Structure

Physi-Chem Properties

Molecular Weight:  366.17
Volume:  356.577
LogP:  1.604
LogD:  1.095
LogS:  -3.911
# Rotatable Bonds:  5
TPSA:  94.59
# H-Bond Aceptor:  7
# H-Bond Donor:  1
# Rings:  4
# Heavy Atoms:  7

MedChem Properties

QED Drug-Likeness Score:  0.454
Synthetic Accessibility Score:  5.883
Fsp3:  0.789
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  1
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.253
MDCK Permeability:  2.808478348015342e-05
Pgp-inhibitor:  0.005
Pgp-substrate:  0.934
Human Intestinal Absorption (HIA):  0.029
20% Bioavailability (F20%):  0.662
30% Bioavailability (F30%):  0.664

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.741
Plasma Protein Binding (PPB):  35.263397216796875%
Volume Distribution (VD):  1.169
Pgp-substrate:  46.67270278930664%

ADMET: Metabolism

CYP1A2-inhibitor:  0.039
CYP1A2-substrate:  0.137
CYP2C19-inhibitor:  0.048
CYP2C19-substrate:  0.55
CYP2C9-inhibitor:  0.016
CYP2C9-substrate:  0.028
CYP2D6-inhibitor:  0.026
CYP2D6-substrate:  0.086
CYP3A4-inhibitor:  0.482
CYP3A4-substrate:  0.284

ADMET: Excretion

Clearance (CL):  2.196
Half-life (T1/2):  0.765

ADMET: Toxicity

hERG Blockers:  0.03
Human Hepatotoxicity (H-HT):  0.481
Drug-inuced Liver Injury (DILI):  0.804
AMES Toxicity:  0.929
Rat Oral Acute Toxicity:  0.451
Maximum Recommended Daily Dose:  0.142
Skin Sensitization:  0.381
Carcinogencity:  0.132
Eye Corrosion:  0.005
Eye Irritation:  0.065
Respiratory Toxicity:  0.261

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

  Natural Product: NPC240838

Natural Product ID:  NPC240838
Common Name*:   Anguidin
IUPAC Name:   n.a.
Synonyms:   Anguidin; Diacetoxyscirpenol
Standard InCHIKey:  AUGQEEXBDZWUJY-NMAPUUFXSA-N
Standard InCHI:  InChI=1S/C19H26O7/c1-10-5-6-18(8-23-11(2)20)13(7-10)26-16-14(22)15(25-12(3)21)17(18,4)19(16)9-24-19/h7,13-16,22H,5-6,8-9H2,1-4H3/t13-,14-,15-,16-,17-,18-,19+/m1/s1
SMILES:  CC(=O)OC[C@]12CCC(=C[C@H]1O[C@H]1[C@]3([C@]2(C)[C@H](OC(=O)C)[C@H]1O)CO3)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL433680
PubChem CID:   15571694
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001550] Sesquiterpenoids
          • [CHEMONTID:0001789] Trichothecenes

*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
NPO30443 Myrothecium verrucaria Species Stachybotryaceae Eukaryota n.a. n.a. n.a. PMID[10075777]
NPO30443 Myrothecium verrucaria Species Stachybotryaceae Eukaryota n.a. n.a. n.a. PMID[13678412]
NPO30443 Myrothecium verrucaria Species Stachybotryaceae Eukaryota n.a. n.a. n.a. PMID[21539317]
NPO30443 Myrothecium verrucaria Species Stachybotryaceae Eukaryota n.a. n.a. n.a. Database[HerDing]

