Natural Product: NPC161778

Natural Product ID:  NPC161778
Common Name:   Orthosiphonol
IUPAC Name:   (4aS,10aS)-6,8-dihydroxy-5-methoxy-1,1,4a-trimethyl-7-propan-2-yl-3,4,10,10a-tetrahydro-2H-phenanthren-9-one
Synonyms:   Orthosiphonol
Molecular Formula:   C21H30O4
Standard InCHIKey:  DTHWSUAQUGVGLC-ZSEKCTLFSA-N
Standard InCHI:  InChI=1S/C21H30O4/c1-11(2)14-17(23)15-12(22)10-13-20(3,4)8-7-9-21(13,5)16(15)19(25-6)18(14)24/h11,13,23-24H,7-10H2,1-6H3/t13-,21-/m0/s1
Canonical SMILES:  COc1c(O)c(C(C)C)c(c2c1[C@@]1(C)CCCC([C@@H]1CC2=O)(C)C)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
NPO997 Peltodon longipes Species Lamiaceae Eukaryota roots Santa Maria, South Brazil 2007-DEC PMID[21775156]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT783 Cell Line MIA PaCa-2 Homo sapiens IC50 > 100000 nM 26110443
NPT2 Others Unspecified IC50 > 80000 nM 27338658

  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 NPC161778 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
0.9932 High Similarity NPC273248
0.9533 High Similarity NPC276815
0.9533 High Similarity NPC25850
0.947 High Similarity NPC283301
0.9355 High Similarity NPC102372
0.9241 High Similarity NPC92079
0.9167 High Similarity NPC208120
0.9167 High Similarity NPC29055
0.9167 High Similarity NPC173587
0.9114 High Similarity NPC232936
0.9108 High Similarity NPC146584
0.9108 High Similarity NPC21016
0.9097 High Similarity NPC155302
0.9097 High Similarity NPC161947
0.9097 High Similarity NPC84571
0.9057 High Similarity NPC213416
0.9045 High Similarity NPC475055
0.9038 High Similarity NPC87431
0.9038 High Similarity NPC311740
0.8968 High Similarity NPC37543
0.8968 High Similarity NPC199463
0.8961 High Similarity NPC472048
0.8954 High Similarity NPC218628
0.8924 High Similarity NPC270837
0.8924 High Similarity NPC236132
0.8924 High Similarity NPC220313
0.8903 High Similarity NPC14561
0.8903 High Similarity NPC77807
0.8903 High Similarity NPC5379
0.8903 High Similarity NPC474167
0.8903 High Similarity NPC470762
0.8861 High Similarity NPC294965
0.8861 High Similarity NPC470694
0.8854 High Similarity NPC228785
0.8854 High Similarity NPC14353
0.8854 High Similarity NPC56085
0.8846 High Similarity NPC178976
0.8846 High Similarity NPC179732
0.8824 High Similarity NPC50269
0.8797 High Similarity NPC61010
0.8797 High Similarity NPC40491
0.8797 High Similarity NPC278052
0.8797 High Similarity NPC66288
0.8797 High Similarity NPC32694
0.879 High Similarity NPC100123
0.879 High Similarity NPC45846
0.8774 High Similarity NPC107109
0.8758 High Similarity NPC303989
0.875 High Similarity NPC26386
0.875 High Similarity NPC25361
0.8742 High Similarity NPC215612
0.8734 High Similarity NPC45146
0.8734 High Similarity NPC235018
0.8734 High Similarity NPC320359
0.8734 High Similarity NPC80375
0.8734 High Similarity NPC119224
0.8726 High Similarity NPC300727
0.8726 High Similarity NPC241904
0.8726 High Similarity NPC165977
0.8726 High Similarity NPC217677
0.8718 High Similarity NPC134287
0.8718 High Similarity NPC130589
0.8712 High Similarity NPC158226
0.871 High Similarity NPC149889
0.871 High Similarity NPC312338
0.8704 High Similarity NPC165979
0.8704 High Similarity NPC163130
0.8696 High Similarity NPC37870
0.8693 High Similarity NPC476058
0.8688 High Similarity NPC152659
0.8688 High Similarity NPC236521
0.8688 High Similarity NPC101769
0.8688 High Similarity NPC248638
0.8688 High Similarity NPC197168
0.8688 High Similarity NPC7483
0.8679 High Similarity NPC472275
0.8679 High Similarity NPC65746
0.8675 High Similarity NPC309169
0.8675 High Similarity NPC196941
0.8671 High Similarity NPC235448
0.8671 High Similarity NPC476242
0.8662 High Similarity NPC274730
0.8662 High Similarity NPC142339
0.8654 High Similarity NPC93552
0.8654 High Similarity NPC477047
0.8654 High Similarity NPC477048
0.8636 High Similarity NPC134293
