Structure

Physi-Chem Properties

Molecular Weight:  580.27
Volume:  597.846
LogP:  4.404
LogD:  3.124
LogS:  -4.486
# Rotatable Bonds:  10
TPSA:  122.27
# H-Bond Aceptor:  9
# H-Bond Donor:  0
# Rings:  4
# Heavy Atoms:  9

MedChem Properties

QED Drug-Likeness Score:  0.266
Synthetic Accessibility Score:  5.356
Fsp3:  0.545
Lipinski Rule-of-5:  Accepted
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:  -5.03
MDCK Permeability:  3.4898988815257326e-05
Pgp-inhibitor:  1.0
Pgp-substrate:  0.003
Human Intestinal Absorption (HIA):  0.282
20% Bioavailability (F20%):  0.957
30% Bioavailability (F30%):  0.96

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.053
Plasma Protein Binding (PPB):  92.33782196044922%
Volume Distribution (VD):  1.931
Pgp-substrate:  9.295437812805176%

ADMET: Metabolism

CYP1A2-inhibitor:  0.044
CYP1A2-substrate:  0.049
CYP2C19-inhibitor:  0.334
CYP2C19-substrate:  0.103
CYP2C9-inhibitor:  0.907
CYP2C9-substrate:  0.085
CYP2D6-inhibitor:  0.074
CYP2D6-substrate:  0.056
CYP3A4-inhibitor:  0.9
CYP3A4-substrate:  0.602

ADMET: Excretion

Clearance (CL):  3.745
Half-life (T1/2):  0.491

ADMET: Toxicity

hERG Blockers:  0.007
Human Hepatotoxicity (H-HT):  0.965
Drug-inuced Liver Injury (DILI):  0.974
AMES Toxicity:  0.044
Rat Oral Acute Toxicity:  0.923
Maximum Recommended Daily Dose:  0.917
Skin Sensitization:  0.084
Carcinogencity:  0.183
Eye Corrosion:  0.004
Eye Irritation:  0.048
Respiratory Toxicity:  0.907

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

  Natural Product: NPC270364

Natural Product ID:  NPC270364
Common Name*:   ARUXHDLPKVRONO-DUPHUTJUSA-N
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  ARUXHDLPKVRONO-DUPHUTJUSA-N
Standard InCHI:  InChI=1S/C33H40O9/c1-18-15-26-25(32(26,6)7)14-13-24(17-39-20(3)34)29(40-21(4)35)27-28(41-31(38)23-11-9-8-10-12-23)19(2)16-33(27,30(18)37)42-22(5)36/h8-13,15,19,25-29H,14,16-17H2,1-7H3/b18-15+,24-13+/t19-,25-,26+,27+,28-,29-,33+/m0/s1
SMILES:  CC(=O)OC/C/1=CC[C@H]2[C@H](C2(C)C)/C=C(/C(=O)[C@@]2([C@@H]([C@H]1OC(=O)C)[C@@H](OC(=O)c1ccccc1)[C@H](C2)C)OC(=O)C)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL556064
PubChem CID:   44241675
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001551] 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
NPO520 Euphorbia lathyris Species Euphorbiaceae Eukaryota n.a. n.a. n.a. PMID[12542364]
NPO10036 Bruguiera cylindrica Species Rhizophoraceae Eukaryota Fruits n.a. n.a. PMID[15165157]
NPO2462 Machilus robusta Species Lauraceae Eukaryota n.a. bark n.a. PMID[21627109]
NPO2462 Machilus robusta Species Lauraceae Eukaryota bark n.a. n.a. PMID[21627109]
NPO520 Euphorbia lathyris Species Euphorbiaceae Eukaryota n.a. n.a. n.a. PMID[30817151]
NPO9866 Symphytum tuberosum Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO520 Euphorbia lathyris Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO4235 Thymus magnus Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO4235 Thymus magnus Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO520 Euphorbia lathyris Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO9866 Symphytum tuberosum Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO520 Euphorbia lathyris Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO520 Euphorbia lathyris Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO520 Euphorbia lathyris Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5571 Jacobaea arnautorum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4494 Ecbolium linneanum Species Acanthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8283 Pseudophegopteris subaurita Species Thelypteridaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10733 Plantago uniflora Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2462 Machilus robusta Species Lauraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10036 Bruguiera cylindrica Species Rhizophoraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9866 Symphytum tuberosum Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10479 Ophiocoma echinata Species Ophiocomidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3940 Erioderma chilense Species Pannariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4235 Thymus magnus Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10959 Kalanchoe marmorata Species Crassulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1000 Thymus transcaucasicus Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10833 Heteromma simplicifolium n.a. n.a. n.a. 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
NPT2 Others Unspecified Activity = 15.0 % PMID[565759]
NPT2 Others Unspecified IC50 = 248.3 ug.mL-1 PMID[565759]
NPT2 Others Unspecified Ratio IC50 = 4.36 n.a. PMID[565759]
NPT35 Others n.a. LogP = 6.1 n.a. PMID[565759]

