Natural Product: NPC477691

Natural Product ID:  NPC477691
Common Name:   Busseihydroquinone C
IUPAC Name:   7-hydroxy-10-methoxy-3-methyl-3-(4-methylpent-3-enyl)benzo[f]chromene-8-carboxylic acid
Synonyms:   Busseihydroquinone C
Molecular Formula:   C22H24O5
Standard InCHIKey:  MPFRBGNULMTVEA-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C22H24O5/c1-13(2)6-5-10-22(3)11-9-14-17(27-22)8-7-15-19(14)18(26-4)12-16(20(15)23)21(24)25/h6-9,11-12,23H,5,10H2,1-4H3,(H,24,25)
Canonical SMILES:  COc1cc(C(=O)O)c(c2c1c1C=CC(Oc1cc2)(C)CCC=C(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
NPO33631 Pentas bussei Species Rubiaceae Eukaryota Roots Mombasa, coastal region of Kenya 2010-JUL PMID[22709138]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT6 Organism Plasmodium falciparum Plasmodium falciparum IC50 = 32650 nM 22709138
NPT6 Organism Plasmodium falciparum Plasmodium falciparum IC50 = 60080 nM 22709138
NPT83 Cell Line MCF7 Homo sapiens LD50 > 271.62 nM 22709138

