Structure

Physi-Chem Properties

Molecular Weight:  346.21
Volume:  364.798
LogP:  2.298
LogD:  2.056
LogS:  -3.946
# Rotatable Bonds:  2
TPSA:  63.6
# H-Bond Aceptor:  4
# H-Bond Donor:  1
# Rings:  4
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.585
Synthetic Accessibility Score:  5.725
Fsp3:  0.81
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  2
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.775
MDCK Permeability:  2.831728670571465e-05
Pgp-inhibitor:  0.987
Pgp-substrate:  0.001
Human Intestinal Absorption (HIA):  0.007
20% Bioavailability (F20%):  0.383
30% Bioavailability (F30%):  0.166

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.78
Plasma Protein Binding (PPB):  75.03955841064453%
Volume Distribution (VD):  0.729
Pgp-substrate:  25.59857940673828%

ADMET: Metabolism

CYP1A2-inhibitor:  0.05
CYP1A2-substrate:  0.588
CYP2C19-inhibitor:  0.048
CYP2C19-substrate:  0.761
CYP2C9-inhibitor:  0.111
CYP2C9-substrate:  0.068
CYP2D6-inhibitor:  0.012
CYP2D6-substrate:  0.319
CYP3A4-inhibitor:  0.832
CYP3A4-substrate:  0.283

ADMET: Excretion

Clearance (CL):  6.53
Half-life (T1/2):  0.238

ADMET: Toxicity

hERG Blockers:  0.623
Human Hepatotoxicity (H-HT):  0.205
Drug-inuced Liver Injury (DILI):  0.185
AMES Toxicity:  0.066
Rat Oral Acute Toxicity:  0.982
Maximum Recommended Daily Dose:  0.976
Skin Sensitization:  0.943
Carcinogencity:  0.871
Eye Corrosion:  0.208
Eye Irritation:  0.19
Respiratory Toxicity:  0.979

Download Data

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

  Natural Product: NPC470386

Natural Product ID:  NPC470386
Common Name*:   Methylgeopyxin B
IUPAC Name:   n.a.
Synonyms:   Methylgeopyxin B
Standard InCHIKey:  GAOPBOSWKOSYEQ-HYTLULFISA-N
Standard InCHI:  InChI=1S/C21H30O4/c1-12-13-6-7-14-19(2)8-5-9-20(3,18(24)25-4)15(19)10-16(22)21(14,11-13)17(12)23/h13-16,22H,1,5-11H2,2-4H3/t13-,14+,15+,16+,19+,20-,21-/m1/s1
SMILES:  CC12CCCC(C1CC(C34C2CCC(C3)C(=C)C4=O)O)(C)C(=O)OC
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL2022264
PubChem CID:   57380182
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001551] Diterpenoids
          • [CHEMONTID:0003782] Kaurane diterpenoids

*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
NPO33235 geopyxis sp. az0066 Species Pyronemataceae Eukaryota n.a. n.a. n.a. PMID[22264149]
NPO32738 geopyxis aff. majalis Species Pyronemataceae Eukaryota n.a. n.a. n.a. PMID[22264149]

☑ 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
NPT397 Cell Line NCI-H460 Homo sapiens IC50 = 920.0 nM PMID[550511]
NPT395 Cell Line SF-268 Homo sapiens IC50 = 690.0 nM PMID[550511]
NPT83 Cell Line MCF7 Homo sapiens IC50 = 630.0 nM PMID[550511]
NPT82 Cell Line MDA-MB-231 Homo sapiens IC50 = 910.0 nM PMID[550511]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 1480.0 nM PMID[550511]

