Natural Product: NPC471238

Natural Product ID:  NPC471238
Common Name:   3,9,13-Trihydroxymegastigman-7-Ene
IUPAC Name:   (1S,4S,5R)-4-[(E,3R)-3-hydroxybut-1-enyl]-5-(hydroxymethyl)-3,3-dimethylcyclohexan-1-ol
Synonyms:  
Molecular Formula:   C13H24O3
Standard InCHIKey:  WEVMBOVJPQRPQV-OVPAZRRRSA-N
Standard InCHI:  InChI=1S/C13H24O3/c1-9(15)4-5-12-10(8-14)6-11(16)7-13(12,2)3/h4-5,9-12,14-16H,6-8H2,1-3H3/b5-4+/t9-,10+,11+,12+/m1/s1
Canonical SMILES:  OC[C@@H]1C[C@H](O)CC([C@H]1/C=C/[C@H](O)C)(C)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
NPO32875 cinnamomum wilsonii Species Lauraceae Eukaryota Leaves PMID[23822611]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT81 Cell Line A549 Homo sapiens IC50 > 10000 nM 10.6019/CHEMBL1201861
NPT116 Cell Line HL-60 Homo sapiens IC50 > 10000 nM 19581457
NPT83 Cell Line MCF7 Homo sapiens IC50 > 10000 nM 24689881
NPT659 Cell Line SMMC-7721 Homo sapiens IC50 > 10000 nM 10.1021/np50041a029
NPT660 Cell Line SW480 Homo sapiens IC50 > 10000 nM DrugMatrix in vitro pharmacology data

  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 NPC471238 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
0.9545 High Similarity NPC471272
0.9254 High Similarity NPC471268
0.9254 High Similarity NPC471271
0.8971 High Similarity NPC477792
0.8806 High Similarity NPC96484
0.8732 High Similarity NPC253190
0.8714 High Similarity NPC306727
0.8696 High Similarity NPC23954
0.8611 High Similarity NPC149550
0.8611 High Similarity NPC85105
0.8571 High Similarity NPC68443
0.8551 High Similarity NPC92801
0.8551 High Similarity NPC34834
0.8514 High Similarity NPC96362
0.8514 High Similarity NPC95124
0.8514 High Similarity NPC471266
0.8493 Intermediate Similarity NPC11908
0.8472 Intermediate Similarity NPC265588
0.8451 Intermediate Similarity NPC476366
0.8451 Intermediate Similarity NPC201048
0.8429 Intermediate Similarity NPC164022
0.8406 Intermediate Similarity NPC471560
0.8406 Intermediate Similarity NPC9942
0.8406 Intermediate Similarity NPC474248
0.84 Intermediate Similarity NPC471270
0.84 Intermediate Similarity NPC476646
0.8382 Intermediate Similarity NPC68703
0.8382 Intermediate Similarity NPC69649
0.8356 Intermediate Similarity NPC470711
0.8356 Intermediate Similarity NPC91594
0.8356 Intermediate Similarity NPC470758
0.8333 Intermediate Similarity NPC291503
0.8333 Intermediate Similarity NPC83200
0.831 Intermediate Similarity NPC220939
0.831 Intermediate Similarity NPC265485
0.8267 Intermediate Similarity NPC236707
0.8243 Intermediate Similarity NPC83351
0.8243 Intermediate Similarity NPC167891
0.8243 Intermediate Similarity NPC476314
0.8235 Intermediate Similarity NPC202017
0.8219 Intermediate Similarity NPC470749
0.8209 Intermediate Similarity NPC225415
0.8209 Intermediate Similarity NPC300593
0.8209 Intermediate Similarity NPC68656
0.8194 Intermediate Similarity NPC477138
0.8194 Intermediate Similarity NPC243342
0.8194 Intermediate Similarity NPC91858
0.8182 Intermediate Similarity NPC185605
0.8169 Intermediate Similarity NPC167706
0.8169 Intermediate Similarity NPC242001
0.8158 Intermediate Similarity NPC249423
0.8133 Intermediate Similarity NPC209430
