Natural Product: NPC205618

Natural Product ID:  NPC205618
Common Name:   Guaianediol
IUPAC Name:   (1R,3aS,4S,8aR)-1,4-dimethyl-7-propan-2-yl-2,3,3a,5,6,8a-hexahydroazulene-1,4-diol
Synonyms:   (-)-Alismoxide; Guaianediol
Molecular Formula:   C15H26O2
Standard InCHIKey:  IWQURBSTAIRNAE-LJISPDSOSA-N
Standard InCHI:  InChI=1S/C15H26O2/c1-10(2)11-5-7-14(3,16)12-6-8-15(4,17)13(12)9-11/h9-10,12-13,16-17H,5-8H2,1-4H3/t12-,13+,14-,15+/m0/s1
Canonical SMILES:  CC(C1=C[C@@H]2[C@@H]([C@@](CC1)(C)O)CC[C@@]2(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
NPO29956 Sanicula lamelligera Species Apiaceae Eukaryota Whole plants Mountain Emei, Sichuan Province, China 2008-OCT PMID[21561060]
NPO4048 Inga longispica Species Oecophoridae Eukaryota UNPD*
NPO29956 Sanicula lamelligera Species Apiaceae Eukaryota Whole Plants PMID[21561060]
NPO791 Laburnum anagyroides Species Fabaceae Eukaryota UNPD*
NPO60 Neoshirakia japonica Species Euphorbiaceae Eukaryota UNPD*
NPO10306 Alisma orienatale Species Alismataceae Eukaryota TM-MC*
NPO14364.1 Alisma plantago-aquatica subsp. orientale Subspecies Alismataceae Eukaryota TM-MC*
NPO3061 Alisma orientalis Species Alismataceae Eukaryota TM-MC*
NPO7730 Commiphora myrrha Species Burseraceae Eukaryota TCMID*

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT168 Cell Line P388 Mus musculus Activity = 1 ug/ml 8759167
NPT81 Cell Line A549 Homo sapiens Activity = 2.5 ug/ml 8759167
NPT170 Cell Line SK-MEL-28 Homo sapiens Activity = 5 ug/ml 8759167
NPT139 Cell Line HT-29 Homo sapiens Activity = 5 ug/ml 8759167
NPT83 Cell Line MCF7 Homo sapiens IC50 > 64400 nM 21561060
NPT81 Cell Line A549 Homo sapiens IC50 > 64400 nM 21561060
NPT659 Cell Line SMMC-7721 Homo sapiens IC50 > 64400 nM 21561060
NPT116 Cell Line HL-60 Homo sapiens IC50 > 64400 nM 21561060
NPT113 Cell Line RAW264.7 Mus musculus IC50 > 64400 nM 21561060
NPT24 Organism Human immunodeficiency virus 1 Human immunodeficiency virus 1 EC50 > 420200 nM 21561060
NPT1452 Cell Line C8166 Homo sapiens CC50 > 420200 nM 21561060
NPT660 Cell Line SW480 Homo sapiens IC50 > 64400 nM 21561060

