Structure

Physi-Chem Properties

Molecular Weight:  235.08
Volume:  231.971
LogP:  2.088
LogD:  1.937
LogS:  -4.203
# Rotatable Bonds:  3
TPSA:  48.0
# H-Bond Aceptor:  5
# H-Bond Donor:  0
# Rings:  2
# Heavy Atoms:  5

MedChem Properties

QED Drug-Likeness Score:  0.75
Synthetic Accessibility Score:  3.065
Fsp3:  0.25
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.452
MDCK Permeability:  2.4927867343649268e-05
Pgp-inhibitor:  0.001
Pgp-substrate:  0.002
Human Intestinal Absorption (HIA):  0.008
20% Bioavailability (F20%):  0.01
30% Bioavailability (F30%):  0.241

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.997
Plasma Protein Binding (PPB):  54.65658950805664%
Volume Distribution (VD):  1.138
Pgp-substrate:  47.98518371582031%

ADMET: Metabolism

CYP1A2-inhibitor:  0.863
CYP1A2-substrate:  0.803
CYP2C19-inhibitor:  0.413
CYP2C19-substrate:  0.901
CYP2C9-inhibitor:  0.154
CYP2C9-substrate:  0.774
CYP2D6-inhibitor:  0.019
CYP2D6-substrate:  0.853
CYP3A4-inhibitor:  0.127
CYP3A4-substrate:  0.837

ADMET: Excretion

Clearance (CL):  6.855
Half-life (T1/2):  0.553

ADMET: Toxicity

hERG Blockers:  0.007
Human Hepatotoxicity (H-HT):  0.384
Drug-inuced Liver Injury (DILI):  0.577
AMES Toxicity:  0.162
Rat Oral Acute Toxicity:  0.23
Maximum Recommended Daily Dose:  0.048
Skin Sensitization:  0.682
Carcinogencity:  0.317
Eye Corrosion:  0.006
Eye Irritation:  0.189
Respiratory Toxicity:  0.161

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

  Natural Product: NPC476462

Natural Product ID:  NPC476462
Common Name*:   3,7-Dimethoxy-2-Methyl-1,4-Benzoxazine-4-Carbaldehyde
IUPAC Name:   3,7-dimethoxy-2-methyl-1,4-benzoxazine-4-carbaldehyde
Synonyms:  
Standard InCHIKey:  PTTIXXJFMSKCPB-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C12H13NO4/c1-8-12(16-3)13(7-14)10-5-4-9(15-2)6-11(10)17-8/h4-7H,1-3H3
SMILES:  CC1=C(N(C2=C(O1)C=C(C=C2)OC)C=O)OC
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL71325
PubChem CID:   44310862
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0001396] Benzoxazines

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

  Species Source

Organism ID Organism Name Taxonomy Level Family SuperKingdom Isolation Part Collection Location Collection Time Reference
NPO4868 Capparis sikkimensis Species Capparaceae Eukaryota n.a. n.a. n.a. PMID[12798338]
NPO4868 Capparis sikkimensis Species Capparaceae Eukaryota n.a. n.a. n.a. Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

  NP Quantity Composition/Concentration

Organism ID NP ID Organism Material Preparation Organism Part NP Quantity (Standard) NP Quantity (Minimum) NP Quantity (Maximum) Quantity Unit Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT180 Cell Line HCT-8 Homo sapiens ED50 > 20.0 ug ml-1 PMID[517655]
NPT180 Cell Line HCT-8 Homo sapiens Inhibition = 39.0 % PMID[517655]
NPT1535 Cell Line U-87 MG Homo sapiens ED50 > 20.0 ug ml-1 PMID[517655]
NPT1535 Cell Line U-87 MG Homo sapiens Inhibition = 19.0 % PMID[517655]
NPT1178 Cell Line KB 3-1 Homo sapiens ED50 > 20.0 ug ml-1 PMID[517655]
NPT1178 Cell Line KB 3-1 Homo sapiens Inhibition = 20.0 % PMID[517655]
NPT306 Cell Line PC-3 Homo sapiens ED50 > 20.0 ug ml-1 PMID[517655]
NPT306 Cell Line PC-3 Homo sapiens Inhibition = 37.0 % PMID[517655]
NPT81 Cell Line A549 Homo sapiens ED50 > 20.0 ug ml-1 PMID[517655]
NPT81 Cell Line A549 Homo sapiens Inhibition = 36.0 % PMID[517655]
NPT83 Cell Line MCF7 Homo sapiens ED50 > 20.0 ug ml-1 PMID[517655]
NPT83 Cell Line MCF7 Homo sapiens Inhibition = 49.0 % PMID[517655]
NPT27 Others Unspecified ED50 > 20.0 ug ml-1 PMID[517655]
NPT27 Others Unspecified Inhibition = 22.0 % PMID[517655]
NPT2 Others Unspecified ED50 = 20.0 ug ml-1 PMID[517655]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

  Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available 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 NPC476462 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
0.9851 High Similarity NPC260601
0.7987 Intermediate Similarity NPC473769
0.773 Intermediate Similarity NPC290069
0.7683 Intermediate Similarity NPC220560
0.758 Intermediate Similarity NPC112766
0.7434 Intermediate Similarity NPC168750
0.7421 Intermediate Similarity NPC70549
0.74 Intermediate Similarity NPC476475
0.7343 Intermediate Similarity NPC315632
0.7222 Intermediate Similarity NPC306366
0.7174 Intermediate Similarity NPC264782
0.7133 Intermediate Similarity NPC297584
0.7067 Intermediate Similarity NPC208022
0.7055 Intermediate Similarity NPC301163
0.7047 Intermediate Similarity NPC473987
0.6988 Remote Similarity NPC204179
0.6813 Remote Similarity NPC314948
0.6807 Remote Similarity NPC231862
0.6779 Remote Similarity NPC250476
0.674 Remote Similarity NPC471825
0.6724 Remote Similarity NPC287152
0.6721 Remote Similarity NPC478049
0.6667 Remote Similarity NPC57105
0.6648 Remote Similarity NPC116096
0.6647 Remote Similarity NPC314861
0.6627 Remote Similarity NPC315257
0.6607 Remote Similarity NPC93653
0.6601 Remote Similarity NPC231382
0.6596 Remote Similarity NPC226914
0.6592 Remote Similarity NPC262725
0.6519 Remote Similarity NPC313918
0.6491 Remote Similarity NPC70172
0.6481 Remote Similarity NPC473874
0.6474 Remote Similarity NPC470484
0.6452 Remote Similarity NPC313466
0.6442 Remote Similarity NPC110337
0.6438 Remote Similarity NPC314113
0.6425 Remote Similarity NPC98197
0.6412 Remote Similarity NPC19023
0.6408 Remote Similarity NPC255721
0.64 Remote Similarity NPC73280
0.6383 Remote Similarity NPC220408
0.6383 Remote Similarity NPC76327
0.6364 Remote Similarity NPC302546
0.6364 Remote Similarity NPC95977
0.6343 Remote Similarity NPC471648
0.6339 Remote Similarity NPC217294
0.6292 Remote Similarity NPC315631
0.6288 Remote Similarity NPC47422
0.6278 Remote Similarity NPC472163
0.627 Remote Similarity NPC1820
0.6257 Remote Similarity NPC316161
0.6243 Remote Similarity NPC234933
0.6233 Remote Similarity NPC322735
0.6221 Remote Similarity NPC235628
0.6221 Remote Similarity NPC320064
0.6212 Remote Similarity NPC30749
0.6212 Remote Similarity NPC268223
0.6211 Remote Similarity NPC113236
0.6211 Remote Similarity NPC214036
0.6207 Remote Similarity NPC299582
0.619 Remote Similarity NPC329190
0.6188 Remote Similarity NPC197335
0.6175 Remote Similarity NPC313886
0.6173 Remote Similarity NPC47986
0.6169 Remote Similarity NPC195120
0.6159 Remote Similarity NPC308197
0.6158 Remote Similarity NPC112937
0.6154 Remote Similarity NPC314659
0.6149 Remote Similarity NPC118511
0.614 Remote Similarity NPC10730
0.614 Remote Similarity NPC10875
0.6138 Remote Similarity NPC106141
0.6105 Remote Similarity NPC272706
0.6099 Remote Similarity NPC118776
0.6099 Remote Similarity NPC311660
0.6099 Remote Similarity NPC288305
0.6096 Remote Similarity NPC475411
0.6092 Remote Similarity NPC230942
0.6092 Remote Similarity NPC315498
0.6092 Remote Similarity NPC257763
0.6089 Remote Similarity NPC182853
0.6089 Remote Similarity NPC87560
0.6087 Remote Similarity NPC138365
0.6084 Remote Similarity NPC473653
0.608 Remote Similarity NPC305542
0.608 Remote Similarity NPC471652
0.6074 Remote Similarity NPC204156
0.6071 Remote Similarity NPC70201
0.6064 Remote Similarity NPC206109
0.6064 Remote Similarity NPC114039
0.6058 Remote Similarity NPC16649
0.6054 Remote Similarity NPC87391
0.6045 Remote Similarity NPC1527
0.6037 Remote Similarity NPC212850
0.6037 Remote Similarity NPC83289
