Natural Product: NPC232258

Natural Product ID:  NPC232258
Common Name:   Withalongolide M
IUPAC Name:   (2R)-2-[(1S)-1-[(3R,8S,9S,13S,14S,17R)-3-hydroxy-13-methyl-1-oxo-3,4,6,7,8,9,11,12,14,15,16,17-dodecahydro-2H-cyclopenta[a]phenanthren-17-yl]ethyl]-5-methyl-4-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-2,3-dihydropyran-6-one
Synonyms:   Withalongolide M
Molecular Formula:   C33H48O10
Standard InCHIKey:  CLUVBNATYXEVRS-UJQMTUMNSA-N
Standard InCHI:  InChI=1S/C33H48O10/c1-15-18(14-41-32-30(39)29(38)28(37)26(13-34)43-32)11-25(42-31(15)40)16(2)22-6-7-23-20-5-4-17-10-19(35)12-24(36)27(17)21(20)8-9-33(22,23)3/h16,19-23,25-26,28-30,32,34-35,37-39H,4-14H2,1-3H3/t16-,19+,20+,21-,22+,23-,25+,26+,28+,29-,30+,32+,33+/m0/s1
Canonical SMILES:  OC[C@H]1O[C@@H](OCC2=C(C)C(=O)O[C@H](C2)[C@H]([C@H]2CC[C@@H]3[C@]2(C)CC[C@H]2[C@H]3CCC3=C2C(=O)C[C@@H](C3)O)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
NPO14874 Physalis longifolia Species Solanaceae Eukaryota Aerial parts PMID[22098611]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT169 Cell Line B16-F10 Mus musculus IC50 > 10000 nM 22098611
NPT170 Cell Line SK-MEL-28 Homo sapiens IC50 > 10000 nM 22098611
NPT2 Others Unspecified IC50 > 10000 nM 22098611

  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 NPC232258 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 NPC129434
0.9727 High Similarity NPC291564
0.9316 High Similarity NPC245094
0.9224 High Similarity NPC318135
0.9076 High Similarity NPC476966
0.9 High Similarity NPC173347
0.8966 High Similarity NPC170084
0.8966 High Similarity NPC476204
0.8926 High Similarity NPC231240
0.8852 High Similarity NPC316915
0.8839 High Similarity NPC477073
0.8829 High Similarity NPC477070
0.8829 High Similarity NPC477069
0.8803 High Similarity NPC202051
0.8761 High Similarity NPC477253
0.8761 High Similarity NPC233003
0.8696 High Similarity NPC207637
0.8684 High Similarity NPC477074
0.8684 High Similarity NPC251309
0.8678 High Similarity NPC311534
0.8644 High Similarity NPC278163
0.8644 High Similarity NPC187950
0.8632 High Similarity NPC477071
0.8621 High Similarity NPC477252
0.8584 High Similarity NPC129340
0.8571 High Similarity NPC195708
0.8559 High Similarity NPC476127
0.8559 High Similarity NPC476150
0.8559 High Similarity NPC470312
0.8547 High Similarity NPC473617
0.8547 High Similarity NPC473828
0.8547 High Similarity NPC239293
0.8496 Intermediate Similarity NPC265655
0.8468 Intermediate Similarity NPC223741
0.8462 Intermediate Similarity NPC474483
0.8455 Intermediate Similarity NPC471407
0.8455 Intermediate Similarity NPC473593
0.8448 Intermediate Similarity NPC116024
0.8448 Intermediate Similarity NPC473882
0.8448 Intermediate Similarity NPC220293
0.8443 Intermediate Similarity NPC42399
0.843 Intermediate Similarity NPC7850
0.843 Intermediate Similarity NPC6615
0.8421 Intermediate Similarity NPC114961
0.8421 Intermediate Similarity NPC475243
0.8421 Intermediate Similarity NPC27551
0.8421 Intermediate Similarity NPC90630
0.8407 Intermediate Similarity NPC295389
0.8393 Intermediate Similarity NPC162033
0.8362 Intermediate Similarity NPC260665
