Structure

Physi-Chem Properties

Molecular Weight:  588.26
Volume:  580.187
LogP:  1.776
LogD:  1.327
LogS:  -4.399
# Rotatable Bonds:  8
TPSA:  169.05
# H-Bond Aceptor:  11
# H-Bond Donor:  4
# Rings:  5
# Heavy Atoms:  11

MedChem Properties

QED Drug-Likeness Score:  0.223
Synthetic Accessibility Score:  5.132
Fsp3:  0.645
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:  -5.705
MDCK Permeability:  8.100603008642793e-05
Pgp-inhibitor:  0.958
Pgp-substrate:  1.0
Human Intestinal Absorption (HIA):  0.804
20% Bioavailability (F20%):  0.946
30% Bioavailability (F30%):  0.991

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.144
Plasma Protein Binding (PPB):  32.130043029785156%
Volume Distribution (VD):  0.908
Pgp-substrate:  31.349197387695312%

ADMET: Metabolism

CYP1A2-inhibitor:  0.008
CYP1A2-substrate:  0.044
CYP2C19-inhibitor:  0.009
CYP2C19-substrate:  0.319
CYP2C9-inhibitor:  0.006
CYP2C9-substrate:  0.038
CYP2D6-inhibitor:  0.019
CYP2D6-substrate:  0.051
CYP3A4-inhibitor:  0.101
CYP3A4-substrate:  0.397

ADMET: Excretion

Clearance (CL):  3.202
Half-life (T1/2):  0.521

ADMET: Toxicity

hERG Blockers:  0.557
Human Hepatotoxicity (H-HT):  0.916
Drug-inuced Liver Injury (DILI):  0.631
AMES Toxicity:  0.056
Rat Oral Acute Toxicity:  0.752
Maximum Recommended Daily Dose:  0.967
Skin Sensitization:  0.145
Carcinogencity:  0.018
Eye Corrosion:  0.003
Eye Irritation:  0.013
Respiratory Toxicity:  0.975

