Natural Product: NPC179170

Natural Product ID:  NPC179170
Common Name:   3-Hydroxytanshinone
IUPAC Name:   (7S)-7-hydroxy-1,6,6-trimethyl-8,9-dihydro-7H-naphtho[1,2-g][1]benzofuran-10,11-dione
Synonyms:   3-Hydroxytanshinone
Molecular Formula:   C19H18O4
Standard InCHIKey:  PTDUBPDLRWKSBQ-ZDUSSCGKSA-N
Standard InCHI:  InChI=1S/C19H18O4/c1-9-8-23-18-11-4-6-12-10(5-7-13(20)19(12,2)3)15(11)17(22)16(21)14(9)18/h4,6,8,13,20H,5,7H2,1-3H3/t13-/m0/s1
Canonical SMILES:  O[C@H]1CCc2c(C1(C)C)ccc1c2C(=O)C(=O)c2c1occ2C
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
NPO5800 Radix salviae Species Lymnaeidae Eukaryota TCMSP*
NPO5743 Salvia miltiorrhiza Species Lamiaceae Eukaryota TCMID*

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT113 Cell Line RAW264.7 Mus musculus IC50 = 12850 nM 16872829
NPT113 Cell Line RAW264.7 Mus musculus IC50 > 20000 nM 16872829

