Natural Product: NPC477737

Natural Product ID:  NPC477737
Common Name:   Phyllaemblic Acid Methy Ester
IUPAC Name:   methyl (2S,3aR,4R,4'S,5'R,6S,7aR)-4'-benzoyloxy-3a,4-dihydroxy-5'-methyl-3-oxospiro[5,6,7,7a-tetrahydro-4H-1-benzofuran-2,2'-oxane]-6-carboxylate
Synonyms:   Phyllaemblic Acid Methy Ester
Molecular Formula:   C22H26O9
Standard InCHIKey:  WOAOYJSNCNMIET-LMEHYVAVSA-N
Standard InCHI:  InChI=1S/C22H26O9/c1-12-11-29-21(10-15(12)30-19(25)13-6-4-3-5-7-13)20(26)22(27)16(23)8-14(18(24)28-2)9-17(22)31-21/h3-7,12,14-17,23,27H,8-11H2,1-2H3/t12-,14+,15+,16-,17-,21+,22-/m1/s1
Canonical SMILES:  COC(=O)[C@H]1C[C@@H](O)[C@]2([C@@H](C1)O[C@@]1(C2=O)OC[C@H]([C@H](C1)OC(=O)c1ccccc1)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
NPO28450 Phyllanthus emblica Species Phyllanthaceae Eukaryota Roots Simao city, Yunnan Province, China 2007-MAY PMID[19374435]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT165 Cell Line HeLa Homo sapiens CC50 = 213.6 ug/ml 19374435
NPT3494 Organism Coxsackievirus Coxsackievirus IC50 = 21.8 ug/ml 19374435
NPT2 Others Unspecified Ratio CC50/IC50 = 9.8 19374435

