Structure

Physi-Chem Properties

Molecular Weight:  101.05
Volume:  101.045
LogP:  0.486
LogD:  -0.467
LogS:  0.302
# Rotatable Bonds:  1
TPSA:  49.66
# H-Bond Aceptor:  3
# H-Bond Donor:  1
# Rings:  0
# Heavy Atoms:  3

MedChem Properties

QED Drug-Likeness Score:  0.295
Synthetic Accessibility Score:  3.046
Fsp3:  0.5
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  1
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.545
MDCK Permeability:  2.7730298825190403e-05
Pgp-inhibitor:  0.0
Pgp-substrate:  0.001
Human Intestinal Absorption (HIA):  0.015
20% Bioavailability (F20%):  0.006
30% Bioavailability (F30%):  0.02

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.994
Plasma Protein Binding (PPB):  52.53559112548828%
Volume Distribution (VD):  0.735
Pgp-substrate:  65.62340545654297%

ADMET: Metabolism

CYP1A2-inhibitor:  0.325
CYP1A2-substrate:  0.166
CYP2C19-inhibitor:  0.098
CYP2C19-substrate:  0.076
CYP2C9-inhibitor:  0.008
CYP2C9-substrate:  0.691
CYP2D6-inhibitor:  0.005
CYP2D6-substrate:  0.219
CYP3A4-inhibitor:  0.008
CYP3A4-substrate:  0.171

ADMET: Excretion

Clearance (CL):  2.692
Half-life (T1/2):  0.741

ADMET: Toxicity

hERG Blockers:  0.052
Human Hepatotoxicity (H-HT):  0.03
Drug-inuced Liver Injury (DILI):  0.122
AMES Toxicity:  0.081
Rat Oral Acute Toxicity:  0.679
Maximum Recommended Daily Dose:  0.022
Skin Sensitization:  0.659
Carcinogencity:  0.677
Eye Corrosion:  0.993
Eye Irritation:  0.992
Respiratory Toxicity:  0.562

Download Data

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

  Natural Product: NPC60249

Natural Product ID:  NPC60249
Common Name*:   Subavenoside D
IUPAC Name:   (2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[[5-(hydroxymethyl)-3-methoxy-7H-dibenzo[1,2-a:3',4'-d][7]annulen-2-yl]oxy]oxane-3,4,5-triol
Synonyms:   Subavenoside D
Standard InCHIKey:  SABDCGUULUIQAJ-XNBWIAOKSA-N
Standard InCHI:  InChI=1S/C23H26O8/c1-29-17-8-15-13(10-24)7-6-12-4-2-3-5-14(12)16(15)9-18(17)30-23-22(28)21(27)20(26)19(11-25)31-23/h2-5,7-9,19-28H,6,10-11H2,1H3/t19-,20-,21+,22-,23-/m1/s1
SMILES:  OC[C@H]1O[C@@H](Oc2cc3c(cc2OC)C(=CCc2c3cccc2)CO)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL2152483
PubChem CID:   71461984
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:0004165] Phenolic glycosides

*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]
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]
NPO11699 Ecballium elaterium Species Cucurbitaceae 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]
NPO4138 Betula platyphylla Species Betulaceae 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]
NPO12544 Dioscorea olfersiana Species Dioscoreaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10737 Asteriscus aquaticus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9305 Iotrochota purpurea Species Iotrochotidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5823 Helichrysum auriceps Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9922 Myelobia smerintha Species Crambidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10900 Cinnamomum subavenium Species Lauraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11553 Phebalium dentatum Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7709 Spiracantha cornifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3736 Scrophularia koelzii Species Scrophulariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9672 Lotus ucrainicus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12188 Datisca glomerata Species Datiscaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7045 Viviparus japonicus Species Viviparidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2608 Solanum andigena Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8035 Tylophora tanakae Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10393 Ophidiaster ophidianus Species Ophidiasteridae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9509 Charpentiera obovata Species Amaranthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4493 Polygonum flaccidum Species Polygonaceae 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]
NPO11811 Capparis ovata Species Capparaceae 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]
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]
NPO761 Fagus fusca 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]
NPO12436 Quercus imbricaria Species Fagaceae 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 = 50700.0 nM PMID[516101]

