Structure

Physi-Chem Properties

Molecular Weight:  626.38
Volume:  672.069
LogP:  9.116
LogD:  5.269
LogS:  -6.356
# Rotatable Bonds:  20
TPSA:  119.34
# H-Bond Aceptor:  8
# H-Bond Donor:  2
# Rings:  3
# Heavy Atoms:  8

MedChem Properties

QED Drug-Likeness Score:  0.095
Synthetic Accessibility Score:  6.123
Fsp3:  0.622
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  1
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.991
MDCK Permeability:  3.232011295040138e-05
Pgp-inhibitor:  0.736
Pgp-substrate:  0.877
Human Intestinal Absorption (HIA):  0.019
20% Bioavailability (F20%):  0.921
30% Bioavailability (F30%):  0.967

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.006
Plasma Protein Binding (PPB):  98.96165466308594%
Volume Distribution (VD):  2.962
Pgp-substrate:  1.1561769247055054%

ADMET: Metabolism

CYP1A2-inhibitor:  0.083
CYP1A2-substrate:  0.594
CYP2C19-inhibitor:  0.724
CYP2C19-substrate:  0.167
CYP2C9-inhibitor:  0.829
CYP2C9-substrate:  0.949
CYP2D6-inhibitor:  0.023
CYP2D6-substrate:  0.031
CYP3A4-inhibitor:  0.788
CYP3A4-substrate:  0.309

ADMET: Excretion

Clearance (CL):  5.436
Half-life (T1/2):  0.046

ADMET: Toxicity

hERG Blockers:  0.007
Human Hepatotoxicity (H-HT):  0.958
Drug-inuced Liver Injury (DILI):  0.956
AMES Toxicity:  0.013
Rat Oral Acute Toxicity:  0.958
Maximum Recommended Daily Dose:  0.982
Skin Sensitization:  0.087
Carcinogencity:  0.02
Eye Corrosion:  0.003
Eye Irritation:  0.015
Respiratory Toxicity:  0.939

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

  Natural Product: NPC104924

Natural Product ID:  NPC104924
Common Name*:   Lipidyl Pseudopterane A
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  VBMMZFOCKDLDJI-LTCBTEPNSA-N
Standard InCHI:  InChI=1S/C37H54O8/c1-7-8-9-10-11-12-13-14-15-16-17-18-19-20-32(38)45-35-28-23-31(44-37(28)41)33(25(4)5)30-22-27(36(40)42-6)29(43-30)21-26(24(2)3)34(35)39/h22-23,26,31,33-35,39H,2,4,7-21H2,1,3,5-6H3/t26-,31-,33+,34-,35-/m1/s1
SMILES:  CCCCCCCCCCCCCCCC(=O)O[C@H]1[C@H](O)[C@H](Cc2oc([C@@H]([C@H]3C=C1C(=O)O3)C(=C)C)cc2C(=O)OC)C(=C)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL508425
PubChem CID:   44563511
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0000076] Furans
        • [CHEMONTID:0004758] Furoic acid and derivatives
          • [CHEMONTID:0004805] Furoic acid esters

*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
NPO26598 Antillogorgia acerosa Species Gorgoniidae Eukaryota n.a. n.a. n.a. PMID[19061360]
NPO27037 Hornschuchia obliqua Species Annonaceae Eukaryota n.a. Brazilian n.a. PMID[26135746]
NPO25476 Peridinium bipes Species Peridiniaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO25476 Peridinium bipes Species Peridiniaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO13810 Magnolia champaca Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO26466 Eucalyptus youngiana Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25898 Symplocos spicata Species Symplocaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25762 Lomatia tinctoria Species Proteaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26762 Pachymedusa dacnicolor Species Hylidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23569 Roubieva multifida n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO26270 Paronychia chionaea Species Caryophyllaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24034 Geraea viscida Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26012 Bothriocline calycina Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25476 Peridinium bipes Species Peridiniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26089 Vismia martiana Species Hypericaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24864 Senecio umgeniensis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14910 Artemisia inculta Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29037 Boletus peckii Species Boletaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6960 Larrea nitida Species Zygophyllaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26829 Passiflora hybr Species Passifloraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16889 Cardamine diphylla Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26598 Antillogorgia acerosa Species Gorgoniidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26436 Citrus glauca Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26569 Sigmadocia pumila Species Chalinidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13810 Magnolia champaca Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27037 Hornschuchia obliqua Species Annonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26666 Filipendula hexapetala Species Rosaceae 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
NPT178 Individual Protein Protein-tyrosine phosphatase 1B Homo sapiens IC50 = 71.0 ug.mL-1 PMID[454315]

