Structure

Physi-Chem Properties

Molecular Weight:  582.15
Volume:  582.261
LogP:  5.279
LogD:  3.694
LogS:  -4.431
# Rotatable Bonds:  11
TPSA:  119.73
# H-Bond Aceptor:  10
# H-Bond Donor:  0
# Rings:  5
# Heavy Atoms:  10

MedChem Properties

QED Drug-Likeness Score:  0.153
Synthetic Accessibility Score:  2.612
Fsp3:  0.121
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:  -4.934
MDCK Permeability:  5.956184395472519e-05
Pgp-inhibitor:  1.0
Pgp-substrate:  0.0
Human Intestinal Absorption (HIA):  0.013
20% Bioavailability (F20%):  0.005
30% Bioavailability (F30%):  0.012

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.039
Plasma Protein Binding (PPB):  94.62747955322266%
Volume Distribution (VD):  0.39
Pgp-substrate:  7.499934196472168%

ADMET: Metabolism

CYP1A2-inhibitor:  0.126
CYP1A2-substrate:  0.879
CYP2C19-inhibitor:  0.812
CYP2C19-substrate:  0.067
CYP2C9-inhibitor:  0.931
CYP2C9-substrate:  0.927
CYP2D6-inhibitor:  0.0
CYP2D6-substrate:  0.333
CYP3A4-inhibitor:  0.205
CYP3A4-substrate:  0.205

ADMET: Excretion

Clearance (CL):  4.643
Half-life (T1/2):  0.478

ADMET: Toxicity

hERG Blockers:  0.057
Human Hepatotoxicity (H-HT):  0.005
Drug-inuced Liver Injury (DILI):  0.967
AMES Toxicity:  0.108
Rat Oral Acute Toxicity:  0.057
Maximum Recommended Daily Dose:  0.051
Skin Sensitization:  0.855
Carcinogencity:  0.118
Eye Corrosion:  0.003
Eye Irritation:  0.495
Respiratory Toxicity:  0.092

Download Data

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

  Natural Product: NPC280893

Natural Product ID:  NPC280893
Common Name*:   5,3'-Dibenzoyloxy-3,6,7,4'-Tetramethoxyflavone
IUPAC Name:   [5-(5-benzoyloxy-3,6,7-trimethoxy-4-oxochromen-2-yl)-2-methoxyphenyl] benzoate
Synonyms:  
Standard InCHIKey:  YCVPZUVDLDIFOQ-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C33H26O10/c1-37-22-16-15-21(17-23(22)42-32(35)19-11-7-5-8-12-19)28-31(40-4)27(34)26-24(41-28)18-25(38-2)29(39-3)30(26)43-33(36)20-13-9-6-10-14-20/h5-18H,1-4H3
SMILES:  COc1ccc(cc1OC(=O)c1ccccc1)c1oc2cc(OC)c(c(c2c(=O)c1OC)OC(=O)c1ccccc1)OC
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL442648
PubChem CID:   11006401
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0001645] Depsides and depsidones

*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
NPO14602 Vitex negundo Species Lamiaceae Eukaryota leaves n.a. n.a. PMID[12828478]
NPO14602 Vitex negundo Species Lamiaceae Eukaryota n.a. root n.a. PMID[15520511]
NPO14602 Vitex negundo Species Lamiaceae Eukaryota seeds n.a. n.a. PMID[15620254]
NPO14602 Vitex negundo Species Lamiaceae Eukaryota seeds n.a. n.a. PMID[1624939]
NPO14602 Vitex negundo Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[17027268]
NPO14602 Vitex negundo Species Lamiaceae Eukaryota Seeds n.a. n.a. PMID[19715321]
NPO14602 Vitex negundo Species Lamiaceae Eukaryota Seeds n.a. n.a. PMID[19931461]
NPO14602 Vitex negundo Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[23403897]
NPO14602 Vitex negundo Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO14602 Vitex negundo Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14602 Vitex negundo Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO14602 Vitex negundo Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO14602 Vitex negundo Species Lamiaceae 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
NPT1851 Cell Line Col2 Homo sapiens ED50 > 20.0 ug ml-1 PMID[460921]
NPT737 Cell Line HUVEC Homo sapiens ED50 > 20.0 ug ml-1 PMID[460921]
NPT91 Cell Line KB Homo sapiens ED50 > 20.0 ug ml-1 PMID[460921]
NPT858 Cell Line LNCaP Homo sapiens ED50 > 20.0 ug ml-1 PMID[460921]
NPT1034 Cell Line Lu1 Homo sapiens ED50 = 6.5 ug ml-1 PMID[460921]
NPT27 Others Unspecified ED50 = 4.3 ug ml-1 PMID[460921]

