Structure

Physi-Chem Properties

Molecular Weight:  768.28
Volume:  719.642
LogP:  0.468
LogD:  -0.052
LogS:  -3.151
# Rotatable Bonds:  11
TPSA:  271.34
# H-Bond Aceptor:  18
# H-Bond Donor:  6
# Rings:  6
# Heavy Atoms:  18

MedChem Properties

QED Drug-Likeness Score:  0.088
Synthetic Accessibility Score:  7.221
Fsp3:  0.75
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.498
MDCK Permeability:  0.00038805234362371266
Pgp-inhibitor:  0.999
Pgp-substrate:  0.998
Human Intestinal Absorption (HIA):  0.944
20% Bioavailability (F20%):  0.646
30% Bioavailability (F30%):  0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.086
Plasma Protein Binding (PPB):  43.09801483154297%
Volume Distribution (VD):  0.51
Pgp-substrate:  30.030874252319336%

ADMET: Metabolism

CYP1A2-inhibitor:  0.003
CYP1A2-substrate:  0.192
CYP2C19-inhibitor:  0.005
CYP2C19-substrate:  0.401
CYP2C9-inhibitor:  0.002
CYP2C9-substrate:  0.009
CYP2D6-inhibitor:  0.006
CYP2D6-substrate:  0.056
CYP3A4-inhibitor:  0.161
CYP3A4-substrate:  0.132

ADMET: Excretion

Clearance (CL):  1.386
Half-life (T1/2):  0.592

ADMET: Toxicity

hERG Blockers:  0.293
Human Hepatotoxicity (H-HT):  0.829
Drug-inuced Liver Injury (DILI):  0.924
AMES Toxicity:  0.05
Rat Oral Acute Toxicity:  0.361
Maximum Recommended Daily Dose:  0.675
Skin Sensitization:  0.122
Carcinogencity:  0.044
Eye Corrosion:  0.003
Eye Irritation:  0.008
Respiratory Toxicity:  0.349

Download Data

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

  Natural Product: NPC471089

Natural Product ID:  NPC471089
Common Name*:   Yadanzioside G
IUPAC Name:   n.a.
Synonyms:   Yadanzioside G
Standard InCHIKey:  YNYBTCKMNHXXGZ-FIHJRPEFSA-N
Standard InCHI:  InChI=1S/C36H48O18/c1-13(33(4,5)54-15(3)38)8-20(39)53-26-28-35-12-49-36(28,32(47)48-7)29(45)25(44)27(35)34(6)10-17(21(40)14(2)16(34)9-19(35)52-30(26)46)50-31-24(43)23(42)22(41)18(11-37)51-31/h8,10,14,16,18-19,22-29,31,37,41-45H,9,11-12H2,1-7H3/b13-8+/t14-,16-,18+,19+,22+,23-,24+,25+,26+,27+,28+,29-,31+,34-,35+,36+/m0/s1
SMILES:  OC[C@H]1O[C@@H](OC2=C[C@@]3(C)[C@H]([C@@H](C2=O)C)C[C@@H]2[C@@]45[C@@H]3[C@@H](O)[C@H](O)[C@@]([C@@H]5[C@H](C(=O)O2)OC(=O)/C=C(/C(OC(=O)C)(C)C)C)(OC4)C(=O)OC)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL2368538
PubChem CID:   73354401
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001283] Terpene lactones
          • [CHEMONTID:0002119] Quassinoids

