Structure

Physi-Chem Properties

Molecular Weight:  238.19
Volume:  265.827
LogP:  2.938
LogD:  2.581
LogS:  -3.328
# Rotatable Bonds:  1
TPSA:  40.46
# H-Bond Aceptor:  2
# H-Bond Donor:  2
# Rings:  2
# Heavy Atoms:  2

MedChem Properties

QED Drug-Likeness Score:  0.69
Synthetic Accessibility Score:  4.349
Fsp3:  0.867
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.41
MDCK Permeability:  2.5090534109040163e-05
Pgp-inhibitor:  0.001
Pgp-substrate:  0.081
Human Intestinal Absorption (HIA):  0.003
20% Bioavailability (F20%):  0.82
30% Bioavailability (F30%):  0.032

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.224
Plasma Protein Binding (PPB):  85.39525604248047%
Volume Distribution (VD):  1.347
Pgp-substrate:  14.885379791259766%

ADMET: Metabolism

CYP1A2-inhibitor:  0.045
CYP1A2-substrate:  0.231
CYP2C19-inhibitor:  0.03
CYP2C19-substrate:  0.86
CYP2C9-inhibitor:  0.05
CYP2C9-substrate:  0.44
CYP2D6-inhibitor:  0.012
CYP2D6-substrate:  0.196
CYP3A4-inhibitor:  0.144
CYP3A4-substrate:  0.306

ADMET: Excretion

Clearance (CL):  8.243
Half-life (T1/2):  0.463

ADMET: Toxicity

hERG Blockers:  0.027
Human Hepatotoxicity (H-HT):  0.056
Drug-inuced Liver Injury (DILI):  0.048
AMES Toxicity:  0.017
Rat Oral Acute Toxicity:  0.832
Maximum Recommended Daily Dose:  0.889
Skin Sensitization:  0.098
Carcinogencity:  0.068
Eye Corrosion:  0.025
Eye Irritation:  0.718
Respiratory Toxicity:  0.753

