Natural Product: NPC477614

Natural Product ID:  NPC477614
Common Name:   Secosterol
IUPAC Name:   (1aR,3S,4aS,7S,8aS)-3-[(1S,2R,3R)-3-[(2R,5S)-5,6-dimethylheptan-2-yl]-2-(2-hydroxyethyl)-2-methylcyclopentyl]-7-hydroxy-4a-methyl-2,3,5,6,7,8-hexahydro-1aH-naphtho[4,4a-b]oxiren-4-one
Synonyms:   secosterol
Molecular Formula:   C28H48O4
Standard InCHIKey:  DIFSFFZHWQSHBX-CLECVEASSA-N
Standard InCHI:  InChI=1S/C28H48O4/c1-17(2)18(3)7-8-19(4)22-9-10-23(26(22,5)13-14-29)21-15-24-28(32-24)16-20(30)11-12-27(28,6)25(21)31/h17-24,29-30H,7-16H2,1-6H3/t18-,19+,20-,21-,22+,23-,24+,26+,27+,28+/m0/s1
Canonical SMILES:  OCC[C@]1(C)[C@H](CC[C@H]1[C@@H]1C[C@H]2O[C@]32[C@](C1=O)(C)CC[C@@H](C3)O)[C@@H](CC[C@@H](C(C)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
NPO32480 pachyclavularia violacea Species Clavulariidae Eukaryota PMID[12350166]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT168 Cell Line P388 Mus musculus IC50 > 1 ug/ml 12350166
NPT81 Cell Line A549 Homo sapiens IC50 > 1 ug/ml 12350166
NPT139 Cell Line HT-29 Homo sapiens IC50 > 1 ug/ml 12350166
NPT170 Cell Line SK-MEL-28 Homo sapiens IC50 > 1 ug/ml 12350166

  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 NPC477614 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 NPC226491
0.9318 High Similarity NPC17336
0.9186 High Similarity NPC61688
0.9111 High Similarity NPC111187
0.9111 High Similarity NPC190080
0.9048 High Similarity NPC50438
0.8941 High Similarity NPC473350
0.8824 High Similarity NPC475689
0.8736 High Similarity NPC263802
0.8681 High Similarity NPC62407
0.8681 High Similarity NPC287354
0.8667 High Similarity NPC476189
0.8621 High Similarity NPC474215
0.8621 High Similarity NPC475729
0.8605 High Similarity NPC477434
0.8602 High Similarity NPC476294
0.8554 High Similarity NPC475725
0.8409 Intermediate Similarity NPC302111
0.8391 Intermediate Similarity NPC473336
0.8391 Intermediate Similarity NPC471044
0.8333 Intermediate Similarity NPC24705
0.8333 Intermediate Similarity NPC200580
0.8333 Intermediate Similarity NPC56962
0.8333 Intermediate Similarity NPC477440
0.8333 Intermediate Similarity NPC477443
0.8315 Intermediate Similarity NPC202937
0.8276 Intermediate Similarity NPC227170
0.8256 Intermediate Similarity NPC254123
0.8247 Intermediate Similarity NPC34562
0.8242 Intermediate Similarity NPC477444
0.8242 Intermediate Similarity NPC477442
0.8242 Intermediate Similarity NPC476296
0.8242 Intermediate Similarity NPC477433
0.8235 Intermediate Similarity NPC275243
0.8202 Intermediate Similarity NPC80700
0.8202 Intermediate Similarity NPC83242
0.8191 Intermediate Similarity NPC477264
0.8191 Intermediate Similarity NPC193785
0.8191 Intermediate Similarity NPC116683
0.8172 Intermediate Similarity NPC470424
0.8172 Intermediate Similarity NPC477495
0.8152 Intermediate Similarity NPC52756
0.8144 Intermediate Similarity NPC471254
0.8132 Intermediate Similarity NPC67653
0.8132 Intermediate Similarity NPC471459
0.8111 Intermediate Similarity NPC239938
0.8095 Intermediate Similarity NPC472487
0.8095 Intermediate Similarity NPC472486
0.809 Intermediate Similarity NPC477445
0.809 Intermediate Similarity NPC477205
