)30(20(3)4)40(26,8)14-12-38(24,6)18-28(42)32(22)44/h15,19-20,27-28,30,41-42,46-47H,9-14,16-18H2,1-8H3/t27-,28-,30+,37-,38-,39+,40+/m1/s1
Canonical SMILES:  O[C@@H]1C[C@@]2(C)CC[C@]3(C(=C(C(=O)[C@@H]3C(C)C)O)CC2=C(C1=O)CCC1=C2C=C3C(=O)C(=C([C@]3(CC[C@@]2(C[C@H](C1=O)O)C)C)C(C)C)O)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
NPO33327 cercospora sp. Species Mycosphaerellaceae Eukaryota PMID[24576210]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT393 Cell Line HCT-116 Homo sapiens Ratio = 1.2 16987657
NPT393 Cell Line HCT-116 Homo sapiens Ratio = 1.3 17095213
NPT393 Cell Line HCT-116 Homo sapiens Ratio = 1.4 17095213
NPT165 Cell Line HeLa Homo sapiens IC50 = 19300 nM 19928902
NPT83 Cell Line MCF7 Homo sapiens IC50 = 46100 nM 19928902
NPT81 Cell Line A549 Homo sapiens IC50 = 29700 nM 19928902
NPT2 Others Unspecified IC50 = 8160 nM 19928902
NPT393 Cell Line HCT-116 Homo sapiens IC50 = 21300 nM 19928902

  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 NPC471815 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
0.785 Intermediate Similarity NPC321556
0.7826 Intermediate Similarity NPC74086
0.7789 Intermediate Similarity NPC32037
0.7778 Intermediate Similarity NPC134826
0.77 Intermediate Similarity NPC474328
0.7647 Intermediate Similarity NPC472073
0.7647 Intermediate Similarity NPC472074
0.7624 Intermediate Similarity NPC280725
0.76 Intermediate Similarity NPC211230
0.7568 Intermediate Similarity NPC136922
0.7553 Intermediate Similarity NPC136150
0.7551 Intermediate Similarity NPC471722
0.7526 Intermediate Similarity NPC475022
0.7526 Intermediate Similarity NPC183736
0.7526 Intermediate Similarity NPC118648
0.7526 Intermediate Similarity NPC222613
0.7525 Intermediate Similarity NPC196485
0.7525 Intermediate Similarity NPC245972
0.7525 Intermediate Similarity NPC23170
0.7475 Intermediate Similarity NPC119416
0.7474 Intermediate Similarity NPC103486
0.7426 Intermediate Similarity NPC250575
0.74 Intermediate Similarity NPC85173
0.74 Intermediate Similarity NPC191684
0.74 Intermediate Similarity NPC129913
0.74 Intermediate Similarity NPC126993
0.7379 Intermediate Similarity NPC305483
0.7379 Intermediate Similarity NPC96859
0.7379 Intermediate Similarity NPC117133
0.7379 Intermediate Similarity NPC328162
0.7374 Intermediate Similarity NPC474677
0.7353 Intermediate Similarity NPC474882
0.7347 Intermediate Similarity NPC474733
0.7347 Intermediate Similarity NPC474732
0.7347 Intermediate Similarity NPC72133
0.7347 Intermediate Similarity NPC51014
0.7347 Intermediate Similarity NPC31564
0.7347 Intermediate Similarity NPC145879
0.7347 Intermediate Similarity NPC474778
0.7327 Intermediate Similarity NPC168027
0.7327 Intermediate Similarity NPC185936
0.732 Intermediate Similarity NPC473246
0.7308 Intermediate Similarity NPC43747
0.73 Intermediate Similarity NPC1015
0.73 Intermediate Similarity NPC123912
0.73 Intermediate Similarity NPC474245
0.73 Intermediate Similarity NPC275740
0.73 Intermediate Similarity NPC86319
0.73 Intermediate Similarity NPC68148
0.73 Intermediate Similarity NPC65615
