Structure

Physi-Chem Properties

Molecular Weight:  390.15
Volume:  359.548
LogP:  -0.266
LogD:  0.68
LogS:  -1.022
# Rotatable Bonds:  5
TPSA:  155.14
# H-Bond Aceptor:  10
# H-Bond Donor:  5
# Rings:  3
# Heavy Atoms:  10

MedChem Properties

QED Drug-Likeness Score:  0.336
Synthetic Accessibility Score:  4.69
Fsp3:  0.824
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
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:  -5.862
MDCK Permeability:  0.0001704913447611034
Pgp-inhibitor:  0.001
Pgp-substrate:  0.683
Human Intestinal Absorption (HIA):  0.911
20% Bioavailability (F20%):  0.012
30% Bioavailability (F30%):  0.994

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.408
Plasma Protein Binding (PPB):  20.51336669921875%
Volume Distribution (VD):  0.307
Pgp-substrate:  53.96754837036133%

ADMET: Metabolism

CYP1A2-inhibitor:  0.008
CYP1A2-substrate:  0.144
CYP2C19-inhibitor:  0.011
CYP2C19-substrate:  0.671
CYP2C9-inhibitor:  0.001
CYP2C9-substrate:  0.066
CYP2D6-inhibitor:  0.002
CYP2D6-substrate:  0.093
CYP3A4-inhibitor:  0.005
CYP3A4-substrate:  0.079

ADMET: Excretion

Clearance (CL):  1.992
Half-life (T1/2):  0.81

ADMET: Toxicity

hERG Blockers:  0.037
Human Hepatotoxicity (H-HT):  0.377
Drug-inuced Liver Injury (DILI):  0.691
AMES Toxicity:  0.147
Rat Oral Acute Toxicity:  0.193
Maximum Recommended Daily Dose:  0.067
Skin Sensitization:  0.058
Carcinogencity:  0.919
Eye Corrosion:  0.003
Eye Irritation:  0.012
Respiratory Toxicity:  0.923

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Similar NPs/Drugs  

  Natural Product: NPC4899

Natural Product ID:  NPC4899
Common Name*:   Methyl (1S,4As,6S,7R,7As)-6-Hydroxy-7-Methyl-1-[3,4,5-Trihydroxy-6-(Hydroxymethyl)Oxan-2-Yl]Oxy-1,4A,5,6,7,7A-Hexahydrocyclopenta[C]Pyran-4-Carboxylate
IUPAC Name:   methyl (1S,4aS,6S,7R,7aS)-6-hydroxy-7-methyl-1-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylate
Synonyms:  
Standard InCHIKey:  AMBQHHVBBHTQBF-PTGPOGFDSA-N
Standard InCHI:  InChI=1S/C17H26O10/c1-6-9(19)3-7-8(15(23)24-2)5-25-16(11(6)7)27-17-14(22)13(21)12(20)10(4-18)26-17/h5-7,9-14,16-22H,3-4H2,1-2H3/t6-,7+,9-,10?,11+,12?,13?,14?,16-,17?/m0/s1
SMILES:  C[C@H]1[C@H](C[C@@H]2C(=CO[C@H]([C@H]12)OC1C(C(C(C(CO)O1)O)O)O)C(=O)OC)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL2135791
PubChem CID:   354446
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0002049] Terpene glycosides
          • [CHEMONTID:0004081] Iridoid O-glycosides

