Structure

Physi-Chem Properties

Molecular Weight:  522.33
Volume:  576.514
LogP:  5.498
LogD:  4.51
LogS:  -5.655
# Rotatable Bonds:  8
TPSA:  69.67
# H-Bond Aceptor:  5
# H-Bond Donor:  0
# Rings:  3
# Heavy Atoms:  5

MedChem Properties

QED Drug-Likeness Score:  0.209
Synthetic Accessibility Score:  4.886
Fsp3:  0.606
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Rejected
GSK Rule:  Rejected
BMS Rule:  1
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.922
MDCK Permeability:  1.665041418164037e-05
Pgp-inhibitor:  0.999
Pgp-substrate:  0.01
Human Intestinal Absorption (HIA):  0.003
20% Bioavailability (F20%):  0.861
30% Bioavailability (F30%):  0.899

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.063
Plasma Protein Binding (PPB):  96.36766052246094%
Volume Distribution (VD):  1.459
Pgp-substrate:  5.870802879333496%

ADMET: Metabolism

CYP1A2-inhibitor:  0.479
CYP1A2-substrate:  0.412
CYP2C19-inhibitor:  0.868
CYP2C19-substrate:  0.906
CYP2C9-inhibitor:  0.806
CYP2C9-substrate:  0.099
CYP2D6-inhibitor:  0.948
CYP2D6-substrate:  0.622
CYP3A4-inhibitor:  0.933
CYP3A4-substrate:  0.825

ADMET: Excretion

Clearance (CL):  3.325
Half-life (T1/2):  0.314

ADMET: Toxicity

hERG Blockers:  0.536
Human Hepatotoxicity (H-HT):  0.942
Drug-inuced Liver Injury (DILI):  0.441
AMES Toxicity:  0.037
Rat Oral Acute Toxicity:  0.724
Maximum Recommended Daily Dose:  0.961
Skin Sensitization:  0.96
Carcinogencity:  0.116
Eye Corrosion:  0.005
Eye Irritation:  0.026
Respiratory Toxicity:  0.972

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

  Natural Product: NPC473431

Natural Product ID:  NPC473431
Common Name*:   13Z,17Z-Globostellatic Acid X Methyl Ester
IUPAC Name:   methyl (3Z,3aS,5aR,6R,7R,9aR,9bS)-7-acetyloxy-3-[(3E,5Z,7E)-6,10-dimethylundeca-3,5,7,9-tetraen-2-ylidene]-3a,6,9a-trimethyl-2-oxo-1,4,5,5a,7,8,9,9b-octahydrocyclopenta[a]naphthalene-6-carboxylate
Synonyms:   13Z,17Z-Globostellatic Acid X Methyl Ester
Standard InCHIKey:  GRNXZFQSLPDVMF-XPXWRWOCSA-N
Standard InCHI:  InChI=1S/C33H46O5/c1-21(2)12-10-13-22(3)14-11-15-23(4)29-25(35)20-27-31(6)19-17-28(38-24(5)34)33(8,30(36)37-9)26(31)16-18-32(27,29)7/h10-15,26-28H,16-20H2,1-9H3/b13-10+,15-11+,22-14-,29-23+/t26-,27+,28-,31+,32+,33-/m1/s1
SMILES:  CC(=CC=CC(=CC=CC(=C1C(=O)CC2C1(CCC3C2(CCC(C3(C)C(=O)OC)OC(=O)C)C)C)C)C)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL429988
PubChem CID:   44434364
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001553] Triterpenoids

*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
NPO28502 Rhabdastrella globostellata Species Ancorinidae Eukaryota n.a. n.a. n.a. PMID[11858759]
NPO28502 Rhabdastrella globostellata Species Ancorinidae Eukaryota n.a. n.a. n.a. PMID[16499318]
NPO28502 Rhabdastrella globostellata Species Ancorinidae Eukaryota n.a. n.a. n.a. PMID[16562838]
NPO28502 Rhabdastrella globostellata Species Ancorinidae Eukaryota n.a. n.a. n.a. PMID[17524651]
NPO28502 Rhabdastrella globostellata Species Ancorinidae Eukaryota n.a. n.a. n.a. PMID[20627740]
NPO28502 Rhabdastrella globostellata Species Ancorinidae Eukaryota n.a. n.a. n.a. PMID[20718449]
NPO28502 Rhabdastrella globostellata Species Ancorinidae 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
NPT737 Cell Line HUVEC Homo sapiens IC50 = 400.0 nM PMID[510406]
NPT111 Cell Line K562 Homo sapiens IC50 = 22000.0 nM PMID[510406]
NPT737 Cell Line HUVEC Homo sapiens Ratio IC50 = 25.0 n.a. PMID[510406]
NPT111 Cell Line K562 Homo sapiens Ratio IC50 = 55.0 n.a. PMID[510406]
NPT737 Cell Line HUVEC Homo sapiens Ratio IC50 = 19.0 n.a. PMID[510406]
NPT737 Cell Line HUVEC Homo sapiens Ratio IC50 = 25.0 n.a. PMID[510407]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 9800.0 nM PMID[510406]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 7900.0 nM PMID[510406]

