Structure

Physi-Chem Properties

Molecular Weight:  216.15
Volume:  249.128
LogP:  4.254
LogD:  4.388
LogS:  -5.112
# Rotatable Bonds:  0
TPSA:  13.14
# H-Bond Aceptor:  1
# H-Bond Donor:  0
# Rings:  2
# Heavy Atoms:  1

MedChem Properties

QED Drug-Likeness Score:  0.587
Synthetic Accessibility Score:  3.791
Fsp3:  0.467
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.703
MDCK Permeability:  3.08726193907205e-05
Pgp-inhibitor:  0.467
Pgp-substrate:  0.018
Human Intestinal Absorption (HIA):  0.018
20% Bioavailability (F20%):  0.142
30% Bioavailability (F30%):  0.008

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.375
Plasma Protein Binding (PPB):  96.35075378417969%
Volume Distribution (VD):  0.604
Pgp-substrate:  0.882634699344635%

ADMET: Metabolism

CYP1A2-inhibitor:  0.764
CYP1A2-substrate:  0.535
CYP2C19-inhibitor:  0.705
CYP2C19-substrate:  0.103
CYP2C9-inhibitor:  0.543
CYP2C9-substrate:  0.775
CYP2D6-inhibitor:  0.362
CYP2D6-substrate:  0.882
CYP3A4-inhibitor:  0.373
CYP3A4-substrate:  0.213

ADMET: Excretion

Clearance (CL):  6.466
Half-life (T1/2):  0.511

ADMET: Toxicity

hERG Blockers:  0.008
Human Hepatotoxicity (H-HT):  0.19
Drug-inuced Liver Injury (DILI):  0.523
AMES Toxicity:  0.008
Rat Oral Acute Toxicity:  0.043
Maximum Recommended Daily Dose:  0.484
Skin Sensitization:  0.807
Carcinogencity:  0.099
Eye Corrosion:  0.004
Eye Irritation:  0.049
Respiratory Toxicity:  0.329

Download Data

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

  Natural Product: NPC22678

Natural Product ID:  NPC22678
Common Name*:   Isofuranodiene
IUPAC Name:   (5E,9E)-3,6,10-trimethyl-4,7,8,11-tetrahydrocyclodeca[b]furan
Synonyms:   Isofuranodiene
Standard InCHIKey:  VMDXHYHOJPKFEK-IAVOFVOCSA-N
Standard InCHI:  InChI=1S/C15H20O/c1-11-5-4-6-12(2)9-15-14(8-7-11)13(3)10-16-15/h6-7,10H,4-5,8-9H2,1-3H3/b11-7+,12-6+
SMILES:  C/C/1=CCc2c(C)coc2C/C(=C/CC1)/C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL324514
PubChem CID:   636458
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001550] Sesquiterpenoids
          • [CHEMONTID:0002456] Germacrane sesquiterpenoids