0.8361 Intermediate Similarity NPC47113
0.8361 Intermediate Similarity NPC174367
0.8348 Intermediate Similarity NPC285410
0.8348 Intermediate Similarity NPC292196
0.8348 Intermediate Similarity NPC263827
0.8348 Intermediate Similarity NPC250481
0.8333 Intermediate Similarity NPC412
0.8333 Intermediate Similarity NPC246205
0.8333 Intermediate Similarity NPC258789
0.8333 Intermediate Similarity NPC194310
0.8333 Intermediate Similarity NPC118225
0.8333 Intermediate Similarity NPC258815
0.8333 Intermediate Similarity NPC241310
0.8333 Intermediate Similarity NPC131841
0.8333 Intermediate Similarity NPC169727
0.8333 Intermediate Similarity NPC475182
0.8333 Intermediate Similarity NPC47567
0.8333 Intermediate Similarity NPC475364
0.8333 Intermediate Similarity NPC31522
0.832 Intermediate Similarity NPC471855
0.8319 Intermediate Similarity NPC258592
0.8319 Intermediate Similarity NPC178548
0.8319 Intermediate Similarity NPC474179
0.8319 Intermediate Similarity NPC475834
0.8293 Intermediate Similarity NPC329784
0.8293 Intermediate Similarity NPC471357
0.8293 Intermediate Similarity NPC146456
0.8293 Intermediate Similarity NPC469757
0.8293 Intermediate Similarity NPC117702
0.8293 Intermediate Similarity NPC470516
0.8293 Intermediate Similarity NPC240070
0.8291 Intermediate Similarity NPC475163
0.8291 Intermediate Similarity NPC74727
0.8291 Intermediate Similarity NPC165439
0.8279 Intermediate Similarity NPC177820
0.8279 Intermediate Similarity NPC30188
0.8279 Intermediate Similarity NPC248202
0.8279 Intermediate Similarity NPC130229
0.8279 Intermediate Similarity NPC3381
0.8276 Intermediate Similarity NPC474265
0.8276 Intermediate Similarity NPC210420
0.8276 Intermediate Similarity NPC471967
0.8264 Intermediate Similarity NPC23786
0.8264 Intermediate Similarity NPC156789
0.8264 Intermediate Similarity NPC470265
0.8261 Intermediate Similarity NPC154856
0.8261 Intermediate Similarity NPC83005
0.8261 Intermediate Similarity NPC52241
0.8261 Intermediate Similarity NPC475317
0.8254 Intermediate Similarity NPC469749
0.8254 Intermediate Similarity NPC32793
0.8254 Intermediate Similarity NPC116075
0.8254 Intermediate Similarity NPC247190
0.8254 Intermediate Similarity NPC146857
0.825 Intermediate Similarity NPC129393
0.825 Intermediate Similarity NPC476849
0.825 Intermediate Similarity NPC251226
0.825 Intermediate Similarity NPC281840
0.8246 Intermediate Similarity NPC300614
0.8246 Intermediate Similarity NPC90946
0.8246 Intermediate Similarity NPC285576
0.824 Intermediate Similarity NPC213634
0.8235 Intermediate Similarity NPC45475
0.8235 Intermediate Similarity NPC86020
0.8235 Intermediate Similarity NPC475632
0.8235 Intermediate Similarity NPC475913
0.8226 Intermediate Similarity NPC473620
0.8205 Intermediate Similarity NPC200944
0.8205 Intermediate Similarity NPC75167
0.8205 Intermediate Similarity NPC311592
0.8205 Intermediate Similarity NPC73986
0.8205 Intermediate Similarity NPC73455
0.8197 Intermediate Similarity NPC41129
0.8197 Intermediate Similarity NPC27363
0.8197 Intermediate Similarity NPC160084
0.819 Intermediate Similarity NPC31839
0.819 Intermediate Similarity NPC11035
