Natural Product: NPC21667

Natural Product ID:  NPC21667
Common Name:   Holamine
IUPAC Name:   1-[(3R,8S,9S,10R,13S,14S,17S)-3-amino-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]ethanone
Synonyms:   Holamine
Molecular Formula:   C21H33NO
Standard InCHIKey:  GPRZXDPWGLHIQE-QYYVTAPASA-N
Standard InCHI:  InChI=1S/C21H33NO/c1-13(23)17-6-7-18-16-5-4-14-12-15(22)8-10-20(14,2)19(16)9-11-21(17,18)3/h4,15-19H,5-12,22H2,1-3H3/t15-,16+,17-,18+,19+,20+,21-/m1/s1
Canonical SMILES:  N[C@@H]1CC[C@]2(C(=CC[C@@H]3[C@@H]2CC[C@]2([C@H]3CC[C@@H]2C(=O)C)C)C1)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
NPO32911 holarrhena curtisii Species Apocynaceae Eukaryota PMID[9834146]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT168 Cell Line P388 Mus musculus IC50 = 0.85 ug/ml 10.6019/CHEMBL1201861
NPT168 Cell Line P388 Mus musculus IC50 = 0.83 ug/ml 10.6019/CHEMBL1201861
NPT168 Cell Line P388 Mus musculus IC50 = 0.91 ug/ml 10.6019/CHEMBL1201861
NPT633 Organism Leishmania donovani Leishmania donovani IC50 = 0.39 ug/ml 15646539
NPT116 Cell Line HL-60 Homo sapiens IC50 = 0.2 ug/ml PubChem BioAssay data set

