Structure

Physi-Chem Properties

Molecular Weight:  756.59
Volume:  850.068
LogP:  14.061
LogD:  5.33
LogS:  -7.597
# Rotatable Bonds:  36
TPSA:  99.13
# H-Bond Aceptor:  7
# H-Bond Donor:  1
# Rings:  2
# Heavy Atoms:  7

MedChem Properties

QED Drug-Likeness Score:  0.042
Synthetic Accessibility Score:  4.255
Fsp3:  0.809
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  2
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.395
MDCK Permeability:  1.055146071848867e-06
Pgp-inhibitor:  0.004
Pgp-substrate:  0.002
Human Intestinal Absorption (HIA):  0.004
20% Bioavailability (F20%):  1.0
30% Bioavailability (F30%):  0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.017
Plasma Protein Binding (PPB):  104.48053741455078%
Volume Distribution (VD):  4.964
Pgp-substrate:  0.36273691058158875%

ADMET: Metabolism

CYP1A2-inhibitor:  0.018
CYP1A2-substrate:  0.157
CYP2C19-inhibitor:  0.115
CYP2C19-substrate:  0.059
CYP2C9-inhibitor:  0.023
CYP2C9-substrate:  0.961
CYP2D6-inhibitor:  0.016
CYP2D6-substrate:  0.005
CYP3A4-inhibitor:  0.134
CYP3A4-substrate:  0.022

ADMET: Excretion

Clearance (CL):  3.713
Half-life (T1/2):  0.001

ADMET: Toxicity

hERG Blockers:  0.717
Human Hepatotoxicity (H-HT):  0.126
Drug-inuced Liver Injury (DILI):  0.913
AMES Toxicity:  0.187
Rat Oral Acute Toxicity:  0.04
Maximum Recommended Daily Dose:  0.318
Skin Sensitization:  0.964
Carcinogencity:  0.01
Eye Corrosion:  0.003
Eye Irritation:  0.013
Respiratory Toxicity:  0.277

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

  Natural Product: NPC470918

Natural Product ID:  NPC470918
Common Name*:   Manzamenone N
IUPAC Name:   trimethyl (1R,2R)-1,6-dihexadecyl-3-oxo-1,2,4,5-tetrahydroindene-2,4,7-tricarboxylate
Synonyms:   Manzamenone N
Standard InCHIKey:  ATDXPMMPVODFGD-CNVMDVFESA-N
Standard InCHI:  InChI=1S/C47H80O7/c1-6-8-10-12-14-16-18-20-22-24-26-28-30-32-34-37-36-39(45(49)52-3)42-41(40(37)46(50)53-4)38(43(44(42)48)47(51)54-5)35-33-31-29-27-25-23-21-19-17-15-13-11-9-7-2/h38-39,43H,6-36H2,1-5H3/t38-,39?,43+/m0/s1
SMILES:  CCCCCCCCCCCCCCCCC1C(C(=O)C2=C1C(=C(CC2C(=O)OC)CCCCCCCCCCCCCCCC)C(=O)OC)C(=O)OC
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL2314096
PubChem CID:   71518712
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000264] Organic acids and derivatives
      • [CHEMONTID:0000265] Carboxylic acids and derivatives
        • [CHEMONTID:0001986] Tricarboxylic acids and derivatives

*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
NPO32577 plakortis sp. Species Plakinidae Eukaryota n.a. Caribbean n.a. PMID[11720540]
NPO32577 plakortis sp. Species Plakinidae Eukaryota n.a. n.a. n.a. PMID[14738400]
NPO32577 plakortis sp. Species Plakinidae Eukaryota n.a. rock wall at 96 m depth, near Blue Hole, Orote Peninsula, Guam n.a. PMID[19618913]
NPO32577 plakortis sp. Species Plakinidae Eukaryota n.a. n.a. n.a. PMID[20235550]
NPO32577 plakortis sp. Species Plakinidae Eukaryota n.a. Okinawan n.a. PMID[23186727]
NPO32577 plakortis sp. Species Plakinidae Eukaryota n.a. n.a. n.a. PMID[7760075]
NPO32577 plakortis sp. Species Plakinidae Eukaryota n.a. n.a. n.a. PMID[9722495]

