Structure

Physi-Chem Properties

Molecular Weight:  284.14
Volume:  304.767
LogP:  4.289
LogD:  3.915
LogS:  -3.442
# Rotatable Bonds:  2
TPSA:  49.69
# H-Bond Aceptor:  3
# H-Bond Donor:  2
# Rings:  3
# Heavy Atoms:  3

MedChem Properties

QED Drug-Likeness Score:  0.869
Synthetic Accessibility Score:  3.269
Fsp3:  0.333
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:  -4.591
MDCK Permeability:  1.1986685422016308e-05
Pgp-inhibitor:  0.005
Pgp-substrate:  0.024
Human Intestinal Absorption (HIA):  0.007
20% Bioavailability (F20%):  0.118
30% Bioavailability (F30%):  0.09

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.086
Plasma Protein Binding (PPB):  95.18950653076172%
Volume Distribution (VD):  1.269
Pgp-substrate:  3.8263306617736816%

ADMET: Metabolism

CYP1A2-inhibitor:  0.31
CYP1A2-substrate:  0.267
CYP2C19-inhibitor:  0.878
CYP2C19-substrate:  0.269
CYP2C9-inhibitor:  0.748
CYP2C9-substrate:  0.966
CYP2D6-inhibitor:  0.812
CYP2D6-substrate:  0.861
CYP3A4-inhibitor:  0.751
CYP3A4-substrate:  0.293

ADMET: Excretion

Clearance (CL):  14.336
Half-life (T1/2):  0.516

ADMET: Toxicity

hERG Blockers:  0.073
Human Hepatotoxicity (H-HT):  0.076
Drug-inuced Liver Injury (DILI):  0.286
AMES Toxicity:  0.233
Rat Oral Acute Toxicity:  0.355
Maximum Recommended Daily Dose:  0.041
Skin Sensitization:  0.666
Carcinogencity:  0.44
Eye Corrosion:  0.132
Eye Irritation:  0.955
Respiratory Toxicity:  0.314

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  Natural Product: NPC123175

Natural Product ID:  NPC123175
Common Name*:   Meso-3,3'-Didemethoxynectandrin B
IUPAC Name:   4-[(2R,3R,4S,5S)-5-(4-hydroxyphenyl)-3,4-dimethyloxolan-2-yl]phenol
Synonyms:   Meso-3,3'-Didemethoxynectandrin B
Standard InCHIKey:  PIBJADPEZQHMQS-FRVJLOGJSA-N
Standard InCHI:  InChI=1S/C18H20O3/c1-11-12(2)18(14-5-9-16(20)10-6-14)21-17(11)13-3-7-15(19)8-4-13/h3-12,17-20H,1-2H3/t11-,12+,17-,18+
SMILES:  C[C@H]1[C@@H](C)[C@H](c2ccc(cc2)O)O[C@@H]1c1ccc(cc1)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL2147417
PubChem CID:   14213224
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0001392] Lignans, neolignans and related compounds
      • [CHEMONTID:0003686] Furanoid lignans
        • [CHEMONTID:0001604] Tetrahydrofuran lignans
          • [CHEMONTID:0003423] 7,7'-epoxylignans