0.8634 High Similarity NPC239752
0.8634 High Similarity NPC473286
0.8634 High Similarity NPC326520
0.8634 High Similarity NPC472450
0.8634 High Similarity NPC275780
0.8627 High Similarity NPC251188
0.8627 High Similarity NPC52692
0.8625 High Similarity NPC25152
0.8616 High Similarity NPC185617
0.8616 High Similarity NPC297212
0.8616 High Similarity NPC475886
0.8616 High Similarity NPC474287
0.8608 High Similarity NPC36852
0.8608 High Similarity NPC78225
0.8608 High Similarity NPC469584
0.8608 High Similarity NPC78103
0.8608 High Similarity NPC262286
0.8608 High Similarity NPC219867
0.8608 High Similarity NPC180011
0.8608 High Similarity NPC79053
0.8608 High Similarity NPC236796
0.8599 High Similarity NPC68727
0.8599 High Similarity NPC39184
0.859 High Similarity NPC470338
0.859 High Similarity NPC268992
0.859 High Similarity NPC51824
0.859 High Similarity NPC113608
0.859 High Similarity NPC164912
0.859 High Similarity NPC470337
0.8589 High Similarity NPC49487
0.8589 High Similarity NPC476637
0.8589 High Similarity NPC99613
0.8581 High Similarity NPC472279
0.8581 High Similarity NPC294646
0.858 High Similarity NPC29160
0.858 High Similarity NPC39091
0.858 High Similarity NPC170245
0.8571 High Similarity NPC240508
0.8571 High Similarity NPC189473
0.8571 High Similarity NPC303460
0.8571 High Similarity NPC306321
0.8571 High Similarity NPC23298
0.8571 High Similarity NPC131451
0.8571 High Similarity NPC207690
0.8571 High Similarity NPC15329
0.8571 High Similarity NPC146134
0.8562 High Similarity NPC475883
0.8562 High Similarity NPC472906
0.8562 High Similarity NPC278427
0.8562 High Similarity NPC474186
0.8562 High Similarity NPC474187
0.8562 High Similarity NPC266314
0.8562 High Similarity NPC474351
0.8553 High Similarity NPC250214
0.8553 High Similarity NPC315157
0.8553 High Similarity NPC185258
0.8553 High Similarity NPC95936
0.8553 High Similarity NPC172770
0.8553 High Similarity NPC85121
0.8553 High Similarity NPC46736
0.8544 High Similarity NPC68093
0.8544 High Similarity NPC138243
0.8544 High Similarity NPC115853
0.8544 High Similarity NPC191146
0.8543 High Similarity NPC11314
0.8537 High Similarity NPC124470
0.8537 High Similarity NPC109827
0.8535 High Similarity NPC127172
0.8535 High Similarity NPC250557
0.8535 High Similarity NPC124714
0.8535 High Similarity NPC89474
0.8528 High Similarity NPC6588
0.8528 High Similarity NPC117854
0.8528 High Similarity NPC126204
0.8528 High Similarity NPC477154
0.8528 High Similarity NPC234331
0.8526 High Similarity NPC78505
0.8526 High Similarity NPC302783
0.8526 High Similarity NPC45291
0.8526 High Similarity NPC19980
0.8526 High Similarity NPC473201
0.8526 High Similarity NPC75377
0.8526 High Similarity NPC118427
0.8516 High Similarity NPC102003
0.8516 High Similarity NPC92722
0.8509 High Similarity NPC52204
0.8509 High Similarity NPC229632
0.8503 High Similarity NPC77179
0.8503 High Similarity NPC23553
0.85 High Similarity NPC36217
0.85 High Similarity NPC200746
0.85 High Similarity NPC476980
0.85 High Similarity NPC476280
0.85 High Similarity NPC246478
0.8491 Intermediate Similarity NPC245758
0.8491 Intermediate Similarity NPC222814
0.8491 Intermediate Similarity NPC302258
0.8491 Intermediate Similarity NPC136674
0.8491 Intermediate Similarity NPC472913
0.8491 Intermediate Similarity NPC187745
0.8491 Intermediate Similarity NPC161960
0.8491 Intermediate Similarity NPC472911
0.8491 Intermediate Similarity NPC472910
0.8491 Intermediate Similarity NPC96167
0.8491 Intermediate Similarity NPC223787
0.8491 Intermediate Similarity NPC472914
0.8491 Intermediate Similarity NPC304008
0.8481 Intermediate Similarity NPC234485
0.8481 Intermediate Similarity NPC16286
0.8481 Intermediate Similarity NPC113906
0.8476 Intermediate Similarity NPC475805
0.8471 Intermediate Similarity NPC471982
0.8471 Intermediate Similarity NPC35763

