Structure

Physi-Chem Properties

Molecular Weight:  222.2
Volume:  262.957
LogP:  4.092
LogD:  3.949
LogS:  -4.429
# Rotatable Bonds:  1
TPSA:  20.23
# H-Bond Aceptor:  1
# H-Bond Donor:  1
# Rings:  1
# Heavy Atoms:  1

MedChem Properties

QED Drug-Likeness Score:  0.663
Synthetic Accessibility Score:  4.22
Fsp3:  0.733
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:  -4.459
MDCK Permeability:  2.870857497327961e-05
Pgp-inhibitor:  0.001
Pgp-substrate:  0.004
Human Intestinal Absorption (HIA):  0.019
20% Bioavailability (F20%):  0.021
30% Bioavailability (F30%):  0.835

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.709
Plasma Protein Binding (PPB):  89.79833221435547%
Volume Distribution (VD):  1.392
Pgp-substrate:  4.854087829589844%

ADMET: Metabolism

CYP1A2-inhibitor:  0.116
CYP1A2-substrate:  0.383
CYP2C19-inhibitor:  0.307
CYP2C19-substrate:  0.85
CYP2C9-inhibitor:  0.247
CYP2C9-substrate:  0.395
CYP2D6-inhibitor:  0.159
CYP2D6-substrate:  0.064
CYP3A4-inhibitor:  0.86
CYP3A4-substrate:  0.539

ADMET: Excretion

Clearance (CL):  8.532
Half-life (T1/2):  0.289

ADMET: Toxicity

hERG Blockers:  0.027
Human Hepatotoxicity (H-HT):  0.131
Drug-inuced Liver Injury (DILI):  0.031
AMES Toxicity:  0.003
Rat Oral Acute Toxicity:  0.033
Maximum Recommended Daily Dose:  0.968
Skin Sensitization:  0.638
Carcinogencity:  0.092
Eye Corrosion:  0.296
Eye Irritation:  0.788
Respiratory Toxicity:  0.104

Download Data

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  Natural Product: NPC68014

Natural Product ID:  NPC68014
Common Name*:   1(10)E,5E-Germacradien-4Beta-Ol
IUPAC Name:   (1S,2E,4S,7E)-1,7-dimethyl-4-propan-2-ylcyclodeca-2,7-dien-1-ol
Synonyms:  
Standard InCHIKey:  RHCTXHCNRLCYBN-LDKNCKFKSA-N
Standard InCHI:  InChI=1S/C15H26O/c1-12(2)14-8-7-13(3)6-5-10-15(4,16)11-9-14/h6,9,11-12,14,16H,5,7-8,10H2,1-4H3/b11-9+,13-6+/t14-,15+/m1/s1
SMILES:  C/C/1=CCC[C@](C)(O)/C=C/[C@@H](CC1)C(C)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL463044
PubChem CID:   11148775
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001550] Sesquiterpenoids
          • [CHEMONTID:0002456] Germacrane sesquiterpenoids

