Structure

Physi-Chem Properties

Molecular Weight:  392.29
Volume:  433.799
LogP:  6.412
LogD:  4.595
LogS:  -4.547
# Rotatable Bonds:  8
TPSA:  55.76
# H-Bond Aceptor:  4
# H-Bond Donor:  1
# Rings:  2
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.373
Synthetic Accessibility Score:  4.368
Fsp3:  0.792
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Rejected
BMS Rule:  1
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.16
MDCK Permeability:  1.980524029931985e-05
Pgp-inhibitor:  0.652
Pgp-substrate:  0.0
Human Intestinal Absorption (HIA):  0.004
20% Bioavailability (F20%):  0.013
30% Bioavailability (F30%):  0.026

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.332
Plasma Protein Binding (PPB):  95.44986724853516%
Volume Distribution (VD):  1.627
Pgp-substrate:  1.9132109880447388%

ADMET: Metabolism

CYP1A2-inhibitor:  0.028
CYP1A2-substrate:  0.605
CYP2C19-inhibitor:  0.045
CYP2C19-substrate:  0.93
CYP2C9-inhibitor:  0.146
CYP2C9-substrate:  0.958
CYP2D6-inhibitor:  0.03
CYP2D6-substrate:  0.572
CYP3A4-inhibitor:  0.124
CYP3A4-substrate:  0.089

ADMET: Excretion

Clearance (CL):  2.925
Half-life (T1/2):  0.138

ADMET: Toxicity

hERG Blockers:  0.022
Human Hepatotoxicity (H-HT):  0.468
Drug-inuced Liver Injury (DILI):  0.017
AMES Toxicity:  0.002
Rat Oral Acute Toxicity:  0.047
Maximum Recommended Daily Dose:  0.177
Skin Sensitization:  0.915
Carcinogencity:  0.068
Eye Corrosion:  0.113
Eye Irritation:  0.208
Respiratory Toxicity:  0.587

Download Data

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

  Natural Product: NPC172309

Natural Product ID:  NPC172309
Common Name*:   (-)-Muqubilin A
IUPAC Name:   (2S)-2-[(3R,6S)-6-methyl-6-[(E)-4-methyl-6-(2,6,6-trimethylcyclohexen-1-yl)hex-3-enyl]dioxan-3-yl]propanoic acid
Synonyms:   (-)-Muqubilin A
Standard InCHIKey:  ZJKZMXQQSDVDLA-HGMMXSCQSA-N
Standard InCHI:  InChI=1S/C24H40O4/c1-17(11-12-20-18(2)10-8-14-23(20,4)5)9-7-15-24(6)16-13-21(27-28-24)19(3)22(25)26/h9,19,21H,7-8,10-16H2,1-6H3,(H,25,26)/b17-9+/t19-,21+,24-/m0/s1
SMILES:  C/C(=CCC[C@@]1(C)CC[C@H]([C@H](C)C(=O)O)OO1)/CCC1=C(C)CCCC1(C)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL463702
PubChem CID:   21600068
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001550] Sesquiterpenoids

*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
NPO5207 Diacarnus erythraeanus Species Podospongiidae Eukaryota n.a. n.a. n.a. PMID[11325240]
NPO5207 Diacarnus erythraeanus Species Podospongiidae Eukaryota n.a. Red Sea n.a. PMID[11325240]
NPO5207 Diacarnus erythraeanus Species Podospongiidae Eukaryota n.a. Red Sea n.a. PMID[23977995]
NPO40711 Diacarnus cf. spinopoculum Strain Podospongiidae Eukaryota n.a. n.a. n.a. PMID[9514009]