☑ 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 NPC473431 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 NPC473280
1.0 High Similarity NPC473435
1.0 High Similarity NPC471078
0.9556 High Similarity NPC106425
0.9556 High Similarity NPC151725
0.9556 High Similarity NPC122324
0.9432 High Similarity NPC474842
0.9432 High Similarity NPC475965
0.9341 High Similarity NPC471153
0.9255 High Similarity NPC320447
0.9247 High Similarity NPC35751
0.9239 High Similarity NPC2049
0.9239 High Similarity NPC110937
0.9231 High Similarity NPC88310
0.9158 High Similarity NPC475526
0.9158 High Similarity NPC72151
0.9158 High Similarity NPC473283
0.9158 High Similarity NPC329345
0.8989 High Similarity NPC80335
0.8947 High Similarity NPC115899
0.8878 High Similarity NPC473284
0.8854 High Similarity NPC32577
0.8854 High Similarity NPC155332
0.8854 High Similarity NPC114540
0.8842 High Similarity NPC266955
0.8791 High Similarity NPC161638
0.8788 High Similarity NPC473482
0.8788 High Similarity NPC318363
0.8788 High Similarity NPC475418
0.875 High Similarity NPC194028
0.875 High Similarity NPC282524
0.875 High Similarity NPC168319
0.87 High Similarity NPC475065
0.8571 High Similarity NPC292491
0.8571 High Similarity NPC472220
0.8571 High Similarity NPC310752
0.8571 High Similarity NPC475050
0.8571 High Similarity NPC97884
0.8542 High Similarity NPC57079
0.8542 High Similarity NPC108368
0.8526 High Similarity NPC250757
0.8526 High Similarity NPC301534
0.8526 High Similarity NPC327788
0.85 High Similarity NPC329048
0.85 High Similarity NPC330011
0.8462 Intermediate Similarity NPC141292
0.8438 Intermediate Similarity NPC26413
0.8404 Intermediate Similarity NPC79117
0.84 Intermediate Similarity NPC469874
0.84 Intermediate Similarity NPC266570
0.8387 Intermediate Similarity NPC471896
0.8352 Intermediate Similarity NPC264127
0.8352 Intermediate Similarity NPC195640
0.8351 Intermediate Similarity NPC471582
0.8333 Intermediate Similarity NPC139566
0.8317 Intermediate Similarity NPC220974
0.8316 Intermediate Similarity NPC124207
0.8316 Intermediate Similarity NPC474690
0.8298 Intermediate Similarity NPC473986
0.8298 Intermediate Similarity NPC474018
0.828 Intermediate Similarity NPC475049
0.828 Intermediate Similarity NPC474570
0.8265 Intermediate Similarity NPC475392
0.8265 Intermediate Similarity NPC475202
0.8265 Intermediate Similarity NPC475385
0.8242 Intermediate Similarity NPC323765
0.8229 Intermediate Similarity NPC180950
0.8211 Intermediate Similarity NPC474185
0.82 Intermediate Similarity NPC36321
0.8191 Intermediate Similarity NPC8062
0.8191 Intermediate Similarity NPC148414
0.8191 Intermediate Similarity NPC175628
0.8191 Intermediate Similarity NPC111585
0.8182 Intermediate Similarity NPC473514
0.8173 Intermediate Similarity NPC474315
0.8172 Intermediate Similarity NPC473879
0.8163 Intermediate Similarity NPC252295
0.8155 Intermediate Similarity NPC170221
0.8155 Intermediate Similarity NPC10064
0.8144 Intermediate Similarity NPC120708
0.8144 Intermediate Similarity NPC98874
0.8125 Intermediate Similarity NPC159410
0.8125 Intermediate Similarity NPC74751
0.8125 Intermediate Similarity NPC78580
0.8125 Intermediate Similarity NPC84893
0.8125 Intermediate Similarity NPC184006
0.8125 Intermediate Similarity NPC23621
0.8125 Intermediate Similarity NPC470697
0.8125 Intermediate Similarity NPC299100
0.8125 Intermediate Similarity NPC38830
0.8105 Intermediate Similarity NPC471901
0.8105 Intermediate Similarity NPC218301
0.8105 Intermediate Similarity NPC26888
0.81 Intermediate Similarity NPC22388
0.81 Intermediate Similarity NPC473163
0.8085 Intermediate Similarity NPC471043
0.8085 Intermediate Similarity NPC475921
0.8085 Intermediate Similarity NPC50070
0.8085 Intermediate Similarity NPC474704
0.8085 Intermediate Similarity NPC474889
0.8081 Intermediate Similarity NPC477521
0.8077 Intermediate Similarity NPC6206
0.8065 Intermediate Similarity NPC162107
