Structure

Physi-Chem Properties

Molecular Weight:  276.17
Volume:  307.22
LogP:  3.806
LogD:  2.69
LogS:  -3.524
# Rotatable Bonds:  8
TPSA:  57.53
# H-Bond Aceptor:  3
# H-Bond Donor:  2
# Rings:  1
# Heavy Atoms:  3

MedChem Properties

QED Drug-Likeness Score:  0.703
Synthetic Accessibility Score:  2.913
Fsp3:  0.471
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
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:  -4.652
MDCK Permeability:  2.4143015252775513e-05
Pgp-inhibitor:  0.0
Pgp-substrate:  0.047
Human Intestinal Absorption (HIA):  0.024
20% Bioavailability (F20%):  0.006
30% Bioavailability (F30%):  0.017

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.237
Plasma Protein Binding (PPB):  96.00209045410156%
Volume Distribution (VD):  0.192
Pgp-substrate:  1.9030770063400269%

ADMET: Metabolism

CYP1A2-inhibitor:  0.142
CYP1A2-substrate:  0.887
CYP2C19-inhibitor:  0.044
CYP2C19-substrate:  0.793
CYP2C9-inhibitor:  0.066
CYP2C9-substrate:  0.969
CYP2D6-inhibitor:  0.008
CYP2D6-substrate:  0.752
CYP3A4-inhibitor:  0.017
CYP3A4-substrate:  0.11

ADMET: Excretion

Clearance (CL):  4.075
Half-life (T1/2):  0.874

ADMET: Toxicity

hERG Blockers:  0.047
Human Hepatotoxicity (H-HT):  0.298
Drug-inuced Liver Injury (DILI):  0.02
AMES Toxicity:  0.012
Rat Oral Acute Toxicity:  0.06
Maximum Recommended Daily Dose:  0.831
Skin Sensitization:  0.636
Carcinogencity:  0.168
Eye Corrosion:  0.007
Eye Irritation:  0.471
Respiratory Toxicity:  0.417

Download Data

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

  Natural Product: NPC469481

Natural Product ID:  NPC469481
Common Name*:   Lorneic Acid B
IUPAC Name:   (E)-4-[2-(1-hydroxyhexyl)-4-methylphenyl]but-3-enoic acid
Synonyms:  
Standard InCHIKey:  UPEPIFABRQWHTB-VOTSOKGWSA-N
Standard InCHI:  InChI=1S/C17H24O3/c1-3-4-5-8-16(18)15-12-13(2)10-11-14(15)7-6-9-17(19)20/h6-7,10-12,16,18H,3-5,8-9H2,1-2H3,(H,19,20)/b7-6+
SMILES:  CCCCCC(c1cc(C)ccc1/C=C/CC(=O)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1079948
PubChem CID:   44605342
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0003909] Fatty Acyls
        • [CHEMONTID:0001334] Fatty 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
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[10344559]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[10344578]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[10348041]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[10604756]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[10695669]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[10724004]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[10994816]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[11099231]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[11132958]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[11374972]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[11473415]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[14738393]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. Australian n.a. PMID[15497950]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[15813185]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[15844966]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[15974616]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[16180833]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[1666120]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[16724845]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[16830891]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[16872146]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[17125235]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[17315965]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[17551212]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[17608531]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[17844998]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[17887721]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[17917237]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[18044841]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[18081255]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. Indonesian n.a. PMID[18081255]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[18205372]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[18327911]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. Northwest Territories, Canada 1995 PMID[18327911]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[18666798]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[18776684]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[19007176]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[19129624]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[19191549]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[19856955]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[19883065]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[20092333]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[20545334]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[20836523]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[21028889]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[21028891]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. mycelium n.a. PMID[21090727]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[21314175]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. mycelium n.a. PMID[21639131]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[21728289]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. latex n.a. PMID[21751787]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[21807523]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[21873059]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. latex n.a. PMID[21879726]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. mycelium n.a. PMID[22145663]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[22574670]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[22583058]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[22591466]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[22758660]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[22775474]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[23387796]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[23662937]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[24592993]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[24754815]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[24878306]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[24964393]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[25211234]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[25455147]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[25495422]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[25537064]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[25918793]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[25934225]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[26035239]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[26465675]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[26798949]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[26905826]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[31013087]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[31298537]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[31894983]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[32298122]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[8501018]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. mycelium n.a. PMID[8784423]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[8931733]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[8982334]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[9031666]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[9031676]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[9066767]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[9066768]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[9186568]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[9531983]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. mycelium n.a. PMID[9711246]

