Natural Product: NPC186042

Natural Product ID:  NPC186042
Common Name:   Apocynol A
IUPAC Name:   (4R)-4-[(E,3R)-3-hydroxybut-1-enyl]-3-(hydroxymethyl)-5,5-dimethylcyclohex-2-en-1-one
Synonyms:  
Molecular Formula:   C13H20O3
Standard InCHIKey:  NSPUEQDFCJBNBF-DMKSKQPMSA-N
Standard InCHI:  InChI=1S/C13H20O3/c1-9(15)4-5-12-10(8-14)6-11(16)7-13(12,2)3/h4-6,9,12,14-15H,7-8H2,1-3H3/b5-4+/t9-,12+/m1/s1
Canonical SMILES:  OCC1=CC(=O)CC([C@H]1/C=C/[C@H](O)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
NPO16145 Apocynum venetum Species Apocynaceae Eukaryota TCM_Taiwan*
NPO32875 cinnamomum wilsonii Species Lauraceae Eukaryota Leaves PMID[23822611]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT660 Cell Line SW480 Homo sapiens IC50 > 10000 nM 23822611
NPT83 Cell Line MCF7 Homo sapiens IC50 > 10000 nM 23822611
NPT81 Cell Line A549 Homo sapiens IC50 > 10000 nM 23822611
NPT659 Cell Line SMMC-7721 Homo sapiens IC50 > 10000 nM 23822611
NPT116 Cell Line HL-60 Homo sapiens IC50 > 10000 nM 23822611

  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 NPC186042 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
0.9286 High Similarity NPC215050
0.9143 High Similarity NPC201562
0.9143 High Similarity NPC323437
0.9143 High Similarity NPC29542
0.9118 High Similarity NPC117804
0.9041 High Similarity NPC475994
0.8919 High Similarity NPC308038
0.8919 High Similarity NPC19900
0.8816 High Similarity NPC158411
0.8816 High Similarity NPC38796
0.8767 High Similarity NPC263582
0.8732 High Similarity NPC95863
0.8696 High Similarity NPC269985
0.8649 High Similarity NPC74995
0.863 High Similarity NPC114236
0.8571 High Similarity NPC93590
0.8533 High Similarity NPC62336
0.8481 Intermediate Similarity NPC476426
0.8451 Intermediate Similarity NPC136473
0.8429 Intermediate Similarity NPC106613
0.8421 Intermediate Similarity NPC152061
0.8375 Intermediate Similarity NPC194417
0.8312 Intermediate Similarity NPC148685
0.8312 Intermediate Similarity NPC172013
0.8312 Intermediate Similarity NPC104120
0.8312 Intermediate Similarity NPC157895
0.8312 Intermediate Similarity NPC45495
0.8267 Intermediate Similarity NPC470525
0.825 Intermediate Similarity NPC474853
0.825 Intermediate Similarity NPC179006
0.8205 Intermediate Similarity NPC6663
0.8182 Intermediate Similarity NPC281138
0.8182 Intermediate Similarity NPC7232
0.8158 Intermediate Similarity NPC197659
0.8158 Intermediate Similarity NPC203403
0.8148 Intermediate Similarity NPC472985
0.8148 Intermediate Similarity NPC472974
0.8148 Intermediate Similarity NPC472986
0.8125 Intermediate Similarity NPC476412
0.8108 Intermediate Similarity NPC153660
0.8077 Intermediate Similarity NPC271104
0.8077 Intermediate Similarity NPC471514
0.8052 Intermediate Similarity NPC297996
0.8052 Intermediate Similarity NPC471409
0.8052 Intermediate Similarity NPC275494
0.8049 Intermediate Similarity NPC287079
0.8026 Intermediate Similarity NPC469646
0.8 Intermediate Similarity NPC105173
0.7975 Intermediate Similarity NPC136150
0.7971 Intermediate Similarity NPC269737
0.7952 Intermediate Similarity NPC474854
0.7922 Intermediate Similarity NPC257666
