Structure

Physi-Chem Properties

Molecular Weight:  164.08
Volume:  179.994
LogP:  3.08
LogD:  2.835
LogS:  -2.367
# Rotatable Bonds:  1
TPSA:  40.46
# H-Bond Aceptor:  2
# H-Bond Donor:  2
# Rings:  1
# Heavy Atoms:  2

MedChem Properties

QED Drug-Likeness Score:  0.626
Synthetic Accessibility Score:  2.485
Fsp3:  0.2
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.562
MDCK Permeability:  1.820874967961572e-05
Pgp-inhibitor:  0.002
Pgp-substrate:  0.001
Human Intestinal Absorption (HIA):  0.004
20% Bioavailability (F20%):  0.904
30% Bioavailability (F30%):  0.17

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.091
Plasma Protein Binding (PPB):  91.09404754638672%
Volume Distribution (VD):  0.831
Pgp-substrate:  9.747885704040527%

ADMET: Metabolism

CYP1A2-inhibitor:  0.922
CYP1A2-substrate:  0.926
CYP2C19-inhibitor:  0.235
CYP2C19-substrate:  0.11
CYP2C9-inhibitor:  0.306
CYP2C9-substrate:  0.807
CYP2D6-inhibitor:  0.616
CYP2D6-substrate:  0.833
CYP3A4-inhibitor:  0.17
CYP3A4-substrate:  0.227

ADMET: Excretion

Clearance (CL):  17.232
Half-life (T1/2):  0.778

ADMET: Toxicity

hERG Blockers:  0.028
Human Hepatotoxicity (H-HT):  0.051
Drug-inuced Liver Injury (DILI):  0.348
AMES Toxicity:  0.291
Rat Oral Acute Toxicity:  0.462
Maximum Recommended Daily Dose:  0.902
Skin Sensitization:  0.928
Carcinogencity:  0.283
Eye Corrosion:  0.669
Eye Irritation:  0.97
Respiratory Toxicity:  0.723

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Similar NPs/Drugs  

  Natural Product: NPC166788

Natural Product ID:  NPC166788
Common Name*:   Thymoquinone
IUPAC Name:   2-methyl-5-propan-2-ylcyclohexa-2,5-diene-1,4-dione
Synonyms:   Thymoquinone
Standard InCHIKey:  KEQHJBNSCLWCAE-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C10H12O2/c1-6(2)8-5-9(11)7(3)4-10(8)12/h4-6H,1-3H3
SMILES:  CC(C)C1=CC(=O)C(=CC1=O)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1672002
PubChem CID:   10281
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0004603] Organic oxygen compounds
      • [CHEMONTID:0000323] Organooxygen compounds
        • [CHEMONTID:0001831] Carbonyl compounds
          • [CHEMONTID:0000118] Ketones
            • [CHEMONTID:0003487] Cyclic ketones
              • [CHEMONTID:0002495] Quinones
                • [CHEMONTID:0002384] Benzoquinones
                  • [CHEMONTID:0002494] P-benzoquinones