  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 NPC477737 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
0.9384 High Similarity NPC477735
0.932 High Similarity NPC477736
0.9214 High Similarity NPC77493
0.9172 High Similarity NPC471103
0.9048 High Similarity NPC133430
0.9048 High Similarity NPC469477
0.9041 High Similarity NPC51602
0.9007 High Similarity NPC477190
0.9007 High Similarity NPC43304
0.9007 High Similarity NPC477188
0.8986 High Similarity NPC473670
0.8986 High Similarity NPC21410
0.8958 High Similarity NPC127857
0.8947 High Similarity NPC66193
0.8926 High Similarity NPC106895
0.8904 High Similarity NPC250046
0.8904 High Similarity NPC60509
0.8904 High Similarity NPC81698
0.8889 High Similarity NPC471134
0.8867 High Similarity NPC181924
0.8867 High Similarity NPC469417
0.8859 High Similarity NPC472549
0.8859 High Similarity NPC282239
0.8844 High Similarity NPC198455
0.8844 High Similarity NPC165260
0.8844 High Similarity NPC161239
0.8844 High Similarity NPC7095
0.8839 High Similarity NPC102465
0.8831 High Similarity NPC61891
0.8828 High Similarity NPC471100
0.8828 High Similarity NPC471107
0.8808 High Similarity NPC49297
0.8808 High Similarity NPC469399
0.88 High Similarity NPC217091
0.8792 High Similarity NPC146310
0.8792 High Similarity NPC219419
0.8784 High Similarity NPC101043
0.8784 High Similarity NPC306799
0.8767 High Similarity NPC469513
0.8766 High Similarity NPC471493
0.875 High Similarity NPC182869
0.8742 High Similarity NPC472393
0.8733 High Similarity NPC259144
0.8733 High Similarity NPC114357
0.8733 High Similarity NPC155329
0.8733 High Similarity NPC5115
0.8725 High Similarity NPC477905
0.8725 High Similarity NPC472548
0.8718 High Similarity NPC40138
0.8716 High Similarity NPC112216
0.8701 High Similarity NPC329960
0.8701 High Similarity NPC150893
0.8701 High Similarity NPC295408
0.8701 High Similarity NPC322420
0.8684 High Similarity NPC471102
0.8667 High Similarity NPC304876
0.8667 High Similarity NPC472005
0.8667 High Similarity NPC472022
0.8667 High Similarity NPC11588
0.8667 High Similarity NPC472030
0.8667 High Similarity NPC248265
0.8667 High Similarity NPC249471
0.8667 High Similarity NPC473414
0.8667 High Similarity NPC242262
0.8667 High Similarity NPC237549
0.8667 High Similarity NPC257213
0.8667 High Similarity NPC158333
0.8667 High Similarity NPC265395
0.8667 High Similarity NPC1173
0.8667 High Similarity NPC229545
0.8667 High Similarity NPC256142
0.8667 High Similarity NPC134685
0.8636 High Similarity NPC275477
0.8609 High Similarity NPC114410
0.8609 High Similarity NPC26033
0.8609 High Similarity NPC251139
0.8609 High Similarity NPC112523
0.8609 High Similarity NPC228204
0.8591 High Similarity NPC470245
0.8591 High Similarity NPC473214
0.8591 High Similarity NPC91730
0.8591 High Similarity NPC254558
0.859 High Similarity NPC324769
0.859 High Similarity NPC325732
0.8571 High Similarity NPC301946
0.8571 High Similarity NPC277053
0.8553 High Similarity NPC154675
0.8552 High Similarity NPC291599
0.8552 High Similarity NPC118080
0.8552 High Similarity NPC41481
0.8552 High Similarity NPC27377
0.8552 High Similarity NPC472576
0.8552 High Similarity NPC87448
0.8552 High Similarity NPC97947
0.8544 High Similarity NPC477471
0.8544 High Similarity NPC477466
0.8544 High Similarity NPC477473
0.8544 High Similarity NPC477469
0.8543 High Similarity NPC77719
0.8533 High Similarity NPC470153
0.8533 High Similarity NPC197037
0.8526 High Similarity NPC477627
0.8523 High Similarity NPC476975
0.8523 High Similarity NPC473215
0.8503 High Similarity NPC471912
0.8503 High Similarity NPC80895
0.8497 Intermediate Similarity NPC469771
0.8493 Intermediate Similarity NPC472546
0.8487 Intermediate Similarity NPC469730