0.73 Intermediate Similarity NPC31985
0.7282 Intermediate Similarity NPC127063
0.7273 Intermediate Similarity NPC58063
0.7273 Intermediate Similarity NPC287079
0.7273 Intermediate Similarity NPC475740
0.7273 Intermediate Similarity NPC136548
0.7273 Intermediate Similarity NPC141292
0.7265 Intermediate Similarity NPC290261
0.7255 Intermediate Similarity NPC12722
0.7245 Intermediate Similarity NPC470574
0.7245 Intermediate Similarity NPC197823
0.7245 Intermediate Similarity NPC470177
0.7238 Intermediate Similarity NPC471717
0.7238 Intermediate Similarity NPC235464
0.7238 Intermediate Similarity NPC166745
0.7238 Intermediate Similarity NPC147954
0.7222 Intermediate Similarity NPC173321
0.7216 Intermediate Similarity NPC476082
0.7216 Intermediate Similarity NPC278648
0.7216 Intermediate Similarity NPC470165
0.7204 Intermediate Similarity NPC470525
0.72 Intermediate Similarity NPC131470
0.72 Intermediate Similarity NPC143767
0.72 Intermediate Similarity NPC471724
0.72 Intermediate Similarity NPC310752
0.72 Intermediate Similarity NPC44181
0.72 Intermediate Similarity NPC292491
0.7188 Intermediate Similarity NPC225515
0.7188 Intermediate Similarity NPC101012
0.7188 Intermediate Similarity NPC55869
0.7184 Intermediate Similarity NPC474690
0.7184 Intermediate Similarity NPC49670
0.7184 Intermediate Similarity NPC473162
0.7184 Intermediate Similarity NPC299100
0.7184 Intermediate Similarity NPC166906
0.7182 Intermediate Similarity NPC295244
0.7172 Intermediate Similarity NPC89077
0.717 Intermediate Similarity NPC474720
0.717 Intermediate Similarity NPC327431
0.717 Intermediate Similarity NPC112167
0.717 Intermediate Similarity NPC157787
0.7158 Intermediate Similarity NPC27817
0.7158 Intermediate Similarity NPC229204
0.7157 Intermediate Similarity NPC272746
0.7157 Intermediate Similarity NPC131872
0.7157 Intermediate Similarity NPC19114
0.7157 Intermediate Similarity NPC473998
0.7157 Intermediate Similarity NPC99380
0.7143 Intermediate Similarity NPC108078
0.7143 Intermediate Similarity NPC237712
0.7143 Intermediate Similarity NPC85774
0.7143 Intermediate Similarity NPC472265
0.7143 Intermediate Similarity NPC221758
0.7143 Intermediate Similarity NPC59453
0.7143 Intermediate Similarity NPC214043
0.7143 Intermediate Similarity NPC161147
0.7143 Intermediate Similarity NPC473161
0.713 Intermediate Similarity NPC111323
0.7129 Intermediate Similarity NPC77168
0.7129 Intermediate Similarity NPC84271
0.7129 Intermediate Similarity NPC186688
0.7129 Intermediate Similarity NPC268406
0.7129 Intermediate Similarity NPC473999
0.7129 Intermediate Similarity NPC76879
0.7129 Intermediate Similarity NPC309603
0.7129 Intermediate Similarity NPC26959
0.7129 Intermediate Similarity NPC102414
0.7115 Intermediate Similarity NPC279313
0.7115 Intermediate Similarity NPC470016
0.7115 Intermediate Similarity NPC317586
0.7115 Intermediate Similarity NPC473170
0.7115 Intermediate Similarity NPC139459
0.7115 Intermediate Similarity NPC180950
0.7113 Intermediate Similarity NPC48362
0.7105 Intermediate Similarity NPC82759
