Structure

Physi-Chem Properties

Molecular Weight:  430.16
Volume:  424.005
LogP:  1.431
LogD:  1.868
LogS:  -3.08
# Rotatable Bonds:  5
TPSA:  128.84
# H-Bond Aceptor:  8
# H-Bond Donor:  5
# Rings:  4
# Heavy Atoms:  8

MedChem Properties

QED Drug-Likeness Score:  0.472
Synthetic Accessibility Score:  3.973
Fsp3:  0.391
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  1
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.222
MDCK Permeability:  6.4868754634517245e-06
Pgp-inhibitor:  0.126
Pgp-substrate:  0.038
Human Intestinal Absorption (HIA):  0.869
20% Bioavailability (F20%):  0.125
30% Bioavailability (F30%):  0.87

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.256
Plasma Protein Binding (PPB):  86.12316131591797%
Volume Distribution (VD):  0.653
Pgp-substrate:  4.574615478515625%

ADMET: Metabolism

CYP1A2-inhibitor:  0.101
CYP1A2-substrate:  0.12
CYP2C19-inhibitor:  0.024
CYP2C19-substrate:  0.102
CYP2C9-inhibitor:  0.019
CYP2C9-substrate:  0.212
CYP2D6-inhibitor:  0.088
CYP2D6-substrate:  0.335
CYP3A4-inhibitor:  0.056
CYP3A4-substrate:  0.169

ADMET: Excretion

Clearance (CL):  6.044
Half-life (T1/2):  0.798

ADMET: Toxicity

hERG Blockers:  0.273
Human Hepatotoxicity (H-HT):  0.262
Drug-inuced Liver Injury (DILI):  0.096
AMES Toxicity:  0.783
Rat Oral Acute Toxicity:  0.061
Maximum Recommended Daily Dose:  0.47
Skin Sensitization:  0.926
Carcinogencity:  0.242
Eye Corrosion:  0.003
Eye Irritation:  0.035
Respiratory Toxicity:  0.049

Download Data

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

  Natural Product: NPC48309

Natural Product ID:  NPC48309
Common Name*:   Subavenoside A
IUPAC Name:   (2R,3R,4S,5S,6R)-2-[(2-hydroxy-3-methoxy-7H-dibenzo[1,2-a:3',4'-c][7]annulen-5-yl)methoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
Synonyms:   Subavenoside A
Standard InCHIKey:  JGDPINWXRGNXOI-XNBWIAOKSA-N
Standard InCHI:  InChI=1S/C23H26O8/c1-29-18-9-15-13(11-30-23-22(28)21(27)20(26)19(10-24)31-23)7-6-12-4-2-3-5-14(12)16(15)8-17(18)25/h2-5,7-9,19-28H,6,10-11H2,1H3/t19-,20-,21+,22-,23-/m1/s1
SMILES:  COc1cc2C(=CCc3ccccc3-c2cc1O)CO[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL2152482
PubChem CID:   71453067
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
NPO9305 Iotrochota purpurea Species Iotrochotidae Eukaryota n.a. n.a. n.a. PMID[10924179]
NPO8035 Tylophora tanakae Species Apocynaceae Eukaryota n.a. n.a. n.a. PMID[12350151]
NPO10900 Cinnamomum subavenium Species Lauraceae Eukaryota stems Wulai Hsiang, Taipei County, Taiwan 2005-MAY PMID[17253858]
NPO2298 Streptomyces platensis Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[19581087]
NPO2298 Streptomyces platensis Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[20299229]
NPO4138 Betula platyphylla Species Betulaceae Eukaryota bark n.a. n.a. PMID[20363129]
NPO2298 Streptomyces platensis Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[21214253]
NPO10900 Cinnamomum subavenium Species Lauraceae Eukaryota Leaves n.a. n.a. PMID[23025417]
NPO9305 Iotrochota purpurea Species Iotrochotidae Eukaryota n.a. n.a. n.a. PMID[23131412]
NPO10900 Cinnamomum subavenium Species Lauraceae Eukaryota stem bark Laifeng, Hubei Province, China 2012-JUL PMID[26087384]
NPO11699 Ecballium elaterium Species Cucurbitaceae Eukaryota Fruit juice n.a. n.a. PMID[3404148]
NPO11699 Ecballium elaterium Species Cucurbitaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO4138 Betula platyphylla Species Betulaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO4138 Betula platyphylla Species Betulaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11699 Ecballium elaterium Species Cucurbitaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO4138 Betula platyphylla Species Betulaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO4138 Betula platyphylla Species Betulaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO761 Fagus fusca Species Fagaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12888 Echinus microtuberculatus Species Echinidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1182 Croton montevidensis Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12436 Quercus imbricaria Species Fagaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12308 Metridium senile Species Metridiidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11699 Ecballium elaterium Species Cucurbitaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12669 Cassine papillosa Species Celastraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6253 Conus pulicarius Species Conidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4138 Betula platyphylla Species Betulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2298 Streptomyces platensis Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO5384 Ligustrum obtusifolium Species Oleaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12544 Dioscorea olfersiana Species Dioscoreaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20291 Phyllanthus oligospermus Species Phyllanthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11256 Pseudowintera colorata Species Winteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9305 Iotrochota purpurea Species Iotrochotidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10737 Asteriscus aquaticus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5823 Helichrysum auriceps Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10900 Cinnamomum subavenium Species Lauraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9922 Myelobia smerintha Species Crambidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11553 Phebalium dentatum Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3736 Scrophularia koelzii Species Scrophulariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7709 Spiracantha cornifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12188 Datisca glomerata Species Datiscaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9672 Lotus ucrainicus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7045 Viviparus japonicus Species Viviparidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8035 Tylophora tanakae Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2608 Solanum andigena Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9509 Charpentiera obovata Species Amaranthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10393 Ophidiaster ophidianus Species Ophidiasteridae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5008 Hubertia tomentosa Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15252 Clathria prolifera Species Microcionidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4493 Polygonum flaccidum Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8477 Myristica cagayanensis Species Myristicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3378 Alstonia undulifolia Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11811 Capparis ovata Species Capparaceae 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
NPT2 Others Unspecified IC50 = 141600.0 nM PMID[548366]

