Natural Product: NPC11379

Natural Product ID:  NPC11379
Common Name:   Protostemodiol
IUPAC Name:   (5Z)-5-[(2S)-2-[(3S,8S,9R,9aS)-8-hydroxy-3-[(2S,4S)-4-methyl-5-oxooxolan-2-yl]-2,3,5,6,7,8,9,9a-octahydro-1H-pyrrolo[1,2-a]azepin-9-yl]-1-hydroxypropylidene]-4-methoxy-3-methylfuran-2-one
Synonyms:   Protostemodiol
Molecular Formula:   C23H33NO7
Standard InCHIKey:  OYRUSEHZRBXHJH-SXKCXTSXSA-N
Standard InCHI:  InChI=1S/C23H33NO7/c1-11-10-17(30-22(11)27)14-7-8-15-18(16(25)6-5-9-24(14)15)12(2)19(26)21-20(29-4)13(3)23(28)31-21/h11-12,14-18,25-26H,5-10H2,1-4H3/b21-19-/t11-,12-,14-,15-,16-,17-,18+/m0/s1
Canonical SMILES:  COC1=C(C)C(=O)O/C/1=C(/[C@H]([C@H]1[C@@H](O)CCCN2[C@H]1CC[C@H]2[C@@H]1C[C@@H](C(=O)O1)C)C)O
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
NPO28230 Stemona japonica Species Stemonaceae Eukaryota Stems and leaves PMID[18163592]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT4586 Individual Protein Nicotinic acetylcholine receptor alpha1 subunit Heliothis virescens IC50 = 10000 nM 11429990