0.7103 Intermediate Similarity NPC99411
0.71 Intermediate Similarity NPC475772
0.7091 Intermediate Similarity NPC472925
0.7087 Intermediate Similarity NPC475255
0.7087 Intermediate Similarity NPC472942
0.7087 Intermediate Similarity NPC69454
0.7083 Intermediate Similarity NPC108955
0.7075 Intermediate Similarity NPC103051
0.7071 Intermediate Similarity NPC469948
0.7071 Intermediate Similarity NPC132228
0.7071 Intermediate Similarity NPC8518
0.7071 Intermediate Similarity NPC36350
0.7071 Intermediate Similarity NPC202868
0.7071 Intermediate Similarity NPC263997
0.7071 Intermediate Similarity NPC15807
0.7064 Intermediate Similarity NPC2436
0.7064 Intermediate Similarity NPC213366
0.7064 Intermediate Similarity NPC216245
0.7064 Intermediate Similarity NPC470251
0.7064 Intermediate Similarity NPC135854
0.7059 Intermediate Similarity NPC69622
0.7059 Intermediate Similarity NPC474209
0.7059 Intermediate Similarity NPC475823
0.7059 Intermediate Similarity NPC183283
0.7059 Intermediate Similarity NPC477711
0.7059 Intermediate Similarity NPC48010
0.7053 Intermediate Similarity NPC189485
0.7053 Intermediate Similarity NPC475994
0.7048 Intermediate Similarity NPC301534
0.7048 Intermediate Similarity NPC250757
0.7048 Intermediate Similarity NPC192428
0.7048 Intermediate Similarity NPC249954
0.7048 Intermediate Similarity NPC471463
0.7037 Intermediate Similarity NPC53222
0.7037 Intermediate Similarity NPC473424
0.703 Intermediate Similarity NPC230387
0.703 Intermediate Similarity NPC475001
0.703 Intermediate Similarity NPC472802
0.703 Intermediate Similarity NPC328539
0.703 Intermediate Similarity NPC185059
0.703 Intermediate Similarity NPC242864
0.7021 Intermediate Similarity NPC250621
0.7021 Intermediate Similarity NPC110725
0.7019 Intermediate Similarity NPC217624
0.7019 Intermediate Similarity NPC8993
0.7019 Intermediate Similarity NPC473172
0.7019 Intermediate Similarity NPC111015
0.7019 Intermediate Similarity NPC181393
0.7019 Intermediate Similarity NPC78159
0.7019 Intermediate Similarity NPC469406
0.7018 Intermediate Similarity NPC472929
0.7018 Intermediate Similarity NPC472926
0.701 Intermediate Similarity NPC116797
0.701 Intermediate Similarity NPC121984
0.7009 Intermediate Similarity NPC88198
0.7009 Intermediate Similarity NPC144956
0.7009 Intermediate Similarity NPC266955
0.7 Intermediate Similarity NPC327115
0.7 Intermediate Similarity NPC20688
0.7 Intermediate Similarity NPC472974
0.7 Intermediate Similarity NPC94755
0.7 Intermediate Similarity NPC94666
0.6991 Remote Similarity NPC472928
0.699 Remote Similarity NPC233116
0.699 Remote Similarity NPC110657
0.699 Remote Similarity NPC174167
0.699 Remote Similarity NPC86266
0.699 Remote Similarity NPC63748
0.699 Remote Similarity NPC26888
0.699 Remote Similarity NPC155304
0.699 Remote Similarity NPC470036
0.699 Remote Similarity NPC473167
0.699 Remote Similarity NPC248913
0.699 Remote Similarity NPC212301
0.699 Remote Similarity NPC475806

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC471815 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
