Natural Product: NPC111585

Natural Product ID:  NPC111585
Common Name:   Tsugaric Acid A
IUPAC Name:   (2R)-2-[(3R,5R,10S,13R,14R,17R)-3-acetyloxy-4,4,10,13,14-pentamethyl-2,3,5,6,7,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-17-yl]-6-methylhept-5-enoic acid
Synonyms:  
Molecular Formula:   C32H50O4
Standard InCHIKey:  FIWGZIBLJWZUEA-CAHOJKFZSA-N
Standard InCHI:  InChI=1S/C32H50O4/c1-20(2)10-9-11-22(28(34)35)23-14-18-32(8)25-12-13-26-29(4,5)27(36-21(3)33)16-17-30(26,6)24(25)15-19-31(23,32)7/h10,22-23,26-27H,9,11-19H2,1-8H3,(H,34,35)/t22-,23-,26+,27-,30-,31-,32+/m1/s1
Canonical SMILES:  CC(=CCC[C@H]([C@H]1CC[C@@]2([C@]1(C)CCC1=C2CC[C@@H]2[C@]1(C)CC[C@H](C2(C)C)OC(=O)C)C)C(=O)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
NPO2085 Ganoderma tsugae Species Ganodermataceae Eukaryota PMID[10785428]
NPO25269 Ganoderma lucidum Species Ganodermataceae Eukaryota TM-MC*
NPO16609 Ganoderma sinense Species Ganodermataceae Eukaryota TM-MC*

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT2 Others Unspecified ED50 = 6.8 ug/ml 10785428
NPT550 Cell Line T-24 Homo sapiens ED50 = 3.1 ug/ml 10785428