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

  Species Source

Organism ID Organism Name Taxonomy Level Family SuperKingdom Isolation Part Collection Location Collection Time Reference
NPO6836 Alpinia blepharocalyx Species Zingiberaceae Eukaryota seeds Mengha, Yunnan Province, China 1991-Aug PMID[11277741]
NPO6836 Alpinia blepharocalyx Species Zingiberaceae Eukaryota seeds n.a. n.a. PMID[11325233]
NPO6836 Alpinia blepharocalyx Species Zingiberaceae Eukaryota Seeds n.a. n.a. PMID[11430002]
NPO8788 Renealmia nicolaioides Species Zingiberaceae Eukaryota n.a. n.a. n.a. PMID[12444686]
NPO3261 Aplysina archeri Species Aplysinidae Eukaryota n.a. n.a. n.a. PMID[1324982]
NPO6457 Pinus strobus Species Pinaceae Eukaryota n.a. heartwood n.a. PMID[13465274]
NPO17593 Pinus sylvestris Species Pinaceae Eukaryota n.a. n.a. n.a. PMID[1536925]
NPO14054 Penicillium janczewskii Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[16180822]
NPO422 Euphorbia cornigera Species Euphorbiaceae Eukaryota n.a. n.a. n.a. PMID[17512094]
NPO422 Euphorbia cornigera Species Euphorbiaceae Eukaryota n.a. n.a. n.a. PMID[19376614]
NPO13135 Campylotropis hirtella Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[19481938]
NPO17593 Pinus sylvestris Species Pinaceae Eukaryota n.a. seed n.a. PMID[24225786]
NPO12796 Periploca sepium Species Apocynaceae Eukaryota n.a. n.a. n.a. PMID[28294615]
NPO865 Dendrobium loddigesii Species Orchidaceae Eukaryota n.a. n.a. n.a. PMID[31291099]
NPO2697 Monodora tenuifolia Species Annonaceae Eukaryota n.a. n.a. n.a. PMID[3509958]
NPO6836 Alpinia blepharocalyx Species Zingiberaceae Eukaryota n.a. n.a. n.a. PMID[9461664]
NPO13135 Campylotropis hirtella Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO6836 Alpinia blepharocalyx Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO12796 Periploca sepium Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO865 Dendrobium loddigesii Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO6731 Ononis spinosa Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO7773 Crinum moorei Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO4564 Anguilla japonica Species Anguillidae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO17593 Pinus sylvestris Species Pinaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO6836 Alpinia blepharocalyx Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO24089 Alcea rosea Species Malvaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO865 Dendrobium loddigesii Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO13135 Campylotropis hirtella Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO2408 Millettia laurentii Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO6731 Ononis spinosa Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO12796 Periploca sepium Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO4564 Anguilla japonica Species Anguillidae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7773 Crinum moorei Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO17593 Pinus sylvestris Species Pinaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO17593 Pinus sylvestris Species Pinaceae 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]
NPO12796 Periploca sepium Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO24089 Alcea rosea Species Malvaceae 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]
NPO865 Dendrobium loddigesii Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO5261 Sideroxylon cubense Species Sapotaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6836 Alpinia blepharocalyx Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10638 Plectranthus myrianthus Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1257 Distephanus angulifolius Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1489 Pseudoplexaura flagellosa Species Plexauridae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2250 Hylocomium splendens Species Hylocomiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11576 Glycosmis macrophylla Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3873 Crotalaria candicans Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1390 Melolontha melolontha Species Scarabaeidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO295 Kokoona reflexa Species Celastraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1242 Balanops australiana Species Balanopaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11843 Stephania zippeliana Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12796 Periploca sepium Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3261 Aplysina archeri Species Aplysinidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24089 Alcea rosea Species Malvaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12565 Hypericum polyanthemum Species Hypericaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9319 Pterocaulon virgatum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5975 Aspergillus carneus Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11190 Veronica polita Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25760 Aspergillus striatus Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18993 Araiostegiella perdurans Species Davalliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3554 Aonidiella aurantii Species Diaspididae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10922 Pentaclethra macrophylla Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21720 Talaromyces variabilis Species Trichocomaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13135 Campylotropis hirtella Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10605 Tristania conferta Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5043 Eria japonica Species Orchidaceae 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]
NPO2408 Millettia laurentii Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22691 Mentha cardiaca Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17593 Pinus sylvestris Species Pinaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5584 Aldisa sanguinea Species Dorididae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1815 Breonia chinensis Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15487 Gymnopus confluens Species Omphalotaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4564 Anguilla japonica Species Anguillidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14054 Penicillium janczewskii Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8788 Renealmia nicolaioides Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12091 Martensia denticulata Species Delesseriaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO422 Euphorbia cornigera Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6289 Ceropegia dichotoma Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2993 0totodarus sloanii Species Ommastrephidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9704 Sonneratia caseolaris Species Lythraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4949 Salvia yosgadensis Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7760 Macrolepiota neomastoidea Species Agaricaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6231 Cortinarius odoratus Species Cortinariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO849 Euonymus tingens Species Celastraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5456 Juniperus drupacea Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3956 Maesa ramentacea Species Primulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23384 Rhodiola semenovii Species Crassulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3743 Sideritis brevibracteata Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6457 Pinus strobus Species Pinaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8934 Gypsophila perfoliata Species Caryophyllaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO526 Salvia sessei Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO865 Dendrobium loddigesii Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7449 Eleutherobia albiflora Species Alcyoniidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4274 Alcyonium utinomii Species Alcyoniidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7606 Salacia lehmbachii Species Celastraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6731 Ononis spinosa Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11747 Ocimum tenuiflorum 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]
NPO7007 Eucalyptus jenseni Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9532 Vernonia cistifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12205 Eucalyptus apodophylla Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2697 Monodora tenuifolia Species Annonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8058 Pluchea odorata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3408 Viguiera decurrens Species Asteraceae 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
NPT6 Organism Plasmodium falciparum Plasmodium falciparum IC50 < 5.0 ug.mL-1 PMID[452400]