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC161778 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
0.858 High Similarity NPD7473 Discontinued
0.8509 High Similarity NPD6232 Discontinued
0.8418 Intermediate Similarity NPD2801 Approved
0.8187 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.8141 Intermediate Similarity NPD2532 Approved
0.8141 Intermediate Similarity NPD2534 Approved
0.8141 Intermediate Similarity NPD2533 Approved
0.8133 Intermediate Similarity NPD6651 Approved
0.8125 Intermediate Similarity NPD1934 Approved
0.7939 Intermediate Similarity NPD5494 Approved
0.7935 Intermediate Similarity NPD2800 Approved
0.7929 Intermediate Similarity NPD5844 Phase 1
0.7892 Intermediate Similarity NPD6959 Discontinued
0.7866 Intermediate Similarity NPD3882 Suspended
0.7857 Intermediate Similarity NPD6166 Phase 2
0.7857 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.7857 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.7848 Intermediate Similarity NPD1511 Approved
0.7792 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.775 Intermediate Similarity NPD1512 Approved
0.7688 Intermediate Similarity NPD7422 Clinical (unspecified phase)
0.7688 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.7684 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7669 Intermediate Similarity NPD4380 Phase 2
0.7661 Intermediate Similarity NPD3818 Discontinued
0.7651 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7643 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7636 Intermediate Similarity NPD1465 Phase 2
0.7625 Intermediate Similarity NPD7390 Discontinued
0.759 Intermediate Similarity NPD3817 Phase 2
0.7572 Intermediate Similarity NPD7074 Phase 3
0.756 Intermediate Similarity NPD6234 Discontinued
0.7548 Intermediate Similarity NPD1607 Approved
0.7543 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.7532 Intermediate Similarity NPD943 Approved
0.753 Intermediate Similarity NPD7819 Suspended
0.7529 Intermediate Similarity NPD5711 Approved
0.7529 Intermediate Similarity NPD5710 Approved
0.7516 Intermediate Similarity NPD2935 Discontinued
0.7514 Intermediate Similarity NPD7054 Approved
0.7485 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.7471 Intermediate Similarity NPD7472 Approved
0.747 Intermediate Similarity NPD37 Approved
0.7469 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.7455 Intermediate Similarity NPD6599 Discontinued
0.7452 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.7452 Intermediate Similarity NPD1510 Phase 2
0.7419 Intermediate Similarity NPD1240 Approved
0.7405 Intermediate Similarity NPD6099 Approved
0.7405 Intermediate Similarity NPD6100 Approved
0.7403 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7396 Intermediate Similarity NPD7075 Discontinued
0.7337 Intermediate Similarity NPD4965 Approved
0.7337 Intermediate Similarity NPD4967 Phase 2
0.7337 Intermediate Similarity NPD4966 Approved
0.733 Intermediate Similarity NPD6797 Phase 2
0.7321 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.7289 Intermediate Similarity NPD3226 Approved
0.7288 Intermediate Similarity NPD7251 Discontinued
0.7267 Intermediate Similarity NPD1247 Approved
0.7262 Intermediate Similarity NPD6801 Discontinued
0.7257 Intermediate Similarity NPD7228 Approved
0.725 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.725 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.725 Intermediate Similarity NPD2346 Discontinued
0.7247 Intermediate Similarity NPD7808 Phase 3