Download Data

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

  Natural Product: NPC164022

Natural Product ID:  NPC164022
Common Name*:   Oplodiol
IUPAC Name:   (1R,4S,4aR,8aR)-4,8a-dimethyl-6-propan-2-yl-1,2,3,4a,5,8-hexahydronaphthalene-1,4-diol
Synonyms:   Oplodiol
Standard InCHIKey:  SOZSXJHFVBBAOY-TUVASFSCSA-N
Standard InCHI:  InChI=1S/C15H26O2/c1-10(2)11-5-7-14(3)12(9-11)15(4,17)8-6-13(14)16/h5,10,12-13,16-17H,6-9H2,1-4H3/t12-,13-,14-,15+/m1/s1
SMILES:  CC(C1=CC[C@@]2([C@@H](C1)[C@@](C)(O)CC[C@H]2O)C)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL465432
PubChem CID:   12313756
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
NPO6915 Chloranthus japonicus Species Chloranthaceae Eukaryota n.a. whole plant n.a. DOI[10.1016/j.phytol.2016.01.005]
NPO31430 Renealmia cincinnata Species Zingiberaceae Eukaryota n.a. fruit n.a. PMID[10643672]
NPO11575 Artemisia japonica Species Asteraceae Eukaryota n.a. aerial part n.a. PMID[11440075]
NPO10294 Homalomena aromatica Species Araceae Eukaryota n.a. root n.a. PMID[1368861]
NPO4044 Homalomena occulta Species Araceae Eukaryota n.a. aerial part n.a. PMID[17511005]
NPO18811 Magnolia biondii Species Magnoliaceae Eukaryota n.a. flower bud n.a. PMID[17628872]
NPO6915 Chloranthus japonicus Species Chloranthaceae Eukaryota n.a. whole plant n.a. PMID[18451544]
NPO4044 Homalomena occulta Species Araceae Eukaryota n.a. rhizome n.a. PMID[18649899]
NPO14969 Hedychium spicatum Species Zingiberaceae Eukaryota n.a. rhizome n.a. PMID[19027298]
NPO31423 Illicium oligandrum Species Schisandraceae Eukaryota pericarps n.a. n.a. PMID[19159273]
NPO14969 Hedychium spicatum Species Zingiberaceae Eukaryota rhizomes n.a. n.a. PMID[19332371]
NPO18811 Magnolia biondii Species Magnoliaceae Eukaryota n.a. n.a. n.a. PMID[19370929]
NPO13135 Campylotropis hirtella Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[19481938]
NPO31423 Illicium oligandrum Species Schisandraceae Eukaryota stem bark n.a. n.a. PMID[19496609]
NPO14969 Hedychium spicatum Species Zingiberaceae Eukaryota rhizomes n.a. n.a. PMID[19782567]
NPO6915 Chloranthus japonicus Species Chloranthaceae Eukaryota whole plants Suiling district, Heilongjiang Province, China 2008-AUG PMID[21142110]
NPO6915 Chloranthus japonicus Species Chloranthaceae Eukaryota Whole plant Suiling district, Heilongjiang Province, China 2008-AUG PMID[21142110]
NPO6915 Chloranthus japonicus Species Chloranthaceae Eukaryota n.a. whole plant n.a. PMID[21142110]
NPO31423 Illicium oligandrum Species Schisandraceae Eukaryota n.a. stem n.a. PMID[21524101]
NPO6915 Chloranthus japonicus Species Chloranthaceae Eukaryota n.a. whole plant n.a. PMID[21650224]
NPO6915 Chloranthus japonicus Species Chloranthaceae Eukaryota n.a. n.a. n.a. PMID[21650224]
NPO4044 Homalomena occulta Species Araceae Eukaryota n.a. rhizome n.a. PMID[22573367]
NPO10294 Homalomena aromatica Species Araceae Eukaryota n.a. rhizome n.a. PMID[23177818]
NPO14969 Hedychium spicatum Species Zingiberaceae Eukaryota n.a. rhizome n.a. PMID[23422227]
NPO29799 Renealmia thyrsoidea Species Zingiberaceae Eukaryota n.a. leaf n.a. PMID[25251262]
NPO31423 Illicium oligandrum Species Schisandraceae Eukaryota n.a. root n.a. PMID[25966312]
NPO17346 Salvia plebeia Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[27933899]
NPO12796 Periploca sepium Species Apocynaceae Eukaryota n.a. n.a. n.a. PMID[28294615]
NPO17346 Salvia plebeia Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[28960981]
NPO865 Dendrobium loddigesii Species Orchidaceae Eukaryota n.a. n.a. n.a. PMID[31291099]
NPO18811 Magnolia biondii Species Magnoliaceae Eukaryota n.a. flower bud n.a. PMID[7779269]
NPO364 Chimonanthus praecox Species Calycanthaceae Eukaryota n.a. leaf n.a. Database[Article]
NPO10294 Homalomena aromatica Species Araceae Eukaryota n.a. root n.a. Database[Article]
NPO364 Chimonanthus praecox Species Calycanthaceae Eukaryota n.a. fruit n.a. Database[Article]