  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 NPC111585 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
1.0 High Similarity NPC148414
1.0 High Similarity NPC175628
0.9882 High Similarity NPC26888
0.9881 High Similarity NPC474889
0.9765 High Similarity NPC471896
0.9412 High Similarity NPC233836
0.9412 High Similarity NPC187376
0.9412 High Similarity NPC159046
0.9326 High Similarity NPC69548
0.9326 High Similarity NPC184848
0.9302 High Similarity NPC242864
0.9294 High Similarity NPC28252
0.9294 High Similarity NPC55309
0.9231 High Similarity NPC477813
0.9222 High Similarity NPC120708
0.9213 High Similarity NPC159410
0.9205 High Similarity NPC297265
0.9195 High Similarity NPC77168
0.9195 High Similarity NPC474704
0.9195 High Similarity NPC475921
0.9195 High Similarity NPC84271
0.9195 High Similarity NPC102414
0.9186 High Similarity NPC474684
0.9186 High Similarity NPC142361
0.9111 High Similarity NPC279974
0.9101 High Similarity NPC470224
0.9091 High Similarity NPC469400
0.907 High Similarity NPC325594
0.9011 High Similarity NPC327788
0.9 High Similarity NPC469406
0.8989 High Similarity NPC189520
0.8989 High Similarity NPC23434
0.8977 High Similarity NPC474570
0.8966 High Similarity NPC167877
0.8901 High Similarity NPC317586
0.8901 High Similarity NPC162001
0.8901 High Similarity NPC222845
0.8901 High Similarity NPC473648
0.8901 High Similarity NPC470016
0.8901 High Similarity NPC45324
0.8889 High Similarity NPC470375
0.8889 High Similarity NPC141497
0.8889 High Similarity NPC107674
0.8889 High Similarity NPC170220
0.8889 High Similarity NPC470376
0.8876 High Similarity NPC20388
0.8876 High Similarity NPC120840
0.8876 High Similarity NPC113989
0.8864 High Similarity NPC4309
0.8851 High Similarity NPC264127
0.8851 High Similarity NPC474970
0.8851 High Similarity NPC94755
0.8851 High Similarity NPC73038
0.8851 High Similarity NPC155011
0.883 High Similarity NPC473514
0.8817 High Similarity NPC119036
0.8804 High Similarity NPC173272
0.8791 High Similarity NPC166906
0.8778 High Similarity NPC77099
0.8778 High Similarity NPC110657
0.8778 High Similarity NPC60755
0.8778 High Similarity NPC285184
0.8778 High Similarity NPC212301
0.8778 High Similarity NPC86266
0.8778 High Similarity NPC470590
0.8764 High Similarity NPC30522
0.8737 High Similarity NPC473788
0.8737 High Similarity NPC475558
0.8721 High Similarity NPC471037
0.8706 High Similarity NPC38350
0.8706 High Similarity NPC201912
0.8706 High Similarity NPC327002
0.8696 High Similarity NPC469599
0.8696 High Similarity NPC48330
0.869 High Similarity NPC327674
0.8681 High Similarity NPC86368
0.8681 High Similarity NPC38232
0.8667 High Similarity NPC44240
0.8667 High Similarity NPC474728
0.8652 High Similarity NPC472220
0.8652 High Similarity NPC471722
0.8652 High Similarity NPC97884
0.8652 High Similarity NPC183546
0.8652 High Similarity NPC294480
0.8636 High Similarity NPC72133
0.8621 High Similarity NPC100391
0.8621 High Similarity NPC165064
0.8617 High Similarity NPC186810
0.8617 High Similarity NPC48647
0.8605 High Similarity NPC296367
0.8605 High Similarity NPC260956
0.8602 High Similarity NPC7124
0.8602 High Similarity NPC96859
0.8602 High Similarity NPC328162
0.8602 High Similarity NPC305483
0.8602 High Similarity NPC42042
0.8587 High Similarity NPC471720
0.8587 High Similarity NPC184006
0.8587 High Similarity NPC49670
0.8587 High Similarity NPC474922
0.8587 High Similarity NPC296164
0.8587 High Similarity NPC74751
0.8587 High Similarity NPC23621
0.8587 High Similarity NPC78580
0.8571 High Similarity NPC154101
0.8571 High Similarity NPC160506
0.8571 High Similarity NPC471901
0.8556 High Similarity NPC54689
