Structure

Physi-Chem Properties

Molecular Weight:  586.24
Volume:  577.551
LogP:  2.039
LogD:  1.731
LogS:  -4.399
# Rotatable Bonds:  7
TPSA:  165.89
# H-Bond Aceptor:  11
# H-Bond Donor:  3
# Rings:  5
# Heavy Atoms:  11

MedChem Properties

QED Drug-Likeness Score:  0.348
Synthetic Accessibility Score:  5.615
Fsp3:  0.613
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:  -5.365
MDCK Permeability:  5.323768709786236e-05
Pgp-inhibitor:  0.999
Pgp-substrate:  0.994
Human Intestinal Absorption (HIA):  0.332
20% Bioavailability (F20%):  0.993
30% Bioavailability (F30%):  0.991

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.445
Plasma Protein Binding (PPB):  61.544837951660156%
Volume Distribution (VD):  0.642
Pgp-substrate:  20.843576431274414%

ADMET: Metabolism

CYP1A2-inhibitor:  0.019
CYP1A2-substrate:  0.071
CYP2C19-inhibitor:  0.03
CYP2C19-substrate:  0.269
CYP2C9-inhibitor:  0.052
CYP2C9-substrate:  0.044
CYP2D6-inhibitor:  0.011
CYP2D6-substrate:  0.041
CYP3A4-inhibitor:  0.587
CYP3A4-substrate:  0.491

ADMET: Excretion

Clearance (CL):  3.088
Half-life (T1/2):  0.054

ADMET: Toxicity

hERG Blockers:  0.027
Human Hepatotoxicity (H-HT):  0.542
Drug-inuced Liver Injury (DILI):  0.573
AMES Toxicity:  0.016
Rat Oral Acute Toxicity:  0.352
Maximum Recommended Daily Dose:  0.735
Skin Sensitization:  0.187
Carcinogencity:  0.127
Eye Corrosion:  0.003
Eye Irritation:  0.01
Respiratory Toxicity:  0.978

