Structure

Physi-Chem Properties

Molecular Weight:  442.38
Volume:  499.598
LogP:  6.406
LogD:  5.008
LogS:  -5.945
# Rotatable Bonds:  0
TPSA:  37.3
# H-Bond Aceptor:  2
# H-Bond Donor:  1
# Rings:  5
# Heavy Atoms:  2

MedChem Properties

QED Drug-Likeness Score:  0.423
Synthetic Accessibility Score:  5.0
Fsp3:  0.967
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.935
MDCK Permeability:  1.0517016562516801e-05
Pgp-inhibitor:  0.968
Pgp-substrate:  0.0
Human Intestinal Absorption (HIA):  0.033
20% Bioavailability (F20%):  0.98
30% Bioavailability (F30%):  0.988

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.719
Plasma Protein Binding (PPB):  95.2622299194336%
Volume Distribution (VD):  1.289
Pgp-substrate:  2.631955623626709%

ADMET: Metabolism

CYP1A2-inhibitor:  0.022
CYP1A2-substrate:  0.315
CYP2C19-inhibitor:  0.034
CYP2C19-substrate:  0.94
CYP2C9-inhibitor:  0.131
CYP2C9-substrate:  0.098
CYP2D6-inhibitor:  0.019
CYP2D6-substrate:  0.339
CYP3A4-inhibitor:  0.696
CYP3A4-substrate:  0.443

ADMET: Excretion

Clearance (CL):  17.165
Half-life (T1/2):  0.109

ADMET: Toxicity

hERG Blockers:  0.894
Human Hepatotoxicity (H-HT):  0.354
Drug-inuced Liver Injury (DILI):  0.032
AMES Toxicity:  0.009
Rat Oral Acute Toxicity:  0.981
Maximum Recommended Daily Dose:  0.942
Skin Sensitization:  0.877
Carcinogencity:  0.495
Eye Corrosion:  0.134
Eye Irritation:  0.031
Respiratory Toxicity:  0.974

