Structure

Physi-Chem Properties

Molecular Weight:  258.16
Volume:  295.793
LogP:  4.298
LogD:  3.902
LogS:  -4.55
# Rotatable Bonds:  7
TPSA:  37.3
# H-Bond Aceptor:  2
# H-Bond Donor:  1
# Rings:  1
# Heavy Atoms:  2

MedChem Properties

QED Drug-Likeness Score:  0.72
Synthetic Accessibility Score:  2.563
Fsp3:  0.353
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:  -4.667
MDCK Permeability:  2.5619085135986097e-05
Pgp-inhibitor:  0.001
Pgp-substrate:  0.001
Human Intestinal Absorption (HIA):  0.005
20% Bioavailability (F20%):  0.003
30% Bioavailability (F30%):  0.004

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.222
Plasma Protein Binding (PPB):  98.57212829589844%
Volume Distribution (VD):  0.427
Pgp-substrate:  0.6575857400894165%

ADMET: Metabolism

CYP1A2-inhibitor:  0.652
CYP1A2-substrate:  0.902
CYP2C19-inhibitor:  0.174
CYP2C19-substrate:  0.608
CYP2C9-inhibitor:  0.368
CYP2C9-substrate:  0.985
CYP2D6-inhibitor:  0.038
CYP2D6-substrate:  0.902
CYP3A4-inhibitor:  0.065
CYP3A4-substrate:  0.132

ADMET: Excretion

Clearance (CL):  2.931
Half-life (T1/2):  0.851

ADMET: Toxicity

hERG Blockers:  0.1
Human Hepatotoxicity (H-HT):  0.525
Drug-inuced Liver Injury (DILI):  0.045
AMES Toxicity:  0.017
Rat Oral Acute Toxicity:  0.044
Maximum Recommended Daily Dose:  0.339
Skin Sensitization:  0.939
Carcinogencity:  0.406
Eye Corrosion:  0.15
Eye Irritation:  0.906
Respiratory Toxicity:  0.86

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Structure MOL file  
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  Natural Product: NPC267704

Natural Product ID:  NPC267704
Common Name*:   Lorneic Acid A
IUPAC Name:   (E)-4-[2-[(E)-hex-1-enyl]-4-methylphenyl]but-3-enoic acid
Synonyms:  
Standard InCHIKey:  BPISPUIKHXBPSU-CDJQDVQCSA-N
Standard InCHI:  InChI=1S/C17H22O2/c1-3-4-5-6-8-16-13-14(2)11-12-15(16)9-7-10-17(18)19/h6-9,11-13H,3-5,10H2,1-2H3,(H,18,19)/b8-6+,9-7+
SMILES:  CCCC/C=C/c1cc(C)ccc1/C=C/CC(=O)O
Synthetic Gene Cluster:   BGC0001200;
ChEMBL Identifier:   CHEMBL1079947
PubChem CID:   44605341
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0002448] Benzenoids
      • [CHEMONTID:0002279] Benzene and substituted derivatives
        • [CHEMONTID:0000037] Styrenes

*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 = 12600.0 nM PMID[483140]