*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
NPO15243 Pimenta dioica Species Myrtaceae Eukaryota n.a. n.a. n.a. PMID[10869193]
NPO19472 Thymus vulgaris Species Lamiaceae Eukaryota Leaves n.a. n.a. PMID[12088434]
NPO27360 Pyracantha fortuneana Species Rosaceae Eukaryota fruit n.a. n.a. PMID[16872137]
NPO15243 Pimenta dioica Species Myrtaceae Eukaryota Berries n.a. n.a. PMID[18314960]
NPO11654 Eusynstyela misakiensis Species n.a. n.a. n.a. n.a. n.a. PMID[19505081]
NPO19472 Thymus vulgaris Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[21707257]
NPO15436 Brucea mollis Species Simaroubaceae Eukaryota stems n.a. n.a. PMID[22070654]
NPO15436 Brucea mollis Species Simaroubaceae Eukaryota n.a. stem n.a. PMID[22070654]
NPO15436 Brucea mollis Species Simaroubaceae Eukaryota n.a. stem n.a. PMID[24199564]
NPO22667 Plectranthus amboinicus Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[24491635]
NPO2136 Nigella glandulifera Species Ranunculaceae Eukaryota Seeds n.a. n.a. PMID[24593120]
NPO2136 Nigella glandulifera Species Ranunculaceae Eukaryota n.a. n.a. n.a. PMID[26227777]
NPO11654 Eusynstyela misakiensis Species n.a. n.a. n.a. n.a. n.a. PMID[7931370]
NPO15243 Pimenta dioica Species Myrtaceae Eukaryota Plant n.a. n.a. Database[FooDB]
NPO23226 Satureja montana Species Lamiaceae Eukaryota Plant n.a. n.a. Database[FooDB]
NPO19472 Thymus vulgaris Species Lamiaceae Eukaryota Shoot n.a. n.a. Database[FooDB]
NPO19472 Thymus vulgaris Species Lamiaceae Eukaryota n.a. n.a. Database[FooDB]
NPO15243 Pimenta dioica Species Myrtaceae Eukaryota n.a. n.a. Database[FooDB]
NPO19472 Thymus vulgaris Species Lamiaceae Eukaryota Essential Oil n.a. n.a. Database[FooDB]
NPO15243 Pimenta dioica Species Myrtaceae Eukaryota n.a. n.a. Database[FooDB]
NPO15243 Pimenta dioica Species Myrtaceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO19472 Thymus vulgaris Species Lamiaceae Eukaryota n.a. n.a. Database[FooDB]
NPO19472 Thymus vulgaris Species Lamiaceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO15243 Pimenta dioica Species Myrtaceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO15243 Pimenta dioica Species Myrtaceae Eukaryota Leaf Essent. Oil n.a. n.a. Database[FooDB]
NPO19472 Thymus vulgaris Species Lamiaceae Eukaryota Plant n.a. n.a. Database[FooDB]
NPO15243 Pimenta dioica Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO12935 Thymus quinquecostatus Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO19472 Thymus vulgaris Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO19472 Thymus vulgaris Species Lamiaceae Eukaryota n.a. n.a. Database[Phenol-Explorer]
NPO23226 Satureja montana Species Lamiaceae Eukaryota n.a. n.a. Database[Phenol-Explorer]
NPO15243 Pimenta dioica Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO12935 Thymus quinquecostatus Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO19472 Thymus vulgaris Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15243 Pimenta dioica Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO19472 Thymus vulgaris Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO2136 Nigella glandulifera Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO19472 Thymus vulgaris Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO12935 Thymus quinquecostatus Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO15243 Pimenta dioica Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15618 Teucrium luteum Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12935 Thymus quinquecostatus Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1685 Mespilodaphne pretiosa n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO6262 Rumphella aggregata Species Plexauridae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2136 Nigella glandulifera Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3209 Anchusa strigosa Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13652 Laurilia sulcata Species Corticiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22667 Plectranthus amboinicus Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19472 Thymus vulgaris Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15532 Polygala crotalarioides Species Polygalaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11654 Eusynstyela misakiensis Species n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO27360 Pyracantha fortuneana Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14275 Carissa opaca Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3904 Casearia esculenta Species Salicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15436 Brucea mollis Species Simaroubaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15152 Fagara leprieurii n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO14854 Stereocaulon ramulosum Species Stereocaulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12504 Penstemon acuminatus Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23226 Satureja montana Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]

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

  NP Quantity Composition/Concentration

Organism ID NP ID Organism Material Preparation Organism Part NP Quantity (Standard) NP Quantity (Minimum) NP Quantity (Maximum) Quantity Unit Reference
NPO23226 NPC166788 n.a. Plant 3.8 0.1 7.5 mg/100g Database [DUKE]