0.8487 Intermediate Similarity NPC473632
0.8487 Intermediate Similarity NPC132599
0.8483 Intermediate Similarity NPC477904
0.8483 Intermediate Similarity NPC100913
0.8483 Intermediate Similarity NPC97667
0.8483 Intermediate Similarity NPC183270
0.8483 Intermediate Similarity NPC275592
0.8483 Intermediate Similarity NPC90614
0.8483 Intermediate Similarity NPC171207
0.8483 Intermediate Similarity NPC472547
0.8467 Intermediate Similarity NPC222102
0.8467 Intermediate Similarity NPC476173
0.8467 Intermediate Similarity NPC469448
0.8467 Intermediate Similarity NPC303429
0.8456 Intermediate Similarity NPC217918
0.8435 Intermediate Similarity NPC477894
0.8431 Intermediate Similarity NPC11410
0.8429 Intermediate Similarity NPC301857
0.8425 Intermediate Similarity NPC213567
0.8425 Intermediate Similarity NPC16912
0.8421 Intermediate Similarity NPC471135
0.8411 Intermediate Similarity NPC469415
0.8389 Intermediate Similarity NPC170668
0.8378 Intermediate Similarity NPC241951
0.8378 Intermediate Similarity NPC470152
0.8378 Intermediate Similarity NPC475759
0.8366 Intermediate Similarity NPC473611
0.8366 Intermediate Similarity NPC469422
0.8366 Intermediate Similarity NPC34066
0.8366 Intermediate Similarity NPC469456
0.8365 Intermediate Similarity NPC469420
0.8345 Intermediate Similarity NPC39549
0.8333 Intermediate Similarity NPC205389
0.8333 Intermediate Similarity NPC138798
0.8322 Intermediate Similarity NPC476973
0.8322 Intermediate Similarity NPC29704
0.8322 Intermediate Similarity NPC177940
0.8322 Intermediate Similarity NPC472575
0.8322 Intermediate Similarity NPC472572
0.8322 Intermediate Similarity NPC158663
0.8322 Intermediate Similarity NPC473088
0.8322 Intermediate Similarity NPC472568
0.8322 Intermediate Similarity NPC471104
0.8322 Intermediate Similarity NPC174982
0.8322 Intermediate Similarity NPC70403
0.8322 Intermediate Similarity NPC470159
0.8322 Intermediate Similarity NPC470157
0.8322 Intermediate Similarity NPC200471
0.8322 Intermediate Similarity NPC472571
0.8322 Intermediate Similarity NPC96903
0.8322 Intermediate Similarity NPC469349
0.8322 Intermediate Similarity NPC184817
0.8322 Intermediate Similarity NPC171525
0.8313 Intermediate Similarity NPC469419
0.8312 Intermediate Similarity NPC475638
0.8312 Intermediate Similarity NPC475548
0.8312 Intermediate Similarity NPC290683
0.8311 Intermediate Similarity NPC91703
0.8311 Intermediate Similarity NPC95449
0.8311 Intermediate Similarity NPC163087
0.828 Intermediate Similarity NPC55744
0.8276 Intermediate Similarity NPC472551
0.8276 Intermediate Similarity NPC472545
0.8272 Intermediate Similarity NPC469421
0.8258 Intermediate Similarity NPC322048
0.8258 Intermediate Similarity NPC318447
0.8255 Intermediate Similarity NPC472569
0.8255 Intermediate Similarity NPC11685
0.8255 Intermediate Similarity NPC57628
0.8255 Intermediate Similarity NPC95810
0.8255 Intermediate Similarity NPC470231
0.8255 Intermediate Similarity NPC95265
0.8255 Intermediate Similarity NPC25768
0.8255 Intermediate Similarity NPC188865
0.8255 Intermediate Similarity NPC70716
0.8255 Intermediate Similarity NPC163719
0.8255 Intermediate Similarity NPC125106
0.8255 Intermediate Similarity NPC476974
0.8255 Intermediate Similarity NPC472570
0.8255 Intermediate Similarity NPC472573
0.8255 Intermediate Similarity NPC475122
0.8247 Intermediate Similarity NPC469398
0.8243 Intermediate Similarity NPC34012
0.8239 Intermediate Similarity NPC27712
0.8239 Intermediate Similarity NPC262819
0.8239 Intermediate Similarity NPC477491
0.8235 Intermediate Similarity NPC283875
0.8235 Intermediate Similarity NPC138641
0.8235 Intermediate Similarity NPC22571
0.8235 Intermediate Similarity NPC469647
0.8235 Intermediate Similarity NPC469648