☑ 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 NPC48309 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
0.9706 High Similarity NPC60249
0.9632 High Similarity NPC76871
0.9481 High Similarity NPC199459
0.9481 High Similarity NPC177035
0.9481 High Similarity NPC52277
0.9357 High Similarity NPC286245
0.9357 High Similarity NPC272619
0.9348 High Similarity NPC472711
0.9286 High Similarity NPC471065
0.9286 High Similarity NPC253015
0.9286 High Similarity NPC473045
0.9286 High Similarity NPC25292
0.927 High Similarity NPC138738
0.927 High Similarity NPC304152
0.927 High Similarity NPC470413
0.9254 High Similarity NPC65942
0.9254 High Similarity NPC248307
0.9214 High Similarity NPC477898
0.9214 High Similarity NPC470950
0.9214 High Similarity NPC278961
0.9214 High Similarity NPC185307
0.9214 High Similarity NPC46092
0.9214 High Similarity NPC113680
0.9214 High Similarity NPC473044
0.9191 High Similarity NPC35731
0.9155 High Similarity NPC190714
0.9155 High Similarity NPC99515
0.9149 High Similarity NPC84181
0.9149 High Similarity NPC283995
0.9149 High Similarity NPC129417
0.9149 High Similarity NPC470235
0.9143 High Similarity NPC472714
0.9143 High Similarity NPC5262
0.9143 High Similarity NPC476356
0.9143 High Similarity NPC189115
0.9137 High Similarity NPC106944
0.9124 High Similarity NPC101624
0.9124 High Similarity NPC184938
0.9104 High Similarity NPC307110
0.9097 High Similarity NPC44452
0.9085 High Similarity NPC38041
0.9085 High Similarity NPC18979
0.9085 High Similarity NPC279298
0.9085 High Similarity NPC22150
0.9071 High Similarity NPC469661
0.9051 High Similarity NPC476411
0.9051 High Similarity NPC187194
0.9051 High Similarity NPC470881
0.9044 High Similarity NPC97316
0.9041 High Similarity NPC21902
0.903 High Similarity NPC474178
0.903 High Similarity NPC245826
0.903 High Similarity NPC252307
0.9028 High Similarity NPC175976
0.9021 High Similarity NPC112861
0.9014 High Similarity NPC472712
0.9014 High Similarity NPC118385
0.9014 High Similarity NPC187774
0.9014 High Similarity NPC472713
0.9014 High Similarity NPC473046
0.9007 High Similarity NPC469559
0.9007 High Similarity NPC140502
0.8978 High Similarity NPC6836
0.8958 High Similarity NPC224674
0.8958 High Similarity NPC275284
0.8958 High Similarity NPC114505
0.8958 High Similarity NPC193473
0.8958 High Similarity NPC15956
0.8958 High Similarity NPC213074
0.8958 High Similarity NPC31325
0.8958 High Similarity NPC39657
0.8955 High Similarity NPC106511
0.8951 High Similarity NPC469586
0.8951 High Similarity NPC475096
0.8929 High Similarity NPC98777
0.8929 High Similarity NPC212770
0.8929 High Similarity NPC156376
0.8913 High Similarity NPC107478
0.8905 High Similarity NPC106739
0.8905 High Similarity NPC252833
0.8905 High Similarity NPC471505
0.8905 High Similarity NPC254275
0.8904 High Similarity NPC9933
0.8904 High Similarity NPC182368
0.8904 High Similarity NPC145979
0.8904 High Similarity NPC469707
0.8904 High Similarity NPC185955
0.8904 High Similarity NPC225815
0.8904 High Similarity NPC214326
0.8904 High Similarity NPC469706
0.8904 High Similarity NPC260781
0.8904 High Similarity NPC218041
0.8897 High Similarity NPC80600
0.8897 High Similarity NPC472024
0.8889 High Similarity NPC125755
0.8873 High Similarity NPC475084
0.8873 High Similarity NPC246947
0.8857 High Similarity NPC65530