Download Data

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

  Natural Product: NPC155329

Natural Product ID:  NPC155329
Common Name*:   OVMSOCFBDVBLFW-SSXYINQQSA-N
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  OVMSOCFBDVBLFW-SSXYINQQSA-N
Standard InCHI:  InChI=1S/C31H38O11/c1-15-19(34)13-31(38)26(41-27(37)18-10-8-7-9-11-18)24-29(6,20(35)12-21-30(24,14-39-21)42-17(3)33)25(36)23(40-16(2)32)22(15)28(31,4)5/h7-11,19-21,23-24,26,34-35,38H,12-14H2,1-6H3/t19-,20+,21+,23+,24?,26-,29+,30-,31+/m0/s1
SMILES:  CC1=C2[C@H](C(=O)[C@]3(C)[C@@H](C[C@@H]4[C@@](CO4)(C3[C@@H]([C@](C[C@@H]1O)(C2(C)C)O)OC(=O)c1ccccc1)OC(=O)C)O)OC(=O)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1590876
PubChem CID:   9938327
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
NPO11554 Taxus sumatrana Species Taxaceae Eukaryota n.a. leaf n.a. DOI[10.1016/j.tet.2004.10.110]
NPO11554 Taxus sumatrana Species Taxaceae Eukaryota n.a. twig n.a. DOI[10.1016/j.tet.2004.10.110]
NPO29841 Taxus yunnanensis Species Taxaceae Eukaryota n.a. n.a. n.a. PMID[12217376]
NPO29841 Taxus yunnanensis Species Taxaceae Eukaryota wood n.a. n.a. PMID[12444707]
NPO11554 Taxus sumatrana Species Taxaceae Eukaryota leaves and twigs n.a. n.a. PMID[12502326]
NPO24820 Taxus cuspidata Species Taxaceae Eukaryota n.a. Japan n.a. PMID[14987066]
NPO11554 Taxus sumatrana Species Taxaceae Eukaryota n.a. twig n.a. PMID[15679325]
NPO11554 Taxus sumatrana Species Taxaceae Eukaryota n.a. leaf n.a. PMID[15679325]
NPO11554 Taxus sumatrana Species Taxaceae Eukaryota n.a. n.a. n.a. PMID[15679325]
NPO24820 Taxus cuspidata Species Taxaceae Eukaryota n.a. n.a. n.a. PMID[15844936]
NPO24820 Taxus cuspidata Species Taxaceae Eukaryota n.a. n.a. n.a. PMID[15974623]
NPO24820 Taxus cuspidata Species Taxaceae Eukaryota n.a. Japan n.a. PMID[15974623]
NPO11554 Taxus sumatrana Species Taxaceae Eukaryota n.a. n.a. n.a. PMID[18220355]
NPO29841 Taxus yunnanensis Species Taxaceae Eukaryota wood Yunnang Province, China 2000-OCT PMID[21138310]
NPO29841 Taxus yunnanensis Species Taxaceae Eukaryota n.a. xylem n.a. PMID[21138310]
NPO5067 Taxus baccata Species Taxaceae Eukaryota n.a. n.a. n.a. PMID[23265441]
NPO5067 Taxus baccata Species Taxaceae Eukaryota n.a. n.a. n.a. PMID[7561894]
NPO5067 Taxus baccata Species Taxaceae Eukaryota n.a. n.a. n.a. PMID[7908950]
NPO5067 Taxus baccata Species Taxaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO11554 Taxus sumatrana Species Taxaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO29841 Taxus yunnanensis Species Taxaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO24820 Taxus cuspidata Species Taxaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO11554 Taxus sumatrana Species Taxaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO24820 Taxus cuspidata Species Taxaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO5067 Taxus baccata Species Taxaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15125.2 Taxus wallichiana var. wallichiana Varieties Taxaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO29841 Taxus yunnanensis Species Taxaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO24820 Taxus cuspidata Species Taxaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO5067 Taxus baccata Species Taxaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO24820 Taxus cuspidata Species Taxaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15125.2 Taxus wallichiana var. wallichiana Varieties Taxaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11554 Taxus sumatrana Species Taxaceae 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
NPT56 Individual Protein Beta-lactamase AmpC Escherichia coli K-12 Potency = 70794.6 nM PMID[555940]
NPT477 Individual Protein DNA dC->dU-editing enzyme APOBEC-3G Homo sapiens Potency n.a. 10000.0 nM PMID[555940]
NPT10 Individual Protein Geminin Homo sapiens Potency n.a. 16360.1 nM PMID[555940]
NPT478 Individual Protein Ataxin-2 Homo sapiens Potency n.a. 28183.8 nM PMID[555940]
NPT101 Individual Protein Glucagon-like peptide 1 receptor Homo sapiens Potency n.a. 12589.3 nM PMID[555940]
NPT50 Individual Protein Tyrosyl-DNA phosphodiesterase 1 Homo sapiens Potency n.a. 5804.8 nM PMID[555940]
NPT50 Individual Protein Tyrosyl-DNA phosphodiesterase 1 Homo sapiens Potency n.a. 7307.8 nM PMID[555940]
NPT2 Others Unspecified Potency n.a. 3162.3 nM PMID[555940]
NPT2 Others Unspecified Potency n.a. 28183.8 nM PMID[555940]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum Potency n.a. 11689.1 nM PMID[555940]
NPT2 Others Unspecified Potency n.a. 7943.3 nM PMID[555940]
NPT2 Others Unspecified AbsAC26_uM n.a. 6.46 uM PMID[555940]