  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 NPC21667 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
0.8427 Intermediate Similarity NPC476754
0.8315 Intermediate Similarity NPC476752
0.8315 Intermediate Similarity NPC476753
0.8191 Intermediate Similarity NPC58200
0.8182 Intermediate Similarity NPC20610
0.814 Intermediate Similarity NPC182106
0.814 Intermediate Similarity NPC311769
0.8105 Intermediate Similarity NPC98765
0.8101 Intermediate Similarity NPC110615
0.8077 Intermediate Similarity NPC182815
0.7979 Intermediate Similarity NPC239768
0.7979 Intermediate Similarity NPC128698
0.7978 Intermediate Similarity NPC249312
0.7975 Intermediate Similarity NPC282593
0.7975 Intermediate Similarity NPC159577
0.7975 Intermediate Similarity NPC35734
0.7938 Intermediate Similarity NPC230677
0.7875 Intermediate Similarity NPC115023
0.7875 Intermediate Similarity NPC470078
0.7865 Intermediate Similarity NPC259252
0.7778 Intermediate Similarity NPC251705
0.7778 Intermediate Similarity NPC303613
0.7778 Intermediate Similarity NPC474228
0.7755 Intermediate Similarity NPC233256
0.7755 Intermediate Similarity NPC195841
0.775 Intermediate Similarity NPC307176
0.775 Intermediate Similarity NPC477856
0.775 Intermediate Similarity NPC214770
0.7692 Intermediate Similarity NPC323005
0.7684 Intermediate Similarity NPC140685
0.7654 Intermediate Similarity NPC234707
0.7625 Intermediate Similarity NPC139397
0.759 Intermediate Similarity NPC293803
0.7586 Intermediate Similarity NPC215474
0.7561 Intermediate Similarity NPC470044
0.7561 Intermediate Similarity NPC470045
0.7558 Intermediate Similarity NPC12035
0.7531 Intermediate Similarity NPC40574
0.7531 Intermediate Similarity NPC251929
0.7531 Intermediate Similarity NPC2634
0.7531 Intermediate Similarity NPC260040
0.7531 Intermediate Similarity NPC265782
0.75 Intermediate Similarity NPC69408
0.7471 Intermediate Similarity NPC329782
0.7471 Intermediate Similarity NPC152039
0.7471 Intermediate Similarity NPC118329
0.747 Intermediate Similarity NPC255021
0.747 Intermediate Similarity NPC309852
0.7449 Intermediate Similarity NPC152718
0.7439 Intermediate Similarity NPC54123
0.7439 Intermediate Similarity NPC21773
0.7439 Intermediate Similarity NPC305501
0.7436 Intermediate Similarity NPC469662
0.7386 Intermediate Similarity NPC472312
0.7386 Intermediate Similarity NPC283277
0.7353 Intermediate Similarity NPC175585
0.7326 Intermediate Similarity NPC82635
0.7326 Intermediate Similarity NPC470052
0.7308 Intermediate Similarity NPC202118
0.7308 Intermediate Similarity NPC197238
0.7284 Intermediate Similarity NPC39157
0.7284 Intermediate Similarity NPC82477
0.7284 Intermediate Similarity NPC296697
0.7284 Intermediate Similarity NPC142754
0.7273 Intermediate Similarity NPC226509
0.7262 Intermediate Similarity NPC476904
0.725 Intermediate Similarity NPC189917
0.725 Intermediate Similarity NPC43300
0.725 Intermediate Similarity NPC96812
0.725 Intermediate Similarity NPC107704
0.725 Intermediate Similarity NPC39462
0.725 Intermediate Similarity NPC168824
0.7241 Intermediate Similarity NPC211322
0.7216 Intermediate Similarity NPC184033
0.7209 Intermediate Similarity NPC91665
0.7195 Intermediate Similarity NPC286814
0.7176 Intermediate Similarity NPC473171
0.7176 Intermediate Similarity NPC255650
0.716 Intermediate Similarity NPC220210
0.716 Intermediate Similarity NPC176107
0.716 Intermediate Similarity NPC20181
0.7159 Intermediate Similarity NPC474509
0.7143 Intermediate Similarity NPC24733
0.7129 Intermediate Similarity NPC119329
0.7129 Intermediate Similarity NPC469958
0.7128 Intermediate Similarity NPC84171
0.7093 Intermediate Similarity NPC7214
0.7079 Intermediate Similarity NPC147066
0.7079 Intermediate Similarity NPC474122
0.7059 Intermediate Similarity NPC474797
0.7059 Intermediate Similarity NPC474796