  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 NPC179170 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
0.9863 High Similarity NPC145830
0.96 High Similarity NPC221992
0.9597 High Similarity NPC88958
0.9536 High Similarity NPC10051
0.9536 High Similarity NPC299094
0.9521 High Similarity NPC281398
0.9396 High Similarity NPC144010
0.9252 High Similarity NPC93241
0.9252 High Similarity NPC27798
0.9184 High Similarity NPC117674
0.9007 High Similarity NPC192069
0.8938 High Similarity NPC44602
0.8812 High Similarity NPC472784
0.8808 High Similarity NPC233763
0.879 High Similarity NPC140952
0.8784 High Similarity NPC18904
0.8774 High Similarity NPC44606
0.8742 High Similarity NPC245522
0.8742 High Similarity NPC114513
0.8734 High Similarity NPC472299
0.8726 High Similarity NPC81405
0.8684 High Similarity NPC478166
0.8599 High Similarity NPC290927
0.8599 High Similarity NPC23559
0.859 High Similarity NPC471613
0.8589 High Similarity NPC473945
0.8581 High Similarity NPC472298
0.8571 High Similarity NPC478018
0.8553 High Similarity NPC123153
0.8553 High Similarity NPC53016
0.8535 High Similarity NPC282793
0.8535 High Similarity NPC10429
0.8516 High Similarity NPC95526
0.8509 High Similarity NPC472780
0.8509 High Similarity NPC472783
0.85 High Similarity NPC287559
0.8481 Intermediate Similarity NPC469966
0.8467 Intermediate Similarity NPC265181
0.8466 Intermediate Similarity NPC136641
0.8457 Intermediate Similarity NPC56358
0.8452 Intermediate Similarity NPC252208
0.8447 Intermediate Similarity NPC472782
0.8447 Intermediate Similarity NPC472781
0.8447 Intermediate Similarity NPC18986
0.8438 Intermediate Similarity NPC473282
0.8438 Intermediate Similarity NPC217602
0.8438 Intermediate Similarity NPC317900
0.8438 Intermediate Similarity NPC476404
0.8438 Intermediate Similarity NPC294300
0.8438 Intermediate Similarity NPC104380
0.8431 Intermediate Similarity NPC158871
0.8431 Intermediate Similarity NPC163948
0.8421 Intermediate Similarity NPC52412
0.8421 Intermediate Similarity NPC263337
0.8418 Intermediate Similarity NPC24232
0.8405 Intermediate Similarity NPC100849
0.8405 Intermediate Similarity NPC121995
0.84 Intermediate Similarity NPC177262
0.8393 Intermediate Similarity NPC295914
0.8385 Intermediate Similarity NPC476349
0.8385 Intermediate Similarity NPC476350
0.8377 Intermediate Similarity NPC185456
0.8377 Intermediate Similarity NPC290038
0.8375 Intermediate Similarity NPC304692
0.8365 Intermediate Similarity NPC472786
0.8365 Intermediate Similarity NPC158261
0.8365 Intermediate Similarity NPC25351
0.8365 Intermediate Similarity NPC42458
0.8364 Intermediate Similarity NPC472660
0.8354 Intermediate Similarity NPC270312
0.8354 Intermediate Similarity NPC41689
0.8344 Intermediate Similarity NPC226578
0.8344 Intermediate Similarity NPC472664
0.8344 Intermediate Similarity NPC202260
0.8344 Intermediate Similarity NPC233707
0.8323 Intermediate Similarity NPC474611
0.8323 Intermediate Similarity NPC478019
0.8313 Intermediate Similarity NPC41880
0.8313 Intermediate Similarity NPC478161
0.8313 Intermediate Similarity NPC478159
0.8313 Intermediate Similarity NPC104736
0.8303 Intermediate Similarity NPC255787
0.8293 Intermediate Similarity NPC308156
0.8282 Intermediate Similarity NPC269117
0.8282 Intermediate Similarity NPC24761
0.828 Intermediate Similarity NPC280025
0.8269 Intermediate Similarity NPC224418
0.8261 Intermediate Similarity NPC247677
0.8261 Intermediate Similarity NPC160015
0.825 Intermediate Similarity NPC208806
0.825 Intermediate Similarity NPC75310
0.8247 Intermediate Similarity NPC103134
0.8247 Intermediate Similarity NPC69755
0.8239 Intermediate Similarity NPC294511
0.8239 Intermediate Similarity NPC121615
0.8228 Intermediate Similarity NPC212257
0.8217 Intermediate Similarity NPC478163
0.821 Intermediate Similarity NPC296957
0.821 Intermediate Similarity NPC96342
0.821 Intermediate Similarity NPC164110
0.821 Intermediate Similarity NPC212967
0.821 Intermediate Similarity NPC260902