☑ 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 NPC280893 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
0.9484 High Similarity NPC276059
0.9484 High Similarity NPC241774
0.9484 High Similarity NPC34725
0.9484 High Similarity NPC122623
0.9423 High Similarity NPC257277
0.9321 High Similarity NPC280493
0.929 High Similarity NPC474388
0.929 High Similarity NPC472535
0.929 High Similarity NPC474170
0.9226 High Similarity NPC259058
0.9226 High Similarity NPC177839
0.9226 High Similarity NPC201547
0.9172 High Similarity NPC186507
0.9161 High Similarity NPC69752
0.9161 High Similarity NPC181250
0.9125 High Similarity NPC188967
0.9091 High Similarity NPC476370
0.9062 High Similarity NPC154304
0.9062 High Similarity NPC190487
0.9045 High Similarity NPC198615
0.9045 High Similarity NPC474663
0.9036 High Similarity NPC476374
0.9032 High Similarity NPC205522
0.9032 High Similarity NPC85233
0.9032 High Similarity NPC299923
0.8994 High Similarity NPC471746
0.8987 High Similarity NPC134677
0.8982 High Similarity NPC99591
0.8981 High Similarity NPC29056
0.8968 High Similarity NPC40818
0.8968 High Similarity NPC310259
0.8968 High Similarity NPC302408
0.8968 High Similarity NPC215932
0.8968 High Similarity NPC106461
0.8968 High Similarity NPC110639
0.8968 High Similarity NPC283002
0.8968 High Similarity NPC14958
0.8957 High Similarity NPC272064
0.8944 High Similarity NPC238405
0.8944 High Similarity NPC257914
0.8944 High Similarity NPC104459
0.8938 High Similarity NPC178854
0.8917 High Similarity NPC474648
0.8903 High Similarity NPC165512
0.8903 High Similarity NPC136278
0.8902 High Similarity NPC475369
0.8896 High Similarity NPC475144
0.8889 High Similarity NPC470416
0.8882 High Similarity NPC183
0.8875 High Similarity NPC32557
0.8875 High Similarity NPC189960
0.8855 High Similarity NPC476180
0.8854 High Similarity NPC63256
0.8854 High Similarity NPC10304
0.8854 High Similarity NPC183236
0.8848 High Similarity NPC475214
0.8839 High Similarity NPC113089
0.8839 High Similarity NPC23955
0.8837 High Similarity NPC226725
0.8834 High Similarity NPC196179
0.8834 High Similarity NPC34089
0.883 High Similarity NPC36138
0.8827 High Similarity NPC204854
0.8827 High Similarity NPC176300
0.8827 High Similarity NPC253634
0.8827 High Similarity NPC261004
0.8827 High Similarity NPC288669
0.8827 High Similarity NPC115798
0.8827 High Similarity NPC22472
0.8827 High Similarity NPC18772
0.8827 High Similarity NPC4481
0.8827 High Similarity NPC19687
0.8827 High Similarity NPC300943
0.8827 High Similarity NPC152166
0.8827 High Similarity NPC193842
0.8827 High Similarity NPC9609
0.8827 High Similarity NPC7846
0.8827 High Similarity NPC18607
0.8827 High Similarity NPC25495
0.8827 High Similarity NPC105242
0.8827 High Similarity NPC287458
0.8827 High Similarity NPC191459
0.8827 High Similarity NPC143828
0.8827 High Similarity NPC130894
0.8812 High Similarity NPC472408
0.8812 High Similarity NPC476289
0.8812 High Similarity NPC246204
0.8812 High Similarity NPC86485
0.8802 High Similarity NPC475434
0.8802 High Similarity NPC476365
0.8795 High Similarity NPC295082
0.879 High Similarity NPC117463
0.8788 High Similarity NPC142614
0.878 High Similarity NPC108767
0.8779 High Similarity NPC154527
0.8774 High Similarity NPC70853
0.8774 High Similarity NPC9966
0.8773 High Similarity NPC131557
