Structure

Physi-Chem Properties

Molecular Weight:  800.11
Volume:  719.699
LogP:  1.813
LogD:  1.34
LogS:  -2.412
# Rotatable Bonds:  13
TPSA:  385.26
# H-Bond Aceptor:  22
# H-Bond Donor:  13
# Rings:  5
# Heavy Atoms:  22

MedChem Properties

QED Drug-Likeness Score:  0.065
Synthetic Accessibility Score:  4.23
Fsp3:  0.171
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  1
Golden Triangle Rule:  Rejected
Chelating Alert:  1
PAINS Alert:  1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -6.968
MDCK Permeability:  7.754069883958437e-06
Pgp-inhibitor:  0.0
Pgp-substrate:  0.0
Human Intestinal Absorption (HIA):  0.975
20% Bioavailability (F20%):  1.0
30% Bioavailability (F30%):  1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.004
Plasma Protein Binding (PPB):  83.76806640625%
Volume Distribution (VD):  0.357
Pgp-substrate:  18.5189266204834%

ADMET: Metabolism

CYP1A2-inhibitor:  0.514
CYP1A2-substrate:  0.004
CYP2C19-inhibitor:  0.013
CYP2C19-substrate:  0.014
CYP2C9-inhibitor:  0.388
CYP2C9-substrate:  0.013
CYP2D6-inhibitor:  0.0
CYP2D6-substrate:  0.05
CYP3A4-inhibitor:  0.023
CYP3A4-substrate:  0.011

ADMET: Excretion

Clearance (CL):  8.618
Half-life (T1/2):  0.983

ADMET: Toxicity

hERG Blockers:  0.022
Human Hepatotoxicity (H-HT):  0.081
Drug-inuced Liver Injury (DILI):  0.973
AMES Toxicity:  0.019
Rat Oral Acute Toxicity:  0.0
Maximum Recommended Daily Dose:  0.002
Skin Sensitization:  0.954
Carcinogencity:  0.003
Eye Corrosion:  0.006
Eye Irritation:  0.937
Respiratory Toxicity:  0.001

Download Data

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

  Natural Product: NPC134925

Natural Product ID:  NPC134925
Common Name*:   JQVXKQDWMIXILH-ZVLUUUFJSA-N
IUPAC Name:   n.a.
Synonyms:   1,3,4,5 Tetra-O-Galloylquinic Acid
Standard InCHIKey:  JQVXKQDWMIXILH-ZVLUUUFJSA-N
Standard InCHI:  InChI=1S/C35H28O22/c36-15-1-11(2-16(37)25(15)44)30(48)54-23-9-35(34(52)53,57-33(51)14-7-21(42)28(47)22(43)8-14)10-24(55-31(49)12-3-17(38)26(45)18(39)4-12)29(23)56-32(50)13-5-19(40)27(46)20(41)6-13/h1-8,23-24,29,36-47H,9-10H2,(H,52,53)/t23-,24-,29-,35+/m1/s1
SMILES:  O=C(c1cc(O)c(c(c1)O)O)O[C@@H]1C[C@](C[C@H]([C@H]1OC(=O)c1cc(O)c(c(c1)O)O)OC(=O)c1cc(O)c(c(c1)O)O)(OC(=O)c1cc(O)c(c(c1)O)O)C(=O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL36985
PubChem CID:   n.a.
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0004603] Organic oxygen compounds
      • [CHEMONTID:0000323] Organooxygen compounds
        • [CHEMONTID:0000129] Alcohols and polyols
          • [CHEMONTID:0001292] Cyclic alcohols and derivatives
            • [CHEMONTID:0002509] Cyclitols and derivatives
              • [CHEMONTID:0002512] Quinic acids and derivatives
                • [CHEMONTID:0002513] O-galloylquinic acids and derivatives

*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
NPO32818 lepidobotrys staudtii Species Lepidobotryaceae Eukaryota n.a. Cameroon n.a. PMID[11430019]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

