Natural Product: NPC297985

Natural Product ID:  NPC297985
Common Name:   Penisimplicissin
IUPAC Name:   (3R)-4,6-dimethoxy-3-(6-methyl-4-oxopyran-3-yl)-3H-2-benzofuran-1-one
Synonyms:   Penisimplicissin
Molecular Formula:   C16H14O6
Standard InCHIKey:  FKFNGBPZNWNWSG-HNNXBMFYSA-N
Standard InCHI:  InChI=1S/C16H14O6/c1-8-4-12(17)11(7-21-8)15-14-10(16(18)22-15)5-9(19-2)6-13(14)20-3/h4-7,15H,1-3H3/t15-/m0/s1
Canonical SMILES:  COc1cc(OC)c2c(c1)C(=O)O[C@H]2c1coc(cc1=O)C
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
NPO29761 Penicillium rubrum Species Trichocomaceae Eukaryota PMID[22295871]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT116 Cell Line HL-60 Homo sapiens GI50 = 1479.11 nM 10.6019/CHEMBL1201861
NPT404 Cell Line CCRF-CEM Homo sapiens GI50 = 199.53 nM 10.6019/CHEMBL1201861

  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 NPC297985 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
0.9854 High Similarity NPC184702
0.9429 High Similarity NPC470932
0.9149 High Similarity NPC471644
0.9149 High Similarity NPC471640
0.9097 High Similarity NPC52106
0.9085 High Similarity NPC472006
0.9085 High Similarity NPC277369
0.9085 High Similarity NPC471639
0.9085 High Similarity NPC215451
0.9085 High Similarity NPC471643
0.9078 High Similarity NPC90411
0.9034 High Similarity NPC153417
0.9028 High Similarity NPC107625
0.9021 High Similarity NPC27106
0.9014 High Similarity NPC469579
0.9007 High Similarity NPC109007
0.898 High Similarity NPC473732
0.8951 High Similarity NPC51106
0.8944 High Similarity NPC67650
0.8944 High Similarity NPC1704
0.8919 High Similarity NPC475116
0.8897 High Similarity NPC472033
0.8851 High Similarity NPC240768
0.8851 High Similarity NPC200773
0.8836 High Similarity NPC472036
0.8828 High Similarity NPC472034
0.8819 High Similarity NPC469542
0.8811 High Similarity NPC470856
0.8803 High Similarity NPC268052
0.88 High Similarity NPC79998
0.8794 High Similarity NPC135837
0.8792 High Similarity NPC271681
0.8786 High Similarity NPC470844
0.8784 High Similarity NPC119929
0.8784 High Similarity NPC295036
0.8776 High Similarity NPC172329
0.8776 High Similarity NPC240253
0.8776 High Similarity NPC240622
0.8776 High Similarity NPC2569
0.8776 High Similarity NPC471642
0.8776 High Similarity NPC471641
0.8767 High Similarity NPC470357
0.875 High Similarity NPC474385
0.8742 High Similarity NPC150227
0.8742 High Similarity NPC301897
0.8741 High Similarity NPC136095
0.8732 High Similarity NPC191835
0.8725 High Similarity NPC70016
0.8725 High Similarity NPC215921
0.8716 High Similarity NPC4423
0.8716 High Similarity NPC77325
0.8716 High Similarity NPC88445
0.8714 High Similarity NPC311339
0.8707 High Similarity NPC8817
0.8707 High Similarity NPC137296
0.8699 High Similarity NPC171656
0.8699 High Similarity NPC213482
0.8699 High Similarity NPC312789
0.8699 High Similarity NPC75694
0.8696 High Similarity NPC473271
0.869 High Similarity NPC478202
0.8684 High Similarity NPC77679
0.8684 High Similarity NPC190020
0.8684 High Similarity NPC84935
0.8681 High Similarity NPC475730
0.8681 High Similarity NPC158634
0.8675 High Similarity NPC199926
0.8675 High Similarity NPC99381
0.8671 High Similarity NPC92655
0.8671 High Similarity NPC32360
0.8671 High Similarity NPC275356
0.8662 High Similarity NPC70380
0.8662 High Similarity NPC268081
0.8658 High Similarity NPC470107
0.8658 High Similarity NPC179178
0.8658 High Similarity NPC96501
0.8658 High Similarity NPC474660
0.8658 High Similarity NPC469670
0.8658 High Similarity NPC191104
0.8658 High Similarity NPC469619
0.8652 High Similarity NPC182496
0.8652 High Similarity NPC180905
0.8649 High Similarity NPC215711
0.8649 High Similarity NPC73411
0.8643 High Similarity NPC182428
0.8639 High Similarity NPC473927
0.863 High Similarity NPC210425
0.863 High Similarity NPC277426
0.863 High Similarity NPC86373
0.863 High Similarity NPC280404
0.8627 High Similarity NPC325122
