Structure

Physi-Chem Properties

Molecular Weight:  152.07
Volume:  138.988
LogP:  -2.238
LogD:  -2.27
LogS:  -0.029
# Rotatable Bonds:  4
TPSA:  101.15
# H-Bond Aceptor:  5
# H-Bond Donor:  5
# Rings:  0
# Heavy Atoms:  5

MedChem Properties

QED Drug-Likeness Score:  0.296
Synthetic Accessibility Score:  3.423
Fsp3:  1.0
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.249
MDCK Permeability:  0.0032576946541666985
Pgp-inhibitor:  0.004
Pgp-substrate:  0.039
Human Intestinal Absorption (HIA):  0.53
20% Bioavailability (F20%):  0.241
30% Bioavailability (F30%):  0.969

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.291
Plasma Protein Binding (PPB):  10.66808795928955%
Volume Distribution (VD):  0.411
Pgp-substrate:  82.45759582519531%

ADMET: Metabolism

CYP1A2-inhibitor:  0.016
CYP1A2-substrate:  0.035
CYP2C19-inhibitor:  0.01
CYP2C19-substrate:  0.068
CYP2C9-inhibitor:  0.001
CYP2C9-substrate:  0.091
CYP2D6-inhibitor:  0.001
CYP2D6-substrate:  0.117
CYP3A4-inhibitor:  0.004
CYP3A4-substrate:  0.017

ADMET: Excretion

Clearance (CL):  1.757
Half-life (T1/2):  0.752

ADMET: Toxicity

hERG Blockers:  0.086
Human Hepatotoxicity (H-HT):  0.04
Drug-inuced Liver Injury (DILI):  0.033
AMES Toxicity:  0.054
Rat Oral Acute Toxicity:  0.005
Maximum Recommended Daily Dose:  0.002
Skin Sensitization:  0.064
Carcinogencity:  0.014
Eye Corrosion:  0.004
Eye Irritation:  0.682
Respiratory Toxicity:  0.016

Download Data

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

  Natural Product: NPC187058

Natural Product ID:  NPC187058
Common Name*:   (2S,4R)-Pentane-1,2,3,4,5-Pentol
IUPAC Name:   (2S,4R)-pentane-1,2,3,4,5-pentol
Synonyms:  
Standard InCHIKey:  HEBKCHPVOIAQTA-NGQZWQHPSA-N
Standard InCHI:  InChI=1S/C5H12O5/c6-1-3(8)5(10)4(9)2-7/h3-10H,1-2H2/t3-,4+,5?
SMILES:  C([C@@H](C([C@@H](CO)O)O)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1865120
PubChem CID:   6912
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0004603] Organic oxygen compounds
      • [CHEMONTID:0000323] Organooxygen compounds
        • [CHEMONTID:0000011] Carbohydrates and carbohydrate conjugates
          • [CHEMONTID:0002210] Sugar alcohols

