Structure

Physi-Chem Properties

Molecular Weight:  222.2
Volume:  257.037
LogP:  4.938
LogD:  4.324
LogS:  -4.224
# Rotatable Bonds:  1
TPSA:  20.23
# H-Bond Aceptor:  1
# H-Bond Donor:  1
# Rings:  2
# Heavy Atoms:  1

MedChem Properties

QED Drug-Likeness Score:  0.669
Synthetic Accessibility Score:  4.02
Fsp3:  0.867
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:  -4.354
MDCK Permeability:  1.7975011360249482e-05
Pgp-inhibitor:  0.03
Pgp-substrate:  0.004
Human Intestinal Absorption (HIA):  0.003
20% Bioavailability (F20%):  0.867
30% Bioavailability (F30%):  0.645

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.078
Plasma Protein Binding (PPB):  94.2582015991211%
Volume Distribution (VD):  1.009
Pgp-substrate:  3.269573211669922%

ADMET: Metabolism

CYP1A2-inhibitor:  0.576
CYP1A2-substrate:  0.437
CYP2C19-inhibitor:  0.181
CYP2C19-substrate:  0.911
CYP2C9-inhibitor:  0.337
CYP2C9-substrate:  0.143
CYP2D6-inhibitor:  0.011
CYP2D6-substrate:  0.107
CYP3A4-inhibitor:  0.308
CYP3A4-substrate:  0.606

ADMET: Excretion

Clearance (CL):  12.588
Half-life (T1/2):  0.345

ADMET: Toxicity

hERG Blockers:  0.037
Human Hepatotoxicity (H-HT):  0.396
Drug-inuced Liver Injury (DILI):  0.19
AMES Toxicity:  0.008
Rat Oral Acute Toxicity:  0.058
Maximum Recommended Daily Dose:  0.024
Skin Sensitization:  0.117
Carcinogencity:  0.141
Eye Corrosion:  0.282
Eye Irritation:  0.463
Respiratory Toxicity:  0.341