☑ 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
NPT730 Cell Line MC-38 Mus musculus Selectivity = -150.0 zone unit PMID[471347]
NPT730 Cell Line MC-38 Mus musculus Selectivity = 0.0 zone unit PMID[471347]
NPT137 Cell Line L1210 Mus musculus Selectivity = 150.0 zone unit PMID[471347]
NPT404 Cell Line CCRF-CEM Homo sapiens IC50 < 1.0 nM PMID[471347]
NPT116 Cell Line HL-60 Homo sapiens IC50 < 1.0 nM PMID[471347]
NPT112 Cell Line MOLT-4 Homo sapiens IC50 < 1.0 nM PMID[471347]
NPT81 Cell Line A549 Homo sapiens IC50 < 1.0 nM PMID[471347]
NPT405 Cell Line NCI-H226 Homo sapiens IC50 < 1.0 nM PMID[471347]
NPT455 Cell Line NCI-H522 Homo sapiens IC50 < 1.0 nM PMID[471347]
NPT407 Cell Line COLO 205 Homo sapiens IC50 < 1.0 nM PMID[471347]
NPT393 Cell Line HCT-116 Homo sapiens IC50 < 1.0 nM PMID[471347]
NPT148 Cell Line HCT-15 Homo sapiens IC50 < 1.0 nM PMID[471347]
NPT387 Cell Line M14 Homo sapiens IC50 < 1.0 nM PMID[471347]
NPT147 Cell Line SK-MEL-2 Homo sapiens IC50 < 1.0 nM PMID[471347]
NPT398 Cell Line UACC-62 Homo sapiens IC50 < 1.0 nM PMID[471347]
NPT401 Cell Line 786-0 Homo sapiens IC50 < 1.0 nM PMID[471347]
NPT376 Cell Line A498 Homo sapiens IC50 < 1.0 nM PMID[471347]
NPT406 Cell Line RXF 393 Homo sapiens IC50 < 1.0 nM PMID[471347]
NPT83 Cell Line MCF7 Homo sapiens IC50 < 1.0 nM PMID[471347]
NPT400 Cell Line MDA-MB-435 Homo sapiens IC50 < 1.0 nM PMID[471347]
NPT367 Cell Line MDA-N Homo sapiens IC50 < 1.0 nM PMID[471347]
NPT1864 Cell Line L5178Y Mus musculus LC50 = 0.002 ug.mL-1 PMID[471348]
NPT111 Cell Line K562 Homo sapiens EC50 = 2.7 nM PMID[471349]
NPT1197 Individual Protein Huntingtin Homo sapiens Potency = 100.0 nM PMID[471351]
NPT537 Individual Protein Ras-related protein Rab-9A Homo sapiens Potency = 1995.3 nM PMID[471351]
NPT531 Individual Protein Nuclear receptor ROR-gamma Mus musculus Potency = 1.6 nM PMID[471351]
NPT54 Individual Protein Nonstructural protein 1 Influenza A virus Potency = 7943.3 nM PMID[471351]
NPT538 Individual Protein Niemann-Pick C1 protein Homo sapiens Potency = 89.1 nM PMID[471351]
NPT531 Individual Protein Nuclear receptor ROR-gamma Mus musculus Potency = 31.6 nM PMID[471351]
NPT152 Individual Protein Nuclear factor erythroid 2-related factor 2 Homo sapiens Potency n.a. 18.4 nM PMID[471351]
NPT2892 Individual Protein X-box-binding protein 1 Homo sapiens IC50 = 160.0 nM PMID[471351]
NPT539 Individual Protein Cellular tumor antigen p53 Homo sapiens Potency n.a. 31622.8 nM PMID[471351]
NPT5 Individual Protein Histone-lysine N-methyltransferase, H3 lysine-9 specific 3 Homo sapiens Potency n.a. 794.3 nM PMID[471351]
NPT2893 Individual Protein DNA damage-inducible transcript 3 protein Mus musculus IC50 > 160.0 nM PMID[471351]
NPT64 Individual Protein ATPase family AAA domain-containing protein 5 Homo sapiens Potency n.a. 18.3 nM PMID[471351]
NPT1861 Individual Protein Mitochondrial import inner membrane translocase subunit TIM10 Saccharomyces cerevisiae S288c IC50 = 30800.0 nM PMID[471351]
NPT15 Cell Line Jurkat Homo sapiens IC50 < 160.0 nM PMID[471351]
NPT64 Individual Protein ATPase family AAA domain-containing protein 5 Homo sapiens Potency n.a. 17.7 nM PMID[471351]
NPT64 Individual Protein ATPase family AAA domain-containing protein 5 Homo sapiens Potency n.a. 44.5 nM PMID[471351]
NPT10 Individual Protein Geminin Homo sapiens Potency n.a. 58.0 nM PMID[471351]