☑ 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 NPC60249 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
0.9925 High Similarity NPC76871
0.9706 High Similarity NPC48309
0.9333 High Similarity NPC187194
0.9333 High Similarity NPC476411
0.9286 High Similarity NPC25292
0.9286 High Similarity NPC473045
0.927 High Similarity NPC138738
0.927 High Similarity NPC470413
0.9214 High Similarity NPC470950
0.9214 High Similarity NPC185307
0.9214 High Similarity NPC473044
0.9214 High Similarity NPC46092
0.9197 High Similarity NPC199459
0.9197 High Similarity NPC52277
0.9197 High Similarity NPC177035
0.9179 High Similarity NPC80600
0.9179 High Similarity NPC472024
0.9155 High Similarity NPC190714
0.9155 High Similarity NPC99515
0.9149 High Similarity NPC283995
0.9149 High Similarity NPC129417
0.9149 High Similarity NPC470235
0.9143 High Similarity NPC246947
0.9143 High Similarity NPC476356
0.9143 High Similarity NPC189115
0.9137 High Similarity NPC106944
0.9111 High Similarity NPC9912
0.9104 High Similarity NPC248355
0.9104 High Similarity NPC166040
0.9104 High Similarity NPC270849
0.9104 High Similarity NPC26653
0.9097 High Similarity NPC44452
0.9085 High Similarity NPC38041
0.9085 High Similarity NPC286245
0.9085 High Similarity NPC43508
0.9085 High Similarity NPC476301
0.9085 High Similarity NPC272619
0.9085 High Similarity NPC18979
0.9085 High Similarity NPC279298
0.9085 High Similarity NPC22150
0.9071 High Similarity NPC472711
0.9071 High Similarity NPC469661
0.9044 High Similarity NPC97316
0.9041 High Similarity NPC21902
0.9041 High Similarity NPC474442
0.903 High Similarity NPC302378
0.9028 High Similarity NPC175976
0.9021 High Similarity NPC112861
0.9014 High Similarity NPC471667
0.9014 High Similarity NPC471065
0.9014 High Similarity NPC217635
0.9014 High Similarity NPC253015
0.9014 High Similarity NPC471063
0.9014 High Similarity NPC79429
0.9007 High Similarity NPC469559
0.8993 High Similarity NPC304152
0.8978 High Similarity NPC25821
0.8971 High Similarity NPC65942
0.8971 High Similarity NPC248307
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
0.8951 High Similarity NPC475096
0.8951 High Similarity NPC469586
0.8944 High Similarity NPC278961
0.8944 High Similarity NPC113680
0.8944 High Similarity NPC477898
0.8929 High Similarity NPC212770
0.8929 High Similarity NPC98777
0.8929 High Similarity NPC156376
0.8913 High Similarity NPC251981
0.8913 High Similarity NPC48863
0.8913 High Similarity NPC13745
0.8913 High Similarity NPC35731
0.8889 High Similarity NPC276753
0.8889 High Similarity NPC125755
0.8889 High Similarity NPC205796
0.8881 High Similarity NPC84181
0.8873 High Similarity NPC5262
0.8873 High Similarity NPC475084
0.8873 High Similarity NPC472714
0.8873 High Similarity NPC302506
0.8857 High Similarity NPC65530
0.8857 High Similarity NPC59324
0.8849 High Similarity NPC79957
0.8849 High Similarity NPC101624
0.8849 High Similarity NPC184938
0.8841 High Similarity NPC69513
0.8841 High Similarity NPC215833
0.8841 High Similarity NPC49074
0.8836 High Similarity NPC51328
0.8836 High Similarity NPC55158
0.8836 High Similarity NPC286235
0.8828 High Similarity NPC227902
0.8824 High Similarity NPC86030
0.8824 High Similarity NPC307110