*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
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota Flowers n.a. n.a. DOI[10.1002/elan.200403102]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota Flowers n.a. n.a. DOI[10.1016/j.foodchem.2012.02.124]
NPO28245 Strychnos nux-vomica Species Loganiaceae Eukaryota n.a. seed n.a. PMID[10.1016/j.tet.2012.03.006]
NPO28245 Strychnos nux-vomica Species Loganiaceae Eukaryota n.a. seed n.a. DOI[10.1016/j.tet.2012.03.006]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota Flowers n.a. n.a. PMID[11077184]
NPO5881 Catharanthus roseus Species Apocynaceae Eukaryota n.a. n.a. n.a. PMID[12628396]
NPO28245 Strychnos nux-vomica Species Loganiaceae Eukaryota n.a. seed n.a. PMID[16317898]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota Flowers n.a. n.a. PMID[17328234]
NPO28245 Strychnos nux-vomica Species Loganiaceae Eukaryota n.a. seed n.a. PMID[17449162]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota Flower buds n.a. n.a. PMID[18321056]
NPO28245 Strychnos nux-vomica Species Loganiaceae Eukaryota n.a. seed n.a. PMID[19235686]
NPO5881 Catharanthus roseus Species Apocynaceae Eukaryota Hairy roots n.a. n.a. PMID[19271765]
NPO28245 Strychnos nux-vomica Species Loganiaceae Eukaryota n.a. n.a. n.a. PMID[19666019]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota n.a. flower n.a. PMID[21804227]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota flower buds Henan province, China 2005-MAY PMID[21942812]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota n.a. flower bud n.a. PMID[21942812]
NPO28245 Strychnos nux-vomica Species Loganiaceae Eukaryota n.a. seed n.a. PMID[22707864]
NPO28245 Strychnos nux-vomica Species Loganiaceae Eukaryota n.a. n.a. n.a. PMID[23088673]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota n.a. leaf n.a. PMID[23265495]
NPO28245 Strychnos nux-vomica Species Loganiaceae Eukaryota n.a. seed n.a. PMID[2393954]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota Flower buds n.a. n.a. PMID[24279769]
NPO28245 Strychnos nux-vomica Species Loganiaceae Eukaryota n.a. seed n.a. PMID[25594733]
NPO5881 Catharanthus roseus Species Apocynaceae Eukaryota n.a. n.a. n.a. PMID[26285573]
NPO9090 Patrinia villosa Species Caprifoliaceae Eukaryota n.a. leaf n.a. PMID[27019553]
NPO12588 Cornus officinalis Species Cornaceae Eukaryota Fruits n.a. n.a. PMID[29140705]
NPO5881 Catharanthus roseus Species Apocynaceae Eukaryota n.a. n.a. n.a. PMID[6619887]
NPO5881 Catharanthus roseus Species Apocynaceae Eukaryota n.a. n.a. n.a. PMID[6631435]
NPO5881 Catharanthus roseus Species Apocynaceae Eukaryota n.a. n.a. n.a. PMID[7264679]
NPO5881 Catharanthus roseus Species Apocynaceae Eukaryota n.a. n.a. n.a. PMID[7264682]
NPO5881 Catharanthus roseus Species Apocynaceae Eukaryota n.a. n.a. n.a. PMID[7320741]
NPO28245 Strychnos nux-vomica Species Loganiaceae Eukaryota n.a. seed n.a. PMID[7912074]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO9090 Patrinia villosa Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO8516 Dipsacus asperoides Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO5881 Catharanthus roseus Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO12588 Cornus officinalis Species Cornaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO6067 Strychnos ignatii Species Loganiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO28245 Strychnos nux-vomica Species Loganiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO16412 Menyanthes trifoliata Species Menyanthaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO6067 Strychnos ignatii Species Loganiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO8516 Dipsacus asperoides Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO28245 Strychnos nux-vomica Species Loganiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO5881 Catharanthus roseus Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO16412 Menyanthes trifoliata Species Menyanthaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO12588 Cornus officinalis Species Cornaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO9090 Patrinia villosa Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO28245 Strychnos nux-vomica Species Loganiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO6067 Strychnos ignatii Species Loganiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO8516 Dipsacus asperoides Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO5881 Catharanthus roseus Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO16412 Menyanthes trifoliata Species Menyanthaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO9090 Patrinia villosa Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO12588 Cornus officinalis Species Cornaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO8516 Dipsacus asperoides Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO9090 Patrinia villosa Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO12588 Cornus officinalis Species Cornaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO6067 Strychnos ignatii Species Loganiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO8516 Dipsacus asperoides Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28245 Strychnos nux-vomica Species Loganiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16412 Menyanthes trifoliata Species Menyanthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5881 Catharanthus roseus Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12588 Cornus officinalis Species Cornaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6067 Strychnos ignatii Species Loganiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9090 Patrinia villosa Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

  NP Quantity Composition/Concentration

Organism ID NP ID Organism Material Preparation Organism Part NP Quantity (Standard) NP Quantity (Minimum) NP Quantity (Maximum) Quantity Unit Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT10 Individual Protein Geminin Homo sapiens Potency n.a. 9200.0 nM PMID[465030]
NPT2 Others Unspecified Potency n.a. 354.8 nM PMID[465030]

☑ 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 NPC4899 and all remaining natural products in the NPASS database.
●  The right table: Most similar natural products (Tc>=0.56 or Top200).