0.819 Intermediate Similarity NPC190837
0.8189 Intermediate Similarity NPC329636
0.8182 Intermediate Similarity NPC159456
0.8182 Intermediate Similarity NPC46570
0.8182 Intermediate Similarity NPC4021
0.8182 Intermediate Similarity NPC67569
0.8174 Intermediate Similarity NPC137917
0.8167 Intermediate Similarity NPC122971
0.8167 Intermediate Similarity NPC197003
0.8167 Intermediate Similarity NPC190939
0.816 Intermediate Similarity NPC471352
0.816 Intermediate Similarity NPC469755
0.816 Intermediate Similarity NPC469753
0.816 Intermediate Similarity NPC329986
0.816 Intermediate Similarity NPC10823
0.816 Intermediate Similarity NPC140092
0.816 Intermediate Similarity NPC180079
0.816 Intermediate Similarity NPC471361
0.816 Intermediate Similarity NPC86159
0.816 Intermediate Similarity NPC251866
0.816 Intermediate Similarity NPC284406
0.816 Intermediate Similarity NPC17896
0.816 Intermediate Similarity NPC70542
0.816 Intermediate Similarity NPC89514
0.816 Intermediate Similarity NPC232785
0.816 Intermediate Similarity NPC9499
0.816 Intermediate Similarity NPC6108
0.816 Intermediate Similarity NPC125077
0.816 Intermediate Similarity NPC469751
0.816 Intermediate Similarity NPC219085
0.816 Intermediate Similarity NPC469754
0.816 Intermediate Similarity NPC471360
0.816 Intermediate Similarity NPC276838
0.816 Intermediate Similarity NPC469752
0.816 Intermediate Similarity NPC188234
0.816 Intermediate Similarity NPC471359
0.816 Intermediate Similarity NPC471358
0.816 Intermediate Similarity NPC197707
0.8151 Intermediate Similarity NPC203862
0.8151 Intermediate Similarity NPC55296
0.8151 Intermediate Similarity NPC473405
0.8145 Intermediate Similarity NPC298841
0.8136 Intermediate Similarity NPC110861
0.8136 Intermediate Similarity NPC474557
0.8136 Intermediate Similarity NPC181145
0.813 Intermediate Similarity NPC469841
0.813 Intermediate Similarity NPC473474
0.813 Intermediate Similarity NPC469842
0.8125 Intermediate Similarity NPC158350
0.8125 Intermediate Similarity NPC194716
0.812 Intermediate Similarity NPC195132
0.812 Intermediate Similarity NPC64106
0.812 Intermediate Similarity NPC80843
0.812 Intermediate Similarity NPC212968
0.812 Intermediate Similarity NPC65590
0.812 Intermediate Similarity NPC1046
0.812 Intermediate Similarity NPC130427
0.812 Intermediate Similarity NPC161434
0.812 Intermediate Similarity NPC470543
0.812 Intermediate Similarity NPC236217
0.812 Intermediate Similarity NPC48249
0.812 Intermediate Similarity NPC125923
0.8115 Intermediate Similarity NPC269642
0.8115 Intermediate Similarity NPC28532
0.8115 Intermediate Similarity NPC107493
0.8103 Intermediate Similarity NPC242611
0.8103 Intermediate Similarity NPC78046
0.8103 Intermediate Similarity NPC274507
0.8103 Intermediate Similarity NPC269095
0.8103 Intermediate Similarity NPC220984
0.8099 Intermediate Similarity NPC308459
0.8099 Intermediate Similarity NPC48692
0.8099 Intermediate Similarity NPC473130

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC232258 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
0.8333 Intermediate Similarity NPD8132 Clinical (unspecified phase)