0.8824 High Similarity NPC5851
0.8819 High Similarity NPC161700
0.8819 High Similarity NPC277867
0.8811 High Similarity NPC478239
0.8803 High Similarity NPC471908
0.8786 High Similarity NPC203230
0.8786 High Similarity NPC242028
0.8786 High Similarity NPC25695
0.8786 High Similarity NPC172818
0.8786 High Similarity NPC164857
0.8777 High Similarity NPC470881
0.8776 High Similarity NPC98624
0.8776 High Similarity NPC475224
0.8768 High Similarity NPC162093
0.8768 High Similarity NPC299144
0.8767 High Similarity NPC130449
0.8767 High Similarity NPC270751
0.8767 High Similarity NPC248132
0.875 High Similarity NPC164183
0.875 High Similarity NPC179521
0.875 High Similarity NPC472712
0.875 High Similarity NPC472713
0.875 High Similarity NPC76176
0.875 High Similarity NPC469313
0.875 High Similarity NPC118385
0.875 High Similarity NPC138227
0.875 High Similarity NPC474178
0.875 High Similarity NPC187774
0.875 High Similarity NPC72529
0.875 High Similarity NPC473046
0.875 High Similarity NPC245826
0.875 High Similarity NPC252307
0.875 High Similarity NPC168579
0.8741 High Similarity NPC253878
0.8741 High Similarity NPC140502
0.8741 High Similarity NPC157816
0.8731 High Similarity NPC109822
0.8731 High Similarity NPC94276
0.8725 High Similarity NPC78809
0.8714 High Similarity NPC470236
0.8705 High Similarity NPC294166
0.8705 High Similarity NPC115022
0.8705 High Similarity NPC6836
0.8699 High Similarity NPC15538
0.8699 High Similarity NPC473480
0.8696 High Similarity NPC475067
0.8681 High Similarity NPC252169
0.8681 High Similarity NPC37793
0.8676 High Similarity NPC147821
0.8676 High Similarity NPC118787
0.8676 High Similarity NPC183181
0.8676 High Similarity NPC319625
0.8676 High Similarity NPC106511
0.8676 High Similarity NPC41706
0.8676 High Similarity NPC163332
0.8676 High Similarity NPC111247
0.8676 High Similarity NPC292056
0.8671 High Similarity NPC471414
0.8671 High Similarity NPC186406
0.8671 High Similarity NPC210192
0.8662 High Similarity NPC22517
0.8652 High Similarity NPC37468
0.8649 High Similarity NPC183380
0.8649 High Similarity NPC225815
0.8649 High Similarity NPC260781
0.8649 High Similarity NPC472709
0.8649 High Similarity NPC472710
0.8649 High Similarity NPC214326
0.8649 High Similarity NPC469707
0.8649 High Similarity NPC158635
0.8649 High Similarity NPC182368
0.8649 High Similarity NPC229882
0.8649 High Similarity NPC218041
0.8649 High Similarity NPC469706
0.8649 High Similarity NPC145979
0.8649 High Similarity NPC9933
0.8649 High Similarity NPC185955
0.8643 High Similarity NPC87696
0.8643 High Similarity NPC107478
0.8643 High Similarity NPC170694
0.8643 High Similarity NPC478085
0.8639 High Similarity NPC116229
0.8633 High Similarity NPC219671
0.8633 High Similarity NPC85799
0.8633 High Similarity NPC104077
0.8633 High Similarity NPC252833
0.8633 High Similarity NPC26080
0.8633 High Similarity NPC254275
0.8633 High Similarity NPC303422
0.8633 High Similarity NPC471505
0.8633 High Similarity NPC147616
0.8633 High Similarity NPC165686
0.8633 High Similarity NPC259742
0.8633 High Similarity NPC106739
0.863 High Similarity NPC199928
0.863 High Similarity NPC93610
0.863 High Similarity NPC241846
0.8621 High Similarity NPC232228
0.8613 High Similarity NPC470084