*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
NPO163 Daucus carota Species Apiaceae Eukaryota n.a. n.a. DOI[10.1016/0045-6535(91)90110-Y]
NPO163 Daucus carota Species Apiaceae Eukaryota n.a. n.a. n.a. DOI[10.1016/j.jfca.2004.07.004]
NPO14582 Spinacia oleracea Species Chenopodiaceae Eukaryota n.a. n.a. n.a. DOI[10.1016/j.jfca.2005.08.001]
NPO163 Daucus carota Species Apiaceae Eukaryota n.a. n.a. n.a. DOI[10.1016/j.jfca.2005.08.001]
NPO163 Daucus carota Species Apiaceae Eukaryota n.a. retail stores, supermarkets and market stalls in Forssa and in the Helsinki area 2003–2005 DOI[10.1016/j.jfca.2006.05.007]
NPO1576 Anthriscus sylvestris Species Apiaceae Eukaryota n.a. root n.a. PMID[10230514]
NPO163 Daucus carota Species Apiaceae Eukaryota n.a. n.a. 1996-Sep PMID[10352947]
NPO23577 Wolfiporia cocos Species Coriolaceae Eukaryota n.a. n.a. n.a. PMID[11975480]
NPO3854 Ruta graveolens Species Rutaceae Eukaryota leaves n.a. n.a. PMID[12568545]
NPO29463 Pogostemon cablin Species Lamiaceae Eukaryota n.a. leaf n.a. PMID[12575075]
NPO29463 Pogostemon cablin Species Lamiaceae Eukaryota n.a. stem n.a. PMID[12575075]
NPO1576 Anthriscus sylvestris Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[12956064]
NPO29463 Pogostemon cablin Species Lamiaceae Eukaryota n.a. whole plant n.a. PMID[15577255]
NPO163 Daucus carota Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[15877880]
NPO163 Daucus carota Species Apiaceae Eukaryota n.a. Northeastern Regional Plant Introduction Station at Geneva 1966, 1967, and 1968 crop seasons PMID[18460139]
NPO14582 Spinacia oleracea Species Chenopodiaceae Eukaryota n.a. n.a. n.a. PMID[18460139]
NPO163 Daucus carota Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[18460139]
NPO3854 Ruta graveolens Species Rutaceae Eukaryota n.a. n.a. n.a. PMID[19191562]
NPO23577 Wolfiporia cocos Species Coriolaceae Eukaryota epidermis of the sclerotia n.a. n.a. PMID[19746919]
NPO163 Daucus carota Species Apiaceae Eukaryota n.a. exocarp n.a. PMID[21800857]
NPO163 Daucus carota Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[21800857]
NPO163 Daucus carota Species Apiaceae Eukaryota n.a. root n.a. PMID[21800857]
NPO1576 Anthriscus sylvestris Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[25608854]
NPO29401 Bupleurum chinense Species Apiaceae Eukaryota roots n.a. n.a. PMID[26259802]
NPO23577 Wolfiporia cocos Species Coriolaceae Eukaryota n.a. n.a. n.a. PMID[27808511]
NPO3854 Ruta graveolens Species Rutaceae Eukaryota Whole Plants n.a. n.a. PMID[28093914]
NPO163 Daucus carota Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[2831703]
NPO29463 Pogostemon cablin Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[30188125]
NPO14582 Spinacia oleracea Species Chenopodiaceae Eukaryota n.a. n.a. n.a. PMID[6821187]
NPO163 Daucus carota Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[6821187]
NPO23577 Wolfiporia cocos Species Coriolaceae Eukaryota n.a. n.a. n.a. PMID[8984162]
NPO14582 Spinacia oleracea Species Chenopodiaceae Eukaryota n.a. leaf n.a. PMID[9433811]
NPO29401 Bupleurum chinense Species Apiaceae Eukaryota n.a. n.a. n.a. Database[Article]
NPO14582 Spinacia oleracea Species Chenopodiaceae Eukaryota n.a. n.a. Database[FooDB]
NPO14582 Spinacia oleracea Species Chenopodiaceae Eukaryota Leaves n.a. Database[FooDB]
NPO14582 Spinacia oleracea Species Chenopodiaceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO163 Daucus carota Species Apiaceae Eukaryota Roots n.a. Database[FooDB]
NPO163 Daucus carota Species Apiaceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO14582 Spinacia oleracea Species Chenopodiaceae Eukaryota Plant n.a. n.a. Database[FooDB]
NPO163 Daucus carota Species Apiaceae Eukaryota Plant n.a. n.a. Database[FooDB]
NPO163 Daucus carota Species Apiaceae Eukaryota Root n.a. n.a. Database[FooDB]
NPO163 Daucus carota Species Apiaceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO163 Daucus carota Species Apiaceae Eukaryota Shoot n.a. n.a. Database[FooDB]
NPO163 Daucus carota Species Apiaceae Eukaryota Tissue Culture n.a. n.a. Database[FooDB]
NPO163 Daucus carota Species Apiaceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO163 Daucus carota Species Apiaceae Eukaryota n.a. n.a. Database[FooDB]
