Natural Product: NPC471547

Natural Product ID:  NPC471547
Common Name:   2-O-Methyl 4A-O-[(2S,3R,4S,5S,6R)-3,4,5-Trihydroxy-6-(Hydroxymethyl)Oxan-2-Yl] (2S,4Ar,6Ar,6As,6Br,8Ar,9R,10R,11S,12As,13R,14Bs)-10-[(2S,3R,4R,5R)-3,4-Dihydroxy-5-[(2S,3R,4S,5S,6R)-3,4,5-Trihydroxy-6-(Hydroxymethyl)Oxan-2-Yl]Oxyoxan-2-Yl]Oxy-11,13-Dihydroxy-9-(Hydroxymethyl)-2,6A,6B,9,12A-Pentamethyl-1,3,4,5,6,6A,7,8,8A,10,11,12,13,14B-Tetradecahydropicene-2,4A-Dicarboxylate
IUPAC Name:   2-O-methyl 4a-O-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (2S,4aR,6aR,6aS,6bR,8aR,9R,10R,11S,12aS,13R,14bS)-10-[(2S,3R,4R,5R)-3,4-dihydroxy-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-11,13-dihydroxy-9-(hydroxymethyl)-2,6a,6b,9,12a-pentamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-2,4a-dicarboxylate
Synonyms:  
Molecular Formula:   C48H76O22
Standard InCHIKey:  QCEJNSUFOBLNLD-MTJZKYCXSA-N
Standard InCHI:  InChI=1S/C48H76O22/c1-43(41(62)64-6)9-11-48(42(63)70-40-35(61)32(58)29(55)25(17-50)67-40)12-10-46(4)20(21(48)14-43)13-22(52)36-44(2)15-23(53)37(45(3,19-51)27(44)7-8-47(36,46)5)69-38-33(59)30(56)26(18-65-38)68-39-34(60)31(57)28(54)24(16-49)66-39/h13,21-40,49-61H,7-12,14-19H2,1-6H3/t21-,22+,23-,24+,25+,26+,27+,28+,29+,30-,31-,32-,33+,34+,35+,36+,37-,38-,39-,40-,43-,44-,45-,46+,47+,48-/m0/s1
Canonical SMILES:  OC[C@H]1O[C@@H](O[C@@H]2CO[C@H]([C@@H]([C@H]2O)O)O[C@H]2[C@@H](O)C[C@]3([C@H]([C@]2(C)CO)CC[C@@]2([C@@H]3[C@H](O)C=C3[C@@]2(C)CC[C@@]2([C@H]3C[C@](C)(CC2)C(=O)OC)C(=O)O[C@@H]2O[C@H](CO)[C@H]([C@@H]([C@H]2O)O)O)C)C)[C@@H]([C@H]([C@@H]1O)O)O
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
NPO17551 Phytolacca americana Species Phytolaccaceae Eukaryota roots PMID[18177012]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT81 Cell Line A549 Homo sapiens Activity > 100 nM 16413779
NPT1374 Cell Line WI-38 Homo sapiens IC50 > 100000 nM 16413779
NPT1475 Cell Line WI-38 VA13 Homo sapiens IC50 = 94000 nM 16413779
NPT65 Cell Line HepG2 Homo sapiens IC50 > 100000 nM 16413779
NPT668 Individual Protein P-glycoprotein 1 Homo sapiens Activity = 121 % 8893846
NPT668 Individual Protein P-glycoprotein 1 Homo sapiens Activity = 119 % 8893846
NPT668 Individual Protein P-glycoprotein 1 Homo sapiens Activity = 124 % 8893846
NPT81 Cell Line A549 Homo sapiens Activity > 100 nM 17417907

  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 NPC471547 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
0.9725 High Similarity NPC471548
0.972 High Similarity NPC96641
0.972 High Similarity NPC473343
0.972 High Similarity NPC163183
0.972 High Similarity NPC150400
0.972 High Similarity NPC134835
0.972 High Similarity NPC73318
0.9633 High Similarity NPC473405
0.9626 High Similarity NPC104400
0.9626 High Similarity NPC471383
0.9626 High Similarity NPC104071
0.9626 High Similarity NPC324875
0.9626 High Similarity NPC276093
0.9626 High Similarity NPC109079
0.9626 High Similarity NPC79718
0.9626 High Similarity NPC473383
0.9626 High Similarity NPC475504
0.9626 High Similarity NPC292677
0.9626 High Similarity NPC101744
0.9626 High Similarity NPC473373
