Structure

Physi-Chem Properties

Molecular Weight:  658.42
Volume:  733.059
LogP:  4.537
LogD:  3.408
LogS:  -4.983
# Rotatable Bonds:  12
TPSA:  96.36
# H-Bond Aceptor:  6
# H-Bond Donor:  2
# Rings:  3
# Heavy Atoms:  6

MedChem Properties

QED Drug-Likeness Score:  0.076
Synthetic Accessibility Score:  5.632
Fsp3:  0.548
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  1
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.104
MDCK Permeability:  1.2974866876902524e-05
Pgp-inhibitor:  0.981
Pgp-substrate:  0.995
Human Intestinal Absorption (HIA):  0.01
20% Bioavailability (F20%):  0.006
30% Bioavailability (F30%):  0.038

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.762
Plasma Protein Binding (PPB):  98.12891387939453%
Volume Distribution (VD):  2.062
Pgp-substrate:  3.2873659133911133%

ADMET: Metabolism

CYP1A2-inhibitor:  0.016
CYP1A2-substrate:  0.276
CYP2C19-inhibitor:  0.551
CYP2C19-substrate:  0.904
CYP2C9-inhibitor:  0.307
CYP2C9-substrate:  0.984
CYP2D6-inhibitor:  0.894
CYP2D6-substrate:  0.912
CYP3A4-inhibitor:  0.96
CYP3A4-substrate:  0.724

ADMET: Excretion

Clearance (CL):  2.665
Half-life (T1/2):  0.07

ADMET: Toxicity

hERG Blockers:  0.181
Human Hepatotoxicity (H-HT):  0.599
Drug-inuced Liver Injury (DILI):  0.087
AMES Toxicity:  0.033
Rat Oral Acute Toxicity:  0.041
Maximum Recommended Daily Dose:  0.983
Skin Sensitization:  0.927
Carcinogencity:  0.912
Eye Corrosion:  0.003
Eye Irritation:  0.008
Respiratory Toxicity:  0.963

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

  Natural Product: NPC102843

Natural Product ID:  NPC102843
Common Name*:   [(1S,3R)-3-Hydroxy-4-[(3E,5E,7E,9E,11E,13E,15E)-18-[(1R,3S,6S)-3-Hydroxy-1,5,5-Trimethyl-7-Oxabicyclo[4.1.0]Heptan-6-Yl]-3,7,12,16-Tetramethyl-17-Oxooctadeca-1,3,5,7,9,11,13,15-Octaenylidene]-3,5,5-Trimethylcyclohexyl] Acetate
IUPAC Name:   [(1S,3R)-3-hydroxy-4-[(3E,5E,7E,9E,11E,13E,15E)-18-[(1R,3S,6S)-3-hydroxy-1,5,5-trimethyl-7-oxabicyclo[4.1.0]heptan-6-yl]-3,7,12,16-tetramethyl-17-oxooctadeca-1,3,5,7,9,11,13,15-octaenylidene]-3,5,5-trimethylcyclohexyl] acetate
Synonyms:  
Standard InCHIKey:  SJWWTRQNNRNTPU-ABBNZJFMSA-N
Standard InCHI:  InChI=1S/C42H58O6/c1-29(18-14-19-31(3)22-23-37-38(6,7)26-35(47-33(5)43)27-40(37,10)46)16-12-13-17-30(2)20-15-21-32(4)36(45)28-42-39(8,9)24-34(44)25-41(42,11)48-42/h12-22,34-35,44,46H,24-28H2,1-11H3/b13-12+,18-14+,20-15+,29-16+,30-17+,31-19+,32-21+/t23?,34-,35-,40+,41+,42-/m0/s1
SMILES:  C/C(=CC=CC=C(C=CC=C(C(=O)C[C@]12O[C@]2(C)C[C@H](CC1(C)C)O)/C)/C)/C=C/C=C(/C=C=C1C(C)(C)C[C@@H](C[C@@]1(C)O)OC(=O)C)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1575074
PubChem CID:   5281239
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001554] Tetraterpenoids
          • [CHEMONTID:0001277] Carotenoids
            • [CHEMONTID:0001410] Xanthophylls