Download Data

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

  Natural Product: NPC92867

Natural Product ID:  NPC92867
Common Name*:   Taxumairol K
IUPAC Name:   n.a.
Synonyms:   Taxumairol K
Standard InCHIKey:  IEMBQVLDTQOXFV-LPRGFTSCSA-N
Standard InCHI:  InChI=1S/C31H40O11/c1-15-19(34)13-30(28(4,5)38)22(15)23(36)25(41-27(37)18-10-8-7-9-11-18)29(6)20(35)12-21-31(14-39-21,42-17(3)33)24(29)26(30)40-16(2)32/h7-11,19-21,23-26,34-36,38H,12-14H2,1-6H3/t19-,20-,21+,23+,24-,25-,26-,29+,30-,31-/m0/s1
SMILES:  CC1=C2[C@H]([C@@H]([C@]3(C)[C@H](C[C@@H]4[C@@](CO4)([C@H]3[C@@H]([C@@]2(C[C@@H]1O)C(C)(C)O)OC(=O)C)OC(=O)C)O)OC(=O)c1ccccc1)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL509773
PubChem CID:   10769688
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001551] Diterpenoids
          • [CHEMONTID:0000676] Taxanes 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
NPO27746 Taxus mairei Species Taxaceae Eukaryota stem bark n.a. n.a. PMID[11473432]
NPO25366 Sapium indicum Species Euphorbiaceae Eukaryota Fruits n.a. n.a. PMID[12713411]
NPO23788 Beauveria bassiana Species Cordycipitaceae Eukaryota n.a. n.a. n.a. PMID[16124776]
NPO6645.1 Picea jezoensis var. jezoensis Varieties Pinaceae Eukaryota bark n.a. n.a. PMID[17907781]
NPO23788 Beauveria bassiana Species Cordycipitaceae Eukaryota n.a. n.a. n.a. PMID[18804027]
NPO6645.1 Picea jezoensis var. jezoensis Varieties Pinaceae Eukaryota bark n.a. n.a. PMID[19646881]
NPO23788 Beauveria bassiana Species Cordycipitaceae Eukaryota n.a. n.a. n.a. PMID[20233596]
NPO25054 Phaleria macrocarpa Species Thymelaeaceae Eukaryota nut shell n.a. n.a. PMID[23044367]
NPO25252 Nannocystis exedens Species Nannocystaceae Bacteria n.a. n.a. n.a. PMID[24460410]
NPO25311 Guettarda platypoda Species Rubiaceae Eukaryota n.a. n.a. n.a. PMID[2553871]
NPO23788 Beauveria bassiana Species Cordycipitaceae Eukaryota n.a. n.a. n.a. PMID[32058711]
NPO23788 Beauveria bassiana Species Cordycipitaceae Eukaryota n.a. n.a. n.a. PMID[8557595]
NPO27746 Taxus mairei Species Taxaceae Eukaryota Roots n.a. n.a. PMID[8991951]
NPO27746 Taxus mairei Species Taxaceae Eukaryota n.a. n.a. n.a. PMID[9644081]
NPO23788 Beauveria bassiana Species Cordycipitaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO24278 Pistacia chinensis Species Anacardiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO24373 Lobelia inflata Species Campanulaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO24373 Lobelia inflata Species Campanulaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO23788 Beauveria bassiana Species Cordycipitaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO24852 Helicia nilagirica Species Proteaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22283 Alhagi maurorum Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO27746 Taxus mairei Species Taxaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO24278 Pistacia chinensis Species Anacardiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO24278 Pistacia chinensis Species Anacardiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO24461 Clusia sandiensis Species Clusiidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25366 Sapium indicum Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24607 Goniothalamus dolichocarpus Species Annonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24852 Helicia nilagirica Species Proteaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3721 Achyranthes obtusifolia Species Amaranthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24278 Pistacia chinensis Species Anacardiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24882 Erythrophleum chlorostachys Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6645.1 Picea jezoensis var. jezoensis Varieties Pinaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27390 Vernonia brevifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27746 Taxus mairei Species Taxaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24802 Diploprion bifasciatum Species Serranidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25252 Nannocystis exedens Species Nannocystaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO24730 Lactarius deliciosus Species Russulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25277 Seiridium cupressi Species Sporocadaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25441 Desmodium pulchellu Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20264 Moonia heterophylla n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO23788 Beauveria bassiana Species Cordycipitaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28460 Achyrocline tomentosa Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22152 Tecoma undulata Species Bignoniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15482 Vanderbylia fraxinea Species Polyporaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25389 Allium angulosum Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25466 Lecanora sulphurella Species Lecanoraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24566 Marasmiellus ramealis Species Omphalotaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25492 Botryllus leachi Species Styelidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22283 Alhagi maurorum Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18706 Anemone thalictroides Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24373 Lobelia inflata Species Campanulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23994 Ormosia macrophylla Species Limoniidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23894 Pulicaria insignis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25054 Phaleria macrocarpa Species Thymelaeaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22618 Psolus eximius Species Psolidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14189 Osmundaria spiralis Species Rhodomelaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25311 Guettarda platypoda Species Rubiaceae 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
NPT165 Cell Line HeLa Homo sapiens IC50 = 9.2 ug.mL-1 PMID[448145]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 40.0 ug.mL-1 PMID[448145]