0.9626 High Similarity NPC10320
0.9626 High Similarity NPC139044
0.9626 High Similarity NPC469946
0.9626 High Similarity NPC102439
0.9626 High Similarity NPC257468
0.9626 High Similarity NPC139894
0.9626 High Similarity NPC475516
0.9537 High Similarity NPC309714
0.9537 High Similarity NPC46665
0.9537 High Similarity NPC114304
0.9537 High Similarity NPC251263
0.9537 High Similarity NPC475287
0.9537 High Similarity NPC475467
0.9537 High Similarity NPC258885
0.9537 High Similarity NPC133818
0.9537 High Similarity NPC114287
0.9537 High Similarity NPC151543
0.9537 High Similarity NPC219180
0.9537 High Similarity NPC192600
0.9537 High Similarity NPC323341
0.9537 High Similarity NPC124296
0.9537 High Similarity NPC166422
0.9537 High Similarity NPC174720
0.9537 High Similarity NPC241909
0.9537 High Similarity NPC295823
0.9537 High Similarity NPC155410
0.9537 High Similarity NPC473826
0.9533 High Similarity NPC179434
0.9533 High Similarity NPC164419
0.9455 High Similarity NPC300419
0.945 High Similarity NPC475486
0.945 High Similarity NPC70809
0.945 High Similarity NPC67857
0.945 High Similarity NPC476068
0.945 High Similarity NPC204414
0.945 High Similarity NPC469782
0.945 High Similarity NPC161717
0.945 High Similarity NPC250247
0.945 High Similarity NPC471385
0.945 High Similarity NPC57484
0.945 High Similarity NPC294453
0.945 High Similarity NPC224381
0.945 High Similarity NPC76972
0.945 High Similarity NPC227551
0.945 High Similarity NPC473714
0.945 High Similarity NPC54636
0.945 High Similarity NPC471550
0.945 High Similarity NPC100639
0.945 High Similarity NPC309907
0.945 High Similarity NPC305981
0.945 High Similarity NPC298034
0.945 High Similarity NPC60557
0.945 High Similarity NPC65105
0.945 High Similarity NPC79643
0.945 High Similarity NPC119592
0.945 High Similarity NPC475160
0.945 High Similarity NPC236638
0.945 High Similarity NPC123199
0.945 High Similarity NPC261506
0.945 High Similarity NPC202828
0.945 High Similarity NPC164389
0.945 High Similarity NPC293330
0.945 High Similarity NPC43550
0.945 High Similarity NPC71065
0.945 High Similarity NPC4328
0.945 High Similarity NPC475140
0.945 High Similarity NPC41061
0.9439 High Similarity NPC56713
0.9439 High Similarity NPC68419
0.9439 High Similarity NPC136877
0.9439 High Similarity NPC174679
0.9439 High Similarity NPC475296
0.9439 High Similarity NPC7870
0.9439 High Similarity NPC59804
0.9439 High Similarity NPC90856
0.9439 High Similarity NPC108709
0.9439 High Similarity NPC279554
0.9439 High Similarity NPC270667
0.9439 High Similarity NPC199457
0.9439 High Similarity NPC474589
0.9439 High Similarity NPC102914
0.9439 High Similarity NPC29069
0.9439 High Similarity NPC75747
0.9439 High Similarity NPC110139
0.9439 High Similarity NPC164194
0.9439 High Similarity NPC127056
0.9375 High Similarity NPC268184
0.9369 High Similarity NPC237191
0.9369 High Similarity NPC475899
0.9364 High Similarity NPC37134
0.9364 High Similarity NPC75287
0.9364 High Similarity NPC476992
0.9364 High Similarity NPC160415
0.9364 High Similarity NPC161674
0.9364 High Similarity NPC305267