*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
NPO12011 Crataegus pinnatifida Species Rosaceae Eukaryota n.a. fruit n.a. PMID[15739361]
NPO12011 Crataegus pinnatifida Species Rosaceae Eukaryota n.a. seed n.a. PMID[23845552]
NPO12011 Crataegus pinnatifida Species Rosaceae Eukaryota seeds n.a. n.a. PMID[23999046]
NPO12011 Crataegus pinnatifida Species Rosaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO12011 Crataegus pinnatifida Species Rosaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO12011 Crataegus pinnatifida Species Rosaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO12011 Crataegus pinnatifida Species Rosaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO12011 Crataegus pinnatifida Species Rosaceae 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
NPT47 Individual Protein ATP-dependent DNA helicase Q1 Homo sapiens Potency = 354.8 nM PMID[515526]
NPT48 Individual Protein Lysine-specific demethylase 4D-like Homo sapiens Potency = 39810.7 nM PMID[515526]
NPT51 Individual Protein Microtubule-associated protein tau Homo sapiens Potency = 25118.9 nM PMID[515526]
NPT3 Individual Protein Thioredoxin glutathione reductase Schistosoma mansoni Potency = 3162.3 nM PMID[515526]
NPT226 Individual Protein Beta-2 adrenergic receptor Homo sapiens Potency n.a. 28183.8 nM PMID[515526]
NPT539 Individual Protein Cellular tumor antigen p53 Homo sapiens Potency n.a. 35481.3 nM PMID[515526]
NPT5 Individual Protein Histone-lysine N-methyltransferase, H3 lysine-9 specific 3 Homo sapiens Potency n.a. 6309.6 nM PMID[515526]
NPT198 Individual Protein Vitamin D receptor Homo sapiens Potency n.a. 89125.1 nM PMID[515526]
NPT65 Cell Line HepG2 Homo sapiens Potency n.a. 35481.3 nM PMID[515526]
NPT154 Individual Protein Mothers against decapentaplegic homolog 3 Homo sapiens Potency n.a. 11220.2 nM PMID[515526]
NPT10 Individual Protein Geminin Homo sapiens Potency n.a. 20596.2 nM PMID[515526]
NPT501 Individual Protein Alpha-galactosidase A Homo sapiens Potency n.a. 50118.7 nM PMID[515526]
NPT10 Individual Protein Geminin Homo sapiens Potency n.a. 16360.1 nM PMID[515526]
NPT478 Individual Protein Ataxin-2 Homo sapiens Potency n.a. 35481.3 nM PMID[515526]
NPT152 Individual Protein Nuclear factor erythroid 2-related factor 2 Homo sapiens Potency n.a. 22387.2 nM PMID[515526]
NPT50 Individual Protein Tyrosyl-DNA phosphodiesterase 1 Homo sapiens Potency n.a. 25929.0 nM PMID[515526]
NPT535 Individual Protein Parathyroid hormone receptor Homo sapiens Potency n.a. 50118.7 nM PMID[515526]
NPT2 Others Unspecified Potency = 31622.8 nM PMID[515526]
NPT2 Others Unspecified Potency n.a. 707.9 nM PMID[515526]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum Potency n.a. 2616.9 nM PMID[515526]
NPT7 Individual Protein Thioredoxin reductase 1, cytoplasmic Rattus norvegicus Potency n.a. 35481.3 nM PMID[515526]
NPT2 Others Unspecified Potency n.a. 22387.2 nM PMID[515526]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum Potency n.a. 9285.0 nM PMID[515526]
NPT2 Others Unspecified Potency n.a. 19952.6 nM PMID[515526]