☑ 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 NPC155329 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 NPC259144
1.0 High Similarity NPC114357
0.9931 High Similarity NPC11588
0.9931 High Similarity NPC219419
0.9931 High Similarity NPC248265
0.9931 High Similarity NPC134685
0.9931 High Similarity NPC229545
0.9792 High Similarity NPC197037
0.9722 High Similarity NPC91730
0.9583 High Similarity NPC217918
0.9474 High Similarity NPC471493
0.9459 High Similarity NPC473670
0.9459 High Similarity NPC21410
0.9388 High Similarity NPC471103
0.9375 High Similarity NPC38696
0.931 High Similarity NPC127857
0.9257 High Similarity NPC101043
0.9257 High Similarity NPC51602
0.9257 High Similarity NPC306799
0.9252 High Similarity NPC60509
0.9252 High Similarity NPC81698
0.9252 High Similarity NPC250046
0.9205 High Similarity NPC472393
0.9189 High Similarity NPC165260
0.9189 High Similarity NPC7095
0.9189 High Similarity NPC161239
0.9189 High Similarity NPC198455
0.9139 High Similarity NPC217091
0.9139 High Similarity NPC106895
0.9103 High Similarity NPC182869
0.9103 High Similarity NPC34012
0.9073 High Similarity NPC282239
0.9073 High Similarity NPC132599
0.9073 High Similarity NPC228204
0.9073 High Similarity NPC26033
0.9073 High Similarity NPC473632
0.9073 High Similarity NPC469730
0.906 High Similarity NPC112216
0.9048 High Similarity NPC471100
0.9048 High Similarity NPC471107
0.9007 High Similarity NPC473414
0.9007 High Similarity NPC472030
0.9007 High Similarity NPC265395
0.9007 High Similarity NPC472005
0.9007 High Similarity NPC257213
0.9007 High Similarity NPC242262
0.9007 High Similarity NPC249471
0.9007 High Similarity NPC237549
0.9007 High Similarity NPC304876
0.9007 High Similarity NPC256142
0.9007 High Similarity NPC472022
0.9007 High Similarity NPC1173
0.9007 High Similarity NPC158333
0.8947 High Similarity NPC112523
0.8947 High Similarity NPC473611
0.8947 High Similarity NPC472549
0.8947 High Similarity NPC114410
0.8919 High Similarity NPC277053
0.8919 High Similarity NPC301946
0.8912 High Similarity NPC477894
0.8896 High Similarity NPC471102
0.8889 High Similarity NPC11410
0.8882 High Similarity NPC77719
0.8874 High Similarity NPC470153
0.8851 High Similarity NPC471912
0.8851 High Similarity NPC80895
0.8844 High Similarity NPC472546
0.8836 High Similarity NPC472547
0.8831 High Similarity NPC469771
0.8824 High Similarity NPC251139
0.8816 High Similarity NPC472548
0.8808 High Similarity NPC470245
0.8808 High Similarity NPC254558
0.8808 High Similarity NPC473214
0.8776 High Similarity NPC87448
0.8776 High Similarity NPC118080
0.8776 High Similarity NPC291599
0.8776 High Similarity NPC27377
0.8776 High Similarity NPC41481
0.8776 High Similarity NPC472576
0.8776 High Similarity NPC97947
0.8759 High Similarity NPC472372
0.8759 High Similarity NPC472374
0.8758 High Similarity NPC133430
0.8758 High Similarity NPC469477
0.8742 High Similarity NPC476975
0.8742 High Similarity NPC473215
0.8733 High Similarity NPC477737
0.8733 High Similarity NPC474935
0.8707 High Similarity NPC97667
0.8707 High Similarity NPC100913
0.8707 High Similarity NPC90614
0.8707 High Similarity NPC171207
0.8707 High Similarity NPC275592
0.8699 High Similarity NPC39549
0.8693 High Similarity NPC477905
0.8693 High Similarity NPC138641
0.8693 High Similarity NPC469648
0.8693 High Similarity NPC22571
0.8693 High Similarity NPC469647
0.8693 High Similarity NPC283875
0.869 High Similarity NPC477896
0.869 High Similarity NPC477893
0.8675 High Similarity NPC132652
