Structure

Physi-Chem Properties

Molecular Weight:  638.48
Volume:  687.887
LogP:  8.011
LogD:  4.723
LogS:  -5.42
# Rotatable Bonds:  25
TPSA:  132.75
# H-Bond Aceptor:  8
# H-Bond Donor:  5
# Rings:  3
# Heavy Atoms:  8

MedChem Properties

QED Drug-Likeness Score:  0.07
Synthetic Accessibility Score:  4.835
Fsp3:  0.892
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:  -5.268
MDCK Permeability:  1.0370063137088437e-05
Pgp-inhibitor:  0.054
Pgp-substrate:  0.982
Human Intestinal Absorption (HIA):  0.02
20% Bioavailability (F20%):  1.0
30% Bioavailability (F30%):  0.598

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.003
Plasma Protein Binding (PPB):  96.7200698852539%
Volume Distribution (VD):  0.811
Pgp-substrate:  3.8424298763275146%

ADMET: Metabolism

CYP1A2-inhibitor:  0.012
CYP1A2-substrate:  0.67
CYP2C19-inhibitor:  0.041
CYP2C19-substrate:  0.056
CYP2C9-inhibitor:  0.067
CYP2C9-substrate:  0.943
CYP2D6-inhibitor:  0.004
CYP2D6-substrate:  0.078
CYP3A4-inhibitor:  0.115
CYP3A4-substrate:  0.022

ADMET: Excretion

Clearance (CL):  6.028
Half-life (T1/2):  0.087

ADMET: Toxicity

hERG Blockers:  0.414
Human Hepatotoxicity (H-HT):  0.338
Drug-inuced Liver Injury (DILI):  0.04
AMES Toxicity:  0.046
Rat Oral Acute Toxicity:  0.38
Maximum Recommended Daily Dose:  0.924
Skin Sensitization:  0.961
Carcinogencity:  0.071
Eye Corrosion:  0.003
Eye Irritation:  0.013
Respiratory Toxicity:  0.711

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

  Natural Product: NPC91067

Natural Product ID:  NPC91067
Common Name*:   Glacin B
IUPAC Name:   (2S)-4-[(2R,8R)-8-[(2R,5R)-5-[(2R,5S)-5-[(5S,6S)-5,6-dihydroxyhexadecyl]oxolan-2-yl]oxolan-2-yl]-2,8-dihydroxyoctyl]-2-methyl-2H-furan-5-one
Synonyms:  
Standard InCHIKey:  CXWUDOBKRFRXAX-KWENDKABSA-N
Standard InCHI:  InChI=1S/C37H66O8/c1-3-4-5-6-7-8-9-12-18-31(39)32(40)19-15-14-17-30-21-22-35(44-30)36-24-23-34(45-36)33(41)20-13-10-11-16-29(38)26-28-25-27(2)43-37(28)42/h25,27,29-36,38-41H,3-24,26H2,1-2H3/t27-,29+,30-,31-,32-,33+,34+,35+,36+/m0/s1
SMILES:  CCCCCCCCCC[C@@H]([C@H](CCCC[C@H]1CC[C@@H](O1)[C@H]1CC[C@@H](O1)[C@@H](CCCCC[C@H](CC1=C[C@@H](OC1=O)C)O)O)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL455824
PubChem CID:   44559068
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0003909] Fatty Acyls
        • [CHEMONTID:0001334] Fatty alcohols
          • [CHEMONTID:0002518] Annonaceous acetogenins