☑ 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
NPT85 Organism Filobasidiella neoformans Cryptococcus neoformans IC50 = 4.0 ug.mL-1 PMID[511531]
NPT20 Organism Candida albicans Candida albicans IC50 = 32.0 ug.mL-1 PMID[511531]
NPT330 Organism Trichophyton mentagrophytes Trichophyton mentagrophytes IC50 > 32.0 ug.mL-1 PMID[511531]
NPT21 Organism Aspergillus niger Aspergillus niger IC50 > 32.0 ug.mL-1 PMID[511531]
NPT729 Organism Micrococcus luteus Micrococcus luteus MIC > 32.0 ug.mL-1 PMID[511531]
NPT79 Organism Bacillus subtilis Bacillus subtilis MIC > 32.0 ug.mL-1 PMID[511531]
NPT16 Organism Staphylococcus aureus Staphylococcus aureus MIC > 32.0 ug.mL-1 PMID[511531]
NPT19 Organism Escherichia coli Escherichia coli MIC = 32.0 ug.mL-1 PMID[511531]

☑ 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 NPC470918 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
0.7927 Intermediate Similarity NPC244166
0.7619 Intermediate Similarity NPC473223
0.7586 Intermediate Similarity NPC471325
0.7586 Intermediate Similarity NPC42470
0.7525 Intermediate Similarity NPC137286
0.7525 Intermediate Similarity NPC71220
0.7447 Intermediate Similarity NPC248193
0.7444 Intermediate Similarity NPC78089
0.7442 Intermediate Similarity NPC128276
0.7442 Intermediate Similarity NPC315765
0.7416 Intermediate Similarity NPC475989
0.7391 Intermediate Similarity NPC473658
0.7391 Intermediate Similarity NPC26078
0.7386 Intermediate Similarity NPC282293
0.7368 Intermediate Similarity NPC53685
0.7363 Intermediate Similarity NPC107787
0.7356 Intermediate Similarity NPC178277
0.734 Intermediate Similarity NPC166110
0.7326 Intermediate Similarity NPC103987
0.7326 Intermediate Similarity NPC57744
0.7326 Intermediate Similarity NPC53581
0.7312 Intermediate Similarity NPC307092
0.7312 Intermediate Similarity NPC51358
0.7312 Intermediate Similarity NPC284561
0.7303 Intermediate Similarity NPC240302
0.7283 Intermediate Similarity NPC477228
0.7273 Intermediate Similarity NPC206079
0.7273 Intermediate Similarity NPC74673
0.7273 Intermediate Similarity NPC223904
0.7273 Intermediate Similarity NPC69271
0.7234 Intermediate Similarity NPC161638
0.7234 Intermediate Similarity NPC212679
0.7234 Intermediate Similarity NPC469595
0.7234 Intermediate Similarity NPC220454
0.7234 Intermediate Similarity NPC469372
0.7222 Intermediate Similarity NPC469561
0.7222 Intermediate Similarity NPC193198
0.7222 Intermediate Similarity NPC271784
0.7188 Intermediate Similarity NPC470697
0.7184 Intermediate Similarity NPC220155
0.7174 Intermediate Similarity NPC316426
0.7174 Intermediate Similarity NPC315395
0.7174 Intermediate Similarity NPC279859
0.7174 Intermediate Similarity NPC261721
0.7174 Intermediate Similarity NPC38576
0.7159 Intermediate Similarity NPC150646
0.7159 Intermediate Similarity NPC469620