0.7922 Intermediate Similarity NPC97377
0.7922 Intermediate Similarity NPC86917
0.7922 Intermediate Similarity NPC471061
0.7922 Intermediate Similarity NPC266193
0.7901 Intermediate Similarity NPC230527
0.7901 Intermediate Similarity NPC7927
0.7895 Intermediate Similarity NPC166018
0.7895 Intermediate Similarity NPC225665
0.7895 Intermediate Similarity NPC474011
0.7895 Intermediate Similarity NPC169056
0.7882 Intermediate Similarity NPC475806
0.7875 Intermediate Similarity NPC279186
0.7867 Intermediate Similarity NPC275098
0.7867 Intermediate Similarity NPC247586
0.7857 Intermediate Similarity NPC472983
0.7857 Intermediate Similarity NPC472973
0.7857 Intermediate Similarity NPC309603
0.7857 Intermediate Similarity NPC473999
0.7857 Intermediate Similarity NPC123912
0.7848 Intermediate Similarity NPC306095
0.7848 Intermediate Similarity NPC2482
0.7831 Intermediate Similarity NPC312561
0.7821 Intermediate Similarity NPC478122
0.7808 Intermediate Similarity NPC45264
0.7805 Intermediate Similarity NPC471224
0.7805 Intermediate Similarity NPC274724
0.7805 Intermediate Similarity NPC474083
0.7805 Intermediate Similarity NPC15807
0.7794 Intermediate Similarity NPC311852
0.7792 Intermediate Similarity NPC250621
0.7792 Intermediate Similarity NPC151622
0.7792 Intermediate Similarity NPC7629
0.7792 Intermediate Similarity NPC472305
0.7791 Intermediate Similarity NPC474736
0.7778 Intermediate Similarity NPC251475
0.7778 Intermediate Similarity NPC169941
0.7778 Intermediate Similarity NPC64600
0.7765 Intermediate Similarity NPC134321
0.7765 Intermediate Similarity NPC48010
0.7761 Intermediate Similarity NPC48891
0.775 Intermediate Similarity NPC14151
0.775 Intermediate Similarity NPC121984
0.775 Intermediate Similarity NPC116797
0.775 Intermediate Similarity NPC470298
0.7733 Intermediate Similarity NPC319163
0.7733 Intermediate Similarity NPC67076
0.7711 Intermediate Similarity NPC222613
0.7711 Intermediate Similarity NPC82979
0.7711 Intermediate Similarity NPC470955
0.7711 Intermediate Similarity NPC475022
0.7711 Intermediate Similarity NPC198761
0.7711 Intermediate Similarity NPC118648
0.7711 Intermediate Similarity NPC94666
0.7703 Intermediate Similarity NPC250928
0.7703 Intermediate Similarity NPC471560
0.7703 Intermediate Similarity NPC10758
0.7701 Intermediate Similarity NPC8993
0.7692 Intermediate Similarity NPC34110
0.7692 Intermediate Similarity NPC476007
0.7692 Intermediate Similarity NPC325946
0.7692 Intermediate Similarity NPC85105
0.7692 Intermediate Similarity NPC149550
0.7692 Intermediate Similarity NPC82666
0.7683 Intermediate Similarity NPC227064
0.7683 Intermediate Similarity NPC214043
0.7683 Intermediate Similarity NPC321187
0.7683 Intermediate Similarity NPC227132
0.7683 Intermediate Similarity NPC58841
0.7683 Intermediate Similarity NPC329043
0.7683 Intermediate Similarity NPC161423
0.7683 Intermediate Similarity NPC472326
0.7683 Intermediate Similarity NPC40687
0.7683 Intermediate Similarity NPC473246
0.7683 Intermediate Similarity NPC85774
0.7674 Intermediate Similarity NPC472978
0.7674 Intermediate Similarity NPC116726
0.7674 Intermediate Similarity NPC473998