0.8667 High Similarity NPC92867
0.8667 High Similarity NPC311825
0.8662 High Similarity NPC476077
0.8654 High Similarity NPC469399
0.8649 High Similarity NPC16912
0.863 High Similarity NPC472551
0.863 High Similarity NPC472545
0.8627 High Similarity NPC472398
0.8611 High Similarity NPC80599
0.8609 High Similarity NPC20255
0.86 High Similarity NPC470152
0.86 High Similarity NPC475759
0.86 High Similarity NPC241951
0.859 High Similarity NPC469417
0.8581 High Similarity NPC5115
0.8581 High Similarity NPC477904
0.8581 High Similarity NPC183270
0.8571 High Similarity NPC102465
0.8571 High Similarity NPC145649
0.8571 High Similarity NPC233581
0.8543 High Similarity NPC29704
0.8543 High Similarity NPC171525
0.8543 High Similarity NPC473088
0.8543 High Similarity NPC471104
0.8543 High Similarity NPC472571
0.8543 High Similarity NPC469349
0.8543 High Similarity NPC472575
0.8543 High Similarity NPC472568
0.8543 High Similarity NPC472556
0.8543 High Similarity NPC470157
0.8543 High Similarity NPC470159
0.8543 High Similarity NPC70403
0.8543 High Similarity NPC96903
0.8543 High Similarity NPC200471
0.8543 High Similarity NPC476973
0.8543 High Similarity NPC472572
0.8543 High Similarity NPC184817
0.8543 High Similarity NPC158663
0.8543 High Similarity NPC177940
0.8543 High Similarity NPC174982
0.8543 High Similarity NPC125882
0.8533 High Similarity NPC95449
0.8533 High Similarity NPC163087
0.8526 High Similarity NPC70344
0.8523 High Similarity NPC213567
0.85 High Similarity NPC471134
0.8491 Intermediate Similarity NPC55744
0.8491 Intermediate Similarity NPC477190
0.8491 Intermediate Similarity NPC477188
0.8491 Intermediate Similarity NPC43304
0.8487 Intermediate Similarity NPC469513
0.8483 Intermediate Similarity NPC472394
0.8483 Intermediate Similarity NPC209851
0.8477 Intermediate Similarity NPC475122
0.8477 Intermediate Similarity NPC472573
0.8477 Intermediate Similarity NPC34943
0.8477 Intermediate Similarity NPC70716
0.8477 Intermediate Similarity NPC163719
0.8477 Intermediate Similarity NPC125106
0.8477 Intermediate Similarity NPC95265
0.8477 Intermediate Similarity NPC472570
0.8477 Intermediate Similarity NPC95810
0.8477 Intermediate Similarity NPC57628
0.8477 Intermediate Similarity NPC11685
0.8477 Intermediate Similarity NPC188865
0.8477 Intermediate Similarity NPC25768
0.8477 Intermediate Similarity NPC476974
0.8477 Intermediate Similarity NPC472569
0.8477 Intermediate Similarity NPC470231
0.8471 Intermediate Similarity NPC33372
0.8471 Intermediate Similarity NPC67246
0.8462 Intermediate Similarity NPC471623
0.8446 Intermediate Similarity NPC184109
0.8438 Intermediate Similarity NPC329960
0.8438 Intermediate Similarity NPC66193
0.8438 Intermediate Similarity NPC150893
0.8438 Intermediate Similarity NPC295408
0.8435 Intermediate Similarity NPC17877
0.8435 Intermediate Similarity NPC195647
0.8435 Intermediate Similarity NPC472577
0.8435 Intermediate Similarity NPC66761
0.8435 Intermediate Similarity NPC291638
0.8431 Intermediate Similarity NPC473760
0.8412 Intermediate Similarity NPC471754
0.8412 Intermediate Similarity NPC475336
0.8412 Intermediate Similarity NPC473300
0.8412 Intermediate Similarity NPC324251
0.8412 Intermediate Similarity NPC453583
0.8412 Intermediate Similarity NPC317882
0.8412 Intermediate Similarity NPC206211
0.8412 Intermediate Similarity NPC471629
0.8412 Intermediate Similarity NPC306001
0.8412 Intermediate Similarity NPC275170
0.8412 Intermediate Similarity NPC473400
0.8411 Intermediate Similarity NPC91703
0.84 Intermediate Similarity NPC224491