*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
NPO6333 Annona glabra Species Annonaceae Eukaryota n.a. stem wood n.a. DOI[10.1021/np100247r]
NPO6333 Annona glabra Species Annonaceae Eukaryota n.a. n.a. n.a. PMID[10395501]
NPO6333 Annona glabra Species Annonaceae Eukaryota n.a. n.a. n.a. PMID[10425140]
NPO6333 Annona glabra Species Annonaceae Eukaryota Fruits n.a. n.a. PMID[15568797]
NPO6333 Annona glabra Species Annonaceae Eukaryota stem Taipei Botanical Garden, Taipei, Taiwan, China 2006-MAR PMID[20828184]
NPO6333 Annona glabra Species Annonaceae Eukaryota fruits n.a. n.a. PMID[25499882]
NPO6333 Annona glabra Species Annonaceae Eukaryota n.a. n.a. n.a. PMID[9584397]
NPO6333 Annona glabra Species Annonaceae Eukaryota n.a. n.a. n.a. PMID[9599260]
NPO6333 Annona glabra Species Annonaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO6333 Annona glabra Species Annonaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO6333 Annona glabra Species Annonaceae 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
NPT81 Cell Line A549 Homo sapiens ED50 = 1.29 ug ml-1 PMID[494323]
NPT83 Cell Line MCF7 Homo sapiens ED50 = 5.2 10'-2 ug/ml PMID[494323]
NPT139 Cell Line HT-29 Homo sapiens ED50 = 8.68 10'-2 ug/ml PMID[494323]
NPT376 Cell Line A498 Homo sapiens ED50 = 2.61 ug ml-1 PMID[494323]
NPT306 Cell Line PC-3 Homo sapiens ED50 = 5.59 10'-2 ug/ml PMID[494323]
NPT783 Cell Line MIA PaCa-2 Homo sapiens ED50 = 2.74 10'-2 ug/ml PMID[494323]
NPT306 Cell Line PC-3 Homo sapiens ED50 = 5.6 10'-2 ug/ml PMID[494324]
NPT783 Cell Line MIA PaCa-2 Homo sapiens ED50 = 1.5 10'-2 ug/ml PMID[494324]
NPT81 Cell Line A549 Homo sapiens ED50 = 1.3 ug ml-1 PMID[494324]
NPT83 Cell Line MCF7 Homo sapiens ED50 = 5.2 10'-2 ug/ml PMID[494324]
NPT139 Cell Line HT-29 Homo sapiens ED50 = 8.7 10'-2 ug/ml PMID[494324]
NPT376 Cell Line A498 Homo sapiens ED50 = 2.6 ug ml-1 PMID[494324]
NPT306 Cell Line PC-3 Homo sapiens ED50 = 1.2 ug ml-1 PMID[494325]
NPT783 Cell Line MIA PaCa-2 Homo sapiens ED50 = 2.8 10'-1 ug/ml PMID[494325]
NPT81 Cell Line A549 Homo sapiens ED50 = 1.6 10'-1 ug/ml PMID[494325]
NPT83 Cell Line MCF7 Homo sapiens ED50 = 1.8 10'-3 ug/ml PMID[494325]
NPT139 Cell Line HT-29 Homo sapiens ED50 = 1.9 10'-2 ug/ml PMID[494325]
NPT376 Cell Line A498 Homo sapiens ED50 = 1.4 ug ml-1 PMID[494325]
NPT176 Organism Artemia salina Artemia salina LC50 = 0.27 ug.mL-1 PMID[494323]
NPT140 Organism Artemia Artemia LC50 = 0.27 ug.mL-1 PMID[494324]
NPT140 Organism Artemia Artemia LC50 = 0.31 ug.mL-1 PMID[494325]

