Structure

Physi-Chem Properties

Molecular Weight:  570.15
Volume:  561.681
LogP:  4.388
LogD:  3.289
LogS:  -5.416
# Rotatable Bonds:  5
TPSA:  151.98
# H-Bond Aceptor:  10
# H-Bond Donor:  4
# Rings:  6
# Heavy Atoms:  10

MedChem Properties

QED Drug-Likeness Score:  0.255
Synthetic Accessibility Score:  4.004
Fsp3:  0.188
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:  -5.394
MDCK Permeability:  1.3069517990516033e-05
Pgp-inhibitor:  0.575
Pgp-substrate:  0.0
Human Intestinal Absorption (HIA):  0.128
20% Bioavailability (F20%):  0.002
30% Bioavailability (F30%):  0.371

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.001
Plasma Protein Binding (PPB):  97.71710968017578%
Volume Distribution (VD):  0.603
Pgp-substrate:  2.6773993968963623%

ADMET: Metabolism

CYP1A2-inhibitor:  0.227
CYP1A2-substrate:  0.838
CYP2C19-inhibitor:  0.962
CYP2C19-substrate:  0.059
CYP2C9-inhibitor:  0.911
CYP2C9-substrate:  0.974
CYP2D6-inhibitor:  0.42
CYP2D6-substrate:  0.915
CYP3A4-inhibitor:  0.889
CYP3A4-substrate:  0.194

ADMET: Excretion

Clearance (CL):  6.741
Half-life (T1/2):  0.084

ADMET: Toxicity

hERG Blockers:  0.099
Human Hepatotoxicity (H-HT):  0.154
Drug-inuced Liver Injury (DILI):  0.961
AMES Toxicity:  0.501
Rat Oral Acute Toxicity:  0.893
Maximum Recommended Daily Dose:  0.568
Skin Sensitization:  0.679
Carcinogencity:  0.068
Eye Corrosion:  0.003
Eye Irritation:  0.616
Respiratory Toxicity:  0.169

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

  Natural Product: NPC287789

Natural Product ID:  NPC287789
Common Name*:   (2S)-3-[(2S,3S)-5,7-Dihydroxy-2-(4-Methoxyphenyl)-4-Oxo-2,3-Dihydrochromen-3-Yl]-5,7-Dihydroxy-2-(4-Methoxyphenyl)-2,3-Dihydrochromen-4-One
IUPAC Name:   (2S)-3-[(2S,3S)-5,7-dihydroxy-2-(4-methoxyphenyl)-4-oxo-2,3-dihydrochromen-3-yl]-5,7-dihydroxy-2-(4-methoxyphenyl)-2,3-dihydrochromen-4-one
Synonyms:  
Standard InCHIKey:  BTCICADMSGBCKA-VGVWILAUSA-N
Standard InCHI:  InChI=1S/C32H26O10/c1-39-19-7-3-15(4-8-19)31-27(29(37)25-21(35)11-17(33)13-23(25)41-31)28-30(38)26-22(36)12-18(34)14-24(26)42-32(28)16-5-9-20(40-2)10-6-16/h3-14,27-28,31-36H,1-2H3/t27-,28?,31-,32-/m1/s1
SMILES:  COc1ccc(cc1)[C@H]1Oc2cc(O)cc(c2C(=O)C1[C@H]1[C@H](Oc2c(C1=O)c(O)cc(c2)O)c1ccc(cc1)OC)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1545093
PubChem CID:   16745525
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0000334] Flavonoids
        • [CHEMONTID:0001586] Biflavonoids and polyflavonoids

