Structure

Physi-Chem Properties

Molecular Weight:  594.45
Volume:  650.425
LogP:  7.517
LogD:  4.582
LogS:  -5.715
# Rotatable Bonds:  26
TPSA:  120.36
# H-Bond Aceptor:  7
# H-Bond Donor:  4
# Rings:  2
# Heavy Atoms:  7

MedChem Properties

QED Drug-Likeness Score:  0.081
Synthetic Accessibility Score:  4.379
Fsp3:  0.857
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:  -5.264
MDCK Permeability:  2.7369887902750634e-05
Pgp-inhibitor:  0.133
Pgp-substrate:  0.995
Human Intestinal Absorption (HIA):  0.016
20% Bioavailability (F20%):  1.0
30% Bioavailability (F30%):  0.973

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.004
Plasma Protein Binding (PPB):  97.19181060791016%
Volume Distribution (VD):  0.843
Pgp-substrate:  2.2249441146850586%

ADMET: Metabolism

CYP1A2-inhibitor:  0.028
CYP1A2-substrate:  0.362
CYP2C19-inhibitor:  0.065
CYP2C19-substrate:  0.048
CYP2C9-inhibitor:  0.086
CYP2C9-substrate:  0.977
CYP2D6-inhibitor:  0.005
CYP2D6-substrate:  0.122
CYP3A4-inhibitor:  0.166
CYP3A4-substrate:  0.018

ADMET: Excretion

Clearance (CL):  6.319
Half-life (T1/2):  0.498

ADMET: Toxicity

hERG Blockers:  0.088
Human Hepatotoxicity (H-HT):  0.531
Drug-inuced Liver Injury (DILI):  0.052
AMES Toxicity:  0.02
Rat Oral Acute Toxicity:  0.192
Maximum Recommended Daily Dose:  0.87
Skin Sensitization:  0.947
Carcinogencity:  0.033
Eye Corrosion:  0.003
Eye Irritation:  0.016
Respiratory Toxicity:  0.793

Download Data

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

  Natural Product: NPC219498

Natural Product ID:  NPC219498
Common Name*:   Annoreticuin-9-One
IUPAC Name:   (2S)-4-[(2R,13R)-2,13-dihydroxy-13-[(2R,5R)-5-[(1R)-1-hydroxytridecyl]oxolan-2-yl]-7-oxotridecyl]-2-methyl-2H-furan-5-one
Synonyms:   Annoreticuin-9-One
Standard InCHIKey:  QCICHLFBIUXRKT-DOXWYWRGSA-N
Standard InCHI:  InChI=1S/C35H62O7/c1-3-4-5-6-7-8-9-10-11-14-21-31(38)33-23-24-34(42-33)32(39)22-15-12-13-18-29(36)19-16-17-20-30(37)26-28-25-27(2)41-35(28)40/h25,27,30-34,37-39H,3-24,26H2,1-2H3/t27-,30+,31+,32+,33+,34+/m0/s1
SMILES:  CCCCCCCCCCCC[C@H]([C@H]1CC[C@@H](O1)[C@@H](CCCCCC(=O)CCCC[C@H](CC1=C[C@@H](OC1=O)C)O)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL503350
PubChem CID:   10054216
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
NPO2884 Annona squamosa Species Annonaceae Eukaryota seeds n.a. n.a. PMID[11141125]
NPO2884 Annona squamosa Species Annonaceae Eukaryota n.a. n.a. n.a. PMID[12398544]
NPO2884 Annona squamosa Species Annonaceae Eukaryota n.a. n.a. n.a. PMID[18419154]
NPO2884 Annona squamosa Species Annonaceae Eukaryota n.a. n.a. n.a. PMID[19296389]
NPO2884 Annona squamosa Species Annonaceae Eukaryota n.a. n.a. n.a. PMID[21910504]
NPO2884 Annona squamosa Species Annonaceae Eukaryota n.a. seed n.a. PMID[22011319]
NPO2884 Annona squamosa Species Annonaceae Eukaryota seeds n.a. n.a. PMID[22011319]
NPO2884 Annona squamosa Species Annonaceae Eukaryota Barks n.a. n.a. PMID[2348205]
NPO2884 Annona squamosa Species Annonaceae Eukaryota n.a. fruit n.a. PMID[8786370]
NPO2884 Annona squamosa Species Annonaceae Eukaryota bark n.a. n.a. PMID[9214729]
NPO2884 Annona squamosa Species Annonaceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO2884 Annona squamosa Species Annonaceae Eukaryota n.a. n.a. Database[FooDB]
NPO2884 Annona squamosa Species Annonaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO2884 Annona squamosa Species Annonaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO2884 Annona squamosa Species Annonaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO2884 Annona squamosa 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 = 2.7 10'-1 ug/ml PMID[489689]
NPT83 Cell Line MCF7 Homo sapiens ED50 > 1.0 ug ml-1 PMID[489689]
NPT139 Cell Line HT-29 Homo sapiens ED50 > 1.0 ug ml-1 PMID[489689]
NPT376 Cell Line A498 Homo sapiens ED50 > 1.0 ug ml-1 PMID[489689]
NPT306 Cell Line PC-3 Homo sapiens ED50 = 9.6 10'-3 ug/ml PMID[489689]
NPT783 Cell Line MIA PaCa-2 Homo sapiens ED50 = 2.4 10'-4 ug/ml PMID[489689]
NPT140 Organism Artemia Artemia LC50 = 0.41 ug.mL-1 PMID[489689]