  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 NPC11379 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
0.8607 High Similarity NPC173173
0.8333 Intermediate Similarity NPC230849
0.8319 Intermediate Similarity NPC174463
0.8235 Intermediate Similarity NPC65045
0.8211 Intermediate Similarity NPC469999
0.7967 Intermediate Similarity NPC470000
0.7899 Intermediate Similarity NPC43648
0.7891 Intermediate Similarity NPC215507
0.784 Intermediate Similarity NPC323168
0.784 Intermediate Similarity NPC111162
0.784 Intermediate Similarity NPC477990
0.784 Intermediate Similarity NPC477989
0.784 Intermediate Similarity NPC293550
0.7642 Intermediate Similarity NPC469997
0.7638 Intermediate Similarity NPC326386
0.7638 Intermediate Similarity NPC471087
0.7638 Intermediate Similarity NPC477985
0.7627 Intermediate Similarity NPC271562
0.752 Intermediate Similarity NPC138534
0.752 Intermediate Similarity NPC477986
0.7462 Intermediate Similarity NPC471086
0.7395 Intermediate Similarity NPC471844
0.7377 Intermediate Similarity NPC58281
0.7368 Intermediate Similarity NPC133089
0.7348 Intermediate Similarity NPC477988
0.7302 Intermediate Similarity NPC235625
0.7293 Intermediate Similarity NPC120335
0.7176 Intermediate Similarity NPC329401
0.7176 Intermediate Similarity NPC477987
0.7155 Intermediate Similarity NPC471843
0.709 Intermediate Similarity NPC307165
0.7083 Intermediate Similarity NPC265094
0.7069 Intermediate Similarity NPC150041
0.6949 Remote Similarity NPC476344
0.6917 Remote Similarity NPC474371
0.6875 Remote Similarity NPC471846
0.6875 Remote Similarity NPC471845
0.6875 Remote Similarity NPC39041
0.6875 Remote Similarity NPC202722
0.6875 Remote Similarity NPC241294
0.685 Remote Similarity NPC193471
0.685 Remote Similarity NPC130124
0.6769 Remote Similarity NPC106791
0.6769 Remote Similarity NPC201889
0.6748 Remote Similarity NPC64168
0.6746 Remote Similarity NPC469603
0.6742 Remote Similarity NPC23963
0.6741 Remote Similarity NPC476951
0.6721 Remote Similarity NPC287638
0.6721 Remote Similarity NPC194750
0.6721 Remote Similarity NPC473289
0.6721 Remote Similarity NPC233274
0.6693 Remote Similarity NPC30911
0.6693 Remote Similarity NPC316984
0.6667 Remote Similarity NPC173690
0.6667 Remote Similarity NPC6271
0.6667 Remote Similarity NPC279833
0.6667 Remote Similarity NPC80439
0.6641 Remote Similarity NPC469466
0.6641 Remote Similarity NPC284656
0.6639 Remote Similarity NPC188785
0.6636 Remote Similarity NPC216090
0.6623 Remote Similarity NPC475342
0.6587 Remote Similarity NPC474099
0.6562 Remote Similarity NPC168758
0.6562 Remote Similarity NPC181510
0.6562 Remote Similarity NPC47857
0.656 Remote Similarity NPC93179
0.6544 Remote Similarity NPC309525
0.6532 Remote Similarity NPC68001
0.6532 Remote Similarity NPC474827
0.6532 Remote Similarity NPC199831
0.6532 Remote Similarity NPC474828
0.6522 Remote Similarity NPC469861
0.6522 Remote Similarity NPC469860
0.6522 Remote Similarity NPC130436
0.6522 Remote Similarity NPC470539
0.6512 Remote Similarity NPC314550
0.648 Remote Similarity NPC469604
0.648 Remote Similarity NPC44514
0.6391 Remote Similarity NPC476956
0.6391 Remote Similarity NPC476952
0.6364 Remote Similarity NPC470538
0.6349 Remote Similarity NPC133420
0.6343 Remote Similarity NPC471261
0.6338 Remote Similarity NPC313348
0.6338 Remote Similarity NPC475987
0.632 Remote Similarity NPC474244
0.6319 Remote Similarity NPC45813
0.6271 Remote Similarity NPC322966
0.626 Remote Similarity NPC276995
0.626 Remote Similarity NPC52820
0.626 Remote Similarity NPC76660
0.6259 Remote Similarity NPC470537
0.6259 Remote Similarity NPC280903