Download Data

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

  Natural Product: NPC79576

Natural Product ID:  NPC79576
Common Name*:   T-Cadinol
IUPAC Name:   (1S,4S,4aR,8aR)-1,6-dimethyl-4-propan-2-yl-3,4,4a,7,8,8a-hexahydro-2H-naphthalen-1-ol
Synonyms:  
Standard InCHIKey:  LHYHMMRYTDARSZ-XQLPTFJDSA-N
Standard InCHI:  InChI=1S/C15H26O/c1-10(2)12-7-8-15(4,16)14-6-5-11(3)9-13(12)14/h9-10,12-14,16H,5-8H2,1-4H3/t12-,13-,14+,15-/m0/s1
SMILES:  CC(C)[C@@H]1CC[C@@](C)([C@@H]2CCC(=C[C@@H]12)C)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL2228955
PubChem CID:   160799
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001550] 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
NPO1048 Ajuga reptans Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[15043410]
NPO15538 Eucalyptus citriodora Species Myrtaceae Eukaryota Leaves the campus of Panjab University, Chandigarh, India PMID[16989303]
NPO10932 Melissa officinalis Species Lamiaceae Eukaryota stems and leaves n.a. n.a. PMID[18004816]
NPO13135 Campylotropis hirtella Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[19481938]
NPO10932 Melissa officinalis Species Lamiaceae Eukaryota Leaves; Stems n.a. n.a. PMID[19653667]
NPO10932 Melissa officinalis Species Lamiaceae Eukaryota fresh leaves and stems n.a. n.a. PMID[19653667]
NPO8666 Acorus tatarinowii Species Acoraceae Eukaryota n.a. n.a. n.a. PMID[20476749]
NPO11100 Artemisia capillaris Species Asteraceae Eukaryota n.a. whole plant n.a. PMID[21428416]
NPO20414 Ocimum basilicum Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[21574561]
NPO5681 Acorus gramineus Species Acoraceae Eukaryota Rhizomes n.a. n.a. PMID[21936523]
NPO5681 Acorus gramineus Species Acoraceae Eukaryota n.a. rhizome n.a. PMID[21936523]
NPO24241 Taiwania cryptomerioides Species Cupressaceae Eukaryota n.a. twig n.a. PMID[22474975]
NPO11100 Artemisia capillaris Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[22870812]
NPO5681 Acorus gramineus Species Acoraceae Eukaryota rhizomes n.a. n.a. PMID[22951040]
NPO11100 Artemisia capillaris Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[23435948]
NPO8666 Acorus tatarinowii Species Acoraceae Eukaryota n.a. rhizome n.a. PMID[23713285]
NPO20414 Ocimum basilicum Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[23747095]
NPO15538 Eucalyptus citriodora Species Myrtaceae Eukaryota Essential oil n.a. n.a. PMID[24641242]
NPO11100 Artemisia capillaris Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[25737008]
NPO8666 Acorus tatarinowii Species Acoraceae Eukaryota rhizomes n.a. n.a. PMID[26296476]
NPO8666 Acorus tatarinowii Species Acoraceae Eukaryota n.a. n.a. n.a. PMID[26305406]
NPO12796 Periploca sepium Species Apocynaceae Eukaryota n.a. n.a. n.a. PMID[28294615]
NPO8666 Acorus tatarinowii Species Acoraceae Eukaryota Rhizomes n.a. n.a. PMID[29116780]
NPO20414 Ocimum basilicum Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[29192771]
NPO865 Dendrobium loddigesii Species Orchidaceae Eukaryota n.a. n.a. n.a. PMID[31291099]
NPO24241 Taiwania cryptomerioides Species Cupressaceae Eukaryota n.a. n.a. n.a. PMID[31347365]
NPO24241 Taiwania cryptomerioides Species Cupressaceae Eukaryota n.a. n.a. n.a. PMID[9014350]
NPO20414 Ocimum basilicum Species Lamiaceae Eukaryota n.a. n.a. Database[FooDB]
NPO20414 Ocimum basilicum Species Lamiaceae Eukaryota Flower n.a. n.a. Database[FooDB]
NPO8545 Hyssopus officinalis Species Lamiaceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO20414 Ocimum basilicum Species Lamiaceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO8545 Hyssopus officinalis Species Lamiaceae Eukaryota Plant n.a. n.a. Database[FooDB]
NPO10932 Melissa officinalis Species Lamiaceae Eukaryota Plant n.a. n.a. Database[FooDB]
NPO20414 Ocimum basilicum Species Lamiaceae Eukaryota Plant n.a. n.a. Database[FooDB]
NPO20414 Ocimum basilicum Species Lamiaceae Eukaryota Root n.a. n.a. Database[FooDB]
NPO8545 Hyssopus officinalis Species Lamiaceae Eukaryota Shoot n.a. n.a. Database[FooDB]
NPO10932 Melissa officinalis Species Lamiaceae Eukaryota Shoot n.a. n.a. Database[FooDB]
NPO20414 Ocimum basilicum Species Lamiaceae Eukaryota Shoot Essent. Oil n.a. n.a. Database[FooDB]
NPO20414 Ocimum basilicum Species Lamiaceae Eukaryota Sprout Seedling n.a. n.a. Database[FooDB]
NPO20414 Ocimum basilicum Species Lamiaceae Eukaryota Stem n.a. n.a. Database[FooDB]
NPO10932 Melissa officinalis Species Lamiaceae Eukaryota Tissue Culture n.a. n.a. Database[FooDB]
NPO8545 Hyssopus officinalis Species Lamiaceae Eukaryota n.a. n.a. Database[FooDB]
NPO10932 Melissa officinalis Species Lamiaceae Eukaryota n.a. n.a. Database[FooDB]
NPO20414 Ocimum basilicum Species Lamiaceae Eukaryota n.a. n.a. Database[FooDB]
NPO8545 Hyssopus officinalis Species Lamiaceae Eukaryota Flower n.a. n.a. Database[FooDB]
NPO7730 Commiphora myrrha Species Burseraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO1048 Ajuga reptans Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO18328 Leontopodium alpinum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO5681 Acorus gramineus Species Acoraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO865 Dendrobium loddigesii Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO12796 Periploca sepium Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO6731 Ononis spinosa Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO10932 Melissa officinalis Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO7773 Crinum moorei Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO24241 Taiwania cryptomerioides Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO20414 Ocimum basilicum Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO11100 Artemisia capillaris Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO13135 Campylotropis hirtella Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO8666 Acorus tatarinowii Species Acoraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO20414 Ocimum basilicum Species Lamiaceae Eukaryota n.a. n.a. Database[Phenol-Explorer]
NPO8545 Hyssopus officinalis Species Lamiaceae Eukaryota n.a. n.a. Database[Phenol-Explorer]