☑ 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 NPC219498 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 NPC308412
1.0 High Similarity NPC204686
1.0 High Similarity NPC210218
1.0 High Similarity NPC134885
1.0 High Similarity NPC473687
1.0 High Similarity NPC134807
0.9875 High Similarity NPC82795
0.9875 High Similarity NPC473669
0.9875 High Similarity NPC473478
0.9875 High Similarity NPC103284
0.9875 High Similarity NPC231009
0.9875 High Similarity NPC110710
0.9875 High Similarity NPC107986
0.9875 High Similarity NPC473651
0.9875 High Similarity NPC286338
0.9875 High Similarity NPC66346
0.9875 High Similarity NPC132496
0.9875 High Similarity NPC283085
0.9875 High Similarity NPC1083
0.9875 High Similarity NPC223871
0.9753 High Similarity NPC142117
0.9753 High Similarity NPC232555
0.9753 High Similarity NPC107717
0.9753 High Similarity NPC171174
0.9753 High Similarity NPC231096
0.9753 High Similarity NPC134865
0.9753 High Similarity NPC475581
0.9753 High Similarity NPC279267
0.9753 High Similarity NPC240695
0.9753 High Similarity NPC114694
0.9753 High Similarity NPC69082
0.9753 High Similarity NPC103523
0.9753 High Similarity NPC62118
0.9639 High Similarity NPC14901
0.9639 High Similarity NPC130359
0.9634 High Similarity NPC178215
0.9625 High Similarity NPC144415
0.9518 High Similarity NPC40376
0.9518 High Similarity NPC20339
0.9518 High Similarity NPC133730
0.9518 High Similarity NPC100454
0.9518 High Similarity NPC61257
0.9518 High Similarity NPC39754
0.9518 High Similarity NPC191929
0.9518 High Similarity NPC274446
0.9518 High Similarity NPC287164
0.9518 High Similarity NPC233551
0.9518 High Similarity NPC81045
0.9518 High Similarity NPC169511
0.9518 High Similarity NPC21208
0.9518 High Similarity NPC242364
0.9518 High Similarity NPC320569
0.9518 High Similarity NPC172821
0.9518 High Similarity NPC280621
0.9518 High Similarity NPC171135
0.9518 High Similarity NPC261952
0.9518 High Similarity NPC48338
0.9518 High Similarity NPC151403
0.9518 High Similarity NPC234077
0.9512 High Similarity NPC112685
0.9512 High Similarity NPC477015
0.9506 High Similarity NPC156804
0.9506 High Similarity NPC163093
0.95 High Similarity NPC475159
0.95 High Similarity NPC473529
0.95 High Similarity NPC473712
0.95 High Similarity NPC131002
0.95 High Similarity NPC180363
0.95 High Similarity NPC473780
0.95 High Similarity NPC65930
0.95 High Similarity NPC73310
0.95 High Similarity NPC329829
0.95 High Similarity NPC11332
0.95 High Similarity NPC94875
0.95 High Similarity NPC145914
0.9405 High Similarity NPC81778
0.9405 High Similarity NPC477011
0.9405 High Similarity NPC42598
0.9405 High Similarity NPC91067
0.9405 High Similarity NPC318963
0.9405 High Similarity NPC280612
0.9405 High Similarity NPC40066
0.9405 High Similarity NPC20621
0.9405 High Similarity NPC139418
0.9405 High Similarity NPC473504
0.9405 High Similarity NPC93794
0.939 High Similarity NPC329615
0.939 High Similarity NPC471567
0.939 High Similarity NPC322529
0.939 High Similarity NPC477013
0.939 High Similarity NPC477014
0.939 High Similarity NPC182383
0.939 High Similarity NPC120398
0.939 High Similarity NPC329838
0.9383 High Similarity NPC253801
0.9302 High Similarity NPC11456
0.9294 High Similarity NPC239517
0.9294 High Similarity NPC473904
0.9277 High Similarity NPC241360
0.9277 High Similarity NPC293136
0.9277 High Similarity NPC477010
0.9277 High Similarity NPC132940
0.9277 High Similarity NPC47937
0.9176 High Similarity NPC477016
0.9176 High Similarity NPC477017
0.9167 High Similarity NPC20533