0.7232 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7222 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7205 Intermediate Similarity NPD1549 Phase 2
0.7202 Intermediate Similarity NPD7411 Suspended
0.7193 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.7191 Intermediate Similarity NPD6559 Discontinued
0.7186 Intermediate Similarity NPD7458 Discontinued
0.7169 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7152 Intermediate Similarity NPD230 Phase 1
0.7128 Intermediate Similarity NPD6778 Approved
0.7128 Intermediate Similarity NPD7501 Clinical (unspecified phase)
0.7128 Intermediate Similarity NPD6780 Approved
0.7128 Intermediate Similarity NPD6776 Approved
0.7128 Intermediate Similarity NPD6782 Approved
0.7128 Intermediate Similarity NPD6777 Approved
0.7128 Intermediate Similarity NPD6781 Approved
0.7128 Intermediate Similarity NPD6779 Approved
0.7119 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.7117 Intermediate Similarity NPD7003 Approved
0.7117 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7093 Intermediate Similarity NPD3749 Approved
0.7091 Intermediate Similarity NPD6799 Approved
0.7088 Intermediate Similarity NPD8150 Discontinued
0.7086 Intermediate Similarity NPD3926 Phase 2
0.7081 Intermediate Similarity NPD5405 Approved
0.7081 Intermediate Similarity NPD5404 Approved
0.7081 Intermediate Similarity NPD2796 Approved
0.7081 Intermediate Similarity NPD5408 Approved
0.7081 Intermediate Similarity NPD5406 Approved
0.7076 Intermediate Similarity NPD5402 Approved
0.707 Intermediate Similarity NPD1699 Clinical (unspecified phase)
0.7069 Intermediate Similarity NPD7199 Phase 2
0.7045 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.7035 Intermediate Similarity NPD7768 Phase 2
0.7017 Intermediate Similarity NPD8313 Approved
0.7017 Intermediate Similarity NPD8312 Approved
0.7016 Intermediate Similarity NPD7435 Discontinued
0.7012 Intermediate Similarity NPD3750 Approved
0.7012 Intermediate Similarity NPD4628 Phase 3
0.701 Intermediate Similarity NPD8151 Discontinued
0.7006 Intermediate Similarity NPD3027 Phase 3
0.6989 Remote Similarity NPD7184 Clinical (unspecified phase)
0.6987 Remote Similarity NPD9494 Approved
0.6981 Remote Similarity NPD3620 Phase 2
0.6981 Remote Similarity NPD3619 Clinical (unspecified phase)
0.6968 Remote Similarity NPD1470 Approved
0.6954 Remote Similarity NPD919 Approved
0.6952 Remote Similarity NPD6534 Approved
0.6952 Remote Similarity NPD6535 Approved
0.6951 Remote Similarity NPD6674 Discontinued
0.6937 Remote Similarity NPD447 Suspended
0.6928 Remote Similarity NPD1201 Approved
0.6927 Remote Similarity NPD7698 Approved
0.6927 Remote Similarity NPD7696 Phase 3
0.6927 Remote Similarity NPD7697 Approved
0.6914 Remote Similarity NPD2799 Discontinued
0.6909 Remote Similarity NPD8166 Discontinued
0.6902 Remote Similarity NPD8434 Phase 2
0.6891 Remote Similarity NPD7870 Phase 2
0.6891 Remote Similarity NPD7871 Phase 2
0.6886 Remote Similarity NPD6143 Clinical (unspecified phase)
0.6879 Remote Similarity NPD1530 Clinical (unspecified phase)
0.6875 Remote Similarity NPD6823 Phase 2
0.6872 Remote Similarity NPD3751 Discontinued
0.6872 Remote Similarity NPD7701 Phase 2
0.6855 Remote Similarity NPD7985 Registered
0.6853 Remote Similarity NPD7801 Approved
0.6848 Remote Similarity NPD7421 Clinical (unspecified phase)
0.6842 Remote Similarity NPD7699 Phase 2
0.6842 Remote Similarity NPD7700 Phase 2
0.6839 Remote Similarity NPD4379 Clinical (unspecified phase)