*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
NPO2300 Actinidia deliciosa Species Actinidiaceae Eukaryota Fruits Spanish DOI[10.1021/jf00010a019]
NPO2300 Actinidia deliciosa Species Actinidiaceae Eukaryota Fruits n.a. DOI[10.1021/jf00016a013]
NPO2300 Actinidia deliciosa Species Actinidiaceae Eukaryota n.a. Germany DOI[10.1021/jf00016a013]
NPO2300 Actinidia deliciosa Species Actinidiaceae Eukaryota n.a. Italy DOI[10.1021/jf00016a013]
NPO22741 Curcuma kwangsiensis Species Zingiberaceae Eukaryota n.a. rhizome n.a. DOI[10.1021/np100392m]
NPO2300 Actinidia deliciosa Species Actinidiaceae Eukaryota Fruits Turkey DOI[10.1111/j.1745-4557.2003.tb00250.x]
NPO2300 Actinidia deliciosa Species Actinidiaceae Eukaryota Fruits n.a. DOI[10.17660/ActaHortic.2003.610.16]
NPO15544 Cnidium monnieri Species Apiaceae Eukaryota n.a. fruit n.a. PMID[10785419]
NPO2300 Actinidia deliciosa Species Actinidiaceae Eukaryota Fruits n.a. PMID[10794642]
NPO2300 Actinidia deliciosa Species Actinidiaceae Eukaryota Fruits n.a. PMID[10820090]
NPO2300 Actinidia deliciosa Species Actinidiaceae Eukaryota Fruits n.a. PMID[11754554]
NPO24124 Curcuma longa Species Zingiberaceae Eukaryota n.a. n.a. n.a. PMID[12350137]
NPO24124 Curcuma longa Species Zingiberaceae Eukaryota rhizome n.a. n.a. PMID[12617587]
NPO2300 Actinidia deliciosa Species Actinidiaceae Eukaryota Fruits n.a. PMID[15315387]
NPO2300 Actinidia deliciosa Species Actinidiaceae Eukaryota Fruits n.a. PMID[16076125]
NPO2300 Actinidia deliciosa Species Actinidiaceae Eukaryota Fruits n.a. PMID[16920856]
NPO2300 Actinidia deliciosa Species Actinidiaceae Eukaryota Fruits n.a. PMID[19358604]
NPO22741 Curcuma kwangsiensis Species Zingiberaceae Eukaryota Rhizomes n.a. n.a. PMID[20879743]
NPO2300 Actinidia deliciosa Species Actinidiaceae Eukaryota Fruits n.a. PMID[21190690]
NPO15544 Cnidium monnieri Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[21625478]
NPO22741 Curcuma kwangsiensis Species Zingiberaceae Eukaryota n.a. n.a. n.a. PMID[21807513]
NPO15544 Cnidium monnieri Species Apiaceae Eukaryota fruits n.a. n.a. PMID[22932311]
NPO6674 Burkholderia ambifaria Species Burkholderiaceae Bacteria n.a. n.a. n.a. PMID[22988812]
NPO24124 Curcuma longa Species Zingiberaceae Eukaryota Rhizomes n.a. n.a. PMID[23153397]
NPO2300 Actinidia deliciosa Species Actinidiaceae Eukaryota n.a. Germany PMID[23394984]
NPO2300 Actinidia deliciosa Species Actinidiaceae Eukaryota n.a. New Zealand PMID[23394984]
NPO2300 Actinidia deliciosa Species Actinidiaceae Eukaryota Fruits n.a. PMID[23394984]
NPO15544 Cnidium monnieri Species Apiaceae Eukaryota n.a. fruit n.a. PMID[23721280]
NPO2618 Curcuma wenyujin Species Zingiberaceae Eukaryota n.a. rhizome n.a. PMID[23738470]
NPO2618 Curcuma wenyujin Species Zingiberaceae Eukaryota n.a. root n.a. PMID[23738470]
NPO18068 Curcuma phaeocaulis Species Zingiberaceae Eukaryota rhizomes n.a. n.a. PMID[23755850]
NPO24124 Curcuma longa Species Zingiberaceae Eukaryota n.a. leaf n.a. PMID[23901173]
NPO2300 Actinidia deliciosa Species Actinidiaceae Eukaryota Fruits n.a. PMID[2413754]
NPO17386 Securidaca longepedunculata Species Polygalaceae Eukaryota n.a. n.a. n.a. PMID[24216090]
NPO2618 Curcuma wenyujin Species Zingiberaceae Eukaryota Rhizomes n.a. n.a. PMID[25275213]
NPO24124 Curcuma longa Species Zingiberaceae Eukaryota n.a. n.a. n.a. PMID[28068085]
NPO11257 Momordica dioica Species Cucurbitaceae Eukaryota n.a. n.a. n.a. PMID[30673219]
NPO8286 Porophyllum ruderale Species Asteraceae Eukaryota n.a. Along the Valencian coast, Spain 2020-Jun&Jul PMID[35161358]
NPO2300 Actinidia deliciosa Species Actinidiaceae Eukaryota Fruits n.a. PMID[9542132]
NPO24124 Curcuma longa Species Zingiberaceae Eukaryota n.a. n.a. n.a. PMID[9584408]
NPO11719 Lamellomorpha strongylata Species Vulcanellidae Eukaryota n.a. n.a. n.a. PMID[9644054]
NPO7929 Curcuma zedoaria Species Zingiberaceae Eukaryota n.a. n.a. n.a. PMID[9868158]
NPO33283 zedoariae rhizoma n.a. n.a. n.a. n.a. n.a. n.a. PMID[9871681]
NPO24124 Curcuma longa Species Zingiberaceae Eukaryota Rhizome Essent. Oil n.a. n.a. Database[FooDB]
NPO24124 Curcuma longa Species Zingiberaceae Eukaryota Root n.a. n.a. Database[FooDB]
NPO24124 Curcuma longa Species Zingiberaceae Eukaryota Essential Oil n.a. n.a. Database[FooDB]
NPO24124 Curcuma longa Species Zingiberaceae Eukaryota n.a. n.a. Database[FooDB]
NPO24124 Curcuma longa Species Zingiberaceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO24124 Curcuma longa Species Zingiberaceae Eukaryota Rhizome n.a. n.a. Database[FooDB]
NPO24124 Curcuma longa Species Zingiberaceae Eukaryota n.a. n.a. Database[FooDB]
NPO7929 Curcuma zedoaria Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO11097 Lepidium apetalum Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO15544 Cnidium monnieri Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO24124 Curcuma longa Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO22741 Curcuma kwangsiensis Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO13613 Lophophora williamsii Species Cactaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO12662 Torilis japonica Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO24124 Curcuma longa Species Zingiberaceae Eukaryota n.a. n.a. Database[Phenol-Explorer]