*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
NPO7067 Stellera chamaejasme Species Thymelaeaceae Eukaryota n.a. root n.a. PMID[15997133]
NPO7067 Stellera chamaejasme Species Thymelaeaceae Eukaryota n.a. root n.a. PMID[16141313]
NPO7067 Stellera chamaejasme Species Thymelaeaceae Eukaryota n.a. callus n.a. PMID[22368856]
NPO7067 Stellera chamaejasme Species Thymelaeaceae Eukaryota n.a. n.a. n.a. PMID[23611151]
NPO7067 Stellera chamaejasme Species Thymelaeaceae Eukaryota roots n.a. n.a. PMID[24931277]
NPO7067 Stellera chamaejasme Species Thymelaeaceae Eukaryota n.a. n.a. n.a. PMID[26562066]
NPO7067 Stellera chamaejasme Species Thymelaeaceae Eukaryota n.a. root n.a. Database[Article]
NPO7067 Stellera chamaejasme Species Thymelaeaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO7067 Stellera chamaejasme Species Thymelaeaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7067 Stellera chamaejasme Species Thymelaeaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO7067 Stellera chamaejasme Species Thymelaeaceae 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
NPT46 Individual Protein Thyroid hormone receptor beta-1 Homo sapiens Potency = 70794.6 nM PMID[475138]
NPT1197 Individual Protein Huntingtin Homo sapiens Potency = 1122.0 nM PMID[475138]
NPT51 Individual Protein Microtubule-associated protein tau Homo sapiens Potency = 11220.2 nM PMID[475138]
NPT531 Individual Protein Nuclear receptor ROR-gamma Mus musculus Potency = 22387.2 nM PMID[475138]
NPT54 Individual Protein Nonstructural protein 1 Influenza A virus Potency = 316.2 nM PMID[475138]
NPT51 Individual Protein Microtubule-associated protein tau Homo sapiens Potency = 17782.8 nM PMID[475138]
NPT1254 Individual Protein Streptokinase A Streptococcus pyogenes serotype M1 EC50 = 1611.0 nM PMID[475138]
NPT58 Individual Protein Bloom syndrome protein Homo sapiens Potency = 15848.9 nM PMID[475138]
NPT1254 Individual Protein Streptokinase A Streptococcus pyogenes serotype M1 EC50 = 1705.0 nM PMID[475138]
NPT59 Individual Protein DNA polymerase beta Homo sapiens Potency = 79432.8 nM PMID[475138]
NPT532 Individual Protein Lysine-specific demethylase 4A Homo sapiens Potency n.a. 50118.7 nM PMID[475138]
NPT2892 Individual Protein X-box-binding protein 1 Homo sapiens IC50 > 10000.0 nM PMID[475138]
NPT2893 Individual Protein DNA damage-inducible transcript 3 protein Mus musculus IC50 > 10000.0 nM PMID[475138]
NPT65 Cell Line HepG2 Homo sapiens Potency n.a. 25118.9 nM PMID[475138]
NPT154 Individual Protein Mothers against decapentaplegic homolog 3 Homo sapiens Potency n.a. 14125.4 nM PMID[475138]
NPT10 Individual Protein Geminin Homo sapiens Potency n.a. 5.8 nM PMID[475138]
NPT100 Individual Protein Glutaminase kidney isoform, mitochondrial Homo sapiens Potency n.a. 14125.4 nM PMID[475138]
NPT101 Individual Protein Glucagon-like peptide 1 receptor Homo sapiens Potency n.a. 11220.2 nM PMID[475138]
NPT50 Individual Protein Tyrosyl-DNA phosphodiesterase 1 Homo sapiens Potency n.a. 29092.9 nM PMID[475138]
NPT160 Individual Protein TAR DNA-binding protein 43 Homo sapiens Potency n.a. 35481.3 nM PMID[475138]
NPT11 Individual Protein Guanine nucleotide-binding protein G(s), subunit alpha Homo sapiens Potency n.a. 35481.3 nM PMID[475138]
NPT197 Protein-Protein Interaction Menin/Histone-lysine N-methyltransferase MLL Homo sapiens Potency = 39810.7 nM PMID[475138]
NPT174 Organism Streptococcus Streptococcus EC50 = 2418.0 nM PMID[475138]
NPT1252 Organism Streptococcus sp. 'group A' Streptococcus sp. 'group A' EC50 = 2338.0 nM PMID[475138]
NPT312 Organism Saccharomyces cerevisiae Saccharomyces cerevisiae Potency = 19952.6 nM PMID[475138]
NPT536 Uncleic Acid microRNA 21 Homo sapiens Potency = 16481.6 nM PMID[475138]
NPT2 Others Unspecified Potency = 29092.9 nM PMID[475138]
NPT2 Others Unspecified AC50 = 7403.0 nM PMID[475138]
NPT2 Others Unspecified Potency n.a. 17782.8 nM PMID[475138]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum Potency n.a. 13115.4 nM PMID[475138]
NPT2 Others Unspecified AC50 = 10600.0 nM PMID[475138]
NPT803 Individual Protein Flap endonuclease 1 Homo sapiens Potency n.a. 50118.7 nM PMID[475138]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum Potency n.a. 10417.9 nM PMID[475138]
NPT861 Individual Protein Isocitrate dehydrogenase [NADP] cytoplasmic Homo sapiens Potency n.a. 63095.7 nM PMID[475138]
NPT2 Others Unspecified Potency n.a. 18356.4 nM PMID[475138]
NPT861 Individual Protein Isocitrate dehydrogenase [NADP] cytoplasmic Homo sapiens Potency n.a. 29092.9 nM PMID[475138]
NPT920 Individual Protein Alpha-synuclein Homo sapiens Potency n.a. 35481.3 nM PMID[475138]
NPT2 Others Unspecified Potency n.a. 28183.8 nM PMID[475138]