0.7158 Intermediate Similarity NPC472705
0.7158 Intermediate Similarity NPC478243
0.7158 Intermediate Similarity NPC478244
0.7143 Intermediate Similarity NPC115786
0.7143 Intermediate Similarity NPC2049
0.7143 Intermediate Similarity NPC238197
0.7143 Intermediate Similarity NPC110937
0.7143 Intermediate Similarity NPC475100
0.7129 Intermediate Similarity NPC271059
0.7129 Intermediate Similarity NPC25666
0.7128 Intermediate Similarity NPC95364
0.7128 Intermediate Similarity NPC142159
0.7126 Intermediate Similarity NPC41780
0.7126 Intermediate Similarity NPC187568
0.7113 Intermediate Similarity NPC209355
0.7111 Intermediate Similarity NPC35556
0.7111 Intermediate Similarity NPC321289
0.7111 Intermediate Similarity NPC327969
0.7111 Intermediate Similarity NPC475690
0.7097 Intermediate Similarity NPC478144
0.7097 Intermediate Similarity NPC478145
0.7083 Intermediate Similarity NPC476597
0.7083 Intermediate Similarity NPC476598
0.7079 Intermediate Similarity NPC302426
0.7079 Intermediate Similarity NPC276356
0.7071 Intermediate Similarity NPC471932
0.7065 Intermediate Similarity NPC21471
0.7065 Intermediate Similarity NPC33570
0.7065 Intermediate Similarity NPC189311
0.7059 Intermediate Similarity NPC119493
0.7059 Intermediate Similarity NPC287878
0.7059 Intermediate Similarity NPC472868
0.7059 Intermediate Similarity NPC189616
0.7045 Intermediate Similarity NPC222210
0.7045 Intermediate Similarity NPC299235
0.7045 Intermediate Similarity NPC63445
0.7045 Intermediate Similarity NPC471220
0.7041 Intermediate Similarity NPC121036
0.7041 Intermediate Similarity NPC472674
0.7033 Intermediate Similarity NPC16488
0.7033 Intermediate Similarity NPC475947
0.7033 Intermediate Similarity NPC215294
0.7033 Intermediate Similarity NPC318468
0.7033 Intermediate Similarity NPC258985
0.7021 Intermediate Similarity NPC471956
0.7021 Intermediate Similarity NPC190718
0.7021 Intermediate Similarity NPC472302
0.701 Intermediate Similarity NPC148463
0.701 Intermediate Similarity NPC477130
0.701 Intermediate Similarity NPC477129
0.701 Intermediate Similarity NPC476596
0.7 Intermediate Similarity NPC25684
0.7 Intermediate Similarity NPC35089
0.7 Intermediate Similarity NPC255580
0.7 Intermediate Similarity NPC301477
0.7 Intermediate Similarity NPC39411
0.7 Intermediate Similarity NPC281949
0.7 Intermediate Similarity NPC10276
0.6989 Remote Similarity NPC220478
0.6989 Remote Similarity NPC474045
0.6989 Remote Similarity NPC234038
0.6989 Remote Similarity NPC261253
0.6981 Remote Similarity NPC474315
0.6979 Remote Similarity NPC284185
0.6979 Remote Similarity NPC471329
0.6979 Remote Similarity NPC473986
0.6979 Remote Similarity NPC193396
0.6979 Remote Similarity NPC32944
0.6979 Remote Similarity NPC261607
0.6979 Remote Similarity NPC123177
0.6979 Remote Similarity NPC150978
0.6979 Remote Similarity NPC70595