☑ 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 NPC270364 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
0.9769 High Similarity NPC276652
0.969 High Similarity NPC475262
0.969 High Similarity NPC290833
0.969 High Similarity NPC265459
0.9621 High Similarity NPC473654
0.9615 High Similarity NPC285221
0.9615 High Similarity NPC194769
0.9612 High Similarity NPC472250
0.9606 High Similarity NPC42234
0.9542 High Similarity NPC86772
0.9478 High Similarity NPC477094
0.9478 High Similarity NPC477096
0.947 High Similarity NPC272523
0.947 High Similarity NPC325805
0.9457 High Similarity NPC477360
0.9398 High Similarity NPC251294
0.9398 High Similarity NPC475660
0.9333 High Similarity NPC82467
0.9328 High Similarity NPC473497
0.9318 High Similarity NPC477358
0.9313 High Similarity NPC477368
0.9302 High Similarity NPC475671
0.9302 High Similarity NPC475452
0.927 High Similarity NPC477095
0.9242 High Similarity NPC79699
0.9242 High Similarity NPC232888
0.9242 High Similarity NPC477367
0.9237 High Similarity NPC477364
0.9191 High Similarity NPC153214
0.9191 High Similarity NPC45307
0.9185 High Similarity NPC474303
0.9185 High Similarity NPC475413
0.9167 High Similarity NPC477359
0.9154 High Similarity NPC272946
0.9134 High Similarity NPC8990
0.9071 High Similarity NPC477099
0.9071 High Similarity NPC477097
0.9071 High Similarity NPC477101
0.9071 High Similarity NPC125033
0.9062 High Similarity NPC477369
0.9008 High Similarity NPC122504
0.9008 High Similarity NPC475508
0.9008 High Similarity NPC3450
0.8993 High Similarity NPC170668
0.8955 High Similarity NPC472247
0.8936 High Similarity NPC232583
0.8936 High Similarity NPC25484
0.8929 High Similarity NPC205389
0.8905 High Similarity NPC187566
0.8881 High Similarity NPC477098
0.8881 High Similarity NPC153617
0.8881 High Similarity NPC477100
0.8872 High Similarity NPC233860
0.8806 High Similarity NPC472248
0.8741 High Similarity NPC324898
0.8741 High Similarity NPC298547
0.8741 High Similarity NPC134937
0.8741 High Similarity NPC28836
0.8731 High Similarity NPC239358
0.8712 High Similarity NPC477370
0.8702 High Similarity NPC477366
0.8702 High Similarity NPC477363
0.8692 High Similarity NPC477362
0.8676 High Similarity NPC200154
0.8676 High Similarity NPC149401
0.8676 High Similarity NPC279637
0.8647 High Similarity NPC37968
0.8636 High Similarity NPC477357
0.8636 High Similarity NPC477365
0.8633 High Similarity NPC242355
0.8613 High Similarity NPC202729
0.8603 High Similarity NPC311492
0.8593 High Similarity NPC233692
0.8551 High Similarity NPC27721
0.8551 High Similarity NPC205305
0.8551 High Similarity NPC327511
0.8511 High Similarity NPC191387
0.8511 High Similarity NPC131966
0.8489 Intermediate Similarity NPC121268
0.8489 Intermediate Similarity NPC473301
0.8489 Intermediate Similarity NPC53361
0.844 Intermediate Similarity NPC475135
0.8378 Intermediate Similarity NPC70344
0.831 Intermediate Similarity NPC183540
0.8224 Intermediate Similarity NPC55744
0.8222 Intermediate Similarity NPC472706
0.8207 Intermediate Similarity NPC475552
0.8176 Intermediate Similarity NPC22571
0.8176 Intermediate Similarity NPC283875
0.8176 Intermediate Similarity NPC469647
0.8176 Intermediate Similarity NPC469648
0.8176 Intermediate Similarity NPC138641
0.8148 Intermediate Similarity NPC476599
0.8138 Intermediate Similarity NPC471162
0.8138 Intermediate Similarity NPC471100
0.8138 Intermediate Similarity NPC134131
0.8138 Intermediate Similarity NPC25043
0.8138 Intermediate Similarity NPC471107
0.8134 Intermediate Similarity NPC472704
0.8125 Intermediate Similarity NPC95449
0.8108 Intermediate Similarity NPC472398
0.8106 Intermediate Similarity NPC473243
0.8095 Intermediate Similarity NPC473403
0.8067 Intermediate Similarity NPC469456
0.806 Intermediate Similarity NPC472703
0.8054 Intermediate Similarity NPC233581