☑ 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 NPC287789 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 NPC271741
0.9933 High Similarity NPC198489
0.9933 High Similarity NPC61112
0.9866 High Similarity NPC258474
0.9866 High Similarity NPC201227
0.98 High Similarity NPC309648
0.9669 High Similarity NPC69531
0.9605 High Similarity NPC1796
0.9605 High Similarity NPC475184
0.9542 High Similarity NPC51247
0.9539 High Similarity NPC32867
0.9481 High Similarity NPC42965
0.9481 High Similarity NPC226462
0.9481 High Similarity NPC98023
0.9477 High Similarity NPC257166
0.9474 High Similarity NPC134171
0.9474 High Similarity NPC300668
0.9419 High Similarity NPC301256
0.9419 High Similarity NPC312273
0.9416 High Similarity NPC295090
0.9416 High Similarity NPC51760
0.9416 High Similarity NPC105584
0.9416 High Similarity NPC15815
0.9408 High Similarity NPC121568
0.9363 High Similarity NPC473010
0.9359 High Similarity NPC473012
0.9355 High Similarity NPC195136
0.9346 High Similarity NPC182555
0.9346 High Similarity NPC37253
0.9346 High Similarity NPC66441
0.9346 High Similarity NPC79375
0.9342 High Similarity NPC174086
0.9299 High Similarity NPC63438
0.9299 High Similarity NPC473009
0.9276 High Similarity NPC178484
0.9272 High Similarity NPC3642
0.9262 High Similarity NPC311144
0.9231 High Similarity NPC121647
0.9226 High Similarity NPC208258
0.9226 High Similarity NPC318527
0.9226 High Similarity NPC323627
0.9226 High Similarity NPC324358
0.9226 High Similarity NPC322459
0.9221 High Similarity NPC150908
0.9221 High Similarity NPC205026
0.9221 High Similarity NPC215203
0.9221 High Similarity NPC158027
0.9221 High Similarity NPC52611
0.9221 High Similarity NPC100049
0.9221 High Similarity NPC121649
0.9221 High Similarity NPC248739
0.9221 High Similarity NPC265624
0.9221 High Similarity NPC14606
0.9221 High Similarity NPC159707
0.9221 High Similarity NPC186227
0.9216 High Similarity NPC39154
0.9216 High Similarity NPC78324
0.9216 High Similarity NPC115601
0.9216 High Similarity NPC208011
0.9205 High Similarity NPC122894
0.92 High Similarity NPC299011
0.9195 High Similarity NPC113770
0.9182 High Similarity NPC251336
0.9182 High Similarity NPC224851
0.9177 High Similarity NPC38591
0.9156 High Similarity NPC72425
0.9156 High Similarity NPC194593
0.9156 High Similarity NPC303485
0.9156 High Similarity NPC71061
0.9156 High Similarity NPC290830
0.9145 High Similarity NPC473016
0.9139 High Similarity NPC308200
0.9133 High Similarity NPC303185
0.9133 High Similarity NPC184649
0.9119 High Similarity NPC477840
0.9114 High Similarity NPC15374
0.9114 High Similarity NPC473011
0.9091 High Similarity NPC43345
0.9085 High Similarity NPC29777
0.9085 High Similarity NPC471115
0.9079 High Similarity NPC39195
0.9079 High Similarity NPC145467
0.9073 High Similarity NPC470132
0.9073 High Similarity NPC470134
0.9073 High Similarity NPC470131
0.9073 High Similarity NPC470133
0.9073 High Similarity NPC109183
0.9073 High Similarity NPC473078
0.9073 High Similarity NPC228779
0.9062 High Similarity NPC320741
0.9062 High Similarity NPC171985
0.9051 High Similarity NPC18380
0.9045 High Similarity NPC123544
0.9038 High Similarity NPC56049
0.9038 High Similarity NPC54830
0.9032 High Similarity NPC324447
0.9026 High Similarity NPC222713
0.9026 High Similarity NPC148945
