Natural Product: NPC477463

Natural Product ID:  NPC477463
Common Name:   Madhucoside A
IUPAC Name:   [(2S,3R,4S,5S)-3-[(2S,3R,4R,5R,6S)-3-[(2S,3R,4S,5R)-3-[(2S,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy-5-hydroxy-4-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-4,5-dihydroxy-6-methyloxan-2-yl]oxy-4,5-dihydroxyoxan-2-yl] (4aS,6aR,6aS,6bR,8R,8aR,9R,10R,11S,12aR,14bR)-9-[[(2R,3R,4S,5S,6R)-3-[(2S,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-8,10,11-trihydroxy-2,2,6a,6b,9,12a-hexamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylate
Synonyms:  
Molecular Formula:   C68H110O35
Standard InCHIKey:  HHOQWUGAARBPKE-ZNOJLHKGSA-N
Standard InCHI:  InChI=1S/C68H110O35/c1-26-36(76)40(80)43(83)53(95-26)98-44-33(75)20-91-56(48(44)102-59-52(86)68(89,22-71)25-94-59)99-47-41(81)37(77)27(2)96-57(47)100-45-38(78)32(74)19-90-54(45)103-60(87)66-13-11-61(3,4)15-29(66)28-9-10-35-62(5)16-31(73)50(84)63(6,49(62)30(72)17-65(35,8)64(28,7)12-14-66)23-92-55-46(42(82)39(79)34(18-69)97-55)101-58-51(85)67(88,21-70)24-93-58/h9,26-27,29-59,69-86,88-89H,10-25H2,1-8H3/t26-,27-,29+,30+,31-,32-,33+,34+,35+,36-,37-,38-,39+,40+,41+,42-,43+,44-,45+,46+,47+,48+,49+,50-,51-,52-,53-,54-,55+,56-,57-,58-,59-,62+,63-,64+,65+,66-,67+,68+/m0/s1
Canonical SMILES:  OC[C@H]1O[C@@H](OC[C@]2(C)[C@@H](O)[C@@H](O)C[C@]3([C@H]2[C@H](O)C[C@@]2([C@@H]3CC=C3[C@@]2(C)CC[C@@]2([C@@H]3CC(CC2)(C)C)C(=O)O[C@@H]2OC[C@@H]([C@@H]([C@H]2O[C@@H]2O[C@@H](C)[C@@H]([C@H]([C@H]2O[C@@H]2OC[C@H]([C@@H]([C@H]2O[C@@H]2OC[C@]([C@H]2O)(O)CO)O[C@@H]2O[C@@H](C)[C@@H]([C@H]([C@H]2O)O)O)O)O)O)O)O)C)C)[C@@H]([C@H]([C@@H]1O)O)O[C@@H]1OC[C@]([C@H]1O)(O)CO
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
NPO31375 Madhuca indica Species Sapotaceae Eukaryota PMID[15104500]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT2 Others Unspecified IC50 = 21.9 ug/ml 15104500
NPT2 Others Unspecified IC50 = 138.3 ug/ml 15104500

  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 NPC477463 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
0.982 High Similarity NPC477464
0.973 High Similarity NPC475899
0.9646 High Similarity NPC275225
0.9646 High Similarity NPC293031
0.9646 High Similarity NPC51099
0.9646 High Similarity NPC68767
0.9558 High Similarity NPC153673
0.9558 High Similarity NPC37860
0.9558 High Similarity NPC267694
0.9558 High Similarity NPC144644
0.9558 High Similarity NPC142151
0.9558 High Similarity NPC110385
0.9469 High Similarity NPC471577
0.9459 High Similarity NPC224381
0.9459 High Similarity NPC305981
0.9459 High Similarity NPC4328
0.9459 High Similarity NPC236638
0.9459 High Similarity NPC309907
0.9459 High Similarity NPC469782
0.9459 High Similarity NPC227551
0.9459 High Similarity NPC471550
0.9459 High Similarity NPC161717
0.9459 High Similarity NPC119592
0.9459 High Similarity NPC476068
0.9459 High Similarity NPC43550
0.9459 High Similarity NPC250247
0.9459 High Similarity NPC60557
0.9459 High Similarity NPC65105
0.9459 High Similarity NPC41061
0.9459 High Similarity NPC76972
0.9459 High Similarity NPC79643