  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 NPC60249 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
0.8542 High Similarity NPD6674 Discontinued
0.8286 Intermediate Similarity NPD3027 Phase 3
0.8239 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.8239 Intermediate Similarity NPD1613 Approved
0.8235 Intermediate Similarity NPD3705 Approved
0.8151 Intermediate Similarity NPD7266 Discontinued
0.8102 Intermediate Similarity NPD1091 Approved
0.8 Intermediate Similarity NPD37 Approved
0.7974 Intermediate Similarity NPD1653 Approved
0.7962 Intermediate Similarity NPD4966 Approved
0.7962 Intermediate Similarity NPD4967 Phase 2
0.7962 Intermediate Similarity NPD4965 Approved
0.7958 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7919 Intermediate Similarity NPD5698 Clinical (unspecified phase)
0.7887 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7875 Intermediate Similarity NPD7199 Phase 2
0.7862 Intermediate Similarity NPD6234 Discontinued
0.7853 Intermediate Similarity NPD7228 Approved
0.7763 Intermediate Similarity NPD5058 Phase 3
0.7762 Intermediate Similarity NPD2861 Phase 2
0.7758 Intermediate Similarity NPD7074 Phase 3
0.7754 Intermediate Similarity NPD1357 Approved
0.7722 Intermediate Similarity NPD8455 Phase 2
0.7704 Intermediate Similarity NPD5283 Phase 1
0.7697 Intermediate Similarity NPD7054 Approved
0.7669 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7651 Intermediate Similarity NPD4108 Discontinued
0.7651 Intermediate Similarity NPD7472 Approved
0.7636 Intermediate Similarity NPD3818 Discontinued
0.7619 Intermediate Similarity NPD3619 Clinical (unspecified phase)
0.7619 Intermediate Similarity NPD3620 Phase 2
0.7619 Intermediate Similarity NPD4060 Phase 1
0.7597 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7591 Intermediate Similarity NPD7157 Approved
0.7586 Intermediate Similarity NPD4908 Phase 1
0.7584 Intermediate Similarity NPD4538 Approved
0.7584 Intermediate Similarity NPD4537 Clinical (unspecified phase)
0.7584 Intermediate Similarity NPD4536 Approved
0.7571 Intermediate Similarity NPD5125 Phase 3
0.7571 Intermediate Similarity NPD5126 Approved
0.756 Intermediate Similarity NPD7240 Approved
0.7534 Intermediate Similarity NPD4625 Phase 3
0.7515 Intermediate Similarity NPD7808 Phase 3
0.75 Intermediate Similarity NPD7843 Approved
0.75 Intermediate Similarity NPD6797 Phase 2
0.7485 Intermediate Similarity NPD5844 Phase 1
0.7483 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7469 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.7465 Intermediate Similarity NPD1610 Phase 2
0.7463 Intermediate Similarity NPD2684 Approved
0.7456 Intermediate Similarity NPD7251 Discontinued
0.745 Intermediate Similarity NPD5735 Approved
0.7438 Intermediate Similarity NPD1934 Approved
0.7434 Intermediate Similarity NPD1375 Discontinued
0.7426 Intermediate Similarity NPD228 Approved
0.7417 Intermediate Similarity NPD5960 Phase 3
0.7417 Intermediate Similarity NPD5588 Approved
0.7412 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.7399 Intermediate Similarity NPD6843 Phase 3
0.7399 Intermediate Similarity NPD6842 Approved
0.7399 Intermediate Similarity NPD6841 Approved
0.7394 Intermediate Similarity NPD3787 Discontinued
0.7384 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7361 Intermediate Similarity NPD2982 Phase 2
0.7361 Intermediate Similarity NPD2983 Phase 2
0.7355 Intermediate Similarity NPD2677 Approved
