Natural Product: NPC477606

Natural Product ID:  NPC477606
Common Name:   [(3R,4R,10R,13S,17R)-4-hydroxy-10,13-dimethyl-17-[(2R)-6-methyl-1-sulfonatooxyheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] sulfate
IUPAC Name:   [(3R,4R,10R,13S,17R)-4-hydroxy-10,13-dimethyl-17-[(2R)-6-methyl-1-sulfonatooxyheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] sulfate
Synonyms:  
Molecular Formula:   C27H46O9S2.2Na
Standard InCHIKey:  KURJUQGKEGKWDS-GZLPDTPUSA-L
Standard InCHI:  InChI=1S/C27H46O9S2.2Na/c1-17(2)6-5-7-18(16-35-37(29,30)31)20-10-11-21-19-8-9-23-25(28)24(36-38(32,33)34)13-15-27(23,4)22(19)12-14-26(20,21)3;;/h9,17-22,24-25,28H,5-8,10-16H2,1-4H3,(H,29,30,31)(H,32,33,34);;/q;2*+1/p-2/t18-,19?,20+,21?,22?,24+,25+,26+,27+;;/m0../s1
Canonical SMILES:  CC(CCC[C@H]([C@H]1CCC2[C@]1(C)CCC1C2CC=C2[C@]1(C)CC[C@H]([C@@H]2O)OS(=O)(=O)[O-])COS(=O)(=O)[O-])C.[Na+].[Na+]
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
NPO33590 Ophiotrix fragilis Species NA NA Bay of Naples PMID[8145229]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT404 Cell Line CCRF-CEM Homo sapiens EC50 = 241000 nM 8145229
NPT24 Organism Human immunodeficiency virus 1 Human immunodeficiency virus 1 IC50 > 322000 nM 8145229
NPT404 Cell Line CCRF-CEM Homo sapiens EC50 = 80000 nM 8145229
NPT3795 Organism Human immunodeficiency virus 2 Human immunodeficiency virus 2 IC50 > 161000 nM 8145229

  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 NPC477606 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
0.9639 High Similarity NPC477604
0.954 High Similarity NPC477605
0.9277 High Similarity NPC317458
0.9048 High Similarity NPC474634
0.9036 High Similarity NPC473534
0.8966 High Similarity NPC474668
0.8941 High Similarity NPC185568
0.8941 High Similarity NPC478102
0.881 High Similarity NPC474531
0.8795 High Similarity NPC47982
0.8795 High Similarity NPC209430
0.8795 High Similarity NPC81306
0.8795 High Similarity NPC84694
0.8795 High Similarity NPC109546
0.8795 High Similarity NPC30986
0.8795 High Similarity NPC143182
0.8795 High Similarity NPC28862
0.8706 High Similarity NPC101462
0.8706 High Similarity NPC477599
0.869 High Similarity NPC236112
0.869 High Similarity NPC234193
0.8675 High Similarity NPC474216
0.8675 High Similarity NPC475337
0.8636 High Similarity NPC470620
0.8636 High Similarity NPC475313
0.8588 High Similarity NPC23852
0.8588 High Similarity NPC209620
0.8588 High Similarity NPC264245
0.8571 High Similarity NPC328714
0.8539 High Similarity NPC67872
0.8539 High Similarity NPC133588
0.8523 High Similarity NPC6391
0.8523 High Similarity NPC261266
0.8506 High Similarity NPC205845
0.8488 Intermediate Similarity NPC189972
0.8488 Intermediate Similarity NPC49964
0.8488 Intermediate Similarity NPC30166
0.8488 Intermediate Similarity NPC50964
0.8471 Intermediate Similarity NPC164840
0.8471 Intermediate Similarity NPC241290
0.8471 Intermediate Similarity NPC209944
0.8462 Intermediate Similarity NPC41554
0.8462 Intermediate Similarity NPC97404
0.8452 Intermediate Similarity NPC167891
0.8452 Intermediate Similarity NPC473943
0.8452 Intermediate Similarity NPC83351
0.8444 Intermediate Similarity NPC470361