0.816 Intermediate Similarity NPD7319 Approved
0.8087 Intermediate Similarity NPD6686 Approved
0.8065 Intermediate Similarity NPD7507 Approved
0.8051 Intermediate Similarity NPD8133 Approved
0.8033 Intermediate Similarity NPD8033 Approved
0.8 Intermediate Similarity NPD6412 Phase 2
0.8 Intermediate Similarity NPD8295 Clinical (unspecified phase)
0.7951 Intermediate Similarity NPD8377 Approved
0.7951 Intermediate Similarity NPD8294 Approved
0.7903 Intermediate Similarity NPD8328 Phase 3
0.7886 Intermediate Similarity NPD8378 Approved
0.7886 Intermediate Similarity NPD7503 Approved
0.7886 Intermediate Similarity NPD8296 Approved
0.7886 Intermediate Similarity NPD8380 Approved
0.7886 Intermediate Similarity NPD8335 Approved
0.7886 Intermediate Similarity NPD8379 Approved
0.7851 Intermediate Similarity NPD7115 Discovery
0.7787 Intermediate Similarity NPD7328 Approved
0.7787 Intermediate Similarity NPD7327 Approved
0.7742 Intermediate Similarity NPD8513 Phase 3
0.7724 Intermediate Similarity NPD7516 Approved
0.7656 Intermediate Similarity NPD7736 Approved
0.76 Intermediate Similarity NPD8516 Approved
0.76 Intermediate Similarity NPD8515 Approved
0.76 Intermediate Similarity NPD8517 Approved
0.7578 Intermediate Similarity NPD8293 Discontinued
0.7417 Intermediate Similarity NPD4061 Clinical (unspecified phase)
0.7402 Intermediate Similarity NPD6370 Approved
0.7287 Intermediate Similarity NPD7492 Approved
0.7244 Intermediate Similarity NPD6319 Approved
0.7244 Intermediate Similarity NPD6054 Approved
0.7244 Intermediate Similarity NPD6059 Approved
0.7241 Intermediate Similarity NPD7638 Approved
0.7231 Intermediate Similarity NPD6616 Approved
0.7227 Intermediate Similarity NPD8170 Clinical (unspecified phase)
0.7213 Intermediate Similarity NPD5955 Clinical (unspecified phase)
0.7179 Intermediate Similarity NPD7639 Approved
0.7179 Intermediate Similarity NPD7640 Approved
0.7176 Intermediate Similarity NPD7078 Approved
0.7154 Intermediate Similarity NPD8413 Clinical (unspecified phase)
0.7097 Intermediate Similarity NPD8297 Approved
0.7097 Intermediate Similarity NPD6882 Approved
0.7059 Intermediate Similarity NPD7632 Discontinued
0.7054 Intermediate Similarity NPD6015 Approved
0.7054 Intermediate Similarity NPD6016 Approved
0.7008 Intermediate Similarity NPD6009 Approved
0.7 Intermediate Similarity NPD5988 Approved
0.6967 Remote Similarity NPD5954 Clinical (unspecified phase)
0.696 Remote Similarity NPD6053 Discontinued
0.6957 Remote Similarity NPD6399 Phase 3
0.6949 Remote Similarity NPD4225 Approved
0.693 Remote Similarity NPD6698 Approved
0.693 Remote Similarity NPD46 Approved
0.6911 Remote Similarity NPD5345 Clinical (unspecified phase)
0.6905 Remote Similarity NPD4632 Approved
0.6897 Remote Similarity NPD7748 Approved
0.6885 Remote Similarity NPD6402 Approved
0.6885 Remote Similarity NPD5739 Approved
0.6885 Remote Similarity NPD7128 Approved
0.6885 Remote Similarity NPD6675 Approved
0.6864 Remote Similarity NPD7902 Approved
0.6855 Remote Similarity NPD6372 Approved
0.6855 Remote Similarity NPD6373 Approved
0.6818 Remote Similarity NPD6067 Discontinued
0.68 Remote Similarity NPD6371 Approved