☑ 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
NPT116 Cell Line HL-60 Homo sapiens IC50 = 28000.0 nM PMID[572455]
NPT139 Cell Line HT-29 Homo sapiens IC50 = 47000.0 nM PMID[572455]
NPT859 Cell Line HFF Homo sapiens IC50 = 33000.0 nM PMID[572455]
NPT66 Individual Protein Acetylcholinesterase Electrophorus electricus Inhibition = 7.9 % PMID[572456]
NPT1217 Individual Protein Botulinum neurotoxin type A Clostridium botulinum Ratio = 0.38 /M/s PMID[572461]
NPT165 Cell Line HeLa Homo sapiens IC50 = 2060.0 nM PMID[572462]
NPT83 Cell Line MCF7 Homo sapiens IC50 = 6190.0 nM PMID[572462]
NPT3414 Individual Protein Serine/threonine-protein kinase PLK2 Homo sapiens IC50 = 14720.0 nM PMID[572462]
NPT3358 Individual Protein Serine/threonine-protein kinase PLK3 Homo sapiens IC50 > 50000.0 nM PMID[572462]
NPT404 Cell Line CCRF-CEM Homo sapiens EC50 = 300.0 nM PMID[572464]
NPT2251 Cell Line ADR5000 cell line EC50 = 300.0 nM PMID[572464]
NPT2251 Cell Line ADR5000 cell line EC50 = 300.0 nM PMID[572466]
NPT404 Cell Line CCRF-CEM Homo sapiens EC50 = 300.0 nM PMID[572466]
NPT2615 Cell Line HEK-293T Homo sapiens CC50 = 140.0 ug.mL-1 PMID[572467]
NPT65 Cell Line HepG2 Homo sapiens Activity = 3.3 % PMID[572468]
NPT65 Cell Line HepG2 Homo sapiens Activity = 91.8 % PMID[572468]
NPT179 Cell Line A2780 Homo sapiens IC50 = 7900.0 nM PMID[572469]
NPT381 Cell Line OVCAR-8 Homo sapiens IC50 = 11600.0 nM PMID[572469]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 28000.0 nM PMID[572455]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 32000.0 nM PMID[572455]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 27000.0 nM PMID[572455]
NPT67 Individual Protein Cholinesterase Equus caballus Inhibition = -0.33 % PMID[572456]
NPT1365 Organism Trichoplusia ni Trichoplusia ni mortality = 26.7 % PMID[572457]
NPT1365 Organism Trichoplusia ni Trichoplusia ni DC50 = 19.3 microg/cm2 PMID[572457]
NPT1365 Organism Trichoplusia ni Trichoplusia ni FDI = 100.0 % PMID[572457]
NPT489 Organism Coptotermes formosanus Coptotermes formosanus Activity = 93.1 mg PMID[572458]
NPT489 Organism Coptotermes formosanus Coptotermes formosanus Activity = 80.6 mg PMID[572458]
NPT489 Organism Coptotermes formosanus Coptotermes formosanus Activity = 75.4 mg PMID[572458]
NPT489 Organism Coptotermes formosanus Coptotermes formosanus Activity = 74.0 mg PMID[572458]
NPT489 Organism Coptotermes formosanus Coptotermes formosanus Activity = 83.5 mg PMID[572458]
NPT489 Organism Coptotermes formosanus Coptotermes formosanus Activity = 0.0 mg PMID[572458]
NPT489 Organism Coptotermes formosanus Coptotermes formosanus mortality = 5.0 % PMID[572458]
NPT489 Organism Coptotermes formosanus Coptotermes formosanus mortality = 11.7 % PMID[572458]
NPT489 Organism Coptotermes formosanus Coptotermes formosanus mortality = 8.3 % PMID[572458]
NPT489 Organism Coptotermes formosanus Coptotermes formosanus mortality = 6.7 % PMID[572458]
NPT489 Organism Coptotermes formosanus Coptotermes formosanus mortality = 1.7 % PMID[572458]
NPT489 Organism Coptotermes formosanus Coptotermes formosanus mortality = 10.0 % PMID[572458]
NPT489 Organism Coptotermes formosanus Coptotermes formosanus mortality = 3.3 % PMID[572458]
NPT489 Organism Coptotermes formosanus Coptotermes formosanus mortality = 0.0 % PMID[572458]
NPT489 Organism Coptotermes formosanus Coptotermes formosanus mortality = 18.3 % PMID[572458]
NPT489 Organism Coptotermes formosanus Coptotermes formosanus mortality = 100.0 % PMID[572458]
NPT72 Individual Protein Solute carrier organic anion transporter family member 1B3 Homo sapiens Inhibition = 98.24 % PMID[572459]
NPT73 Individual Protein Solute carrier organic anion transporter family member 1B1 Homo sapiens Inhibition = 126.43 % PMID[572459]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 101900.0 nM PMID[572460]
NPT831 Individual Protein Serine/threonine-protein kinase PLK1 Homo sapiens IC50 = 2180.0 nM PMID[572462]
NPT2 Others Unspecified Ratio IC50 = 7.0 n.a. PMID[572462]
NPT3697 Organism Leishmania tropica Leishmania tropica IC50 = 1.16 ug.mL-1 PMID[572463]
NPT1021 Organism Leishmania infantum Leishmania infantum IC50 = 1.47 ug.mL-1 PMID[572463]
NPT29 Organism Rattus norvegicus Rattus norvegicus Cmax = 0.4 ug.mL-1 PMID[572463]
NPT29 Organism Rattus norvegicus Rattus norvegicus Cmax = 0.9 ug.mL-1 PMID[572463]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum EC50 > 80000.0 nM PMID[572464]
NPT2262 Organism Human herpesvirus 5 strain AD169 Human herpesvirus 5 strain AD169 EC50 > 10000.0 nM PMID[572464]
NPT2 Others Unspecified Activity = 24.0 % PMID[572465]
NPT2 Others Unspecified Activity = 33.0 % PMID[572465]
NPT2 Others Unspecified Activity = 40.0 % PMID[572465]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum EC50 > 80000.0 nM PMID[572466]
NPT2262 Organism Human herpesvirus 5 strain AD169 Human herpesvirus 5 strain AD169 EC50 > 10000.0 nM PMID[572466]
NPT831 Individual Protein Serine/threonine-protein kinase PLK1 Homo sapiens INH = 2.19 ug ml-1 PMID[572467]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum IC50 = 1200.0 nM PMID[572469]
NPT35 Others n.a. Solubility = 467.8 ug.mL-1 PMID[572469]
NPT2 Others Unspecified IC50 = 7800.0 nM PMID[572469]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum IC50 = 25000.0 nM PMID[572469]
NPT2 Others Unspecified Ratio IC50 = 2.3 n.a. PMID[572469]
NPT2 Others Unspecified IC50 = 17800.0 nM PMID[572469]
NPT20555 ORGANISM SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 Hit score = 0.1059 n.a. PMID[572470]
NPT20555 ORGANISM SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 Hit score = 0.2773 n.a. PMID[572470]
NPT20555 ORGANISM SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 IC50 > 20000.0 nM PMID[572471]
NPT20555 ORGANISM SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 IC50 > 19952.62 nM PMID[572471]
NPT2 Others Unspecified IC50 = 130000.0 nM PMID[572472]