0.8434 Intermediate Similarity NPC107059
0.8434 Intermediate Similarity NPC244488
0.8434 Intermediate Similarity NPC247325
0.8434 Intermediate Similarity NPC321381
0.8434 Intermediate Similarity NPC321016
0.8409 Intermediate Similarity NPC266511
0.8404 Intermediate Similarity NPC477226
0.8391 Intermediate Similarity NPC475789
0.8391 Intermediate Similarity NPC207013
0.8372 Intermediate Similarity NPC82986
0.8372 Intermediate Similarity NPC474752
0.8372 Intermediate Similarity NPC474731
0.8372 Intermediate Similarity NPC474759
0.8372 Intermediate Similarity NPC7505
0.8372 Intermediate Similarity NPC47761
0.8372 Intermediate Similarity NPC474683
0.8352 Intermediate Similarity NPC329596
0.8352 Intermediate Similarity NPC11216
0.8352 Intermediate Similarity NPC3345
0.8352 Intermediate Similarity NPC291484
0.8352 Intermediate Similarity NPC80561
0.8352 Intermediate Similarity NPC204188
0.8333 Intermediate Similarity NPC318495
0.8333 Intermediate Similarity NPC280556
0.8333 Intermediate Similarity NPC198968
0.8333 Intermediate Similarity NPC155986
0.8315 Intermediate Similarity NPC94462
0.8315 Intermediate Similarity NPC152808
0.8315 Intermediate Similarity NPC293287
0.8315 Intermediate Similarity NPC478094
0.8313 Intermediate Similarity NPC257347
0.8313 Intermediate Similarity NPC288035
0.8313 Intermediate Similarity NPC230301
0.8313 Intermediate Similarity NPC304309
0.8313 Intermediate Similarity NPC162742
0.8313 Intermediate Similarity NPC136188
0.8313 Intermediate Similarity NPC285893
0.8313 Intermediate Similarity NPC22105
0.8313 Intermediate Similarity NPC134847
0.8313 Intermediate Similarity NPC141071
0.8313 Intermediate Similarity NPC28657
0.8313 Intermediate Similarity NPC471723
0.8295 Intermediate Similarity NPC238485
0.8295 Intermediate Similarity NPC474047
0.8276 Intermediate Similarity NPC87489
0.8276 Intermediate Similarity NPC470049
0.8276 Intermediate Similarity NPC296701
0.8276 Intermediate Similarity NPC218616
0.8276 Intermediate Similarity NPC202389
0.8256 Intermediate Similarity NPC22403
0.8256 Intermediate Similarity NPC13554
0.8242 Intermediate Similarity NPC105495
0.8235 Intermediate Similarity NPC275910
0.8235 Intermediate Similarity NPC477522
0.8235 Intermediate Similarity NPC87604
0.8222 Intermediate Similarity NPC477600
0.8222 Intermediate Similarity NPC149224
0.8214 Intermediate Similarity NPC134330
0.8214 Intermediate Similarity NPC240604
0.8214 Intermediate Similarity NPC129165
0.8214 Intermediate Similarity NPC113733
0.8214 Intermediate Similarity NPC300324
0.8214 Intermediate Similarity NPC274079
0.8214 Intermediate Similarity NPC189883
0.8214 Intermediate Similarity NPC477925
0.8202 Intermediate Similarity NPC274448
0.8202 Intermediate Similarity NPC318390
0.8193 Intermediate Similarity NPC469533
0.8193 Intermediate Similarity NPC469593
0.8193 Intermediate Similarity NPC469534
0.8182 Intermediate Similarity NPC470384
0.8152 Intermediate Similarity NPC295668
0.814 Intermediate Similarity NPC474132
0.814 Intermediate Similarity NPC1319
0.8118 Intermediate Similarity NPC214570
0.8118 Intermediate Similarity NPC34019
0.8118 Intermediate Similarity NPC91594