  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 NPC477691 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 NPC477690
0.9603 High Similarity NPC477692
0.9521 High Similarity NPC60389
0.9481 High Similarity NPC477689
0.9388 High Similarity NPC211565
0.9272 High Similarity NPC175978
0.9156 High Similarity NPC44199
0.9145 High Similarity NPC217447
0.9085 High Similarity NPC135522
0.9057 High Similarity NPC76647
0.9007 High Similarity NPC37139
0.8968 High Similarity NPC146211
0.8961 High Similarity NPC280530
0.8961 High Similarity NPC169990
0.8961 High Similarity NPC95842
0.8961 High Similarity NPC210942
0.8961 High Similarity NPC178964
0.8961 High Similarity NPC329844
0.8947 High Similarity NPC97028
0.8947 High Similarity NPC233267
0.8947 High Similarity NPC288036
0.8947 High Similarity NPC65589
0.8947 High Similarity NPC97029
0.8947 High Similarity NPC10027
0.8947 High Similarity NPC158338
0.8947 High Similarity NPC65775
0.8947 High Similarity NPC100985
0.8947 High Similarity NPC70764
0.8947 High Similarity NPC291049
0.8917 High Similarity NPC143050
0.891 High Similarity NPC263483
0.8896 High Similarity NPC281272
0.8896 High Similarity NPC273483
0.8896 High Similarity NPC271681
0.8889 High Similarity NPC295036
0.8889 High Similarity NPC158866
0.8889 High Similarity NPC227122
0.8882 High Similarity NPC27221
0.8882 High Similarity NPC256672
0.8882 High Similarity NPC105415
0.8882 High Similarity NPC7025
0.8875 High Similarity NPC30027
0.8874 High Similarity NPC163846
0.8874 High Similarity NPC225173
0.8861 High Similarity NPC66288
0.8854 High Similarity NPC186113
0.8854 High Similarity NPC474373
0.8831 High Similarity NPC258249
0.8831 High Similarity NPC39819
0.8831 High Similarity NPC474417
0.8831 High Similarity NPC133856
0.8831 High Similarity NPC149526
0.8827 High Similarity NPC109827
0.8827 High Similarity NPC124470
0.8824 High Similarity NPC266499
0.882 High Similarity NPC234331
0.8816 High Similarity NPC125801
0.8816 High Similarity NPC22005
0.8816 High Similarity NPC7943
0.8816 High Similarity NPC123202
0.8805 High Similarity NPC473961
0.8797 High Similarity NPC47623
0.8792 High Similarity NPC124365
0.879 High Similarity NPC164110
0.879 High Similarity NPC212967
0.879 High Similarity NPC246647
0.879 High Similarity NPC268360
0.879 High Similarity NPC96342
0.8782 High Similarity NPC166054
0.8782 High Similarity NPC66029
0.8782 High Similarity NPC55662
0.8774 High Similarity NPC40356
0.8774 High Similarity NPC154683
0.8766 High Similarity NPC294646
0.8766 High Similarity NPC120105
0.8766 High Similarity NPC150928
0.8766 High Similarity NPC101957
0.8766 High Similarity NPC470107
0.8766 High Similarity NPC119929
0.8765 High Similarity NPC99613
0.8765 High Similarity NPC49487
0.8758 High Similarity NPC37135
0.8758 High Similarity NPC186397
0.8758 High Similarity NPC172329
0.8758 High Similarity NPC29160
0.8758 High Similarity NPC5537
0.8758 High Similarity NPC2569
0.875 High Similarity NPC207690
0.875 High Similarity NPC300540
0.875 High Similarity NPC270837
0.8742 High Similarity NPC274085
0.8742 High Similarity NPC89664
0.8742 High Similarity NPC24761
0.8726 High Similarity NPC180924
0.8726 High Similarity NPC474360
0.8725 High Similarity NPC168471
0.8718 High Similarity NPC472799
0.8712 High Similarity NPC313304
0.8712 High Similarity NPC241874