  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 NPC205618 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
1.0 High Similarity NPC261782
1.0 High Similarity NPC469326
0.95 High Similarity NPC63111
0.9375 High Similarity NPC144647
0.9231 High Similarity NPC471781
0.9167 High Similarity NPC469321
0.8852 High Similarity NPC52431
0.8852 High Similarity NPC310228
0.8833 High Similarity NPC278550
0.8333 Intermediate Similarity NPC469324
0.8261 Intermediate Similarity NPC41886
0.8125 Intermediate Similarity NPC252809
0.8116 Intermediate Similarity NPC470041
0.8056 Intermediate Similarity NPC126969
0.7971 Intermediate Similarity NPC474900
0.7969 Intermediate Similarity NPC5698
0.7941 Intermediate Similarity NPC136813
0.7887 Intermediate Similarity NPC469320
0.7879 Intermediate Similarity NPC474480
0.7869 Intermediate Similarity NPC192962
0.7846 Intermediate Similarity NPC323153
0.7826 Intermediate Similarity NPC224532
0.7778 Intermediate Similarity NPC274396
0.7746 Intermediate Similarity NPC471660
0.7692 Intermediate Similarity NPC184049
0.7692 Intermediate Similarity NPC99480
0.7681 Intermediate Similarity NPC472255
0.7681 Intermediate Similarity NPC472253
0.7647 Intermediate Similarity NPC238352
0.7647 Intermediate Similarity NPC477009
0.7639 Intermediate Similarity NPC300940
0.7632 Intermediate Similarity NPC30675
0.7612 Intermediate Similarity NPC211291
0.7612 Intermediate Similarity NPC133368
0.7576 Intermediate Similarity NPC135648
0.7571 Intermediate Similarity NPC167527
0.7568 Intermediate Similarity NPC152017
0.7538 Intermediate Similarity NPC475830
0.7536 Intermediate Similarity NPC469328
0.7536 Intermediate Similarity NPC272125
0.7534 Intermediate Similarity NPC471659
0.7463 Intermediate Similarity NPC274704
0.7436 Intermediate Similarity NPC133844
0.7432 Intermediate Similarity NPC77501
0.7432 Intermediate Similarity NPC85831
0.7432 Intermediate Similarity NPC265921
0.7432 Intermediate Similarity NPC215215
0.7391 Intermediate Similarity NPC471200
0.7353 Intermediate Similarity NPC279200
0.7342 Intermediate Similarity NPC471340
0.7333 Intermediate Similarity NPC115719
0.7333 Intermediate Similarity NPC471658
0.7333 Intermediate Similarity NPC124289
0.7333 Intermediate Similarity NPC142759
0.7333 Intermediate Similarity NPC25908
0.7333 Intermediate Similarity NPC473437
0.7333 Intermediate Similarity NPC141346
0.7308 Intermediate Similarity NPC471661
0.7297 Intermediate Similarity NPC309178
0.7273 Intermediate Similarity NPC471890
0.7273 Intermediate Similarity NPC66677
0.7273 Intermediate Similarity NPC84185
0.726 Intermediate Similarity NPC469737
0.7237 Intermediate Similarity NPC471454
0.7215 Intermediate Similarity NPC470614
0.7215 Intermediate Similarity NPC472465
0.7215 Intermediate Similarity NPC1272
0.7206 Intermediate Similarity NPC15152
0.7206 Intermediate Similarity NPC210346
0.72 Intermediate Similarity NPC319090
0.72 Intermediate Similarity NPC113639
0.72 Intermediate Similarity NPC23231
0.72 Intermediate Similarity NPC60818
0.72 Intermediate Similarity NPC328104
0.7183 Intermediate Similarity NPC477791
0.7179 Intermediate Similarity NPC26117
0.7162 Intermediate Similarity NPC14352
0.7162 Intermediate Similarity NPC234527
0.716 Intermediate Similarity NPC146850
0.716 Intermediate Similarity NPC287015
0.7143 Intermediate Similarity NPC157781
0.7143 Intermediate Similarity NPC179169
0.7143 Intermediate Similarity NPC35519
0.7143 Intermediate Similarity NPC61503
0.7143 Intermediate Similarity NPC470944
0.7143 Intermediate Similarity NPC306195
0.7143 Intermediate Similarity NPC187619
0.7143 Intermediate Similarity NPC181255
0.7123 Intermediate Similarity NPC254845
0.7105 Intermediate Similarity NPC215481
0.7105 Intermediate Similarity NPC476317
0.7105 Intermediate Similarity NPC310643
0.7101 Intermediate Similarity NPC473508