NPO12662 Torilis japonica Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7929 Curcuma zedoaria Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11257 Momordica dioica Species Cucurbitaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15544 Cnidium monnieri Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO13613 Lophophora williamsii Species Cactaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO24124 Curcuma longa Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO2300 Actinidia deliciosa Species Actinidiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22741 Curcuma kwangsiensis Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11097 Lepidium apetalum Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11257 Momordica dioica Species Cucurbitaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO2618 Curcuma wenyujin Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO22741 Curcuma kwangsiensis Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO7929 Curcuma zedoaria Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO24124 Curcuma longa Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO11097 Lepidium apetalum Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO11097 Lepidium apetalum Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO12662 Torilis japonica Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO15544 Cnidium monnieri Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO2618 Curcuma wenyujin Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO7929 Curcuma zedoaria Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO22741 Curcuma kwangsiensis Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO24124 Curcuma longa Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO18068 Curcuma phaeocaulis Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO900 Cnidium monieri Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO8286 Porophyllum ruderale Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3385 Cassine transvaalensis Species Celastraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24124 Curcuma longa Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9512 Phlomis fruticosa Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13613 Lophophora williamsii Species Cactaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5827 Dalea tuberculata Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12192 Coronilla scorpioides Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10738 Cotoneaster horizontalis Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11097 Lepidium apetalum Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16164 Podocarpus urbani Species Podocarpaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11555 Pterocaulon purpurascens Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7345 Ptilonia magellanica Species Bonnemaisoniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6674 Burkholderia ambifaria Species Burkholderiaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO9928 Cephalaria cilicica Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8484 Codonopsis lanceolata Species Campanulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9040 Elsinoe annonae Species Elsinoaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO936 Pinalia spicata Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11257 Momordica dioica Species Cucurbitaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11815 Mikania hirsutissima Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2618 Curcuma wenyujin Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2300 Actinidia deliciosa Species Actinidiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12662 Torilis japonica Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11719 Lamellomorpha strongylata Species Vulcanellidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4964 Traversia baccharoides Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12891 Minasia alpestris Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22741 Curcuma kwangsiensis Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17386 Securidaca longepedunculata Species Polygalaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7929 Curcuma zedoaria Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10399 Manfreda virginica Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5013 Loranthus spicatus Species Loranthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7048 Eucalyptus rariflora Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19898 Stevia lucida Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5392 Pachycereus pecten-aboriginum Species Cactaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4236 Microscleroderma spirophora Species Scleritodermidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15544 Cnidium monnieri Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9307 Ficus indica Species Ficidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14610 Ophiopogon intermedius Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6256 Eucalyptus umbra Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1185 Stereocaulon strictum Species Stereocaulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12998 Salvia rubescens Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3740 Trisetum flavescens Species Poaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO468 Dryopteris oligophlebia Species Dryopteridaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18068 Curcuma phaeocaulis Species Zingiberaceae 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
NPT112 Cell Line MOLT-4 Homo sapiens IC50 = 39.65 ug.mL-1 PMID[491427]
NPT112 Cell Line MOLT-4 Homo sapiens IC50 = 23.0 ug.mL-1 PMID[491427]
NPT112 Cell Line MOLT-4 Homo sapiens Ratio IC50 = 86.0 n.a. PMID[491427]
NPT112 Cell Line MOLT-4 Homo sapiens Activity = 32.17 % PMID[491427]
NPT165 Cell Line HeLa Homo sapiens IC50 = 0.6 ug.mL-1 PMID[491427]
NPT65 Cell Line HepG2 Homo sapiens IC50 = 0.6 ug.mL-1 PMID[491427]
NPT116 Cell Line HL-60 Homo sapiens IC50 = 0.6 ug.mL-1 PMID[491427]
NPT306 Cell Line PC-3 Homo sapiens IC50 = 0.6 ug.mL-1 PMID[491427]
NPT515 Cell Line SGC-7901 Homo sapiens IC50 = 0.6 ug.mL-1 PMID[491427]
NPT453 Cell Line HT-1080 Homo sapiens IC50 = 0.6 ug.mL-1 PMID[491427]
NPT112 Cell Line MOLT-4 Homo sapiens Activity = 10.74 % PMID[491427]
NPT32 Organism Mus musculus Mus musculus Inhibition = 72.9 % PMID[491425]
NPT32 Organism Mus musculus Mus musculus Inhibition = 74.3 % PMID[491425]
NPT29 Organism Rattus norvegicus Rattus norvegicus Inhibition = -0.5 % PMID[491425]
NPT32 Organism Mus musculus Mus musculus Inhibition = 96.1 % PMID[491425]
NPT23712 CELL-LINE KG-1a Homo sapiens IC50 = 50.08 ug.mL-1 PMID[491427]
NPT23712 CELL-LINE KG-1a Homo sapiens IC20 = 25.0 ug ml-1 PMID[491427]
NPT23712 CELL-LINE KG-1a Homo sapiens Ratio IC50 = 77.0 n.a. PMID[491427]
NPT23712 CELL-LINE KG-1a Homo sapiens Activity = 58.08 % PMID[491427]
NPT23712 CELL-LINE KG-1a Homo sapiens Activity = 19.58 % PMID[491427]

