Natural Product: NPC99480

Natural Product ID:  NPC99480
Common Name:   Ent-Spathulenol
IUPAC Name:   (1aS,4aS,7R,7aS,7bS)-1,1,7-trimethyl-4-methylidene-1a,2,3,4a,5,6,7a,7b-octahydrocyclopropa[h]azulen-7-ol
Synonyms:   Ent-Spathulenol
Molecular Formula:   C15H24O
Standard InCHIKey:  FRMCCTDTYSRUBE-HYFYGGESSA-N
Standard InCHI:  InChI=1S/C15H24O/c1-9-5-6-11-13(14(11,2)3)12-10(9)7-8-15(12,4)16/h10-13,16H,1,5-8H2,2-4H3/t10-,11+,12+,13+,15-/m1/s1
Canonical SMILES:  C=C1CC[C@H]2[C@@H]([C@@H]3[C@@H]1CC[C@@]3(C)O)C2(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
NPO29956 Sanicula lamelligera Species Apiaceae Eukaryota Whole plants Mountain Emei, Sichuan Province, China 2008-OCT PMID[21561060]
NPO11438 Angelica gigas Species Apiaceae Eukaryota TM-MC*
NPO163 Daucus carota Species Apiaceae Eukaryota TM-MC*
NPO8698 Zanthoxylum schinifolium Species Rutaceae Eukaryota TM-MC*
NPO15462 Angelica sinensis Species Apiaceae Eukaryota TM-MC*
NPO21355 Elsholtzia ciliata Species Lamiaceae Eukaryota TM-MC*
NPO20553 Zingiber officinale Species Zingiberaceae Eukaryota TM-MC*
NPO26589 Artemisia annua Species Asteraceae Eukaryota TM-MC*
NPO8874 Glehnia littoralis Species Apiaceae Eukaryota TM-MC*
NPO523 Tussilago farfara Species Asteraceae Eukaryota TCMID*
NPO10506 Artemisia apiacea Species Asteraceae Eukaryota TM-MC*
NPO1436 Houttuynia cordata Species Saururaceae Eukaryota TM-MC*
NPO4776 Cassia roxburghii Species Fabaceae Eukaryota UNPD*
NPO11100 Artemisia capillaris Species Asteraceae Eukaryota TM-MC*
NPO4391 Hypericum perforatum Species Hypericaceae Eukaryota TM-MC*
NPO13389 Cystoseira barbatula Species Sargassaceae Eukaryota UNPD*
NPO28688 Aster tataricus Species Asteraceae Eukaryota TM-MC*
NPO13274 Illicium verum Species Schisandraceae Eukaryota TM-MC*
NPO16087 Atractylodes lancea Species Asteraceae Eukaryota TM-MC*
NPO28807 Laggera pterodonta Species Asteraceae Eukaryota TM-MC*
NPO20902 Atractylodes macrocephala Species Asteraceae Eukaryota TM-MC*
NPO23548 Leonurus japonicus Species Lamiaceae Eukaryota TM-MC*
NPO14236 Physalis coztomatl Species Solanaceae Eukaryota UNPD*
NPO25825 Saussurea costus Species Asteraceae Eukaryota TM-MC*
NPO18951 Ligusticum sinense Species Apiaceae Eukaryota TM-MC*
NPO30691 Porella chilensis Species Porellaceae Eukaryota Argentine PMID[21384863]
NPO22258 Chrysanthemum indicum Species Asteraceae Eukaryota TM-MC*
NPO11474 Ligusticum jeholense Species Apiaceae Eukaryota TM-MC*
NPO20440 Chrysanthemum x morifolium Species Asteraceae Eukaryota TM-MC*
NPO2154 Ligusticum tenuissimum Species Apiaceae Eukaryota TM-MC*
NPO14567 Ursinia anethoides Species Asteraceae Eukaryota UNPD*
NPO17295 Chrysanthemum zawadskii Species Asteraceae Eukaryota TM-MC*
NPO18811 Magnolia biondii Species Magnoliaceae Eukaryota TM-MC*
NPO18894 Karenia mikimotoi Species Kareniaceae Eukaryota UNPD*
NPO9546 Cinamomum cassia NA NA NA TM-MC*
NPO15064 Magnolia denudata Species Magnoliaceae Eukaryota TM-MC*