NPO15538 Eucalyptus citriodora Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO5681 Acorus gramineus Species Acoraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7730 Commiphora myrrha Species Burseraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO1048 Ajuga reptans Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO20414 Ocimum basilicum Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO18328 Leontopodium alpinum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO8666 Acorus tatarinowii Species Acoraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO13135 Campylotropis hirtella Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7773 Crinum moorei Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO10932 Melissa officinalis Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO865 Dendrobium loddigesii Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11100 Artemisia capillaris Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO24241 Taiwania cryptomerioides Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO12796 Periploca sepium Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO6731 Ononis spinosa Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO8666 Acorus tatarinowii Species Acoraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO1048 Ajuga reptans Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO12796 Periploca sepium Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO11100 Artemisia capillaris Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO24241 Taiwania cryptomerioides Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO20414 Ocimum basilicum Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO865 Dendrobium loddigesii Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO6731 Ononis spinosa Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO865 Dendrobium loddigesii Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO11100 Artemisia capillaris Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO5681 Acorus gramineus Species Acoraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO8666 Acorus tatarinowii Species Acoraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO12796 Periploca sepium Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO9532 Vernonia cistifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8666 Acorus tatarinowii Species Acoraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14477 Comamonas testosteroni Species Comamonadaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO10638 Plectranthus myrianthus Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO526 Salvia sessei Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13135 Campylotropis hirtella Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3867 Smallanthus glabratus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6731 Ononis spinosa Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6289 Ceropegia dichotoma Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3873 Crotalaria candicans Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5456 Juniperus drupacea Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1048 Ajuga reptans Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15538 Eucalyptus citriodora Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7773 Crinum moorei Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11843 Stephania zippeliana Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8545 Hyssopus officinalis Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12205 Eucalyptus apodophylla Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12565 Hypericum polyanthemum Species Hypericaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11576 Glycosmis macrophylla Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10605 Tristania conferta Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1257 Distephanus angulifolius Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22691 Mentha cardiaca Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11100 Artemisia capillaris Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24071 Girgensohnia diptera Species Chenopodiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12796 Periploca sepium Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11190 Veronica polita Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1815 Breonia chinensis Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9319 Pterocaulon virgatum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10922 Pentaclethra macrophylla Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8432 Haminoea orbignyana Species Haminoeidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21720 Talaromyces variabilis Species Trichocomaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10932 Melissa officinalis Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9704 Sonneratia caseolaris Species Lythraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7822.1 Eucalyptus globulus subsp. bicostata Subspecies Myrtaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20414 Ocimum basilicum Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5043 Eria japonica Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18328 Leontopodium alpinum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23384 Rhodiola semenovii Species Crassulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7730 Commiphora myrrha Species Burseraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8934 Gypsophila perfoliata Species Caryophyllaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO865 Dendrobium loddigesii Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24241 Taiwania cryptomerioides Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12091 Martensia denticulata Species Delesseriaceae 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
NPO8545 NPC79576 Other Leaf 3.005 0.01 6 mg/100g Database [DUKE]
NPO20414 NPC79576 Raw Plant 0.05 0.05 0.05 mg/100g Database [DUKE]
NPO8545 NPC79576 Other Shoot 1.505 0.01 3 mg/100g Database [DUKE]
NPO10932 NPC79576 Other Shoot 1.35 0.3 2.4 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
NPT461 Cell Line PANC-1 Homo sapiens PC50 = 21.3 uM PMID[489211]
NPT783 Cell Line MIA PaCa-2 Homo sapiens PC50 = 10.7 uM PMID[489211]
NPT2309 Cell Line CAPAN-1 Homo sapiens PC50 = 10.7 uM PMID[489211]
NPT2107 Cell Line PSN1 Homo sapiens PC50 = 19.7 uM PMID[489211]
NPT835 Organism Gloeophyllum trabeum Gloeophyllum trabeum Inhibition = 100.0 % PMID[489209]
NPT2549 Organism Laetiporus sulphureus Laetiporus sulphureus Inhibition = 100.0 % PMID[489209]
NPT834 Organism Trametes versicolor Trametes versicolor Inhibition = 51.4 % PMID[489209]
NPT2550 Organism Lenzites betulinus Lenzites betulinus Inhibition = 100.0 % PMID[489209]
NPT35 Others n.a. log K = 1.55 n.a. PMID[489210]
NPT2 Others Unspecified PC50 = 45.1 uM PMID[489211]
NPT728 Individual Protein Serine/threonine-protein kinase AKT Homo sapiens Inhibition = 100.0 % PMID[489211]