☑ 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 NPC91067 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 NPC93794
1.0 High Similarity NPC42598
1.0 High Similarity NPC473504
1.0 High Similarity NPC81778
1.0 High Similarity NPC318963
1.0 High Similarity NPC20621
1.0 High Similarity NPC40066
0.9881 High Similarity NPC239517
0.988 High Similarity NPC81045
0.988 High Similarity NPC242364
0.988 High Similarity NPC261952
0.988 High Similarity NPC100454
0.988 High Similarity NPC320569
0.988 High Similarity NPC274446
0.988 High Similarity NPC191929
0.988 High Similarity NPC172821
0.988 High Similarity NPC169511
0.988 High Similarity NPC287164
0.988 High Similarity NPC151403
0.988 High Similarity NPC61257
0.988 High Similarity NPC234077
0.988 High Similarity NPC171135
0.988 High Similarity NPC133730
0.988 High Similarity NPC39754
0.9759 High Similarity NPC258068
0.9759 High Similarity NPC476583
0.9759 High Similarity NPC20533
0.9643 High Similarity NPC20339
0.9643 High Similarity NPC21208
0.9643 High Similarity NPC233551
0.9643 High Similarity NPC280621
0.9643 High Similarity NPC40376
0.9643 High Similarity NPC320458
0.9643 High Similarity NPC48338
0.9643 High Similarity NPC473905
0.9639 High Similarity NPC107717
0.9639 High Similarity NPC241360
0.9639 High Similarity NPC231096
0.9639 High Similarity NPC473840
0.9639 High Similarity NPC142117
0.9639 High Similarity NPC132940
0.9639 High Similarity NPC475581
0.9639 High Similarity NPC114694
0.9639 High Similarity NPC171174
0.9639 High Similarity NPC25703
0.9639 High Similarity NPC240695
0.9639 High Similarity NPC219652
0.9639 High Similarity NPC134865
0.9639 High Similarity NPC103523
0.9639 High Similarity NPC62118
0.9639 High Similarity NPC232555
0.9639 High Similarity NPC282815
0.9639 High Similarity NPC293136
0.9529 High Similarity NPC477011
0.9524 High Similarity NPC178215
0.9518 High Similarity NPC110710
0.9518 High Similarity NPC132496
0.9518 High Similarity NPC231009
0.9518 High Similarity NPC473669
0.9518 High Similarity NPC292809
0.9518 High Similarity NPC283085
0.9518 High Similarity NPC329615
0.9518 High Similarity NPC473651
0.9518 High Similarity NPC319036
0.9518 High Similarity NPC329838
0.9518 High Similarity NPC470400
0.9518 High Similarity NPC39167
0.9518 High Similarity NPC82795
0.9518 High Similarity NPC66346
0.9518 High Similarity NPC107986
0.9518 High Similarity NPC473478
0.9518 High Similarity NPC473671
0.9518 High Similarity NPC1083
0.9518 High Similarity NPC235809
0.9518 High Similarity NPC103284
0.9518 High Similarity NPC286338
0.9518 High Similarity NPC25764
0.9518 High Similarity NPC475268
0.9518 High Similarity NPC202055
0.9518 High Similarity NPC473156
0.9518 High Similarity NPC77871
0.9518 High Similarity NPC39279
0.9518 High Similarity NPC9678
0.9518 High Similarity NPC223871
0.9419 High Similarity NPC473904
0.9405 High Similarity NPC219498
0.9405 High Similarity NPC308412
0.9405 High Similarity NPC210218
0.9405 High Similarity NPC204686
0.9405 High Similarity NPC134885
0.9405 High Similarity NPC473687
0.9405 High Similarity NPC69082
0.9405 High Similarity NPC279267
0.9405 High Similarity NPC134807
0.9398 High Similarity NPC156804
0.9302 High Similarity NPC139418
0.9302 High Similarity NPC130359
0.9302 High Similarity NPC14901
0.9294 High Similarity NPC159750
0.9294 High Similarity NPC154097
0.9294 High Similarity NPC473995
0.9294 High Similarity NPC470401
0.9294 High Similarity NPC473649
0.9286 High Similarity NPC120398
0.9286 High Similarity NPC477014
0.9286 High Similarity NPC477013