0.7826 Intermediate Similarity NPD8259 Clinical (unspecified phase)
0.7708 Intermediate Similarity NPD5279 Phase 3
0.7212 Intermediate Similarity NPD5220 Clinical (unspecified phase)
0.7212 Intermediate Similarity NPD5222 Approved
0.7212 Intermediate Similarity NPD5221 Approved
0.7157 Intermediate Similarity NPD6079 Approved
0.7143 Intermediate Similarity NPD4786 Approved
0.7143 Intermediate Similarity NPD5173 Approved
0.7129 Intermediate Similarity NPD5328 Approved
0.7083 Intermediate Similarity NPD4695 Discontinued
0.7071 Intermediate Similarity NPD1696 Phase 3
0.7048 Intermediate Similarity NPD4697 Phase 3
0.7009 Intermediate Similarity NPD5285 Approved
0.7009 Intermediate Similarity NPD5286 Approved
0.7009 Intermediate Similarity NPD4696 Approved
0.7 Intermediate Similarity NPD3618 Phase 1
0.7 Intermediate Similarity NPD4694 Approved
0.7 Intermediate Similarity NPD5280 Approved
0.6981 Remote Similarity NPD4755 Approved
0.6961 Remote Similarity NPD4753 Phase 2
0.6961 Remote Similarity NPD7285 Clinical (unspecified phase)
0.6944 Remote Similarity NPD5223 Approved
0.6939 Remote Similarity NPD3667 Approved
0.6881 Remote Similarity NPD5226 Approved
0.6881 Remote Similarity NPD5211 Phase 2
0.6881 Remote Similarity NPD4633 Approved
0.6881 Remote Similarity NPD5224 Approved
0.6881 Remote Similarity NPD5225 Approved
0.6852 Remote Similarity NPD4700 Approved
0.6832 Remote Similarity NPD5690 Phase 2
0.6818 Remote Similarity NPD5174 Approved
0.6818 Remote Similarity NPD5175 Approved
0.68 Remote Similarity NPD3666 Approved
0.68 Remote Similarity NPD3665 Phase 1
0.68 Remote Similarity NPD3133 Approved
0.6792 Remote Similarity NPD4629 Approved
0.6792 Remote Similarity NPD5210 Approved
0.6783 Remote Similarity NPD8297 Approved
0.6762 Remote Similarity NPD4202 Approved
0.6757 Remote Similarity NPD5141 Approved
0.6733 Remote Similarity NPD5329 Approved
0.6726 Remote Similarity NPD4729 Approved
0.6726 Remote Similarity NPD6881 Approved
0.6726 Remote Similarity NPD4730 Approved
0.6726 Remote Similarity NPD7320 Approved
0.6726 Remote Similarity NPD6899 Approved
0.6701 Remote Similarity NPD3617 Approved
0.6699 Remote Similarity NPD4518 Approved
0.6696 Remote Similarity NPD6675 Approved
0.6696 Remote Similarity NPD6649 Approved
0.6696 Remote Similarity NPD7128 Approved
0.6696 Remote Similarity NPD6650 Approved
0.6696 Remote Similarity NPD6402 Approved
0.6696 Remote Similarity NPD4768 Approved
0.6696 Remote Similarity NPD4767 Approved
0.6696 Remote Similarity NPD8130 Phase 1
0.6696 Remote Similarity NPD5739 Approved
0.6667 Remote Similarity NPD6084 Phase 2
0.6667 Remote Similarity NPD6083 Phase 2
0.6667 Remote Similarity NPD6372 Approved
0.6667 Remote Similarity NPD6373 Approved
0.6667 Remote Similarity NPD6411 Approved
0.6667 Remote Similarity NPD4754 Approved
0.6667 Remote Similarity NPD7515 Phase 2
0.6638 Remote Similarity NPD6882 Approved
0.6637 Remote Similarity NPD5697 Approved
0.6636 Remote Similarity NPD5695 Phase 3
0.6634 Remote Similarity NPD4197 Approved
0.6609 Remote Similarity NPD5247 Approved