☑ 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 NPC22678 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
0.9541 High Similarity NPC227660
0.9009 High Similarity NPC205523
0.8929 High Similarity NPC79202
0.8929 High Similarity NPC59035
0.887 High Similarity NPC97566
0.885 High Similarity NPC217180
0.885 High Similarity NPC312525
0.8814 High Similarity NPC216810
0.8739 High Similarity NPC184391
0.8644 High Similarity NPC118853
0.8571 High Similarity NPC471074
0.8571 High Similarity NPC473885
0.8532 High Similarity NPC42471
0.8487 Intermediate Similarity NPC178382
0.8376 Intermediate Similarity NPC137710
0.8361 Intermediate Similarity NPC329707
0.8348 Intermediate Similarity NPC28054
0.8347 Intermediate Similarity NPC83301
0.8293 Intermediate Similarity NPC59502
0.8291 Intermediate Similarity NPC187547
0.8291 Intermediate Similarity NPC21831
0.8291 Intermediate Similarity NPC206007
0.8279 Intermediate Similarity NPC141059
0.8254 Intermediate Similarity NPC200718
0.8241 Intermediate Similarity NPC156768
0.8226 Intermediate Similarity NPC45947
0.819 Intermediate Similarity NPC150895
0.816 Intermediate Similarity NPC477645
0.8136 Intermediate Similarity NPC243704
0.812 Intermediate Similarity NPC45536
0.8067 Intermediate Similarity NPC473969
0.8062 Intermediate Similarity NPC286130
0.8051 Intermediate Similarity NPC131801
0.8033 Intermediate Similarity NPC243269
0.8033 Intermediate Similarity NPC188377
0.8033 Intermediate Similarity NPC65735
0.8031 Intermediate Similarity NPC293253
0.8016 Intermediate Similarity NPC475092
0.8 Intermediate Similarity NPC105249
0.8 Intermediate Similarity NPC246214
0.7969 Intermediate Similarity NPC106247
0.7966 Intermediate Similarity NPC476031
0.7966 Intermediate Similarity NPC476014
0.7953 Intermediate Similarity NPC473982
0.7949 Intermediate Similarity NPC252004
0.7934 Intermediate Similarity NPC115859
0.7907 Intermediate Similarity NPC324117
0.7907 Intermediate Similarity NPC209858
0.7899 Intermediate Similarity NPC208906
0.7899 Intermediate Similarity NPC212918
0.7899 Intermediate Similarity NPC144745
0.7895 Intermediate Similarity NPC471521
0.7895 Intermediate Similarity NPC473356
0.787 Intermediate Similarity NPC146316
0.7826 Intermediate Similarity NPC177331
0.782 Intermediate Similarity NPC248795
0.7815 Intermediate Similarity NPC474987
0.7797 Intermediate Similarity NPC292036
0.7787 Intermediate Similarity NPC79557
0.7786 Intermediate Similarity NPC307401
0.7786 Intermediate Similarity NPC473268
0.7769 Intermediate Similarity NPC265793
0.7769 Intermediate Similarity NPC4898
0.776 Intermediate Similarity NPC470858
0.7742 Intermediate Similarity NPC141252
0.7742 Intermediate Similarity NPC11799
0.7734 Intermediate Similarity NPC136340
0.7727 Intermediate Similarity NPC472376
0.7727 Intermediate Similarity NPC177262
0.7724 Intermediate Similarity NPC477967
0.7724 Intermediate Similarity NPC317217
0.7717 Intermediate Similarity NPC50583
0.7712 Intermediate Similarity NPC53953
0.7692 Intermediate Similarity NPC54626
0.7692 Intermediate Similarity NPC57879
0.7686 Intermediate Similarity NPC87466
0.7686 Intermediate Similarity NPC254958
0.7686 Intermediate Similarity NPC291619
0.7685 Intermediate Similarity NPC233791
0.768 Intermediate Similarity NPC474829
0.768 Intermediate Similarity NPC75557
0.768 Intermediate Similarity NPC71274
0.7669 Intermediate Similarity NPC233707
0.7669 Intermediate Similarity NPC202260
0.7667 Intermediate Similarity NPC316062
0.7661 Intermediate Similarity NPC16922
0.7661 Intermediate Similarity NPC476351
0.7652 Intermediate Similarity NPC64157
0.7652 Intermediate Similarity NPC215109
0.7652 Intermediate Similarity NPC278832
0.7652 Intermediate Similarity NPC170604
0.7642 Intermediate Similarity NPC1848
0.7627 Intermediate Similarity NPC26157
0.7627 Intermediate Similarity NPC1811
0.7623 Intermediate Similarity NPC67345
0.7623 Intermediate Similarity NPC244862
0.7619 Intermediate Similarity NPC329922
0.7619 Intermediate Similarity NPC474260
0.7619 Intermediate Similarity NPC81912
0.7619 Intermediate Similarity NPC329694