*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
NPO14948 Brucea javanica Species Simaroubaceae Eukaryota n.a. seed n.a. DOI[10.1016/0031-9422(96)00258-0]
NPO14948 Brucea javanica Species Simaroubaceae Eukaryota n.a. fruit n.a. DOI[10.1016/S1383-5769(99)00023-9]
NPO14948 Brucea javanica Species Simaroubaceae Eukaryota n.a. n.a. n.a. PMID[10086989]
NPO14948 Brucea javanica Species Simaroubaceae Eukaryota n.a. n.a. n.a. PMID[1512598]
NPO14948 Brucea javanica Species Simaroubaceae Eukaryota Seeds n.a. n.a. PMID[15165151]
NPO14948 Brucea javanica Species Simaroubaceae Eukaryota fruit Indonesia n.a. PMID[17896817]
NPO14948 Brucea javanica Species Simaroubaceae Eukaryota n.a. Vietnam n.a. PMID[19026551]
NPO14948 Brucea javanica Species Simaroubaceae Eukaryota seeds n.a. n.a. PMID[20050684]
NPO21014 Brucea antidysenterica Species Simaroubaceae Eukaryota n.a. n.a. n.a. PMID[2089121]
NPO14948 Brucea javanica Species Simaroubaceae Eukaryota Seeds n.a. n.a. PMID[22506620]
NPO21014 Brucea antidysenterica Species Simaroubaceae Eukaryota n.a. n.a. n.a. PMID[3379416]
NPO21014 Brucea antidysenterica Species Simaroubaceae Eukaryota n.a. n.a. n.a. PMID[3443857]
NPO21014 Brucea antidysenterica Species Simaroubaceae Eukaryota n.a. n.a. n.a. PMID[3760882]
NPO21014 Brucea antidysenterica Species Simaroubaceae Eukaryota n.a. n.a. n.a. PMID[3841557]
NPO14948 Brucea javanica Species Simaroubaceae Eukaryota n.a. n.a. n.a. PMID[6481366]
NPO21014 Brucea antidysenterica Species Simaroubaceae Eukaryota n.a. n.a. n.a. PMID[7288443]
NPO14948 Brucea javanica Species Simaroubaceae Eukaryota n.a. n.a. n.a. PMID[7561896]
NPO21014 Brucea antidysenterica Species Simaroubaceae Eukaryota n.a. n.a. n.a. PMID[8133299]
NPO21014 Brucea antidysenterica Species Simaroubaceae Eukaryota n.a. xylem n.a. PMID[8133299]
NPO21014 Brucea antidysenterica Species Simaroubaceae Eukaryota n.a. n.a. n.a. PMID[8691212]
NPO21014 Brucea antidysenterica Species Simaroubaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO14948 Brucea javanica Species Simaroubaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO21014 Brucea antidysenterica Species Simaroubaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14948 Brucea javanica Species Simaroubaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14948 Brucea javanica Species Simaroubaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO14948 Brucea javanica Species Simaroubaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO21014 Brucea antidysenterica Species Simaroubaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14948 Brucea javanica Species Simaroubaceae 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
NPT759 Cell Line H9 Homo sapiens IC50 = 37000.0 nM PMID[483186]
NPT168 Cell Line P388 Mus musculus ED50 = 1.25 ug ml-1 PMID[483187]
NPT137 Cell Line L1210 Mus musculus ED50 = 2.58 ug ml-1 PMID[483187]
NPT24 Organism Human immunodeficiency virus 1 Human immunodeficiency virus 1 EC50 = 23000.0 nM PMID[483186]
NPT27 Others Unspecified Therapeutic index = 1.6 n.a. PMID[483186]
NPT786 Organism Tobacco mosaic virus Tobacco mosaic virus Inhibition = 33.7 % PMID[483188]

