Structure

Physi-Chem Properties

Molecular Weight:  308.24
Volume:  329.325
LogP:  2.609
LogD:  2.889
LogS:  -1.322
# Rotatable Bonds:  0
TPSA:  60.69
# H-Bond Aceptor:  3
# H-Bond Donor:  3
# Rings:  4
# Heavy Atoms:  3

MedChem Properties

QED Drug-Likeness Score:  0.645
Synthetic Accessibility Score:  4.308
Fsp3:  1.0
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:  -4.75
MDCK Permeability:  1.9445529687800445e-05
Pgp-inhibitor:  0.958
Pgp-substrate:  0.997
Human Intestinal Absorption (HIA):  0.014
20% Bioavailability (F20%):  0.713
30% Bioavailability (F30%):  0.96

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.468
Plasma Protein Binding (PPB):  32.58827590942383%
Volume Distribution (VD):  1.269
Pgp-substrate:  36.15350341796875%

ADMET: Metabolism

CYP1A2-inhibitor:  0.036
CYP1A2-substrate:  0.48
CYP2C19-inhibitor:  0.014
CYP2C19-substrate:  0.781
CYP2C9-inhibitor:  0.012
CYP2C9-substrate:  0.064
CYP2D6-inhibitor:  0.002
CYP2D6-substrate:  0.147
CYP3A4-inhibitor:  0.144
CYP3A4-substrate:  0.16

ADMET: Excretion

Clearance (CL):  16.208
Half-life (T1/2):  0.591

ADMET: Toxicity

hERG Blockers:  0.165
Human Hepatotoxicity (H-HT):  0.489
Drug-inuced Liver Injury (DILI):  0.043
AMES Toxicity:  0.021
Rat Oral Acute Toxicity:  0.152
Maximum Recommended Daily Dose:  0.908
Skin Sensitization:  0.954
Carcinogencity:  0.642
Eye Corrosion:  0.976
Eye Irritation:  0.305
Respiratory Toxicity:  0.974

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  Natural Product: NPC44122

Natural Product ID:  NPC44122
Common Name*:   5Alpha-Androstane-3Alpha,11Beta,17Beta-Triol
IUPAC Name:   (3S,5S,8S,9S,10S,11R,13S,14S,17S)-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-3,11,17-triol
Synonyms:  
Standard InCHIKey:  FNICIUSFFWRLFW-FXKJLIGKSA-N
Standard InCHI:  InChI=1S/C19H32O3/c1-18-8-7-12(20)9-11(18)3-4-13-14-5-6-16(22)19(14,2)10-15(21)17(13)18/h11-17,20-22H,3-10H2,1-2H3/t11-,12-,13-,14-,15+,16-,17+,18-,19-/m0/s1
SMILES:  C[C@]12CC[C@@H](C[C@@H]1CC[C@H]1[C@@H]3CC[C@@H]([C@@]3(C)C[C@H]([C@H]21)O)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1908026
PubChem CID:   57396177
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000258] Steroids and steroid derivatives
        • [CHEMONTID:0003568] Androstane steroids
          • [CHEMONTID:0001467] Androgens and derivatives

