Structure

Physi-Chem Properties

Molecular Weight:  406.15
Volume:  368.338
LogP:  -0.277
LogD:  -0.198
LogS:  -0.832
# Rotatable Bonds:  5
TPSA:  164.37
# H-Bond Aceptor:  11
# H-Bond Donor:  5
# Rings:  3
# Heavy Atoms:  11

MedChem Properties

QED Drug-Likeness Score:  0.315
Synthetic Accessibility Score:  4.841
Fsp3:  0.824
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.938
MDCK Permeability:  0.00011953939974773675
Pgp-inhibitor:  0.001
Pgp-substrate:  0.936
Human Intestinal Absorption (HIA):  0.584
20% Bioavailability (F20%):  0.005
30% Bioavailability (F30%):  0.992

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.236
Plasma Protein Binding (PPB):  21.147945404052734%
Volume Distribution (VD):  0.434
Pgp-substrate:  56.4305419921875%

ADMET: Metabolism

CYP1A2-inhibitor:  0.011
CYP1A2-substrate:  0.875
CYP2C19-inhibitor:  0.019
CYP2C19-substrate:  0.658
CYP2C9-inhibitor:  0.003
CYP2C9-substrate:  0.024
CYP2D6-inhibitor:  0.006
CYP2D6-substrate:  0.096
CYP3A4-inhibitor:  0.007
CYP3A4-substrate:  0.112

ADMET: Excretion

Clearance (CL):  2.145
Half-life (T1/2):  0.895

ADMET: Toxicity

hERG Blockers:  0.034
Human Hepatotoxicity (H-HT):  0.319
Drug-inuced Liver Injury (DILI):  0.695
AMES Toxicity:  0.238
Rat Oral Acute Toxicity:  0.056
Maximum Recommended Daily Dose:  0.382
Skin Sensitization:  0.304
Carcinogencity:  0.937
Eye Corrosion:  0.003
Eye Irritation:  0.182
Respiratory Toxicity:  0.956

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  Natural Product: NPC231710

Natural Product ID:  NPC231710
Common Name*:   (7Alpha-Hydroxy)-Morroniside
IUPAC Name:   methyl (1S,3S,4aS,8S,8aS)-3-hydroxy-1-methyl-8-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,3,4,4a,8,8a-hexahydropyrano[3,4-c]pyran-5-carboxylate
Synonyms:   (7Alpha-Hydroxy)-Morroniside
Standard InCHIKey:  YTZSBJLNMIQROD-VYDXWPHLSA-N
Standard InCHI:  InChI=1S/C17H26O11/c1-6-11-7(3-10(19)26-6)8(15(23)24-2)5-25-16(11)28-17-14(22)13(21)12(20)9(4-18)27-17/h5-7,9-14,16-22H,3-4H2,1-2H3/t6-,7+,9+,10-,11+,12+,13-,14+,16-,17-/m0/s1
SMILES:  OC[C@H]1O[C@@H](O[C@@H]2OC=C([C@@H]3[C@H]2[C@H](C)O[C@@H](C3)O)C(=O)OC)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL2152455
PubChem CID:   21593530
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0004603] Organic oxygen compounds
      • [CHEMONTID:0000323] Organooxygen compounds
        • [CHEMONTID:0000011] Carbohydrates and carbohydrate conjugates
          • [CHEMONTID:0002105] Glycosyl compounds
            • [CHEMONTID:0002207] O-glycosyl compounds

