Natural Product: NPC197751

Natural Product ID:  NPC197751
Common Name:   Cyathusal A
IUPAC Name:   9,10-dihydroxy-8-methoxy-1-oxo-3-[(E)-prop-1-enyl]-6H-pyrano[4,3-c]isochromene-7-carbaldehyde
Synonyms:  
Molecular Formula:   C17H14O7
Standard InCHIKey:  SHZXMBWJQUATLH-ONEGZZNKSA-N
Standard InCHI:  InChI=1S/C17H14O7/c1-3-4-8-5-11-13(17(21)24-8)12-10(7-23-11)9(6-18)16(22-2)15(20)14(12)19/h3-6,19-20H,7H2,1-2H3/b4-3+
Canonical SMILES:  C/C=C/c1cc2OCc3c(c2c(=O)o1)c(O)c(c(c3C=O)OC)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
NPO28590 Cyathus stercoreus Species Nidulariaceae Eukaryota PMID[17511503]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT2 Others Unspecified EC50 = 7860 nM 17511503
NPT1 Others Radical scavenging activity EC50 = 41590 nM 17511503

  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 NPC197751 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
0.9799 High Similarity NPC16286
0.961 High Similarity NPC317781
0.9548 High Similarity NPC327652
0.9487 High Similarity NPC329119
0.9481 High Similarity NPC474779
0.9419 High Similarity NPC474763
0.9351 High Similarity NPC315157
0.9097 High Similarity NPC227062
0.9032 High Similarity NPC82592
0.9032 High Similarity NPC16082
0.8974 High Similarity NPC150227
0.8968 High Similarity NPC281477
0.8938 High Similarity NPC191930
0.8917 High Similarity NPC77679
0.8917 High Similarity NPC84935
0.8917 High Similarity NPC190020
0.891 High Similarity NPC79998
0.891 High Similarity NPC199926
0.8903 High Similarity NPC295646
0.8896 High Similarity NPC96501
0.8875 High Similarity NPC249181
0.8827 High Similarity NPC283041
0.8824 High Similarity NPC251188
0.8805 High Similarity NPC36217
0.879 High Similarity NPC39184
0.879 High Similarity NPC38898
0.8782 High Similarity NPC199773
0.8774 High Similarity NPC31132
0.8765 High Similarity NPC20237
0.8758 High Similarity NPC186686
0.8758 High Similarity NPC260946
0.8734 High Similarity NPC54928
0.8733 High Similarity NPC187690
0.8726 High Similarity NPC192189
0.872 High Similarity NPC109827
0.872 High Similarity NPC124470
0.8718 High Similarity NPC204350
0.8718 High Similarity NPC70016
0.8718 High Similarity NPC215921
0.8718 High Similarity NPC256406
0.8716 High Similarity NPC471690
0.871 High Similarity NPC69430
0.871 High Similarity NPC264550
0.871 High Similarity NPC142876
0.871 High Similarity NPC139293
0.871 High Similarity NPC40290
0.871 High Similarity NPC264289
0.871 High Similarity NPC200060
0.871 High Similarity NPC333691
0.871 High Similarity NPC195763
0.8704 High Similarity NPC275780
0.8704 High Similarity NPC303174
0.8704 High Similarity NPC239752
0.8704 High Similarity NPC472450
0.8701 High Similarity NPC137296
0.8696 High Similarity NPC474162
0.8696 High Similarity NPC294965
0.8696 High Similarity NPC201800
0.8696 High Similarity NPC474150
0.8693 High Similarity NPC75694
0.8688 High Similarity NPC200594
0.8688 High Similarity NPC471973
0.8688 High Similarity NPC228785
0.8688 High Similarity NPC292415
0.8688 High Similarity NPC56085
0.8688 High Similarity NPC14353
0.8679 High Similarity NPC136674
0.8679 High Similarity NPC222689
0.8679 High Similarity NPC302258
0.8679 High Similarity NPC178976
0.8679 High Similarity NPC35598
0.8675 High Similarity NPC139350
0.8671 High Similarity NPC134287
0.8671 High Similarity NPC130589
0.8671 High Similarity NPC20541
0.8662 High Similarity NPC471982
0.8662 High Similarity NPC209487
0.8662 High Similarity NPC131266
0.8662 High Similarity NPC216769
0.8662 High Similarity NPC100263
0.8662 High Similarity NPC245382
0.8662 High Similarity NPC180388
0.8662 High Similarity NPC181209
0.8662 High Similarity NPC35763
0.8662 High Similarity NPC100971
0.8662 High Similarity NPC121522