NPO14582 Spinacia oleracea Species Chenopodiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO1484 Bupleurum scorzonerifolium Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO8416 Picrorhiza kurrooa Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO29401 Bupleurum chinense Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO3854 Ruta graveolens Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO26429 Capsella bursa-pastoris Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO29463 Pogostemon cablin Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO163 Daucus carota Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO1576 Anthriscus sylvestris Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO3107 Bupleurum falcatum Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO14582 Spinacia oleracea Species Chenopodiaceae Eukaryota n.a. n.a. Database[Phenol-Explorer]
NPO163 Daucus carota Species Apiaceae Eukaryota n.a. n.a. Database[Phenol-Explorer]
NPO3854 Ruta graveolens Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14582 Spinacia oleracea Species Chenopodiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO1484 Bupleurum scorzonerifolium Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO163 Daucus carota Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO8416 Picrorhiza kurrooa Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO23577 Wolfiporia cocos Species Coriolaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO26429 Capsella bursa-pastoris Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO1576 Anthriscus sylvestris Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO29401 Bupleurum chinense Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14720 Neopicrorhiza scrophulariiflora Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO29463 Pogostemon cablin Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO3107 Bupleurum falcatum Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO1484 Bupleurum scorzonerifolium Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO163 Daucus carota Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO29401 Bupleurum chinense Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO26429 Capsella bursa-pastoris Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO3854 Ruta graveolens Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO29463 Pogostemon cablin Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO14582 Spinacia oleracea Species Chenopodiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO3107 Bupleurum falcatum Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO3107 Bupleurum falcatum Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO163 Daucus carota Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO14720 Neopicrorhiza scrophulariiflora Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO29463 Pogostemon cablin Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO1484 Bupleurum scorzonerifolium Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO29401 Bupleurum chinense Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO8416 Picrorhiza kurrooa Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO23577 Wolfiporia cocos Species Coriolaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO29463 Pogostemon cablin Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1576 Anthriscus sylvestris Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO163 Daucus carota Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14582 Spinacia oleracea Species Chenopodiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14720 Neopicrorhiza scrophulariiflora Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1484 Bupleurum scorzonerifolium Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29401 Bupleurum chinense Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26429 Capsella bursa-pastoris Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23577 Wolfiporia cocos Species Coriolaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3107 Bupleurum falcatum Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8416 Picrorhiza kurrooa Species Plantaginaceae 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
NPO14582 NPC187058 n.a. n.a. 107 n.a. n.a. mg/100g of DW PMID[6821187]
NPO163 NPC187058 n.a. n.a. 86.5 n.a. n.a. mg/100g of DW PMID[6821187]
NPO2776.1 NPC187058 n.a. n.a. 131 n.a. n.a. mg/100g of DW PMID[6821187]
NPO7576.1 NPC187058 n.a. n.a. 300 n.a. n.a. mg/100g of DW PMID[6821187]