*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
NPO1751 Ribes nigrum Species n.a. n.a. Fruit n.a. n.a. DOI[10.1016/S0963-9969(99)00095-2]
NPO14178 Leonurus persicus Species Lamiaceae Eukaryota Aerial parts n.a. n.a. PMID[10395493]
NPO15442 Magnolia sieboldii Species Magnoliaceae Eukaryota n.a. n.a. n.a. PMID[11534769]
NPO13392 Caiophora coronata Species Loasaceae Eukaryota n.a. n.a. n.a. PMID[14695811]
NPO1751 Ribes nigrum Species n.a. n.a. n.a. fruit n.a. PMID[16417304]
NPO14284 Delphinium shawurense Species Ranunculaceae Eukaryota n.a. n.a. n.a. PMID[20351801]
NPO15400 Krameria lappacea Species Krameriaceae Eukaryota n.a. root n.a. PMID[21800856]
NPO15442 Magnolia sieboldii Species Magnoliaceae Eukaryota stem bark n.a. n.a. PMID[8988596]
NPO1751 Ribes nigrum Species n.a. n.a. n.a. n.a. Database[FooDB]
NPO1751 Ribes nigrum Species n.a. n.a. Bulb n.a. n.a. Database[FooDB]
NPO1751 Ribes nigrum Species n.a. n.a. Fruit n.a. n.a. Database[FooDB]
NPO1751 Ribes nigrum Species n.a. n.a. Fruit Juice n.a. n.a. Database[FooDB]
NPO1751 Ribes nigrum Species n.a. n.a. Leaf n.a. n.a. Database[FooDB]
NPO1751 Ribes nigrum Species n.a. n.a. Seed n.a. n.a. Database[FooDB]
NPO1751 Ribes nigrum Species n.a. n.a. Seed Essent. Oil n.a. n.a. Database[FooDB]
NPO1751 Ribes nigrum Species n.a. n.a. Fruits n.a. Database[FooDB]
NPO558 Limnophila rugosa Species Limoniidae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO15442 Magnolia sieboldii Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO16741 Codonopsis pilosula Species Campanulaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO14178 Leonurus persicus Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO15442 Magnolia sieboldii Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14673 Lathyrus nissolia Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14178 Leonurus persicus Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO16741 Codonopsis pilosula Species Campanulaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO1751 Ribes nigrum Species n.a. n.a. n.a. n.a. n.a. Database[TCMID]
NPO558 Limnophila rugosa Species Limoniidae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO2458 Aconitum violaceum Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO558 Limnophila rugosa Species Limoniidae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO16741 Codonopsis pilosula Species Campanulaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO16741 Codonopsis pilosula Species Campanulaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO13311 Agelas linnaei Species Agelasidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15400 Krameria lappacea Species Krameriaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14673 Lathyrus nissolia Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10191 Ormosia balansae Species Limoniidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14178 Leonurus persicus Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15626 Alternaria japonica Species Pleosporaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO315 Krameria interior Species Krameriaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14284 Delphinium shawurense Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1751 Ribes nigrum Species n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO9860.1 Pinus brutia var. eldarica Varieties Pinaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7713 Euplotes raikovi Species Euplotidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13477 Cyberlindnera jadinii Species Phaffomycetaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28601 Aspergillus falconensis Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO965 Bleekeria vitiensis Species Plesiopidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO558 Limnophila rugosa Species Limoniidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12982 Dysidea amblia Species Dysideidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2458 Aconitum violaceum Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3244 Ascidia ahodori Species Ascidiidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5464 Baliospermum axillare Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4512 Fagraea gracilipes Species Gentianaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15160 Gutierrezia lucida Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3949 Ceramium rubrum Species Ceramiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3420 Alsomitra graciliflora Species Cucurbitaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13160 Garcinia xipshuanbannaensis Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15442 Magnolia sieboldii Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9820 Nepeta erecta Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14043 Caulerpa serrulata Species Caulerpaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6347 Iryanthera paraensis Species Myristicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13392 Caiophora coronata Species Loasaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15253 Helichrysum graveolens Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10887 Pseudeurotium zonatum Species Pseudeurotiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15864 Skimmia wallichii Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16741 Codonopsis pilosula Species Campanulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11912 Peltogyne porphyrocardia Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12756 Roboastra tigris Species Polyceridae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11128 Ratibida mexicana 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
NPT325 Individual Protein Cyclooxygenase-2 Ovis aries IC50 > 50000.0 nM PMID[558526]
NPT570 Individual Protein Arachidonate 5-lipoxygenase Homo sapiens IC50 > 50000.0 nM PMID[558526]
NPT324 Individual Protein Cyclooxygenase-1 Ovis aries IC50 > 50000.0 nM PMID[558526]
NPT956 Individual Protein Prostaglandin E synthase Homo sapiens IC50 > 50000.0 nM PMID[558526]
NPT32 Organism Mus musculus Mus musculus Inhibition = 14.0 % PMID[558526]
NPT32 Organism Mus musculus Mus musculus Inhibition = 52.0 % PMID[558526]
NPT32 Organism Mus musculus Mus musculus Inhibition = 72.0 % PMID[558526]
NPT32 Organism Mus musculus Mus musculus ID50 = 0.36 umol/cm2 PMID[558526]
NPT2 Others Unspecified IC50 > 20000.0 nM PMID[558526]