  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 NPC155329 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
0.8827 High Similarity NPD8368 Discontinued
0.8667 High Similarity NPD8407 Phase 2
0.8563 High Similarity NPD8434 Phase 2
0.8462 Intermediate Similarity NPD8361 Approved
0.8462 Intermediate Similarity NPD8435 Approved
0.8462 Intermediate Similarity NPD8360 Approved
0.8276 Intermediate Similarity NPD8485 Approved
0.8193 Intermediate Similarity NPD8470 Clinical (unspecified phase)
0.8182 Intermediate Similarity NPD7236 Approved
0.8136 Intermediate Similarity NPD8486 Clinical (unspecified phase)
0.8129 Intermediate Similarity NPD8424 Clinical (unspecified phase)
0.8038 Intermediate Similarity NPD7239 Suspended
0.8024 Intermediate Similarity NPD7799 Discontinued
0.7714 Intermediate Similarity NPD8150 Discontinued
0.759 Intermediate Similarity NPD7057 Phase 3
0.759 Intermediate Similarity NPD7058 Phase 2
0.7582 Intermediate Similarity NPD7966 Clinical (unspecified phase)
0.7566 Intermediate Similarity NPD8462 Phase 1
0.7547 Intermediate Similarity NPD6190 Approved
0.7545 Intermediate Similarity NPD7075 Discontinued
0.7542 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.747 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.741 Intermediate Similarity NPD6801 Discontinued
0.7409 Intermediate Similarity NPD8404 Phase 2
0.7394 Intermediate Similarity NPD6599 Discontinued
0.7375 Intermediate Similarity NPD4628 Phase 3
0.7361 Intermediate Similarity NPD2629 Approved
0.736 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7321 Intermediate Similarity NPD5402 Approved
0.7273 Intermediate Similarity NPD5952 Clinical (unspecified phase)
0.7241 Intermediate Similarity NPD7473 Discontinued
0.7219 Intermediate Similarity NPD3817 Phase 2
0.7192 Intermediate Similarity NPD4198 Discontinued
0.7186 Intermediate Similarity NPD4380 Phase 2
0.716 Intermediate Similarity NPD7819 Suspended
0.7143 Intermediate Similarity NPD7435 Discontinued
0.7134 Intermediate Similarity NPD6799 Approved
0.7108 Intermediate Similarity NPD5403 Approved
0.7105 Intermediate Similarity NPD8319 Approved
0.7105 Intermediate Similarity NPD8320 Phase 1
0.7102 Intermediate Similarity NPD3751 Discontinued
0.7095 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.7093 Intermediate Similarity NPD5537 Clinical (unspecified phase)
0.7081 Intermediate Similarity NPD6535 Approved
0.7081 Intermediate Similarity NPD6534 Approved
0.707 Intermediate Similarity NPD7961 Discontinued
0.7069 Intermediate Similarity NPD6232 Discontinued
0.7062 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.7062 Intermediate Similarity NPD5844 Phase 1
0.7059 Intermediate Similarity NPD7700 Phase 2
0.7059 Intermediate Similarity NPD7699 Phase 2
0.7055 Intermediate Similarity NPD8166 Discontinued
0.7049 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7039 Intermediate Similarity NPD6764 Approved
0.7039 Intermediate Similarity NPD6765 Approved
0.6989 Remote Similarity NPD6168 Clinical (unspecified phase)
0.6989 Remote Similarity NPD6166 Phase 2
0.6989 Remote Similarity NPD6167 Clinical (unspecified phase)
0.6988 Remote Similarity NPD5401 Approved
0.6977 Remote Similarity NPD3882 Suspended
0.6977 Remote Similarity NPD4868 Clinical (unspecified phase)
0.6968 Remote Similarity NPD6007 Clinical (unspecified phase)