☑ 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
NPT116 Cell Line HL-60 Homo sapiens GI50 = 1770.0 nM PMID[564063]
NPT112 Cell Line MOLT-4 Homo sapiens GI50 > 5000.0 nM PMID[564063]
NPT81 Cell Line A549 Homo sapiens GI50 > 5000.0 nM PMID[564063]
NPT394 Cell Line EKVX Homo sapiens GI50 > 5000.0 nM PMID[564063]
NPT379 Cell Line HOP-62 Homo sapiens GI50 > 5000.0 nM PMID[564063]
NPT372 Cell Line HOP-92 Homo sapiens GI50 > 5000.0 nM PMID[564063]
NPT405 Cell Line NCI-H226 Homo sapiens GI50 > 5000.0 nM PMID[564063]
NPT370 Cell Line NCI-H23 Homo sapiens GI50 > 5000.0 nM PMID[564063]
NPT388 Cell Line NCI-H322M Homo sapiens GI50 > 5000.0 nM PMID[564063]
NPT397 Cell Line NCI-H460 Homo sapiens GI50 > 5000.0 nM PMID[564063]
NPT407 Cell Line COLO 205 Homo sapiens GI50 > 5000.0 nM PMID[564063]
NPT391 Cell Line HCC 2998 Homo sapiens GI50 > 5000.0 nM PMID[564063]
NPT393 Cell Line HCT-116 Homo sapiens GI50 > 5000.0 nM PMID[564063]
NPT148 Cell Line HCT-15 Homo sapiens GI50 > 5000.0 nM PMID[564063]
NPT139 Cell Line HT-29 Homo sapiens GI50 > 5000.0 nM PMID[564063]
NPT386 Cell Line KM12 Homo sapiens GI50 > 5000.0 nM PMID[564063]
NPT323 Cell Line SW-620 Homo sapiens GI50 > 5000.0 nM PMID[564063]
NPT395 Cell Line SF-268 Homo sapiens GI50 > 5000.0 nM PMID[564063]
NPT399 Cell Line SF-295 Homo sapiens GI50 > 5000.0 nM PMID[564063]
NPT374 Cell Line SF-539 Homo sapiens GI50 > 5000.0 nM PMID[564063]
NPT383 Cell Line SNB-19 Homo sapiens GI50 > 5000.0 nM PMID[564063]
NPT392 Cell Line SNB-75 Homo sapiens GI50 > 5000.0 nM PMID[564063]
NPT380 Cell Line U-251 Homo sapiens GI50 > 5000.0 nM PMID[564063]
NPT390 Cell Line LOX IMVI Homo sapiens GI50 = 2170.0 nM PMID[564063]
NPT387 Cell Line M14 Homo sapiens GI50 > 5000.0 nM PMID[564063]
NPT147 Cell Line SK-MEL-2 Homo sapiens GI50 > 5000.0 nM PMID[564063]
NPT170 Cell Line SK-MEL-28 Homo sapiens GI50 = 430.0 nM PMID[564063]
NPT373 Cell Line SK-MEL-5 Homo sapiens GI50 > 5000.0 nM PMID[564063]
NPT403 Cell Line UACC-257 Homo sapiens GI50 > 5000.0 nM PMID[564063]
NPT458 Cell Line IGROV-1 Homo sapiens GI50 = 1110.0 nM PMID[564063]
NPT377 Cell Line OVCAR-3 Homo sapiens GI50 > 5000.0 nM PMID[564063]
NPT456 Cell Line OVCAR-4 Homo sapiens GI50 > 5000.0 nM PMID[564063]
NPT382 Cell Line OVCAR-5 Homo sapiens GI50 > 5000.0 nM PMID[564063]
NPT381 Cell Line OVCAR-8 Homo sapiens GI50 > 5000.0 nM PMID[564063]
NPT146 Cell Line SK-OV-3 Homo sapiens GI50 > 5000.0 nM PMID[564063]
NPT401 Cell Line 786-0 Homo sapiens GI50 > 5000.0 nM PMID[564063]
NPT376 Cell Line A498 Homo sapiens GI50 > 5000.0 nM PMID[564063]
NPT369 Cell Line ACHN Homo sapiens GI50 > 5000.0 nM PMID[564063]