0.8556 High Similarity NPC275740
0.8556 High Similarity NPC86319
0.8556 High Similarity NPC128496
0.8542 High Similarity NPC22388
0.8539 High Similarity NPC33768
0.8539 High Similarity NPC162107
0.8539 High Similarity NPC46912
0.8539 High Similarity NPC96496
0.8539 High Similarity NPC312215
0.8523 High Similarity NPC98270
0.8511 High Similarity NPC108078
0.8511 High Similarity NPC320306
0.8511 High Similarity NPC141401
0.8506 High Similarity NPC69279
0.8506 High Similarity NPC83569
0.8495 Intermediate Similarity NPC195715
0.8495 Intermediate Similarity NPC23241
0.8495 Intermediate Similarity NPC84383
0.8495 Intermediate Similarity NPC474727
0.8488 Intermediate Similarity NPC147066
0.8488 Intermediate Similarity NPC473420
0.8478 Intermediate Similarity NPC152897
0.8478 Intermediate Similarity NPC474436
0.8478 Intermediate Similarity NPC477855
0.8478 Intermediate Similarity NPC287118
0.8478 Intermediate Similarity NPC473690
0.8478 Intermediate Similarity NPC63118
0.8478 Intermediate Similarity NPC66429
0.8478 Intermediate Similarity NPC49776
0.8478 Intermediate Similarity NPC471902
0.8471 Intermediate Similarity NPC477371
0.8469 Intermediate Similarity NPC278628
0.8469 Intermediate Similarity NPC475494
0.8469 Intermediate Similarity NPC231530
0.8462 Intermediate Similarity NPC123854
0.8462 Intermediate Similarity NPC191684
0.8462 Intermediate Similarity NPC477149
0.8462 Intermediate Similarity NPC477147
0.8454 Intermediate Similarity NPC180204
0.8444 Intermediate Similarity NPC52169
0.8444 Intermediate Similarity NPC471724
0.8444 Intermediate Similarity NPC182797
0.8444 Intermediate Similarity NPC143767
0.8444 Intermediate Similarity NPC131470
0.8444 Intermediate Similarity NPC24816
0.8444 Intermediate Similarity NPC246708
0.8444 Intermediate Similarity NPC40552
0.8438 Intermediate Similarity NPC99411
0.8427 Intermediate Similarity NPC91525
0.8427 Intermediate Similarity NPC12774
0.8427 Intermediate Similarity NPC9892
0.8427 Intermediate Similarity NPC329943
0.8427 Intermediate Similarity NPC6979
0.8427 Intermediate Similarity NPC212843
0.8427 Intermediate Similarity NPC2783
0.8427 Intermediate Similarity NPC10005
0.8421 Intermediate Similarity NPC477854
0.8409 Intermediate Similarity NPC475509
0.8409 Intermediate Similarity NPC59453
0.8409 Intermediate Similarity NPC221758
0.8409 Intermediate Similarity NPC473246
0.8404 Intermediate Similarity NPC327179
0.8404 Intermediate Similarity NPC456
0.8404 Intermediate Similarity NPC230151
0.8404 Intermediate Similarity NPC328371
0.8404 Intermediate Similarity NPC472941
0.84 Intermediate Similarity NPC265655
0.8391 Intermediate Similarity NPC73882
0.8391 Intermediate Similarity NPC133391
0.8391 Intermediate Similarity NPC240302
0.8387 Intermediate Similarity NPC184870
0.8384 Intermediate Similarity NPC220974
0.837 Intermediate Similarity NPC475416
0.837 Intermediate Similarity NPC150383
0.8367 Intermediate Similarity NPC472227
0.8367 Intermediate Similarity NPC472228
0.8367 Intermediate Similarity NPC471293
0.8353 Intermediate Similarity NPC321514
0.8352 Intermediate Similarity NPC198664
0.8352 Intermediate Similarity NPC59263
0.8352 Intermediate Similarity NPC475049
0.8352 Intermediate Similarity NPC130520
0.8352 Intermediate Similarity NPC476733
0.8352 Intermediate Similarity NPC127689
0.8352 Intermediate Similarity NPC474245
0.8352 Intermediate Similarity NPC121798
0.8352 Intermediate Similarity NPC263393
0.8352 Intermediate Similarity NPC215029
0.8352 Intermediate Similarity NPC61543
0.8352 Intermediate Similarity NPC225585
0.8352 Intermediate Similarity NPC32830
0.8352 Intermediate Similarity NPC470588