0.76 Intermediate Similarity NPC477965
0.76 Intermediate Similarity NPC477038
0.7594 Intermediate Similarity NPC130976
0.7581 Intermediate Similarity NPC263870
0.7581 Intermediate Similarity NPC289911
0.7581 Intermediate Similarity NPC36255
0.7581 Intermediate Similarity NPC283284
0.7581 Intermediate Similarity NPC471549
0.7581 Intermediate Similarity NPC323118
0.7581 Intermediate Similarity NPC473379
0.7559 Intermediate Similarity NPC474830
0.7559 Intermediate Similarity NPC290955
0.7559 Intermediate Similarity NPC246392
0.7542 Intermediate Similarity NPC23332
0.7541 Intermediate Similarity NPC293424
0.754 Intermediate Similarity NPC179354
0.754 Intermediate Similarity NPC471559
0.752 Intermediate Similarity NPC475818
0.752 Intermediate Similarity NPC272899
0.7519 Intermediate Similarity NPC66246
0.7519 Intermediate Similarity NPC170546
0.75 Intermediate Similarity NPC279877
0.75 Intermediate Similarity NPC474279
0.75 Intermediate Similarity NPC263337
0.75 Intermediate Similarity NPC219969
0.75 Intermediate Similarity NPC474438
0.75 Intermediate Similarity NPC140688
0.75 Intermediate Similarity NPC159786
0.75 Intermediate Similarity NPC26532
0.75 Intermediate Similarity NPC474136
0.7481 Intermediate Similarity NPC201370
0.7481 Intermediate Similarity NPC473983
0.7481 Intermediate Similarity NPC148374
0.7481 Intermediate Similarity NPC218204
0.7481 Intermediate Similarity NPC473681
0.7481 Intermediate Similarity NPC470740
0.7481 Intermediate Similarity NPC61157
0.7481 Intermediate Similarity NPC18904
0.748 Intermediate Similarity NPC46536
0.748 Intermediate Similarity NPC138139
0.748 Intermediate Similarity NPC23086
0.748 Intermediate Similarity NPC74612
0.7462 Intermediate Similarity NPC282230
0.7462 Intermediate Similarity NPC183348
0.746 Intermediate Similarity NPC83115
0.746 Intermediate Similarity NPC130275
0.7459 Intermediate Similarity NPC469954
0.7458 Intermediate Similarity NPC183648
0.7444 Intermediate Similarity NPC303217
0.7442 Intermediate Similarity NPC208389
0.744 Intermediate Similarity NPC174915
0.744 Intermediate Similarity NPC314329
0.744 Intermediate Similarity NPC270807
0.7438 Intermediate Similarity NPC11821
0.7422 Intermediate Similarity NPC471554
0.7422 Intermediate Similarity NPC83178
0.7422 Intermediate Similarity NPC319140
0.7422 Intermediate Similarity NPC473355
0.7422 Intermediate Similarity NPC471573
0.7422 Intermediate Similarity NPC95567
0.7422 Intermediate Similarity NPC471501
0.7422 Intermediate Similarity NPC137570
0.7422 Intermediate Similarity NPC476016
0.7414 Intermediate Similarity NPC298087
0.7407 Intermediate Similarity NPC474615
0.7405 Intermediate Similarity NPC471817
0.7405 Intermediate Similarity NPC196979
0.7405 Intermediate Similarity NPC15083
0.7405 Intermediate Similarity NPC279596
0.7405 Intermediate Similarity NPC470977
0.7405 Intermediate Similarity NPC470976
0.7402 Intermediate Similarity NPC230979
0.7402 Intermediate Similarity NPC303010
0.7395 Intermediate Similarity NPC277525
0.7391 Intermediate Similarity NPC84479
0.7391 Intermediate Similarity NPC38209
0.7391 Intermediate Similarity NPC158871
0.7385 Intermediate Similarity NPC939
0.7377 Intermediate Similarity NPC470860
0.7377 Intermediate Similarity NPC76844
0.7368 Intermediate Similarity NPC217226
0.7364 Intermediate Similarity NPC327527
0.7364 Intermediate Similarity NPC207294
0.7364 Intermediate Similarity NPC476917
0.7364 Intermediate Similarity NPC112706
0.7364 Intermediate Similarity NPC477123
0.7364 Intermediate Similarity NPC477039
0.7364 Intermediate Similarity NPC477966
0.7364 Intermediate Similarity NPC477040
0.7353 Intermediate Similarity NPC282973
0.7348 Intermediate Similarity NPC471006
0.7344 Intermediate Similarity NPC52035
0.7344 Intermediate Similarity NPC473626
0.7339 Intermediate Similarity NPC35744
0.7338 Intermediate Similarity NPC114513
0.7338 Intermediate Similarity NPC56731
0.7338 Intermediate Similarity NPC245522
0.7328 Intermediate Similarity NPC298190
0.7328 Intermediate Similarity NPC61788
0.7319 Intermediate Similarity NPC64568