☑ 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 NPC470386 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
1.0 High Similarity NPC470385
0.9886 High Similarity NPC470232
0.9775 High Similarity NPC329910
0.9775 High Similarity NPC470387
0.9773 High Similarity NPC475118
0.977 High Similarity NPC198242
0.977 High Similarity NPC211403
0.9663 High Similarity NPC470229
0.956 High Similarity NPC471038
0.9551 High Similarity NPC47853
0.9457 High Similarity NPC470388
0.9355 High Similarity NPC289148
0.9355 High Similarity NPC46848
0.9355 High Similarity NPC163963
0.9355 High Similarity NPC52899
0.9348 High Similarity NPC474793
0.9341 High Similarity NPC29410
0.9341 High Similarity NPC200054
0.9326 High Similarity NPC470230
0.9326 High Similarity NPC250753
0.931 High Similarity NPC259009
0.9255 High Similarity NPC88203
0.9255 High Similarity NPC214946
0.9255 High Similarity NPC246736
0.9255 High Similarity NPC275990
0.9255 High Similarity NPC76866
0.9255 High Similarity NPC304832
0.9255 High Similarity NPC148628
0.9255 High Similarity NPC286519
0.9247 High Similarity NPC287676
0.9231 High Similarity NPC98639
0.9213 High Similarity NPC80401
0.9158 High Similarity NPC216114
0.9158 High Similarity NPC209298
0.9158 High Similarity NPC87927
0.9158 High Similarity NPC122811
0.9158 High Similarity NPC139347
0.9158 High Similarity NPC277074
0.9149 High Similarity NPC236585
0.9149 High Similarity NPC471790
0.914 High Similarity NPC162459
0.914 High Similarity NPC78427
0.914 High Similarity NPC98837
0.914 High Similarity NPC16911
0.914 High Similarity NPC20479
0.914 High Similarity NPC38296
0.914 High Similarity NPC89099
0.914 High Similarity NPC38471
0.914 High Similarity NPC28864
0.913 High Similarity NPC13949
0.9111 High Similarity NPC476168
0.9101 High Similarity NPC471043
0.9091 High Similarity NPC153604
0.908 High Similarity NPC190704
0.908 High Similarity NPC471034
0.9062 High Similarity NPC84928
0.9062 High Similarity NPC98603
0.9043 High Similarity NPC267921
0.9043 High Similarity NPC293866
0.9032 High Similarity NPC10864
0.9011 High Similarity NPC181594
0.9011 High Similarity NPC144739
0.9011 High Similarity NPC294263
0.8969 High Similarity NPC138908
0.8969 High Similarity NPC200957
0.8958 High Similarity NPC96217
0.8947 High Similarity NPC148279
0.8947 High Similarity NPC252614
0.8947 High Similarity NPC71706
0.8936 High Similarity NPC26270
0.8913 High Similarity NPC29247
0.8913 High Similarity NPC261333
0.8913 High Similarity NPC302008
0.8913 High Similarity NPC292374
0.8913 High Similarity NPC111524
0.8913 High Similarity NPC191094
0.8913 High Similarity NPC101233
0.8913 High Similarity NPC289539
0.8913 High Similarity NPC91772
0.8913 High Similarity NPC104371
0.8913 High Similarity NPC129004
0.8913 High Similarity NPC215271
0.8913 High Similarity NPC153775
0.8901 High Similarity NPC299185
0.8878 High Similarity NPC201908
0.8878 High Similarity NPC166993
0.8878 High Similarity NPC186054
0.8878 High Similarity NPC176949
0.8866 High Similarity NPC202793
0.8866 High Similarity NPC474558
0.8854 High Similarity NPC475803
0.8854 High Similarity NPC309388
0.8851 High Similarity NPC291320
0.8851 High Similarity NPC471036
0.8842 High Similarity NPC37047
0.8842 High Similarity NPC180733
0.8842 High Similarity NPC41971
0.8842 High Similarity NPC94906
0.8817 High Similarity NPC210214
0.8817 High Similarity NPC288906
0.8817 High Similarity NPC231060
0.8817 High Similarity NPC84018