☑ 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 NPC92867 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 NPC311825
0.9927 High Similarity NPC20255
0.9854 High Similarity NPC125882
0.9781 High Similarity NPC34943
0.964 High Similarity NPC240115
0.9635 High Similarity NPC192658
0.9571 High Similarity NPC473760
0.9559 High Similarity NPC9905
0.95 High Similarity NPC209592
0.95 High Similarity NPC48599
0.9489 High Similarity NPC162613
0.9489 High Similarity NPC87934
0.9301 High Similarity NPC31829
0.9225 High Similarity NPC312393
0.922 High Similarity NPC38696
0.9178 High Similarity NPC473632
0.9178 High Similarity NPC132599
0.9178 High Similarity NPC469730
0.9161 High Similarity NPC327031
0.9149 High Similarity NPC95449
0.9143 High Similarity NPC472576
0.9143 High Similarity NPC27377
0.9143 High Similarity NPC41481
0.9143 High Similarity NPC97947
0.9143 High Similarity NPC266374
0.9143 High Similarity NPC87448
0.9143 High Similarity NPC291599
0.9143 High Similarity NPC118080
0.9091 High Similarity NPC478263
0.9071 High Similarity NPC171207
0.9071 High Similarity NPC472547
0.9071 High Similarity NPC90614
0.9071 High Similarity NPC100913
0.9071 High Similarity NPC275592
0.9071 High Similarity NPC97667
0.9048 High Similarity NPC473611
0.9021 High Similarity NPC478264
0.9007 High Similarity NPC16912
0.8958 High Similarity NPC473602
0.8951 High Similarity NPC475759
0.8951 High Similarity NPC241951
0.8951 High Similarity NPC470152
0.8944 High Similarity NPC34012
0.8929 High Similarity NPC39549
0.8904 High Similarity NPC476173
0.8897 High Similarity NPC132652
0.8897 High Similarity NPC217918
0.8889 High Similarity NPC158663
0.8889 High Similarity NPC470157
0.8889 High Similarity NPC200471
0.8889 High Similarity NPC472571
0.8889 High Similarity NPC470159
0.8889 High Similarity NPC472568
0.8889 High Similarity NPC70403
0.8889 High Similarity NPC469349
0.8889 High Similarity NPC471104
0.8889 High Similarity NPC473088
0.8889 High Similarity NPC174982
0.8889 High Similarity NPC472556
0.8889 High Similarity NPC171525
0.8889 High Similarity NPC476973
0.8889 High Similarity NPC177940
0.8889 High Similarity NPC472572
0.8889 High Similarity NPC184817
0.8889 High Similarity NPC472575
0.8889 High Similarity NPC96903
0.8889 High Similarity NPC29704
0.8881 High Similarity NPC163087
0.8857 High Similarity NPC472551
0.8857 High Similarity NPC472545
0.8844 High Similarity NPC197037
0.8836 High Similarity NPC76103
0.8819 High Similarity NPC25768
0.8819 High Similarity NPC475122
0.8819 High Similarity NPC125106
0.8819 High Similarity NPC95265
0.8819 High Similarity NPC11685
0.8819 High Similarity NPC163719
0.8819 High Similarity NPC472570
0.8819 High Similarity NPC70716
0.8819 High Similarity NPC472569
0.8819 High Similarity NPC95810
0.8819 High Similarity NPC472573
0.8819 High Similarity NPC57628
0.8819 High Similarity NPC476974
0.8819 High Similarity NPC188865
0.8786 High Similarity NPC195647
0.8786 High Similarity NPC66761
0.8786 High Similarity NPC472577
0.8786 High Similarity NPC291638
0.8786 High Similarity NPC17877
0.8784 High Similarity NPC138641
0.8784 High Similarity NPC145649
0.8784 High Similarity NPC283875
0.8784 High Similarity NPC233581
0.8784 High Similarity NPC22571
0.8784 High Similarity NPC469648
0.8784 High Similarity NPC469647
0.8776 High Similarity NPC91730
0.875 High Similarity NPC477894
0.875 High Similarity NPC91703
0.875 High Similarity NPC476077