0.9459 High Similarity NPC123199
0.9459 High Similarity NPC71065
0.9459 High Similarity NPC473714
0.9459 High Similarity NPC294453
0.9459 High Similarity NPC475160
0.9459 High Similarity NPC57484
0.9459 High Similarity NPC54636
0.9459 High Similarity NPC70809
0.9459 High Similarity NPC475140
0.9459 High Similarity NPC471385
0.9459 High Similarity NPC204414
0.9459 High Similarity NPC293330
0.9459 High Similarity NPC298034
0.9459 High Similarity NPC202828
0.9459 High Similarity NPC100639
0.9459 High Similarity NPC67857
0.9459 High Similarity NPC261506
0.9386 High Similarity NPC473645
0.9381 High Similarity NPC237191
0.9381 High Similarity NPC36831
0.9369 High Similarity NPC473826
0.9369 High Similarity NPC251263
0.9369 High Similarity NPC96641
0.9369 High Similarity NPC46665
0.9369 High Similarity NPC241909
0.9369 High Similarity NPC73318
0.9369 High Similarity NPC295823
0.9369 High Similarity NPC475287
0.9369 High Similarity NPC475467
0.9369 High Similarity NPC309714
0.9369 High Similarity NPC473343
0.9369 High Similarity NPC133818
0.9369 High Similarity NPC323341
0.9369 High Similarity NPC174720
0.9369 High Similarity NPC166422
0.9369 High Similarity NPC192600
0.9369 High Similarity NPC114304
0.9369 High Similarity NPC155410
0.9369 High Similarity NPC219180
0.9369 High Similarity NPC114287
0.9369 High Similarity NPC151543
0.9369 High Similarity NPC150400
0.9369 High Similarity NPC134835
0.9369 High Similarity NPC163183
0.9298 High Similarity NPC207738
0.9292 High Similarity NPC123522
0.9292 High Similarity NPC85154
0.9292 High Similarity NPC68175
0.9292 High Similarity NPC470876
0.9292 High Similarity NPC110633
0.9292 High Similarity NPC33012
0.9292 High Similarity NPC473452
0.9292 High Similarity NPC475209
0.9292 High Similarity NPC8524
0.9292 High Similarity NPC286457
0.9292 High Similarity NPC475514
0.9292 High Similarity NPC191827
0.9292 High Similarity NPC309223
0.9292 High Similarity NPC69811
0.9292 High Similarity NPC148417
0.9292 High Similarity NPC102505
0.9292 High Similarity NPC185466
0.9292 High Similarity NPC220160
0.9292 High Similarity NPC104137
0.9292 High Similarity NPC136768
0.9279 High Similarity NPC473383
0.9279 High Similarity NPC102439
0.9279 High Similarity NPC257468
0.9279 High Similarity NPC104400
0.9279 High Similarity NPC109079
0.9279 High Similarity NPC471383
0.9279 High Similarity NPC10320
0.9279 High Similarity NPC101744
0.9279 High Similarity NPC79718
0.9279 High Similarity NPC139894
0.9279 High Similarity NPC324875
0.9279 High Similarity NPC475516
0.9279 High Similarity NPC473373
0.9279 High Similarity NPC104071
0.9279 High Similarity NPC292677
0.9279 High Similarity NPC276093
0.9279 High Similarity NPC469946
0.9279 High Similarity NPC475504
0.9279 High Similarity NPC139044
0.9217 High Similarity NPC476991
0.9217 High Similarity NPC268184
0.9211 High Similarity NPC232237
0.9211 High Similarity NPC105800
0.9204 High Similarity NPC476992
0.9204 High Similarity NPC51465
0.9204 High Similarity NPC160415
0.9204 High Similarity NPC75287