  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 NPC22678 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
0.7712 Intermediate Similarity NPD1241 Discontinued
0.7537 Intermediate Similarity NPD2343 Clinical (unspecified phase)
0.744 Intermediate Similarity NPD1547 Clinical (unspecified phase)
0.7244 Intermediate Similarity NPD3972 Approved
0.7167 Intermediate Similarity NPD2181 Clinical (unspecified phase)
0.7132 Intermediate Similarity NPD1876 Approved
0.7077 Intermediate Similarity NPD1049 Clinical (unspecified phase)
0.7045 Intermediate Similarity NPD6832 Phase 2
0.7029 Intermediate Similarity NPD1471 Phase 3
0.7029 Intermediate Similarity NPD2344 Approved
0.7023 Intermediate Similarity NPD1019 Discontinued
0.6977 Remote Similarity NPD9717 Approved
0.6963 Remote Similarity NPD3142 Approved
0.6963 Remote Similarity NPD3140 Approved
0.6905 Remote Similarity NPD9092 Discovery
0.6901 Remote Similarity NPD643 Clinical (unspecified phase)
0.6894 Remote Similarity NPD2798 Approved
0.6875 Remote Similarity NPD17 Approved
0.6846 Remote Similarity NPD5616 Clinical (unspecified phase)
0.6835 Remote Similarity NPD2796 Approved
0.6833 Remote Similarity NPD3134 Approved
0.6831 Remote Similarity NPD2309 Approved
0.6829 Remote Similarity NPD1609 Clinical (unspecified phase)
0.6828 Remote Similarity NPD920 Approved
0.6818 Remote Similarity NPD2797 Approved
0.6818 Remote Similarity NPD3267 Approved
0.6818 Remote Similarity NPD3266 Approved
0.6809 Remote Similarity NPD1243 Approved
0.6806 Remote Similarity NPD642 Clinical (unspecified phase)
0.6797 Remote Similarity NPD1651 Approved
0.6797 Remote Similarity NPD5585 Approved
0.6777 Remote Similarity NPD1358 Approved
0.6763 Remote Similarity NPD2799 Discontinued
0.6752 Remote Similarity NPD1238 Approved
0.6744 Remote Similarity NPD3412 Clinical (unspecified phase)
0.6721 Remote Similarity NPD2684 Approved
0.6721 Remote Similarity NPD2182 Approved
0.6719 Remote Similarity NPD9545 Approved
0.6719 Remote Similarity NPD1894 Discontinued
0.6718 Remote Similarity NPD1608 Approved
0.6716 Remote Similarity NPD9494 Approved
0.6712 Remote Similarity NPD3873 Phase 3
0.6712 Remote Similarity NPD3869 Phase 3
0.6711 Remote Similarity NPD6280 Approved
0.6711 Remote Similarity NPD6279 Approved
0.6692 Remote Similarity NPD1203 Approved
0.6691 Remote Similarity NPD3268 Approved
0.6691 Remote Similarity NPD2313 Discontinued
0.669 Remote Similarity NPD7421 Clinical (unspecified phase)
0.6667 Remote Similarity NPD1899 Clinical (unspecified phase)
0.6643 Remote Similarity NPD4628 Phase 3
0.6615 Remote Similarity NPD1778 Approved
0.6612 Remote Similarity NPD9697 Approved
0.6597 Remote Similarity NPD3887 Approved
0.6596 Remote Similarity NPD1551 Phase 2
0.6594 Remote Similarity NPD4307 Phase 2
0.6562 Remote Similarity NPD9493 Approved
0.6549 Remote Similarity NPD1552 Clinical (unspecified phase)
0.6549 Remote Similarity NPD2346 Discontinued
0.6549 Remote Similarity NPD1550 Clinical (unspecified phase)
0.6547 Remote Similarity NPD4618 Approved
0.6547 Remote Similarity NPD4622 Approved
0.6547 Remote Similarity NPD6355 Discontinued
0.6547 Remote Similarity NPD1933 Approved
