Structure

Physi-Chem Properties

Molecular Weight:  492.16
Volume:  467.672
LogP:  0.786
LogD:  0.714
LogS:  -1.975
# Rotatable Bonds:  8
TPSA:  175.37
# H-Bond Aceptor:  11
# H-Bond Donor:  6
# Rings:  4
# Heavy Atoms:  11

MedChem Properties

QED Drug-Likeness Score:  0.159
Synthetic Accessibility Score:  4.764
Fsp3:  0.458
Lipinski Rule-of-5:  Rejected
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:  -6.065
MDCK Permeability:  4.320597508922219e-05
Pgp-inhibitor:  0.001
Pgp-substrate:  0.902
Human Intestinal Absorption (HIA):  0.681
20% Bioavailability (F20%):  0.106
30% Bioavailability (F30%):  0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.195
Plasma Protein Binding (PPB):  69.48604583740234%
Volume Distribution (VD):  0.406
Pgp-substrate:  29.860458374023438%

ADMET: Metabolism

CYP1A2-inhibitor:  0.046
CYP1A2-substrate:  0.024
CYP2C19-inhibitor:  0.027
CYP2C19-substrate:  0.086
CYP2C9-inhibitor:  0.021
CYP2C9-substrate:  0.096
CYP2D6-inhibitor:  0.005
CYP2D6-substrate:  0.11
CYP3A4-inhibitor:  0.089
CYP3A4-substrate:  0.111

ADMET: Excretion

Clearance (CL):  1.495
Half-life (T1/2):  0.934

ADMET: Toxicity

hERG Blockers:  0.03
Human Hepatotoxicity (H-HT):  0.068
Drug-inuced Liver Injury (DILI):  0.799
AMES Toxicity:  0.14
Rat Oral Acute Toxicity:  0.729
Maximum Recommended Daily Dose:  0.564
Skin Sensitization:  0.468
Carcinogencity:  0.901
Eye Corrosion:  0.003
Eye Irritation:  0.015
Respiratory Toxicity:  0.566

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

  Natural Product: NPC254819

Natural Product ID:  NPC254819
Common Name*:   Eurostoside
IUPAC Name:   [(1S,4aR,5S,7aS)-5-hydroxy-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-7-yl]methyl (E)-3-(4-hydroxyphenyl)prop-2-enoate
Synonyms:   Eurostoside
Standard InCHIKey:  DQTBTFHCLVMGBP-WXUDOLSOSA-N
Standard InCHI:  InChI=1S/C24H28O11/c25-10-17-20(29)21(30)22(31)24(34-17)35-23-19-13(9-16(27)15(19)7-8-32-23)11-33-18(28)6-3-12-1-4-14(26)5-2-12/h1-9,15-17,19-27,29-31H,10-11H2/b6-3+/t15-,16+,17+,19+,20+,21-,22+,23-,24-/m0/s1
SMILES:  OC[C@H]1O[C@@H](O[C@@H]2OC=C[C@@H]3[C@H]2C(=C[C@H]3O)COC(=O)/C=C/c2ccc(cc2)O)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1080020
PubChem CID:   20839507
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0002049] Terpene glycosides
          • [CHEMONTID:0004081] Iridoid O-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
NPO3618 Pinus pinea Species Pinaceae Eukaryota n.a. n.a. n.a. PMID[12428002]
NPO10780 Bletilla striata Species Orchidaceae Eukaryota n.a. n.a. n.a. PMID[15686910]
NPO23142 Lamium album Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[19904996]
NPO3618 Pinus pinea Species Pinaceae Eukaryota n.a. seed n.a. PMID[22533651]
NPO10780 Bletilla striata Species Orchidaceae Eukaryota Fibrous Roots n.a. n.a. PMID[25760525]
NPO10780 Bletilla striata Species Orchidaceae Eukaryota n.a. n.a. n.a. PMID[31415170]
NPO10780 Bletilla striata Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO14719 Tephrosia noctiflora Species Geometridae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO14719 Tephrosia noctiflora Species Geometridae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO10780 Bletilla striata Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO10780 Bletilla striata Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO10780 Bletilla striata Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO23142 Lamium album Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10780 Bletilla striata Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13244 Pomacea canaliculata Species Ampullariidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16178 Aster maximus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17590 Usnea bayleyi Species Parmeliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16938 Limnodynastes salmini Species Myobatrachidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14719 Tephrosia noctiflora Species Geometridae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4315 Fagara tessmannii n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO19003 Isodon pleiophyllus Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14404 Agave kerchovei Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15093 Carpinus laxiflora Species Betulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3618 Pinus pinea Species Pinaceae 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
NPT191 Organism Hepatitis C virus Hepatitis C virus Inhibition = 46.6 % PMID[557344]
NPT191 Organism Hepatitis C virus Hepatitis C virus Inhibition = 56.6 % PMID[557344]
NPT191 Organism Hepatitis C virus Hepatitis C virus IC50 = 20.0 ug.mL-1 PMID[557344]