0.9204 High Similarity NPC161674
0.9204 High Similarity NPC26626
0.9204 High Similarity NPC305267
0.9204 High Similarity NPC288205
0.9204 High Similarity NPC58448
0.9204 High Similarity NPC471384
0.9196 High Similarity NPC124296
0.9196 High Similarity NPC258885
0.9189 High Similarity NPC179434
0.9189 High Similarity NPC164419
0.913 High Similarity NPC135849
0.913 High Similarity NPC25663
0.913 High Similarity NPC473386
0.913 High Similarity NPC51564
0.9123 High Similarity NPC475119
0.9123 High Similarity NPC471547
0.9123 High Similarity NPC471580
0.9123 High Similarity NPC473824
0.9123 High Similarity NPC300419
0.9115 High Similarity NPC475486
0.9115 High Similarity NPC164389
0.9099 High Similarity NPC279554
0.9099 High Similarity NPC75747
0.9099 High Similarity NPC270667
0.9099 High Similarity NPC199457
0.9099 High Similarity NPC127056
0.9099 High Similarity NPC59804
0.9099 High Similarity NPC164194
0.9099 High Similarity NPC102914
0.9099 High Similarity NPC29069
0.9099 High Similarity NPC56713
0.9099 High Similarity NPC136877
0.9099 High Similarity NPC110139
0.9099 High Similarity NPC108709
0.9099 High Similarity NPC174679
0.9099 High Similarity NPC7870
0.9099 High Similarity NPC68419
0.9099 High Similarity NPC474589
0.9099 High Similarity NPC475296
0.9099 High Similarity NPC90856
0.9043 High Similarity NPC471548
0.9043 High Similarity NPC473459
0.9043 High Similarity NPC470514
0.9043 High Similarity NPC470513
0.9035 High Similarity NPC37134
0.9035 High Similarity NPC291903
0.9027 High Similarity NPC189884
0.9027 High Similarity NPC138334
0.9027 High Similarity NPC47063
0.9027 High Similarity NPC269315
0.9027 High Similarity NPC271138
0.9027 High Similarity NPC475208
0.9027 High Similarity NPC238935
0.9027 High Similarity NPC204458
0.9018 High Similarity NPC473481
0.9018 High Similarity NPC297208
0.9018 High Similarity NPC235841
0.9018 High Similarity NPC30397
0.9018 High Similarity NPC211798
0.9018 High Similarity NPC108748
0.9009 High Similarity NPC57362
0.9009 High Similarity NPC127853
0.9009 High Similarity NPC306746
0.9009 High Similarity NPC167383
0.9009 High Similarity NPC237503
0.9009 High Similarity NPC204407
0.9 High Similarity NPC45606
0.9 High Similarity NPC220838
0.8992 High Similarity NPC470218
0.8983 High Similarity NPC256983
0.8966 High Similarity NPC473401
0.8957 High Similarity NPC323359
0.8957 High Similarity NPC473405
0.8938 High Similarity NPC37739
0.8938 High Similarity NPC116794
0.8938 High Similarity NPC48249
0.8938 High Similarity NPC80843

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC477463 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
0.8376 Intermediate Similarity NPD8133 Approved
0.8361 Intermediate Similarity NPD8328 Phase 3
0.8348 Intermediate Similarity NPD8132 Clinical (unspecified phase)
0.8167 Intermediate Similarity NPD8295 Clinical (unspecified phase)
0.7967 Intermediate Similarity NPD8377 Approved
0.7967 Intermediate Similarity NPD8294 Approved
0.7903 Intermediate Similarity NPD8335 Approved