0.6037 Remote Similarity NPC189724
0.6031 Remote Similarity NPC15987
0.6029 Remote Similarity NPC118154
0.6029 Remote Similarity NPC157983
0.6025 Remote Similarity NPC29650
0.6023 Remote Similarity NPC24954
0.6022 Remote Similarity NPC66083
0.601 Remote Similarity NPC140296
0.6 Remote Similarity NPC274732
0.6 Remote Similarity NPC128633
0.6 Remote Similarity NPC42591
0.6 Remote Similarity NPC118189
0.599 Remote Similarity NPC198160
0.599 Remote Similarity NPC212123
0.5989 Remote Similarity NPC127362
0.5988 Remote Similarity NPC244338
0.5987 Remote Similarity NPC298796
0.5987 Remote Similarity NPC321869
0.5979 Remote Similarity NPC214368
0.5978 Remote Similarity NPC471604
0.5976 Remote Similarity NPC242000
0.5975 Remote Similarity NPC200555
0.5975 Remote Similarity NPC196026
0.5968 Remote Similarity NPC61350
0.5959 Remote Similarity NPC241263
0.5957 Remote Similarity NPC45389
0.5956 Remote Similarity NPC5167
0.5946 Remote Similarity NPC469829
0.5943 Remote Similarity NPC285635
0.5935 Remote Similarity NPC314702
0.5931 Remote Similarity NPC44836
0.5931 Remote Similarity NPC134702
0.5924 Remote Similarity NPC190461
0.5924 Remote Similarity NPC270301
0.5922 Remote Similarity NPC76478
0.5921 Remote Similarity NPC265547
0.5921 Remote Similarity NPC96705
0.5921 Remote Similarity NPC152306
0.592 Remote Similarity NPC116178
0.5918 Remote Similarity NPC9336
0.5918 Remote Similarity NPC329358
0.5917 Remote Similarity NPC473934
0.5916 Remote Similarity NPC198401
0.5912 Remote Similarity NPC283079
0.5909 Remote Similarity NPC163200
0.5906 Remote Similarity NPC40209
0.5904 Remote Similarity NPC110741
0.5895 Remote Similarity NPC473004
0.5894 Remote Similarity NPC251071
0.5893 Remote Similarity NPC247298
0.5892 Remote Similarity NPC469831
0.5891 Remote Similarity NPC321166
0.5891 Remote Similarity NPC217903
0.589 Remote Similarity NPC245115
0.5889 Remote Similarity NPC85482
0.5885 Remote Similarity NPC108847
0.5882 Remote Similarity NPC281356
0.5879 Remote Similarity NPC288943
0.5879 Remote Similarity NPC473432
0.5871 Remote Similarity NPC295479
0.5871 Remote Similarity NPC220241
0.5871 Remote Similarity NPC218303
0.587 Remote Similarity NPC85613
0.5864 Remote Similarity NPC279401
0.5864 Remote Similarity NPC78284
0.5864 Remote Similarity NPC79293
0.5864 Remote Similarity NPC266425
0.5862 Remote Similarity NPC148391
0.586 Remote Similarity NPC62069
0.5858 Remote Similarity NPC9373
0.5857 Remote Similarity NPC13249
0.5856 Remote Similarity NPC83198
0.5856 Remote Similarity NPC204908
0.5849 Remote Similarity NPC172403
0.5848 Remote Similarity NPC37144
0.5848 Remote Similarity NPC59907
0.5847 Remote Similarity NPC283152
0.5842 Remote Similarity NPC469390
0.5842 Remote Similarity NPC470483
0.5838 Remote Similarity NPC26872
0.5833 Remote Similarity NPC234772
0.5829 Remote Similarity NPC16249
0.5829 Remote Similarity NPC169742
0.5829 Remote Similarity NPC123323
0.5825 Remote Similarity NPC127085
0.5824 Remote Similarity NPC245974
0.5822 Remote Similarity NPC35543
0.5819 Remote Similarity NPC177404
0.5817 Remote Similarity NPC148124
0.5806 Remote Similarity NPC180006
0.5806 Remote Similarity NPC235190
0.5801 Remote Similarity NPC258773
0.58 Remote Similarity NPC308392
0.5796 Remote Similarity NPC217277
0.5796 Remote Similarity NPC315807
0.5796 Remote Similarity NPC472518
0.5796 Remote Similarity NPC273772
0.5796 Remote Similarity NPC109675
0.5793 Remote Similarity NPC209195
0.5793 Remote Similarity NPC13826
0.5793 Remote Similarity NPC307875
0.5792 Remote Similarity NPC227060
0.5792 Remote Similarity NPC198498
0.5792 Remote Similarity NPC317145