0.6961 Remote Similarity NPD8312 Approved
0.6961 Remote Similarity NPD8313 Approved
0.6959 Remote Similarity NPD5760 Phase 2
0.6959 Remote Similarity NPD2393 Clinical (unspecified phase)
0.6959 Remote Similarity NPD5761 Phase 2
0.6954 Remote Similarity NPD3412 Clinical (unspecified phase)
0.6944 Remote Similarity NPD7251 Discontinued
0.6943 Remote Similarity NPD7008 Discontinued
0.6936 Remote Similarity NPD4381 Clinical (unspecified phase)
0.6923 Remote Similarity NPD7458 Discontinued
0.6923 Remote Similarity NPD3226 Approved
0.6923 Remote Similarity NPD7875 Clinical (unspecified phase)
0.6923 Remote Similarity NPD7874 Approved
0.691 Remote Similarity NPD3818 Discontinued
0.6906 Remote Similarity NPD7808 Phase 3
0.6901 Remote Similarity NPD1934 Approved
0.6895 Remote Similarity NPD6781 Approved
0.6895 Remote Similarity NPD6780 Approved
0.6895 Remote Similarity NPD6778 Approved
0.6895 Remote Similarity NPD6782 Approved
0.6895 Remote Similarity NPD6779 Approved
0.6895 Remote Similarity NPD6777 Approved
0.6895 Remote Similarity NPD6776 Approved
0.6892 Remote Similarity NPD690 Clinical (unspecified phase)
0.6889 Remote Similarity NPD7993 Clinical (unspecified phase)
0.6889 Remote Similarity NPD6797 Phase 2
0.6886 Remote Similarity NPD2532 Approved
0.6886 Remote Similarity NPD2534 Approved
0.6886 Remote Similarity NPD4378 Clinical (unspecified phase)
0.6886 Remote Similarity NPD2533 Approved
0.6885 Remote Similarity NPD6784 Approved
0.6885 Remote Similarity NPD6785 Approved
0.6875 Remote Similarity NPD3787 Discontinued
0.6875 Remote Similarity NPD230 Phase 1
0.686 Remote Similarity NPD2801 Approved
0.6857 Remote Similarity NPD5494 Approved
0.6852 Remote Similarity NPD7305 Phase 1
0.6848 Remote Similarity NPD6398 Clinical (unspecified phase)
0.6842 Remote Similarity NPD7411 Suspended
0.6833 Remote Similarity NPD7074 Phase 3
0.6828 Remote Similarity NPD6831 Clinical (unspecified phase)
0.6821 Remote Similarity NPD7741 Discontinued
0.6821 Remote Similarity NPD8443 Clinical (unspecified phase)
0.6818 Remote Similarity NPD8127 Discontinued
0.6802 Remote Similarity NPD37 Approved
0.6792 Remote Similarity NPD3764 Approved
0.6788 Remote Similarity NPD7698 Approved
0.6788 Remote Similarity NPD7696 Phase 3
0.6788 Remote Similarity NPD7421 Clinical (unspecified phase)
0.6788 Remote Similarity NPD7697 Approved
0.6786 Remote Similarity NPD8389 Clinical (unspecified phase)
0.6782 Remote Similarity NPD4967 Phase 2
0.6782 Remote Similarity NPD4965 Approved
0.6782 Remote Similarity NPD4966 Approved
0.6779 Remote Similarity NPD5951 Approved
0.6778 Remote Similarity NPD7054 Approved
0.6768 Remote Similarity NPD2346 Discontinued
0.6766 Remote Similarity NPD3300 Phase 2
0.6759 Remote Similarity NPD5345 Clinical (unspecified phase)
0.6758 Remote Similarity NPD7685 Pre-registration
0.6758 Remote Similarity NPD6559 Discontinued
0.6753 Remote Similarity NPD7871 Phase 2
0.6753 Remote Similarity NPD7870 Phase 2
0.674 Remote Similarity NPD7472 Approved
0.6735 Remote Similarity NPD7701 Phase 2
0.6735 Remote Similarity NPD2181 Clinical (unspecified phase)
0.6735 Remote Similarity NPD4141 Clinical (unspecified phase)
0.6727 Remote Similarity NPD970 Clinical (unspecified phase)
0.6717 Remote Similarity NPD7801 Approved
0.6712 Remote Similarity NPD2182 Approved
0.6711 Remote Similarity NPD6010 Discontinued