0.7097 Intermediate Similarity NPC329773
0.7077 Intermediate Similarity NPC218525
0.7077 Intermediate Similarity NPC45387
0.7067 Intermediate Similarity NPC329090
0.7067 Intermediate Similarity NPC27395
0.7059 Intermediate Similarity NPC162109
0.7042 Intermediate Similarity NPC311736
0.7042 Intermediate Similarity NPC230107
0.7037 Intermediate Similarity NPC90446
0.7037 Intermediate Similarity NPC116613
0.7037 Intermediate Similarity NPC124172
0.7027 Intermediate Similarity NPC471662
0.7013 Intermediate Similarity NPC186109
0.7 Intermediate Similarity NPC300593
0.7 Intermediate Similarity NPC309300
0.6988 Remote Similarity NPC191283
0.6986 Remote Similarity NPC74722
0.6986 Remote Similarity NPC304690
0.6984 Remote Similarity NPC214584
0.6984 Remote Similarity NPC26906
0.6974 Remote Similarity NPC251435
0.6974 Remote Similarity NPC313185
0.6974 Remote Similarity NPC89374
0.6962 Remote Similarity NPC186072
0.6962 Remote Similarity NPC324772
0.6962 Remote Similarity NPC471656
0.6962 Remote Similarity NPC164218
0.6944 Remote Similarity NPC73603
0.6944 Remote Similarity NPC163290
0.6941 Remote Similarity NPC301969
0.6941 Remote Similarity NPC470832
0.6941 Remote Similarity NPC37607
0.6933 Remote Similarity NPC310608
0.6933 Remote Similarity NPC474140
0.6933 Remote Similarity NPC476709
0.6923 Remote Similarity NPC87604
0.6923 Remote Similarity NPC477522
0.6914 Remote Similarity NPC110778
0.6914 Remote Similarity NPC477818
0.6901 Remote Similarity NPC300442
0.6892 Remote Similarity NPC475728
0.6892 Remote Similarity NPC133873
0.6883 Remote Similarity NPC315261
0.6883 Remote Similarity NPC96319
0.6875 Remote Similarity NPC177112
0.6875 Remote Similarity NPC15978
0.6875 Remote Similarity NPC71506
0.6875 Remote Similarity NPC320525
0.6867 Remote Similarity NPC152808
0.6867 Remote Similarity NPC201273
0.6867 Remote Similarity NPC293287
0.6867 Remote Similarity NPC24277
0.6866 Remote Similarity NPC119425
0.686 Remote Similarity NPC94127
0.6835 Remote Similarity NPC204270
0.6829 Remote Similarity NPC475798
0.6829 Remote Similarity NPC209802
0.6829 Remote Similarity NPC127606
0.6818 Remote Similarity NPC67584
0.6818 Remote Similarity NPC52044
0.6812 Remote Similarity NPC99487
0.6812 Remote Similarity NPC66020
0.6806 Remote Similarity NPC162309
0.6806 Remote Similarity NPC267027
0.68 Remote Similarity NPC469343
0.6795 Remote Similarity NPC318495
0.6795 Remote Similarity NPC198968
0.6795 Remote Similarity NPC476439
0.6795 Remote Similarity NPC155986
0.6786 Remote Similarity NPC271967
0.6782 Remote Similarity NPC40821
0.6782 Remote Similarity NPC32862
0.6782 Remote Similarity NPC272293
0.6765 Remote Similarity NPC10017
0.6761 Remote Similarity NPC219940
0.6761 Remote Similarity NPC287744
0.6761 Remote Similarity NPC140233
0.6757 Remote Similarity NPC90115
0.6757 Remote Similarity NPC22301
0.6757 Remote Similarity NPC217570
0.6753 Remote Similarity NPC12696
0.675 Remote Similarity NPC156658
0.675 Remote Similarity NPC258965
0.6747 Remote Similarity NPC474349
0.6747 Remote Similarity NPC471185
0.6747 Remote Similarity NPC474189
0.6742 Remote Similarity NPC213078
0.6714 Remote Similarity NPC79576
0.6714 Remote Similarity NPC194208
0.6714 Remote Similarity NPC282694
0.6712 Remote Similarity NPC82337
0.6709 Remote Similarity NPC477514
0.6707 Remote Similarity NPC193870
0.6707 Remote Similarity NPC320548
0.6707 Remote Similarity NPC141941
0.6707 Remote Similarity NPC477667
0.6706 Remote Similarity NPC2158
0.6706 Remote Similarity NPC470542
0.6705 Remote Similarity NPC473258
0.6667 Remote Similarity NPC170148
0.6667 Remote Similarity NPC321381
0.6667 Remote Similarity NPC209620
0.6667 Remote Similarity NPC6605
0.6667 Remote Similarity NPC122239
0.6667 Remote Similarity NPC23852
0.6667 Remote Similarity NPC161493
0.6667 Remote Similarity NPC321016