0.6541 Remote Similarity NPD4359 Approved
0.6538 Remote Similarity NPD5691 Approved
0.6535 Remote Similarity NPD690 Clinical (unspecified phase)
0.6531 Remote Similarity NPD6273 Approved
0.6529 Remote Similarity NPD164 Approved
0.6525 Remote Similarity NPD3748 Approved
0.6522 Remote Similarity NPD8032 Phase 2
0.6519 Remote Similarity NPD5647 Approved
0.6515 Remote Similarity NPD1281 Approved
0.6508 Remote Similarity NPD7843 Approved
0.6508 Remote Similarity NPD5535 Approved
0.6504 Remote Similarity NPD290 Approved
0.6503 Remote Similarity NPD1549 Phase 2
0.6494 Remote Similarity NPD919 Approved
0.6494 Remote Similarity NPD5537 Clinical (unspecified phase)
0.6484 Remote Similarity NPD7157 Approved
0.6475 Remote Similarity NPD1240 Approved
0.6463 Remote Similarity NPD4662 Approved
0.6463 Remote Similarity NPD4661 Approved
0.6458 Remote Similarity NPD2800 Approved
0.6457 Remote Similarity NPD592 Approved
0.6457 Remote Similarity NPD594 Approved
0.6454 Remote Similarity NPD5689 Approved
0.6454 Remote Similarity NPD5688 Approved
0.6449 Remote Similarity NPD6798 Discontinued
0.6449 Remote Similarity NPD411 Approved
0.6439 Remote Similarity NPD3496 Discontinued
0.6434 Remote Similarity NPD6005 Phase 3
0.6434 Remote Similarity NPD2355 Clinical (unspecified phase)
0.6434 Remote Similarity NPD6002 Phase 3
0.6434 Remote Similarity NPD6006 Clinical (unspecified phase)
0.6434 Remote Similarity NPD6003 Clinical (unspecified phase)
0.6434 Remote Similarity NPD2353 Approved
0.6434 Remote Similarity NPD6004 Phase 3
0.6429 Remote Similarity NPD447 Suspended
0.6423 Remote Similarity NPD968 Approved
0.641 Remote Similarity NPD1247 Approved
0.6408 Remote Similarity NPD4308 Phase 3
0.64 Remote Similarity NPD2067 Discontinued
0.6395 Remote Similarity NPD6799 Approved
0.6385 Remote Similarity NPD5536 Phase 2
0.6383 Remote Similarity NPD1607 Approved
0.6378 Remote Similarity NPD821 Approved
0.6376 Remote Similarity NPD5586 Clinical (unspecified phase)
0.637 Remote Similarity NPD1283 Approved
0.637 Remote Similarity NPD3295 Clinical (unspecified phase)
0.6369 Remote Similarity NPD6808 Phase 2
0.6369 Remote Similarity NPD5668 Clinical (unspecified phase)
0.6364 Remote Similarity NPD4477 Approved
0.6364 Remote Similarity NPD4476 Approved
0.6364 Remote Similarity NPD4947 Clinical (unspecified phase)
0.6358 Remote Similarity NPD6599 Discontinued
0.6357 Remote Similarity NPD2979 Phase 3
0.6357 Remote Similarity NPD2557 Approved
0.6351 Remote Similarity NPD2532 Approved
0.6351 Remote Similarity NPD2533 Approved
0.6351 Remote Similarity NPD2534 Approved
0.6351 Remote Similarity NPD4378 Clinical (unspecified phase)
0.635 Remote Similarity NPD454 Approved
0.6345 Remote Similarity NPD2654 Approved
0.6343 Remote Similarity NPD1481 Phase 2
0.6331 Remote Similarity NPD6859 Clinical (unspecified phase)
0.6331 Remote Similarity NPD1699 Clinical (unspecified phase)
0.6324 Remote Similarity NPD6362 Approved
0.6308 Remote Similarity NPD3596 Phase 2
0.6301 Remote Similarity NPD3750 Approved
0.6299 Remote Similarity NPD2296 Approved
0.6294 Remote Similarity NPD1510 Phase 2
0.6291 Remote Similarity NPD2651 Approved