0.8857 High Similarity NPC59324
0.8849 High Similarity NPC142547
0.8849 High Similarity NPC135777
0.8841 High Similarity NPC132895
0.8836 High Similarity NPC51328
0.8836 High Similarity NPC55158
0.8836 High Similarity NPC286235
0.8832 High Similarity NPC9912
0.8828 High Similarity NPC227902
0.8824 High Similarity NPC26653
0.8824 High Similarity NPC86030
0.8824 High Similarity NPC166040
0.8824 High Similarity NPC270849
0.8824 High Similarity NPC5851
0.8824 High Similarity NPC248355
0.8819 High Similarity NPC161700
0.8819 High Similarity NPC277867
0.8819 High Similarity NPC34587
0.8819 High Similarity NPC252292
0.8819 High Similarity NPC43508
0.8819 High Similarity NPC34927
0.8819 High Similarity NPC476301
0.8819 High Similarity NPC100998
0.8819 High Similarity NPC476382
0.8815 High Similarity NPC165045
0.8815 High Similarity NPC79715
0.8815 High Similarity NPC231607
0.8815 High Similarity NPC118533
0.8815 High Similarity NPC108659
0.8815 High Similarity NPC264900
0.8811 High Similarity NPC265154
0.8811 High Similarity NPC478239
0.8803 High Similarity NPC471908
0.8794 High Similarity NPC193666
0.8794 High Similarity NPC123526
0.8794 High Similarity NPC88640
0.8786 High Similarity NPC203230
0.8786 High Similarity NPC242028
0.8784 High Similarity NPC474442
0.8776 High Similarity NPC475224
0.8776 High Similarity NPC98624
0.8768 High Similarity NPC201587
0.8768 High Similarity NPC253105
0.8768 High Similarity NPC470270
0.8767 High Similarity NPC130449
0.8767 High Similarity NPC248132
0.8759 High Similarity NPC64201
0.8759 High Similarity NPC181079
0.8759 High Similarity NPC241522
0.8759 High Similarity NPC187998
0.8759 High Similarity NPC145305
0.8759 High Similarity NPC242807
0.8759 High Similarity NPC42300
0.8759 High Similarity NPC153739
0.8759 High Similarity NPC77040
0.8759 High Similarity NPC173308
0.8759 High Similarity NPC92164
0.8759 High Similarity NPC174495
0.8759 High Similarity NPC257582
0.8759 High Similarity NPC275950
0.875 High Similarity NPC302378
0.875 High Similarity NPC164183
0.875 High Similarity NPC72529
0.875 High Similarity NPC76176
0.875 High Similarity NPC469313
0.875 High Similarity NPC138227
0.875 High Similarity NPC79429
0.875 High Similarity NPC471063
0.875 High Similarity NPC471667
0.875 High Similarity NPC217635
0.875 High Similarity NPC168579
0.8741 High Similarity NPC253878
0.8741 High Similarity NPC94179
0.8741 High Similarity NPC157816
0.8725 High Similarity NPC78809
0.8723 High Similarity NPC474039
0.8714 High Similarity NPC79957
0.8705 High Similarity NPC25821
0.8705 High Similarity NPC169973
0.8699 High Similarity NPC15538
0.8699 High Similarity NPC473480
0.8699 High Similarity NPC232992
0.8696 High Similarity NPC277804
0.8696 High Similarity NPC475067
0.8696 High Similarity NPC476345
0.869 High Similarity NPC110763
0.869 High Similarity NPC189239
0.869 High Similarity NPC166506
0.869 High Similarity NPC197352
0.8686 High Similarity NPC184092
0.8686 High Similarity NPC475875
0.8681 High Similarity NPC252169
0.8681 High Similarity NPC37793
0.8676 High Similarity NPC147821
0.8676 High Similarity NPC118787
0.8676 High Similarity NPC163332
0.8676 High Similarity NPC183181
0.8676 High Similarity NPC319625
0.8676 High Similarity NPC41706
0.8676 High Similarity NPC111247
0.8676 High Similarity NPC5428
0.8676 High Similarity NPC292056