*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
NPO12029 Sicana odorifera Species Cucurbitaceae Eukaryota n.a. n.a. n.a. PMID[11312792]
NPO15997 Aglaia cordata Species Meliaceae Eukaryota n.a. n.a. n.a. PMID[11754603]
NPO11261 Euclea natalensis Species Ebenaceae Eukaryota root bark n.a. n.a. PMID[15568795]
NPO25076 Salicornia herbacea Species Chenopodiaceae Eukaryota n.a. whole plant n.a. PMID[16276965]
NPO11796 Morus australis Species Moraceae Eukaryota n.a. root n.a. PMID[17405024]
NPO22561 Dickeya chrysanthemi Species Pectobacteriaceae Bacteria n.a. n.a. n.a. PMID[18803373]
NPO25076 Salicornia herbacea Species Chenopodiaceae Eukaryota n.a. n.a. n.a. PMID[22652051]
NPO11796 Morus australis Species Moraceae Eukaryota Root Bark n.a. n.a. PMID[27908762]
NPO11796 Morus australis Species Moraceae Eukaryota n.a. n.a. n.a. PMID[9358644]
NPO11796 Morus australis Species Moraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO13749 Luvunga scandens Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO14334 Picea jezoensis Species Pinaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO13749 Luvunga scandens Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15723 Bupleurum aureum Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14334 Picea jezoensis Species Pinaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11796 Morus australis Species Moraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15723 Bupleurum aureum Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO14624 Pertusaria pseudocorallina Species Pertusariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5208 Ligusticum lucidum Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4299 Michelia longifolia Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1159 Artemisia laciniata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13028 Trichoscypha acuminata Species Anacardiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23600 Bridelia moonii Species Phyllanthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27213 Nephrolepis biserrata Species Lomariopsidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15723 Bupleurum aureum Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9541 Suaeda salsa Species Chenopodiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13749 Luvunga scandens Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25076 Salicornia herbacea Species Chenopodiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1836 Eupatorium recurvans Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12505 Stigmodera macularia Species Buprestidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15302 Acronychia acidula Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14893 Streptomyces eurocidicus Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO14334 Picea jezoensis Species Pinaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15813 Spiraea formosa Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11261 Euclea natalensis Species Ebenaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22561 Dickeya chrysanthemi Species Pectobacteriaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO7859 Euonymus atropurpurea Species Celastraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10595 Othonna cylindrica Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15903 Goupia tomentosa Species Goupiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13481 Laurencia claviformis Species Rhodomelaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7047 Psiadia arabica Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13356 Thalictrum fauriei Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16742.1 Syringa pubescens subsp. patula Subspecies Oleaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6038 Acanthamoeba culbertsoni Species Acanthamoebidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2740 Pteris plumbea Species Pteridaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15997 Aglaia cordata Species Meliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13232 Gaillardia tontalensis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13895 Sessibugula translucens n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO12805 Othonna intermedia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15092 Alternaria infectoria Species Pleosporaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14746 Uroblaniulus canadensis Species Parajulidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9145 Herbertus aduncus Species Herbertaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15398 Rhizopus stolonifer Species Rhizopodaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14467 Senecio taiwanensis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14061 Tetraploa aristata Species Tetraplosphaeriaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12291 Rhodococcus ruber Species 0cardiaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO12029 Sicana odorifera Species Cucurbitaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11796 Morus australis Species Moraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14205 Uraria picta Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15628 Strychnos panamensis Species Loganiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10093 Castanopsis hystrix Species Fagaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11598 Callitris macleayana Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26219 Sorbus coronata Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14873 Pityrodia ternifolia Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8604 Helichrysum zeyheri Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15410 Erlangea cordifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9204 Streptomyces argillaceus Species Streptomycetaceae Bacteria 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
NPT704 Individual Protein UDP-glucuronosyltransferase 2B15 Homo sapiens Activity = 9.7 pm/min/mg PMID[474406]
NPT904 Individual Protein UDP-glucuronosyltransferase 2B17 Homo sapiens Activity = 8.0 pm/min/mg PMID[474406]
NPT701 Individual Protein UDP-glucuronosyltransferase 2B4 Homo sapiens Activity = 0.0 pm/min/mg PMID[474406]
NPT697 Individual Protein UDP-glucuronosyltransferase 2B7 Homo sapiens Activity = 8.8 total picomoles PMID[474406]
NPT902 Individual Protein UDP-glucuronosyltransferase 1A4 Homo sapiens Activity = 15.0 pm/min/mg PMID[474407]
NPT697 Individual Protein UDP-glucuronosyltransferase 2B7 Homo sapiens Activity = 0.7 total picomoles PMID[474407]