  Chemically structural similarity: II. Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC476462 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
0.7613 Intermediate Similarity NPD1678 Clinical (unspecified phase)
0.7436 Intermediate Similarity NPD8330 Clinical (unspecified phase)
0.7358 Intermediate Similarity NPD4201 Clinical (unspecified phase)
0.7338 Intermediate Similarity NPD254 Approved
0.7285 Intermediate Similarity NPD822 Approved
0.7285 Intermediate Similarity NPD5788 Clinical (unspecified phase)
0.7273 Intermediate Similarity NPD2241 Approved
0.725 Intermediate Similarity NPD4205 Phase 3
0.7248 Intermediate Similarity NPD1393 Approved
0.7192 Intermediate Similarity NPD848 Approved
0.7192 Intermediate Similarity NPD849 Approved
0.7192 Intermediate Similarity NPD850 Approved
0.7169 Intermediate Similarity NPD5847 Phase 1
0.7143 Intermediate Similarity NPD1440 Discontinued
0.708 Intermediate Similarity NPD9376 Approved
0.7019 Intermediate Similarity NPD789 Phase 2
0.7 Intermediate Similarity NPD4020 Clinical (unspecified phase)
0.6968 Remote Similarity NPD7753 Approved
0.6968 Remote Similarity NPD7752 Approved
0.6951 Remote Similarity NPD5294 Clinical (unspecified phase)
0.6923 Remote Similarity NPD5719 Approved
0.6906 Remote Similarity NPD6621 Clinical (unspecified phase)
0.6903 Remote Similarity NPD1422 Approved
0.6894 Remote Similarity NPD3627 Approved
0.6882 Remote Similarity NPD5858 Discontinued
0.6853 Remote Similarity NPD1408 Clinical (unspecified phase)
0.6829 Remote Similarity NPD4255 Phase 1
0.6818 Remote Similarity NPD4586 Phase 3
0.6815 Remote Similarity NPD4598 Approved
0.6815 Remote Similarity NPD4597 Approved
0.6813 Remote Similarity NPD2114 Discontinued
0.6807 Remote Similarity NPD1012 Discontinued
0.6805 Remote Similarity NPD7126 Discontinued
0.6797 Remote Similarity NPD756 Suspended
0.6788 Remote Similarity NPD1769 Discontinued
0.6763 Remote Similarity NPD1212 Approved
0.6746 Remote Similarity NPD2162 Clinical (unspecified phase)
0.6742 Remote Similarity NPD4587 Phase 3
0.6733 Remote Similarity NPD9723 Approved
0.6731 Remote Similarity NPD204 Clinical (unspecified phase)
0.6721 Remote Similarity NPD6034 Phase 2
0.6706 Remote Similarity NPD6379 Discontinued
0.669 Remote Similarity NPD7534 Approved
0.669 Remote Similarity NPD7533 Approved
0.6686 Remote Similarity NPD6654 Clinical (unspecified phase)
0.6667 Remote Similarity NPD1191 Discontinued
0.6667 Remote Similarity NPD308 Approved
0.6667 Remote Similarity NPD3538 Suspended
0.6667 Remote Similarity NPD2200 Suspended
0.6647 Remote Similarity NPD6060 Clinical (unspecified phase)
0.6646 Remote Similarity NPD521 Clinical (unspecified phase)
0.6644 Remote Similarity NPD2594 Approved
0.6644 Remote Similarity NPD2595 Approved
0.6609 Remote Similarity NPD6645 Clinical (unspecified phase)
0.6608 Remote Similarity NPD2249 Approved
0.6608 Remote Similarity NPD2247 Approved
0.6601 Remote Similarity NPD1314 Clinical (unspecified phase)
0.6591 Remote Similarity NPD6211 Clinical (unspecified phase)
0.6584 Remote Similarity NPD5307 Clinical (unspecified phase)
0.6575 Remote Similarity NPD4428 Discontinued
0.6571 Remote Similarity NPD5334 Clinical (unspecified phase)
0.6571 Remote Similarity NPD5521 Clinical (unspecified phase)
0.6552 Remote Similarity NPD5938 Phase 3
0.6543 Remote Similarity NPD1305 Clinical (unspecified phase)