☑ 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 NPC123175 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 NPC176730
0.9633 High Similarity NPC476266
0.9252 High Similarity NPC265211
0.9252 High Similarity NPC306045
0.913 High Similarity NPC150026
0.9 High Similarity NPC42911
0.9 High Similarity NPC290353
0.9 High Similarity NPC153795
0.8972 High Similarity NPC92623
0.8972 High Similarity NPC135464
0.8898 High Similarity NPC81641
0.8889 High Similarity NPC473451
0.8879 High Similarity NPC154899
0.8879 High Similarity NPC233396
0.8814 High Similarity NPC257682
0.8814 High Similarity NPC146355
0.8814 High Similarity NPC131747
0.8807 High Similarity NPC201959
0.8684 High Similarity NPC301651
0.8684 High Similarity NPC473556
0.8678 High Similarity NPC21867
0.8678 High Similarity NPC128208
0.8678 High Similarity NPC184733
0.8678 High Similarity NPC129570
0.8678 High Similarity NPC11258
0.8678 High Similarity NPC282703
0.8678 High Similarity NPC45774
0.8644 High Similarity NPC174977
0.8644 High Similarity NPC255026
0.8624 High Similarity NPC113457
0.8585 High Similarity NPC51333
0.8585 High Similarity NPC78119
0.8585 High Similarity NPC132078
0.8585 High Similarity NPC216468
0.8583 High Similarity NPC124030
0.8571 High Similarity NPC82664
0.8571 High Similarity NPC216520
0.8571 High Similarity NPC132271
0.8571 High Similarity NPC473388
0.8571 High Similarity NPC292730
0.8537 High Similarity NPC145305
0.8537 High Similarity NPC241522
0.8537 High Similarity NPC42300
0.8537 High Similarity NPC92164
0.8537 High Similarity NPC242807
0.8537 High Similarity NPC64201
0.8537 High Similarity NPC187998
0.8537 High Similarity NPC153739
0.8537 High Similarity NPC257582
0.8537 High Similarity NPC174495
0.8537 High Similarity NPC77040
0.8525 High Similarity NPC470084
0.8525 High Similarity NPC39064
0.8525 High Similarity NPC47283
0.8512 High Similarity NPC206882
0.8505 High Similarity NPC213730
0.8476 Intermediate Similarity NPC26244
0.8468 Intermediate Similarity NPC40432
0.8468 Intermediate Similarity NPC161557
0.8468 Intermediate Similarity NPC476166
0.8468 Intermediate Similarity NPC236014
0.8468 Intermediate Similarity NPC17343
0.8468 Intermediate Similarity NPC207892
0.8468 Intermediate Similarity NPC300875
0.8468 Intermediate Similarity NPC280653
0.8468 Intermediate Similarity NPC27843
0.8468 Intermediate Similarity NPC115207
0.8468 Intermediate Similarity NPC164574
0.8468 Intermediate Similarity NPC129106
0.8468 Intermediate Similarity NPC268917
0.8468 Intermediate Similarity NPC206224
0.8468 Intermediate Similarity NPC7171
0.8468 Intermediate Similarity NPC158079
0.8468 Intermediate Similarity NPC75440
0.8468 Intermediate Similarity NPC150011
0.8468 Intermediate Similarity NPC277804
0.8468 Intermediate Similarity NPC228346
0.8468 Intermediate Similarity NPC118114
0.8468 Intermediate Similarity NPC129784
0.8468 Intermediate Similarity NPC196765
0.8468 Intermediate Similarity NPC12875
0.8468 Intermediate Similarity NPC228369
0.8455 Intermediate Similarity NPC475875
0.8448 Intermediate Similarity NPC474933
0.843 Intermediate Similarity NPC148627
0.8426 Intermediate Similarity NPC91461
0.8426 Intermediate Similarity NPC7686
0.8426 Intermediate Similarity NPC40258
0.8421 Intermediate Similarity NPC141003
0.8421 Intermediate Similarity NPC35344
0.8417 Intermediate Similarity NPC31344
0.8417 Intermediate Similarity NPC317769
0.8411 Intermediate Similarity NPC92730
0.8403 Intermediate Similarity NPC216929
0.8403 Intermediate Similarity NPC57268
0.8403 Intermediate Similarity NPC312713
0.8403 Intermediate Similarity NPC172676
0.8403 Intermediate Similarity NPC126935
0.8403 Intermediate Similarity NPC65933
0.84 Intermediate Similarity NPC13005
0.84 Intermediate Similarity NPC181049
0.84 Intermediate Similarity NPC207400
0.8393 Intermediate Similarity NPC474272
0.8387 Intermediate Similarity NPC27187
