Structure

Physi-Chem Properties

Molecular Weight:  512.17
Volume:  494.007
LogP:  5.341
LogD:  3.597
LogS:  -4.429
# Rotatable Bonds:  2
TPSA:  104.06
# H-Bond Aceptor:  6
# H-Bond Donor:  3
# Rings:  4
# Heavy Atoms:  8

MedChem Properties

QED Drug-Likeness Score:  0.474
Synthetic Accessibility Score:  5.229
Fsp3:  0.692
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  1
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.688
MDCK Permeability:  1.73402986547444e-05
Pgp-inhibitor:  0.873
Pgp-substrate:  0.002
Human Intestinal Absorption (HIA):  0.018
20% Bioavailability (F20%):  0.004
30% Bioavailability (F30%):  0.01

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.534
Plasma Protein Binding (PPB):  99.1704330444336%
Volume Distribution (VD):  1.556
Pgp-substrate:  1.7144719362258911%

ADMET: Metabolism

CYP1A2-inhibitor:  0.073
CYP1A2-substrate:  0.639
CYP2C19-inhibitor:  0.151
CYP2C19-substrate:  0.68
CYP2C9-inhibitor:  0.554
CYP2C9-substrate:  0.781
CYP2D6-inhibitor:  0.144
CYP2D6-substrate:  0.353
CYP3A4-inhibitor:  0.535
CYP3A4-substrate:  0.447

ADMET: Excretion

Clearance (CL):  8.023
Half-life (T1/2):  0.045

ADMET: Toxicity

hERG Blockers:  0.023
Human Hepatotoxicity (H-HT):  0.406
Drug-inuced Liver Injury (DILI):  0.286
AMES Toxicity:  0.038
Rat Oral Acute Toxicity:  0.303
Maximum Recommended Daily Dose:  0.884
Skin Sensitization:  0.128
Carcinogencity:  0.671
Eye Corrosion:  0.003
Eye Irritation:  0.054
Respiratory Toxicity:  0.972

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  Natural Product: NPC301846

Natural Product ID:  NPC301846
Common Name*:   (3R,4As,10Ar)-3-Chloro-10A-[[(1S,3S,6S)-3-Chloro-6-Hydroxy-2,2,6-Trimethylcyclohexyl]Methyl]-6,8-Dihydroxy-2,2,7-Trimethyl-4,4A-Dihydro-3H-Benzo[G]Chromene-5,10-Dione
IUPAC Name:   (3R,4aS,10aR)-3-chloro-10a-[[(1S,3S,6S)-3-chloro-6-hydroxy-2,2,6-trimethylcyclohexyl]methyl]-6,8-dihydroxy-2,2,7-trimethyl-4,4a-dihydro-3H-benzo[g]chromene-5,10-dione
Synonyms:  
Standard InCHIKey:  AOSGMEAISQAECD-CJWPEDLKSA-N
Standard InCHI:  InChI=1S/C26H34Cl2O6/c1-12-15(29)9-13-19(20(12)30)21(31)14-10-18(28)24(4,5)34-26(14,22(13)32)11-16-23(2,3)17(27)7-8-25(16,6)33/h9,14,16-18,29-30,33H,7-8,10-11H2,1-6H3/t14-,16+,17+,18-,25+,26-/m1/s1
SMILES:  O=C1c2c(O)c(C)c(cc2C(=O)[C@]2([C@@H]1C[C@@H](Cl)C(O2)(C)C)C[C@@H]1[C@@](C)(O)CC[C@@H](C1(C)C)Cl)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL516528
PubChem CID:   11214440
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0001640] Naphthopyrans
        • [CHEMONTID:0001641] Naphthopyranones

*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. Indonesian n.a. PMID[18081255]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. 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
NPT16 Organism Staphylococcus aureus Staphylococcus aureus MIC = 1.95 ug.mL-1 PMID[461138]
NPT1531 Organism Enterococcus faecium Enterococcus faecium MIC = 3.9 ug.mL-1 PMID[461138]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 2.4 ug.mL-1 PMID[461138]