NPO1918 Magnolia kobus Species Magnoliaceae Eukaryota TM-MC*
NPO2360 Jatropha mahafalensis Species Euphorbiaceae Eukaryota UNPD*
NPO8255 Cinnamomum aromaticum Species Lauraceae Eukaryota TM-MC*
NPO27288 Citrus maxima Species Rutaceae Eukaryota TM-MC*
NPO15294 Magnolia salicifolia Species Magnoliaceae Eukaryota TM-MC*
NPO14407 Stachyurus praecox Species Stachyuraceae Eukaryota UNPD*
NPO22033 Cnidium officinale Species Apiaceae Eukaryota TM-MC*
NPO25197 Magnolia sprengeri Species Magnoliaceae Eukaryota TM-MC*
NPO10423 Sibthorpia europaea Species Plantaginaceae Eukaryota UNPD*
NPO5649 Coptis chinensis Species Ranunculaceae Eukaryota TM-MC*
NPO23256 Mentha arvensis Species Lamiaceae Eukaryota TM-MC*
NPO4424 Salvia amplexicaulis Species Lamiaceae Eukaryota UNPD*
NPO22622 Coptis deltoidea Species Ranunculaceae Eukaryota TM-MC*
NPO13857 Mentha canadensis Species Lamiaceae Eukaryota TM-MC*
NPO20523 Bacillus subtilis Species Bacillaceae Bacteria UNPD*
NPO13757 Coptis japonica Species Ranunculaceae Eukaryota TM-MC*
NPO18046 Mosla chinensis Species Lamiaceae Eukaryota TM-MC*
NPO15275 Briareum asbestinum Species Briareidae Eukaryota UNPD*
NPO29008 Coptis teeta Species Ranunculaceae Eukaryota TM-MC*
NPO12182 Murraya exotica Species Rutaceae Eukaryota TM-MC*
NPO13247 Stevia pilosa Species Asteraceae Eukaryota UNPD*
NPO15020 Flindersia amboinensis Species Rutaceae Eukaryota UNPD*
NPO22741 Curcuma kwangsiensis Species Zingiberaceae Eukaryota TM-MC*
NPO2715 Murraya paniculata Species Rutaceae Eukaryota TM-MC*
NPO15862 Eminium lehmannii Species Araceae Eukaryota UNPD*
NPO24124 Curcuma longa Species Zingiberaceae Eukaryota TM-MC*
NPO14108 Nardostachys jatamansi Species Caprifoliaceae Eukaryota TM-MC*
NPO8520 Mucor spinosus Species Mucoraceae Eukaryota UNPD*
NPO18068 Curcuma phaeocaulis Species Zingiberaceae Eukaryota TM-MC*
NPO29141 Panax ginseng Species Araliaceae Eukaryota TM-MC*
NPO28017 Aster altaicus Species Asteraceae Eukaryota UNPD*
NPO2618 Curcuma wenyujin Species Zingiberaceae Eukaryota TM-MC*
NPO21891 Panax notoginseng Species Araliaceae Eukaryota TM-MC*
NPO11872 Eleutherococcus senticosus Species Araliaceae Eukaryota TM-MC*
NPO7929 Curcuma zedoaria Species Zingiberaceae Eukaryota TM-MC*
NPO8650 Perilla frutescens Species Lamiaceae Eukaryota TM-MC*
NPO25682 Acorus calamus Species Acoraceae Eukaryota TM-MC*
NPO22796 Cyperus rotundus Species Cyperaceae Eukaryota TM-MC*
NPO29463 Pogostemon cablin Species Lamiaceae Eukaryota TM-MC*
NPO18007 Agrimonia pilosa Species Rosaceae Eukaryota TM-MC*
NPO16039 Scutellaria barbata Species Lamiaceae Eukaryota TM-MC*
NPO29956 Sanicula lamelligera Species Apiaceae Eukaryota Whole Plants PMID[21561060]
NPO12935 Thymus quinquecostatus Species Lamiaceae Eukaryota TM-MC*
NPO30347 Porella densifolia Species Porellaceae Eukaryota PMID[21384863]
NPO19472 Thymus vulgaris Species Lamiaceae Eukaryota TM-MC*
NPO30691 Porella chilensis Species Porellaceae Eukaryota PMID[21384863]
NPO5315 Zanthoxylum bungeanum Species Rutaceae Eukaryota TM-MC*