☑ 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
NPT199 Individual Protein DNA polymerase kappa Homo sapiens Potency n.a. 37685.8 nM PMID[451317]
NPT20555 ORGANISM SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 Hit score = 0.1332 n.a. PMID[451318]

☑ 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 NPC187058 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 NPC127074
1.0 High Similarity NPC197207
1.0 High Similarity NPC182541
1.0 High Similarity NPC149070
0.9062 High Similarity NPC66052
0.9062 High Similarity NPC86412
0.9062 High Similarity NPC293908
0.9062 High Similarity NPC192065
0.9062 High Similarity NPC325034
0.8966 High Similarity NPC33415
0.8966 High Similarity NPC301586
0.8621 High Similarity NPC320326
0.7838 Intermediate Similarity NPC227707
0.7838 Intermediate Similarity NPC266553
0.7838 Intermediate Similarity NPC111882
0.7838 Intermediate Similarity NPC88278
0.7838 Intermediate Similarity NPC102981
0.7838 Intermediate Similarity NPC99573
0.7647 Intermediate Similarity NPC227267
0.7586 Intermediate Similarity NPC157340
0.7586 Intermediate Similarity NPC199270
0.7436 Intermediate Similarity NPC298699
0.7436 Intermediate Similarity NPC228782
0.7436 Intermediate Similarity NPC313565
0.7436 Intermediate Similarity NPC213159
0.7436 Intermediate Similarity NPC86191
0.7436 Intermediate Similarity NPC320189
0.7436 Intermediate Similarity NPC134252
0.7436 Intermediate Similarity NPC291502
0.7436 Intermediate Similarity NPC259982
0.7436 Intermediate Similarity NPC317182
0.7333 Intermediate Similarity NPC140389
0.7333 Intermediate Similarity NPC88887
0.725 Intermediate Similarity NPC29721
0.725 Intermediate Similarity NPC320240
0.725 Intermediate Similarity NPC70756
0.7097 Intermediate Similarity NPC252154
0.7097 Intermediate Similarity NPC560
0.7073 Intermediate Similarity NPC207656
0.7073 Intermediate Similarity NPC107091
0.7 Intermediate Similarity NPC114270
0.7 Intermediate Similarity NPC245688
0.6905 Remote Similarity NPC255377
0.6905 Remote Similarity NPC176017
0.6905 Remote Similarity NPC73906
0.6905 Remote Similarity NPC92246
0.6905 Remote Similarity NPC289758
0.6905 Remote Similarity NPC285364
0.6905 Remote Similarity NPC199857
0.6905 Remote Similarity NPC21209
0.6905 Remote Similarity NPC69445
0.6905 Remote Similarity NPC165846
0.6897 Remote Similarity NPC219266
0.6774 Remote Similarity NPC232554
0.6774 Remote Similarity NPC213764
0.6744 Remote Similarity NPC252918
0.6744 Remote Similarity NPC277475
0.6744 Remote Similarity NPC314613
0.6744 Remote Similarity NPC321087
0.6744 Remote Similarity NPC88638
0.6744 Remote Similarity NPC230789
0.6667 Remote Similarity NPC242655
0.6667 Remote Similarity NPC52403
0.6667 Remote Similarity NPC270088
0.6667 Remote Similarity NPC38891
0.6667 Remote Similarity NPC325345
0.6667 Remote Similarity NPC39977
0.6667 Remote Similarity NPC159845
0.6591 Remote Similarity NPC172086
0.6591 Remote Similarity NPC247546
0.6591 Remote Similarity NPC112363
0.6591 Remote Similarity NPC14144
0.6571 Remote Similarity NPC321170
0.6571 Remote Similarity NPC266566
0.6571 Remote Similarity NPC31433
0.65 Remote Similarity NPC320331
0.6471 Remote Similarity NPC110884