☑ 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 NPC166788 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
0.8864 High Similarity NPC477686
0.881 High Similarity NPC111474
0.8723 High Similarity NPC176819
0.8723 High Similarity NPC118788
0.8723 High Similarity NPC163984
0.8723 High Similarity NPC58970
0.8667 High Similarity NPC191337
0.8478 Intermediate Similarity NPC262558
0.8478 Intermediate Similarity NPC8610
0.8333 Intermediate Similarity NPC32351
0.8333 Intermediate Similarity NPC228776
0.8085 Intermediate Similarity NPC471752
0.8043 Intermediate Similarity NPC471753
0.8043 Intermediate Similarity NPC25771
0.8 Intermediate Similarity NPC471751
0.7959 Intermediate Similarity NPC15325
0.7917 Intermediate Similarity NPC91962
0.7857 Intermediate Similarity NPC38497
0.7843 Intermediate Similarity NPC268564
0.7843 Intermediate Similarity NPC23117
0.7843 Intermediate Similarity NPC37644
0.7826 Intermediate Similarity NPC292463
0.7826 Intermediate Similarity NPC216921
0.78 Intermediate Similarity NPC64866
0.7778 Intermediate Similarity NPC311852
0.7674 Intermediate Similarity NPC185839
0.7619 Intermediate Similarity NPC269641
0.7556 Intermediate Similarity NPC113082
0.75 Intermediate Similarity NPC14002
0.75 Intermediate Similarity NPC474805
0.75 Intermediate Similarity NPC45283
0.75 Intermediate Similarity NPC296311
0.75 Intermediate Similarity NPC180840
0.7447 Intermediate Similarity NPC301972
0.7407 Intermediate Similarity NPC473733
0.7381 Intermediate Similarity NPC12889
0.7358 Intermediate Similarity NPC5626
0.7358 Intermediate Similarity NPC100809
0.7358 Intermediate Similarity NPC209431
0.7347 Intermediate Similarity NPC236355
0.7347 Intermediate Similarity NPC14917
0.7347 Intermediate Similarity NPC4079
0.7308 Intermediate Similarity NPC137396
0.7255 Intermediate Similarity NPC220191
0.7222 Intermediate Similarity NPC275472
0.7174 Intermediate Similarity NPC101147
0.717 Intermediate Similarity NPC474141
0.7143 Intermediate Similarity NPC266979
0.7143 Intermediate Similarity NPC170799
0.7143 Intermediate Similarity NPC281195
0.7143 Intermediate Similarity NPC308108
0.7119 Intermediate Similarity NPC212210
0.7119 Intermediate Similarity NPC150162
0.7115 Intermediate Similarity NPC22329
0.7083 Intermediate Similarity NPC106819
0.7059 Intermediate Similarity NPC145311
0.7037 Intermediate Similarity NPC317796
0.7018 Intermediate Similarity NPC472304
0.7018 Intermediate Similarity NPC276764
0.7 Intermediate Similarity NPC100380
0.7 Intermediate Similarity NPC470329
0.7 Intermediate Similarity NPC251118
0.6964 Remote Similarity NPC193695
0.6964 Remote Similarity NPC283502
0.6964 Remote Similarity NPC268185
0.6957 Remote Similarity NPC217923
0.6949 Remote Similarity NPC165695
0.6949 Remote Similarity NPC288253
0.6949 Remote Similarity NPC32285
0.6923 Remote Similarity NPC225974
0.6909 Remote Similarity NPC297280
0.6897 Remote Similarity NPC127582
0.6889 Remote Similarity NPC24833
0.6863 Remote Similarity NPC324812
0.6852 Remote Similarity NPC295777
0.6852 Remote Similarity NPC69898
0.6842 Remote Similarity NPC27610
0.6842 Remote Similarity NPC56905
0.6809 Remote Similarity NPC18205
0.6809 Remote Similarity NPC12319
0.6792 Remote Similarity NPC30433
0.6792 Remote Similarity NPC27438
0.678 Remote Similarity NPC213152
0.678 Remote Similarity NPC269737
0.678 Remote Similarity NPC97322
0.6774 Remote Similarity NPC475523
0.6744 Remote Similarity NPC213749
0.6744 Remote Similarity NPC304788
0.6739 Remote Similarity NPC130923
0.6739 Remote Similarity NPC155880
0.6739 Remote Similarity NPC92863
0.6727 Remote Similarity NPC202850
0.6727 Remote Similarity NPC474127
0.6727 Remote Similarity NPC63396