☑ 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 NPC44122 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
0.9672 High Similarity NPC281540
0.9672 High Similarity NPC159654
0.9672 High Similarity NPC167995
0.9672 High Similarity NPC118937
0.9531 High Similarity NPC477820
0.9385 High Similarity NPC251201
0.9385 High Similarity NPC232925
0.9385 High Similarity NPC63588
0.9194 High Similarity NPC114891
0.9104 High Similarity NPC470610
0.9077 High Similarity NPC472741
0.9062 High Similarity NPC142712
0.9032 High Similarity NPC148174
0.9032 High Similarity NPC218585
0.9032 High Similarity NPC71460
0.8971 High Similarity NPC304499
0.8971 High Similarity NPC48795
0.8939 High Similarity NPC66407
0.8923 High Similarity NPC63190
0.8923 High Similarity NPC475884
0.8923 High Similarity NPC48079
0.8923 High Similarity NPC473230
0.8906 High Similarity NPC474380
0.8906 High Similarity NPC41577
0.8906 High Similarity NPC473276
0.8841 High Similarity NPC317242
0.8824 High Similarity NPC153719
0.8806 High Similarity NPC282454
0.875 High Similarity NPC69149
0.8714 High Similarity NPC163597
0.8696 High Similarity NPC477508
0.8676 High Similarity NPC252182
0.8676 High Similarity NPC157422
0.8676 High Similarity NPC109457
0.8676 High Similarity NPC127094
0.8676 High Similarity NPC470071
0.8676 High Similarity NPC187471
0.8676 High Similarity NPC1340
0.8676 High Similarity NPC478103
0.8676 High Similarity NPC100586
0.8657 High Similarity NPC107919
0.8657 High Similarity NPC241085
0.8657 High Similarity NPC299948
0.8657 High Similarity NPC470830
0.8657 High Similarity NPC254037
0.8657 High Similarity NPC129829
0.8615 High Similarity NPC475943
0.8615 High Similarity NPC190827
0.8615 High Similarity NPC243469
0.8594 High Similarity NPC209686
0.8594 High Similarity NPC236099
0.8594 High Similarity NPC249078
0.8592 High Similarity NPC105208
0.8592 High Similarity NPC185915
0.8592 High Similarity NPC128951
0.8592 High Similarity NPC476233
0.8592 High Similarity NPC477227
0.8592 High Similarity NPC192046
0.8592 High Similarity NPC302578
0.8548 High Similarity NPC476735
0.8529 High Similarity NPC192192
0.8529 High Similarity NPC231945
0.8507 High Similarity NPC474756
0.8472 Intermediate Similarity NPC18857
0.8472 Intermediate Similarity NPC477817
0.8472 Intermediate Similarity NPC477819
0.8472 Intermediate Similarity NPC67657
0.8451 Intermediate Similarity NPC470145
0.8429 Intermediate Similarity NPC10476
0.8429 Intermediate Similarity NPC228994
0.8429 Intermediate Similarity NPC192501
0.8406 Intermediate Similarity NPC195530
0.8406 Intermediate Similarity NPC473279
0.8387 Intermediate Similarity NPC236588
0.8387 Intermediate Similarity NPC135438
0.8356 Intermediate Similarity NPC287452
0.8333 Intermediate Similarity NPC80463
0.8333 Intermediate Similarity NPC260116
0.8333 Intermediate Similarity NPC138502
0.831 Intermediate Similarity NPC243027
0.831 Intermediate Similarity NPC158208
0.831 Intermediate Similarity NPC196136
0.831 Intermediate Similarity NPC3403
0.8308 Intermediate Similarity NPC290791
0.8308 Intermediate Similarity NPC292419
0.8286 Intermediate Similarity NPC473238
0.8286 Intermediate Similarity NPC472341
0.8286 Intermediate Similarity NPC232112
0.8243 Intermediate Similarity NPC78545
0.8243 Intermediate Similarity NPC71535
0.8219 Intermediate Similarity NPC471045
0.8219 Intermediate Similarity NPC42853
0.8194 Intermediate Similarity NPC14112
0.8194 Intermediate Similarity NPC38141
0.8194 Intermediate Similarity NPC86305
0.8169 Intermediate Similarity NPC478130
0.8169 Intermediate Similarity NPC475458
0.8143 Intermediate Similarity NPC157777
0.8143 Intermediate Similarity NPC89310
0.8143 Intermediate Similarity NPC320549
0.8143 Intermediate Similarity NPC151018
0.8143 Intermediate Similarity NPC58057
0.8143 Intermediate Similarity NPC131506
0.8143 Intermediate Similarity NPC156277