0.9026 High Similarity NPC316960
0.9026 High Similarity NPC476553
0.9026 High Similarity NPC476551
0.9026 High Similarity NPC78835
0.9026 High Similarity NPC111112
0.9026 High Similarity NPC309512
0.9026 High Similarity NPC204561
0.9026 High Similarity NPC67322
0.9026 High Similarity NPC317715
0.9026 High Similarity NPC138299
0.9026 High Similarity NPC476552
0.902 High Similarity NPC132345
0.902 High Similarity NPC288840
0.902 High Similarity NPC291746
0.902 High Similarity NPC471114
0.9018 High Similarity NPC168789
0.9013 High Similarity NPC261271
0.9013 High Similarity NPC475348
0.9007 High Similarity NPC271288
0.9007 High Similarity NPC39045
0.9007 High Similarity NPC470135
0.9007 High Similarity NPC470136
0.9 High Similarity NPC202981
0.8994 High Similarity NPC477841
0.8993 High Similarity NPC284550
0.8993 High Similarity NPC129853
0.8993 High Similarity NPC110228
0.8993 High Similarity NPC76445
0.8993 High Similarity NPC188243
0.8993 High Similarity NPC6407
0.8987 High Similarity NPC184326
0.8987 High Similarity NPC292863
0.8957 High Similarity NPC472454
0.8957 High Similarity NPC477529
0.8957 High Similarity NPC186847
0.8957 High Similarity NPC257667
0.8954 High Similarity NPC152233
0.8954 High Similarity NPC35150
0.8954 High Similarity NPC106328
0.8951 High Similarity NPC107627
0.8951 High Similarity NPC53252
0.8947 High Similarity NPC472629
0.8944 High Similarity NPC82330
0.894 High Similarity NPC278249
0.894 High Similarity NPC125894
0.894 High Similarity NPC85162
0.894 High Similarity NPC77794
0.894 High Similarity NPC107177
0.894 High Similarity NPC223812
0.894 High Similarity NPC81697
0.8931 High Similarity NPC137232
0.8931 High Similarity NPC175513
0.8931 High Similarity NPC114652
0.8926 High Similarity NPC140890
0.8926 High Similarity NPC222342
0.8926 High Similarity NPC329203
0.8926 High Similarity NPC265871
0.8926 High Similarity NPC150648
0.8926 High Similarity NPC274784
0.8926 High Similarity NPC310135
0.8926 High Similarity NPC316480
0.8926 High Similarity NPC225153
0.8926 High Similarity NPC20709
0.8924 High Similarity NPC195167
0.8924 High Similarity NPC55443
0.8924 High Similarity NPC18699
0.891 High Similarity NPC203080
0.891 High Similarity NPC112701
0.891 High Similarity NPC326592
0.891 High Similarity NPC109594
0.8903 High Similarity NPC312549
0.8903 High Similarity NPC209142
0.8896 High Similarity NPC287884
0.8896 High Similarity NPC8704
0.8889 High Similarity NPC296998
0.8889 High Similarity NPC10990
0.8889 High Similarity NPC473077
0.8889 High Similarity NPC300988
0.8882 High Similarity NPC282957
0.8882 High Similarity NPC473014
0.8882 High Similarity NPC131568
0.8882 High Similarity NPC131579
0.8882 High Similarity NPC473013
0.8882 High Similarity NPC87486
0.8882 High Similarity NPC124780
0.8882 High Similarity NPC235217
0.8882 High Similarity NPC470890
0.8882 High Similarity NPC169471
0.8882 High Similarity NPC469664
0.8882 High Similarity NPC473015
0.8882 High Similarity NPC194949
0.8875 High Similarity NPC219927
0.8874 High Similarity NPC125855
0.8874 High Similarity NPC107572
0.8874 High Similarity NPC227579
0.8874 High Similarity NPC324436
0.8874 High Similarity NPC76372
0.8874 High Similarity NPC220998
0.8874 High Similarity NPC223500
0.8874 High Similarity NPC64915
0.8874 High Similarity NPC166934
0.8874 High Similarity NPC1089