0.8133 Intermediate Similarity NPC30986
0.8116 Intermediate Similarity NPC171225
0.8116 Intermediate Similarity NPC114651
0.8082 Intermediate Similarity NPC69383
0.8082 Intermediate Similarity NPC133580
0.8082 Intermediate Similarity NPC313179
0.8082 Intermediate Similarity NPC32832
0.8082 Intermediate Similarity NPC171148
0.806 Intermediate Similarity NPC81615
0.8056 Intermediate Similarity NPC471799
0.8056 Intermediate Similarity NPC182717
0.8052 Intermediate Similarity NPC296701
0.8052 Intermediate Similarity NPC218616
0.8052 Intermediate Similarity NPC87489
0.8052 Intermediate Similarity NPC259858
0.803 Intermediate Similarity NPC240506
0.8028 Intermediate Similarity NPC145498
0.8026 Intermediate Similarity NPC295131
0.8026 Intermediate Similarity NPC281880
0.8026 Intermediate Similarity NPC234193
0.8026 Intermediate Similarity NPC206062
0.8 Intermediate Similarity NPC276616
0.8 Intermediate Similarity NPC208999
0.8 Intermediate Similarity NPC245795
0.7973 Intermediate Similarity NPC477925
0.7973 Intermediate Similarity NPC274079
0.7973 Intermediate Similarity NPC106432
0.7973 Intermediate Similarity NPC1973
0.7973 Intermediate Similarity NPC167873
0.7971 Intermediate Similarity NPC475897
0.7971 Intermediate Similarity NPC267027
0.7971 Intermediate Similarity NPC476406
0.7949 Intermediate Similarity NPC82623
0.7949 Intermediate Similarity NPC79945
0.7945 Intermediate Similarity NPC469534
0.7945 Intermediate Similarity NPC469593
0.7945 Intermediate Similarity NPC469533
0.7945 Intermediate Similarity NPC471797
0.7941 Intermediate Similarity NPC144650
0.7941 Intermediate Similarity NPC290367
0.7941 Intermediate Similarity NPC96793
0.7941 Intermediate Similarity NPC323424
0.7941 Intermediate Similarity NPC107540
0.7922 Intermediate Similarity NPC159148
0.7922 Intermediate Similarity NPC264245
0.7917 Intermediate Similarity NPC110799
0.7895 Intermediate Similarity NPC308038
0.7895 Intermediate Similarity NPC81306
0.7895 Intermediate Similarity NPC47982
0.7895 Intermediate Similarity NPC28862
0.7895 Intermediate Similarity NPC109546
0.7895 Intermediate Similarity NPC84694
0.7895 Intermediate Similarity NPC143182
0.7887 Intermediate Similarity NPC473893
0.7875 Intermediate Similarity NPC299068
0.7875 Intermediate Similarity NPC139724
0.7867 Intermediate Similarity NPC203403
0.7867 Intermediate Similarity NPC74995
0.7867 Intermediate Similarity NPC471798
0.7857 Intermediate Similarity NPC139207
0.7857 Intermediate Similarity NPC185874
0.7857 Intermediate Similarity NPC477791
0.7857 Intermediate Similarity NPC476650
0.7848 Intermediate Similarity NPC231310
0.7848 Intermediate Similarity NPC238485
0.7848 Intermediate Similarity NPC102048
0.7838 Intermediate Similarity NPC66566
0.7838 Intermediate Similarity NPC313185
0.7838 Intermediate Similarity NPC477923
0.7826 Intermediate Similarity NPC258595
0.7826 Intermediate Similarity NPC287339
0.7826 Intermediate Similarity NPC60837
0.7826 Intermediate Similarity NPC208198
0.7826 Intermediate Similarity NPC172613
0.7826 Intermediate Similarity NPC11555
0.7826 Intermediate Similarity NPC2728
0.7826 Intermediate Similarity NPC282619