☑ 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
NPT273 Individual Protein Phosphodiesterase 5A Homo sapiens IC50 = 87100.0 nM PMID[485127]

☑ 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 NPC469481 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
0.875 High Similarity NPC133308
0.8526 High Similarity NPC1793
0.8491 Intermediate Similarity NPC471188
0.8447 Intermediate Similarity NPC471133
0.844 Intermediate Similarity NPC212891
0.8431 Intermediate Similarity NPC19856
0.8396 Intermediate Similarity NPC95126
0.8396 Intermediate Similarity NPC475002
0.8387 Intermediate Similarity NPC304538
0.8387 Intermediate Similarity NPC267704
0.835 Intermediate Similarity NPC472222
0.835 Intermediate Similarity NPC472221
0.8304 Intermediate Similarity NPC234337
0.8304 Intermediate Similarity NPC183339
0.8304 Intermediate Similarity NPC133389
0.8286 Intermediate Similarity NPC27252
0.8286 Intermediate Similarity NPC472980
0.8286 Intermediate Similarity NPC472979
0.828 Intermediate Similarity NPC172984
0.8273 Intermediate Similarity NPC105141
0.8273 Intermediate Similarity NPC242764
0.8269 Intermediate Similarity NPC243601
0.8265 Intermediate Similarity NPC314690
0.8265 Intermediate Similarity NPC128645
0.8235 Intermediate Similarity NPC289117
0.8211 Intermediate Similarity NPC93843
0.8211 Intermediate Similarity NPC474211
0.8208 Intermediate Similarity NPC149455
0.8208 Intermediate Similarity NPC64642
0.8208 Intermediate Similarity NPC472982
0.819 Intermediate Similarity NPC94751
0.819 Intermediate Similarity NPC142326
0.8173 Intermediate Similarity NPC315794
0.8172 Intermediate Similarity NPC103326
0.8172 Intermediate Similarity NPC87299
0.8172 Intermediate Similarity NPC329319
0.8172 Intermediate Similarity NPC99394
0.8158 Intermediate Similarity NPC293831
0.8158 Intermediate Similarity NPC369
0.8144 Intermediate Similarity NPC199567
0.8105 Intermediate Similarity NPC474354
0.8091 Intermediate Similarity NPC221275
0.8087 Intermediate Similarity NPC182333
0.8087 Intermediate Similarity NPC273336
0.8065 Intermediate Similarity NPC117180
0.8039 Intermediate Similarity NPC175852
0.8039 Intermediate Similarity NPC210529
0.8039 Intermediate Similarity NPC160548
0.8036 Intermediate Similarity NPC45794
0.8017 Intermediate Similarity NPC77691
0.8 Intermediate Similarity NPC168855
0.7982 Intermediate Similarity NPC66208
0.798 Intermediate Similarity NPC79917
0.7965 Intermediate Similarity NPC254233
0.7963 Intermediate Similarity NPC273837
0.7928 Intermediate Similarity NPC186933
0.7925 Intermediate Similarity NPC471186
0.7905 Intermediate Similarity NPC160382
0.7885 Intermediate Similarity NPC225079
0.7879 Intermediate Similarity NPC26224
0.7879 Intermediate Similarity NPC70940
0.7879 Intermediate Similarity NPC274455
0.7879 Intermediate Similarity NPC86670
0.7872 Intermediate Similarity NPC242628
0.7872 Intermediate Similarity NPC133050
0.787 Intermediate Similarity NPC318327
0.7864 Intermediate Similarity NPC229242
0.7857 Intermediate Similarity NPC304760
0.785 Intermediate Similarity NPC136962
0.7818 Intermediate Similarity NPC111108
0.7815 Intermediate Similarity NPC253681
0.7815 Intermediate Similarity NPC5486
0.781 Intermediate Similarity NPC25458
0.781 Intermediate Similarity NPC304873
0.7788 Intermediate Similarity NPC217621
0.7759 Intermediate Similarity NPC472981
0.7757 Intermediate Similarity NPC243677
0.7748 Intermediate Similarity NPC302371
0.7732 Intermediate Similarity NPC99482
0.7727 Intermediate Similarity NPC474057
0.7727 Intermediate Similarity NPC132720
0.7727 Intermediate Similarity NPC63345
0.7714 Intermediate Similarity NPC136810
0.7714 Intermediate Similarity NPC128248
0.7714 Intermediate Similarity NPC133809
0.7712 Intermediate Similarity NPC307139
0.7706 Intermediate Similarity NPC470039
0.7685 Intermediate Similarity NPC472315
0.7685 Intermediate Similarity NPC477251
0.7685 Intermediate Similarity NPC475203
0.7685 Intermediate Similarity NPC472316
0.7685 Intermediate Similarity NPC474376
0.7679 Intermediate Similarity NPC196673
0.7677 Intermediate Similarity NPC329064
0.7672 Intermediate Similarity NPC470585
0.7672 Intermediate Similarity NPC478121
0.767 Intermediate Similarity NPC21959
