Structure

Physi-Chem Properties

Molecular Weight:  920.29
Volume:  873.805
LogP:  1.599
LogD:  1.131
LogS:  -4.113
# Rotatable Bonds:  15
TPSA:  278.78
# H-Bond Aceptor:  21
# H-Bond Donor:  1
# Rings:  7
# Heavy Atoms:  21

MedChem Properties

QED Drug-Likeness Score:  0.238
Synthetic Accessibility Score:  7.785
Fsp3:  0.511
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:  -5.321
MDCK Permeability:  0.00014797048061154783
Pgp-inhibitor:  1.0
Pgp-substrate:  0.012
Human Intestinal Absorption (HIA):  0.842
20% Bioavailability (F20%):  0.998
30% Bioavailability (F30%):  0.978

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.041
Plasma Protein Binding (PPB):  60.15538787841797%
Volume Distribution (VD):  1.868
Pgp-substrate:  15.657551765441895%

ADMET: Metabolism

CYP1A2-inhibitor:  0.172
CYP1A2-substrate:  0.021
CYP2C19-inhibitor:  0.103
CYP2C19-substrate:  0.056
CYP2C9-inhibitor:  0.303
CYP2C9-substrate:  0.009
CYP2D6-inhibitor:  0.887
CYP2D6-substrate:  0.019
CYP3A4-inhibitor:  0.924
CYP3A4-substrate:  0.256

ADMET: Excretion

Clearance (CL):  3.044
Half-life (T1/2):  0.297

ADMET: Toxicity

hERG Blockers:  0.236
Human Hepatotoxicity (H-HT):  0.966
Drug-inuced Liver Injury (DILI):  0.987
AMES Toxicity:  0.034
Rat Oral Acute Toxicity:  0.057
Maximum Recommended Daily Dose:  0.016
Skin Sensitization:  0.076
Carcinogencity:  0.041
Eye Corrosion:  0.003
Eye Irritation:  0.02
Respiratory Toxicity:  0.053

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

  Natural Product: NPC328928

Natural Product ID:  NPC328928
Common Name*:   Hyponine E
IUPAC Name:   n.a.
Synonyms:   Hyponine E
Standard InCHIKey:  PMRSIAJYXABCTQ-IWYQQVOHSA-N
Standard InCHI:  InChI=1S/C45H48N2O19/c1-21-22(2)38(52)65-35-33(60-24(4)49)37(62-26(6)51)44(20-58-23(3)48)36(61-25(5)50)32(63-39(53)27-12-9-15-46-18-27)30-34(64-41(55)29-14-11-17-57-29)45(44,43(35,8)56)66-42(30,7)19-59-40(54)28-13-10-16-47-31(21)28/h9-18,21-22,30,32-37,56H,19-20H2,1-8H3/t21?,22?,30-,32-,33+,34-,35+,36-,37+,42+,43+,44-,45+/m1/s1
SMILES:  CC1C(C(=O)OC2C(C(C3(C(C(C4C(C3(C2(C)O)OC4(COC(=O)C5=C1N=CC=C5)C)OC(=O)C6=CC=CO6)OC(=O)C7=CN=CC=C7)OC(=O)C)COC(=O)C)OC(=O)C)OC(=O)C)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL501685
PubChem CID:   44583772
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000279] Alkaloids and derivatives