NPT308 Cell Line CAKI-1 Homo sapiens GI50 > 5000.0 nM PMID[564063]
NPT406 Cell Line RXF 393 Homo sapiens GI50 > 5000.0 nM PMID[564063]
NPT368 Cell Line SN12C Homo sapiens GI50 > 5000.0 nM PMID[564063]
NPT384 Cell Line TK-10 Homo sapiens GI50 > 5000.0 nM PMID[564063]
NPT371 Cell Line UO-31 Homo sapiens GI50 > 5000.0 nM PMID[564063]
NPT306 Cell Line PC-3 Homo sapiens GI50 > 5000.0 nM PMID[564063]
NPT83 Cell Line MCF7 Homo sapiens GI50 > 5000.0 nM PMID[564063]
NPT82 Cell Line MDA-MB-231 Homo sapiens GI50 > 5000.0 nM PMID[564063]
NPT400 Cell Line MDA-MB-435 Homo sapiens GI50 > 5000.0 nM PMID[564063]
NPT367 Cell Line MDA-N Homo sapiens GI50 > 5000.0 nM PMID[564063]
NPT457 Cell Line BT-549 Homo sapiens GI50 > 5000.0 nM PMID[564063]
NPT396 Cell Line T47D Homo sapiens GI50 > 5000.0 nM PMID[564063]
NPT137 Cell Line L1210 Mus musculus Activity = 110.0 Zone units PMID[564063]
NPT168 Cell Line P388 Mus musculus Activity = 110.0 Zone units PMID[564063]
NPT6285 Cell Line PO3 Homo sapiens Activity = 40.0 Zone units PMID[564063]
NPT730 Cell Line MC-38 Mus musculus Activity = 60.0 Zone units PMID[564063]
NPT6227 Cell Line CX-1 Homo sapiens Activity = 100.0 Zone units PMID[564063]
NPT5027 Cell Line Hs 683 Homo sapiens Activity = 30.0 % PMID[564064]
NPT3190 Cell Line NHDF Homo sapiens IC50 = 26000.0 nM PMID[564064]
NPT941 Cell Line HaCaT Homo sapiens IC50 = 23000.0 nM PMID[564064]
NPT1723 Cell Line HBL-100 Homo sapiens IC50 = 3000.0 nM PMID[564064]
NPT169 Cell Line B16-F10 Mus musculus IC50 = 3000.0 nM PMID[564064]
NPT114 Cell Line LoVo Homo sapiens IC50 = 6000.0 nM PMID[564064]
NPT306 Cell Line PC-3 Homo sapiens IC50 = 8000.0 nM PMID[564064]
NPT83 Cell Line MCF7 Homo sapiens IC50 = 7000.0 nM PMID[564064]
NPT81 Cell Line A549 Homo sapiens IC50 = 3000.0 nM PMID[564064]
NPT170 Cell Line SK-MEL-28 Homo sapiens IC50 = 8000.0 nM PMID[564064]
NPT380 Cell Line U-251 Homo sapiens IC50 = 8000.0 nM PMID[564064]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Activity = 80.0 Zone units PMID[564063]
NPT2 Others Unspecified Activity = 30.0 % PMID[564064]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 7000.0 nM PMID[564064]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 4000.0 nM PMID[564064]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum IC50 = 5600.0 nM PMID[564065]
NPT1666 Organism Plasmodium falciparum D6 Plasmodium falciparum D6 IC50 = 8600.0 nM PMID[564065]
NPT2 Others Unspecified Ratio IC50 = 2.2 n.a. PMID[564065]
NPT2 Others Unspecified Ratio IC50 = 1.4 n.a. PMID[564065]
NPT2 Others Unspecified GI50 > 5000 nM PMID[15481972]