0.6444 Remote Similarity NPC325822
0.6444 Remote Similarity NPC82512
0.6444 Remote Similarity NPC42503
0.6444 Remote Similarity NPC61270
0.6444 Remote Similarity NPC299781
0.6444 Remote Similarity NPC157193
0.6444 Remote Similarity NPC282143
0.6364 Remote Similarity NPC272307
0.6341 Remote Similarity NPC35661
0.6333 Remote Similarity NPC299484
0.6304 Remote Similarity NPC322158
0.6304 Remote Similarity NPC329128
0.6304 Remote Similarity NPC323574
0.6279 Remote Similarity NPC62014
0.625 Remote Similarity NPC275462
0.6207 Remote Similarity NPC236761
0.617 Remote Similarity NPC233726
0.617 Remote Similarity NPC23134
0.617 Remote Similarity NPC326533
0.617 Remote Similarity NPC124963
0.617 Remote Similarity NPC329095
0.6111 Remote Similarity NPC267243
0.6111 Remote Similarity NPC122962
0.6111 Remote Similarity NPC317060
0.6087 Remote Similarity NPC46254
0.6061 Remote Similarity NPC128335
0.6042 Remote Similarity NPC277878
0.6042 Remote Similarity NPC320043
0.6042 Remote Similarity NPC103672
0.6042 Remote Similarity NPC321102
0.6042 Remote Similarity NPC322803
0.6042 Remote Similarity NPC278465
0.6042 Remote Similarity NPC325153
0.6 Remote Similarity NPC294703
0.5952 Remote Similarity NPC100742
0.5952 Remote Similarity NPC121018
0.5952 Remote Similarity NPC192402
0.5952 Remote Similarity NPC19044
0.5952 Remote Similarity NPC97444
0.5952 Remote Similarity NPC24751
0.5946 Remote Similarity NPC193062
0.5946 Remote Similarity NPC72324
0.5946 Remote Similarity NPC319034
0.5946 Remote Similarity NPC66124
0.5946 Remote Similarity NPC1748
0.5938 Remote Similarity NPC87529
0.5938 Remote Similarity NPC94144
0.5918 Remote Similarity NPC145112
0.5918 Remote Similarity NPC242073
0.5918 Remote Similarity NPC323361
0.5918 Remote Similarity NPC317626
0.5918 Remote Similarity NPC67660
0.5918 Remote Similarity NPC269166
0.5918 Remote Similarity NPC130683
0.5918 Remote Similarity NPC246558
0.5918 Remote Similarity NPC19676
0.5918 Remote Similarity NPC89145
0.5918 Remote Similarity NPC314821
0.5918 Remote Similarity NPC107914
0.5918 Remote Similarity NPC317501
0.5918 Remote Similarity NPC323401
0.5918 Remote Similarity NPC165198
0.5918 Remote Similarity NPC157514
0.5918 Remote Similarity NPC196612
0.5918 Remote Similarity NPC58629
0.5897 Remote Similarity NPC474914
0.5897 Remote Similarity NPC313405
0.5897 Remote Similarity NPC474392
0.5897 Remote Similarity NPC5505
0.5882 Remote Similarity NPC39869
0.5882 Remote Similarity NPC276332
0.5833 Remote Similarity NPC200772
0.58 Remote Similarity NPC6883
0.58 Remote Similarity NPC303727
0.58 Remote Similarity NPC327257
0.5758 Remote Similarity NPC304786
0.5758 Remote Similarity NPC190797
0.5714 Remote Similarity NPC300235
0.5714 Remote Similarity NPC52362
0.5714 Remote Similarity NPC476149
0.5714 Remote Similarity NPC244869
0.5714 Remote Similarity NPC238135
0.5714 Remote Similarity NPC476136
0.5714 Remote Similarity NPC279895
0.5682 Remote Similarity NPC319680
0.5667 Remote Similarity NPC163707
0.5652 Remote Similarity NPC8597
0.5641 Remote Similarity NPC168052
0.5641 Remote Similarity NPC97967
0.5641 Remote Similarity NPC191084
0.5641 Remote Similarity NPC250870