0.7671 Intermediate Similarity NPC96962
0.7671 Intermediate Similarity NPC114651
0.7662 Intermediate Similarity NPC474885
0.7654 Intermediate Similarity NPC103486
0.7647 Intermediate Similarity NPC473100
0.7647 Intermediate Similarity NPC214387
0.7647 Intermediate Similarity NPC2983
0.7639 Intermediate Similarity NPC474304
0.7639 Intermediate Similarity NPC474329
0.7625 Intermediate Similarity NPC160582
0.7625 Intermediate Similarity NPC472301
0.7625 Intermediate Similarity NPC472478
0.7619 Intermediate Similarity NPC58063
0.7619 Intermediate Similarity NPC136548
0.7614 Intermediate Similarity NPC476245
0.7614 Intermediate Similarity NPC259286
0.76 Intermediate Similarity NPC173321
0.76 Intermediate Similarity NPC34834
0.7595 Intermediate Similarity NPC239098
0.7595 Intermediate Similarity NPC231739
0.7595 Intermediate Similarity NPC192006
0.7595 Intermediate Similarity NPC178852
0.759 Intermediate Similarity NPC70685
0.759 Intermediate Similarity NPC52628
0.759 Intermediate Similarity NPC470574
0.759 Intermediate Similarity NPC36350
0.7586 Intermediate Similarity NPC69454
0.7586 Intermediate Similarity NPC472930
0.7586 Intermediate Similarity NPC109305
0.7568 Intermediate Similarity NPC469679
0.7568 Intermediate Similarity NPC469688
0.7568 Intermediate Similarity NPC471238
0.7564 Intermediate Similarity NPC180886
0.7561 Intermediate Similarity NPC49019
0.7561 Intermediate Similarity NPC297398
0.7558 Intermediate Similarity NPC230332
0.7558 Intermediate Similarity NPC477147
0.7558 Intermediate Similarity NPC477149
0.7558 Intermediate Similarity NPC281942
0.7558 Intermediate Similarity NPC128672
0.7558 Intermediate Similarity NPC232426
0.7558 Intermediate Similarity NPC473099
0.7532 Intermediate Similarity NPC227814
0.7532 Intermediate Similarity NPC144995
0.7532 Intermediate Similarity NPC470299
0.7531 Intermediate Similarity NPC226068
0.7529 Intermediate Similarity NPC471793
0.7529 Intermediate Similarity NPC193843
0.7529 Intermediate Similarity NPC249889
0.7529 Intermediate Similarity NPC104560
0.7529 Intermediate Similarity NPC471791
0.7529 Intermediate Similarity NPC158778
0.7528 Intermediate Similarity NPC249954
0.75 Intermediate Similarity NPC469994
0.75 Intermediate Similarity NPC107540
0.75 Intermediate Similarity NPC476043
0.75 Intermediate Similarity NPC299100
0.75 Intermediate Similarity NPC472490
0.75 Intermediate Similarity NPC473226
0.75 Intermediate Similarity NPC474884
0.75 Intermediate Similarity NPC170394
0.75 Intermediate Similarity NPC474778
0.75 Intermediate Similarity NPC472976
0.75 Intermediate Similarity NPC84790
0.75 Intermediate Similarity NPC53685
0.75 Intermediate Similarity NPC472977
0.75 Intermediate Similarity NPC474732
0.75 Intermediate Similarity NPC322159
0.75 Intermediate Similarity NPC229204
0.75 Intermediate Similarity NPC196227
0.75 Intermediate Similarity NPC327115

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC186042 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
0.7683 Intermediate Similarity NPD3665 Phase 1
0.7683 Intermediate Similarity NPD3666 Approved
0.7683 Intermediate Similarity NPD3133 Approved
