Drug Information

Drug ID:  NPD9014
Drug Name:  L-Citrulline
Molecular Formula:  C6H13N3O3
Canonical SMILES:  OC(=N)NCCC[C@@H](C(=O)O)N
Standard InCHI:  InChI=1S/C6H13N3O3/c7-4(5(10)11)2-1-3-9-6(8)12/h4H,1-3,7H2,(H,10,11)(H3,8,9,12)/t4-/m0/s1
Standard InCHIKey:  RHGKLRLOHDJJDR-BYPYZUCNSA-N
Max Developmental Stage:  Approved
Max Developmental Stage Source:  DrugBank

  Structural Similarity Between NPASS Natural Products and NPD9014

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
Tanimoto coefficient is calculated based on PubChem 881-bit substructure fingerprints.


  Similar Natural Products

High Similarity Level: Tc>=0.85; Intermediate Similarity Level: 0.7 <= Tc < 0.85; Remote Similarity Level: 0.65 <= Tc < 0.7

Similarity Level Similarity Score Natural Product ID
High Similarity 1.0 NPC118429
High Similarity 0.9322 NPC226453
High Similarity 0.9322 NPC103130
High Similarity 0.9016 NPC327985
High Similarity 0.8594 NPC133183
Intermediate Similarity 0.8333 NPC328457
Intermediate Similarity 0.8254 NPC278881
Intermediate Similarity 0.8125 NPC325534
Intermediate Similarity 0.7857 NPC93081
Intermediate Similarity 0.7857 NPC140872
Intermediate Similarity 0.7759 NPC202525
Intermediate Similarity 0.7667 NPC10915
Intermediate Similarity 0.7581 NPC11433
Intermediate Similarity 0.7581 NPC245346
Intermediate Similarity 0.7581 NPC302003
Intermediate Similarity 0.75 NPC322206
Intermediate Similarity 0.7333 NPC245768
Intermediate Similarity 0.7143 NPC278209
Intermediate Similarity 0.7119 NPC112890
Intermediate Similarity 0.7119 NPC316231
Intermediate Similarity 0.7119 NPC324825
Intermediate Similarity 0.7018 NPC118459
Intermediate Similarity 0.7018 NPC327698
Remote Similarity 0.6964 NPC276294
Remote Similarity 0.6935 NPC183845
Remote Similarity 0.6935 NPC279661
Remote Similarity 0.6923 NPC268927
Remote Similarity 0.6923 NPC64250
Remote Similarity 0.6923 NPC276928
Remote Similarity 0.6812 NPC287693
Remote Similarity 0.6774 NPC190184
Remote Similarity 0.6774 NPC197087
Remote Similarity 0.6769 NPC189301
Remote Similarity 0.6769 NPC176164
Remote Similarity 0.6761 NPC322274
Remote Similarity 0.6719 NPC38463
Remote Similarity 0.6719 NPC325985
Remote Similarity 0.6714 NPC196359
Remote Similarity 0.6714 NPC78312
Remote Similarity 0.6714 NPC135539
Remote Similarity 0.6714 NPC221764
Remote Similarity 0.6667 NPC254541
Remote Similarity 0.6667 NPC320598
Remote Similarity 0.6622 NPC320221
Remote Similarity 0.662 NPC81647
Remote Similarity 0.6557 NPC162620
Remote Similarity 0.6557 NPC62045
Remote Similarity 0.6557 NPC245027
Remote Similarity 0.6557 NPC226027
Remote Similarity 0.6557 NPC43204
Remote Similarity 0.6557 NPC84636
Remote Similarity 0.6557 NPC174246
Remote Similarity 0.6528 NPC15864
Remote Similarity 0.65 NPC101249
Remote Similarity 0.6494 NPC191774
Remote Similarity 0.6452 NPC137958
Remote Similarity 0.6452 NPC273330
Remote Similarity 0.6441 NPC329263
Remote Similarity 0.6418 NPC321536
Remote Similarity 0.6418 NPC317143
Remote Similarity 0.6418 NPC316826