0.9167 High Similarity NPC258068
0.9167 High Similarity NPC477012
0.9167 High Similarity NPC476583
0.9157 High Similarity NPC319036
0.9157 High Similarity NPC477018
0.9157 High Similarity NPC9678
0.9157 High Similarity NPC100921
0.9157 High Similarity NPC292809
0.9157 High Similarity NPC25764
0.9157 High Similarity NPC39167
0.9157 High Similarity NPC202055
0.9157 High Similarity NPC235809
0.9157 High Similarity NPC473156
0.9157 High Similarity NPC470400
0.9157 High Similarity NPC39279
0.9157 High Similarity NPC475268
0.9157 High Similarity NPC473671
0.9157 High Similarity NPC77871
0.908 High Similarity NPC473663
0.908 High Similarity NPC475173
0.908 High Similarity NPC473723
0.908 High Similarity NPC473561
0.9059 High Similarity NPC320458
0.9059 High Similarity NPC89001
0.9059 High Similarity NPC473905
0.9048 High Similarity NPC473840
0.9048 High Similarity NPC219652
0.9048 High Similarity NPC282815
0.9048 High Similarity NPC25703
0.9048 High Similarity NPC309211
0.8966 High Similarity NPC473707
0.8941 High Similarity NPC159750
0.8941 High Similarity NPC473995
0.8941 High Similarity NPC470401
0.8941 High Similarity NPC473649
0.8941 High Similarity NPC154097
0.8652 High Similarity NPC473520
0.8444 Intermediate Similarity NPC162205
0.8444 Intermediate Similarity NPC288240
0.8444 Intermediate Similarity NPC273579
0.8444 Intermediate Similarity NPC295204
0.8333 Intermediate Similarity NPC30515
0.8276 Intermediate Similarity NPC21469
0.8242 Intermediate Similarity NPC81419
0.8242 Intermediate Similarity NPC179746
0.8222 Intermediate Similarity NPC51004
0.8222 Intermediate Similarity NPC473619
0.8132 Intermediate Similarity NPC12172
0.8132 Intermediate Similarity NPC473321
0.8132 Intermediate Similarity NPC208886
0.8132 Intermediate Similarity NPC184463
0.8118 Intermediate Similarity NPC47653
0.8111 Intermediate Similarity NPC307411
0.8111 Intermediate Similarity NPC295312
0.8065 Intermediate Similarity NPC36954
0.8046 Intermediate Similarity NPC284472
0.8046 Intermediate Similarity NPC229799
0.8046 Intermediate Similarity NPC286770
0.8043 Intermediate Similarity NPC476300
0.8043 Intermediate Similarity NPC475912
0.8025 Intermediate Similarity NPC84038
0.8022 Intermediate Similarity NPC473448
0.8022 Intermediate Similarity NPC476004
0.8022 Intermediate Similarity NPC474761
0.8 Intermediate Similarity NPC187268
0.8 Intermediate Similarity NPC202672
0.8 Intermediate Similarity NPC473326
0.7978 Intermediate Similarity NPC469483
0.7976 Intermediate Similarity NPC475711
0.7957 Intermediate Similarity NPC474035
0.7957 Intermediate Similarity NPC81386
0.7955 Intermediate Similarity NPC474251
0.7931 Intermediate Similarity NPC474959
0.7931 Intermediate Similarity NPC475046
0.7931 Intermediate Similarity NPC310450
0.7931 Intermediate Similarity NPC11383
0.7927 Intermediate Similarity NPC474705
0.7912 Intermediate Similarity NPC474032
0.7889 Intermediate Similarity NPC179659
0.7889 Intermediate Similarity NPC160138
0.7882 Intermediate Similarity NPC93763
0.7882 Intermediate Similarity NPC279214
0.7882 Intermediate Similarity NPC221095
0.7882 Intermediate Similarity NPC108816
0.7872 Intermediate Similarity NPC270013
0.7872 Intermediate Similarity NPC14961
0.7857 Intermediate Similarity NPC123360
0.7849 Intermediate Similarity NPC469692
0.7849 Intermediate Similarity NPC212486
0.7849 Intermediate Similarity NPC469645
0.7841 Intermediate Similarity NPC475947
0.7841 Intermediate Similarity NPC169575
0.7841 Intermediate Similarity NPC116543
0.7841 Intermediate Similarity NPC40746