0.8621 High Similarity NPC49108
0.8621 High Similarity NPC250755
0.8618 High Similarity NPC470625
0.8618 High Similarity NPC472050
0.8611 High Similarity NPC472515
0.8601 High Similarity NPC472602
0.8601 High Similarity NPC212693
0.8601 High Similarity NPC253616
0.8601 High Similarity NPC103001
0.8601 High Similarity NPC233780
0.8601 High Similarity NPC33144
0.8601 High Similarity NPC94248
0.8601 High Similarity NPC478200
0.86 High Similarity NPC106372
0.86 High Similarity NPC58668
0.86 High Similarity NPC115324
0.8592 High Similarity NPC235115
0.8591 High Similarity NPC237440
0.8591 High Similarity NPC198927
0.8591 High Similarity NPC270160
0.8582 High Similarity NPC175943
0.8582 High Similarity NPC223354
0.8582 High Similarity NPC247743
0.8581 High Similarity NPC74539
0.8581 High Similarity NPC210320
0.8581 High Similarity NPC304443
0.8581 High Similarity NPC14098
0.8571 High Similarity NPC294365
0.8571 High Similarity NPC134621
0.8571 High Similarity NPC316535
0.8571 High Similarity NPC208584
0.8571 High Similarity NPC49282
0.8571 High Similarity NPC473692
0.8562 High Similarity NPC473395
0.8562 High Similarity NPC167663
0.8562 High Similarity NPC263483
0.8562 High Similarity NPC313036
0.8553 High Similarity NPC82592
0.8553 High Similarity NPC16082
0.8552 High Similarity NPC53649
0.8552 High Similarity NPC478217
0.8552 High Similarity NPC472603
0.8552 High Similarity NPC478201
0.8552 High Similarity NPC472035
0.8552 High Similarity NPC313123
0.8543 High Similarity NPC175978
0.8543 High Similarity NPC207624
0.8542 High Similarity NPC36414
0.8535 High Similarity NPC472895
0.8533 High Similarity NPC473466
0.8533 High Similarity NPC216917
0.8533 High Similarity NPC475460
0.8531 High Similarity NPC254741
0.8531 High Similarity NPC472516
0.8516 High Similarity NPC117985
0.8514 High Similarity NPC260946
0.8514 High Similarity NPC237208
0.8511 High Similarity NPC153783
0.8506 High Similarity NPC279732
0.8506 High Similarity NPC470339
0.8503 High Similarity NPC475201
0.8503 High Similarity NPC478203
0.8503 High Similarity NPC126882
0.8503 High Similarity NPC66404
0.8503 High Similarity NPC210966
0.8503 High Similarity NPC95123
0.8503 High Similarity NPC189650
0.85 High Similarity NPC477412
0.8497 Intermediate Similarity NPC474983
0.8493 Intermediate Similarity NPC105648
0.8493 Intermediate Similarity NPC18714
0.8487 Intermediate Similarity NPC186507
0.8487 Intermediate Similarity NPC281477
0.8483 Intermediate Similarity NPC472601
0.8483 Intermediate Similarity NPC165172
0.8483 Intermediate Similarity NPC472600
0.8483 Intermediate Similarity NPC262635
0.8478 Intermediate Similarity NPC475496
0.8478 Intermediate Similarity NPC49852
0.8477 Intermediate Similarity NPC228662
0.8477 Intermediate Similarity NPC193976
0.8477 Intermediate Similarity NPC23668
0.8472 Intermediate Similarity NPC46947
0.8467 Intermediate Similarity NPC476684
0.8467 Intermediate Similarity NPC317492
0.8462 Intermediate Similarity NPC50455
0.8462 Intermediate Similarity NPC61141
0.8462 Intermediate Similarity NPC160425
0.8462 Intermediate Similarity NPC242712
0.8456 Intermediate Similarity NPC17816
0.8456 Intermediate Similarity NPC77903
0.8456 Intermediate Similarity NPC53362
0.8456 Intermediate Similarity NPC166583
0.8456 Intermediate Similarity NPC17101
0.8456 Intermediate Similarity NPC474999
0.8452 Intermediate Similarity NPC313368
0.8452 Intermediate Similarity NPC472055
0.8451 Intermediate Similarity NPC292998
0.8446 Intermediate Similarity NPC474446
0.8446 Intermediate Similarity NPC83272
0.8446 Intermediate Similarity NPC29577
0.8446 Intermediate Similarity NPC257558
0.8446 Intermediate Similarity NPC246903
0.8442 Intermediate Similarity NPC269495
0.8442 Intermediate Similarity NPC246466
0.8435 Intermediate Similarity NPC73028
0.8435 Intermediate Similarity NPC310340
0.8435 Intermediate Similarity NPC159721
0.8435 Intermediate Similarity NPC472344