0.6291 Remote Similarity NPD2649 Approved
0.6289 Remote Similarity NPD4575 Clinical (unspecified phase)
0.6288 Remote Similarity NPD3445 Approved
0.6288 Remote Similarity NPD4196 Clinical (unspecified phase)
0.6288 Remote Similarity NPD3444 Approved
0.6288 Remote Similarity NPD3443 Approved
0.6286 Remote Similarity NPD6233 Phase 2
0.6286 Remote Similarity NPD4062 Phase 3
0.6276 Remote Similarity NPD2897 Discontinued
0.6275 Remote Similarity NPD7577 Discontinued
0.6269 Remote Similarity NPD1535 Discovery
0.626 Remote Similarity NPD1237 Approved
0.6259 Remote Similarity NPD2354 Approved
0.625 Remote Similarity NPD2935 Discontinued
0.6242 Remote Similarity NPD5494 Approved
0.6242 Remote Similarity NPD7410 Clinical (unspecified phase)
0.6241 Remote Similarity NPD4626 Approved
0.6234 Remote Similarity NPD5761 Phase 2
0.6234 Remote Similarity NPD7819 Suspended
0.6234 Remote Similarity NPD5760 Phase 2
0.6226 Remote Similarity NPD3926 Phase 2
0.6224 Remote Similarity NPD743 Approved
0.6216 Remote Similarity NPD7440 Discontinued
0.6214 Remote Similarity NPD1296 Phase 2
0.6214 Remote Similarity NPD3764 Approved
0.6212 Remote Similarity NPD6581 Approved
0.6212 Remote Similarity NPD6580 Approved
0.6211 Remote Similarity NPD7893 Clinical (unspecified phase)
0.6209 Remote Similarity NPD5890 Approved
0.6209 Remote Similarity NPD5889 Approved
0.6209 Remote Similarity NPD7411 Suspended
0.62 Remote Similarity NPD5049 Phase 3
0.62 Remote Similarity NPD2186 Approved
0.6194 Remote Similarity NPD8443 Clinical (unspecified phase)
0.6194 Remote Similarity NPD3847 Discontinued
0.619 Remote Similarity NPD7003 Approved
0.619 Remote Similarity NPD4109 Clinical (unspecified phase)
0.619 Remote Similarity NPD4110 Phase 3
0.6184 Remote Similarity NPD5808 Clinical (unspecified phase)
0.6181 Remote Similarity NPD7033 Discontinued
0.6179 Remote Similarity NPD9261 Approved
0.6176 Remote Similarity NPD5327 Phase 3
0.6173 Remote Similarity NPD3050 Clinical (unspecified phase)
0.6172 Remote Similarity NPD1139 Approved
0.6172 Remote Similarity NPD1137 Approved
0.617 Remote Similarity NPD4870 Approved
0.6165 Remote Similarity NPD6830 Clinical (unspecified phase)
0.6165 Remote Similarity NPD3049 Approved
0.6164 Remote Similarity NPD4534 Discontinued
0.6164 Remote Similarity NPD970 Clinical (unspecified phase)
0.6164 Remote Similarity NPD2424 Discontinued
0.6164 Remote Similarity NPD5958 Discontinued
0.6159 Remote Similarity NPD6765 Approved
0.6159 Remote Similarity NPD6764 Approved
0.6159 Remote Similarity NPD5403 Approved
0.6159 Remote Similarity NPD6980 Clinical (unspecified phase)
0.6159 Remote Similarity NPD6559 Discontinued
0.6154 Remote Similarity NPD6653 Approved
0.6154 Remote Similarity NPD3882 Suspended
0.6148 Remote Similarity NPD6287 Discontinued
0.6143 Remote Similarity NPD5952 Clinical (unspecified phase)
0.6143 Remote Similarity NPD2598 Clinical (unspecified phase)
0.6142 Remote Similarity NPD5451 Approved
0.614 Remote Similarity NPD9257 Approved
0.614 Remote Similarity NPD9259 Approved
0.6138 Remote Similarity NPD6100 Approved
0.6138 Remote Similarity NPD2531 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