0.8065 Intermediate Similarity NPC46912
0.8061 Intermediate Similarity NPC292133
0.8061 Intermediate Similarity NPC108078
0.8061 Intermediate Similarity NPC89225
0.8061 Intermediate Similarity NPC474785
0.8061 Intermediate Similarity NPC474938
0.8061 Intermediate Similarity NPC23680
0.8043 Intermediate Similarity NPC76333
0.8043 Intermediate Similarity NPC98270
0.8041 Intermediate Similarity NPC473648
0.8041 Intermediate Similarity NPC279974
0.8041 Intermediate Similarity NPC139459
0.8041 Intermediate Similarity NPC195715
0.8041 Intermediate Similarity NPC23241
0.8041 Intermediate Similarity NPC148523
0.8041 Intermediate Similarity NPC280725
0.8021 Intermediate Similarity NPC473690
0.8021 Intermediate Similarity NPC287118
0.8021 Intermediate Similarity NPC471902
0.802 Intermediate Similarity NPC180204
0.802 Intermediate Similarity NPC312900
0.8 Intermediate Similarity NPC118174
0.8 Intermediate Similarity NPC476888
0.8 Intermediate Similarity NPC93744
0.8 Intermediate Similarity NPC475665
0.8 Intermediate Similarity NPC470960
0.8 Intermediate Similarity NPC474955
0.798 Intermediate Similarity NPC477813
0.798 Intermediate Similarity NPC119036
0.7959 Intermediate Similarity NPC472806
0.7959 Intermediate Similarity NPC58052
0.7959 Intermediate Similarity NPC307164
0.7959 Intermediate Similarity NPC111684
0.7959 Intermediate Similarity NPC242848
0.7959 Intermediate Similarity NPC167193
0.7957 Intermediate Similarity NPC9892
0.7957 Intermediate Similarity NPC325594
0.7957 Intermediate Similarity NPC10005
0.7957 Intermediate Similarity NPC329943
0.7957 Intermediate Similarity NPC91525
0.7955 Intermediate Similarity NPC471151
0.7938 Intermediate Similarity NPC477129
0.7938 Intermediate Similarity NPC477130
0.7938 Intermediate Similarity NPC49670
0.7938 Intermediate Similarity NPC56525
0.7935 Intermediate Similarity NPC100391
0.7935 Intermediate Similarity NPC475509
0.7925 Intermediate Similarity NPC475970
0.7921 Intermediate Similarity NPC40918
0.7921 Intermediate Similarity NPC476890
0.7917 Intermediate Similarity NPC475416
0.7917 Intermediate Similarity NPC470230
0.7912 Intermediate Similarity NPC240302
0.7912 Intermediate Similarity NPC100297
0.7905 Intermediate Similarity NPC16270
0.79 Intermediate Similarity NPC470906
0.79 Intermediate Similarity NPC117685
0.7895 Intermediate Similarity NPC1015
0.7895 Intermediate Similarity NPC474679
0.7895 Intermediate Similarity NPC73995
0.7895 Intermediate Similarity NPC84271
0.7895 Intermediate Similarity NPC31985
0.7895 Intermediate Similarity NPC77168
0.7895 Intermediate Similarity NPC102414
0.7895 Intermediate Similarity NPC128496
0.7895 Intermediate Similarity NPC284561
0.7895 Intermediate Similarity NPC474844
0.7889 Intermediate Similarity NPC269791
0.7885 Intermediate Similarity NPC220155
0.7885 Intermediate Similarity NPC102843
0.7879 Intermediate Similarity NPC253826
0.7879 Intermediate Similarity NPC226986
0.7872 Intermediate Similarity NPC142361
0.7872 Intermediate Similarity NPC474684
0.7872 Intermediate Similarity NPC38885
0.7872 Intermediate Similarity NPC181327
0.7872 Intermediate Similarity NPC96496
0.7864 Intermediate Similarity NPC189863
0.7857 Intermediate Similarity NPC317586
0.7857 Intermediate Similarity NPC470016
0.7857 Intermediate Similarity NPC209355
0.7857 Intermediate Similarity NPC274417
0.7857 Intermediate Similarity NPC33473
0.7857 Intermediate Similarity NPC84383
0.7857 Intermediate Similarity NPC210214
0.785 Intermediate Similarity NPC52634
0.785 Intermediate Similarity NPC122056
0.7849 Intermediate Similarity NPC470574
0.7849 Intermediate Similarity NPC470223
0.7843 Intermediate Similarity NPC112009
0.7843 Intermediate Similarity NPC470954
0.7843 Intermediate Similarity NPC471364
0.7843 Intermediate Similarity NPC476889
0.7843 Intermediate Similarity NPC471365
0.7843 Intermediate Similarity NPC132395
0.7835 Intermediate Similarity NPC38232
0.7835 Intermediate Similarity NPC86368