0.7353 Intermediate Similarity NPD7685 Pre-registration
0.7353 Intermediate Similarity NPD6559 Discontinued
0.732 Intermediate Similarity NPD5762 Approved
0.732 Intermediate Similarity NPD5763 Approved
0.732 Intermediate Similarity NPD2029 Clinical (unspecified phase)
0.731 Intermediate Similarity NPD8651 Approved
0.7305 Intermediate Similarity NPD6166 Phase 2
0.7305 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.7305 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.7301 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7297 Intermediate Similarity NPD7095 Approved
0.7292 Intermediate Similarity NPD2981 Phase 2
0.729 Intermediate Similarity NPD4628 Phase 3
0.7284 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7284 Intermediate Similarity NPD2977 Approved
0.7284 Intermediate Similarity NPD2978 Approved
0.7279 Intermediate Similarity NPD3018 Phase 2
0.7278 Intermediate Similarity NPD5261 Clinical (unspecified phase)
0.7267 Intermediate Similarity NPD4140 Approved
0.7267 Intermediate Similarity NPD1558 Phase 1
0.7241 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.7239 Intermediate Similarity NPD2560 Approved
0.7239 Intermediate Similarity NPD2563 Approved
0.7237 Intermediate Similarity NPD7097 Phase 1
0.7219 Intermediate Similarity NPD3751 Discontinued
0.7203 Intermediate Similarity NPD6516 Phase 2
0.7203 Intermediate Similarity NPD5846 Approved
0.72 Intermediate Similarity NPD6233 Phase 2
0.7186 Intermediate Similarity NPD6071 Discontinued
0.7183 Intermediate Similarity NPD1548 Phase 1
0.7179 Intermediate Similarity NPD6331 Phase 2
0.7179 Intermediate Similarity NPD4110 Phase 3
0.7179 Intermediate Similarity NPD6658 Clinical (unspecified phase)
0.7179 Intermediate Similarity NPD4109 Clinical (unspecified phase)
0.7178 Intermediate Similarity NPD1465 Phase 2
0.7176 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.7168 Intermediate Similarity NPD8313 Approved
0.7168 Intermediate Similarity NPD8312 Approved
0.7153 Intermediate Similarity NPD3022 Approved
0.7153 Intermediate Similarity NPD3021 Approved
0.7152 Intermediate Similarity NPD7975 Clinical (unspecified phase)
0.7152 Intermediate Similarity NPD5837 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD4005 Discontinued
0.7143 Intermediate Similarity NPD2969 Approved
0.7143 Intermediate Similarity NPD2970 Approved
0.7134 Intermediate Similarity NPD5241 Discontinued
0.7134 Intermediate Similarity NPD3817 Phase 2
0.7133 Intermediate Similarity NPD5111 Phase 2
0.7133 Intermediate Similarity NPD6798 Discontinued
0.7133 Intermediate Similarity NPD5110 Phase 2
0.7133 Intermediate Similarity NPD6410 Clinical (unspecified phase)
0.7133 Intermediate Similarity NPD5109 Approved
0.7132 Intermediate Similarity NPD290 Approved
0.7126 Intermediate Similarity NPD8127 Discontinued
0.7125 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7123 Intermediate Similarity NPD4749 Approved
0.7123 Intermediate Similarity NPD3600 Clinical (unspecified phase)
0.7123 Intermediate Similarity NPD5327 Phase 3
0.7123 Intermediate Similarity NPD3685 Discontinued
0.7115 Intermediate Similarity NPD5177 Phase 3
0.7115 Intermediate Similarity NPD4236 Phase 3
0.7115 Intermediate Similarity NPD4237 Approved
0.7115 Intermediate Similarity NPD4162 Approved
0.7115 Intermediate Similarity NPD3060 Approved
0.7107 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7107 Intermediate Similarity NPD4123 Phase 3