0.6609 Remote Similarity NPD5249 Phase 3
0.6609 Remote Similarity NPD7290 Approved
0.6609 Remote Similarity NPD5251 Approved
0.6609 Remote Similarity NPD5250 Approved
0.6609 Remote Similarity NPD5248 Approved
0.6609 Remote Similarity NPD7102 Approved
0.6609 Remote Similarity NPD6883 Approved
0.6604 Remote Similarity NPD5133 Approved
0.6604 Remote Similarity NPD6399 Phase 3
0.6579 Remote Similarity NPD6011 Approved
0.6579 Remote Similarity NPD5168 Approved
0.6579 Remote Similarity NPD5128 Approved
0.6562 Remote Similarity NPD8264 Approved
0.6552 Remote Similarity NPD6617 Approved
0.6552 Remote Similarity NPD6869 Approved
0.6552 Remote Similarity NPD6847 Approved
0.6542 Remote Similarity NPD5282 Discontinued
0.6542 Remote Similarity NPD7748 Approved
0.6538 Remote Similarity NPD5737 Approved
0.6538 Remote Similarity NPD6672 Approved
0.6522 Remote Similarity NPD6012 Approved
0.6522 Remote Similarity NPD6013 Approved
0.6522 Remote Similarity NPD6014 Approved
0.6509 Remote Similarity NPD6050 Approved
0.6509 Remote Similarity NPD5284 Approved
0.6509 Remote Similarity NPD5281 Approved
0.6505 Remote Similarity NPD3574 Clinical (unspecified phase)
0.6491 Remote Similarity NPD5701 Approved
0.6476 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6476 Remote Similarity NPD6101 Approved
0.6471 Remote Similarity NPD3668 Phase 3
0.6466 Remote Similarity NPD5134 Clinical (unspecified phase)
0.6466 Remote Similarity NPD4634 Approved
0.6466 Remote Similarity NPD5169 Approved
0.6466 Remote Similarity NPD5135 Approved
0.6458 Remote Similarity NPD6926 Approved
0.6458 Remote Similarity NPD5733 Approved
0.6458 Remote Similarity NPD6924 Approved
0.6444 Remote Similarity NPD2664 Clinical (unspecified phase)
0.6436 Remote Similarity NPD4223 Phase 3
0.6436 Remote Similarity NPD4221 Approved
0.6421 Remote Similarity NPD5276 Approved
0.6421 Remote Similarity NPD7152 Approved
0.6421 Remote Similarity NPD7151 Approved
0.6421 Remote Similarity NPD7150 Approved
0.6415 Remote Similarity NPD4096 Approved
0.6415 Remote Similarity NPD5692 Phase 3
0.641 Remote Similarity NPD5217 Approved
0.641 Remote Similarity NPD6401 Clinical (unspecified phase)
0.641 Remote Similarity NPD5216 Approved
0.641 Remote Similarity NPD5215 Approved
0.641 Remote Similarity NPD5127 Approved
0.64 Remote Similarity NPD7509 Discontinued
0.6383 Remote Similarity NPD6923 Approved
0.6383 Remote Similarity NPD6922 Approved
0.6373 Remote Similarity NPD5362 Discontinued
0.6373 Remote Similarity NPD4788 Approved
0.6364 Remote Similarity NPD5784 Clinical (unspecified phase)
0.6364 Remote Similarity NPD7902 Approved
0.6355 Remote Similarity NPD5694 Approved
0.6333 Remote Similarity NPD6868 Approved
0.633 Remote Similarity NPD1698 Clinical (unspecified phase)
0.6327 Remote Similarity NPD6933 Approved
0.6316 Remote Similarity NPD7143 Approved
0.6316 Remote Similarity NPD7144 Approved
0.6306 Remote Similarity NPD5696 Approved
0.6303 Remote Similarity NPD4632 Approved
0.6296 Remote Similarity NPD5779 Approved
0.6296 Remote Similarity NPD5778 Approved