0.7903 Intermediate Similarity NPD8378 Approved
0.7903 Intermediate Similarity NPD8380 Approved
0.7903 Intermediate Similarity NPD8379 Approved
0.7903 Intermediate Similarity NPD8296 Approved
0.7795 Intermediate Similarity NPD7507 Approved
0.776 Intermediate Similarity NPD8517 Approved
0.776 Intermediate Similarity NPD8516 Approved
0.776 Intermediate Similarity NPD8515 Approved
0.776 Intermediate Similarity NPD8033 Approved
0.7712 Intermediate Similarity NPD6412 Phase 2
0.7674 Intermediate Similarity NPD7736 Approved
0.7647 Intermediate Similarity NPD6686 Approved
0.7619 Intermediate Similarity NPD8513 Phase 3
0.7615 Intermediate Similarity NPD7319 Approved
0.76 Intermediate Similarity NPD7516 Approved
0.752 Intermediate Similarity NPD7328 Approved
0.752 Intermediate Similarity NPD7327 Approved
0.7462 Intermediate Similarity NPD8293 Discontinued
0.7459 Intermediate Similarity NPD8413 Clinical (unspecified phase)
0.7395 Intermediate Similarity NPD8170 Clinical (unspecified phase)
0.7368 Intermediate Similarity NPD7748 Approved
0.7328 Intermediate Similarity NPD7902 Approved
0.7287 Intermediate Similarity NPD6370 Approved
0.7209 Intermediate Similarity NPD7503 Approved
0.7193 Intermediate Similarity NPD7515 Phase 2
0.7176 Intermediate Similarity NPD7492 Approved
0.7132 Intermediate Similarity NPD6059 Approved
0.7132 Intermediate Similarity NPD6054 Approved
0.7121 Intermediate Similarity NPD6616 Approved
0.7069 Intermediate Similarity NPD7900 Approved
0.7069 Intermediate Similarity NPD7901 Clinical (unspecified phase)
0.7068 Intermediate Similarity NPD7078 Approved
0.7016 Intermediate Similarity NPD4061 Clinical (unspecified phase)
0.6984 Remote Similarity NPD6882 Approved
0.6984 Remote Similarity NPD8297 Approved
0.6983 Remote Similarity NPD8171 Discontinued
0.697 Remote Similarity NPD6067 Discontinued
0.6947 Remote Similarity NPD6015 Approved
0.6947 Remote Similarity NPD6016 Approved
0.6899 Remote Similarity NPD6009 Approved
0.6897 Remote Similarity NPD8034 Phase 2
0.6897 Remote Similarity NPD8035 Phase 2
0.6894 Remote Similarity NPD5988 Approved
0.687 Remote Similarity NPD6319 Approved
0.6833 Remote Similarity NPD7638 Approved
0.6825 Remote Similarity NPD5955 Clinical (unspecified phase)
0.68 Remote Similarity NPD5345 Clinical (unspecified phase)
0.68 Remote Similarity NPD7320 Approved
0.6797 Remote Similarity NPD4632 Approved
0.6777 Remote Similarity NPD7639 Approved
0.6777 Remote Similarity NPD7640 Approved
0.6774 Remote Similarity NPD7128 Approved
0.6774 Remote Similarity NPD6675 Approved
0.6774 Remote Similarity NPD6402 Approved
0.6774 Remote Similarity NPD5739 Approved
0.6763 Remote Similarity NPD8450 Suspended
0.6746 Remote Similarity NPD6372 Approved
0.6746 Remote Similarity NPD6373 Approved
0.6695 Remote Similarity NPD6399 Phase 3
0.6691 Remote Similarity NPD8074 Phase 3
0.6691 Remote Similarity NPD8449 Approved
0.6667 Remote Similarity NPD7520 Clinical (unspecified phase)
0.6667 Remote Similarity NPD6899 Approved
0.6667 Remote Similarity NPD6881 Approved