*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
NPO1152 Tripterygium hypoglaucum Species Celastraceae Eukaryota n.a. root n.a. DOI[10.1016/S0040-4039(99)00339-1]
NPO1152 Tripterygium hypoglaucum Species Celastraceae Eukaryota n.a. root n.a. PMID[10746886]
NPO1152 Tripterygium hypoglaucum Species Celastraceae Eukaryota n.a. root n.a. PMID[10757718]
NPO1152 Tripterygium hypoglaucum Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[10757718]
NPO1152 Tripterygium hypoglaucum Species Celastraceae Eukaryota root bark Kunming, Yunnan, China n.a. PMID[10757718]
NPO1152 Tripterygium hypoglaucum Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[22256754]
NPO1152 Tripterygium hypoglaucum Species Celastraceae Eukaryota n.a. root n.a. PMID[22256754]
NPO1152 Tripterygium hypoglaucum Species Celastraceae Eukaryota n.a. root n.a. PMID[23252270]
NPO1152 Tripterygium hypoglaucum Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[2534610]
NPO1152 Tripterygium hypoglaucum Species Celastraceae Eukaryota n.a. n.a. n.a. Europe PMC[535601]
NPO1152 Tripterygium hypoglaucum Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[8328267]
NPO1152 Tripterygium hypoglaucum Species Celastraceae Eukaryota n.a. n.a. n.a. Database[Article]
NPO1152 Tripterygium hypoglaucum Species Celastraceae Eukaryota n.a. leaf n.a. Database[Article]
NPO1152 Tripterygium hypoglaucum Species Celastraceae Eukaryota n.a. root n.a. Database[Article]
NPO1152 Tripterygium hypoglaucum Species Celastraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO1152 Tripterygium hypoglaucum Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[Phytochemistry, 2000, 53, 715-722.]
NPO1152 Tripterygium hypoglaucum Species Celastraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO1152 Tripterygium hypoglaucum Species Celastraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO1152 Tripterygium hypoglaucum Species Celastraceae Eukaryota n.a. n.a. n.a. Database[Title]
NPO1152 Tripterygium hypoglaucum Species Celastraceae Eukaryota root bark n.a. n.a. Database[Title]
NPO1152 Tripterygium hypoglaucum Species Celastraceae Eukaryota root bark Kunming, Yunnan, China n.a. Database[Title]
NPO1152 Tripterygium hypoglaucum Species Celastraceae 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
NPT759 Cell Line H9 Homo sapiens IC50 = 1.95 ug.mL-1 PMID[468683]
NPT24 Organism Human immunodeficiency virus 1 Human immunodeficiency virus 1 EC50 = 0.17 ug.mL-1 PMID[468683]
NPT27 Others Unspecified Ratio IC50/EC50 = 11.3 n.a. PMID[468683]

