Natural Product: NPC151481

Natural Product ID:  NPC151481
Common Name:   Latrunculeic Acid
IUPAC Name:   (2Z,6Z,8S)-3,8-dimethyl-10-[(2R)-6-oxo-2,3-dihydropyran-2-yl]deca-2,6-dienoic acid
Synonyms:   Latrunculeic Acid
Molecular Formula:   C17H24O4
Standard InCHIKey:  OHWFPMKLBOHSHY-WKTSBRCASA-N
Standard InCHI:  InChI=1S/C17H24O4/c1-13(6-3-4-7-14(2)12-16(18)19)10-11-15-8-5-9-17(20)21-15/h3,5-6,9,12-13,15H,4,7-8,10-11H2,1-2H3,(H,18,19)/b6-3-,14-12-/t13-,15+/m1/s1
Canonical SMILES:  C[C@@H](CC[C@@H]1CC=CC(=O)O1)/C=CCC/C(=CC(=O)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
NPO3492 Negombata magnifica Species Latrunculiidae Eukaryota PMID[15217296]
NPO19376 Cacospongia mycofijiensis Species Thorectidae Eukaryota PMID[18942825]
NPO3492 Negombata magnifica Species Latrunculiidae Eukaryota PMID[18942825]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT400 Cell Line MDA-MB-435 Homo sapiens Ratio IC50 = 0.5 Open TG-GATES in vivo data: Hematology
NPT393 Cell Line HCT-116 Homo sapiens IC50 = 48000 nM 24417583
NPT400 Cell Line MDA-MB-435 Homo sapiens IC50 = 26100 nM 10.1016/S0960-894X(97)00029-2