Similarity Score Similarity Level Natural Product ID
1.0 High Similarity NPC474730
1.0 High Similarity NPC35185
1.0 High Similarity NPC177013
0.9895 High Similarity NPC37240
0.9691 High Similarity NPC170432
0.9688 High Similarity NPC475928
0.9684 High Similarity NPC3488
0.9684 High Similarity NPC287539
0.9592 High Similarity NPC197813
0.9592 High Similarity NPC80338
0.9592 High Similarity NPC148270
0.9381 High Similarity NPC106668
0.9307 High Similarity NPC193741
0.9293 High Similarity NPC127235
0.9286 High Similarity NPC27687
0.9126 High Similarity NPC475924
0.9126 High Similarity NPC475851
0.9109 High Similarity NPC110701
0.9062 High Similarity NPC161293
0.8854 High Similarity NPC63897
0.88 High Similarity NPC304163
0.8763 High Similarity NPC93869
0.8763 High Similarity NPC6765
0.866 High Similarity NPC274588
0.8614 High Similarity NPC80144
0.8544 High Similarity NPC41681
0.8542 High Similarity NPC65665
0.8542 High Similarity NPC216826
0.8542 High Similarity NPC231710
0.8542 High Similarity NPC270908
0.8542 High Similarity NPC470573
0.8542 High Similarity NPC120021
0.8515 High Similarity NPC67296
0.85 High Similarity NPC49833
0.85 High Similarity NPC249171
0.85 High Similarity NPC37866
0.8485 Intermediate Similarity NPC170527
0.84 Intermediate Similarity NPC304445
0.84 Intermediate Similarity NPC472290
0.84 Intermediate Similarity NPC236580
0.835 Intermediate Similarity NPC473148
0.8333 Intermediate Similarity NPC216911
0.83 Intermediate Similarity NPC284063
0.8265 Intermediate Similarity NPC235051
0.8235 Intermediate Similarity NPC476320
0.8235 Intermediate Similarity NPC306344
0.8235 Intermediate Similarity NPC476211
0.8235 Intermediate Similarity NPC255677
0.8235 Intermediate Similarity NPC22149
0.8218 Intermediate Similarity NPC261372
0.8218 Intermediate Similarity NPC263674
0.8218 Intermediate Similarity NPC86843
0.8218 Intermediate Similarity NPC58267
0.8173 Intermediate Similarity NPC329834
0.8163 Intermediate Similarity NPC117596
0.8155 Intermediate Similarity NPC298255
0.8155 Intermediate Similarity NPC27474
0.8155 Intermediate Similarity NPC476230
0.8155 Intermediate Similarity NPC28304
0.8137 Intermediate Similarity NPC472015
0.8125 Intermediate Similarity NPC470657
0.8119 Intermediate Similarity NPC474297
0.8081 Intermediate Similarity NPC66504
0.8081 Intermediate Similarity NPC472124
0.8081 Intermediate Similarity NPC472126
0.8081 Intermediate Similarity NPC472125
0.8077 Intermediate Similarity NPC261117
0.8077 Intermediate Similarity NPC310804
0.8077 Intermediate Similarity NPC195510
0.8077 Intermediate Similarity NPC222062
0.8077 Intermediate Similarity NPC13171
0.8041 Intermediate Similarity NPC31349
0.8036 Intermediate Similarity NPC13710
0.802 Intermediate Similarity NPC167893
0.8 Intermediate Similarity NPC329704
0.8 Intermediate Similarity NPC118761
0.8 Intermediate Similarity NPC197541
0.8 Intermediate Similarity NPC267869
0.8 Intermediate Similarity NPC61201
0.8 Intermediate Similarity NPC284929
0.8 Intermediate Similarity NPC234304
0.7981 Intermediate Similarity NPC476228
0.798 Intermediate Similarity NPC307699
0.798 Intermediate Similarity NPC246173
0.7941 Intermediate Similarity NPC241911
0.7925 Intermediate Similarity NPC86095
0.7905 Intermediate Similarity NPC250545
0.7885 Intermediate Similarity NPC473146
0.7879 Intermediate Similarity NPC50464
0.7879 Intermediate Similarity NPC93190
0.7864 Intermediate Similarity NPC471150
0.7833 Intermediate Similarity NPC155529
0.7826 Intermediate Similarity NPC470829
0.7826 Intermediate Similarity NPC473228
0.78 Intermediate Similarity NPC303451
0.78 Intermediate Similarity NPC6414
0.7778 Intermediate Similarity NPC254538
0.7778 Intermediate Similarity NPC474285
0.775 Intermediate Similarity NPC213634
0.7745 Intermediate Similarity NPC71589
0.7736 Intermediate Similarity NPC94919
0.7736 Intermediate Similarity NPC471599
0.7723 Intermediate Similarity NPC274274