☑ 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 NPC79576 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
1.0 High Similarity NPC194208
1.0 High Similarity NPC282694
0.8852 High Similarity NPC174956
0.875 High Similarity NPC94192
0.8636 High Similarity NPC242992
0.8636 High Similarity NPC23954
0.8636 High Similarity NPC164022
0.8615 High Similarity NPC476431
0.8548 High Similarity NPC81615
0.8507 High Similarity NPC220939
0.8507 High Similarity NPC265485
0.85 High Similarity NPC189290
0.85 High Similarity NPC474769
0.8485 Intermediate Similarity NPC92801
0.8475 Intermediate Similarity NPC179024
0.8438 Intermediate Similarity NPC279434
0.8421 Intermediate Similarity NPC35519
0.8421 Intermediate Similarity NPC306195
0.8421 Intermediate Similarity NPC179169
0.8421 Intermediate Similarity NPC181255
0.8421 Intermediate Similarity NPC157781
0.8358 Intermediate Similarity NPC167706
0.8281 Intermediate Similarity NPC64123
0.8246 Intermediate Similarity NPC214584
0.8246 Intermediate Similarity NPC26906
0.8235 Intermediate Similarity NPC182717
0.8226 Intermediate Similarity NPC135648
0.8182 Intermediate Similarity NPC96484
0.8182 Intermediate Similarity NPC208999
0.8167 Intermediate Similarity NPC39068
0.8167 Intermediate Similarity NPC264779
0.8154 Intermediate Similarity NPC202017
0.8143 Intermediate Similarity NPC76966
0.8143 Intermediate Similarity NPC186554
0.8143 Intermediate Similarity NPC265588
0.8116 Intermediate Similarity NPC100334
0.8116 Intermediate Similarity NPC201048
0.8116 Intermediate Similarity NPC476366
0.8103 Intermediate Similarity NPC177112
0.8103 Intermediate Similarity NPC71506
0.8088 Intermediate Similarity NPC110799
0.7941 Intermediate Similarity NPC475728
0.7917 Intermediate Similarity NPC207772
0.7917 Intermediate Similarity NPC253561
0.7917 Intermediate Similarity NPC80088
0.7887 Intermediate Similarity NPC46160
0.7887 Intermediate Similarity NPC290598
0.7887 Intermediate Similarity NPC122418
0.7887 Intermediate Similarity NPC30590
0.7887 Intermediate Similarity NPC470749
0.7887 Intermediate Similarity NPC27765
0.7887 Intermediate Similarity NPC265328
0.7887 Intermediate Similarity NPC120098
0.7887 Intermediate Similarity NPC202642
0.7887 Intermediate Similarity NPC189883
0.7887 Intermediate Similarity NPC472305
0.7857 Intermediate Similarity NPC22134
0.7857 Intermediate Similarity NPC243342
0.7857 Intermediate Similarity NPC91858
0.7857 Intermediate Similarity NPC477138
0.7846 Intermediate Similarity NPC101128
0.7846 Intermediate Similarity NPC225415
0.7808 Intermediate Similarity NPC291379
0.7794 Intermediate Similarity NPC474248
0.7778 Intermediate Similarity NPC90979
0.7778 Intermediate Similarity NPC470758
0.7778 Intermediate Similarity NPC34177
0.7778 Intermediate Similarity NPC214570
0.7778 Intermediate Similarity NPC472805
0.7778 Intermediate Similarity NPC257666
0.7778 Intermediate Similarity NPC101475
0.7778 Intermediate Similarity NPC471798
0.7778 Intermediate Similarity NPC34110
0.7778 Intermediate Similarity NPC157996
0.7778 Intermediate Similarity NPC40394
0.7778 Intermediate Similarity NPC266193
0.7778 Intermediate Similarity NPC470711
0.7761 Intermediate Similarity NPC269077
0.7761 Intermediate Similarity NPC253303
0.7761 Intermediate Similarity NPC197805
0.7761 Intermediate Similarity NPC139207
0.7761 Intermediate Similarity NPC185874
0.7761 Intermediate Similarity NPC171225
0.7746 Intermediate Similarity NPC66566
0.7746 Intermediate Similarity NPC121744
0.7746 Intermediate Similarity NPC322353
0.7746 Intermediate Similarity NPC291503
0.7746 Intermediate Similarity NPC477923
0.7746 Intermediate Similarity NPC138374
0.7746 Intermediate Similarity NPC32832
0.7746 Intermediate Similarity NPC118508
0.7746 Intermediate Similarity NPC471723
0.7746 Intermediate Similarity NPC141071
0.7746 Intermediate Similarity NPC34700
0.7746 Intermediate Similarity NPC257347
0.7727 Intermediate Similarity NPC258595
0.7719 Intermediate Similarity NPC100445
0.7714 Intermediate Similarity NPC471799
0.7681 Intermediate Similarity NPC145498
0.7681 Intermediate Similarity NPC34834