0.8068 Intermediate Similarity NPC327451
0.8068 Intermediate Similarity NPC15091
0.8046 Intermediate Similarity NPC469745
0.8043 Intermediate Similarity NPC77756
0.8041 Intermediate Similarity NPC46848
0.8022 Intermediate Similarity NPC471221
0.8022 Intermediate Similarity NPC90676
0.8 Intermediate Similarity NPC475031
0.8 Intermediate Similarity NPC163685
0.8 Intermediate Similarity NPC476726
0.8 Intermediate Similarity NPC476727
0.8 Intermediate Similarity NPC235109
0.8 Intermediate Similarity NPC472745
0.798 Intermediate Similarity NPC88469
0.7978 Intermediate Similarity NPC219535
0.7978 Intermediate Similarity NPC319909
0.7978 Intermediate Similarity NPC25037
0.7978 Intermediate Similarity NPC34984
0.7978 Intermediate Similarity NPC237938
0.7976 Intermediate Similarity NPC21220
0.7976 Intermediate Similarity NPC125767
0.7976 Intermediate Similarity NPC159789
0.7961 Intermediate Similarity NPC476964
0.7959 Intermediate Similarity NPC275990
0.7959 Intermediate Similarity NPC470172
0.7955 Intermediate Similarity NPC268040
0.7955 Intermediate Similarity NPC317066
0.7938 Intermediate Similarity NPC94906
0.7917 Intermediate Similarity NPC170978
0.7907 Intermediate Similarity NPC471769
0.7895 Intermediate Similarity NPC82633
0.7882 Intermediate Similarity NPC474020
0.7879 Intermediate Similarity NPC473406
0.7879 Intermediate Similarity NPC471253
0.7872 Intermediate Similarity NPC161035
0.7865 Intermediate Similarity NPC292458
0.7865 Intermediate Similarity NPC268578
0.7865 Intermediate Similarity NPC472847
0.7865 Intermediate Similarity NPC217559
0.7857 Intermediate Similarity NPC178853
0.7849 Intermediate Similarity NPC88337
0.7849 Intermediate Similarity NPC475211
0.7841 Intermediate Similarity NPC475743
0.7835 Intermediate Similarity NPC98837
0.7835 Intermediate Similarity NPC474793
0.7835 Intermediate Similarity NPC38296
0.7835 Intermediate Similarity NPC20479
0.7835 Intermediate Similarity NPC472028
0.7835 Intermediate Similarity NPC471038
0.7835 Intermediate Similarity NPC253995
0.7835 Intermediate Similarity NPC28864
0.7835 Intermediate Similarity NPC162459
0.7835 Intermediate Similarity NPC38471
0.7826 Intermediate Similarity NPC3032
0.7826 Intermediate Similarity NPC476379
0.7826 Intermediate Similarity NPC473319
0.7826 Intermediate Similarity NPC476435
0.7826 Intermediate Similarity NPC131104
0.7816 Intermediate Similarity NPC320144
0.7816 Intermediate Similarity NPC80891
0.7816 Intermediate Similarity NPC201276
0.7812 Intermediate Similarity NPC476728
0.7802 Intermediate Similarity NPC476717
0.7802 Intermediate Similarity NPC472272
0.7802 Intermediate Similarity NPC477441
0.78 Intermediate Similarity NPC327093
0.78 Intermediate Similarity NPC470167
0.7791 Intermediate Similarity NPC221420
0.7791 Intermediate Similarity NPC471151
0.7791 Intermediate Similarity NPC476233
0.7791 Intermediate Similarity NPC23884
0.7791 Intermediate Similarity NPC143250
0.7789 Intermediate Similarity NPC470423
0.7778 Intermediate Similarity NPC304832
0.7778 Intermediate Similarity NPC473299
0.7778 Intermediate Similarity NPC124544
0.7778 Intermediate Similarity NPC76866
0.7778 Intermediate Similarity NPC246736