0.7723 Intermediate Similarity NPC294643
0.7723 Intermediate Similarity NPC473150
0.7714 Intermediate Similarity NPC186861
0.7714 Intermediate Similarity NPC244878
0.7714 Intermediate Similarity NPC471381
0.7706 Intermediate Similarity NPC219900
0.7706 Intermediate Similarity NPC392
0.7706 Intermediate Similarity NPC177524
0.7699 Intermediate Similarity NPC277583
0.7692 Intermediate Similarity NPC27363
0.767 Intermediate Similarity NPC101051
0.767 Intermediate Similarity NPC472873
0.7658 Intermediate Similarity NPC471251
0.7642 Intermediate Similarity NPC158350
0.7642 Intermediate Similarity NPC219038
0.7642 Intermediate Similarity NPC20673
0.7636 Intermediate Similarity NPC208307
0.7636 Intermediate Similarity NPC471250
0.7636 Intermediate Similarity NPC118225
0.7619 Intermediate Similarity NPC151093
0.7596 Intermediate Similarity NPC54731
0.7596 Intermediate Similarity NPC306041
0.7586 Intermediate Similarity NPC281840
0.7581 Intermediate Similarity NPC289700
0.7581 Intermediate Similarity NPC62172
0.7581 Intermediate Similarity NPC127656
0.7576 Intermediate Similarity NPC474949
0.7576 Intermediate Similarity NPC476015
0.7576 Intermediate Similarity NPC475019
0.7576 Intermediate Similarity NPC474762
0.7568 Intermediate Similarity NPC124053
0.7568 Intermediate Similarity NPC106760
0.7568 Intermediate Similarity NPC114961
0.7568 Intermediate Similarity NPC50223
0.7568 Intermediate Similarity NPC27551
0.7565 Intermediate Similarity NPC475309
0.7563 Intermediate Similarity NPC469750
0.7563 Intermediate Similarity NPC250556
0.7551 Intermediate Similarity NPC3464
0.7551 Intermediate Similarity NPC474780
0.7551 Intermediate Similarity NPC475963
0.7551 Intermediate Similarity NPC151176
0.7549 Intermediate Similarity NPC470379
0.7549 Intermediate Similarity NPC470373
0.7544 Intermediate Similarity NPC106228
0.7544 Intermediate Similarity NPC88945
0.7544 Intermediate Similarity NPC138372
0.7525 Intermediate Similarity NPC215556
0.7525 Intermediate Similarity NPC92974
0.7523 Intermediate Similarity NPC85670
0.7523 Intermediate Similarity NPC54737
0.7522 Intermediate Similarity NPC132668
0.7521 Intermediate Similarity NPC42675
0.75 Intermediate Similarity NPC469543
0.75 Intermediate Similarity NPC186148
0.75 Intermediate Similarity NPC74139
0.75 Intermediate Similarity NPC117702
0.75 Intermediate Similarity NPC240070
0.75 Intermediate Similarity NPC19028
0.75 Intermediate Similarity NPC163228
0.75 Intermediate Similarity NPC329784
0.75 Intermediate Similarity NPC179412
0.75 Intermediate Similarity NPC146456
0.75 Intermediate Similarity NPC471356
0.75 Intermediate Similarity NPC471357
0.75 Intermediate Similarity NPC9674
0.75 Intermediate Similarity NPC469757
0.7479 Intermediate Similarity NPC318135
0.7478 Intermediate Similarity NPC473304
0.7477 Intermediate Similarity NPC59489
0.7477 Intermediate Similarity NPC139838
0.7477 Intermediate Similarity NPC98859
0.7477 Intermediate Similarity NPC4637
0.7477 Intermediate Similarity NPC471401
0.7476 Intermediate Similarity NPC320089
0.7475 Intermediate Similarity NPC149725
0.7475 Intermediate Similarity NPC47958
0.7475 Intermediate Similarity NPC304509
0.7475 Intermediate Similarity NPC329749
0.746 Intermediate Similarity NPC322503
0.746 Intermediate Similarity NPC75616
0.746 Intermediate Similarity NPC470143
0.7459 Intermediate Similarity NPC173347
0.7458 Intermediate Similarity NPC216866
0.7456 Intermediate Similarity NPC106446
0.7456 Intermediate Similarity NPC178289
0.7455 Intermediate Similarity NPC287269
0.7451 Intermediate Similarity NPC297474
0.7451 Intermediate Similarity NPC216284
0.7451 Intermediate Similarity NPC54065
0.7451 Intermediate Similarity NPC206614
0.7451 Intermediate Similarity NPC474323
0.7438 Intermediate Similarity NPC245094
0.7438 Intermediate Similarity NPC311534
0.7436 Intermediate Similarity NPC470312
0.7436 Intermediate Similarity NPC108072
0.7434 Intermediate Similarity NPC243572