0.7821 Intermediate Similarity NPC155521
0.7821 Intermediate Similarity NPC93590
0.7821 Intermediate Similarity NPC50964
0.7821 Intermediate Similarity NPC202389
0.7821 Intermediate Similarity NPC49964
0.7821 Intermediate Similarity NPC109938
0.7821 Intermediate Similarity NPC122945
0.7808 Intermediate Similarity NPC474140
0.7808 Intermediate Similarity NPC130665
0.7794 Intermediate Similarity NPC174956
0.7794 Intermediate Similarity NPC474155
0.7794 Intermediate Similarity NPC473759
0.7792 Intermediate Similarity NPC157895
0.7792 Intermediate Similarity NPC241290
0.7792 Intermediate Similarity NPC287749
0.7792 Intermediate Similarity NPC113024
0.7792 Intermediate Similarity NPC209944
0.7792 Intermediate Similarity NPC104120
0.7792 Intermediate Similarity NPC148685
0.7792 Intermediate Similarity NPC164840
0.7778 Intermediate Similarity NPC189745
0.7763 Intermediate Similarity NPC300499
0.7763 Intermediate Similarity NPC474216
0.7763 Intermediate Similarity NPC244385
0.7763 Intermediate Similarity NPC6978
0.7763 Intermediate Similarity NPC138621
0.7763 Intermediate Similarity NPC167037
0.7761 Intermediate Similarity NPC99487
0.7761 Intermediate Similarity NPC66020
0.775 Intermediate Similarity NPC471267
0.775 Intermediate Similarity NPC470360
0.775 Intermediate Similarity NPC109528
0.7746 Intermediate Similarity NPC167527
0.7746 Intermediate Similarity NPC117804
0.7733 Intermediate Similarity NPC470362
0.7733 Intermediate Similarity NPC247325
0.7733 Intermediate Similarity NPC129165
0.7733 Intermediate Similarity NPC134330
0.7733 Intermediate Similarity NPC244488
0.7722 Intermediate Similarity NPC134481
0.7722 Intermediate Similarity NPC105173
0.7722 Intermediate Similarity NPC317458
0.7722 Intermediate Similarity NPC470558
0.7722 Intermediate Similarity NPC470384
0.7714 Intermediate Similarity NPC279434
0.7714 Intermediate Similarity NPC326310
0.7714 Intermediate Similarity NPC149680
0.7703 Intermediate Similarity NPC309178
0.7703 Intermediate Similarity NPC100334
0.7692 Intermediate Similarity NPC311891
0.7692 Intermediate Similarity NPC47761
0.7692 Intermediate Similarity NPC209620
0.7692 Intermediate Similarity NPC48891
0.7692 Intermediate Similarity NPC23852
0.7683 Intermediate Similarity NPC133588
0.7681 Intermediate Similarity NPC309300
0.7681 Intermediate Similarity NPC101128
0.7671 Intermediate Similarity NPC469343
0.7671 Intermediate Similarity NPC242992
0.7662 Intermediate Similarity NPC152061
0.7662 Intermediate Similarity NPC273410
0.7662 Intermediate Similarity NPC470429
0.7662 Intermediate Similarity NPC80530
0.7654 Intermediate Similarity NPC473226
0.7654 Intermediate Similarity NPC261266
0.7647 Intermediate Similarity NPC207007
0.7647 Intermediate Similarity NPC321867
0.7647 Intermediate Similarity NPC68679
0.7647 Intermediate Similarity NPC475251
0.7647 Intermediate Similarity NPC225342
0.7639 Intermediate Similarity NPC210323

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC471238 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
0.8082 Intermediate Similarity NPD8264 Approved
0.7647 Intermediate Similarity NPD368 Approved
0.7564 Intermediate Similarity NPD7525 Registered