☑ 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 NPC254819 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
0.9466 High Similarity NPC220936
0.9466 High Similarity NPC31745
0.9318 High Similarity NPC49597
0.9274 High Similarity NPC52097
0.9219 High Similarity NPC253595
0.9206 High Similarity NPC126991
0.9206 High Similarity NPC83218
0.9194 High Similarity NPC11724
0.9185 High Similarity NPC293154
0.9179 High Similarity NPC46644
0.9141 High Similarity NPC225307
0.9134 High Similarity NPC252114
0.9134 High Similarity NPC471157
0.9118 High Similarity NPC473281
0.9118 High Similarity NPC77922
0.9113 High Similarity NPC476872
0.9062 High Similarity NPC156692
0.9062 High Similarity NPC471882
0.9062 High Similarity NPC173150
0.9062 High Similarity NPC106677
0.9062 High Similarity NPC35288
0.9062 High Similarity NPC471881
0.9062 High Similarity NPC288416
0.9062 High Similarity NPC45224
0.9044 High Similarity NPC152796
0.9044 High Similarity NPC475213
0.9023 High Similarity NPC472132
0.8978 High Similarity NPC296659
0.8978 High Similarity NPC202391
0.8978 High Similarity NPC184464
0.8978 High Similarity NPC251062
0.8931 High Similarity NPC478255
0.8905 High Similarity NPC263397
0.8905 High Similarity NPC237872
0.8905 High Similarity NPC302286
0.8905 High Similarity NPC116104
0.8905 High Similarity NPC88754
0.8897 High Similarity NPC137501
0.8897 High Similarity NPC7518
0.8897 High Similarity NPC159387
0.8897 High Similarity NPC154262
0.8872 High Similarity NPC169398
0.8841 High Similarity NPC63304
0.8837 High Similarity NPC61181
0.8806 High Similarity NPC476870
0.8797 High Similarity NPC28637
0.8788 High Similarity NPC138777
0.8788 High Similarity NPC235294
0.8788 High Similarity NPC281798
0.8788 High Similarity NPC46137
0.8788 High Similarity NPC219677
0.8788 High Similarity NPC225384
0.8788 High Similarity NPC246869
0.8786 High Similarity NPC18789
0.8786 High Similarity NPC473149
0.8779 High Similarity NPC295970
0.8779 High Similarity NPC229784
0.8779 High Similarity NPC477293
0.8779 High Similarity NPC477294
0.8777 High Similarity NPC475528
0.8769 High Similarity NPC103533
0.8768 High Similarity NPC186296
0.8732 High Similarity NPC69367
0.8722 High Similarity NPC473924
0.8722 High Similarity NPC473285
0.8714 High Similarity NPC143246
0.8714 High Similarity NPC475539
0.8714 High Similarity NPC37838
0.8714 High Similarity NPC474268
0.8714 High Similarity NPC119773
0.8705 High Similarity NPC478240
0.8702 High Similarity NPC232880
0.8676 High Similarity NPC469364
0.8676 High Similarity NPC65262
0.8676 High Similarity NPC101686
0.8662 High Similarity NPC96599
0.8662 High Similarity NPC478236
0.8662 High Similarity NPC478234
0.8657 High Similarity NPC254398
0.8626 High Similarity NPC476873
0.8611 High Similarity NPC203664
0.8603 High Similarity NPC166180
0.8601 High Similarity NPC117346
0.8601 High Similarity NPC240592
0.8593 High Similarity NPC886
0.8593 High Similarity NPC34293
0.8593 High Similarity NPC471883
0.8593 High Similarity NPC287597
0.8582 High Similarity NPC473147
0.8548 High Similarity NPC313193
0.8542 High Similarity NPC269914
0.8542 High Similarity NPC158546
0.8542 High Similarity NPC478249
0.8542 High Similarity NPC289021
0.8529 High Similarity NPC263829
0.8507 High Similarity NPC475824
0.8483 Intermediate Similarity NPC194705
0.8478 Intermediate Similarity NPC321184
0.8478 Intermediate Similarity NPC321638
0.8478 Intermediate Similarity NPC171134
0.8478 Intermediate Similarity NPC226005
0.8478 Intermediate Similarity NPC328273
0.8472 Intermediate Similarity NPC147224
0.8467 Intermediate Similarity NPC157554
0.8467 Intermediate Similarity NPC470572
0.8467 Intermediate Similarity NPC471345
0.8462 Intermediate Similarity NPC308178
0.8429 Intermediate Similarity NPC296643