NPT64 Individual Protein ATPase family AAA domain-containing protein 5 Homo sapiens Potency n.a. 39.7 nM PMID[471351]
NPT159 Individual Protein Aberrant vpr protein Human immunodeficiency virus 1 Potency n.a. 3162.3 nM PMID[471351]
NPT64 Individual Protein ATPase family AAA domain-containing protein 5 Homo sapiens Potency n.a. 28.1 nM PMID[471351]
NPT64 Individual Protein ATPase family AAA domain-containing protein 5 Homo sapiens Potency n.a. 56.1 nM PMID[471351]
NPT66 Individual Protein Acetylcholinesterase Electrophorus electricus Inhibition = 23.78 % PMID[471352]
NPT50 Individual Protein Tyrosyl-DNA phosphodiesterase 1 Homo sapiens Potency n.a. 16.4 nM PMID[471351]
NPT160 Individual Protein TAR DNA-binding protein 43 Homo sapiens Potency n.a. 35481.3 nM PMID[471351]
NPT50 Individual Protein Tyrosyl-DNA phosphodiesterase 1 Homo sapiens Potency n.a. 20.6 nM PMID[471351]
NPT154 Individual Protein Mothers against decapentaplegic homolog 3 Homo sapiens Potency n.a. 36.6 nM PMID[471351]
NPT152 Individual Protein Nuclear factor erythroid 2-related factor 2 Homo sapiens Potency n.a. 2592.9 nM PMID[471351]
NPT2 Others Unspecified Relative activity = 423.0 n.a. PMID[471347]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Concentration = 0.24 ug ml-1 PMID[471347]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Selectivity = -100.0 zone unit PMID[471347]
NPT22117 CELL-LINE NCI-H125 Homo sapiens Selectivity = 0.0 zone unit PMID[471347]
NPT32 Organism Mus musculus Mus musculus LD50 = 23.0 mg.kg-1 PMID[471349]
NPT32 Organism Mus musculus Mus musculus Activity = 23.0 n.a. PMID[471349]
NPT312 Organism Saccharomyces cerevisiae Saccharomyces cerevisiae Ratio = 342.9 n.a. PMID[471350]
NPT312 Organism Saccharomyces cerevisiae Saccharomyces cerevisiae Activity = 342.9 n.a. PMID[471350]
NPT312 Organism Saccharomyces cerevisiae Saccharomyces cerevisiae Potency = 6309.6 nM PMID[471351]
NPT536 Uncleic Acid microRNA 21 Homo sapiens Potency = 4.6 nM PMID[471351]
NPT2 Others Unspecified Potency = 51.7 nM PMID[471351]
NPT2 Others Unspecified Potency n.a. 16.4 nM PMID[471351]
NPT2 Others Unspecified IC50 < 160.0 nM PMID[471351]
NPT2 Others Unspecified IC50 > 80000.0 nM PMID[471351]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum Potency n.a. 4653.5 nM PMID[471351]
NPT586 Organism Giardia Giardia Potency n.a. 130.9 nM PMID[471351]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum Potency n.a. 3.3 nM PMID[471351]
NPT586 Organism Giardia Giardia Potency n.a. 5160.9 nM PMID[471351]
NPT2 Others Unspecified AC50 > 70000.0 nM PMID[471351]
NPT2 Others Unspecified AC50 < 260.0 nM PMID[471351]
NPT2 Others Unspecified Potency n.a. 7079.5 nM PMID[471351]
NPT67 Individual Protein Cholinesterase Equus caballus Inhibition = 12.32 % PMID[471352]
NPT2 Others Unspecified Potency n.a. 206.0 nM PMID[471351]
NPT920 Individual Protein Alpha-synuclein Homo sapiens Potency n.a. 5623.4 nM PMID[471351]
NPT861 Individual Protein Isocitrate dehydrogenase [NADP] cytoplasmic Homo sapiens Potency n.a. 730.8 nM PMID[471351]
NPT2 Others Unspecified Potency n.a. 89125.1 nM PMID[471351]
NPT2 Others Unspecified Potency n.a. 145.8 nM PMID[471351]
NPT2 Others Unspecified Potency n.a. 31622.8 nM PMID[471351]
NPT2 Others Unspecified Potency n.a. 3162.3 nM PMID[471351]
NPT2 Others Unspecified Potency n.a. 562.3 nM PMID[471351]