☑ 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 NPC102843 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
0.8846 High Similarity NPC128828
0.8476 Intermediate Similarity NPC72151
0.8381 Intermediate Similarity NPC320447
0.8302 Intermediate Similarity NPC478057
0.8286 Intermediate Similarity NPC115862
0.8286 Intermediate Similarity NPC282524
0.8241 Intermediate Similarity NPC473284
0.8224 Intermediate Similarity NPC239162
0.8208 Intermediate Similarity NPC478156
0.8198 Intermediate Similarity NPC475970
0.8174 Intermediate Similarity NPC472759
0.8174 Intermediate Similarity NPC329080
0.8165 Intermediate Similarity NPC322903
0.8148 Intermediate Similarity NPC34768
0.8131 Intermediate Similarity NPC329345
0.8131 Intermediate Similarity NPC473283
0.8131 Intermediate Similarity NPC471938
0.8131 Intermediate Similarity NPC95899
0.8131 Intermediate Similarity NPC475526
0.8125 Intermediate Similarity NPC474271
0.8119 Intermediate Similarity NPC232202
0.8113 Intermediate Similarity NPC115899
0.8103 Intermediate Similarity NPC67569
0.8095 Intermediate Similarity NPC316598
0.8087 Intermediate Similarity NPC236918
0.8087 Intermediate Similarity NPC156745
0.8077 Intermediate Similarity NPC202833
0.8077 Intermediate Similarity NPC471153
0.807 Intermediate Similarity NPC153651
0.807 Intermediate Similarity NPC474518
0.8058 Intermediate Similarity NPC103527
0.8056 Intermediate Similarity NPC118911
0.8056 Intermediate Similarity NPC471937
0.8053 Intermediate Similarity NPC73314
0.8037 Intermediate Similarity NPC475091
0.8037 Intermediate Similarity NPC475038
0.8037 Intermediate Similarity NPC109195
0.8037 Intermediate Similarity NPC471914
0.8037 Intermediate Similarity NPC476081
0.8036 Intermediate Similarity NPC90952
0.8034 Intermediate Similarity NPC23786
0.8034 Intermediate Similarity NPC470265
0.8019 Intermediate Similarity NPC35751
0.8019 Intermediate Similarity NPC266955
0.8018 Intermediate Similarity NPC474567
0.8017 Intermediate Similarity NPC475885
0.8017 Intermediate Similarity NPC185876
0.8017 Intermediate Similarity NPC19336
0.8017 Intermediate Similarity NPC476962
0.8 Intermediate Similarity NPC21326
0.8 Intermediate Similarity NPC472760
0.8 Intermediate Similarity NPC287668
0.7983 Intermediate Similarity NPC293112
0.7981 Intermediate Similarity NPC88310
0.7966 Intermediate Similarity NPC469789
0.7965 Intermediate Similarity NPC472757
0.7965 Intermediate Similarity NPC122056
0.7963 Intermediate Similarity NPC475050
0.7946 Intermediate Similarity NPC317107
0.7944 Intermediate Similarity NPC111292
0.7931 Intermediate Similarity NPC470186
0.7931 Intermediate Similarity NPC180640
0.7931 Intermediate Similarity NPC476960
0.7928 Intermediate Similarity NPC475941
0.7928 Intermediate Similarity NPC475065
0.7928 Intermediate Similarity NPC474901
0.7928 Intermediate Similarity NPC87335
0.7921 Intermediate Similarity NPC104560
0.7917 Intermediate Similarity NPC471940
0.7913 Intermediate Similarity NPC10721
0.7913 Intermediate Similarity NPC469684
0.7909 Intermediate Similarity NPC179380
0.7909 Intermediate Similarity NPC302788
0.7909 Intermediate Similarity NPC187435
0.7909 Intermediate Similarity NPC67321
0.7905 Intermediate Similarity NPC234993
0.7905 Intermediate Similarity NPC242848
0.7905 Intermediate Similarity NPC134072
0.7905 Intermediate Similarity NPC301534
0.7905 Intermediate Similarity NPC250757
0.7899 Intermediate Similarity NPC145238
0.7899 Intermediate Similarity NPC172154
0.7899 Intermediate Similarity NPC81736
0.7895 Intermediate Similarity NPC238667
0.7895 Intermediate Similarity NPC80650
0.7895 Intermediate Similarity NPC472400
0.7885 Intermediate Similarity NPC473431
0.7885 Intermediate Similarity NPC473280
0.7885 Intermediate Similarity NPC473435
0.7885 Intermediate Similarity NPC471078
0.7881 Intermediate Similarity NPC19464
0.7876 Intermediate Similarity NPC4573
0.7876 Intermediate Similarity NPC317687
0.7876 Intermediate Similarity NPC277769
0.787 Intermediate Similarity NPC32577
0.787 Intermediate Similarity NPC155332
0.787 Intermediate Similarity NPC162973
0.787 Intermediate Similarity NPC164551
0.787 Intermediate Similarity NPC114540
