Natural Product: NPC477272

Natural Product ID:  NPC477272
Common Name:   Prolificin A
IUPAC Name:   1-[(2R,3S)-2-[(3E)-4,8-dimethylnona-3,7-dienyl]-5,7-dihydroxy-2-methyl-3-(3-methylbut-2-enyl)-3,4-dihydrochromen-8-yl]-2-methylbutan-1-one
Synonyms:  
Molecular Formula:   C31H46O4
Standard InCHIKey:  KNWRSKBHVUABNU-YIYKOETFSA-N
Standard InCHI:  InChI=1S/C31H46O4/c1-9-23(7)29(34)28-27(33)19-26(32)25-18-24(16-15-21(4)5)31(8,35-30(25)28)17-11-14-22(6)13-10-12-20(2)3/h12,14-15,19,23-24,32-33H,9-11,13,16-18H2,1-8H3/b22-14+/t23?,24-,31+/m0/s1
Canonical SMILES:  CCC(C(=O)c1c(O)cc(c2c1O[C@](C)(CC/C=C(/CCC=C(C)C)C)[C@H](C2)CC=C(C)C)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
NPO5547 Hypericum prolificum Species Hypericaceae Eukaryota aerial parts PMID[17125240]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT83 Cell Line MCF7 Homo sapiens IC50 = 23700 nM 17125240
NPT397 Cell Line NCI-H460 Homo sapiens IC50 = 29900 nM 17125240
NPT395 Cell Line SF-268 Homo sapiens IC50 = 30900 nM 17125240
NPT196 Cell Line AGS Homo sapiens IC50 = 32400 nM 17125240
NPT393 Cell Line HCT-116 Homo sapiens IC50 = 35100 nM 17125240