☑ 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 NPC240838 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
0.9778 High Similarity NPC476057
0.9778 High Similarity NPC182811
0.9778 High Similarity NPC347923
0.967 High Similarity NPC79449
0.967 High Similarity NPC274458
0.967 High Similarity NPC474957
0.9565 High Similarity NPC79631
0.9462 High Similarity NPC26557
0.9362 High Similarity NPC475986
0.9362 High Similarity NPC252242
0.9362 High Similarity NPC200672
0.9362 High Similarity NPC214714
0.9362 High Similarity NPC475956
0.9263 High Similarity NPC474783
0.9263 High Similarity NPC260809
0.9263 High Similarity NPC232515
0.9111 High Similarity NPC197107
0.9072 High Similarity NPC29389
0.9072 High Similarity NPC469960
0.9072 High Similarity NPC93026
0.9072 High Similarity NPC265502
0.898 High Similarity NPC469959
0.898 High Similarity NPC469957
0.898 High Similarity NPC472263
0.898 High Similarity NPC108682
0.8713 High Similarity NPC41551
0.8713 High Similarity NPC50223
0.8646 High Similarity NPC65700
0.8557 High Similarity NPC13743
0.8557 High Similarity NPC98813
0.8544 High Similarity NPC313921
0.8544 High Similarity NPC98038
0.8462 Intermediate Similarity NPC287075
0.8462 Intermediate Similarity NPC101965
0.8462 Intermediate Similarity NPC101400
0.8381 Intermediate Similarity NPC305044
0.8381 Intermediate Similarity NPC265290
0.83 Intermediate Similarity NPC123505
0.8218 Intermediate Similarity NPC169843
0.8148 Intermediate Similarity NPC475130
0.8148 Intermediate Similarity NPC474286
0.8132 Intermediate Similarity NPC231601
0.8095 Intermediate Similarity NPC71680
0.8077 Intermediate Similarity NPC77089
0.8065 Intermediate Similarity NPC477668
0.8061 Intermediate Similarity NPC57664
0.8 Intermediate Similarity NPC299527
0.8 Intermediate Similarity NPC15551
0.7921 Intermediate Similarity NPC475617
0.79 Intermediate Similarity NPC222303
0.7872 Intermediate Similarity NPC137253
0.7864 Intermediate Similarity NPC472822
0.7857 Intermediate Similarity NPC472467
0.7857 Intermediate Similarity NPC281775
0.785 Intermediate Similarity NPC241477
0.785 Intermediate Similarity NPC126691
0.7843 Intermediate Similarity NPC470972
0.7822 Intermediate Similarity NPC130792
0.78 Intermediate Similarity NPC96597
0.78 Intermediate Similarity NPC205143
0.78 Intermediate Similarity NPC239547
0.78 Intermediate Similarity NPC91197
0.78 Intermediate Similarity NPC125551
0.78 Intermediate Similarity NPC309503
0.78 Intermediate Similarity NPC155319
0.78 Intermediate Similarity NPC210337
0.7788 Intermediate Similarity NPC475290
0.7788 Intermediate Similarity NPC470980
0.7778 Intermediate Similarity NPC477089
0.7767 Intermediate Similarity NPC472821
0.7767 Intermediate Similarity NPC473523
0.7767 Intermediate Similarity NPC474124
0.7757 Intermediate Similarity NPC474750
0.7748 Intermediate Similarity NPC278681
0.7742 Intermediate Similarity NPC477667
0.7732 Intermediate Similarity NPC202886
0.7727 Intermediate Similarity NPC290693
0.7714 Intermediate Similarity NPC472820
0.7706 Intermediate Similarity NPC216665
0.77 Intermediate Similarity NPC113433
0.77 Intermediate Similarity NPC88009
0.7692 Intermediate Similarity NPC152966
0.7692 Intermediate Similarity NPC473577
0.7692 Intermediate Similarity NPC473543
0.7692 Intermediate Similarity NPC474550
0.7692 Intermediate Similarity NPC200861
0.7692 Intermediate Similarity NPC475585
0.7679 Intermediate Similarity NPC112936
0.767 Intermediate Similarity NPC475344
0.767 Intermediate Similarity NPC476471
0.766 Intermediate Similarity NPC186155
0.766 Intermediate Similarity NPC78673
0.766 Intermediate Similarity NPC160517
0.7658 Intermediate Similarity NPC16701
0.7653 Intermediate Similarity NPC472468
0.7653 Intermediate Similarity NPC234335
0.7647 Intermediate Similarity NPC230546
0.7647 Intermediate Similarity NPC473510
0.7629 Intermediate Similarity NPC477748
0.7624 Intermediate Similarity NPC475032
0.7624 Intermediate Similarity NPC475033
0.7619 Intermediate Similarity NPC220217