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC297985 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
0.8803 High Similarity NPD970 Clinical (unspecified phase)
0.8699 High Similarity NPD2533 Approved
0.8699 High Similarity NPD2532 Approved
0.8699 High Similarity NPD2534 Approved
0.8581 High Similarity NPD920 Approved
0.8531 High Similarity NPD2796 Approved
0.8487 Intermediate Similarity NPD7819 Suspended
0.8483 Intermediate Similarity NPD1243 Approved
0.8462 Intermediate Similarity NPD3748 Approved
0.8446 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.8311 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.8217 Intermediate Similarity NPD5494 Approved
0.8207 Intermediate Similarity NPD1510 Phase 2
0.8176 Intermediate Similarity NPD3750 Approved
0.8153 Intermediate Similarity NPD919 Approved
0.8133 Intermediate Similarity NPD6799 Approved
0.8089 Intermediate Similarity NPD3749 Approved
0.8077 Intermediate Similarity NPD3817 Phase 2
0.8056 Intermediate Similarity NPD1240 Approved
0.8054 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.8052 Intermediate Similarity NPD6599 Discontinued
0.8041 Intermediate Similarity NPD1549 Phase 2
0.8013 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.8 Intermediate Similarity NPD5710 Approved
0.8 Intermediate Similarity NPD5711 Approved
0.7987 Intermediate Similarity NPD2800 Approved
0.7974 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7973 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.7973 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.7961 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.7949 Intermediate Similarity NPD1934 Approved
0.7949 Intermediate Similarity NPD6801 Discontinued
0.7945 Intermediate Similarity NPD1607 Approved
0.7937 Intermediate Similarity NPD1247 Approved
0.7935 Intermediate Similarity NPD4380 Phase 2
0.7914 Intermediate Similarity NPD3818 Discontinued
0.7911 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7911 Intermediate Similarity NPD3882 Suspended
0.7898 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7888 Intermediate Similarity NPD6232 Discontinued
0.7885 Intermediate Similarity NPD7411 Suspended
0.7877 Intermediate Similarity NPD230 Phase 1
0.7862 Intermediate Similarity NPD7075 Discontinued
0.7853 Intermediate Similarity NPD7473 Discontinued
0.7848 Intermediate Similarity NPD5402 Approved
0.7826 Intermediate Similarity NPD6959 Discontinued
0.7793 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7785 Intermediate Similarity NPD2801 Approved
0.7785 Intermediate Similarity NPD2935 Discontinued
0.7778 Intermediate Similarity NPD1511 Approved
0.7758 Intermediate Similarity NPD5844 Phase 1
0.7756 Intermediate Similarity NPD3226 Approved
0.7755 Intermediate Similarity NPD1899 Clinical (unspecified phase)
0.775 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.7748 Intermediate Similarity NPD2654 Approved
0.7733 Intermediate Similarity NPD2346 Discontinued
0.773 Intermediate Similarity NPD3926 Phase 2
0.7727 Intermediate Similarity NPD5401 Approved
0.7677 Intermediate Similarity NPD1512 Approved
0.7673 Intermediate Similarity NPD1465 Phase 2
0.7667 Intermediate Similarity NPD1551 Phase 2
0.7655 Intermediate Similarity NPD6832 Phase 2
0.7632 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7628 Intermediate Similarity NPD5403 Approved
0.7625 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.7625 Intermediate Similarity NPD5353 Approved
0.7613 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.761 Intermediate Similarity NPD37 Approved