0.8662 High Similarity NPC269451
0.8662 High Similarity NPC291802
0.8659 High Similarity NPC163130
0.8659 High Similarity NPC165979
0.8659 High Similarity NPC26568
0.8654 High Similarity NPC85131
0.865 High Similarity NPC472452
0.865 High Similarity NPC39091
0.865 High Similarity NPC43319
0.8645 High Similarity NPC254702
0.8645 High Similarity NPC80710
0.8645 High Similarity NPC194653
0.8645 High Similarity NPC139364
0.8645 High Similarity NPC203747
0.8642 High Similarity NPC7483
0.8642 High Similarity NPC234004
0.8642 High Similarity NPC270837
0.8642 High Similarity NPC470772
0.8642 High Similarity NPC220313
0.8642 High Similarity NPC474350
0.8642 High Similarity NPC23298
0.8642 High Similarity NPC189473
0.8642 High Similarity NPC101769
0.8636 High Similarity NPC32058
0.8636 High Similarity NPC85734
0.8636 High Similarity NPC138978
0.8634 High Similarity NPC349525
0.8634 High Similarity NPC40491
0.8634 High Similarity NPC311740
0.8634 High Similarity NPC473106
0.8634 High Similarity NPC61010
0.8634 High Similarity NPC474187
0.8634 High Similarity NPC278052
0.8634 High Similarity NPC103201
0.8631 High Similarity NPC113446
0.8627 High Similarity NPC257025
0.8625 High Similarity NPC235448
0.8625 High Similarity NPC95936
0.8625 High Similarity NPC210459
0.8625 High Similarity NPC100123
0.8625 High Similarity NPC470339
0.8625 High Similarity NPC74178
0.8625 High Similarity NPC250214
0.8625 High Similarity NPC184755
0.8625 High Similarity NPC45846
0.8618 High Similarity NPC299154
0.8618 High Similarity NPC82913
0.8618 High Similarity NPC314271
0.8616 High Similarity NPC14561
0.8616 High Similarity NPC472455
0.8616 High Similarity NPC195796
0.8616 High Similarity NPC291878
0.8616 High Similarity NPC5379
0.8616 High Similarity NPC278778
0.8616 High Similarity NPC35038
0.8616 High Similarity NPC471985
0.8616 High Similarity NPC77807
0.8614 High Similarity NPC233956
0.8614 High Similarity NPC181523
0.8608 High Similarity NPC144801
0.8608 High Similarity NPC291510
0.8608 High Similarity NPC116850
0.8608 High Similarity NPC197188
0.8608 High Similarity NPC238672
0.8608 High Similarity NPC43872
0.8608 High Similarity NPC298802
0.8608 High Similarity NPC93552
0.8608 High Similarity NPC124714
0.8606 High Similarity NPC20543
0.8606 High Similarity NPC246716
0.8606 High Similarity NPC239440
0.8606 High Similarity NPC1827
0.8606 High Similarity NPC10576
0.8599 High Similarity NPC19980
0.8599 High Similarity NPC200773
0.8599 High Similarity NPC240768
0.8599 High Similarity NPC45291
0.8598 High Similarity NPC218226
0.8598 High Similarity NPC272485
0.8598 High Similarity NPC234331
0.8598 High Similarity NPC471288
0.8598 High Similarity NPC292788
0.859 High Similarity NPC137062
0.859 High Similarity NPC183950
0.859 High Similarity NPC171916
0.859 High Similarity NPC287101
0.859 High Similarity NPC223579
0.859 High Similarity NPC52005
0.859 High Similarity NPC38545
0.8589 High Similarity NPC85057
0.8589 High Similarity NPC326520
0.8589 High Similarity NPC471788
0.8589 High Similarity NPC293319
0.8589 High Similarity NPC130920
0.8589 High Similarity NPC470773
0.8581 High Similarity NPC8817
0.8581 High Similarity NPC476463
0.8581 High Similarity NPC125449
0.8581 High Similarity NPC188074
0.858 High Similarity NPC261470
0.858 High Similarity NPC8300
0.858 High Similarity NPC229632
0.8571 High Similarity NPC84571
0.8571 High Similarity NPC474287
0.8571 High Similarity NPC472055
0.8571 High Similarity NPC321399
0.8571 High Similarity NPC476980
0.8571 High Similarity NPC139036
0.8571 High Similarity NPC24627
0.8571 High Similarity NPC299436
0.8571 High Similarity NPC118256
0.8571 High Similarity NPC475886
0.8571 High Similarity NPC474960
0.8571 High Similarity NPC119209