☑ 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 NPC104924 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
0.964 High Similarity NPC254198
0.9097 High Similarity NPC37488
0.9078 High Similarity NPC107571
0.9078 High Similarity NPC474615
0.9065 High Similarity NPC159786
0.9054 High Similarity NPC474219
0.9054 High Similarity NPC474378
0.8913 High Similarity NPC136340
0.8865 High Similarity NPC303217
0.8844 High Similarity NPC474317
0.8836 High Similarity NPC195920
0.8776 High Similarity NPC475864
0.8699 High Similarity NPC110305
0.8658 High Similarity NPC474220
0.8658 High Similarity NPC474255
0.8658 High Similarity NPC471618
0.8621 High Similarity NPC282973
0.86 High Similarity NPC474270
0.86 High Similarity NPC475904
0.8571 High Similarity NPC22248
0.8542 High Similarity NPC473268
0.8389 Intermediate Similarity NPC267004
0.8389 Intermediate Similarity NPC307346
0.8389 Intermediate Similarity NPC218712
0.8389 Intermediate Similarity NPC261733
0.8288 Intermediate Similarity NPC286130
0.8252 Intermediate Similarity NPC17681
0.8194 Intermediate Similarity NPC97740
0.8194 Intermediate Similarity NPC45358
0.8187 Intermediate Similarity NPC261184
0.8176 Intermediate Similarity NPC188649
0.816 Intermediate Similarity NPC294512
0.8156 Intermediate Similarity NPC329922
0.8156 Intermediate Similarity NPC329694
0.8156 Intermediate Similarity NPC81912
0.8156 Intermediate Similarity NPC474260
0.8138 Intermediate Similarity NPC474407
0.8138 Intermediate Similarity NPC474426
0.8138 Intermediate Similarity NPC474425
0.8137 Intermediate Similarity NPC121995
0.8125 Intermediate Similarity NPC88841
0.8125 Intermediate Similarity NPC14822
0.8125 Intermediate Similarity NPC288602
0.8101 Intermediate Similarity NPC472777
0.8101 Intermediate Similarity NPC472776
0.8101 Intermediate Similarity NPC472778
0.8099 Intermediate Similarity NPC471554
0.8099 Intermediate Similarity NPC473355
0.8099 Intermediate Similarity NPC471573
0.8099 Intermediate Similarity NPC471501
0.8099 Intermediate Similarity NPC476016
0.8086 Intermediate Similarity NPC270312
0.8082 Intermediate Similarity NPC106247
0.8067 Intermediate Similarity NPC248795
0.8063 Intermediate Similarity NPC95472
0.8063 Intermediate Similarity NPC303210
0.8063 Intermediate Similarity NPC239270
0.8063 Intermediate Similarity NPC68848
0.8063 Intermediate Similarity NPC49009
0.8063 Intermediate Similarity NPC169
0.8061 Intermediate Similarity NPC472584
0.805 Intermediate Similarity NPC474611
0.8042 Intermediate Similarity NPC474279
0.8042 Intermediate Similarity NPC474438
0.8041 Intermediate Similarity NPC215109
0.8041 Intermediate Similarity NPC170604
0.8038 Intermediate Similarity NPC474542
0.8027 Intermediate Similarity NPC14650
0.8026 Intermediate Similarity NPC137295
0.8025 Intermediate Similarity NPC89131
0.8012 Intermediate Similarity NPC283209
0.8012 Intermediate Similarity NPC56953
0.8012 Intermediate Similarity NPC285567
0.8012 Intermediate Similarity NPC176413
0.8 Intermediate Similarity NPC120220
0.8 Intermediate Similarity NPC211625
0.8 Intermediate Similarity NPC287559
0.8 Intermediate Similarity NPC323118
0.7987 Intermediate Similarity NPC88007
0.7987 Intermediate Similarity NPC194499
0.7987 Intermediate Similarity NPC173544
0.7975 Intermediate Similarity NPC301233
0.7974 Intermediate Similarity NPC10302
0.7974 Intermediate Similarity NPC105381
0.7972 Intermediate Similarity NPC474830
0.7972 Intermediate Similarity NPC137570
0.7963 Intermediate Similarity NPC56358
0.7962 Intermediate Similarity NPC121615
0.7962 Intermediate Similarity NPC240768
0.7962 Intermediate Similarity NPC200773
0.7962 Intermediate Similarity NPC294511
0.7959 Intermediate Similarity NPC288209
0.7958 Intermediate Similarity NPC71274
0.7958 Intermediate Similarity NPC75557
0.795 Intermediate Similarity NPC18986
0.795 Intermediate Similarity NPC300680
0.7945 Intermediate Similarity NPC473344
0.7945 Intermediate Similarity NPC471545
0.7945 Intermediate Similarity NPC471544
0.7943 Intermediate Similarity NPC475818
0.7939 Intermediate Similarity NPC475641