0.821 Intermediate Similarity NPC246647
0.82 Intermediate Similarity NPC324117
0.8193 Intermediate Similarity NPC291742
0.8187 Intermediate Similarity NPC154683
0.8187 Intermediate Similarity NPC263676
0.8187 Intermediate Similarity NPC40356
0.8176 Intermediate Similarity NPC472787
0.8176 Intermediate Similarity NPC472661
0.8171 Intermediate Similarity NPC283209
0.817 Intermediate Similarity NPC470407
0.8165 Intermediate Similarity NPC211625
0.8165 Intermediate Similarity NPC474107
0.816 Intermediate Similarity NPC472877
0.8153 Intermediate Similarity NPC302987
0.815 Intermediate Similarity NPC472663
0.815 Intermediate Similarity NPC472662
0.8148 Intermediate Similarity NPC180924
0.8148 Intermediate Similarity NPC7059
0.8137 Intermediate Similarity NPC122365
0.8129 Intermediate Similarity NPC64568
0.8129 Intermediate Similarity NPC329493
0.8125 Intermediate Similarity NPC156244
0.8125 Intermediate Similarity NPC470569
0.8125 Intermediate Similarity NPC475777
0.8113 Intermediate Similarity NPC228842
0.811 Intermediate Similarity NPC68848
0.811 Intermediate Similarity NPC79571
0.8108 Intermediate Similarity NPC57552
0.8092 Intermediate Similarity NPC307401
0.8092 Intermediate Similarity NPC42400
0.8089 Intermediate Similarity NPC62799
0.8086 Intermediate Similarity NPC148938
0.8086 Intermediate Similarity NPC3898
0.8084 Intermediate Similarity NPC296558
0.8084 Intermediate Similarity NPC191012
0.8079 Intermediate Similarity NPC209858
0.8077 Intermediate Similarity NPC476944
0.8075 Intermediate Similarity NPC38361
0.8075 Intermediate Similarity NPC67654
0.8075 Intermediate Similarity NPC178932
0.8075 Intermediate Similarity NPC114880
0.8075 Intermediate Similarity NPC130015
0.8072 Intermediate Similarity NPC475779
0.8063 Intermediate Similarity NPC290954
0.8063 Intermediate Similarity NPC148423
0.8063 Intermediate Similarity NPC135303
0.8063 Intermediate Similarity NPC470568
0.8063 Intermediate Similarity NPC255641
0.8063 Intermediate Similarity NPC472406
0.8061 Intermediate Similarity NPC285567
0.8052 Intermediate Similarity NPC1268
0.8049 Intermediate Similarity NPC8389
0.8038 Intermediate Similarity NPC71821
0.8038 Intermediate Similarity NPC300540
0.8037 Intermediate Similarity NPC478223
0.8037 Intermediate Similarity NPC194499
0.8036 Intermediate Similarity NPC186392
0.8026 Intermediate Similarity NPC46896
0.8025 Intermediate Similarity NPC235333
0.8025 Intermediate Similarity NPC469336
0.8025 Intermediate Similarity NPC474000
0.8025 Intermediate Similarity NPC213608
0.8025 Intermediate Similarity NPC1477
0.8025 Intermediate Similarity NPC469385
0.8025 Intermediate Similarity NPC472785
0.8025 Intermediate Similarity NPC214632
0.8025 Intermediate Similarity NPC475770
0.8024 Intermediate Similarity NPC314653
0.8024 Intermediate Similarity NPC316262
0.8013 Intermediate Similarity NPC267632
0.8013 Intermediate Similarity NPC243577
0.8012 Intermediate Similarity NPC232645
0.8012 Intermediate Similarity NPC474417
0.8012 Intermediate Similarity NPC116604
0.8012 Intermediate Similarity NPC149526
0.8012 Intermediate Similarity NPC72958
0.8012 Intermediate Similarity NPC193998
0.8 Intermediate Similarity NPC296030
0.8 Intermediate Similarity NPC470810
0.8 Intermediate Similarity NPC313368
0.8 Intermediate Similarity NPC214493
0.8 Intermediate Similarity NPC188649
0.8 Intermediate Similarity NPC39929
0.8 Intermediate Similarity NPC478002
0.7989 Intermediate Similarity NPC228209
0.7988 Intermediate Similarity NPC268360
0.7988 Intermediate Similarity NPC67197
0.7988 Intermediate Similarity NPC269495
0.7988 Intermediate Similarity NPC475237
0.7988 Intermediate Similarity NPC294512
0.7988 Intermediate Similarity NPC475641
0.7988 Intermediate Similarity NPC272196
0.7988 Intermediate Similarity NPC472823
0.7987 Intermediate Similarity NPC198427
0.7977 Intermediate Similarity NPC104682
0.7976 Intermediate Similarity NPC125465
0.7975 Intermediate Similarity NPC297531
0.7975 Intermediate Similarity NPC49282