0.7778 Intermediate Similarity NPC286519
0.7778 Intermediate Similarity NPC148628
0.7778 Intermediate Similarity NPC214946
0.7778 Intermediate Similarity NPC88203
0.7766 Intermediate Similarity NPC216137
0.7765 Intermediate Similarity NPC35871
0.7765 Intermediate Similarity NPC273366
0.7765 Intermediate Similarity NPC68565
0.7755 Intermediate Similarity NPC180733
0.7755 Intermediate Similarity NPC41971
0.7755 Intermediate Similarity NPC37047
0.7755 Intermediate Similarity NPC293866
0.7753 Intermediate Similarity NPC289486
0.7753 Intermediate Similarity NPC61107
0.7738 Intermediate Similarity NPC232112
0.7732 Intermediate Similarity NPC253586
0.7727 Intermediate Similarity NPC16449
0.7727 Intermediate Similarity NPC470609
0.7727 Intermediate Similarity NPC474714
0.7727 Intermediate Similarity NPC477851
0.7723 Intermediate Similarity NPC470587
0.7723 Intermediate Similarity NPC200957
0.7723 Intermediate Similarity NPC37600
0.7723 Intermediate Similarity NPC295366
0.7723 Intermediate Similarity NPC138908
0.7708 Intermediate Similarity NPC263135
0.7708 Intermediate Similarity NPC288906
0.7708 Intermediate Similarity NPC305808
0.7708 Intermediate Similarity NPC470031
0.7701 Intermediate Similarity NPC34046
0.7701 Intermediate Similarity NPC171426
0.7701 Intermediate Similarity NPC324700
0.7701 Intermediate Similarity NPC185465
0.7701 Intermediate Similarity NPC80089
0.7701 Intermediate Similarity NPC224802
0.77 Intermediate Similarity NPC87927
0.77 Intermediate Similarity NPC107385
0.7692 Intermediate Similarity NPC473062
0.7684 Intermediate Similarity NPC474379
0.7677 Intermediate Similarity NPC259654
0.7677 Intermediate Similarity NPC14634
0.7677 Intermediate Similarity NPC298266
0.7677 Intermediate Similarity NPC236585
0.7677 Intermediate Similarity NPC253886
0.7677 Intermediate Similarity NPC121218
0.7677 Intermediate Similarity NPC289148
0.7677 Intermediate Similarity NPC52899
0.7677 Intermediate Similarity NPC75941
0.7677 Intermediate Similarity NPC163963
0.7674 Intermediate Similarity NPC475742
0.7674 Intermediate Similarity NPC5767
0.7667 Intermediate Similarity NPC472744
0.766 Intermediate Similarity NPC46758
0.7653 Intermediate Similarity NPC89099
0.7647 Intermediate Similarity NPC201908
0.7647 Intermediate Similarity NPC176949
0.7647 Intermediate Similarity NPC475458
0.7647 Intermediate Similarity NPC166993
0.7642 Intermediate Similarity NPC470116
0.7642 Intermediate Similarity NPC238667
0.7642 Intermediate Similarity NPC470115
0.764 Intermediate Similarity NPC50658
0.764 Intermediate Similarity NPC58631
0.7629 Intermediate Similarity NPC200054
0.7629 Intermediate Similarity NPC329910
0.7629 Intermediate Similarity NPC29410
0.7619 Intermediate Similarity NPC89310
0.7619 Intermediate Similarity NPC187471
0.7619 Intermediate Similarity NPC252182
0.7619 Intermediate Similarity NPC1340
0.7619 Intermediate Similarity NPC470071
0.7619 Intermediate Similarity NPC151018

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC477614 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
0.7976 Intermediate Similarity NPD3703 Phase 2
0.7701 Intermediate Similarity NPD6115 Approved
