Structure

Physi-Chem Properties

Molecular Weight:  818.31
Volume:  825.024
LogP:  4.456
LogD:  1.992
LogS:  -4.141
# Rotatable Bonds:  16
TPSA:  201.17
# H-Bond Aceptor:  15
# H-Bond Donor:  0
# Rings:  4
# Heavy Atoms:  15

MedChem Properties

QED Drug-Likeness Score:  0.181
Synthetic Accessibility Score:  5.83
Fsp3:  0.455
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.232
MDCK Permeability:  5.849952140124515e-05
Pgp-inhibitor:  1.0
Pgp-substrate:  0.001
Human Intestinal Absorption (HIA):  0.839
20% Bioavailability (F20%):  0.994
30% Bioavailability (F30%):  0.987

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.037
Plasma Protein Binding (PPB):  85.80792236328125%
Volume Distribution (VD):  2.273
Pgp-substrate:  11.813438415527344%

ADMET: Metabolism

CYP1A2-inhibitor:  0.034
CYP1A2-substrate:  0.011
CYP2C19-inhibitor:  0.114
CYP2C19-substrate:  0.053
CYP2C9-inhibitor:  0.838
CYP2C9-substrate:  0.028
CYP2D6-inhibitor:  0.977
CYP2D6-substrate:  0.037
CYP3A4-inhibitor:  0.885
CYP3A4-substrate:  0.361

ADMET: Excretion

Clearance (CL):  3.369
Half-life (T1/2):  0.813

ADMET: Toxicity

hERG Blockers:  0.014
Human Hepatotoxicity (H-HT):  0.99
Drug-inuced Liver Injury (DILI):  0.978
AMES Toxicity:  0.013
Rat Oral Acute Toxicity:  0.46
Maximum Recommended Daily Dose:  0.006
Skin Sensitization:  0.063
Carcinogencity:  0.067
Eye Corrosion:  0.014
Eye Irritation:  0.157
Respiratory Toxicity:  0.016

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

  Natural Product: NPC475660

Natural Product ID:  NPC475660
Common Name*:   Euphotuckeyanol
IUPAC Name:   [(1R,2R,3aR,5S,6E,9S,10S,11R,13R,13aS)-1,3a,9,10,13-pentaacetyloxy-2-benzoyloxy-2,5,8,8-tetramethyl-12-methylidene-4-oxo-1,3,5,9,10,11,13,13a-octahydrocyclopenta[12]annulen-11-yl] benzoate
Synonyms:   Euphotuckeyanol
Standard InCHIKey:  FFSRBMPSPCZRMK-GWPHZUIASA-N
Standard InCHI:  InChI=1S/C44H50O15/c1-24-21-22-42(8,9)39(56-29(6)48)36(54-27(4)46)35(57-40(51)31-17-13-11-14-18-31)25(2)34(53-26(3)45)33-38(55-28(5)47)43(10,23-44(33,37(24)50)58-30(7)49)59-41(52)32-19-15-12-16-20-32/h11-22,24,33-36,38-39H,2,23H2,1,3-10H3/b22-21+/t24-,33-,34-,35+,36+,38+,39+,43+,44+/m0/s1
SMILES:  CC(=O)O[C@H]1C(=C)[C@@H](OC(=O)c2ccccc2)[C@@H](OC(=O)C)[C@@H](OC(=O)C)C(C)(C)/C=C/[C@@H](C(=O)[C@@]2([C@@H]1[C@@H](OC(=O)C)[C@](C2)(C)OC(=O)c1ccccc1)OC(=O)C)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL510846
PubChem CID:   44588923
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001551] Diterpenoids
          • [CHEMONTID:0002877] Jatrophane and cyclojatrophane diterpenoids

*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
NPO15009 Euphorbia lagascae Species Euphorbiaceae Eukaryota n.a. n.a. n.a. PMID[18824363]
NPO15009 Euphorbia lagascae Species Euphorbiaceae Eukaryota Seeds n.a. n.a. PMID[6736971]
NPO15009 Euphorbia lagascae Species Euphorbiaceae 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
NPT668 Individual Protein P-glycoprotein 1 Homo sapiens Ratio = 81.0 n.a. PMID[463124]
NPT668 Individual Protein P-glycoprotein 1 Homo sapiens Flu intensity = 1127.4 n.a. PMID[463124]
NPT668 Individual Protein P-glycoprotein 1 Homo sapiens Ratio = 106.2 n.a. PMID[463124]
NPT668 Individual Protein P-glycoprotein 1 Homo sapiens Flu intensity = 1476.7 n.a. PMID[463124]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. ID50 = 45.0 ug ml-1 PMID[463124]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. ID50 = 22.8 ug ml-1 PMID[463124]
NPT35 Others n.a. LogP = 6.7 n.a. PMID[463124]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. FICI = 0.08 n.a. PMID[463124]