☑ 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 NPC328928 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
0.9738 High Similarity NPC326930
0.9738 High Similarity NPC475301
0.961 High Similarity NPC13603
0.9571 High Similarity NPC473833
0.9567 High Similarity NPC85879
0.9567 High Similarity NPC53255
0.9432 High Similarity NPC475533
0.9391 High Similarity NPC324619
0.9391 High Similarity NPC475315
0.9208 High Similarity NPC471979
0.9163 High Similarity NPC471978
0.895 High Similarity NPC471015
0.8874 High Similarity NPC327769
0.8824 High Similarity NPC10904
0.8814 High Similarity NPC471013
0.8814 High Similarity NPC148896
0.8814 High Similarity NPC180668
0.8712 High Similarity NPC35208
0.8707 High Similarity NPC244839
0.8707 High Similarity NPC320324
0.8707 High Similarity NPC319880
0.8696 High Similarity NPC475631
0.8696 High Similarity NPC475600
0.8696 High Similarity NPC87152
0.8696 High Similarity NPC476110
0.8675 High Similarity NPC327904
0.8675 High Similarity NPC38959
0.867 High Similarity NPC237702
0.8664 High Similarity NPC475303
0.8664 High Similarity NPC292416
0.8664 High Similarity NPC473689
0.8664 High Similarity NPC475596
0.8658 High Similarity NPC475644
0.8658 High Similarity NPC471977
0.8658 High Similarity NPC471190
0.8658 High Similarity NPC470486
0.8646 High Similarity NPC76565
0.8644 High Similarity NPC253482
0.8632 High Similarity NPC475406
0.8627 High Similarity NPC30456
0.8615 High Similarity NPC146824
0.8613 High Similarity NPC475648
0.8609 High Similarity NPC475137
0.8609 High Similarity NPC475498
0.8578 High Similarity NPC475362
0.8571 High Similarity NPC473506
0.8553 High Similarity NPC475426
0.8534 High Similarity NPC122968
0.8534 High Similarity NPC477787
0.8534 High Similarity NPC328186
0.8534 High Similarity NPC228377
0.8528 High Similarity NPC328154
0.8504 High Similarity NPC316841
0.8491 Intermediate Similarity NPC148860
0.8485 Intermediate Similarity NPC57797
0.8485 Intermediate Similarity NPC250807
0.8475 Intermediate Similarity NPC170751
0.8455 Intermediate Similarity NPC475601
0.8448 Intermediate Similarity NPC473850
0.8442 Intermediate Similarity NPC477911
0.8426 Intermediate Similarity NPC96801
0.8426 Intermediate Similarity NPC150698
0.8398 Intermediate Similarity NPC477912
0.8391 Intermediate Similarity NPC301368
0.8391 Intermediate Similarity NPC84815
0.839 Intermediate Similarity NPC471004
0.8384 Intermediate Similarity NPC471016
0.8362 Intermediate Similarity NPC127720
0.8362 Intermediate Similarity NPC477788
0.8362 Intermediate Similarity NPC127026
0.8341 Intermediate Similarity NPC470306
0.8326 Intermediate Similarity NPC471980
0.8312 Intermediate Similarity NPC472555
0.8312 Intermediate Similarity NPC469748
0.8304 Intermediate Similarity NPC471014
0.8304 Intermediate Similarity NPC6981
0.8304 Intermediate Similarity NPC475408
0.827 Intermediate Similarity NPC477906
0.8268 Intermediate Similarity NPC62367
0.8268 Intermediate Similarity NPC144779
0.8268 Intermediate Similarity NPC294579
0.8233 Intermediate Similarity NPC216428
0.8225 Intermediate Similarity NPC477908
0.8225 Intermediate Similarity NPC206343
0.822 Intermediate Similarity NPC211920
0.822 Intermediate Similarity NPC124029
0.8217 Intermediate Similarity NPC4421
0.8213 Intermediate Similarity NPC477900
0.8213 Intermediate Similarity NPC477899
0.8213 Intermediate Similarity NPC477902
0.819 Intermediate Similarity NPC6576
0.819 Intermediate Similarity NPC158020
0.819 Intermediate Similarity NPC212768
0.819 Intermediate Similarity NPC473089
0.819 Intermediate Similarity NPC75600
0.819 Intermediate Similarity NPC473115
0.8182 Intermediate Similarity NPC477909
0.8182 Intermediate Similarity NPC477907
0.8182 Intermediate Similarity NPC42678
0.8151 Intermediate Similarity NPC91125
0.8139 Intermediate Similarity NPC319128
0.8139 Intermediate Similarity NPC228331
0.8136 Intermediate Similarity NPC26881
0.8128 Intermediate Similarity NPC235364