0.6212 Remote Similarity NPC469597
0.6186 Remote Similarity NPC52533
0.6183 Remote Similarity NPC470534
0.6176 Remote Similarity NPC88190
0.6167 Remote Similarity NPC476019
0.6167 Remote Similarity NPC159568
0.616 Remote Similarity NPC26597
0.6159 Remote Similarity NPC316133
0.6159 Remote Similarity NPC318445
0.6154 Remote Similarity NPC470536
0.6154 Remote Similarity NPC298484
0.6143 Remote Similarity NPC314282
0.6127 Remote Similarity NPC478139
0.6124 Remote Similarity NPC176773
0.6122 Remote Similarity NPC473955
0.6119 Remote Similarity NPC30196
0.6111 Remote Similarity NPC474348
0.6102 Remote Similarity NPC469483
0.6094 Remote Similarity NPC477001
0.6094 Remote Similarity NPC477000
0.6094 Remote Similarity NPC75523
0.6087 Remote Similarity NPC273185
0.6084 Remote Similarity NPC315011
0.6077 Remote Similarity NPC470535
0.6077 Remote Similarity NPC15413
0.6074 Remote Similarity NPC147707
0.6074 Remote Similarity NPC6531
0.6069 Remote Similarity NPC471256
0.6068 Remote Similarity NPC277918
0.6066 Remote Similarity NPC469998
0.6065 Remote Similarity NPC315809
0.6065 Remote Similarity NPC314050
0.6063 Remote Similarity NPC86077
0.6061 Remote Similarity NPC474411
0.6061 Remote Similarity NPC474431
0.6043 Remote Similarity NPC314629
0.6031 Remote Similarity NPC218602
0.6028 Remote Similarity NPC317654
0.6028 Remote Similarity NPC96010
0.6015 Remote Similarity NPC261750
0.6015 Remote Similarity NPC60432
0.6015 Remote Similarity NPC1111
0.6015 Remote Similarity NPC474995
0.6014 Remote Similarity NPC25025
0.6 Remote Similarity NPC172821
0.6 Remote Similarity NPC61257
0.6 Remote Similarity NPC320569
0.6 Remote Similarity NPC191929
0.6 Remote Similarity NPC314451
0.6 Remote Similarity NPC261952
0.6 Remote Similarity NPC171135
0.6 Remote Similarity NPC313342
0.6 Remote Similarity NPC169511
0.6 Remote Similarity NPC274446
0.6 Remote Similarity NPC151403
0.6 Remote Similarity NPC234077
0.6 Remote Similarity NPC39754
0.6 Remote Similarity NPC81045
0.6 Remote Similarity NPC100454
0.6 Remote Similarity NPC133730
0.6 Remote Similarity NPC313333
0.6 Remote Similarity NPC242364
0.6 Remote Similarity NPC287164
0.6 Remote Similarity NPC288629
0.6 Remote Similarity NPC314512
0.5985 Remote Similarity NPC113012
0.5985 Remote Similarity NPC122926
0.5984 Remote Similarity NPC118844
0.5984 Remote Similarity NPC110875
0.5984 Remote Similarity NPC299808
0.5984 Remote Similarity NPC72183
0.5983 Remote Similarity NPC475947
0.5972 Remote Similarity NPC90814
0.5972 Remote Similarity NPC316401
0.5972 Remote Similarity NPC189393
0.5966 Remote Similarity NPC241360
0.5966 Remote Similarity NPC293136
0.5966 Remote Similarity NPC132940
0.5956 Remote Similarity NPC209734
0.5954 Remote Similarity NPC70235
0.595 Remote Similarity NPC91067
0.595 Remote Similarity NPC42598
0.595 Remote Similarity NPC212664
0.595 Remote Similarity NPC93794
0.595 Remote Similarity NPC40066
0.595 Remote Similarity NPC318963
0.595 Remote Similarity NPC20621
0.595 Remote Similarity NPC81778
0.595 Remote Similarity NPC473504
0.5944 Remote Similarity NPC315387
0.5944 Remote Similarity NPC316205
0.5942 Remote Similarity NPC477140
0.5942 Remote Similarity NPC139867
0.5942 Remote Similarity NPC477143
0.594 Remote Similarity NPC147238
0.5938 Remote Similarity NPC189609
0.5938 Remote Similarity NPC291500
0.5938 Remote Similarity NPC140591
0.5938 Remote Similarity NPC303653
0.5938 Remote Similarity NPC197835
0.5935 Remote Similarity NPC473520
0.5935 Remote Similarity NPC179746
0.5935 Remote Similarity NPC81419
0.5926 Remote Similarity NPC472536
0.5926 Remote Similarity NPC103391