NPO523 Tussilago farfara Species Asteraceae Eukaryota TCM_Taiwan*
NPO9650 Zanthoxylum nitidum Species Rutaceae Eukaryota TM-MC*
NPO2921 Angelica acutiloba Species Apiaceae Eukaryota TM-MC*
NPO9290 Zanthoxylum piperitum Species Rutaceae Eukaryota TM-MC*

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT2 Others Unspecified Inhibition = 33 % 21384863
NPT2 Others Unspecified Activity = 33 % 21384863
NPT18 Organism Pseudomonas aeruginosa Pseudomonas aeruginosa Inhibition = 41 % 21384863
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
NPT2 Others Unspecified Ratio CC50/EC50 = 1.6 21561060
NPT24 Organism Human immunodeficiency virus 1 Human immunodeficiency virus 1 EC50 = 103600 nM 21561060
NPT1452 Cell Line C8166 Homo sapiens CC50 = 170500 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 NPC99480 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 NPC184049
0.8644 High Similarity NPC52431
0.8644 High Similarity NPC310228
0.8361 Intermediate Similarity NPC15152
0.8333 Intermediate Similarity NPC471660
0.8197 Intermediate Similarity NPC252809
0.8182 Intermediate Similarity NPC127997
0.8182 Intermediate Similarity NPC95969
0.8125 Intermediate Similarity NPC469328
0.8088 Intermediate Similarity NPC471659
0.8033 Intermediate Similarity NPC469321
0.8033 Intermediate Similarity NPC5698
0.8 Intermediate Similarity NPC278550
0.7966 Intermediate Similarity NPC45387
0.7937 Intermediate Similarity NPC474480
0.7903 Intermediate Similarity NPC162109
0.7903 Intermediate Similarity NPC323153
0.7857 Intermediate Similarity NPC471658
0.7778 Intermediate Similarity NPC63111
0.7705 Intermediate Similarity NPC291147
0.7692 Intermediate Similarity NPC238352
0.7692 Intermediate Similarity NPC477009
0.7692 Intermediate Similarity NPC261782
0.7692 Intermediate Similarity NPC205618
0.7692 Intermediate Similarity NPC469326
0.7619 Intermediate Similarity NPC135648
0.7538 Intermediate Similarity NPC219940
0.7536 Intermediate Similarity NPC471662
0.7463 Intermediate Similarity NPC136813
0.7432 Intermediate Similarity NPC471656
0.7391 Intermediate Similarity NPC133873
0.7333 Intermediate Similarity NPC471661
0.7333 Intermediate Similarity NPC192962
0.7286 Intermediate Similarity NPC41886
0.7273 Intermediate Similarity NPC90803
0.7273 Intermediate Similarity NPC23145
0.7273 Intermediate Similarity NPC90506
0.7258 Intermediate Similarity NPC39068
0.7258 Intermediate Similarity NPC274396
0.7258 Intermediate Similarity NPC264779
0.7246 Intermediate Similarity NPC144647
0.7231 Intermediate Similarity NPC210346
0.7231 Intermediate Similarity NPC147524
0.7206 Intermediate Similarity NPC74885
0.7206 Intermediate Similarity NPC308522
0.7164 Intermediate Similarity NPC300442
0.7143 Intermediate Similarity NPC471781
0.7123 Intermediate Similarity NPC126969
0.7121 Intermediate Similarity NPC211291
0.7121 Intermediate Similarity NPC133368
0.7101 Intermediate Similarity NPC167527
0.7083 Intermediate Similarity NPC309178