  NP Quantity Composition/Concentration

Organism ID NP ID Organism Material Preparation Organism Part NP Quantity (Standard) NP Quantity (Minimum) NP Quantity (Maximum) Quantity Unit Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT759 Cell Line H9 Homo sapiens Inhibition = 25.0 % PMID[458257]
NPT672 Cell Line TE-671 Homo sapiens ED50 > 10.0 ug ml-1 PMID[458258]
NPT180 Cell Line HCT-8 Homo sapiens ED50 > 10.0 ug ml-1 PMID[458258]
NPT81 Cell Line A549 Homo sapiens ED50 > 10.0 ug ml-1 PMID[458258]
NPT91 Cell Line KB Homo sapiens ED50 > 10.0 ug ml-1 PMID[458258]
NPT459 Individual Protein Human immunodeficiency virus type 1 reverse transcriptase Human immunodeficiency virus 1 IC50 = 800.0 nM PMID[458259]
NPT316 Protein Family Protein kinase C (PKC) Homo sapiens IC50 = 64000.0 nM PMID[458256]
NPT727 Protein Family Protein kinase C, PKC; classical/novel Homo sapiens Phorbol displacement <= 50.0 uM PMID[458256]
NPT2 Others Unspecified Inhibition = 94.0 % PMID[458257]
NPT2 Others Unspecified Inhibition = 84.0 % PMID[458257]
NPT2 Others Unspecified Inhibition = 36.0 % PMID[458257]
NPT24 Organism Human immunodeficiency virus 1 Human immunodeficiency virus 1 Inhibition = 66.0 % PMID[458257]
NPT24 Organism Human immunodeficiency virus 1 Human immunodeficiency virus 1 Inhibition = 52.0 % PMID[458257]
NPT24 Organism Human immunodeficiency virus 1 Human immunodeficiency virus 1 Inhibition = 15.0 % PMID[458257]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. ED50 = 0.43 ug ml-1 PMID[458258]
NPT24 Organism Human immunodeficiency virus 1 Human immunodeficiency virus 1 EC50 = 500.0 nM PMID[458259]
NPT27 Others Unspecified TI = 20.0 n.a. PMID[458259]
NPT3795 Organism Human immunodeficiency virus 2 Human immunodeficiency virus 2 EC50 = 10000000.0 nM PMID[458259]
NPT2 Others Unspecified IC50 = 800.0 nM PMID[458259]