0.8143 Intermediate Similarity NPC111234
0.8133 Intermediate Similarity NPC469745
0.8116 Intermediate Similarity NPC131892
0.8116 Intermediate Similarity NPC327728
0.8116 Intermediate Similarity NPC213178
0.8116 Intermediate Similarity NPC324607
0.8116 Intermediate Similarity NPC99264
0.8116 Intermediate Similarity NPC6120
0.8116 Intermediate Similarity NPC321732
0.8116 Intermediate Similarity NPC470833
0.8108 Intermediate Similarity NPC49599
0.8108 Intermediate Similarity NPC24504
0.8108 Intermediate Similarity NPC476176
0.8108 Intermediate Similarity NPC49627
0.8088 Intermediate Similarity NPC204233
0.8082 Intermediate Similarity NPC307336
0.8082 Intermediate Similarity NPC207010
0.8082 Intermediate Similarity NPC475031
0.8082 Intermediate Similarity NPC317913
0.8082 Intermediate Similarity NPC64081
0.8082 Intermediate Similarity NPC260301
0.8082 Intermediate Similarity NPC474574
0.806 Intermediate Similarity NPC472946
0.8056 Intermediate Similarity NPC230704
0.8056 Intermediate Similarity NPC231680
0.8056 Intermediate Similarity NPC240235
0.8056 Intermediate Similarity NPC97534
0.8056 Intermediate Similarity NPC70982
0.8056 Intermediate Similarity NPC178383
0.8056 Intermediate Similarity NPC273366
0.8056 Intermediate Similarity NPC195155
0.8056 Intermediate Similarity NPC91387
0.8056 Intermediate Similarity NPC212879
0.8056 Intermediate Similarity NPC270306
0.8056 Intermediate Similarity NPC231256
0.8056 Intermediate Similarity NPC185536
0.8056 Intermediate Similarity NPC104387
0.8056 Intermediate Similarity NPC212733
0.8056 Intermediate Similarity NPC174964
0.8028 Intermediate Similarity NPC310766
0.8028 Intermediate Similarity NPC253805
0.8026 Intermediate Similarity NPC475388
0.8026 Intermediate Similarity NPC296734
0.8026 Intermediate Similarity NPC470611
0.8 Intermediate Similarity NPC7479
0.8 Intermediate Similarity NPC47149
0.8 Intermediate Similarity NPC248944
0.8 Intermediate Similarity NPC45296
0.8 Intermediate Similarity NPC257296
0.7973 Intermediate Similarity NPC472499
0.7973 Intermediate Similarity NPC475
0.7973 Intermediate Similarity NPC244385
0.7973 Intermediate Similarity NPC471769
0.7973 Intermediate Similarity NPC472501
0.7973 Intermediate Similarity NPC167037
0.7973 Intermediate Similarity NPC472502
0.7973 Intermediate Similarity NPC6978
0.7973 Intermediate Similarity NPC147993
0.7973 Intermediate Similarity NPC138621
0.7973 Intermediate Similarity NPC472500
0.7973 Intermediate Similarity NPC301707
0.7971 Intermediate Similarity NPC475893
0.7971 Intermediate Similarity NPC469987
0.7945 Intermediate Similarity NPC472486
0.7945 Intermediate Similarity NPC91573
0.7945 Intermediate Similarity NPC475742
0.7945 Intermediate Similarity NPC78067
0.7945 Intermediate Similarity NPC93662
0.7945 Intermediate Similarity NPC278091
0.7945 Intermediate Similarity NPC477601
0.7945 Intermediate Similarity NPC472487
0.7945 Intermediate Similarity NPC4209
0.7945 Intermediate Similarity NPC5767
0.7945 Intermediate Similarity NPC477602
0.7945 Intermediate Similarity NPC473916
0.7937 Intermediate Similarity NPC3025
0.7922 Intermediate Similarity NPC478054
0.7922 Intermediate Similarity NPC141941
0.7922 Intermediate Similarity NPC110778
0.7922 Intermediate Similarity NPC193870
0.7922 Intermediate Similarity NPC232023
0.7922 Intermediate Similarity NPC477818
0.7922 Intermediate Similarity NPC327451
0.7917 Intermediate Similarity NPC254509
0.7917 Intermediate Similarity NPC25511
0.7917 Intermediate Similarity NPC280026
0.7917 Intermediate Similarity NPC62657
0.7917 Intermediate Similarity NPC49168
0.7917 Intermediate Similarity NPC308440
0.7917 Intermediate Similarity NPC192638
0.7917 Intermediate Similarity NPC254340
0.7917 Intermediate Similarity NPC196358
0.7917 Intermediate Similarity NPC5046
0.7917 Intermediate Similarity NPC145552
0.7917 Intermediate Similarity NPC167702
0.7917 Intermediate Similarity NPC472503