☑ 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 NPC475660 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
0.9771 High Similarity NPC285221
0.9771 High Similarity NPC194769
0.9695 High Similarity NPC290833
0.9695 High Similarity NPC265459
0.9695 High Similarity NPC475262
0.963 High Similarity NPC82467
0.9624 High Similarity NPC272523
0.9624 High Similarity NPC325805
0.9624 High Similarity NPC276652
0.9618 High Similarity NPC472250
0.9562 High Similarity NPC477095
0.9549 High Similarity NPC86772
0.9493 High Similarity NPC205389
0.9481 High Similarity NPC473654
0.9398 High Similarity NPC79699
0.9398 High Similarity NPC270364
0.9357 High Similarity NPC25484
0.9357 High Similarity NPC232583
0.9343 High Similarity NPC477094
0.9343 High Similarity NPC45307
0.9343 High Similarity NPC477096
0.9338 High Similarity NPC473497
0.9323 High Similarity NPC153617
0.9265 High Similarity NPC251294
0.9197 High Similarity NPC474303
0.9197 High Similarity NPC475413
0.9185 High Similarity NPC477358
0.9161 High Similarity NPC477100
0.9161 High Similarity NPC477098
0.9065 High Similarity NPC153214
0.9058 High Similarity NPC242355
0.9058 High Similarity NPC187566
0.9051 High Similarity NPC53361
0.9051 High Similarity NPC121268
0.9051 High Similarity NPC473301
0.9023 High Similarity NPC42234
0.9023 High Similarity NPC475508
0.9007 High Similarity NPC170668
0.8978 High Similarity NPC327511
0.8978 High Similarity NPC205305
0.8971 High Similarity NPC149401
0.8971 High Similarity NPC279637
0.8971 High Similarity NPC472247
0.8951 High Similarity NPC477101
0.8951 High Similarity NPC477099
0.8951 High Similarity NPC477097
0.8897 High Similarity NPC134937
0.8897 High Similarity NPC298547
0.8897 High Similarity NPC324898
0.8889 High Similarity NPC233860
0.8889 High Similarity NPC477360
0.8881 High Similarity NPC272946
0.8857 High Similarity NPC475135
0.8824 High Similarity NPC472248
0.8819 High Similarity NPC125033
0.8768 High Similarity NPC202729
0.8759 High Similarity NPC311492
0.8759 High Similarity NPC28836
0.8759 High Similarity NPC477368
0.875 High Similarity NPC239358
0.8741 High Similarity NPC122504
0.8741 High Similarity NPC475671
0.8741 High Similarity NPC475452
0.8741 High Similarity NPC3450
0.8705 High Similarity NPC27721
0.8696 High Similarity NPC200154
0.8696 High Similarity NPC232888
0.8696 High Similarity NPC477367
0.8686 High Similarity NPC477364
0.8649 High Similarity NPC70344
0.8623 High Similarity NPC477359
0.8613 High Similarity NPC233692
0.8609 High Similarity NPC55744
0.8571 High Similarity NPC8990
0.8531 High Similarity NPC191387
0.8531 High Similarity NPC131966
0.8507 High Similarity NPC477369
0.8435 Intermediate Similarity NPC254558
0.8414 Intermediate Similarity NPC471100
0.8414 Intermediate Similarity NPC471107
0.8403 Intermediate Similarity NPC95449
0.8357 Intermediate Similarity NPC471911
0.8357 Intermediate Similarity NPC4242
0.8345 Intermediate Similarity NPC470231
0.8333 Intermediate Similarity NPC469456
0.8288 Intermediate Similarity NPC25043
0.8288 Intermediate Similarity NPC134131
0.8264 Intermediate Similarity NPC266374
0.8255 Intermediate Similarity NPC51602
0.8231 Intermediate Similarity NPC475552
0.8214 Intermediate Similarity NPC472394
0.8212 Intermediate Similarity NPC282239
0.8207 Intermediate Similarity NPC182869
0.82 Intermediate Similarity NPC469648
0.82 Intermediate Similarity NPC22571
0.82 Intermediate Similarity NPC469647
0.82 Intermediate Similarity NPC138641
0.82 Intermediate Similarity NPC283875
0.8194 Intermediate Similarity NPC162613
0.8194 Intermediate Similarity NPC87934
0.8188 Intermediate Similarity NPC477370
0.8175 Intermediate Similarity NPC477366
0.8175 Intermediate Similarity NPC477363
0.8163 Intermediate Similarity NPC127857
0.8162 Intermediate Similarity NPC477362
0.8158 Intermediate Similarity NPC106895