0.871 High Similarity NPC478148
0.871 High Similarity NPC72958
0.871 High Similarity NPC232645
0.8701 High Similarity NPC329933
0.8701 High Similarity NPC223988
0.8693 High Similarity NPC71055
0.8693 High Similarity NPC34802
0.8688 High Similarity NPC144843
0.8688 High Similarity NPC294965
0.8688 High Similarity NPC329760
0.8688 High Similarity NPC229632
0.8684 High Similarity NPC134621
0.8684 High Similarity NPC469953
0.8684 High Similarity NPC311741
0.8684 High Similarity NPC234629
0.8675 High Similarity NPC476473
0.8671 High Similarity NPC67197
0.8671 High Similarity NPC476981
0.8667 High Similarity NPC470454
0.8667 High Similarity NPC199533
0.8662 High Similarity NPC148938
0.8662 High Similarity NPC149618
0.8662 High Similarity NPC99199
0.8662 High Similarity NPC89625
0.8659 High Similarity NPC158226
0.8658 High Similarity NPC1268
0.8654 High Similarity NPC87708
0.8654 High Similarity NPC474843
0.865 High Similarity NPC165979
0.865 High Similarity NPC163130
0.8645 High Similarity NPC325983
0.8645 High Similarity NPC37348
0.8645 High Similarity NPC202595
0.8645 High Similarity NPC13282
0.8645 High Similarity NPC474660
0.8645 High Similarity NPC205766
0.8642 High Similarity NPC37870
0.8634 High Similarity NPC474350
0.8634 High Similarity NPC156082
0.8634 High Similarity NPC197168
0.8627 High Similarity NPC469758
0.8627 High Similarity NPC267509
0.8627 High Similarity NPC237208
0.8627 High Similarity NPC196114
0.8627 High Similarity NPC473927
0.8618 High Similarity NPC95123
0.8618 High Similarity NPC189650
0.8618 High Similarity NPC66404
0.8618 High Similarity NPC260152
0.8618 High Similarity NPC295696
0.8618 High Similarity NPC71739
0.8618 High Similarity NPC471305
0.8616 High Similarity NPC45846
0.8609 High Similarity NPC250755
0.8609 High Similarity NPC474300
0.8608 High Similarity NPC4547
0.8606 High Similarity NPC181523
0.86 High Similarity NPC183642
0.86 High Similarity NPC310370
0.8599 High Similarity NPC472462
0.8599 High Similarity NPC235333
0.8599 High Similarity NPC214632
0.8599 High Similarity NPC72370
0.8589 High Similarity NPC473094
0.8589 High Similarity NPC225419
0.8581 High Similarity NPC269420
0.8581 High Similarity NPC474052
0.8581 High Similarity NPC115861
0.858 High Similarity NPC239752
0.858 High Similarity NPC472450
0.858 High Similarity NPC112981
0.858 High Similarity NPC275780
0.858 High Similarity NPC25361
0.8571 High Similarity NPC137296
0.8571 High Similarity NPC472402
0.8571 High Similarity NPC118027
0.8571 High Similarity NPC56433
0.8571 High Similarity NPC312929
0.8571 High Similarity NPC190648
0.8571 High Similarity NPC245584
0.8571 High Similarity NPC126767
0.8571 High Similarity NPC470694
0.8571 High Similarity NPC289042
0.8562 High Similarity NPC469764
0.8562 High Similarity NPC29577
0.8562 High Similarity NPC476980
0.8562 High Similarity NPC470810
0.8562 High Similarity NPC284495
0.8562 High Similarity NPC32470
0.8562 High Similarity NPC119224
0.8562 High Similarity NPC478019
0.8562 High Similarity NPC186325
0.8562 High Similarity NPC131766
0.8554 High Similarity NPC289147
0.8553 High Similarity NPC158542
0.8553 High Similarity NPC226636
0.8553 High Similarity NPC84266
0.8553 High Similarity NPC165977
0.8553 High Similarity NPC196448
0.8553 High Similarity NPC11561
0.8553 High Similarity NPC217677