0.8773 High Similarity NPC98892
0.8773 High Similarity NPC477164
0.8765 High Similarity NPC7973
0.8765 High Similarity NPC93376
0.8765 High Similarity NPC163524
0.8765 High Similarity NPC110070
0.8765 High Similarity NPC287979
0.8765 High Similarity NPC305663
0.8765 High Similarity NPC472438
0.8765 High Similarity NPC227192
0.8765 High Similarity NPC203891
0.8765 High Similarity NPC189179
0.8765 High Similarity NPC101830
0.8765 High Similarity NPC78302
0.8765 High Similarity NPC185526
0.8765 High Similarity NPC176665
0.8765 High Similarity NPC224137
0.8765 High Similarity NPC477895
0.8765 High Similarity NPC75215
0.8765 High Similarity NPC29841
0.8765 High Similarity NPC235215
0.8758 High Similarity NPC284353
0.8758 High Similarity NPC222185
0.875 High Similarity NPC301123
0.875 High Similarity NPC166201
0.8735 High Similarity NPC155264
0.8735 High Similarity NPC67450
0.8735 High Similarity NPC193881
0.8735 High Similarity NPC210460
0.8734 High Similarity NPC261548
0.8728 High Similarity NPC104910
0.8728 High Similarity NPC474093
0.8726 High Similarity NPC216314
0.8726 High Similarity NPC195919
0.8726 High Similarity NPC231013
0.8726 High Similarity NPC120924
0.8721 High Similarity NPC297503
0.8721 High Similarity NPC97119
0.8721 High Similarity NPC135831
0.871 High Similarity NPC124467
0.871 High Similarity NPC214919
0.871 High Similarity NPC29536
0.8704 High Similarity NPC292107
0.8704 High Similarity NPC55619
0.8704 High Similarity NPC245546
0.8704 High Similarity NPC49824
0.8704 High Similarity NPC98661
0.8704 High Similarity NPC43243
0.8704 High Similarity NPC268161
0.8704 High Similarity NPC266960
0.8704 High Similarity NPC100916
0.8704 High Similarity NPC180340
0.8704 High Similarity NPC474520
0.8704 High Similarity NPC247017
0.8704 High Similarity NPC200388
0.8704 High Similarity NPC474983
0.8704 High Similarity NPC265511
0.8696 High Similarity NPC279930
0.8696 High Similarity NPC128961
0.869 High Similarity NPC72696
0.8688 High Similarity NPC208043
0.8688 High Similarity NPC76376
0.8688 High Similarity NPC308451
0.8688 High Similarity NPC236769
0.8688 High Similarity NPC226973
0.8683 High Similarity NPC243877
0.8679 High Similarity NPC238366
0.8678 High Similarity NPC475179
0.8667 High Similarity NPC414831
0.8663 High Similarity NPC47883
0.8662 High Similarity NPC471590
0.8655 High Similarity NPC35167
0.8655 High Similarity NPC98546
0.8655 High Similarity NPC139571
0.8655 High Similarity NPC297807
0.8655 High Similarity NPC217520
0.865 High Similarity NPC112954
0.865 High Similarity NPC19097
0.8647 High Similarity NPC264735
0.8645 High Similarity NPC474037
0.8645 High Similarity NPC58229
0.8642 High Similarity NPC26227
0.8642 High Similarity NPC163780
0.8642 High Similarity NPC50715
0.8642 High Similarity NPC20830
0.8642 High Similarity NPC183597
0.8642 High Similarity NPC138360
0.8642 High Similarity NPC214138
0.8642 High Similarity NPC167815
0.8642 High Similarity NPC256612
0.8642 High Similarity NPC201136
0.8642 High Similarity NPC146165
0.8642 High Similarity NPC196439
0.8642 High Similarity NPC44079
0.8642 High Similarity NPC92659
0.8642 High Similarity NPC208197
0.8642 High Similarity NPC128863
0.8642 High Similarity NPC4455
0.8642 High Similarity NPC2476
0.8642 High Similarity NPC201451
0.8642 High Similarity NPC227325
0.8642 High Similarity NPC280339