0.8118 Intermediate Similarity NPC477924
0.8105 Intermediate Similarity NPC72204
0.8105 Intermediate Similarity NPC288970
0.8095 Intermediate Similarity NPC66566
0.8095 Intermediate Similarity NPC477923
0.809 Intermediate Similarity NPC469878
0.809 Intermediate Similarity NPC470077
0.809 Intermediate Similarity NPC124172
0.809 Intermediate Similarity NPC231310
0.8068 Intermediate Similarity NPC470614
0.8068 Intermediate Similarity NPC1272
0.8068 Intermediate Similarity NPC7988
0.8065 Intermediate Similarity NPC275671
0.8046 Intermediate Similarity NPC322313
0.8046 Intermediate Similarity NPC236237
0.8046 Intermediate Similarity NPC26117
0.8046 Intermediate Similarity NPC102253
0.8023 Intermediate Similarity NPC18603
0.8023 Intermediate Similarity NPC285761
0.8023 Intermediate Similarity NPC244385
0.8023 Intermediate Similarity NPC307965
0.8023 Intermediate Similarity NPC6978
0.8023 Intermediate Similarity NPC76931
0.8023 Intermediate Similarity NPC167037
0.8023 Intermediate Similarity NPC138621
0.8023 Intermediate Similarity NPC476314
0.8023 Intermediate Similarity NPC477514
0.8 Intermediate Similarity NPC46160
0.8 Intermediate Similarity NPC470360
0.8 Intermediate Similarity NPC202642
0.8 Intermediate Similarity NPC237460
0.8 Intermediate Similarity NPC73875
0.8 Intermediate Similarity NPC96319
0.8 Intermediate Similarity NPC157257
0.8 Intermediate Similarity NPC476894
0.8 Intermediate Similarity NPC470362
0.7979 Intermediate Similarity NPC310013
0.7979 Intermediate Similarity NPC109305
0.7978 Intermediate Similarity NPC82623
0.7955 Intermediate Similarity NPC470383
0.7955 Intermediate Similarity NPC6707
0.7955 Intermediate Similarity NPC476646
0.7935 Intermediate Similarity NPC475664
0.7935 Intermediate Similarity NPC471952
0.7931 Intermediate Similarity NPC273410
0.7931 Intermediate Similarity NPC80530
0.7917 Intermediate Similarity NPC88009
0.7912 Intermediate Similarity NPC299068
0.7912 Intermediate Similarity NPC139724
0.7912 Intermediate Similarity NPC474970
0.7912 Intermediate Similarity NPC71520
0.7912 Intermediate Similarity NPC24277
0.7912 Intermediate Similarity NPC269058
0.7912 Intermediate Similarity NPC125399
0.7907 Intermediate Similarity NPC470758
0.7907 Intermediate Similarity NPC470711
0.7895 Intermediate Similarity NPC127718
0.7895 Intermediate Similarity NPC65402
0.7889 Intermediate Similarity NPC238992
0.7889 Intermediate Similarity NPC209802
0.7889 Intermediate Similarity NPC15534
0.7882 Intermediate Similarity NPC121744
0.7882 Intermediate Similarity NPC185536
0.7882 Intermediate Similarity NPC118508
0.7882 Intermediate Similarity NPC322353
0.7872 Intermediate Similarity NPC473998
0.7872 Intermediate Similarity NPC189520
0.7865 Intermediate Similarity NPC47763
0.7865 Intermediate Similarity NPC201852
0.7865 Intermediate Similarity NPC248886
0.7865 Intermediate Similarity NPC5985
0.7857 Intermediate Similarity NPC474140
0.7857 Intermediate Similarity NPC230546
0.7857 Intermediate Similarity NPC473510
0.7857 Intermediate Similarity NPC471799
0.7849 Intermediate Similarity NPC472240

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC477606 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