0.7059 Intermediate Similarity NPC329866
0.7045 Intermediate Similarity NPC215843
0.7045 Intermediate Similarity NPC90965
0.7045 Intermediate Similarity NPC170793
0.7037 Intermediate Similarity NPC92327
0.7024 Intermediate Similarity NPC265789
0.7024 Intermediate Similarity NPC223187
0.7024 Intermediate Similarity NPC190035
0.7011 Intermediate Similarity NPC470557
0.7 Intermediate Similarity NPC320514
0.7 Intermediate Similarity NPC472239
0.7 Intermediate Similarity NPC474001
0.7 Intermediate Similarity NPC34193
0.699 Remote Similarity NPC476756
0.699 Remote Similarity NPC244982
0.6989 Remote Similarity NPC43308
0.6988 Remote Similarity NPC477857
0.6962 Remote Similarity NPC213152
0.6962 Remote Similarity NPC60565
0.6957 Remote Similarity NPC147513
0.6957 Remote Similarity NPC75810
0.6941 Remote Similarity NPC474488
0.6939 Remote Similarity NPC247220
0.6932 Remote Similarity NPC469996
0.6923 Remote Similarity NPC470046
0.6923 Remote Similarity NPC470047
0.6909 Remote Similarity NPC35037
0.6889 Remote Similarity NPC201912
0.6889 Remote Similarity NPC4166
0.6889 Remote Similarity NPC38350
0.6883 Remote Similarity NPC230823
0.6883 Remote Similarity NPC49575
0.6883 Remote Similarity NPC267626
0.6883 Remote Similarity NPC55004
0.6882 Remote Similarity NPC157479
0.6875 Remote Similarity NPC165695
0.6869 Remote Similarity NPC167419
0.6869 Remote Similarity NPC474164
0.6867 Remote Similarity NPC260474
0.6867 Remote Similarity NPC188292
0.6867 Remote Similarity NPC310992
0.6854 Remote Similarity NPC477371
0.6848 Remote Similarity NPC214043
0.6848 Remote Similarity NPC82902
0.6848 Remote Similarity NPC221758
0.6848 Remote Similarity NPC59453
0.6848 Remote Similarity NPC85774
0.6835 Remote Similarity NPC127582
0.6824 Remote Similarity NPC5701
0.6824 Remote Similarity NPC181204
0.6824 Remote Similarity NPC225467
0.6813 Remote Similarity NPC260956
0.6813 Remote Similarity NPC193347
0.6813 Remote Similarity NPC3511
0.6813 Remote Similarity NPC311092
0.6813 Remote Similarity NPC472867
0.6813 Remote Similarity NPC142253
0.679 Remote Similarity NPC475124
0.679 Remote Similarity NPC212210
0.679 Remote Similarity NPC285371
0.6786 Remote Similarity NPC256846
0.6778 Remote Similarity NPC472478
0.6778 Remote Similarity NPC250632
0.6774 Remote Similarity NPC29447
0.6774 Remote Similarity NPC471224
0.6774 Remote Similarity NPC469948
0.6774 Remote Similarity NPC474218
0.6774 Remote Similarity NPC470223
0.6762 Remote Similarity NPC24596
0.6739 Remote Similarity NPC83569
0.6739 Remote Similarity NPC41539
0.6739 Remote Similarity NPC69279
0.6729 Remote Similarity NPC79238
0.6709 Remote Similarity NPC276764
0.6709 Remote Similarity NPC472304
0.6705 Remote Similarity NPC469796
0.6705 Remote Similarity NPC474463
0.6705 Remote Similarity NPC469793
0.6703 Remote Similarity NPC477372
0.6702 Remote Similarity NPC470050
0.6702 Remote Similarity NPC474732
0.6702 Remote Similarity NPC470051
0.6702 Remote Similarity NPC31564
0.6702 Remote Similarity NPC145879
0.6702 Remote Similarity NPC51014
0.6702 Remote Similarity NPC474778
0.6702 Remote Similarity NPC469994
0.6702 Remote Similarity NPC474733
0.6667 Remote Similarity NPC473246
0.6667 Remote Similarity NPC237712
0.6667 Remote Similarity NPC87141
0.6667 Remote Similarity NPC16287
0.6667 Remote Similarity NPC124358
0.6667 Remote Similarity NPC87552
0.6667 Remote Similarity NPC135005
0.6667 Remote Similarity NPC144258
0.6667 Remote Similarity NPC181743
0.6667 Remote Similarity NPC178025
0.6667 Remote Similarity NPC472306
0.6667 Remote Similarity NPC159497
0.6636 Remote Similarity NPC472313
0.6635 Remote Similarity NPC475239
0.6632 Remote Similarity NPC475740
0.6632 Remote Similarity NPC90652
0.6632 Remote Similarity NPC317590
0.6632 Remote Similarity NPC58063
0.6632 Remote Similarity NPC93778
0.6632 Remote Similarity NPC136948
0.6632 Remote Similarity NPC96496