0.75 Intermediate Similarity NPD3701 Clinical (unspecified phase)
0.7436 Intermediate Similarity NPD7645 Phase 2
0.7368 Intermediate Similarity NPD6942 Approved
0.7368 Intermediate Similarity NPD7339 Approved
0.7308 Intermediate Similarity NPD7322 Clinical (unspecified phase)
0.7273 Intermediate Similarity NPD342 Phase 1
0.7237 Intermediate Similarity NPD6924 Approved
0.7237 Intermediate Similarity NPD6926 Approved
0.7215 Intermediate Similarity NPD6929 Approved
0.72 Intermediate Similarity NPD7151 Approved
0.72 Intermediate Similarity NPD7152 Approved
0.72 Intermediate Similarity NPD7150 Approved
0.7143 Intermediate Similarity NPD4751 Clinical (unspecified phase)
0.7125 Intermediate Similarity NPD7509 Discontinued
0.7125 Intermediate Similarity NPD6931 Approved
0.7125 Intermediate Similarity NPD7332 Phase 2
0.7125 Intermediate Similarity NPD6930 Phase 2
0.7125 Intermediate Similarity NPD7514 Phase 3
0.7089 Intermediate Similarity NPD7145 Approved
0.7067 Intermediate Similarity NPD7143 Approved
0.7067 Intermediate Similarity NPD7144 Approved
0.7051 Intermediate Similarity NPD6933 Approved
0.7037 Intermediate Similarity NPD6902 Approved
0.6988 Remote Similarity NPD7338 Clinical (unspecified phase)
0.6962 Remote Similarity NPD5776 Phase 2
0.6962 Remote Similarity NPD6925 Approved
0.6951 Remote Similarity NPD3667 Approved
0.6933 Remote Similarity NPD6922 Approved
0.6933 Remote Similarity NPD6923 Approved
0.6912 Remote Similarity NPD4219 Approved
0.6867 Remote Similarity NPD6695 Phase 3
0.6824 Remote Similarity NPD3618 Phase 1
0.6786 Remote Similarity NPD4786 Approved
0.675 Remote Similarity NPD6932 Approved
0.6707 Remote Similarity NPD4748 Discontinued
0.6706 Remote Similarity NPD6893 Approved
0.6667 Remote Similarity NPD4732 Discontinued
0.6667 Remote Similarity NPD5784 Clinical (unspecified phase)
0.6629 Remote Similarity NPD6079 Approved
0.6627 Remote Similarity NPD6898 Phase 1
0.6591 Remote Similarity NPD5328 Approved
0.6588 Remote Similarity NPD3666 Approved
0.6588 Remote Similarity NPD3665 Phase 1
0.6588 Remote Similarity NPD3133 Approved
0.6582 Remote Similarity NPD4784 Approved
0.6582 Remote Similarity NPD4785 Approved
0.6559 Remote Similarity NPD4225 Approved
0.6556 Remote Similarity NPD4202 Approved
0.6552 Remote Similarity NPD7750 Discontinued
0.6552 Remote Similarity NPD7524 Approved
0.6538 Remote Similarity NPD4243 Approved
0.6526 Remote Similarity NPD5211 Phase 2
0.6512 Remote Similarity NPD1696 Phase 3
0.6506 Remote Similarity NPD4819 Approved
0.6506 Remote Similarity NPD4822 Approved
0.6506 Remote Similarity NPD4820 Approved
0.6506 Remote Similarity NPD4821 Approved
0.6489 Remote Similarity NPD7639 Approved
0.6489 Remote Similarity NPD7640 Approved
0.6463 Remote Similarity NPD4271 Approved
0.6463 Remote Similarity NPD4268 Approved
0.6444 Remote Similarity NPD7515 Phase 2
0.6437 Remote Similarity NPD4519 Discontinued
0.6437 Remote Similarity NPD4623 Approved
0.6437 Remote Similarity NPD5279 Phase 3
0.6392 Remote Similarity NPD5141 Approved
0.6386 Remote Similarity NPD4195 Approved
0.6386 Remote Similarity NPD6683 Phase 2
0.6383 Remote Similarity NPD7638 Approved
