Natural Product: NPC135438

Natural Product ID:  NPC135438
Common Name:   Labdanediol
IUPAC Name:   (1R,2R,4aS,8aS)-1-[(3S)-5-hydroxy-3-methylpentyl]-2,5,5,8a-tetramethyl-3,4,4a,6,7,8-hexahydro-1H-naphthalen-2-ol
Synonyms:   Labdanediol
Molecular Formula:   C20H38O2
Standard InCHIKey:  MCHQEVJMCLOQAZ-VBYALHQYSA-N
Standard InCHI:  InChI=1S/C20H38O2/c1-15(10-14-21)7-8-17-19(4)12-6-11-18(2,3)16(19)9-13-20(17,5)22/h15-17,21-22H,6-14H2,1-5H3/t15-,16-,17+,19-,20+/m0/s1
Canonical SMILES:  OCC[C@H](CC[C@H]1[C@](C)(O)CC[C@@H]2[C@]1(C)CCCC2(C)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
NPO275 Amphilophis odorata NA NA NA UNPD*
NPO17959 Berberis repens Species Berberidaceae Eukaryota UNPD*
NPO7932 Ips confusus Species Curculionidae Eukaryota UNPD*
NPO1509 Hippeastrum papilio Species Amaryllidaceae Eukaryota UNPD*
NPO8268 Croton laccifer Species Euphorbiaceae Eukaryota UNPD*
NPO5143 Millettia ferruginea Species Fabaceae Eukaryota UNPD*
NPO11973 Gymnothorax javanicus Species Muraenidae Eukaryota UNPD*
NPO7057 Ptarmica ptarmicifolia NA NA NA UNPD*
NPO623 Amaranthus hypochondriacus Species Amaranthaceae Eukaryota UNPD*
NPO1870 Polyporus dryadeus Species Polyporaceae Eukaryota UNPD*
NPO3423 Teucrium asiaticum Species Lamiaceae Eukaryota UNPD*
NPO780 Senecio viscosus Species Asteraceae Eukaryota UNPD*
NPO2302 Sedum litoreum Species Crassulaceae Eukaryota UNPD*
NPO6480 Zanthoxylum fraxineum Species Rutaceae Eukaryota UNPD*
NPO3829 Euphorbia myrsinites Species Euphorbiaceae Eukaryota UNPD*
NPO6081 Limnocharis flava Species Alismataceae Eukaryota UNPD*
NPO5481 Fomes robiniae Species Coriolaceae Eukaryota UNPD*
NPO4182 Hygrophorus chrysodon Species Hygrophoraceae Eukaryota UNPD*
NPO4007 Vicia amurensis Species Fabaceae Eukaryota UNPD*
NPO2862 Dendrilla cavernosa Species Darwinellidae Eukaryota UNPD*
NPO26520 Wyethia mollis Species Asteraceae Eukaryota UNPD*
NPO25934 Diphasiastrum thyoides Species Lycopodiaceae Eukaryota UNPD*
NPO5918 Thermopsis dolichocarpa Species Fabaceae Eukaryota UNPD*
NPO7216 Helicteres angustifolia Species Malvaceae Eukaryota UNPD*

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT113 Cell Line RAW264.7 Mus musculus Activity = 40 % 20447741
NPT113 Cell Line RAW264.7 Mus musculus IC50 = 25000 nM 20447741
NPT113 Cell Line RAW264.7 Mus musculus IC50 = 15000 nM 20447741