0.7042 Intermediate Similarity NPC469737
0.7031 Intermediate Similarity NPC10017
0.7031 Intermediate Similarity NPC474769
0.7031 Intermediate Similarity NPC189290
0.7015 Intermediate Similarity NPC140233
0.7015 Intermediate Similarity NPC309300
0.7015 Intermediate Similarity NPC287744
0.6986 Remote Similarity NPC77501
0.6957 Remote Similarity NPC472253
0.6957 Remote Similarity NPC477791
0.6957 Remote Similarity NPC472255
0.6944 Remote Similarity NPC234527
0.6944 Remote Similarity NPC195489
0.6944 Remote Similarity NPC14352
0.6935 Remote Similarity NPC286752
0.6923 Remote Similarity NPC475968
0.6901 Remote Similarity NPC18543
0.6901 Remote Similarity NPC475728
0.6892 Remote Similarity NPC310643
0.6866 Remote Similarity NPC279200
0.6857 Remote Similarity NPC224532
0.6849 Remote Similarity NPC196358
0.6849 Remote Similarity NPC145552
0.6849 Remote Similarity NPC5046
0.6849 Remote Similarity NPC49168
0.6849 Remote Similarity NPC254509
0.6812 Remote Similarity NPC162309
0.6812 Remote Similarity NPC272125
0.6806 Remote Similarity NPC164045
0.68 Remote Similarity NPC471454
0.679 Remote Similarity NPC45957
0.679 Remote Similarity NPC471657
0.678 Remote Similarity NPC100445
0.6769 Remote Similarity NPC475830
0.6757 Remote Similarity NPC313185
0.6757 Remote Similarity NPC70982
0.6757 Remote Similarity NPC230704
0.6757 Remote Similarity NPC251435
0.6757 Remote Similarity NPC200243
0.6727 Remote Similarity NPC246165
0.6724 Remote Similarity NPC87439
0.6719 Remote Similarity NPC179024
0.6719 Remote Similarity NPC3025
0.6716 Remote Similarity NPC41160
0.6712 Remote Similarity NPC300940
0.6712 Remote Similarity NPC469320
0.6712 Remote Similarity NPC472506
0.6711 Remote Similarity NPC42853
0.6711 Remote Similarity NPC472342
0.6711 Remote Similarity NPC321690
0.6667 Remote Similarity NPC27243
0.6667 Remote Similarity NPC476737
0.6667 Remote Similarity NPC15162
0.6667 Remote Similarity NPC182848
0.6667 Remote Similarity NPC254845
0.6667 Remote Similarity NPC165069
0.6667 Remote Similarity NPC476317
0.6667 Remote Similarity NPC470041
0.6667 Remote Similarity NPC19569
0.6667 Remote Similarity NPC472472
0.6667 Remote Similarity NPC61503
0.6667 Remote Similarity NPC215481
0.6627 Remote Similarity NPC170775
0.6625 Remote Similarity NPC242016
0.6623 Remote Similarity NPC49599
0.6623 Remote Similarity NPC49627
0.6622 Remote Similarity NPC27395
0.6622 Remote Similarity NPC476736
0.6622 Remote Similarity NPC329090
0.662 Remote Similarity NPC160209
0.6615 Remote Similarity NPC65786
0.6615 Remote Similarity NPC119425
0.6615 Remote Similarity NPC101285
0.6615 Remote Similarity NPC7491
0.6615 Remote Similarity NPC13789
0.6615 Remote Similarity NPC27853
0.6613 Remote Similarity NPC179169
0.6613 Remote Similarity NPC181255
0.6613 Remote Similarity NPC306195
0.6613 Remote Similarity NPC157781
0.6613 Remote Similarity NPC35519
0.6579 Remote Similarity NPC331618
0.6579 Remote Similarity NPC34019
0.6579 Remote Similarity NPC257191