  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 NPC473431 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
0.8352 Intermediate Similarity NPD5330 Approved
0.8352 Intermediate Similarity NPD7146 Approved
0.8352 Intermediate Similarity NPD7334 Approved
0.8352 Intermediate Similarity NPD6684 Approved
0.8352 Intermediate Similarity NPD7521 Approved
0.8352 Intermediate Similarity NPD6409 Approved
0.8172 Intermediate Similarity NPD5737 Approved
0.8172 Intermediate Similarity NPD6672 Approved
0.8172 Intermediate Similarity NPD6903 Approved
0.8172 Intermediate Similarity NPD7513 Clinical (unspecified phase)
0.8125 Intermediate Similarity NPD7901 Clinical (unspecified phase)
0.8125 Intermediate Similarity NPD7748 Approved
0.8125 Intermediate Similarity NPD7900 Approved
0.7885 Intermediate Similarity NPD6899 Approved
0.7885 Intermediate Similarity NPD6881 Approved
0.7879 Intermediate Similarity NPD7902 Approved
0.7864 Intermediate Similarity NPD6675 Approved
0.7864 Intermediate Similarity NPD6402 Approved
0.7864 Intermediate Similarity NPD7128 Approved
0.7864 Intermediate Similarity NPD5739 Approved
0.7857 Intermediate Similarity NPD6356 Clinical (unspecified phase)
0.7835 Intermediate Similarity NPD6399 Phase 3
0.783 Intermediate Similarity NPD8130 Phase 1
0.7788 Intermediate Similarity NPD5697 Approved
0.7766 Intermediate Similarity NPD3618 Phase 1
0.7757 Intermediate Similarity NPD8297 Approved
0.7736 Intermediate Similarity NPD7102 Approved
0.7736 Intermediate Similarity NPD6883 Approved
0.7736 Intermediate Similarity NPD7290 Approved
0.7732 Intermediate Similarity NPD5694 Approved
0.7732 Intermediate Similarity NPD6050 Approved
0.7732 Intermediate Similarity NPD6079 Approved
0.7732 Intermediate Similarity NPD7515 Phase 2
0.7714 Intermediate Similarity NPD7320 Approved
0.7708 Intermediate Similarity NPD6673 Approved
0.7708 Intermediate Similarity NPD5328 Approved
0.7708 Intermediate Similarity NPD6080 Approved
0.7708 Intermediate Similarity NPD6904 Approved
0.77 Intermediate Similarity NPD6083 Phase 2
0.77 Intermediate Similarity NPD6084 Phase 2
0.7684 Intermediate Similarity NPD3573 Approved
0.7664 Intermediate Similarity NPD6847 Approved
0.7664 Intermediate Similarity NPD6649 Approved
0.7664 Intermediate Similarity NPD6650 Approved
0.7664 Intermediate Similarity NPD6617 Approved
0.7664 Intermediate Similarity NPD6869 Approved
0.7642 Intermediate Similarity NPD6013 Approved
0.7642 Intermediate Similarity NPD6012 Approved
0.7642 Intermediate Similarity NPD6014 Approved
0.7642 Intermediate Similarity NPD6372 Approved
0.7642 Intermediate Similarity NPD6373 Approved
0.7636 Intermediate Similarity NPD7115 Discovery
0.7629 Intermediate Similarity NPD5692 Phase 3
0.7629 Intermediate Similarity NPD5207 Approved
0.7624 Intermediate Similarity NPD7638 Approved
0.7619 Intermediate Similarity NPD5701 Approved
0.7593 Intermediate Similarity NPD6882 Approved
0.7551 Intermediate Similarity NPD6411 Approved
0.7551 Intermediate Similarity NPD8035 Phase 2
0.7551 Intermediate Similarity NPD8034 Phase 2
0.7549 Intermediate Similarity NPD7640 Approved
0.7549 Intermediate Similarity NPD7639 Approved
0.7547 Intermediate Similarity NPD6011 Approved