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC21667 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
0.775 Intermediate Similarity NPD4747 Approved
0.7722 Intermediate Similarity NPD3621 Clinical (unspecified phase)
0.7625 Intermediate Similarity NPD4137 Phase 3
0.7531 Intermediate Similarity NPD4691 Approved
0.75 Intermediate Similarity NPD3527 Clinical (unspecified phase)
0.747 Intermediate Similarity NPD5733 Approved
0.7447 Intermediate Similarity NPD5769 Clinical (unspecified phase)
0.7262 Intermediate Similarity NPD4058 Approved
0.7262 Intermediate Similarity NPD4687 Approved
0.7229 Intermediate Similarity NPD5276 Approved
0.6848 Remote Similarity NPD4786 Approved
0.6813 Remote Similarity NPD4223 Phase 3
0.6813 Remote Similarity NPD4221 Approved
0.6774 Remote Similarity NPD5329 Approved
0.6703 Remote Similarity NPD8028 Phase 2
0.6702 Remote Similarity NPD6098 Approved
0.6667 Remote Similarity NPD4197 Approved
0.663 Remote Similarity NPD3667 Approved
0.6562 Remote Similarity NPD6672 Approved
0.6562 Remote Similarity NPD5737 Approved
0.6556 Remote Similarity NPD4777 Suspended
0.6556 Remote Similarity NPD4776 Phase 2
0.6526 Remote Similarity NPD4693 Phase 3
0.6526 Remote Similarity NPD7521 Approved
0.6526 Remote Similarity NPD5330 Approved
0.6526 Remote Similarity NPD4689 Approved
0.6526 Remote Similarity NPD7146 Approved
0.6526 Remote Similarity NPD7334 Approved
0.6526 Remote Similarity NPD6684 Approved
0.6526 Remote Similarity NPD4138 Approved
0.6526 Remote Similarity NPD4688 Approved
0.6526 Remote Similarity NPD6409 Approved
0.6526 Remote Similarity NPD4690 Approved
0.6526 Remote Similarity NPD5205 Approved
0.6512 Remote Similarity NPD6939 Phase 2
0.6512 Remote Similarity NPD6938 Clinical (unspecified phase)
0.6495 Remote Similarity NPD5328 Approved
0.6495 Remote Similarity NPD6673 Approved
0.6495 Remote Similarity NPD6080 Approved
0.6495 Remote Similarity NPD6904 Approved
0.6489 Remote Similarity NPD3133 Approved
0.6489 Remote Similarity NPD3666 Approved
0.6489 Remote Similarity NPD3668 Phase 3
0.6489 Remote Similarity NPD3665 Phase 1
0.6429 Remote Similarity NPD4096 Approved
0.6392 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6392 Remote Similarity NPD6903 Approved
0.6392 Remote Similarity NPD5208 Approved
0.6374 Remote Similarity NPD3617 Approved
0.6364 Remote Similarity NPD6079 Approved
0.6354 Remote Similarity NPD5690 Phase 2
0.6354 Remote Similarity NPD3618 Phase 1
0.6354 Remote Similarity NPD4694 Approved
0.6354 Remote Similarity NPD5280 Approved
0.6327 Remote Similarity NPD4753 Phase 2
0.6304 Remote Similarity NPD7155 Clinical (unspecified phase)
0.63 Remote Similarity NPD6399 Phase 3
0.6275 Remote Similarity NPD5349 Clinical (unspecified phase)
0.625 Remote Similarity NPD4243 Approved
0.625 Remote Similarity NPD5365 Phase 2
0.62 Remote Similarity NPD5693 Phase 1
0.62 Remote Similarity NPD6050 Approved
0.6186 Remote Similarity NPD5279 Phase 3
0.6186 Remote Similarity NPD3574 Clinical (unspecified phase)
0.6176 Remote Similarity NPD6356 Clinical (unspecified phase)
0.6173 Remote Similarity NPD287 Approved
0.617 Remote Similarity NPD4139 Approved
0.617 Remote Similarity NPD857 Phase 3
0.617 Remote Similarity NPD4692 Approved
0.6139 Remote Similarity NPD4202 Approved
0.6129 Remote Similarity NPD4195 Approved
0.6111 Remote Similarity NPD4785 Approved
0.6111 Remote Similarity NPD7333 Discontinued
0.6111 Remote Similarity NPD4784 Approved
0.61 Remote Similarity NPD5207 Approved
0.61 Remote Similarity NPD5692 Phase 3
0.6095 Remote Similarity NPD6404 Discontinued
0.6078 Remote Similarity NPD6001 Approved
0.6064 Remote Similarity NPD4695 Discontinued
0.6058 Remote Similarity NPD6083 Phase 2
0.6058 Remote Similarity NPD6084 Phase 2
0.6044 Remote Similarity NPD6942 Approved