0.6289 Remote Similarity NPD4687 Approved
0.6262 Remote Similarity NPD5785 Approved
0.626 Remote Similarity NPD6054 Approved
0.625 Remote Similarity NPD5167 Approved
0.625 Remote Similarity NPD5363 Approved
0.6237 Remote Similarity NPD3704 Approved
0.623 Remote Similarity NPD6335 Approved
0.6226 Remote Similarity NPD6903 Approved
0.6224 Remote Similarity NPD7339 Approved
0.6224 Remote Similarity NPD6942 Approved
0.6207 Remote Similarity NPD7899 Clinical (unspecified phase)
0.62 Remote Similarity NPD7322 Clinical (unspecified phase)
0.6198 Remote Similarity NPD6274 Approved
0.619 Remote Similarity NPD4688 Approved
0.619 Remote Similarity NPD7334 Approved
0.619 Remote Similarity NPD5330 Approved
0.619 Remote Similarity NPD7146 Approved
0.619 Remote Similarity NPD4690 Approved
0.619 Remote Similarity NPD4693 Phase 3
0.619 Remote Similarity NPD6409 Approved
0.619 Remote Similarity NPD5205 Approved
0.619 Remote Similarity NPD4689 Approved
0.619 Remote Similarity NPD7521 Approved
0.619 Remote Similarity NPD6684 Approved
0.619 Remote Similarity NPD4138 Approved
0.6186 Remote Similarity NPD6371 Approved
0.6182 Remote Similarity NPD5654 Approved
0.6179 Remote Similarity NPD7101 Approved
0.6179 Remote Similarity NPD7100 Approved
0.6168 Remote Similarity NPD6080 Approved
0.6168 Remote Similarity NPD6904 Approved
0.6168 Remote Similarity NPD6673 Approved
0.616 Remote Similarity NPD6370 Approved
0.6148 Remote Similarity NPD6009 Approved
0.6148 Remote Similarity NPD6317 Approved
0.6148 Remote Similarity NPD7115 Discovery
0.6139 Remote Similarity NPD6929 Approved
0.6129 Remote Similarity NPD6319 Approved
0.6129 Remote Similarity NPD6059 Approved
0.6122 Remote Similarity NPD4058 Approved
0.6111 Remote Similarity NPD5207 Approved
0.61 Remote Similarity NPD4756 Discovery
0.61 Remote Similarity NPD5776 Phase 2
0.61 Remote Similarity NPD6925 Approved
0.61 Remote Similarity NPD6932 Approved
0.6098 Remote Similarity NPD6314 Approved
0.6098 Remote Similarity NPD6313 Approved
0.6095 Remote Similarity NPD7520 Clinical (unspecified phase)
0.6091 Remote Similarity NPD7901 Clinical (unspecified phase)
0.6091 Remote Similarity NPD7900 Approved
0.608 Remote Similarity NPD6016 Approved
0.608 Remote Similarity NPD6291 Clinical (unspecified phase)
0.608 Remote Similarity NPD6015 Approved
0.6078 Remote Similarity NPD6930 Phase 2
0.6078 Remote Similarity NPD7525 Registered
0.6078 Remote Similarity NPD6931 Approved
0.6078 Remote Similarity NPD7332 Phase 2
0.6075 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6071 Remote Similarity NPD5959 Approved
0.6064 Remote Similarity NPD7331 Phase 2
0.6063 Remote Similarity NPD7492 Approved
0.6058 Remote Similarity NPD6695 Phase 3

Structure

External Identifiers

PubChem CID   90670424
ChEMBL   CHEMBL3234413
ZINC  

Physicochemical Properties

Molecular Weight:  660.37
ALogP:  0.5989
MLogP:  4.98
XLogP:  5.652
# Rotatable Bonds:  17
Polar Surface Area:  149.2
# H-Bond Aceptor:  8
# H-Bond Donor:  4
# Rings:  6
# Heavy Atoms:  48

Download Data

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