NPO12796 Periploca sepium Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO18811 Magnolia biondii Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO17346 Salvia plebeia Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO13135 Campylotropis hirtella Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO6915 Chloranthus japonicus Species Chloranthaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO11575 Artemisia japonica Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO865 Dendrobium loddigesii Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO7773 Crinum moorei Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO6731 Ononis spinosa Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO865 Dendrobium loddigesii Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO6915 Chloranthus japonicus Species Chloranthaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO17346 Salvia plebeia Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO6731 Ononis spinosa Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14969 Hedychium spicatum Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO12796 Periploca sepium Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO18811 Magnolia biondii Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7773 Crinum moorei Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO13135 Campylotropis hirtella Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11575 Artemisia japonica Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO4044 Homalomena occulta Species Araceae 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]
NPO18811 Magnolia biondii Species Magnoliaceae 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]
NPO17346 Salvia plebeia Species Lamiaceae 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]
NPO18811 Magnolia biondii Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO865 Dendrobium loddigesii Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO4044 Homalomena occulta Species Araceae 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]
NPO12091 Martensia denticulata Species Delesseriaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5043 Eria japonica Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6915 Chloranthus japonicus Species Chloranthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18811 Magnolia biondii Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO526 Salvia sessei Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8934 Gypsophila perfoliata Species Caryophyllaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6731 Ononis spinosa Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9532 Vernonia cistifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2244 Coscinoderma matthewsi Species Spongiidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12205 Eucalyptus apodophylla Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13135 Campylotropis hirtella Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1815 Breonia chinensis Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11576 Glycosmis macrophylla Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11575 Artemisia japonica Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9704 Sonneratia caseolaris Species Lythraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23384 Rhodiola semenovii Species Crassulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4044 Homalomena occulta Species Araceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6289 Ceropegia dichotoma Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO865 Dendrobium loddigesii Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10605 Tristania conferta Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5456 Juniperus drupacea Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10638 Plectranthus myrianthus Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22691 Mentha cardiaca Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7773 Crinum moorei Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3873 Crotalaria candicans Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11843 Stephania zippeliana Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1257 Distephanus angulifolius Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12565 Hypericum polyanthemum Species Hypericaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17346 Salvia plebeia Species Lamiaceae 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]
NPO9319 Pterocaulon virgatum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2653 Cheilanthes farinosa Species Pteridaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO364 Chimonanthus praecox Species Calycanthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21720 Talaromyces variabilis Species Trichocomaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10922 Pentaclethra macrophylla Species Fabaceae 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]
NPO10294 Homalomena aromatica Species Araceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14969 Hedychium spicatum 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
NPT34 Cell Line BV-2 Mus musculus IC50 = 63500.0 nM PMID[489647]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum IC50 < 5.0 ug.mL-1 PMID[489646]