☑ 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 NPC301846 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
0.9873 High Similarity NPC108948
0.9748 High Similarity NPC184518
0.9623 High Similarity NPC311679
0.9623 High Similarity NPC131078
0.9437 High Similarity NPC73544
0.9273 High Similarity NPC471684
0.9042 High Similarity NPC158699
0.8848 High Similarity NPC471685
0.8772 High Similarity NPC471686
0.8563 High Similarity NPC471687
0.8204 Intermediate Similarity NPC470564
0.8176 Intermediate Similarity NPC181560
0.8176 Intermediate Similarity NPC169452
0.8129 Intermediate Similarity NPC470563
0.8113 Intermediate Similarity NPC242994
0.8113 Intermediate Similarity NPC138099
0.8107 Intermediate Similarity NPC470559
0.8101 Intermediate Similarity NPC471905
0.8086 Intermediate Similarity NPC471906
0.8081 Intermediate Similarity NPC316262
0.8081 Intermediate Similarity NPC314653
0.8075 Intermediate Similarity NPC193555
0.807 Intermediate Similarity NPC470561
0.807 Intermediate Similarity NPC475106
0.8038 Intermediate Similarity NPC191976
0.8038 Intermediate Similarity NPC254847
0.8012 Intermediate Similarity NPC246638
0.8 Intermediate Similarity NPC474004
0.8 Intermediate Similarity NPC143438
0.7988 Intermediate Similarity NPC470570
0.7987 Intermediate Similarity NPC53206
0.7987 Intermediate Similarity NPC53414
0.7963 Intermediate Similarity NPC474961
0.7963 Intermediate Similarity NPC135524
0.7963 Intermediate Similarity NPC308572
0.7941 Intermediate Similarity NPC272196
0.7941 Intermediate Similarity NPC474637
0.7941 Intermediate Similarity NPC201127
0.7939 Intermediate Similarity NPC37709
0.7931 Intermediate Similarity NPC125465
0.7927 Intermediate Similarity NPC34482
0.7901 Intermediate Similarity NPC305845
0.7901 Intermediate Similarity NPC110810
0.7901 Intermediate Similarity NPC204045
0.7898 Intermediate Similarity NPC313717
0.7898 Intermediate Similarity NPC470562
0.7898 Intermediate Similarity NPC470565
0.7898 Intermediate Similarity NPC315306
0.7898 Intermediate Similarity NPC277865
0.7895 Intermediate Similarity NPC472617
0.7888 Intermediate Similarity NPC190457
0.7875 Intermediate Similarity NPC53001
0.787 Intermediate Similarity NPC472211
0.7866 Intermediate Similarity NPC48762
0.7866 Intermediate Similarity NPC244691
0.7866 Intermediate Similarity NPC21599
0.7866 Intermediate Similarity NPC193703
0.7865 Intermediate Similarity NPC264922
0.7857 Intermediate Similarity NPC305965
0.7853 Intermediate Similarity NPC470560
0.7849 Intermediate Similarity NPC472618
0.7849 Intermediate Similarity NPC313368
0.7848 Intermediate Similarity NPC267205
0.7841 Intermediate Similarity NPC286074
0.7841 Intermediate Similarity NPC54903
0.7836 Intermediate Similarity NPC197326
0.7831 Intermediate Similarity NPC289042
0.7831 Intermediate Similarity NPC118027
0.7831 Intermediate Similarity NPC245584
0.7831 Intermediate Similarity NPC312929
0.7831 Intermediate Similarity NPC56433
0.7831 Intermediate Similarity NPC190648
0.7831 Intermediate Similarity NPC126767
0.7826 Intermediate Similarity NPC87723
0.7821 Intermediate Similarity NPC303910
0.7818 Intermediate Similarity NPC117716
0.7818 Intermediate Similarity NPC28632
0.7818 Intermediate Similarity NPC470673
0.7818 Intermediate Similarity NPC12402
0.7818 Intermediate Similarity NPC470674
0.7818 Intermediate Similarity NPC474630
0.7816 Intermediate Similarity NPC100849
0.7812 Intermediate Similarity NPC474311
0.7811 Intermediate Similarity NPC40356
0.7811 Intermediate Similarity NPC142527
0.7811 Intermediate Similarity NPC154683
0.7805 Intermediate Similarity NPC295712
0.7805 Intermediate Similarity NPC313047
0.7805 Intermediate Similarity NPC293545
0.7805 Intermediate Similarity NPC451542
0.7805 Intermediate Similarity NPC474203
0.7805 Intermediate Similarity NPC174905
0.7803 Intermediate Similarity NPC61382
0.7803 Intermediate Similarity NPC219686
0.7803 Intermediate Similarity NPC103816
0.7799 Intermediate Similarity NPC44437
0.7799 Intermediate Similarity NPC166480
0.7799 Intermediate Similarity NPC282780
0.7798 Intermediate Similarity NPC294646
