Natural Product: NPC469611

Natural Product ID:  NPC469611
Common Name:   Expansol B
IUPAC Name:   2-[[3-hydroxy-4-[(2R)-2-hydroxy-6-methylheptan-2-yl]phenyl]methyl]-5-(3-hydroxy-5-methylphenoxy)-3-methylphenol
Synonyms:   expansol B
Molecular Formula:   C29H36O5
Standard InCHIKey:  GGHNFGXGXUVHRJ-GDLZYMKVSA-N
Standard InCHI:  InChI=1S/C29H36O5/c1-18(2)7-6-10-29(5,33)26-9-8-21(15-28(26)32)14-25-20(4)13-24(17-27(25)31)34-23-12-19(3)11-22(30)16-23/h8-9,11-13,15-18,30-33H,6-7,10,14H2,1-5H3/t29-/m1/s1
Canonical SMILES:  CC(CCC[C@](c1ccc(cc1O)Cc1c(C)cc(cc1O)Oc1cc(C)cc(c1)O)(O)C)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
NPO28107 Penicillium expansum Species Aspergillaceae Eukaryota PMID[20415462]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT116 Cell Line HL-60 Homo sapiens IC50 = 1900 nM DrugMatrix in vitro pharmacology data
NPT81 Cell Line A549 Homo sapiens IC50 = 5400 nM DrugMatrix in vitro pharmacology data

