Natural Product: NPC113976

Natural Product ID:  NPC113976
Common Name:   3-Epicaryoptin
IUPAC Name:   [(3S,4R,4aR,5S,7R,8S,8aR)-8-[(3aS,5S,6aS)-3a,4,5,6a-tetrahydrofuro[2,3-b]furan-5-yl]-3,5-diacetyloxy-7,8-dimethylspiro[2,3,5,6,7,8a-hexahydro-1H-naphthalene-4,2'-oxirane]-4a-yl]methyl acetate
Synonyms:  
Molecular Formula:   C26H36O9
Standard InCHIKey:  QVORLEZTALRJNW-WBTQUOTHSA-N
Standard InCHI:  InChI=1S/C26H36O9/c1-14-10-22(34-17(4)29)25(12-31-15(2)27)19(6-7-20(33-16(3)28)26(25)13-32-26)24(14,5)21-11-18-8-9-30-23(18)35-21/h8-9,14,18-23H,6-7,10-13H2,1-5H3/t14-,18-,19-,20+,21+,22+,23+,24+,25+,26-/m1/s1
Canonical SMILES:  CC(=O)OC[C@@]12[C@@H](OC(=O)C)C[C@H]([C@]([C@H]1CC[C@@H]([C@@]12CO1)OC(=O)C)(C)[C@H]1O[C@H]2[C@@H](C1)C=CO2)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
NPO33100 clerodendron sp. Species Lamiaceae Eukaryota PMID[12617583]
NPO16812 Ajuga bracteosa Species Lamiaceae Eukaryota Aerial parts PMID[21539300]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT1193 Organism Athalia rosae ruficornis Athalia rosae ruficornis Activity = 80 % 10.1016/S0305-1978(03)00160-1
NPT1369 Organism Henosepilachna vigintioctopunctata Henosepilachna vigintioctopunctata Activity = 9.37 % 10.1016/S0367-326X(99)00033-7
NPT1369 Organism Henosepilachna vigintioctopunctata Henosepilachna vigintioctopunctata Activity = 31.93 % 10.1016/S0367-326X(99)00033-7
NPT1369 Organism Henosepilachna vigintioctopunctata Henosepilachna vigintioctopunctata Activity = 31.07 % 10.1016/S0367-326X(99)00033-7
NPT1369 Organism Henosepilachna vigintioctopunctata Henosepilachna vigintioctopunctata Activity = 23.56 % 10.1016/S0367-326X(99)00033-7
NPT1369 Organism Henosepilachna vigintioctopunctata Henosepilachna vigintioctopunctata Activity = 16.12 % 10.1016/S0367-326X(99)00033-7
NPT1369 Organism Henosepilachna vigintioctopunctata Henosepilachna vigintioctopunctata Activity = 37.02 % 10.1016/S0367-326X(99)00033-7
NPT776 Organism Spodoptera littoralis Spodoptera littoralis Activity = 100 % 12617583
NPT1175 Organism Spodoptera litura Spodoptera litura Activity = 8.8 % 12617583
NPT1175 Organism Spodoptera litura Spodoptera litura Activity = 12.8 % 12617583
NPT1175 Organism Spodoptera litura Spodoptera litura Activity = 64.8 % 12617583
NPT1175 Organism Spodoptera litura Spodoptera litura Activity = 56.8 % 12617583
NPT1175 Organism Spodoptera litura Spodoptera litura Activity = 261.6 ug 12617583
NPT1175 Organism Spodoptera litura Spodoptera litura Activity = 250.2 ug 12617583
NPT1194 Organism Earias vitella Earias vitella Activity = 8 % 12617583
NPT1194 Organism Earias vitella Earias vitella Activity = 60.4 % 12617583
NPT1194 Organism Earias vitella Earias vitella Activity = 52 % 12617583
NPT1194 Organism Earias vitella Earias vitella Activity = 57.4 ug 12617583
NPT1194 Organism Earias vitella Earias vitella Activity = 53.2 ug 12617583
NPT1175 Organism Spodoptera litura Spodoptera litura Activity = 73.4 % 12617583
NPT1175 Organism Spodoptera litura Spodoptera litura Activity = 82.6 % 12617583