☑ 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 NPC172309 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 NPC14044
1.0 High Similarity NPC117960
0.9487 High Similarity NPC476983
0.9474 High Similarity NPC82488
0.9474 High Similarity NPC308545
0.9375 High Similarity NPC476982
0.9375 High Similarity NPC262085
0.925 High Similarity NPC471344
0.9231 High Similarity NPC476988
0.9136 High Similarity NPC476104
0.9091 High Similarity NPC476986
0.9091 High Similarity NPC470905
0.9079 High Similarity NPC152754
0.9079 High Similarity NPC59602
0.9079 High Similarity NPC469514
0.9079 High Similarity NPC476987
0.9 High Similarity NPC476100
0.8961 High Similarity NPC476264
0.8961 High Similarity NPC476325
0.8889 High Similarity NPC471343
0.8846 High Similarity NPC121200
0.881 High Similarity NPC469866
0.881 High Similarity NPC471342
0.8734 High Similarity NPC254996
0.8734 High Similarity NPC268502
0.8718 High Similarity NPC281296
0.8675 High Similarity NPC475181
0.8642 High Similarity NPC474605
0.8642 High Similarity NPC475395
0.8642 High Similarity NPC476292
0.8642 High Similarity NPC476984
0.859 High Similarity NPC476985
0.859 High Similarity NPC474316
0.859 High Similarity NPC475744
0.8571 High Similarity NPC330016
0.8481 Intermediate Similarity NPC469867
0.8462 Intermediate Similarity NPC199445
0.8462 Intermediate Similarity NPC60718
0.8442 Intermediate Similarity NPC167145
0.8375 Intermediate Similarity NPC321514
0.8354 Intermediate Similarity NPC474447
0.8293 Intermediate Similarity NPC327002
0.8272 Intermediate Similarity NPC113363
0.825 Intermediate Similarity NPC122847
0.8214 Intermediate Similarity NPC120158
0.8214 Intermediate Similarity NPC475193
0.8182 Intermediate Similarity NPC36491
0.8171 Intermediate Similarity NPC274522
0.8171 Intermediate Similarity NPC476265
0.8125 Intermediate Similarity NPC239127
0.8095 Intermediate Similarity NPC69469
0.8095 Intermediate Similarity NPC477373
0.8049 Intermediate Similarity NPC327674
0.8023 Intermediate Similarity NPC73038
0.8022 Intermediate Similarity NPC132824
0.8 Intermediate Similarity NPC255060
0.7978 Intermediate Similarity NPC6255
0.7978 Intermediate Similarity NPC324341
0.7978 Intermediate Similarity NPC288833
0.7978 Intermediate Similarity NPC966
0.7978 Intermediate Similarity NPC282616
0.7978 Intermediate Similarity NPC471588
0.7978 Intermediate Similarity NPC155120
0.7978 Intermediate Similarity NPC228784
0.7975 Intermediate Similarity NPC474543
0.7975 Intermediate Similarity NPC238425
0.7975 Intermediate Similarity NPC472018
0.7955 Intermediate Similarity NPC97577
0.7952 Intermediate Similarity NPC37038
0.7931 Intermediate Similarity NPC477926
0.7931 Intermediate Similarity NPC312215
0.7931 Intermediate Similarity NPC96496
0.7931 Intermediate Similarity NPC173089
0.7931 Intermediate Similarity NPC158141
0.7927 Intermediate Similarity NPC179028
0.7907 Intermediate Similarity NPC76333
0.7889 Intermediate Similarity NPC118490
0.7875 Intermediate Similarity NPC474551
0.7865 Intermediate Similarity NPC86372
0.7865 Intermediate Similarity NPC130278
0.7865 Intermediate Similarity NPC172361
0.7857 Intermediate Similarity NPC79277
0.7857 Intermediate Similarity NPC473420
0.7857 Intermediate Similarity NPC475481
0.7849 Intermediate Similarity NPC174663
0.7848 Intermediate Similarity NPC126061
0.7848 Intermediate Similarity NPC160817
0.7841 Intermediate Similarity NPC474511
0.7841 Intermediate Similarity NPC294480
0.7841 Intermediate Similarity NPC1753
0.7831 Intermediate Similarity NPC231431
0.7826 Intermediate Similarity NPC201657
0.7816 Intermediate Similarity NPC324063
0.7816 Intermediate Similarity NPC475753
0.7816 Intermediate Similarity NPC212843
0.7816 Intermediate Similarity NPC473226
0.7802 Intermediate Similarity NPC191412
0.7802 Intermediate Similarity NPC6818
0.7802 Intermediate Similarity NPC148964
0.7802 Intermediate Similarity NPC23621
0.7802 Intermediate Similarity NPC184006
0.7802 Intermediate Similarity NPC78580