0.8158 Intermediate Similarity NPC217091
0.8134 Intermediate Similarity NPC473243
0.8133 Intermediate Similarity NPC96308
0.8133 Intermediate Similarity NPC471103
0.8129 Intermediate Similarity NPC37968
0.8125 Intermediate Similarity NPC9905
0.8121 Intermediate Similarity NPC76103
0.8121 Intermediate Similarity NPC473403
0.8116 Intermediate Similarity NPC477365
0.8116 Intermediate Similarity NPC477357
0.8108 Intermediate Similarity NPC312393
0.8105 Intermediate Similarity NPC472393
0.8092 Intermediate Similarity NPC473611
0.8092 Intermediate Similarity NPC21410
0.8092 Intermediate Similarity NPC473670
0.8085 Intermediate Similarity NPC475569
0.8082 Intermediate Similarity NPC192658
0.8082 Intermediate Similarity NPC472546
0.8082 Intermediate Similarity NPC183540
0.8079 Intermediate Similarity NPC233581
0.8079 Intermediate Similarity NPC145649
0.8069 Intermediate Similarity NPC211137
0.8069 Intermediate Similarity NPC48017
0.8069 Intermediate Similarity NPC473060
0.8069 Intermediate Similarity NPC184747
0.8069 Intermediate Similarity NPC147880
0.8069 Intermediate Similarity NPC473758
0.8069 Intermediate Similarity NPC473109
0.8069 Intermediate Similarity NPC200592
0.8069 Intermediate Similarity NPC473112
0.8069 Intermediate Similarity NPC473085
0.8069 Intermediate Similarity NPC473613
0.8069 Intermediate Similarity NPC476094
0.8069 Intermediate Similarity NPC473440
0.8069 Intermediate Similarity NPC4341
0.8069 Intermediate Similarity NPC473081
0.8069 Intermediate Similarity NPC43241
0.8067 Intermediate Similarity NPC473214
0.8067 Intermediate Similarity NPC112216
0.8067 Intermediate Similarity NPC470245
0.8067 Intermediate Similarity NPC7095
0.8054 Intermediate Similarity NPC327031
0.8052 Intermediate Similarity NPC471102
0.8043 Intermediate Similarity NPC476599
0.8042 Intermediate Similarity NPC195647
0.8042 Intermediate Similarity NPC472577
0.8042 Intermediate Similarity NPC66761
0.8042 Intermediate Similarity NPC17877
0.8042 Intermediate Similarity NPC291638
0.8039 Intermediate Similarity NPC11410
0.8026 Intermediate Similarity NPC242262
0.8026 Intermediate Similarity NPC158333
0.8026 Intermediate Similarity NPC249471
0.8026 Intermediate Similarity NPC472030
0.8026 Intermediate Similarity NPC472005
0.8026 Intermediate Similarity NPC265395
0.8026 Intermediate Similarity NPC472022
0.8026 Intermediate Similarity NPC77719
0.8026 Intermediate Similarity NPC237549
0.8026 Intermediate Similarity NPC257213
0.8026 Intermediate Similarity NPC256142
0.8026 Intermediate Similarity NPC304876
0.8026 Intermediate Similarity NPC473414
0.8026 Intermediate Similarity NPC1173
0.8013 Intermediate Similarity NPC472398
0.8013 Intermediate Similarity NPC101043
0.8013 Intermediate Similarity NPC306799
0.8 Intermediate Similarity NPC472371
0.8 Intermediate Similarity NPC475652
0.8 Intermediate Similarity NPC60509
0.8 Intermediate Similarity NPC472395
0.8 Intermediate Similarity NPC473215
0.8 Intermediate Similarity NPC476975
0.8 Intermediate Similarity NPC250046
0.8 Intermediate Similarity NPC81698
0.8 Intermediate Similarity NPC214550
0.8 Intermediate Similarity NPC210591
0.7987 Intermediate Similarity NPC478263
0.7987 Intermediate Similarity NPC209592
0.7987 Intermediate Similarity NPC48599
0.7986 Intermediate Similarity NPC472706
0.7974 Intermediate Similarity NPC26033
0.7974 Intermediate Similarity NPC472549
0.7974 Intermediate Similarity NPC228204
0.7974 Intermediate Similarity NPC473632
0.7974 Intermediate Similarity NPC469730
0.7974 Intermediate Similarity NPC114410
0.7974 Intermediate Similarity NPC132599
0.7974 Intermediate Similarity NPC112523
0.7974 Intermediate Similarity NPC251139
0.7973 Intermediate Similarity NPC34943
0.7972 Intermediate Similarity NPC474608
0.7959 Intermediate Similarity NPC63737
0.7949 Intermediate Similarity NPC476077