  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 NPC469611 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
0.9921 High Similarity NPC469610
0.992 High Similarity NPC8899
0.9453 High Similarity NPC472590
0.9297 High Similarity NPC222108
0.9297 High Similarity NPC96719
0.9291 High Similarity NPC46978
0.9286 High Similarity NPC113495
0.9173 High Similarity NPC35550
0.9154 High Similarity NPC473309
0.9154 High Similarity NPC160623
0.9154 High Similarity NPC471517
0.9147 High Similarity NPC16577
0.9147 High Similarity NPC471519
0.9147 High Similarity NPC471518
0.9141 High Similarity NPC473221
0.907 High Similarity NPC215300
0.9062 High Similarity NPC170485
0.9062 High Similarity NPC82299
0.9055 High Similarity NPC270030
0.9048 High Similarity NPC74137
0.9023 High Similarity NPC11727
0.9023 High Similarity NPC15109
0.9008 High Similarity NPC282508
0.8992 High Similarity NPC53781
0.8984 High Similarity NPC105031
0.8976 High Similarity NPC96940
0.8971 High Similarity NPC71046
0.8955 High Similarity NPC141717
0.8947 High Similarity NPC473107
0.8931 High Similarity NPC254000
0.8923 High Similarity NPC38017
0.8915 High Similarity NPC26879
0.8915 High Similarity NPC50315
0.8915 High Similarity NPC283049
0.8915 High Similarity NPC230479
0.8906 High Similarity NPC138248
0.8906 High Similarity NPC228503
0.8889 High Similarity NPC218753
0.8889 High Similarity NPC102639
0.8881 High Similarity NPC37410
0.8855 High Similarity NPC93962
0.8855 High Similarity NPC472797
0.8846 High Similarity NPC473134
0.8837 High Similarity NPC278955
0.8837 High Similarity NPC105718
0.8815 High Similarity NPC472648
0.8815 High Similarity NPC170328
0.8815 High Similarity NPC133463
0.8815 High Similarity NPC191462
0.8815 High Similarity NPC206525
0.8815 High Similarity NPC472649
0.8815 High Similarity NPC472647
0.8815 High Similarity NPC472800
0.8797 High Similarity NPC472798
0.8788 High Similarity NPC474481
0.8779 High Similarity NPC38664
0.8779 High Similarity NPC53986
0.8777 High Similarity NPC469795
0.8759 High Similarity NPC182509
0.8759 High Similarity NPC174787
0.8759 High Similarity NPC213607
0.8759 High Similarity NPC273623
0.875 High Similarity NPC71465
0.875 High Similarity NPC472646
0.875 High Similarity NPC266006
0.8741 High Similarity NPC125579
0.8741 High Similarity NPC313081
0.8741 High Similarity NPC258780
0.873 High Similarity NPC137294
0.873 High Similarity NPC184302
0.873 High Similarity NPC85895
0.8722 High Similarity NPC211413
0.8722 High Similarity NPC164804
0.8722 High Similarity NPC293203
0.8722 High Similarity NPC244888
0.8722 High Similarity NPC68205
0.8722 High Similarity NPC118683
0.8696 High Similarity NPC472089
0.8696 High Similarity NPC265075
0.8686 High Similarity NPC275061
0.8686 High Similarity NPC220344
0.8686 High Similarity NPC243996
0.8686 High Similarity NPC132804
0.8682 High Similarity NPC38761
0.8682 High Similarity NPC261992
0.8682 High Similarity NPC76465
0.8676 High Similarity NPC471522
0.8676 High Similarity NPC126101
0.8676 High Similarity NPC234952
0.8672 High Similarity NPC54972
0.8672 High Similarity NPC193364
0.8672 High Similarity NPC476633
0.8667 High Similarity NPC476615
0.8667 High Similarity NPC476616
0.8667 High Similarity NPC476617
0.8657 High Similarity NPC13005
0.8652 High Similarity NPC471608
0.8651 High Similarity NPC190514