0.7863 Intermediate Similarity NPC114939
0.7863 Intermediate Similarity NPC475003
0.7863 Intermediate Similarity NPC145074
0.7863 Intermediate Similarity NPC41123
0.7857 Intermediate Similarity NPC478209
0.7857 Intermediate Similarity NPC472215
0.7857 Intermediate Similarity NPC472214
0.7851 Intermediate Similarity NPC236999
0.785 Intermediate Similarity NPC47024
0.785 Intermediate Similarity NPC306856
0.785 Intermediate Similarity NPC474718
0.785 Intermediate Similarity NPC16601
0.785 Intermediate Similarity NPC470074
0.7845 Intermediate Similarity NPC124676
0.7845 Intermediate Similarity NPC108581
0.7845 Intermediate Similarity NPC709
0.7845 Intermediate Similarity NPC478206
0.7845 Intermediate Similarity NPC146280
0.7845 Intermediate Similarity NPC251310
0.7845 Intermediate Similarity NPC284707
0.7845 Intermediate Similarity NPC234522
0.7845 Intermediate Similarity NPC478205
0.7845 Intermediate Similarity NPC50774
0.7843 Intermediate Similarity NPC471342
0.7843 Intermediate Similarity NPC469866
0.7838 Intermediate Similarity NPC476802
0.7838 Intermediate Similarity NPC472217
0.7838 Intermediate Similarity NPC318363
0.7838 Intermediate Similarity NPC475418
0.7838 Intermediate Similarity NPC89171
0.7838 Intermediate Similarity NPC472219
0.7838 Intermediate Similarity NPC472218
0.7838 Intermediate Similarity NPC473482
0.7833 Intermediate Similarity NPC471939
0.7833 Intermediate Similarity NPC473635
0.783 Intermediate Similarity NPC136781
0.783 Intermediate Similarity NPC473963
0.7826 Intermediate Similarity NPC471127
0.7826 Intermediate Similarity NPC270478
0.7826 Intermediate Similarity NPC154363
0.7826 Intermediate Similarity NPC234858
0.7815 Intermediate Similarity NPC11895
0.781 Intermediate Similarity NPC266899
0.781 Intermediate Similarity NPC134067
0.781 Intermediate Similarity NPC111273
0.781 Intermediate Similarity NPC180950
0.7807 Intermediate Similarity NPC477126
0.7807 Intermediate Similarity NPC159333
0.7807 Intermediate Similarity NPC25909
0.7798 Intermediate Similarity NPC469980
0.7798 Intermediate Similarity NPC104161
0.7798 Intermediate Similarity NPC120321
0.7798 Intermediate Similarity NPC118902
0.7798 Intermediate Similarity NPC476848
0.7798 Intermediate Similarity NPC131366
0.7797 Intermediate Similarity NPC472401
0.7788 Intermediate Similarity NPC158523
0.7788 Intermediate Similarity NPC146945
0.7788 Intermediate Similarity NPC207689
0.7788 Intermediate Similarity NPC171888
0.7788 Intermediate Similarity NPC475937
0.7788 Intermediate Similarity NPC476023
0.7788 Intermediate Similarity NPC474315
0.7778 Intermediate Similarity NPC242666
0.7778 Intermediate Similarity NPC308824
0.7778 Intermediate Similarity NPC5989
0.7778 Intermediate Similarity NPC471412
0.7778 Intermediate Similarity NPC471108
0.7778 Intermediate Similarity NPC255081
0.7778 Intermediate Similarity NPC268958
0.7778 Intermediate Similarity NPC5991
0.7778 Intermediate Similarity NPC22628
0.7778 Intermediate Similarity NPC275696
0.7778 Intermediate Similarity NPC475958
0.7778 Intermediate Similarity NPC112613
0.7778 Intermediate Similarity NPC46848
0.7768 Intermediate Similarity NPC474243
0.7759 Intermediate Similarity NPC183580
0.7759 Intermediate Similarity NPC478204
0.7759 Intermediate Similarity NPC27999
0.7759 Intermediate Similarity NPC140055
0.7759 Intermediate Similarity NPC286528
0.7759 Intermediate Similarity NPC20302
0.7759 Intermediate Similarity NPC470492
0.7759 Intermediate Similarity NPC477116
0.7759 Intermediate Similarity NPC312824
0.7759 Intermediate Similarity NPC470493
0.7759 Intermediate Similarity NPC53396
0.7759 Intermediate Similarity NPC98249
0.7759 Intermediate Similarity NPC167606
0.7757 Intermediate Similarity NPC57079
0.7757 Intermediate Similarity NPC216478
0.7757 Intermediate Similarity NPC108368
0.7757 Intermediate Similarity NPC119036
0.7757 Intermediate Similarity NPC478056
0.7757 Intermediate Similarity NPC72647
0.7757 Intermediate Similarity NPC107806
0.775 Intermediate Similarity NPC473709
0.775 Intermediate Similarity NPC8369
0.775 Intermediate Similarity NPC8374
0.775 Intermediate Similarity NPC473919