☑ 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 NPC164022 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
0.9552 High Similarity NPC92801
0.913 High Similarity NPC167706
0.913 High Similarity NPC23954
0.9104 High Similarity NPC185874
0.9104 High Similarity NPC139207
0.8889 High Similarity NPC265588
0.8857 High Similarity NPC242992
0.8857 High Similarity NPC471272
0.875 High Similarity NPC291503
0.8732 High Similarity NPC265485
0.8732 High Similarity NPC182717
0.8732 High Similarity NPC220939
0.8696 High Similarity NPC208999
0.8696 High Similarity NPC96484
0.8657 High Similarity NPC101128
0.8649 High Similarity NPC300499
0.8636 High Similarity NPC79576
0.8636 High Similarity NPC282694
0.8636 High Similarity NPC194208
0.863 High Similarity NPC106432
0.863 High Similarity NPC1973
0.863 High Similarity NPC167873
0.8611 High Similarity NPC91858
0.8611 High Similarity NPC477138
0.8611 High Similarity NPC201048
0.8611 High Similarity NPC243342
0.8611 High Similarity NPC476366
0.8611 High Similarity NPC100334
0.8592 High Similarity NPC110799
0.8551 High Similarity NPC269077
0.8551 High Similarity NPC253303
0.8533 High Similarity NPC80530
0.8533 High Similarity NPC291379
0.8533 High Similarity NPC273410
0.8529 High Similarity NPC208198
0.8529 High Similarity NPC60837
0.8529 High Similarity NPC282619
0.8529 High Similarity NPC11555
0.8529 High Similarity NPC2728
0.8529 High Similarity NPC172613
0.8514 High Similarity NPC471798
0.8514 High Similarity NPC472805
0.8514 High Similarity NPC101475
0.8514 High Similarity NPC34177
0.8514 High Similarity NPC214570
0.8514 High Similarity NPC90979
0.8514 High Similarity NPC470758
0.8514 High Similarity NPC157996
0.8514 High Similarity NPC470711
0.8514 High Similarity NPC40394
0.8514 High Similarity NPC130136
0.8493 Intermediate Similarity NPC477923
0.8493 Intermediate Similarity NPC66566
0.8472 Intermediate Similarity NPC474140
0.8472 Intermediate Similarity NPC471799
0.8472 Intermediate Similarity NPC68443
0.8451 Intermediate Similarity NPC34834
0.8429 Intermediate Similarity NPC244790
0.8429 Intermediate Similarity NPC471238
0.8421 Intermediate Similarity NPC102253
0.8421 Intermediate Similarity NPC322313
0.8421 Intermediate Similarity NPC236237
0.84 Intermediate Similarity NPC98386
0.84 Intermediate Similarity NPC474989
0.84 Intermediate Similarity NPC167037
0.84 Intermediate Similarity NPC99168
0.84 Intermediate Similarity NPC22955
0.84 Intermediate Similarity NPC158662
0.84 Intermediate Similarity NPC275910
0.84 Intermediate Similarity NPC244385
0.84 Intermediate Similarity NPC470396
0.84 Intermediate Similarity NPC196753
0.84 Intermediate Similarity NPC230295
0.84 Intermediate Similarity NPC6978
0.84 Intermediate Similarity NPC138621
0.84 Intermediate Similarity NPC253807
0.84 Intermediate Similarity NPC285761
0.8382 Intermediate Similarity NPC225415
0.8382 Intermediate Similarity NPC144650
0.8378 Intermediate Similarity NPC120098
0.8378 Intermediate Similarity NPC202642
0.8378 Intermediate Similarity NPC73875
0.8378 Intermediate Similarity NPC27765
0.8378 Intermediate Similarity NPC477925
0.8378 Intermediate Similarity NPC122418
0.8378 Intermediate Similarity NPC265328
0.8378 Intermediate Similarity NPC189883
0.8378 Intermediate Similarity NPC470749
0.8378 Intermediate Similarity NPC46160
0.8378 Intermediate Similarity NPC274079
0.8378 Intermediate Similarity NPC30590
0.8378 Intermediate Similarity NPC290598
0.8356 Intermediate Similarity NPC471797
0.8333 Intermediate Similarity NPC477792
0.8333 Intermediate Similarity NPC242001
0.8312 Intermediate Similarity NPC476646
0.831 Intermediate Similarity NPC474248
0.8289 Intermediate Similarity NPC53744
0.8289 Intermediate Similarity NPC1319
0.8267 Intermediate Similarity NPC155986
0.8267 Intermediate Similarity NPC283619
0.8267 Intermediate Similarity NPC91594
0.8267 Intermediate Similarity NPC318495