☑ 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 NPC471089 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 NPC190065
1.0 High Similarity NPC141215
0.992 High Similarity NPC295885
0.992 High Similarity NPC140045
0.992 High Similarity NPC596
0.9919 High Similarity NPC262813
0.984 High Similarity NPC251998
0.9516 High Similarity NPC309096
0.9516 High Similarity NPC54614
0.9435 High Similarity NPC475636
0.9435 High Similarity NPC295220
0.9365 High Similarity NPC478154
0.9291 High Similarity NPC478151
0.9286 High Similarity NPC478155
0.9286 High Similarity NPC25998
0.9274 High Similarity NPC87662
0.9213 High Similarity NPC478153
0.9213 High Similarity NPC478152
0.9213 High Similarity NPC478150
0.9206 High Similarity NPC477196
0.9134 High Similarity NPC477197
0.9134 High Similarity NPC329993
0.9134 High Similarity NPC45346
0.9134 High Similarity NPC301639
0.9134 High Similarity NPC478065
0.9134 High Similarity NPC478064
0.9134 High Similarity NPC475377
0.9134 High Similarity NPC262796
0.9134 High Similarity NPC264566
0.9134 High Similarity NPC172374
0.9134 High Similarity NPC173435
0.9134 High Similarity NPC475167
0.9134 High Similarity NPC476074
0.9134 High Similarity NPC134914
0.9127 High Similarity NPC477191
0.9127 High Similarity NPC477194
0.9127 High Similarity NPC477193
0.9127 High Similarity NPC477192
0.9113 High Similarity NPC91693
0.9113 High Similarity NPC18945
0.9113 High Similarity NPC227397
0.9113 High Similarity NPC105926
0.9113 High Similarity NPC265557
0.9062 High Similarity NPC476776
0.9062 High Similarity NPC477195
0.9055 High Similarity NPC252657
0.9055 High Similarity NPC107536
0.9055 High Similarity NPC244296
0.9055 High Similarity NPC273878
0.9055 High Similarity NPC141600
0.9055 High Similarity NPC11577
0.9055 High Similarity NPC477077
0.9055 High Similarity NPC88311
0.9055 High Similarity NPC269484
0.9055 High Similarity NPC472267
0.9055 High Similarity NPC9470
0.9055 High Similarity NPC470913
0.9055 High Similarity NPC252289
0.9055 High Similarity NPC280029
0.9055 High Similarity NPC115656
0.9055 High Similarity NPC470518
0.9055 High Similarity NPC477076
0.9055 High Similarity NPC305793
0.9055 High Similarity NPC477079
0.9055 High Similarity NPC82380
0.9055 High Similarity NPC97918
0.9055 High Similarity NPC1314
0.9048 High Similarity NPC470780
0.904 High Similarity NPC24651
0.904 High Similarity NPC476729
0.9032 High Similarity NPC312833
0.8984 High Similarity NPC271610
0.8984 High Similarity NPC476775
0.8984 High Similarity NPC476780
0.8984 High Similarity NPC476774
0.8976 High Similarity NPC477075
0.8976 High Similarity NPC477078
0.8976 High Similarity NPC475281
0.8976 High Similarity NPC329923
0.8968 High Similarity NPC285091
0.8952 High Similarity NPC275675
0.8923 High Similarity NPC476777
0.8923 High Similarity NPC476778
0.8915 High Similarity NPC46823
0.8915 High Similarity NPC71391
0.8915 High Similarity NPC312650
0.8915 High Similarity NPC30279
0.8915 High Similarity NPC192765
0.8915 High Similarity NPC178264
0.8915 High Similarity NPC473918
0.8915 High Similarity NPC277212
0.8906 High Similarity NPC265841
0.8906 High Similarity NPC47995
0.8906 High Similarity NPC470912
0.8889 High Similarity NPC470922
0.8855 High Similarity NPC279915
0.8855 High Similarity NPC110700
0.8846 High Similarity NPC225791
0.8846 High Similarity NPC476779