☑ 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 NPC134925 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
0.9662 High Similarity NPC252979
0.94 High Similarity NPC477334
0.9329 High Similarity NPC43123
0.9267 High Similarity NPC42464
0.9226 High Similarity NPC210501
0.9226 High Similarity NPC318826
0.9226 High Similarity NPC114791
0.9226 High Similarity NPC141331
0.9226 High Similarity NPC104222
0.9221 High Similarity NPC239019
0.9221 High Similarity NPC247629
0.9205 High Similarity NPC306343
0.92 High Similarity NPC142528
0.9161 High Similarity NPC238419
0.9161 High Similarity NPC172419
0.9128 High Similarity NPC477333
0.906 High Similarity NPC50221
0.906 High Similarity NPC114242
0.8933 High Similarity NPC226738
0.8933 High Similarity NPC22176
0.8933 High Similarity NPC190587
0.8933 High Similarity NPC121573
0.891 High Similarity NPC145425
0.8903 High Similarity NPC44260
0.8903 High Similarity NPC3746
0.8903 High Similarity NPC16024
0.8903 High Similarity NPC205037
0.8903 High Similarity NPC61152
0.8867 High Similarity NPC284948
0.8867 High Similarity NPC220664
0.8867 High Similarity NPC319628
0.8867 High Similarity NPC37331
0.8867 High Similarity NPC303090
0.8827 High Similarity NPC43918
0.8827 High Similarity NPC261411
0.8827 High Similarity NPC190204
0.8827 High Similarity NPC217781
0.88 High Similarity NPC477335
0.88 High Similarity NPC35702
0.88 High Similarity NPC297517
0.88 High Similarity NPC224389
0.88 High Similarity NPC13818
0.88 High Similarity NPC471027
0.88 High Similarity NPC206095
0.879 High Similarity NPC203757
0.8773 High Similarity NPC198125
0.8773 High Similarity NPC149300
0.8773 High Similarity NPC95421
0.8765 High Similarity NPC175793
0.8765 High Similarity NPC49983
0.8765 High Similarity NPC317671
0.8765 High Similarity NPC142707
0.8765 High Similarity NPC26536
0.8742 High Similarity NPC192831
0.8742 High Similarity NPC277315
0.8742 High Similarity NPC258469
0.8742 High Similarity NPC472016
0.8742 High Similarity NPC43158
0.8734 High Similarity NPC470896
0.8734 High Similarity NPC473275
0.872 High Similarity NPC47521
0.8718 High Similarity NPC163883
0.8718 High Similarity NPC93498
0.8712 High Similarity NPC311389
0.8712 High Similarity NPC470271
0.8704 High Similarity NPC162169
0.8704 High Similarity NPC166851
0.8701 High Similarity NPC192568
0.8701 High Similarity NPC120621
0.8701 High Similarity NPC248257
0.8701 High Similarity NPC471076
0.8688 High Similarity NPC476373
0.8667 High Similarity NPC12218
0.8667 High Similarity NPC100251
0.8667 High Similarity NPC65333
0.8667 High Similarity NPC105525
0.8667 High Similarity NPC476370
0.8667 High Similarity NPC225036
0.8667 High Similarity NPC75763
0.8662 High Similarity NPC19380
0.8662 High Similarity NPC146277
0.8645 High Similarity NPC75945
0.8645 High Similarity NPC92117
0.8636 High Similarity NPC229264
0.8636 High Similarity NPC322660
0.8616 High Similarity NPC104983
0.8616 High Similarity NPC250436
0.8616 High Similarity NPC300845
0.8616 High Similarity NPC88803
0.8616 High Similarity NPC291948
0.8614 High Similarity NPC476374
0.8614 High Similarity NPC98583
0.8606 High Similarity NPC470272
0.86 High Similarity NPC24295
0.86 High Similarity NPC283560
0.86 High Similarity NPC219428
0.86 High Similarity NPC239943
0.86 High Similarity NPC37250
0.86 High Similarity NPC152942
0.86 High Similarity NPC302857
0.86 High Similarity NPC278068
0.86 High Similarity NPC142703
0.8598 High Similarity NPC31034
0.8596 High Similarity NPC269625
0.858 High Similarity NPC476372
0.858 High Similarity NPC476371
0.8562 High Similarity NPC156818