0.7671 Intermediate Similarity NPC474989
0.7671 Intermediate Similarity NPC205455
0.7671 Intermediate Similarity NPC98386
0.7671 Intermediate Similarity NPC318136
0.7671 Intermediate Similarity NPC186191
0.7671 Intermediate Similarity NPC253807
0.7671 Intermediate Similarity NPC275910
0.7671 Intermediate Similarity NPC285761
0.7671 Intermediate Similarity NPC196753
0.7671 Intermediate Similarity NPC300499
0.7671 Intermediate Similarity NPC158662
0.7671 Intermediate Similarity NPC470396
0.7671 Intermediate Similarity NPC230295
0.7671 Intermediate Similarity NPC99168
0.7671 Intermediate Similarity NPC22955
0.7656 Intermediate Similarity NPC66020
0.7656 Intermediate Similarity NPC240506
0.7647 Intermediate Similarity NPC216460
0.7647 Intermediate Similarity NPC244790
0.7639 Intermediate Similarity NPC470362
0.7639 Intermediate Similarity NPC7629
0.7639 Intermediate Similarity NPC151622
0.7639 Intermediate Similarity NPC134330
0.7639 Intermediate Similarity NPC129165
0.7639 Intermediate Similarity NPC106364
0.7639 Intermediate Similarity NPC240604
0.7639 Intermediate Similarity NPC106432
0.7639 Intermediate Similarity NPC73875
0.7639 Intermediate Similarity NPC237460
0.7639 Intermediate Similarity NPC300324
0.7612 Intermediate Similarity NPC286669
0.7612 Intermediate Similarity NPC222366
0.7612 Intermediate Similarity NPC476039
0.7612 Intermediate Similarity NPC473929
0.7606 Intermediate Similarity NPC471797
0.76 Intermediate Similarity NPC119229
0.7576 Intermediate Similarity NPC68656
0.7576 Intermediate Similarity NPC96793
0.7576 Intermediate Similarity NPC290367
0.7576 Intermediate Similarity NPC144650
0.7576 Intermediate Similarity NPC323424
0.7571 Intermediate Similarity NPC242001
0.7571 Intermediate Similarity NPC471272
0.7571 Intermediate Similarity NPC477792
0.7568 Intermediate Similarity NPC53744
0.7568 Intermediate Similarity NPC80530
0.7568 Intermediate Similarity NPC170394
0.7568 Intermediate Similarity NPC273410
0.7568 Intermediate Similarity NPC1319
0.7538 Intermediate Similarity NPC41160
0.7534 Intermediate Similarity NPC132542
0.7534 Intermediate Similarity NPC477427
0.7534 Intermediate Similarity NPC474826
0.7534 Intermediate Similarity NPC91594
0.7534 Intermediate Similarity NPC477924
0.7534 Intermediate Similarity NPC477426
0.7534 Intermediate Similarity NPC318495
0.7534 Intermediate Similarity NPC477425
0.7534 Intermediate Similarity NPC130136
0.7534 Intermediate Similarity NPC198968
0.7534 Intermediate Similarity NPC283619
0.7534 Intermediate Similarity NPC155986
0.75 Intermediate Similarity NPC30166
0.75 Intermediate Similarity NPC101307
0.75 Intermediate Similarity NPC285893
0.75 Intermediate Similarity NPC133580
0.75 Intermediate Similarity NPC87489
0.75 Intermediate Similarity NPC88454
0.75 Intermediate Similarity NPC28657
0.75 Intermediate Similarity NPC304309
0.75 Intermediate Similarity NPC117607
0.75 Intermediate Similarity NPC230301
0.75 Intermediate Similarity NPC134847
0.75 Intermediate Similarity NPC136188
0.75 Intermediate Similarity NPC288035
0.75 Intermediate Similarity NPC162742
0.75 Intermediate Similarity NPC22105
0.7467 Intermediate Similarity NPC476809
0.7467 Intermediate Similarity NPC236237
0.7467 Intermediate Similarity NPC102253
0.7467 Intermediate Similarity NPC236112
0.7467 Intermediate Similarity NPC295131
0.7467 Intermediate Similarity NPC13554
0.7467 Intermediate Similarity NPC322313
0.7467 Intermediate Similarity NPC472301
0.7465 Intermediate Similarity NPC474140
0.7465 Intermediate Similarity NPC68443
0.7465 Intermediate Similarity NPC201373
0.7465 Intermediate Similarity NPC259049
0.7463 Intermediate Similarity NPC208198
0.7463 Intermediate Similarity NPC282619
0.7463 Intermediate Similarity NPC60837
0.7463 Intermediate Similarity NPC471200
0.7463 Intermediate Similarity NPC2728
0.7463 Intermediate Similarity NPC11555
0.7463 Intermediate Similarity NPC163678
0.7463 Intermediate Similarity NPC172613
0.746 Intermediate Similarity NPC278550
0.7458 Intermediate Similarity NPC329773
0.7432 Intermediate Similarity NPC6978