  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 NPC475660 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
0.8163 Intermediate Similarity NPD7236 Approved
0.8013 Intermediate Similarity NPD7239 Suspended
0.8 Intermediate Similarity NPD7799 Discontinued
0.7655 Intermediate Similarity NPD7966 Clinical (unspecified phase)
0.7606 Intermediate Similarity NPD6007 Clinical (unspecified phase)
0.7547 Intermediate Similarity NPD7058 Phase 2
0.7547 Intermediate Similarity NPD7057 Phase 3
0.7388 Intermediate Similarity NPD2181 Clinical (unspecified phase)
0.7313 Intermediate Similarity NPD2067 Discontinued
0.7305 Intermediate Similarity NPD7457 Clinical (unspecified phase)
0.7278 Intermediate Similarity NPD7685 Pre-registration
0.7239 Intermediate Similarity NPD2182 Approved
0.723 Intermediate Similarity NPD7961 Discontinued
0.7211 Intermediate Similarity NPD5952 Clinical (unspecified phase)
0.7208 Intermediate Similarity NPD4628 Phase 3
0.7176 Intermediate Similarity NPD8368 Discontinued
0.7174 Intermediate Similarity NPD690 Clinical (unspecified phase)
0.7151 Intermediate Similarity NPD8407 Phase 2
0.7133 Intermediate Similarity NPD6287 Discontinued
0.7125 Intermediate Similarity NPD6599 Discontinued
0.7113 Intermediate Similarity NPD3412 Clinical (unspecified phase)
0.7069 Intermediate Similarity NPD8434 Phase 2
0.7069 Intermediate Similarity NPD8424 Clinical (unspecified phase)
0.705 Intermediate Similarity NPD2629 Approved
0.7029 Intermediate Similarity NPD6858 Approved
0.7029 Intermediate Similarity NPD7094 Approved
0.7023 Intermediate Similarity NPD1238 Approved
0.7 Intermediate Similarity NPD4198 Discontinued
0.6994 Remote Similarity NPD7096 Clinical (unspecified phase)
0.6989 Remote Similarity NPD8435 Approved
0.6977 Remote Similarity NPD6765 Approved
0.6977 Remote Similarity NPD6764 Approved
0.6972 Remote Similarity NPD7741 Discontinued
0.697 Remote Similarity NPD7075 Discontinued
0.6963 Remote Similarity NPD6685 Approved
0.6962 Remote Similarity NPD6799 Approved
0.6943 Remote Similarity NPD6190 Approved
0.6943 Remote Similarity NPD3887 Approved
0.694 Remote Similarity NPD164 Approved
0.6928 Remote Similarity NPD5537 Clinical (unspecified phase)
0.6914 Remote Similarity NPD8055 Clinical (unspecified phase)
0.6908 Remote Similarity NPD6355 Discontinued
0.6893 Remote Similarity NPD8360 Approved
0.6893 Remote Similarity NPD8361 Approved
0.6871 Remote Similarity NPD5667 Approved
0.6835 Remote Similarity NPD1609 Clinical (unspecified phase)
0.6829 Remote Similarity NPD6801 Discontinued
0.6821 Remote Similarity NPD3764 Approved
0.6818 Remote Similarity NPD6784 Approved
0.6818 Remote Similarity NPD6785 Approved
0.6802 Remote Similarity NPD8470 Clinical (unspecified phase)
0.6795 Remote Similarity NPD7702 Clinical (unspecified phase)
0.6788 Remote Similarity NPD5760 Phase 2
0.6788 Remote Similarity NPD5761 Phase 2
0.678 Remote Similarity NPD8150 Discontinued
0.6779 Remote Similarity NPD5740 Clinical (unspecified phase)
0.6779 Remote Similarity NPD6085 Phase 2
0.677 Remote Similarity NPD6273 Approved
0.6758 Remote Similarity NPD8485 Approved
0.6757 Remote Similarity NPD1876 Approved
0.6755 Remote Similarity NPD7008 Discontinued
0.6747 Remote Similarity NPD3817 Phase 2
0.6747 Remote Similarity NPD5402 Approved