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  Natural Product: NPC68426

Natural Product ID:  NPC68426
Common Name*:   15Alpha-Hydroxyfriedelan-3-One
IUPAC Name:   (4R,4aS,6aS,6aS,6bR,7S,8aR,12aR,14aS,14bS)-7-hydroxy-4,4a,6a,6b,8a,11,11,14a-octamethyl-2,4,5,6,6a,7,8,9,10,12,12a,13,14,14b-tetradecahydro-1H-picen-3-one
Synonyms:  
Standard InCHIKey:  MYVWXXMGILJAQC-ZHGVIFCFSA-N
Standard InCHI:  InChI=1S/C30H50O2/c1-19-20(31)9-10-21-27(19,5)12-11-22-28(21,6)15-16-29(7)23-17-25(2,3)13-14-26(23,4)18-24(32)30(22,29)8/h19,21-24,32H,9-18H2,1-8H3/t19-,21+,22-,23+,24-,26+,27+,28-,29-,30-/m0/s1
SMILES:  C[C@H]1C(=O)CC[C@@H]2[C@]1(C)CC[C@H]1[C@@]2(C)CC[C@@]2(C)[C@@H]3CC(C)(C)CC[C@]3(C)C[C@@H]([C@]12C)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL514442
PubChem CID:   15038301
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
NPO24176 Streptomyces fradiae Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[10757717]
NPO2353 Bituminaria bituminosa Species Fabaceae Eukaryota n.a. aerial part n.a. PMID[12943781]
NPO7484 Salacia chinensis Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[12951446]
NPO7484 Salacia chinensis Species Celastraceae Eukaryota stems Thailand n.a. PMID[14510595]
NPO14555 Porella swartziana Species Porellaceae Eukaryota n.a. Argentine n.a. PMID[14738381]
NPO14555 Porella swartziana Species Porellaceae Eukaryota n.a. n.a. n.a. PMID[14738381]
NPO12977 Solenopsis invicta Species Formicidae Eukaryota n.a. n.a. n.a. PMID[21905650]
NPO23289 Heracleum sphondylium Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[24697288]
NPO14826 Streptomyces mobaraensis Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[32998509]
NPO9420 Aspergillus arenarius Species Aspergillaceae Eukaryota sclerotia n.a. n.a. PMID[9599285]
NPO15961 Sida cordifolia Species Malvaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO23289 Heracleum sphondylium Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO15510 Kummerowia striata Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO5728 Gerbera piloselloides Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO16847 Consolida ajacis Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO12416 Quercus mongolica Species Fagaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO5728 Gerbera piloselloides Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO12450 Cneorum pulverulentum Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO23289 Heracleum sphondylium Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO12416 Quercus mongolica Species Fagaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15961 Sida cordifolia Species Malvaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14869 Ormosia panamensis Species Limoniidae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO16847 Consolida ajacis Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15510 Kummerowia striata Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO5728 Gerbera piloselloides Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO16847 Consolida ajacis Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO12416 Quercus mongolica Species Fagaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO16175 Trichia floriformis Species Trichiidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15858 Phoebe formosana Species Lauraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13859 Senecio flavus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14869 Ormosia panamensis Species Limoniidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13230 Pedicularis condensata Species Orobanchaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15015 Meconopsis napaulensis Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2353 Bituminaria bituminosa Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11599 Elaeagnus commutata Species Elaeagnaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5728 Gerbera piloselloides Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16678 Flindersia brayleyana Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9420 Aspergillus arenarius Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13710 Lyophyllum shimeji Species Lyophyllaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12450 Cneorum pulverulentum Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3391 Jungermannia obovata Species Jungermanniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12680 Perityle vaseyi Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15272 Mascarenhasia arborescens Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12555 Aspergillus quadrilineatus Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14826 Streptomyces mobaraensis Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO12416 Quercus mongolica Species Fagaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5078 Turraeanthus mannii Species Meliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23289 Heracleum sphondylium Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15510 Kummerowia striata Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15393 Eucalyptus flocktoniae Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15961 Sida cordifolia Species Malvaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16428 Millettia conraui Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26017 Dalbergia stipulacea Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24176 Streptomyces fradiae Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO13375 Palafoxia rosea Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14218 Spodoptera littoralis Species 0ctuidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16847 Consolida ajacis Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24732 Cereus weberi Species Sagartiidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16516 Centaurea seridis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15138 Rheum webbianum Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4267 Ceratocystis clavigera Species Ceratocystidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16758 Satureja cuneifolia Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4935 Dinemasporium strigosum Species Chaetosphaeriaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12977 Solenopsis invicta Species Formicidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13548 Chrozophora obliqua Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15755 Thymbra spicata Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14555 Porella swartziana Species Porellaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8499 Osmerus mordax Species Osmeridae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5269 Coleus garckeanus Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11194 Bombus hortorum Species Apidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14034 Salvia coulteri Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7484 Salacia chinensis Species Celastraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5552 Solanum sisymbriifolium Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9780 Merremia umbellata Species Convolvulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11881 Adenopeltis colliguaya Species Euphorbiaceae 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
NPT68 Individual Protein Aldose reductase Rattus norvegicus IC50 > 100000.0 nM PMID[544028]
NPT68 Individual Protein Aldose reductase Rattus norvegicus Inhibition = 8.0 % PMID[544028]