  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 NPC79576 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
0.7826 Intermediate Similarity NPD4243 Approved
0.7606 Intermediate Similarity NPD4785 Approved
0.7606 Intermediate Similarity NPD4784 Approved
0.7568 Intermediate Similarity NPD7645 Phase 2
0.75 Intermediate Similarity NPD4190 Phase 3
0.75 Intermediate Similarity NPD6942 Approved
0.75 Intermediate Similarity NPD7339 Approved
0.75 Intermediate Similarity NPD5275 Approved
0.7467 Intermediate Similarity NPD7525 Registered
0.7397 Intermediate Similarity NPD3701 Clinical (unspecified phase)
0.7273 Intermediate Similarity NPD368 Approved
0.7143 Intermediate Similarity NPD342 Phase 1
0.7105 Intermediate Similarity NPD4195 Approved
0.6914 Remote Similarity NPD3618 Phase 1
0.6892 Remote Similarity NPD6924 Approved
0.6892 Remote Similarity NPD6926 Approved
0.6835 Remote Similarity NPD3667 Approved
0.6835 Remote Similarity NPD4221 Approved
0.6835 Remote Similarity NPD4223 Phase 3
0.68 Remote Similarity NPD8264 Approved
0.6795 Remote Similarity NPD4748 Discontinued
0.6711 Remote Similarity NPD6933 Approved
0.6707 Remote Similarity NPD3574 Clinical (unspecified phase)
0.6667 Remote Similarity NPD5328 Approved
0.6667 Remote Similarity NPD4786 Approved
0.6667 Remote Similarity NPD4197 Approved
0.6628 Remote Similarity NPD4202 Approved
0.6627 Remote Similarity NPD4751 Clinical (unspecified phase)
0.6622 Remote Similarity NPD7151 Approved
0.6622 Remote Similarity NPD7152 Approved
0.6622 Remote Similarity NPD7150 Approved
0.6585 Remote Similarity NPD5329 Approved
0.6582 Remote Similarity NPD4695 Discontinued
0.6582 Remote Similarity NPD7509 Discontinued
0.6575 Remote Similarity NPD6923 Approved
0.6575 Remote Similarity NPD6922 Approved
0.6512 Remote Similarity NPD7515 Phase 2
0.6512 Remote Similarity NPD6079 Approved
0.6506 Remote Similarity NPD4690 Approved
0.6506 Remote Similarity NPD4519 Discontinued
0.6506 Remote Similarity NPD5280 Approved
0.6506 Remote Similarity NPD5205 Approved
0.6506 Remote Similarity NPD4688 Approved
0.6506 Remote Similarity NPD4623 Approved
0.6506 Remote Similarity NPD4694 Approved
0.6506 Remote Similarity NPD4689 Approved
0.6506 Remote Similarity NPD4138 Approved
0.6506 Remote Similarity NPD4693 Phase 3
0.6506 Remote Similarity NPD5690 Phase 2
0.65 Remote Similarity NPD388 Approved
0.65 Remote Similarity NPD386 Approved
0.6486 Remote Similarity NPD7143 Approved
0.6486 Remote Similarity NPD7144 Approved
0.6463 Remote Similarity NPD3133 Approved
0.6463 Remote Similarity NPD3665 Phase 1
0.6463 Remote Similarity NPD3666 Approved
0.6429 Remote Similarity NPD3573 Approved
0.6393 Remote Similarity NPD384 Approved
0.6393 Remote Similarity NPD385 Approved
0.6389 Remote Similarity NPD7331 Phase 2
0.6375 Remote Similarity NPD6931 Approved
0.6375 Remote Similarity NPD6930 Phase 2
0.6364 Remote Similarity NPD7748 Approved
0.6353 Remote Similarity NPD4722 Approved
0.6353 Remote Similarity NPD4723 Approved