  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 NPC219498 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
0.7826 Intermediate Similarity NPD46 Approved
0.7826 Intermediate Similarity NPD6698 Approved
0.7624 Intermediate Similarity NPD7899 Clinical (unspecified phase)
0.7447 Intermediate Similarity NPD7838 Discovery
0.7238 Intermediate Similarity NPD6371 Approved
0.7188 Intermediate Similarity NPD7983 Approved
0.7143 Intermediate Similarity NPD1698 Clinical (unspecified phase)
0.71 Intermediate Similarity NPD8029 Clinical (unspecified phase)
0.7083 Intermediate Similarity NPD5785 Approved
0.7048 Intermediate Similarity NPD6686 Approved
0.6915 Remote Similarity NPD1733 Clinical (unspecified phase)
0.6915 Remote Similarity NPD5363 Approved
0.6852 Remote Similarity NPD8413 Clinical (unspecified phase)
0.6778 Remote Similarity NPD4756 Discovery
0.6771 Remote Similarity NPD4250 Approved
0.6771 Remote Similarity NPD4251 Approved
0.6765 Remote Similarity NPD4225 Approved
0.6747 Remote Similarity NPD3197 Phase 1
0.6737 Remote Similarity NPD6082 Clinical (unspecified phase)
0.6702 Remote Similarity NPD7154 Phase 3
0.6702 Remote Similarity NPD5362 Discontinued
0.6667 Remote Similarity NPD4249 Approved
0.6633 Remote Similarity NPD1695 Approved
0.6596 Remote Similarity NPD4269 Approved
0.6596 Remote Similarity NPD4270 Approved
0.6559 Remote Similarity NPD5790 Clinical (unspecified phase)
0.6559 Remote Similarity NPD4252 Approved
0.6512 Remote Similarity NPD4247 Clinical (unspecified phase)
0.6495 Remote Similarity NPD5786 Approved
0.6489 Remote Similarity NPD5369 Approved
0.6476 Remote Similarity NPD5344 Discontinued
0.6421 Remote Similarity NPD6435 Approved
0.6421 Remote Similarity NPD4752 Clinical (unspecified phase)
0.6404 Remote Similarity NPD7115 Discovery
0.6392 Remote Similarity NPD1694 Approved
0.6373 Remote Similarity NPD5282 Discontinued
0.6354 Remote Similarity NPD6110 Phase 1
0.6344 Remote Similarity NPD4268 Approved
0.6344 Remote Similarity NPD4271 Approved
0.6344 Remote Similarity NPD5784 Clinical (unspecified phase)
0.6339 Remote Similarity NPD6053 Discontinued
0.6325 Remote Similarity NPD8516 Approved
0.6325 Remote Similarity NPD8517 Approved
0.6325 Remote Similarity NPD8515 Approved
0.6325 Remote Similarity NPD8513 Phase 3
0.6289 Remote Similarity NPD6400 Clinical (unspecified phase)
0.6286 Remote Similarity NPD7638 Approved
0.6275 Remote Similarity NPD5778 Approved
0.6275 Remote Similarity NPD5779 Approved
0.625 Remote Similarity NPD5209 Approved
0.625 Remote Similarity NPD7839 Suspended
0.6235 Remote Similarity NPD2664 Clinical (unspecified phase)
0.6226 Remote Similarity NPD7640 Approved
0.6226 Remote Similarity NPD7639 Approved