0.8733 High Similarity NPC11410
0.8725 High Similarity NPC471135
0.8725 High Similarity NPC11588
0.8725 High Similarity NPC248265
0.8725 High Similarity NPC134685
0.8725 High Similarity NPC229545
0.8716 High Similarity NPC96308
0.8716 High Similarity NPC470153
0.8714 High Similarity NPC474608
0.8707 High Similarity NPC471101
0.8707 High Similarity NPC476975
0.8707 High Similarity NPC266265
0.8707 High Similarity NPC92293
0.8707 High Similarity NPC301556
0.8707 High Similarity NPC270590
0.8699 High Similarity NPC474935
0.8686 High Similarity NPC58061
0.8681 High Similarity NPC472546
0.8667 High Similarity NPC259144
0.8667 High Similarity NPC155329
0.8667 High Similarity NPC251139
0.8667 High Similarity NPC114357
0.8652 High Similarity NPC477893
0.8652 High Similarity NPC477896
0.8649 High Similarity NPC470245
0.8649 High Similarity NPC473214
0.8639 High Similarity NPC281717
0.8618 High Similarity NPC319404
0.8611 High Similarity NPC224491
0.8609 High Similarity NPC290683
0.8609 High Similarity NPC475638
0.8609 High Similarity NPC475548
0.8601 High Similarity NPC473301
0.86 High Similarity NPC219419
0.8592 High Similarity NPC472374
0.8592 High Similarity NPC472372
0.8591 High Similarity NPC471103
0.8591 High Similarity NPC472398
0.8591 High Similarity NPC469415
0.8582 High Similarity NPC28836
0.8582 High Similarity NPC311492
0.8581 High Similarity NPC473215
0.8571 High Similarity NPC233692
0.8571 High Similarity NPC239358
0.8553 High Similarity NPC318447
0.8553 High Similarity NPC322048
0.8552 High Similarity NPC182869
0.8552 High Similarity NPC140021
0.8543 High Similarity NPC469422
0.8543 High Similarity NPC34066
0.8542 High Similarity NPC473085
0.8542 High Similarity NPC473060
0.8542 High Similarity NPC184747
0.8542 High Similarity NPC473081
0.8542 High Similarity NPC476094
0.8542 High Similarity NPC43241
0.8542 High Similarity NPC473758
0.8542 High Similarity NPC211137
0.8542 High Similarity NPC473613
0.8542 High Similarity NPC48017
0.8542 High Similarity NPC200592
0.8542 High Similarity NPC473112
0.8542 High Similarity NPC147880
0.8542 High Similarity NPC473109
0.8542 High Similarity NPC4341
0.8531 High Similarity NPC183122
0.8531 High Similarity NPC283375
0.8523 High Similarity NPC303429
0.8523 High Similarity NPC222102
0.8523 High Similarity NPC469448
0.8511 High Similarity NPC472248
0.8503 High Similarity NPC127857
0.8493 Intermediate Similarity NPC131966
0.8493 Intermediate Similarity NPC191387
0.8487 Intermediate Similarity NPC323001
0.8487 Intermediate Similarity NPC70344
0.8487 Intermediate Similarity NPC326235
0.8477 Intermediate Similarity NPC469477
0.8477 Intermediate Similarity NPC133430
0.8472 Intermediate Similarity NPC210591
0.8472 Intermediate Similarity NPC475652
0.8472 Intermediate Similarity NPC214550
0.8467 Intermediate Similarity NPC51602
0.8467 Intermediate Similarity NPC284022
0.8462 Intermediate Similarity NPC471134
0.8456 Intermediate Similarity NPC81698
0.8456 Intermediate Similarity NPC250046
0.8456 Intermediate Similarity NPC60509
0.8442 Intermediate Similarity NPC326328
0.8442 Intermediate Similarity NPC323356
0.8442 Intermediate Similarity NPC309991
0.8442 Intermediate Similarity NPC471138
0.844 Intermediate Similarity NPC238370
0.844 Intermediate Similarity NPC233860
0.8429 Intermediate Similarity NPC147561
0.8421 Intermediate Similarity NPC473670
0.8421 Intermediate Similarity NPC469398
0.8421 Intermediate Similarity NPC21410