0.7939 Intermediate Similarity NPC475237
0.7937 Intermediate Similarity NPC472779
0.7937 Intermediate Similarity NPC116639
0.7937 Intermediate Similarity NPC269495
0.7937 Intermediate Similarity NPC140952
0.7937 Intermediate Similarity NPC262872
0.7935 Intermediate Similarity NPC7388
0.7931 Intermediate Similarity NPC45947
0.7927 Intermediate Similarity NPC296558
0.7925 Intermediate Similarity NPC41880
0.7925 Intermediate Similarity NPC469485
0.7922 Intermediate Similarity NPC316535
0.7922 Intermediate Similarity NPC62799
0.7919 Intermediate Similarity NPC186626
0.7917 Intermediate Similarity NPC325176
0.7914 Intermediate Similarity NPC475779
0.7914 Intermediate Similarity NPC86800
0.7911 Intermediate Similarity NPC114880
0.7911 Intermediate Similarity NPC256141
0.7902 Intermediate Similarity NPC216810
0.7901 Intermediate Similarity NPC92589
0.7898 Intermediate Similarity NPC327059
0.7898 Intermediate Similarity NPC470908
0.7898 Intermediate Similarity NPC321387
0.7888 Intermediate Similarity NPC477402
0.7888 Intermediate Similarity NPC279732
0.7885 Intermediate Similarity NPC329180
0.7875 Intermediate Similarity NPC195954
0.7875 Intermediate Similarity NPC45101
0.7875 Intermediate Similarity NPC304692
0.7875 Intermediate Similarity NPC81405
0.7871 Intermediate Similarity NPC250228
0.7866 Intermediate Similarity NPC473908
0.7862 Intermediate Similarity NPC281258
0.7862 Intermediate Similarity NPC75310
0.7862 Intermediate Similarity NPC470331
0.7862 Intermediate Similarity NPC264943
0.7853 Intermediate Similarity NPC472664
0.7853 Intermediate Similarity NPC276735
0.7848 Intermediate Similarity NPC474772
0.7848 Intermediate Similarity NPC474744
0.7848 Intermediate Similarity NPC470380
0.7848 Intermediate Similarity NPC190217
0.7848 Intermediate Similarity NPC472423
0.7848 Intermediate Similarity NPC23253
0.7844 Intermediate Similarity NPC247964
0.7843 Intermediate Similarity NPC242756
0.7843 Intermediate Similarity NPC171870
0.784 Intermediate Similarity NPC304839
0.784 Intermediate Similarity NPC263432
0.784 Intermediate Similarity NPC207978
0.784 Intermediate Similarity NPC69028
0.784 Intermediate Similarity NPC220582
0.784 Intermediate Similarity NPC329938
0.7834 Intermediate Similarity NPC104172
0.7834 Intermediate Similarity NPC307052
0.7834 Intermediate Similarity NPC139966
0.7834 Intermediate Similarity NPC88886
0.7832 Intermediate Similarity NPC474829
0.7826 Intermediate Similarity NPC84349
0.7826 Intermediate Similarity NPC475226
0.7826 Intermediate Similarity NPC307383
0.7821 Intermediate Similarity NPC473133
0.7821 Intermediate Similarity NPC61284
0.7821 Intermediate Similarity NPC113428
0.7821 Intermediate Similarity NPC91902
0.7821 Intermediate Similarity NPC47388
0.7821 Intermediate Similarity NPC202494
0.7821 Intermediate Similarity NPC470670
0.7817 Intermediate Similarity NPC476351
0.7812 Intermediate Similarity NPC104736
0.7806 Intermediate Similarity NPC30890
0.7806 Intermediate Similarity NPC297788
0.7805 Intermediate Similarity NPC470875
0.7801 Intermediate Similarity NPC1848
0.7801 Intermediate Similarity NPC79557
0.7799 Intermediate Similarity NPC34965
0.7799 Intermediate Similarity NPC183536
0.7792 Intermediate Similarity NPC476164
0.7792 Intermediate Similarity NPC476310
0.7792 Intermediate Similarity NPC84479
0.7791 Intermediate Similarity NPC45124
0.7791 Intermediate Similarity NPC30655
0.7791 Intermediate Similarity NPC74854
0.7791 Intermediate Similarity NPC477405
0.7791 Intermediate Similarity NPC472773
0.7791 Intermediate Similarity NPC269117
0.7785 Intermediate Similarity NPC180351
0.7785 Intermediate Similarity NPC106025
0.7785 Intermediate Similarity NPC214454
0.7785 Intermediate Similarity NPC477240
0.7785 Intermediate Similarity NPC472421
0.7785 Intermediate Similarity NPC62354
0.7785 Intermediate Similarity NPC476509
0.7778 Intermediate Similarity NPC333139
0.7778 Intermediate Similarity NPC43761
0.7778 Intermediate Similarity NPC470856
0.7778 Intermediate Similarity NPC476349
0.7778 Intermediate Similarity NPC470789