0.8054 Intermediate Similarity NPC145649
0.8041 Intermediate Similarity NPC254558
0.8013 Intermediate Similarity NPC11410
0.7987 Intermediate Similarity NPC51602
0.7986 Intermediate Similarity NPC470278
0.7972 Intermediate Similarity NPC170718
0.7958 Intermediate Similarity NPC52523
0.7958 Intermediate Similarity NPC217673
0.7945 Intermediate Similarity NPC470231
0.7943 Intermediate Similarity NPC4242
0.7943 Intermediate Similarity NPC471911
0.7931 Intermediate Similarity NPC51181
0.7931 Intermediate Similarity NPC182869
0.7929 Intermediate Similarity NPC475569
0.7929 Intermediate Similarity NPC238370
0.7929 Intermediate Similarity NPC472394
0.7917 Intermediate Similarity NPC162613
0.7917 Intermediate Similarity NPC87934
0.7914 Intermediate Similarity NPC82712
0.7914 Intermediate Similarity NPC147561
0.7902 Intermediate Similarity NPC475373
0.7899 Intermediate Similarity NPC472707
0.7891 Intermediate Similarity NPC127857
0.7874 Intermediate Similarity NPC469636
0.7867 Intermediate Similarity NPC471103
0.7862 Intermediate Similarity NPC266374
0.7857 Intermediate Similarity NPC72915
0.7847 Intermediate Similarity NPC9905
0.7846 Intermediate Similarity NPC307651
0.7829 Intermediate Similarity NPC251139
0.7829 Intermediate Similarity NPC282239
0.7829 Intermediate Similarity NPC473670
0.7829 Intermediate Similarity NPC473611
0.7829 Intermediate Similarity NPC21410
0.7817 Intermediate Similarity NPC329913
0.7808 Intermediate Similarity NPC472546
0.7808 Intermediate Similarity NPC192658
0.78 Intermediate Similarity NPC112216
0.78 Intermediate Similarity NPC7095
0.7792 Intermediate Similarity NPC159692
0.7785 Intermediate Similarity NPC161151
0.7778 Intermediate Similarity NPC106895
0.7778 Intermediate Similarity NPC217091
0.7778 Intermediate Similarity NPC184109
0.7778 Intermediate Similarity NPC50872
0.7762 Intermediate Similarity NPC17877
0.7762 Intermediate Similarity NPC473399
0.7762 Intermediate Similarity NPC473216
0.7762 Intermediate Similarity NPC195647
0.7762 Intermediate Similarity NPC291638
0.7762 Intermediate Similarity NPC66761
0.7762 Intermediate Similarity NPC472577
0.7761 Intermediate Similarity NPC472708
0.7755 Intermediate Similarity NPC477894
0.7754 Intermediate Similarity NPC121272
0.7748 Intermediate Similarity NPC161955
0.7748 Intermediate Similarity NPC306799
0.7748 Intermediate Similarity NPC101043
0.7746 Intermediate Similarity NPC472656
0.7733 Intermediate Similarity NPC250046
0.7733 Intermediate Similarity NPC60509
0.7733 Intermediate Similarity NPC81698
0.773 Intermediate Similarity NPC469519
0.7727 Intermediate Similarity NPC472393
0.7722 Intermediate Similarity NPC477491
0.7718 Intermediate Similarity NPC478263
0.7718 Intermediate Similarity NPC312393
0.7712 Intermediate Similarity NPC473632
0.7712 Intermediate Similarity NPC469730
0.7712 Intermediate Similarity NPC132599
0.7703 Intermediate Similarity NPC34943
0.7692 Intermediate Similarity NPC82899
0.7692 Intermediate Similarity NPC474608
0.7692 Intermediate Similarity NPC270699
0.7692 Intermediate Similarity NPC48929
0.7692 Intermediate Similarity NPC126516
0.7692 Intermediate Similarity NPC203486
0.7682 Intermediate Similarity NPC470245
0.7682 Intermediate Similarity NPC473214
0.7682 Intermediate Similarity NPC165260
0.7682 Intermediate Similarity NPC198455
0.7682 Intermediate Similarity NPC161239
0.7681 Intermediate Similarity NPC246166
0.7677 Intermediate Similarity NPC471102
0.7676 Intermediate Similarity NPC469499
0.7671 Intermediate Similarity NPC48017
0.7671 Intermediate Similarity NPC147880
0.7671 Intermediate Similarity NPC473440
0.7671 Intermediate Similarity NPC200592
0.7671 Intermediate Similarity NPC4341
0.7671 Intermediate Similarity NPC473112
0.7671 Intermediate Similarity NPC211137
0.7671 Intermediate Similarity NPC476094
0.7671 Intermediate Similarity NPC43241