0.8817 High Similarity NPC263135
0.8817 High Similarity NPC138245
0.8804 High Similarity NPC224060
0.8804 High Similarity NPC244356
0.8791 High Similarity NPC149761
0.8791 High Similarity NPC180849
0.8791 High Similarity NPC261994
0.8791 High Similarity NPC470378
0.8788 High Similarity NPC273155
0.8788 High Similarity NPC231278
0.8788 High Similarity NPC63841
0.8788 High Similarity NPC218123
0.8788 High Similarity NPC112895
0.8763 High Similarity NPC159442
0.8763 High Similarity NPC469985
0.875 High Similarity NPC75941
0.875 High Similarity NPC146683
0.875 High Similarity NPC14634
0.8737 High Similarity NPC472028
0.8723 High Similarity NPC104568
0.8723 High Similarity NPC264979
0.8723 High Similarity NPC140242
0.8723 High Similarity NPC135548
0.8723 High Similarity NPC219353
0.8723 High Similarity NPC234564
0.8687 High Similarity NPC88833
0.8687 High Similarity NPC96333
0.8687 High Similarity NPC61071
0.8687 High Similarity NPC471474
0.8673 High Similarity NPC301787
0.8673 High Similarity NPC96268
0.8673 High Similarity NPC101842
0.8673 High Similarity NPC13149
0.8667 High Similarity NPC174619
0.866 High Similarity NPC124544
0.8636 High Similarity NPC118800
0.8632 High Similarity NPC253586
0.8632 High Similarity NPC96839
0.8617 High Similarity NPC266431
0.8614 High Similarity NPC471093
0.8602 High Similarity NPC59170
0.8602 High Similarity NPC59350
0.86 High Similarity NPC473410
0.86 High Similarity NPC471094
0.86 High Similarity NPC232133
0.86 High Similarity NPC211224
0.86 High Similarity NPC469984
0.8586 High Similarity NPC222833
0.8586 High Similarity NPC103172
0.8586 High Similarity NPC295366
0.8586 High Similarity NPC12823
0.8586 High Similarity NPC56656
0.8586 High Similarity NPC4115
0.8586 High Similarity NPC164600
0.8586 High Similarity NPC37600
0.8571 High Similarity NPC312900
0.8571 High Similarity NPC56413
0.8571 High Similarity NPC470310
0.8557 High Similarity NPC253886
0.8557 High Similarity NPC121218
0.8557 High Similarity NPC295276
0.8556 High Similarity NPC471042
0.8542 High Similarity NPC114274
0.8529 High Similarity NPC329953
0.8529 High Similarity NPC29505
0.8529 High Similarity NPC470281
0.8515 High Similarity NPC469983
0.8511 High Similarity NPC64006
0.8495 Intermediate Similarity NPC476934
0.8495 Intermediate Similarity NPC278106
0.8478 Intermediate Similarity NPC213832
0.8478 Intermediate Similarity NPC57954
0.8469 Intermediate Similarity NPC170615
0.8462 Intermediate Similarity NPC57469
0.8462 Intermediate Similarity NPC33768
0.8462 Intermediate Similarity NPC165895
0.8454 Intermediate Similarity NPC108371
0.8454 Intermediate Similarity NPC293890
0.8454 Intermediate Similarity NPC127408
0.8454 Intermediate Similarity NPC55503
0.8454 Intermediate Similarity NPC156324
0.8454 Intermediate Similarity NPC291785
0.8444 Intermediate Similarity NPC102292
0.8431 Intermediate Similarity NPC320383
0.8431 Intermediate Similarity NPC49730
0.8431 Intermediate Similarity NPC85391
0.8431 Intermediate Similarity NPC137104
0.8431 Intermediate Similarity NPC474786
0.8431 Intermediate Similarity NPC98069
0.8427 Intermediate Similarity NPC471037
0.8421 Intermediate Similarity NPC197158
0.8421 Intermediate Similarity NPC471624
0.8421 Intermediate Similarity NPC29112
0.8416 Intermediate Similarity NPC55973
0.8416 Intermediate Similarity NPC469729
0.8416 Intermediate Similarity NPC469733
0.8404 Intermediate Similarity NPC82138
0.8404 Intermediate Similarity NPC471902

