Natural Product: NPC476944

Natural Product ID:  NPC476944
Common Name:   (2S,4aR,6aR,8R,10aR,10bR)-2-(furan-3-yl)-8-hydroxy-6a,10b-dimethyl-7-methylidene-2,4a,5,6,8,9,10,10a-octahydro-1H-benzo[f]isochromen-4-one
IUPAC Name:   (2S,4aR,6aR,8R,10aR,10bR)-2-(furan-3-yl)-8-hydroxy-6a,10b-dimethyl-7-methylidene-2,4a,5,6,8,9,10,10a-octahydro-1H-benzo[f]isochromen-4-one
Synonyms:  
Molecular Formula:   C20H26O4
Standard InCHIKey:  SMEKOFCCRYVWBV-KCMORZRYSA-N
Standard InCHI:  InChI=1S/C20H26O4/c1-12-15(21)4-5-17-19(12,2)8-6-14-18(22)24-16(10-20(14,17)3)13-7-9-23-11-13/h7,9,11,14-17,21H,1,4-6,8,10H2,2-3H3/t14-,15+,16-,17-,19-,20-/m0/s1
Canonical SMILES:  O=C1O[C@@H](C[C@]2([C@H]1CC[C@@]1([C@@H]2CC[C@H](C1=C)O)C)C)c1ccoc1
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
NPO33579 Croton laui Species Euphorbiaceae Eukaryota Twigs Hainan Province, China PMID[24735527]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT116 Cell Line HL-60 Homo sapiens IC50 >= 10000 nM 24735527
NPT168 Cell Line P388 Mus musculus IC50 >= 10000 nM 24735527
NPT16 Organism Staphylococcus aureus Staphylococcus aureus MIC > 150000 nM 24735527
NPT1277 Organism Staphylococcus epidermidis ATCC 12228 Staphylococcus epidermidis ATCC 12228 MIC > 150000 nM 24735527
NPT2 Others Unspecified MIC > 150000 nM 24735527
NPT79 Organism Bacillus subtilis Bacillus subtilis MIC > 150000 nM 24735527
NPT19 Organism Escherichia coli Escherichia coli MIC > 150000 nM 24735527
NPT2909 Organism Shigella flexneri Shigella flexneri MIC > 150000 nM 24735527
NPT18 Organism Pseudomonas aeruginosa Pseudomonas aeruginosa MIC > 150000 nM 24735527
NPT20 Organism Candida albicans Candida albicans MIC > 150000 nM 24735527
NPT1533 Organism Saccharomyces Saccharomyces MIC > 150000 nM 24735527
NPT327 Organism Microsporum gypseum Microsporum gypseum MIC > 150000 nM 24735527
NPT329 Organism Trichophyton rubrum Trichophyton rubrum MIC > 150000 nM 24735527