0.8828 High Similarity NPC470475
0.8828 High Similarity NPC470476
0.881 High Similarity NPC202666
0.881 High Similarity NPC262199
0.881 High Similarity NPC14617
0.881 High Similarity NPC471964
0.881 High Similarity NPC471961
0.881 High Similarity NPC67251
0.88 High Similarity NPC470779
0.879 High Similarity NPC127530
0.879 High Similarity NPC473920
0.879 High Similarity NPC279143
0.875 High Similarity NPC476008
0.875 High Similarity NPC470516
0.874 High Similarity NPC247315
0.874 High Similarity NPC30188
0.874 High Similarity NPC471962
0.874 High Similarity NPC471963
0.874 High Similarity NPC177820
0.873 High Similarity NPC40775
0.873 High Similarity NPC471965
0.873 High Similarity NPC235438
0.873 High Similarity NPC249848
0.873 High Similarity NPC107966
0.872 High Similarity NPC107338
0.872 High Similarity NPC109607
0.8692 High Similarity NPC43589
0.8692 High Similarity NPC300655
0.8692 High Similarity NPC311178
0.8692 High Similarity NPC222951
0.8672 High Similarity NPC477745
0.8661 High Similarity NPC30735
0.8661 High Similarity NPC281148
0.8661 High Similarity NPC478066
0.8661 High Similarity NPC235405
0.8657 High Similarity NPC79250
0.8657 High Similarity NPC290746
0.864 High Similarity NPC476529
0.864 High Similarity NPC475775
0.864 High Similarity NPC470777
0.8626 High Similarity NPC183816
0.8626 High Similarity NPC475444
0.8626 High Similarity NPC471855
0.8626 High Similarity NPC322904
0.8626 High Similarity NPC475177
0.8626 High Similarity NPC196874
0.8626 High Similarity NPC319719
0.8626 High Similarity NPC473679
0.8626 High Similarity NPC233223
0.8626 High Similarity NPC324933
0.8615 High Similarity NPC476966
0.8594 High Similarity NPC469842
0.8594 High Similarity NPC469841
0.8594 High Similarity NPC470477
0.8594 High Similarity NPC7850
0.8594 High Similarity NPC6615
0.8583 High Similarity NPC213952
0.8583 High Similarity NPC162574
0.8571 High Similarity NPC476127
0.8571 High Similarity NPC476150
0.8561 High Similarity NPC168879
0.856 High Similarity NPC17772
0.856 High Similarity NPC297179
0.855 High Similarity NPC476852
0.8548 High Similarity NPC173686
0.8548 High Similarity NPC16081
0.8538 High Similarity NPC45606
0.8538 High Similarity NPC220838
0.8538 High Similarity NPC476859
0.8527 High Similarity NPC181066
0.8527 High Similarity NPC470218
0.8527 High Similarity NPC469947
0.8519 High Similarity NPC477232
0.8519 High Similarity NPC477233
0.8516 High Similarity NPC257211
0.8504 High Similarity NPC222580
0.8504 High Similarity NPC86222
0.8504 High Similarity NPC297263
0.8504 High Similarity NPC223301
0.8504 High Similarity NPC476204
0.8504 High Similarity NPC114484
0.8504 High Similarity NPC301449
0.8504 High Similarity NPC104372
0.8504 High Similarity NPC22956
0.8504 High Similarity NPC64715
0.8504 High Similarity NPC62725
0.8504 High Similarity NPC159309
0.8504 High Similarity NPC170084
0.8504 High Similarity NPC75417
0.8504 High Similarity NPC11242
0.8504 High Similarity NPC171544
0.8504 High Similarity NPC31838
0.8492 Intermediate Similarity NPC122971
0.8492 Intermediate Similarity NPC35405
0.8492 Intermediate Similarity NPC309780
0.8492 Intermediate Similarity NPC472949
0.8492 Intermediate Similarity NPC114441
0.8492 Intermediate Similarity NPC180550
0.8492 Intermediate Similarity NPC157868
0.8492 Intermediate Similarity NPC39211
0.8492 Intermediate Similarity NPC6377