  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 NPC92867 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
0.7895 Intermediate Similarity NPD7236 Approved
0.7818 Intermediate Similarity NPD8470 Clinical (unspecified phase)
0.7756 Intermediate Similarity NPD7239 Suspended
0.7708 Intermediate Similarity NPD6007 Clinical (unspecified phase)
0.7679 Intermediate Similarity NPD8368 Discontinued
0.7661 Intermediate Similarity NPD8434 Phase 2
0.7647 Intermediate Similarity NPD8407 Phase 2
0.7551 Intermediate Similarity NPD5952 Clinical (unspecified phase)
0.7545 Intermediate Similarity NPD7799 Discontinued
0.7536 Intermediate Similarity NPD2629 Approved
0.7471 Intermediate Similarity NPD8361 Approved
0.7471 Intermediate Similarity NPD8360 Approved
0.7419 Intermediate Similarity NPD4628 Phase 3
0.7371 Intermediate Similarity NPD8435 Approved
0.7324 Intermediate Similarity NPD7741 Discontinued
0.7317 Intermediate Similarity NPD7057 Phase 3
0.7317 Intermediate Similarity NPD7058 Phase 2
0.7257 Intermediate Similarity NPD8424 Clinical (unspecified phase)
0.7222 Intermediate Similarity NPD8485 Approved
0.72 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7171 Intermediate Similarity NPD7966 Clinical (unspecified phase)
0.7152 Intermediate Similarity NPD6190 Approved
0.7143 Intermediate Similarity NPD8127 Discontinued
0.7122 Intermediate Similarity NPD2181 Clinical (unspecified phase)
0.7104 Intermediate Similarity NPD8486 Clinical (unspecified phase)
0.7101 Intermediate Similarity NPD6831 Clinical (unspecified phase)
0.7086 Intermediate Similarity NPD7008 Discontinued
0.7081 Intermediate Similarity NPD6273 Approved
0.7044 Intermediate Similarity NPD7274 Clinical (unspecified phase)
0.7039 Intermediate Similarity NPD3764 Approved
0.6994 Remote Similarity NPD5844 Phase 1
0.6993 Remote Similarity NPD4198 Discontinued
0.6981 Remote Similarity NPD8166 Discontinued
0.6978 Remote Similarity NPD2182 Approved
0.6971 Remote Similarity NPD7685 Pre-registration
0.6966 Remote Similarity NPD8150 Discontinued
0.6964 Remote Similarity NPD7075 Discontinued
0.6928 Remote Similarity NPD37 Approved
0.6923 Remote Similarity NPD5951 Approved
0.6923 Remote Similarity NPD690 Clinical (unspecified phase)
0.6909 Remote Similarity NPD4380 Phase 2
0.6905 Remote Similarity NPD4965 Approved
0.6905 Remote Similarity NPD4967 Phase 2
0.6905 Remote Similarity NPD4966 Approved
0.6905 Remote Similarity NPD4868 Clinical (unspecified phase)
0.6903 Remote Similarity NPD230 Phase 1
0.6899 Remote Similarity NPD6004 Phase 3
0.6899 Remote Similarity NPD6006 Clinical (unspecified phase)
0.6899 Remote Similarity NPD6005 Phase 3
0.6899 Remote Similarity NPD6003 Clinical (unspecified phase)
0.6899 Remote Similarity NPD6002 Phase 3
0.6886 Remote Similarity NPD5761 Phase 2
0.6886 Remote Similarity NPD7819 Suspended
0.6886 Remote Similarity NPD5760 Phase 2
0.6886 Remote Similarity NPD7096 Clinical (unspecified phase)
0.6883 Remote Similarity NPD6663 Approved
0.6883 Remote Similarity NPD7961 Discontinued
0.6875 Remote Similarity NPD6398 Clinical (unspecified phase)
0.6871 Remote Similarity NPD5126 Approved
0.6871 Remote Similarity NPD5125 Phase 3
0.6861 Remote Similarity NPD6647 Phase 2
0.6845 Remote Similarity NPD5402 Approved
0.6842 Remote Similarity NPD5736 Approved