0.8103 Intermediate Similarity NPC477910
0.8085 Intermediate Similarity NPC477903
0.8052 Intermediate Similarity NPC472553
0.8043 Intermediate Similarity NPC477901
0.7983 Intermediate Similarity NPC264674
0.7922 Intermediate Similarity NPC48042
0.7922 Intermediate Similarity NPC304179
0.7922 Intermediate Similarity NPC472550
0.7901 Intermediate Similarity NPC238278
0.7884 Intermediate Similarity NPC134384
0.7884 Intermediate Similarity NPC311196
0.786 Intermediate Similarity NPC213143
0.7842 Intermediate Similarity NPC14116
0.7842 Intermediate Similarity NPC285411
0.7826 Intermediate Similarity NPC289086
0.7802 Intermediate Similarity NPC63041
0.7768 Intermediate Similarity NPC472752
0.7759 Intermediate Similarity NPC233727
0.7731 Intermediate Similarity NPC319556
0.7659 Intermediate Similarity NPC107123
0.7647 Intermediate Similarity NPC207531
0.7595 Intermediate Similarity NPC476467
0.7573 Intermediate Similarity NPC30570
0.7563 Intermediate Similarity NPC165837
0.7521 Intermediate Similarity NPC292517
0.7521 Intermediate Similarity NPC280473
0.7521 Intermediate Similarity NPC323551
0.751 Intermediate Similarity NPC187494
0.749 Intermediate Similarity NPC41724
0.749 Intermediate Similarity NPC51008
0.748 Intermediate Similarity NPC476090
0.7479 Intermediate Similarity NPC40919
0.7479 Intermediate Similarity NPC470189
0.7469 Intermediate Similarity NPC162812
0.7452 Intermediate Similarity NPC478045
0.7441 Intermediate Similarity NPC75179
0.7426 Intermediate Similarity NPC470190
0.7418 Intermediate Similarity NPC253314
0.7403 Intermediate Similarity NPC183537
0.7384 Intermediate Similarity NPC475835
0.7373 Intermediate Similarity NPC15406
0.7362 Intermediate Similarity NPC210296
0.7362 Intermediate Similarity NPC119134
0.7355 Intermediate Similarity NPC62844
0.7355 Intermediate Similarity NPC193361
0.7349 Intermediate Similarity NPC24019
0.7344 Intermediate Similarity NPC124313
0.7341 Intermediate Similarity NPC108342
0.7338 Intermediate Similarity NPC191489
0.7336 Intermediate Similarity NPC77878
0.7312 Intermediate Similarity NPC182907
0.7312 Intermediate Similarity NPC189903
0.7302 Intermediate Similarity NPC90875
0.73 Intermediate Similarity NPC472436
0.7297 Intermediate Similarity NPC134637
0.7293 Intermediate Similarity NPC315634
0.7293 Intermediate Similarity NPC88923
0.7293 Intermediate Similarity NPC100734
0.7291 Intermediate Similarity NPC233334
0.7277 Intermediate Similarity NPC470279
0.7273 Intermediate Similarity NPC236668
0.7266 Intermediate Similarity NPC84164
0.7266 Intermediate Similarity NPC207283
0.7262 Intermediate Similarity NPC258048
0.7262 Intermediate Similarity NPC255800
0.7262 Intermediate Similarity NPC96584
0.7243 Intermediate Similarity NPC146976
0.7224 Intermediate Similarity NPC314270
0.7216 Intermediate Similarity NPC166722
0.7194 Intermediate Similarity NPC22481
0.7191 Intermediate Similarity NPC152620
0.7186 Intermediate Similarity NPC472435
0.7183 Intermediate Similarity NPC201508
0.7177 Intermediate Similarity NPC210434
0.7171 Intermediate Similarity NPC188400
0.7171 Intermediate Similarity NPC246381
0.717 Intermediate Similarity NPC284685
0.7167 Intermediate Similarity NPC193238
0.7149 Intermediate Similarity NPC322482
0.7149 Intermediate Similarity NPC470020
0.7143 Intermediate Similarity NPC278525
0.7138 Intermediate Similarity NPC196449
0.7138 Intermediate Similarity NPC314222
0.7126 Intermediate Similarity NPC270515
0.7125 Intermediate Similarity NPC309498
0.7105 Intermediate Similarity NPC129897
0.7101 Intermediate Similarity NPC32451
0.7101 Intermediate Similarity NPC328559
0.7097 Intermediate Similarity NPC54066
0.7094 Intermediate Similarity NPC103230
0.709 Intermediate Similarity NPC111732
0.7074 Intermediate Similarity NPC227824
0.7059 Intermediate Similarity NPC70155
0.7059 Intermediate Similarity NPC473639
0.7052 Intermediate Similarity NPC215837
0.704 Intermediate Similarity NPC122463