☑ 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 NPC267704 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
0.8621 High Similarity NPC26224
0.8462 Intermediate Similarity NPC155429
0.8434 Intermediate Similarity NPC242628
0.8387 Intermediate Similarity NPC469481
0.8202 Intermediate Similarity NPC86670
0.8202 Intermediate Similarity NPC274455
0.8202 Intermediate Similarity NPC70940
0.8191 Intermediate Similarity NPC128248
0.8191 Intermediate Similarity NPC136810
0.8191 Intermediate Similarity NPC133809
0.8191 Intermediate Similarity NPC225079
0.8023 Intermediate Similarity NPC44830
0.7978 Intermediate Similarity NPC329064
0.7959 Intermediate Similarity NPC142326
0.7959 Intermediate Similarity NPC94751
0.7949 Intermediate Similarity NPC6107
0.7938 Intermediate Similarity NPC472221
0.7938 Intermediate Similarity NPC472222
0.7912 Intermediate Similarity NPC86987
0.7901 Intermediate Similarity NPC54269
0.7872 Intermediate Similarity NPC133135
0.7872 Intermediate Similarity NPC226041
0.7872 Intermediate Similarity NPC251579
0.7865 Intermediate Similarity NPC322387
0.7857 Intermediate Similarity NPC50192
0.7849 Intermediate Similarity NPC172925
0.7821 Intermediate Similarity NPC113837
0.7821 Intermediate Similarity NPC289915
0.7789 Intermediate Similarity NPC120393
0.7766 Intermediate Similarity NPC469893
0.7717 Intermediate Similarity NPC475059
0.7717 Intermediate Similarity NPC475023
0.7708 Intermediate Similarity NPC221825
0.77 Intermediate Similarity NPC21929
0.7692 Intermediate Similarity NPC298115
0.7684 Intermediate Similarity NPC469892
0.7684 Intermediate Similarity NPC469891
0.7684 Intermediate Similarity NPC469890
0.7674 Intermediate Similarity NPC127343
0.7647 Intermediate Similarity NPC103488
0.7647 Intermediate Similarity NPC95126
0.7647 Intermediate Similarity NPC475002
0.7634 Intermediate Similarity NPC155232
0.7634 Intermediate Similarity NPC475057
0.7634 Intermediate Similarity NPC153885
0.7629 Intermediate Similarity NPC264728
0.7624 Intermediate Similarity NPC475006
0.7614 Intermediate Similarity NPC285773
0.76 Intermediate Similarity NPC37914
0.7576 Intermediate Similarity NPC329282
0.7561 Intermediate Similarity NPC158028
0.7561 Intermediate Similarity NPC280135
0.7561 Intermediate Similarity NPC193578
0.7561 Intermediate Similarity NPC1008
0.7561 Intermediate Similarity NPC39799
0.7561 Intermediate Similarity NPC135433
0.7561 Intermediate Similarity NPC226999
0.7561 Intermediate Similarity NPC87099
0.7556 Intermediate Similarity NPC160339
0.7556 Intermediate Similarity NPC307
0.7553 Intermediate Similarity NPC238219
0.7529 Intermediate Similarity NPC3190
0.7529 Intermediate Similarity NPC249018
0.7527 Intermediate Similarity NPC220596
0.7527 Intermediate Similarity NPC133461
0.7527 Intermediate Similarity NPC125226
0.75 Intermediate Similarity NPC32203
0.75 Intermediate Similarity NPC206800
0.75 Intermediate Similarity NPC323103
0.75 Intermediate Similarity NPC103387
0.75 Intermediate Similarity NPC471186
0.7476 Intermediate Similarity NPC133308
0.7475 Intermediate Similarity NPC247976
0.7474 Intermediate Similarity NPC260233
0.7471 Intermediate Similarity NPC157055
0.7471 Intermediate Similarity NPC121800
0.7471 Intermediate Similarity NPC285716
0.7471 Intermediate Similarity NPC17408
0.7468 Intermediate Similarity NPC198023
0.7468 Intermediate Similarity NPC155172
0.7468 Intermediate Similarity NPC32312
0.7447 Intermediate Similarity NPC314690
0.7429 Intermediate Similarity NPC471721
0.7419 Intermediate Similarity NPC173413
0.7416 Intermediate Similarity NPC270507
0.7404 Intermediate Similarity NPC66208
0.7391 Intermediate Similarity NPC153308
0.7375 Intermediate Similarity NPC178527
0.7363 Intermediate Similarity NPC474211
0.7363 Intermediate Similarity NPC164526
0.7358 Intermediate Similarity NPC221275
0.7356 Intermediate Similarity NPC170484
0.7356 Intermediate Similarity NPC159661
0.7342 Intermediate Similarity NPC88566
0.7342 Intermediate Similarity NPC45756
0.734 Intermediate Similarity NPC284475
0.7333 Intermediate Similarity NPC44546
0.7333 Intermediate Similarity NPC93287
0.732 Intermediate Similarity NPC239185