☑ 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 NPC68014 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
0.8462 Intermediate Similarity NPC208638
0.8214 Intermediate Similarity NPC181872
0.8214 Intermediate Similarity NPC155025
0.8136 Intermediate Similarity NPC300593
0.8125 Intermediate Similarity NPC194586
0.8125 Intermediate Similarity NPC209279
0.8125 Intermediate Similarity NPC68889
0.8125 Intermediate Similarity NPC67761
0.8125 Intermediate Similarity NPC180871
0.8125 Intermediate Similarity NPC88079
0.8125 Intermediate Similarity NPC108494
0.8125 Intermediate Similarity NPC51758
0.8077 Intermediate Similarity NPC329773
0.7931 Intermediate Similarity NPC99487
0.7925 Intermediate Similarity NPC26906
0.7925 Intermediate Similarity NPC214584
0.7917 Intermediate Similarity NPC188596
0.7797 Intermediate Similarity NPC225342
0.7778 Intermediate Similarity NPC35519
0.7778 Intermediate Similarity NPC294358
0.7778 Intermediate Similarity NPC306195
0.7778 Intermediate Similarity NPC179169
0.7778 Intermediate Similarity NPC157781
0.7778 Intermediate Similarity NPC71506
0.7778 Intermediate Similarity NPC40417
0.7778 Intermediate Similarity NPC177112
0.7778 Intermediate Similarity NPC181255
0.7759 Intermediate Similarity NPC475931
0.7705 Intermediate Similarity NPC308844
0.7667 Intermediate Similarity NPC174956
0.7667 Intermediate Similarity NPC473508
0.7627 Intermediate Similarity NPC66020
0.75 Intermediate Similarity NPC321867
0.75 Intermediate Similarity NPC210346
0.75 Intermediate Similarity NPC68679
0.75 Intermediate Similarity NPC207007
0.7407 Intermediate Similarity NPC474460
0.7407 Intermediate Similarity NPC182102
0.7407 Intermediate Similarity NPC26960
0.7368 Intermediate Similarity NPC227135
0.7368 Intermediate Similarity NPC251666
0.7368 Intermediate Similarity NPC329686
0.7368 Intermediate Similarity NPC232247
0.7347 Intermediate Similarity NPC56917
0.7333 Intermediate Similarity NPC240506
0.7333 Intermediate Similarity NPC176621
0.7302 Intermediate Similarity NPC267027
0.7302 Intermediate Similarity NPC311736
0.7273 Intermediate Similarity NPC244038
0.7255 Intermediate Similarity NPC15162
0.7241 Intermediate Similarity NPC274396
0.7213 Intermediate Similarity NPC469728
0.72 Intermediate Similarity NPC218918
0.72 Intermediate Similarity NPC120926
0.7188 Intermediate Similarity NPC163290
0.7167 Intermediate Similarity NPC122239
0.7143 Intermediate Similarity NPC35756
0.7119 Intermediate Similarity NPC278550
0.7097 Intermediate Similarity NPC473759
0.7097 Intermediate Similarity NPC81615
0.7097 Intermediate Similarity NPC474480
0.7097 Intermediate Similarity NPC474155
0.7091 Intermediate Similarity NPC131623
0.7069 Intermediate Similarity NPC148216
0.7069 Intermediate Similarity NPC148163
0.7069 Intermediate Similarity NPC130209
0.7049 Intermediate Similarity NPC323153
0.7049 Intermediate Similarity NPC471081
0.7031 Intermediate Similarity NPC197089
0.7031 Intermediate Similarity NPC279434
0.7 Intermediate Similarity NPC226848
0.6981 Remote Similarity NPC24824
0.6981 Remote Similarity NPC210560
0.6981 Remote Similarity NPC165651
0.6964 Remote Similarity NPC27438
0.6949 Remote Similarity NPC48891
0.6949 Remote Similarity NPC473865
0.6949 Remote Similarity NPC474643
0.6935 Remote Similarity NPC64985
0.6923 Remote Similarity NPC73603
0.6923 Remote Similarity NPC136813
0.6897 Remote Similarity NPC105780
0.6897 Remote Similarity NPC168518
0.6897 Remote Similarity NPC474127
0.6885 Remote Similarity NPC5698
0.6885 Remote Similarity NPC469321
0.6875 Remote Similarity NPC19569
0.6833 Remote Similarity NPC11130
0.6818 Remote Similarity NPC224532
0.6812 Remote Similarity NPC190859
0.678 Remote Similarity NPC474644
0.678 Remote Similarity NPC298299