  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 NPC151481 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
0.8571 High Similarity NPC316185
0.8333 Intermediate Similarity NPC315843
0.8312 Intermediate Similarity NPC44261
0.8267 Intermediate Similarity NPC139712
0.8235 Intermediate Similarity NPC96414
0.8182 Intermediate Similarity NPC26223
0.8169 Intermediate Similarity NPC473361
0.8169 Intermediate Similarity NPC59558
0.8169 Intermediate Similarity NPC329904
0.8169 Intermediate Similarity NPC4299
0.8116 Intermediate Similarity NPC201356
0.8082 Intermediate Similarity NPC107654
0.8082 Intermediate Similarity NPC470686
0.8077 Intermediate Similarity NPC16488
0.806 Intermediate Similarity NPC26810
0.803 Intermediate Similarity NPC159650
0.803 Intermediate Similarity NPC22897
0.8028 Intermediate Similarity NPC101622
0.8 Intermediate Similarity NPC315394
0.8 Intermediate Similarity NPC315395
0.8 Intermediate Similarity NPC316426
0.7941 Intermediate Similarity NPC217940
0.7917 Intermediate Similarity NPC469660
0.7895 Intermediate Similarity NPC209135
0.7895 Intermediate Similarity NPC108816
0.7895 Intermediate Similarity NPC474816
0.7895 Intermediate Similarity NPC93763
0.7887 Intermediate Similarity NPC313444
0.7857 Intermediate Similarity NPC146811
0.7826 Intermediate Similarity NPC148233
0.7826 Intermediate Similarity NPC25747
0.7826 Intermediate Similarity NPC308457
0.7821 Intermediate Similarity NPC112868
0.7821 Intermediate Similarity NPC325031
0.7821 Intermediate Similarity NPC315731
0.7808 Intermediate Similarity NPC477087
0.7808 Intermediate Similarity NPC472254
0.7808 Intermediate Similarity NPC477086
0.7794 Intermediate Similarity NPC55376
0.7763 Intermediate Similarity NPC471225
0.7763 Intermediate Similarity NPC262747
0.7746 Intermediate Similarity NPC472266
0.7746 Intermediate Similarity NPC194871
0.7733 Intermediate Similarity NPC329852
0.7727 Intermediate Similarity NPC129150
0.7727 Intermediate Similarity NPC294938
0.7722 Intermediate Similarity NPC85772
0.7714 Intermediate Similarity NPC282760
0.7714 Intermediate Similarity NPC273600
0.7714 Intermediate Similarity NPC19769
0.7714 Intermediate Similarity NPC471556
0.7714 Intermediate Similarity NPC471566
0.7703 Intermediate Similarity NPC327383
0.7703 Intermediate Similarity NPC222244
0.7703 Intermediate Similarity NPC477085
0.7703 Intermediate Similarity NPC185186
0.7703 Intermediate Similarity NPC16349
0.7683 Intermediate Similarity NPC316138
0.7683 Intermediate Similarity NPC313658
0.7671 Intermediate Similarity NPC315597
0.7671 Intermediate Similarity NPC316029
0.7671 Intermediate Similarity NPC476037
0.7671 Intermediate Similarity NPC315285
0.7662 Intermediate Similarity NPC267231
0.7654 Intermediate Similarity NPC471494
0.7654 Intermediate Similarity NPC67081
0.7654 Intermediate Similarity NPC471223
0.7647 Intermediate Similarity NPC19241
0.7639 Intermediate Similarity NPC238223
0.7639 Intermediate Similarity NPC470256
0.7639 Intermediate Similarity NPC475760
0.7639 Intermediate Similarity NPC310210
0.7632 Intermediate Similarity NPC469880
0.7625 Intermediate Similarity NPC161045
0.7625 Intermediate Similarity NPC474809
0.7619 Intermediate Similarity NPC3952
0.7612 Intermediate Similarity NPC223679
0.7612 Intermediate Similarity NPC254095
0.7606 Intermediate Similarity NPC248125
0.7606 Intermediate Similarity NPC124586
0.7606 Intermediate Similarity NPC315115
0.76 Intermediate Similarity NPC259599
0.76 Intermediate Similarity NPC294434
0.76 Intermediate Similarity NPC117746
0.76 Intermediate Similarity NPC476355
0.76 Intermediate Similarity NPC15499
0.76 Intermediate Similarity NPC474758
0.7595 Intermediate Similarity NPC184208
0.7595 Intermediate Similarity NPC475944
0.7595 Intermediate Similarity NPC8538
0.7564 Intermediate Similarity NPC471537
0.7564 Intermediate Similarity NPC226226
0.7564 Intermediate Similarity NPC55304
0.7561 Intermediate Similarity NPC234038
0.7561 Intermediate Similarity NPC311163
0.7534 Intermediate Similarity NPC470693
0.7532 Intermediate Similarity NPC475711
0.7532 Intermediate Similarity NPC84360
0.7532 Intermediate Similarity NPC7563