0.7619 Intermediate Similarity NPC186668
0.7619 Intermediate Similarity NPC119855
0.7619 Intermediate Similarity NPC472818
0.76 Intermediate Similarity NPC220221
0.7596 Intermediate Similarity NPC474775
0.7589 Intermediate Similarity NPC213761
0.7589 Intermediate Similarity NPC35171
0.7576 Intermediate Similarity NPC470187
0.7573 Intermediate Similarity NPC472554
0.7573 Intermediate Similarity NPC11974
0.7573 Intermediate Similarity NPC280991
0.757 Intermediate Similarity NPC187876
0.757 Intermediate Similarity NPC128133
0.7568 Intermediate Similarity NPC203862
0.7568 Intermediate Similarity NPC185287
0.7568 Intermediate Similarity NPC157380
0.7551 Intermediate Similarity NPC472466
0.7551 Intermediate Similarity NPC3952
0.7549 Intermediate Similarity NPC212465
0.7549 Intermediate Similarity NPC177232
0.7547 Intermediate Similarity NPC475781
0.7545 Intermediate Similarity NPC471633
0.7545 Intermediate Similarity NPC84949
0.7545 Intermediate Similarity NPC69576
0.7545 Intermediate Similarity NPC106446
0.7545 Intermediate Similarity NPC31354
0.7545 Intermediate Similarity NPC43213
0.7544 Intermediate Similarity NPC115349
0.7527 Intermediate Similarity NPC474894
0.7525 Intermediate Similarity NPC98165
0.7524 Intermediate Similarity NPC181104
0.7524 Intermediate Similarity NPC472819
0.7524 Intermediate Similarity NPC288502
0.7524 Intermediate Similarity NPC103298
0.7524 Intermediate Similarity NPC201144
0.7524 Intermediate Similarity NPC475335
0.7524 Intermediate Similarity NPC475331
0.7524 Intermediate Similarity NPC80809
0.7524 Intermediate Similarity NPC121518
0.7522 Intermediate Similarity NPC79579
0.75 Intermediate Similarity NPC255143
0.75 Intermediate Similarity NPC472214
0.75 Intermediate Similarity NPC61527
0.75 Intermediate Similarity NPC472552
0.75 Intermediate Similarity NPC181298
0.75 Intermediate Similarity NPC472215
0.7477 Intermediate Similarity NPC472825
0.7477 Intermediate Similarity NPC199428
0.7477 Intermediate Similarity NPC5311
0.7477 Intermediate Similarity NPC193382
0.7477 Intermediate Similarity NPC99620
0.7477 Intermediate Similarity NPC310341
0.7477 Intermediate Similarity NPC10150
0.7476 Intermediate Similarity NPC38855
0.7476 Intermediate Similarity NPC167974
0.7476 Intermediate Similarity NPC79303
0.7475 Intermediate Similarity NPC477749
0.7475 Intermediate Similarity NPC249034
0.7474 Intermediate Similarity NPC83702
0.7474 Intermediate Similarity NPC116613
0.7473 Intermediate Similarity NPC40049
0.7473 Intermediate Similarity NPC186109
0.7453 Intermediate Similarity NPC54737
0.7453 Intermediate Similarity NPC60315
0.7453 Intermediate Similarity NPC85670
0.7451 Intermediate Similarity NPC473244
0.7451 Intermediate Similarity NPC231751
0.7449 Intermediate Similarity NPC133450
0.7449 Intermediate Similarity NPC261320
0.7449 Intermediate Similarity NPC246028
0.7449 Intermediate Similarity NPC49783
0.7434 Intermediate Similarity NPC291820
0.7434 Intermediate Similarity NPC304260
0.7434 Intermediate Similarity NPC29639
0.7434 Intermediate Similarity NPC81222
0.7434 Intermediate Similarity NPC44899
0.7434 Intermediate Similarity NPC5883
0.7431 Intermediate Similarity NPC470076
0.7429 Intermediate Similarity NPC160583
0.7429 Intermediate Similarity NPC475334
0.7429 Intermediate Similarity NPC196471
0.7429 Intermediate Similarity NPC10232
0.7429 Intermediate Similarity NPC475623
0.7429 Intermediate Similarity NPC473694
0.7429 Intermediate Similarity NPC189588
0.7429 Intermediate Similarity NPC187302
0.7429 Intermediate Similarity NPC97487
0.7419 Intermediate Similarity NPC474739
0.7411 Intermediate Similarity NPC473852
0.7411 Intermediate Similarity NPC471355
0.7411 Intermediate Similarity NPC243196
0.7411 Intermediate Similarity NPC474418
0.7411 Intermediate Similarity NPC471351
0.7411 Intermediate Similarity NPC93883
0.7411 Intermediate Similarity NPC158344
0.7411 Intermediate Similarity NPC471353
0.7411 Intermediate Similarity NPC27507
0.7411 Intermediate Similarity NPC84987