0.8387 Intermediate Similarity NPC470225
0.8381 Intermediate Similarity NPC151715
0.8362 Intermediate Similarity NPC85292
0.8362 Intermediate Similarity NPC54507
0.8362 Intermediate Similarity NPC141090
0.8362 Intermediate Similarity NPC229147
0.8361 Intermediate Similarity NPC230479
0.8361 Intermediate Similarity NPC283049
0.8361 Intermediate Similarity NPC50315
0.8361 Intermediate Similarity NPC262573
0.8361 Intermediate Similarity NPC26879
0.8361 Intermediate Similarity NPC471215
0.8348 Intermediate Similarity NPC12656
0.8348 Intermediate Similarity NPC120280
0.8333 Intermediate Similarity NPC36016
0.8333 Intermediate Similarity NPC100099
0.8333 Intermediate Similarity NPC158331
0.8333 Intermediate Similarity NPC294741
0.832 Intermediate Similarity NPC271945
0.832 Intermediate Similarity NPC181497
0.832 Intermediate Similarity NPC162801
0.8319 Intermediate Similarity NPC63345
0.8319 Intermediate Similarity NPC470414
0.8318 Intermediate Similarity NPC225464
0.8304 Intermediate Similarity NPC262365
0.8302 Intermediate Similarity NPC313650
0.8293 Intermediate Similarity NPC165045
0.8293 Intermediate Similarity NPC118533
0.8291 Intermediate Similarity NPC195466
0.8276 Intermediate Similarity NPC464
0.8276 Intermediate Similarity NPC53906
0.8276 Intermediate Similarity NPC185541
0.8273 Intermediate Similarity NPC323810
0.8268 Intermediate Similarity NPC287745
0.8268 Intermediate Similarity NPC471942
0.8268 Intermediate Similarity NPC97834
0.8268 Intermediate Similarity NPC115335
0.8268 Intermediate Similarity NPC67247
0.8268 Intermediate Similarity NPC193026
0.8268 Intermediate Similarity NPC225696
0.8268 Intermediate Similarity NPC198154
0.8268 Intermediate Similarity NPC187616
0.8268 Intermediate Similarity NPC296915
0.8268 Intermediate Similarity NPC49603
0.8268 Intermediate Similarity NPC223008
0.8264 Intermediate Similarity NPC38761
0.8264 Intermediate Similarity NPC471693
0.8264 Intermediate Similarity NPC76465
0.8254 Intermediate Similarity NPC204215
0.8254 Intermediate Similarity NPC175067
0.8254 Intermediate Similarity NPC471505
0.8254 Intermediate Similarity NPC4940
0.825 Intermediate Similarity NPC54972
0.825 Intermediate Similarity NPC193364
0.8235 Intermediate Similarity NPC282255
0.8235 Intermediate Similarity NPC3239
0.8226 Intermediate Similarity NPC53986
0.8226 Intermediate Similarity NPC471064
0.8226 Intermediate Similarity NPC38664
0.822 Intermediate Similarity NPC131118
0.8214 Intermediate Similarity NPC251306
0.8203 Intermediate Similarity NPC99572
0.8203 Intermediate Similarity NPC135777
0.8203 Intermediate Similarity NPC126409
0.8203 Intermediate Similarity NPC142547
0.8198 Intermediate Similarity NPC138942
0.8197 Intermediate Similarity NPC294156
0.8197 Intermediate Similarity NPC256015
0.8197 Intermediate Similarity NPC106914
0.8197 Intermediate Similarity NPC18449
0.8197 Intermediate Similarity NPC246648
0.8197 Intermediate Similarity NPC197351
0.8197 Intermediate Similarity NPC34902
0.8197 Intermediate Similarity NPC86502
0.8197 Intermediate Similarity NPC121783
0.8197 Intermediate Similarity NPC134195
0.819 Intermediate Similarity NPC180508
0.819 Intermediate Similarity NPC228287
0.819 Intermediate Similarity NPC304541
0.819 Intermediate Similarity NPC473137
0.819 Intermediate Similarity NPC276737
0.819 Intermediate Similarity NPC45040
0.819 Intermediate Similarity NPC22610
0.8189 Intermediate Similarity NPC85435
0.8189 Intermediate Similarity NPC26394
0.8182 Intermediate Similarity NPC305205
0.8182 Intermediate Similarity NPC168829
0.8182 Intermediate Similarity NPC62351
0.8175 Intermediate Similarity NPC237424
0.8175 Intermediate Similarity NPC238168
0.8174 Intermediate Similarity NPC228425
0.8167 Intermediate Similarity NPC102639
0.816 Intermediate Similarity NPC93962
0.816 Intermediate Similarity NPC214246
0.8158 Intermediate Similarity NPC183700
0.8158 Intermediate Similarity NPC44732