  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 NPC135438 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
0.963 High Similarity NPC236588
0.8833 High Similarity NPC80463
0.8833 High Similarity NPC260116
0.8571 High Similarity NPC471269
0.8548 High Similarity NPC48079
0.8548 High Similarity NPC476928
0.8545 High Similarity NPC36002
0.8545 High Similarity NPC102336
0.85 High Similarity NPC114891
0.85 High Similarity NPC290791
0.85 High Similarity NPC292419
0.8448 Intermediate Similarity NPC47663
0.8413 Intermediate Similarity NPC472741
0.8413 Intermediate Similarity NPC475893
0.8413 Intermediate Similarity NPC2648
0.8393 Intermediate Similarity NPC53209
0.8387 Intermediate Similarity NPC142712
0.8387 Intermediate Similarity NPC44122
0.8361 Intermediate Similarity NPC118937
0.8361 Intermediate Similarity NPC281540
0.8361 Intermediate Similarity NPC159654
0.8361 Intermediate Similarity NPC167995
0.8333 Intermediate Similarity NPC148174
0.8333 Intermediate Similarity NPC71460
0.8333 Intermediate Similarity NPC218585
0.8305 Intermediate Similarity NPC95958
0.8281 Intermediate Similarity NPC107919
0.8281 Intermediate Similarity NPC241085
0.8281 Intermediate Similarity NPC129829
0.8281 Intermediate Similarity NPC299948
0.8281 Intermediate Similarity NPC254037
0.8281 Intermediate Similarity NPC470833
0.8281 Intermediate Similarity NPC66407
0.8281 Intermediate Similarity NPC210323
0.8281 Intermediate Similarity NPC470830
0.8254 Intermediate Similarity NPC204233
0.8254 Intermediate Similarity NPC475884
0.8254 Intermediate Similarity NPC473230
0.8254 Intermediate Similarity NPC63190
0.8226 Intermediate Similarity NPC41577
0.8226 Intermediate Similarity NPC473276
0.8226 Intermediate Similarity NPC474380
0.8154 Intermediate Similarity NPC282454
0.8154 Intermediate Similarity NPC192192
0.8154 Intermediate Similarity NPC231945
0.8136 Intermediate Similarity NPC476735
0.8125 Intermediate Similarity NPC469987
0.8125 Intermediate Similarity NPC474756
0.8113 Intermediate Similarity NPC14552
0.8065 Intermediate Similarity NPC69149
0.8065 Intermediate Similarity NPC101128
0.8033 Intermediate Similarity NPC95804
0.8033 Intermediate Similarity NPC185547
0.803 Intermediate Similarity NPC157777
0.803 Intermediate Similarity NPC252182
0.803 Intermediate Similarity NPC109457
0.803 Intermediate Similarity NPC187471
0.803 Intermediate Similarity NPC195530
0.803 Intermediate Similarity NPC131506
0.803 Intermediate Similarity NPC473279
0.803 Intermediate Similarity NPC1340
0.803 Intermediate Similarity NPC167706
0.803 Intermediate Similarity NPC100586
0.803 Intermediate Similarity NPC470071
0.803 Intermediate Similarity NPC127094
0.803 Intermediate Similarity NPC157422
0.8 Intermediate Similarity NPC477820
0.7969 Intermediate Similarity NPC41542
0.7969 Intermediate Similarity NPC269077
0.7969 Intermediate Similarity NPC253303
0.7969 Intermediate Similarity NPC139207
0.7969 Intermediate Similarity NPC472984
0.7969 Intermediate Similarity NPC185874
0.7937 Intermediate Similarity NPC243469
0.7937 Intermediate Similarity NPC230047
0.7937 Intermediate Similarity NPC258595
0.7937 Intermediate Similarity NPC472946
0.7937 Intermediate Similarity NPC475943
0.7937 Intermediate Similarity NPC19311
0.7937 Intermediate Similarity NPC190827
0.791 Intermediate Similarity NPC473238
0.791 Intermediate Similarity NPC472341
0.791 Intermediate Similarity NPC153719
0.791 Intermediate Similarity NPC253805
0.791 Intermediate Similarity NPC81759
0.7903 Intermediate Similarity NPC236099
0.7903 Intermediate Similarity NPC209686
0.7903 Intermediate Similarity NPC249078
0.7879 Intermediate Similarity NPC232925
0.7879 Intermediate Similarity NPC251201
0.7879 Intermediate Similarity NPC63588
0.7846 Intermediate Similarity NPC244790
0.7833 Intermediate Similarity NPC87296
0.7833 Intermediate Similarity NPC215671
0.7833 Intermediate Similarity NPC475515
0.7818 Intermediate Similarity NPC316035
0.7797 Intermediate Similarity NPC3025
0.7794 Intermediate Similarity NPC475793
0.7794 Intermediate Similarity NPC237510
0.7794 Intermediate Similarity NPC304499