  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 NPC104924 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
0.7778 Intermediate Similarity NPD5537 Clinical (unspecified phase)
0.7778 Intermediate Similarity NPD8434 Phase 2
0.775 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.7716 Intermediate Similarity NPD7075 Discontinued
0.7662 Intermediate Similarity NPD4628 Phase 3
0.7628 Intermediate Similarity NPD6799 Approved
0.7578 Intermediate Similarity NPD6801 Discontinued
0.7531 Intermediate Similarity NPD7819 Suspended
0.75 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.7485 Intermediate Similarity NPD5402 Approved
0.7484 Intermediate Similarity NPD5403 Approved
0.7484 Intermediate Similarity NPD920 Approved
0.7468 Intermediate Similarity NPD5401 Approved
0.7456 Intermediate Similarity NPD3818 Discontinued
0.7453 Intermediate Similarity NPD4380 Phase 2
0.7453 Intermediate Similarity NPD6599 Discontinued
0.7384 Intermediate Similarity NPD6559 Discontinued
0.7383 Intermediate Similarity NPD6832 Phase 2
0.7378 Intermediate Similarity NPD3817 Phase 2
0.7372 Intermediate Similarity NPD1243 Approved
0.7358 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7355 Intermediate Similarity NPD2343 Clinical (unspecified phase)
0.7355 Intermediate Similarity NPD2344 Approved
0.7333 Intermediate Similarity NPD3882 Suspended
0.7333 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7325 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7317 Intermediate Similarity NPD5761 Phase 2
0.7317 Intermediate Similarity NPD5760 Phase 2
0.731 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.7301 Intermediate Similarity NPD7411 Suspended
0.729 Intermediate Similarity NPD2796 Approved
0.7273 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.7256 Intermediate Similarity NPD1934 Approved
0.7255 Intermediate Similarity NPD447 Suspended
0.7251 Intermediate Similarity NPD7893 Clinical (unspecified phase)
0.725 Intermediate Similarity NPD2532 Approved
0.725 Intermediate Similarity NPD2534 Approved
0.725 Intermediate Similarity NPD2533 Approved
0.7248 Intermediate Similarity NPD5647 Approved
0.7233 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.7226 Intermediate Similarity NPD2799 Discontinued
0.7212 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7211 Intermediate Similarity NPD9717 Approved
0.7202 Intermediate Similarity NPD5494 Approved
0.72 Intermediate Similarity NPD8313 Approved
0.72 Intermediate Similarity NPD8312 Approved
0.7197 Intermediate Similarity NPD1549 Phase 2
0.719 Intermediate Similarity NPD7966 Clinical (unspecified phase)
0.7186 Intermediate Similarity NPD3749 Approved
0.7178 Intermediate Similarity NPD3226 Approved
0.7176 Intermediate Similarity NPD3926 Phase 2
0.7171 Intermediate Similarity NPD2313 Discontinued
0.717 Intermediate Similarity NPD2309 Approved
0.7168 Intermediate Similarity NPD7074 Phase 3
0.7152 Intermediate Similarity NPD2800 Approved
0.7152 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD919 Approved
0.7143 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.7135 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.7135 Intermediate Similarity NPD6166 Phase 2
0.7135 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.7134 Intermediate Similarity NPD6002 Phase 3