0.6044 Remote Similarity NPD7339 Approved
0.6042 Remote Similarity NPD4788 Approved
0.604 Remote Similarity NPD5284 Approved
0.604 Remote Similarity NPD5694 Approved
0.604 Remote Similarity NPD5281 Approved
0.602 Remote Similarity NPD4519 Discontinued
0.602 Remote Similarity NPD4623 Approved
0.6019 Remote Similarity NPD7812 Clinical (unspecified phase)
0.6019 Remote Similarity NPD4629 Approved
0.6019 Remote Similarity NPD5210 Approved
0.5962 Remote Similarity NPD5221 Approved
0.5962 Remote Similarity NPD5222 Approved
0.5962 Remote Similarity NPD5220 Clinical (unspecified phase)
0.5962 Remote Similarity NPD4697 Phase 3
0.5922 Remote Similarity NPD5771 Approved
0.5905 Remote Similarity NPD4755 Approved
0.5905 Remote Similarity NPD5173 Approved
0.587 Remote Similarity NPD5275 Approved
0.587 Remote Similarity NPD4190 Phase 3
0.5865 Remote Similarity NPD5695 Phase 3
0.5849 Remote Similarity NPD5696 Approved
0.5825 Remote Similarity NPD5133 Approved
0.581 Remote Similarity NPD7614 Phase 1
0.581 Remote Similarity NPD7732 Phase 3
0.58 Remote Similarity NPD3573 Approved
0.5794 Remote Similarity NPD4700 Approved
0.5794 Remote Similarity NPD5286 Approved
0.5794 Remote Similarity NPD4696 Approved
0.5794 Remote Similarity NPD5285 Approved
0.578 Remote Similarity NPD6052 Approved
0.5772 Remote Similarity NPD6330 Clinical (unspecified phase)
0.5769 Remote Similarity NPD5707 Approved
0.5758 Remote Similarity NPD7520 Clinical (unspecified phase)
0.5755 Remote Similarity NPD4657 Approved
0.5755 Remote Similarity NPD4655 Approved
0.5743 Remote Similarity NPD4518 Approved
0.5743 Remote Similarity NPD4722 Approved
0.5743 Remote Similarity NPD4723 Approved
0.5741 Remote Similarity NPD5223 Approved
0.5728 Remote Similarity NPD7515 Phase 2
0.5714 Remote Similarity NPD7148 Clinical (unspecified phase)
0.5714 Remote Similarity NPD7147 Phase 3
0.5714 Remote Similarity NPD5654 Approved
0.5688 Remote Similarity NPD6024 Approved
0.5688 Remote Similarity NPD5211 Phase 2
0.5688 Remote Similarity NPD5226 Approved
0.5688 Remote Similarity NPD6027 Approved
0.5688 Remote Similarity NPD4633 Approved
0.5688 Remote Similarity NPD5225 Approved
0.5688 Remote Similarity NPD5224 Approved
0.5688 Remote Similarity NPD5091 Approved
0.5686 Remote Similarity NPD7285 Clinical (unspecified phase)
0.5684 Remote Similarity NPD1402 Approved
0.568 Remote Similarity NPD6914 Discontinued
0.5676 Remote Similarity NPD7128 Approved
0.5676 Remote Similarity NPD6402 Approved
0.5676 Remote Similarity NPD6675 Approved
0.5676 Remote Similarity NPD5739 Approved
0.5667 Remote Similarity NPD6923 Approved
0.5667 Remote Similarity NPD6922 Approved
0.5667 Remote Similarity NPD6909 Approved
0.5667 Remote Similarity NPD6908 Approved
0.5652 Remote Similarity NPD7336 Phase 2
0.5652 Remote Similarity NPD7335 Phase 2
0.5652 Remote Similarity NPD7337 Clinical (unspecified phase)
0.5638 Remote Similarity NPD3701 Clinical (unspecified phase)
0.5636 Remote Similarity NPD4754 Approved
0.5636 Remote Similarity NPD5175 Approved
0.5636 Remote Similarity NPD5174 Approved
0.5631 Remote Similarity NPD6934 Discontinued
0.5625 Remote Similarity NPD6614 Approved
0.5619 Remote Similarity NPD7901 Clinical (unspecified phase)
0.5619 Remote Similarity NPD7748 Approved
0.5619 Remote Similarity NPD7900 Approved
0.5607 Remote Similarity NPD5959 Approved
0.5604 Remote Similarity NPD7144 Approved
0.5604 Remote Similarity NPD7143 Approved

Structure

External Identifiers

PubChem CID   12310548
ChEMBL   CHEMBL465586
ZINC  

Physicochemical Properties

Molecular Weight:  315.26
ALogP:  -0.0286
MLogP:  3.55
XLogP:  4.766
# Rotatable Bonds:  5
Polar Surface Area:  43.09
# H-Bond Aceptor:  2
# H-Bond Donor:  1
# Rings:  4
# Heavy Atoms:  23

Download Data

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