  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 NPC470386 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
0.8242 Intermediate Similarity NPD7520 Clinical (unspecified phase)
0.7917 Intermediate Similarity NPD8035 Phase 2
0.7917 Intermediate Similarity NPD8034 Phase 2
0.7917 Intermediate Similarity NPD6079 Approved
0.7895 Intermediate Similarity NPD5328 Approved
0.7865 Intermediate Similarity NPD6697 Approved
0.7865 Intermediate Similarity NPD6118 Approved
0.7865 Intermediate Similarity NPD6114 Approved
0.7865 Intermediate Similarity NPD6115 Approved
0.785 Intermediate Similarity NPD4632 Approved
0.78 Intermediate Similarity NPD7638 Approved
0.7788 Intermediate Similarity NPD5697 Approved
0.7778 Intermediate Similarity NPD5220 Clinical (unspecified phase)
0.7778 Intermediate Similarity NPD5221 Approved
0.7778 Intermediate Similarity NPD5222 Approved
0.7748 Intermediate Similarity NPD6319 Approved
0.7732 Intermediate Similarity NPD7515 Phase 2
0.7727 Intermediate Similarity NPD3703 Phase 2
0.7723 Intermediate Similarity NPD7640 Approved
0.7723 Intermediate Similarity NPD7639 Approved
0.7714 Intermediate Similarity NPD6011 Approved
0.7714 Intermediate Similarity NPD6899 Approved
0.7714 Intermediate Similarity NPD6881 Approved
0.77 Intermediate Similarity NPD5173 Approved
0.7692 Intermediate Similarity NPD6675 Approved
0.7692 Intermediate Similarity NPD6402 Approved
0.7692 Intermediate Similarity NPD7128 Approved
0.7692 Intermediate Similarity NPD5739 Approved
0.7642 Intermediate Similarity NPD6014 Approved
0.7642 Intermediate Similarity NPD6012 Approved
0.7642 Intermediate Similarity NPD6013 Approved
0.764 Intermediate Similarity NPD6117 Approved
0.7636 Intermediate Similarity NPD6009 Approved
0.7634 Intermediate Similarity NPD4788 Approved
0.7619 Intermediate Similarity NPD5701 Approved
0.76 Intermediate Similarity NPD4697 Phase 3
0.7579 Intermediate Similarity NPD3618 Phase 1
0.7576 Intermediate Similarity NPD7748 Approved
0.757 Intermediate Similarity NPD6883 Approved
0.757 Intermediate Similarity NPD7102 Approved
0.757 Intermediate Similarity NPD7290 Approved
0.757 Intermediate Similarity NPD4634 Approved
0.7556 Intermediate Similarity NPD6116 Phase 1
0.7549 Intermediate Similarity NPD4696 Approved
0.7549 Intermediate Similarity NPD5285 Approved
0.7549 Intermediate Similarity NPD5286 Approved
0.7547 Intermediate Similarity NPD7320 Approved
0.7525 Intermediate Similarity NPD4755 Approved
0.7524 Intermediate Similarity NPD6008 Approved
0.75 Intermediate Similarity NPD6649 Approved
0.75 Intermediate Similarity NPD6847 Approved
0.75 Intermediate Similarity NPD6869 Approved
0.75 Intermediate Similarity NPD6650 Approved
0.75 Intermediate Similarity NPD8130 Phase 1
0.75 Intermediate Similarity NPD6617 Approved
0.7478 Intermediate Similarity NPD7492 Approved
0.7477 Intermediate Similarity NPD6373 Approved
0.7477 Intermediate Similarity NPD6372 Approved
0.7476 Intermediate Similarity NPD5223 Approved
0.7475 Intermediate Similarity NPD6399 Phase 3
0.7436 Intermediate Similarity NPD7736 Approved
0.7434 Intermediate Similarity NPD6054 Approved
0.7431 Intermediate Similarity NPD8297 Approved
0.7431 Intermediate Similarity NPD6882 Approved
0.7416 Intermediate Similarity NPD6113 Clinical (unspecified phase)