  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 NPC44122 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
0.8806 High Similarity NPD4787 Phase 1
0.8657 High Similarity NPD4267 Clinical (unspecified phase)
0.8261 Intermediate Similarity NPD4245 Approved
0.8261 Intermediate Similarity NPD4244 Approved
0.8143 Intermediate Similarity NPD4809 Clinical (unspecified phase)
0.8143 Intermediate Similarity NPD4808 Clinical (unspecified phase)
0.8116 Intermediate Similarity NPD3699 Clinical (unspecified phase)
0.8116 Intermediate Similarity NPD3700 Clinical (unspecified phase)
0.8116 Intermediate Similarity NPD3698 Phase 2
0.8082 Intermediate Similarity NPD6116 Phase 1
0.8 Intermediate Similarity NPD6928 Phase 2
0.7945 Intermediate Similarity NPD6117 Approved
0.7917 Intermediate Similarity NPD6113 Clinical (unspecified phase)
0.7808 Intermediate Similarity NPD3703 Phase 2
0.7763 Intermediate Similarity NPD7525 Registered
0.7733 Intermediate Similarity NPD6115 Approved
0.7733 Intermediate Similarity NPD6697 Approved
0.7733 Intermediate Similarity NPD6118 Approved
0.7733 Intermediate Similarity NPD6114 Approved
0.75 Intermediate Similarity NPD4789 Approved
0.7467 Intermediate Similarity NPD3701 Clinical (unspecified phase)
0.7465 Intermediate Similarity NPD5361 Clinical (unspecified phase)
0.7465 Intermediate Similarity NPD5360 Phase 3
0.7286 Intermediate Similarity NPD3171 Clinical (unspecified phase)
0.7273 Intermediate Similarity NPD3671 Phase 1
0.7162 Intermediate Similarity NPD5777 Approved
0.7105 Intermediate Similarity NPD6942 Approved
0.7105 Intermediate Similarity NPD7339 Approved
0.7089 Intermediate Similarity NPD4748 Discontinued
0.7073 Intermediate Similarity NPD7520 Clinical (unspecified phase)
0.7049 Intermediate Similarity NPD384 Approved
0.7049 Intermediate Similarity NPD385 Approved
0.6986 Remote Similarity NPD6705 Phase 1
0.6962 Remote Similarity NPD7645 Phase 2
0.6933 Remote Similarity NPD4758 Discontinued
0.6897 Remote Similarity NPD8171 Discontinued
0.6883 Remote Similarity NPD3702 Approved
0.6829 Remote Similarity NPD4788 Approved
0.6712 Remote Similarity NPD4224 Phase 2
0.6711 Remote Similarity NPD6081 Approved
0.6711 Remote Similarity NPD4243 Approved
0.6705 Remote Similarity NPD4202 Approved
0.6667 Remote Similarity NPD6701 Clinical (unspecified phase)
0.6667 Remote Similarity NPD6700 Approved
0.6625 Remote Similarity NPD5364 Discontinued
0.6591 Remote Similarity NPD8035 Phase 2
0.6591 Remote Similarity NPD6703 Approved
0.6591 Remote Similarity NPD6702 Approved
0.6591 Remote Similarity NPD8034 Phase 2
0.6588 Remote Similarity NPD3618 Phase 1
0.6556 Remote Similarity NPD7991 Discontinued
0.6552 Remote Similarity NPD5328 Approved
0.6548 Remote Similarity NPD4786 Approved
0.6548 Remote Similarity NPD3133 Approved
0.6548 Remote Similarity NPD3666 Approved
0.6548 Remote Similarity NPD3665 Phase 1
0.6538 Remote Similarity NPD4784 Approved
0.6538 Remote Similarity NPD4785 Approved
0.6538 Remote Similarity NPD6924 Approved
0.6538 Remote Similarity NPD6926 Approved