0.75 Intermediate Similarity NPD4623 Approved
0.75 Intermediate Similarity NPD3618 Phase 1
0.75 Intermediate Similarity NPD4519 Discontinued
0.75 Intermediate Similarity NPD5279 Phase 3
0.7439 Intermediate Similarity NPD3667 Approved
0.7381 Intermediate Similarity NPD1696 Phase 3
0.7375 Intermediate Similarity NPD5784 Clinical (unspecified phase)
0.7273 Intermediate Similarity NPD6079 Approved
0.7262 Intermediate Similarity NPD4786 Approved
0.7241 Intermediate Similarity NPD5328 Approved
0.7222 Intermediate Similarity NPD368 Approved
0.7215 Intermediate Similarity NPD8264 Approved
0.7195 Intermediate Similarity NPD8259 Clinical (unspecified phase)
0.7195 Intermediate Similarity NPD4695 Discontinued
0.7101 Intermediate Similarity NPD342 Phase 1
0.7079 Intermediate Similarity NPD7515 Phase 2
0.7067 Intermediate Similarity NPD7331 Phase 2
0.7045 Intermediate Similarity NPD4753 Phase 2
0.7042 Intermediate Similarity NPD287 Approved
0.7024 Intermediate Similarity NPD4223 Phase 3
0.7024 Intermediate Similarity NPD4221 Approved
0.7 Intermediate Similarity NPD4202 Approved
0.6977 Remote Similarity NPD5363 Approved
0.6966 Remote Similarity NPD5785 Approved
0.6957 Remote Similarity NPD5222 Approved
0.6957 Remote Similarity NPD5220 Clinical (unspecified phase)
0.6957 Remote Similarity NPD5221 Approved
0.6947 Remote Similarity NPD5211 Phase 2
0.6941 Remote Similarity NPD6110 Phase 1
0.6897 Remote Similarity NPD5690 Phase 2
0.6882 Remote Similarity NPD5173 Approved
0.686 Remote Similarity NPD4197 Approved
0.6848 Remote Similarity NPD4629 Approved
0.6848 Remote Similarity NPD5210 Approved
0.6824 Remote Similarity NPD4269 Approved
0.6824 Remote Similarity NPD4270 Approved
0.6804 Remote Similarity NPD5141 Approved
0.6786 Remote Similarity NPD4252 Approved
0.6782 Remote Similarity NPD5329 Approved
0.6782 Remote Similarity NPD1694 Approved
0.6774 Remote Similarity NPD4697 Phase 3
0.6747 Remote Similarity NPD4268 Approved
0.6747 Remote Similarity NPD4271 Approved
0.6747 Remote Similarity NPD3617 Approved
0.6744 Remote Similarity NPD5362 Discontinued
0.6739 Remote Similarity NPD7748 Approved
0.6737 Remote Similarity NPD5286 Approved
0.6737 Remote Similarity NPD4696 Approved
0.6737 Remote Similarity NPD5285 Approved
0.6711 Remote Similarity NPD7341 Phase 2
0.6705 Remote Similarity NPD6684 Approved
0.6705 Remote Similarity NPD4693 Phase 3
0.6705 Remote Similarity NPD5205 Approved
0.6705 Remote Similarity NPD4689 Approved
0.6705 Remote Similarity NPD4138 Approved
0.6705 Remote Similarity NPD5280 Approved
0.6705 Remote Similarity NPD4688 Approved
0.6705 Remote Similarity NPD4690 Approved
0.6705 Remote Similarity NPD7521 Approved
0.6705 Remote Similarity NPD7334 Approved
0.6705 Remote Similarity NPD6409 Approved
0.6705 Remote Similarity NPD7146 Approved
0.6705 Remote Similarity NPD5330 Approved
0.6705 Remote Similarity NPD4694 Approved
0.6702 Remote Similarity NPD4755 Approved
0.6667 Remote Similarity NPD3668 Phase 3
0.6667 Remote Similarity NPD5223 Approved
0.6667 Remote Similarity NPD4195 Approved
0.663 Remote Similarity NPD5779 Approved
0.663 Remote Similarity NPD5778 Approved