0.9286 High Similarity NPC471567
0.9286 High Similarity NPC322529
0.9186 High Similarity NPC89001
0.9176 High Similarity NPC47937
0.9176 High Similarity NPC477015
0.9176 High Similarity NPC112685
0.9167 High Similarity NPC163093
0.9157 High Similarity NPC473780
0.9157 High Similarity NPC11332
0.9157 High Similarity NPC94875
0.9157 High Similarity NPC73310
0.9157 High Similarity NPC329829
0.9157 High Similarity NPC145914
0.9157 High Similarity NPC475159
0.9157 High Similarity NPC180363
0.9157 High Similarity NPC473712
0.9157 High Similarity NPC131002
0.9157 High Similarity NPC473529
0.9157 High Similarity NPC65930
0.908 High Similarity NPC477016
0.908 High Similarity NPC280612
0.908 High Similarity NPC477017
0.9059 High Similarity NPC477018
0.9059 High Similarity NPC100921
0.9059 High Similarity NPC182383
0.9048 High Similarity NPC144415
0.9048 High Similarity NPC253801
0.8989 High Similarity NPC473561
0.8989 High Similarity NPC11456
0.8989 High Similarity NPC475173
0.8989 High Similarity NPC473723
0.8989 High Similarity NPC473663
0.8989 High Similarity NPC473520
0.8953 High Similarity NPC309211
0.8953 High Similarity NPC477010
0.8876 High Similarity NPC473707
0.8851 High Similarity NPC477012
0.837 Intermediate Similarity NPC179746
0.837 Intermediate Similarity NPC81419
0.8261 Intermediate Similarity NPC30515
0.8261 Intermediate Similarity NPC12172
0.8261 Intermediate Similarity NPC208886
0.8191 Intermediate Similarity NPC36954
0.8172 Intermediate Similarity NPC476300
0.8152 Intermediate Similarity NPC473619
0.8152 Intermediate Similarity NPC51004
0.8125 Intermediate Similarity NPC187268
0.8065 Intermediate Similarity NPC473321
0.8065 Intermediate Similarity NPC184463
0.8061 Intermediate Similarity NPC86077
0.8043 Intermediate Similarity NPC295312
0.8043 Intermediate Similarity NPC92974
0.8043 Intermediate Similarity NPC307411
0.8 Intermediate Similarity NPC21469
0.7979 Intermediate Similarity NPC475912
0.7979 Intermediate Similarity NPC273579
0.7979 Intermediate Similarity NPC295204
0.7979 Intermediate Similarity NPC288240
0.7979 Intermediate Similarity NPC162205
0.7957 Intermediate Similarity NPC474761
0.7957 Intermediate Similarity NPC476004
0.7938 Intermediate Similarity NPC473326
0.7935 Intermediate Similarity NPC202672
0.7935 Intermediate Similarity NPC58219
0.7935 Intermediate Similarity NPC177629
0.7917 Intermediate Similarity NPC279621
0.7917 Intermediate Similarity NPC476315
0.7912 Intermediate Similarity NPC469483
0.7907 Intermediate Similarity NPC475711
0.7895 Intermediate Similarity NPC474035
0.7895 Intermediate Similarity NPC81386
0.7849 Intermediate Similarity NPC474032
0.7841 Intermediate Similarity NPC133226
0.7841 Intermediate Similarity NPC470147
0.7826 Intermediate Similarity NPC160138
0.7826 Intermediate Similarity NPC186148
0.7812 Intermediate Similarity NPC270013
0.7812 Intermediate Similarity NPC14961
0.7812 Intermediate Similarity NPC471141
0.7812 Intermediate Similarity NPC471142
0.7789 Intermediate Similarity NPC212486
0.7778 Intermediate Similarity NPC286770
0.7778 Intermediate Similarity NPC284472
0.7778 Intermediate Similarity NPC229799
0.7778 Intermediate Similarity NPC116543
0.7766 Intermediate Similarity NPC478004
0.7766 Intermediate Similarity NPC478003
0.7766 Intermediate Similarity NPC474232
0.7766 Intermediate Similarity NPC158388
0.7766 Intermediate Similarity NPC473448
0.7755 Intermediate Similarity NPC161855
0.7755 Intermediate Similarity NPC471144
0.7745 Intermediate Similarity NPC26617
0.7742 Intermediate Similarity NPC473715