  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 NPC471089 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
0.881 High Similarity NPD8328 Phase 3
0.8189 Intermediate Similarity NPD8295 Clinical (unspecified phase)
0.812 Intermediate Similarity NPD7736 Approved
0.806 Intermediate Similarity NPD7319 Approved
0.7939 Intermediate Similarity NPD8516 Approved
0.7939 Intermediate Similarity NPD8517 Approved
0.7939 Intermediate Similarity NPD8515 Approved
0.7939 Intermediate Similarity NPD8513 Phase 3
0.791 Intermediate Similarity NPD8293 Discontinued
0.7879 Intermediate Similarity NPD6370 Approved
0.784 Intermediate Similarity NPD6686 Approved
0.7836 Intermediate Similarity NPD7507 Approved
0.7778 Intermediate Similarity NPD8132 Clinical (unspecified phase)
0.7761 Intermediate Similarity NPD7492 Approved
0.7727 Intermediate Similarity NPD6054 Approved
0.7704 Intermediate Similarity NPD6616 Approved
0.7698 Intermediate Similarity NPD5345 Clinical (unspecified phase)
0.7674 Intermediate Similarity NPD8133 Approved
0.7669 Intermediate Similarity NPD8335 Approved
0.7669 Intermediate Similarity NPD8380 Approved
0.7669 Intermediate Similarity NPD7503 Approved
0.7669 Intermediate Similarity NPD8379 Approved
0.7669 Intermediate Similarity NPD8378 Approved
0.7669 Intermediate Similarity NPD8296 Approved
0.7647 Intermediate Similarity NPD7078 Approved
0.7594 Intermediate Similarity NPD6319 Approved
0.7594 Intermediate Similarity NPD8377 Approved
0.7594 Intermediate Similarity NPD8294 Approved
0.7594 Intermediate Similarity NPD6059 Approved
0.7537 Intermediate Similarity NPD6015 Approved
0.7537 Intermediate Similarity NPD8033 Approved
0.7537 Intermediate Similarity NPD6016 Approved
0.7519 Intermediate Similarity NPD7516 Approved
0.7481 Intermediate Similarity NPD5988 Approved
0.7462 Intermediate Similarity NPD8297 Approved
0.7462 Intermediate Similarity NPD6882 Approved
0.7444 Intermediate Similarity NPD7328 Approved
0.7444 Intermediate Similarity NPD7327 Approved
0.7368 Intermediate Similarity NPD6009 Approved
0.7368 Intermediate Similarity NPD7115 Discovery
0.7344 Intermediate Similarity NPD6412 Phase 2
0.7252 Intermediate Similarity NPD6650 Approved
0.7252 Intermediate Similarity NPD8413 Clinical (unspecified phase)
0.7252 Intermediate Similarity NPD6649 Approved
0.7231 Intermediate Similarity NPD6373 Approved
0.7231 Intermediate Similarity NPD4061 Clinical (unspecified phase)
0.7231 Intermediate Similarity NPD6372 Approved
0.7176 Intermediate Similarity NPD5955 Clinical (unspecified phase)
0.7154 Intermediate Similarity NPD6881 Approved
0.7154 Intermediate Similarity NPD6899 Approved
0.7153 Intermediate Similarity NPD6921 Approved
0.7143 Intermediate Similarity NPD8074 Phase 3
0.7143 Intermediate Similarity NPD4632 Approved
0.7132 Intermediate Similarity NPD6402 Approved
0.7132 Intermediate Similarity NPD5739 Approved
0.7132 Intermediate Similarity NPD7128 Approved
0.7132 Intermediate Similarity NPD6675 Approved
0.7121 Intermediate Similarity NPD8130 Phase 1
0.7092 Intermediate Similarity NPD6033 Approved
0.7077 Intermediate Similarity NPD5697 Approved