  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 NPC4899 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
0.7706 Intermediate Similarity NPD6686 Approved
0.7563 Intermediate Similarity NPD7507 Approved
0.7522 Intermediate Similarity NPD8133 Approved
0.7377 Intermediate Similarity NPD7319 Approved
0.7373 Intermediate Similarity NPD7503 Approved
0.7297 Intermediate Similarity NPD6412 Phase 2
0.7281 Intermediate Similarity NPD6053 Discontinued
0.7115 Intermediate Similarity NPD46 Approved
0.7115 Intermediate Similarity NPD6698 Approved
0.6975 Remote Similarity NPD7328 Approved
0.6975 Remote Similarity NPD7327 Approved
0.6942 Remote Similarity NPD8513 Phase 3
0.6917 Remote Similarity NPD7516 Approved
0.6897 Remote Similarity NPD8413 Clinical (unspecified phase)
0.686 Remote Similarity NPD8294 Approved
0.686 Remote Similarity NPD8377 Approved
0.6842 Remote Similarity NPD7899 Clinical (unspecified phase)
0.6803 Remote Similarity NPD8379 Approved
0.6803 Remote Similarity NPD8516 Approved
0.6803 Remote Similarity NPD8296 Approved
0.6803 Remote Similarity NPD8515 Approved
0.6803 Remote Similarity NPD8335 Approved
0.6803 Remote Similarity NPD8517 Approved
0.6803 Remote Similarity NPD8378 Approved
0.6803 Remote Similarity NPD8033 Approved
0.6803 Remote Similarity NPD8380 Approved
0.675 Remote Similarity NPD6009 Approved
0.6748 Remote Similarity NPD6370 Approved
0.6746 Remote Similarity NPD7736 Approved
0.6721 Remote Similarity NPD6319 Approved
0.6695 Remote Similarity NPD6882 Approved
0.6667 Remote Similarity NPD8170 Clinical (unspecified phase)
0.6667 Remote Similarity NPD6435 Approved
0.6667 Remote Similarity NPD8293 Discontinued
0.6667 Remote Similarity NPD8029 Clinical (unspecified phase)
0.6667 Remote Similarity NPD6371 Approved
0.664 Remote Similarity NPD7492 Approved
0.6639 Remote Similarity NPD4632 Approved
0.6612 Remote Similarity NPD8137 Clinical (unspecified phase)
0.6587 Remote Similarity NPD6616 Approved
0.6585 Remote Similarity NPD6054 Approved
0.6574 Remote Similarity NPD7983 Approved
0.6571 Remote Similarity NPD4249 Approved
0.656 Remote Similarity NPD7829 Approved
0.656 Remote Similarity NPD7830 Approved
0.6555 Remote Similarity NPD8297 Approved
0.6535 Remote Similarity NPD7078 Approved
0.6532 Remote Similarity NPD6015 Approved
0.6532 Remote Similarity NPD6016 Approved
0.6522 Remote Similarity NPD4056 Clinical (unspecified phase)
0.6522 Remote Similarity NPD4057 Clinical (unspecified phase)
0.6509 Remote Similarity NPD4250 Approved
0.6509 Remote Similarity NPD4251 Approved
0.6481 Remote Similarity NPD7838 Discovery
0.648 Remote Similarity NPD8080 Discontinued
0.648 Remote Similarity NPD5988 Approved
0.6471 Remote Similarity NPD5368 Approved
0.6452 Remote Similarity NPD6059 Approved
0.6441 Remote Similarity NPD8132 Clinical (unspecified phase)
0.6429 Remote Similarity NPD8328 Phase 3
0.6423 Remote Similarity NPD7641 Discontinued
0.641 Remote Similarity NPD5697 Approved
0.64 Remote Similarity NPD8274 Clinical (unspecified phase)
0.6389 Remote Similarity NPD1695 Approved