  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 NPC280893 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
0.8994 High Similarity NPD3817 Phase 2
0.858 High Similarity NPD2801 Approved
0.8538 High Similarity NPD4338 Clinical (unspecified phase)
0.8528 High Similarity NPD5402 Approved
0.8452 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.8452 Intermediate Similarity NPD6166 Phase 2
0.8452 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.8434 Intermediate Similarity NPD5494 Approved
0.8421 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.8373 Intermediate Similarity NPD919 Approved
0.8365 Intermediate Similarity NPD6799 Approved
0.8364 Intermediate Similarity NPD3882 Suspended
0.8324 Intermediate Similarity NPD7808 Phase 3
0.8274 Intermediate Similarity NPD1247 Approved
0.8253 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.821 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.8208 Intermediate Similarity NPD6797 Phase 2
0.8198 Intermediate Similarity NPD5844 Phase 1
0.8182 Intermediate Similarity NPD6801 Discontinued
0.8176 Intermediate Similarity NPD3926 Phase 2
0.8161 Intermediate Similarity NPD7251 Discontinued
0.8148 Intermediate Similarity NPD1512 Approved
0.8133 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.8118 Intermediate Similarity NPD6232 Discontinued
0.8098 Intermediate Similarity NPD5403 Approved
0.8095 Intermediate Similarity NPD7075 Discontinued
0.8092 Intermediate Similarity NPD7054 Approved
0.8086 Intermediate Similarity NPD5401 Approved
0.8081 Intermediate Similarity NPD7473 Discontinued
0.8072 Intermediate Similarity NPD1934 Approved
0.8061 Intermediate Similarity NPD6599 Discontinued
0.8046 Intermediate Similarity NPD7472 Approved
0.8038 Intermediate Similarity NPD2796 Approved
0.8035 Intermediate Similarity NPD3818 Discontinued
0.8025 Intermediate Similarity NPD1511 Approved
0.8024 Intermediate Similarity NPD7819 Suspended
0.8023 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.8012 Intermediate Similarity NPD7411 Suspended
0.7975 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.7944 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7943 Intermediate Similarity NPD7074 Phase 3
0.7917 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7886 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.7866 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.7824 Intermediate Similarity NPD7768 Phase 2
0.7811 Intermediate Similarity NPD1465 Phase 2
0.7778 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.7778 Intermediate Similarity NPD3749 Approved
0.7771 Intermediate Similarity NPD920 Approved
0.776 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.775 Intermediate Similarity NPD3748 Approved
0.7746 Intermediate Similarity NPD6959 Discontinued
0.7738 Intermediate Similarity NPD4380 Phase 2
0.7673 Intermediate Similarity NPD1933 Approved
0.7673 Intermediate Similarity NPD447 Suspended
0.7669 Intermediate Similarity NPD1243 Approved
0.7661 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.7657 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7651 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7614 Intermediate Similarity NPD7784 Clinical (unspecified phase)
0.76 Intermediate Similarity NPD3787 Discontinued
0.758 Intermediate Similarity NPD6832 Phase 2
0.7531 Intermediate Similarity NPD1510 Phase 2