0.6791 Remote Similarity NPD8074 Phase 3
0.6774 Remote Similarity NPD6881 Approved
0.6774 Remote Similarity NPD6899 Approved
0.6774 Remote Similarity NPD7320 Approved
0.6746 Remote Similarity NPD6649 Approved
0.6746 Remote Similarity NPD6650 Approved
0.6746 Remote Similarity NPD8130 Phase 1
0.6741 Remote Similarity NPD6033 Approved
0.6724 Remote Similarity NPD7515 Phase 2
0.6723 Remote Similarity NPD6084 Phase 2
0.6723 Remote Similarity NPD6083 Phase 2
0.6695 Remote Similarity NPD5695 Phase 3
0.6694 Remote Similarity NPD5701 Approved
0.6694 Remote Similarity NPD5697 Approved
0.6694 Remote Similarity NPD7899 Clinical (unspecified phase)
0.6667 Remote Similarity NPD7290 Approved
0.6667 Remote Similarity NPD7102 Approved
0.6667 Remote Similarity NPD4634 Approved
0.6667 Remote Similarity NPD6883 Approved
0.6667 Remote Similarity NPD8171 Discontinued
0.6618 Remote Similarity NPD8336 Approved
0.6618 Remote Similarity NPD8337 Approved
0.6614 Remote Similarity NPD6617 Approved
0.6614 Remote Similarity NPD6869 Approved
0.6614 Remote Similarity NPD6847 Approved
0.6613 Remote Similarity NPD6008 Approved
0.661 Remote Similarity NPD7901 Clinical (unspecified phase)
0.661 Remote Similarity NPD7900 Approved
0.6594 Remote Similarity NPD7260 Phase 2
0.6587 Remote Similarity NPD6013 Approved
0.6587 Remote Similarity NPD6014 Approved
0.6587 Remote Similarity NPD6012 Approved
0.6581 Remote Similarity NPD6411 Approved
0.6581 Remote Similarity NPD8035 Phase 2
0.6581 Remote Similarity NPD8034 Phase 2
0.6567 Remote Similarity NPD7604 Phase 2
0.6552 Remote Similarity NPD5328 Approved
0.6549 Remote Similarity NPD4786 Approved
0.6547 Remote Similarity NPD6845 Suspended
0.6541 Remote Similarity NPD5983 Phase 2
0.6529 Remote Similarity NPD8029 Clinical (unspecified phase)
0.6525 Remote Similarity NPD5778 Approved
0.6525 Remote Similarity NPD5779 Approved
0.6508 Remote Similarity NPD6011 Approved
0.6493 Remote Similarity NPD8080 Discontinued
0.6484 Remote Similarity NPD6401 Clinical (unspecified phase)
0.6471 Remote Similarity NPD6336 Discontinued
0.6466 Remote Similarity NPD6672 Approved
0.6466 Remote Similarity NPD5737 Approved
0.6466 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6446 Remote Similarity NPD4755 Approved
0.6444 Remote Similarity NPD7829 Approved
0.6444 Remote Similarity NPD7830 Approved
0.6441 Remote Similarity NPD6079 Approved
0.6441 Remote Similarity NPD7983 Approved
0.6441 Remote Similarity NPD7637 Suspended
0.6435 Remote Similarity NPD7334 Approved
0.6435 Remote Similarity NPD6409 Approved
0.6435 Remote Similarity NPD7521 Approved
0.6435 Remote Similarity NPD7146 Approved
0.6435 Remote Similarity NPD5330 Approved
0.6435 Remote Similarity NPD6684 Approved
0.6435 Remote Similarity NPD3618 Phase 1
0.6429 Remote Similarity NPD8338 Approved
0.642 Remote Similarity NPD7799 Discontinued
0.6419 Remote Similarity NPD7625 Phase 1
0.6418 Remote Similarity NPD6921 Approved
0.6412 Remote Similarity NPD6940 Discontinued
0.641 Remote Similarity NPD6101 Approved
0.641 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6404 Remote Similarity NPD6400 Clinical (unspecified phase)