0.6774 Remote Similarity NPC135648
0.6774 Remote Similarity NPC252809
0.6774 Remote Similarity NPC234264
0.6774 Remote Similarity NPC47840
0.6769 Remote Similarity NPC202017
0.6769 Remote Similarity NPC326310
0.6765 Remote Similarity NPC471660
0.6765 Remote Similarity NPC472254
0.6727 Remote Similarity NPC100445
0.6724 Remote Similarity NPC192962
0.6719 Remote Similarity NPC309300
0.6719 Remote Similarity NPC107540
0.6716 Remote Similarity NPC471560
0.6716 Remote Similarity NPC473893
0.6716 Remote Similarity NPC74722
0.6716 Remote Similarity NPC304690
0.6667 Remote Similarity NPC474495
0.6667 Remote Similarity NPC55412
0.6667 Remote Similarity NPC275098
0.6667 Remote Similarity NPC477791
0.6667 Remote Similarity NPC79576
0.6667 Remote Similarity NPC4881
0.6667 Remote Similarity NPC249645
0.6667 Remote Similarity NPC41160
0.6667 Remote Similarity NPC282694
0.6667 Remote Similarity NPC194208
0.6667 Remote Similarity NPC39068
0.6667 Remote Similarity NPC63111
0.6667 Remote Similarity NPC278895
0.6667 Remote Similarity NPC473672
0.6667 Remote Similarity NPC114651
0.6667 Remote Similarity NPC259299
0.662 Remote Similarity NPC170148
0.6615 Remote Similarity NPC61503
0.6615 Remote Similarity NPC187619
0.6613 Remote Similarity NPC309825
0.661 Remote Similarity NPC189677
0.661 Remote Similarity NPC63396
0.661 Remote Similarity NPC202850
0.6607 Remote Similarity NPC62755
0.6604 Remote Similarity NPC86538
0.6567 Remote Similarity NPC117804
0.6567 Remote Similarity NPC272961
0.6567 Remote Similarity NPC305698
0.6567 Remote Similarity NPC167527
0.6567 Remote Similarity NPC96484
0.6567 Remote Similarity NPC471238
0.6562 Remote Similarity NPC124112
0.6538 Remote Similarity NPC144023
0.6522 Remote Similarity NPC471272
0.6522 Remote Similarity NPC23954
0.6515 Remote Similarity NPC230107
0.6515 Remote Similarity NPC250977
0.6515 Remote Similarity NPC162309
0.6508 Remote Similarity NPC469694
0.65 Remote Similarity NPC281590
0.65 Remote Similarity NPC218525
0.6471 Remote Similarity NPC15934
0.6471 Remote Similarity NPC136473
0.6471 Remote Similarity NPC329989
0.6471 Remote Similarity NPC255042
0.6471 Remote Similarity NPC239373
0.6471 Remote Similarity NPC182840
0.6471 Remote Similarity NPC103213
0.6471 Remote Similarity NPC474900
0.6471 Remote Similarity NPC474248
0.6471 Remote Similarity NPC29091
0.6462 Remote Similarity NPC475704
0.6462 Remote Similarity NPC323424
0.6462 Remote Similarity NPC110241
0.6462 Remote Similarity NPC96793
0.6452 Remote Similarity NPC10017
0.6441 Remote Similarity NPC474496
0.6441 Remote Similarity NPC165755
0.6429 Remote Similarity NPC130665
0.6429 Remote Similarity NPC220939
0.6429 Remote Similarity NPC265485
0.6429 Remote Similarity NPC329763
0.6418 Remote Similarity NPC69649
0.6418 Remote Similarity NPC171225
0.6418 Remote Similarity NPC68703
0.6418 Remote Similarity NPC82337
0.6415 Remote Similarity NPC177470
0.6406 Remote Similarity NPC274704
0.6393 Remote Similarity NPC24443
0.6393 Remote Similarity NPC179024
0.6393 Remote Similarity NPC141699
0.6389 Remote Similarity NPC236228
0.6389 Remote Similarity NPC310643
0.6389 Remote Similarity NPC256720
0.6389 Remote Similarity NPC471658
0.6379 Remote Similarity NPC59408
0.6379 Remote Similarity NPC71053
0.6379 Remote Similarity NPC151782
0.6377 Remote Similarity NPC286154
0.6377 Remote Similarity NPC189745
0.6377 Remote Similarity NPC34834
0.6364 Remote Similarity NPC471200
0.6364 Remote Similarity NPC140501
0.6364 Remote Similarity NPC205618
0.6364 Remote Similarity NPC261782
0.6364 Remote Similarity NPC87439
0.6364 Remote Similarity NPC469326
0.6346 Remote Similarity NPC183670
0.6338 Remote Similarity NPC476366
0.6338 Remote Similarity NPC471659
0.6338 Remote Similarity NPC309178
0.6338 Remote Similarity NPC206875