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC111585 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
0.8889 High Similarity NPD6399 Phase 3
0.8587 High Similarity NPD7748 Approved
0.8571 High Similarity NPD8034 Phase 2
0.8571 High Similarity NPD8035 Phase 2
0.8409 Intermediate Similarity NPD4786 Approved
0.8352 Intermediate Similarity NPD5328 Approved
0.8316 Intermediate Similarity NPD7902 Approved
0.8315 Intermediate Similarity NPD7520 Clinical (unspecified phase)
0.8298 Intermediate Similarity NPD5695 Phase 3
0.8283 Intermediate Similarity NPD7128 Approved
0.8283 Intermediate Similarity NPD6402 Approved
0.8283 Intermediate Similarity NPD6675 Approved
0.8283 Intermediate Similarity NPD5739 Approved
0.8242 Intermediate Similarity NPD6672 Approved
0.8242 Intermediate Similarity NPD5737 Approved
0.8222 Intermediate Similarity NPD3618 Phase 1
0.8222 Intermediate Similarity NPD7146 Approved
0.8222 Intermediate Similarity NPD5330 Approved
0.8222 Intermediate Similarity NPD7334 Approved
0.8222 Intermediate Similarity NPD6409 Approved
0.8222 Intermediate Similarity NPD6684 Approved
0.8222 Intermediate Similarity NPD7521 Approved
0.8182 Intermediate Similarity NPD3667 Approved
0.8172 Intermediate Similarity NPD7515 Phase 2
0.8172 Intermediate Similarity NPD6079 Approved
0.8125 Intermediate Similarity NPD6083 Phase 2
0.8125 Intermediate Similarity NPD6084 Phase 2
0.8119 Intermediate Similarity NPD6881 Approved
0.8119 Intermediate Similarity NPD7320 Approved
0.8119 Intermediate Similarity NPD6899 Approved
0.8058 Intermediate Similarity NPD8130 Phase 1
0.8043 Intermediate Similarity NPD6903 Approved
0.8043 Intermediate Similarity NPD7513 Clinical (unspecified phase)
0.8041 Intermediate Similarity NPD7638 Approved
0.8039 Intermediate Similarity NPD6372 Approved
0.8039 Intermediate Similarity NPD6373 Approved
0.802 Intermediate Similarity NPD5697 Approved
0.802 Intermediate Similarity NPD5701 Approved
0.8 Intermediate Similarity NPD7901 Clinical (unspecified phase)
0.8 Intermediate Similarity NPD7900 Approved
0.7981 Intermediate Similarity NPD8297 Approved
0.7961 Intermediate Similarity NPD7102 Approved
0.7961 Intermediate Similarity NPD6883 Approved
0.7961 Intermediate Similarity NPD7290 Approved
0.7959 Intermediate Similarity NPD7640 Approved
0.7959 Intermediate Similarity NPD7639 Approved
0.7941 Intermediate Similarity NPD6011 Approved
0.7917 Intermediate Similarity NPD6356 Clinical (unspecified phase)
0.7895 Intermediate Similarity NPD4202 Approved
0.7885 Intermediate Similarity NPD6649 Approved
0.7885 Intermediate Similarity NPD6401 Clinical (unspecified phase)
0.7885 Intermediate Similarity NPD6650 Approved
0.7885 Intermediate Similarity NPD6869 Approved
0.7885 Intermediate Similarity NPD6617 Approved
0.7885 Intermediate Similarity NPD6847 Approved
0.7864 Intermediate Similarity NPD6012 Approved
0.7864 Intermediate Similarity NPD6014 Approved
0.7864 Intermediate Similarity NPD6013 Approved
0.7857 Intermediate Similarity NPD5696 Approved
0.7835 Intermediate Similarity NPD5222 Approved
0.7835 Intermediate Similarity NPD4697 Phase 3
0.7835 Intermediate Similarity NPD5221 Approved
0.7835 Intermediate Similarity NPD5220 Clinical (unspecified phase)
0.7826 Intermediate Similarity NPD5279 Phase 3
0.7826 Intermediate Similarity NPD6098 Approved
0.781 Intermediate Similarity NPD6882 Approved
0.7802 Intermediate Similarity NPD3133 Approved
0.7802 Intermediate Similarity NPD3666 Approved
0.7802 Intermediate Similarity NPD3668 Phase 3