0.6372 Remote Similarity NPD7638 Approved
0.6356 Remote Similarity NPD6881 Approved
0.6356 Remote Similarity NPD5345 Clinical (unspecified phase)
0.6356 Remote Similarity NPD6899 Approved
0.6341 Remote Similarity NPD8295 Clinical (unspecified phase)
0.6333 Remote Similarity NPD6650 Approved
0.6333 Remote Similarity NPD6649 Approved
0.6328 Remote Similarity NPD8451 Approved
0.6325 Remote Similarity NPD7128 Approved
0.6325 Remote Similarity NPD5739 Approved
0.6325 Remote Similarity NPD6402 Approved
0.6325 Remote Similarity NPD6675 Approved
0.6321 Remote Similarity NPD1733 Clinical (unspecified phase)
0.6321 Remote Similarity NPD6082 Clinical (unspecified phase)
0.6316 Remote Similarity NPD7640 Approved
0.6316 Remote Similarity NPD7639 Approved
0.6303 Remote Similarity NPD6012 Approved
0.6303 Remote Similarity NPD6013 Approved
0.6303 Remote Similarity NPD6372 Approved
0.6303 Remote Similarity NPD6373 Approved
0.6303 Remote Similarity NPD6014 Approved
0.6299 Remote Similarity NPD7642 Approved
0.6286 Remote Similarity NPD7154 Phase 3
0.6286 Remote Similarity NPD5362 Discontinued
0.6279 Remote Similarity NPD8074 Phase 3
0.6279 Remote Similarity NPD8448 Approved
0.6271 Remote Similarity NPD5701 Approved
0.627 Remote Similarity NPD8444 Approved
0.627 Remote Similarity NPD5983 Phase 2
0.625 Remote Similarity NPD7102 Approved
0.625 Remote Similarity NPD6883 Approved
0.625 Remote Similarity NPD7290 Approved
0.625 Remote Similarity NPD1698 Clinical (unspecified phase)
0.6231 Remote Similarity NPD8337 Approved
0.6231 Remote Similarity NPD8336 Approved
0.6222 Remote Similarity NPD7966 Clinical (unspecified phase)
0.6218 Remote Similarity NPD7320 Approved
0.6218 Remote Similarity NPD6011 Approved
0.6216 Remote Similarity NPD5778 Approved
0.6216 Remote Similarity NPD5779 Approved
0.621 Remote Similarity NPD7115 Discovery
0.6198 Remote Similarity NPD6847 Approved
0.6198 Remote Similarity NPD6869 Approved
0.6198 Remote Similarity NPD8130 Phase 1
0.6198 Remote Similarity NPD6617 Approved
0.6195 Remote Similarity NPD7839 Suspended
0.6182 Remote Similarity NPD5785 Approved
0.6172 Remote Similarity NPD7604 Phase 2
0.6167 Remote Similarity NPD4061 Clinical (unspecified phase)
0.6154 Remote Similarity NPD5790 Clinical (unspecified phase)
0.6142 Remote Similarity NPD8269 Approved
0.6142 Remote Similarity NPD8267 Approved
0.6142 Remote Similarity NPD8268 Approved
0.6142 Remote Similarity NPD8266 Approved
0.614 Remote Similarity NPD6083 Phase 2
0.614 Remote Similarity NPD6084 Phase 2
0.6136 Remote Similarity NPD8392 Approved
0.6136 Remote Similarity NPD8391 Approved
0.6136 Remote Similarity NPD8390 Approved
0.6132 Remote Similarity NPD4788 Approved
0.6124 Remote Similarity NPD8341 Approved
0.6124 Remote Similarity NPD8299 Approved
0.6124 Remote Similarity NPD8342 Approved
0.6124 Remote Similarity NPD8340 Approved
0.6117 Remote Similarity NPD4238 Approved
0.6117 Remote Similarity NPD4802 Phase 2
0.6116 Remote Similarity NPD4634 Approved
0.6111 Remote Similarity NPD5786 Approved