  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 NPC68014 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
0.75 Intermediate Similarity NPD368 Approved
0.7069 Intermediate Similarity NPD342 Phase 1
0.6667 Remote Similarity NPD4219 Approved
0.6364 Remote Similarity NPD4265 Approved
0.625 Remote Similarity NPD8264 Approved
0.6216 Remote Similarity NPD7322 Clinical (unspecified phase)
0.6154 Remote Similarity NPD4192 Approved
0.6154 Remote Similarity NPD4193 Approved
0.6154 Remote Similarity NPD4194 Approved
0.6154 Remote Similarity NPD4191 Approved
0.6078 Remote Similarity NPD319 Phase 1
0.6053 Remote Similarity NPD7514 Phase 3
0.6053 Remote Similarity NPD7332 Phase 2
0.5972 Remote Similarity NPD4732 Discontinued
0.5915 Remote Similarity NPD7143 Approved
0.5915 Remote Similarity NPD7144 Approved
0.589 Remote Similarity NPD4785 Approved
0.589 Remote Similarity NPD4784 Approved
0.5844 Remote Similarity NPD4820 Approved
0.5844 Remote Similarity NPD4821 Approved
0.5844 Remote Similarity NPD4819 Approved
0.5844 Remote Similarity NPD4822 Approved
0.5833 Remote Similarity NPD4243 Approved
0.5833 Remote Similarity NPD7151 Approved
0.5833 Remote Similarity NPD7152 Approved
0.5833 Remote Similarity NPD7150 Approved
0.5797 Remote Similarity NPD7331 Phase 2
0.5789 Remote Similarity NPD7145 Approved
0.5789 Remote Similarity NPD5784 Clinical (unspecified phase)
0.5775 Remote Similarity NPD6923 Approved
0.5775 Remote Similarity NPD6922 Approved
0.5769 Remote Similarity NPD6902 Approved
0.5763 Remote Similarity NPD4220 Pre-registration
0.5676 Remote Similarity NPD6926 Approved
0.5676 Remote Similarity NPD6924 Approved
0.5658 Remote Similarity NPD5776 Phase 2
0.5658 Remote Similarity NPD6925 Approved
0.5658 Remote Similarity NPD6932 Approved
0.5652 Remote Similarity NPD2685 Clinical (unspecified phase)
0.5641 Remote Similarity NPD6931 Approved
0.5641 Remote Similarity NPD6930 Phase 2
0.5625 Remote Similarity NPD5362 Discontinued
0.5625 Remote Similarity NPD5332 Approved
0.5625 Remote Similarity NPD5331 Approved
0.561 Remote Similarity NPD4519 Discontinued
0.561 Remote Similarity NPD4623 Approved
0.56 Remote Similarity NPD5275 Approved
0.56 Remote Similarity NPD4190 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