0.6344 Remote Similarity NPD5220 Clinical (unspecified phase)
0.6344 Remote Similarity NPD5222 Approved
0.6344 Remote Similarity NPD5221 Approved
0.6316 Remote Similarity NPD5285 Approved
0.6316 Remote Similarity NPD4696 Approved
0.6316 Remote Similarity NPD5286 Approved
0.631 Remote Similarity NPD5790 Clinical (unspecified phase)
0.6308 Remote Similarity NPD384 Approved
0.6308 Remote Similarity NPD385 Approved
0.6296 Remote Similarity NPD4190 Phase 3
0.6296 Remote Similarity NPD5275 Approved
0.6277 Remote Similarity NPD4755 Approved
0.6277 Remote Similarity NPD5173 Approved
0.6264 Remote Similarity NPD7087 Discontinued
0.6264 Remote Similarity NPD7637 Suspended
0.625 Remote Similarity NPD5344 Discontinued
0.625 Remote Similarity NPD5223 Approved
0.6211 Remote Similarity NPD5290 Discontinued
0.6207 Remote Similarity NPD3668 Phase 3
0.6196 Remote Similarity NPD5778 Approved
0.6196 Remote Similarity NPD5779 Approved
0.6196 Remote Similarity NPD6399 Phase 3
0.6186 Remote Similarity NPD5224 Approved
0.6186 Remote Similarity NPD5225 Approved
0.6186 Remote Similarity NPD5226 Approved
0.6186 Remote Similarity NPD4633 Approved
0.617 Remote Similarity NPD4697 Phase 3
0.6163 Remote Similarity NPD4270 Approved
0.6163 Remote Similarity NPD4269 Approved
0.6154 Remote Similarity NPD7136 Phase 2
0.6146 Remote Similarity NPD4700 Approved
0.6136 Remote Similarity NPD7520 Clinical (unspecified phase)
0.6129 Remote Similarity NPD7748 Approved
0.6122 Remote Similarity NPD5174 Approved
0.6122 Remote Similarity NPD5175 Approved
0.6119 Remote Similarity NPD9410 Clinical (unspecified phase)
0.6118 Remote Similarity NPD8259 Clinical (unspecified phase)
0.6118 Remote Similarity NPD4695 Discontinued
0.6105 Remote Similarity NPD7902 Approved
0.6092 Remote Similarity NPD5332 Approved
0.6092 Remote Similarity NPD5331 Approved
0.6092 Remote Similarity NPD5362 Discontinued
0.6087 Remote Similarity NPD6411 Approved
0.6047 Remote Similarity NPD4790 Discontinued
0.6044 Remote Similarity NPD4753 Phase 2
0.6 Remote Similarity NPD4194 Approved
0.6 Remote Similarity NPD4192 Approved
0.6 Remote Similarity NPD4193 Approved
0.6 Remote Similarity NPD4191 Approved
0.5979 Remote Similarity NPD6648 Approved
0.5978 Remote Similarity NPD5785 Approved
0.5977 Remote Similarity NPD4223 Phase 3
0.5977 Remote Similarity NPD4752 Clinical (unspecified phase)
0.5977 Remote Similarity NPD4221 Approved
0.596 Remote Similarity NPD4754 Approved
0.5955 Remote Similarity NPD1694 Approved
0.5955 Remote Similarity NPD5363 Approved
0.5941 Remote Similarity NPD5697 Approved
0.593 Remote Similarity NPD5368 Approved
0.593 Remote Similarity NPD4252 Approved
0.5909 Remote Similarity NPD4265 Approved
0.5909 Remote Similarity NPD7154 Phase 3
0.5895 Remote Similarity NPD5210 Approved
0.5895 Remote Similarity NPD4629 Approved
0.5889 Remote Similarity NPD5690 Phase 2
0.5889 Remote Similarity NPD5786 Approved
0.5889 Remote Similarity NPD4249 Approved
0.5882 Remote Similarity NPD6881 Approved
0.5882 Remote Similarity NPD4730 Approved
0.5882 Remote Similarity NPD6011 Approved
0.5882 Remote Similarity NPD6899 Approved
0.5882 Remote Similarity NPD4729 Approved