0.7802 Intermediate Similarity NPC114159
0.7802 Intermediate Similarity NPC222047
0.7791 Intermediate Similarity NPC165064
0.7766 Intermediate Similarity NPC35239
0.7753 Intermediate Similarity NPC474700
0.7753 Intermediate Similarity NPC25906
0.7753 Intermediate Similarity NPC270768
0.7753 Intermediate Similarity NPC290972
0.7753 Intermediate Similarity NPC263393
0.7753 Intermediate Similarity NPC61543
0.7753 Intermediate Similarity NPC155479
0.7753 Intermediate Similarity NPC64872
0.7753 Intermediate Similarity NPC256902
0.7753 Intermediate Similarity NPC130520
0.7753 Intermediate Similarity NPC475921
0.7753 Intermediate Similarity NPC127689
0.7753 Intermediate Similarity NPC121798
0.7753 Intermediate Similarity NPC474570
0.7753 Intermediate Similarity NPC474704
0.7753 Intermediate Similarity NPC118193
0.7753 Intermediate Similarity NPC234346
0.7753 Intermediate Similarity NPC59263
0.7753 Intermediate Similarity NPC293048
0.7753 Intermediate Similarity NPC225585
0.7742 Intermediate Similarity NPC261935
0.7742 Intermediate Similarity NPC124246
0.7742 Intermediate Similarity NPC106112
0.7742 Intermediate Similarity NPC187933
0.7738 Intermediate Similarity NPC104545
0.7738 Intermediate Similarity NPC103634
0.7733 Intermediate Similarity NPC474552
0.7727 Intermediate Similarity NPC171722
0.7727 Intermediate Similarity NPC167877
0.7722 Intermediate Similarity NPC69462
0.7717 Intermediate Similarity NPC266899
0.7717 Intermediate Similarity NPC263347
0.7717 Intermediate Similarity NPC148523
0.7717 Intermediate Similarity NPC23241
0.7717 Intermediate Similarity NPC195715
0.7711 Intermediate Similarity NPC280654
0.7711 Intermediate Similarity NPC74410
0.7711 Intermediate Similarity NPC110094
0.7711 Intermediate Similarity NPC239098
0.7711 Intermediate Similarity NPC260385
0.7701 Intermediate Similarity NPC329738
0.7692 Intermediate Similarity NPC229281
0.7692 Intermediate Similarity NPC118519
0.7692 Intermediate Similarity NPC298554
0.7692 Intermediate Similarity NPC158059
0.7692 Intermediate Similarity NPC202728
0.7683 Intermediate Similarity NPC180886
0.7683 Intermediate Similarity NPC266119
0.7674 Intermediate Similarity NPC312480
0.7667 Intermediate Similarity NPC273621
0.7667 Intermediate Similarity NPC126369
0.7667 Intermediate Similarity NPC193750
0.7667 Intermediate Similarity NPC210037
0.7667 Intermediate Similarity NPC227467
0.7667 Intermediate Similarity NPC120968
0.7667 Intermediate Similarity NPC290614
0.7667 Intermediate Similarity NPC46281
0.7667 Intermediate Similarity NPC470589
0.7667 Intermediate Similarity NPC477872
0.7667 Intermediate Similarity NPC18872
0.7667 Intermediate Similarity NPC111110
0.7667 Intermediate Similarity NPC7260
0.766 Intermediate Similarity NPC29765
0.766 Intermediate Similarity NPC271614
0.766 Intermediate Similarity NPC111214
0.766 Intermediate Similarity NPC164349
0.7654 Intermediate Similarity NPC103958
0.7654 Intermediate Similarity NPC161923
0.7654 Intermediate Similarity NPC301065
0.7654 Intermediate Similarity NPC283908
0.7654 Intermediate Similarity NPC183503
0.7647 Intermediate Similarity NPC229584
0.7647 Intermediate Similarity NPC142244
0.7647 Intermediate Similarity NPC90055
0.7647 Intermediate Similarity NPC278459
0.7647 Intermediate Similarity NPC14151
0.7647 Intermediate Similarity NPC14203
0.764 Intermediate Similarity NPC182797
0.764 Intermediate Similarity NPC247406
0.764 Intermediate Similarity NPC104560
0.764 Intermediate Similarity NPC470417
0.764 Intermediate Similarity NPC48866
0.764 Intermediate Similarity NPC183546
0.764 Intermediate Similarity NPC52169
0.7634 Intermediate Similarity NPC116457
0.7634 Intermediate Similarity NPC469528
0.7634 Intermediate Similarity NPC98874
0.7634 Intermediate Similarity NPC472806
0.7634 Intermediate Similarity NPC469369
0.7634 Intermediate Similarity NPC167193
0.7619 Intermediate Similarity NPC246458
0.7619 Intermediate Similarity NPC477371
0.7619 Intermediate Similarity NPC199595
0.7614 Intermediate Similarity NPC470415