0.7802 Intermediate Similarity NPD3665 Phase 1
0.7789 Intermediate Similarity NPD6411 Approved
0.7789 Intermediate Similarity NPD5284 Approved
0.7789 Intermediate Similarity NPD5281 Approved
0.7789 Intermediate Similarity NPD6050 Approved
0.7766 Intermediate Similarity NPD6673 Approved
0.7766 Intermediate Similarity NPD6080 Approved
0.7766 Intermediate Similarity NPD6904 Approved
0.7755 Intermediate Similarity NPD5173 Approved
0.7755 Intermediate Similarity NPD4755 Approved
0.7753 Intermediate Similarity NPD7525 Registered
0.7701 Intermediate Similarity NPD6117 Approved
0.7684 Intermediate Similarity NPD5692 Phase 3
0.7614 Intermediate Similarity NPD6116 Phase 1
0.7604 Intermediate Similarity NPD5694 Approved
0.76 Intermediate Similarity NPD5286 Approved
0.76 Intermediate Similarity NPD4700 Approved
0.76 Intermediate Similarity NPD4696 Approved
0.76 Intermediate Similarity NPD5285 Approved
0.7593 Intermediate Similarity NPD6868 Approved
0.7586 Intermediate Similarity NPD6942 Approved
0.7586 Intermediate Similarity NPD7339 Approved
0.7582 Intermediate Similarity NPD4223 Phase 3
0.7582 Intermediate Similarity NPD4221 Approved
0.7579 Intermediate Similarity NPD5764 Clinical (unspecified phase)
0.7579 Intermediate Similarity NPD4753 Phase 2
0.7579 Intermediate Similarity NPD6101 Approved
0.7573 Intermediate Similarity NPD6008 Approved
0.7528 Intermediate Similarity NPD6697 Approved
0.7528 Intermediate Similarity NPD6118 Approved
0.7528 Intermediate Similarity NPD6115 Approved
0.7528 Intermediate Similarity NPD6114 Approved
0.7527 Intermediate Similarity NPD5329 Approved
0.7525 Intermediate Similarity NPD5223 Approved
0.7523 Intermediate Similarity NPD7115 Discovery
0.75 Intermediate Similarity NPD5207 Approved
0.7474 Intermediate Similarity NPD5208 Approved
0.7471 Intermediate Similarity NPD6113 Clinical (unspecified phase)
0.7455 Intermediate Similarity NPD6335 Approved
0.7451 Intermediate Similarity NPD5224 Approved
0.7451 Intermediate Similarity NPD5211 Phase 2
0.7451 Intermediate Similarity NPD5225 Approved
0.7451 Intermediate Similarity NPD5226 Approved
0.7451 Intermediate Similarity NPD4633 Approved
0.7449 Intermediate Similarity NPD6001 Approved
0.7447 Intermediate Similarity NPD5280 Approved
0.7447 Intermediate Similarity NPD4694 Approved
0.7447 Intermediate Similarity NPD3574 Clinical (unspecified phase)
0.7447 Intermediate Similarity NPD5690 Phase 2
0.7431 Intermediate Similarity NPD6274 Approved
0.7423 Intermediate Similarity NPD5693 Phase 1
0.7419 Intermediate Similarity NPD4197 Approved
0.7407 Intermediate Similarity NPD4632 Approved
0.7396 Intermediate Similarity NPD6051 Approved
0.7387 Intermediate Similarity NPD7101 Approved
0.7387 Intermediate Similarity NPD7100 Approved
0.7379 Intermediate Similarity NPD5175 Approved
0.7379 Intermediate Similarity NPD5174 Approved
0.7379 Intermediate Similarity NPD4754 Approved
0.7368 Intermediate Similarity NPD3573 Approved
0.7364 Intermediate Similarity NPD6317 Approved
0.7333 Intermediate Similarity NPD5784 Clinical (unspecified phase)
0.7308 Intermediate Similarity NPD5141 Approved
0.7303 Intermediate Similarity NPD3701 Clinical (unspecified phase)
0.7297 Intermediate Similarity NPD6313 Approved
0.7297 Intermediate Similarity NPD6314 Approved
0.7283 Intermediate Similarity NPD4692 Approved
0.7283 Intermediate Similarity NPD4139 Approved
0.7282 Intermediate Similarity NPD7632 Discontinued
0.7263 Intermediate Similarity NPD4688 Approved
0.7263 Intermediate Similarity NPD5205 Approved