  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 NPC287789 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
0.9221 High Similarity NPD8443 Clinical (unspecified phase)
0.9051 High Similarity NPD6959 Discontinued
0.8882 High Similarity NPD7852 Clinical (unspecified phase)
0.8792 High Similarity NPD1552 Clinical (unspecified phase)
0.8792 High Similarity NPD1550 Clinical (unspecified phase)
0.8765 High Similarity NPD6167 Clinical (unspecified phase)
0.8765 High Similarity NPD6168 Clinical (unspecified phase)
0.8765 High Similarity NPD6166 Phase 2
0.8733 High Similarity NPD1549 Phase 2
0.8662 High Similarity NPD7411 Suspended
0.8636 High Similarity NPD7410 Clinical (unspecified phase)
0.8636 High Similarity NPD4378 Clinical (unspecified phase)
0.8599 High Similarity NPD4380 Phase 2
0.8562 High Similarity NPD7768 Phase 2
0.8553 High Similarity NPD2393 Clinical (unspecified phase)
0.8509 High Similarity NPD4381 Clinical (unspecified phase)
0.8494 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.8491 Intermediate Similarity NPD1934 Approved
0.8477 Intermediate Similarity NPD2796 Approved
0.8438 Intermediate Similarity NPD7819 Suspended
0.8411 Intermediate Similarity NPD1510 Phase 2
0.8395 Intermediate Similarity NPD3749 Approved
0.8395 Intermediate Similarity NPD7075 Discontinued
0.8393 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.8333 Intermediate Similarity NPD7074 Phase 3
0.8333 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.8293 Intermediate Similarity NPD5494 Approved
0.8274 Intermediate Similarity NPD7054 Approved
0.8267 Intermediate Similarity NPD1240 Approved
0.8225 Intermediate Similarity NPD7472 Approved
0.821 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.821 Intermediate Similarity NPD2801 Approved
0.8187 Intermediate Similarity NPD7808 Phase 3
0.8176 Intermediate Similarity NPD6797 Phase 2
0.8158 Intermediate Similarity NPD1607 Approved
0.8155 Intermediate Similarity NPD7473 Discontinued
0.8129 Intermediate Similarity NPD7251 Discontinued
0.8121 Intermediate Similarity NPD4908 Phase 1
0.8101 Intermediate Similarity NPD1511 Approved
0.8084 Intermediate Similarity NPD6232 Discontinued
0.8037 Intermediate Similarity NPD6801 Discontinued
0.8035 Intermediate Similarity NPD8312 Approved
0.8035 Intermediate Similarity NPD8313 Approved
0.8025 Intermediate Similarity NPD3750 Approved
0.8013 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.8 Intermediate Similarity NPD1512 Approved
0.8 Intermediate Similarity NPD3818 Discontinued
0.8 Intermediate Similarity NPD3882 Suspended
0.7987 Intermediate Similarity NPD7390 Discontinued
0.7987 Intermediate Similarity NPD6799 Approved
0.7962 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7962 Intermediate Similarity NPD2800 Approved
0.7949 Intermediate Similarity NPD2344 Approved
0.7939 Intermediate Similarity NPD3817 Phase 2
0.7914 Intermediate Similarity NPD6599 Discontinued
0.7898 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7874 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.7849 Intermediate Similarity NPD5844 Phase 1
0.784 Intermediate Similarity NPD5403 Approved
0.7831 Intermediate Similarity NPD5402 Approved
0.7821 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7816 Intermediate Similarity NPD6559 Discontinued
0.7778 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7771 Intermediate Similarity NPD1551 Phase 2
0.7771 Intermediate Similarity NPD8455 Phase 2