  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 NPC240838 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
0.7374 Intermediate Similarity NPD6698 Approved
0.7374 Intermediate Similarity NPD46 Approved
0.7345 Intermediate Similarity NPD7328 Approved
0.7345 Intermediate Similarity NPD7327 Approved
0.7304 Intermediate Similarity NPD7503 Approved
0.7304 Intermediate Similarity NPD8033 Approved
0.7281 Intermediate Similarity NPD7516 Approved
0.7217 Intermediate Similarity NPD8377 Approved
0.7217 Intermediate Similarity NPD8294 Approved
0.7212 Intermediate Similarity NPD7638 Approved
0.72 Intermediate Similarity NPD7838 Discovery
0.7155 Intermediate Similarity NPD8296 Approved
0.7155 Intermediate Similarity NPD8335 Approved
0.7155 Intermediate Similarity NPD8380 Approved
0.7155 Intermediate Similarity NPD8378 Approved
0.7155 Intermediate Similarity NPD8379 Approved
0.7143 Intermediate Similarity NPD7640 Approved
0.7143 Intermediate Similarity NPD7639 Approved
0.71 Intermediate Similarity NPD6051 Approved
0.7091 Intermediate Similarity NPD4061 Clinical (unspecified phase)
0.7075 Intermediate Similarity NPD5344 Discontinued
0.7064 Intermediate Similarity NPD6412 Phase 2
0.7054 Intermediate Similarity NPD6053 Discontinued
0.7027 Intermediate Similarity NPD6371 Approved
0.7 Intermediate Similarity NPD6686 Approved
0.697 Remote Similarity NPD4249 Approved
0.6917 Remote Similarity NPD7507 Approved
0.69 Remote Similarity NPD4251 Approved
0.69 Remote Similarity NPD4250 Approved
0.69 Remote Similarity NPD7524 Approved
0.6875 Remote Similarity NPD4821 Approved
0.6875 Remote Similarity NPD4819 Approved
0.6875 Remote Similarity NPD5790 Clinical (unspecified phase)
0.6875 Remote Similarity NPD4822 Approved
0.6875 Remote Similarity NPD4820 Approved
0.6869 Remote Similarity NPD6082 Clinical (unspecified phase)
0.681 Remote Similarity NPD7115 Discovery
0.678 Remote Similarity NPD6319 Approved
0.6768 Remote Similarity NPD7338 Clinical (unspecified phase)
0.6757 Remote Similarity NPD7899 Clinical (unspecified phase)
0.6748 Remote Similarity NPD7319 Approved
0.6729 Remote Similarity NPD4225 Approved
0.6726 Remote Similarity NPD5955 Clinical (unspecified phase)
0.6696 Remote Similarity NPD4632 Approved
0.6667 Remote Similarity NPD6648 Approved
0.6667 Remote Similarity NPD4271 Approved
0.6667 Remote Similarity NPD4268 Approved
0.6667 Remote Similarity NPD6695 Phase 3
0.6636 Remote Similarity NPD6084 Phase 2
0.6636 Remote Similarity NPD6083 Phase 2
0.6635 Remote Similarity NPD7637 Suspended
0.6606 Remote Similarity NPD4159 Approved
0.6604 Remote Similarity NPD5695 Phase 3
0.66 Remote Similarity NPD6400 Clinical (unspecified phase)
0.6574 Remote Similarity NPD8029 Clinical (unspecified phase)
0.6569 Remote Similarity NPD4751 Clinical (unspecified phase)
0.6566 Remote Similarity NPD6435 Approved
0.6552 Remote Similarity NPD8133 Approved
0.6545 Remote Similarity NPD7632 Discontinued
0.6522 Remote Similarity NPD8413 Clinical (unspecified phase)
0.6518 Remote Similarity NPD6675 Approved
0.6518 Remote Similarity NPD6008 Approved
0.6518 Remote Similarity NPD6402 Approved