0.7664 Intermediate Similarity NPC280616
0.7664 Intermediate Similarity NPC242913
0.7664 Intermediate Similarity NPC171831
0.7658 Intermediate Similarity NPC471189
0.7634 Intermediate Similarity NPC66655
0.7632 Intermediate Similarity NPC92
0.7632 Intermediate Similarity NPC469663
0.7632 Intermediate Similarity NPC472862
0.7627 Intermediate Similarity NPC121168
0.7624 Intermediate Similarity NPC220596
0.7624 Intermediate Similarity NPC317645
0.7619 Intermediate Similarity NPC128723
0.7615 Intermediate Similarity NPC249811
0.7615 Intermediate Similarity NPC21929
0.7611 Intermediate Similarity NPC93181
0.7611 Intermediate Similarity NPC476357
0.7611 Intermediate Similarity NPC306740
0.7607 Intermediate Similarity NPC241001
0.7604 Intermediate Similarity NPC475199
0.7604 Intermediate Similarity NPC103387
0.7604 Intermediate Similarity NPC323103
0.7604 Intermediate Similarity NPC283012
0.76 Intermediate Similarity NPC220893
0.7596 Intermediate Similarity NPC289201
0.7596 Intermediate Similarity NPC253423
0.7596 Intermediate Similarity NPC324602
0.7596 Intermediate Similarity NPC226041
0.7593 Intermediate Similarity NPC105899
0.7593 Intermediate Similarity NPC321670
0.7593 Intermediate Similarity NPC472919
0.7593 Intermediate Similarity NPC303141
0.7589 Intermediate Similarity NPC306977
0.7589 Intermediate Similarity NPC206414
0.7589 Intermediate Similarity NPC272524
0.7589 Intermediate Similarity NPC26615
0.7589 Intermediate Similarity NPC287055
0.7589 Intermediate Similarity NPC242957
0.7586 Intermediate Similarity NPC472708
0.7579 Intermediate Similarity NPC121800
0.7579 Intermediate Similarity NPC328178
0.7576 Intermediate Similarity NPC322387
0.7576 Intermediate Similarity NPC89377
0.7573 Intermediate Similarity NPC172925
0.7573 Intermediate Similarity NPC206764
0.757 Intermediate Similarity NPC82426
0.757 Intermediate Similarity NPC91820
0.757 Intermediate Similarity NPC255676
0.7568 Intermediate Similarity NPC476003
0.7565 Intermediate Similarity NPC477136
0.7563 Intermediate Similarity NPC85511
0.7563 Intermediate Similarity NPC228739
0.7553 Intermediate Similarity NPC224544
0.7551 Intermediate Similarity NPC58616
0.7551 Intermediate Similarity NPC475710
0.7545 Intermediate Similarity NPC469511
0.7545 Intermediate Similarity NPC31274
0.7545 Intermediate Similarity NPC317305
0.7544 Intermediate Similarity NPC9274
0.7542 Intermediate Similarity NPC167323
0.7542 Intermediate Similarity NPC269923
0.7526 Intermediate Similarity NPC270507
0.7526 Intermediate Similarity NPC44830
0.7524 Intermediate Similarity NPC474073
0.7523 Intermediate Similarity NPC83409
0.7523 Intermediate Similarity NPC37914
0.7523 Intermediate Similarity NPC185763
0.7523 Intermediate Similarity NPC37115
0.7522 Intermediate Similarity NPC153053
0.7522 Intermediate Similarity NPC169616
0.7522 Intermediate Similarity NPC190212
0.7521 Intermediate Similarity NPC133302
0.75 Intermediate Similarity NPC321852
0.75 Intermediate Similarity NPC56168
0.75 Intermediate Similarity NPC475225
0.75 Intermediate Similarity NPC234376
0.75 Intermediate Similarity NPC328694
0.7479 Intermediate Similarity NPC478058
0.7479 Intermediate Similarity NPC223351
0.7478 Intermediate Similarity NPC219112
0.7478 Intermediate Similarity NPC477137
0.7478 Intermediate Similarity NPC308311
0.7478 Intermediate Similarity NPC470820
0.7478 Intermediate Similarity NPC158157
0.7478 Intermediate Similarity NPC38893
0.7477 Intermediate Similarity NPC75272
0.7477 Intermediate Similarity NPC154905
0.7477 Intermediate Similarity NPC284477
0.7477 Intermediate Similarity NPC471954
0.7477 Intermediate Similarity NPC60373
0.7477 Intermediate Similarity NPC318154
0.7476 Intermediate Similarity NPC325292
0.7476 Intermediate Similarity NPC138117
0.7474 Intermediate Similarity NPC469894
0.7474 Intermediate Similarity NPC170484
0.7459 Intermediate Similarity NPC115797
0.7459 Intermediate Similarity NPC51448
0.7456 Intermediate Similarity NPC41851
0.7455 Intermediate Similarity NPC211439
0.7455 Intermediate Similarity NPC112903
0.7453 Intermediate Similarity NPC51333
0.7453 Intermediate Similarity NPC78119
0.7453 Intermediate Similarity NPC216468
0.7453 Intermediate Similarity NPC221825