NPT1194 Organism Earias vitella Earias vitella Activity = 73 % 12617583
NPT1194 Organism Earias vitella Earias vitella Activity = 79.76 % 12617583

  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 NPC113976 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 NPC198549
0.9556 High Similarity NPC12297
0.9278 High Similarity NPC291414
0.9 High Similarity NPC305939
0.8911 High Similarity NPC86217
0.828 Intermediate Similarity NPC474008
0.8261 Intermediate Similarity NPC471367
0.8105 Intermediate Similarity NPC470872
0.8085 Intermediate Similarity NPC471369
0.8022 Intermediate Similarity NPC471217
0.8022 Intermediate Similarity NPC471216
0.7959 Intermediate Similarity NPC163902
0.7941 Intermediate Similarity NPC119467
0.7941 Intermediate Similarity NPC475767
0.7935 Intermediate Similarity NPC71541
0.7917 Intermediate Similarity NPC263079
0.79 Intermediate Similarity NPC171598
0.7895 Intermediate Similarity NPC471368
0.7843 Intermediate Similarity NPC317019
0.78 Intermediate Similarity NPC471362
0.78 Intermediate Similarity NPC471372
0.78 Intermediate Similarity NPC472189
0.7789 Intermediate Similarity NPC235402
0.7788 Intermediate Similarity NPC120009
0.7778 Intermediate Similarity NPC475307
0.7757 Intermediate Similarity NPC206618
0.7755 Intermediate Similarity NPC471371
0.7755 Intermediate Similarity NPC471370
0.7745 Intermediate Similarity NPC318917
0.7745 Intermediate Similarity NPC472186
0.7745 Intermediate Similarity NPC476800
0.7745 Intermediate Similarity NPC471366
0.7745 Intermediate Similarity NPC157739
0.7714 Intermediate Similarity NPC470062
0.7714 Intermediate Similarity NPC470058
0.7714 Intermediate Similarity NPC85593
0.7714 Intermediate Similarity NPC470043
0.7714 Intermediate Similarity NPC470060
0.7714 Intermediate Similarity NPC470059
0.7714 Intermediate Similarity NPC470064
0.7714 Intermediate Similarity NPC470061
0.7714 Intermediate Similarity NPC470057
0.7714 Intermediate Similarity NPC31430
0.767 Intermediate Similarity NPC324598
0.767 Intermediate Similarity NPC473545
0.767 Intermediate Similarity NPC473204
0.767 Intermediate Similarity NPC472187
0.7664 Intermediate Similarity NPC128795
0.7664 Intermediate Similarity NPC38948
0.7664 Intermediate Similarity NPC48548
0.7664 Intermediate Similarity NPC135015
0.7664 Intermediate Similarity NPC217921
0.7658 Intermediate Similarity NPC243981
0.7647 Intermediate Similarity NPC471770
0.7647 Intermediate Similarity NPC473555
0.7647 Intermediate Similarity NPC97867
0.7647 Intermediate Similarity NPC278939
0.7647 Intermediate Similarity NPC472188
0.7624 Intermediate Similarity NPC230347
0.7624 Intermediate Similarity NPC286612
0.7624 Intermediate Similarity NPC275310
0.7619 Intermediate Similarity NPC474575
0.7593 Intermediate Similarity NPC316974
0.7593 Intermediate Similarity NPC40728
0.7573 Intermediate Similarity NPC477928
0.757 Intermediate Similarity NPC125423
0.757 Intermediate Similarity NPC88013
0.757 Intermediate Similarity NPC475074
0.7551 Intermediate Similarity NPC144069
0.7549 Intermediate Similarity NPC94905
0.7549 Intermediate Similarity NPC8954