0.6534 Remote Similarity NPD3580 Discontinued
0.6534 Remote Similarity NPD5900 Clinical (unspecified phase)
0.6533 Remote Similarity NPD1158 Phase 2
0.6529 Remote Similarity NPD6533 Clinical (unspecified phase)
0.6527 Remote Similarity NPD3778 Approved
0.6514 Remote Similarity NPD5132 Clinical (unspecified phase)
0.6514 Remote Similarity NPD5603 Clinical (unspecified phase)
0.65 Remote Similarity NPD5373 Approved
0.65 Remote Similarity NPD5374 Approved
0.6494 Remote Similarity NPD5078 Clinical (unspecified phase)
0.6474 Remote Similarity NPD4606 Clinical (unspecified phase)
0.6464 Remote Similarity NPD6393 Clinical (unspecified phase)
0.646 Remote Similarity NPD965 Approved
0.6453 Remote Similarity NPD4943 Phase 2
0.6453 Remote Similarity NPD4944 Phase 2
0.6442 Remote Similarity NPD1084 Clinical (unspecified phase)
0.6441 Remote Similarity NPD795 Clinical (unspecified phase)
0.6438 Remote Similarity NPD7083 Clinical (unspecified phase)
0.6429 Remote Similarity NPD3537 Clinical (unspecified phase)
0.642 Remote Similarity NPD4498 Clinical (unspecified phase)
0.6416 Remote Similarity NPD3511 Discontinued
0.6412 Remote Similarity NPD3558 Approved
0.6412 Remote Similarity NPD3556 Approved
0.6412 Remote Similarity NPD3557 Approved
0.6412 Remote Similarity NPD3559 Clinical (unspecified phase)
0.6412 Remote Similarity NPD3560 Approved
0.6407 Remote Similarity NPD6357 Discontinued
0.6406 Remote Similarity NPD7263 Phase 2
0.6405 Remote Similarity NPD2990 Approved
0.6405 Remote Similarity NPD1160 Phase 2
0.6405 Remote Similarity NPD2987 Approved
0.64 Remote Similarity NPD6365 Clinical (unspecified phase)
0.6395 Remote Similarity NPD313 Approved
0.6393 Remote Similarity NPD6136 Phase 2
0.6384 Remote Similarity NPD3793 Phase 3
0.6383 Remote Similarity NPD9507 Approved
0.6374 Remote Similarity NPD4515 Suspended
0.6364 Remote Similarity NPD2673 Approved
0.6364 Remote Similarity NPD2671 Approved
0.6353 Remote Similarity NPD6668 Clinical (unspecified phase)
0.6353 Remote Similarity NPD2842 Clinical (unspecified phase)
0.6339 Remote Similarity NPD7326 Phase 3
0.6339 Remote Similarity NPD1898 Discontinued
0.6335 Remote Similarity NPD9245 Clinical (unspecified phase)
0.6331 Remote Similarity NPD980 Clinical (unspecified phase)
0.6329 Remote Similarity NPD9694 Discovery
0.6324 Remote Similarity NPD4325 Phase 2
0.6324 Remote Similarity NPD4324 Phase 2
0.631 Remote Similarity NPD5582 Discontinued
0.6307 Remote Similarity NPD6607 Clinical (unspecified phase)
0.6304 Remote Similarity NPD6880 Phase 3
0.6298 Remote Similarity NPD6338 Approved
0.6298 Remote Similarity NPD6337 Approved
0.629 Remote Similarity NPD7125 Discontinued
0.628 Remote Similarity NPD3301 Approved
0.6264 Remote Similarity NPD2341 Discontinued
0.6264 Remote Similarity NPD5677 Discontinued
0.6259 Remote Similarity NPD9342 Approved
0.625 Remote Similarity NPD7064 Clinical (unspecified phase)
0.625 Remote Similarity NPD2216 Approved
0.625 Remote Similarity NPD2215 Approved
0.625 Remote Similarity NPD814 Clinical (unspecified phase)
0.6235 Remote Similarity NPD2366 Approved
0.623 Remote Similarity NPD7566 Clinical (unspecified phase)
0.6229 Remote Similarity NPD6457 Approved
0.6229 Remote Similarity NPD2681 Approved
0.6229 Remote Similarity NPD2680 Approved
0.6222 Remote Similarity NPD6496 Clinical (unspecified phase)