  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 NPC270364 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
0.8138 Intermediate Similarity NPD7236 Approved
0.7987 Intermediate Similarity NPD7239 Suspended
0.764 Intermediate Similarity NPD7799 Discontinued
0.7615 Intermediate Similarity NPD2181 Clinical (unspecified phase)
0.7571 Intermediate Similarity NPD6007 Clinical (unspecified phase)
0.7516 Intermediate Similarity NPD7057 Phase 3
0.7516 Intermediate Similarity NPD7058 Phase 2
0.75 Intermediate Similarity NPD7966 Clinical (unspecified phase)
0.7462 Intermediate Similarity NPD2182 Approved
0.7273 Intermediate Similarity NPD2067 Discontinued
0.7266 Intermediate Similarity NPD7457 Clinical (unspecified phase)
0.7192 Intermediate Similarity NPD7961 Discontinued
0.7176 Intermediate Similarity NPD6685 Approved
0.7154 Intermediate Similarity NPD164 Approved
0.7132 Intermediate Similarity NPD690 Clinical (unspecified phase)
0.7071 Intermediate Similarity NPD3412 Clinical (unspecified phase)
0.6985 Remote Similarity NPD6858 Approved
0.6985 Remote Similarity NPD7094 Approved
0.6972 Remote Similarity NPD6287 Discontinued
0.6966 Remote Similarity NPD5740 Clinical (unspecified phase)
0.6966 Remote Similarity NPD6085 Phase 2
0.6947 Remote Similarity NPD5765 Approved
0.6941 Remote Similarity NPD7685 Pre-registration
0.6941 Remote Similarity NPD8368 Discontinued
0.6936 Remote Similarity NPD8424 Clinical (unspecified phase)
0.6929 Remote Similarity NPD7741 Discontinued
0.6919 Remote Similarity NPD8407 Phase 2
0.6912 Remote Similarity NPD1609 Clinical (unspecified phase)
0.6912 Remote Similarity NPD6912 Phase 3
0.6863 Remote Similarity NPD6006 Clinical (unspecified phase)
0.6863 Remote Similarity NPD6003 Clinical (unspecified phase)
0.6863 Remote Similarity NPD6005 Phase 3
0.6863 Remote Similarity NPD6004 Phase 3
0.6863 Remote Similarity NPD6002 Phase 3
0.6846 Remote Similarity NPD1238 Approved
0.6839 Remote Similarity NPD4628 Phase 3
0.6824 Remote Similarity NPD5952 Clinical (unspecified phase)
0.6818 Remote Similarity NPD5738 Clinical (unspecified phase)
0.6809 Remote Similarity NPD9545 Approved
0.6788 Remote Similarity NPD5537 Clinical (unspecified phase)
0.677 Remote Similarity NPD6599 Discontinued
0.6763 Remote Similarity NPD2629 Approved
0.6748 Remote Similarity NPD5761 Phase 2
0.6748 Remote Similarity NPD5760 Phase 2
0.6744 Remote Similarity NPD6765 Approved
0.6744 Remote Similarity NPD6764 Approved
0.6743 Remote Similarity NPD8434 Phase 2
0.6714 Remote Similarity NPD4198 Discontinued
0.6692 Remote Similarity NPD6647 Phase 2
0.6691 Remote Similarity NPD6831 Clinical (unspecified phase)
0.6688 Remote Similarity NPD7137 Phase 2
0.6667 Remote Similarity NPD3764 Approved
0.6667 Remote Similarity NPD8435 Approved
0.6646 Remote Similarity NPD7096 Clinical (unspecified phase)
0.6645 Remote Similarity NPD7702 Clinical (unspecified phase)
0.6627 Remote Similarity NPD7075 Discontinued
0.6625 Remote Similarity NPD6273 Approved
0.6623 Remote Similarity NPD7305 Phase 1
0.6604 Remote Similarity NPD6799 Approved
0.66 Remote Similarity NPD7008 Discontinued
0.6599 Remote Similarity NPD1876 Approved
0.6591 Remote Similarity NPD8055 Clinical (unspecified phase)