0.6741 Remote Similarity NPD5765 Approved
0.6735 Remote Similarity NPD3972 Approved
0.6728 Remote Similarity NPD5403 Approved
0.6728 Remote Similarity NPD6980 Clinical (unspecified phase)
0.6714 Remote Similarity NPD6912 Phase 3
0.6708 Remote Similarity NPD5401 Approved
0.6691 Remote Similarity NPD1237 Approved
0.6689 Remote Similarity NPD6832 Phase 2
0.6688 Remote Similarity NPD6002 Phase 3
0.6688 Remote Similarity NPD6006 Clinical (unspecified phase)
0.6688 Remote Similarity NPD2353 Approved
0.6688 Remote Similarity NPD6003 Clinical (unspecified phase)
0.6688 Remote Similarity NPD2355 Clinical (unspecified phase)
0.6688 Remote Similarity NPD5763 Approved
0.6688 Remote Similarity NPD6005 Phase 3
0.6688 Remote Similarity NPD6004 Phase 3
0.6688 Remote Similarity NPD5762 Approved
0.6687 Remote Similarity NPD7819 Suspended
0.6667 Remote Similarity NPD7305 Phase 1
0.6667 Remote Similarity NPD7713 Phase 3
0.6649 Remote Similarity NPD8486 Clinical (unspecified phase)
0.6647 Remote Similarity NPD8127 Discontinued
0.6646 Remote Similarity NPD7458 Discontinued
0.6644 Remote Similarity NPD17 Approved
0.6642 Remote Similarity NPD7798 Approved
0.663 Remote Similarity NPD7879 Clinical (unspecified phase)
0.6624 Remote Similarity NPD7137 Phase 2
0.6624 Remote Similarity NPD2796 Approved
0.6621 Remote Similarity NPD9545 Approved
0.6619 Remote Similarity NPD6831 Clinical (unspecified phase)
0.6618 Remote Similarity NPD1929 Approved
0.6618 Remote Similarity NPD1931 Clinical (unspecified phase)
0.6618 Remote Similarity NPD5738 Clinical (unspecified phase)
0.6618 Remote Similarity NPD1930 Approved
0.6605 Remote Similarity NPD8389 Clinical (unspecified phase)
0.6605 Remote Similarity NPD7004 Clinical (unspecified phase)
0.6604 Remote Similarity NPD7421 Clinical (unspecified phase)
0.6588 Remote Similarity NPD5494 Approved
0.6582 Remote Similarity NPD2343 Clinical (unspecified phase)
0.6573 Remote Similarity NPD5951 Approved
0.6566 Remote Similarity NPD6385 Approved
0.6566 Remote Similarity NPD6386 Approved
0.6554 Remote Similarity NPD4807 Approved
0.6554 Remote Similarity NPD4806 Approved
0.6538 Remote Similarity NPD6653 Approved
0.6531 Remote Similarity NPD5306 Approved
0.6531 Remote Similarity NPD5305 Approved
0.6522 Remote Similarity NPD5048 Discontinued
0.6522 Remote Similarity NPD2354 Approved
0.6515 Remote Similarity NPD1202 Approved
0.6514 Remote Similarity NPD7804 Clinical (unspecified phase)
0.651 Remote Similarity NPD1608 Approved
0.651 Remote Similarity NPD6637 Approved
0.6509 Remote Similarity NPD4868 Clinical (unspecified phase)
0.6509 Remote Similarity NPD3882 Suspended
0.6506 Remote Similarity NPD4380 Phase 2
0.6496 Remote Similarity NPD6647 Phase 2
0.6486 Remote Similarity NPD4106 Approved
0.6486 Remote Similarity NPD4135 Approved
0.6486 Remote Similarity NPD4136 Approved
0.6474 Remote Similarity NPD230 Phase 1
0.6474 Remote Similarity NPD7184 Clinical (unspecified phase)
0.6471 Remote Similarity NPD7055 Discontinued
0.6456 Remote Similarity NPD7033 Discontinued
0.6456 Remote Similarity NPD3748 Approved
0.6456 Remote Similarity NPD2799 Discontinued
0.6455 Remote Similarity NPD7497 Discontinued
0.6452 Remote Similarity NPD6233 Phase 2
0.6452 Remote Similarity NPD8032 Phase 2
0.6452 Remote Similarity NPD6663 Approved