  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 NPC477272 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
0.9851 High Similarity NPC474487
0.9851 High Similarity NPC474504
0.9851 High Similarity NPC470671
0.9851 High Similarity NPC470672
0.9559 High Similarity NPC470668
0.9559 High Similarity NPC470669
0.9559 High Similarity NPC131130
0.95 High Similarity NPC477955
0.9429 High Similarity NPC271288
0.9429 High Similarity NPC470673
0.9429 High Similarity NPC117716
0.9429 High Similarity NPC470674
0.9424 High Similarity NPC144499
0.942 High Similarity NPC471587
0.9412 High Similarity NPC156910
0.9412 High Similarity NPC174999
0.9366 High Similarity NPC145467
0.9362 High Similarity NPC470676
0.9362 High Similarity NPC285630
0.9362 High Similarity NPC473135
0.9362 High Similarity NPC127059
0.9362 High Similarity NPC473132
0.9357 High Similarity NPC106985
0.9357 High Similarity NPC166138
0.9357 High Similarity NPC18585
0.9357 High Similarity NPC219915
0.9348 High Similarity NPC23257
0.9333 High Similarity NPC93756
0.9333 High Similarity NPC108113
0.9301 High Similarity NPC473016
0.9296 High Similarity NPC47388
0.9296 High Similarity NPC308200
0.9296 High Similarity NPC473133
0.9296 High Similarity NPC470670
0.9296 High Similarity NPC91902
0.9291 High Similarity NPC473014
0.9291 High Similarity NPC235217
0.9291 High Similarity NPC131579
0.9291 High Similarity NPC131568
0.9281 High Similarity NPC69769
0.927 High Similarity NPC187826
0.9265 High Similarity NPC125920
0.9265 High Similarity NPC144027
0.9265 High Similarity NPC236974
0.9259 High Similarity NPC10971
0.9236 High Similarity NPC471115
0.9236 High Similarity NPC29777
0.9231 High Similarity NPC39195
0.922 High Similarity NPC278249
0.922 High Similarity NPC107177
0.922 High Similarity NPC478086
0.922 High Similarity NPC223812
0.922 High Similarity NPC316816
0.922 High Similarity NPC214166
0.922 High Similarity NPC125894
0.922 High Similarity NPC85162
0.922 High Similarity NPC81697
0.922 High Similarity NPC77794
0.922 High Similarity NPC185276
0.922 High Similarity NPC11700
0.922 High Similarity NPC38219
0.9214 High Similarity NPC64908
0.9214 High Similarity NPC156190
0.9214 High Similarity NPC282300
0.9214 High Similarity NPC147688
0.9214 High Similarity NPC96408
0.9214 High Similarity NPC17170
0.9214 High Similarity NPC205006
0.9214 High Similarity NPC156590
0.9214 High Similarity NPC166689
0.9214 High Similarity NPC118840
0.9214 High Similarity NPC279650
0.9214 High Similarity NPC258630
0.9209 High Similarity NPC216978
0.9209 High Similarity NPC55018
0.9209 High Similarity NPC19476
0.9209 High Similarity NPC220062
0.9209 High Similarity NPC301217
0.9209 High Similarity NPC303633
0.9209 High Similarity NPC241975
0.9209 High Similarity NPC96565
0.9209 High Similarity NPC139554
0.9197 High Similarity NPC101752
0.9197 High Similarity NPC151113
0.9197 High Similarity NPC60667
0.9185 High Similarity NPC27490
0.9172 High Similarity NPC305965
0.9172 High Similarity NPC178484
0.9167 High Similarity NPC471114
0.9161 High Similarity NPC10990
0.9161 High Similarity NPC473077
0.9161 High Similarity NPC300988
0.9161 High Similarity NPC283234
0.9161 High Similarity NPC296998
0.9155 High Similarity NPC473013
0.9155 High Similarity NPC470890
0.9155 High Similarity NPC311741
0.9155 High Similarity NPC197252