0.7527 Intermediate Similarity NPD4752 Clinical (unspecified phase)
0.7524 Intermediate Similarity NPD6008 Approved
0.75 Intermediate Similarity NPD5695 Phase 3
0.7474 Intermediate Similarity NPD1694 Approved
0.7451 Intermediate Similarity NPD5696 Approved
0.7426 Intermediate Similarity NPD5222 Approved
0.7426 Intermediate Similarity NPD5220 Clinical (unspecified phase)
0.7426 Intermediate Similarity NPD5221 Approved
0.7423 Intermediate Similarity NPD5208 Approved
0.74 Intermediate Similarity NPD6001 Approved
0.7396 Intermediate Similarity NPD6098 Approved
0.7396 Intermediate Similarity NPD3574 Clinical (unspecified phase)
0.7379 Intermediate Similarity NPD5286 Approved
0.7379 Intermediate Similarity NPD4696 Approved
0.7379 Intermediate Similarity NPD5285 Approved
0.7374 Intermediate Similarity NPD5693 Phase 1
0.7374 Intermediate Similarity NPD5284 Approved
0.7374 Intermediate Similarity NPD5281 Approved
0.7374 Intermediate Similarity NPD7637 Suspended
0.7368 Intermediate Similarity NPD4786 Approved
0.7368 Intermediate Similarity NPD3668 Phase 3
0.7368 Intermediate Similarity NPD3665 Phase 1
0.7368 Intermediate Similarity NPD3666 Approved
0.7368 Intermediate Similarity NPD3133 Approved
0.7353 Intermediate Similarity NPD4755 Approved
0.7353 Intermediate Similarity NPD5173 Approved
0.7347 Intermediate Similarity NPD5764 Clinical (unspecified phase)
0.7347 Intermediate Similarity NPD6101 Approved
0.734 Intermediate Similarity NPD3667 Approved
0.7339 Intermediate Similarity NPD6401 Clinical (unspecified phase)
0.73 Intermediate Similarity NPD4202 Approved
0.7292 Intermediate Similarity NPD7520 Clinical (unspecified phase)
0.7282 Intermediate Similarity NPD4225 Approved
0.7281 Intermediate Similarity NPD6319 Approved
0.7255 Intermediate Similarity NPD4697 Phase 3
0.7238 Intermediate Similarity NPD4633 Approved
0.7238 Intermediate Similarity NPD5226 Approved
0.7238 Intermediate Similarity NPD5225 Approved
0.7238 Intermediate Similarity NPD5224 Approved
0.7238 Intermediate Similarity NPD5211 Phase 2
0.7232 Intermediate Similarity NPD6868 Approved
0.7222 Intermediate Similarity NPD4058 Approved
0.7216 Intermediate Similarity NPD5279 Phase 3
0.7212 Intermediate Similarity NPD4700 Approved
0.7193 Intermediate Similarity NPD7101 Approved
0.7193 Intermediate Similarity NPD7100 Approved
0.7179 Intermediate Similarity NPD7492 Approved
0.7172 Intermediate Similarity NPD4753 Phase 2
0.717 Intermediate Similarity NPD5174 Approved
0.717 Intermediate Similarity NPD5175 Approved
0.7157 Intermediate Similarity NPD5654 Approved
0.7143 Intermediate Similarity NPD5223 Approved
0.7143 Intermediate Similarity NPD7736 Approved
0.713 Intermediate Similarity NPD6054 Approved
0.7129 Intermediate Similarity NPD5779 Approved
0.7129 Intermediate Similarity NPD5778 Approved
0.7119 Intermediate Similarity NPD6616 Approved
0.7105 Intermediate Similarity NPD6335 Approved
0.7103 Intermediate Similarity NPD5141 Approved
0.7091 Intermediate Similarity NPD4634 Approved
0.708 Intermediate Similarity NPD6274 Approved
0.7059 Intermediate Similarity NPD8293 Discontinued
0.7059 Intermediate Similarity NPD7078 Approved
0.7054 Intermediate Similarity NPD4632 Approved