  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 NPC476944 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
0.9433 High Similarity NPC346
0.9416 High Similarity NPC476943
0.9366 High Similarity NPC250228
0.9343 High Similarity NPC310830
0.931 High Similarity NPC469503
0.9247 High Similarity NPC178932
0.9247 High Similarity NPC282445
0.9236 High Similarity NPC195325
0.9184 High Similarity NPC35000
0.9184 High Similarity NPC469336
0.9161 High Similarity NPC262198
0.9137 High Similarity NPC220094
0.9116 High Similarity NPC57998
0.9116 High Similarity NPC30222
0.9103 High Similarity NPC472654
0.9085 High Similarity NPC267632
0.9085 High Similarity NPC476946
0.9078 High Similarity NPC205765
0.906 High Similarity NPC472772
0.906 High Similarity NPC249021
0.9021 High Similarity NPC142113
0.9007 High Similarity NPC200782
0.9 High Similarity NPC475967
0.8958 High Similarity NPC41182
0.894 High Similarity NPC335761
0.8933 High Similarity NPC261597
0.8933 High Similarity NPC299038
0.8929 High Similarity NPC470742
0.8926 High Similarity NPC281258
0.8926 High Similarity NPC44675
0.8926 High Similarity NPC214541
0.8919 High Similarity NPC33938
0.8919 High Similarity NPC75906
0.8912 High Similarity NPC477404
0.8912 High Similarity NPC469335
0.8912 High Similarity NPC470997
0.8912 High Similarity NPC196864
0.8912 High Similarity NPC159927
0.8912 High Similarity NPC476122
0.8904 High Similarity NPC476941
0.8904 High Similarity NPC476942
0.8889 High Similarity NPC251865
0.8882 High Similarity NPC472771
0.8882 High Similarity NPC82851
0.8882 High Similarity NPC69028
0.8882 High Similarity NPC5079
0.8881 High Similarity NPC121158
0.8874 High Similarity NPC474611
0.8836 High Similarity NPC476937
0.8836 High Similarity NPC221809
0.8836 High Similarity NPC470941
0.8836 High Similarity NPC476938
0.8824 High Similarity NPC39986
0.8824 High Similarity NPC234660
0.8824 High Similarity NPC302369
0.8824 High Similarity NPC472773
0.8824 High Similarity NPC198047
0.8824 High Similarity NPC477405
0.8824 High Similarity NPC51568
0.8824 High Similarity NPC134254
0.8819 High Similarity NPC223415
0.8816 High Similarity NPC477402
0.8816 High Similarity NPC472653
0.8811 High Similarity NPC20500
0.8808 High Similarity NPC45101
0.8808 High Similarity NPC36655
0.8803 High Similarity NPC90953
0.88 High Similarity NPC264943
0.8792 High Similarity NPC476201
0.8792 High Similarity NPC476939
0.8792 High Similarity NPC476940
0.8792 High Similarity NPC44577
0.8786 High Similarity NPC92941
0.8768 High Similarity NPC61788
0.8766 High Similarity NPC476857
0.8766 High Similarity NPC470182
0.8766 High Similarity NPC470940
0.8766 High Similarity NPC476856
0.8766 High Similarity NPC276551
0.8766 High Similarity NPC476858
0.8758 High Similarity NPC263432
0.8758 High Similarity NPC207978
0.8758 High Similarity NPC211777
0.8758 High Similarity NPC193798
0.8758 High Similarity NPC329938
0.875 High Similarity NPC307383
0.875 High Similarity NPC62103
0.875 High Similarity NPC20578
0.875 High Similarity NPC477403
0.8741 High Similarity NPC67003
0.8733 High Similarity NPC114880
0.8716 High Similarity NPC234494
0.8716 High Similarity NPC69647
0.8716 High Similarity NPC470998
0.8716 High Similarity NPC125182
0.8716 High Similarity NPC211625
0.8714 High Similarity NPC471998
0.871 High Similarity NPC93172
0.871 High Similarity NPC23387