0.6724 Remote Similarity NPC203233
0.6724 Remote Similarity NPC96551
0.6724 Remote Similarity NPC259261
0.6724 Remote Similarity NPC473494
0.6724 Remote Similarity NPC285594
0.6667 Remote Similarity NPC200831
0.6667 Remote Similarity NPC167256
0.6667 Remote Similarity NPC155198
0.6667 Remote Similarity NPC115385
0.6667 Remote Similarity NPC188292
0.6667 Remote Similarity NPC224103
0.6667 Remote Similarity NPC260474
0.6667 Remote Similarity NPC322457
0.6667 Remote Similarity NPC151919
0.6667 Remote Similarity NPC229046
0.6667 Remote Similarity NPC22098
0.6667 Remote Similarity NPC195246
0.6667 Remote Similarity NPC46565
0.6667 Remote Similarity NPC87141
0.6667 Remote Similarity NPC276009
0.6667 Remote Similarity NPC299369
0.6613 Remote Similarity NPC137163
0.661 Remote Similarity NPC25853
0.661 Remote Similarity NPC79756
0.6607 Remote Similarity NPC188789
0.66 Remote Similarity NPC114841
0.6562 Remote Similarity NPC469914
0.6562 Remote Similarity NPC256846
0.6562 Remote Similarity NPC474060
0.6557 Remote Similarity NPC4638
0.6557 Remote Similarity NPC6697
0.6557 Remote Similarity NPC285371
0.6557 Remote Similarity NPC475124
0.6552 Remote Similarity NPC139056
0.6552 Remote Similarity NPC94991
0.6552 Remote Similarity NPC60772
0.6552 Remote Similarity NPC30215
0.6552 Remote Similarity NPC320421
0.6552 Remote Similarity NPC266295
0.6522 Remote Similarity NPC254764
0.6508 Remote Similarity NPC106613
0.65 Remote Similarity NPC475795
0.65 Remote Similarity NPC64985
0.65 Remote Similarity NPC260573
0.6491 Remote Similarity NPC20603
0.6481 Remote Similarity NPC148056
0.6462 Remote Similarity NPC2634
0.6462 Remote Similarity NPC265782
0.6462 Remote Similarity NPC251929
0.6452 Remote Similarity NPC470688
0.6441 Remote Similarity NPC143834
0.6429 Remote Similarity NPC129710
0.6429 Remote Similarity NPC189677
0.6415 Remote Similarity NPC267110
0.6406 Remote Similarity NPC310992
0.6393 Remote Similarity NPC151728
0.6393 Remote Similarity NPC474658
0.6393 Remote Similarity NPC190049
0.6393 Remote Similarity NPC477830
0.6393 Remote Similarity NPC57463
0.6379 Remote Similarity NPC71755
0.6379 Remote Similarity NPC192427
0.6379 Remote Similarity NPC165808
0.6364 Remote Similarity NPC170167
0.6364 Remote Similarity NPC474539
0.6364 Remote Similarity NPC216407
0.6364 Remote Similarity NPC54123
0.6364 Remote Similarity NPC474562
0.6349 Remote Similarity NPC166791
0.6349 Remote Similarity NPC100719
0.6349 Remote Similarity NPC322035
0.6308 Remote Similarity NPC139397
0.6308 Remote Similarity NPC136473
0.6296 Remote Similarity NPC116906
0.6296 Remote Similarity NPC474391
0.6296 Remote Similarity NPC236338
0.6296 Remote Similarity NPC27264
0.6296 Remote Similarity NPC20934
0.6296 Remote Similarity NPC288381
0.629 Remote Similarity NPC169275
0.629 Remote Similarity NPC52449
0.629 Remote Similarity NPC474400
0.629 Remote Similarity NPC34622
0.629 Remote Similarity NPC473902
0.6275 Remote Similarity NPC6963
0.6275 Remote Similarity NPC267514
0.6275 Remote Similarity NPC106547
0.6275 Remote Similarity NPC304079
0.6275 Remote Similarity NPC145755
0.6271 Remote Similarity NPC471619
0.6269 Remote Similarity NPC474228
0.6269 Remote Similarity NPC276336
0.6269 Remote Similarity NPC303613
0.625 Remote Similarity NPC290350
0.625 Remote Similarity NPC269985
0.625 Remote Similarity NPC4370
0.625 Remote Similarity NPC168521
0.625 Remote Similarity NPC33761
0.623 Remote Similarity NPC294304
0.623 Remote Similarity NPC228574
0.623 Remote Similarity NPC60565
0.6212 Remote Similarity NPC203819
0.6212 Remote Similarity NPC260040
0.6212 Remote Similarity NPC307176
0.6207 Remote Similarity NPC141699
0.619 Remote Similarity NPC98897