0.5875 Remote Similarity NPD3700 Clinical (unspecified phase)
0.5875 Remote Similarity NPD4267 Clinical (unspecified phase)
0.5875 Remote Similarity NPD3699 Clinical (unspecified phase)
0.587 Remote Similarity NPD5764 Clinical (unspecified phase)
0.587 Remote Similarity NPD6051 Approved
0.587 Remote Similarity NPD6101 Approved
0.5867 Remote Similarity NPD4246 Clinical (unspecified phase)
0.5859 Remote Similarity NPD7632 Discontinued
0.5843 Remote Similarity NPD6400 Clinical (unspecified phase)
0.5843 Remote Similarity NPD4197 Approved
0.5842 Remote Similarity NPD6402 Approved
0.5842 Remote Similarity NPD4768 Approved
0.5842 Remote Similarity NPD7128 Approved
0.5842 Remote Similarity NPD6675 Approved
0.5842 Remote Similarity NPD5739 Approved
0.5842 Remote Similarity NPD4767 Approved
0.5825 Remote Similarity NPD6013 Approved
0.5825 Remote Similarity NPD6012 Approved
0.5825 Remote Similarity NPD6014 Approved
0.5824 Remote Similarity NPD4250 Approved
0.5824 Remote Similarity NPD4251 Approved
0.5806 Remote Similarity NPD3168 Discontinued
0.5802 Remote Similarity NPD4787 Phase 1
0.5795 Remote Similarity NPD6435 Approved
0.5789 Remote Similarity NPD7901 Clinical (unspecified phase)
0.5789 Remote Similarity NPD7900 Approved
0.5784 Remote Similarity NPD5701 Approved
0.5778 Remote Similarity NPD6082 Clinical (unspecified phase)
0.5778 Remote Similarity NPD5329 Approved
0.5769 Remote Similarity NPD5134 Clinical (unspecified phase)
0.5769 Remote Similarity NPD5250 Approved
0.5769 Remote Similarity NPD4634 Approved
0.5769 Remote Similarity NPD5248 Approved
0.5769 Remote Similarity NPD7102 Approved
0.5769 Remote Similarity NPD5249 Phase 3
0.5769 Remote Similarity NPD6883 Approved
0.5769 Remote Similarity NPD7290 Approved
0.5769 Remote Similarity NPD5169 Approved
0.5769 Remote Similarity NPD5247 Approved
0.5769 Remote Similarity NPD5251 Approved
0.5769 Remote Similarity NPD5135 Approved
0.5758 Remote Similarity NPD4159 Approved
0.5745 Remote Similarity NPD5284 Approved
0.5745 Remote Similarity NPD8035 Phase 2
0.5745 Remote Similarity NPD8034 Phase 2
0.5745 Remote Similarity NPD5281 Approved
0.5741 Remote Similarity NPD7115 Discovery
0.5732 Remote Similarity NPD4809 Clinical (unspecified phase)
0.5732 Remote Similarity NPD4808 Clinical (unspecified phase)
0.573 Remote Similarity NPD4788 Approved
0.5729 Remote Similarity NPD1698 Clinical (unspecified phase)
0.5728 Remote Similarity NPD5168 Approved
0.5728 Remote Similarity NPD6686 Approved
0.5728 Remote Similarity NPD5128 Approved
0.5728 Remote Similarity NPD7320 Approved
0.5714 Remote Similarity NPD5217 Approved

Structure

External Identifiers

PubChem CID   71746440
ChEMBL   CHEMBL2407097
ZINC  

Physicochemical Properties

Molecular Weight:  228.17
ALogP:  -0.1558
MLogP:  2.56
XLogP:  1.484
# Rotatable Bonds:  9
Polar Surface Area:  60.69
# H-Bond Aceptor:  3
# H-Bond Donor:  3
# Rings:  1
# Heavy Atoms:  16

Download Data

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Structure MOL file  
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Biological Activities  
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