0.9155 High Similarity NPC236766
0.9155 High Similarity NPC326500
0.9155 High Similarity NPC473015
0.9155 High Similarity NPC311144
0.9155 High Similarity NPC209040
0.9155 High Similarity NPC234629
0.9149 High Similarity NPC220998
0.9149 High Similarity NPC214236
0.9149 High Similarity NPC328164
0.9149 High Similarity NPC32739
0.9149 High Similarity NPC265040
0.9149 High Similarity NPC227579
0.9149 High Similarity NPC325346
0.9149 High Similarity NPC10937
0.9149 High Similarity NPC299080
0.9149 High Similarity NPC324436
0.9149 High Similarity NPC76372
0.9149 High Similarity NPC223500
0.9149 High Similarity NPC276565
0.9149 High Similarity NPC204469
0.9149 High Similarity NPC296917
0.9149 High Similarity NPC64915
0.9149 High Similarity NPC66515
0.9149 High Similarity NPC182852
0.9149 High Similarity NPC161506
0.9149 High Similarity NPC293852
0.9149 High Similarity NPC324134
0.9149 High Similarity NPC217083
0.9149 High Similarity NPC78803
0.9149 High Similarity NPC297600
0.9149 High Similarity NPC194432
0.9149 High Similarity NPC167624
0.9149 High Similarity NPC107572
0.9149 High Similarity NPC37496
0.9149 High Similarity NPC78
0.9149 High Similarity NPC202981
0.9149 High Similarity NPC166482
0.9149 High Similarity NPC59739
0.9149 High Similarity NPC62840
0.9149 High Similarity NPC306829
0.9149 High Similarity NPC11561
0.9149 High Similarity NPC76338
0.9149 High Similarity NPC177354
0.9149 High Similarity NPC40833
0.9149 High Similarity NPC166934
0.9149 High Similarity NPC148757
0.9149 High Similarity NPC125855
0.9149 High Similarity NPC228504
0.9149 High Similarity NPC226636
0.9149 High Similarity NPC1089
0.9143 High Similarity NPC172986
0.9143 High Similarity NPC159275
0.9143 High Similarity NPC261227
0.9143 High Similarity NPC150522
0.9143 High Similarity NPC305355
0.9143 High Similarity NPC76445
0.9143 High Similarity NPC475680
0.9143 High Similarity NPC235239
0.9143 High Similarity NPC129853
0.9143 High Similarity NPC270883
0.9143 High Similarity NPC284550
0.9143 High Similarity NPC241100
0.9137 High Similarity NPC470399
0.9137 High Similarity NPC183639
0.9137 High Similarity NPC201395
0.9137 High Similarity NPC21350
0.9137 High Similarity NPC219584
0.9137 High Similarity NPC199458
0.9137 High Similarity NPC470083
0.913 High Similarity NPC470398
0.913 High Similarity NPC470397
0.9118 High Similarity NPC25937
0.9118 High Similarity NPC203817
0.9111 High Similarity NPC5515
0.9111 High Similarity NPC324482
0.9111 High Similarity NPC270369
0.9103 High Similarity NPC158866
0.9103 High Similarity NPC150928
0.9097 High Similarity NPC160821
0.9097 High Similarity NPC296869
0.9097 High Similarity NPC132592
0.9091 High Similarity NPC246948
0.9091 High Similarity NPC472629
0.9091 High Similarity NPC475052
0.9091 High Similarity NPC82534
0.9091 High Similarity NPC142405
0.9091 High Similarity NPC176229
0.9091 High Similarity NPC195621
0.9091 High Similarity NPC154217
0.9091 High Similarity NPC187282
0.9091 High Similarity NPC20488
0.9091 High Similarity NPC88964
0.9091 High Similarity NPC301276
0.9091 High Similarity NPC290133
0.9091 High Similarity NPC24136
0.9091 High Similarity NPC214774
0.9091 High Similarity NPC124729
0.9091 High Similarity NPC267375
0.9091 High Similarity NPC54577
0.9091 High Similarity NPC111786
0.9091 High Similarity NPC329678
0.9091 High Similarity NPC312973