0.8313 Intermediate Similarity NPD7339 Approved
0.8313 Intermediate Similarity NPD6942 Approved
0.8046 Intermediate Similarity NPD7525 Registered
0.8 Intermediate Similarity NPD3701 Clinical (unspecified phase)
0.7826 Intermediate Similarity NPD4751 Clinical (unspecified phase)
0.7791 Intermediate Similarity NPD6933 Approved
0.7692 Intermediate Similarity NPD4786 Approved
0.7634 Intermediate Similarity NPD7524 Approved
0.7558 Intermediate Similarity NPD6924 Approved
0.7558 Intermediate Similarity NPD6926 Approved
0.7528 Intermediate Similarity NPD6929 Approved
0.75 Intermediate Similarity NPD3668 Phase 3
0.7473 Intermediate Similarity NPD3667 Approved
0.7444 Intermediate Similarity NPD6931 Approved
0.7444 Intermediate Similarity NPD6930 Phase 2
0.7391 Intermediate Similarity NPD6695 Phase 3
0.7356 Intermediate Similarity NPD4785 Approved
0.7356 Intermediate Similarity NPD4784 Approved
0.7333 Intermediate Similarity NPD7645 Phase 2
0.7326 Intermediate Similarity NPD7152 Approved
0.7326 Intermediate Similarity NPD7150 Approved
0.7326 Intermediate Similarity NPD7151 Approved
0.7326 Intermediate Similarity NPD4243 Approved
0.7312 Intermediate Similarity NPD7338 Clinical (unspecified phase)
0.7303 Intermediate Similarity NPD5776 Phase 2
0.7303 Intermediate Similarity NPD6925 Approved
0.7294 Intermediate Similarity NPD6922 Approved
0.7294 Intermediate Similarity NPD6923 Approved
0.7292 Intermediate Similarity NPD5328 Approved
0.7273 Intermediate Similarity NPD8264 Approved
0.7253 Intermediate Similarity NPD4748 Discontinued
0.7253 Intermediate Similarity NPD7514 Phase 3
0.7222 Intermediate Similarity NPD7322 Clinical (unspecified phase)
0.7222 Intermediate Similarity NPD7145 Approved
0.7209 Intermediate Similarity NPD7143 Approved
0.7209 Intermediate Similarity NPD7144 Approved
0.7174 Intermediate Similarity NPD6902 Approved
0.7158 Intermediate Similarity NPD3618 Phase 1
0.7143 Intermediate Similarity NPD6079 Approved
0.7083 Intermediate Similarity NPD7750 Discontinued
0.7071 Intermediate Similarity NPD6399 Phase 3
0.7065 Intermediate Similarity NPD7332 Phase 2
0.7065 Intermediate Similarity NPD7509 Discontinued
0.7053 Intermediate Similarity NPD6893 Approved
0.699 Remote Similarity NPD7639 Approved
0.699 Remote Similarity NPD7640 Approved
0.6947 Remote Similarity NPD3133 Approved
0.6947 Remote Similarity NPD3666 Approved
0.6947 Remote Similarity NPD3665 Phase 1
0.6923 Remote Similarity NPD6932 Approved
0.69 Remote Similarity NPD4202 Approved
0.6897 Remote Similarity NPD4267 Clinical (unspecified phase)
0.6893 Remote Similarity NPD7638 Approved
0.6889 Remote Similarity NPD4190 Phase 3
0.6889 Remote Similarity NPD5275 Approved
0.6863 Remote Similarity NPD5221 Approved
0.6863 Remote Similarity NPD5222 Approved
0.6863 Remote Similarity NPD4697 Phase 3
0.6863 Remote Similarity NPD5220 Clinical (unspecified phase)
0.6857 Remote Similarity NPD5211 Phase 2
0.6814 Remote Similarity NPD7115 Discovery
0.6809 Remote Similarity NPD6898 Phase 1
0.68 Remote Similarity NPD7087 Discontinued
0.6796 Remote Similarity NPD5173 Approved
0.6796 Remote Similarity NPD4755 Approved