0.6216 Remote Similarity NPD4061 Clinical (unspecified phase)
0.6211 Remote Similarity NPD4821 Approved
0.6211 Remote Similarity NPD4819 Approved
0.6211 Remote Similarity NPD4822 Approved
0.6211 Remote Similarity NPD4820 Approved
0.6211 Remote Similarity NPD5368 Approved
0.6207 Remote Similarity NPD3704 Approved
0.6196 Remote Similarity NPD8039 Approved
0.619 Remote Similarity NPD4246 Clinical (unspecified phase)
0.6186 Remote Similarity NPD5332 Approved
0.6186 Remote Similarity NPD5331 Approved
0.6146 Remote Similarity NPD4790 Discontinued
0.6139 Remote Similarity NPD5370 Suspended
0.6117 Remote Similarity NPD6399 Phase 3
0.6116 Remote Similarity NPD7507 Approved
0.6092 Remote Similarity NPD2685 Clinical (unspecified phase)
0.6083 Remote Similarity NPD7642 Approved
0.6083 Remote Similarity NPD7829 Approved
0.6083 Remote Similarity NPD7830 Approved
0.6075 Remote Similarity NPD6648 Approved
0.6068 Remote Similarity NPD7641 Discontinued
0.6066 Remote Similarity NPD8074 Phase 3
0.6049 Remote Similarity NPD4266 Approved
0.6049 Remote Similarity NPD3194 Approved
0.6049 Remote Similarity NPD3728 Approved
0.6049 Remote Similarity NPD3195 Phase 2
0.6049 Remote Similarity NPD3730 Approved
0.6049 Remote Similarity NPD3196 Approved
0.6038 Remote Similarity NPD7902 Approved
0.6036 Remote Similarity NPD6412 Phase 2
0.6023 Remote Similarity NPD6108 Clinical (unspecified phase)
0.6019 Remote Similarity NPD4810 Clinical (unspecified phase)
0.6018 Remote Similarity NPD5955 Clinical (unspecified phase)
0.5968 Remote Similarity NPD7319 Approved
0.5965 Remote Similarity NPD7116 Clinical (unspecified phase)
0.5952 Remote Similarity NPD69 Approved
0.5952 Remote Similarity NPD9119 Approved
0.5952 Remote Similarity NPD6109 Phase 1
0.5926 Remote Similarity NPD3172 Approved
0.5917 Remote Similarity NPD8033 Approved
0.5917 Remote Similarity NPD8444 Approved
0.5913 Remote Similarity NPD8297 Approved
0.5905 Remote Similarity NPD7748 Approved
0.5891 Remote Similarity NPD7966 Clinical (unspecified phase)
0.5877 Remote Similarity NPD2067 Discontinued
0.5875 Remote Similarity NPD6927 Phase 3
0.5873 Remote Similarity NPD7260 Phase 2
0.5865 Remote Similarity NPD7637 Suspended
0.5862 Remote Similarity NPD4632 Approved
0.5847 Remote Similarity NPD7500 Approved
0.5843 Remote Similarity NPD7331 Phase 2
0.5833 Remote Similarity NPD9118 Approved
0.5833 Remote Similarity NPD8377 Approved
0.5833 Remote Similarity NPD8294 Approved
0.5827 Remote Similarity NPD6845 Suspended
0.5826 Remote Similarity NPD2204 Approved
0.5825 Remote Similarity NPD6101 Approved
0.5825 Remote Similarity NPD5764 Clinical (unspecified phase)
0.5804 Remote Similarity NPD6008 Approved
0.5798 Remote Similarity NPD7328 Approved
0.5798 Remote Similarity NPD7327 Approved