0.7054 Intermediate Similarity NPD6858 Approved
0.7054 Intermediate Similarity NPD7094 Approved
0.7033 Intermediate Similarity NPD4687 Approved
0.7033 Intermediate Similarity NPD5733 Approved
0.7019 Intermediate Similarity NPD5959 Approved
0.7018 Intermediate Similarity NPD6317 Approved
0.7009 Intermediate Similarity NPD6370 Approved
0.7 Intermediate Similarity NPD7285 Clinical (unspecified phase)
0.699 Remote Similarity NPD4629 Approved
0.699 Remote Similarity NPD5210 Approved
0.6983 Remote Similarity NPD6059 Approved
0.6979 Remote Similarity NPD4223 Phase 3
0.6979 Remote Similarity NPD4221 Approved
0.6979 Remote Similarity NPD5209 Approved
0.6972 Remote Similarity NPD6412 Phase 2
0.6966 Remote Similarity NPD4137 Phase 3
0.6957 Remote Similarity NPD8039 Approved
0.6957 Remote Similarity NPD6313 Approved
0.6957 Remote Similarity NPD6314 Approved
0.6939 Remote Similarity NPD5329 Approved
0.6931 Remote Similarity NPD5785 Approved
0.6923 Remote Similarity NPD6016 Approved
0.6923 Remote Similarity NPD6908 Approved
0.6923 Remote Similarity NPD6015 Approved
0.6923 Remote Similarity NPD6909 Approved
0.6916 Remote Similarity NPD7632 Discontinued
0.6909 Remote Similarity NPD4729 Approved
0.6909 Remote Similarity NPD4730 Approved
0.6889 Remote Similarity NPD4747 Approved
0.6889 Remote Similarity NPD4691 Approved
0.6881 Remote Similarity NPD4768 Approved
0.6881 Remote Similarity NPD4767 Approved
0.6875 Remote Similarity NPD5369 Approved
0.687 Remote Similarity NPD6009 Approved
0.6869 Remote Similarity NPD5280 Approved
0.6869 Remote Similarity NPD4694 Approved
0.6864 Remote Similarity NPD5988 Approved
0.6852 Remote Similarity NPD6052 Approved
0.6852 Remote Similarity NPD4754 Approved
0.6837 Remote Similarity NPD4197 Approved
0.6832 Remote Similarity NPD6051 Approved
0.6818 Remote Similarity NPD6614 Approved
0.6813 Remote Similarity NPD5777 Approved
0.6813 Remote Similarity NPD5276 Approved
0.6807 Remote Similarity NPD8328 Phase 3
0.6807 Remote Similarity NPD7604 Phase 2
0.6804 Remote Similarity NPD6435 Approved
0.6786 Remote Similarity NPD5248 Approved
0.6786 Remote Similarity NPD5251 Approved
0.6786 Remote Similarity NPD5247 Approved
0.6786 Remote Similarity NPD5250 Approved
0.6786 Remote Similarity NPD5249 Phase 3
0.678 Remote Similarity NPD6291 Clinical (unspecified phase)
0.678 Remote Similarity NPD5983 Phase 2
0.6771 Remote Similarity NPD7525 Registered
0.6771 Remote Similarity NPD8259 Clinical (unspecified phase)
0.6768 Remote Similarity NPD5363 Approved
0.6762 Remote Similarity NPD7732 Phase 3
0.6757 Remote Similarity NPD5168 Approved
0.6757 Remote Similarity NPD5128 Approved
0.6737 Remote Similarity NPD3617 Approved
0.6737 Remote Similarity NPD5784 Clinical (unspecified phase)
0.6726 Remote Similarity NPD5215 Approved
0.6726 Remote Similarity NPD5217 Approved
0.6726 Remote Similarity NPD5216 Approved
0.6702 Remote Similarity NPD6117 Approved
0.67 Remote Similarity NPD4689 Approved
0.67 Remote Similarity NPD4693 Phase 3
0.67 Remote Similarity NPD5205 Approved
0.67 Remote Similarity NPD5690 Phase 2
0.67 Remote Similarity NPD4688 Approved
0.67 Remote Similarity NPD4138 Approved
0.67 Remote Similarity NPD4690 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