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC477737 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
0.8451 Intermediate Similarity NPD7966 Clinical (unspecified phase)
0.8242 Intermediate Similarity NPD8407 Phase 2
0.8171 Intermediate Similarity NPD8368 Discontinued
0.8148 Intermediate Similarity NPD7799 Discontinued
0.7843 Intermediate Similarity NPD7236 Approved
0.7733 Intermediate Similarity NPD8435 Approved
0.7719 Intermediate Similarity NPD8434 Phase 2
0.7707 Intermediate Similarity NPD7239 Suspended
0.7688 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.7665 Intermediate Similarity NPD8470 Clinical (unspecified phase)
0.7662 Intermediate Similarity NPD6190 Approved
0.7661 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7654 Intermediate Similarity NPD7075 Discontinued
0.7644 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.763 Intermediate Similarity NPD8360 Approved
0.763 Intermediate Similarity NPD8361 Approved
0.7605 Intermediate Similarity NPD3818 Discontinued
0.7588 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.7546 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.7531 Intermediate Similarity NPD3817 Phase 2
0.7516 Intermediate Similarity NPD6801 Discontinued
0.7514 Intermediate Similarity NPD8424 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD5952 Clinical (unspecified phase)
0.7471 Intermediate Similarity NPD6797 Phase 2
0.7456 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.7452 Intermediate Similarity NPD6799 Approved
0.7444 Intermediate Similarity NPD8486 Clinical (unspecified phase)
0.7427 Intermediate Similarity NPD7251 Discontinued
0.7427 Intermediate Similarity NPD6559 Discontinued
0.7423 Intermediate Similarity NPD5402 Approved
0.7414 Intermediate Similarity NPD8150 Discontinued
0.7405 Intermediate Similarity NPD8389 Clinical (unspecified phase)
0.7391 Intermediate Similarity NPD4380 Phase 2
0.7391 Intermediate Similarity NPD6599 Discontinued
0.7384 Intermediate Similarity NPD7808 Phase 3
0.7378 Intermediate Similarity NPD7058 Phase 2
0.7378 Intermediate Similarity NPD7057 Phase 3
0.7378 Intermediate Similarity NPD3882 Suspended
0.7312 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7312 Intermediate Similarity NPD5403 Approved
0.731 Intermediate Similarity NPD7074 Phase 3
0.7296 Intermediate Similarity NPD5401 Approved
0.7294 Intermediate Similarity NPD3751 Discontinued
0.7292 Intermediate Similarity NPD5125 Phase 3
0.7292 Intermediate Similarity NPD5126 Approved
0.7283 Intermediate Similarity NPD8320 Phase 1
0.7283 Intermediate Similarity NPD8319 Approved
0.7278 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.7278 Intermediate Similarity NPD8485 Approved
0.7278 Intermediate Similarity NPD6166 Phase 2
0.7278 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.7273 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7263 Intermediate Similarity NPD6535 Approved
0.7263 Intermediate Similarity NPD6534 Approved
0.7262 Intermediate Similarity NPD3787 Discontinued
0.7261 Intermediate Similarity NPD4628 Phase 3
0.7251 Intermediate Similarity NPD7054 Approved
0.7234 Intermediate Similarity NPD2629 Approved
0.7228 Intermediate Similarity NPD7435 Discontinued
0.7225 Intermediate Similarity NPD7685 Pre-registration
0.7209 Intermediate Similarity NPD7472 Approved
0.7195 Intermediate Similarity NPD37 Approved
0.7195 Intermediate Similarity NPD1934 Approved
0.7183 Intermediate Similarity NPD4198 Discontinued
0.7181 Intermediate Similarity NPD6007 Clinical (unspecified phase)
0.7169 Intermediate Similarity NPD4965 Approved
0.7169 Intermediate Similarity NPD4967 Phase 2
0.7169 Intermediate Similarity NPD4966 Approved
0.7168 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7152 Intermediate Similarity NPD7819 Suspended
0.7152 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD5494 Approved
0.7143 Intermediate Similarity NPD7699 Phase 2
0.7143 Intermediate Similarity NPD7700 Phase 2
0.7143 Intermediate Similarity NPD8313 Approved
0.7143 Intermediate Similarity NPD8312 Approved
0.7125 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7118 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7113 Intermediate Similarity NPD690 Clinical (unspecified phase)
0.7105 Intermediate Similarity NPD8462 Phase 1
0.7083 Intermediate Similarity NPD5537 Clinical (unspecified phase)
0.7083 Intermediate Similarity NPD6234 Discontinued
0.7078 Intermediate Similarity NPD230 Phase 1
0.7071 Intermediate Similarity NPD2181 Clinical (unspecified phase)
0.707 Intermediate Similarity NPD7266 Discontinued
0.7065 Intermediate Similarity NPD6781 Approved
0.7065 Intermediate Similarity NPD6776 Approved
0.7065 Intermediate Similarity NPD6780 Approved
0.7065 Intermediate Similarity NPD6779 Approved
0.7065 Intermediate Similarity NPD6778 Approved
0.7065 Intermediate Similarity NPD6782 Approved
0.7065 Intermediate Similarity NPD6777 Approved
0.7044 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7035 Intermediate Similarity NPD7473 Discontinued
0.703 Intermediate Similarity NPD7411 Suspended
0.7 Intermediate Similarity NPD7874 Approved
0.7 Intermediate Similarity NPD7875 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD2067 Discontinued