0.6333 Remote Similarity NPD4755 Approved
0.6329 Remote Similarity NPD3617 Approved
0.6296 Remote Similarity NPD4692 Approved
0.6296 Remote Similarity NPD4139 Approved
0.6279 Remote Similarity NPD4753 Phase 2
0.6265 Remote Similarity NPD3668 Phase 3
0.625 Remote Similarity NPD6929 Approved
0.625 Remote Similarity NPD7341 Phase 2
0.6222 Remote Similarity NPD4697 Phase 3
0.6222 Remote Similarity NPD5221 Approved
0.6222 Remote Similarity NPD5220 Clinical (unspecified phase)
0.6222 Remote Similarity NPD5222 Approved
0.6203 Remote Similarity NPD6932 Approved
0.6196 Remote Similarity NPD4700 Approved
0.6196 Remote Similarity NPD5286 Approved
0.6196 Remote Similarity NPD4696 Approved
0.6196 Remote Similarity NPD5285 Approved
0.6154 Remote Similarity NPD5173 Approved
0.6154 Remote Similarity NPD7902 Approved
0.6145 Remote Similarity NPD6695 Phase 3
0.6143 Remote Similarity NPD1145 Discontinued
0.6136 Remote Similarity NPD5281 Approved
0.6136 Remote Similarity NPD5284 Approved
0.6129 Remote Similarity NPD5223 Approved
0.6125 Remote Similarity NPD7322 Clinical (unspecified phase)
0.6118 Remote Similarity NPD5279 Phase 3
0.6087 Remote Similarity NPD5290 Discontinued
0.6076 Remote Similarity NPD1346 Approved
0.6071 Remote Similarity NPD7338 Clinical (unspecified phase)
0.6067 Remote Similarity NPD6399 Phase 3
0.6064 Remote Similarity NPD4633 Approved
0.6064 Remote Similarity NPD5211 Phase 2
0.6064 Remote Similarity NPD5224 Approved
0.6064 Remote Similarity NPD5225 Approved
0.6064 Remote Similarity NPD5226 Approved
0.6049 Remote Similarity NPD6683 Phase 2
0.6023 Remote Similarity NPD4096 Approved
0.6 Remote Similarity NPD4754 Approved
0.6 Remote Similarity NPD5175 Approved
0.6 Remote Similarity NPD6893 Approved
0.6 Remote Similarity NPD1799 Clinical (unspecified phase)
0.6 Remote Similarity NPD5174 Approved
0.6 Remote Similarity NPD5776 Phase 2
0.6 Remote Similarity NPD6925 Approved
0.6 Remote Similarity NPD1696 Phase 3
0.6 Remote Similarity NPD7520 Clinical (unspecified phase)
0.6 Remote Similarity NPD3621 Clinical (unspecified phase)
0.5976 Remote Similarity NPD7514 Phase 3
0.5976 Remote Similarity NPD7332 Phase 2
0.5965 Remote Similarity NPD319 Phase 1
0.5938 Remote Similarity NPD5141 Approved
0.5934 Remote Similarity NPD4629 Approved
0.5934 Remote Similarity NPD5210 Approved
0.5934 Remote Similarity NPD5695 Phase 3
0.593 Remote Similarity NPD6098 Approved
0.5926 Remote Similarity NPD7145 Approved
0.5921 Remote Similarity NPD15 Approved
0.5921 Remote Similarity NPD791 Approved
0.5921 Remote Similarity NPD4137 Phase 3
0.5914 Remote Similarity NPD7638 Approved
0.5909 Remote Similarity NPD7285 Clinical (unspecified phase)
0.5904 Remote Similarity NPD6898 Phase 1
0.5902 Remote Similarity NPD367 Approved
0.5889 Remote Similarity NPD5133 Approved
0.5876 Remote Similarity NPD7128 Approved
0.5876 Remote Similarity NPD6402 Approved
0.5876 Remote Similarity NPD4767 Approved
0.5876 Remote Similarity NPD4768 Approved