0.7532 Intermediate Similarity NPC116177
0.7532 Intermediate Similarity NPC320630
0.7531 Intermediate Similarity NPC474865
0.7531 Intermediate Similarity NPC196487
0.7531 Intermediate Similarity NPC14575
0.7531 Intermediate Similarity NPC126518
0.75 Intermediate Similarity NPC115179
0.75 Intermediate Similarity NPC203335
0.75 Intermediate Similarity NPC212598
0.75 Intermediate Similarity NPC122627
0.75 Intermediate Similarity NPC82465
0.75 Intermediate Similarity NPC132286
0.75 Intermediate Similarity NPC313677
0.75 Intermediate Similarity NPC285840
0.75 Intermediate Similarity NPC133450
0.75 Intermediate Similarity NPC323251
0.75 Intermediate Similarity NPC327041
0.75 Intermediate Similarity NPC106040
0.747 Intermediate Similarity NPC160138
0.747 Intermediate Similarity NPC199382
0.7467 Intermediate Similarity NPC329890
0.7465 Intermediate Similarity NPC182794
0.7465 Intermediate Similarity NPC470688
0.7465 Intermediate Similarity NPC471565
0.7463 Intermediate Similarity NPC249850
0.7463 Intermediate Similarity NPC135863
0.7463 Intermediate Similarity NPC293437
0.7442 Intermediate Similarity NPC109406
0.7439 Intermediate Similarity NPC163606
0.7439 Intermediate Similarity NPC11804
0.7439 Intermediate Similarity NPC261380
0.7436 Intermediate Similarity NPC248775
0.7436 Intermediate Similarity NPC279532
0.7432 Intermediate Similarity NPC476012
0.7432 Intermediate Similarity NPC202011
0.7429 Intermediate Similarity NPC179087
0.7429 Intermediate Similarity NPC68110
0.7429 Intermediate Similarity NPC473737
0.7429 Intermediate Similarity NPC155849
0.7429 Intermediate Similarity NPC210303
0.7429 Intermediate Similarity NPC44343
0.7412 Intermediate Similarity NPC177668
0.7407 Intermediate Similarity NPC42476
0.7407 Intermediate Similarity NPC315559
0.7407 Intermediate Similarity NPC250315
0.7407 Intermediate Similarity NPC40746
0.7407 Intermediate Similarity NPC169575
0.7403 Intermediate Similarity NPC68819
0.7403 Intermediate Similarity NPC477202
0.7403 Intermediate Similarity NPC123360
0.7397 Intermediate Similarity NPC474823
0.7397 Intermediate Similarity NPC276290
0.7391 Intermediate Similarity NPC79756
0.7368 Intermediate Similarity NPC114727
0.7368 Intermediate Similarity NPC476590
0.7368 Intermediate Similarity NPC140287
0.7361 Intermediate Similarity NPC475555
0.7361 Intermediate Similarity NPC37382
0.7361 Intermediate Similarity NPC475675
0.7361 Intermediate Similarity NPC191233
0.7353 Intermediate Similarity NPC21946
0.7349 Intermediate Similarity NPC186332
0.7349 Intermediate Similarity NPC305475
0.7349 Intermediate Similarity NPC475461
0.7349 Intermediate Similarity NPC47220
0.7342 Intermediate Similarity NPC470148
0.7342 Intermediate Similarity NPC86971
0.7342 Intermediate Similarity NPC469617
0.7342 Intermediate Similarity NPC180725
0.7342 Intermediate Similarity NPC470149
0.7342 Intermediate Similarity NPC178277
0.7333 Intermediate Similarity NPC477084
0.7333 Intermediate Similarity NPC163003
0.7333 Intermediate Similarity NPC293114
0.7333 Intermediate Similarity NPC475762
0.7333 Intermediate Similarity NPC67076
0.7333 Intermediate Similarity NPC319163
0.7326 Intermediate Similarity NPC206679
0.7326 Intermediate Similarity NPC114172
0.7326 Intermediate Similarity NPC471324
0.7326 Intermediate Similarity NPC476084
0.7326 Intermediate Similarity NPC476075
0.7324 Intermediate Similarity NPC34883
0.7317 Intermediate Similarity NPC160517
0.7317 Intermediate Similarity NPC186155
0.7317 Intermediate Similarity NPC31086
0.7317 Intermediate Similarity NPC70424
0.7317 Intermediate Similarity NPC78673
0.7317 Intermediate Similarity NPC243618
0.7317 Intermediate Similarity NPC161670
0.7317 Intermediate Similarity NPC476804
0.7313 Intermediate Similarity NPC96663
0.7308 Intermediate Similarity NPC477203
0.7308 Intermediate Similarity NPC187568
0.7308 Intermediate Similarity NPC57744
0.7308 Intermediate Similarity NPC41780
0.7308 Intermediate Similarity NPC316324
0.7308 Intermediate Similarity NPC476439
0.7308 Intermediate Similarity NPC474026
0.7297 Intermediate Similarity NPC265574
0.7297 Intermediate Similarity NPC475004