0.9364 High Similarity NPC58448
0.9364 High Similarity NPC26626
0.9364 High Similarity NPC288205
0.9364 High Similarity NPC471384
0.9364 High Similarity NPC291903
0.9364 High Similarity NPC51465
0.9358 High Similarity NPC475208
0.9358 High Similarity NPC238935
0.9352 High Similarity NPC30397
0.9352 High Similarity NPC108748
0.9352 High Similarity NPC211798
0.9352 High Similarity NPC235841
0.9352 High Similarity NPC473481
0.9352 High Similarity NPC297208
0.9346 High Similarity NPC237503
0.9346 High Similarity NPC167383
0.9346 High Similarity NPC57362
0.9346 High Similarity NPC306746
0.9346 High Similarity NPC204407
0.9346 High Similarity NPC127853
0.9286 High Similarity NPC477464
0.9286 High Similarity NPC471577
0.9286 High Similarity NPC473401
0.9279 High Similarity NPC475119
0.9279 High Similarity NPC323359
0.9279 High Similarity NPC185466
0.9279 High Similarity NPC470876
0.9279 High Similarity NPC286457
0.9279 High Similarity NPC309223
0.9279 High Similarity NPC475514
0.9279 High Similarity NPC68175
0.9279 High Similarity NPC33012
0.9279 High Similarity NPC69811
0.9279 High Similarity NPC191827
0.9279 High Similarity NPC473452
0.9279 High Similarity NPC8524
0.9279 High Similarity NPC85154
0.9279 High Similarity NPC148417
0.9279 High Similarity NPC104137
0.9279 High Similarity NPC473824
0.9279 High Similarity NPC475209
0.9279 High Similarity NPC136768
0.9279 High Similarity NPC102505
0.9279 High Similarity NPC110633
0.9279 High Similarity NPC123522
0.9279 High Similarity NPC220160
0.9266 High Similarity NPC116794
0.9266 High Similarity NPC48249
0.9266 High Similarity NPC1046
0.9266 High Similarity NPC80843
0.9266 High Similarity NPC256798
0.9266 High Similarity NPC128925
0.9259 High Similarity NPC476882
0.9259 High Similarity NPC476887
0.9259 High Similarity NPC476883
0.9259 High Similarity NPC220984
0.9259 High Similarity NPC476884
0.9259 High Similarity NPC274507
0.9259 High Similarity NPC476886
0.9259 High Similarity NPC269095
0.9259 High Similarity NPC476880
0.9259 High Similarity NPC476885
0.9259 High Similarity NPC476881
0.9259 High Similarity NPC78046
0.9252 High Similarity NPC476123
0.9252 High Similarity NPC284807
0.9252 High Similarity NPC177246
0.9252 High Similarity NPC28198
0.9204 High Similarity NPC37860
0.9204 High Similarity NPC144644
0.9204 High Similarity NPC473645
0.9204 High Similarity NPC110385
0.9204 High Similarity NPC142151
0.9204 High Similarity NPC267694
0.9204 High Similarity NPC153673
0.9196 High Similarity NPC473459
0.9196 High Similarity NPC109588
0.9196 High Similarity NPC232237
0.9196 High Similarity NPC276758
0.9196 High Similarity NPC18233
0.9196 High Similarity NPC36831
0.9196 High Similarity NPC105800
0.9182 High Similarity NPC47063
0.9182 High Similarity NPC271138
0.9182 High Similarity NPC138334

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC471547 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
0.8649 High Similarity NPD8132 Clinical (unspecified phase)
0.8644 High Similarity NPD8328 Phase 3
0.8509 High Similarity NPD8133 Approved
0.8448 Intermediate Similarity NPD8295 Clinical (unspecified phase)