  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 NPC469481 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
0.8431 Intermediate Similarity NPD5700 Clinical (unspecified phase)
0.8039 Intermediate Similarity NPD9495 Approved
0.7928 Intermediate Similarity NPD5951 Approved
0.7879 Intermediate Similarity NPD1086 Approved
0.7879 Intermediate Similarity NPD1090 Approved
0.7879 Intermediate Similarity NPD1089 Approved
0.7778 Intermediate Similarity NPD800 Approved
0.7768 Intermediate Similarity NPD2629 Approved
0.7745 Intermediate Similarity NPD1693 Approved
0.7736 Intermediate Similarity NPD6647 Phase 2
0.7736 Intermediate Similarity NPD5738 Clinical (unspecified phase)
0.7723 Intermediate Similarity NPD1088 Approved
0.7706 Intermediate Similarity NPD6831 Clinical (unspecified phase)
0.7679 Intermediate Similarity NPD4869 Clinical (unspecified phase)
0.7634 Intermediate Similarity NPD9294 Approved
0.7619 Intermediate Similarity NPD2066 Phase 3
0.7576 Intermediate Similarity NPD1087 Approved
0.7573 Intermediate Similarity NPD6048 Clinical (unspecified phase)
0.7573 Intermediate Similarity NPD6049 Phase 2
0.7573 Intermediate Similarity NPD688 Clinical (unspecified phase)
0.7568 Intermediate Similarity NPD2181 Clinical (unspecified phase)
0.7551 Intermediate Similarity NPD5734 Clinical (unspecified phase)
0.7544 Intermediate Similarity NPD4198 Discontinued
0.7526 Intermediate Similarity NPD3971 Phase 1
0.7521 Intermediate Similarity NPD4626 Approved
0.7521 Intermediate Similarity NPD7163 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD1989 Approved
0.748 Intermediate Similarity NPD7008 Discontinued
0.7476 Intermediate Similarity NPD845 Approved
0.7451 Intermediate Similarity NPD1239 Approved
0.7431 Intermediate Similarity NPD5048 Discontinued
0.7411 Intermediate Similarity NPD4141 Clinical (unspecified phase)
0.7373 Intermediate Similarity NPD5125 Phase 3
0.7373 Intermediate Similarity NPD5126 Approved
0.7368 Intermediate Similarity NPD6010 Discontinued
0.735 Intermediate Similarity NPD2227 Clinical (unspecified phase)
0.7347 Intermediate Similarity NPD9491 Approved
0.7339 Intermediate Similarity NPD1237 Approved
0.7339 Intermediate Similarity NPD5952 Clinical (unspecified phase)
0.7317 Intermediate Similarity NPD5736 Approved
0.7308 Intermediate Similarity NPD5122 Clinical (unspecified phase)
0.7288 Intermediate Similarity NPD5691 Approved
0.7281 Intermediate Similarity NPD7635 Approved
0.7264 Intermediate Similarity NPD1564 Approved
0.7264 Intermediate Similarity NPD1566 Phase 3
0.7264 Intermediate Similarity NPD1565 Approved
0.7255 Intermediate Similarity NPD5346 Phase 2
0.7255 Intermediate Similarity NPD5347 Phase 2
0.7248 Intermediate Similarity NPD1931 Clinical (unspecified phase)
0.7248 Intermediate Similarity NPD1929 Approved
0.7248 Intermediate Similarity NPD1930 Approved
0.7248 Intermediate Similarity NPD5765 Approved
0.7236 Intermediate Similarity NPD5740 Clinical (unspecified phase)
0.7236 Intermediate Similarity NPD6085 Phase 2
0.7232 Intermediate Similarity NPD2182 Approved
0.7228 Intermediate Similarity NPD4793 Discontinued
0.7207 Intermediate Similarity NPD6685 Approved
0.7203 Intermediate Similarity NPD3091 Approved
0.7184 Intermediate Similarity NPD9258 Approved