0.6979 Remote Similarity NPC300312
0.6979 Remote Similarity NPC221282
0.6979 Remote Similarity NPC111114
0.6979 Remote Similarity NPC74103
0.6979 Remote Similarity NPC296114
0.6979 Remote Similarity NPC474018
0.6979 Remote Similarity NPC472953
0.6977 Remote Similarity NPC469641
0.6977 Remote Similarity NPC476355
0.6977 Remote Similarity NPC294434
0.6977 Remote Similarity NPC259599
0.6977 Remote Similarity NPC15499
0.6977 Remote Similarity NPC469643
0.6977 Remote Similarity NPC117746
0.6977 Remote Similarity NPC140287
0.697 Remote Similarity NPC239895
0.697 Remote Similarity NPC202705
0.697 Remote Similarity NPC47834
0.6966 Remote Similarity NPC63649
0.6966 Remote Similarity NPC264227
0.6966 Remote Similarity NPC276647
0.6966 Remote Similarity NPC268502
0.6966 Remote Similarity NPC472965
0.6966 Remote Similarity NPC254996
0.6966 Remote Similarity NPC471299
0.6966 Remote Similarity NPC469690
0.6966 Remote Similarity NPC472013
0.6966 Remote Similarity NPC622
0.6966 Remote Similarity NPC476624
0.6961 Remote Similarity NPC475526
0.6961 Remote Similarity NPC473283
0.6961 Remote Similarity NPC329345
0.6957 Remote Similarity NPC320801
0.6957 Remote Similarity NPC477576
0.6957 Remote Similarity NPC477575
0.6957 Remote Similarity NPC159635
0.6947 Remote Similarity NPC173042
0.6947 Remote Similarity NPC32922
0.6947 Remote Similarity NPC280833
0.6939 Remote Similarity NPC474490
0.6939 Remote Similarity NPC473648
0.6939 Remote Similarity NPC31021
0.6939 Remote Similarity NPC20546
0.6939 Remote Similarity NPC295347
0.6939 Remote Similarity NPC171395
0.6932 Remote Similarity NPC316500
0.6932 Remote Similarity NPC195785
0.6932 Remote Similarity NPC476794
0.6932 Remote Similarity NPC472014
0.6932 Remote Similarity NPC316324
0.6932 Remote Similarity NPC65603
0.6932 Remote Similarity NPC470240
0.6932 Remote Similarity NPC15975
0.6931 Remote Similarity NPC99411
0.6931 Remote Similarity NPC244456
0.6931 Remote Similarity NPC469657
0.6931 Remote Similarity NPC473514
0.6923 Remote Similarity NPC91034
0.6923 Remote Similarity NPC296367
0.6923 Remote Similarity NPC186276
0.6923 Remote Similarity NPC173609
0.6915 Remote Similarity NPC72513
0.6915 Remote Similarity NPC181327
0.6907 Remote Similarity NPC472871
0.6907 Remote Similarity NPC469692
0.6907 Remote Similarity NPC469645
0.6907 Remote Similarity NPC1108
0.6907 Remote Similarity NPC271652
0.69 Remote Similarity NPC64742
0.69 Remote Similarity NPC471717
0.6897 Remote Similarity NPC68624
0.6897 Remote Similarity NPC228978
0.6893 Remote Similarity NPC309190
0.6893 Remote Similarity NPC470297
0.6889 Remote Similarity NPC47747
0.6882 Remote Similarity NPC177932
0.6882 Remote Similarity NPC470048
0.6882 Remote Similarity NPC125290
0.6875 Remote Similarity NPC280592
0.6875 Remote Similarity NPC253144
0.6875 Remote Similarity NPC477147