Remote Similarity 0.6418 NPC321468
Remote Similarity 0.6418 NPC327748
Remote Similarity 0.6406 NPC60672
Remote Similarity 0.6406 NPC322091
Remote Similarity 0.6364 NPC317147
Remote Similarity 0.6364 NPC318260
Remote Similarity 0.6324 NPC327170
Remote Similarity 0.6324 NPC143722
Remote Similarity 0.6324 NPC329564
Remote Similarity 0.6316 NPC327272
Remote Similarity 0.6316 NPC121517
Remote Similarity 0.6316 NPC168375
Remote Similarity 0.6316 NPC326992
Remote Similarity 0.6308 NPC322573
Remote Similarity 0.6271 NPC323974
Remote Similarity 0.6271 NPC198301
Remote Similarity 0.625 NPC274499
Remote Similarity 0.625 NPC333075
Remote Similarity 0.625 NPC8488
Remote Similarity 0.6164 NPC107224
Remote Similarity 0.6129 NPC153370
Remote Similarity 0.6102 NPC291186
Remote Similarity 0.6102 NPC167986
Remote Similarity 0.6094 NPC155156
Remote Similarity 0.6094 NPC200550
Remote Similarity 0.6087 NPC177191
Remote Similarity 0.6087 NPC68974
Remote Similarity 0.6066 NPC297220
Remote Similarity 0.6061 NPC2801
Remote Similarity 0.6056 NPC289691
Remote Similarity 0.6032 NPC328378
Remote Similarity 0.6024 NPC199072
Remote Similarity 0.6 NPC132307
Remote Similarity 0.6 NPC325097
Remote Similarity 0.6 NPC126925
Remote Similarity 0.6 NPC273037
Remote Similarity 0.6 NPC40511
Remote Similarity 0.5972 NPC160661
Remote Similarity 0.5972 NPC174304
Remote Similarity 0.5972 NPC325597
Remote Similarity 0.5968 NPC136159
Remote Similarity 0.5949 NPC315780
Remote Similarity 0.5909 NPC321118
Remote Similarity 0.5909 NPC316889
Remote Similarity 0.5846 NPC322946
Remote Similarity 0.5844 NPC315897
Remote Similarity 0.5844 NPC185084
Remote Similarity 0.5833 NPC315744
Remote Similarity 0.5821 NPC327831
Remote Similarity 0.5811 NPC222327
Remote Similarity 0.5811 NPC188231
Remote Similarity 0.5806 NPC195448
Remote Similarity 0.5806 NPC136476
Remote Similarity 0.5806 NPC49952
Remote Similarity 0.5797 NPC190385
Remote Similarity 0.5763 NPC326212
Remote Similarity 0.5763 NPC237525
Remote Similarity 0.5763 NPC66043
Remote Similarity 0.5763 NPC53449
Remote Similarity 0.5758 NPC189178
Remote Similarity 0.5758 NPC263065
Remote Similarity 0.5747 NPC304454
Remote Similarity 0.5733 NPC319046
Remote Similarity 0.5692 NPC125736
Remote Similarity 0.5692 NPC110136
Remote Similarity 0.5692 NPC50457
Remote Similarity 0.569 NPC18188
Remote Similarity 0.5658 NPC126779
Remote Similarity 0.5645 NPC208793
Remote Similarity 0.5645 NPC285322
Remote Similarity 0.5618 NPC304455
Remote Similarity 0.5614 NPC116709
Remote Similarity 0.5614 NPC272614
Remote Similarity 0.5614 NPC21290
Remote Similarity 0.5606 NPC29950
Remote Similarity 0.5606 NPC155512
Remote Similarity 0.5606 NPC19576
Remote Similarity 0.56 NPC118524

Drug Structure

External Identifiers

TTD  
DrugBank   DB00155
ChEMBL   CHEMBL444814
IUPHAR/BPS  
PharmaGKB   PA164747225
KEGG Drug  
PubChem CID  
ChEBI   16349
CAS Number  372-75-8

Drug Properties

Molecular Weight  175.10
ALogP  -1.7857
MLogP  1.46
XLogP  -2.513
HDA  6
HBD  5
Rotatable Bonds  9
TPSA  119.43
RO5 Violation  0