0.76 Intermediate Similarity NPD2799 Discontinued
0.76 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.7582 Intermediate Similarity NPD4628 Phase 3
0.7578 Intermediate Similarity NPD4966 Approved
0.7578 Intermediate Similarity NPD4967 Phase 2
0.7578 Intermediate Similarity NPD4965 Approved
0.7578 Intermediate Similarity NPD7768 Phase 2
0.7576 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.7561 Intermediate Similarity NPD7229 Phase 3
0.7551 Intermediate Similarity NPD1296 Phase 2
0.7551 Intermediate Similarity NPD2313 Discontinued
0.7551 Intermediate Similarity NPD3764 Approved
0.7518 Intermediate Similarity NPD17 Approved
0.7517 Intermediate Similarity NPD1019 Discontinued
0.7515 Intermediate Similarity NPD6559 Discontinued
0.7515 Intermediate Similarity NPD5242 Approved
0.75 Intermediate Similarity NPD1876 Approved
0.75 Intermediate Similarity NPD2344 Approved
0.75 Intermediate Similarity NPD1471 Phase 3
0.7485 Intermediate Similarity NPD6234 Discontinued
0.7471 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.747 Intermediate Similarity NPD6166 Phase 2
0.747 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.747 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.7468 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7456 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7448 Intermediate Similarity NPD3266 Approved
0.7448 Intermediate Similarity NPD3267 Approved
0.7447 Intermediate Similarity NPD5691 Approved
0.744 Intermediate Similarity NPD7054 Approved
0.7432 Intermediate Similarity NPD1699 Clinical (unspecified phase)
0.7413 Intermediate Similarity NPD1547 Clinical (unspecified phase)
0.7407 Intermediate Similarity NPD4288 Approved
0.74 Intermediate Similarity NPD447 Suspended
0.7397 Intermediate Similarity NPD2798 Approved
0.7396 Intermediate Similarity NPD7472 Approved
0.7396 Intermediate Similarity NPD7074 Phase 3
0.7394 Intermediate Similarity NPD7199 Phase 2
0.7386 Intermediate Similarity NPD2343 Clinical (unspecified phase)
0.7381 Intermediate Similarity NPD7893 Clinical (unspecified phase)
0.7376 Intermediate Similarity NPD9545 Approved
0.7368 Intermediate Similarity NPD7033 Discontinued
0.7368 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.7365 Intermediate Similarity NPD2403 Approved
0.7361 Intermediate Similarity NPD1608 Approved
0.7361 Intermediate Similarity NPD9717 Approved
0.7361 Intermediate Similarity NPD3972 Approved
0.7353 Intermediate Similarity NPD6797 Phase 2
0.7353 Intermediate Similarity NPD5953 Discontinued
0.7351 Intermediate Similarity NPD6651 Approved
0.7349 Intermediate Similarity NPD6808 Phase 2
0.7337 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.7337 Intermediate Similarity NPD7286 Phase 2
0.7333 Intermediate Similarity NPD4307 Phase 2
0.7333 Intermediate Similarity NPD2979 Phase 3
0.7333 Intermediate Similarity NPD943 Approved
0.733 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.732 Intermediate Similarity NPD6100 Approved
0.732 Intermediate Similarity NPD6099 Approved
0.731 Intermediate Similarity NPD7251 Discontinued
0.7308 Intermediate Similarity NPD2309 Approved
0.7305 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7299 Intermediate Similarity NPD2181 Clinical (unspecified phase)
0.7292 Intermediate Similarity NPD422 Phase 1
0.7292 Intermediate Similarity NPD1281 Approved
0.7278 Intermediate Similarity NPD3751 Discontinued
0.7278 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7273 Intermediate Similarity NPD5537 Clinical (unspecified phase)
0.7267 Intermediate Similarity NPD7808 Phase 3