0.6591 Remote Similarity NPD6785 Approved
0.6591 Remote Similarity NPD6784 Approved
0.6582 Remote Similarity NPD6190 Approved
0.6582 Remote Similarity NPD3887 Approved
0.6575 Remote Similarity NPD3972 Approved
0.6575 Remote Similarity NPD6637 Approved
0.6573 Remote Similarity NPD8361 Approved
0.6573 Remote Similarity NPD8360 Approved
0.657 Remote Similarity NPD8470 Clinical (unspecified phase)
0.6554 Remote Similarity NPD6362 Approved
0.6545 Remote Similarity NPD7819 Suspended
0.6536 Remote Similarity NPD230 Phase 1
0.6536 Remote Similarity NPD6355 Discontinued
0.6533 Remote Similarity NPD6832 Phase 2
0.6519 Remote Similarity NPD1237 Approved
0.6513 Remote Similarity NPD7713 Phase 3
0.6494 Remote Similarity NPD6653 Approved
0.6486 Remote Similarity NPD5667 Approved
0.6485 Remote Similarity NPD6801 Discontinued
0.6483 Remote Similarity NPD17 Approved
0.6474 Remote Similarity NPD2796 Approved
0.6461 Remote Similarity NPD8150 Discontinued
0.646 Remote Similarity NPD8389 Clinical (unspecified phase)
0.646 Remote Similarity NPD7004 Clinical (unspecified phase)
0.6456 Remote Similarity NPD7421 Clinical (unspecified phase)
0.6452 Remote Similarity NPD2569 Approved
0.6452 Remote Similarity NPD2567 Approved
0.6448 Remote Similarity NPD8485 Approved
0.6444 Remote Similarity NPD1931 Clinical (unspecified phase)
0.6444 Remote Similarity NPD1929 Approved
0.6444 Remote Similarity NPD1930 Approved
0.6433 Remote Similarity NPD2343 Clinical (unspecified phase)
0.6433 Remote Similarity NPD5762 Approved
0.6433 Remote Similarity NPD5763 Approved
0.6424 Remote Similarity NPD7055 Discontinued
0.6414 Remote Similarity NPD5585 Approved
0.6412 Remote Similarity NPD8127 Discontinued
0.6408 Remote Similarity NPD5951 Approved
0.6408 Remote Similarity NPD4766 Approved
0.6407 Remote Similarity NPD5402 Approved
0.6407 Remote Similarity NPD3817 Phase 2
0.6405 Remote Similarity NPD8032 Phase 2
0.6405 Remote Similarity NPD6663 Approved
0.64 Remote Similarity NPD5647 Approved
0.638 Remote Similarity NPD920 Approved
0.638 Remote Similarity NPD5403 Approved
0.638 Remote Similarity NPD6980 Clinical (unspecified phase)
0.6358 Remote Similarity NPD2533 Approved
0.6358 Remote Similarity NPD2534 Approved
0.6358 Remote Similarity NPD5401 Approved
0.6358 Remote Similarity NPD5736 Approved
0.6358 Remote Similarity NPD2532 Approved
0.6351 Remote Similarity NPD1608 Approved
0.635 Remote Similarity NPD5048 Discontinued
0.6345 Remote Similarity NPD7009 Phase 2
0.6344 Remote Similarity NPD8486 Clinical (unspecified phase)
0.6343 Remote Similarity NPD2066 Phase 3
0.6336 Remote Similarity NPD1202 Approved
0.6329 Remote Similarity NPD2355 Clinical (unspecified phase)
0.6329 Remote Similarity NPD2353 Approved
0.6319 Remote Similarity NPD7879 Clinical (unspecified phase)
0.6312 Remote Similarity NPD6398 Clinical (unspecified phase)
0.631 Remote Similarity NPD8443 Clinical (unspecified phase)
0.6306 Remote Similarity NPD3748 Approved
0.6306 Remote Similarity NPD2799 Discontinued
0.6306 Remote Similarity NPD7033 Discontinued
0.6303 Remote Similarity NPD6591 Clinical (unspecified phase)
0.6303 Remote Similarity NPD7458 Discontinued
0.6299 Remote Similarity NPD9259 Approved
0.6299 Remote Similarity NPD9257 Approved