*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
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota Flowers n.a. n.a. DOI[10.1002/elan.200403102]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota Flowers n.a. n.a. DOI[10.1016/j.foodchem.2012.02.124]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota Flowers n.a. n.a. PMID[11077184]
NPO6092 Symphyocladia latiuscula Species Rhodomelaceae Eukaryota n.a. n.a. n.a. PMID[11141124]
NPO3699 Acacia aulacocarpa Species Fabaceae Eukaryota n.a. leaf n.a. PMID[11735581]
NPO6092 Symphyocladia latiuscula Species Rhodomelaceae Eukaryota n.a. n.a. n.a. PMID[15844965]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota Flowers n.a. n.a. PMID[17328234]
NPO6092 Symphyocladia latiuscula Species Rhodomelaceae Eukaryota n.a. n.a. n.a. PMID[17602526]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota Flower buds n.a. n.a. PMID[18321056]
NPO10548 Stephania viridiflavens Species Menispermaceae Eukaryota n.a. root n.a. PMID[20645211]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota n.a. flower n.a. PMID[21804227]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota n.a. flower bud n.a. PMID[21942812]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota flower buds Henan province, China 2005-MAY PMID[21942812]
NPO14197 Patrinia scabra Species Caprifoliaceae Eukaryota Roots n.a. n.a. PMID[23002924]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota n.a. leaf n.a. PMID[23265495]
NPO22355 Flacourtia indica Species Salicaceae Eukaryota n.a. n.a. n.a. PMID[23354072]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota Flower buds n.a. n.a. PMID[24279769]
NPO11907 Streptomyces nitrosporeus Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[25304895]
NPO12588 Cornus officinalis Species Cornaceae Eukaryota Fruits n.a. n.a. PMID[29140705]
NPO14197 Patrinia scabra Species Caprifoliaceae Eukaryota Roots n.a. n.a. PMID[29799195]
NPO26277 Euphorbia hirta Species Euphorbiaceae Eukaryota n.a. n.a. n.a. PMID[32141299]
NPO11907 Streptomyces nitrosporeus Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[8609080]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO3853 Aspidosperma subincanum Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO10548 Stephania viridiflavens Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO12588 Cornus officinalis Species Cornaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO14197 Patrinia scabra Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO26277 Euphorbia hirta Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO19948 Neolentinus lepideus Species Gloeophyllaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7569 Guatteria boliviana Species Annonaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO26277 Euphorbia hirta Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO3853 Aspidosperma subincanum Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO16539 Viguiera puruana Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO12588 Cornus officinalis Species Cornaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO4823 Psiadia dentata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO8418 Anemone flaccida Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14197 Patrinia scabra Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO10548 Stephania viridiflavens Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO12588 Cornus officinalis Species Cornaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO10548 Stephania viridiflavens Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO12588 Cornus officinalis Species Cornaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO26277 Euphorbia hirta Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO3853 Aspidosperma subincanum Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26277 Euphorbia hirta Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14921 Anisothrix integra Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6729 Juniperus brevifolia Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9983.1 Ambrosia artemisiifolia var. elatior Varieties Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8254 Melicope lasioneura Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6237 Cryptocarya aschersoniana Species Lauraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6543 Parachlorella kessleri Species n.a. Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22355 Flacourtia indica Species Salicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16539 Viguiera puruana Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2588 Erodium malacoides Species Geraniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO471 Ardisia neriifolia Species Primulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14197 Patrinia scabra Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4823 Psiadia dentata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12588 Cornus officinalis Species Cornaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3597 Rheedia acuminata Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19948 Neolentinus lepideus Species Gloeophyllaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10470 Pimpinella major Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6092 Symphyocladia latiuscula Species Rhodomelaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10548 Stephania viridiflavens Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8418 Anemone flaccida Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10458 Pithecollobium dulce n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO5155 Peritassa compta Species Celastraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6207 Porthetria dispar n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO5196 Eupatorium argentinum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19646 Cynthia papillosa n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO22459 Impatiens capensis Species Balsaminaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22065 Montana elegans Species Tettigoniidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7569 Guatteria boliviana Species Annonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10942 Retama sphaerocarpa Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3699 Acacia aulacocarpa Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16965 Lyngbya aestuarii Species Oscillatoriaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO11907 Streptomyces nitrosporeus 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
NPT165 Cell Line HeLa Homo sapiens IC50 > 50000.0 nM PMID[470920]
NPT38 Individual Protein Signal transducer and activator of transcription 3 Homo sapiens IC50 = 7000.0 nM PMID[470921]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 > 50000.0 nM PMID[470920]