0.5876 Remote Similarity NPD6675 Approved
0.5876 Remote Similarity NPD5739 Approved
0.5862 Remote Similarity NPD7524 Approved
0.5862 Remote Similarity NPD7750 Discontinued
0.5857 Remote Similarity NPD287 Approved
0.5851 Remote Similarity NPD7639 Approved
0.5851 Remote Similarity NPD7640 Approved
0.5844 Remote Similarity NPD4691 Approved
0.5844 Remote Similarity NPD4747 Approved
0.5843 Remote Similarity NPD3168 Discontinued
0.5824 Remote Similarity NPD7900 Approved
0.5824 Remote Similarity NPD7901 Clinical (unspecified phase)
0.5824 Remote Similarity NPD6001 Approved
0.5816 Remote Similarity NPD5701 Approved
0.5816 Remote Similarity NPD5697 Approved
0.5806 Remote Similarity NPD6083 Phase 2
0.5806 Remote Similarity NPD6084 Phase 2
0.5797 Remote Similarity NPD4219 Approved
0.5795 Remote Similarity NPD5208 Approved
0.5795 Remote Similarity NPD4518 Approved
0.5765 Remote Similarity NPD4788 Approved
0.5761 Remote Similarity NPD6356 Clinical (unspecified phase)
0.5758 Remote Similarity NPD4729 Approved
0.5758 Remote Similarity NPD5128 Approved
0.5758 Remote Similarity NPD4730 Approved
0.5758 Remote Similarity NPD7320 Approved
0.5758 Remote Similarity NPD6899 Approved
0.5758 Remote Similarity NPD6011 Approved
0.5758 Remote Similarity NPD6881 Approved
0.5747 Remote Similarity NPD5330 Approved
0.5747 Remote Similarity NPD7521 Approved
0.5747 Remote Similarity NPD7334 Approved
0.5747 Remote Similarity NPD6409 Approved
0.5747 Remote Similarity NPD7146 Approved
0.5747 Remote Similarity NPD6684 Approved
0.5745 Remote Similarity NPD5696 Approved
0.5745 Remote Similarity NPD4225 Approved
0.573 Remote Similarity NPD6051 Approved
0.573 Remote Similarity NPD6080 Approved
0.573 Remote Similarity NPD5764 Clinical (unspecified phase)
0.573 Remote Similarity NPD6673 Approved
0.573 Remote Similarity NPD6101 Approved
0.573 Remote Similarity NPD6904 Approved
0.5714 Remote Similarity NPD6902 Approved
0.5714 Remote Similarity NPD4267 Clinical (unspecified phase)
0.57 Remote Similarity NPD6373 Approved
0.57 Remote Similarity NPD6012 Approved
0.57 Remote Similarity NPD6013 Approved
0.57 Remote Similarity NPD6014 Approved
0.57 Remote Similarity NPD6372 Approved
0.5692 Remote Similarity NPD9410 Clinical (unspecified phase)
0.5676 Remote Similarity NPD371 Approved
0.5667 Remote Similarity NPD5207 Approved
0.5667 Remote Similarity NPD4001 Clinical (unspecified phase)
0.5667 Remote Similarity NPD5692 Phase 3
0.5652 Remote Similarity NPD5707 Approved
0.5644 Remote Similarity NPD5250 Approved
0.5644 Remote Similarity NPD5169 Approved
0.5644 Remote Similarity NPD5249 Phase 3
0.5644 Remote Similarity NPD6883 Approved
0.5644 Remote Similarity NPD7290 Approved
0.5644 Remote Similarity NPD5251 Approved
0.5644 Remote Similarity NPD5248 Approved
0.5644 Remote Similarity NPD5134 Clinical (unspecified phase)
0.5644 Remote Similarity NPD7102 Approved
0.5644 Remote Similarity NPD5247 Approved
0.5644 Remote Similarity NPD4634 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