0.753 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.7528 Intermediate Similarity NPD3751 Discontinued
0.7515 Intermediate Similarity NPD3750 Approved
0.75 Intermediate Similarity NPD1549 Phase 2
0.75 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7485 Intermediate Similarity NPD2935 Discontinued
0.7471 Intermediate Similarity NPD3226 Approved
0.747 Intermediate Similarity NPD6190 Approved
0.7455 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7453 Intermediate Similarity NPD1899 Clinical (unspecified phase)
0.7443 Intermediate Similarity NPD7199 Phase 2
0.7439 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.7439 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.7407 Intermediate Similarity NPD8090 Clinical (unspecified phase)
0.7391 Intermediate Similarity NPD1240 Approved
0.7391 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7381 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7377 Intermediate Similarity NPD8313 Approved
0.7377 Intermediate Similarity NPD8312 Approved
0.7375 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7363 Intermediate Similarity NPD6559 Discontinued
0.736 Intermediate Similarity NPD5242 Approved
0.7329 Intermediate Similarity NPD6233 Phase 2
0.731 Intermediate Similarity NPD1653 Approved
0.7301 Intermediate Similarity NPD1607 Approved
0.7283 Intermediate Similarity NPD6386 Approved
0.7283 Intermediate Similarity NPD6385 Approved
0.7273 Intermediate Similarity NPD1551 Phase 2
0.7268 Intermediate Similarity NPD7435 Discontinued
0.7267 Intermediate Similarity NPD2313 Discontinued
0.7257 Intermediate Similarity NPD5353 Approved
0.7239 Intermediate Similarity NPD230 Phase 1
0.7228 Intermediate Similarity NPD7549 Discontinued
0.7212 Intermediate Similarity NPD2799 Discontinued
0.7202 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7178 Intermediate Similarity NPD943 Approved
0.7176 Intermediate Similarity NPD7390 Discontinued
0.7166 Intermediate Similarity NPD8150 Discontinued
0.7166 Intermediate Similarity NPD8434 Phase 2
0.716 Intermediate Similarity NPD6798 Discontinued
0.7151 Intermediate Similarity NPD8127 Discontinued
0.7143 Intermediate Similarity NPD7870 Phase 2
0.7143 Intermediate Similarity NPD7871 Phase 2
0.7143 Intermediate Similarity NPD37 Approved
0.7136 Intermediate Similarity NPD7875 Clinical (unspecified phase)
0.7136 Intermediate Similarity NPD7874 Approved
0.7135 Intermediate Similarity NPD2533 Approved
0.7135 Intermediate Similarity NPD2534 Approved
0.7135 Intermediate Similarity NPD2532 Approved
0.7127 Intermediate Similarity NPD2403 Approved
0.7126 Intermediate Similarity NPD2346 Discontinued
0.712 Intermediate Similarity NPD5953 Discontinued
0.7119 Intermediate Similarity NPD4965 Approved
0.7119 Intermediate Similarity NPD4967 Phase 2
0.7119 Intermediate Similarity NPD4966 Approved
0.7113 Intermediate Similarity NPD6781 Approved
0.7113 Intermediate Similarity NPD6782 Approved
0.7113 Intermediate Similarity NPD6780 Approved
0.7113 Intermediate Similarity NPD6776 Approved
0.7113 Intermediate Similarity NPD6779 Approved
0.7113 Intermediate Similarity NPD6778 Approved
0.7113 Intermediate Similarity NPD6777 Approved
0.7102 Intermediate Similarity NPD8455 Phase 2
0.7101 Intermediate Similarity NPD4628 Phase 3
0.7093 Intermediate Similarity NPD1940 Clinical (unspecified phase)
0.7092 Intermediate Similarity NPD7698 Approved
0.7092 Intermediate Similarity NPD7696 Phase 3