0.7184 Intermediate Similarity NPD3672 Approved
0.7184 Intermediate Similarity NPD3673 Approved
0.7184 Intermediate Similarity NPD9256 Approved
0.717 Intermediate Similarity NPD1809 Phase 2
0.717 Intermediate Similarity NPD844 Approved
0.717 Intermediate Similarity NPD2859 Approved
0.717 Intermediate Similarity NPD2860 Approved
0.7143 Intermediate Similarity NPD1710 Approved
0.7143 Intermediate Similarity NPD2342 Discontinued
0.7143 Intermediate Similarity NPD226 Approved
0.713 Intermediate Similarity NPD3020 Approved
0.7103 Intermediate Similarity NPD288 Approved
0.7097 Intermediate Similarity NPD6007 Clinical (unspecified phase)
0.7087 Intermediate Similarity NPD6663 Approved
0.7083 Intermediate Similarity NPD5305 Approved
0.7083 Intermediate Similarity NPD5306 Approved
0.7075 Intermediate Similarity NPD2934 Approved
0.7075 Intermediate Similarity NPD2933 Approved
0.7075 Intermediate Similarity NPD1432 Clinical (unspecified phase)
0.7073 Intermediate Similarity NPD1283 Approved
0.7059 Intermediate Similarity NPD7741 Discontinued
0.7037 Intermediate Similarity NPD9612 Approved
0.7037 Intermediate Similarity NPD9609 Approved
0.7037 Intermediate Similarity NPD9611 Approved
0.7027 Intermediate Similarity NPD164 Approved
0.7027 Intermediate Similarity NPD5909 Discontinued
0.7025 Intermediate Similarity NPD4135 Approved
0.7025 Intermediate Similarity NPD4136 Approved
0.7025 Intermediate Similarity NPD4106 Approved
0.7 Intermediate Similarity NPD854 Approved
0.7 Intermediate Similarity NPD855 Approved
0.6992 Remote Similarity NPD182 Clinical (unspecified phase)
0.699 Remote Similarity NPD1101 Approved
0.6981 Remote Similarity NPD1066 Discontinued
0.6981 Remote Similarity NPD1563 Approved
0.6967 Remote Similarity NPD3092 Approved
0.6967 Remote Similarity NPD4806 Approved
0.6967 Remote Similarity NPD4807 Approved
0.6967 Remote Similarity NPD5618 Discontinued
0.6953 Remote Similarity NPD7715 Approved
0.6953 Remote Similarity NPD7714 Approved
0.6942 Remote Similarity NPD3019 Approved
0.6942 Remote Similarity NPD2932 Approved
0.6942 Remote Similarity NPD3095 Discontinued
0.6939 Remote Similarity NPD9490 Approved
0.6923 Remote Similarity NPD7159 Clinical (unspecified phase)
0.6916 Remote Similarity NPD4814 Discontinued
0.6909 Remote Similarity NPD1616 Discontinued
0.6899 Remote Similarity NPD4140 Approved
0.6897 Remote Similarity NPD6124 Clinical (unspecified phase)
0.6891 Remote Similarity NPD6775 Clinical (unspecified phase)
0.6891 Remote Similarity NPD7325 Clinical (unspecified phase)
0.6891 Remote Similarity NPD694 Clinical (unspecified phase)
0.6891 Remote Similarity NPD3123 Discovery
0.6887 Remote Similarity NPD159 Clinical (unspecified phase)
0.6875 Remote Similarity NPD3046 Approved
0.6875 Remote Similarity NPD179 Clinical (unspecified phase)
0.6875 Remote Similarity NPD3048 Approved
0.6875 Remote Similarity NPD3047 Approved
0.6875 Remote Similarity NPD9716 Approved
0.687 Remote Similarity NPD5240 Approved
0.687 Remote Similarity NPD5237 Approved
0.687 Remote Similarity NPD5235 Approved
0.687 Remote Similarity NPD2067 Discontinued
0.687 Remote Similarity NPD5239 Approved
0.687 Remote Similarity NPD5236 Approved
0.686 Remote Similarity NPD4102 Approved
0.686 Remote Similarity NPD4105 Approved