  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 NPC123175 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
0.8762 High Similarity NPD3020 Approved
0.8476 Intermediate Similarity NPD2860 Approved
0.8476 Intermediate Similarity NPD2859 Approved
0.8443 Intermediate Similarity NPD2861 Phase 2
0.8381 Intermediate Similarity NPD2934 Approved
0.8381 Intermediate Similarity NPD2933 Approved
0.825 Intermediate Similarity NPD1610 Phase 2
0.8226 Intermediate Similarity NPD4908 Phase 1
0.8095 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.807 Intermediate Similarity NPD3022 Approved
0.807 Intermediate Similarity NPD3021 Approved
0.8037 Intermediate Similarity NPD1432 Clinical (unspecified phase)
0.7917 Intermediate Similarity NPD3091 Approved
0.7917 Intermediate Similarity NPD1548 Phase 1
0.7874 Intermediate Similarity NPD3027 Phase 3
0.7826 Intermediate Similarity NPD2684 Approved
0.7823 Intermediate Similarity NPD3600 Clinical (unspecified phase)
0.7807 Intermediate Similarity NPD968 Approved
0.7805 Intermediate Similarity NPD3092 Approved
0.7797 Intermediate Similarity NPD5283 Phase 1
0.7787 Intermediate Similarity NPD5238 Clinical (unspecified phase)
0.7768 Intermediate Similarity NPD940 Approved
0.7768 Intermediate Similarity NPD846 Approved
0.768 Intermediate Similarity NPD6582 Phase 2
0.768 Intermediate Similarity NPD6583 Phase 3
0.7679 Intermediate Similarity NPD1242 Phase 1
0.7674 Intermediate Similarity NPD3764 Approved
0.7667 Intermediate Similarity NPD7157 Approved
0.7647 Intermediate Similarity NPD2229 Approved
0.7647 Intermediate Similarity NPD2228 Approved
0.7647 Intermediate Similarity NPD2234 Approved
0.7642 Intermediate Similarity NPD2668 Approved
0.7642 Intermediate Similarity NPD2667 Approved
0.7638 Intermediate Similarity NPD6584 Phase 3
0.7623 Intermediate Similarity NPD7741 Discontinued
0.7615 Intermediate Similarity NPD845 Approved
0.7607 Intermediate Similarity NPD5451 Approved
0.7607 Intermediate Similarity NPD4750 Phase 3
0.7578 Intermediate Similarity NPD5736 Approved
0.7568 Intermediate Similarity NPD288 Approved
0.7563 Intermediate Similarity NPD7843 Approved
0.7559 Intermediate Similarity NPD3094 Phase 2
0.7557 Intermediate Similarity NPD4060 Phase 1
0.754 Intermediate Similarity NPD5327 Phase 3
0.754 Intermediate Similarity NPD4749 Approved
0.754 Intermediate Similarity NPD4659 Approved
0.7524 Intermediate Similarity NPD111 Approved
0.7521 Intermediate Similarity NPD6671 Approved
0.75 Intermediate Similarity NPD5126 Approved
0.75 Intermediate Similarity NPD5125 Phase 3
0.75 Intermediate Similarity NPD5735 Approved
0.75 Intermediate Similarity NPD3095 Discontinued
0.75 Intermediate Similarity NPD6355 Discontinued
0.7481 Intermediate Similarity NPD2029 Clinical (unspecified phase)
0.748 Intermediate Similarity NPD9545 Approved
0.7479 Intermediate Similarity NPD228 Approved
0.7477 Intermediate Similarity NPD844 Approved
0.7477 Intermediate Similarity NPD1809 Phase 2
0.7462 Intermediate Similarity NPD4625 Phase 3
0.746 Intermediate Similarity NPD1608 Approved
0.7424 Intermediate Similarity NPD3619 Clinical (unspecified phase)
0.7424 Intermediate Similarity NPD1613 Approved
0.7424 Intermediate Similarity NPD2238 Phase 2
0.7424 Intermediate Similarity NPD3620 Phase 2
0.7424 Intermediate Similarity NPD4140 Approved
0.7424 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7422 Intermediate Similarity NPD4104 Clinical (unspecified phase)
0.7422 Intermediate Similarity NPD4103 Phase 2