0.7798 Intermediate Similarity NPC147735
0.7798 Intermediate Similarity NPC470568
0.7791 Intermediate Similarity NPC290550
0.7784 Intermediate Similarity NPC142846
0.7784 Intermediate Similarity NPC94781
0.7778 Intermediate Similarity NPC4547
0.7778 Intermediate Similarity NPC280497
0.7771 Intermediate Similarity NPC136878
0.7771 Intermediate Similarity NPC473135
0.7771 Intermediate Similarity NPC271944
0.7771 Intermediate Similarity NPC85393
0.7771 Intermediate Similarity NPC473132
0.7771 Intermediate Similarity NPC470676
0.7771 Intermediate Similarity NPC108129
0.7771 Intermediate Similarity NPC110882
0.7765 Intermediate Similarity NPC182921
0.7765 Intermediate Similarity NPC474824
0.7765 Intermediate Similarity NPC218870
0.7765 Intermediate Similarity NPC470408
0.7765 Intermediate Similarity NPC214632
0.7758 Intermediate Similarity NPC227841
0.7753 Intermediate Similarity NPC474857
0.7753 Intermediate Similarity NPC118128
0.7751 Intermediate Similarity NPC478148
0.7751 Intermediate Similarity NPC470569
0.775 Intermediate Similarity NPC249272
0.7738 Intermediate Similarity NPC329933
0.7738 Intermediate Similarity NPC120171
0.7738 Intermediate Similarity NPC474310
0.7733 Intermediate Similarity NPC158542
0.7727 Intermediate Similarity NPC17274
0.7727 Intermediate Similarity NPC120857
0.7727 Intermediate Similarity NPC476056
0.7727 Intermediate Similarity NPC85047
0.7725 Intermediate Similarity NPC34802
0.7725 Intermediate Similarity NPC5568
0.7719 Intermediate Similarity NPC66508
0.7719 Intermediate Similarity NPC226656
0.7719 Intermediate Similarity NPC275575
0.7716 Intermediate Similarity NPC13715
0.7709 Intermediate Similarity NPC469393
0.7706 Intermediate Similarity NPC470353
0.7706 Intermediate Similarity NPC45934
0.7697 Intermediate Similarity NPC471682
0.7697 Intermediate Similarity NPC100242
0.7692 Intermediate Similarity NPC290954
0.7692 Intermediate Similarity NPC205766
0.7692 Intermediate Similarity NPC151292
0.7692 Intermediate Similarity NPC315520
0.7692 Intermediate Similarity NPC255641
0.7688 Intermediate Similarity NPC239118
0.7688 Intermediate Similarity NPC228654
0.7688 Intermediate Similarity NPC202225
0.7688 Intermediate Similarity NPC270899
0.7688 Intermediate Similarity NPC12070
0.7688 Intermediate Similarity NPC324736
0.7684 Intermediate Similarity NPC193222
0.7684 Intermediate Similarity NPC76647
0.7683 Intermediate Similarity NPC92079
0.768 Intermediate Similarity NPC470334
0.7679 Intermediate Similarity NPC112816
0.7674 Intermediate Similarity NPC470354
0.7674 Intermediate Similarity NPC470352
0.7674 Intermediate Similarity NPC192587
0.7674 Intermediate Similarity NPC474861
0.767 Intermediate Similarity NPC472049
0.7669 Intermediate Similarity NPC103337
0.7669 Intermediate Similarity NPC114620
0.7665 Intermediate Similarity NPC143685
0.7665 Intermediate Similarity NPC285122
0.7663 Intermediate Similarity NPC191606
0.7661 Intermediate Similarity NPC178964
0.7661 Intermediate Similarity NPC280530
0.7661 Intermediate Similarity NPC329844
0.7661 Intermediate Similarity NPC95842
0.7657 Intermediate Similarity NPC470694
0.7657 Intermediate Similarity NPC94796
0.7657 Intermediate Similarity NPC473022
0.7657 Intermediate Similarity NPC245122
0.7651 Intermediate Similarity NPC10764
0.7651 Intermediate Similarity NPC29932
0.7651 Intermediate Similarity NPC19896
0.7647 Intermediate Similarity NPC470675
0.7647 Intermediate Similarity NPC473131
0.7647 Intermediate Similarity NPC474417
0.7647 Intermediate Similarity NPC149526
0.7647 Intermediate Similarity NPC230848
0.7644 Intermediate Similarity NPC284495
0.7644 Intermediate Similarity NPC470342
0.7644 Intermediate Similarity NPC472060
0.7644 Intermediate Similarity NPC472052
0.764 Intermediate Similarity NPC283088
0.764 Intermediate Similarity NPC20734
0.764 Intermediate Similarity NPC290803
0.7636 Intermediate Similarity NPC257644
0.7636 Intermediate Similarity NPC291078
0.7636 Intermediate Similarity NPC73061
0.7633 Intermediate Similarity NPC280753
0.7633 Intermediate Similarity NPC44378
0.7633 Intermediate Similarity NPC80370
0.7633 Intermediate Similarity NPC477221