0.6835 Remote Similarity NPD2935 Discontinued
0.6835 Remote Similarity NPD6685 Approved
0.6826 Remote Similarity NPD6801 Discontinued
0.6824 Remote Similarity NPD7457 Clinical (unspecified phase)
0.6824 Remote Similarity NPD6234 Discontinued
0.6813 Remote Similarity NPD7879 Clinical (unspecified phase)
0.6809 Remote Similarity NPD7497 Discontinued
0.6807 Remote Similarity NPD6599 Discontinued
0.6795 Remote Similarity NPD6355 Discontinued
0.6792 Remote Similarity NPD7266 Discontinued
0.6792 Remote Similarity NPD5762 Approved
0.6792 Remote Similarity NPD5763 Approved
0.6782 Remote Similarity NPD7473 Discontinued
0.678 Remote Similarity NPD6764 Approved
0.678 Remote Similarity NPD6765 Approved
0.6776 Remote Similarity NPD5740 Clinical (unspecified phase)
0.6776 Remote Similarity NPD6085 Phase 2
0.6761 Remote Similarity NPD4141 Clinical (unspecified phase)
0.6757 Remote Similarity NPD3412 Clinical (unspecified phase)
0.6752 Remote Similarity NPD6653 Approved
0.6747 Remote Similarity NPD7458 Discontinued
0.6747 Remote Similarity NPD6591 Clinical (unspecified phase)
0.6743 Remote Similarity NPD7228 Approved
0.6735 Remote Similarity NPD9545 Approved
0.6727 Remote Similarity NPD5403 Approved
0.6708 Remote Similarity NPD7421 Clinical (unspecified phase)
0.6707 Remote Similarity NPD7004 Clinical (unspecified phase)
0.6707 Remote Similarity NPD2534 Approved
0.6707 Remote Similarity NPD2532 Approved
0.6707 Remote Similarity NPD2533 Approved
0.6705 Remote Similarity NPD6232 Discontinued
0.6704 Remote Similarity NPD8312 Approved
0.6704 Remote Similarity NPD8313 Approved
0.6701 Remote Similarity NPD8462 Phase 1
0.6691 Remote Similarity NPD164 Approved
0.6686 Remote Similarity NPD2393 Clinical (unspecified phase)
0.6685 Remote Similarity NPD6559 Discontinued
0.6667 Remote Similarity NPD6287 Discontinued
0.6667 Remote Similarity NPD4807 Approved
0.6667 Remote Similarity NPD7305 Phase 1
0.6667 Remote Similarity NPD4806 Approved
0.6667 Remote Similarity NPD7094 Approved
0.6667 Remote Similarity NPD7314 Clinical (unspecified phase)
0.6667 Remote Similarity NPD7003 Approved
0.6667 Remote Similarity NPD4381 Clinical (unspecified phase)
0.6667 Remote Similarity NPD3750 Approved
0.6667 Remote Similarity NPD6858 Approved
0.6667 Remote Similarity NPD2799 Discontinued
0.665 Remote Similarity NPD8404 Phase 2
0.6648 Remote Similarity NPD3818 Discontinued
0.6647 Remote Similarity NPD7199 Phase 2
0.6647 Remote Similarity NPD3817 Phase 2
0.6647 Remote Similarity NPD5808 Clinical (unspecified phase)
0.6646 Remote Similarity NPD6799 Approved
0.6646 Remote Similarity NPD970 Clinical (unspecified phase)
0.6644 Remote Similarity NPD5306 Approved
0.6644 Remote Similarity NPD5305 Approved
0.6644 Remote Similarity NPD7163 Clinical (unspecified phase)
0.6642 Remote Similarity NPD1238 Approved
0.663 Remote Similarity NPD6784 Approved
0.663 Remote Similarity NPD6785 Approved
0.6629 Remote Similarity NPD7993 Clinical (unspecified phase)
0.6627 Remote Similarity NPD1934 Approved
0.6619 Remote Similarity NPD1929 Approved
0.6619 Remote Similarity NPD1931 Clinical (unspecified phase)
0.6619 Remote Similarity NPD5738 Clinical (unspecified phase)
0.6619 Remote Similarity NPD1930 Approved
0.6619 Remote Similarity NPD5765 Approved