0.7414 Intermediate Similarity NPD6616 Approved
0.7404 Intermediate Similarity NPD5225 Approved
0.7404 Intermediate Similarity NPD5226 Approved
0.7404 Intermediate Similarity NPD5224 Approved
0.7404 Intermediate Similarity NPD5211 Phase 2
0.7404 Intermediate Similarity NPD4633 Approved
0.7383 Intermediate Similarity NPD5345 Clinical (unspecified phase)
0.7379 Intermediate Similarity NPD4700 Approved
0.7368 Intermediate Similarity NPD4786 Approved
0.7368 Intermediate Similarity NPD6016 Approved
0.7368 Intermediate Similarity NPD6015 Approved
0.7368 Intermediate Similarity NPD5983 Phase 2
0.7353 Intermediate Similarity NPD7902 Approved
0.735 Intermediate Similarity NPD7078 Approved
0.734 Intermediate Similarity NPD3667 Approved
0.7339 Intermediate Similarity NPD6401 Clinical (unspecified phase)
0.7333 Intermediate Similarity NPD5174 Approved
0.7333 Intermediate Similarity NPD5175 Approved
0.7304 Intermediate Similarity NPD6370 Approved
0.7304 Intermediate Similarity NPD5988 Approved
0.73 Intermediate Similarity NPD4202 Approved
0.7281 Intermediate Similarity NPD6059 Approved
0.7264 Intermediate Similarity NPD5141 Approved
0.7241 Intermediate Similarity NPD7604 Phase 2
0.7238 Intermediate Similarity NPD7632 Discontinued
0.7232 Intermediate Similarity NPD6868 Approved
0.7232 Intermediate Similarity NPD6274 Approved
0.7216 Intermediate Similarity NPD3574 Clinical (unspecified phase)
0.7203 Intermediate Similarity NPD8293 Discontinued
0.7191 Intermediate Similarity NPD4808 Clinical (unspecified phase)
0.7191 Intermediate Similarity NPD4809 Clinical (unspecified phase)
0.7188 Intermediate Similarity NPD3133 Approved
0.7188 Intermediate Similarity NPD3665 Phase 1
0.7188 Intermediate Similarity NPD3666 Approved
0.7184 Intermediate Similarity NPD6083 Phase 2
0.7184 Intermediate Similarity NPD6084 Phase 2
0.717 Intermediate Similarity NPD4754 Approved
0.7168 Intermediate Similarity NPD6317 Approved
0.7168 Intermediate Similarity NPD7115 Discovery
0.7159 Intermediate Similarity NPD3699 Clinical (unspecified phase)
0.7159 Intermediate Similarity NPD3700 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD3573 Approved
0.7119 Intermediate Similarity NPD6336 Discontinued
0.7105 Intermediate Similarity NPD6313 Approved
0.7105 Intermediate Similarity NPD6335 Approved
0.7105 Intermediate Similarity NPD6314 Approved
0.7094 Intermediate Similarity NPD8328 Phase 3
0.7083 Intermediate Similarity NPD7319 Approved
0.7071 Intermediate Similarity NPD6672 Approved
0.7071 Intermediate Similarity NPD5737 Approved
0.7071 Intermediate Similarity NPD7513 Clinical (unspecified phase)
0.7064 Intermediate Similarity NPD5168 Approved
0.7064 Intermediate Similarity NPD4729 Approved
0.7064 Intermediate Similarity NPD4730 Approved
0.7064 Intermediate Similarity NPD5128 Approved
0.7059 Intermediate Similarity NPD7901 Clinical (unspecified phase)
0.7059 Intermediate Similarity NPD7900 Approved
0.7054 Intermediate Similarity NPD8133 Approved
0.7043 Intermediate Similarity NPD7101 Approved
0.7043 Intermediate Similarity NPD7100 Approved
0.7041 Intermediate Similarity NPD5330 Approved
0.7041 Intermediate Similarity NPD6409 Approved
0.7041 Intermediate Similarity NPD7146 Approved
0.7041 Intermediate Similarity NPD6684 Approved