  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 NPC301846 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
0.8038 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.7758 Intermediate Similarity NPD7390 Discontinued
0.75 Intermediate Similarity NPD6959 Discontinued
0.743 Intermediate Similarity NPD7473 Discontinued
0.7294 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.7263 Intermediate Similarity NPD6232 Discontinued
0.7257 Intermediate Similarity NPD7819 Suspended
0.7249 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7233 Intermediate Similarity NPD1470 Approved
0.7229 Intermediate Similarity NPD5405 Approved
0.7229 Intermediate Similarity NPD5404 Approved
0.7229 Intermediate Similarity NPD5408 Approved
0.7229 Intermediate Similarity NPD6100 Approved
0.7229 Intermediate Similarity NPD5406 Approved
0.7229 Intermediate Similarity NPD6099 Approved
0.7216 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.7193 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.7193 Intermediate Similarity NPD2534 Approved
0.7193 Intermediate Similarity NPD2533 Approved
0.7193 Intermediate Similarity NPD2532 Approved
0.7169 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.7135 Intermediate Similarity NPD7075 Discontinued
0.7128 Intermediate Similarity NPD8150 Discontinued
0.7119 Intermediate Similarity NPD8438 Clinical (unspecified phase)
0.7101 Intermediate Similarity NPD2800 Approved
0.7086 Intermediate Similarity NPD4380 Phase 2
0.7062 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.7062 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7059 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7041 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7039 Intermediate Similarity NPD3749 Approved
0.703 Intermediate Similarity NPD943 Approved
0.7029 Intermediate Similarity NPD3226 Approved
0.6995 Remote Similarity NPD2403 Approved
0.6994 Remote Similarity NPD7422 Clinical (unspecified phase)
0.6989 Remote Similarity NPD6599 Discontinued
0.6981 Remote Similarity NPD1201 Approved
0.6949 Remote Similarity NPD7411 Suspended
0.6946 Remote Similarity NPD1607 Approved
0.6946 Remote Similarity NPD6651 Approved
0.6935 Remote Similarity NPD8320 Phase 1
0.6935 Remote Similarity NPD8319 Approved
0.6907 Remote Similarity NPD6534 Approved
0.6907 Remote Similarity NPD6535 Approved
0.6902 Remote Similarity NPD6167 Clinical (unspecified phase)
0.6902 Remote Similarity NPD6166 Phase 2
0.6902 Remote Similarity NPD6168 Clinical (unspecified phase)
0.6889 Remote Similarity NPD3882 Suspended
0.6888 Remote Similarity NPD7700 Phase 2
0.6888 Remote Similarity NPD7699 Phase 2
0.6884 Remote Similarity NPD7435 Discontinued
0.6882 Remote Similarity NPD5844 Phase 1
0.6882 Remote Similarity NPD7804 Clinical (unspecified phase)
0.6879 Remote Similarity NPD3300 Phase 2
0.6868 Remote Similarity NPD5494 Approved
0.6864 Remote Similarity NPD1510 Phase 2
0.6857 Remote Similarity NPD1512 Approved
0.6842 Remote Similarity NPD1549 Phase 2
0.6826 Remote Similarity NPD1240 Approved
0.6818 Remote Similarity NPD6779 Approved
0.6818 Remote Similarity NPD6782 Approved
0.6818 Remote Similarity NPD6780 Approved
0.6818 Remote Similarity NPD6777 Approved