0.7794 Intermediate Similarity NPC10476
0.7794 Intermediate Similarity NPC201048
0.7794 Intermediate Similarity NPC192501
0.7794 Intermediate Similarity NPC228994
0.7794 Intermediate Similarity NPC476366
0.7794 Intermediate Similarity NPC477508
0.7778 Intermediate Similarity NPC198540
0.7778 Intermediate Similarity NPC94897
0.7778 Intermediate Similarity NPC147343
0.7778 Intermediate Similarity NPC176309
0.7778 Intermediate Similarity NPC287550
0.7778 Intermediate Similarity NPC144650
0.7778 Intermediate Similarity NPC84030
0.7778 Intermediate Similarity NPC223468
0.7761 Intermediate Similarity NPC478103
0.7761 Intermediate Similarity NPC8004
0.7761 Intermediate Similarity NPC127283
0.7727 Intermediate Similarity NPC9942
0.7692 Intermediate Similarity NPC101307
0.7692 Intermediate Similarity NPC88454
0.7692 Intermediate Similarity NPC117607
0.7681 Intermediate Similarity NPC196136
0.7681 Intermediate Similarity NPC317242
0.7681 Intermediate Similarity NPC91387
0.7681 Intermediate Similarity NPC158208
0.7681 Intermediate Similarity NPC3403
0.7681 Intermediate Similarity NPC472952
0.7681 Intermediate Similarity NPC270306
0.7681 Intermediate Similarity NPC472950
0.7681 Intermediate Similarity NPC243027
0.7681 Intermediate Similarity NPC231680
0.7656 Intermediate Similarity NPC172613
0.7656 Intermediate Similarity NPC282619
0.7656 Intermediate Similarity NPC208198
0.7656 Intermediate Similarity NPC2728
0.7656 Intermediate Similarity NPC60837
0.7656 Intermediate Similarity NPC11555
0.7656 Intermediate Similarity NPC64123
0.7647 Intermediate Similarity NPC232112
0.7647 Intermediate Similarity NPC470610
0.7647 Intermediate Similarity NPC477229
0.7647 Intermediate Similarity NPC211009
0.7647 Intermediate Similarity NPC68426
0.7647 Intermediate Similarity NPC282905
0.7612 Intermediate Similarity NPC45296
0.7576 Intermediate Similarity NPC276616
0.7576 Intermediate Similarity NPC478228
0.7576 Intermediate Similarity NPC245795
0.7571 Intermediate Similarity NPC91573
0.7571 Intermediate Similarity NPC470145
0.7571 Intermediate Similarity NPC63958
0.7571 Intermediate Similarity NPC163597
0.7571 Intermediate Similarity NPC470749
0.7544 Intermediate Similarity NPC307022
0.7541 Intermediate Similarity NPC474769
0.7541 Intermediate Similarity NPC162685
0.7541 Intermediate Similarity NPC189290
0.7538 Intermediate Similarity NPC473929
0.7538 Intermediate Similarity NPC476406
0.7536 Intermediate Similarity NPC159325
0.7536 Intermediate Similarity NPC476736
0.7536 Intermediate Similarity NPC48795
0.7536 Intermediate Similarity NPC475458
0.7536 Intermediate Similarity NPC74639
0.7536 Intermediate Similarity NPC478130
0.7536 Intermediate Similarity NPC472503
0.7536 Intermediate Similarity NPC168511
0.7536 Intermediate Similarity NPC308440
0.75 Intermediate Similarity NPC68656
0.75 Intermediate Similarity NPC151018
0.75 Intermediate Similarity NPC111234
0.75 Intermediate Similarity NPC89310
0.75 Intermediate Similarity NPC320549
0.75 Intermediate Similarity NPC301226
0.75 Intermediate Similarity NPC156277
0.75 Intermediate Similarity NPC58057
0.7465 Intermediate Similarity NPC105208
0.7465 Intermediate Similarity NPC474574
0.7465 Intermediate Similarity NPC133596
0.7465 Intermediate Similarity NPC128951
0.7465 Intermediate Similarity NPC23884
0.7465 Intermediate Similarity NPC470711
0.7465 Intermediate Similarity NPC475031
0.7465 Intermediate Similarity NPC64081
0.7465 Intermediate Similarity NPC185915
0.7465 Intermediate Similarity NPC11907
0.7465 Intermediate Similarity NPC476233
0.7465 Intermediate Similarity NPC302578
0.7465 Intermediate Similarity NPC192046
0.7465 Intermediate Similarity NPC477227
0.7465 Intermediate Similarity NPC470758
0.7465 Intermediate Similarity NPC169994
0.7463 Intermediate Similarity NPC213178
0.7463 Intermediate Similarity NPC327728
0.7463 Intermediate Similarity NPC131892
0.7463 Intermediate Similarity NPC6120
0.7458 Intermediate Similarity NPC32222
0.7458 Intermediate Similarity NPC202146
0.7429 Intermediate Similarity NPC231256
0.7429 Intermediate Similarity NPC273366