0.6774 Remote Similarity NPD6683 Phase 2
0.6774 Remote Similarity NPD4195 Approved
0.6768 Remote Similarity NPD6051 Approved
0.6768 Remote Similarity NPD4753 Phase 2
0.6762 Remote Similarity NPD4159 Approved
0.6731 Remote Similarity NPD4225 Approved
0.6731 Remote Similarity NPD5290 Discontinued
0.6729 Remote Similarity NPD5141 Approved
0.6701 Remote Similarity NPD7520 Clinical (unspecified phase)
0.67 Remote Similarity NPD7136 Phase 2
0.6667 Remote Similarity NPD4700 Approved
0.6667 Remote Similarity NPD4696 Approved
0.6667 Remote Similarity NPD5285 Approved
0.6667 Remote Similarity NPD5286 Approved
0.6636 Remote Similarity NPD4754 Approved
0.6634 Remote Similarity NPD7515 Phase 2
0.6634 Remote Similarity NPD7637 Suspended
0.6633 Remote Similarity NPD5279 Phase 3
0.6604 Remote Similarity NPD5223 Approved
0.6562 Remote Similarity NPD4221 Approved
0.6562 Remote Similarity NPD4223 Phase 3
0.6552 Remote Similarity NPD7516 Approved
0.6542 Remote Similarity NPD4633 Approved
0.6542 Remote Similarity NPD5226 Approved
0.6542 Remote Similarity NPD5224 Approved
0.6542 Remote Similarity NPD5225 Approved
0.6531 Remote Similarity NPD5329 Approved
0.6514 Remote Similarity NPD6675 Approved
0.6514 Remote Similarity NPD6402 Approved
0.6514 Remote Similarity NPD7128 Approved
0.6514 Remote Similarity NPD4767 Approved
0.6514 Remote Similarity NPD4768 Approved
0.6514 Remote Similarity NPD5739 Approved
0.6486 Remote Similarity NPD6373 Approved
0.6486 Remote Similarity NPD6372 Approved
0.6481 Remote Similarity NPD5175 Approved
0.6481 Remote Similarity NPD5174 Approved
0.6476 Remote Similarity NPD6083 Phase 2
0.6476 Remote Similarity NPD6084 Phase 2
0.6466 Remote Similarity NPD7328 Approved
0.6466 Remote Similarity NPD7327 Approved
0.646 Remote Similarity NPD8297 Approved
0.6442 Remote Similarity NPD4629 Approved
0.6442 Remote Similarity NPD5210 Approved
0.6441 Remote Similarity NPD8033 Approved
0.6429 Remote Similarity NPD4197 Approved
0.6429 Remote Similarity NPD4634 Approved
0.6396 Remote Similarity NPD4729 Approved
0.6396 Remote Similarity NPD7320 Approved
0.6396 Remote Similarity NPD6881 Approved
0.6396 Remote Similarity NPD6899 Approved
0.6396 Remote Similarity NPD4730 Approved
0.6389 Remote Similarity NPD7632 Discontinued
0.6372 Remote Similarity NPD6401 Clinical (unspecified phase)
0.6372 Remote Similarity NPD6650 Approved
0.6372 Remote Similarity NPD6649 Approved
0.6356 Remote Similarity NPD8377 Approved
0.6356 Remote Similarity NPD8294 Approved
0.6346 Remote Similarity NPD7748 Approved
0.6337 Remote Similarity NPD6672 Approved
0.6337 Remote Similarity NPD5737 Approved
0.6327 Remote Similarity NPD4788 Approved
0.6316 Remote Similarity NPD6882 Approved
0.6316 Remote Similarity NPD5784 Clinical (unspecified phase)
0.6311 Remote Similarity NPD8034 Phase 2
0.6311 Remote Similarity NPD8035 Phase 2
0.6306 Remote Similarity NPD6412 Phase 2
0.6306 Remote Similarity NPD5697 Approved
0.6306 Remote Similarity NPD5701 Approved
0.6303 Remote Similarity NPD7503 Approved
0.6303 Remote Similarity NPD8296 Approved
0.6303 Remote Similarity NPD8380 Approved
0.6303 Remote Similarity NPD8379 Approved