0.6518 Remote Similarity NPD7128 Approved
0.6518 Remote Similarity NPD5739 Approved
0.6466 Remote Similarity NPD8297 Approved
0.646 Remote Similarity NPD5697 Approved
0.646 Remote Similarity NPD5701 Approved
0.646 Remote Similarity NPD5954 Clinical (unspecified phase)
0.6458 Remote Similarity NPD3701 Clinical (unspecified phase)
0.6444 Remote Similarity NPD2685 Clinical (unspecified phase)
0.6442 Remote Similarity NPD1695 Approved
0.6423 Remote Similarity NPD7492 Approved
0.6422 Remote Similarity NPD5696 Approved
0.6415 Remote Similarity NPD6399 Phase 3
0.6408 Remote Similarity NPD7750 Discontinued
0.6404 Remote Similarity NPD6881 Approved
0.6404 Remote Similarity NPD6899 Approved
0.6404 Remote Similarity NPD7320 Approved
0.6389 Remote Similarity NPD4792 Clinical (unspecified phase)
0.6387 Remote Similarity NPD6009 Approved
0.6381 Remote Similarity NPD5785 Approved
0.6371 Remote Similarity NPD6616 Approved
0.6364 Remote Similarity NPD6059 Approved
0.6364 Remote Similarity NPD5368 Approved
0.6364 Remote Similarity NPD6930 Phase 2
0.6364 Remote Similarity NPD6931 Approved
0.6364 Remote Similarity NPD6054 Approved
0.6348 Remote Similarity NPD6013 Approved
0.6348 Remote Similarity NPD6372 Approved
0.6348 Remote Similarity NPD6014 Approved
0.6348 Remote Similarity NPD6012 Approved
0.6348 Remote Similarity NPD6373 Approved
0.6341 Remote Similarity NPD7604 Phase 2
0.6337 Remote Similarity NPD5362 Discontinued
0.6337 Remote Similarity NPD7154 Phase 3
0.6321 Remote Similarity NPD7983 Approved
0.6321 Remote Similarity NPD5693 Phase 1
0.632 Remote Similarity NPD7078 Approved
0.632 Remote Similarity NPD8293 Discontinued
0.6311 Remote Similarity NPD6015 Approved
0.6311 Remote Similarity NPD5983 Phase 2
0.6311 Remote Similarity NPD7521 Approved
0.6311 Remote Similarity NPD7334 Approved
0.6311 Remote Similarity NPD8515 Approved
0.6311 Remote Similarity NPD8513 Phase 3
0.6311 Remote Similarity NPD5330 Approved
0.6311 Remote Similarity NPD7146 Approved
0.6311 Remote Similarity NPD6409 Approved
0.6311 Remote Similarity NPD6684 Approved
0.6311 Remote Similarity NPD8516 Approved
0.6311 Remote Similarity NPD8517 Approved
0.6311 Remote Similarity NPD6016 Approved
0.6293 Remote Similarity NPD6883 Approved
0.6293 Remote Similarity NPD7102 Approved
0.6293 Remote Similarity NPD7290 Approved
0.6293 Remote Similarity NPD4634 Approved
0.6289 Remote Similarity NPD6933 Approved
0.6286 Remote Similarity NPD4753 Phase 2
0.6275 Remote Similarity NPD3133 Approved
0.6275 Remote Similarity NPD3665 Phase 1
0.6275 Remote Similarity NPD3666 Approved
0.627 Remote Similarity NPD7736 Approved
0.6263 Remote Similarity NPD6929 Approved
0.6262 Remote Similarity NPD5778 Approved
0.6262 Remote Similarity NPD5779 Approved
0.6261 Remote Similarity NPD5345 Clinical (unspecified phase)
0.6261 Remote Similarity NPD6011 Approved
0.626 Remote Similarity NPD5988 Approved
0.626 Remote Similarity NPD6370 Approved
0.6239 Remote Similarity NPD6617 Approved
0.6239 Remote Similarity NPD8130 Phase 1
0.6239 Remote Similarity NPD6847 Approved
0.6239 Remote Similarity NPD6650 Approved