  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 NPC172309 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
0.8182 Intermediate Similarity NPD6411 Approved
0.7955 Intermediate Similarity NPD5764 Clinical (unspecified phase)
0.7955 Intermediate Similarity NPD6101 Approved
0.75 Intermediate Similarity NPD5779 Approved
0.75 Intermediate Similarity NPD5778 Approved
0.75 Intermediate Similarity NPD6399 Phase 3
0.7391 Intermediate Similarity NPD7515 Phase 2
0.7241 Intermediate Similarity NPD5369 Approved
0.7234 Intermediate Similarity NPD7748 Approved
0.7191 Intermediate Similarity NPD4786 Approved
0.7188 Intermediate Similarity NPD6083 Phase 2
0.7188 Intermediate Similarity NPD6084 Phase 2
0.7188 Intermediate Similarity NPD7902 Approved
0.7159 Intermediate Similarity NPD3667 Approved
0.7158 Intermediate Similarity NPD5695 Phase 3
0.7126 Intermediate Similarity NPD5368 Approved
0.7093 Intermediate Similarity NPD5784 Clinical (unspecified phase)
0.7053 Intermediate Similarity NPD5282 Discontinued
0.7033 Intermediate Similarity NPD6409 Approved
0.7033 Intermediate Similarity NPD7146 Approved
0.7033 Intermediate Similarity NPD6684 Approved
0.7033 Intermediate Similarity NPD5330 Approved
0.7033 Intermediate Similarity NPD7521 Approved
0.7033 Intermediate Similarity NPD7334 Approved
0.703 Intermediate Similarity NPD6402 Approved
0.703 Intermediate Similarity NPD5739 Approved
0.703 Intermediate Similarity NPD6675 Approved
0.703 Intermediate Similarity NPD7128 Approved
0.7021 Intermediate Similarity NPD5281 Approved
0.7021 Intermediate Similarity NPD5284 Approved
0.7 Intermediate Similarity NPD3665 Phase 1
0.7 Intermediate Similarity NPD3666 Approved
0.7 Intermediate Similarity NPD7331 Phase 2
0.7 Intermediate Similarity NPD3133 Approved
0.6989 Remote Similarity NPD4753 Phase 2
0.6966 Remote Similarity NPD4269 Approved
0.6966 Remote Similarity NPD6435 Approved
0.6966 Remote Similarity NPD4270 Approved
0.6941 Remote Similarity NPD8039 Approved
0.6939 Remote Similarity NPD5696 Approved
0.6932 Remote Similarity NPD4819 Approved
0.6932 Remote Similarity NPD4695 Discontinued
0.6932 Remote Similarity NPD4822 Approved
0.6932 Remote Similarity NPD4821 Approved
0.6932 Remote Similarity NPD4820 Approved
0.6915 Remote Similarity NPD6698 Approved
0.6915 Remote Similarity NPD46 Approved
0.6893 Remote Similarity NPD6881 Approved
0.6893 Remote Similarity NPD6899 Approved
0.6893 Remote Similarity NPD7320 Approved
0.6889 Remote Similarity NPD7154 Phase 3
0.6882 Remote Similarity NPD5737 Approved
0.6882 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6882 Remote Similarity NPD6672 Approved
0.6882 Remote Similarity NPD6903 Approved
0.6875 Remote Similarity NPD7900 Approved
0.6875 Remote Similarity NPD7341 Phase 2
0.6875 Remote Similarity NPD7901 Clinical (unspecified phase)
0.6848 Remote Similarity NPD3574 Clinical (unspecified phase)
0.6848 Remote Similarity NPD5279 Phase 3
0.6848 Remote Similarity NPD3618 Phase 1
0.6842 Remote Similarity NPD7637 Suspended
0.6842 Remote Similarity NPD7983 Approved