0.8425 Intermediate Similarity NPC478241
0.8425 Intermediate Similarity NPC89693
0.8425 Intermediate Similarity NPC229548
0.8421 Intermediate Similarity NPC146540
0.8417 Intermediate Similarity NPC202700
0.8414 Intermediate Similarity NPC474620
0.8413 Intermediate Similarity NPC175771
0.8409 Intermediate Similarity NPC267733
0.8409 Intermediate Similarity NPC276047
0.8406 Intermediate Similarity NPC260425
0.8406 Intermediate Similarity NPC476376
0.8406 Intermediate Similarity NPC78363
0.8397 Intermediate Similarity NPC145287
0.8369 Intermediate Similarity NPC204644
0.8357 Intermediate Similarity NPC476442
0.8357 Intermediate Similarity NPC215512
0.8357 Intermediate Similarity NPC186406
0.8345 Intermediate Similarity NPC89105
0.8345 Intermediate Similarity NPC64141
0.8345 Intermediate Similarity NPC100389
0.8345 Intermediate Similarity NPC472350
0.8345 Intermediate Similarity NPC68092
0.8345 Intermediate Similarity NPC476383
0.8345 Intermediate Similarity NPC220942
0.8345 Intermediate Similarity NPC205195
0.8345 Intermediate Similarity NPC81515
0.8345 Intermediate Similarity NPC197316
0.8333 Intermediate Similarity NPC103409
0.8333 Intermediate Similarity NPC186418
0.8333 Intermediate Similarity NPC37468
0.8322 Intermediate Similarity NPC212808
0.8311 Intermediate Similarity NPC475484
0.831 Intermediate Similarity NPC110063
0.831 Intermediate Similarity NPC194938
0.8308 Intermediate Similarity NPC469686
0.8298 Intermediate Similarity NPC157816
0.8298 Intermediate Similarity NPC140502
0.8298 Intermediate Similarity NPC145319
0.8295 Intermediate Similarity NPC469702
0.8295 Intermediate Similarity NPC282409
0.8288 Intermediate Similarity NPC475379
0.8268 Intermediate Similarity NPC148055
0.8264 Intermediate Similarity NPC97240
0.8261 Intermediate Similarity NPC185778
0.8255 Intermediate Similarity NPC475378
0.8254 Intermediate Similarity NPC157338
0.8252 Intermediate Similarity NPC287615
0.8252 Intermediate Similarity NPC83743
0.8252 Intermediate Similarity NPC262182
0.8252 Intermediate Similarity NPC216819
0.8248 Intermediate Similarity NPC114116
0.8244 Intermediate Similarity NPC471067
0.8239 Intermediate Similarity NPC478250
0.8239 Intermediate Similarity NPC105005
0.8239 Intermediate Similarity NPC40305
0.8239 Intermediate Similarity NPC478239
0.8231 Intermediate Similarity NPC478235
0.8231 Intermediate Similarity NPC201402
0.8231 Intermediate Similarity NPC469548
0.8231 Intermediate Similarity NPC469704
0.8231 Intermediate Similarity NPC476448
0.8231 Intermediate Similarity NPC469703
0.8231 Intermediate Similarity NPC160854
0.8231 Intermediate Similarity NPC476445
0.8227 Intermediate Similarity NPC47471
0.8227 Intermediate Similarity NPC476385
0.8227 Intermediate Similarity NPC476377
0.8227 Intermediate Similarity NPC134405
0.8209 Intermediate Similarity NPC175333
0.8207 Intermediate Similarity NPC189631
0.8207 Intermediate Similarity NPC120728
0.8194 Intermediate Similarity NPC320734
0.8182 Intermediate Similarity NPC476867
0.8182 Intermediate Similarity NPC297342
0.8182 Intermediate Similarity NPC178449
0.8182 Intermediate Similarity NPC232228
0.8182 Intermediate Similarity NPC470907
0.8182 Intermediate Similarity NPC292443
0.8182 Intermediate Similarity NPC141455
0.8182 Intermediate Similarity NPC296954
0.8182 Intermediate Similarity NPC300894
0.8182 Intermediate Similarity NPC232454
0.8182 Intermediate Similarity NPC196063
0.8176 Intermediate Similarity NPC469699
0.8176 Intermediate Similarity NPC229354
0.8176 Intermediate Similarity NPC257847
0.8169 Intermediate Similarity NPC222433
0.8169 Intermediate Similarity NPC265648
0.8168 Intermediate Similarity NPC55608
0.8163 Intermediate Similarity NPC77310
0.8156 Intermediate Similarity NPC475530
0.8156 Intermediate Similarity NPC473799