  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 NPC328928 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
0.78 Intermediate Similarity NPD8468 Phase 2
0.761 Intermediate Similarity NPD1483 Discontinued
0.7569 Intermediate Similarity NPD6525 Clinical (unspecified phase)
0.7542 Intermediate Similarity NPD4989 Phase 2
0.7448 Intermediate Similarity NPD7069 Discontinued
0.7391 Intermediate Similarity NPD7886 Phase 2
0.7391 Intermediate Similarity NPD7885 Phase 2
0.7338 Intermediate Similarity NPD7708 Approved
0.7331 Intermediate Similarity NPD4373 Phase 2
0.7293 Intermediate Similarity NPD7803 Approved
0.7288 Intermediate Similarity NPD6477 Clinical (unspecified phase)
0.728 Intermediate Similarity NPD5801 Clinical (unspecified phase)
0.728 Intermediate Similarity NPD8052 Clinical (unspecified phase)
0.7251 Intermediate Similarity NPD6962 Phase 2
0.7229 Intermediate Similarity NPD5640 Discontinued
0.7227 Intermediate Similarity NPD7396 Approved
0.7211 Intermediate Similarity NPD4952 Phase 3
0.717 Intermediate Similarity NPD7955 Approved
0.717 Intermediate Similarity NPD7956 Approved
0.7166 Intermediate Similarity NPD8479 Phase 2
0.7165 Intermediate Similarity NPD8101 Phase 3
0.7143 Intermediate Similarity NPD6530 Approved
0.7143 Intermediate Similarity NPD6531 Approved
0.7131 Intermediate Similarity NPD4396 Clinical (unspecified phase)
0.7117 Intermediate Similarity NPD3217 Phase 2
0.7116 Intermediate Similarity NPD7862 Clinical (unspecified phase)
0.7114 Intermediate Similarity NPD3326 Clinical (unspecified phase)
0.7093 Intermediate Similarity NPD7417 Discontinued
0.709 Intermediate Similarity NPD5866 Approved
0.7075 Intermediate Similarity NPD5022 Discontinued
0.707 Intermediate Similarity NPD5891 Approved
0.707 Intermediate Similarity NPD3006 Discontinued
0.7068 Intermediate Similarity NPD8091 Phase 3
0.705 Intermediate Similarity NPD8100 Phase 3
0.7049 Intermediate Similarity NPD7927 Clinical (unspecified phase)
0.7034 Intermediate Similarity NPD5482 Discontinued
0.7012 Intermediate Similarity NPD2831 Approved
0.7 Intermediate Similarity NPD6716 Phase 1
0.6993 Remote Similarity NPD8465 Approved
0.6993 Remote Similarity NPD8467 Approved
0.6993 Remote Similarity NPD8466 Approved
0.6984 Remote Similarity NPD3925 Approved
0.6962 Remote Similarity NPD6790 Phase 1
0.6958 Remote Similarity NPD6276 Discontinued
0.6957 Remote Similarity NPD7426 Phase 1
0.6953 Remote Similarity NPD8460 Approved
0.6953 Remote Similarity NPD8459 Approved
0.695 Remote Similarity NPD6825 Phase 1
0.6948 Remote Similarity NPD7395 Discontinued
0.6947 Remote Similarity NPD5483 Clinical (unspecified phase)
0.6943 Remote Similarity NPD8304 Clinical (unspecified phase)
0.6942 Remote Similarity NPD3946 Clinical (unspecified phase)
0.694 Remote Similarity NPD4889 Approved
0.6939 Remote Similarity NPD6262 Clinical (unspecified phase)
0.6929 Remote Similarity NPD7268 Clinical (unspecified phase)
0.6926 Remote Similarity NPD6741 Clinical (unspecified phase)
0.6923 Remote Similarity NPD3794 Approved
0.6923 Remote Similarity NPD3795 Approved
0.6923 Remote Similarity NPD7571 Clinical (unspecified phase)
0.692 Remote Similarity NPD5975 Clinical (unspecified phase)
0.6908 Remote Similarity NPD8404 Phase 2
0.6907 Remote Similarity NPD6569 Phase 2