  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 NPC91067 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
0.7957 Intermediate Similarity NPD46 Approved
0.7957 Intermediate Similarity NPD6698 Approved
0.7745 Intermediate Similarity NPD7899 Clinical (unspecified phase)
0.7579 Intermediate Similarity NPD7838 Discovery
0.732 Intermediate Similarity NPD7983 Approved
0.7228 Intermediate Similarity NPD8029 Clinical (unspecified phase)
0.717 Intermediate Similarity NPD6686 Approved
0.7037 Intermediate Similarity NPD6371 Approved
0.6972 Remote Similarity NPD8413 Clinical (unspecified phase)
0.6875 Remote Similarity NPD1733 Clinical (unspecified phase)
0.6765 Remote Similarity NPD1698 Clinical (unspecified phase)
0.6735 Remote Similarity NPD4250 Approved
0.6735 Remote Similarity NPD4251 Approved
0.67 Remote Similarity NPD5785 Approved
0.6633 Remote Similarity NPD4249 Approved
0.66 Remote Similarity NPD1695 Approved
0.6571 Remote Similarity NPD4225 Approved
0.6531 Remote Similarity NPD5363 Approved
0.6531 Remote Similarity NPD6082 Clinical (unspecified phase)
0.6512 Remote Similarity NPD3197 Phase 1
0.6495 Remote Similarity NPD7154 Phase 3
0.6495 Remote Similarity NPD5362 Discontinued
0.6449 Remote Similarity NPD5344 Discontinued
0.6441 Remote Similarity NPD8515 Approved
0.6441 Remote Similarity NPD8517 Approved
0.6441 Remote Similarity NPD8516 Approved
0.6441 Remote Similarity NPD8513 Phase 3
0.6383 Remote Similarity NPD4756 Discovery
0.6354 Remote Similarity NPD5790 Clinical (unspecified phase)
0.6316 Remote Similarity NPD6053 Discontinued
0.6292 Remote Similarity NPD4247 Clinical (unspecified phase)
0.6262 Remote Similarity NPD7638 Approved
0.623 Remote Similarity NPD7507 Approved
0.6226 Remote Similarity NPD7839 Suspended
0.6224 Remote Similarity NPD4269 Approved
0.6224 Remote Similarity NPD4752 Clinical (unspecified phase)
0.6224 Remote Similarity NPD4270 Approved
0.6204 Remote Similarity NPD7639 Approved
0.6204 Remote Similarity NPD7640 Approved
0.6198 Remote Similarity NPD7830 Approved
0.6198 Remote Similarity NPD7829 Approved
0.6195 Remote Similarity NPD4061 Clinical (unspecified phase)
0.619 Remote Similarity NPD5282 Discontinued
0.6186 Remote Similarity NPD4252 Approved
0.6179 Remote Similarity NPD8074 Phase 3
0.6162 Remote Similarity NPD6110 Phase 1
0.6146 Remote Similarity NPD4268 Approved
0.6146 Remote Similarity NPD4271 Approved
0.614 Remote Similarity NPD5955 Clinical (unspecified phase)
0.6139 Remote Similarity NPD5786 Approved
0.6122 Remote Similarity NPD5369 Approved
0.6122 Remote Similarity NPD4790 Discontinued
0.6102 Remote Similarity NPD7115 Discovery
0.61 Remote Similarity NPD6400 Clinical (unspecified phase)
0.6095 Remote Similarity NPD5779 Approved
0.6095 Remote Similarity NPD5778 Approved
0.608 Remote Similarity NPD7319 Approved
0.6066 Remote Similarity NPD7642 Approved
0.6061 Remote Similarity NPD6435 Approved
0.6055 Remote Similarity NPD6648 Approved
0.605 Remote Similarity NPD7641 Discontinued
0.604 Remote Similarity NPD1694 Approved
0.6033 Remote Similarity NPD8033 Approved
0.602 Remote Similarity NPD4822 Approved
0.602 Remote Similarity NPD4821 Approved
0.602 Remote Similarity NPD4819 Approved
0.602 Remote Similarity NPD4820 Approved
0.6 Remote Similarity NPD7966 Clinical (unspecified phase)
0.6 Remote Similarity NPD5331 Approved
0.6 Remote Similarity NPD5332 Approved
0.6 Remote Similarity NPD8039 Approved
0.5979 Remote Similarity NPD5784 Clinical (unspecified phase)