  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 NPC254819 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
0.8345 Intermediate Similarity NPD7266 Discontinued
0.7905 Intermediate Similarity NPD1653 Approved
0.7761 Intermediate Similarity NPD1091 Approved
0.7593 Intermediate Similarity NPD7685 Pre-registration
0.7389 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.7383 Intermediate Similarity NPD6190 Approved
0.7328 Intermediate Similarity NPD969 Suspended
0.7287 Intermediate Similarity NPD1358 Approved
0.726 Intermediate Similarity NPD4978 Clinical (unspecified phase)
0.7248 Intermediate Similarity NPD1652 Phase 2
0.7209 Intermediate Similarity NPD3134 Approved
0.7197 Intermediate Similarity NPD8455 Phase 2
0.7123 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.7123 Intermediate Similarity NPD4340 Discontinued
0.7123 Intermediate Similarity NPD5124 Phase 1
0.7086 Intermediate Similarity NPD4628 Phase 3
0.708 Intermediate Similarity NPD9545 Approved
0.7063 Intermediate Similarity NPD2861 Phase 2
0.703 Intermediate Similarity NPD7228 Approved
0.703 Intermediate Similarity NPD3818 Discontinued
0.7027 Intermediate Similarity NPD7097 Phase 1
0.7025 Intermediate Similarity NPD37 Approved
0.7019 Intermediate Similarity NPD6234 Discontinued
0.7006 Intermediate Similarity NPD4380 Phase 2
0.7 Intermediate Similarity NPD4967 Phase 2
0.7 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD4966 Approved
0.7 Intermediate Similarity NPD4965 Approved
0.7 Intermediate Similarity NPD422 Phase 1
0.6978 Remote Similarity NPD5126 Approved
0.6978 Remote Similarity NPD5125 Phase 3
0.6964 Remote Similarity NPD6559 Discontinued
0.6959 Remote Similarity NPD6653 Approved
0.6948 Remote Similarity NPD6143 Clinical (unspecified phase)
0.6933 Remote Similarity NPD7199 Phase 2
0.6923 Remote Similarity NPD4338 Clinical (unspecified phase)
0.6918 Remote Similarity NPD3764 Approved
0.6906 Remote Similarity NPD1357 Approved
0.6887 Remote Similarity NPD5762 Approved
0.6887 Remote Similarity NPD5763 Approved
0.6886 Remote Similarity NPD7054 Approved
0.6886 Remote Similarity NPD7804 Clinical (unspecified phase)
0.6883 Remote Similarity NPD5058 Phase 3
0.6882 Remote Similarity NPD8312 Approved
0.6882 Remote Similarity NPD8313 Approved
0.6879 Remote Similarity NPD3705 Approved
0.6875 Remote Similarity NPD5647 Approved
0.6875 Remote Similarity NPD6007 Clinical (unspecified phase)
0.6871 Remote Similarity NPD6233 Phase 2
0.6849 Remote Similarity NPD3027 Phase 3
0.6845 Remote Similarity NPD7472 Approved
0.6824 Remote Similarity NPD1612 Clinical (unspecified phase)
0.6824 Remote Similarity NPD1613 Approved
0.6824 Remote Similarity NPD4060 Phase 1
0.6824 Remote Similarity NPD7966 Clinical (unspecified phase)
0.6815 Remote Similarity NPD5403 Approved
0.6806 Remote Similarity NPD3094 Phase 2
0.6805 Remote Similarity NPD6797 Phase 2
0.6797 Remote Similarity NPD6674 Discontinued
0.679 Remote Similarity NPD4868 Clinical (unspecified phase)
0.6783 Remote Similarity NPD4379 Clinical (unspecified phase)
0.6781 Remote Similarity NPD4908 Phase 1
0.6779 Remote Similarity NPD6355 Discontinued
0.6779 Remote Similarity NPD230 Phase 1
0.6765 Remote Similarity NPD7843 Approved
0.6765 Remote Similarity NPD7251 Discontinued