☑ 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 NPC68426 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 NPC282905
1.0 High Similarity NPC477229
0.9853 High Similarity NPC159325
0.9853 High Similarity NPC168511
0.971 High Similarity NPC267753
0.9571 High Similarity NPC108840
0.9565 High Similarity NPC130011
0.9403 High Similarity NPC180777
0.9403 High Similarity NPC2568
0.9403 High Similarity NPC103647
0.9403 High Similarity NPC260319
0.9155 High Similarity NPC195155
0.9155 High Similarity NPC97534
0.9155 High Similarity NPC174964
0.9143 High Similarity NPC81759
0.9041 High Similarity NPC472608
0.9041 High Similarity NPC26029
0.9028 High Similarity NPC475742
0.9028 High Similarity NPC5767
0.9 High Similarity NPC290058
0.9 High Similarity NPC247195
0.8933 High Similarity NPC50658
0.8904 High Similarity NPC221420
0.8904 High Similarity NPC23884
0.8873 High Similarity NPC232112
0.8841 High Similarity NPC475977
0.8784 High Similarity NPC243594
0.8784 High Similarity NPC31031
0.8732 High Similarity NPC89310
0.8732 High Similarity NPC320549
0.8732 High Similarity NPC151018
0.8732 High Similarity NPC58057
0.8732 High Similarity NPC156277
0.8714 High Similarity NPC213178
0.8714 High Similarity NPC131892
0.8714 High Similarity NPC327728
0.8714 High Similarity NPC6120
0.8696 High Similarity NPC472984
0.8684 High Similarity NPC280781
0.8684 High Similarity NPC48756
0.8684 High Similarity NPC476071
0.8657 High Similarity NPC290791
0.8657 High Similarity NPC292419
0.8649 High Similarity NPC143133
0.8649 High Similarity NPC298168
0.863 High Similarity NPC273366
0.859 High Similarity NPC25037
0.859 High Similarity NPC105895
0.859 High Similarity NPC34984
0.8571 High Similarity NPC469724
0.8571 High Similarity NPC100917
0.8571 High Similarity NPC31187
0.8571 High Similarity NPC281203
0.8514 High Similarity NPC472486
0.8514 High Similarity NPC472487
0.8493 Intermediate Similarity NPC254340
0.8481 Intermediate Similarity NPC62572
0.8429 Intermediate Similarity NPC204233
0.84 Intermediate Similarity NPC472746
0.84 Intermediate Similarity NPC475031
0.8378 Intermediate Similarity NPC21220
0.8378 Intermediate Similarity NPC159789
0.8378 Intermediate Similarity NPC125767
0.8378 Intermediate Similarity NPC212733
0.8333 Intermediate Similarity NPC61107
0.8333 Intermediate Similarity NPC289486
0.8333 Intermediate Similarity NPC30583
0.831 Intermediate Similarity NPC474954
0.831 Intermediate Similarity NPC469987
0.831 Intermediate Similarity NPC475893
0.8267 Intermediate Similarity NPC4209
0.825 Intermediate Similarity NPC133954
0.8243 Intermediate Similarity NPC280026
0.8243 Intermediate Similarity NPC133922
0.8243 Intermediate Similarity NPC167702
0.8228 Intermediate Similarity NPC475726
0.8228 Intermediate Similarity NPC269684
0.8228 Intermediate Similarity NPC472743
0.8205 Intermediate Similarity NPC328264
0.8205 Intermediate Similarity NPC271572
0.8205 Intermediate Similarity NPC474870
0.8194 Intermediate Similarity NPC321732
0.8194 Intermediate Similarity NPC324607
0.8182 Intermediate Similarity NPC320144
0.8158 Intermediate Similarity NPC317913
0.8158 Intermediate Similarity NPC207010
0.8158 Intermediate Similarity NPC112463
0.8148 Intermediate Similarity NPC213412
0.8148 Intermediate Similarity NPC74363
0.8148 Intermediate Similarity NPC475862
0.8148 Intermediate Similarity NPC187545
0.8143 Intermediate Similarity NPC80463
0.8143 Intermediate Similarity NPC260116
0.8125 Intermediate Similarity NPC474482
0.8125 Intermediate Similarity NPC475745
0.8125 Intermediate Similarity NPC219535
0.8125 Intermediate Similarity NPC237938
0.8125 Intermediate Similarity NPC474996
0.8108 Intermediate Similarity NPC310766
0.8101 Intermediate Similarity NPC268040
0.8077 Intermediate Similarity NPC261616
0.8056 Intermediate Similarity NPC473225
0.8052 Intermediate Similarity NPC324700
0.8052 Intermediate Similarity NPC185465