0.7266 Intermediate Similarity NPD1241 Discontinued
0.7233 Intermediate Similarity NPD6273 Approved
0.7222 Intermediate Similarity NPD6385 Approved
0.7222 Intermediate Similarity NPD6386 Approved
0.7215 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7215 Intermediate Similarity NPD7390 Discontinued
0.7211 Intermediate Similarity NPD1203 Approved
0.7208 Intermediate Similarity NPD2438 Suspended
0.7205 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7203 Intermediate Similarity NPD9268 Approved
0.72 Intermediate Similarity NPD411 Approved
0.72 Intermediate Similarity NPD8434 Phase 2
0.72 Intermediate Similarity NPD3268 Approved
0.7181 Intermediate Similarity NPD1008 Clinical (unspecified phase)
0.7176 Intermediate Similarity NPD7228 Approved
0.7171 Intermediate Similarity NPD1933 Approved
0.7168 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.7153 Intermediate Similarity NPD4626 Approved
0.7143 Intermediate Similarity NPD4308 Phase 3
0.7143 Intermediate Similarity NPD3787 Discontinued
0.7143 Intermediate Similarity NPD1283 Approved
0.7143 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7123 Intermediate Similarity NPD9269 Phase 2
0.7119 Intermediate Similarity NPD4287 Approved
0.7119 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7113 Intermediate Similarity NPD9493 Approved
0.711 Intermediate Similarity NPD3658 Clinical (unspecified phase)
0.7095 Intermediate Similarity NPD2797 Approved
0.7089 Intermediate Similarity NPD3887 Approved
0.7083 Intermediate Similarity NPD1651 Approved
0.7073 Intermediate Similarity NPD6279 Approved
0.7073 Intermediate Similarity NPD6280 Approved
0.7065 Intermediate Similarity NPD5005 Approved
0.7065 Intermediate Similarity NPD5006 Approved
0.7059 Intermediate Similarity NPD5124 Phase 1
0.7059 Intermediate Similarity NPD7784 Clinical (unspecified phase)
0.7059 Intermediate Similarity NPD6355 Discontinued
0.7059 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.7055 Intermediate Similarity NPD3705 Approved
0.7051 Intermediate Similarity NPD6006 Clinical (unspecified phase)
0.7051 Intermediate Similarity NPD6004 Phase 3
0.7051 Intermediate Similarity NPD6005 Phase 3
0.7051 Intermediate Similarity NPD6002 Phase 3
0.7051 Intermediate Similarity NPD6003 Clinical (unspecified phase)
0.7039 Intermediate Similarity NPD8032 Phase 2
0.703 Intermediate Similarity NPD5760 Phase 2
0.703 Intermediate Similarity NPD5761 Phase 2
0.7029 Intermediate Similarity NPD8313 Approved
0.7029 Intermediate Similarity NPD8312 Approved
0.7029 Intermediate Similarity NPD2182 Approved
0.7025 Intermediate Similarity NPD7003 Approved
0.7021 Intermediate Similarity NPD8151 Discontinued
0.7012 Intermediate Similarity NPD7615 Clinical (unspecified phase)
0.7011 Intermediate Similarity NPD7240 Approved
0.7 Intermediate Similarity NPD1609 Clinical (unspecified phase)
0.6994 Remote Similarity NPD7458 Discontinued
0.6987 Remote Similarity NPD5406 Approved
0.6987 Remote Similarity NPD5404 Approved
0.6987 Remote Similarity NPD5405 Approved
0.6987 Remote Similarity NPD2531 Phase 2
0.6987 Remote Similarity NPD5408 Approved
0.698 Remote Similarity NPD1470 Approved
0.6962 Remote Similarity NPD1652 Phase 2

Structure

External Identifiers

PubChem CID   11659452
ChEMBL   CHEMBL2024577
ZINC  

Physicochemical Properties

Molecular Weight:  302.08
ALogP:  -0.558
MLogP:  2.56
XLogP:  1.25
# Rotatable Bonds:  6
Polar Surface Area:  71.06
# H-Bond Aceptor:  4
# H-Bond Donor:  0
# Rings:  3
# Heavy Atoms:  22

Download Data

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