  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 NPC48309 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
0.8551 High Similarity NPD3027 Phase 3
0.8403 Intermediate Similarity NPD7266 Discontinued
0.8288 Intermediate Similarity NPD6674 Discontinued
0.8239 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.8239 Intermediate Similarity NPD1613 Approved
0.8235 Intermediate Similarity NPD3705 Approved
0.8089 Intermediate Similarity NPD6234 Discontinued
0.8075 Intermediate Similarity NPD7228 Approved
0.8 Intermediate Similarity NPD37 Approved
0.7974 Intermediate Similarity NPD1653 Approved
0.7962 Intermediate Similarity NPD4966 Approved
0.7962 Intermediate Similarity NPD4965 Approved
0.7962 Intermediate Similarity NPD4967 Phase 2
0.7958 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7887 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7862 Intermediate Similarity NPD3619 Clinical (unspecified phase)
0.7862 Intermediate Similarity NPD3620 Phase 2
0.7842 Intermediate Similarity NPD1091 Approved
0.7758 Intermediate Similarity NPD7074 Phase 3
0.7754 Intermediate Similarity NPD1357 Approved
0.7704 Intermediate Similarity NPD5283 Phase 1
0.7697 Intermediate Similarity NPD7054 Approved
0.7687 Intermediate Similarity NPD228 Approved
0.7682 Intermediate Similarity NPD5698 Clinical (unspecified phase)
0.7654 Intermediate Similarity NPD7199 Phase 2
0.7651 Intermediate Similarity NPD4108 Discontinued
0.7651 Intermediate Similarity NPD7472 Approved
0.7639 Intermediate Similarity NPD2861 Phase 2
0.7636 Intermediate Similarity NPD3818 Discontinued
0.7597 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7588 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7571 Intermediate Similarity NPD5125 Phase 3
0.7571 Intermediate Similarity NPD5126 Approved
0.756 Intermediate Similarity NPD7685 Pre-registration
0.756 Intermediate Similarity NPD7240 Approved
0.755 Intermediate Similarity NPD2029 Clinical (unspecified phase)
0.7532 Intermediate Similarity NPD5058 Phase 3
0.75 Intermediate Similarity NPD4060 Phase 1
0.75 Intermediate Similarity NPD2977 Approved
0.75 Intermediate Similarity NPD2978 Approved
0.75 Intermediate Similarity NPD8455 Phase 2
0.75 Intermediate Similarity NPD6797 Phase 2
0.7483 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.7466 Intermediate Similarity NPD4908 Phase 1
0.7456 Intermediate Similarity NPD7251 Discontinued
0.7455 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7438 Intermediate Similarity NPD1934 Approved
0.7415 Intermediate Similarity NPD4625 Phase 3
0.7412 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.7412 Intermediate Similarity NPD7808 Phase 3
0.7407 Intermediate Similarity NPD3021 Approved
0.7407 Intermediate Similarity NPD3022 Approved
0.7365 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7362 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.7361 Intermediate Similarity NPD2983 Phase 2
0.7361 Intermediate Similarity NPD2982 Phase 2
0.7351 Intermediate Similarity NPD4538 Approved
0.7351 Intermediate Similarity NPD4536 Approved
0.7351 Intermediate Similarity NPD4537 Clinical (unspecified phase)
0.7343 Intermediate Similarity NPD1610 Phase 2
0.7338 Intermediate Similarity NPD7157 Approved
0.7305 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.7305 Intermediate Similarity NPD6166 Phase 2