0.5977 Remote Similarity NPD4246 Clinical (unspecified phase)
0.595 Remote Similarity NPD8294 Approved
0.595 Remote Similarity NPD8377 Approved
0.5917 Remote Similarity NPD7328 Approved
0.5917 Remote Similarity NPD7327 Approved
0.5902 Remote Similarity NPD8380 Approved
0.5902 Remote Similarity NPD8379 Approved
0.5902 Remote Similarity NPD8296 Approved
0.5902 Remote Similarity NPD8444 Approved
0.5902 Remote Similarity NPD8335 Approved
0.5902 Remote Similarity NPD8378 Approved
0.59 Remote Similarity NPD5209 Approved
0.5889 Remote Similarity NPD2685 Clinical (unspecified phase)
0.5877 Remote Similarity NPD6412 Phase 2
0.5877 Remote Similarity NPD5954 Clinical (unspecified phase)
0.5868 Remote Similarity NPD7516 Approved
0.5862 Remote Similarity NPD6421 Discontinued
0.5859 Remote Similarity NPD5368 Approved
0.5859 Remote Similarity NPD7260 Phase 2
0.5843 Remote Similarity NPD2664 Clinical (unspecified phase)
0.584 Remote Similarity NPD8273 Phase 1
0.584 Remote Similarity NPD8451 Approved
0.5833 Remote Similarity NPD3730 Approved
0.5833 Remote Similarity NPD4266 Approved
0.5833 Remote Similarity NPD3196 Approved
0.5833 Remote Similarity NPD3194 Approved
0.5833 Remote Similarity NPD3728 Approved
0.5833 Remote Similarity NPD3195 Phase 2
0.5833 Remote Similarity NPD7500 Approved
0.5824 Remote Similarity NPD3704 Approved
0.5814 Remote Similarity NPD6845 Suspended
0.5812 Remote Similarity NPD2204 Approved
0.5812 Remote Similarity NPD7116 Clinical (unspecified phase)
0.581 Remote Similarity NPD5370 Suspended
0.5794 Remote Similarity NPD8448 Approved
0.5794 Remote Similarity NPD6399 Phase 3
0.5772 Remote Similarity NPD8267 Approved
0.5772 Remote Similarity NPD8266 Approved
0.5772 Remote Similarity NPD8268 Approved
0.5772 Remote Similarity NPD8269 Approved
0.5763 Remote Similarity NPD8297 Approved
0.5747 Remote Similarity NPD6109 Phase 1
0.5747 Remote Similarity NPD69 Approved
0.5747 Remote Similarity NPD9119 Approved
0.5727 Remote Similarity NPD7902 Approved
0.5726 Remote Similarity NPD2067 Discontinued
0.5714 Remote Similarity NPD8133 Approved
0.5714 Remote Similarity NPD3172 Approved
0.5714 Remote Similarity NPD4632 Approved
0.5702 Remote Similarity NPD7505 Discontinued
0.5701 Remote Similarity NPD4810 Clinical (unspecified phase)
0.5701 Remote Similarity NPD7637 Suspended
0.5691 Remote Similarity NPD6319 Approved
0.568 Remote Similarity NPD8328 Phase 3
0.5669 Remote Similarity NPD7078 Approved
0.5664 Remote Similarity NPD7632 Discontinued
0.5663 Remote Similarity NPD6927 Phase 3
0.566 Remote Similarity NPD6101 Approved
0.566 Remote Similarity NPD5764 Clinical (unspecified phase)
0.5659 Remote Similarity NPD8392 Approved
0.5659 Remote Similarity NPD8391 Approved
0.5659 Remote Similarity NPD8390 Approved
0.5652 Remote Similarity NPD6008 Approved
0.5652 Remote Similarity NPD6108 Clinical (unspecified phase)
0.5645 Remote Similarity NPD7503 Approved
0.5641 Remote Similarity NPD8132 Clinical (unspecified phase)
0.5636 Remote Similarity NPD4792 Clinical (unspecified phase)
0.5635 Remote Similarity NPD8340 Approved
0.5635 Remote Similarity NPD8342 Approved
0.5635 Remote Similarity NPD8341 Approved
0.5635 Remote Similarity NPD8299 Approved
0.5635 Remote Similarity NPD7492 Approved
0.5632 Remote Similarity NPD9118 Approved
0.5625 Remote Similarity NPD7736 Approved
0.56 Remote Similarity NPD8080 Discontinued

  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