0.8643 High Similarity NPC473845
0.8636 High Similarity NPC211179
0.8636 High Similarity NPC38604
0.8636 High Similarity NPC39064
0.8636 High Similarity NPC47283
0.8633 High Similarity NPC472088
0.8633 High Similarity NPC472087
0.8623 High Similarity NPC308768
0.8623 High Similarity NPC234568
0.8623 High Similarity NPC12668
0.8623 High Similarity NPC198038
0.8615 High Similarity NPC159132
0.8613 High Similarity NPC56329
0.8613 High Similarity NPC200935
0.8613 High Similarity NPC266453
0.8613 High Similarity NPC470308
0.8613 High Similarity NPC230919
0.8613 High Similarity NPC22902
0.8613 High Similarity NPC470307
0.8613 High Similarity NPC242715
0.8605 High Similarity NPC188997
0.8605 High Similarity NPC77789
0.8605 High Similarity NPC36016
0.8605 High Similarity NPC18128
0.8605 High Similarity NPC100099
0.8603 High Similarity NPC111655
0.8603 High Similarity NPC200557
0.8603 High Similarity NPC108198
0.8603 High Similarity NPC10314
0.8603 High Similarity NPC69029
0.8603 High Similarity NPC294884
0.8603 High Similarity NPC158142
0.8593 High Similarity NPC77196
0.8593 High Similarity NPC36661
0.8582 High Similarity NPC15543
0.8582 High Similarity NPC181497
0.8582 High Similarity NPC271945
0.8582 High Similarity NPC150011
0.8582 High Similarity NPC206224
0.8582 High Similarity NPC280653
0.8582 High Similarity NPC162801
0.8582 High Similarity NPC236014
0.8582 High Similarity NPC129106
0.8582 High Similarity NPC196765
0.8582 High Similarity NPC300875
0.8582 High Similarity NPC164574
0.8582 High Similarity NPC118114
0.8582 High Similarity NPC268917
0.8582 High Similarity NPC228369
0.8582 High Similarity NPC469907
0.8582 High Similarity NPC476166
0.8582 High Similarity NPC12875
0.8582 High Similarity NPC149633
0.8582 High Similarity NPC207892
0.8582 High Similarity NPC17343
0.8582 High Similarity NPC129784
0.8571 High Similarity NPC472796
0.8571 High Similarity NPC469630
0.8571 High Similarity NPC33270
0.8571 High Similarity NPC163508
0.8571 High Similarity NPC15860
0.8571 High Similarity NPC470759
0.8571 High Similarity NPC474933
0.8571 High Similarity NPC219070
0.8571 High Similarity NPC173203
0.8571 High Similarity NPC472795
0.8571 High Similarity NPC127894
0.8571 High Similarity NPC69261
0.8571 High Similarity NPC134360
0.8551 High Similarity NPC243759
0.8551 High Similarity NPC55947
0.8551 High Similarity NPC32630
0.8551 High Similarity NPC184613
0.8551 High Similarity NPC105847
0.8551 High Similarity NPC218131
0.855 High Similarity NPC188022
0.855 High Similarity NPC102540
0.855 High Similarity NPC103420
0.855 High Similarity NPC285040
0.855 High Similarity NPC476254
0.855 High Similarity NPC131397
0.855 High Similarity NPC293801
0.855 High Similarity NPC17809
0.8542 High Similarity NPC158784
0.854 High Similarity NPC327735
0.854 High Similarity NPC173660
0.854 High Similarity NPC162659
0.854 High Similarity NPC202846
0.854 High Similarity NPC265433
0.854 High Similarity NPC205442
0.854 High Similarity NPC143139
0.854 High Similarity NPC270456
0.854 High Similarity NPC30632
0.854 High Similarity NPC248727
0.8531 High Similarity NPC212142
0.8529 High Similarity NPC209199
0.8529 High Similarity NPC125649
0.8529 High Similarity NPC317380
0.8529 High Similarity NPC296915
0.8529 High Similarity NPC115335
0.8529 High Similarity NPC66840
0.8529 High Similarity NPC97834