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC179170 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
0.8467 Intermediate Similarity NPD1471 Phase 3
0.8224 Intermediate Similarity NPD2344 Approved
0.8113 Intermediate Similarity NPD3226 Approved
0.8105 Intermediate Similarity NPD2346 Discontinued
0.8105 Intermediate Similarity NPD2343 Clinical (unspecified phase)
0.8013 Intermediate Similarity NPD2309 Approved
0.7829 Intermediate Similarity NPD8434 Phase 2
0.7824 Intermediate Similarity NPD7893 Clinical (unspecified phase)
0.7812 Intermediate Similarity NPD6273 Approved
0.7805 Intermediate Similarity NPD5760 Phase 2
0.7805 Intermediate Similarity NPD5761 Phase 2
0.7771 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7742 Intermediate Similarity NPD2799 Discontinued
0.7722 Intermediate Similarity NPD4628 Phase 3
0.7697 Intermediate Similarity NPD2313 Discontinued
0.7697 Intermediate Similarity NPD7819 Suspended
0.7669 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7651 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.7644 Intermediate Similarity NPD6559 Discontinued
0.7635 Intermediate Similarity NPD3972 Approved
0.7633 Intermediate Similarity NPD6959 Discontinued
0.7619 Intermediate Similarity NPD5537 Clinical (unspecified phase)
0.761 Intermediate Similarity NPD7003 Approved
0.7588 Intermediate Similarity NPD6808 Phase 2
0.7576 Intermediate Similarity NPD7411 Suspended
0.756 Intermediate Similarity NPD3749 Approved
0.7546 Intermediate Similarity NPD920 Approved
0.7545 Intermediate Similarity NPD5616 Clinical (unspecified phase)
0.753 Intermediate Similarity NPD6280 Approved
0.753 Intermediate Similarity NPD6279 Approved
0.7468 Intermediate Similarity NPD2796 Approved
0.7455 Intermediate Similarity NPD7458 Discontinued
0.745 Intermediate Similarity NPD1547 Clinical (unspecified phase)
0.744 Intermediate Similarity NPD2296 Approved
0.7438 Intermediate Similarity NPD2800 Approved
0.7427 Intermediate Similarity NPD1247 Approved
0.7423 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.7423 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7423 Intermediate Similarity NPD2532 Approved
0.7423 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.7423 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7423 Intermediate Similarity NPD2534 Approved
0.7423 Intermediate Similarity NPD2533 Approved
0.741 Intermediate Similarity NPD6599 Discontinued
0.7407 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.7399 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.7384 Intermediate Similarity NPD6232 Discontinued
0.7381 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7381 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.7375 Intermediate Similarity NPD1549 Phase 2
0.7371 Intermediate Similarity NPD5844 Phase 1
0.7368 Intermediate Similarity NPD5494 Approved
0.7356 Intermediate Similarity NPD7473 Discontinued
0.7345 Intermediate Similarity NPD6764 Approved
0.7345 Intermediate Similarity NPD6765 Approved
0.732 Intermediate Similarity NPD2798 Approved
0.7315 Intermediate Similarity NPD3412 Clinical (unspecified phase)
0.7312 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.7312 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.7305 Intermediate Similarity NPD4380 Phase 2
0.7303 Intermediate Similarity NPD1876 Approved
0.7296 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.729 Intermediate Similarity NPD5952 Clinical (unspecified phase)
0.7255 Intermediate Similarity NPD1470 Approved
0.7251 Intermediate Similarity NPD7075 Discontinued
0.725 Intermediate Similarity NPD2935 Discontinued
0.7248 Intermediate Similarity NPD1651 Approved
0.7241 Intermediate Similarity NPD3926 Phase 2
0.7222 Intermediate Similarity NPD1243 Approved
0.7219 Intermediate Similarity NPD6801 Discontinued
0.7209 Intermediate Similarity NPD919 Approved
0.7193 Intermediate Similarity NPD3882 Suspended
0.7193 Intermediate Similarity NPD7768 Phase 2
0.719 Intermediate Similarity NPD1283 Approved
0.7188 Intermediate Similarity NPD1510 Phase 2
0.7182 Intermediate Similarity NPD6784 Approved
0.7182 Intermediate Similarity NPD6785 Approved
0.7174 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.717 Intermediate Similarity NPD1607 Approved
0.7167 Intermediate Similarity NPD8313 Approved
0.7167 Intermediate Similarity NPD8312 Approved
0.7152 Intermediate Similarity NPD4140 Approved
0.7143 Intermediate Similarity NPD1551 Phase 2
0.7134 Intermediate Similarity NPD3268 Approved
0.7119 Intermediate Similarity NPD3818 Discontinued
0.7119 Intermediate Similarity NPD7177 Discontinued
0.7118 Intermediate Similarity NPD6844 Discontinued
0.7118 Intermediate Similarity NPD1934 Approved
0.7115 Intermediate Similarity NPD6832 Phase 2
0.7108 Intermediate Similarity NPD7422 Clinical (unspecified phase)
0.7089 Intermediate Similarity NPD8032 Phase 2
0.707 Intermediate Similarity NPD7008 Discontinued
0.7065 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7052 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.7048 Intermediate Similarity NPD6799 Approved
0.7044 Intermediate Similarity NPD1240 Approved
0.7044 Intermediate Similarity NPD2979 Phase 3