0.6642 Remote Similarity NPD6033 Approved
0.6641 Remote Similarity NPD8130 Phase 1
0.6641 Remote Similarity NPD6649 Approved
0.6641 Remote Similarity NPD7115 Discovery
0.6641 Remote Similarity NPD6650 Approved
0.664 Remote Similarity NPD6008 Approved
0.6587 Remote Similarity NPD5697 Approved
0.6587 Remote Similarity NPD5701 Approved
0.6587 Remote Similarity NPD5954 Clinical (unspecified phase)
0.6577 Remote Similarity NPD7645 Phase 2
0.6562 Remote Similarity NPD7290 Approved
0.6562 Remote Similarity NPD7102 Approved
0.6562 Remote Similarity NPD6883 Approved
0.6512 Remote Similarity NPD6869 Approved
0.6512 Remote Similarity NPD6847 Approved
0.6512 Remote Similarity NPD6617 Approved
0.6484 Remote Similarity NPD6013 Approved
0.6484 Remote Similarity NPD6012 Approved
0.6484 Remote Similarity NPD6014 Approved
0.6475 Remote Similarity NPD6083 Phase 2
0.6475 Remote Similarity NPD6084 Phase 2
0.6471 Remote Similarity NPD7604 Phase 2
0.6444 Remote Similarity NPD5983 Phase 2
0.6443 Remote Similarity NPD7625 Phase 1
0.6423 Remote Similarity NPD4225 Approved
0.6406 Remote Similarity NPD6011 Approved
0.6385 Remote Similarity NPD6401 Clinical (unspecified phase)
0.6377 Remote Similarity NPD6336 Discontinued
0.6356 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6341 Remote Similarity NPD4755 Approved
0.6333 Remote Similarity NPD6411 Approved
0.6325 Remote Similarity NPD3618 Phase 1
0.6324 Remote Similarity NPD6921 Approved
0.6311 Remote Similarity NPD6356 Clinical (unspecified phase)
0.6308 Remote Similarity NPD4634 Approved
0.6303 Remote Similarity NPD5328 Approved
0.6293 Remote Similarity NPD4786 Approved
0.6281 Remote Similarity NPD4202 Approved
0.6271 Remote Similarity NPD3573 Approved
0.627 Remote Similarity NPD7632 Discontinued
0.6261 Remote Similarity NPD3667 Approved
0.625 Remote Similarity NPD6698 Approved
0.625 Remote Similarity NPD46 Approved
0.624 Remote Similarity NPD5285 Approved
0.624 Remote Similarity NPD4696 Approved
0.624 Remote Similarity NPD5286 Approved
0.624 Remote Similarity NPD4700 Approved
0.6228 Remote Similarity NPD7525 Registered
0.6218 Remote Similarity NPD6903 Approved
0.6207 Remote Similarity NPD3669 Approved
0.6207 Remote Similarity NPD3670 Clinical (unspecified phase)
0.6198 Remote Similarity NPD6079 Approved
0.6197 Remote Similarity NPD5956 Approved
0.6194 Remote Similarity NPD6274 Approved
0.6194 Remote Similarity NPD6940 Discontinued
0.6186 Remote Similarity NPD7334 Approved
0.6186 Remote Similarity NPD7146 Approved
0.6186 Remote Similarity NPD6409 Approved
0.6186 Remote Similarity NPD6684 Approved
0.6186 Remote Similarity NPD5330 Approved
0.6186 Remote Similarity NPD7521 Approved
0.6179 Remote Similarity NPD5695 Phase 3
0.6176 Remote Similarity NPD7100 Approved
0.6176 Remote Similarity NPD7101 Approved
0.617 Remote Similarity NPD8336 Approved
0.617 Remote Similarity NPD8337 Approved
0.6167 Remote Similarity NPD6101 Approved
0.6167 Remote Similarity NPD5764 Clinical (unspecified phase)
0.616 Remote Similarity NPD5696 Approved