0.8083 Intermediate Similarity NPD8377 Approved
0.8083 Intermediate Similarity NPD8294 Approved
0.807 Intermediate Similarity NPD6686 Approved
0.8017 Intermediate Similarity NPD8296 Approved
0.8017 Intermediate Similarity NPD8335 Approved
0.8017 Intermediate Similarity NPD8379 Approved
0.8017 Intermediate Similarity NPD8380 Approved
0.8017 Intermediate Similarity NPD8378 Approved
0.7903 Intermediate Similarity NPD7507 Approved
0.7869 Intermediate Similarity NPD8513 Phase 3
0.7869 Intermediate Similarity NPD8516 Approved
0.7869 Intermediate Similarity NPD8033 Approved
0.7869 Intermediate Similarity NPD8517 Approved
0.7869 Intermediate Similarity NPD8515 Approved
0.7826 Intermediate Similarity NPD6412 Phase 2
0.7717 Intermediate Similarity NPD7319 Approved
0.7705 Intermediate Similarity NPD7516 Approved
0.7636 Intermediate Similarity NPD7748 Approved
0.7623 Intermediate Similarity NPD7327 Approved
0.7623 Intermediate Similarity NPD7328 Approved
0.7589 Intermediate Similarity NPD7902 Approved
0.7455 Intermediate Similarity NPD7515 Phase 2
0.744 Intermediate Similarity NPD7503 Approved
0.7417 Intermediate Similarity NPD8413 Clinical (unspecified phase)
0.7364 Intermediate Similarity NPD7736 Approved
0.7321 Intermediate Similarity NPD7900 Approved
0.7321 Intermediate Similarity NPD7901 Clinical (unspecified phase)
0.7304 Intermediate Similarity NPD7640 Approved
0.7304 Intermediate Similarity NPD7639 Approved
0.725 Intermediate Similarity NPD4061 Clinical (unspecified phase)
0.7217 Intermediate Similarity NPD7638 Approved
0.7203 Intermediate Similarity NPD8170 Clinical (unspecified phase)
0.7154 Intermediate Similarity NPD8293 Discontinued
0.7049 Intermediate Similarity NPD5955 Clinical (unspecified phase)
0.7025 Intermediate Similarity NPD5345 Clinical (unspecified phase)
0.6991 Remote Similarity NPD8035 Phase 2
0.6991 Remote Similarity NPD8034 Phase 2
0.6984 Remote Similarity NPD7115 Discovery
0.6977 Remote Similarity NPD6370 Approved
0.6935 Remote Similarity NPD6882 Approved
0.6935 Remote Similarity NPD8297 Approved
0.6894 Remote Similarity NPD8074 Phase 3
0.687 Remote Similarity NPD7492 Approved
0.685 Remote Similarity NPD6009 Approved
0.6822 Remote Similarity NPD7645 Phase 2
0.6822 Remote Similarity NPD6054 Approved
0.6822 Remote Similarity NPD6319 Approved
0.6822 Remote Similarity NPD6059 Approved
0.6818 Remote Similarity NPD6616 Approved
0.6803 Remote Similarity NPD5954 Clinical (unspecified phase)
0.6794 Remote Similarity NPD6067 Discontinued
0.6783 Remote Similarity NPD8171 Discontinued
0.6783 Remote Similarity NPD6399 Phase 3
0.678 Remote Similarity NPD4225 Approved
0.6767 Remote Similarity NPD7078 Approved
0.6757 Remote Similarity NPD7520 Clinical (unspecified phase)
0.6754 Remote Similarity NPD46 Approved
0.6754 Remote Similarity NPD6698 Approved
0.675 Remote Similarity NPD7632 Discontinued
0.6746 Remote Similarity NPD4632 Approved
0.6721 Remote Similarity NPD6402 Approved
0.6721 Remote Similarity NPD5739 Approved
0.6721 Remote Similarity NPD7128 Approved
0.6721 Remote Similarity NPD6675 Approved