0.8562 High Similarity NPC160512
0.8562 High Similarity NPC289322
0.8562 High Similarity NPC68324
0.8562 High Similarity NPC38779
0.8562 High Similarity NPC114179
0.8543 High Similarity NPC476820
0.8543 High Similarity NPC295492
0.8543 High Similarity NPC474875
0.8543 High Similarity NPC274891
0.8543 High Similarity NPC476819
0.8543 High Similarity NPC205751
0.8543 High Similarity NPC26241
0.8543 High Similarity NPC303683
0.8535 High Similarity NPC140151
0.8529 High Similarity NPC135831
0.8529 High Similarity NPC297503
0.8529 High Similarity NPC97119
0.8523 High Similarity NPC18646
0.8519 High Similarity NPC266365
0.8509 High Similarity NPC471750
0.8509 High Similarity NPC87317
0.85 High Similarity NPC318432
0.8491 Intermediate Similarity NPC469888
0.8485 Intermediate Similarity NPC473818
0.8476 Intermediate Similarity NPC142614
0.8471 Intermediate Similarity NPC8940
0.8467 Intermediate Similarity NPC156892
0.8466 Intermediate Similarity NPC291957
0.8466 Intermediate Similarity NPC4013
0.8466 Intermediate Similarity NPC14030
0.8466 Intermediate Similarity NPC90905
0.8457 Intermediate Similarity NPC289346
0.8457 Intermediate Similarity NPC24164
0.8457 Intermediate Similarity NPC53889
0.8443 Intermediate Similarity NPC5786
0.8443 Intermediate Similarity NPC102851
0.8442 Intermediate Similarity NPC229036
0.8434 Intermediate Similarity NPC658
0.8434 Intermediate Similarity NPC197708
0.843 Intermediate Similarity NPC112380
0.8428 Intermediate Similarity NPC83663
0.8428 Intermediate Similarity NPC475216
0.8428 Intermediate Similarity NPC475595
0.8428 Intermediate Similarity NPC475162
0.8428 Intermediate Similarity NPC266084
0.8428 Intermediate Similarity NPC475145
0.8428 Intermediate Similarity NPC473544
0.8415 Intermediate Similarity NPC227297
0.8415 Intermediate Similarity NPC470898
0.8412 Intermediate Similarity NPC198902
0.8402 Intermediate Similarity NPC472723
0.8389 Intermediate Similarity NPC1321
0.8389 Intermediate Similarity NPC304929
0.8389 Intermediate Similarity NPC156124
0.8387 Intermediate Similarity NPC108455
0.8383 Intermediate Similarity NPC476365
0.8382 Intermediate Similarity NPC475179
0.8375 Intermediate Similarity NPC281703
0.8375 Intermediate Similarity NPC125487
0.8365 Intermediate Similarity NPC75695
0.8354 Intermediate Similarity NPC33298
0.8354 Intermediate Similarity NPC285108
0.8353 Intermediate Similarity NPC293626
0.8353 Intermediate Similarity NPC196127
0.8353 Intermediate Similarity NPC217387
0.8353 Intermediate Similarity NPC258044
0.8353 Intermediate Similarity NPC37668
0.8353 Intermediate Similarity NPC253521
0.8353 Intermediate Similarity NPC113836
0.8353 Intermediate Similarity NPC267680
0.8333 Intermediate Similarity NPC68517
0.8333 Intermediate Similarity NPC98356
0.8324 Intermediate Similarity NPC469650
0.8324 Intermediate Similarity NPC104910
0.8324 Intermediate Similarity NPC474093
0.8323 Intermediate Similarity NPC280493
0.8313 Intermediate Similarity NPC474656
0.8313 Intermediate Similarity NPC471823
0.8304 Intermediate Similarity NPC80956
0.8294 Intermediate Similarity NPC61904
0.8294 Intermediate Similarity NPC144097
0.8286 Intermediate Similarity NPC201814
0.8282 Intermediate Similarity NPC287872
0.8282 Intermediate Similarity NPC74319
0.8278 Intermediate Similarity NPC233350
0.8278 Intermediate Similarity NPC182217
0.8278 Intermediate Similarity NPC70680
0.8276 Intermediate Similarity NPC469649
0.8276 Intermediate Similarity NPC260521
0.8276 Intermediate Similarity NPC30011
0.8276 Intermediate Similarity NPC97817
0.8276 Intermediate Similarity NPC72554
0.8274 Intermediate Similarity NPC180768