☑ 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 NPC231710 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 NPC270908
1.0 High Similarity NPC470573
1.0 High Similarity NPC65665
1.0 High Similarity NPC216826
1.0 High Similarity NPC120021
0.9425 High Similarity NPC472124
0.9425 High Similarity NPC472125
0.9425 High Similarity NPC472126
0.931 High Similarity NPC307699
0.9091 High Similarity NPC117596
0.8901 High Similarity NPC101051
0.8889 High Similarity NPC61201
0.8737 High Similarity NPC222062
0.8696 High Similarity NPC469543
0.869 High Similarity NPC323472
0.8667 High Similarity NPC6414
0.8667 High Similarity NPC303451
0.8646 High Similarity NPC267869
0.8646 High Similarity NPC284929
0.8646 High Similarity NPC197541
0.8646 High Similarity NPC234304
0.8646 High Similarity NPC118761
0.8542 High Similarity NPC4899
0.8542 High Similarity NPC177013
0.8542 High Similarity NPC35185
0.8542 High Similarity NPC195510
0.8542 High Similarity NPC474730
0.8542 High Similarity NPC13171
0.8526 High Similarity NPC22149
0.8526 High Similarity NPC255677
0.8526 High Similarity NPC306344
0.8469 Intermediate Similarity NPC41681
0.8454 Intermediate Similarity NPC37240
0.8438 Intermediate Similarity NPC28304
0.8438 Intermediate Similarity NPC298255
0.8404 Intermediate Similarity NPC161293
0.8351 Intermediate Similarity NPC310804
0.8351 Intermediate Similarity NPC261117
0.8351 Intermediate Similarity NPC106668
0.8298 Intermediate Similarity NPC170204
0.8283 Intermediate Similarity NPC170432
0.8265 Intermediate Similarity NPC475928
0.8265 Intermediate Similarity NPC27687
0.8247 Intermediate Similarity NPC3488
0.8247 Intermediate Similarity NPC287539
0.8211 Intermediate Similarity NPC241911
0.82 Intermediate Similarity NPC148270
0.82 Intermediate Similarity NPC254538
0.82 Intermediate Similarity NPC474285
0.82 Intermediate Similarity NPC197813
0.82 Intermediate Similarity NPC80338
0.8182 Intermediate Similarity NPC86095
0.8163 Intermediate Similarity NPC250545
0.8 Intermediate Similarity NPC63897
0.7961 Intermediate Similarity NPC193741
0.7921 Intermediate Similarity NPC127235
0.781 Intermediate Similarity NPC475851
0.781 Intermediate Similarity NPC475924
0.7767 Intermediate Similarity NPC110701
0.7677 Intermediate Similarity NPC198422
0.7677 Intermediate Similarity NPC472015
0.7677 Intermediate Similarity NPC40182
0.7653 Intermediate Similarity NPC306041
0.7629 Intermediate Similarity NPC71589
0.7629 Intermediate Similarity NPC294293
0.7624 Intermediate Similarity NPC304163
0.7624 Intermediate Similarity NPC80144
0.7609 Intermediate Similarity NPC266718
0.7604 Intermediate Similarity NPC477749
0.7576 Intermediate Similarity NPC472290
0.7551 Intermediate Similarity NPC6765
0.7551 Intermediate Similarity NPC93869
0.7527 Intermediate Similarity NPC470124
0.7526 Intermediate Similarity NPC320552
0.7525 Intermediate Similarity NPC67296
0.75 Intermediate Similarity NPC49833
0.75 Intermediate Similarity NPC327253
0.75 Intermediate Similarity NPC249171
0.7475 Intermediate Similarity NPC54731
0.7475 Intermediate Similarity NPC143446
0.7449 Intermediate Similarity NPC477348
0.7449 Intermediate Similarity NPC238264
0.7449 Intermediate Similarity NPC25701
0.7449 Intermediate Similarity NPC274588
0.7449 Intermediate Similarity NPC2003
0.7449 Intermediate Similarity NPC477345
0.7429 Intermediate Similarity NPC219900
0.7429 Intermediate Similarity NPC392
0.7429 Intermediate Similarity NPC177524
0.7429 Intermediate Similarity NPC473807
0.7423 Intermediate Similarity NPC470379
0.7423 Intermediate Similarity NPC470373
0.7423 Intermediate Similarity NPC9447
0.7419 Intermediate Similarity NPC475035
0.74 Intermediate Similarity NPC304445
0.74 Intermediate Similarity NPC236580
0.7396 Intermediate Similarity NPC477748
0.7379 Intermediate Similarity NPC473148
0.7379 Intermediate Similarity NPC197736
0.7368 Intermediate Similarity NPC74139
0.7368 Intermediate Similarity NPC475037
0.7363 Intermediate Similarity NPC127295