0.6288 Remote Similarity NPD1693 Approved
0.6284 Remote Similarity NPD4806 Approved
0.6284 Remote Similarity NPD4807 Approved
0.6277 Remote Similarity NPD5909 Discontinued
0.6276 Remote Similarity NPD7610 Discontinued
0.6275 Remote Similarity NPD6039 Approved
0.6269 Remote Similarity NPD9495 Approved
0.6267 Remote Similarity NPD2198 Approved
0.6267 Remote Similarity NPD2199 Approved
0.6259 Remote Similarity NPD5306 Approved
0.6259 Remote Similarity NPD5305 Approved
0.6258 Remote Similarity NPD642 Clinical (unspecified phase)
0.6258 Remote Similarity NPD4378 Clinical (unspecified phase)
0.6257 Remote Similarity NPD5494 Approved
0.625 Remote Similarity NPD3661 Approved
0.625 Remote Similarity NPD3662 Phase 3
0.625 Remote Similarity NPD3663 Approved
0.625 Remote Similarity NPD3664 Approved
0.6241 Remote Similarity NPD4141 Clinical (unspecified phase)
0.6241 Remote Similarity NPD1989 Approved
0.6234 Remote Similarity NPD6859 Clinical (unspecified phase)
0.6234 Remote Similarity NPD2313 Discontinued
0.6231 Remote Similarity NPD3672 Approved
0.6231 Remote Similarity NPD3673 Approved
0.6229 Remote Similarity NPD7893 Clinical (unspecified phase)
0.6228 Remote Similarity NPD6385 Approved
0.6228 Remote Similarity NPD6386 Approved
0.6228 Remote Similarity NPD7411 Suspended
0.6226 Remote Similarity NPD1471 Phase 3
0.6225 Remote Similarity NPD3267 Approved
0.6225 Remote Similarity NPD3266 Approved
0.6224 Remote Similarity NPD2652 Approved
0.6224 Remote Similarity NPD2650 Approved
0.6222 Remote Similarity NPD7798 Approved
0.6213 Remote Similarity NPD5353 Approved
0.6212 Remote Similarity NPD5122 Clinical (unspecified phase)
0.6211 Remote Similarity NPD2575 Approved
0.6211 Remote Similarity NPD8166 Discontinued
0.6211 Remote Similarity NPD1878 Clinical (unspecified phase)
0.6207 Remote Similarity NPD9493 Approved
0.6207 Remote Similarity NPD4230 Clinical (unspecified phase)
0.6205 Remote Similarity NPD3226 Approved
0.62 Remote Similarity NPD4359 Approved
0.6199 Remote Similarity NPD919 Approved
0.6197 Remote Similarity NPD969 Suspended
0.6193 Remote Similarity NPD7804 Clinical (unspecified phase)
0.6188 Remote Similarity NPD970 Clinical (unspecified phase)
0.6184 Remote Similarity NPD1019 Discontinued
0.6184 Remote Similarity NPD2798 Approved
0.6184 Remote Similarity NPD2788 Approved
0.6176 Remote Similarity NPD4868 Clinical (unspecified phase)
0.6176 Remote Similarity NPD3882 Suspended
0.6173 Remote Similarity NPD2354 Approved
0.617 Remote Similarity NPD4233 Approved
0.617 Remote Similarity NPD4234 Approved
0.6168 Remote Similarity NPD4380 Phase 2
0.6158 Remote Similarity NPD7497 Discontinued
0.6154 Remote Similarity NPD4307 Phase 2
0.6154 Remote Similarity NPD8462 Phase 1
0.6154 Remote Similarity NPD7460 Discontinued
0.6149 Remote Similarity NPD7184 Clinical (unspecified phase)
0.6149 Remote Similarity NPD7163 Clinical (unspecified phase)
0.6149 Remote Similarity NPD2800 Approved
0.6149 Remote Similarity NPD1243 Approved
0.6136 Remote Similarity NPD1088 Approved
0.6135 Remote Similarity NPD6652 Clinical (unspecified phase)
0.6135 Remote Similarity NPD643 Clinical (unspecified phase)
0.6131 Remote Similarity NPD1932 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