0.6403 Remote Similarity NPD5956 Approved
0.6393 Remote Similarity NPD5696 Approved
0.6387 Remote Similarity NPD4202 Approved
0.6372 Remote Similarity NPD3667 Approved
0.6371 Remote Similarity NPD5211 Phase 2
0.6364 Remote Similarity NPD8137 Clinical (unspecified phase)
0.6356 Remote Similarity NPD7838 Discovery
0.6356 Remote Similarity NPD5785 Approved
0.6348 Remote Similarity NPD7520 Clinical (unspecified phase)
0.6341 Remote Similarity NPD5286 Approved
0.6341 Remote Similarity NPD5285 Approved
0.6341 Remote Similarity NPD4700 Approved
0.6341 Remote Similarity NPD4696 Approved
0.6325 Remote Similarity NPD6903 Approved
0.6324 Remote Similarity NPD7642 Approved
0.6303 Remote Similarity NPD5693 Phase 1
0.6303 Remote Similarity NPD5281 Approved
0.6303 Remote Similarity NPD5284 Approved
0.6296 Remote Similarity NPD8444 Approved
0.6296 Remote Similarity NPD8274 Clinical (unspecified phase)
0.6293 Remote Similarity NPD5279 Phase 3
0.629 Remote Similarity NPD5344 Discontinued
0.6288 Remote Similarity NPD6274 Approved
0.6271 Remote Similarity NPD7285 Clinical (unspecified phase)
0.6271 Remote Similarity NPD4753 Phase 2
0.627 Remote Similarity NPD5141 Approved
0.6269 Remote Similarity NPD7100 Approved
0.6269 Remote Similarity NPD7101 Approved
0.6261 Remote Similarity NPD3665 Phase 1
0.6261 Remote Similarity NPD3133 Approved
0.6261 Remote Similarity NPD3666 Approved
0.624 Remote Similarity NPD5225 Approved
0.624 Remote Similarity NPD5226 Approved
0.624 Remote Similarity NPD5224 Approved
0.624 Remote Similarity NPD4633 Approved
0.6232 Remote Similarity NPD8451 Approved
0.623 Remote Similarity NPD4697 Phase 3
0.623 Remote Similarity NPD5220 Clinical (unspecified phase)
0.623 Remote Similarity NPD5222 Approved
0.623 Remote Similarity NPD5221 Approved
0.622 Remote Similarity NPD4767 Approved
0.622 Remote Similarity NPD4768 Approved
0.6207 Remote Similarity NPD1694 Approved
0.6197 Remote Similarity NPD8449 Approved
0.6194 Remote Similarity NPD6335 Approved
0.619 Remote Similarity NPD5175 Approved
0.619 Remote Similarity NPD5174 Approved
0.6187 Remote Similarity NPD8448 Approved
0.6179 Remote Similarity NPD5173 Approved
0.6176 Remote Similarity NPD6908 Approved
0.6176 Remote Similarity NPD6909 Approved
0.617 Remote Similarity NPD8390 Approved
0.617 Remote Similarity NPD6914 Discontinued
0.617 Remote Similarity NPD8392 Approved
0.617 Remote Similarity NPD8391 Approved
0.6167 Remote Similarity NPD6050 Approved
0.6165 Remote Similarity NPD6868 Approved
0.6161 Remote Similarity NPD6115 Approved
0.6161 Remote Similarity NPD6114 Approved
0.6161 Remote Similarity NPD6697 Approved
0.6161 Remote Similarity NPD6118 Approved
0.616 Remote Similarity NPD5223 Approved
0.6154 Remote Similarity NPD3574 Clinical (unspecified phase)

Structure

External Identifiers

PubChem CID   56926294
ChEMBL   CHEMBL1934465
ZINC  

Physicochemical Properties

Molecular Weight:  604.32
ALogP:  -1.013
MLogP:  3.99
XLogP:  2.555
# Rotatable Bonds:  14
Polar Surface Area:  162.98
# H-Bond Aceptor:  10
# H-Bond Donor:  5
# Rings:  6
# Heavy Atoms:  43

Download Data

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