0.8052 Intermediate Similarity NPC34046
0.8052 Intermediate Similarity NPC224802
0.8052 Intermediate Similarity NPC171426
0.8052 Intermediate Similarity NPC80089
0.8049 Intermediate Similarity NPC73064
0.8028 Intermediate Similarity NPC142712
0.8025 Intermediate Similarity NPC292553
0.7975 Intermediate Similarity NPC469745
0.7952 Intermediate Similarity NPC230387
0.7949 Intermediate Similarity NPC201276
0.7949 Intermediate Similarity NPC73013
0.7949 Intermediate Similarity NPC80891
0.7927 Intermediate Similarity NPC72638
0.7927 Intermediate Similarity NPC477579
0.7927 Intermediate Similarity NPC95594
0.7927 Intermediate Similarity NPC83242
0.7927 Intermediate Similarity NPC235341
0.7927 Intermediate Similarity NPC472738
0.7927 Intermediate Similarity NPC471737
0.7917 Intermediate Similarity NPC48079
0.7917 Intermediate Similarity NPC41542
0.7901 Intermediate Similarity NPC264665
0.7901 Intermediate Similarity NPC474233
0.7901 Intermediate Similarity NPC171789
0.7901 Intermediate Similarity NPC180834
0.7901 Intermediate Similarity NPC473299
0.7901 Intermediate Similarity NPC74595
0.7887 Intermediate Similarity NPC230047
0.7887 Intermediate Similarity NPC19311
0.7867 Intermediate Similarity NPC475230
0.7867 Intermediate Similarity NPC253805
0.7867 Intermediate Similarity NPC211009
0.7857 Intermediate Similarity NPC69627
0.7848 Intermediate Similarity NPC470609
0.7838 Intermediate Similarity NPC108131
0.7838 Intermediate Similarity NPC476731
0.7831 Intermediate Similarity NPC88716
0.7831 Intermediate Similarity NPC171203
0.7831 Intermediate Similarity NPC142415
0.7831 Intermediate Similarity NPC68160
0.7831 Intermediate Similarity NPC307426
0.7831 Intermediate Similarity NPC18064
0.7831 Intermediate Similarity NPC102683
0.7831 Intermediate Similarity NPC98442
0.7831 Intermediate Similarity NPC293564
0.7831 Intermediate Similarity NPC51700
0.7831 Intermediate Similarity NPC4643
0.7831 Intermediate Similarity NPC242468
0.7831 Intermediate Similarity NPC130577
0.7831 Intermediate Similarity NPC57469
0.7808 Intermediate Similarity NPC472741
0.7805 Intermediate Similarity NPC294438
0.7805 Intermediate Similarity NPC264317
0.7805 Intermediate Similarity NPC131350
0.7791 Intermediate Similarity NPC472148
0.7791 Intermediate Similarity NPC472147
0.7778 Intermediate Similarity NPC327451
0.7765 Intermediate Similarity NPC50443
0.7765 Intermediate Similarity NPC18536
0.7765 Intermediate Similarity NPC472146
0.7765 Intermediate Similarity NPC291028
0.7765 Intermediate Similarity NPC185529
0.7763 Intermediate Similarity NPC472854
0.7763 Intermediate Similarity NPC162164
0.775 Intermediate Similarity NPC12933
0.775 Intermediate Similarity NPC3915
0.775 Intermediate Similarity NPC58631
0.7738 Intermediate Similarity NPC40552
0.7738 Intermediate Similarity NPC473242
0.7738 Intermediate Similarity NPC473319
0.7738 Intermediate Similarity NPC472739
0.7738 Intermediate Similarity NPC470629
0.7738 Intermediate Similarity NPC474512
0.7738 Intermediate Similarity NPC17733
0.7738 Intermediate Similarity NPC181225
0.7738 Intermediate Similarity NPC290690
0.7738 Intermediate Similarity NPC3032
0.7738 Intermediate Similarity NPC52169
0.7738 Intermediate Similarity NPC131104
0.7738 Intermediate Similarity NPC182797
0.7738 Intermediate Similarity NPC246708
0.7738 Intermediate Similarity NPC474719
0.7733 Intermediate Similarity NPC473267
0.7733 Intermediate Similarity NPC126642
0.7733 Intermediate Similarity NPC301226
0.7722 Intermediate Similarity NPC201459
0.7711 Intermediate Similarity NPC2783
0.7711 Intermediate Similarity NPC12774
0.7711 Intermediate Similarity NPC269396
0.7711 Intermediate Similarity NPC56588
0.7711 Intermediate Similarity NPC158393
0.7711 Intermediate Similarity NPC98236
0.7703 Intermediate Similarity NPC469941
0.7703 Intermediate Similarity NPC252032
0.7703 Intermediate Similarity NPC178541
0.7703 Intermediate Similarity NPC319671