0.8267 Intermediate Similarity NPC477924
0.8267 Intermediate Similarity NPC198968
0.8261 Intermediate Similarity NPC258595
0.8243 Intermediate Similarity NPC133580
0.8243 Intermediate Similarity NPC121744
0.8243 Intermediate Similarity NPC118508
0.8243 Intermediate Similarity NPC32832
0.8243 Intermediate Similarity NPC322353
0.8243 Intermediate Similarity NPC141071
0.8243 Intermediate Similarity NPC471723
0.8243 Intermediate Similarity NPC257347
0.8243 Intermediate Similarity NPC34700
0.8243 Intermediate Similarity NPC138374
0.8219 Intermediate Similarity NPC259049
0.8219 Intermediate Similarity NPC95165
0.8205 Intermediate Similarity NPC30166
0.8205 Intermediate Similarity NPC87489
0.8194 Intermediate Similarity NPC145498
0.8182 Intermediate Similarity NPC287749
0.8182 Intermediate Similarity NPC236112
0.8182 Intermediate Similarity NPC295131
0.8182 Intermediate Similarity NPC13554
0.8182 Intermediate Similarity NPC96362
0.8169 Intermediate Similarity NPC245795
0.8169 Intermediate Similarity NPC94192
0.8169 Intermediate Similarity NPC276616
0.8158 Intermediate Similarity NPC186191
0.8158 Intermediate Similarity NPC72507
0.8158 Intermediate Similarity NPC205455
0.8158 Intermediate Similarity NPC318136
0.8148 Intermediate Similarity NPC189777
0.8143 Intermediate Similarity NPC473929
0.8143 Intermediate Similarity NPC202017
0.8133 Intermediate Similarity NPC300324
0.8133 Intermediate Similarity NPC253190
0.8133 Intermediate Similarity NPC470362
0.8133 Intermediate Similarity NPC321016
0.8133 Intermediate Similarity NPC129165
0.8133 Intermediate Similarity NPC321381
0.8133 Intermediate Similarity NPC237460
0.8133 Intermediate Similarity NPC134330
0.8133 Intermediate Similarity NPC63958
0.8133 Intermediate Similarity NPC96319
0.8133 Intermediate Similarity NPC240604
0.8133 Intermediate Similarity NPC107059
0.8133 Intermediate Similarity NPC106364
0.8125 Intermediate Similarity NPC290731
0.8116 Intermediate Similarity NPC96793
0.8116 Intermediate Similarity NPC290367
0.8116 Intermediate Similarity NPC68656
0.8116 Intermediate Similarity NPC323424
0.8108 Intermediate Similarity NPC306727
0.8101 Intermediate Similarity NPC159168
0.8101 Intermediate Similarity NPC64600
0.8101 Intermediate Similarity NPC253402
0.8101 Intermediate Similarity NPC207013
0.8088 Intermediate Similarity NPC475251
0.8082 Intermediate Similarity NPC471271
0.8082 Intermediate Similarity NPC471268
0.8077 Intermediate Similarity NPC249423
0.8077 Intermediate Similarity NPC242350
0.8077 Intermediate Similarity NPC6707
0.8077 Intermediate Similarity NPC474531
0.8077 Intermediate Similarity NPC473420
0.8056 Intermediate Similarity NPC476431
0.8056 Intermediate Similarity NPC9942
0.8056 Intermediate Similarity NPC210323
0.8056 Intermediate Similarity NPC471560
0.8052 Intermediate Similarity NPC472463
0.8052 Intermediate Similarity NPC328714
0.8052 Intermediate Similarity NPC209430
0.8052 Intermediate Similarity NPC470429
0.8052 Intermediate Similarity NPC30986
0.8028 Intermediate Similarity NPC197805
0.8028 Intermediate Similarity NPC171225
0.8026 Intermediate Similarity NPC470428
0.8026 Intermediate Similarity NPC85105
0.8026 Intermediate Similarity NPC197659
0.8026 Intermediate Similarity NPC149550
0.8 Intermediate Similarity NPC478102
0.8 Intermediate Similarity NPC28657
0.8 Intermediate Similarity NPC288035
0.8 Intermediate Similarity NPC124172
0.8 Intermediate Similarity NPC46320
0.8 Intermediate Similarity NPC3403
0.8 Intermediate Similarity NPC231310
0.8 Intermediate Similarity NPC285893
0.8 Intermediate Similarity NPC162742
0.8 Intermediate Similarity NPC230301
0.8 Intermediate Similarity NPC238992
0.8 Intermediate Similarity NPC136188
0.8 Intermediate Similarity NPC22105
0.8 Intermediate Similarity NPC470077
0.8 Intermediate Similarity NPC304309
0.8 Intermediate Similarity NPC471200
0.8 Intermediate Similarity NPC134847
0.7975 Intermediate Similarity NPC202389