0.645 Remote Similarity NPD8443 Clinical (unspecified phase)
0.6449 Remote Similarity NPD5909 Discontinued
0.6447 Remote Similarity NPD5647 Approved
0.6446 Remote Similarity NPD6591 Clinical (unspecified phase)
0.6443 Remote Similarity NPD8462 Phase 1
0.6441 Remote Similarity NPD7993 Clinical (unspecified phase)
0.6437 Remote Similarity NPD7784 Clinical (unspecified phase)
0.6433 Remote Similarity NPD919 Approved
0.6429 Remote Similarity NPD7095 Approved
0.6429 Remote Similarity NPD6039 Approved
0.6424 Remote Similarity NPD920 Approved
0.6419 Remote Similarity NPD5125 Phase 3
0.6419 Remote Similarity NPD5126 Approved
0.6418 Remote Similarity NPD1989 Approved
0.6415 Remote Similarity NPD2438 Suspended
0.6405 Remote Similarity NPD5736 Approved
0.6405 Remote Similarity NPD5204 Approved
0.6402 Remote Similarity NPD4378 Clinical (unspecified phase)
0.64 Remote Similarity NPD7473 Discontinued
0.6397 Remote Similarity NPD2066 Phase 3
0.6395 Remote Similarity NPD7009 Phase 2
0.6392 Remote Similarity NPD2569 Approved
0.6392 Remote Similarity NPD2567 Approved
0.6387 Remote Similarity NPD6798 Discontinued
0.6387 Remote Similarity NPD2313 Discontinued
0.6387 Remote Similarity NPD6859 Clinical (unspecified phase)
0.6382 Remote Similarity NPD6362 Approved
0.6382 Remote Similarity NPD3267 Approved
0.6382 Remote Similarity NPD3266 Approved
0.6379 Remote Similarity NPD3926 Phase 2
0.6379 Remote Similarity NPD5242 Approved
0.6375 Remote Similarity NPD1471 Phase 3
0.6374 Remote Similarity NPD4381 Clinical (unspecified phase)
0.6369 Remote Similarity NPD7411 Suspended
0.6364 Remote Similarity NPD7893 Clinical (unspecified phase)
0.6364 Remote Similarity NPD8297 Approved
0.6358 Remote Similarity NPD8166 Discontinued
0.6353 Remote Similarity NPD5353 Approved
0.6351 Remote Similarity NPD4102 Approved
0.6351 Remote Similarity NPD5585 Approved
0.6351 Remote Similarity NPD4105 Approved
0.6347 Remote Similarity NPD3226 Approved
0.6341 Remote Similarity NPD6143 Clinical (unspecified phase)
0.634 Remote Similarity NPD2788 Approved
0.634 Remote Similarity NPD2798 Approved
0.6335 Remote Similarity NPD4534 Discontinued
0.6335 Remote Similarity NPD5958 Discontinued
0.6335 Remote Similarity NPD8320 Phase 1
0.6335 Remote Similarity NPD8319 Approved
0.6333 Remote Similarity NPD8312 Approved
0.6333 Remote Similarity NPD8313 Approved
0.6327 Remote Similarity NPD7610 Discontinued
0.6316 Remote Similarity NPD2198 Approved
0.6316 Remote Similarity NPD2199 Approved
0.6309 Remote Similarity NPD7163 Clinical (unspecified phase)
0.6306 Remote Similarity NPD4307 Phase 2
0.6304 Remote Similarity NPD1932 Approved
0.6303 Remote Similarity NPD642 Clinical (unspecified phase)
0.6299 Remote Similarity NPD3662 Phase 3
0.6299 Remote Similarity NPD3664 Approved
0.6299 Remote Similarity NPD3663 Approved
0.6299 Remote Similarity NPD7084 Phase 3
0.6299 Remote Similarity NPD3661 Approved
0.6294 Remote Similarity NPD4141 Clinical (unspecified phase)
0.6294 Remote Similarity NPD7460 Discontinued
0.6284 Remote Similarity NPD6319 Approved
0.6282 Remote Similarity NPD3268 Approved

  Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity
B: biological targets similarity
C: networks similarity
D: cell-based bioactivity similarity
E: similarity based on clinical data