0.6575 Remote Similarity NPC111234
0.6575 Remote Similarity NPC469343
0.6562 Remote Similarity NPC178223
0.6562 Remote Similarity NPC283655
0.6562 Remote Similarity NPC277917
0.6562 Remote Similarity NPC89069
0.6562 Remote Similarity NPC166894
0.6562 Remote Similarity NPC218525
0.6557 Remote Similarity NPC131623
0.6557 Remote Similarity NPC329773
0.6538 Remote Similarity NPC80622
0.6538 Remote Similarity NPC476625
0.6538 Remote Similarity NPC156658
0.6538 Remote Similarity NPC164218
0.6538 Remote Similarity NPC258965
0.6533 Remote Similarity NPC201263
0.6533 Remote Similarity NPC319090
0.6533 Remote Similarity NPC328104
0.6533 Remote Similarity NPC113639
0.6533 Remote Similarity NPC3403
0.6528 Remote Similarity NPC474900
0.6528 Remote Similarity NPC22301
0.6522 Remote Similarity NPC101128
0.65 Remote Similarity NPC471340
0.65 Remote Similarity NPC260852
0.6494 Remote Similarity NPC477522
0.6494 Remote Similarity NPC477817
0.6494 Remote Similarity NPC65897
0.6494 Remote Similarity NPC302041
0.6494 Remote Similarity NPC469324
0.6494 Remote Similarity NPC477819
0.6494 Remote Similarity NPC85346
0.6494 Remote Similarity NPC477514
0.6494 Remote Similarity NPC472501
0.6486 Remote Similarity NPC474140
0.6479 Remote Similarity NPC33583
0.6479 Remote Similarity NPC161612
0.6471 Remote Similarity NPC274704
0.6452 Remote Similarity NPC26906
0.6452 Remote Similarity NPC214584
0.6447 Remote Similarity NPC315261
0.6447 Remote Similarity NPC124289
0.6447 Remote Similarity NPC91573
0.6447 Remote Similarity NPC96319
0.6447 Remote Similarity NPC38141
0.6447 Remote Similarity NPC141346
0.6447 Remote Similarity NPC25908
0.6447 Remote Similarity NPC473437
0.6447 Remote Similarity NPC142759
0.6447 Remote Similarity NPC20466
0.6447 Remote Similarity NPC115719
0.6441 Remote Similarity NPC229403
0.6438 Remote Similarity NPC45296
0.6429 Remote Similarity NPC258595
0.6429 Remote Similarity NPC64123
0.6418 Remote Similarity NPC95958
0.641 Remote Similarity NPC1319
0.6406 Remote Similarity NPC32222
0.6406 Remote Similarity NPC202146
0.64 Remote Similarity NPC7382
0.64 Remote Similarity NPC206875
0.64 Remote Similarity NPC25511
0.64 Remote Similarity NPC62657
0.64 Remote Similarity NPC192638

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC99480 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
0.7286 Intermediate Similarity NPD4243 Approved
0.7083 Intermediate Similarity NPD4785 Approved
0.7083 Intermediate Similarity NPD4784 Approved
0.6986 Remote Similarity NPD4190 Phase 3
0.6986 Remote Similarity NPD5275 Approved
0.6623 Remote Similarity NPD4195 Approved
0.6622 Remote Similarity NPD6924 Approved
0.6622 Remote Similarity NPD6926 Approved
0.6447 Remote Similarity NPD6933 Approved
0.6447 Remote Similarity NPD3701 Clinical (unspecified phase)
0.6375 Remote Similarity NPD4223 Phase 3
0.6375 Remote Similarity NPD4221 Approved
0.6316 Remote Similarity NPD6942 Approved
0.6316 Remote Similarity NPD7339 Approved