0.871 High Similarity NPC470875
0.871 High Similarity NPC97574
0.8707 High Similarity NPC471174
0.8707 High Similarity NPC216755
0.8707 High Similarity NPC255414
0.8701 High Similarity NPC224394
0.8701 High Similarity NPC469338
0.8701 High Similarity NPC419
0.8701 High Similarity NPC663
0.8701 High Similarity NPC292389
0.8693 High Similarity NPC25255
0.869 High Similarity NPC243577
0.8686 High Similarity NPC112706
0.8686 High Similarity NPC207294
0.8684 High Similarity NPC472777
0.8684 High Similarity NPC472776
0.8684 High Similarity NPC472778
0.8684 High Similarity NPC187149
0.8676 High Similarity NPC138139
0.8676 High Similarity NPC46536
0.8676 High Similarity NPC74612
0.8675 High Similarity NPC469850
0.8675 High Similarity NPC476262
0.8662 High Similarity NPC42400
0.8658 High Similarity NPC46551
0.8654 High Similarity NPC476850
0.8654 High Similarity NPC476853
0.8654 High Similarity NPC476861
0.8654 High Similarity NPC472282
0.8654 High Similarity NPC472651
0.8654 High Similarity NPC472774
0.8654 High Similarity NPC472775
0.8645 High Similarity NPC271657
0.8645 High Similarity NPC469849
0.8645 High Similarity NPC123088
0.8645 High Similarity NPC476860
0.8636 High Similarity NPC18347
0.8636 High Similarity NPC149896
0.8636 High Similarity NPC117986
0.8633 High Similarity NPC89133
0.863 High Similarity NPC137295
0.8627 High Similarity NPC475226
0.8627 High Similarity NPC262872
0.8621 High Similarity NPC52412
0.8618 High Similarity NPC107646
0.8618 High Similarity NPC126723
0.8618 High Similarity NPC209364
0.8618 High Similarity NPC469485
0.8611 High Similarity NPC56197
0.8603 High Similarity NPC179354
0.86 High Similarity NPC18135
0.8599 High Similarity NPC471397
0.8599 High Similarity NPC271235
0.8599 High Similarity NPC472652
0.8592 High Similarity NPC46896
0.8581 High Similarity NPC288602
0.8581 High Similarity NPC88841
0.8581 High Similarity NPC165218
0.8571 High Similarity NPC185456
0.8571 High Similarity NPC5676
0.8562 High Similarity NPC167142
0.8562 High Similarity NPC470741
0.8562 High Similarity NPC173544
0.8562 High Similarity NPC304692
0.8562 High Similarity NPC286722
0.8562 High Similarity NPC472283
0.8553 High Similarity NPC75310
0.8553 High Similarity NPC92979
0.8544 High Similarity NPC82602
0.8543 High Similarity NPC268905
0.8542 High Similarity NPC202260
0.854 High Similarity NPC23086
0.8535 High Similarity NPC173516
0.8535 High Similarity NPC100333
0.8533 High Similarity NPC212257
0.8533 High Similarity NPC156189
0.8531 High Similarity NPC186626
0.8521 High Similarity NPC158525
0.8521 High Similarity NPC476947
0.8516 High Similarity NPC290400
0.8516 High Similarity NPC470792
0.8516 High Similarity NPC96443
0.8516 High Similarity NPC472767
0.8516 High Similarity NPC188649
0.8516 High Similarity NPC18986
0.8514 High Similarity NPC62799
0.8514 High Similarity NPC471292
0.8511 High Similarity NPC218838
0.8506 High Similarity NPC140952
0.8506 High Similarity NPC475295
0.8506 High Similarity NPC473473
0.8503 High Similarity NPC199044
0.8503 High Similarity NPC238843
0.85 High Similarity NPC298190
0.8497 Intermediate Similarity NPC263265
0.8497 Intermediate Similarity NPC41880
0.8497 Intermediate Similarity NPC104736
0.8497 Intermediate Similarity NPC60973
0.8489 Intermediate Similarity NPC198904
0.8481 Intermediate Similarity NPC160651
0.8481 Intermediate Similarity NPC296558