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC469611 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
0.9147 High Similarity NPD4625 Phase 3
0.907 High Similarity NPD4908 Phase 1
0.8976 High Similarity NPD4749 Approved
0.8931 High Similarity NPD4907 Clinical (unspecified phase)
0.8672 High Similarity NPD1610 Phase 2
0.8647 High Similarity NPD6410 Clinical (unspecified phase)
0.8478 Intermediate Similarity NPD6099 Approved
0.8478 Intermediate Similarity NPD6100 Approved
0.8359 Intermediate Similarity NPD1548 Phase 1
0.8358 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.8284 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.8209 Intermediate Similarity NPD6917 Clinical (unspecified phase)
0.8148 Intermediate Similarity NPD2861 Phase 2
0.8116 Intermediate Similarity NPD1613 Approved
0.8116 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.8112 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.806 Intermediate Similarity NPD6696 Suspended
0.7985 Intermediate Similarity NPD3600 Clinical (unspecified phase)
0.7984 Intermediate Similarity NPD6671 Approved
0.7937 Intermediate Similarity NPD4750 Phase 3
0.7917 Intermediate Similarity NPD5698 Clinical (unspecified phase)
0.7899 Intermediate Similarity NPD3027 Phase 3
0.7891 Intermediate Similarity NPD7447 Phase 1
0.7862 Intermediate Similarity NPD3750 Approved
0.7857 Intermediate Similarity NPD4060 Phase 1
0.7842 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7836 Intermediate Similarity NPD422 Phase 1
0.7786 Intermediate Similarity NPD7340 Approved
0.7746 Intermediate Similarity NPD4097 Suspended
0.774 Intermediate Similarity NPD7466 Approved
0.774 Intermediate Similarity NPD3892 Phase 2
0.7721 Intermediate Similarity NPD5327 Phase 3
0.7703 Intermediate Similarity NPD7213 Phase 3
0.7703 Intermediate Similarity NPD7212 Phase 2
0.7681 Intermediate Similarity NPD6584 Phase 3
0.7676 Intermediate Similarity NPD5735 Approved
0.7662 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.7651 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7651 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.7643 Intermediate Similarity NPD6959 Discontinued
0.7643 Intermediate Similarity NPD7095 Approved
0.7622 Intermediate Similarity NPD6353 Approved
0.7597 Intermediate Similarity NPD7819 Suspended
0.7595 Intermediate Similarity NPD7229 Phase 3
0.7562 Intermediate Similarity NPD7473 Discontinued
0.7557 Intermediate Similarity NPD1398 Phase 1
0.7556 Intermediate Similarity NPD4626 Approved
0.7554 Intermediate Similarity NPD4624 Approved
0.7552 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.7552 Intermediate Similarity NPD5124 Phase 1
0.7551 Intermediate Similarity NPD6674 Discontinued
0.7533 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.7532 Intermediate Similarity NPD7199 Phase 2
0.752 Intermediate Similarity NPD846 Approved
0.752 Intermediate Similarity NPD940 Approved
0.7517 Intermediate Similarity NPD3748 Approved
0.75 Intermediate Similarity NPD3018 Phase 2
0.75 Intermediate Similarity NPD2342 Discontinued
0.75 Intermediate Similarity NPD7768 Phase 2
0.7484 Intermediate Similarity NPD6232 Discontinued
0.7483 Intermediate Similarity NPD4140 Approved
0.7483 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7483 Intermediate Similarity NPD7037 Approved
0.7482 Intermediate Similarity NPD2797 Approved
0.7481 Intermediate Similarity NPD5535 Approved
0.7481 Intermediate Similarity NPD7635 Approved
0.7469 Intermediate Similarity NPD5844 Phase 1
0.7467 Intermediate Similarity NPD7040 Clinical (unspecified phase)
0.7467 Intermediate Similarity NPD7041 Phase 2
0.7465 Intermediate Similarity NPD6812 Clinical (unspecified phase)
0.7464 Intermediate Similarity NPD6582 Phase 2
0.7464 Intermediate Similarity NPD6583 Phase 3
0.7452 Intermediate Similarity NPD3749 Approved
0.7445 Intermediate Similarity NPD1611 Approved
0.744 Intermediate Similarity NPD1242 Phase 1
0.7438 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7424 Intermediate Similarity NPD5283 Phase 1
0.7419 Intermediate Similarity NPD37 Approved
0.7415 Intermediate Similarity NPD5763 Approved
0.7415 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.7415 Intermediate Similarity NPD5762 Approved
0.7415 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.741 Intermediate Similarity NPD8651 Approved
0.7405 Intermediate Similarity NPD6234 Discontinued
0.74 Intermediate Similarity NPD6815 Approved
0.7391 Intermediate Similarity NPD1608 Approved
0.7389 Intermediate Similarity NPD4966 Approved
0.7389 Intermediate Similarity NPD4965 Approved
0.7389 Intermediate Similarity NPD4967 Phase 2
0.7379 Intermediate Similarity NPD1607 Approved
0.7372 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7365 Intermediate Similarity NPD1549 Phase 2
0.7361 Intermediate Similarity NPD2238 Phase 2
0.736 Intermediate Similarity NPD3020 Approved
0.7353 Intermediate Similarity NPD5691 Approved
0.7351 Intermediate Similarity NPD1511 Approved
0.7343 Intermediate Similarity NPD3268 Approved
0.7338 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7338 Intermediate Similarity NPD2983 Phase 2
0.7338 Intermediate Similarity NPD2982 Phase 2
0.7313 Intermediate Similarity NPD7157 Approved
0.7308 Intermediate Similarity NPD1934 Approved
0.7292 Intermediate Similarity NPD7265 Discontinued