0.6837 Remote Similarity NPD4755 Approved
0.6827 Remote Similarity NPD6373 Approved
0.6827 Remote Similarity NPD6372 Approved
0.6813 Remote Similarity NPD3668 Phase 3
0.6809 Remote Similarity NPD7285 Clinical (unspecified phase)
0.6809 Remote Similarity NPD5328 Approved
0.6804 Remote Similarity NPD1698 Clinical (unspecified phase)
0.6796 Remote Similarity NPD5701 Approved
0.6796 Remote Similarity NPD5697 Approved
0.6778 Remote Similarity NPD4752 Clinical (unspecified phase)
0.6778 Remote Similarity NPD4223 Phase 3
0.6778 Remote Similarity NPD4221 Approved
0.6771 Remote Similarity NPD4202 Approved
0.6762 Remote Similarity NPD7102 Approved
0.6762 Remote Similarity NPD7290 Approved
0.6762 Remote Similarity NPD6883 Approved
0.6742 Remote Similarity NPD4252 Approved
0.6742 Remote Similarity NPD8259 Clinical (unspecified phase)
0.6739 Remote Similarity NPD5329 Approved
0.6739 Remote Similarity NPD7520 Clinical (unspecified phase)
0.6739 Remote Similarity NPD5363 Approved
0.6737 Remote Similarity NPD5785 Approved
0.6735 Remote Similarity NPD7839 Suspended
0.6731 Remote Similarity NPD6686 Approved
0.6705 Remote Similarity NPD4271 Approved
0.6705 Remote Similarity NPD4268 Approved
0.6703 Remote Similarity NPD5362 Discontinued
0.67 Remote Similarity NPD5285 Approved
0.67 Remote Similarity NPD4696 Approved
0.67 Remote Similarity NPD5286 Approved
0.67 Remote Similarity NPD4700 Approved
0.6698 Remote Similarity NPD6847 Approved
0.6698 Remote Similarity NPD6650 Approved
0.6698 Remote Similarity NPD6617 Approved
0.6698 Remote Similarity NPD6869 Approved
0.6698 Remote Similarity NPD6649 Approved
0.6698 Remote Similarity NPD8130 Phase 1
0.6667 Remote Similarity NPD5786 Approved
0.6667 Remote Similarity NPD6422 Discontinued
0.6667 Remote Similarity NPD6014 Approved
0.6667 Remote Similarity NPD6012 Approved
0.6667 Remote Similarity NPD8035 Phase 2
0.6667 Remote Similarity NPD8034 Phase 2
0.6667 Remote Similarity NPD6013 Approved
0.6667 Remote Similarity NPD6098 Approved
0.6667 Remote Similarity NPD6079 Approved
0.6636 Remote Similarity NPD6882 Approved
0.6636 Remote Similarity NPD8297 Approved
0.6635 Remote Similarity NPD6412 Phase 2
0.6633 Remote Similarity NPD4629 Approved
0.6633 Remote Similarity NPD5210 Approved
0.6632 Remote Similarity NPD6080 Approved
0.6632 Remote Similarity NPD6904 Approved
0.6632 Remote Similarity NPD6673 Approved
0.663 Remote Similarity NPD4197 Approved
0.6628 Remote Similarity NPD6924 Approved
0.6628 Remote Similarity NPD6926 Approved
0.66 Remote Similarity NPD4225 Approved
0.6596 Remote Similarity NPD3573 Approved
0.6571 Remote Similarity NPD6011 Approved
0.6569 Remote Similarity NPD4633 Approved
0.6569 Remote Similarity NPD5224 Approved
0.6569 Remote Similarity NPD5211 Phase 2
0.6569 Remote Similarity NPD5226 Approved
0.6569 Remote Similarity NPD5225 Approved
0.6556 Remote Similarity NPD5790 Clinical (unspecified phase)
0.6556 Remote Similarity NPD7525 Registered
0.6545 Remote Similarity NPD7115 Discovery
0.6543 Remote Similarity NPD3197 Phase 1