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC477691 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
0.8904 High Similarity NPD2935 Discontinued
0.8716 High Similarity NPD2346 Discontinued
0.8701 High Similarity NPD3226 Approved
0.8599 High Similarity NPD7819 Suspended
0.8571 High Similarity NPD6232 Discontinued
0.8442 Intermediate Similarity NPD2532 Approved
0.8442 Intermediate Similarity NPD2533 Approved
0.8442 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.8442 Intermediate Similarity NPD2534 Approved
0.8424 Intermediate Similarity NPD5844 Phase 1
0.8421 Intermediate Similarity NPD3750 Approved
0.8415 Intermediate Similarity NPD7473 Discontinued
0.8375 Intermediate Similarity NPD7768 Phase 2
0.8333 Intermediate Similarity NPD2799 Discontinued
0.8299 Intermediate Similarity NPD2313 Discontinued
0.8289 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.8282 Intermediate Similarity NPD6959 Discontinued
0.8278 Intermediate Similarity NPD5406 Approved
0.8278 Intermediate Similarity NPD5408 Approved
0.8278 Intermediate Similarity NPD5405 Approved
0.8278 Intermediate Similarity NPD5404 Approved
0.825 Intermediate Similarity NPD2801 Approved
0.8228 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.821 Intermediate Similarity NPD3749 Approved
0.8205 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.8158 Intermediate Similarity NPD1551 Phase 2
0.8137 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.8125 Intermediate Similarity NPD7411 Suspended
0.8117 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.8098 Intermediate Similarity NPD7075 Discontinued
0.8092 Intermediate Similarity NPD3748 Approved
0.8092 Intermediate Similarity NPD4308 Phase 3
0.8086 Intermediate Similarity NPD5402 Approved
0.8065 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.8065 Intermediate Similarity NPD7003 Approved
0.8059 Intermediate Similarity NPD6559 Discontinued
0.8057 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.8046 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.8025 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.8024 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.7974 Intermediate Similarity NPD1510 Phase 2
0.7965 Intermediate Similarity NPD8313 Approved
0.7965 Intermediate Similarity NPD8312 Approved
0.7963 Intermediate Similarity NPD6801 Discontinued
0.7961 Intermediate Similarity NPD1607 Approved
0.7959 Intermediate Similarity NPD1203 Approved
0.795 Intermediate Similarity NPD4380 Phase 2
0.795 Intermediate Similarity NPD6599 Discontinued
0.7949 Intermediate Similarity NPD4628 Phase 3
0.7935 Intermediate Similarity NPD1549 Phase 2
0.7933 Intermediate Similarity NPD3764 Approved
0.7922 Intermediate Similarity NPD2796 Approved
0.7911 Intermediate Similarity NPD1511 Approved
0.7892 Intermediate Similarity NPD5494 Approved
0.7891 Intermediate Similarity NPD1283 Approved
0.7875 Intermediate Similarity NPD920 Approved
0.7871 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.7871 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.7867 Intermediate Similarity NPD4625 Phase 3
0.7866 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.7866 Intermediate Similarity NPD3817 Phase 2
0.7857 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.7853 Intermediate Similarity NPD1934 Approved
0.7838 Intermediate Similarity NPD2797 Approved
0.7829 Intermediate Similarity NPD1240 Approved
0.7829 Intermediate Similarity NPD4307 Phase 2
0.7818 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7815 Intermediate Similarity NPD1699 Clinical (unspecified phase)
0.7815 Intermediate Similarity NPD411 Approved
0.7812 Intermediate Similarity NPD1512 Approved
0.7805 Intermediate Similarity NPD1465 Phase 2
0.78 Intermediate Similarity NPD6832 Phase 2
0.7799 Intermediate Similarity NPD6799 Approved
0.7798 Intermediate Similarity NPD5710 Approved
0.7798 Intermediate Similarity NPD5711 Approved
0.7778 Intermediate Similarity NPD447 Suspended
0.7778 Intermediate Similarity NPD1899 Clinical (unspecified phase)
0.7771 Intermediate Similarity NPD1243 Approved
0.7771 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.7756 Intermediate Similarity NPD2344 Approved
0.7755 Intermediate Similarity NPD9717 Approved
0.775 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.775 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7722 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7719 Intermediate Similarity NPD7177 Discontinued
0.7719 Intermediate Similarity NPD3818 Discontinued
0.7718 Intermediate Similarity NPD1470 Approved
0.7712 Intermediate Similarity NPD2979 Phase 3
0.7711 Intermediate Similarity NPD3882 Suspended
0.7702 Intermediate Similarity NPD6273 Approved
0.7701 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.7697 Intermediate Similarity NPD3268 Approved
0.7688 Intermediate Similarity NPD7390 Discontinued
0.7687 Intermediate Similarity NPD1281 Approved
0.7687 Intermediate Similarity NPD1611 Approved
0.7671 Intermediate Similarity NPD4626 Approved
0.7667 Intermediate Similarity NPD2798 Approved
0.7658 Intermediate Similarity NPD2800 Approved
0.7654 Intermediate Similarity NPD5403 Approved
0.7643 Intermediate Similarity NPD2343 Clinical (unspecified phase)
0.7628 Intermediate Similarity NPD7033 Discontinued
0.7627 Intermediate Similarity NPD8150 Discontinued