0.6239 Remote Similarity NPD6649 Approved
0.6239 Remote Similarity NPD6869 Approved
0.6214 Remote Similarity NPD1733 Clinical (unspecified phase)
0.62 Remote Similarity NPD7514 Phase 3
0.62 Remote Similarity NPD7525 Registered
0.619 Remote Similarity NPD6903 Approved
0.619 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6186 Remote Similarity NPD6882 Approved
0.6182 Remote Similarity NPD4755 Approved
0.6176 Remote Similarity NPD5331 Approved
0.6176 Remote Similarity NPD5332 Approved
0.6168 Remote Similarity NPD5281 Approved
0.6168 Remote Similarity NPD5284 Approved
0.6168 Remote Similarity NPD6411 Approved
0.6168 Remote Similarity NPD7087 Discontinued
0.6162 Remote Similarity NPD5784 Clinical (unspecified phase)
0.6139 Remote Similarity NPD5369 Approved
0.6139 Remote Similarity NPD4790 Discontinued
0.6139 Remote Similarity NPD6902 Approved
0.6111 Remote Similarity NPD4202 Approved
0.6111 Remote Similarity NPD6336 Discontinued
0.6106 Remote Similarity NPD5211 Phase 2
0.6102 Remote Similarity NPD6401 Clinical (unspecified phase)
0.61 Remote Similarity NPD4195 Approved
0.6082 Remote Similarity NPD6926 Approved
0.6082 Remote Similarity NPD6924 Approved
0.6078 Remote Similarity NPD4270 Approved
0.6078 Remote Similarity NPD4752 Clinical (unspecified phase)
0.6078 Remote Similarity NPD4269 Approved
0.6078 Remote Similarity NPD3667 Approved
0.6071 Remote Similarity NPD5285 Approved
0.6071 Remote Similarity NPD5286 Approved
0.6071 Remote Similarity NPD4700 Approved
0.6071 Remote Similarity NPD4696 Approved
0.6068 Remote Similarity NPD8132 Clinical (unspecified phase)
0.6063 Remote Similarity NPD8074 Phase 3
0.6061 Remote Similarity NPD5776 Phase 2
0.6061 Remote Similarity NPD6932 Approved
0.6061 Remote Similarity NPD6925 Approved
0.6058 Remote Similarity NPD6893 Approved
0.6058 Remote Similarity NPD1694 Approved
0.6055 Remote Similarity NPD5282 Discontinued
0.6042 Remote Similarity NPD4243 Approved
0.604 Remote Similarity NPD7332 Phase 2
0.6034 Remote Similarity NPD6685 Approved
0.6033 Remote Similarity NPD6274 Approved
0.602 Remote Similarity NPD6942 Approved
0.602 Remote Similarity NPD7339 Approved
0.6 Remote Similarity NPD5786 Approved
0.6 Remote Similarity NPD6356 Clinical (unspecified phase)
0.6 Remote Similarity NPD1698 Clinical (unspecified phase)
0.6 Remote Similarity NPD4629 Approved
0.6 Remote Similarity NPD7260 Phase 2
0.6 Remote Similarity NPD5141 Approved
0.6 Remote Similarity NPD6098 Approved
0.6 Remote Similarity NPD5210 Approved
0.6 Remote Similarity NPD7145 Approved
0.5981 Remote Similarity NPD6080 Approved
0.5981 Remote Similarity NPD5764 Clinical (unspecified phase)
0.5981 Remote Similarity NPD6904 Approved
0.5981 Remote Similarity NPD6101 Approved
0.5981 Remote Similarity NPD6673 Approved
0.5965 Remote Similarity NPD5225 Approved
0.5965 Remote Similarity NPD4633 Approved
0.5965 Remote Similarity NPD5224 Approved
0.5965 Remote Similarity NPD5226 Approved

  Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity
B: biological targets similarity
C: networks similarity
D: cell-based bioactivity similarity
E: similarity based on clinical data