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC135438 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
0.8281 Intermediate Similarity NPD4267 Clinical (unspecified phase)
0.7879 Intermediate Similarity NPD4787 Phase 1
0.7778 Intermediate Similarity NPD384 Approved
0.7778 Intermediate Similarity NPD385 Approved
0.75 Intermediate Similarity NPD4809 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD4808 Clinical (unspecified phase)
0.7463 Intermediate Similarity NPD3699 Clinical (unspecified phase)
0.7463 Intermediate Similarity NPD3700 Clinical (unspecified phase)
0.7385 Intermediate Similarity NPD3171 Clinical (unspecified phase)
0.7324 Intermediate Similarity NPD6117 Approved
0.7313 Intermediate Similarity NPD5361 Clinical (unspecified phase)
0.7313 Intermediate Similarity NPD5360 Phase 3
0.7286 Intermediate Similarity NPD6113 Clinical (unspecified phase)
0.7273 Intermediate Similarity NPD388 Approved
0.7273 Intermediate Similarity NPD386 Approved
0.7222 Intermediate Similarity NPD6116 Phase 1
0.7183 Intermediate Similarity NPD3703 Phase 2
0.7162 Intermediate Similarity NPD7525 Registered
0.7123 Intermediate Similarity NPD6697 Approved
0.7123 Intermediate Similarity NPD6115 Approved
0.7123 Intermediate Similarity NPD6118 Approved
0.7123 Intermediate Similarity NPD6114 Approved
0.7101 Intermediate Similarity NPD4245 Approved
0.7101 Intermediate Similarity NPD4244 Approved
0.7101 Intermediate Similarity NPD4789 Approved
0.7059 Intermediate Similarity NPD6705 Phase 1
0.7027 Intermediate Similarity NPD7645 Phase 2
0.697 Remote Similarity NPD371 Approved
0.6957 Remote Similarity NPD3698 Phase 2
0.6761 Remote Similarity NPD4758 Discontinued
0.6712 Remote Similarity NPD7339 Approved
0.6712 Remote Similarity NPD6942 Approved
0.6711 Remote Similarity NPD6928 Phase 2
0.6667 Remote Similarity NPD3671 Phase 1
0.6622 Remote Similarity NPD3701 Clinical (unspecified phase)
0.6575 Remote Similarity NPD6924 Approved
0.6575 Remote Similarity NPD6926 Approved
0.6522 Remote Similarity NPD4224 Phase 2
0.65 Remote Similarity NPD7520 Clinical (unspecified phase)
0.6494 Remote Similarity NPD4748 Discontinued
0.6486 Remote Similarity NPD3702 Approved
0.6447 Remote Similarity NPD5364 Discontinued
0.64 Remote Similarity NPD6933 Approved
0.6351 Remote Similarity NPD1810 Approved
0.6351 Remote Similarity NPD1811 Approved
0.6316 Remote Similarity NPD367 Approved
0.6301 Remote Similarity NPD4243 Approved
0.6301 Remote Similarity NPD6081 Approved
0.6282 Remote Similarity NPD7509 Discontinued
0.625 Remote Similarity NPD4788 Approved
0.622 Remote Similarity NPD3618 Phase 1
0.619 Remote Similarity NPD5328 Approved
0.6173 Remote Similarity NPD4786 Approved
0.6133 Remote Similarity NPD4784 Approved
0.6133 Remote Similarity NPD4785 Approved
0.6125 Remote Similarity NPD3667 Approved
0.6118 Remote Similarity NPD6701 Clinical (unspecified phase)
0.6118 Remote Similarity NPD6700 Approved
0.6081 Remote Similarity NPD5777 Approved
0.6081 Remote Similarity NPD7152 Approved
0.6081 Remote Similarity NPD7151 Approved
0.6081 Remote Similarity NPD7150 Approved