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC11379 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
0.6693 Remote Similarity NPD2204 Approved
0.6462 Remote Similarity NPD1376 Discontinued
0.6316 Remote Similarity NPD8137 Clinical (unspecified phase)
0.6269 Remote Similarity NPD7641 Discontinued
0.6268 Remote Similarity NPD6845 Suspended
0.6222 Remote Similarity NPD2132 Phase 3
0.6204 Remote Similarity NPD8080 Discontinued
0.6187 Remote Similarity NPD8451 Approved
0.6159 Remote Similarity NPD7642 Approved
0.6143 Remote Similarity NPD8448 Approved
0.6131 Remote Similarity NPD8274 Clinical (unspecified phase)
0.6127 Remote Similarity NPD8390 Approved
0.6127 Remote Similarity NPD8391 Approved
0.6127 Remote Similarity NPD8392 Approved
0.6084 Remote Similarity NPD2101 Approved
0.6071 Remote Similarity NPD8273 Phase 1
0.6 Remote Similarity NPD8341 Approved
0.6 Remote Similarity NPD8342 Approved
0.6 Remote Similarity NPD8299 Approved
0.6 Remote Similarity NPD8340 Approved
0.5942 Remote Similarity NPD1689 Approved
0.5891 Remote Similarity NPD2259 Approved
0.5891 Remote Similarity NPD2258 Approved
0.585 Remote Similarity NPD8415 Approved
0.5845 Remote Similarity NPD3677 Clinical (unspecified phase)
0.5828 Remote Similarity NPD6077 Discontinued
0.5811 Remote Similarity NPD8387 Clinical (unspecified phase)
0.5809 Remote Similarity NPD7915 Approved
0.5809 Remote Similarity NPD7916 Approved
0.5806 Remote Similarity NPD5781 Clinical (unspecified phase)
0.5794 Remote Similarity NPD5349 Clinical (unspecified phase)
0.5763 Remote Similarity NPD882 Phase 2
0.5763 Remote Similarity NPD883 Phase 2
0.5762 Remote Similarity NPD2569 Approved
0.5762 Remote Similarity NPD2567 Approved
0.5753 Remote Similarity NPD3661 Approved
0.5753 Remote Similarity NPD3662 Phase 3
0.5753 Remote Similarity NPD3664 Approved
0.5753 Remote Similarity NPD3663 Approved
0.5753 Remote Similarity NPD7260 Phase 2
0.5748 Remote Similarity NPD3715 Approved
0.5748 Remote Similarity NPD3714 Approved
0.5748 Remote Similarity NPD3713 Approved
0.5746 Remote Similarity NPD6421 Discontinued
0.5746 Remote Similarity NPD6420 Discontinued
0.5743 Remote Similarity NPD4619 Approved
0.5743 Remote Similarity NPD4621 Approved
0.5734 Remote Similarity NPD4816 Clinical (unspecified phase)
0.5725 Remote Similarity NPD961 Discontinued
0.5714 Remote Similarity NPD2613 Approved
0.5705 Remote Similarity NPD3089 Approved
0.5705 Remote Similarity NPD2566 Approved
0.5705 Remote Similarity NPD2574 Discontinued
0.5705 Remote Similarity NPD3088 Approved
0.5705 Remote Similarity NPD3614 Approved
0.5705 Remote Similarity NPD4746 Phase 3
0.5705 Remote Similarity NPD2572 Clinical (unspecified phase)
0.5705 Remote Similarity NPD3087 Approved
0.5705 Remote Similarity NPD2570 Approved
0.5705 Remote Similarity NPD2573 Approved
0.5705 Remote Similarity NPD3616 Approved
0.5705 Remote Similarity NPD4745 Approved
0.5705 Remote Similarity NPD2571 Approved
0.5705 Remote Similarity NPD3615 Approved
0.5705 Remote Similarity NPD3090 Approved
0.5704 Remote Similarity NPD7830 Approved
0.5704 Remote Similarity NPD7829 Approved
0.5674 Remote Similarity NPD8266 Approved
0.5674 Remote Similarity NPD8267 Approved
0.5674 Remote Similarity NPD8269 Approved
0.5674 Remote Similarity NPD7739 Clinical (unspecified phase)
0.5674 Remote Similarity NPD8268 Approved
0.5645 Remote Similarity NPD46 Approved
0.5645 Remote Similarity NPD6698 Approved
0.5643 Remote Similarity NPD2495 Phase 3
0.5641 Remote Similarity NPD2575 Approved
0.5639 Remote Similarity NPD8307 Discontinued
0.5639 Remote Similarity NPD7899 Clinical (unspecified phase)
0.5639 Remote Similarity NPD8140 Approved
0.5634 Remote Similarity NPD7624 Clinical (unspecified phase)
0.5634 Remote Similarity NPD7623 Phase 3
0.5629 Remote Similarity NPD4685 Phase 3
0.5629 Remote Similarity NPD4686 Approved
0.5629 Remote Similarity NPD4684 Phase 3
0.5621 Remote Similarity NPD8384 Approved
0.5603 Remote Similarity NPD7299 Clinical (unspecified phase)

Structure

External Identifiers

PubChem CID   54714180
ChEMBL   CHEMBL404867
ZINC  

Physicochemical Properties

Molecular Weight:  435.23
ALogP:  -1.7201
MLogP:  3.11
XLogP:  1.955
# Rotatable Bonds:  10
Polar Surface Area:  105.53
# H-Bond Aceptor:  8
# H-Bond Donor:  2
# Rings:  4
# Heavy Atoms:  31

Download Data

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Structure MOL file  
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Biological Activities  
Similar NPs/Drugs