  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 NPC68426 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
0.8732 High Similarity NPD4808 Clinical (unspecified phase)
0.8732 High Similarity NPD4809 Clinical (unspecified phase)
0.8714 High Similarity NPD3700 Clinical (unspecified phase)
0.8714 High Similarity NPD3699 Clinical (unspecified phase)
0.8378 Intermediate Similarity NPD3703 Phase 2
0.8333 Intermediate Similarity NPD4245 Approved
0.8333 Intermediate Similarity NPD4244 Approved
0.8267 Intermediate Similarity NPD6117 Approved
0.8243 Intermediate Similarity NPD6113 Clinical (unspecified phase)
0.8194 Intermediate Similarity NPD3698 Phase 2
0.8158 Intermediate Similarity NPD6116 Phase 1
0.8082 Intermediate Similarity NPD4789 Approved
0.8056 Intermediate Similarity NPD5360 Phase 3
0.8056 Intermediate Similarity NPD5361 Clinical (unspecified phase)
0.8052 Intermediate Similarity NPD6114 Approved
0.8052 Intermediate Similarity NPD6115 Approved
0.8052 Intermediate Similarity NPD6118 Approved
0.8052 Intermediate Similarity NPD6697 Approved
0.7887 Intermediate Similarity NPD3171 Clinical (unspecified phase)
0.7821 Intermediate Similarity NPD3671 Phase 1
0.7805 Intermediate Similarity NPD7520 Clinical (unspecified phase)
0.7674 Intermediate Similarity NPD7515 Phase 2
0.7534 Intermediate Similarity NPD4224 Phase 2
0.75 Intermediate Similarity NPD4758 Discontinued
0.7303 Intermediate Similarity NPD7748 Approved
0.7273 Intermediate Similarity NPD5777 Approved
0.7273 Intermediate Similarity NPD6081 Approved
0.7237 Intermediate Similarity NPD4267 Clinical (unspecified phase)
0.716 Intermediate Similarity NPD5364 Discontinued
0.7093 Intermediate Similarity NPD3618 Phase 1
0.7079 Intermediate Similarity NPD8034 Phase 2
0.7079 Intermediate Similarity NPD8035 Phase 2
0.7073 Intermediate Similarity NPD7645 Phase 2
0.7065 Intermediate Similarity NPD7902 Approved
0.7059 Intermediate Similarity NPD4786 Approved
0.7045 Intermediate Similarity NPD5328 Approved
0.7024 Intermediate Similarity NPD3667 Approved
0.6941 Remote Similarity NPD4788 Approved
0.6923 Remote Similarity NPD4787 Phase 1
0.6889 Remote Similarity NPD6079 Approved
0.679 Remote Similarity NPD3702 Approved
0.6739 Remote Similarity NPD7900 Approved
0.6739 Remote Similarity NPD7901 Clinical (unspecified phase)
0.6667 Remote Similarity NPD3133 Approved
0.6667 Remote Similarity NPD3665 Phase 1
0.6667 Remote Similarity NPD3666 Approved
0.663 Remote Similarity NPD4202 Approved
0.6479 Remote Similarity NPD3729 Clinical (unspecified phase)
0.6465 Remote Similarity NPD8170 Clinical (unspecified phase)
0.6421 Remote Similarity NPD5222 Approved
0.6421 Remote Similarity NPD5220 Clinical (unspecified phase)
0.6421 Remote Similarity NPD5221 Approved
0.6421 Remote Similarity NPD4697 Phase 3
0.6418 Remote Similarity NPD384 Approved
0.6418 Remote Similarity NPD385 Approved
0.6395 Remote Similarity NPD7525 Registered
0.6395 Remote Similarity NPD6928 Phase 2
0.6392 Remote Similarity NPD8418 Phase 2