0.7317 Intermediate Similarity NPC246822
0.7317 Intermediate Similarity NPC213570
0.7317 Intermediate Similarity NPC139416
0.7308 Intermediate Similarity NPC150196
0.7308 Intermediate Similarity NPC54368
0.7308 Intermediate Similarity NPC238023
0.7308 Intermediate Similarity NPC310758
0.7308 Intermediate Similarity NPC210849
0.7308 Intermediate Similarity NPC248705
0.7303 Intermediate Similarity NPC230068
0.73 Intermediate Similarity NPC329556
0.7294 Intermediate Similarity NPC307195
0.7294 Intermediate Similarity NPC189371
0.7282 Intermediate Similarity NPC318327
0.7273 Intermediate Similarity NPC315216
0.7263 Intermediate Similarity NPC59677
0.7263 Intermediate Similarity NPC188844
0.7263 Intermediate Similarity NPC323420
0.7263 Intermediate Similarity NPC1682
0.7255 Intermediate Similarity NPC100767
0.7255 Intermediate Similarity NPC85560
0.7255 Intermediate Similarity NPC244933
0.7253 Intermediate Similarity NPC474354
0.7253 Intermediate Similarity NPC475710
0.7253 Intermediate Similarity NPC95965
0.7245 Intermediate Similarity NPC229242
0.7245 Intermediate Similarity NPC49994
0.7245 Intermediate Similarity NPC75724
0.7245 Intermediate Similarity NPC134882
0.7241 Intermediate Similarity NPC224544
0.7234 Intermediate Similarity NPC277277
0.7222 Intermediate Similarity NPC288903
0.7222 Intermediate Similarity NPC105141
0.7222 Intermediate Similarity NPC242764
0.7222 Intermediate Similarity NPC477770
0.7222 Intermediate Similarity NPC212891
0.7216 Intermediate Similarity NPC185208
0.7216 Intermediate Similarity NPC219573
0.7212 Intermediate Similarity NPC273837
0.7209 Intermediate Similarity NPC110264
0.7209 Intermediate Similarity NPC175393
0.7204 Intermediate Similarity NPC157778
0.72 Intermediate Similarity NPC304873
0.7196 Intermediate Similarity NPC186933
0.7196 Intermediate Similarity NPC217111
0.7188 Intermediate Similarity NPC289883
0.7179 Intermediate Similarity NPC147062
0.7176 Intermediate Similarity NPC258492
0.7176 Intermediate Similarity NPC96835
0.7172 Intermediate Similarity NPC217621
0.7159 Intermediate Similarity NPC469894
0.7159 Intermediate Similarity NPC272260
0.7157 Intermediate Similarity NPC172483
0.7156 Intermediate Similarity NPC45794
0.7143 Intermediate Similarity NPC477767
0.7143 Intermediate Similarity NPC74458
0.7143 Intermediate Similarity NPC265220
0.7143 Intermediate Similarity NPC168855
0.7143 Intermediate Similarity NPC324602
0.713 Intermediate Similarity NPC9274
0.7129 Intermediate Similarity NPC19856
0.7128 Intermediate Similarity NPC1793
0.7126 Intermediate Similarity NPC298023
0.7126 Intermediate Similarity NPC287790
0.7126 Intermediate Similarity NPC9796
0.7126 Intermediate Similarity NPC3672
0.7108 Intermediate Similarity NPC98880
0.71 Intermediate Similarity NPC476993
0.71 Intermediate Similarity NPC289117
0.71 Intermediate Similarity NPC109514
0.7097 Intermediate Similarity NPC69057
0.7097 Intermediate Similarity NPC43945
0.7091 Intermediate Similarity NPC254233
0.7089 Intermediate Similarity NPC135924
0.7087 Intermediate Similarity NPC83409
0.7087 Intermediate Similarity NPC185763
0.7083 Intermediate Similarity NPC128645
0.7075 Intermediate Similarity NPC292834
0.7075 Intermediate Similarity NPC471188
0.7075 Intermediate Similarity NPC471189
0.7073 Intermediate Similarity NPC267443
0.7071 Intermediate Similarity NPC271475
0.7071 Intermediate Similarity NPC154517
0.7065 Intermediate Similarity NPC53299
0.7065 Intermediate Similarity NPC294134
0.7059 Intermediate Similarity NPC285679
0.7053 Intermediate Similarity NPC84288
0.7051 Intermediate Similarity NPC64270
0.7051 Intermediate Similarity NPC8235
0.7045 Intermediate Similarity NPC245896
0.7045 Intermediate Similarity NPC66270
0.7041 Intermediate Similarity NPC261947
0.7033 Intermediate Similarity NPC172984
0.703 Intermediate Similarity NPC25458
0.7024 Intermediate Similarity NPC95289
0.7024 Intermediate Similarity NPC72670
0.7024 Intermediate Similarity NPC251490
0.7019 Intermediate Similarity NPC249811
0.7019 Intermediate Similarity NPC112903
0.7 Intermediate Similarity NPC80115
0.7 Intermediate Similarity NPC66517