0.6836 Remote Similarity NPD3787 Discontinued
0.6835 Remote Similarity NPD1529 Clinical (unspecified phase)
0.6831 Remote Similarity NPD3534 Clinical (unspecified phase)
0.6826 Remote Similarity NPD3300 Phase 2
0.6813 Remote Similarity NPD7240 Approved
0.6807 Remote Similarity NPD1878 Clinical (unspecified phase)
0.6802 Remote Similarity NPD7875 Clinical (unspecified phase)
0.6802 Remote Similarity NPD7874 Approved
0.6793 Remote Similarity NPD7090 Clinical (unspecified phase)
0.6784 Remote Similarity NPD5808 Clinical (unspecified phase)
0.678 Remote Similarity NPD8127 Discontinued
0.6776 Remote Similarity NPD4419 Clinical (unspecified phase)
0.6774 Remote Similarity NPD3972 Approved
0.6774 Remote Similarity NPD9269 Phase 2
0.677 Remote Similarity NPD1612 Clinical (unspecified phase)
0.677 Remote Similarity NPD1613 Approved
0.6768 Remote Similarity NPD1551 Phase 2
0.6768 Remote Similarity NPD7783 Phase 2
0.6768 Remote Similarity NPD7782 Clinical (unspecified phase)
0.6766 Remote Similarity NPD6190 Approved
0.6765 Remote Similarity NPD920 Approved
0.6755 Remote Similarity NPD7340 Approved
0.675 Remote Similarity NPD2313 Discontinued
0.6746 Remote Similarity NPD7004 Clinical (unspecified phase)
0.6744 Remote Similarity NPD7028 Phase 2
0.6742 Remote Similarity NPD7229 Phase 3
0.674 Remote Similarity NPD7286 Phase 2
0.6727 Remote Similarity NPD2344 Approved
0.672 Remote Similarity NPD6212 Phase 3
0.672 Remote Similarity NPD6214 Clinical (unspecified phase)
0.672 Remote Similarity NPD6213 Phase 3
0.6709 Remote Similarity NPD2798 Approved
0.6709 Remote Similarity NPD6917 Clinical (unspecified phase)
0.6707 Remote Similarity NPD3748 Approved
0.6688 Remote Similarity NPD1283 Approved
0.6687 Remote Similarity NPD4625 Phase 3
0.6667 Remote Similarity NPD5953 Discontinued
0.6667 Remote Similarity NPD1398 Phase 1
0.6667 Remote Similarity NPD5537 Clinical (unspecified phase)
0.6667 Remote Similarity NPD5403 Approved
0.6667 Remote Similarity NPD2403 Approved
0.6649 Remote Similarity NPD2493 Approved
0.6649 Remote Similarity NPD2494 Approved
0.6647 Remote Similarity NPD1243 Approved
0.6646 Remote Similarity NPD6410 Clinical (unspecified phase)
0.6646 Remote Similarity NPD4907 Clinical (unspecified phase)
0.6633 Remote Similarity NPD4583 Approved
0.6633 Remote Similarity NPD4582 Approved
0.663 Remote Similarity NPD7685 Pre-registration
0.6629 Remote Similarity NPD5760 Phase 2
0.6629 Remote Similarity NPD5761 Phase 2
0.6628 Remote Similarity NPD1653 Approved
0.6623 Remote Similarity NPD1651 Approved
0.6618 Remote Similarity NPD4111 Phase 1
0.6618 Remote Similarity NPD4665 Approved
0.6614 Remote Similarity NPD2488 Approved
0.6614 Remote Similarity NPD2490 Approved
0.6611 Remote Similarity NPD5242 Approved
0.6608 Remote Similarity NPD6273 Approved
0.6591 Remote Similarity NPD5353 Approved
0.6585 Remote Similarity NPD4097 Suspended
0.6582 Remote Similarity NPD4002 Approved
0.6582 Remote Similarity NPD6696 Suspended

Structure

External Identifiers

PubChem CID   12972110
ChEMBL   CHEMBL1813348
ZINC  

Physicochemical Properties

Molecular Weight:  346.21
ALogP:  0.2638
MLogP:  3.33
XLogP:  4.676
# Rotatable Bonds:  10
Polar Surface Area:  66.76
# H-Bond Aceptor:  1
# H-Bond Donor:  2
# Rings:  3
# Heavy Atoms:  25

Download Data

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General Info & Identifiers & Properties  
Structure MOL file  
Source Organisms  
Biological Activities  
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