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC151481 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
0.7714 Intermediate Similarity NPD2685 Clinical (unspecified phase)
0.7531 Intermediate Similarity NPD6400 Clinical (unspecified phase)
0.7011 Intermediate Similarity NPD7838 Discovery
0.6867 Remote Similarity NPD5209 Approved
0.6849 Remote Similarity NPD5325 Clinical (unspecified phase)
0.6848 Remote Similarity NPD8029 Clinical (unspecified phase)
0.6818 Remote Similarity NPD46 Approved
0.6818 Remote Similarity NPD5785 Approved
0.6818 Remote Similarity NPD6698 Approved
0.6806 Remote Similarity NPD4193 Approved
0.6806 Remote Similarity NPD4194 Approved
0.6806 Remote Similarity NPD4192 Approved
0.6806 Remote Similarity NPD4191 Approved
0.6786 Remote Similarity NPD7154 Phase 3
0.6774 Remote Similarity NPD6648 Approved
0.6702 Remote Similarity NPD5344 Discontinued
0.6667 Remote Similarity NPD4752 Clinical (unspecified phase)
0.6667 Remote Similarity NPD4225 Approved
0.6628 Remote Similarity NPD5363 Approved
0.6627 Remote Similarity NPD5790 Clinical (unspecified phase)
0.6588 Remote Similarity NPD5362 Discontinued
0.6567 Remote Similarity NPD6927 Phase 3
0.6515 Remote Similarity NPD4220 Pre-registration
0.6463 Remote Similarity NPD4756 Discovery
0.6438 Remote Similarity NPD4246 Clinical (unspecified phase)
0.6437 Remote Similarity NPD1694 Approved
0.6437 Remote Similarity NPD6082 Clinical (unspecified phase)
0.6429 Remote Similarity NPD4822 Approved
0.6429 Remote Similarity NPD4820 Approved
0.6429 Remote Similarity NPD4821 Approved
0.6429 Remote Similarity NPD4819 Approved
0.642 Remote Similarity NPD8039 Approved
0.6395 Remote Similarity NPD5332 Approved
0.6395 Remote Similarity NPD5331 Approved
0.6386 Remote Similarity NPD4271 Approved
0.6386 Remote Similarity NPD4268 Approved
0.6386 Remote Similarity NPD5784 Clinical (unspecified phase)
0.6374 Remote Similarity NPD7637 Suspended
0.6353 Remote Similarity NPD4790 Discontinued
0.6351 Remote Similarity NPD368 Approved
0.6344 Remote Similarity NPD1698 Clinical (unspecified phase)
0.6304 Remote Similarity NPD5778 Approved
0.6304 Remote Similarity NPD5779 Approved
0.6279 Remote Similarity NPD4270 Approved
0.6279 Remote Similarity NPD4269 Approved
0.625 Remote Similarity NPD7640 Approved
0.625 Remote Similarity NPD7639 Approved
0.6235 Remote Similarity NPD4252 Approved
0.6196 Remote Similarity NPD7983 Approved
0.618 Remote Similarity NPD5786 Approved
0.618 Remote Similarity NPD4249 Approved
0.6154 Remote Similarity NPD4247 Clinical (unspecified phase)
0.6146 Remote Similarity NPD7638 Approved
0.6111 Remote Similarity NPD4251 Approved
0.6111 Remote Similarity NPD4250 Approved
0.6105 Remote Similarity NPD4792 Clinical (unspecified phase)
0.6105 Remote Similarity NPD7839 Suspended
0.6067 Remote Similarity NPD1733 Clinical (unspecified phase)
0.6024 Remote Similarity NPD8264 Approved
0.5981 Remote Similarity NPD7115 Discovery
0.5978 Remote Similarity NPD6101 Approved
0.5978 Remote Similarity NPD6051 Approved
0.5978 Remote Similarity NPD5764 Clinical (unspecified phase)
0.5977 Remote Similarity NPD5369 Approved
0.5972 Remote Similarity NPD342 Phase 1
0.5946 Remote Similarity NPD585 Clinical (unspecified phase)
0.5946 Remote Similarity NPD6109 Phase 1
0.5941 Remote Similarity NPD4211 Phase 1
0.5934 Remote Similarity NPD1282 Approved
0.5909 Remote Similarity NPD6435 Approved
0.59 Remote Similarity NPD6647 Phase 2
0.589 Remote Similarity NPD4219 Approved
0.5882 Remote Similarity NPD5343 Approved
0.5882 Remote Similarity NPD7899 Clinical (unspecified phase)
0.5865 Remote Similarity NPD6371 Approved
0.5862 Remote Similarity NPD8259 Clinical (unspecified phase)
0.5851 Remote Similarity NPD4810 Clinical (unspecified phase)
0.5851 Remote Similarity NPD6411 Approved
0.5843 Remote Similarity NPD6110 Phase 1
0.5825 Remote Similarity NPD6686 Approved
0.5824 Remote Similarity NPD6422 Discontinued
0.5821 Remote Similarity NPD4265 Approved
0.5814 Remote Similarity NPD7322 Clinical (unspecified phase)
0.581 Remote Similarity NPD8413 Clinical (unspecified phase)
0.5806 Remote Similarity NPD5370 Suspended
0.5806 Remote Similarity NPD1695 Approved
0.5783 Remote Similarity NPD4732 Discontinued
0.5755 Remote Similarity NPD6053 Discontinued
0.5729 Remote Similarity NPD7748 Approved
0.5688 Remote Similarity NPD7505 Discontinued
0.5686 Remote Similarity NPD5909 Discontinued
0.5682 Remote Similarity NPD7332 Phase 2
0.5682 Remote Similarity NPD7514 Phase 3
0.5682 Remote Similarity NPD5368 Approved
0.5672 Remote Similarity NPD6097 Approved
0.5672 Remote Similarity NPD6096 Approved
0.5667 Remote Similarity NPD6695 Phase 3
0.566 Remote Similarity NPD7116 Clinical (unspecified phase)
0.5652 Remote Similarity NPD6409 Approved
0.5652 Remote Similarity NPD7146 Approved
0.5652 Remote Similarity NPD6684 Approved
0.5652 Remote Similarity NPD5330 Approved
0.5652 Remote Similarity NPD7521 Approved
0.5652 Remote Similarity NPD7334 Approved
0.5644 Remote Similarity NPD7632 Discontinued
0.5641 Remote Similarity NPD2664 Clinical (unspecified phase)
0.5632 Remote Similarity NPD7145 Approved
0.5625 Remote Similarity NPD6399 Phase 3
0.5625 Remote Similarity NPD6108 Clinical (unspecified phase)
0.5625 Remote Similarity NPD7331 Phase 2
0.5618 Remote Similarity NPD6902 Approved
0.5604 Remote Similarity NPD7338 Clinical (unspecified phase)
0.56 Remote Similarity NPD8779 Phase 3

Structure

External Identifiers

PubChem CID   11426344
ChEMBL   CHEMBL512338
ZINC  

Physicochemical Properties

Molecular Weight:  292.17
ALogP:  1.9297
MLogP:  2.89
XLogP:  3.901
# Rotatable Bonds:  11
Polar Surface Area:  63.6
# H-Bond Aceptor:  4
# H-Bond Donor:  1
# Rings:  1
# Heavy Atoms:  21

Download Data

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