  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 NPC470918 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
0.7111 Intermediate Similarity NPD4800 Clinical (unspecified phase)
0.7053 Intermediate Similarity NPD5785 Approved
0.6923 Remote Similarity NPD5209 Approved
0.6897 Remote Similarity NPD8039 Approved
0.6882 Remote Similarity NPD5363 Approved
0.6882 Remote Similarity NPD1694 Approved
0.6809 Remote Similarity NPD5786 Approved
0.6739 Remote Similarity NPD4269 Approved
0.6739 Remote Similarity NPD4270 Approved
0.6739 Remote Similarity NPD4752 Clinical (unspecified phase)
0.6667 Remote Similarity NPD5737 Approved
0.6667 Remote Similarity NPD5362 Discontinued
0.6667 Remote Similarity NPD6672 Approved
0.6633 Remote Similarity NPD5693 Phase 1
0.6633 Remote Similarity NPD6050 Approved
0.663 Remote Similarity NPD5369 Approved
0.6604 Remote Similarity NPD7899 Clinical (unspecified phase)
0.66 Remote Similarity NPD1698 Clinical (unspecified phase)
0.6566 Remote Similarity NPD5779 Approved
0.6566 Remote Similarity NPD5778 Approved
0.6566 Remote Similarity NPD6399 Phase 3
0.6531 Remote Similarity NPD5692 Phase 3
0.6531 Remote Similarity NPD5207 Approved
0.6522 Remote Similarity NPD4252 Approved
0.6465 Remote Similarity NPD5694 Approved
0.6465 Remote Similarity NPD5284 Approved
0.6465 Remote Similarity NPD5281 Approved
0.6458 Remote Similarity NPD7521 Approved
0.6458 Remote Similarity NPD7334 Approved
0.6458 Remote Similarity NPD6409 Approved
0.6458 Remote Similarity NPD6684 Approved
0.6458 Remote Similarity NPD7146 Approved
0.6458 Remote Similarity NPD5330 Approved
0.6436 Remote Similarity NPD6356 Clinical (unspecified phase)
0.6429 Remote Similarity NPD6904 Approved
0.6429 Remote Similarity NPD6080 Approved
0.6429 Remote Similarity NPD7341 Phase 2
0.6429 Remote Similarity NPD6673 Approved
0.6429 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6429 Remote Similarity NPD6101 Approved
0.6429 Remote Similarity NPD1695 Approved
0.6422 Remote Similarity NPD6371 Approved
0.6374 Remote Similarity NPD4756 Discovery
0.6372 Remote Similarity NPD7115 Discovery
0.6337 Remote Similarity NPD7900 Approved
0.6337 Remote Similarity NPD7901 Clinical (unspecified phase)
0.6327 Remote Similarity NPD6903 Approved
0.6327 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6316 Remote Similarity NPD7154 Phase 3
0.6304 Remote Similarity NPD5784 Clinical (unspecified phase)
0.63 Remote Similarity NPD6411 Approved
0.6275 Remote Similarity NPD5654 Approved
0.6263 Remote Similarity NPD7285 Clinical (unspecified phase)
0.62 Remote Similarity NPD46 Approved
0.62 Remote Similarity NPD6698 Approved
0.6186 Remote Similarity NPD6082 Clinical (unspecified phase)
0.6162 Remote Similarity NPD5208 Approved
0.6154 Remote Similarity NPD6083 Phase 2
0.6154 Remote Similarity NPD7902 Approved
0.6154 Remote Similarity NPD5959 Approved
0.6154 Remote Similarity NPD6084 Phase 2
0.6139 Remote Similarity NPD7983 Approved
0.6139 Remote Similarity NPD7637 Suspended
0.6122 Remote Similarity NPD6098 Approved
0.6122 Remote Similarity NPD3574 Clinical (unspecified phase)
0.6122 Remote Similarity NPD5279 Phase 3
0.6117 Remote Similarity NPD5695 Phase 3
0.6095 Remote Similarity NPD5696 Approved
0.6095 Remote Similarity NPD4225 Approved
0.6095 Remote Similarity NPD8029 Clinical (unspecified phase)
0.6058 Remote Similarity NPD7839 Suspended
0.6044 Remote Similarity NPD5733 Approved
0.604 Remote Similarity NPD7838 Discovery
0.6019 Remote Similarity NPD7748 Approved
0.6019 Remote Similarity NPD6001 Approved
0.6019 Remote Similarity NPD5282 Discontinued
0.6018 Remote Similarity NPD6053 Discontinued
0.6 Remote Similarity NPD5954 Clinical (unspecified phase)
0.6 Remote Similarity NPD4518 Approved
0.6 Remote Similarity NPD5276 Approved
0.5979 Remote Similarity NPD5331 Approved
0.5979 Remote Similarity NPD5332 Approved
0.5977 Remote Similarity NPD7331 Phase 2
0.596 Remote Similarity NPD5280 Approved
0.596 Remote Similarity NPD4694 Approved
0.5957 Remote Similarity NPD3617 Approved
0.5943 Remote Similarity NPD7638 Approved