  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 NPC134925 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
0.8867 High Similarity NPD6190 Approved
0.878 High Similarity NPD7993 Clinical (unspecified phase)
0.8616 High Similarity NPD4868 Clinical (unspecified phase)
0.8389 Intermediate Similarity NPD230 Phase 1
0.8036 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.8036 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.8036 Intermediate Similarity NPD6166 Phase 2
0.8023 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.7907 Intermediate Similarity NPD6797 Phase 2
0.7879 Intermediate Similarity NPD3817 Phase 2
0.7861 Intermediate Similarity NPD7251 Discontinued
0.7831 Intermediate Similarity NPD3882 Suspended
0.7816 Intermediate Similarity NPD7808 Phase 3
0.7771 Intermediate Similarity NPD5402 Approved
0.777 Intermediate Similarity NPD9269 Phase 2
0.7711 Intermediate Similarity NPD2801 Approved
0.7711 Intermediate Similarity NPD1465 Phase 2
0.7688 Intermediate Similarity NPD5844 Phase 1
0.7684 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7679 Intermediate Similarity NPD7075 Discontinued
0.7654 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7651 Intermediate Similarity NPD1934 Approved
0.7644 Intermediate Similarity NPD7472 Approved
0.763 Intermediate Similarity NPD3818 Discontinued
0.7607 Intermediate Similarity NPD1512 Approved
0.7605 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7602 Intermediate Similarity NPD6232 Discontinued
0.7586 Intermediate Similarity NPD7054 Approved
0.7569 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7561 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7557 Intermediate Similarity NPD7685 Pre-registration
0.7543 Intermediate Similarity NPD7074 Phase 3
0.753 Intermediate Similarity NPD4380 Phase 2
0.75 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD9268 Approved
0.7485 Intermediate Similarity NPD6799 Approved
0.7485 Intermediate Similarity NPD1511 Approved
0.7471 Intermediate Similarity NPD7473 Discontinued
0.7455 Intermediate Similarity NPD5403 Approved
0.7444 Intermediate Similarity NPD8150 Discontinued
0.744 Intermediate Similarity NPD6801 Discontinued
0.7438 Intermediate Similarity NPD7266 Discontinued
0.7427 Intermediate Similarity NPD6234 Discontinued
0.7414 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.7407 Intermediate Similarity NPD8166 Discontinued
0.7389 Intermediate Similarity NPD943 Approved
0.7386 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.7372 Intermediate Similarity NPD3764 Approved
0.7368 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.7341 Intermediate Similarity NPD6959 Discontinued
0.7333 Intermediate Similarity NPD5401 Approved
0.733 Intermediate Similarity NPD3751 Discontinued
0.733 Intermediate Similarity NPD7228 Approved
0.731 Intermediate Similarity NPD7768 Phase 2
0.7299 Intermediate Similarity NPD3787 Discontinued
0.7278 Intermediate Similarity NPD7411 Suspended
0.7278 Intermediate Similarity NPD8313 Approved
0.7278 Intermediate Similarity NPD8312 Approved
0.7273 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7273 Intermediate Similarity NPD7390 Discontinued
0.7257 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7235 Intermediate Similarity NPD37 Approved
0.7219 Intermediate Similarity NPD6599 Discontinued
0.7215 Intermediate Similarity NPD6233 Phase 2
0.7209 Intermediate Similarity NPD4967 Phase 2
0.7209 Intermediate Similarity NPD4966 Approved
0.7209 Intermediate Similarity NPD4965 Approved
0.7205 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.7202 Intermediate Similarity NPD1653 Approved
0.72 Intermediate Similarity NPD9545 Approved
0.7195 Intermediate Similarity NPD4628 Phase 3
0.7193 Intermediate Similarity NPD7819 Suspended
0.7184 Intermediate Similarity NPD5494 Approved
0.7168 Intermediate Similarity NPD3749 Approved
0.7165 Intermediate Similarity NPD8151 Discontinued
0.7151 Intermediate Similarity NPD5353 Approved
0.7151 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.7126 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.7126 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.7126 Intermediate Similarity NPD7422 Clinical (unspecified phase)
0.7099 Intermediate Similarity NPD1510 Phase 2
0.7093 Intermediate Similarity NPD8455 Phase 2
0.7091 Intermediate Similarity NPD3750 Approved
0.7089 Intermediate Similarity NPD3027 Phase 3
0.7083 Intermediate Similarity NPD7435 Discontinued
0.7073 Intermediate Similarity NPD1549 Phase 2
0.7073 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.707 Intermediate Similarity NPD9494 Approved
0.7065 Intermediate Similarity NPD8434 Phase 2
0.7059 Intermediate Similarity NPD3455 Phase 2
0.7047 Intermediate Similarity NPD8319 Approved
0.7047 Intermediate Similarity NPD8320 Phase 1
0.7045 Intermediate Similarity NPD7199 Phase 2
0.703 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7021 Intermediate Similarity NPD6534 Approved