0.6818 Remote Similarity NPD6776 Approved
0.6818 Remote Similarity NPD6781 Approved
0.6818 Remote Similarity NPD6778 Approved
0.6816 Remote Similarity NPD1934 Approved
0.6816 Remote Similarity NPD6801 Discontinued
0.6811 Remote Similarity NPD7852 Clinical (unspecified phase)
0.68 Remote Similarity NPD7698 Approved
0.68 Remote Similarity NPD7697 Approved
0.68 Remote Similarity NPD7696 Phase 3
0.6796 Remote Similarity NPD7768 Phase 2
0.6793 Remote Similarity NPD5710 Approved
0.6793 Remote Similarity NPD5711 Approved
0.6784 Remote Similarity NPD1552 Clinical (unspecified phase)
0.6784 Remote Similarity NPD2346 Discontinued
0.6784 Remote Similarity NPD1550 Clinical (unspecified phase)
0.6778 Remote Similarity NPD2801 Approved
0.6766 Remote Similarity NPD7870 Phase 2
0.6766 Remote Similarity NPD7871 Phase 2
0.6765 Remote Similarity NPD3299 Clinical (unspecified phase)
0.6763 Remote Similarity NPD3750 Approved
0.6743 Remote Similarity NPD1511 Approved
0.6735 Remote Similarity NPD4360 Phase 2
0.6735 Remote Similarity NPD4363 Phase 3
0.6719 Remote Similarity NPD6785 Approved
0.6719 Remote Similarity NPD6784 Approved
0.6703 Remote Similarity NPD4868 Clinical (unspecified phase)
0.6685 Remote Similarity NPD1465 Phase 2
0.6684 Remote Similarity NPD7251 Discontinued
0.6683 Remote Similarity NPD7874 Approved
0.6683 Remote Similarity NPD7875 Clinical (unspecified phase)
0.6667 Remote Similarity NPD4381 Clinical (unspecified phase)
0.6667 Remote Similarity NPD7701 Phase 2
0.665 Remote Similarity NPD7801 Approved
0.6649 Remote Similarity NPD3751 Discontinued
0.6649 Remote Similarity NPD7808 Phase 3
0.6648 Remote Similarity NPD3817 Phase 2
0.6648 Remote Similarity NPD6799 Approved
0.6646 Remote Similarity NPD3019 Approved
0.6634 Remote Similarity NPD8151 Discontinued
0.6632 Remote Similarity NPD6797 Phase 2
0.6628 Remote Similarity NPD2935 Discontinued
0.6628 Remote Similarity NPD2796 Approved
0.6615 Remote Similarity NPD8312 Approved
0.6615 Remote Similarity NPD8313 Approved
0.6607 Remote Similarity NPD3764 Approved
0.6604 Remote Similarity NPD405 Clinical (unspecified phase)
0.6597 Remote Similarity NPD6559 Discontinued
0.6584 Remote Similarity NPD4196 Clinical (unspecified phase)
0.6579 Remote Similarity NPD7074 Phase 3
0.6571 Remote Similarity NPD7003 Approved
0.6569 Remote Similarity NPD7211 Clinical (unspecified phase)
0.6562 Remote Similarity NPD4338 Clinical (unspecified phase)
0.6557 Remote Similarity NPD5402 Approved
0.6556 Remote Similarity NPD7458 Discontinued
0.6546 Remote Similarity NPD8055 Clinical (unspecified phase)
0.6545 Remote Similarity NPD7993 Clinical (unspecified phase)
0.6543 Remote Similarity NPD2932 Approved
0.6531 Remote Similarity NPD8397 Clinical (unspecified phase)
0.6526 Remote Similarity NPD7054 Approved
0.6526 Remote Similarity NPD6020 Phase 2
0.6513 Remote Similarity NPD8434 Phase 2
0.6497 Remote Similarity NPD7236 Approved
0.6492 Remote Similarity NPD7472 Approved
0.6491 Remote Similarity NPD230 Phase 1
0.6477 Remote Similarity NPD8166 Discontinued
0.6474 Remote Similarity NPD3748 Approved
0.6474 Remote Similarity NPD3818 Discontinued
0.6474 Remote Similarity NPD2799 Discontinued