0.6512 Remote Similarity NPD4751 Clinical (unspecified phase)
0.6506 Remote Similarity NPD3667 Approved
0.6438 Remote Similarity NPD371 Approved
0.6413 Remote Similarity NPD4755 Approved
0.6404 Remote Similarity NPD6079 Approved
0.6375 Remote Similarity NPD6933 Approved
0.6344 Remote Similarity NPD7638 Approved
0.6338 Remote Similarity NPD3198 Approved
0.6282 Remote Similarity NPD7150 Approved
0.6282 Remote Similarity NPD7152 Approved
0.6282 Remote Similarity NPD7151 Approved
0.6277 Remote Similarity NPD5286 Approved
0.6277 Remote Similarity NPD5285 Approved
0.6277 Remote Similarity NPD7639 Approved
0.6277 Remote Similarity NPD7640 Approved
0.6277 Remote Similarity NPD4696 Approved
0.6277 Remote Similarity NPD4700 Approved
0.6265 Remote Similarity NPD7509 Discontinued
0.625 Remote Similarity NPD4190 Phase 3
0.625 Remote Similarity NPD5275 Approved
0.6237 Remote Similarity NPD7920 Phase 3
0.6237 Remote Similarity NPD7919 Phase 3
0.6234 Remote Similarity NPD6923 Approved
0.6234 Remote Similarity NPD6922 Approved
0.6211 Remote Similarity NPD5223 Approved
0.6207 Remote Similarity NPD8308 Discontinued
0.6186 Remote Similarity NPD8170 Clinical (unspecified phase)
0.617 Remote Similarity NPD8088 Phase 1
0.6154 Remote Similarity NPD7143 Approved
0.6154 Remote Similarity NPD7144 Approved
0.6146 Remote Similarity NPD5225 Approved
0.6146 Remote Similarity NPD7632 Discontinued
0.6146 Remote Similarity NPD5226 Approved
0.6146 Remote Similarity NPD4633 Approved
0.6146 Remote Similarity NPD5224 Approved
0.6146 Remote Similarity NPD5211 Phase 2
0.6145 Remote Similarity NPD4195 Approved
0.6145 Remote Similarity NPD6929 Approved
0.6122 Remote Similarity NPD5739 Approved
0.6122 Remote Similarity NPD7128 Approved
0.6122 Remote Similarity NPD6402 Approved
0.6122 Remote Similarity NPD6675 Approved
0.6105 Remote Similarity NPD8418 Phase 2
0.6094 Remote Similarity NPD388 Approved
0.6094 Remote Similarity NPD386 Approved
0.6082 Remote Similarity NPD5175 Approved
0.6082 Remote Similarity NPD4754 Approved
0.6082 Remote Similarity NPD5174 Approved
0.6071 Remote Similarity NPD6930 Phase 2
0.6071 Remote Similarity NPD6931 Approved
0.6044 Remote Similarity NPD7515 Phase 2
0.6042 Remote Similarity NPD4159 Approved
0.602 Remote Similarity NPD5141 Approved
0.6 Remote Similarity NPD4753 Phase 2
0.6 Remote Similarity NPD6899 Approved
0.6 Remote Similarity NPD6881 Approved
0.6 Remote Similarity NPD7320 Approved
0.5978 Remote Similarity NPD6399 Phase 3
0.5977 Remote Similarity NPD7338 Clinical (unspecified phase)
0.596 Remote Similarity NPD4768 Approved
0.596 Remote Similarity NPD4767 Approved
0.5957 Remote Similarity NPD5220 Clinical (unspecified phase)
0.5957 Remote Similarity NPD4697 Phase 3
0.5957 Remote Similarity NPD5222 Approved
0.5957 Remote Similarity NPD5221 Approved
0.5941 Remote Similarity NPD6373 Approved
0.5941 Remote Similarity NPD6372 Approved
0.593 Remote Similarity NPD4221 Approved
0.593 Remote Similarity NPD4223 Phase 3
0.5926 Remote Similarity NPD1810 Approved
0.5926 Remote Similarity NPD1811 Approved