0.6628 Remote Similarity NPD4752 Clinical (unspecified phase)
0.6622 Remote Similarity NPD4246 Clinical (unspecified phase)
0.6598 Remote Similarity NPD5225 Approved
0.6598 Remote Similarity NPD5224 Approved
0.6598 Remote Similarity NPD5226 Approved
0.6598 Remote Similarity NPD4633 Approved
0.6588 Remote Similarity NPD4822 Approved
0.6588 Remote Similarity NPD4819 Approved
0.6588 Remote Similarity NPD4821 Approved
0.6588 Remote Similarity NPD5790 Clinical (unspecified phase)
0.6588 Remote Similarity NPD4820 Approved
0.6585 Remote Similarity NPD8039 Approved
0.6582 Remote Similarity NPD4137 Phase 3
0.6562 Remote Similarity NPD4700 Approved
0.6562 Remote Similarity NPD7640 Approved
0.6562 Remote Similarity NPD7639 Approved
0.6556 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6556 Remote Similarity NPD6903 Approved
0.6556 Remote Similarity NPD4518 Approved
0.6552 Remote Similarity NPD5332 Approved
0.6552 Remote Similarity NPD7154 Phase 3
0.6552 Remote Similarity NPD5331 Approved
0.6548 Remote Similarity NPD7322 Clinical (unspecified phase)
0.6533 Remote Similarity NPD4191 Approved
0.6533 Remote Similarity NPD4192 Approved
0.6533 Remote Similarity NPD4194 Approved
0.6533 Remote Similarity NPD4193 Approved
0.6531 Remote Similarity NPD5174 Approved
0.6531 Remote Similarity NPD5175 Approved
0.6528 Remote Similarity NPD4219 Approved
0.6526 Remote Similarity NPD7902 Approved
0.6526 Remote Similarity NPD6084 Phase 2
0.6526 Remote Similarity NPD6083 Phase 2
0.6522 Remote Similarity NPD5284 Approved
0.6522 Remote Similarity NPD5281 Approved
0.6522 Remote Similarity NPD6411 Approved
0.6517 Remote Similarity NPD3574 Clinical (unspecified phase)
0.6517 Remote Similarity NPD5786 Approved
0.6512 Remote Similarity NPD4790 Discontinued
0.6506 Remote Similarity NPD3701 Clinical (unspecified phase)
0.65 Remote Similarity NPD4747 Approved
0.65 Remote Similarity NPD4691 Approved
0.6489 Remote Similarity NPD1698 Clinical (unspecified phase)
0.6489 Remote Similarity NPD5695 Phase 3
0.6463 Remote Similarity NPD4058 Approved
0.6463 Remote Similarity NPD4687 Approved
0.6458 Remote Similarity NPD7638 Approved
0.6458 Remote Similarity NPD4225 Approved
0.6452 Remote Similarity NPD6399 Phase 3
0.6447 Remote Similarity NPD2664 Clinical (unspecified phase)
0.6437 Remote Similarity NPD5209 Approved
0.6429 Remote Similarity NPD4756 Discovery
0.642 Remote Similarity NPD5276 Approved
0.6413 Remote Similarity NPD4096 Approved
0.641 Remote Similarity NPD3704 Approved
0.6395 Remote Similarity NPD7332 Phase 2
0.6395 Remote Similarity NPD5368 Approved
0.6395 Remote Similarity NPD7514 Phase 3
0.6386 Remote Similarity NPD7339 Approved
0.6386 Remote Similarity NPD6942 Approved
0.6383 Remote Similarity NPD5282 Discontinued
0.6374 Remote Similarity NPD6672 Approved
0.6374 Remote Similarity NPD5737 Approved
0.6364 Remote Similarity NPD4754 Approved
0.6364 Remote Similarity NPD4788 Approved
0.6353 Remote Similarity NPD7145 Approved
0.6344 Remote Similarity NPD7637 Suspended
0.6341 Remote Similarity NPD4732 Discontinued
0.6337 Remote Similarity NPD5697 Approved
0.6322 Remote Similarity NPD5369 Approved