0.7134 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.7134 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.7134 Intermediate Similarity NPD6006 Clinical (unspecified phase)
0.7134 Intermediate Similarity NPD6004 Phase 3
0.7134 Intermediate Similarity NPD6003 Clinical (unspecified phase)
0.7134 Intermediate Similarity NPD6005 Phase 3
0.7126 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7115 Intermediate Similarity NPD7033 Discontinued
0.7111 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.711 Intermediate Similarity NPD7054 Approved
0.7108 Intermediate Similarity NPD2801 Approved
0.7093 Intermediate Similarity NPD7473 Discontinued
0.7089 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.707 Intermediate Similarity NPD1551 Phase 2
0.7069 Intermediate Similarity NPD7472 Approved
0.7059 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7045 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.7045 Intermediate Similarity NPD7808 Phase 3
0.7035 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.7032 Intermediate Similarity NPD6355 Discontinued
0.7032 Intermediate Similarity NPD230 Phase 1
0.7025 Intermediate Similarity NPD1471 Phase 3
0.7024 Intermediate Similarity NPD7768 Phase 2
0.702 Intermediate Similarity NPD1019 Discontinued
0.7018 Intermediate Similarity NPD6808 Phase 2
0.7006 Intermediate Similarity NPD1510 Phase 2
0.6989 Remote Similarity NPD7251 Discontinued
0.6989 Remote Similarity NPD6765 Approved
0.6989 Remote Similarity NPD6764 Approved
0.6987 Remote Similarity NPD6653 Approved
0.698 Remote Similarity NPD1608 Approved
0.6975 Remote Similarity NPD6143 Clinical (unspecified phase)
0.6968 Remote Similarity NPD1240 Approved
0.6962 Remote Similarity NPD2935 Discontinued
0.6959 Remote Similarity NPD1247 Approved
0.6954 Remote Similarity NPD1203 Approved
0.6951 Remote Similarity NPD6980 Clinical (unspecified phase)
0.6933 Remote Similarity NPD7410 Clinical (unspecified phase)
0.6933 Remote Similarity NPD7004 Clinical (unspecified phase)
0.6932 Remote Similarity NPD6797 Phase 2
0.6932 Remote Similarity NPD5953 Discontinued
0.6927 Remote Similarity NPD8055 Clinical (unspecified phase)
0.6923 Remote Similarity NPD1899 Clinical (unspecified phase)
0.6919 Remote Similarity NPD6232 Discontinued
0.6918 Remote Similarity NPD2346 Discontinued
0.6893 Remote Similarity NPD7685 Pre-registration
0.6889 Remote Similarity NPD8150 Discontinued
0.6879 Remote Similarity NPD1607 Approved
0.6879 Remote Similarity NPD6651 Approved
0.6871 Remote Similarity NPD1511 Approved
0.6871 Remote Similarity NPD9545 Approved
0.686 Remote Similarity NPD7199 Phase 2
0.6839 Remote Similarity NPD3268 Approved
0.6839 Remote Similarity NPD411 Approved
0.6833 Remote Similarity NPD6784 Approved
0.6833 Remote Similarity NPD6785 Approved
0.6824 Remote Similarity NPD4965 Approved
0.6824 Remote Similarity NPD4966 Approved
0.6824 Remote Similarity NPD4967 Phase 2
0.6818 Remote Similarity NPD7286 Phase 2
0.6818 Remote Similarity NPD5844 Phase 1
0.6815 Remote Similarity NPD1933 Approved
0.6805 Remote Similarity NPD7972 Discontinued
0.6805 Remote Similarity NPD8455 Phase 2
0.6803 Remote Similarity NPD9092 Discovery
0.68 Remote Similarity NPD1547 Clinical (unspecified phase)
0.6797 Remote Similarity NPD6007 Clinical (unspecified phase)