  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 NPC267704 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
0.8256 Intermediate Similarity NPD5734 Clinical (unspecified phase)
0.8242 Intermediate Similarity NPD6048 Clinical (unspecified phase)
0.8242 Intermediate Similarity NPD6049 Phase 2
0.8235 Intermediate Similarity NPD3971 Phase 1
0.8202 Intermediate Similarity NPD1086 Approved
0.8202 Intermediate Similarity NPD1089 Approved
0.8202 Intermediate Similarity NPD1090 Approved
0.809 Intermediate Similarity NPD800 Approved
0.8022 Intermediate Similarity NPD1088 Approved
0.7865 Intermediate Similarity NPD1087 Approved
0.7849 Intermediate Similarity NPD1693 Approved
0.7849 Intermediate Similarity NPD688 Clinical (unspecified phase)
0.7717 Intermediate Similarity NPD1239 Approved
0.7708 Intermediate Similarity NPD2066 Phase 3
0.7692 Intermediate Similarity NPD5346 Phase 2
0.7692 Intermediate Similarity NPD5347 Phase 2
0.7667 Intermediate Similarity NPD4793 Discontinued
0.7614 Intermediate Similarity NPD9491 Approved
0.7586 Intermediate Similarity NPD226 Approved
0.7553 Intermediate Similarity NPD5122 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD1564 Approved
0.75 Intermediate Similarity NPD1565 Approved
0.75 Intermediate Similarity NPD9716 Approved
0.75 Intermediate Similarity NPD1566 Phase 3
0.7396 Intermediate Similarity NPD1989 Approved
0.7358 Intermediate Similarity NPD5951 Approved
0.734 Intermediate Similarity NPD7609 Phase 3
0.732 Intermediate Similarity NPD3495 Discontinued
0.73 Intermediate Similarity NPD1929 Approved
0.73 Intermediate Similarity NPD1930 Approved
0.73 Intermediate Similarity NPD1931 Clinical (unspecified phase)
0.7263 Intermediate Similarity NPD7631 Approved
0.7241 Intermediate Similarity NPD227 Approved
0.7241 Intermediate Similarity NPD225 Approved
0.7234 Intermediate Similarity NPD3673 Approved
0.7234 Intermediate Similarity NPD3672 Approved
0.7204 Intermediate Similarity NPD1101 Approved
0.7188 Intermediate Similarity NPD1563 Approved
0.7159 Intermediate Similarity NPD9490 Approved
0.7115 Intermediate Similarity NPD6831 Clinical (unspecified phase)
0.7108 Intermediate Similarity NPD9497 Clinical (unspecified phase)
0.7097 Intermediate Similarity NPD650 Approved
0.703 Intermediate Similarity NPD1932 Approved
0.701 Intermediate Similarity NPD1066 Discontinued
0.6981 Remote Similarity NPD4141 Clinical (unspecified phase)
0.6964 Remote Similarity NPD7163 Clinical (unspecified phase)
0.6961 Remote Similarity NPD5700 Clinical (unspecified phase)
0.6869 Remote Similarity NPD5206 Clinical (unspecified phase)
0.6842 Remote Similarity NPD5618 Discontinued
0.6837 Remote Similarity NPD1409 Phase 3
0.6832 Remote Similarity NPD3097 Clinical (unspecified phase)
0.6796 Remote Similarity NPD5765 Approved
0.6796 Remote Similarity NPD5738 Clinical (unspecified phase)
0.6796 Remote Similarity NPD6647 Phase 2
0.6792 Remote Similarity NPD2329 Discontinued
0.6789 Remote Similarity NPD6010 Discontinued
0.6771 Remote Similarity NPD689 Discontinued
0.6768 Remote Similarity NPD4814 Discontinued
0.6762 Remote Similarity NPD6685 Approved
0.6733 Remote Similarity NPD253 Approved