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC205618 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
0.7297 Intermediate Similarity NPD4784 Approved
0.7297 Intermediate Similarity NPD4785 Approved
0.726 Intermediate Similarity NPD4243 Approved
0.7067 Intermediate Similarity NPD6924 Approved
0.7067 Intermediate Similarity NPD6926 Approved
0.6974 Remote Similarity NPD4190 Phase 3
0.6974 Remote Similarity NPD5275 Approved
0.6962 Remote Similarity NPD6931 Approved
0.6962 Remote Similarity NPD6930 Phase 2
0.6883 Remote Similarity NPD6933 Approved
0.6883 Remote Similarity NPD3701 Clinical (unspecified phase)
0.6835 Remote Similarity NPD6929 Approved
0.6835 Remote Similarity NPD4195 Approved
0.6829 Remote Similarity NPD7338 Clinical (unspecified phase)
0.6795 Remote Similarity NPD6932 Approved
0.6786 Remote Similarity NPD4751 Clinical (unspecified phase)
0.6707 Remote Similarity NPD6695 Phase 3
0.6625 Remote Similarity NPD6683 Phase 2
0.6585 Remote Similarity NPD4221 Approved
0.6585 Remote Similarity NPD4223 Phase 3
0.6582 Remote Similarity NPD5776 Phase 2
0.6582 Remote Similarity NPD6925 Approved
0.6548 Remote Similarity NPD6893 Approved
0.6543 Remote Similarity NPD4820 Approved
0.6543 Remote Similarity NPD7525 Registered
0.6543 Remote Similarity NPD7509 Discontinued
0.6543 Remote Similarity NPD4822 Approved
0.6543 Remote Similarity NPD7514 Phase 3
0.6543 Remote Similarity NPD4819 Approved
0.6543 Remote Similarity NPD4821 Approved
0.6538 Remote Similarity NPD7339 Approved
0.6538 Remote Similarity NPD6942 Approved
0.6533 Remote Similarity NPD6923 Approved
0.6533 Remote Similarity NPD6922 Approved
0.65 Remote Similarity NPD7145 Approved
0.6479 Remote Similarity NPD368 Approved
0.6447 Remote Similarity NPD7143 Approved
0.6447 Remote Similarity NPD7144 Approved
0.6429 Remote Similarity NPD4197 Approved
0.6395 Remote Similarity NPD7750 Discontinued
0.6395 Remote Similarity NPD7524 Approved
0.6364 Remote Similarity NPD7150 Approved
0.6364 Remote Similarity NPD7151 Approved
0.6364 Remote Similarity NPD7152 Approved
0.6353 Remote Similarity NPD5329 Approved
0.6341 Remote Similarity NPD4748 Discontinued
0.6341 Remote Similarity NPD7332 Phase 2
0.6322 Remote Similarity NPD4518 Approved
0.631 Remote Similarity NPD5331 Approved
0.631 Remote Similarity NPD5332 Approved
0.631 Remote Similarity NPD5362 Discontinued
0.6296 Remote Similarity NPD4271 Approved
0.6296 Remote Similarity NPD4268 Approved
0.6279 Remote Similarity NPD4688 Approved
0.6279 Remote Similarity NPD5280 Approved
0.6279 Remote Similarity NPD4690 Approved
0.6279 Remote Similarity NPD4138 Approved
0.6279 Remote Similarity NPD4693 Phase 3
0.6279 Remote Similarity NPD5205 Approved
0.6279 Remote Similarity NPD4694 Approved
0.6279 Remote Similarity NPD5690 Phase 2
0.6279 Remote Similarity NPD4689 Approved
0.6265 Remote Similarity NPD4790 Discontinued
0.6265 Remote Similarity NPD6902 Approved
0.6265 Remote Similarity NPD6898 Phase 1
0.6265 Remote Similarity NPD5369 Approved
0.618 Remote Similarity NPD4001 Clinical (unspecified phase)