0.6612 Remote Similarity NPD8397 Clinical (unspecified phase)
0.6608 Remote Similarity NPD7768 Phase 2
0.6606 Remote Similarity NPD8389 Clinical (unspecified phase)
0.6606 Remote Similarity NPD5401 Approved
0.6597 Remote Similarity NPD6912 Phase 3
0.659 Remote Similarity NPD5494 Approved
0.6588 Remote Similarity NPD8455 Phase 2
0.6584 Remote Similarity NPD2343 Clinical (unspecified phase)
0.6584 Remote Similarity NPD7702 Clinical (unspecified phase)
0.6573 Remote Similarity NPD7074 Phase 3
0.6573 Remote Similarity NPD2067 Discontinued
0.6571 Remote Similarity NPD1237 Approved
0.6568 Remote Similarity NPD7411 Suspended
0.6564 Remote Similarity NPD1878 Clinical (unspecified phase)
0.6564 Remote Similarity NPD4109 Clinical (unspecified phase)
0.6564 Remote Similarity NPD4110 Phase 3
0.6554 Remote Similarity NPD7610 Discontinued
0.655 Remote Similarity NPD8443 Clinical (unspecified phase)
0.6548 Remote Similarity NPD3226 Approved
0.6545 Remote Similarity NPD6143 Clinical (unspecified phase)
0.6534 Remote Similarity NPD6167 Clinical (unspecified phase)
0.6534 Remote Similarity NPD6166 Phase 2
0.6534 Remote Similarity NPD6168 Clinical (unspecified phase)
0.6527 Remote Similarity NPD6980 Clinical (unspecified phase)
0.6525 Remote Similarity NPD5048 Discontinued
0.6522 Remote Similarity NPD2438 Suspended
0.6522 Remote Similarity NPD7137 Phase 2
0.6519 Remote Similarity NPD4140 Approved
0.6517 Remote Similarity NPD7804 Clinical (unspecified phase)
0.6517 Remote Similarity NPD7054 Approved
0.6512 Remote Similarity NPD3882 Suspended
0.65 Remote Similarity NPD7240 Approved
0.6497 Remote Similarity NPD6859 Clinical (unspecified phase)
0.6494 Remote Similarity NPD3094 Phase 2
0.6491 Remote Similarity NPD2801 Approved
0.6491 Remote Similarity NPD1465 Phase 2
0.649 Remote Similarity NPD4106 Approved
0.649 Remote Similarity NPD4136 Approved
0.649 Remote Similarity NPD4135 Approved
0.6481 Remote Similarity NPD2346 Discontinued
0.648 Remote Similarity NPD7472 Approved
0.6477 Remote Similarity NPD7184 Clinical (unspecified phase)
0.6474 Remote Similarity NPD6832 Phase 2
0.6471 Remote Similarity NPD6535 Approved
0.6471 Remote Similarity NPD6534 Approved
0.6464 Remote Similarity NPD4338 Clinical (unspecified phase)
0.6463 Remote Similarity NPD2575 Approved
0.646 Remote Similarity NPD3748 Approved
0.646 Remote Similarity NPD7033 Discontinued
0.6458 Remote Similarity NPD7435 Discontinued
0.6456 Remote Similarity NPD6233 Phase 2
0.6455 Remote Similarity NPD7699 Phase 2
0.6455 Remote Similarity NPD7700 Phase 2
0.6454 Remote Similarity NPD5909 Discontinued
0.6452 Remote Similarity NPD5647 Approved
0.645 Remote Similarity NPD3455 Phase 2
0.6449 Remote Similarity NPD9495 Approved
0.6438 Remote Similarity NPD3528 Clinical (unspecified phase)
0.6437 Remote Similarity NPD5537 Clinical (unspecified phase)
0.6433 Remote Similarity NPD7095 Approved
0.6425 Remote Similarity NPD8320 Phase 1
0.6425 Remote Similarity NPD8319 Approved
0.642 Remote Similarity NPD6100 Approved
0.642 Remote Similarity NPD5408 Approved
0.642 Remote Similarity NPD6099 Approved
0.642 Remote Similarity NPD5404 Approved
0.642 Remote Similarity NPD1551 Phase 2
0.642 Remote Similarity NPD5405 Approved
0.642 Remote Similarity NPD5406 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