0.6696 Remote Similarity NPD7983 Approved
0.6694 Remote Similarity NPD6372 Approved
0.6694 Remote Similarity NPD6373 Approved
0.6641 Remote Similarity NPD6015 Approved
0.6641 Remote Similarity NPD6016 Approved
0.6639 Remote Similarity NPD8029 Clinical (unspecified phase)
0.6638 Remote Similarity NPD5778 Approved
0.6638 Remote Similarity NPD5779 Approved
0.6613 Remote Similarity NPD7320 Approved
0.6613 Remote Similarity NPD6899 Approved
0.6613 Remote Similarity NPD6881 Approved
0.6591 Remote Similarity NPD5988 Approved
0.6587 Remote Similarity NPD6649 Approved
0.6587 Remote Similarity NPD6650 Approved
0.6587 Remote Similarity NPD8130 Phase 1
0.6552 Remote Similarity NPD6411 Approved
0.6532 Remote Similarity NPD5697 Approved
0.6532 Remote Similarity NPD5701 Approved
0.6529 Remote Similarity NPD5344 Discontinued
0.6515 Remote Similarity NPD6921 Approved
0.6508 Remote Similarity NPD7290 Approved
0.6508 Remote Similarity NPD6883 Approved
0.6508 Remote Similarity NPD7102 Approved
0.6507 Remote Similarity NPD7625 Phase 1
0.6475 Remote Similarity NPD8450 Suspended
0.6457 Remote Similarity NPD6847 Approved
0.6457 Remote Similarity NPD6617 Approved
0.6457 Remote Similarity NPD6869 Approved
0.6435 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6429 Remote Similarity NPD6012 Approved
0.6429 Remote Similarity NPD6013 Approved
0.6429 Remote Similarity NPD6014 Approved
0.6418 Remote Similarity NPD7604 Phase 2
0.6417 Remote Similarity NPD6084 Phase 2
0.6417 Remote Similarity NPD6083 Phase 2
0.6404 Remote Similarity NPD3618 Phase 1
0.6403 Remote Similarity NPD8449 Approved
0.6391 Remote Similarity NPD5983 Phase 2
0.6379 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6379 Remote Similarity NPD6101 Approved
0.6379 Remote Similarity NPD5328 Approved
0.6372 Remote Similarity NPD4786 Approved
0.637 Remote Similarity NPD8342 Approved
0.637 Remote Similarity NPD8340 Approved
0.637 Remote Similarity NPD8299 Approved
0.637 Remote Similarity NPD8341 Approved
0.635 Remote Similarity NPD6033 Approved
0.6349 Remote Similarity NPD6011 Approved
0.6348 Remote Similarity NPD3573 Approved
0.6341 Remote Similarity NPD5211 Phase 2
0.6339 Remote Similarity NPD3667 Approved
0.6333 Remote Similarity NPD7839 Suspended
0.6328 Remote Similarity NPD6401 Clinical (unspecified phase)
0.6324 Remote Similarity NPD6336 Discontinued
0.632 Remote Similarity NPD6008 Approved
0.6283 Remote Similarity NPD3670 Clinical (unspecified phase)
0.6283 Remote Similarity NPD3669 Approved
0.6281 Remote Similarity NPD4755 Approved
0.6277 Remote Similarity NPD8448 Approved
0.6271 Remote Similarity NPD7637 Suspended
0.6271 Remote Similarity NPD6079 Approved
0.6268 Remote Similarity NPD8387 Clinical (unspecified phase)
0.6261 Remote Similarity NPD6409 Approved
0.6261 Remote Similarity NPD7146 Approved
0.6261 Remote Similarity NPD5330 Approved
0.6261 Remote Similarity NPD7521 Approved
0.6261 Remote Similarity NPD7334 Approved
0.6261 Remote Similarity NPD6684 Approved
0.626 Remote Similarity NPD6940 Discontinued
0.6259 Remote Similarity NPD8391 Approved