  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 NPC166788 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
0.7333 Intermediate Similarity NPD5783 Phase 3
0.7143 Intermediate Similarity NPD287 Approved
0.6667 Remote Similarity NPD8779 Phase 3
0.6462 Remote Similarity NPD4691 Approved
0.6429 Remote Similarity NPD539 Approved
0.6349 Remote Similarity NPD7331 Phase 2
0.6308 Remote Similarity NPD4137 Phase 3
0.6212 Remote Similarity NPD4747 Approved
0.6176 Remote Similarity NPD4058 Approved
0.617 Remote Similarity NPD319 Phase 1
0.6129 Remote Similarity NPD2664 Clinical (unspecified phase)
0.6119 Remote Similarity NPD5276 Approved
0.6094 Remote Similarity NPD6108 Clinical (unspecified phase)
0.6034 Remote Similarity NPD4627 Clinical (unspecified phase)
0.5942 Remote Similarity NPD5733 Approved
0.5942 Remote Similarity NPD4687 Approved
0.5938 Remote Similarity NPD7341 Phase 2
0.5818 Remote Similarity NPD4220 Pre-registration
0.5758 Remote Similarity NPD3709 Clinical (unspecified phase)
0.5714 Remote Similarity NPD4194 Approved
0.5714 Remote Similarity NPD4191 Approved
0.5714 Remote Similarity NPD4192 Approved
0.5714 Remote Similarity NPD4193 Approved
0.5676 Remote Similarity NPD4695 Discontinued
0.5672 Remote Similarity NPD3621 Clinical (unspecified phase)
0.5614 Remote Similarity NPD6927 Phase 3

  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