0.7292 Intermediate Similarity NPD8032 Phase 2
0.7286 Intermediate Similarity NPD1283 Approved
0.7279 Intermediate Similarity NPD1510 Phase 2
0.7278 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7266 Intermediate Similarity NPD2233 Approved
0.7266 Intermediate Similarity NPD2981 Phase 2
0.7266 Intermediate Similarity NPD2232 Approved
0.7266 Intermediate Similarity NPD2230 Approved
0.7261 Intermediate Similarity NPD2801 Approved
0.7255 Intermediate Similarity NPD1512 Approved
0.7252 Intermediate Similarity NPD3022 Approved
0.7252 Intermediate Similarity NPD5451 Approved
0.7252 Intermediate Similarity NPD3021 Approved
0.7244 Intermediate Similarity NPD7615 Clinical (unspecified phase)
0.7244 Intermediate Similarity NPD7411 Suspended
0.7241 Intermediate Similarity NPD3620 Phase 2
0.7241 Intermediate Similarity NPD1240 Approved
0.7241 Intermediate Similarity NPD3619 Clinical (unspecified phase)
0.7237 Intermediate Similarity NPD7837 Clinical (unspecified phase)
0.7234 Intermediate Similarity NPD4339 Clinical (unspecified phase)
0.723 Intermediate Similarity NPD2796 Approved
0.723 Intermediate Similarity NPD1551 Phase 2
0.7226 Intermediate Similarity NPD3226 Approved
0.7226 Intermediate Similarity NPD1651 Approved
0.7222 Intermediate Similarity NPD3764 Approved
0.7222 Intermediate Similarity NPD6798 Discontinued
0.7218 Intermediate Similarity NPD7843 Approved
0.7202 Intermediate Similarity NPD8054 Approved
0.7202 Intermediate Similarity NPD8053 Approved
0.72 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.72 Intermediate Similarity NPD288 Approved
0.7195 Intermediate Similarity NPD7228 Approved
0.7192 Intermediate Similarity NPD6355 Discontinued
0.719 Intermediate Similarity NPD7446 Clinical (unspecified phase)
0.719 Intermediate Similarity NPD2533 Approved
0.719 Intermediate Similarity NPD2532 Approved
0.719 Intermediate Similarity NPD2534 Approved
0.7185 Intermediate Similarity NPD709 Approved
0.7178 Intermediate Similarity NPD6166 Phase 2
0.7178 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.7178 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.7176 Intermediate Similarity NPD2684 Approved
0.7174 Intermediate Similarity NPD1778 Approved
0.7174 Intermediate Similarity NPD17 Approved
0.7174 Intermediate Similarity NPD6516 Phase 2
0.7174 Intermediate Similarity NPD4059 Approved
0.7174 Intermediate Similarity NPD5846 Approved
0.7163 Intermediate Similarity NPD3225 Approved
0.7162 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.7162 Intermediate Similarity NPD4308 Phase 3
0.7162 Intermediate Similarity NPD7033 Discontinued
0.7154 Intermediate Similarity NPD968 Approved
0.7153 Intermediate Similarity NPD3091 Approved
0.7152 Intermediate Similarity NPD5929 Approved
0.7152 Intermediate Similarity NPD7003 Approved
0.7143 Intermediate Similarity NPD6746 Phase 2
0.7143 Intermediate Similarity NPD6090 Discontinued
0.7125 Intermediate Similarity NPD7075 Discontinued
0.7124 Intermediate Similarity NPD7390 Discontinued
0.712 Intermediate Similarity NPD844 Approved
0.712 Intermediate Similarity NPD2859 Approved
0.712 Intermediate Similarity NPD2860 Approved
0.7113 Intermediate Similarity NPD3094 Phase 2
0.7101 Intermediate Similarity NPD3443 Approved
0.7101 Intermediate Similarity NPD3444 Approved
0.7101 Intermediate Similarity NPD3445 Approved
0.7101 Intermediate Similarity NPD6830 Clinical (unspecified phase)
0.7083 Intermediate Similarity NPD7549 Discontinued
0.708 Intermediate Similarity NPD7644 Approved
0.7073 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.7071 Intermediate Similarity NPD1091 Approved
0.7071 Intermediate Similarity NPD1281 Approved
0.7071 Intermediate Similarity NPD3092 Approved
0.707 Intermediate Similarity NPD6599 Discontinued
0.7067 Intermediate Similarity NPD2346 Discontinued
0.7063 Intermediate Similarity NPD3882 Suspended
0.7059 Intermediate Similarity NPD6667 Approved
0.7059 Intermediate Similarity NPD6666 Approved
0.705 Intermediate Similarity NPD2667 Approved
0.705 Intermediate Similarity NPD3019 Approved
0.705 Intermediate Similarity NPD2286 Discontinued
0.705 Intermediate Similarity NPD2668 Approved
0.7047 Intermediate Similarity NPD4108 Discontinued
0.7044 Intermediate Similarity NPD7046 Clinical (unspecified phase)
0.7044 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.7044 Intermediate Similarity NPD1465 Phase 2
0.704 Intermediate Similarity NPD2934 Approved
0.704 Intermediate Similarity NPD2933 Approved
0.7039 Intermediate Similarity NPD4628 Phase 3
0.7032 Intermediate Similarity NPD1940 Clinical (unspecified phase)
0.7032 Intermediate Similarity NPD5261 Clinical (unspecified phase)
0.7029 Intermediate Similarity NPD7741 Discontinued
0.7029 Intermediate Similarity NPD6580 Approved
0.7029 Intermediate Similarity NPD6581 Approved
0.7027 Intermediate Similarity NPD2157 Approved
0.7027 Intermediate Similarity NPD4579 Clinical (unspecified phase)
0.7025 Intermediate Similarity NPD6072 Discontinued

Structure

External Identifiers

PubChem CID   46887020
ChEMBL   CHEMBL1094137
ZINC  

Physicochemical Properties

Molecular Weight:  464.26
ALogP:  0.6956
MLogP:  4.1
XLogP:  7.833
# Rotatable Bonds:  18
Polar Surface Area:  90.15
# H-Bond Aceptor:  1
# H-Bond Donor:  4
# Rings:  3
# Heavy Atoms:  34

Download Data

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