  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 NPC187058 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
1.0 High Similarity NPD8814 Phase 3
0.9062 High Similarity NPD9052 Approved
0.9062 High Similarity NPD9051 Approved
0.9062 High Similarity NPD9053 Approved
0.8966 High Similarity NPD8549 Clinical (unspecified phase)
0.7838 Intermediate Similarity NPD8995 Clinical (unspecified phase)
0.7838 Intermediate Similarity NPD8996 Phase 3
0.7778 Intermediate Similarity NPD8977 Phase 3
0.7778 Intermediate Similarity NPD8976 Approved
0.7586 Intermediate Similarity NPD8226 Approved
0.7436 Intermediate Similarity NPD8958 Phase 2
0.7436 Intermediate Similarity NPD8788 Approved
0.7436 Intermediate Similarity NPD8957 Approved
0.725 Intermediate Similarity NPD9006 Approved
0.7073 Intermediate Similarity NPD9219 Approved
0.7073 Intermediate Similarity NPD9218 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD8225 Phase 3
0.6905 Remote Similarity NPD8994 Approved
0.6905 Remote Similarity NPD8997 Approved
0.6905 Remote Similarity NPD8998 Phase 2
0.6905 Remote Similarity NPD8993 Phase 1
0.6905 Remote Similarity NPD9000 Phase 3
0.6905 Remote Similarity NPD8999 Phase 3
0.6667 Remote Similarity NPD9056 Approved
0.6667 Remote Similarity NPD8988 Clinical (unspecified phase)
0.6667 Remote Similarity NPD9055 Approved
0.6591 Remote Similarity NPD8966 Approved
0.6591 Remote Similarity NPD9003 Clinical (unspecified phase)
0.6591 Remote Similarity NPD9139 Approved
0.6591 Remote Similarity NPD9005 Phase 3
0.6591 Remote Similarity NPD9004 Approved
0.6591 Remote Similarity NPD8965 Approved
0.6571 Remote Similarity NPD8237 Approved
0.6444 Remote Similarity NPD9061 Clinical (unspecified phase)
0.6286 Remote Similarity NPD8235 Approved
0.6286 Remote Similarity NPD8236 Phase 1
0.6286 Remote Similarity NPD8234 Approved
0.617 Remote Similarity NPD904 Phase 3
0.617 Remote Similarity NPD905 Approved
0.617 Remote Similarity NPD9002 Approved
0.617 Remote Similarity NPD9001 Clinical (unspecified phase)
0.6087 Remote Similarity NPD9669 Clinical (unspecified phase)
0.6087 Remote Similarity NPD8964 Approved
0.6042 Remote Similarity NPD65 Approved
0.6042 Remote Similarity NPD8960 Approved
0.6042 Remote Similarity NPD64 Approved
0.6042 Remote Similarity NPD9008 Approved
0.6042 Remote Similarity NPD9009 Approved
0.6042 Remote Similarity NPD9050 Approved
0.6042 Remote Similarity NPD9007 Approved
0.6042 Remote Similarity NPD9049 Discontinued
0.6042 Remote Similarity NPD72 Approved
0.6042 Remote Similarity NPD9010 Approved
0.6042 Remote Similarity NPD66 Approved
0.6042 Remote Similarity NPD9011 Approved
0.5952 Remote Similarity NPD8601 Approved
0.5952 Remote Similarity NPD8605 Approved
0.5952 Remote Similarity NPD8603 Approved
0.5952 Remote Similarity NPD8602 Approved
0.5952 Remote Similarity NPD8599 Approved
0.5952 Remote Similarity NPD8598 Approved
0.5952 Remote Similarity NPD8600 Approved
0.5952 Remote Similarity NPD8604 Approved
0.5918 Remote Similarity NPD893 Approved
0.5918 Remote Similarity NPD889 Approved
0.5918 Remote Similarity NPD888 Phase 3
0.5918 Remote Similarity NPD9036 Phase 3
0.5918 Remote Similarity NPD894 Approved
0.5918 Remote Similarity NPD892 Phase 3
0.5918 Remote Similarity NPD890 Clinical (unspecified phase)
0.5918 Remote Similarity NPD887 Approved
0.5918 Remote Similarity NPD891 Phase 3
0.5918 Remote Similarity NPD895 Approved
0.5918 Remote Similarity NPD9035 Clinical (unspecified phase)
0.5714 Remote Similarity NPD2269 Approved
0.5667 Remote Similarity NPD8224 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