0.6731 Remote Similarity NPD5909 Discontinued
0.6707 Remote Similarity NPD675 Discontinued
0.67 Remote Similarity NPD3093 Approved
0.6667 Remote Similarity NPD3643 Approved
0.6667 Remote Similarity NPD845 Approved
0.6667 Remote Similarity NPD3719 Approved
0.6667 Remote Similarity NPD4198 Discontinued
0.6667 Remote Similarity NPD3644 Approved
0.6667 Remote Similarity NPD4626 Approved
0.6667 Remote Similarity NPD5927 Discontinued
0.6667 Remote Similarity NPD5048 Discontinued
0.6667 Remote Similarity NPD1067 Discontinued
0.6667 Remote Similarity NPD3718 Approved
0.6667 Remote Similarity NPD4199 Phase 3
0.6667 Remote Similarity NPD3642 Approved
0.6634 Remote Similarity NPD2487 Clinical (unspecified phase)
0.6632 Remote Similarity NPD3099 Discontinued
0.6609 Remote Similarity NPD2956 Clinical (unspecified phase)
0.6596 Remote Similarity NPD4544 Approved
0.6574 Remote Similarity NPD1317 Discontinued
0.6569 Remote Similarity NPD5926 Approved
0.6569 Remote Similarity NPD9495 Approved
0.6562 Remote Similarity NPD1282 Approved
0.6545 Remote Similarity NPD7635 Approved
0.6535 Remote Similarity NPD2895 Discontinued
0.6531 Remote Similarity NPD9256 Approved
0.6531 Remote Similarity NPD9258 Approved
0.6522 Remote Similarity NPD3904 Approved
0.6522 Remote Similarity NPD1507 Clinical (unspecified phase)
0.6522 Remote Similarity NPD3903 Approved
0.6522 Remote Similarity NPD3979 Approved
0.6522 Remote Similarity NPD3981 Approved
0.6514 Remote Similarity NPD2181 Clinical (unspecified phase)
0.65 Remote Similarity NPD720 Approved
0.65 Remote Similarity NPD719 Approved
0.6496 Remote Similarity NPD3880 Clinical (unspecified phase)
0.6495 Remote Similarity NPD531 Approved
0.6491 Remote Similarity NPD4479 Discontinued
0.6486 Remote Similarity NPD2652 Approved
0.6486 Remote Similarity NPD1280 Clinical (unspecified phase)
0.6486 Remote Similarity NPD2650 Approved
0.6481 Remote Similarity NPD2182 Approved
0.6471 Remote Similarity NPD9566 Approved
0.6465 Remote Similarity NPD530 Approved
0.646 Remote Similarity NPD3797 Approved
0.6452 Remote Similarity NPD942 Approved
0.6441 Remote Similarity NPD182 Clinical (unspecified phase)
0.6435 Remote Similarity NPD5691 Approved
0.6429 Remote Similarity NPD2629 Approved
0.6422 Remote Similarity NPD5278 Discontinued
0.6415 Remote Similarity NPD164 Approved
0.64 Remote Similarity NPD1508 Approved
0.64 Remote Similarity NPD752 Approved
0.6396 Remote Similarity NPD6858 Approved
0.6396 Remote Similarity NPD7094 Approved
0.6393 Remote Similarity NPD5952 Clinical (unspecified phase)
0.6393 Remote Similarity NPD7008 Discontinued
0.6389 Remote Similarity NPD2342 Discontinued
0.6387 Remote Similarity NPD1283 Approved
0.6374 Remote Similarity NPD9294 Approved
0.6373 Remote Similarity NPD2859 Approved
0.6373 Remote Similarity NPD1809 Phase 2
0.6373 Remote Similarity NPD2860 Approved
0.6373 Remote Similarity NPD844 Approved
0.6348 Remote Similarity NPD3798 Phase 3
0.6346 Remote Similarity NPD3020 Approved
0.6339 Remote Similarity NPD4869 Clinical (unspecified phase)
0.6339 Remote Similarity NPD3598 Phase 3
0.6325 Remote Similarity NPD3881 Discontinued
0.6322 Remote Similarity NPD1673 Approved