0.6322 Remote Similarity NPD6902 Approved
0.6304 Remote Similarity NPD7285 Clinical (unspecified phase)
0.6304 Remote Similarity NPD6101 Approved
0.6304 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6296 Remote Similarity NPD7143 Approved
0.6296 Remote Similarity NPD7144 Approved
0.6292 Remote Similarity NPD6400 Clinical (unspecified phase)
0.6289 Remote Similarity NPD5696 Approved
0.6279 Remote Similarity NPD6929 Approved
0.6279 Remote Similarity NPD7645 Phase 2
0.6275 Remote Similarity NPD5168 Approved
0.6275 Remote Similarity NPD6899 Approved
0.6275 Remote Similarity NPD6011 Approved
0.6275 Remote Similarity NPD4729 Approved
0.6275 Remote Similarity NPD6881 Approved
0.6275 Remote Similarity NPD4730 Approved
0.6265 Remote Similarity NPD6926 Approved
0.6265 Remote Similarity NPD5733 Approved
0.6265 Remote Similarity NPD6924 Approved
0.6264 Remote Similarity NPD4751 Clinical (unspecified phase)
0.6264 Remote Similarity NPD3573 Approved
0.6262 Remote Similarity NPD7115 Discovery
0.625 Remote Similarity NPD6435 Approved
0.6238 Remote Similarity NPD4768 Approved
0.6238 Remote Similarity NPD6675 Approved
0.6238 Remote Similarity NPD5739 Approved
0.6238 Remote Similarity NPD6402 Approved
0.6238 Remote Similarity NPD7128 Approved
0.6238 Remote Similarity NPD4767 Approved
0.6237 Remote Similarity NPD46 Approved
0.6237 Remote Similarity NPD6698 Approved
0.6235 Remote Similarity NPD5776 Phase 2
0.6235 Remote Similarity NPD6925 Approved
0.622 Remote Similarity NPD7152 Approved
0.622 Remote Similarity NPD7151 Approved
0.622 Remote Similarity NPD7150 Approved
0.6214 Remote Similarity NPD6013 Approved
0.6214 Remote Similarity NPD6014 Approved
0.6214 Remote Similarity NPD6012 Approved
0.6211 Remote Similarity NPD7900 Approved
0.6211 Remote Similarity NPD7901 Clinical (unspecified phase)
0.6207 Remote Similarity NPD6930 Phase 2
0.6207 Remote Similarity NPD6931 Approved
0.6203 Remote Similarity NPD6108 Clinical (unspecified phase)
0.6176 Remote Similarity NPD6412 Phase 2
0.6176 Remote Similarity NPD5701 Approved
0.6173 Remote Similarity NPD6923 Approved
0.6173 Remote Similarity NPD6922 Approved
0.617 Remote Similarity NPD4810 Clinical (unspecified phase)
0.6164 Remote Similarity NPD4627 Clinical (unspecified phase)
0.6154 Remote Similarity NPD5169 Approved
0.6154 Remote Similarity NPD5248 Approved
0.6154 Remote Similarity NPD5135 Approved
0.6154 Remote Similarity NPD5134 Clinical (unspecified phase)
0.6154 Remote Similarity NPD5247 Approved
0.6154 Remote Similarity NPD7102 Approved
0.6154 Remote Similarity NPD5249 Phase 3

Structure

External Identifiers

PubChem CID   11053300
ChEMBL   CHEMBL2407705
ZINC  

Physicochemical Properties

Molecular Weight:  224.14
ALogP:  0.4089
MLogP:  2.56
XLogP:  0.72
# Rotatable Bonds:  8
Polar Surface Area:  57.53
# H-Bond Aceptor:  3
# H-Bond Donor:  2
# Rings:  1
# Heavy Atoms:  16

Download Data

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General Info & Identifiers & Properties  
Structure MOL file  
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Biological Activities  
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