0.7363 Intermediate Similarity NPC163362
0.7347 Intermediate Similarity NPC472196
0.7347 Intermediate Similarity NPC238090
0.7347 Intermediate Similarity NPC320089
0.7347 Intermediate Similarity NPC472195
0.734 Intermediate Similarity NPC477746
0.734 Intermediate Similarity NPC477747
0.7327 Intermediate Similarity NPC37866
0.732 Intermediate Similarity NPC202886
0.73 Intermediate Similarity NPC475164
0.73 Intermediate Similarity NPC473605
0.73 Intermediate Similarity NPC475241
0.73 Intermediate Similarity NPC475593
0.73 Intermediate Similarity NPC476066
0.73 Intermediate Similarity NPC473765
0.73 Intermediate Similarity NPC475375
0.73 Intermediate Similarity NPC475540
0.73 Intermediate Similarity NPC170527
0.73 Intermediate Similarity NPC475525
0.7292 Intermediate Similarity NPC473151
0.7292 Intermediate Similarity NPC137368
0.729 Intermediate Similarity NPC83005
0.7282 Intermediate Similarity NPC201191
0.7282 Intermediate Similarity NPC471599
0.7273 Intermediate Similarity NPC159698
0.7255 Intermediate Similarity NPC244878
0.7245 Intermediate Similarity NPC477349
0.7245 Intermediate Similarity NPC472197
0.7238 Intermediate Similarity NPC476738
0.7238 Intermediate Similarity NPC476740
0.7228 Intermediate Similarity NPC278506
0.7216 Intermediate Similarity NPC93190
0.7216 Intermediate Similarity NPC50464
0.7216 Intermediate Similarity NPC285588
0.7212 Intermediate Similarity NPC309398
0.7188 Intermediate Similarity NPC118077
0.7188 Intermediate Similarity NPC142583
0.7188 Intermediate Similarity NPC475186
0.7184 Intermediate Similarity NPC216911
0.7184 Intermediate Similarity NPC476611
0.7184 Intermediate Similarity NPC20673
0.7184 Intermediate Similarity NPC219038
0.7172 Intermediate Similarity NPC474835
0.7172 Intermediate Similarity NPC280390
0.7158 Intermediate Similarity NPC475034
0.7157 Intermediate Similarity NPC61630
0.7157 Intermediate Similarity NPC151093
0.7157 Intermediate Similarity NPC56071
0.7157 Intermediate Similarity NPC169468
0.7157 Intermediate Similarity NPC307517
0.7157 Intermediate Similarity NPC70733
0.7157 Intermediate Similarity NPC81483
0.7143 Intermediate Similarity NPC13710
0.7143 Intermediate Similarity NPC469869
0.7129 Intermediate Similarity NPC284063
0.7129 Intermediate Similarity NPC474297
0.7129 Intermediate Similarity NPC256230
0.7115 Intermediate Similarity NPC121423
0.7113 Intermediate Similarity NPC248312
0.7103 Intermediate Similarity NPC193765
0.71 Intermediate Similarity NPC44682
0.71 Intermediate Similarity NPC475832
0.71 Intermediate Similarity NPC475927
0.71 Intermediate Similarity NPC163409
0.7091 Intermediate Similarity NPC75167
0.7091 Intermediate Similarity NPC311592
0.7087 Intermediate Similarity NPC476211
0.7087 Intermediate Similarity NPC476320
0.7087 Intermediate Similarity NPC473146
0.7083 Intermediate Similarity NPC475019
0.7083 Intermediate Similarity NPC476015
0.7083 Intermediate Similarity NPC474762
0.7083 Intermediate Similarity NPC474949
0.7071 Intermediate Similarity NPC294643
0.7071 Intermediate Similarity NPC329952
0.7071 Intermediate Similarity NPC110072
0.7071 Intermediate Similarity NPC473150
0.7071 Intermediate Similarity NPC274274
0.7071 Intermediate Similarity NPC235051
0.7071 Intermediate Similarity NPC472199
0.7059 Intermediate Similarity NPC476613
0.7059 Intermediate Similarity NPC476612
0.7059 Intermediate Similarity NPC86843
0.7054 Intermediate Similarity NPC474483
0.7053 Intermediate Similarity NPC288471
0.7053 Intermediate Similarity NPC475963
0.7053 Intermediate Similarity NPC3464
0.7053 Intermediate Similarity NPC474780
0.7053 Intermediate Similarity NPC151176
0.7048 Intermediate Similarity NPC151516
0.7048 Intermediate Similarity NPC473816
0.7048 Intermediate Similarity NPC329834
0.7048 Intermediate Similarity NPC474581
0.7048 Intermediate Similarity NPC475367
0.7041 Intermediate Similarity NPC92974
0.7037 Intermediate Similarity NPC315836
0.7037 Intermediate Similarity NPC313668
0.7033 Intermediate Similarity NPC110813