0.7759 Intermediate Similarity NPD5953 Discontinued
0.775 Intermediate Similarity NPD2309 Approved
0.7744 Intermediate Similarity NPD3226 Approved
0.7716 Intermediate Similarity NPD2534 Approved
0.7716 Intermediate Similarity NPD2533 Approved
0.7716 Intermediate Similarity NPD2532 Approved
0.7716 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7716 Intermediate Similarity NPD5401 Approved
0.7707 Intermediate Similarity NPD3748 Approved
0.7707 Intermediate Similarity NPD2799 Discontinued
0.7692 Intermediate Similarity NPD6651 Approved
0.7688 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.767 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.7665 Intermediate Similarity NPD1465 Phase 2
0.7658 Intermediate Similarity NPD6100 Approved
0.7658 Intermediate Similarity NPD6099 Approved
0.7651 Intermediate Similarity NPD1610 Phase 2
0.7637 Intermediate Similarity NPD4363 Phase 3
0.7637 Intermediate Similarity NPD4360 Phase 2
0.7622 Intermediate Similarity NPD920 Approved
0.7616 Intermediate Similarity NPD3926 Phase 2
0.7611 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7595 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.7586 Intermediate Similarity NPD3751 Discontinued
0.7579 Intermediate Similarity NPD8151 Discontinued
0.7578 Intermediate Similarity NPD4628 Phase 3
0.7558 Intermediate Similarity NPD3787 Discontinued
0.7547 Intermediate Similarity NPD2935 Discontinued
0.7543 Intermediate Similarity NPD7286 Phase 2
0.7533 Intermediate Similarity NPD1547 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD7696 Phase 3
0.75 Intermediate Similarity NPD7698 Approved
0.75 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD7697 Approved
0.746 Intermediate Similarity NPD7871 Phase 2
0.746 Intermediate Similarity NPD7870 Phase 2
0.7459 Intermediate Similarity NPD8090 Clinical (unspecified phase)
0.744 Intermediate Similarity NPD7615 Clinical (unspecified phase)
0.7436 Intermediate Similarity NPD3268 Approved
0.7436 Intermediate Similarity NPD2313 Discontinued
0.7433 Intermediate Similarity NPD6779 Approved
0.7433 Intermediate Similarity NPD6780 Approved
0.7433 Intermediate Similarity NPD6781 Approved
0.7433 Intermediate Similarity NPD6782 Approved
0.7433 Intermediate Similarity NPD6776 Approved
0.7433 Intermediate Similarity NPD6777 Approved
0.7433 Intermediate Similarity NPD6778 Approved
0.7425 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7425 Intermediate Similarity NPD7458 Discontinued
0.7419 Intermediate Similarity NPD6832 Phase 2
0.7418 Intermediate Similarity NPD4287 Approved
0.7407 Intermediate Similarity NPD1243 Approved
0.7403 Intermediate Similarity NPD2798 Approved
0.7391 Intermediate Similarity NPD2346 Discontinued
0.7378 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.7375 Intermediate Similarity NPD7033 Discontinued
0.7362 Intermediate Similarity NPD7003 Approved
0.7362 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7356 Intermediate Similarity NPD7229 Phase 3
0.7344 Intermediate Similarity NPD7701 Phase 2
0.7342 Intermediate Similarity NPD943 Approved
0.7338 Intermediate Similarity NPD2797 Approved
0.7338 Intermediate Similarity NPD1203 Approved
0.732 Intermediate Similarity NPD7783 Phase 2
0.732 Intermediate Similarity NPD7782 Clinical (unspecified phase)
0.7316 Intermediate Similarity NPD7435 Discontinued
0.7312 Intermediate Similarity NPD7097 Phase 1
0.7308 Intermediate Similarity NPD8150 Discontinued