0.7105 Intermediate Similarity NPD6355 Discontinued
0.7095 Intermediate Similarity NPD6584 Phase 3
0.7093 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7092 Intermediate Similarity NPD6671 Approved
0.7083 Intermediate Similarity NPD6232 Discontinued
0.7083 Intermediate Similarity NPD3051 Approved
0.7081 Intermediate Similarity NPD3686 Approved
0.7081 Intermediate Similarity NPD3687 Approved
0.7078 Intermediate Similarity NPD6028 Clinical (unspecified phase)
0.7078 Intermediate Similarity NPD6029 Clinical (unspecified phase)
0.7073 Intermediate Similarity NPD2801 Approved
0.707 Intermediate Similarity NPD4535 Phase 3
0.7063 Intermediate Similarity NPD1940 Clinical (unspecified phase)
0.7062 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7059 Intermediate Similarity NPD6653 Approved
0.7039 Intermediate Similarity NPD2238 Phase 2
0.7033 Intermediate Similarity NPD7237 Clinical (unspecified phase)
0.7032 Intermediate Similarity NPD2438 Suspended
0.703 Intermediate Similarity NPD6374 Clinical (unspecified phase)
0.7027 Intermediate Similarity NPD3094 Phase 2
0.7025 Intermediate Similarity NPD5307 Clinical (unspecified phase)
0.7025 Intermediate Similarity NPD6190 Approved
0.7015 Intermediate Similarity NPD291 Approved
0.7012 Intermediate Similarity NPD7945 Clinical (unspecified phase)
0.7006 Intermediate Similarity NPD1652 Phase 2
0.7 Intermediate Similarity NPD5535 Approved
0.7 Intermediate Similarity NPD2489 Approved
0.7 Intermediate Similarity NPD5752 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD27 Approved
0.6994 Remote Similarity NPD7007 Discovery
0.6994 Remote Similarity NPD4675 Approved
0.6994 Remote Similarity NPD4678 Approved
0.6993 Remote Similarity NPD4340 Discontinued
0.6993 Remote Similarity NPD5536 Phase 2
0.6993 Remote Similarity NPD3657 Discovery
0.6981 Remote Similarity NPD6783 Clinical (unspecified phase)
0.6974 Remote Similarity NPD1726 Clinical (unspecified phase)
0.6973 Remote Similarity NPD7680 Approved
0.6972 Remote Similarity NPD709 Approved
0.697 Remote Similarity NPD6818 Clinical (unspecified phase)
0.697 Remote Similarity NPD7819 Suspended
0.697 Remote Similarity NPD5772 Approved
0.697 Remote Similarity NPD5773 Approved
0.6968 Remote Similarity NPD2156 Approved
0.6968 Remote Similarity NPD2154 Approved
0.6968 Remote Similarity NPD2155 Approved
0.6968 Remote Similarity NPD7033 Discontinued
0.6959 Remote Similarity NPD7473 Discontinued
0.6957 Remote Similarity NPD52 Approved
0.6957 Remote Similarity NPD7526 Approved
0.6957 Remote Similarity NPD7527 Clinical (unspecified phase)
0.6948 Remote Similarity NPD6353 Approved
0.6939 Remote Similarity NPD2231 Phase 2
0.6939 Remote Similarity NPD1608 Approved
0.6939 Remote Similarity NPD2235 Phase 2
0.6937 Remote Similarity NPD1774 Approved
0.6934 Remote Similarity NPD968 Approved
0.6933 Remote Similarity NPD6055 Clinical (unspecified phase)
0.6932 Remote Similarity NPD7090 Clinical (unspecified phase)
0.6923 Remote Similarity NPD2161 Phase 2
0.6918 Remote Similarity NPD3496 Discontinued
0.6918 Remote Similarity NPD5084 Clinical (unspecified phase)
0.691 Remote Similarity NPD7906 Approved
0.6908 Remote Similarity NPD6859 Clinical (unspecified phase)
0.6906 Remote Similarity NPD556 Approved
0.6894 Remote Similarity NPD4160 Clinical (unspecified phase)
0.6892 Remote Similarity NPD6583 Phase 3
0.6892 Remote Similarity NPD6582 Phase 2

  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