0.6761 Remote Similarity NPD1610 Phase 2
0.6755 Remote Similarity NPD7033 Discontinued
0.6753 Remote Similarity NPD1878 Clinical (unspecified phase)
0.6748 Remote Similarity NPD7075 Discontinued
0.6747 Remote Similarity NPD7184 Clinical (unspecified phase)
0.6746 Remote Similarity NPD7074 Phase 3
0.6739 Remote Similarity NPD7157 Approved
0.6736 Remote Similarity NPD3225 Approved
0.6732 Remote Similarity NPD2424 Discontinued
0.6727 Remote Similarity NPD8127 Discontinued
0.6725 Remote Similarity NPD7808 Phase 3
0.6716 Remote Similarity NPD2684 Approved
0.6714 Remote Similarity NPD1548 Phase 1
0.6712 Remote Similarity NPD5736 Approved
0.6711 Remote Similarity NPD4140 Approved
0.6708 Remote Similarity NPD6801 Discontinued
0.6691 Remote Similarity NPD694 Clinical (unspecified phase)
0.669 Remote Similarity NPD6362 Approved
0.669 Remote Similarity NPD2797 Approved
0.6689 Remote Similarity NPD4907 Clinical (unspecified phase)
0.6689 Remote Similarity NPD6798 Discontinued
0.6688 Remote Similarity NPD5401 Approved
0.6667 Remote Similarity NPD6002 Phase 3
0.6667 Remote Similarity NPD7240 Approved
0.6667 Remote Similarity NPD6004 Phase 3
0.6667 Remote Similarity NPD6006 Clinical (unspecified phase)
0.6667 Remote Similarity NPD6003 Clinical (unspecified phase)
0.6667 Remote Similarity NPD6005 Phase 3
0.6645 Remote Similarity NPD8166 Discontinued
0.6645 Remote Similarity NPD3750 Approved
0.6645 Remote Similarity NPD5588 Approved
0.6643 Remote Similarity NPD3092 Approved
0.6642 Remote Similarity NPD290 Approved
0.6626 Remote Similarity NPD5402 Approved
0.6625 Remote Similarity NPD7458 Discontinued
0.661 Remote Similarity NPD7879 Clinical (unspecified phase)
0.6604 Remote Similarity NPD6980 Clinical (unspecified phase)
0.6591 Remote Similarity NPD6647 Phase 2
0.6582 Remote Similarity NPD7004 Clinical (unspecified phase)
0.6581 Remote Similarity NPD7421 Clinical (unspecified phase)
0.6579 Remote Similarity NPD4538 Approved
0.6579 Remote Similarity NPD4536 Approved
0.6579 Remote Similarity NPD4537 Clinical (unspecified phase)
0.6577 Remote Similarity NPD6859 Clinical (unspecified phase)
0.6577 Remote Similarity NPD3268 Approved
0.6573 Remote Similarity NPD3496 Discontinued
0.6564 Remote Similarity NPD7096 Clinical (unspecified phase)
0.656 Remote Similarity NPD689 Discontinued
0.6554 Remote Similarity NPD1529 Clinical (unspecified phase)
0.6541 Remote Similarity NPD7314 Clinical (unspecified phase)
0.6538 Remote Similarity NPD6398 Clinical (unspecified phase)
0.6536 Remote Similarity NPD5960 Phase 3
0.6533 Remote Similarity NPD4062 Phase 3
0.6533 Remote Similarity NPD6663 Approved
0.6522 Remote Similarity NPD5535 Approved
0.6519 Remote Similarity NPD6799 Approved
0.6519 Remote Similarity NPD9265 Clinical (unspecified phase)
0.6516 Remote Similarity NPD1549 Phase 2
0.6516 Remote Similarity NPD970 Clinical (unspecified phase)
0.651 Remote Similarity NPD7095 Approved
0.6507 Remote Similarity NPD8651 Approved
0.6503 Remote Similarity NPD4626 Approved
0.6493 Remote Similarity NPD9697 Approved
0.649 Remote Similarity NPD3620 Phase 2
0.649 Remote Similarity NPD3619 Clinical (unspecified phase)
0.6489 Remote Similarity NPD3020 Approved
0.6486 Remote Similarity NPD1530 Clinical (unspecified phase)