0.6316 Remote Similarity NPD5162 Approved
0.6316 Remote Similarity NPD4635 Approved
0.6316 Remote Similarity NPD7325 Clinical (unspecified phase)
0.6311 Remote Similarity NPD1875 Phase 1
0.6311 Remote Similarity NPD288 Approved
0.6306 Remote Similarity NPD6912 Phase 3
0.6296 Remote Similarity NPD5706 Approved
0.6296 Remote Similarity NPD5704 Approved
0.6296 Remote Similarity NPD5705 Approved
0.6293 Remote Similarity NPD5981 Approved
0.6293 Remote Similarity NPD4209 Clinical (unspecified phase)
0.6289 Remote Similarity NPD9259 Approved
0.6289 Remote Similarity NPD9257 Approved
0.6286 Remote Similarity NPD5630 Phase 1
0.6286 Remote Similarity NPD6354 Discontinued
0.6283 Remote Similarity NPD4766 Approved
0.6275 Remote Similarity NPD4094 Approved
0.6275 Remote Similarity NPD1432 Clinical (unspecified phase)
0.6275 Remote Similarity NPD2933 Approved
0.6275 Remote Similarity NPD2934 Approved
0.6273 Remote Similarity NPD5240 Approved
0.6273 Remote Similarity NPD5235 Approved
0.6273 Remote Similarity NPD5237 Approved
0.6273 Remote Similarity NPD4233 Approved
0.6273 Remote Similarity NPD4234 Approved
0.6273 Remote Similarity NPD5236 Approved
0.6273 Remote Similarity NPD5239 Approved
0.6262 Remote Similarity NPD179 Clinical (unspecified phase)
0.6261 Remote Similarity NPD7610 Discontinued
0.6261 Remote Similarity NPD6065 Approved
0.625 Remote Similarity NPD3427 Approved
0.625 Remote Similarity NPD3429 Approved
0.6239 Remote Similarity NPD2932 Approved
0.6239 Remote Similarity NPD5126 Approved
0.6239 Remote Similarity NPD3019 Approved
0.6239 Remote Similarity NPD2345 Approved
0.6239 Remote Similarity NPD5125 Phase 3
0.6238 Remote Similarity NPD159 Clinical (unspecified phase)
0.6235 Remote Similarity NPD173 Clinical (unspecified phase)
0.623 Remote Similarity NPD5736 Approved
0.6228 Remote Similarity NPD3317 Approved
0.6224 Remote Similarity NPD9538 Approved
0.6216 Remote Similarity NPD2201 Approved
0.6214 Remote Similarity NPD1843 Approved
0.6207 Remote Similarity NPD7009 Phase 2
0.6207 Remote Similarity NPD2617 Discontinued
0.6207 Remote Similarity NPD6093 Discontinued
0.6204 Remote Similarity NPD1040 Phase 2
0.6195 Remote Similarity NPD23 Approved
0.619 Remote Similarity NPD7798 Approved
0.619 Remote Similarity NPD9712 Approved
0.618 Remote Similarity NPD292 Approved
0.618 Remote Similarity NPD294 Approved
0.6176 Remote Similarity NPD1202 Approved
0.6154 Remote Similarity NPD1245 Approved
0.6154 Remote Similarity NPD1855 Clinical (unspecified phase)
0.6154 Remote Similarity NPD4657 Approved
0.6154 Remote Similarity NPD5598 Approved
0.6154 Remote Similarity NPD4105 Approved
0.6154 Remote Similarity NPD4102 Approved
0.6154 Remote Similarity NPD5597 Approved
0.6154 Remote Similarity NPD4655 Approved
0.6147 Remote Similarity NPD467 Phase 1
0.6146 Remote Similarity NPD4000 Phase 3
0.6146 Remote Similarity NPD5288 Clinical (unspecified phase)
0.614 Remote Similarity NPD2508 Discontinued
0.6134 Remote Similarity NPD1281 Approved
0.6132 Remote Similarity NPD1616 Discontinued
0.6132 Remote Similarity NPD4760 Clinical (unspecified phase)
0.6126 Remote Similarity NPD1756 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