0.5941 Remote Similarity NPD6051 Approved
0.5938 Remote Similarity NPD4790 Discontinued
0.5918 Remote Similarity NPD4786 Approved
0.5909 Remote Similarity NPD6008 Approved
0.5905 Remote Similarity NPD7732 Phase 3
0.5893 Remote Similarity NPD6373 Approved
0.5893 Remote Similarity NPD6372 Approved
0.5888 Remote Similarity NPD7640 Approved
0.5888 Remote Similarity NPD7639 Approved
0.5888 Remote Similarity NPD6404 Discontinued
0.5876 Remote Similarity NPD4223 Phase 3
0.5876 Remote Similarity NPD4221 Approved
0.5876 Remote Similarity NPD6435 Approved
0.5872 Remote Similarity NPD6052 Approved
0.587 Remote Similarity NPD4687 Approved
0.5862 Remote Similarity NPD2685 Clinical (unspecified phase)
0.5859 Remote Similarity NPD1733 Clinical (unspecified phase)
0.5859 Remote Similarity NPD5329 Approved
0.5841 Remote Similarity NPD5955 Clinical (unspecified phase)
0.5833 Remote Similarity NPD4822 Approved
0.5833 Remote Similarity NPD4819 Approved
0.5833 Remote Similarity NPD5790 Clinical (unspecified phase)
0.5833 Remote Similarity NPD5368 Approved
0.5833 Remote Similarity NPD4695 Discontinued
0.5833 Remote Similarity NPD4820 Approved
0.5833 Remote Similarity NPD4821 Approved
0.5825 Remote Similarity NPD8035 Phase 2
0.5825 Remote Similarity NPD8034 Phase 2
0.5825 Remote Similarity NPD4810 Clinical (unspecified phase)
0.5825 Remote Similarity NPD7515 Phase 2
0.58 Remote Similarity NPD4519 Discontinued
0.58 Remote Similarity NPD3618 Phase 1
0.58 Remote Similarity NPD4623 Approved
0.5795 Remote Similarity NPD6108 Clinical (unspecified phase)
0.5795 Remote Similarity NPD3704 Approved
0.5789 Remote Similarity NPD6650 Approved
0.5789 Remote Similarity NPD4268 Approved
0.5789 Remote Similarity NPD4271 Approved
0.5789 Remote Similarity NPD6649 Approved
0.5784 Remote Similarity NPD4753 Phase 2
0.5784 Remote Similarity NPD5328 Approved
0.5784 Remote Similarity NPD5370 Suspended
0.578 Remote Similarity NPD7632 Discontinued
0.5766 Remote Similarity NPD5739 Approved
0.5766 Remote Similarity NPD7128 Approved
0.5766 Remote Similarity NPD6402 Approved
0.5766 Remote Similarity NPD6675 Approved
0.5758 Remote Similarity NPD3665 Phase 1
0.5758 Remote Similarity NPD3666 Approved
0.5758 Remote Similarity NPD3668 Phase 3
0.5758 Remote Similarity NPD4197 Approved
0.5758 Remote Similarity NPD3133 Approved
0.5755 Remote Similarity NPD4697 Phase 3
0.575 Remote Similarity NPD8517 Approved
0.575 Remote Similarity NPD8516 Approved
0.575 Remote Similarity NPD8515 Approved
0.575 Remote Similarity NPD8513 Phase 3
0.5747 Remote Similarity NPD5325 Clinical (unspecified phase)
0.5743 Remote Similarity NPD3573 Approved
0.5728 Remote Similarity NPD4096 Approved
0.5714 Remote Similarity NPD3667 Approved
0.5714 Remote Similarity NPD4747 Approved
0.5714 Remote Similarity NPD6614 Approved
0.57 Remote Similarity NPD1696 Phase 3
0.5699 Remote Similarity NPD4058 Approved
0.5673 Remote Similarity NPD6079 Approved
0.567 Remote Similarity NPD8259 Clinical (unspecified phase)
0.5664 Remote Similarity NPD7320 Approved
0.5664 Remote Similarity NPD6881 Approved
0.5664 Remote Similarity NPD6899 Approved
0.5664 Remote Similarity NPD6686 Approved
0.566 Remote Similarity NPD4629 Approved
0.566 Remote Similarity NPD5210 Approved
0.5652 Remote Similarity NPD8130 Phase 1
0.5644 Remote Similarity NPD4690 Approved
0.5644 Remote Similarity NPD5690 Phase 2
0.5644 Remote Similarity NPD5205 Approved
0.5644 Remote Similarity NPD4688 Approved
0.5644 Remote Similarity NPD4689 Approved
0.5644 Remote Similarity NPD4693 Phase 3
0.5644 Remote Similarity NPD4138 Approved
0.5632 Remote Similarity NPD2664 Clinical (unspecified phase)
0.5625 Remote Similarity NPD4238 Approved
0.5625 Remote Similarity NPD4802 Phase 2
0.5619 Remote Similarity NPD5133 Approved
0.5614 Remote Similarity NPD4061 Clinical (unspecified phase)
0.5612 Remote Similarity NPD4692 Approved
0.5612 Remote Similarity NPD4139 Approved
0.5604 Remote Similarity NPD4137 Phase 3
0.5603 Remote Similarity NPD8297 Approved
0.56 Remote Similarity NPD6400 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