  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 NPC231710 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
0.7429 Intermediate Similarity NPD6686 Approved
0.697 Remote Similarity NPD6698 Approved
0.697 Remote Similarity NPD46 Approved
0.6957 Remote Similarity NPD8513 Phase 3
0.6937 Remote Similarity NPD8133 Approved
0.6827 Remote Similarity NPD8029 Clinical (unspecified phase)
0.681 Remote Similarity NPD8516 Approved
0.681 Remote Similarity NPD8515 Approved
0.681 Remote Similarity NPD8517 Approved
0.6757 Remote Similarity NPD8413 Clinical (unspecified phase)
0.6583 Remote Similarity NPD7507 Approved
0.6555 Remote Similarity NPD7829 Approved
0.6555 Remote Similarity NPD7830 Approved
0.6526 Remote Similarity NPD7329 Approved
0.6525 Remote Similarity NPD7503 Approved
0.6423 Remote Similarity NPD7319 Approved
0.6417 Remote Similarity NPD8328 Phase 3
0.6408 Remote Similarity NPD7983 Approved
0.6404 Remote Similarity NPD896 Approved
0.6404 Remote Similarity NPD897 Approved
0.6404 Remote Similarity NPD898 Approved
0.6396 Remote Similarity NPD6412 Phase 2
0.6325 Remote Similarity NPD8295 Clinical (unspecified phase)
0.6325 Remote Similarity NPD8137 Clinical (unspecified phase)
0.6311 Remote Similarity NPD7838 Discovery
0.6283 Remote Similarity NPD8132 Clinical (unspecified phase)
0.6271 Remote Similarity NPD7641 Discontinued
0.6263 Remote Similarity NPD6110 Phase 1
0.6261 Remote Similarity NPD6053 Discontinued
0.626 Remote Similarity NPD8074 Phase 3
0.6237 Remote Similarity NPD3181 Approved
0.6198 Remote Similarity NPD8080 Discontinued
0.6195 Remote Similarity NPD5345 Clinical (unspecified phase)
0.6179 Remote Similarity NPD8451 Approved
0.6167 Remote Similarity NPD8294 Approved
0.6167 Remote Similarity NPD8377 Approved
0.6148 Remote Similarity NPD7642 Approved
0.6134 Remote Similarity NPD7327 Approved
0.6134 Remote Similarity NPD7328 Approved
0.6129 Remote Similarity NPD8448 Approved
0.6116 Remote Similarity NPD8378 Approved
0.6116 Remote Similarity NPD8274 Clinical (unspecified phase)
0.6116 Remote Similarity NPD8033 Approved
0.6116 Remote Similarity NPD8444 Approved
0.6116 Remote Similarity NPD8296 Approved
0.6116 Remote Similarity NPD8380 Approved
0.6116 Remote Similarity NPD8335 Approved
0.6116 Remote Similarity NPD8379 Approved
0.6111 Remote Similarity NPD8392 Approved
0.6111 Remote Similarity NPD8390 Approved
0.6111 Remote Similarity NPD8391 Approved
0.6083 Remote Similarity NPD7516 Approved
0.6019 Remote Similarity NPD7839 Suspended
0.5984 Remote Similarity NPD8269 Approved
0.5984 Remote Similarity NPD8268 Approved
0.5984 Remote Similarity NPD8267 Approved
0.5984 Remote Similarity NPD8266 Approved
0.598 Remote Similarity NPD1733 Clinical (unspecified phase)
0.5968 Remote Similarity NPD8342 Approved
0.5968 Remote Similarity NPD8341 Approved
0.5968 Remote Similarity NPD8299 Approved
0.5968 Remote Similarity NPD8340 Approved