0.6468 Remote Similarity NPD4974 Approved
0.6468 Remote Similarity NPD4975 Approved
0.6464 Remote Similarity NPD5808 Clinical (unspecified phase)
0.645 Remote Similarity NPD4625 Phase 3
0.645 Remote Similarity NPD4361 Phase 2
0.645 Remote Similarity NPD4362 Clinical (unspecified phase)
0.6441 Remote Similarity NPD6190 Approved
0.644 Remote Similarity NPD7286 Phase 2
0.6436 Remote Similarity NPD5544 Approved
0.6436 Remote Similarity NPD3787 Discontinued
0.6432 Remote Similarity NPD6212 Phase 3
0.6432 Remote Similarity NPD6213 Phase 3
0.6432 Remote Similarity NPD6214 Clinical (unspecified phase)
0.6425 Remote Similarity NPD7004 Clinical (unspecified phase)
0.6424 Remote Similarity NPD4878 Approved
0.6422 Remote Similarity NPD6823 Phase 2
0.642 Remote Similarity NPD7421 Clinical (unspecified phase)
0.6413 Remote Similarity NPD5760 Phase 2
0.6413 Remote Similarity NPD5761 Phase 2
0.6412 Remote Similarity NPD6410 Clinical (unspecified phase)
0.6409 Remote Similarity NPD7239 Suspended
0.6407 Remote Similarity NPD1164 Approved
0.6404 Remote Similarity NPD4914 Approved
0.6402 Remote Similarity NPD3926 Phase 2
0.64 Remote Similarity NPD2344 Approved
0.64 Remote Similarity NPD1471 Phase 3
0.6384 Remote Similarity NPD1878 Clinical (unspecified phase)
0.6383 Remote Similarity NPD1247 Approved
0.6374 Remote Similarity NPD6663 Approved
0.6373 Remote Similarity NPD5953 Discontinued
0.6372 Remote Similarity NPD8155 Clinical (unspecified phase)
0.6354 Remote Similarity NPD920 Approved
0.6354 Remote Similarity NPD5403 Approved
0.6349 Remote Similarity NPD7229 Phase 3
0.6343 Remote Similarity NPD1551 Phase 2
0.6341 Remote Similarity NPD4387 Approved
0.6341 Remote Similarity NPD4386 Approved
0.6331 Remote Similarity NPD5736 Approved
0.6328 Remote Similarity NPD1243 Approved
0.6325 Remote Similarity NPD9269 Phase 2
0.6324 Remote Similarity NPD7501 Clinical (unspecified phase)
0.6316 Remote Similarity NPD4907 Clinical (unspecified phase)
0.6308 Remote Similarity NPD4419 Clinical (unspecified phase)
0.6303 Remote Similarity NPD3023 Approved
0.6303 Remote Similarity NPD3026 Approved
0.6303 Remote Similarity NPD4879 Approved
0.6302 Remote Similarity NPD7799 Discontinued
0.6302 Remote Similarity NPD7228 Approved
0.6292 Remote Similarity NPD4628 Phase 3
0.6287 Remote Similarity NPD4749 Approved
0.6281 Remote Similarity NPD4287 Approved
0.628 Remote Similarity NPD3025 Approved
0.628 Remote Similarity NPD3024 Approved
0.628 Remote Similarity NPD9268 Approved
0.6279 Remote Similarity NPD7961 Discontinued
0.6277 Remote Similarity NPD919 Approved
0.6277 Remote Similarity NPD5537 Clinical (unspecified phase)
0.6277 Remote Similarity NPD6234 Discontinued
0.627 Remote Similarity NPD37 Approved
0.6266 Remote Similarity NPD4750 Phase 3
0.6257 Remote Similarity NPD4966 Approved
0.6257 Remote Similarity NPD4965 Approved
0.6257 Remote Similarity NPD2354 Approved
0.6257 Remote Similarity NPD2309 Approved
0.6257 Remote Similarity NPD4967 Phase 2
0.6256 Remote Similarity NPD5027 Approved
0.6256 Remote Similarity NPD4915 Approved
0.6256 Remote Similarity NPD4388 Approved
0.6256 Remote Similarity NPD8090 Clinical (unspecified phase)

  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