0.7037 Intermediate Similarity NPD5404 Approved
0.7037 Intermediate Similarity NPD5408 Approved
0.7037 Intermediate Similarity NPD5405 Approved
0.7037 Intermediate Similarity NPD5406 Approved
0.7025 Intermediate Similarity NPD3764 Approved
0.7006 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.7006 Intermediate Similarity NPD6166 Phase 2
0.7006 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.6993 Remote Similarity NPD1281 Approved
0.6993 Remote Similarity NPD1201 Approved
0.6988 Remote Similarity NPD7236 Approved
0.6977 Remote Similarity NPD2801 Approved
0.6975 Remote Similarity NPD7033 Discontinued
0.6975 Remote Similarity NPD4308 Phase 3
0.697 Remote Similarity NPD3750 Approved
0.6959 Remote Similarity NPD5889 Approved
0.6959 Remote Similarity NPD5890 Approved
0.6946 Remote Similarity NPD7390 Discontinued
0.6933 Remote Similarity NPD6099 Approved
0.6933 Remote Similarity NPD2438 Suspended
0.6933 Remote Similarity NPD6100 Approved
0.6933 Remote Similarity NPD4476 Approved
0.6933 Remote Similarity NPD4477 Approved
0.6932 Remote Similarity NPD8127 Discontinued
0.6927 Remote Similarity NPD3751 Discontinued
0.6923 Remote Similarity NPD3266 Approved
0.6923 Remote Similarity NPD4419 Clinical (unspecified phase)
0.6923 Remote Similarity NPD1203 Approved
0.6923 Remote Similarity NPD3267 Approved
0.6918 Remote Similarity NPD6798 Discontinued
0.6918 Remote Similarity NPD1699 Clinical (unspecified phase)
0.6911 Remote Similarity NPD6776 Approved
0.6911 Remote Similarity NPD6782 Approved
0.6911 Remote Similarity NPD6780 Approved
0.6911 Remote Similarity NPD6778 Approved
0.6911 Remote Similarity NPD6781 Approved
0.6911 Remote Similarity NPD6779 Approved
0.6911 Remote Similarity NPD6777 Approved
0.691 Remote Similarity NPD4575 Clinical (unspecified phase)
0.6905 Remote Similarity NPD4661 Approved
0.6905 Remote Similarity NPD4662 Approved
0.6903 Remote Similarity NPD5327 Phase 3
0.6894 Remote Similarity NPD5735 Approved
0.6894 Remote Similarity NPD6355 Discontinued
0.6894 Remote Similarity NPD1899 Clinical (unspecified phase)
0.6893 Remote Similarity NPD7229 Phase 3
0.6893 Remote Similarity NPD5711 Approved
0.6893 Remote Similarity NPD5710 Approved
0.6889 Remote Similarity NPD7804 Clinical (unspecified phase)
0.6882 Remote Similarity NPD7239 Suspended
0.6871 Remote Similarity NPD3748 Approved
0.6859 Remote Similarity NPD8285 Discontinued
0.6852 Remote Similarity NPD6651 Approved
0.6848 Remote Similarity NPD970 Clinical (unspecified phase)
0.6846 Remote Similarity NPD1241 Discontinued
0.6845 Remote Similarity NPD1511 Approved
0.6842 Remote Similarity NPD2649 Approved
0.6842 Remote Similarity NPD2651 Approved
0.6839 Remote Similarity NPD3817 Phase 2
0.6839 Remote Similarity NPD5402 Approved
0.6839 Remote Similarity NPD9717 Approved
0.6839 Remote Similarity NPD1608 Approved
0.6832 Remote Similarity NPD4307 Phase 2
0.6829 Remote Similarity NPD2531 Phase 2
0.6828 Remote Similarity NPD7693 Approved
0.6826 Remote Similarity NPD3295 Clinical (unspecified phase)
0.6824 Remote Similarity NPD5403 Approved
0.6815 Remote Similarity NPD2797 Approved
0.6813 Remote Similarity NPD5953 Discontinued
0.6813 Remote Similarity NPD411 Approved
0.6805 Remote Similarity NPD5401 Approved
0.6804 Remote Similarity NPD7697 Approved
0.6804 Remote Similarity NPD7696 Phase 3
0.6804 Remote Similarity NPD7698 Approved
0.6804 Remote Similarity NPD7435 Discontinued
0.6802 Remote Similarity NPD6585 Discontinued
0.68 Remote Similarity NPD5951 Approved
0.68 Remote Similarity NPD4868 Clinical (unspecified phase)
0.6798 Remote Similarity NPD3787 Discontinued
0.6797 Remote Similarity NPD5691 Approved
0.6791 Remote Similarity NPD4287 Approved
0.6774 Remote Similarity NPD8150 Discontinued
0.6769 Remote Similarity NPD7870 Phase 2
0.6769 Remote Similarity NPD7871 Phase 2
0.6766 Remote Similarity NPD4110 Phase 3
0.6766 Remote Similarity NPD1878 Clinical (unspecified phase)
0.6766 Remote Similarity NPD6398 Clinical (unspecified phase)
0.6766 Remote Similarity NPD4109 Clinical (unspecified phase)
0.6765 Remote Similarity NPD1512 Approved
0.6758 Remote Similarity NPD7074 Phase 3
0.6753 Remote Similarity NPD1778 Approved
0.6753 Remote Similarity NPD3019 Approved
0.6753 Remote Similarity NPD4626 Approved
0.675 Remote Similarity NPD7095 Approved
0.6748 Remote Similarity NPD6353 Approved
0.6747 Remote Similarity NPD2424 Discontinued
0.6746 Remote Similarity NPD6143 Clinical (unspecified phase)
0.674 Remote Similarity NPD2163 Approved
0.6737 Remote Similarity NPD6535 Approved
0.6737 Remote Similarity NPD6534 Approved
0.6736 Remote Similarity NPD7501 Clinical (unspecified phase)
0.6733 Remote Similarity NPD8404 Phase 2
0.673 Remote Similarity NPD9494 Approved

Structure

External Identifiers

PubChem CID   5318350
ChEMBL   CHEMBL377478
ZINC  

Physicochemical Properties

Molecular Weight:  310.12
ALogP:  0.1382
MLogP:  3.11
XLogP:  2.422
# Rotatable Bonds:  4
Polar Surface Area:  67.51
# H-Bond Aceptor:  3
# H-Bond Donor:  1
# Rings:  4
# Heavy Atoms:  23

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Biological Activities  
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