0.6222 Remote Similarity NPD6293 Clinical (unspecified phase)
0.6209 Remote Similarity NPD1420 Approved
0.6209 Remote Similarity NPD1421 Approved
0.6205 Remote Similarity NPD7213 Phase 3
0.6205 Remote Similarity NPD7212 Phase 2
0.6199 Remote Similarity NPD1861 Discovery
0.619 Remote Similarity NPD286 Approved
0.6188 Remote Similarity NPD6104 Discontinued
0.6188 Remote Similarity NPD3386 Phase 2
0.6188 Remote Similarity NPD7149 Clinical (unspecified phase)
0.6176 Remote Similarity NPD4678 Approved
0.6176 Remote Similarity NPD4675 Approved
0.6168 Remote Similarity NPD7447 Phase 1
0.6168 Remote Similarity NPD2335 Discontinued
0.6154 Remote Similarity NPD4993 Discontinued
0.6154 Remote Similarity NPD3563 Approved
0.6154 Remote Similarity NPD3562 Approved
0.6154 Remote Similarity NPD3564 Approved
0.615 Remote Similarity NPD4372 Phase 1
0.6149 Remote Similarity NPD6636 Phase 3
0.6146 Remote Similarity NPD6321 Discontinued
0.6141 Remote Similarity NPD6638 Approved
0.6139 Remote Similarity NPD3514 Clinical (unspecified phase)
0.6126 Remote Similarity NPD1880 Phase 3
0.6118 Remote Similarity NPD8158 Clinical (unspecified phase)
0.6114 Remote Similarity NPD2498 Approved
0.6111 Remote Similarity NPD5600 Discontinued
0.6105 Remote Similarity NPD5515 Phase 2
0.6102 Remote Similarity NPD5183 Approved
0.6102 Remote Similarity NPD5186 Approved
0.6092 Remote Similarity NPD1743 Approved
0.6092 Remote Similarity NPD19 Approved
0.6092 Remote Similarity NPD1742 Approved
0.6074 Remote Similarity NPD3391 Approved
0.6067 Remote Similarity NPD4083 Discontinued
0.6066 Remote Similarity NPD6461 Clinical (unspecified phase)
0.6062 Remote Similarity NPD1621 Discontinued
0.6059 Remote Similarity NPD950 Clinical (unspecified phase)
0.6059 Remote Similarity NPD9596 Approved
0.6059 Remote Similarity NPD9595 Approved
0.6051 Remote Similarity NPD5102 Clinical (unspecified phase)
0.6051 Remote Similarity NPD6644 Discontinued
0.6045 Remote Similarity NPD3984 Clinical (unspecified phase)
0.6045 Remote Similarity NPD3983 Phase 3
0.6043 Remote Similarity NPD5114 Approved
0.6043 Remote Similarity NPD5112 Approved
0.6043 Remote Similarity NPD5113 Approved
0.6042 Remote Similarity NPD5547 Clinical (unspecified phase)
0.6042 Remote Similarity NPD6757 Phase 3
0.6034 Remote Similarity NPD2246 Approved
0.6034 Remote Similarity NPD6063 Approved
0.6034 Remote Similarity NPD2248 Approved
0.6033 Remote Similarity NPD7877 Suspended
0.603 Remote Similarity NPD4206 Approved
0.6024 Remote Similarity NPD7466 Approved
0.6023 Remote Similarity NPD4796 Discontinued
0.6021 Remote Similarity NPD4605 Approved
0.6021 Remote Similarity NPD4604 Approved
0.6013 Remote Similarity NPD3447 Discontinued
0.6012 Remote Similarity NPD3260 Discontinued
0.6012 Remote Similarity NPD2752 Clinical (unspecified phase)
0.6011 Remote Similarity NPD5994 Discontinued
0.6011 Remote Similarity NPD5320 Approved
0.6011 Remote Similarity NPD5319 Approved
0.6011 Remote Similarity NPD565 Phase 2
0.6 Remote Similarity NPD6021 Clinical (unspecified phase)
0.599 Remote Similarity NPD2434 Approved
0.5989 Remote Similarity NPD6608 Clinical (unspecified phase)

  Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity
B: biological targets similarity
C: networks similarity
D: cell-based bioactivity similarity
E: similarity based on clinical data