  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 NPC102843 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
0.7759 Intermediate Similarity NPD7115 Discovery
0.7523 Intermediate Similarity NPD6648 Approved
0.7522 Intermediate Similarity NPD5345 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD7902 Approved
0.7456 Intermediate Similarity NPD4061 Clinical (unspecified phase)
0.7455 Intermediate Similarity NPD5344 Discontinued
0.7453 Intermediate Similarity NPD5778 Approved
0.7453 Intermediate Similarity NPD5779 Approved
0.7431 Intermediate Similarity NPD4225 Approved
0.7391 Intermediate Similarity NPD5955 Clinical (unspecified phase)
0.7383 Intermediate Similarity NPD7748 Approved
0.7368 Intermediate Similarity NPD6899 Approved
0.7368 Intermediate Similarity NPD6881 Approved
0.7364 Intermediate Similarity NPD7640 Approved
0.7364 Intermediate Similarity NPD7639 Approved
0.7358 Intermediate Similarity NPD7637 Suspended
0.7328 Intermediate Similarity NPD6650 Approved
0.7328 Intermediate Similarity NPD8130 Phase 1
0.7328 Intermediate Similarity NPD6649 Approved
0.7281 Intermediate Similarity NPD5697 Approved
0.7273 Intermediate Similarity NPD6319 Approved
0.7273 Intermediate Similarity NPD7638 Approved
0.7265 Intermediate Similarity NPD8297 Approved
0.7241 Intermediate Similarity NPD7102 Approved
0.7241 Intermediate Similarity NPD7290 Approved
0.7241 Intermediate Similarity NPD6883 Approved
0.7222 Intermediate Similarity NPD7900 Approved
0.7222 Intermediate Similarity NPD7901 Clinical (unspecified phase)
0.7196 Intermediate Similarity NPD6411 Approved
0.7196 Intermediate Similarity NPD7515 Phase 2
0.7193 Intermediate Similarity NPD6675 Approved
0.7193 Intermediate Similarity NPD6008 Approved
0.7193 Intermediate Similarity NPD6402 Approved
0.7193 Intermediate Similarity NPD5739 Approved
0.7193 Intermediate Similarity NPD7128 Approved
0.7179 Intermediate Similarity NPD6869 Approved
0.7179 Intermediate Similarity NPD6847 Approved
0.7179 Intermediate Similarity NPD6617 Approved
0.7177 Intermediate Similarity NPD7492 Approved
0.7155 Intermediate Similarity NPD6012 Approved
0.7155 Intermediate Similarity NPD6013 Approved
0.7155 Intermediate Similarity NPD6373 Approved
0.7155 Intermediate Similarity NPD6014 Approved
0.7155 Intermediate Similarity NPD6372 Approved
0.7143 Intermediate Similarity NPD7736 Approved
0.7131 Intermediate Similarity NPD6054 Approved
0.713 Intermediate Similarity NPD5954 Clinical (unspecified phase)
0.712 Intermediate Similarity NPD6616 Approved
0.7119 Intermediate Similarity NPD6882 Approved
0.7097 Intermediate Similarity NPD8328 Phase 3
0.7094 Intermediate Similarity NPD6371 Approved
0.708 Intermediate Similarity NPD5211 Phase 2
0.7069 Intermediate Similarity NPD7320 Approved
0.7069 Intermediate Similarity NPD6011 Approved
0.7069 Intermediate Similarity NPD6686 Approved
0.7063 Intermediate Similarity NPD7078 Approved
0.7059 Intermediate Similarity NPD4632 Approved
0.7037 Intermediate Similarity NPD7983 Approved
0.7016 Intermediate Similarity NPD6370 Approved
0.7009 Intermediate Similarity NPD5764 Clinical (unspecified phase)