0.6899 Remote Similarity NPD7807 Clinical (unspecified phase)
0.6893 Remote Similarity NPD8426 Approved
0.6893 Remote Similarity NPD8425 Approved
0.6877 Remote Similarity NPD7169 Suspended
0.6871 Remote Similarity NPD8429 Approved
0.6871 Remote Similarity NPD8428 Approved
0.6871 Remote Similarity NPD8427 Approved
0.6868 Remote Similarity NPD4369 Phase 2
0.6868 Remote Similarity NPD8350 Clinical (unspecified phase)
0.6867 Remote Similarity NPD3393 Approved
0.6867 Remote Similarity NPD3389 Approved
0.6867 Remote Similarity NPD3394 Approved
0.6865 Remote Similarity NPD5147 Discontinued
0.6863 Remote Similarity NPD6553 Clinical (unspecified phase)
0.6858 Remote Similarity NPD2921 Clinical (unspecified phase)
0.6838 Remote Similarity NPD8356 Approved
0.6836 Remote Similarity NPD8364 Approved
0.6836 Remote Similarity NPD8363 Approved
0.6827 Remote Similarity NPD4667 Clinical (unspecified phase)
0.6815 Remote Similarity NPD3816 Phase 1
0.6815 Remote Similarity NPD3815 Phase 1
0.6813 Remote Similarity NPD1926 Approved
0.6808 Remote Similarity NPD7853 Phase 2
0.68 Remote Similarity NPD7925 Phase 2
0.68 Remote Similarity NPD7924 Phase 2
0.6798 Remote Similarity NPD6298 Discontinued
0.6797 Remote Similarity NPD7416 Clinical (unspecified phase)
0.6795 Remote Similarity NPD6494 Phase 2
0.6795 Remote Similarity NPD7558 Phase 2
0.6789 Remote Similarity NPD2509 Approved
0.6789 Remote Similarity NPD2510 Approved
0.6788 Remote Similarity NPD5450 Discontinued
0.6787 Remote Similarity NPD8365 Clinical (unspecified phase)
0.6782 Remote Similarity NPD5805 Approved
0.6774 Remote Similarity NPD7703 Clinical (unspecified phase)
0.6774 Remote Similarity NPD5416 Discontinued
0.6768 Remote Similarity NPD8279 Clinical (unspecified phase)
0.6767 Remote Similarity NPD8358 Approved
0.6766 Remote Similarity NPD8463 Approved
0.6766 Remote Similarity NPD4926 Clinical (unspecified phase)
0.6765 Remote Similarity NPD3924 Approved
0.6765 Remote Similarity NPD5867 Clinical (unspecified phase)
0.6765 Remote Similarity NPD6228 Discontinued
0.6765 Remote Similarity NPD3923 Approved
0.6765 Remote Similarity NPD3921 Approved
0.6765 Remote Similarity NPD3922 Approved
0.676 Remote Similarity NPD5417 Clinical (unspecified phase)
0.6759 Remote Similarity NPD6242 Discontinued
0.6748 Remote Similarity NPD5429 Discontinued
0.6746 Remote Similarity NPD4429 Discontinued
0.6746 Remote Similarity NPD6568 Discontinued
0.6744 Remote Similarity NPD7589 Clinical (unspecified phase)
0.6742 Remote Similarity NPD8102 Discontinued
0.6739 Remote Similarity NPD7393 Clinical (unspecified phase)
0.6737 Remote Similarity NPD6257 Clinical (unspecified phase)
0.6736 Remote Similarity NPD6361 Phase 2
0.6735 Remote Similarity NPD6987 Phase 1
0.6732 Remote Similarity NPD4923 Phase 1
0.6732 Remote Similarity NPD4328 Approved
0.6732 Remote Similarity NPD8430 Approved
0.6732 Remote Similarity NPD7556 Discontinued
0.6729 Remote Similarity NPD7859 Phase 2
0.6727 Remote Similarity NPD5922 Phase 3
0.6721 Remote Similarity NPD7467 Discontinued
0.6719 Remote Similarity NPD6955 Clinical (unspecified phase)
0.6708 Remote Similarity NPD5228 Phase 3
0.6707 Remote Similarity NPD6567 Clinical (unspecified phase)
0.6706 Remote Similarity NPD8327 Clinical (unspecified phase)
0.6706 Remote Similarity NPD8325 Phase 3