  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 NPC164022 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
0.8421 Intermediate Similarity NPD7525 Registered
0.8289 Intermediate Similarity NPD7645 Phase 2
0.8133 Intermediate Similarity NPD3701 Clinical (unspecified phase)
0.8 Intermediate Similarity NPD6942 Approved
0.8 Intermediate Similarity NPD7339 Approved
0.7826 Intermediate Similarity NPD368 Approved
0.7632 Intermediate Similarity NPD6924 Approved
0.7632 Intermediate Similarity NPD6926 Approved
0.759 Intermediate Similarity NPD3618 Phase 1
0.7532 Intermediate Similarity NPD8264 Approved
0.7531 Intermediate Similarity NPD3667 Approved
0.75 Intermediate Similarity NPD7509 Discontinued
0.75 Intermediate Similarity NPD4748 Discontinued
0.7471 Intermediate Similarity NPD4202 Approved
0.7436 Intermediate Similarity NPD6933 Approved
0.7368 Intermediate Similarity NPD4243 Approved
0.7349 Intermediate Similarity NPD4786 Approved
0.7326 Intermediate Similarity NPD5328 Approved
0.7294 Intermediate Similarity NPD4751 Clinical (unspecified phase)
0.7179 Intermediate Similarity NPD4785 Approved
0.7179 Intermediate Similarity NPD4784 Approved
0.7159 Intermediate Similarity NPD6079 Approved
0.7159 Intermediate Similarity NPD7515 Phase 2
0.7143 Intermediate Similarity NPD3666 Approved
0.7143 Intermediate Similarity NPD3133 Approved
0.7143 Intermediate Similarity NPD7152 Approved
0.7143 Intermediate Similarity NPD4755 Approved
0.7143 Intermediate Similarity NPD3665 Phase 1
0.7143 Intermediate Similarity NPD7151 Approved
0.7143 Intermediate Similarity NPD7150 Approved
0.7105 Intermediate Similarity NPD6922 Approved
0.7105 Intermediate Similarity NPD6923 Approved
0.7089 Intermediate Similarity NPD4190 Phase 3
0.7089 Intermediate Similarity NPD5275 Approved
0.7073 Intermediate Similarity NPD6930 Phase 2
0.7073 Intermediate Similarity NPD6931 Approved
0.7013 Intermediate Similarity NPD7144 Approved
0.7013 Intermediate Similarity NPD7143 Approved
0.6989 Remote Similarity NPD4696 Approved
0.6989 Remote Similarity NPD5285 Approved
0.6989 Remote Similarity NPD4700 Approved
0.6989 Remote Similarity NPD5286 Approved
0.6957 Remote Similarity NPD342 Phase 1
0.6951 Remote Similarity NPD4195 Approved
0.6951 Remote Similarity NPD6929 Approved
0.6941 Remote Similarity NPD7338 Clinical (unspecified phase)
0.6915 Remote Similarity NPD5223 Approved
0.6914 Remote Similarity NPD6932 Approved
0.6848 Remote Similarity NPD5221 Approved
0.6848 Remote Similarity NPD5222 Approved
0.6848 Remote Similarity NPD4697 Phase 3
0.6848 Remote Similarity NPD5220 Clinical (unspecified phase)
0.6842 Remote Similarity NPD4633 Approved
0.6842 Remote Similarity NPD5226 Approved
0.6842 Remote Similarity NPD5211 Phase 2
0.6842 Remote Similarity NPD5224 Approved
0.6842 Remote Similarity NPD5225 Approved
0.6829 Remote Similarity NPD7322 Clinical (unspecified phase)
0.6824 Remote Similarity NPD6695 Phase 3
0.6813 Remote Similarity NPD7748 Approved
0.6782 Remote Similarity NPD5279 Phase 3
0.6774 Remote Similarity NPD7902 Approved