0.6106 Remote Similarity NPD5695 Phase 3
0.6091 Remote Similarity NPD6101 Approved
0.6091 Remote Similarity NPD5764 Clinical (unspecified phase)
0.609 Remote Similarity NPD7260 Phase 2
0.6087 Remote Similarity NPD4225 Approved
0.6077 Remote Similarity NPD6336 Discontinued
0.6068 Remote Similarity NPD8083 Approved
0.6068 Remote Similarity NPD8139 Approved
0.6068 Remote Similarity NPD8084 Approved
0.6068 Remote Similarity NPD8085 Approved
0.6068 Remote Similarity NPD8086 Approved
0.6068 Remote Similarity NPD5211 Phase 2
0.6068 Remote Similarity NPD8082 Approved
0.6068 Remote Similarity NPD8138 Approved
0.605 Remote Similarity NPD6008 Approved
0.6047 Remote Similarity NPD6067 Discontinued
0.6045 Remote Similarity NPD8338 Approved
0.6034 Remote Similarity NPD4696 Approved
0.6034 Remote Similarity NPD5285 Approved
0.6034 Remote Similarity NPD5286 Approved
0.6019 Remote Similarity NPD5363 Approved
0.6018 Remote Similarity NPD5282 Discontinued
0.6017 Remote Similarity NPD8276 Approved
0.6017 Remote Similarity NPD8275 Approved
0.6 Remote Similarity NPD4821 Approved
0.6 Remote Similarity NPD6274 Approved
0.6 Remote Similarity NPD4822 Approved
0.6 Remote Similarity NPD4819 Approved
0.6 Remote Similarity NPD4820 Approved
0.6 Remote Similarity NPD4755 Approved
0.5985 Remote Similarity NPD6033 Approved
0.5984 Remote Similarity NPD5955 Clinical (unspecified phase)
0.5983 Remote Similarity NPD5344 Discontinued
0.5982 Remote Similarity NPD8035 Phase 2
0.5982 Remote Similarity NPD6411 Approved
0.5982 Remote Similarity NPD8034 Phase 2
0.5966 Remote Similarity NPD8081 Approved
0.5966 Remote Similarity NPD5141 Approved
0.5962 Remote Similarity NPD4268 Approved
0.5962 Remote Similarity NPD4271 Approved
0.5948 Remote Similarity NPD5696 Approved
0.5943 Remote Similarity NPD5369 Approved
0.5935 Remote Similarity NPD6401 Clinical (unspecified phase)
0.5932 Remote Similarity NPD5226 Approved
0.5932 Remote Similarity NPD5224 Approved
0.5932 Remote Similarity NPD7632 Discontinued
0.5932 Remote Similarity NPD5225 Approved
0.5932 Remote Similarity NPD4633 Approved
0.5929 Remote Similarity NPD8171 Discontinued
0.5929 Remote Similarity NPD6399 Phase 3
0.5926 Remote Similarity NPD6400 Clinical (unspecified phase)
0.5926 Remote Similarity NPD6845 Suspended
0.5917 Remote Similarity NPD8393 Approved
0.5897 Remote Similarity NPD4700 Approved
0.5896 Remote Similarity NPD5956 Approved
0.5891 Remote Similarity NPD6921 Approved
0.5888 Remote Similarity NPD4269 Approved
0.5888 Remote Similarity NPD4752 Clinical (unspecified phase)
0.5888 Remote Similarity NPD4270 Approved
0.5882 Remote Similarity NPD5175 Approved
0.5882 Remote Similarity NPD5174 Approved
0.5872 Remote Similarity NPD7520 Clinical (unspecified phase)
0.5868 Remote Similarity NPD8307 Discontinued
0.5868 Remote Similarity NPD8140 Approved
0.5859 Remote Similarity NPD7100 Approved
0.5859 Remote Similarity NPD7101 Approved
0.5847 Remote Similarity NPD5223 Approved
0.5841 Remote Similarity NPD7637 Suspended

  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