0.7525 Intermediate Similarity NPC140277
0.7525 Intermediate Similarity NPC211238
0.7523 Intermediate Similarity NPC127153
0.75 Intermediate Similarity NPC18953
0.75 Intermediate Similarity NPC91251
0.75 Intermediate Similarity NPC311223
0.7478 Intermediate Similarity NPC204731
0.7477 Intermediate Similarity NPC470055
0.7477 Intermediate Similarity NPC51719
0.7477 Intermediate Similarity NPC473199
0.7477 Intermediate Similarity NPC470767
0.7477 Intermediate Similarity NPC165405
0.7477 Intermediate Similarity NPC144068
0.7477 Intermediate Similarity NPC470763
0.7477 Intermediate Similarity NPC239961
0.7477 Intermediate Similarity NPC470056
0.7476 Intermediate Similarity NPC266417
0.7475 Intermediate Similarity NPC161560
0.7455 Intermediate Similarity NPC17791
0.7453 Intermediate Similarity NPC127933
0.7453 Intermediate Similarity NPC475889
0.7453 Intermediate Similarity NPC7644
0.7453 Intermediate Similarity NPC7613
0.7449 Intermediate Similarity NPC213658
0.7449 Intermediate Similarity NPC264546
0.7449 Intermediate Similarity NPC45833
0.7449 Intermediate Similarity NPC110365
0.7449 Intermediate Similarity NPC62202
0.7431 Intermediate Similarity NPC51925
0.7431 Intermediate Similarity NPC43976
0.7431 Intermediate Similarity NPC154085
0.7431 Intermediate Similarity NPC125361
0.7431 Intermediate Similarity NPC296761
0.7426 Intermediate Similarity NPC474835
0.7407 Intermediate Similarity NPC293512
0.7407 Intermediate Similarity NPC470169
0.7407 Intermediate Similarity NPC470170
0.7404 Intermediate Similarity NPC216260
0.7404 Intermediate Similarity NPC5358
0.74 Intermediate Similarity NPC474249
0.74 Intermediate Similarity NPC261990
0.7396 Intermediate Similarity NPC127917
0.7391 Intermediate Similarity NPC241192
0.7387 Intermediate Similarity NPC222834
0.7387 Intermediate Similarity NPC470025
0.7387 Intermediate Similarity NPC317460
0.7387 Intermediate Similarity NPC473125
0.7387 Intermediate Similarity NPC328074
0.7387 Intermediate Similarity NPC321272
0.7383 Intermediate Similarity NPC264867
0.7383 Intermediate Similarity NPC81567
0.7383 Intermediate Similarity NPC201880
0.7383 Intermediate Similarity NPC473207
0.7383 Intermediate Similarity NPC470321
0.7379 Intermediate Similarity NPC194132
0.7379 Intermediate Similarity NPC209297
0.7379 Intermediate Similarity NPC475380
0.7374 Intermediate Similarity NPC470260
0.7374 Intermediate Similarity NPC221993
0.7374 Intermediate Similarity NPC75443
0.7374 Intermediate Similarity NPC106332
0.7368 Intermediate Similarity NPC472080
0.7364 Intermediate Similarity NPC177047
0.7364 Intermediate Similarity NPC119550
0.7364 Intermediate Similarity NPC101450
0.7364 Intermediate Similarity NPC316708
0.7358 Intermediate Similarity NPC154452
0.7358 Intermediate Similarity NPC238397
0.7358 Intermediate Similarity NPC471363
0.7358 Intermediate Similarity NPC472815
0.7358 Intermediate Similarity NPC470571
0.7355 Intermediate Similarity NPC42206
0.7353 Intermediate Similarity NPC178949
0.7353 Intermediate Similarity NPC96736
0.7347 Intermediate Similarity NPC471411