0.6774 Remote Similarity NPD5173 Approved
0.6771 Remote Similarity NPD5175 Approved
0.6771 Remote Similarity NPD4754 Approved
0.6771 Remote Similarity NPD5174 Approved
0.6747 Remote Similarity NPD6683 Phase 2
0.6744 Remote Similarity NPD3668 Phase 3
0.6742 Remote Similarity NPD4753 Phase 2
0.6707 Remote Similarity NPD5776 Phase 2
0.6707 Remote Similarity NPD6925 Approved
0.6706 Remote Similarity NPD4223 Phase 3
0.6706 Remote Similarity NPD4221 Approved
0.6703 Remote Similarity NPD6399 Phase 3
0.6702 Remote Similarity NPD5290 Discontinued
0.6701 Remote Similarity NPD5141 Approved
0.6667 Remote Similarity NPD6893 Approved
0.6667 Remote Similarity NPD7514 Phase 3
0.6667 Remote Similarity NPD7332 Phase 2
0.6667 Remote Similarity NPD7520 Clinical (unspecified phase)
0.6633 Remote Similarity NPD6402 Approved
0.6633 Remote Similarity NPD4768 Approved
0.6633 Remote Similarity NPD7128 Approved
0.6633 Remote Similarity NPD5739 Approved
0.6633 Remote Similarity NPD4767 Approved
0.6633 Remote Similarity NPD6675 Approved
0.6627 Remote Similarity NPD7145 Approved
0.6591 Remote Similarity NPD3574 Clinical (unspecified phase)
0.6588 Remote Similarity NPD6898 Phase 1
0.6566 Remote Similarity NPD5701 Approved
0.6566 Remote Similarity NPD5697 Approved
0.6552 Remote Similarity NPD4197 Approved
0.6526 Remote Similarity NPD7638 Approved
0.6517 Remote Similarity NPD7750 Discontinued
0.6517 Remote Similarity NPD7524 Approved
0.6515 Remote Similarity NPD384 Approved
0.6515 Remote Similarity NPD385 Approved
0.65 Remote Similarity NPD4729 Approved
0.65 Remote Similarity NPD5128 Approved
0.65 Remote Similarity NPD6011 Approved
0.65 Remote Similarity NPD4730 Approved
0.65 Remote Similarity NPD6881 Approved
0.65 Remote Similarity NPD6899 Approved
0.65 Remote Similarity NPD7320 Approved
0.6477 Remote Similarity NPD5329 Approved
0.6477 Remote Similarity NPD1696 Phase 3
0.6471 Remote Similarity NPD4695 Discontinued
0.6458 Remote Similarity NPD7639 Approved
0.6458 Remote Similarity NPD7640 Approved
0.6456 Remote Similarity NPD4267 Clinical (unspecified phase)
0.6452 Remote Similarity NPD7901 Clinical (unspecified phase)
0.6452 Remote Similarity NPD7900 Approved
0.6436 Remote Similarity NPD6014 Approved
0.6436 Remote Similarity NPD6012 Approved
0.6436 Remote Similarity NPD6013 Approved
0.6436 Remote Similarity NPD6372 Approved
0.6436 Remote Similarity NPD6373 Approved
0.6404 Remote Similarity NPD4138 Approved
0.6404 Remote Similarity NPD4690 Approved
0.6404 Remote Similarity NPD4519 Discontinued
0.6404 Remote Similarity NPD4693 Phase 3
0.6404 Remote Similarity NPD5690 Phase 2
0.6404 Remote Similarity NPD4689 Approved
0.6404 Remote Similarity NPD5280 Approved
0.6404 Remote Similarity NPD4694 Approved
0.6404 Remote Similarity NPD4623 Approved
0.6404 Remote Similarity NPD5205 Approved
0.6404 Remote Similarity NPD4688 Approved
0.6395 Remote Similarity NPD6902 Approved
0.6383 Remote Similarity NPD5210 Approved
0.6383 Remote Similarity NPD4629 Approved
0.6373 Remote Similarity NPD5250 Approved