0.7305 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.7301 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7292 Intermediate Similarity NPD2981 Phase 2
0.7284 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7279 Intermediate Similarity NPD3018 Phase 2
0.7278 Intermediate Similarity NPD5844 Phase 1
0.7267 Intermediate Similarity NPD1558 Phase 1
0.7257 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7251 Intermediate Similarity NPD6559 Discontinued
0.7246 Intermediate Similarity NPD7843 Approved
0.7244 Intermediate Similarity NPD6190 Approved
0.7241 Intermediate Similarity NPD3600 Clinical (unspecified phase)
0.7226 Intermediate Similarity NPD3060 Approved
0.7222 Intermediate Similarity NPD7237 Clinical (unspecified phase)
0.7219 Intermediate Similarity NPD5735 Approved
0.7208 Intermediate Similarity NPD1375 Discontinued
0.7206 Intermediate Similarity NPD2684 Approved
0.72 Intermediate Similarity NPD6843 Phase 3
0.72 Intermediate Similarity NPD6842 Approved
0.72 Intermediate Similarity NPD6841 Approved
0.719 Intermediate Similarity NPD5588 Approved
0.719 Intermediate Similarity NPD5960 Phase 3
0.7186 Intermediate Similarity NPD6232 Discontinued
0.7186 Intermediate Similarity NPD3787 Discontinued
0.7178 Intermediate Similarity NPD1465 Phase 2
0.7158 Intermediate Similarity NPD7680 Approved
0.7152 Intermediate Similarity NPD7975 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD4005 Discontinued
0.7143 Intermediate Similarity NPD3094 Phase 2
0.7134 Intermediate Similarity NPD2677 Approved
0.7134 Intermediate Similarity NPD5241 Discontinued
0.7133 Intermediate Similarity NPD5111 Phase 2
0.7133 Intermediate Similarity NPD5109 Approved
0.7133 Intermediate Similarity NPD5110 Phase 2
0.7126 Intermediate Similarity NPD7090 Clinical (unspecified phase)
0.7125 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7115 Intermediate Similarity NPD5177 Phase 3
0.7115 Intermediate Similarity NPD4236 Phase 3
0.7115 Intermediate Similarity NPD4237 Approved
0.7107 Intermediate Similarity NPD4160 Clinical (unspecified phase)
0.7097 Intermediate Similarity NPD5763 Approved
0.7097 Intermediate Similarity NPD5762 Approved
0.7093 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7076 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.7075 Intermediate Similarity NPD8651 Approved
0.7073 Intermediate Similarity NPD2801 Approved
0.707 Intermediate Similarity NPD4628 Phase 3
0.7069 Intermediate Similarity NPD8312 Approved
0.7069 Intermediate Similarity NPD8313 Approved
0.7067 Intermediate Similarity NPD7095 Approved
0.7063 Intermediate Similarity NPD1548 Phase 1
0.7063 Intermediate Similarity NPD5261 Clinical (unspecified phase)
0.7059 Intermediate Similarity NPD7473 Discontinued
0.7039 Intermediate Similarity NPD2238 Phase 2
0.7039 Intermediate Similarity NPD4140 Approved
0.7032 Intermediate Similarity NPD2438 Suspended
0.703 Intermediate Similarity NPD2560 Approved
0.703 Intermediate Similarity NPD2563 Approved
0.7025 Intermediate Similarity NPD5307 Clinical (unspecified phase)
0.702 Intermediate Similarity NPD6410 Clinical (unspecified phase)
0.7018 Intermediate Similarity NPD3751 Discontinued
0.7013 Intermediate Similarity NPD7097 Phase 1
0.7012 Intermediate Similarity NPD7945 Clinical (unspecified phase)
0.7007 Intermediate Similarity NPD4749 Approved
0.7 Intermediate Similarity NPD2489 Approved
0.7 Intermediate Similarity NPD27 Approved