0.7347 Intermediate Similarity NPC214315
0.7347 Intermediate Similarity NPC471410
0.7345 Intermediate Similarity NPC212660
0.7339 Intermediate Similarity NPC472988
0.7339 Intermediate Similarity NPC181994
0.7339 Intermediate Similarity NPC473517
0.7339 Intermediate Similarity NPC38217
0.7333 Intermediate Similarity NPC146188
0.7327 Intermediate Similarity NPC120539
0.7327 Intermediate Similarity NPC8729
0.7321 Intermediate Similarity NPC40133
0.7321 Intermediate Similarity NPC470027
0.7321 Intermediate Similarity NPC49413
0.7321 Intermediate Similarity NPC290608
0.7321 Intermediate Similarity NPC44298
0.7321 Intermediate Similarity NPC473128
0.7315 Intermediate Similarity NPC218158
0.7308 Intermediate Similarity NPC311241
0.7308 Intermediate Similarity NPC475446
0.7308 Intermediate Similarity NPC100912
0.7304 Intermediate Similarity NPC153085
0.7304 Intermediate Similarity NPC268326
0.7304 Intermediate Similarity NPC161065
0.73 Intermediate Similarity NPC170633
0.7297 Intermediate Similarity NPC470026
0.7297 Intermediate Similarity NPC272242
0.7297 Intermediate Similarity NPC65167
0.729 Intermediate Similarity NPC165608
0.729 Intermediate Similarity NPC281378
0.729 Intermediate Similarity NPC213190
0.729 Intermediate Similarity NPC134270
0.7281 Intermediate Similarity NPC290693
0.7281 Intermediate Similarity NPC152615
0.7281 Intermediate Similarity NPC203862
0.7273 Intermediate Similarity NPC473570
0.7265 Intermediate Similarity NPC115349
0.7264 Intermediate Similarity NPC21064
0.7264 Intermediate Similarity NPC472554
0.7264 Intermediate Similarity NPC121072
0.7263 Intermediate Similarity NPC472943
0.7263 Intermediate Similarity NPC475456
0.7263 Intermediate Similarity NPC472951
0.7255 Intermediate Similarity NPC246860
0.7253 Intermediate Similarity NPC12680
0.7248 Intermediate Similarity NPC234160
0.7248 Intermediate Similarity NPC184512
0.7248 Intermediate Similarity NPC122816
0.7248 Intermediate Similarity NPC109376
0.7248 Intermediate Similarity NPC471205
0.7245 Intermediate Similarity NPC476725
0.7241 Intermediate Similarity NPC151616
0.7238 Intermediate Similarity NPC72647
0.7238 Intermediate Similarity NPC107806
0.7238 Intermediate Similarity NPC312325

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC113976 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
0.7155 Intermediate Similarity NPD7516 Approved
0.7069 Intermediate Similarity NPD7327 Approved
0.7069 Intermediate Similarity NPD7328 Approved
0.7034 Intermediate Similarity NPD8033 Approved
0.6949 Remote Similarity NPD8294 Approved
0.6949 Remote Similarity NPD8377 Approved
0.6891 Remote Similarity NPD8379 Approved
0.6891 Remote Similarity NPD8296 Approved
0.6891 Remote Similarity NPD7503 Approved
0.6891 Remote Similarity NPD8335 Approved
0.6891 Remote Similarity NPD8378 Approved
0.6891 Remote Similarity NPD8380 Approved
0.6726 Remote Similarity NPD6686 Approved
0.6724 Remote Similarity NPD8133 Approved
0.6696 Remote Similarity NPD6008 Approved
0.6667 Remote Similarity NPD8132 Clinical (unspecified phase)