0.5915 Remote Similarity NPD586 Phase 1
0.5909 Remote Similarity NPD5329 Approved
0.5904 Remote Similarity NPD5776 Phase 2
0.5904 Remote Similarity NPD6925 Approved
0.5904 Remote Similarity NPD6932 Approved
0.59 Remote Similarity NPD7646 Clinical (unspecified phase)
0.59 Remote Similarity NPD5701 Approved
0.59 Remote Similarity NPD5697 Approved
0.5895 Remote Similarity NPD5173 Approved
0.5889 Remote Similarity NPD7513 Clinical (unspecified phase)
0.5882 Remote Similarity NPD7102 Approved
0.5882 Remote Similarity NPD7290 Approved
0.5882 Remote Similarity NPD6883 Approved
0.5862 Remote Similarity NPD6695 Phase 3
0.5843 Remote Similarity NPD7334 Approved
0.5843 Remote Similarity NPD7146 Approved
0.5843 Remote Similarity NPD7521 Approved
0.5843 Remote Similarity NPD5330 Approved
0.5843 Remote Similarity NPD6409 Approved
0.5843 Remote Similarity NPD3574 Clinical (unspecified phase)
0.5843 Remote Similarity NPD6684 Approved
0.5842 Remote Similarity NPD6011 Approved
0.5842 Remote Similarity NPD5128 Approved
0.5842 Remote Similarity NPD4729 Approved
0.5842 Remote Similarity NPD4730 Approved
0.5833 Remote Similarity NPD7145 Approved
0.5833 Remote Similarity NPD5290 Discontinued
0.5833 Remote Similarity NPD3617 Approved
0.5825 Remote Similarity NPD8130 Phase 1
0.5825 Remote Similarity NPD6650 Approved
0.5825 Remote Similarity NPD6617 Approved
0.5825 Remote Similarity NPD6847 Approved
0.5825 Remote Similarity NPD6649 Approved
0.5825 Remote Similarity NPD6869 Approved
0.5825 Remote Similarity NPD6401 Clinical (unspecified phase)
0.5814 Remote Similarity NPD4139 Approved
0.5814 Remote Similarity NPD4692 Approved
0.5795 Remote Similarity NPD3668 Phase 3
0.5795 Remote Similarity NPD4197 Approved
0.5784 Remote Similarity NPD6013 Approved
0.5784 Remote Similarity NPD6014 Approved
0.5784 Remote Similarity NPD6012 Approved
0.5769 Remote Similarity NPD8297 Approved
0.5769 Remote Similarity NPD6882 Approved
0.5765 Remote Similarity NPD6683 Phase 2
0.5745 Remote Similarity NPD7748 Approved
0.573 Remote Similarity NPD6893 Approved
0.5729 Remote Similarity NPD7902 Approved
0.5729 Remote Similarity NPD6083 Phase 2
0.5729 Remote Similarity NPD6084 Phase 2
0.5728 Remote Similarity NPD5249 Phase 3
0.5728 Remote Similarity NPD5169 Approved
0.5728 Remote Similarity NPD5251 Approved
0.5728 Remote Similarity NPD5250 Approved
0.5728 Remote Similarity NPD5247 Approved
0.5728 Remote Similarity NPD5135 Approved
0.5728 Remote Similarity NPD5134 Clinical (unspecified phase)
0.5728 Remote Similarity NPD4634 Approved
0.5728 Remote Similarity NPD5248 Approved
0.5714 Remote Similarity NPD6903 Approved
0.5698 Remote Similarity NPD7514 Phase 3
0.5684 Remote Similarity NPD5210 Approved
0.5684 Remote Similarity NPD4629 Approved
0.5673 Remote Similarity NPD5215 Approved
0.5673 Remote Similarity NPD5127 Approved
0.5673 Remote Similarity NPD5216 Approved
0.5673 Remote Similarity NPD5217 Approved
0.5667 Remote Similarity NPD5279 Phase 3
0.5667 Remote Similarity NPD4689 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