0.6847 Remote Similarity NPD1932 Approved
0.6847 Remote Similarity NPD4817 Approved
0.6847 Remote Similarity NPD4818 Approved
0.6842 Remote Similarity NPD4095 Clinical (unspecified phase)
0.6837 Remote Similarity NPD227 Approved
0.6837 Remote Similarity NPD225 Approved
0.6829 Remote Similarity NPD1281 Approved
0.6822 Remote Similarity NPD3719 Approved
0.6822 Remote Similarity NPD3718 Approved
0.6818 Remote Similarity NPD7305 Phase 1
0.6818 Remote Similarity NPD9712 Approved
0.681 Remote Similarity NPD2201 Approved
0.6807 Remote Similarity NPD3317 Approved
0.6803 Remote Similarity NPD7725 Approved
0.6803 Remote Similarity NPD3412 Clinical (unspecified phase)
0.6796 Remote Similarity NPD9259 Approved
0.6796 Remote Similarity NPD9257 Approved
0.678 Remote Similarity NPD2650 Approved
0.678 Remote Similarity NPD2652 Approved
0.6772 Remote Similarity NPD3663 Approved
0.6772 Remote Similarity NPD5204 Approved
0.6772 Remote Similarity NPD3662 Phase 3
0.6772 Remote Similarity NPD3664 Approved
0.6772 Remote Similarity NPD3661 Approved
0.6769 Remote Similarity NPD4060 Phase 1
0.6762 Remote Similarity NPD689 Discontinued
0.6757 Remote Similarity NPD289 Clinical (unspecified phase)
0.6754 Remote Similarity NPD5705 Approved
0.6754 Remote Similarity NPD5704 Approved
0.6754 Remote Similarity NPD5706 Approved
0.6752 Remote Similarity NPD6912 Phase 3
0.6746 Remote Similarity NPD2628 Approved
0.6746 Remote Similarity NPD2625 Approved
0.6746 Remote Similarity NPD3094 Phase 2
0.6746 Remote Similarity NPD2627 Approved
0.6746 Remote Similarity NPD2159 Approved
0.6746 Remote Similarity NPD2160 Approved
0.6746 Remote Similarity NPD2626 Approved
0.6731 Remote Similarity NPD1282 Approved
0.6727 Remote Similarity NPD9710 Approved
0.6727 Remote Similarity NPD9711 Approved
0.6727 Remote Similarity NPD5926 Approved
0.6726 Remote Similarity NPD310 Approved
0.6726 Remote Similarity NPD311 Approved
0.6726 Remote Similarity NPD314 Approved
0.6726 Remote Similarity NPD10 Approved
0.6726 Remote Similarity NPD315 Approved
0.6726 Remote Similarity NPD309 Approved
0.6724 Remote Similarity NPD4750 Phase 3
0.6723 Remote Similarity NPD690 Clinical (unspecified phase)
0.6721 Remote Similarity NPD1651 Approved
0.6719 Remote Similarity NPD5203 Approved
0.6719 Remote Similarity NPD5201 Approved
0.6719 Remote Similarity NPD4617 Approved
0.6719 Remote Similarity NPD4620 Approved
0.6699 Remote Similarity NPD111 Approved
0.6696 Remote Similarity NPD6406 Approved
0.6696 Remote Similarity NPD4719 Phase 2
0.6696 Remote Similarity NPD940 Approved
0.6696 Remote Similarity NPD846 Approved
0.6696 Remote Similarity NPD9532 Phase 3
0.6695 Remote Similarity NPD7094 Approved
0.6695 Remote Similarity NPD6858 Approved
0.6695 Remote Similarity NPD5277 Phase 2
0.6667 Remote Similarity NPD3528 Clinical (unspecified phase)
0.6667 Remote Similarity NPD1238 Approved
0.6667 Remote Similarity NPD1409 Phase 3
0.6667 Remote Similarity NPD4025 Clinical (unspecified phase)
0.6667 Remote Similarity NPD531 Approved
0.6667 Remote Similarity NPD256 Approved
0.6667 Remote Similarity NPD5454 Clinical (unspecified phase)
0.6667 Remote Similarity NPD1778 Approved
0.6667 Remote Similarity NPD1202 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