0.6706 Remote Similarity NPD8326 Phase 3
0.6693 Remote Similarity NPD7538 Clinical (unspecified phase)
0.6693 Remote Similarity NPD7180 Phase 3
0.6693 Remote Similarity NPD5293 Phase 2
0.6692 Remote Similarity NPD7797 Approved
0.6692 Remote Similarity NPD7967 Discontinued
0.6692 Remote Similarity NPD7796 Approved
0.6691 Remote Similarity NPD6503 Clinical (unspecified phase)
0.668 Remote Similarity NPD5632 Approved
0.668 Remote Similarity NPD7547 Clinical (unspecified phase)
0.668 Remote Similarity NPD5512 Phase 3
0.668 Remote Similarity NPD3354 Phase 2
0.668 Remote Similarity NPD1659 Phase 1
0.6679 Remote Similarity NPD3322 Phase 1
0.6679 Remote Similarity NPD7022 Phase 2
0.6667 Remote Similarity NPD3259 Approved
0.6667 Remote Similarity NPD32 Approved
0.6667 Remote Similarity NPD31 Approved
0.6667 Remote Similarity NPD8359 Phase 2
0.6667 Remote Similarity NPD4122 Approved
0.6667 Remote Similarity NPD4036 Approved
0.6667 Remote Similarity NPD4033 Approved
0.6667 Remote Similarity NPD4038 Approved
0.6667 Remote Similarity NPD7025 Clinical (unspecified phase)
0.6667 Remote Similarity NPD4035 Approved
0.6667 Remote Similarity NPD7994 Phase 2
0.6667 Remote Similarity NPD4034 Approved
0.6667 Remote Similarity NPD3947 Discontinued
0.6667 Remote Similarity NPD5488 Discontinued
0.6667 Remote Similarity NPD4037 Approved
0.6667 Remote Similarity NPD4039 Approved
0.6654 Remote Similarity NPD6974 Phase 3
0.6654 Remote Similarity NPD6247 Clinical (unspecified phase)
0.6653 Remote Similarity NPD5721 Clinical (unspecified phase)
0.6643 Remote Similarity NPD7673 Phase 3
0.6642 Remote Similarity NPD8370 Discontinued
0.6641 Remote Similarity NPD6964 Approved
0.6641 Remote Similarity NPD6963 Approved
0.6632 Remote Similarity NPD8489 Phase 1
0.663 Remote Similarity NPD8461 Discontinued
0.6629 Remote Similarity NPD7660 Clinical (unspecified phase)
0.6628 Remote Similarity NPD3263 Phase 3
0.6627 Remote Similarity NPD3280 Approved
0.6627 Remote Similarity NPD7707 Approved
0.6624 Remote Similarity NPD4375 Approved
0.6618 Remote Similarity NPD8247 Approved
0.6618 Remote Similarity NPD8442 Discontinued
0.6618 Remote Similarity NPD8246 Approved
0.6611 Remote Similarity NPD8063 Discontinued
0.6604 Remote Similarity NPD8017 Clinical (unspecified phase)
0.6604 Remote Similarity NPD8016 Phase 3
0.6601 Remote Similarity NPD2433 Clinical (unspecified phase)
0.6599 Remote Similarity NPD8310 Clinical (unspecified phase)
0.6598 Remote Similarity NPD6874 Approved
0.6591 Remote Similarity NPD4958 Clinical (unspecified phase)
0.6588 Remote Similarity NPD6770 Approved
0.6584 Remote Similarity NPD7053 Clinical (unspecified phase)
0.6576 Remote Similarity NPD8421 Discontinued
0.6576 Remote Similarity NPD6824 Clinical (unspecified phase)
0.6573 Remote Similarity NPD6732 Clinical (unspecified phase)
0.6573 Remote Similarity NPD3507 Phase 2
0.6573 Remote Similarity NPD7010 Phase 3
0.6565 Remote Similarity NPD7031 Phase 1
0.6564 Remote Similarity NPD7676 Clinical (unspecified phase)
0.6564 Remote Similarity NPD7674 Phase 3
0.6564 Remote Similarity NPD7675 Phase 3
0.656 Remote Similarity NPD4506 Discontinued
0.656 Remote Similarity NPD6529 Discontinued
0.6559 Remote Similarity NPD2121 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