0.7308 Intermediate Similarity NPD8434 Phase 2
0.7305 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7299 Intermediate Similarity NPD7199 Phase 2
0.7296 Intermediate Similarity NPD5124 Phase 1
0.7296 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.7289 Intermediate Similarity NPD7422 Clinical (unspecified phase)
0.7288 Intermediate Similarity NPD7228 Approved
0.7284 Intermediate Similarity NPD2343 Clinical (unspecified phase)
0.7267 Intermediate Similarity NPD1548 Phase 1
0.7257 Intermediate Similarity NPD5711 Approved
0.7257 Intermediate Similarity NPD5710 Approved
0.7253 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7244 Intermediate Similarity NPD2861 Phase 2
0.7234 Intermediate Similarity NPD7700 Phase 2
0.7234 Intermediate Similarity NPD7699 Phase 2
0.7233 Intermediate Similarity NPD1613 Approved
0.7233 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7231 Intermediate Similarity NPD7801 Approved
0.7229 Intermediate Similarity NPD7212 Phase 2
0.7229 Intermediate Similarity NPD7213 Phase 3
0.7222 Intermediate Similarity NPD5405 Approved
0.7222 Intermediate Similarity NPD5404 Approved
0.7222 Intermediate Similarity NPD5406 Approved
0.7222 Intermediate Similarity NPD5408 Approved
0.7219 Intermediate Similarity NPD4362 Clinical (unspecified phase)
0.7219 Intermediate Similarity NPD4361 Phase 2
0.7216 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7215 Intermediate Similarity NPD6798 Discontinued
0.7215 Intermediate Similarity NPD3764 Approved
0.7209 Intermediate Similarity NPD2296 Approved
0.72 Intermediate Similarity NPD1247 Approved
0.7193 Intermediate Similarity NPD6844 Discontinued
0.7193 Intermediate Similarity NPD37 Approved
0.7193 Intermediate Similarity NPD7577 Discontinued
0.7191 Intermediate Similarity NPD7893 Clinical (unspecified phase)
0.7188 Intermediate Similarity NPD8319 Approved
0.7188 Intermediate Similarity NPD8320 Phase 1
0.7186 Intermediate Similarity NPD7447 Phase 1
0.7184 Intermediate Similarity NPD6234 Discontinued
0.7179 Intermediate Similarity NPD7874 Approved
0.7179 Intermediate Similarity NPD7875 Clinical (unspecified phase)
0.7168 Intermediate Similarity NPD4965 Approved
0.7168 Intermediate Similarity NPD4967 Phase 2
0.7168 Intermediate Similarity NPD4966 Approved
0.7166 Intermediate Similarity NPD6534 Approved
0.7166 Intermediate Similarity NPD6535 Approved
0.7158 Intermediate Similarity NPD7501 Clinical (unspecified phase)
0.7151 Intermediate Similarity NPD5760 Phase 2
0.7151 Intermediate Similarity NPD5761 Phase 2
0.7143 Intermediate Similarity NPD9717 Approved
0.7143 Intermediate Similarity NPD1608 Approved
0.7143 Intermediate Similarity NPD6273 Approved
0.7115 Intermediate Similarity NPD3267 Approved
0.7115 Intermediate Similarity NPD3266 Approved
0.7115 Intermediate Similarity NPD1470 Approved
0.7113 Intermediate Similarity NPD7584 Approved
0.711 Intermediate Similarity NPD4288 Approved
0.7097 Intermediate Similarity NPD4749 Approved
0.7095 Intermediate Similarity NPD7177 Discontinued
0.7093 Intermediate Similarity NPD6279 Approved
0.7093 Intermediate Similarity NPD6280 Approved
0.7091 Intermediate Similarity NPD2654 Approved
0.7089 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7086 Intermediate Similarity NPD919 Approved
0.7083 Intermediate Similarity NPD6823 Phase 2
0.7081 Intermediate Similarity NPD230 Phase 1
0.7081 Intermediate Similarity NPD1899 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