0.5965 Remote Similarity NPD7899 Clinical (unspecified phase)
0.5941 Remote Similarity NPD3669 Approved
0.5941 Remote Similarity NPD3670 Clinical (unspecified phase)
0.5922 Remote Similarity NPD4249 Approved
0.5905 Remote Similarity NPD6101 Approved
0.5905 Remote Similarity NPD5764 Clinical (unspecified phase)
0.5893 Remote Similarity NPD8139 Approved
0.5893 Remote Similarity NPD8086 Approved
0.5893 Remote Similarity NPD8085 Approved
0.5893 Remote Similarity NPD8083 Approved
0.5893 Remote Similarity NPD8084 Approved
0.5893 Remote Similarity NPD8138 Approved
0.5893 Remote Similarity NPD8082 Approved
0.5888 Remote Similarity NPD5779 Approved
0.5888 Remote Similarity NPD5778 Approved
0.5882 Remote Similarity NPD6400 Clinical (unspecified phase)
0.5865 Remote Similarity NPD4250 Approved
0.5865 Remote Similarity NPD4251 Approved
0.5862 Remote Similarity NPD4061 Clinical (unspecified phase)
0.5841 Remote Similarity NPD8275 Approved
0.5841 Remote Similarity NPD8276 Approved
0.5833 Remote Similarity NPD890 Clinical (unspecified phase)
0.5833 Remote Similarity NPD888 Phase 3
0.5833 Remote Similarity NPD893 Approved
0.5833 Remote Similarity NPD892 Phase 3
0.5833 Remote Similarity NPD891 Phase 3
0.5833 Remote Similarity NPD7966 Clinical (unspecified phase)
0.5827 Remote Similarity NPD7736 Approved
0.5812 Remote Similarity NPD6371 Approved
0.5806 Remote Similarity NPD6370 Approved
0.5804 Remote Similarity NPD5344 Discontinued
0.5794 Remote Similarity NPD6411 Approved
0.5789 Remote Similarity NPD8170 Clinical (unspecified phase)
0.5789 Remote Similarity NPD8081 Approved
0.5785 Remote Similarity NPD6009 Approved
0.578 Remote Similarity NPD1698 Clinical (unspecified phase)
0.5778 Remote Similarity NPD8961 Approved
0.5772 Remote Similarity NPD6319 Approved
0.5766 Remote Similarity NPD7638 Approved
0.5766 Remote Similarity NPD4225 Approved
0.5748 Remote Similarity NPD8293 Discontinued
0.5743 Remote Similarity NPD1779 Approved
0.5743 Remote Similarity NPD1780 Approved
0.5739 Remote Similarity NPD8393 Approved
0.573 Remote Similarity NPD6123 Approved
0.5726 Remote Similarity NPD6921 Approved
0.5714 Remote Similarity NPD7492 Approved
0.5714 Remote Similarity NPD7639 Approved
0.5714 Remote Similarity NPD7640 Approved
0.5714 Remote Similarity NPD6882 Approved
0.569 Remote Similarity NPD8140 Approved
0.569 Remote Similarity NPD8307 Discontinued
0.5686 Remote Similarity NPD6435 Approved
0.5678 Remote Similarity NPD5955 Clinical (unspecified phase)
0.5669 Remote Similarity NPD6616 Approved
0.5667 Remote Similarity NPD4632 Approved
0.5645 Remote Similarity NPD6054 Approved
0.5639 Remote Similarity NPD8387 Clinical (unspecified phase)
0.5631 Remote Similarity NPD7154 Phase 3
0.5625 Remote Similarity NPD7078 Approved
0.56 Remote Similarity NPD6015 Approved
0.56 Remote Similarity NPD6016 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