0.6076 Remote Similarity NPD6930 Phase 2
0.6076 Remote Similarity NPD6931 Approved
0.6053 Remote Similarity NPD8264 Approved
0.6047 Remote Similarity NPD6079 Approved
0.6047 Remote Similarity NPD7515 Phase 2
0.6047 Remote Similarity NPD6703 Approved
0.6047 Remote Similarity NPD6702 Approved
0.6027 Remote Similarity NPD6922 Approved
0.6027 Remote Similarity NPD6923 Approved
0.5977 Remote Similarity NPD4202 Approved
0.5952 Remote Similarity NPD4751 Clinical (unspecified phase)
0.5949 Remote Similarity NPD6929 Approved
0.5946 Remote Similarity NPD2687 Approved
0.5946 Remote Similarity NPD2686 Approved
0.5946 Remote Similarity NPD7144 Approved
0.5946 Remote Similarity NPD2254 Approved
0.5946 Remote Similarity NPD7143 Approved
0.5897 Remote Similarity NPD6932 Approved
0.5862 Remote Similarity NPD8035 Phase 2
0.5862 Remote Similarity NPD8034 Phase 2
0.5854 Remote Similarity NPD6695 Phase 3
0.5846 Remote Similarity NPD3729 Clinical (unspecified phase)
0.5844 Remote Similarity NPD4190 Phase 3
0.5844 Remote Similarity NPD5275 Approved
0.5823 Remote Similarity NPD7322 Clinical (unspecified phase)
0.5795 Remote Similarity NPD8171 Discontinued
0.5783 Remote Similarity NPD3665 Phase 1
0.5783 Remote Similarity NPD7338 Clinical (unspecified phase)
0.5783 Remote Similarity NPD3666 Approved
0.5783 Remote Similarity NPD3133 Approved
0.575 Remote Similarity NPD6683 Phase 2
0.575 Remote Similarity NPD4195 Approved
0.5733 Remote Similarity NPD7532 Clinical (unspecified phase)
0.573 Remote Similarity NPD7748 Approved
0.5714 Remote Similarity NPD6893 Approved
0.5714 Remote Similarity NPD7919 Phase 3
0.5714 Remote Similarity NPD7920 Phase 3
0.5714 Remote Similarity NPD4755 Approved
0.5696 Remote Similarity NPD6925 Approved
0.5696 Remote Similarity NPD5776 Phase 2
0.5679 Remote Similarity NPD7332 Phase 2
0.5679 Remote Similarity NPD7514 Phase 3
0.5663 Remote Similarity NPD3669 Approved
0.5663 Remote Similarity NPD3670 Clinical (unspecified phase)
0.566 Remote Similarity NPD2272 Approved
0.566 Remote Similarity NPD5383 Approved
0.5652 Remote Similarity NPD3198 Approved
0.5652 Remote Similarity NPD7638 Approved
0.5652 Remote Similarity NPD8088 Phase 1
0.5647 Remote Similarity NPD3574 Clinical (unspecified phase)
0.5647 Remote Similarity NPD8308 Discontinued
0.5632 Remote Similarity NPD4753 Phase 2
0.5625 Remote Similarity NPD3617 Approved
0.5625 Remote Similarity NPD7145 Approved
0.561 Remote Similarity NPD6898 Phase 1
0.5606 Remote Similarity NPD615 Clinical (unspecified phase)
0.5604 Remote Similarity NPD4697 Phase 3
0.5604 Remote Similarity NPD5221 Approved
0.5604 Remote Similarity NPD5222 Approved
0.5604 Remote Similarity NPD5220 Clinical (unspecified phase)

Structure

External Identifiers

PubChem CID   11130717
ChEMBL   CHEMBL1172098
ZINC  

Physicochemical Properties

Molecular Weight:  310.29
ALogP:  0.9714
MLogP:  3.44
XLogP:  6.596
# Rotatable Bonds:  12
Polar Surface Area:  40.46
# H-Bond Aceptor:  2
# H-Bond Donor:  2
# Rings:  2
# Heavy Atoms:  22

Download Data

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Biological Activities  
Similar NPs/Drugs