0.7 Intermediate Similarity NPD7199 Phase 2
0.6994 Remote Similarity NPD7228 Approved
0.6993 Remote Similarity NPD3764 Approved
0.6975 Remote Similarity NPD2532 Approved
0.6975 Remote Similarity NPD4378 Clinical (unspecified phase)
0.6975 Remote Similarity NPD2534 Approved
0.6975 Remote Similarity NPD2533 Approved
0.6959 Remote Similarity NPD6232 Discontinued
0.6954 Remote Similarity NPD5844 Phase 1
0.6946 Remote Similarity NPD2801 Approved
0.6944 Remote Similarity NPD8397 Clinical (unspecified phase)
0.6932 Remote Similarity NPD6765 Approved
0.6932 Remote Similarity NPD6764 Approved
0.6918 Remote Similarity NPD1549 Phase 2
0.6909 Remote Similarity NPD7458 Discontinued
0.6901 Remote Similarity NPD969 Suspended
0.6899 Remote Similarity NPD2796 Approved
0.6882 Remote Similarity NPD919 Approved
0.6875 Remote Similarity NPD7421 Clinical (unspecified phase)
0.6872 Remote Similarity NPD8404 Phase 2
0.6862 Remote Similarity NPD7698 Approved
0.6862 Remote Similarity NPD7697 Approved
0.6862 Remote Similarity NPD7696 Phase 3
0.6859 Remote Similarity NPD6355 Discontinued
0.6855 Remote Similarity NPD1550 Clinical (unspecified phase)
0.6855 Remote Similarity NPD2346 Discontinued
0.6855 Remote Similarity NPD1552 Clinical (unspecified phase)
0.6839 Remote Similarity NPD7961 Discontinued
0.6836 Remote Similarity NPD7240 Approved
0.6835 Remote Similarity NPD1510 Phase 2
0.6835 Remote Similarity NPD7033 Discontinued
0.6835 Remote Similarity NPD5048 Discontinued
0.6832 Remote Similarity NPD2575 Approved
0.6829 Remote Similarity NPD1512 Approved
0.6825 Remote Similarity NPD7871 Phase 2
0.6825 Remote Similarity NPD7870 Phase 2
0.6824 Remote Similarity NPD3749 Approved
0.6809 Remote Similarity NPD2182 Approved
0.6807 Remote Similarity NPD6591 Clinical (unspecified phase)
0.6807 Remote Similarity NPD3226 Approved
0.6806 Remote Similarity NPD7701 Phase 2
0.6805 Remote Similarity NPD8443 Clinical (unspecified phase)
0.6803 Remote Similarity NPD9545 Approved
0.6788 Remote Similarity NPD7801 Approved
0.6778 Remote Similarity NPD6784 Approved
0.6778 Remote Similarity NPD6785 Approved
0.6774 Remote Similarity NPD6798 Discontinued
0.6774 Remote Similarity NPD2313 Discontinued
0.6768 Remote Similarity NPD7410 Clinical (unspecified phase)
0.6768 Remote Similarity NPD7004 Clinical (unspecified phase)
0.6763 Remote Similarity NPD1237 Approved
0.6752 Remote Similarity NPD1933 Approved
0.6746 Remote Similarity NPD8455 Phase 2
0.6746 Remote Similarity NPD5761 Phase 2
0.6746 Remote Similarity NPD5760 Phase 2
0.6739 Remote Similarity NPD6212 Phase 3
0.6739 Remote Similarity NPD6214 Clinical (unspecified phase)
0.6739 Remote Similarity NPD6213 Phase 3
0.6732 Remote Similarity NPD2798 Approved
0.6731 Remote Similarity NPD6233 Phase 2
0.673 Remote Similarity NPD2799 Discontinued
0.6724 Remote Similarity NPD3926 Phase 2
0.6711 Remote Similarity NPD3412 Clinical (unspecified phase)
0.6709 Remote Similarity NPD1607 Approved
0.6708 Remote Similarity NPD970 Clinical (unspecified phase)
0.6707 Remote Similarity NPD1511 Approved
0.6705 Remote Similarity NPD1247 Approved
0.6702 Remote Similarity NPD7211 Clinical (unspecified phase)
0.6688 Remote Similarity NPD1240 Approved
0.6688 Remote Similarity NPD943 Approved
0.6687 Remote Similarity NPD2354 Approved
0.6687 Remote Similarity NPD920 Approved
0.6687 Remote Similarity NPD3887 Approved
0.6687 Remote Similarity NPD2935 Discontinued
0.6686 Remote Similarity NPD7852 Clinical (unspecified phase)
0.6684 Remote Similarity NPD8151 Discontinued
0.6667 Remote Similarity NPD1609 Clinical (unspecified phase)
0.6667 Remote Similarity NPD7097 Phase 1
0.665 Remote Similarity NPD8155 Clinical (unspecified phase)
0.6647 Remote Similarity NPD1465 Phase 2
0.6646 Remote Similarity NPD2343 Clinical (unspecified phase)
0.6646 Remote Similarity NPD1471 Phase 3
0.6644 Remote Similarity NPD8515 Approved
0.6644 Remote Similarity NPD8516 Approved
0.6644 Remote Similarity NPD8517 Approved
0.6644 Remote Similarity NPD8513 Phase 3
0.6632 Remote Similarity NPD6823 Phase 2
0.6623 Remote Similarity NPD6287 Discontinued
0.6609 Remote Similarity NPD8127 Discontinued
0.6609 Remote Similarity NPD6959 Discontinued
0.6603 Remote Similarity NPD7008 Discontinued
0.6601 Remote Similarity NPD5667 Approved
0.66 Remote Similarity NPD5306 Approved
0.66 Remote Similarity NPD5305 Approved
0.6597 Remote Similarity NPD4141 Clinical (unspecified phase)
0.6594 Remote Similarity NPD1238 Approved
0.6585 Remote Similarity NPD7274 Clinical (unspecified phase)
0.6584 Remote Similarity NPD1551 Phase 2
0.6575 Remote Similarity NPD6010 Discontinued
0.6571 Remote Similarity NPD5711 Approved
0.6571 Remote Similarity NPD5710 Approved
0.6566 Remote Similarity NPD642 Clinical (unspecified phase)

Structure

External Identifiers

PubChem CID   45268813
ChEMBL   CHEMBL561362
ZINC  

Physicochemical Properties

Molecular Weight:  434.16
ALogP:  -1.7651
MLogP:  2.89
XLogP:  2.024
# Rotatable Bonds:  9
Polar Surface Area:  128.59
# H-Bond Aceptor:  9
# H-Bond Donor:  2
# Rings:  4
# Heavy Atoms:  31

Download Data

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Biological Activities  
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