0.7701 Intermediate Similarity NPD6118 Approved
0.7701 Intermediate Similarity NPD6114 Approved
0.7701 Intermediate Similarity NPD6697 Approved
0.7677 Intermediate Similarity NPD1700 Approved
0.7619 Intermediate Similarity NPD4808 Clinical (unspecified phase)
0.7619 Intermediate Similarity NPD4809 Clinical (unspecified phase)
0.7586 Intermediate Similarity NPD6116 Phase 1
0.7471 Intermediate Similarity NPD6117 Approved
0.7381 Intermediate Similarity NPD3699 Clinical (unspecified phase)
0.7381 Intermediate Similarity NPD3700 Clinical (unspecified phase)
0.7317 Intermediate Similarity NPD3171 Clinical (unspecified phase)
0.7262 Intermediate Similarity NPD5360 Phase 3
0.7262 Intermediate Similarity NPD5361 Clinical (unspecified phase)
0.7241 Intermediate Similarity NPD6113 Clinical (unspecified phase)
0.7238 Intermediate Similarity NPD5345 Clinical (unspecified phase)
0.7115 Intermediate Similarity NPD8170 Clinical (unspecified phase)
0.7093 Intermediate Similarity NPD4245 Approved
0.7093 Intermediate Similarity NPD4244 Approved
0.7093 Intermediate Similarity NPD4789 Approved
0.6977 Remote Similarity NPD3698 Phase 2
0.6977 Remote Similarity NPD4267 Clinical (unspecified phase)
0.6966 Remote Similarity NPD3702 Approved
0.6887 Remote Similarity NPD6008 Approved
0.6887 Remote Similarity NPD6402 Approved
0.6887 Remote Similarity NPD5739 Approved
0.6887 Remote Similarity NPD6675 Approved
0.6887 Remote Similarity NPD7128 Approved
0.6869 Remote Similarity NPD8034 Phase 2
0.6869 Remote Similarity NPD8035 Phase 2
0.6863 Remote Similarity NPD4755 Approved
0.6852 Remote Similarity NPD6373 Approved
0.6852 Remote Similarity NPD6372 Approved
0.6842 Remote Similarity NPD6059 Approved
0.6842 Remote Similarity NPD6054 Approved
0.6837 Remote Similarity NPD5328 Approved
0.6818 Remote Similarity NPD4758 Discontinued
0.6789 Remote Similarity NPD4634 Approved
0.6759 Remote Similarity NPD6881 Approved
0.6759 Remote Similarity NPD7320 Approved
0.6759 Remote Similarity NPD6899 Approved
0.6739 Remote Similarity NPD3671 Phase 1
0.6739 Remote Similarity NPD5364 Discontinued
0.6731 Remote Similarity NPD5286 Approved
0.6731 Remote Similarity NPD4700 Approved
0.6731 Remote Similarity NPD4696 Approved
0.6731 Remote Similarity NPD5285 Approved
0.6727 Remote Similarity NPD6650 Approved
0.6727 Remote Similarity NPD6649 Approved
0.6724 Remote Similarity NPD6370 Approved
0.67 Remote Similarity NPD6079 Approved
0.6696 Remote Similarity NPD6319 Approved
0.6667 Remote Similarity NPD5697 Approved
0.6667 Remote Similarity NPD5701 Approved
0.6638 Remote Similarity NPD6015 Approved
0.6638 Remote Similarity NPD6016 Approved
0.6636 Remote Similarity NPD7102 Approved
0.6636 Remote Similarity NPD7290 Approved
0.6636 Remote Similarity NPD6883 Approved
0.6634 Remote Similarity NPD6399 Phase 3
0.6629 Remote Similarity NPD5777 Approved
0.6629 Remote Similarity NPD6081 Approved
0.661 Remote Similarity NPD7492 Approved
0.6604 Remote Similarity NPD5225 Approved
0.6604 Remote Similarity NPD5226 Approved
0.6604 Remote Similarity NPD5211 Phase 2
0.6604 Remote Similarity NPD4633 Approved
0.6604 Remote Similarity NPD5224 Approved