0.5794 Remote Similarity NPD4792 Clinical (unspecified phase)
0.5785 Remote Similarity NPD8379 Approved
0.5785 Remote Similarity NPD8296 Approved
0.5785 Remote Similarity NPD8380 Approved
0.5785 Remote Similarity NPD8335 Approved
0.5785 Remote Similarity NPD8378 Approved
0.5772 Remote Similarity NPD7492 Approved
0.5766 Remote Similarity NPD6647 Phase 2
0.576 Remote Similarity NPD7736 Approved
0.5755 Remote Similarity NPD7900 Approved
0.5755 Remote Similarity NPD7901 Clinical (unspecified phase)
0.5752 Remote Similarity NPD5954 Clinical (unspecified phase)
0.575 Remote Similarity NPD7516 Approved
0.5741 Remote Similarity NPD6084 Phase 2
0.5741 Remote Similarity NPD6083 Phase 2
0.5739 Remote Similarity NPD6421 Discontinued
0.5728 Remote Similarity NPD6903 Approved
0.5726 Remote Similarity NPD8451 Approved
0.5726 Remote Similarity NPD6616 Approved
0.5726 Remote Similarity NPD8273 Phase 1
0.5714 Remote Similarity NPD7505 Discontinued
0.5714 Remote Similarity NPD6411 Approved
0.5714 Remote Similarity NPD8259 Clinical (unspecified phase)
0.5714 Remote Similarity NPD7515 Phase 2
0.5702 Remote Similarity NPD7320 Approved
0.5702 Remote Similarity NPD6881 Approved
0.5702 Remote Similarity NPD6899 Approved
0.5702 Remote Similarity NPD5345 Clinical (unspecified phase)
0.5702 Remote Similarity NPD6319 Approved
0.5702 Remote Similarity NPD6054 Approved
0.5691 Remote Similarity NPD8328 Phase 3
0.569 Remote Similarity NPD8130 Phase 1
0.569 Remote Similarity NPD6650 Approved
0.569 Remote Similarity NPD6649 Approved
0.5686 Remote Similarity NPD5330 Approved
0.5686 Remote Similarity NPD6422 Discontinued
0.5686 Remote Similarity NPD6684 Approved
0.5686 Remote Similarity NPD7146 Approved
0.5686 Remote Similarity NPD7521 Approved
0.5686 Remote Similarity NPD6409 Approved
0.5686 Remote Similarity NPD7334 Approved
0.568 Remote Similarity NPD8293 Discontinued
0.568 Remote Similarity NPD8448 Approved
0.568 Remote Similarity NPD7078 Approved
0.5679 Remote Similarity NPD29 Approved
0.5679 Remote Similarity NPD28 Approved
0.5676 Remote Similarity NPD7632 Discontinued
0.5664 Remote Similarity NPD6402 Approved
0.5664 Remote Similarity NPD6675 Approved
0.5664 Remote Similarity NPD5739 Approved
0.5664 Remote Similarity NPD7128 Approved
0.5652 Remote Similarity NPD6373 Approved
0.5652 Remote Similarity NPD8132 Clinical (unspecified phase)
0.5652 Remote Similarity NPD6372 Approved
0.5614 Remote Similarity NPD5697 Approved
0.561 Remote Similarity NPD8080 Discontinued
0.561 Remote Similarity NPD6370 Approved
0.5603 Remote Similarity NPD6883 Approved
0.5603 Remote Similarity NPD7102 Approved
0.5603 Remote Similarity NPD7290 Approved
0.56 Remote Similarity NPD4800 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