0.6301 Remote Similarity NPD6923 Approved
0.6301 Remote Similarity NPD6922 Approved
0.6296 Remote Similarity NPD4788 Approved
0.622 Remote Similarity NPD4197 Approved
0.6216 Remote Similarity NPD7143 Approved
0.6216 Remote Similarity NPD7144 Approved
0.6145 Remote Similarity NPD5329 Approved
0.6133 Remote Similarity NPD7151 Approved
0.6133 Remote Similarity NPD7152 Approved
0.6133 Remote Similarity NPD7150 Approved
0.6125 Remote Similarity NPD6931 Approved
0.6125 Remote Similarity NPD6930 Phase 2
0.6125 Remote Similarity NPD7525 Registered
0.6125 Remote Similarity NPD4748 Discontinued
0.6071 Remote Similarity NPD4693 Phase 3
0.6071 Remote Similarity NPD4690 Approved
0.6071 Remote Similarity NPD5280 Approved
0.6071 Remote Similarity NPD4688 Approved
0.6071 Remote Similarity NPD4689 Approved
0.6071 Remote Similarity NPD4138 Approved
0.6071 Remote Similarity NPD5205 Approved
0.6071 Remote Similarity NPD4694 Approved
0.6071 Remote Similarity NPD5690 Phase 2
0.6049 Remote Similarity NPD4139 Approved
0.6049 Remote Similarity NPD4692 Approved
0.6 Remote Similarity NPD4751 Clinical (unspecified phase)
0.6 Remote Similarity NPD6929 Approved
0.5949 Remote Similarity NPD6932 Approved
0.593 Remote Similarity NPD4518 Approved
0.593 Remote Similarity NPD4723 Approved
0.593 Remote Similarity NPD4722 Approved
0.5926 Remote Similarity NPD7509 Discontinued
0.5904 Remote Similarity NPD6695 Phase 3
0.5862 Remote Similarity NPD4753 Phase 2
0.5854 Remote Similarity NPD6902 Approved
0.5843 Remote Similarity NPD5133 Approved
0.5833 Remote Similarity NPD3665 Phase 1
0.5833 Remote Similarity NPD3666 Approved
0.5833 Remote Similarity NPD3133 Approved
0.5833 Remote Similarity NPD7338 Clinical (unspecified phase)
0.5802 Remote Similarity NPD6683 Phase 2
0.5795 Remote Similarity NPD4001 Clinical (unspecified phase)
0.5795 Remote Similarity NPD4096 Approved
0.5765 Remote Similarity NPD6893 Approved
0.575 Remote Similarity NPD6925 Approved
0.575 Remote Similarity NPD5776 Phase 2
0.5732 Remote Similarity NPD7514 Phase 3
0.573 Remote Similarity NPD5284 Approved
0.573 Remote Similarity NPD5281 Approved
0.5679 Remote Similarity NPD7322 Clinical (unspecified phase)
0.5679 Remote Similarity NPD7145 Approved
0.5667 Remote Similarity NPD4202 Approved
0.5647 Remote Similarity NPD4786 Approved
0.5645 Remote Similarity NPD386 Approved
0.5645 Remote Similarity NPD388 Approved
0.5634 Remote Similarity NPD1145 Discontinued
0.5632 Remote Similarity NPD7524 Approved
0.5632 Remote Similarity NPD7750 Discontinued
0.5625 Remote Similarity NPD1346 Approved

Structure

External Identifiers

PubChem CID   13854255
ChEMBL   CHEMBL1774433
ZINC  

Physicochemical Properties

Molecular Weight:  220.18
ALogP:  1.7158
MLogP:  3
XLogP:  4.157
# Rotatable Bonds:  4
Polar Surface Area:  20.23
# H-Bond Aceptor:  1
# H-Bond Donor:  1
# Rings:  3
# Heavy Atoms:  16

Download Data

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Biological Activities  
Similar NPs/Drugs