0.7625 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.7622 Intermediate Similarity NPD7435 Discontinued
0.7619 Intermediate Similarity NPD7783 Phase 2
0.7619 Intermediate Similarity NPD7782 Clinical (unspecified phase)
0.76 Intermediate Similarity NPD1164 Approved
0.7597 Intermediate Similarity NPD4060 Phase 1
0.7588 Intermediate Similarity NPD7229 Phase 3
0.7586 Intermediate Similarity NPD5953 Discontinued
0.7582 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.758 Intermediate Similarity NPD6099 Approved
0.758 Intermediate Similarity NPD6100 Approved
0.7572 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.7572 Intermediate Similarity NPD7286 Phase 2
0.7568 Intermediate Similarity NPD1201 Approved
0.7562 Intermediate Similarity NPD2309 Approved
0.7554 Intermediate Similarity NPD6777 Approved
0.7554 Intermediate Similarity NPD6776 Approved
0.7554 Intermediate Similarity NPD6780 Approved
0.7554 Intermediate Similarity NPD6778 Approved
0.7554 Intermediate Similarity NPD6782 Approved
0.7554 Intermediate Similarity NPD6779 Approved
0.7554 Intermediate Similarity NPD6781 Approved
0.7545 Intermediate Similarity NPD4288 Approved
0.7531 Intermediate Similarity NPD5401 Approved
0.7531 Intermediate Similarity NPD7422 Clinical (unspecified phase)
0.7529 Intermediate Similarity NPD1247 Approved
0.7517 Intermediate Similarity NPD1608 Approved
0.7515 Intermediate Similarity NPD919 Approved
0.75 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD6166 Phase 2
0.7483 Intermediate Similarity NPD5691 Approved
0.7483 Intermediate Similarity NPD1651 Approved
0.7473 Intermediate Similarity NPD6823 Phase 2
0.7471 Intermediate Similarity NPD7054 Approved
0.7468 Intermediate Similarity NPD2438 Suspended
0.7468 Intermediate Similarity NPD4476 Approved
0.7468 Intermediate Similarity NPD4477 Approved
0.7455 Intermediate Similarity NPD7458 Discontinued
0.7436 Intermediate Similarity NPD1933 Approved
0.7433 Intermediate Similarity NPD7698 Approved
0.7433 Intermediate Similarity NPD7696 Phase 3
0.7433 Intermediate Similarity NPD7697 Approved
0.743 Intermediate Similarity NPD8434 Phase 2
0.7429 Intermediate Similarity NPD7074 Phase 3
0.7429 Intermediate Similarity NPD7472 Approved
0.7425 Intermediate Similarity NPD37 Approved
0.7425 Intermediate Similarity NPD6844 Discontinued
0.7417 Intermediate Similarity NPD3225 Approved
0.7417 Intermediate Similarity NPD6696 Suspended
0.7414 Intermediate Similarity NPD3751 Discontinued
0.7414 Intermediate Similarity NPD7893 Clinical (unspecified phase)
0.7412 Intermediate Similarity NPD6234 Discontinued
0.74 Intermediate Similarity NPD1481 Phase 2
0.7397 Intermediate Similarity NPD9493 Approved
0.7396 Intermediate Similarity NPD4966 Approved
0.7396 Intermediate Similarity NPD4967 Phase 2
0.7396 Intermediate Similarity NPD4965 Approved
0.7394 Intermediate Similarity NPD7870 Phase 2
0.7394 Intermediate Similarity NPD7871 Phase 2
0.7386 Intermediate Similarity NPD6797 Phase 2
0.7386 Intermediate Similarity NPD2861 Phase 2
0.7382 Intermediate Similarity NPD7875 Clinical (unspecified phase)
0.7382 Intermediate Similarity NPD7874 Approved
0.7368 Intermediate Similarity NPD3267 Approved
0.7368 Intermediate Similarity NPD3266 Approved
0.7365 Intermediate Similarity NPD7615 Clinical (unspecified phase)
0.7358 Intermediate Similarity NPD2531 Phase 2
0.7355 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7345 Intermediate Similarity NPD7251 Discontinued
0.7333 Intermediate Similarity NPD422 Phase 1
0.7333 Intermediate Similarity NPD1535 Discovery
0.7333 Intermediate Similarity NPD1547 Clinical (unspecified phase)
0.7329 Intermediate Similarity NPD5698 Clinical (unspecified phase)
0.7325 Intermediate Similarity NPD5124 Phase 1
0.7325 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.732 Intermediate Similarity NPD1019 Discontinued
0.7315 Intermediate Similarity NPD17 Approved
0.7312 Intermediate Similarity NPD1471 Phase 3
0.7308 Intermediate Similarity NPD6233 Phase 2
0.7303 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.7303 Intermediate Similarity NPD7808 Phase 3
0.7289 Intermediate Similarity NPD2370 Clinical (unspecified phase)
0.7288 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7283 Intermediate Similarity NPD3787 Discontinued
0.7283 Intermediate Similarity NPD6534 Approved
0.7283 Intermediate Similarity NPD6535 Approved
0.7278 Intermediate Similarity NPD5761 Phase 2
0.7278 Intermediate Similarity NPD5760 Phase 2
0.7278 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7278 Intermediate Similarity NPD8455 Phase 2
0.7277 Intermediate Similarity NPD7701 Phase 2
0.7267 Intermediate Similarity NPD3496 Discontinued
0.7256 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7253 Intermediate Similarity NPD4287 Approved
0.7244 Intermediate Similarity NPD6798 Discontinued
0.7241 Intermediate Similarity NPD3926 Phase 2
0.724 Intermediate Similarity NPD8151 Discontinued

Structure

External Identifiers

PubChem CID   60201022
ChEMBL   CHEMBL2071295
ZINC  

Physicochemical Properties

Molecular Weight:  368.16
ALogP:  1.7838
MLogP:  3.33
XLogP:  4.794
# Rotatable Bonds:  11
Polar Surface Area:  75.99
# H-Bond Aceptor:  2
# H-Bond Donor:  2
# Rings:  3
# Heavy Atoms:  27

Download Data

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General Info & Identifiers & Properties  
Structure MOL file  
Source Organisms  
Biological Activities  
Similar NPs/Drugs