0.7063 Intermediate Similarity NPD4225 Approved
0.7045 Intermediate Similarity NPD6883 Approved
0.7045 Intermediate Similarity NPD7290 Approved
0.7045 Intermediate Similarity NPD7102 Approved
0.7023 Intermediate Similarity NPD7320 Approved
0.6992 Remote Similarity NPD6847 Approved
0.6992 Remote Similarity NPD6617 Approved
0.6992 Remote Similarity NPD6869 Approved
0.697 Remote Similarity NPD6012 Approved
0.697 Remote Similarity NPD6014 Approved
0.697 Remote Similarity NPD6013 Approved
0.6947 Remote Similarity NPD5954 Clinical (unspecified phase)
0.6947 Remote Similarity NPD5701 Approved
0.6939 Remote Similarity NPD7966 Clinical (unspecified phase)
0.6929 Remote Similarity NPD7604 Phase 2
0.6917 Remote Similarity NPD4634 Approved
0.6906 Remote Similarity NPD5983 Phase 2
0.6894 Remote Similarity NPD6011 Approved
0.685 Remote Similarity NPD7902 Approved
0.6831 Remote Similarity NPD6336 Discontinued
0.6828 Remote Similarity NPD7260 Phase 2
0.6818 Remote Similarity NPD7899 Clinical (unspecified phase)
0.6797 Remote Similarity NPD7638 Approved
0.6746 Remote Similarity NPD7748 Approved
0.6744 Remote Similarity NPD7639 Approved
0.6744 Remote Similarity NPD7640 Approved
0.6741 Remote Similarity NPD6401 Clinical (unspecified phase)
0.6738 Remote Similarity NPD8080 Discontinued
0.6726 Remote Similarity NPD7799 Discontinued
0.6667 Remote Similarity NPD6845 Suspended
0.6667 Remote Similarity NPD8170 Clinical (unspecified phase)
0.6667 Remote Similarity NPD6274 Approved
0.6647 Remote Similarity NPD8407 Phase 2
0.6643 Remote Similarity NPD7101 Approved
0.6643 Remote Similarity NPD7100 Approved
0.6641 Remote Similarity NPD5211 Phase 2
0.6617 Remote Similarity NPD6008 Approved
0.6615 Remote Similarity NPD5286 Approved
0.6615 Remote Similarity NPD4696 Approved
0.6615 Remote Similarity NPD5285 Approved
0.6614 Remote Similarity NPD7900 Approved
0.6614 Remote Similarity NPD7901 Clinical (unspecified phase)
0.6589 Remote Similarity NPD6083 Phase 2
0.6589 Remote Similarity NPD6084 Phase 2
0.6589 Remote Similarity NPD4755 Approved
0.6587 Remote Similarity NPD7515 Phase 2
0.6573 Remote Similarity NPD6067 Discontinued
0.6571 Remote Similarity NPD6335 Approved
0.657 Remote Similarity NPD8368 Discontinued
0.6569 Remote Similarity NPD6053 Discontinued
0.6549 Remote Similarity NPD8274 Clinical (unspecified phase)
0.6544 Remote Similarity NPD6371 Approved
0.6541 Remote Similarity NPD5141 Approved
0.6538 Remote Similarity NPD8029 Clinical (unspecified phase)
0.6538 Remote Similarity NPD5696 Approved
0.6533 Remote Similarity NPD8387 Clinical (unspecified phase)
0.6531 Remote Similarity NPD5956 Approved
0.6515 Remote Similarity NPD5224 Approved
0.6515 Remote Similarity NPD5225 Approved
0.6515 Remote Similarity NPD5226 Approved
0.6515 Remote Similarity NPD4633 Approved
0.65 Remote Similarity NPD6317 Approved
0.6489 Remote Similarity NPD4700 Approved
0.6484 Remote Similarity NPD5282 Discontinued
0.6477 Remote Similarity NPD8434 Phase 2
0.6467 Remote Similarity NPD8415 Approved
0.6466 Remote Similarity NPD5175 Approved
0.6466 Remote Similarity NPD5174 Approved
0.6458 Remote Similarity NPD7829 Approved
0.6458 Remote Similarity NPD7830 Approved