0.6602 Remote Similarity NPD4697 Phase 3
0.6598 Remote Similarity NPD7520 Clinical (unspecified phase)
0.6596 Remote Similarity NPD6928 Phase 2
0.6581 Remote Similarity NPD5988 Approved
0.6579 Remote Similarity NPD7115 Discovery
0.6577 Remote Similarity NPD8130 Phase 1
0.6577 Remote Similarity NPD6847 Approved
0.6577 Remote Similarity NPD6869 Approved
0.6577 Remote Similarity NPD6617 Approved
0.6555 Remote Similarity NPD6616 Approved
0.6545 Remote Similarity NPD6013 Approved
0.6545 Remote Similarity NPD4061 Clinical (unspecified phase)
0.6545 Remote Similarity NPD6012 Approved
0.6545 Remote Similarity NPD6014 Approved
0.6542 Remote Similarity NPD5175 Approved
0.6542 Remote Similarity NPD5174 Approved
0.6531 Remote Similarity NPD3618 Phase 1
0.6518 Remote Similarity NPD6882 Approved
0.6518 Remote Similarity NPD8297 Approved
0.6509 Remote Similarity NPD5223 Approved
0.65 Remote Similarity NPD8293 Discontinued
0.65 Remote Similarity NPD7078 Approved
0.6496 Remote Similarity NPD6921 Approved
0.6495 Remote Similarity NPD4786 Approved
0.6486 Remote Similarity NPD5955 Clinical (unspecified phase)
0.6481 Remote Similarity NPD5141 Approved
0.6471 Remote Similarity NPD4202 Approved
0.646 Remote Similarity NPD4632 Approved
0.6455 Remote Similarity NPD6011 Approved
0.6446 Remote Similarity NPD7736 Approved
0.6442 Remote Similarity NPD5220 Clinical (unspecified phase)
0.6442 Remote Similarity NPD5221 Approved
0.6442 Remote Similarity NPD5222 Approved
0.6437 Remote Similarity NPD4224 Phase 2
0.6429 Remote Similarity NPD6401 Clinical (unspecified phase)
0.6422 Remote Similarity NPD4768 Approved
0.6422 Remote Similarity NPD4767 Approved
0.6393 Remote Similarity NPD7319 Approved
0.6392 Remote Similarity NPD4788 Approved
0.6389 Remote Similarity NPD4754 Approved
0.6387 Remote Similarity NPD7604 Phase 2
0.6383 Remote Similarity NPD4238 Approved
0.6383 Remote Similarity NPD4802 Phase 2
0.6381 Remote Similarity NPD5173 Approved
0.6364 Remote Similarity NPD3574 Clinical (unspecified phase)
0.6333 Remote Similarity NPD4787 Phase 1
0.6321 Remote Similarity NPD7638 Approved
0.6311 Remote Similarity NPD6033 Approved
0.6306 Remote Similarity NPD5128 Approved
0.6306 Remote Similarity NPD4730 Approved
0.6306 Remote Similarity NPD4729 Approved
0.6293 Remote Similarity NPD8295 Clinical (unspecified phase)
0.6293 Remote Similarity NPD6009 Approved
0.6289 Remote Similarity NPD3667 Approved
0.6262 Remote Similarity NPD7639 Approved
0.6262 Remote Similarity NPD8418 Phase 2
0.6262 Remote Similarity NPD7640 Approved
0.625 Remote Similarity NPD8132 Clinical (unspecified phase)
0.625 Remote Similarity NPD7525 Registered
0.6226 Remote Similarity NPD6083 Phase 2
0.6226 Remote Similarity NPD6084 Phase 2
0.6218 Remote Similarity NPD5983 Phase 2
0.6216 Remote Similarity NPD6412 Phase 2
0.6216 Remote Similarity NPD5954 Clinical (unspecified phase)
0.6207 Remote Similarity NPD6274 Approved
0.6207 Remote Similarity NPD371 Approved
0.6195 Remote Similarity NPD5248 Approved
0.6195 Remote Similarity NPD5249 Phase 3
0.6195 Remote Similarity NPD5247 Approved
0.6195 Remote Similarity NPD5250 Approved
0.6195 Remote Similarity NPD5251 Approved