0.6479 Remote Similarity NPD3091 Approved
0.6479 Remote Similarity NPD7741 Discontinued
0.6478 Remote Similarity NPD3536 Discontinued
0.6478 Remote Similarity NPD8389 Clinical (unspecified phase)
0.6474 Remote Similarity NPD5698 Clinical (unspecified phase)
0.6454 Remote Similarity NPD9493 Approved
0.6452 Remote Similarity NPD1552 Clinical (unspecified phase)
0.6452 Remote Similarity NPD1550 Clinical (unspecified phase)
0.6447 Remote Similarity NPD5735 Approved
0.6447 Remote Similarity NPD1933 Approved
0.6444 Remote Similarity NPD968 Approved
0.6442 Remote Similarity NPD7411 Suspended
0.6438 Remote Similarity NPD6273 Approved
0.6438 Remote Similarity NPD3685 Discontinued
0.6434 Remote Similarity NPD2934 Approved
0.6434 Remote Similarity NPD2933 Approved
0.6434 Remote Similarity NPD5691 Approved
0.6433 Remote Similarity NPD3751 Discontinued
0.6429 Remote Similarity NPD4108 Discontinued
0.6429 Remote Similarity NPD1510 Phase 2
0.6424 Remote Similarity NPD3817 Phase 2
0.6423 Remote Similarity NPD3021 Approved
0.6423 Remote Similarity NPD3022 Approved
0.6416 Remote Similarity NPD7993 Clinical (unspecified phase)
0.6414 Remote Similarity NPD1535 Discovery
0.641 Remote Similarity NPD5958 Discontinued
0.6408 Remote Similarity NPD5536 Phase 2
0.6402 Remote Similarity NPD1934 Approved
0.64 Remote Similarity NPD5952 Clinical (unspecified phase)
0.64 Remote Similarity NPD1282 Approved
0.6395 Remote Similarity NPD5844 Phase 1
0.6389 Remote Similarity NPD5846 Approved
0.6389 Remote Similarity NPD5238 Clinical (unspecified phase)
0.6389 Remote Similarity NPD6516 Phase 2
0.6387 Remote Similarity NPD2935 Discontinued
0.6387 Remote Similarity NPD1551 Phase 2
0.6385 Remote Similarity NPD2860 Approved
0.6385 Remote Similarity NPD2859 Approved
0.6383 Remote Similarity NPD4198 Discontinued
0.638 Remote Similarity NPD7028 Phase 2
0.638 Remote Similarity NPD6599 Discontinued
0.637 Remote Similarity NPD1481 Phase 2
0.6364 Remote Similarity NPD2393 Clinical (unspecified phase)
0.6364 Remote Similarity NPD1894 Discontinued
0.6364 Remote Similarity NPD7819 Suspended
0.6358 Remote Similarity NPD6410 Clinical (unspecified phase)
0.6351 Remote Similarity NPD1203 Approved
0.6346 Remote Similarity NPD2029 Clinical (unspecified phase)
0.6345 Remote Similarity NPD3847 Discontinued
0.6343 Remote Similarity NPD5738 Clinical (unspecified phase)
0.6341 Remote Similarity NPD7615 Clinical (unspecified phase)
0.6337 Remote Similarity NPD7799 Discontinued
0.6331 Remote Similarity NPD228 Approved
0.6329 Remote Similarity NPD4109 Clinical (unspecified phase)
0.6329 Remote Similarity NPD4110 Phase 3
0.6327 Remote Similarity NPD4749 Approved
0.6325 Remote Similarity NPD8443 Clinical (unspecified phase)
0.6323 Remote Similarity NPD3748 Approved
0.6319 Remote Similarity NPD5585 Approved
0.6319 Remote Similarity NPD5808 Clinical (unspecified phase)
0.6316 Remote Similarity NPD6167 Clinical (unspecified phase)
0.6316 Remote Similarity NPD6168 Clinical (unspecified phase)
0.6316 Remote Similarity NPD1242 Phase 1
0.6316 Remote Similarity NPD6166 Phase 2
0.6313 Remote Similarity NPD8397 Clinical (unspecified phase)
0.6312 Remote Similarity NPD690 Clinical (unspecified phase)
0.6309 Remote Similarity NPD2798 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