0.6454 Remote Similarity NPD6314 Approved
0.6454 Remote Similarity NPD6313 Approved
0.6443 Remote Similarity NPD8338 Approved
0.6439 Remote Similarity NPD5223 Approved
0.6439 Remote Similarity NPD5344 Discontinued
0.6438 Remote Similarity NPD8448 Approved
0.6434 Remote Similarity NPD6908 Approved
0.6434 Remote Similarity NPD6909 Approved
0.6434 Remote Similarity NPD6291 Clinical (unspecified phase)
0.6429 Remote Similarity NPD6868 Approved
0.64 Remote Similarity NPD3573 Approved
0.6397 Remote Similarity NPD4730 Approved
0.6397 Remote Similarity NPD4729 Approved
0.6395 Remote Similarity NPD8337 Approved
0.6395 Remote Similarity NPD8336 Approved
0.6385 Remote Similarity NPD5221 Approved
0.6385 Remote Similarity NPD5220 Clinical (unspecified phase)
0.6385 Remote Similarity NPD5222 Approved
0.6385 Remote Similarity NPD4697 Phase 3
0.6378 Remote Similarity NPD46 Approved
0.6378 Remote Similarity NPD6698 Approved
0.637 Remote Similarity NPD8451 Approved
0.637 Remote Similarity NPD4767 Approved
0.637 Remote Similarity NPD4768 Approved
0.6345 Remote Similarity NPD7642 Approved
0.6336 Remote Similarity NPD5173 Approved
0.6333 Remote Similarity NPD7879 Clinical (unspecified phase)
0.6329 Remote Similarity NPD7625 Phase 1
0.6328 Remote Similarity NPD6079 Approved
0.6319 Remote Similarity NPD8444 Approved
0.6309 Remote Similarity NPD8390 Approved
0.6309 Remote Similarity NPD8392 Approved
0.6309 Remote Similarity NPD8391 Approved
0.6308 Remote Similarity NPD1698 Clinical (unspecified phase)
0.6308 Remote Similarity NPD5695 Phase 3
0.6304 Remote Similarity NPD5247 Approved
0.6304 Remote Similarity NPD5250 Approved
0.6304 Remote Similarity NPD5249 Phase 3
0.6304 Remote Similarity NPD5251 Approved
0.6304 Remote Similarity NPD5248 Approved
0.6301 Remote Similarity NPD8470 Clinical (unspecified phase)
0.6299 Remote Similarity NPD5328 Approved
0.6279 Remote Similarity NPD6399 Phase 3
0.6277 Remote Similarity NPD5128 Approved
0.6269 Remote Similarity NPD7632 Discontinued
0.6268 Remote Similarity NPD8137 Clinical (unspecified phase)
0.624 Remote Similarity NPD1694 Approved
0.6236 Remote Similarity NPD8055 Clinical (unspecified phase)
0.6222 Remote Similarity NPD8435 Approved
0.6222 Remote Similarity NPD4754 Approved
0.622 Remote Similarity NPD6672 Approved
0.622 Remote Similarity NPD5737 Approved
0.6202 Remote Similarity NPD5693 Phase 1
0.6202 Remote Similarity NPD7983 Approved
0.6202 Remote Similarity NPD6411 Approved
0.62 Remote Similarity NPD6914 Discontinued
0.619 Remote Similarity NPD8341 Approved
0.619 Remote Similarity NPD3618 Phase 1
0.619 Remote Similarity NPD8299 Approved
0.619 Remote Similarity NPD8340 Approved
0.619 Remote Similarity NPD8342 Approved
0.6183 Remote Similarity NPD4629 Approved
0.6183 Remote Similarity NPD5210 Approved
0.6154 Remote Similarity NPD5779 Approved
0.6154 Remote Similarity NPD5778 Approved
0.6143 Remote Similarity NPD5215 Approved
0.6143 Remote Similarity NPD5217 Approved
0.6143 Remote Similarity NPD5216 Approved
0.6133 Remote Similarity NPD8360 Approved
0.6133 Remote Similarity NPD8361 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