0.6373 Remote Similarity NPD5169 Approved
0.6373 Remote Similarity NPD5251 Approved
0.6373 Remote Similarity NPD4634 Approved
0.6373 Remote Similarity NPD5134 Clinical (unspecified phase)
0.6373 Remote Similarity NPD7102 Approved
0.6373 Remote Similarity NPD5248 Approved
0.6373 Remote Similarity NPD5247 Approved
0.6373 Remote Similarity NPD5249 Phase 3
0.6373 Remote Similarity NPD6883 Approved
0.6373 Remote Similarity NPD7290 Approved
0.6373 Remote Similarity NPD5135 Approved
0.6354 Remote Similarity NPD4225 Approved
0.6333 Remote Similarity NPD3573 Approved
0.6311 Remote Similarity NPD6617 Approved
0.6311 Remote Similarity NPD6869 Approved
0.6311 Remote Similarity NPD8130 Phase 1
0.6311 Remote Similarity NPD5127 Approved
0.6311 Remote Similarity NPD5217 Approved
0.6311 Remote Similarity NPD6847 Approved
0.6311 Remote Similarity NPD6401 Clinical (unspecified phase)
0.6311 Remote Similarity NPD5216 Approved
0.6311 Remote Similarity NPD6650 Approved
0.6311 Remote Similarity NPD5215 Approved
0.6311 Remote Similarity NPD6649 Approved
0.6304 Remote Similarity NPD3168 Discontinued
0.6279 Remote Similarity NPD8259 Clinical (unspecified phase)
0.6264 Remote Similarity NPD4722 Approved
0.6264 Remote Similarity NPD4723 Approved
0.625 Remote Similarity NPD6084 Phase 2
0.625 Remote Similarity NPD6083 Phase 2
0.625 Remote Similarity NPD8297 Approved
0.625 Remote Similarity NPD6882 Approved
0.625 Remote Similarity NPD4788 Approved
0.6237 Remote Similarity NPD8035 Phase 2
0.6237 Remote Similarity NPD7087 Discontinued
0.6237 Remote Similarity NPD5284 Approved
0.6237 Remote Similarity NPD8034 Phase 2
0.6237 Remote Similarity NPD6411 Approved
0.6237 Remote Similarity NPD5281 Approved
0.6235 Remote Similarity NPD3617 Approved
0.6234 Remote Similarity NPD371 Approved
0.6224 Remote Similarity NPD4159 Approved
0.6222 Remote Similarity NPD6684 Approved
0.6222 Remote Similarity NPD7521 Approved
0.6222 Remote Similarity NPD6409 Approved
0.6222 Remote Similarity NPD5330 Approved
0.6222 Remote Similarity NPD7146 Approved
0.6222 Remote Similarity NPD7334 Approved
0.6211 Remote Similarity NPD5695 Phase 3
0.6207 Remote Similarity NPD4139 Approved
0.6207 Remote Similarity NPD4692 Approved
0.6196 Remote Similarity NPD6051 Approved
0.619 Remote Similarity NPD4632 Approved
0.6176 Remote Similarity NPD5168 Approved
0.6173 Remote Similarity NPD4787 Phase 1
0.6164 Remote Similarity NPD4219 Approved
0.6132 Remote Similarity NPD5167 Approved
0.6117 Remote Similarity NPD4061 Clinical (unspecified phase)
0.6111 Remote Similarity NPD1694 Approved
0.6087 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6087 Remote Similarity NPD6903 Approved
0.6075 Remote Similarity NPD6274 Approved
0.6061 Remote Similarity NPD5344 Discontinued
0.6053 Remote Similarity NPD1145 Discontinued
0.6049 Remote Similarity NPD3699 Clinical (unspecified phase)
0.6049 Remote Similarity NPD3700 Clinical (unspecified phase)
0.6024 Remote Similarity NPD4732 Discontinued
0.6022 Remote Similarity NPD6101 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