0.7009 Intermediate Similarity NPD6101 Approved
0.6983 Remote Similarity NPD5701 Approved
0.6972 Remote Similarity NPD6399 Phase 3
0.696 Remote Similarity NPD7604 Phase 2
0.6957 Remote Similarity NPD5141 Approved
0.6949 Remote Similarity NPD4634 Approved
0.6944 Remote Similarity NPD7838 Discovery
0.6935 Remote Similarity NPD6015 Approved
0.6935 Remote Similarity NPD6016 Approved
0.6929 Remote Similarity NPD8293 Discontinued
0.6909 Remote Similarity NPD5282 Discontinued
0.6903 Remote Similarity NPD4696 Approved
0.6903 Remote Similarity NPD5285 Approved
0.6903 Remote Similarity NPD5286 Approved
0.6887 Remote Similarity NPD3618 Phase 1
0.6885 Remote Similarity NPD6009 Approved
0.6881 Remote Similarity NPD6079 Approved
0.688 Remote Similarity NPD5988 Approved
0.6875 Remote Similarity NPD6084 Phase 2
0.6875 Remote Similarity NPD6083 Phase 2
0.6864 Remote Similarity NPD8132 Clinical (unspecified phase)
0.6857 Remote Similarity NPD7338 Clinical (unspecified phase)
0.6855 Remote Similarity NPD6059 Approved
0.6847 Remote Similarity NPD1698 Clinical (unspecified phase)
0.6822 Remote Similarity NPD3573 Approved
0.6822 Remote Similarity NPD7319 Approved
0.6814 Remote Similarity NPD8029 Clinical (unspecified phase)
0.68 Remote Similarity NPD6921 Approved
0.68 Remote Similarity NPD5983 Phase 2
0.6789 Remote Similarity NPD46 Approved
0.6789 Remote Similarity NPD6698 Approved
0.6789 Remote Similarity NPD5785 Approved
0.6783 Remote Similarity NPD5224 Approved
0.6783 Remote Similarity NPD5226 Approved
0.6783 Remote Similarity NPD7632 Discontinued
0.6783 Remote Similarity NPD4633 Approved
0.6783 Remote Similarity NPD5225 Approved
0.6774 Remote Similarity NPD7101 Approved
0.6774 Remote Similarity NPD7100 Approved
0.6762 Remote Similarity NPD6695 Phase 3
0.675 Remote Similarity NPD6401 Clinical (unspecified phase)
0.6729 Remote Similarity NPD3574 Clinical (unspecified phase)
0.6727 Remote Similarity NPD5284 Approved
0.6727 Remote Similarity NPD5281 Approved
0.6727 Remote Similarity NPD8034 Phase 2
0.6727 Remote Similarity NPD8035 Phase 2
0.6726 Remote Similarity NPD4755 Approved
0.6724 Remote Similarity NPD5174 Approved
0.6724 Remote Similarity NPD5175 Approved
0.6719 Remote Similarity NPD6336 Discontinued
0.6697 Remote Similarity NPD5328 Approved
0.6696 Remote Similarity NPD6356 Clinical (unspecified phase)
0.6696 Remote Similarity NPD5223 Approved
0.6695 Remote Similarity NPD6412 Phase 2
0.6694 Remote Similarity NPD6335 Approved
0.6667 Remote Similarity NPD4202 Approved
0.6667 Remote Similarity NPD8517 Approved
0.6667 Remote Similarity NPD8513 Phase 3
0.6667 Remote Similarity NPD8515 Approved
0.6667 Remote Similarity NPD6274 Approved
0.6667 Remote Similarity NPD5696 Approved
0.6667 Remote Similarity NPD7750 Discontinued
0.6667 Remote Similarity NPD4752 Clinical (unspecified phase)
0.6667 Remote Similarity NPD8516 Approved
0.6637 Remote Similarity NPD5221 Approved
0.6637 Remote Similarity NPD5222 Approved
0.6637 Remote Similarity NPD5220 Clinical (unspecified phase)
0.6637 Remote Similarity NPD7839 Suspended
0.6636 Remote Similarity NPD1694 Approved
0.6636 Remote Similarity NPD5363 Approved