0.6542 Remote Similarity NPD6401 Clinical (unspecified phase)
0.6517 Remote Similarity NPD3732 Approved
0.6505 Remote Similarity NPD5175 Approved
0.6505 Remote Similarity NPD5174 Approved
0.6495 Remote Similarity NPD6050 Approved
0.6489 Remote Similarity NPD4519 Discontinued
0.6489 Remote Similarity NPD4138 Approved
0.6489 Remote Similarity NPD5280 Approved
0.6489 Remote Similarity NPD4694 Approved
0.6489 Remote Similarity NPD4690 Approved
0.6489 Remote Similarity NPD5205 Approved
0.6489 Remote Similarity NPD5690 Phase 2
0.6489 Remote Similarity NPD4689 Approved
0.6489 Remote Similarity NPD4693 Phase 3
0.6489 Remote Similarity NPD4623 Approved
0.6489 Remote Similarity NPD4688 Approved
0.6477 Remote Similarity NPD6933 Approved
0.6471 Remote Similarity NPD5223 Approved
0.6465 Remote Similarity NPD6356 Clinical (unspecified phase)
0.6452 Remote Similarity NPD6400 Clinical (unspecified phase)
0.6452 Remote Similarity NPD7338 Clinical (unspecified phase)
0.6449 Remote Similarity NPD4634 Approved
0.6449 Remote Similarity NPD6371 Approved
0.6447 Remote Similarity NPD4266 Approved
0.6447 Remote Similarity NPD3194 Approved
0.6447 Remote Similarity NPD3729 Clinical (unspecified phase)
0.6447 Remote Similarity NPD3195 Phase 2
0.6447 Remote Similarity NPD3196 Approved
0.6444 Remote Similarity NPD7645 Phase 2
0.6442 Remote Similarity NPD5141 Approved
0.6436 Remote Similarity NPD7638 Approved
0.6415 Remote Similarity NPD5345 Clinical (unspecified phase)
0.64 Remote Similarity NPD5222 Approved
0.64 Remote Similarity NPD5221 Approved
0.64 Remote Similarity NPD7614 Phase 1
0.64 Remote Similarity NPD5220 Clinical (unspecified phase)
0.64 Remote Similarity NPD4697 Phase 3
0.6392 Remote Similarity NPD5692 Phase 3
0.6383 Remote Similarity NPD1694 Approved
0.6381 Remote Similarity NPD4767 Approved
0.6381 Remote Similarity NPD4768 Approved
0.6374 Remote Similarity NPD6930 Phase 2
0.6374 Remote Similarity NPD7509 Discontinued
0.6374 Remote Similarity NPD6931 Approved
0.6373 Remote Similarity NPD7640 Approved
0.6373 Remote Similarity NPD7639 Approved
0.6372 Remote Similarity NPD6319 Approved
0.6364 Remote Similarity NPD7339 Approved
0.6364 Remote Similarity NPD6942 Approved
0.6355 Remote Similarity NPD8132 Clinical (unspecified phase)
0.6354 Remote Similarity NPD5208 Approved
0.6354 Remote Similarity NPD4518 Approved
0.6348 Remote Similarity NPD8328 Phase 3
0.6346 Remote Similarity NPD4754 Approved
0.6344 Remote Similarity NPD4788 Approved
0.6344 Remote Similarity NPD5331 Approved
0.6344 Remote Similarity NPD5332 Approved
0.6344 Remote Similarity NPD6695 Phase 3
0.6337 Remote Similarity NPD5173 Approved
0.6333 Remote Similarity NPD3617 Approved
0.633 Remote Similarity NPD6053 Discontinued
0.6327 Remote Similarity NPD5694 Approved
0.6327 Remote Similarity NPD5693 Phase 1
0.6321 Remote Similarity NPD7899 Clinical (unspecified phase)
0.6316 Remote Similarity NPD3172 Approved
0.6306 Remote Similarity NPD6274 Approved
0.6304 Remote Similarity NPD4139 Approved
0.6304 Remote Similarity NPD4692 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