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC477272 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
0.9021 High Similarity NPD4378 Clinical (unspecified phase)
0.8986 High Similarity NPD8443 Clinical (unspecified phase)
0.8889 High Similarity NPD7410 Clinical (unspecified phase)
0.8803 High Similarity NPD2800 Approved
0.8794 High Similarity NPD1552 Clinical (unspecified phase)
0.8794 High Similarity NPD1550 Clinical (unspecified phase)
0.8732 High Similarity NPD1549 Phase 2
0.8667 High Similarity NPD2393 Clinical (unspecified phase)
0.8667 High Similarity NPD7819 Suspended
0.8643 High Similarity NPD6651 Approved
0.8633 High Similarity NPD1240 Approved
0.8618 High Similarity NPD7075 Discontinued
0.8601 High Similarity NPD970 Clinical (unspecified phase)
0.8543 High Similarity NPD7096 Clinical (unspecified phase)
0.8533 High Similarity NPD7411 Suspended
0.8521 High Similarity NPD1510 Phase 2
0.8511 High Similarity NPD1607 Approved
0.8467 Intermediate Similarity NPD4380 Phase 2
0.8462 Intermediate Similarity NPD2796 Approved
0.8462 Intermediate Similarity NPD6099 Approved
0.8462 Intermediate Similarity NPD6100 Approved
0.8356 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.8355 Intermediate Similarity NPD1934 Approved
0.8333 Intermediate Similarity NPD6959 Discontinued
0.8312 Intermediate Similarity NPD7768 Phase 2
0.8311 Intermediate Similarity NPD1511 Approved
0.8291 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.8288 Intermediate Similarity NPD1243 Approved
0.8264 Intermediate Similarity NPD2799 Discontinued
0.8258 Intermediate Similarity NPD3749 Approved
0.8255 Intermediate Similarity NPD2533 Approved
0.8255 Intermediate Similarity NPD2534 Approved
0.8255 Intermediate Similarity NPD2532 Approved
0.8231 Intermediate Similarity NPD3750 Approved
0.82 Intermediate Similarity NPD1512 Approved
0.8188 Intermediate Similarity NPD6799 Approved
0.8182 Intermediate Similarity NPD2801 Approved
0.8141 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.8137 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.8117 Intermediate Similarity NPD6801 Discontinued
0.8105 Intermediate Similarity NPD6599 Discontinued
0.8099 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.8077 Intermediate Similarity NPD3882 Suspended
0.8041 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.8038 Intermediate Similarity NPD5494 Approved
0.8027 Intermediate Similarity NPD2344 Approved
0.8012 Intermediate Similarity NPD7473 Discontinued
0.7972 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7959 Intermediate Similarity NPD1551 Phase 2
0.7959 Intermediate Similarity NPD2935 Discontinued
0.795 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.795 Intermediate Similarity NPD6166 Phase 2
0.795 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.7939 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.7908 Intermediate Similarity NPD920 Approved
0.7891 Intermediate Similarity NPD3748 Approved
0.7891 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.7881 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.7867 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7866 Intermediate Similarity NPD7074 Phase 3
0.7857 Intermediate Similarity NPD4749 Approved
0.7832 Intermediate Similarity NPD4908 Phase 1
0.7826 Intermediate Similarity NPD6232 Discontinued
0.7818 Intermediate Similarity NPD5953 Discontinued
0.7815 Intermediate Similarity NPD2309 Approved
0.7805 Intermediate Similarity NPD7054 Approved
0.7805 Intermediate Similarity NPD7286 Phase 2
0.7786 Intermediate Similarity NPD9717 Approved
0.7785 Intermediate Similarity NPD3817 Phase 2
0.7778 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7758 Intermediate Similarity NPD7472 Approved
0.7746 Intermediate Similarity NPD1203 Approved
0.7736 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7724 Intermediate Similarity NPD3268 Approved
0.7724 Intermediate Similarity NPD2313 Discontinued
0.7724 Intermediate Similarity NPD6410 Clinical (unspecified phase)
0.7716 Intermediate Similarity NPD5711 Approved
0.7716 Intermediate Similarity NPD5710 Approved
0.7714 Intermediate Similarity NPD422 Phase 1
0.7714 Intermediate Similarity NPD1610 Phase 2
0.7712 Intermediate Similarity NPD7390 Discontinued
0.7692 Intermediate Similarity NPD3226 Approved
0.7692 Intermediate Similarity NPD2798 Approved
0.7687 Intermediate Similarity NPD5124 Phase 1
0.7687 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.7682 Intermediate Similarity NPD2654 Approved
0.7667 Intermediate Similarity NPD2346 Discontinued
0.7665 Intermediate Similarity NPD6559 Discontinued
0.7665 Intermediate Similarity NPD7251 Discontinued
0.7655 Intermediate Similarity NPD4625 Phase 3
0.7636 Intermediate Similarity NPD3818 Discontinued
0.7632 Intermediate Similarity NPD4628 Phase 3
0.7622 Intermediate Similarity NPD2797 Approved
0.7619 Intermediate Similarity NPD7808 Phase 3
0.7619 Intermediate Similarity NPD943 Approved
0.7605 Intermediate Similarity NPD6797 Phase 2
0.759 Intermediate Similarity NPD5844 Phase 1
0.7586 Intermediate Similarity NPD4360 Phase 2
0.7586 Intermediate Similarity NPD6832 Phase 2
0.7586 Intermediate Similarity NPD4363 Phase 3
0.7564 Intermediate Similarity NPD5403 Approved
0.7535 Intermediate Similarity NPD1608 Approved
0.7531 Intermediate Similarity NPD919 Approved
0.7515 Intermediate Similarity NPD2403 Approved