0.7041 Intermediate Similarity NPD7521 Approved
0.7041 Intermediate Similarity NPD7334 Approved
0.7037 Intermediate Similarity NPD4767 Approved
0.7037 Intermediate Similarity NPD4768 Approved
0.703 Intermediate Similarity NPD6411 Approved
0.7011 Intermediate Similarity NPD4224 Phase 2
0.7 Intermediate Similarity NPD4753 Phase 2
0.699 Remote Similarity NPD5695 Phase 3
0.6975 Remote Similarity NPD7507 Approved
0.6952 Remote Similarity NPD4225 Approved
0.6952 Remote Similarity NPD5696 Approved
0.6947 Remote Similarity NPD7525 Registered
0.6937 Remote Similarity NPD5250 Approved
0.6937 Remote Similarity NPD5251 Approved
0.6937 Remote Similarity NPD5169 Approved
0.6937 Remote Similarity NPD5247 Approved
0.6937 Remote Similarity NPD5135 Approved
0.6937 Remote Similarity NPD5134 Clinical (unspecified phase)
0.6937 Remote Similarity NPD5248 Approved
0.6937 Remote Similarity NPD5249 Phase 3
0.6923 Remote Similarity NPD6291 Clinical (unspecified phase)
0.69 Remote Similarity NPD6903 Approved
0.6875 Remote Similarity NPD5217 Approved
0.6875 Remote Similarity NPD5127 Approved
0.6875 Remote Similarity NPD5215 Approved
0.6875 Remote Similarity NPD5216 Approved
0.687 Remote Similarity NPD8295 Clinical (unspecified phase)
0.6869 Remote Similarity NPD5279 Phase 3
0.686 Remote Similarity NPD6033 Approved
0.6847 Remote Similarity NPD4061 Clinical (unspecified phase)
0.6837 Remote Similarity NPD3668 Phase 3
0.6832 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6832 Remote Similarity NPD6101 Approved
0.6827 Remote Similarity NPD5210 Approved
0.6827 Remote Similarity NPD4629 Approved
0.6827 Remote Similarity NPD6356 Clinical (unspecified phase)
0.6818 Remote Similarity NPD6412 Phase 2
0.6813 Remote Similarity NPD6081 Approved
0.6804 Remote Similarity NPD4223 Phase 3
0.6804 Remote Similarity NPD4221 Approved
0.6796 Remote Similarity NPD5779 Approved
0.6796 Remote Similarity NPD5778 Approved
0.678 Remote Similarity NPD6909 Approved
0.678 Remote Similarity NPD6908 Approved
0.6778 Remote Similarity NPD3698 Phase 2
0.6774 Remote Similarity NPD3702 Approved
0.6772 Remote Similarity NPD6334 Approved
0.6772 Remote Similarity NPD6333 Approved
0.6757 Remote Similarity NPD6686 Approved
0.6705 Remote Similarity NPD3171 Clinical (unspecified phase)
0.6703 Remote Similarity NPD4244 Approved
0.6703 Remote Similarity NPD4245 Approved
0.6703 Remote Similarity NPD4789 Approved
0.6699 Remote Similarity NPD5281 Approved
0.6699 Remote Similarity NPD7637 Suspended
0.6699 Remote Similarity NPD5284 Approved
0.6696 Remote Similarity NPD8132 Clinical (unspecified phase)
0.6696 Remote Similarity NPD5167 Approved
0.6667 Remote Similarity NPD5360 Phase 3
0.6667 Remote Similarity NPD6904 Approved
0.6667 Remote Similarity NPD6080 Approved
0.6667 Remote Similarity NPD4197 Approved
0.6667 Remote Similarity NPD5361 Clinical (unspecified phase)
0.6667 Remote Similarity NPD6673 Approved
0.6639 Remote Similarity NPD6921 Approved
0.6637 Remote Similarity NPD5955 Clinical (unspecified phase)
0.6633 Remote Similarity NPD4752 Clinical (unspecified phase)
0.663 Remote Similarity NPD5777 Approved
0.66 Remote Similarity NPD5329 Approved
0.6598 Remote Similarity NPD4695 Discontinued
0.6571 Remote Similarity NPD6001 Approved

  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