0.616 Remote Similarity NPD8029 Clinical (unspecified phase)
0.6148 Remote Similarity NPD8137 Clinical (unspecified phase)
0.6142 Remote Similarity NPD5225 Approved
0.6142 Remote Similarity NPD5226 Approved
0.6142 Remote Similarity NPD4633 Approved
0.6142 Remote Similarity NPD5224 Approved
0.6142 Remote Similarity NPD5211 Phase 2
0.6124 Remote Similarity NPD4768 Approved
0.6124 Remote Similarity NPD4767 Approved
0.6111 Remote Similarity NPD8338 Approved
0.6103 Remote Similarity NPD6335 Approved
0.6094 Remote Similarity NPD5175 Approved
0.6094 Remote Similarity NPD5174 Approved
0.609 Remote Similarity NPD6053 Discontinued
0.6087 Remote Similarity NPD6291 Clinical (unspecified phase)
0.6087 Remote Similarity NPD6909 Approved
0.6087 Remote Similarity NPD6908 Approved
0.6083 Remote Similarity NPD5737 Approved
0.6083 Remote Similarity NPD6672 Approved
0.6077 Remote Similarity NPD7899 Clinical (unspecified phase)
0.6066 Remote Similarity NPD7983 Approved
0.6063 Remote Similarity NPD5223 Approved
0.6063 Remote Similarity NPD5344 Discontinued
0.6053 Remote Similarity NPD6114 Approved
0.6053 Remote Similarity NPD6115 Approved
0.6053 Remote Similarity NPD6697 Approved
0.6053 Remote Similarity NPD6118 Approved
0.6048 Remote Similarity NPD7228 Approved
0.6047 Remote Similarity NPD5141 Approved
0.6034 Remote Similarity NPD1779 Approved
0.6034 Remote Similarity NPD1780 Approved
0.6033 Remote Similarity NPD4753 Phase 2
0.6033 Remote Similarity NPD7285 Clinical (unspecified phase)
0.6031 Remote Similarity NPD4729 Approved
0.6031 Remote Similarity NPD4730 Approved
0.6029 Remote Similarity NPD6317 Approved
0.6017 Remote Similarity NPD3666 Approved
0.6017 Remote Similarity NPD3133 Approved
0.6017 Remote Similarity NPD3665 Phase 1
0.6016 Remote Similarity NPD5779 Approved
0.6016 Remote Similarity NPD5778 Approved
0.6 Remote Similarity NPD7240 Approved
0.6 Remote Similarity NPD5222 Approved
0.6 Remote Similarity NPD7524 Approved
0.6 Remote Similarity NPD4697 Phase 3
0.6 Remote Similarity NPD5220 Clinical (unspecified phase)
0.6 Remote Similarity NPD5221 Approved
0.5986 Remote Similarity NPD8448 Approved
0.5985 Remote Similarity NPD6314 Approved
0.5985 Remote Similarity NPD6313 Approved
0.5972 Remote Similarity NPD8391 Approved
0.5972 Remote Similarity NPD8392 Approved
0.5972 Remote Similarity NPD8390 Approved
0.5971 Remote Similarity NPD8274 Clinical (unspecified phase)
0.5969 Remote Similarity NPD4754 Approved
0.5968 Remote Similarity NPD6001 Approved
0.5968 Remote Similarity NPD5282 Discontinued
0.5965 Remote Similarity NPD6116 Phase 1
0.5957 Remote Similarity NPD8299 Approved
0.5957 Remote Similarity NPD8342 Approved

Structure

External Identifiers

PubChem CID   44566728
ChEMBL   CHEMBL447984
ZINC  

Physicochemical Properties

Molecular Weight:  1486.68
ALogP:  -9.6379
MLogP:  5.09
XLogP:  -2.362
# Rotatable Bonds:  47
Polar Surface Area:  550.89
# H-Bond Aceptor:  35
# H-Bond Donor:  20
# Rings:  12
# Heavy Atoms:  103

Download Data

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Similar NPs/Drugs