0.7422 Intermediate Similarity NPD4339 Clinical (unspecified phase)
0.7417 Intermediate Similarity NPD7635 Approved
0.7417 Intermediate Similarity NPD5535 Approved
0.7417 Intermediate Similarity NPD821 Approved
0.7405 Intermediate Similarity NPD6410 Clinical (unspecified phase)
0.7381 Intermediate Similarity NPD3705 Approved
0.7368 Intermediate Similarity NPD3028 Approved
0.7368 Intermediate Similarity NPD289 Clinical (unspecified phase)
0.7364 Intermediate Similarity NPD4624 Approved
0.7364 Intermediate Similarity NPD6917 Clinical (unspecified phase)
0.736 Intermediate Similarity NPD4059 Approved
0.736 Intermediate Similarity NPD2932 Approved
0.736 Intermediate Similarity NPD6516 Phase 2
0.736 Intermediate Similarity NPD3019 Approved
0.736 Intermediate Similarity NPD5846 Approved
0.735 Intermediate Similarity NPD3134 Approved
0.7348 Intermediate Similarity NPD6663 Approved
0.7344 Intermediate Similarity NPD6696 Suspended
0.7344 Intermediate Similarity NPD8651 Approved
0.7333 Intermediate Similarity NPD5588 Approved
0.7323 Intermediate Similarity NPD2562 Approved
0.7323 Intermediate Similarity NPD2561 Approved
0.7323 Intermediate Similarity NPD2235 Phase 2
0.7323 Intermediate Similarity NPD2233 Approved
0.7323 Intermediate Similarity NPD2230 Approved
0.7323 Intermediate Similarity NPD2232 Approved
0.7323 Intermediate Similarity NPD2231 Phase 2
0.7319 Intermediate Similarity NPD4628 Phase 3
0.7317 Intermediate Similarity NPD3596 Phase 2
0.7313 Intermediate Similarity NPD6353 Approved
0.7313 Intermediate Similarity NPD3054 Approved
0.7313 Intermediate Similarity NPD3052 Approved
0.7311 Intermediate Similarity NPD9380 Clinical (unspecified phase)
0.7311 Intermediate Similarity NPD1792 Phase 2
0.7302 Intermediate Similarity NPD3847 Discontinued
0.7299 Intermediate Similarity NPD7037 Approved
0.7293 Intermediate Similarity NPD5837 Clinical (unspecified phase)
0.7288 Intermediate Similarity NPD290 Approved
0.728 Intermediate Similarity NPD1357 Approved
0.728 Intermediate Similarity NPD4093 Discontinued
0.7273 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7266 Intermediate Similarity NPD3685 Discontinued
0.7259 Intermediate Similarity NPD4537 Clinical (unspecified phase)
0.7259 Intermediate Similarity NPD4536 Approved
0.7259 Intermediate Similarity NPD4978 Clinical (unspecified phase)
0.7259 Intermediate Similarity NPD4538 Approved
0.7252 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7246 Intermediate Similarity NPD5698 Clinical (unspecified phase)
0.7244 Intermediate Similarity NPD5350 Clinical (unspecified phase)
0.7244 Intermediate Similarity NPD422 Phase 1
0.7244 Intermediate Similarity NPD5351 Clinical (unspecified phase)
0.7241 Intermediate Similarity NPD5700 Clinical (unspecified phase)
0.7226 Intermediate Similarity NPD7266 Discontinued
0.7222 Intermediate Similarity NPD4626 Approved
0.7222 Intermediate Similarity NPD17 Approved
0.7218 Intermediate Similarity NPD6405 Approved
0.7218 Intermediate Similarity NPD6407 Approved
0.7214 Intermediate Similarity NPD5058 Phase 3
0.7214 Intermediate Similarity NPD6667 Approved
0.7214 Intermediate Similarity NPD6666 Approved
0.7213 Intermediate Similarity NPD7159 Clinical (unspecified phase)
0.7209 Intermediate Similarity NPD7258 Clinical (unspecified phase)
0.7209 Intermediate Similarity NPD1283 Approved
0.7206 Intermediate Similarity NPD7033 Discontinued
0.7203 Intermediate Similarity NPD1444 Approved
0.7203 Intermediate Similarity NPD1445 Approved