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC197751 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
0.8696 High Similarity NPD6232 Discontinued
0.8693 High Similarity NPD2533 Approved
0.8693 High Similarity NPD2532 Approved
0.8693 High Similarity NPD2534 Approved
0.8544 High Similarity NPD1934 Approved
0.8537 High Similarity NPD7473 Discontinued
0.8491 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.8491 Intermediate Similarity NPD2801 Approved
0.8421 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.8323 Intermediate Similarity NPD3817 Phase 2
0.8269 Intermediate Similarity NPD1511 Approved
0.8165 Intermediate Similarity NPD1512 Approved
0.816 Intermediate Similarity NPD3882 Suspended
0.816 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.8155 Intermediate Similarity NPD3818 Discontinued
0.8148 Intermediate Similarity NPD1465 Phase 2
0.8148 Intermediate Similarity NPD7819 Suspended
0.8107 Intermediate Similarity NPD5844 Phase 1
0.8075 Intermediate Similarity NPD4380 Phase 2
0.8061 Intermediate Similarity NPD919 Approved
0.8036 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.8036 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.8036 Intermediate Similarity NPD6166 Phase 2
0.8026 Intermediate Similarity NPD230 Phase 1
0.8024 Intermediate Similarity NPD5711 Approved
0.8024 Intermediate Similarity NPD5710 Approved
0.8023 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.8 Intermediate Similarity NPD7054 Approved
0.8 Intermediate Similarity NPD7075 Discontinued
0.7987 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.7953 Intermediate Similarity NPD7472 Approved
0.7953 Intermediate Similarity NPD7074 Phase 3
0.7927 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.7904 Intermediate Similarity NPD5494 Approved
0.7898 Intermediate Similarity NPD2800 Approved
0.7871 Intermediate Similarity NPD1510 Phase 2
0.7866 Intermediate Similarity NPD6801 Discontinued
0.7857 Intermediate Similarity NPD1247 Approved
0.7844 Intermediate Similarity NPD6234 Discontinued
0.7803 Intermediate Similarity NPD6797 Phase 2
0.7778 Intermediate Similarity NPD920 Approved
0.7759 Intermediate Similarity NPD7251 Discontinued
0.7753 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7736 Intermediate Similarity NPD3750 Approved
0.7714 Intermediate Similarity NPD7808 Phase 3
0.7707 Intermediate Similarity NPD2935 Discontinued
0.7702 Intermediate Similarity NPD6799 Approved
0.7697 Intermediate Similarity NPD7411 Suspended
0.7679 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.7677 Intermediate Similarity NPD447 Suspended
0.7665 Intermediate Similarity NPD5402 Approved
0.7658 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.7658 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.7657 Intermediate Similarity NPD6559 Discontinued
0.7654 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.7654 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7651 Intermediate Similarity NPD37 Approved
0.7647 Intermediate Similarity NPD6959 Discontinued
0.7643 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.7636 Intermediate Similarity NPD6599 Discontinued
0.7632 Intermediate Similarity NPD9494 Approved
0.7625 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7619 Intermediate Similarity NPD4965 Approved
0.7619 Intermediate Similarity NPD4967 Phase 2
0.7619 Intermediate Similarity NPD4966 Approved
0.7619 Intermediate Similarity NPD7768 Phase 2
0.7613 Intermediate Similarity NPD943 Approved
0.7613 Intermediate Similarity NPD1240 Approved
0.761 Intermediate Similarity NPD1549 Phase 2