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC476944 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
0.88 High Similarity NPD5760 Phase 2
0.88 High Similarity NPD5761 Phase 2
0.7976 Intermediate Similarity NPD8434 Phase 2
0.7763 Intermediate Similarity NPD4628 Phase 3
0.7742 Intermediate Similarity NPD6273 Approved
0.7682 Intermediate Similarity NPD2343 Clinical (unspecified phase)
0.7654 Intermediate Similarity NPD5537 Clinical (unspecified phase)
0.7595 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7574 Intermediate Similarity NPD6764 Approved
0.7574 Intermediate Similarity NPD6765 Approved
0.7566 Intermediate Similarity NPD2346 Discontinued
0.7564 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7516 Intermediate Similarity NPD7819 Suspended
0.7471 Intermediate Similarity NPD6559 Discontinued
0.7434 Intermediate Similarity NPD2799 Discontinued
0.7399 Intermediate Similarity NPD6784 Approved
0.7399 Intermediate Similarity NPD6785 Approved
0.7386 Intermediate Similarity NPD2935 Discontinued
0.7378 Intermediate Similarity NPD3749 Approved
0.7358 Intermediate Similarity NPD920 Approved
0.7342 Intermediate Similarity NPD2534 Approved
0.7342 Intermediate Similarity NPD2532 Approved
0.7342 Intermediate Similarity NPD2533 Approved
0.7338 Intermediate Similarity NPD1471 Phase 3
0.7338 Intermediate Similarity NPD2344 Approved
0.7301 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.7294 Intermediate Similarity NPD5844 Phase 1
0.7284 Intermediate Similarity NPD7411 Suspended
0.7273 Intermediate Similarity NPD7075 Discontinued
0.7267 Intermediate Similarity NPD2313 Discontinued
0.7267 Intermediate Similarity NPD3226 Approved
0.7244 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7233 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7222 Intermediate Similarity NPD6599 Discontinued
0.7197 Intermediate Similarity NPD7003 Approved
0.7197 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7195 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7186 Intermediate Similarity NPD5494 Approved
0.7179 Intermediate Similarity NPD1549 Phase 2
0.7171 Intermediate Similarity NPD4140 Approved
0.7162 Intermediate Similarity NPD2797 Approved
0.7161 Intermediate Similarity NPD1551 Phase 2
0.716 Intermediate Similarity NPD7458 Discontinued
0.7152 Intermediate Similarity NPD3268 Approved
0.7152 Intermediate Similarity NPD2309 Approved
0.7152 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.7134 Intermediate Similarity NPD6801 Discontinued
0.7133 Intermediate Similarity NPD6832 Phase 2
0.7125 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.7117 Intermediate Similarity NPD4380 Phase 2
0.7115 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.7115 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.7108 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7107 Intermediate Similarity NPD7236 Approved
0.7107 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.7097 Intermediate Similarity NPD7033 Discontinued
0.7097 Intermediate Similarity NPD4308 Phase 3
0.7075 Intermediate Similarity NPD9717 Approved
0.707 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7066 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.7051 Intermediate Similarity NPD2796 Approved
0.7047 Intermediate Similarity NPD1203 Approved
0.7041 Intermediate Similarity NPD6959 Discontinued
0.7041 Intermediate Similarity NPD8127 Discontinued
0.7035 Intermediate Similarity NPD3818 Discontinued
0.703 Intermediate Similarity NPD1934 Approved
0.7025 Intermediate Similarity NPD2800 Approved
0.7018 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.7013 Intermediate Similarity NPD1899 Clinical (unspecified phase)
0.7013 Intermediate Similarity NPD447 Suspended
0.7006 Intermediate Similarity NPD7768 Phase 2
0.7 Intermediate Similarity NPD6232 Discontinued
0.6993 Remote Similarity NPD8032 Phase 2
0.6989 Remote Similarity NPD8312 Approved
0.6989 Remote Similarity NPD8313 Approved
0.6981 Remote Similarity NPD3750 Approved
0.6981 Remote Similarity NPD4110 Phase 3
0.6981 Remote Similarity NPD4109 Clinical (unspecified phase)
0.6977 Remote Similarity NPD7473 Discontinued
0.6974 Remote Similarity NPD5952 Clinical (unspecified phase)
0.6959 Remote Similarity NPD1608 Approved
0.6959 Remote Similarity NPD3972 Approved
0.6957 Remote Similarity NPD6799 Approved
0.6946 Remote Similarity NPD5402 Approved
0.6943 Remote Similarity NPD6099 Approved
0.6943 Remote Similarity NPD6100 Approved
0.6928 Remote Similarity NPD3764 Approved
0.6928 Remote Similarity NPD37 Approved
0.6928 Remote Similarity NPD411 Approved
0.6923 Remote Similarity NPD919 Approved
0.6918 Remote Similarity NPD1243 Approved
0.6907 Remote Similarity NPD8404 Phase 2
0.6906 Remote Similarity NPD7879 Clinical (unspecified phase)
0.6905 Remote Similarity NPD4967 Phase 2
0.6905 Remote Similarity NPD4965 Approved
0.6905 Remote Similarity NPD4966 Approved
0.6905 Remote Similarity NPD3882 Suspended
0.6903 Remote Similarity NPD6355 Discontinued
0.6901 Remote Similarity NPD6808 Phase 2
0.6901 Remote Similarity NPD5710 Approved