0.6303 Remote Similarity NPD8378 Approved
0.6303 Remote Similarity NPD8335 Approved
0.63 Remote Similarity NPD7146 Approved
0.63 Remote Similarity NPD4138 Approved
0.63 Remote Similarity NPD6409 Approved
0.63 Remote Similarity NPD3574 Clinical (unspecified phase)
0.63 Remote Similarity NPD4519 Discontinued
0.63 Remote Similarity NPD5205 Approved
0.63 Remote Similarity NPD7334 Approved
0.63 Remote Similarity NPD4688 Approved
0.63 Remote Similarity NPD7521 Approved
0.63 Remote Similarity NPD5330 Approved
0.63 Remote Similarity NPD4689 Approved
0.63 Remote Similarity NPD4623 Approved
0.63 Remote Similarity NPD4690 Approved
0.63 Remote Similarity NPD6684 Approved
0.63 Remote Similarity NPD4693 Phase 3
0.6283 Remote Similarity NPD5135 Approved
0.6283 Remote Similarity NPD5251 Approved
0.6283 Remote Similarity NPD5249 Phase 3
0.6283 Remote Similarity NPD5247 Approved
0.6283 Remote Similarity NPD5248 Approved
0.6283 Remote Similarity NPD6883 Approved
0.6283 Remote Similarity NPD7102 Approved
0.6283 Remote Similarity NPD5134 Clinical (unspecified phase)
0.6283 Remote Similarity NPD5250 Approved
0.6283 Remote Similarity NPD7290 Approved
0.6279 Remote Similarity NPD368 Approved
0.6264 Remote Similarity NPD4787 Phase 1
0.6261 Remote Similarity NPD4632 Approved
0.625 Remote Similarity NPD6011 Approved
0.625 Remote Similarity NPD5128 Approved
0.625 Remote Similarity NPD5168 Approved
0.6228 Remote Similarity NPD6617 Approved
0.6228 Remote Similarity NPD8130 Phase 1
0.6228 Remote Similarity NPD6869 Approved
0.6228 Remote Similarity NPD6847 Approved
0.6216 Remote Similarity NPD6640 Phase 3
0.6196 Remote Similarity NPD4809 Clinical (unspecified phase)
0.6196 Remote Similarity NPD4808 Clinical (unspecified phase)
0.6195 Remote Similarity NPD6014 Approved
0.6195 Remote Similarity NPD6013 Approved
0.6195 Remote Similarity NPD6012 Approved
0.6186 Remote Similarity NPD4695 Discontinued
0.6176 Remote Similarity NPD4723 Approved
0.6176 Remote Similarity NPD4722 Approved
0.6176 Remote Similarity NPD6903 Approved
0.6176 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6168 Remote Similarity NPD7902 Approved
0.6162 Remote Similarity NPD5331 Approved
0.6162 Remote Similarity NPD5332 Approved
0.6162 Remote Similarity NPD5362 Discontinued
0.6146 Remote Similarity NPD3617 Approved
0.6145 Remote Similarity NPD342 Phase 1
0.614 Remote Similarity NPD5169 Approved
0.6139 Remote Similarity NPD4694 Approved
0.6139 Remote Similarity NPD5690 Phase 2
0.6139 Remote Similarity NPD5280 Approved
0.6132 Remote Similarity NPD5695 Phase 3
0.6122 Remote Similarity NPD4790 Discontinued
0.6116 Remote Similarity NPD3095 Discontinued
0.6111 Remote Similarity NPD5696 Approved

Structure

External Identifiers

PubChem CID   24943524;23428165
ChEMBL   CHEMBL355187
ZINC  

Physicochemical Properties

Molecular Weight:  576.24
ALogP:  -1.3597
MLogP:  3.22
XLogP:  5.191
# Rotatable Bonds:  17
Polar Surface Area:  169.85
# H-Bond Aceptor:  9
# H-Bond Donor:  1
# Rings:  4
# Heavy Atoms:  38

Download Data

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Biological Activities  
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