0.6354 Remote Similarity NPD5173 Approved
0.6354 Remote Similarity NPD4755 Approved
0.6353 Remote Similarity NPD3617 Approved
0.6304 Remote Similarity NPD7285 Clinical (unspecified phase)
0.6292 Remote Similarity NPD3668 Phase 3
0.6277 Remote Similarity NPD6399 Phase 3
0.6267 Remote Similarity NPD3198 Approved
0.625 Remote Similarity NPD615 Clinical (unspecified phase)
0.6238 Remote Similarity NPD6920 Discontinued
0.6224 Remote Similarity NPD5285 Approved
0.6224 Remote Similarity NPD5286 Approved
0.6224 Remote Similarity NPD4700 Approved
0.6224 Remote Similarity NPD4696 Approved
0.6214 Remote Similarity NPD8132 Clinical (unspecified phase)
0.6196 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6162 Remote Similarity NPD5223 Approved
0.6154 Remote Similarity NPD3574 Clinical (unspecified phase)
0.6154 Remote Similarity NPD5279 Phase 3
0.6129 Remote Similarity NPD4753 Phase 2
0.6122 Remote Similarity NPD7638 Approved
0.6117 Remote Similarity NPD6415 Discontinued
0.61 Remote Similarity NPD5225 Approved
0.61 Remote Similarity NPD5226 Approved
0.61 Remote Similarity NPD5224 Approved
0.61 Remote Similarity NPD4633 Approved
0.61 Remote Similarity NPD5211 Phase 2
0.6078 Remote Similarity NPD5739 Approved
0.6078 Remote Similarity NPD7128 Approved
0.6078 Remote Similarity NPD6675 Approved
0.6078 Remote Similarity NPD6402 Approved
0.6067 Remote Similarity NPD4223 Phase 3
0.6067 Remote Similarity NPD4221 Approved
0.6061 Remote Similarity NPD7639 Approved
0.6061 Remote Similarity NPD7640 Approved
0.6044 Remote Similarity NPD5329 Approved
0.604 Remote Similarity NPD4754 Approved
0.604 Remote Similarity NPD5175 Approved
0.604 Remote Similarity NPD5174 Approved
0.6023 Remote Similarity NPD4695 Discontinued
0.6 Remote Similarity NPD6942 Approved
0.6 Remote Similarity NPD7339 Approved
0.598 Remote Similarity NPD5141 Approved
0.5978 Remote Similarity NPD5330 Approved
0.5978 Remote Similarity NPD7334 Approved
0.5978 Remote Similarity NPD6684 Approved
0.5978 Remote Similarity NPD7146 Approved
0.5978 Remote Similarity NPD7521 Approved
0.5978 Remote Similarity NPD6409 Approved
0.5963 Remote Similarity NPD8295 Clinical (unspecified phase)
0.5962 Remote Similarity NPD6881 Approved
0.5962 Remote Similarity NPD7320 Approved
0.5962 Remote Similarity NPD6899 Approved
0.5962 Remote Similarity NPD5345 Clinical (unspecified phase)
0.5955 Remote Similarity NPD4139 Approved
0.5955 Remote Similarity NPD4692 Approved
0.5949 Remote Similarity NPD7909 Approved
0.5941 Remote Similarity NPD7632 Discontinued
0.5934 Remote Similarity NPD4197 Approved
0.593 Remote Similarity NPD3701 Clinical (unspecified phase)
0.5922 Remote Similarity NPD4768 Approved
0.5922 Remote Similarity NPD4767 Approved
0.5918 Remote Similarity NPD7614 Phase 1
0.5914 Remote Similarity NPD3573 Approved
0.5905 Remote Similarity NPD6372 Approved
0.5905 Remote Similarity NPD6373 Approved
0.5865 Remote Similarity NPD5701 Approved
0.5865 Remote Similarity NPD5697 Approved
0.5859 Remote Similarity NPD6084 Phase 2