0.6163 Remote Similarity NPD6082 Clinical (unspecified phase)
0.6145 Remote Similarity NPD5368 Approved
0.6145 Remote Similarity NPD5790 Clinical (unspecified phase)
0.6136 Remote Similarity NPD4723 Approved
0.6136 Remote Similarity NPD4722 Approved
0.6111 Remote Similarity NPD5281 Approved
0.6111 Remote Similarity NPD5284 Approved
0.6111 Remote Similarity NPD7087 Discontinued
0.6098 Remote Similarity NPD7322 Clinical (unspecified phase)
0.6092 Remote Similarity NPD4249 Approved
0.6087 Remote Similarity NPD342 Phase 1
0.6071 Remote Similarity NPD4139 Approved
0.6071 Remote Similarity NPD4692 Approved
0.6067 Remote Similarity NPD1695 Approved
0.6067 Remote Similarity NPD4753 Phase 2
0.6049 Remote Similarity NPD1346 Approved
0.6047 Remote Similarity NPD3665 Phase 1
0.6047 Remote Similarity NPD3133 Approved
0.6047 Remote Similarity NPD3666 Approved
0.6047 Remote Similarity NPD4786 Approved
0.6044 Remote Similarity NPD4202 Approved
0.6023 Remote Similarity NPD4251 Approved
0.6023 Remote Similarity NPD4250 Approved
0.6 Remote Similarity NPD6435 Approved
0.6 Remote Similarity NPD4096 Approved
0.6 Remote Similarity NPD4269 Approved
0.6 Remote Similarity NPD4270 Approved
0.6 Remote Similarity NPD3667 Approved
0.5938 Remote Similarity NPD386 Approved
0.5938 Remote Similarity NPD388 Approved
0.5921 Remote Similarity NPD7331 Phase 2
0.5897 Remote Similarity NPD1082 Approved
0.5795 Remote Similarity NPD5363 Approved
0.5789 Remote Similarity NPD7341 Phase 2
0.5789 Remote Similarity NPD4755 Approved
0.5765 Remote Similarity NPD4252 Approved
0.5747 Remote Similarity NPD4788 Approved
0.5745 Remote Similarity NPD5695 Phase 3
0.5745 Remote Similarity NPD5210 Approved
0.5745 Remote Similarity NPD4629 Approved
0.573 Remote Similarity NPD5786 Approved
0.573 Remote Similarity NPD6098 Approved
0.573 Remote Similarity NPD3574 Clinical (unspecified phase)
0.573 Remote Similarity NPD5279 Phase 3
0.5714 Remote Similarity NPD5784 Clinical (unspecified phase)
0.5699 Remote Similarity NPD6399 Phase 3
0.5699 Remote Similarity NPD5133 Approved
0.5673 Remote Similarity NPD6053 Discontinued
0.567 Remote Similarity NPD5285 Approved
0.567 Remote Similarity NPD4696 Approved
0.567 Remote Similarity NPD4700 Approved
0.567 Remote Similarity NPD5286 Approved
0.5644 Remote Similarity NPD7899 Clinical (unspecified phase)
0.5638 Remote Similarity NPD5282 Discontinued
0.5631 Remote Similarity NPD6371 Approved
0.5625 Remote Similarity NPD6083 Phase 2
0.5625 Remote Similarity NPD6084 Phase 2
0.5612 Remote Similarity NPD5223 Approved
0.5604 Remote Similarity NPD5208 Approved

Structure

External Identifiers

PubChem CID   10243299
ChEMBL   CHEMBL456292
ZINC  

Physicochemical Properties

Molecular Weight:  238.19
ALogP:  0.7225
MLogP:  2.89
XLogP:  2.613
# Rotatable Bonds:  7
Polar Surface Area:  40.46
# H-Bond Aceptor:  2
# H-Bond Donor:  2
# Rings:  2
# Heavy Atoms:  17

Download Data

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Biological Activities  
Similar NPs/Drugs