0.6186 Remote Similarity NPD7100 Approved
0.6186 Remote Similarity NPD7101 Approved
0.6176 Remote Similarity NPD4753 Phase 2
0.6174 Remote Similarity NPD8133 Approved
0.6162 Remote Similarity NPD7338 Clinical (unspecified phase)
0.6154 Remote Similarity NPD8171 Discontinued
0.6148 Remote Similarity NPD7507 Approved
0.6148 Remote Similarity NPD6336 Discontinued
0.6147 Remote Similarity NPD7632 Discontinued
0.614 Remote Similarity NPD5216 Approved
0.614 Remote Similarity NPD5215 Approved
0.614 Remote Similarity NPD5217 Approved
0.6126 Remote Similarity NPD6920 Discontinued
0.6116 Remote Similarity NPD8328 Phase 3
0.6102 Remote Similarity NPD6335 Approved
0.6083 Remote Similarity NPD6909 Approved
0.6083 Remote Similarity NPD6908 Approved
0.6075 Remote Similarity NPD7902 Approved
0.6068 Remote Similarity NPD6940 Discontinued
0.6061 Remote Similarity NPD6695 Phase 3
0.6058 Remote Similarity NPD7637 Suspended
0.6053 Remote Similarity NPD5169 Approved
0.6053 Remote Similarity NPD5134 Clinical (unspecified phase)
0.6053 Remote Similarity NPD5135 Approved
0.6038 Remote Similarity NPD6356 Clinical (unspecified phase)
0.6038 Remote Similarity NPD5210 Approved
0.6038 Remote Similarity NPD4629 Approved
0.6036 Remote Similarity NPD4057 Clinical (unspecified phase)
0.6036 Remote Similarity NPD4056 Clinical (unspecified phase)
0.602 Remote Similarity NPD1780 Approved
0.602 Remote Similarity NPD1779 Approved
0.6019 Remote Similarity NPD5696 Approved
0.6017 Remote Similarity NPD6317 Approved
0.6 Remote Similarity NPD3665 Phase 1
0.6 Remote Similarity NPD3666 Approved
0.6 Remote Similarity NPD3133 Approved
0.6 Remote Similarity NPD5127 Approved
0.5966 Remote Similarity NPD6313 Approved
0.5966 Remote Similarity NPD6314 Approved
0.595 Remote Similarity NPD6291 Clinical (unspecified phase)
0.5943 Remote Similarity NPD7748 Approved
0.5943 Remote Similarity NPD5282 Discontinued
0.5934 Remote Similarity NPD229 Approved
0.5932 Remote Similarity NPD6868 Approved
0.5905 Remote Similarity NPD6411 Approved
0.5905 Remote Similarity NPD7515 Phase 2
0.59 Remote Similarity NPD3670 Clinical (unspecified phase)
0.59 Remote Similarity NPD3669 Approved
0.5888 Remote Similarity NPD5695 Phase 3
0.5877 Remote Similarity NPD5168 Approved
0.5849 Remote Similarity NPD5778 Approved
0.5849 Remote Similarity NPD5779 Approved
0.5847 Remote Similarity NPD5167 Approved
0.5842 Remote Similarity NPD3668 Phase 3
0.5825 Remote Similarity NPD7524 Approved
0.5825 Remote Similarity NPD7750 Discontinued
0.5812 Remote Similarity NPD6053 Discontinued
0.5806 Remote Similarity NPD7532 Clinical (unspecified phase)
0.58 Remote Similarity NPD4221 Approved
0.58 Remote Similarity NPD4223 Phase 3

Structure

External Identifiers

PubChem CID   639674
ChEMBL   CHEMBL483640
ZINC  

Physicochemical Properties

Molecular Weight:  448.36
ALogP:  1.0218
MLogP:  4.1
XLogP:  6.887
# Rotatable Bonds:  16
Polar Surface Area:  70.06
# H-Bond Aceptor:  4
# H-Bond Donor:  2
# Rings:  4
# Heavy Atoms:  32

Download Data

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Biological Activities  
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