0.7092 Intermediate Similarity NPD7697 Approved
0.7085 Intermediate Similarity NPD8151 Discontinued
0.7081 Intermediate Similarity NPD7685 Pre-registration
0.7073 Intermediate Similarity NPD4307 Phase 2
0.7063 Intermediate Similarity NPD3267 Approved
0.7063 Intermediate Similarity NPD3266 Approved
0.7063 Intermediate Similarity NPD1203 Approved
0.7062 Intermediate Similarity NPD8285 Discontinued
0.7059 Intermediate Similarity NPD3887 Approved
0.7039 Intermediate Similarity NPD6234 Discontinued
0.7035 Intermediate Similarity NPD3688 Clinical (unspecified phase)
0.7035 Intermediate Similarity NPD3146 Approved
0.7024 Intermediate Similarity NPD2353 Approved
0.7024 Intermediate Similarity NPD2355 Clinical (unspecified phase)
0.7019 Intermediate Similarity NPD1019 Discontinued
0.7015 Intermediate Similarity NPD7782 Clinical (unspecified phase)
0.7015 Intermediate Similarity NPD7783 Phase 2
0.7011 Intermediate Similarity NPD7286 Phase 2
0.7006 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.6981 Remote Similarity NPD9717 Approved
0.6971 Remote Similarity NPD7458 Discontinued
0.6957 Remote Similarity NPD7228 Approved
0.6951 Remote Similarity NPD1296 Phase 2
0.6951 Remote Similarity NPD3268 Approved
0.695 Remote Similarity NPD7701 Phase 2
0.6949 Remote Similarity NPD6844 Discontinued
0.6941 Remote Similarity NPD2800 Approved
0.6939 Remote Similarity NPD7501 Clinical (unspecified phase)
0.6936 Remote Similarity NPD7004 Clinical (unspecified phase)
0.6923 Remote Similarity NPD7229 Phase 3
0.6923 Remote Similarity NPD2344 Approved
0.6923 Remote Similarity NPD1471 Phase 3
0.6923 Remote Similarity NPD5536 Phase 2
0.6918 Remote Similarity NPD1547 Clinical (unspecified phase)
0.6914 Remote Similarity NPD2798 Approved
0.6911 Remote Similarity NPD4287 Approved
0.6905 Remote Similarity NPD4308 Phase 3
0.6899 Remote Similarity NPD17 Approved
0.6898 Remote Similarity NPD7038 Approved
0.6898 Remote Similarity NPD7039 Approved
0.6894 Remote Similarity NPD3225 Approved
0.6889 Remote Similarity NPD6971 Discontinued
0.6875 Remote Similarity NPD8155 Clinical (unspecified phase)
0.6872 Remote Similarity NPD4288 Approved
0.6871 Remote Similarity NPD3018 Phase 2
0.6865 Remote Similarity NPD7893 Clinical (unspecified phase)
0.6864 Remote Similarity NPD5404 Approved
0.6864 Remote Similarity NPD5406 Approved
0.6864 Remote Similarity NPD5408 Approved
0.6864 Remote Similarity NPD5405 Approved
0.686 Remote Similarity NPD2354 Approved
0.6856 Remote Similarity NPD6534 Approved
0.6856 Remote Similarity NPD6535 Approved
0.6852 Remote Similarity NPD2797 Approved
0.6851 Remote Similarity NPD5537 Clinical (unspecified phase)
0.6848 Remote Similarity NPD411 Approved
0.6847 Remote Similarity NPD7801 Approved
0.6842 Remote Similarity NPD2654 Approved
0.6837 Remote Similarity NPD7700 Phase 2
0.6837 Remote Similarity NPD7699 Phase 2
0.6829 Remote Similarity NPD1529 Clinical (unspecified phase)
0.6826 Remote Similarity NPD6355 Discontinued
0.6813 Remote Similarity NPD422 Phase 1
0.6809 Remote Similarity NPD7240 Approved
0.6805 Remote Similarity NPD1509 Clinical (unspecified phase)
0.6805 Remote Similarity NPD7033 Discontinued
0.6802 Remote Similarity NPD7003 Approved
0.6802 Remote Similarity NPD6398 Clinical (unspecified phase)
0.68 Remote Similarity NPD8319 Approved
0.68 Remote Similarity NPD8320 Phase 1

  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