0.6667 Remote Similarity NPD7507 Approved
0.6637 Remote Similarity NPD5954 Clinical (unspecified phase)
0.656 Remote Similarity NPD7736 Approved
0.6557 Remote Similarity NPD6370 Approved
0.6545 Remote Similarity NPD6648 Approved
0.6508 Remote Similarity NPD7319 Approved
0.6486 Remote Similarity NPD5344 Discontinued
0.648 Remote Similarity NPD8293 Discontinued
0.6466 Remote Similarity NPD5955 Clinical (unspecified phase)
0.6452 Remote Similarity NPD7492 Approved
0.6435 Remote Similarity NPD5345 Clinical (unspecified phase)
0.6415 Remote Similarity NPD3168 Discontinued
0.64 Remote Similarity NPD6616 Approved
0.6393 Remote Similarity NPD6054 Approved
0.6379 Remote Similarity NPD4061 Clinical (unspecified phase)
0.6349 Remote Similarity NPD7078 Approved
0.6348 Remote Similarity NPD6412 Phase 2
0.6296 Remote Similarity NPD8171 Discontinued
0.6281 Remote Similarity NPD8295 Clinical (unspecified phase)
0.626 Remote Similarity NPD6059 Approved
0.624 Remote Similarity NPD8328 Phase 3
0.6218 Remote Similarity NPD6882 Approved
0.6214 Remote Similarity NPD3670 Clinical (unspecified phase)
0.6214 Remote Similarity NPD3669 Approved
0.621 Remote Similarity NPD6016 Approved
0.621 Remote Similarity NPD6015 Approved
0.6161 Remote Similarity NPD7638 Approved
0.6161 Remote Similarity NPD4225 Approved
0.616 Remote Similarity NPD5988 Approved
0.6148 Remote Similarity NPD6009 Approved
0.6146 Remote Similarity NPD2686 Approved
0.6146 Remote Similarity NPD2254 Approved
0.6146 Remote Similarity NPD2687 Approved
0.6111 Remote Similarity NPD6067 Discontinued
0.6106 Remote Similarity NPD7640 Approved
0.6106 Remote Similarity NPD7639 Approved
0.6083 Remote Similarity NPD8297 Approved
0.608 Remote Similarity NPD8516 Approved
0.608 Remote Similarity NPD8515 Approved
0.608 Remote Similarity NPD8517 Approved
0.608 Remote Similarity NPD8513 Phase 3
0.6055 Remote Similarity NPD8035 Phase 2
0.6055 Remote Similarity NPD8034 Phase 2
0.6044 Remote Similarity NPD1145 Discontinued
0.6036 Remote Similarity NPD6356 Clinical (unspecified phase)
0.6034 Remote Similarity NPD8170 Clinical (unspecified phase)
0.6019 Remote Similarity NPD1779 Approved
0.6019 Remote Similarity NPD1780 Approved
0.6016 Remote Similarity NPD7115 Discovery
0.6 Remote Similarity NPD6319 Approved
0.6 Remote Similarity NPD6399 Phase 3
0.5981 Remote Similarity NPD7524 Approved
0.5979 Remote Similarity NPD7532 Clinical (unspecified phase)
0.5952 Remote Similarity NPD6921 Approved
0.5946 Remote Similarity NPD7900 Approved
0.5946 Remote Similarity NPD7901 Clinical (unspecified phase)
0.5922 Remote Similarity NPD7525 Registered
0.5922 Remote Similarity NPD6928 Phase 2
0.5902 Remote Similarity NPD4632 Approved
0.5882 Remote Similarity NPD6881 Approved
0.5882 Remote Similarity NPD7320 Approved
0.5882 Remote Similarity NPD6899 Approved
0.5872 Remote Similarity NPD6051 Approved
0.5868 Remote Similarity NPD6650 Approved
0.5868 Remote Similarity NPD6649 Approved
0.5862 Remote Similarity NPD3653 Clinical (unspecified phase)
0.5859 Remote Similarity NPD7604 Phase 2