0.6797 Remote Similarity NPD2798 Approved
0.6795 Remote Similarity NPD6233 Phase 2
0.679 Remote Similarity NPD6398 Clinical (unspecified phase)
0.679 Remote Similarity NPD3750 Approved
0.6788 Remote Similarity NPD1512 Approved
0.6779 Remote Similarity NPD17 Approved
0.6774 Remote Similarity NPD8090 Clinical (unspecified phase)
0.677 Remote Similarity NPD2424 Discontinued
0.6765 Remote Similarity NPD5353 Approved
0.6763 Remote Similarity NPD8127 Discontinued
0.6763 Remote Similarity NPD6959 Discontinued
0.6751 Remote Similarity NPD8404 Phase 2
0.6748 Remote Similarity NPD3887 Approved
0.6748 Remote Similarity NPD2354 Approved
0.6746 Remote Similarity NPD37 Approved
0.6746 Remote Similarity NPD6280 Approved
0.6746 Remote Similarity NPD6279 Approved
0.6744 Remote Similarity NPD6234 Discontinued
0.6743 Remote Similarity NPD4575 Clinical (unspecified phase)
0.6743 Remote Similarity NPD7784 Clinical (unspecified phase)
0.6735 Remote Similarity NPD9493 Approved
0.6732 Remote Similarity NPD6362 Approved
0.6732 Remote Similarity NPD2797 Approved
0.6731 Remote Similarity NPD6798 Discontinued
0.6731 Remote Similarity NPD1699 Clinical (unspecified phase)
0.673 Remote Similarity NPD7097 Phase 1
0.6727 Remote Similarity NPD4662 Approved
0.6727 Remote Similarity NPD4661 Approved
0.6721 Remote Similarity NPD8397 Clinical (unspecified phase)
0.6706 Remote Similarity NPD1465 Phase 2
0.669 Remote Similarity NPD7843 Approved
0.6687 Remote Similarity NPD4308 Phase 3
0.6687 Remote Similarity NPD3748 Approved
0.6687 Remote Similarity NPD6273 Approved
0.6686 Remote Similarity NPD7184 Clinical (unspecified phase)
0.6667 Remote Similarity NPD7458 Discontinued
0.6667 Remote Similarity NPD2296 Approved
0.6667 Remote Similarity NPD5808 Clinical (unspecified phase)
0.6667 Remote Similarity NPD7228 Approved
0.6667 Remote Similarity NPD3751 Discontinued
0.6667 Remote Similarity NPD2163 Approved
0.6649 Remote Similarity NPD7435 Discontinued
0.6648 Remote Similarity NPD2403 Approved
0.6647 Remote Similarity NPD6844 Discontinued
0.6646 Remote Similarity NPD6190 Approved
0.6629 Remote Similarity NPD5710 Approved
0.6629 Remote Similarity NPD5711 Approved
0.6626 Remote Similarity NPD2654 Approved
0.6624 Remote Similarity NPD3764 Approved
0.6623 Remote Similarity NPD3266 Approved
0.6623 Remote Similarity NPD3267 Approved
0.6605 Remote Similarity NPD5763 Approved
0.6605 Remote Similarity NPD5762 Approved
0.6588 Remote Similarity NPD6385 Approved
0.6588 Remote Similarity NPD6386 Approved
0.6582 Remote Similarity NPD4062 Phase 3
0.6575 Remote Similarity NPD4419 Clinical (unspecified phase)
0.6573 Remote Similarity NPD7799 Discontinued
0.6564 Remote Similarity NPD8151 Discontinued
0.6558 Remote Similarity NPD1876 Approved
0.6556 Remote Similarity NPD1778 Approved
0.6554 Remote Similarity NPD7157 Approved
0.6552 Remote Similarity NPD2181 Clinical (unspecified phase)
0.6543 Remote Similarity NPD6100 Approved
0.6543 Remote Similarity NPD6099 Approved
0.6541 Remote Similarity NPD4307 Phase 2
0.6538 Remote Similarity NPD9494 Approved
0.6536 Remote Similarity NPD3972 Approved
0.6534 Remote Similarity NPD7229 Phase 3
0.6534 Remote Similarity NPD3787 Discontinued
0.6531 Remote Similarity NPD7875 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