0.6901 Remote Similarity NPD5711 Approved
0.6899 Remote Similarity NPD6004 Phase 3
0.6899 Remote Similarity NPD6006 Clinical (unspecified phase)
0.6899 Remote Similarity NPD6005 Phase 3
0.6899 Remote Similarity NPD6003 Clinical (unspecified phase)
0.6899 Remote Similarity NPD6002 Phase 3
0.6892 Remote Similarity NPD1547 Clinical (unspecified phase)
0.689 Remote Similarity NPD7239 Suspended
0.6887 Remote Similarity NPD2798 Approved
0.6887 Remote Similarity NPD5647 Approved
0.6879 Remote Similarity NPD1510 Phase 2
0.6867 Remote Similarity NPD1283 Approved
0.6845 Remote Similarity NPD3817 Phase 2
0.6839 Remote Similarity NPD4307 Phase 2
0.6839 Remote Similarity NPD2979 Phase 3
0.6839 Remote Similarity NPD7893 Clinical (unspecified phase)
0.6829 Remote Similarity NPD5403 Approved
0.6821 Remote Similarity NPD3266 Approved
0.6821 Remote Similarity NPD6166 Phase 2
0.6821 Remote Similarity NPD3267 Approved
0.6821 Remote Similarity NPD6168 Clinical (unspecified phase)
0.6821 Remote Similarity NPD6167 Clinical (unspecified phase)
0.6818 Remote Similarity NPD6859 Clinical (unspecified phase)
0.6816 Remote Similarity NPD8055 Clinical (unspecified phase)
0.681 Remote Similarity NPD7410 Clinical (unspecified phase)
0.6803 Remote Similarity NPD5585 Approved
0.6802 Remote Similarity NPD7229 Phase 3
0.68 Remote Similarity NPD7804 Clinical (unspecified phase)
0.6795 Remote Similarity NPD1933 Approved
0.6786 Remote Similarity NPD2801 Approved
0.6776 Remote Similarity NPD6007 Clinical (unspecified phase)
0.6776 Remote Similarity NPD1019 Discontinued
0.6774 Remote Similarity NPD6233 Phase 2
0.6774 Remote Similarity NPD6663 Approved
0.6772 Remote Similarity NPD3748 Approved
0.677 Remote Similarity NPD1878 Clinical (unspecified phase)
0.677 Remote Similarity NPD8166 Discontinued
0.6761 Remote Similarity NPD7074 Phase 3
0.6757 Remote Similarity NPD3412 Clinical (unspecified phase)
0.6757 Remote Similarity NPD17 Approved
0.6752 Remote Similarity NPD6653 Approved
0.6752 Remote Similarity NPD1607 Approved
0.6748 Remote Similarity NPD6143 Clinical (unspecified phase)
0.6746 Remote Similarity NPD5616 Clinical (unspecified phase)
0.6744 Remote Similarity NPD1247 Approved
0.6742 Remote Similarity NPD4338 Clinical (unspecified phase)
0.6732 Remote Similarity NPD5736 Approved
0.6731 Remote Similarity NPD1240 Approved
0.673 Remote Similarity NPD2438 Suspended
0.6726 Remote Similarity NPD6844 Discontinued
0.6725 Remote Similarity NPD6234 Discontinued
0.6723 Remote Similarity NPD7993 Clinical (unspecified phase)
0.671 Remote Similarity NPD1699 Clinical (unspecified phase)
0.671 Remote Similarity NPD6798 Discontinued
0.6709 Remote Similarity NPD7097 Phase 1
0.6707 Remote Similarity NPD5401 Approved
0.6705 Remote Similarity NPD7054 Approved
0.6687 Remote Similarity NPD7440 Discontinued
0.6686 Remote Similarity NPD1465 Phase 2
0.6685 Remote Similarity NPD7685 Pre-registration
0.6685 Remote Similarity NPD8150 Discontinued
0.6667 Remote Similarity NPD7472 Approved
0.6667 Remote Similarity NPD1281 Approved
0.6667 Remote Similarity NPD7615 Clinical (unspecified phase)
0.6648 Remote Similarity NPD7228 Approved
0.6648 Remote Similarity NPD3751 Discontinued
0.6648 Remote Similarity NPD4419 Clinical (unspecified phase)
0.6648 Remote Similarity NPD7177 Discontinued
0.6647 Remote Similarity NPD7199 Phase 2
0.6647 Remote Similarity NPD2296 Approved
0.6646 Remote Similarity NPD1511 Approved
0.6646 Remote Similarity NPD2424 Discontinued
0.6645 Remote Similarity NPD1876 Approved
0.6645 Remote Similarity NPD7008 Discontinued
0.6645 Remote Similarity NPD7095 Approved
0.6644 Remote Similarity NPD1778 Approved
0.6643 Remote Similarity NPD2181 Clinical (unspecified phase)
0.6629 Remote Similarity NPD6797 Phase 2
0.6629 Remote Similarity NPD5953 Discontinued
0.6627 Remote Similarity NPD6280 Approved
0.6627 Remote Similarity NPD6980 Clinical (unspecified phase)
0.6627 Remote Similarity NPD6279 Approved
0.6626 Remote Similarity NPD3887 Approved
0.6625 Remote Similarity NPD4476 Approved
0.6625 Remote Similarity NPD4477 Approved
0.6624 Remote Similarity NPD4060 Phase 1
0.6623 Remote Similarity NPD9494 Approved
0.6622 Remote Similarity NPD9545 Approved
0.661 Remote Similarity NPD7286 Phase 2
0.6608 Remote Similarity NPD7057 Phase 3
0.6608 Remote Similarity NPD7058 Phase 2
0.6601 Remote Similarity NPD6362 Approved
0.66 Remote Similarity NPD3496 Discontinued
0.6599 Remote Similarity NPD9493 Approved
0.6592 Remote Similarity NPD7251 Discontinued
0.6584 Remote Similarity NPD5762 Approved
0.6584 Remote Similarity NPD5763 Approved
0.6582 Remote Similarity NPD4618 Approved
0.6582 Remote Similarity NPD4622 Approved
0.6582 Remote Similarity NPD5123 Clinical (unspecified phase)

Structure

External Identifiers

PubChem CID   90676773
ChEMBL   CHEMBL3263389
ZINC  

Physicochemical Properties

Molecular Weight:  330.18
ALogP:  0.3224
MLogP:  3.22
XLogP:  3.099
# Rotatable Bonds:  4
Polar Surface Area:  59.67
# H-Bond Aceptor:  3
# H-Bond Donor:  1
# Rings:  4
# Heavy Atoms:  24

Download Data

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