0.76 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7595 Intermediate Similarity NPD1551 Phase 2
0.7586 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.7576 Intermediate Similarity NPD3226 Approved
0.7574 Intermediate Similarity NPD3749 Approved
0.756 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.7547 Intermediate Similarity NPD2346 Discontinued
0.7546 Intermediate Similarity NPD7422 Clinical (unspecified phase)
0.7544 Intermediate Similarity NPD7199 Phase 2
0.7531 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.7529 Intermediate Similarity NPD7228 Approved
0.7516 Intermediate Similarity NPD6651 Approved
0.7516 Intermediate Similarity NPD1607 Approved
0.7514 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.7484 Intermediate Similarity NPD2796 Approved
0.7473 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7457 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7455 Intermediate Similarity NPD5403 Approved
0.7455 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7439 Intermediate Similarity NPD5401 Approved
0.7421 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.7421 Intermediate Similarity NPD3748 Approved
0.7389 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7378 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7372 Intermediate Similarity NPD2313 Discontinued
0.7346 Intermediate Similarity NPD1243 Approved
0.7346 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7342 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.7342 Intermediate Similarity NPD5124 Phase 1
0.7308 Intermediate Similarity NPD3027 Phase 3
0.7305 Intermediate Similarity NPD1653 Approved
0.7303 Intermediate Similarity NPD9269 Phase 2
0.7301 Intermediate Similarity NPD4628 Phase 3
0.7287 Intermediate Similarity NPD7501 Clinical (unspecified phase)
0.7278 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7278 Intermediate Similarity NPD1613 Approved
0.7263 Intermediate Similarity NPD7685 Pre-registration
0.7261 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7257 Intermediate Similarity NPD3926 Phase 2
0.7257 Intermediate Similarity NPD5242 Approved
0.7256 Intermediate Similarity NPD6190 Approved
0.7244 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7207 Intermediate Similarity NPD5953 Discontinued
0.7205 Intermediate Similarity NPD2799 Discontinued
0.72 Intermediate Similarity NPD7229 Phase 3
0.7195 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7191 Intermediate Similarity NPD7286 Phase 2
0.7182 Intermediate Similarity NPD8313 Approved
0.7182 Intermediate Similarity NPD8312 Approved
0.7179 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7169 Intermediate Similarity NPD7390 Discontinued
0.7165 Intermediate Similarity NPD8151 Discontinued
0.716 Intermediate Similarity NPD5405 Approved
0.716 Intermediate Similarity NPD5406 Approved
0.716 Intermediate Similarity NPD5408 Approved
0.716 Intermediate Similarity NPD5404 Approved
0.7158 Intermediate Similarity NPD8434 Phase 2
0.7158 Intermediate Similarity NPD8150 Discontinued
0.7151 Intermediate Similarity NPD5353 Approved
0.7135 Intermediate Similarity NPD3751 Discontinued
0.7125 Intermediate Similarity NPD1933 Approved
0.7083 Intermediate Similarity NPD7435 Discontinued
0.7072 Intermediate Similarity NPD7240 Approved
0.7063 Intermediate Similarity NPD4060 Phase 1
0.7049 Intermediate Similarity NPD7090 Clinical (unspecified phase)
0.7044 Intermediate Similarity NPD1699 Clinical (unspecified phase)
0.7044 Intermediate Similarity NPD3764 Approved
0.7039 Intermediate Similarity NPD9268 Approved