0.72 Intermediate Similarity NPD5303 Approved
0.72 Intermediate Similarity NPD5304 Approved
0.72 Intermediate Similarity NPD6580 Approved
0.72 Intermediate Similarity NPD6581 Approved
0.72 Intermediate Similarity NPD1894 Discontinued
0.72 Intermediate Similarity NPD1182 Approved
0.719 Intermediate Similarity NPD6124 Clinical (unspecified phase)
0.7188 Intermediate Similarity NPD1840 Phase 2
0.7176 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7154 Intermediate Similarity NPD2797 Approved
0.7154 Intermediate Similarity NPD1476 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD2342 Discontinued
0.7143 Intermediate Similarity NPD5585 Approved
0.7143 Intermediate Similarity NPD3443 Approved
0.7143 Intermediate Similarity NPD3444 Approved
0.7143 Intermediate Similarity NPD1651 Approved
0.7143 Intermediate Similarity NPD5691 Approved
0.7143 Intermediate Similarity NPD6798 Discontinued
0.7143 Intermediate Similarity NPD6830 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD3445 Approved
0.7132 Intermediate Similarity NPD1669 Approved
0.7132 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.7122 Intermediate Similarity NPD4237 Approved
0.7122 Intermediate Similarity NPD4236 Phase 3
0.712 Intermediate Similarity NPD856 Approved
0.712 Intermediate Similarity NPD16 Approved
0.7113 Intermediate Similarity NPD4160 Clinical (unspecified phase)
0.7109 Intermediate Similarity NPD1091 Approved
0.7101 Intermediate Similarity NPD6002 Phase 3
0.7101 Intermediate Similarity NPD6005 Phase 3
0.7101 Intermediate Similarity NPD6003 Clinical (unspecified phase)
0.7101 Intermediate Similarity NPD5762 Approved
0.7101 Intermediate Similarity NPD6006 Clinical (unspecified phase)
0.7101 Intermediate Similarity NPD6004 Phase 3
0.7101 Intermediate Similarity NPD5763 Approved
0.7097 Intermediate Similarity NPD2557 Approved
0.7092 Intermediate Similarity NPD6815 Approved
0.7087 Intermediate Similarity NPD4589 Approved
0.708 Intermediate Similarity NPD5960 Phase 3
0.7077 Intermediate Similarity NPD1876 Approved
0.7071 Intermediate Similarity NPD6331 Phase 2
0.7071 Intermediate Similarity NPD7466 Approved
0.7069 Intermediate Similarity NPD2555 Approved
0.7069 Intermediate Similarity NPD2550 Approved
0.7069 Intermediate Similarity NPD2558 Approved
0.7069 Intermediate Similarity NPD2553 Approved
0.7069 Intermediate Similarity NPD2549 Approved
0.7069 Intermediate Similarity NPD2552 Approved
0.7068 Intermediate Similarity NPD7095 Approved
0.7059 Intermediate Similarity NPD2157 Approved
0.7059 Intermediate Similarity NPD4097 Suspended
0.705 Intermediate Similarity NPD5958 Discontinued
0.7045 Intermediate Similarity NPD1712 Approved
0.7042 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7042 Intermediate Similarity NPD7212 Phase 2
0.7042 Intermediate Similarity NPD7213 Phase 3
0.7037 Intermediate Similarity NPD1240 Approved
0.7037 Intermediate Similarity NPD1558 Phase 1
0.7034 Intermediate Similarity NPD3047 Approved
0.7034 Intermediate Similarity NPD3048 Approved
0.7034 Intermediate Similarity NPD3046 Approved
0.7009 Intermediate Similarity NPD4189 Approved
0.7009 Intermediate Similarity NPD4188 Approved
0.7 Intermediate Similarity NPD1358 Approved
0.7 Intermediate Similarity NPD2983 Phase 2
0.7 Intermediate Similarity NPD2982 Phase 2

  Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity
B: biological targets similarity
C: networks similarity
D: cell-based bioactivity similarity
E: similarity based on clinical data