0.6707 Remote Similarity NPD7274 Clinical (unspecified phase)
0.6707 Remote Similarity NPD2935 Discontinued
0.6705 Remote Similarity NPD6234 Discontinued
0.6689 Remote Similarity NPD1609 Clinical (unspecified phase)
0.6686 Remote Similarity NPD7004 Clinical (unspecified phase)
0.6686 Remote Similarity NPD7410 Clinical (unspecified phase)
0.6667 Remote Similarity NPD6355 Discontinued
0.6647 Remote Similarity NPD1512 Approved
0.6647 Remote Similarity NPD3750 Approved
0.6647 Remote Similarity NPD6273 Approved
0.6646 Remote Similarity NPD2799 Discontinued
0.6646 Remote Similarity NPD1510 Phase 2
0.663 Remote Similarity NPD7228 Approved
0.6629 Remote Similarity NPD6959 Discontinued
0.6628 Remote Similarity NPD6591 Clinical (unspecified phase)
0.6627 Remote Similarity NPD1549 Phase 2
0.6626 Remote Similarity NPD6651 Approved
0.6623 Remote Similarity NPD7163 Clinical (unspecified phase)
0.6623 Remote Similarity NPD5125 Phase 3
0.6623 Remote Similarity NPD5126 Approved
0.6621 Remote Similarity NPD5048 Discontinued
0.6615 Remote Similarity NPD7497 Discontinued
0.6611 Remote Similarity NPD7852 Clinical (unspecified phase)
0.6606 Remote Similarity NPD6100 Approved
0.6606 Remote Similarity NPD2796 Approved
0.6606 Remote Similarity NPD6099 Approved
0.6601 Remote Similarity NPD9545 Approved
0.6601 Remote Similarity NPD6319 Approved
0.6591 Remote Similarity NPD7768 Phase 2
0.6588 Remote Similarity NPD7422 Clinical (unspecified phase)
0.6587 Remote Similarity NPD2800 Approved
0.6585 Remote Similarity NPD8155 Clinical (unspecified phase)
0.6584 Remote Similarity NPD2313 Discontinued
0.6581 Remote Similarity NPD7457 Clinical (unspecified phase)
0.6579 Remote Similarity NPD6212 Phase 3
0.6579 Remote Similarity NPD6213 Phase 3
0.6579 Remote Similarity NPD6214 Clinical (unspecified phase)
0.6576 Remote Similarity NPD5030 Phase 2
0.6571 Remote Similarity NPD1465 Phase 2
0.6566 Remote Similarity NPD5762 Approved
0.6566 Remote Similarity NPD1550 Clinical (unspecified phase)
0.6566 Remote Similarity NPD7266 Discontinued
0.6566 Remote Similarity NPD1552 Clinical (unspecified phase)
0.6566 Remote Similarity NPD5763 Approved
0.6566 Remote Similarity NPD7702 Clinical (unspecified phase)
0.6564 Remote Similarity NPD6823 Phase 2
0.6562 Remote Similarity NPD8090 Clinical (unspecified phase)
0.6556 Remote Similarity NPD7184 Clinical (unspecified phase)
0.6554 Remote Similarity NPD3749 Approved
0.6554 Remote Similarity NPD2067 Discontinued
0.6552 Remote Similarity NPD1237 Approved
0.6548 Remote Similarity NPD1878 Clinical (unspecified phase)
0.6548 Remote Similarity NPD7003 Approved
0.6548 Remote Similarity NPD7211 Clinical (unspecified phase)
0.6545 Remote Similarity NPD7033 Discontinued
0.6545 Remote Similarity NPD1509 Clinical (unspecified phase)
0.6545 Remote Similarity NPD651 Clinical (unspecified phase)
0.6543 Remote Similarity NPD6233 Phase 2
0.6541 Remote Similarity NPD36 Approved
0.6541 Remote Similarity NPD5034 Approved
0.6541 Remote Similarity NPD6085 Phase 2
0.6541 Remote Similarity NPD4955 Approved
0.6541 Remote Similarity NPD4954 Approved
0.6541 Remote Similarity NPD5028 Approved
0.6541 Remote Similarity NPD5026 Approved
0.6541 Remote Similarity NPD5740 Clinical (unspecified phase)
0.6538 Remote Similarity NPD4807 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