0.6994 Remote Similarity NPD4380 Phase 2
0.6993 Remote Similarity NPD5536 Phase 2
0.6993 Remote Similarity NPD3657 Discovery
0.6986 Remote Similarity NPD3092 Approved
0.6983 Remote Similarity NPD7879 Clinical (unspecified phase)
0.6982 Remote Similarity NPD6071 Discontinued
0.6981 Remote Similarity NPD6783 Clinical (unspecified phase)
0.698 Remote Similarity NPD6584 Phase 3
0.6974 Remote Similarity NPD6233 Phase 2
0.6972 Remote Similarity NPD709 Approved
0.6972 Remote Similarity NPD6671 Approved
0.697 Remote Similarity NPD6818 Clinical (unspecified phase)
0.6966 Remote Similarity NPD5846 Approved
0.6966 Remote Similarity NPD6516 Phase 2
0.6962 Remote Similarity NPD4109 Clinical (unspecified phase)
0.6962 Remote Similarity NPD6658 Clinical (unspecified phase)
0.6962 Remote Similarity NPD6331 Phase 2
0.6962 Remote Similarity NPD4110 Phase 3
0.6941 Remote Similarity NPD2970 Approved
0.6941 Remote Similarity NPD2969 Approved
0.6928 Remote Similarity NPD3817 Phase 2
0.6928 Remote Similarity NPD5837 Clinical (unspecified phase)
0.6923 Remote Similarity NPD8127 Discontinued
0.6918 Remote Similarity NPD5084 Clinical (unspecified phase)
0.691 Remote Similarity NPD7906 Approved
0.6908 Remote Similarity NPD6798 Discontinued
0.6903 Remote Similarity NPD4978 Clinical (unspecified phase)
0.6899 Remote Similarity NPD4162 Approved
0.6894 Remote Similarity NPD7004 Clinical (unspecified phase)
0.6894 Remote Similarity NPD4123 Phase 3
0.6892 Remote Similarity NPD5327 Phase 3
0.6892 Remote Similarity NPD3685 Discontinued
0.689 Remote Similarity NPD7028 Phase 2
0.6886 Remote Similarity NPD3882 Suspended
0.6884 Remote Similarity NPD290 Approved
0.6883 Remote Similarity NPD6355 Discontinued
0.6882 Remote Similarity NPD3051 Approved
0.6875 Remote Similarity NPD7313 Approved
0.6875 Remote Similarity NPD7310 Approved
0.6875 Remote Similarity NPD7312 Approved
0.6875 Remote Similarity NPD7311 Approved
0.6871 Remote Similarity NPD3687 Approved
0.6871 Remote Similarity NPD3686 Approved
0.6867 Remote Similarity NPD6917 Clinical (unspecified phase)
0.6863 Remote Similarity NPD2674 Phase 3
0.6859 Remote Similarity NPD6028 Clinical (unspecified phase)
0.6859 Remote Similarity NPD6029 Clinical (unspecified phase)
0.6855 Remote Similarity NPD4535 Phase 3
0.6854 Remote Similarity NPD4663 Approved
0.6852 Remote Similarity NPD1940 Clinical (unspecified phase)
0.6849 Remote Similarity NPD4626 Approved
0.6846 Remote Similarity NPD1283 Approved
0.6845 Remote Similarity NPD4055 Discovery
0.6839 Remote Similarity NPD6653 Approved
0.6836 Remote Similarity NPD7309 Approved
0.6835 Remote Similarity NPD4664 Clinical (unspecified phase)
0.6832 Remote Similarity NPD7040 Clinical (unspecified phase)
0.6832 Remote Similarity NPD7041 Phase 2
0.6832 Remote Similarity NPD1511 Approved
0.6828 Remote Similarity NPD3091 Approved
0.6826 Remote Similarity NPD6374 Clinical (unspecified phase)
0.6818 Remote Similarity NPD2979 Phase 3
0.6812 Remote Similarity NPD968 Approved
0.68 Remote Similarity NPD7007 Discovery
0.6792 Remote Similarity NPD1652 Phase 2
0.6788 Remote Similarity NPD4675 Approved
0.6788 Remote Similarity NPD4678 Approved
0.6781 Remote Similarity NPD1651 Approved
0.6781 Remote Similarity NPD5691 Approved
0.678 Remote Similarity NPD4578 Approved
0.678 Remote Similarity NPD4577 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