0.7263 Intermediate Similarity NPD4693 Phase 3
0.7263 Intermediate Similarity NPD4689 Approved
0.7263 Intermediate Similarity NPD4138 Approved
0.7263 Intermediate Similarity NPD4690 Approved
0.7257 Intermediate Similarity NPD6908 Approved
0.7257 Intermediate Similarity NPD6909 Approved
0.7253 Intermediate Similarity NPD7645 Phase 2
0.7238 Intermediate Similarity NPD4767 Approved
0.7238 Intermediate Similarity NPD4768 Approved
0.7216 Intermediate Similarity NPD7285 Clinical (unspecified phase)
0.7207 Intermediate Similarity NPD6009 Approved
0.7204 Intermediate Similarity NPD4752 Clinical (unspecified phase)
0.72 Intermediate Similarity NPD4629 Approved
0.72 Intermediate Similarity NPD5654 Approved
0.72 Intermediate Similarity NPD5210 Approved
0.7196 Intermediate Similarity NPD8132 Clinical (unspecified phase)
0.7172 Intermediate Similarity NPD5778 Approved
0.7172 Intermediate Similarity NPD5779 Approved
0.717 Intermediate Similarity NPD6412 Phase 2
0.7168 Intermediate Similarity NPD6319 Approved
0.7158 Intermediate Similarity NPD1694 Approved
0.7143 Intermediate Similarity NPD3617 Approved
0.713 Intermediate Similarity NPD7604 Phase 2
0.7128 Intermediate Similarity NPD4788 Approved
0.7128 Intermediate Similarity NPD5362 Discontinued
0.7105 Intermediate Similarity NPD5983 Phase 2
0.7105 Intermediate Similarity NPD6291 Clinical (unspecified phase)
0.7103 Intermediate Similarity NPD4730 Approved
0.7103 Intermediate Similarity NPD5128 Approved
0.7103 Intermediate Similarity NPD5168 Approved
0.7103 Intermediate Similarity NPD4729 Approved
0.7094 Intermediate Similarity NPD8293 Discontinued
0.7087 Intermediate Similarity NPD6404 Discontinued
0.7079 Intermediate Similarity NPD5733 Approved
0.7071 Intermediate Similarity NPD7637 Suspended
0.7069 Intermediate Similarity NPD7492 Approved
0.7059 Intermediate Similarity NPD5959 Approved
0.7045 Intermediate Similarity NPD4809 Clinical (unspecified phase)
0.7045 Intermediate Similarity NPD4243 Approved
0.7045 Intermediate Similarity NPD4808 Clinical (unspecified phase)
0.7034 Intermediate Similarity NPD7736 Approved
0.7021 Intermediate Similarity NPD6435 Approved
0.7018 Intermediate Similarity NPD6059 Approved
0.7018 Intermediate Similarity NPD6054 Approved
0.7009 Intermediate Similarity NPD6336 Discontinued
0.7009 Intermediate Similarity NPD6616 Approved
0.7 Intermediate Similarity NPD3702 Approved
0.699 Remote Similarity NPD4225 Approved
0.6989 Remote Similarity NPD4695 Discontinued
0.6989 Remote Similarity NPD4748 Discontinued
0.6972 Remote Similarity NPD5250 Approved
0.6972 Remote Similarity NPD5249 Phase 3
0.6972 Remote Similarity NPD5248 Approved
0.6972 Remote Similarity NPD5247 Approved
0.6972 Remote Similarity NPD5135 Approved
0.6972 Remote Similarity NPD5169 Approved
0.6972 Remote Similarity NPD5251 Approved
0.6972 Remote Similarity NPD5134 Clinical (unspecified phase)
0.6972 Remote Similarity NPD4634 Approved
0.697 Remote Similarity NPD4096 Approved

Structure

External Identifiers

PubChem CID   15292985
ChEMBL   CHEMBL497273
ZINC  

Physicochemical Properties

Molecular Weight:  498.37
ALogP:  3.7287
MLogP:  4.54
XLogP:  8.861
# Rotatable Bonds:  16
Polar Surface Area:  63.6
# H-Bond Aceptor:  4
# H-Bond Donor:  1
# Rings:  4
# Heavy Atoms:  36

Download Data

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General Info & Identifiers & Properties  
Structure MOL file  
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Biological Activities  
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