0.7021 Intermediate Similarity NPD6535 Approved
0.7012 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.7012 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD7699 Phase 2
0.7 Intermediate Similarity NPD7700 Phase 2
0.6978 Remote Similarity NPD7240 Approved
0.6978 Remote Similarity NPD6559 Discontinued
0.6966 Remote Similarity NPD5242 Approved
0.6959 Remote Similarity NPD7871 Phase 2
0.6959 Remote Similarity NPD7870 Phase 2
0.6957 Remote Similarity NPD1613 Approved
0.6957 Remote Similarity NPD1612 Clinical (unspecified phase)
0.6954 Remote Similarity NPD7874 Approved
0.6954 Remote Similarity NPD7875 Clinical (unspecified phase)
0.6951 Remote Similarity NPD5405 Approved
0.6951 Remote Similarity NPD5408 Approved
0.6951 Remote Similarity NPD2935 Discontinued
0.6951 Remote Similarity NPD5404 Approved
0.6951 Remote Similarity NPD5406 Approved
0.6951 Remote Similarity NPD1551 Phase 2
0.6947 Remote Similarity NPD8090 Clinical (unspecified phase)
0.6937 Remote Similarity NPD6859 Clinical (unspecified phase)
0.6937 Remote Similarity NPD6798 Discontinued
0.6932 Remote Similarity NPD919 Approved
0.6927 Remote Similarity NPD6779 Approved
0.6927 Remote Similarity NPD6776 Approved
0.6927 Remote Similarity NPD6781 Approved
0.6927 Remote Similarity NPD6778 Approved
0.6927 Remote Similarity NPD6782 Approved
0.6927 Remote Similarity NPD6780 Approved
0.6927 Remote Similarity NPD6777 Approved
0.6923 Remote Similarity NPD2534 Approved
0.6923 Remote Similarity NPD2533 Approved
0.6923 Remote Similarity NPD2532 Approved
0.6879 Remote Similarity NPD6385 Approved
0.6879 Remote Similarity NPD6386 Approved
0.6872 Remote Similarity NPD3926 Phase 2
0.686 Remote Similarity NPD7458 Discontinued
0.6855 Remote Similarity NPD1530 Clinical (unspecified phase)
0.6854 Remote Similarity NPD1247 Approved
0.6852 Remote Similarity NPD1240 Approved
0.6848 Remote Similarity NPD2796 Approved
0.6824 Remote Similarity NPD7004 Clinical (unspecified phase)
0.6821 Remote Similarity NPD7698 Approved
0.6821 Remote Similarity NPD7697 Approved
0.6821 Remote Similarity NPD7696 Phase 3
0.6815 Remote Similarity NPD4379 Clinical (unspecified phase)
0.6813 Remote Similarity NPD1529 Clinical (unspecified phase)
0.681 Remote Similarity NPD447 Suspended
0.6788 Remote Similarity NPD3748 Approved
0.6788 Remote Similarity NPD1509 Clinical (unspecified phase)
0.678 Remote Similarity NPD8155 Clinical (unspecified phase)
0.6768 Remote Similarity NPD7701 Phase 2
0.6768 Remote Similarity NPD1607 Approved
0.676 Remote Similarity NPD8127 Discontinued
0.6703 Remote Similarity NPD7038 Approved
0.6703 Remote Similarity NPD7039 Approved
0.6686 Remote Similarity NPD1878 Clinical (unspecified phase)
0.6686 Remote Similarity NPD7003 Approved
0.6686 Remote Similarity NPD6398 Clinical (unspecified phase)
0.6684 Remote Similarity NPD8485 Approved
0.6667 Remote Similarity NPD7783 Phase 2
0.6667 Remote Similarity NPD7782 Clinical (unspecified phase)
0.6667 Remote Similarity NPD5808 Clinical (unspecified phase)
0.6667 Remote Similarity NPD7801 Approved
0.6667 Remote Similarity NPD7549 Discontinued
0.6667 Remote Similarity NPD7095 Approved
0.665 Remote Similarity NPD7680 Approved
0.6647 Remote Similarity NPD2354 Approved
0.6647 Remote Similarity NPD3887 Approved
0.6615 Remote Similarity NPD7237 Clinical (unspecified phase)
0.6613 Remote Similarity NPD8368 Discontinued
0.6606 Remote Similarity NPD6355 Discontinued
0.6596 Remote Similarity NPD7090 Clinical (unspecified phase)
0.6592 Remote Similarity NPD6971 Discontinued
0.659 Remote Similarity NPD6273 Approved
0.6585 Remote Similarity NPD4062 Phase 3
0.6583 Remote Similarity NPD7211 Clinical (unspecified phase)
0.6582 Remote Similarity NPD8486 Clinical (unspecified phase)
0.6577 Remote Similarity NPD9265 Clinical (unspecified phase)
0.6571 Remote Similarity NPD3226 Approved
0.657 Remote Similarity NPD4357 Discontinued
0.6559 Remote Similarity NPD5953 Discontinued
0.6557 Remote Similarity NPD7784 Clinical (unspecified phase)
0.6545 Remote Similarity NPD8360 Approved
0.6545 Remote Similarity NPD8361 Approved
0.6545 Remote Similarity NPD8435 Approved
0.6538 Remote Similarity NPD7229 Phase 3
0.6528 Remote Similarity NPD6213 Phase 3
0.6528 Remote Similarity NPD6214 Clinical (unspecified phase)
0.6528 Remote Similarity NPD6212 Phase 3
0.6527 Remote Similarity NPD7097 Phase 1
0.6522 Remote Similarity NPD1203 Approved
0.6516 Remote Similarity NPD9493 Approved
0.6515 Remote Similarity NPD6823 Phase 2
0.6512 Remote Similarity NPD7236 Approved
0.6512 Remote Similarity NPD7440 Discontinued
0.6508 Remote Similarity NPD8407 Phase 2
0.6506 Remote Similarity NPD4340 Discontinued
0.6506 Remote Similarity NPD1933 Approved
0.6503 Remote Similarity NPD4908 Phase 1
0.6486 Remote Similarity NPD7177 Discontinued
0.646 Remote Similarity NPD3225 Approved
0.6457 Remote Similarity NPD920 Approved
0.6452 Remote Similarity NPD7286 Phase 2

  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