0.6259 Remote Similarity NPD8392 Approved
0.6259 Remote Similarity NPD8390 Approved
0.625 Remote Similarity NPD4634 Approved
0.624 Remote Similarity NPD5141 Approved
0.6239 Remote Similarity NPD7285 Clinical (unspecified phase)
0.6218 Remote Similarity NPD4202 Approved
0.6207 Remote Similarity NPD7524 Approved
0.6204 Remote Similarity NPD8451 Approved
0.6186 Remote Similarity NPD7838 Discovery
0.6179 Remote Similarity NPD5285 Approved
0.6179 Remote Similarity NPD5286 Approved
0.6179 Remote Similarity NPD4700 Approved
0.6179 Remote Similarity NPD4696 Approved
0.6179 Remote Similarity NPD6648 Approved
0.6176 Remote Similarity NPD7830 Approved
0.6176 Remote Similarity NPD7829 Approved
0.6161 Remote Similarity NPD7525 Registered
0.6154 Remote Similarity NPD6903 Approved
0.6154 Remote Similarity NPD6053 Discontinued
0.6154 Remote Similarity NPD5737 Approved
0.6154 Remote Similarity NPD6672 Approved
0.6148 Remote Similarity NPD8444 Approved
0.6136 Remote Similarity NPD6274 Approved
0.6126 Remote Similarity NPD6697 Approved
0.6126 Remote Similarity NPD6118 Approved
0.6126 Remote Similarity NPD6115 Approved
0.6126 Remote Similarity NPD6114 Approved
0.6124 Remote Similarity NPD6371 Approved
0.6119 Remote Similarity NPD7101 Approved
0.6119 Remote Similarity NPD7100 Approved
0.6116 Remote Similarity NPD5695 Phase 3
0.6115 Remote Similarity NPD8455 Phase 2
0.6115 Remote Similarity NPD8336 Approved
0.6115 Remote Similarity NPD8337 Approved
0.6106 Remote Similarity NPD1779 Approved
0.6106 Remote Similarity NPD1780 Approved
0.6098 Remote Similarity NPD7228 Approved
0.6098 Remote Similarity NPD5696 Approved
0.609 Remote Similarity NPD8137 Clinical (unspecified phase)
0.6087 Remote Similarity NPD3133 Approved
0.6087 Remote Similarity NPD3665 Phase 1
0.6087 Remote Similarity NPD6400 Clinical (unspecified phase)
0.6087 Remote Similarity NPD3666 Approved
0.6084 Remote Similarity NPD8415 Approved
0.608 Remote Similarity NPD5224 Approved
0.608 Remote Similarity NPD5225 Approved
0.608 Remote Similarity NPD5226 Approved
0.608 Remote Similarity NPD4633 Approved
0.6066 Remote Similarity NPD5222 Approved
0.6066 Remote Similarity NPD5220 Clinical (unspecified phase)
0.6066 Remote Similarity NPD5221 Approved
0.6066 Remote Similarity NPD4697 Phase 3
0.6063 Remote Similarity NPD4767 Approved
0.6063 Remote Similarity NPD4768 Approved
0.6061 Remote Similarity NPD8470 Clinical (unspecified phase)
0.6056 Remote Similarity NPD8338 Approved
0.6053 Remote Similarity NPD4752 Clinical (unspecified phase)
0.6045 Remote Similarity NPD6335 Approved
0.6036 Remote Similarity NPD6116 Phase 1
0.6032 Remote Similarity NPD5175 Approved
0.6032 Remote Similarity NPD5174 Approved
0.6029 Remote Similarity NPD6908 Approved

Structure

External Identifiers

PubChem CID   24770100
ChEMBL   CHEMBL256132
ZINC  

Physicochemical Properties

Molecular Weight:  1004.48
ALogP:  -5.275
MLogP:  4.32
XLogP:  -1.021
# Rotatable Bonds:  31
Polar Surface Area:  361.74
# H-Bond Aceptor:  22
# H-Bond Donor:  13
# Rings:  8
# Heavy Atoms:  70

Download Data

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