0.6635 Remote Similarity NPD8259 Clinical (unspecified phase)
0.6613 Remote Similarity NPD8295 Clinical (unspecified phase)
0.6613 Remote Similarity NPD6317 Approved
0.6609 Remote Similarity NPD4700 Approved
0.6589 Remote Similarity NPD7507 Approved
0.6579 Remote Similarity NPD5173 Approved
0.6574 Remote Similarity NPD6684 Approved
0.6574 Remote Similarity NPD7334 Approved
0.6574 Remote Similarity NPD6409 Approved
0.6574 Remote Similarity NPD7146 Approved
0.6574 Remote Similarity NPD5330 Approved
0.6574 Remote Similarity NPD7521 Approved
0.656 Remote Similarity NPD7328 Approved
0.656 Remote Similarity NPD7327 Approved
0.656 Remote Similarity NPD6313 Approved
0.656 Remote Similarity NPD6314 Approved
0.6555 Remote Similarity NPD7899 Clinical (unspecified phase)
0.6549 Remote Similarity NPD4629 Approved
0.6549 Remote Similarity NPD5210 Approved
0.6549 Remote Similarity NPD5695 Phase 3
0.6535 Remote Similarity NPD7503 Approved
0.6535 Remote Similarity NPD6291 Clinical (unspecified phase)
0.6532 Remote Similarity NPD6868 Approved
0.6514 Remote Similarity NPD7524 Approved
0.6508 Remote Similarity NPD7516 Approved
0.65 Remote Similarity NPD4730 Approved
0.65 Remote Similarity NPD4729 Approved
0.6491 Remote Similarity NPD4697 Phase 3
0.6476 Remote Similarity NPD6931 Approved
0.6476 Remote Similarity NPD6930 Phase 2
0.6455 Remote Similarity NPD6903 Approved
0.6455 Remote Similarity NPD5737 Approved
0.6455 Remote Similarity NPD6672 Approved
0.6455 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6422 Remote Similarity NPD5279 Phase 3
0.6415 Remote Similarity NPD5369 Approved
0.6412 Remote Similarity NPD8074 Phase 3
0.6406 Remote Similarity NPD6909 Approved
0.6406 Remote Similarity NPD8378 Approved
0.6406 Remote Similarity NPD8379 Approved
0.6406 Remote Similarity NPD8296 Approved
0.6406 Remote Similarity NPD6908 Approved
0.6406 Remote Similarity NPD8380 Approved
0.6406 Remote Similarity NPD8335 Approved
0.6396 Remote Similarity NPD4753 Phase 2
0.6396 Remote Similarity NPD7285 Clinical (unspecified phase)
0.6393 Remote Similarity NPD5248 Approved
0.6393 Remote Similarity NPD5249 Phase 3
0.6393 Remote Similarity NPD5251 Approved
0.6393 Remote Similarity NPD5247 Approved
0.6393 Remote Similarity NPD5250 Approved
0.6389 Remote Similarity NPD3666 Approved
0.6389 Remote Similarity NPD3133 Approved
0.6389 Remote Similarity NPD3665 Phase 1
0.6389 Remote Similarity NPD4786 Approved
0.6381 Remote Similarity NPD6929 Approved
0.6371 Remote Similarity NPD8133 Approved
0.6364 Remote Similarity NPD6033 Approved
0.6364 Remote Similarity NPD5128 Approved
0.6355 Remote Similarity NPD3667 Approved
0.6355 Remote Similarity NPD5209 Approved
0.6355 Remote Similarity NPD4270 Approved
0.6355 Remote Similarity NPD4269 Approved
0.6341 Remote Similarity NPD5217 Approved
0.6341 Remote Similarity NPD5216 Approved
0.6341 Remote Similarity NPD5215 Approved
0.6339 Remote Similarity NPD5207 Approved
0.6333 Remote Similarity NPD4768 Approved
0.6333 Remote Similarity NPD4767 Approved
0.633 Remote Similarity NPD7520 Clinical (unspecified phase)

  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