0.7033 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.7016 Intermediate Similarity NPD6778 Approved
0.7016 Intermediate Similarity NPD6782 Approved
0.7016 Intermediate Similarity NPD6780 Approved
0.7016 Intermediate Similarity NPD6777 Approved
0.7016 Intermediate Similarity NPD6776 Approved
0.7016 Intermediate Similarity NPD6779 Approved
0.7016 Intermediate Similarity NPD6781 Approved
0.7013 Intermediate Similarity NPD422 Phase 1
0.7012 Intermediate Similarity NPD2343 Clinical (unspecified phase)
0.7006 Intermediate Similarity NPD3787 Discontinued
0.6977 Remote Similarity NPD6386 Approved
0.6977 Remote Similarity NPD6385 Approved
0.6974 Remote Similarity NPD9545 Approved
0.6968 Remote Similarity NPD9717 Approved
0.6959 Remote Similarity NPD7458 Discontinued
0.6959 Remote Similarity NPD5808 Clinical (unspecified phase)
0.6954 Remote Similarity NPD4288 Approved
0.6951 Remote Similarity NPD6100 Approved
0.6951 Remote Similarity NPD6099 Approved
0.6947 Remote Similarity NPD8090 Clinical (unspecified phase)
0.6943 Remote Similarity NPD1203 Approved
0.6928 Remote Similarity NPD6674 Discontinued
0.6919 Remote Similarity NPD7782 Clinical (unspecified phase)
0.6919 Remote Similarity NPD7783 Phase 2
0.6914 Remote Similarity NPD1899 Clinical (unspecified phase)
0.6909 Remote Similarity NPD2344 Approved
0.689 Remote Similarity NPD7033 Discontinued
0.6886 Remote Similarity NPD7003 Approved
0.6886 Remote Similarity NPD8166 Discontinued
0.6883 Remote Similarity NPD4626 Approved
0.6879 Remote Similarity NPD7615 Clinical (unspecified phase)
0.6879 Remote Similarity NPD1283 Approved
0.6869 Remote Similarity NPD7875 Clinical (unspecified phase)
0.6869 Remote Similarity NPD7874 Approved
0.6859 Remote Similarity NPD1608 Approved
0.6856 Remote Similarity NPD5005 Approved
0.6856 Remote Similarity NPD5006 Approved
0.6854 Remote Similarity NPD8127 Discontinued
0.6842 Remote Similarity NPD6534 Approved
0.6842 Remote Similarity NPD9493 Approved
0.6842 Remote Similarity NPD6535 Approved
0.6836 Remote Similarity NPD5537 Clinical (unspecified phase)
0.6835 Remote Similarity NPD2797 Approved
0.6835 Remote Similarity NPD1470 Approved
0.6832 Remote Similarity NPD4907 Clinical (unspecified phase)
0.6832 Remote Similarity NPD411 Approved
0.6832 Remote Similarity NPD3268 Approved
0.6826 Remote Similarity NPD1652 Phase 2
0.6824 Remote Similarity NPD7004 Clinical (unspecified phase)
0.6821 Remote Similarity NPD7698 Approved
0.6821 Remote Similarity NPD7697 Approved
0.6821 Remote Similarity NPD7696 Phase 3
0.6818 Remote Similarity NPD5691 Approved
0.6815 Remote Similarity NPD4379 Clinical (unspecified phase)
0.6813 Remote Similarity NPD6832 Phase 2
0.6809 Remote Similarity NPD4287 Approved
0.6795 Remote Similarity NPD1201 Approved
0.6792 Remote Similarity NPD2798 Approved
0.6788 Remote Similarity NPD4308 Phase 3
0.6788 Remote Similarity NPD7237 Clinical (unspecified phase)
0.6786 Remote Similarity NPD7871 Phase 2
0.6786 Remote Similarity NPD7870 Phase 2

Structure

External Identifiers

PubChem CID   16737098
ChEMBL   CHEMBL375925
ZINC  

Physicochemical Properties

Molecular Weight:  330.07
ALogP:  -0.6447
MLogP:  2.56
XLogP:  1.193
# Rotatable Bonds:  7
Polar Surface Area:  102.29
# H-Bond Aceptor:  4
# H-Bond Donor:  2
# Rings:  3
# Heavy Atoms:  24

Download Data

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General Info & Identifiers & Properties  
Structure MOL file  
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Biological Activities  
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