0.5849 Remote Similarity NPD7338 Clinical (unspecified phase)
0.5847 Remote Similarity NPD6402 Approved
0.5847 Remote Similarity NPD7128 Approved
0.5847 Remote Similarity NPD5357 Phase 1
0.5847 Remote Similarity NPD6675 Approved
0.5847 Remote Similarity NPD5739 Approved
0.5833 Remote Similarity NPD6372 Approved
0.5833 Remote Similarity NPD4250 Approved
0.5833 Remote Similarity NPD4251 Approved
0.5833 Remote Similarity NPD6373 Approved
0.5818 Remote Similarity NPD7838 Discovery
0.5804 Remote Similarity NPD7748 Approved
0.5804 Remote Similarity NPD5282 Discontinued
0.5802 Remote Similarity NPD6033 Approved
0.58 Remote Similarity NPD1810 Approved
0.58 Remote Similarity NPD1811 Approved
0.5798 Remote Similarity NPD5697 Approved
0.5794 Remote Similarity NPD7520 Clinical (unspecified phase)
0.5789 Remote Similarity NPD7902 Approved
0.5785 Remote Similarity NPD7290 Approved
0.5785 Remote Similarity NPD7102 Approved
0.5785 Remote Similarity NPD6883 Approved
0.578 Remote Similarity NPD6903 Approved
0.5776 Remote Similarity NPD1700 Approved
0.5775 Remote Similarity NPD7625 Phase 1
0.5766 Remote Similarity NPD7637 Suspended
0.5755 Remote Similarity NPD6695 Phase 3
0.5741 Remote Similarity NPD4249 Approved
0.5741 Remote Similarity NPD7521 Approved
0.5741 Remote Similarity NPD5330 Approved
0.5741 Remote Similarity NPD7334 Approved
0.5741 Remote Similarity NPD6409 Approved
0.5741 Remote Similarity NPD7146 Approved
0.5741 Remote Similarity NPD6684 Approved
0.5739 Remote Similarity NPD8029 Clinical (unspecified phase)
0.5738 Remote Similarity NPD6847 Approved
0.5738 Remote Similarity NPD6617 Approved
0.5738 Remote Similarity NPD8130 Phase 1
0.5738 Remote Similarity NPD8413 Clinical (unspecified phase)
0.5738 Remote Similarity NPD6869 Approved
0.5703 Remote Similarity NPD5983 Phase 2
0.5702 Remote Similarity NPD6013 Approved
0.5702 Remote Similarity NPD6014 Approved
0.5702 Remote Similarity NPD6012 Approved
0.5701 Remote Similarity NPD6400 Clinical (unspecified phase)
0.5688 Remote Similarity NPD3573 Approved
0.5676 Remote Similarity NPD46 Approved
0.5676 Remote Similarity NPD6698 Approved
0.5673 Remote Similarity NPD7645 Phase 2
0.5667 Remote Similarity NPD5701 Approved
0.5664 Remote Similarity NPD6001 Approved
0.566 Remote Similarity NPD4752 Clinical (unspecified phase)
0.5649 Remote Similarity NPD6336 Discontinued
0.5636 Remote Similarity NPD7513 Clinical (unspecified phase)
0.5636 Remote Similarity NPD5737 Approved
0.5636 Remote Similarity NPD6672 Approved
0.563 Remote Similarity NPD8338 Approved
0.563 Remote Similarity NPD8449 Approved
0.5625 Remote Similarity NPD7515 Phase 2
0.562 Remote Similarity NPD6011 Approved
0.5606 Remote Similarity NPD8074 Phase 3

Structure

External Identifiers

PubChem CID   70697894
ChEMBL   CHEMBL2269693
ZINC  

Physicochemical Properties

Molecular Weight:  492.24
ALogP:  -0.9622
MLogP:  3.33
XLogP:  3.177
# Rotatable Bonds:  13
Polar Surface Area:  109.89
# H-Bond Aceptor:  9
# H-Bond Donor:  0
# Rings:  5
# Heavy Atoms:  35

Download Data

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