0.5859 Remote Similarity NPD6083 Phase 2
0.5854 Remote Similarity NPD6705 Phase 1
0.5851 Remote Similarity NPD6903 Approved
0.5849 Remote Similarity NPD7102 Approved
0.5849 Remote Similarity NPD7290 Approved
0.5849 Remote Similarity NPD6883 Approved
0.5833 Remote Similarity NPD8133 Approved
0.5816 Remote Similarity NPD5210 Approved
0.5816 Remote Similarity NPD4629 Approved
0.581 Remote Similarity NPD6011 Approved
0.581 Remote Similarity NPD4730 Approved
0.581 Remote Similarity NPD5128 Approved
0.581 Remote Similarity NPD5168 Approved
0.581 Remote Similarity NPD4729 Approved
0.5806 Remote Similarity NPD4688 Approved
0.5806 Remote Similarity NPD4689 Approved
0.5806 Remote Similarity NPD4138 Approved
0.5806 Remote Similarity NPD4519 Discontinued
0.5806 Remote Similarity NPD4690 Approved
0.5806 Remote Similarity NPD4623 Approved
0.5806 Remote Similarity NPD4693 Phase 3
0.5806 Remote Similarity NPD5205 Approved
0.5794 Remote Similarity NPD6869 Approved
0.5794 Remote Similarity NPD6649 Approved
0.5794 Remote Similarity NPD6401 Clinical (unspecified phase)
0.5794 Remote Similarity NPD6617 Approved
0.5794 Remote Similarity NPD6847 Approved
0.5794 Remote Similarity NPD8130 Phase 1
0.5794 Remote Similarity NPD6650 Approved
0.5789 Remote Similarity NPD8328 Phase 3
0.5773 Remote Similarity NPD8171 Discontinued
0.5755 Remote Similarity NPD6014 Approved
0.5755 Remote Similarity NPD6012 Approved
0.5755 Remote Similarity NPD6013 Approved
0.575 Remote Similarity NPD371 Approved
0.5741 Remote Similarity NPD6882 Approved
0.5741 Remote Similarity NPD8297 Approved
0.5729 Remote Similarity NPD6701 Clinical (unspecified phase)
0.5729 Remote Similarity NPD6700 Approved
0.5714 Remote Similarity NPD6412 Phase 2
0.5701 Remote Similarity NPD5249 Phase 3
0.5701 Remote Similarity NPD5135 Approved
0.5701 Remote Similarity NPD5250 Approved
0.5701 Remote Similarity NPD5247 Approved
0.5701 Remote Similarity NPD5251 Approved
0.5701 Remote Similarity NPD5248 Approved
0.5701 Remote Similarity NPD5134 Clinical (unspecified phase)
0.5701 Remote Similarity NPD4634 Approved
0.5701 Remote Similarity NPD5169 Approved
0.5688 Remote Similarity NPD8298 Phase 2
0.5684 Remote Similarity NPD5737 Approved
0.5684 Remote Similarity NPD6672 Approved
0.5676 Remote Similarity NPD7115 Discovery
0.567 Remote Similarity NPD6702 Approved
0.567 Remote Similarity NPD6703 Approved
0.567 Remote Similarity NPD6411 Approved
0.5667 Remote Similarity NPD4748 Discontinued
0.5648 Remote Similarity NPD5215 Approved
0.5648 Remote Similarity NPD5217 Approved
0.5648 Remote Similarity NPD5216 Approved
0.5648 Remote Similarity NPD5127 Approved
0.5638 Remote Similarity NPD5690 Phase 2
0.5638 Remote Similarity NPD4694 Approved
0.5638 Remote Similarity NPD5280 Approved
0.5618 Remote Similarity NPD4776 Phase 2
0.5618 Remote Similarity NPD4777 Suspended
0.5607 Remote Similarity NPD4061 Clinical (unspecified phase)
0.56 Remote Similarity NPD7732 Phase 3

  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