0.75 Intermediate Similarity NPD1465 Phase 2
0.7484 Intermediate Similarity NPD7615 Clinical (unspecified phase)
0.7465 Intermediate Similarity NPD1547 Clinical (unspecified phase)
0.7455 Intermediate Similarity NPD3926 Phase 2
0.7443 Intermediate Similarity NPD4362 Clinical (unspecified phase)
0.7443 Intermediate Similarity NPD4361 Phase 2
0.7439 Intermediate Similarity NPD1247 Approved
0.7436 Intermediate Similarity NPD5401 Approved
0.7417 Intermediate Similarity NPD7033 Discontinued
0.7417 Intermediate Similarity NPD4308 Phase 3
0.7412 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.7379 Intermediate Similarity NPD3267 Approved
0.7379 Intermediate Similarity NPD3266 Approved
0.7376 Intermediate Similarity NPD4196 Clinical (unspecified phase)
0.7365 Intermediate Similarity NPD1296 Phase 2
0.7365 Intermediate Similarity NPD411 Approved
0.7358 Intermediate Similarity NPD7458 Discontinued
0.7353 Intermediate Similarity NPD6104 Discontinued
0.7346 Intermediate Similarity NPD5402 Approved
0.7337 Intermediate Similarity NPD1729 Discontinued
0.7333 Intermediate Similarity NPD447 Suspended
0.7333 Intermediate Similarity NPD230 Phase 1
0.7325 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7324 Intermediate Similarity NPD17 Approved
0.7305 Intermediate Similarity NPD1548 Phase 1
0.7305 Intermediate Similarity NPD9545 Approved
0.7303 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.7294 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7292 Intermediate Similarity NPD3972 Approved
0.7289 Intermediate Similarity NPD7229 Phase 3
0.7286 Intermediate Similarity NPD9493 Approved
0.7279 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7278 Intermediate Similarity NPD7501 Clinical (unspecified phase)
0.7273 Intermediate Similarity NPD2424 Discontinued
0.7273 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.726 Intermediate Similarity NPD1164 Approved
0.7257 Intermediate Similarity NPD4287 Approved
0.725 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7248 Intermediate Similarity NPD3764 Approved
0.7239 Intermediate Similarity NPD4288 Approved
0.7239 Intermediate Similarity NPD2296 Approved
0.723 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7222 Intermediate Similarity NPD1201 Approved
0.7219 Intermediate Similarity NPD6355 Discontinued
0.7214 Intermediate Similarity NPD6671 Approved
0.7211 Intermediate Similarity NPD6917 Clinical (unspecified phase)
0.7208 Intermediate Similarity NPD6005 Phase 3
0.7208 Intermediate Similarity NPD6006 Clinical (unspecified phase)
0.7208 Intermediate Similarity NPD1471 Phase 3
0.7208 Intermediate Similarity NPD6003 Clinical (unspecified phase)
0.7208 Intermediate Similarity NPD6002 Phase 3
0.7208 Intermediate Similarity NPD6004 Phase 3
0.7208 Intermediate Similarity NPD2343 Clinical (unspecified phase)
0.7207 Intermediate Similarity NPD8090 Clinical (unspecified phase)
0.7194 Intermediate Similarity NPD1241 Discontinued
0.7192 Intermediate Similarity NPD3225 Approved
0.7179 Intermediate Similarity NPD7003 Approved
0.7178 Intermediate Similarity NPD5761 Phase 2
0.7178 Intermediate Similarity NPD5760 Phase 2
0.7168 Intermediate Similarity NPD8313 Approved
0.7168 Intermediate Similarity NPD8312 Approved
0.716 Intermediate Similarity NPD3446 Phase 1
0.7152 Intermediate Similarity NPD4307 Phase 2
0.7143 Intermediate Similarity NPD5406 Approved
0.7143 Intermediate Similarity NPD5408 Approved
0.7143 Intermediate Similarity NPD1470 Approved
0.7143 Intermediate Similarity NPD5405 Approved
0.7143 Intermediate Similarity NPD5404 Approved
0.7135 Intermediate Similarity NPD7584 Approved
0.7125 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7118 Intermediate Similarity NPD7893 Clinical (unspecified phase)
0.7117 Intermediate Similarity NPD7577 Discontinued
0.7105 Intermediate Similarity NPD1899 Clinical (unspecified phase)
0.7105 Intermediate Similarity NPD1933 Approved
0.7099 Intermediate Similarity NPD6585 Discontinued
0.7095 Intermediate Similarity NPD1019 Discontinued
0.7075 Intermediate Similarity NPD1876 Approved
0.7075 Intermediate Similarity NPD6696 Suspended
0.7063 Intermediate Similarity NPD5049 Phase 3
0.7047 Intermediate Similarity NPD2861 Phase 2
0.7045 Intermediate Similarity NPD8434 Phase 2
0.7039 Intermediate Similarity NPD1613 Approved
0.7039 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7039 Intermediate Similarity NPD3140 Approved
0.7039 Intermediate Similarity NPD4060 Phase 1
0.7039 Intermediate Similarity NPD3142 Approved
0.7032 Intermediate Similarity NPD4476 Approved
0.7032 Intermediate Similarity NPD4477 Approved
0.7025 Intermediate Similarity NPD2354 Approved
0.7024 Intermediate Similarity NPD7199 Phase 2
0.7018 Intermediate Similarity NPD3751 Discontinued
0.7 Intermediate Similarity NPD1008 Clinical (unspecified phase)
0.6982 Remote Similarity NPD3787 Discontinued
0.697 Remote Similarity NPD8455 Phase 2
0.6966 Remote Similarity NPD4626 Approved
0.6959 Remote Similarity NPD8651 Approved

Structure

External Identifiers

PubChem CID   11995285
ChEMBL   CHEMBL448374
ZINC  

Physicochemical Properties

Molecular Weight:  482.34
ALogP:  3.8075
MLogP:  4.43
XLogP:  7.737
# Rotatable Bonds:  21
Polar Surface Area:  66.76
# H-Bond Aceptor:  1
# H-Bond Donor:  2
# Rings:  2
# Heavy Atoms:  35

Download Data

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