Structure

Physi-Chem Properties

Molecular Weight:  686.24
Volume:  641.485
LogP:  -0.217
LogD:  -0.141
LogS:  -1.949
# Rotatable Bonds:  14
TPSA:  260.59
# H-Bond Aceptor:  17
# H-Bond Donor:  8
# Rings:  4
# Heavy Atoms:  17

MedChem Properties

QED Drug-Likeness Score:  0.083
Synthetic Accessibility Score:  5.235
Fsp3:  0.613
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  1
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -6.243
MDCK Permeability:  0.00018786016153171659
Pgp-inhibitor:  0.003
Pgp-substrate:  0.994
Human Intestinal Absorption (HIA):  0.987
20% Bioavailability (F20%):  0.014
30% Bioavailability (F30%):  0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.176
Plasma Protein Binding (PPB):  53.49151611328125%
Volume Distribution (VD):  0.447
Pgp-substrate:  20.769271850585938%

ADMET: Metabolism

CYP1A2-inhibitor:  0.008
CYP1A2-substrate:  0.052
CYP2C19-inhibitor:  0.029
CYP2C19-substrate:  0.111
CYP2C9-inhibitor:  0.004
CYP2C9-substrate:  0.046
CYP2D6-inhibitor:  0.011
CYP2D6-substrate:  0.073
CYP3A4-inhibitor:  0.027
CYP3A4-substrate:  0.098

ADMET: Excretion

Clearance (CL):  0.899
Half-life (T1/2):  0.868

ADMET: Toxicity

hERG Blockers:  0.03
Human Hepatotoxicity (H-HT):  0.195
Drug-inuced Liver Injury (DILI):  0.857
AMES Toxicity:  0.653
Rat Oral Acute Toxicity:  0.068
Maximum Recommended Daily Dose:  0.063
Skin Sensitization:  0.173
Carcinogencity:  0.757
Eye Corrosion:  0.003
Eye Irritation:  0.01
Respiratory Toxicity:  0.242

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

  Natural Product: NPC101686

Natural Product ID:  NPC101686
Common Name*:   Nuzhenide
IUPAC Name:   methyl (5E,6S)-5-ethylidene-4-[2-oxo-2-[[(2R,3S,4S,5R,6R)-3,4,5-trihydroxy-6-[2-(4-hydroxyphenyl)ethoxy]oxan-2-yl]methoxy]ethyl]-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4H-pyran-3-carboxylate
Synonyms:   Nuzhenide
Standard InCHIKey:  STKUCSFEBXPTAY-YTECAPLWSA-N
Standard InCHI:  InChI=1S/C31H42O17/c1-3-16-17(18(28(41)42-2)12-45-29(16)48-31-27(40)24(37)22(35)19(11-32)46-31)10-21(34)44-13-20-23(36)25(38)26(39)30(47-20)43-9-8-14-4-6-15(33)7-5-14/h3-7,12,17,19-20,22-27,29-33,35-40H,8-11,13H2,1-2H3/b16-3+/t17?,19-,20-,22-,23-,24+,25+,26-,27-,29+,30-,31+/m1/s1
SMILES:  C/C=C/1C(CC(=O)OC[C@@H]2[C@H]([C@@H]([C@H]([C@H](OCCc3ccc(cc3)O)O2)O)O)O)C(=CO[C@H]1O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)C(=O)OC
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1076818
PubChem CID:   6440999
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0003918] Saccharolipids

*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
NPO18340 Ligustrum lucidum Species Oleaceae Eukaryota n.a. fruit n.a. PMID[11411539]
NPO19884 Fraxinus excelsior Species Oleaceae Eukaryota n.a. n.a. n.a. PMID[20000781]
NPO19935 Evodia rutaecarpa Species Rutaceae Eukaryota n.a. n.a. n.a. PMID[7463094]
NPO19935 Evodia rutaecarpa Species Rutaceae Eukaryota n.a. n.a. n.a. PMID[8201313]
NPO19935 Evodia rutaecarpa Species Rutaceae Eukaryota n.a. n.a. n.a. PMID[8699182]
NPO18340 Ligustrum lucidum Species Oleaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO19935 Evodia rutaecarpa Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO18340 Ligustrum lucidum Species Oleaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO18340 Ligustrum lucidum Species Oleaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO4877 Euodia officinalis Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO8314 Euodia ruticarpa Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO16845 Euodia bodinieri Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO19935 Evodia rutaecarpa Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO18340 Ligustrum lucidum Species Oleaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO1348 Ligustrum japonicus Species Oleaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO19884 Fraxinus excelsior Species Oleaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18340 Ligustrum lucidum Species Oleaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19935 Evodia rutaecarpa Species Rutaceae 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
NPT520 Cell Line 3T3-L1 Mus musculus Inhibition = -28.3 % PMID[451881]
NPT520 Cell Line 3T3-L1 Mus musculus Inhibition = -15.2 % PMID[451881]
NPT520 Cell Line 3T3-L1 Mus musculus Inhibition = -27.9 % PMID[451881]
NPT520 Cell Line 3T3-L1 Mus musculus Inhibition = -38.2 % PMID[451881]
NPT866 Individual Protein Peroxisome proliferator-activated receptor alpha Homo sapiens Activity = 12.2 % PMID[451881]

☑ 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 NPC101686 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 NPC65262
1.0 High Similarity NPC469364
0.9769 High Similarity NPC169398
0.9343 High Similarity NPC469367
0.9286 High Similarity NPC23677
0.9281 High Similarity NPC212808
0.927 High Similarity NPC296643
0.9203 High Similarity NPC293154
0.9185 High Similarity NPC472132
0.9098 High Similarity NPC46137
0.9098 High Similarity NPC235294
0.9 High Similarity NPC202391
0.9 High Similarity NPC296659
0.8971 High Similarity NPC263829
0.8955 High Similarity NPC138777
0.8955 High Similarity NPC246869
0.8955 High Similarity NPC225384
0.8947 High Similarity NPC469549
0.8939 High Similarity NPC106677
0.8913 High Similarity NPC220936
0.8913 High Similarity NPC31745
0.8797 High Similarity NPC471881
0.8797 High Similarity NPC35288
0.8797 High Similarity NPC471882
0.8797 High Similarity NPC156692
0.8797 High Similarity NPC45224
0.8797 High Similarity NPC288416
0.8797 High Similarity NPC173150
0.8759 High Similarity NPC69367
0.8741 High Similarity NPC474268
0.8741 High Similarity NPC119773
0.8741 High Similarity NPC475539
0.8741 High Similarity NPC143246
0.8732 High Similarity NPC251062
0.8732 High Similarity NPC63304
0.8732 High Similarity NPC184464
0.8722 High Similarity NPC61181
0.8722 High Similarity NPC471157
0.8705 High Similarity NPC476376
0.8702 High Similarity NPC52097
0.869 High Similarity NPC96599
0.8676 High Similarity NPC254819
0.8676 High Similarity NPC478255
0.8676 High Similarity NPC281798
0.8671 High Similarity NPC475528
0.8667 High Similarity NPC253595
0.8662 High Similarity NPC186296
0.8662 High Similarity NPC475213
0.8662 High Similarity NPC152796
0.8657 High Similarity NPC103533
0.8652 High Similarity NPC476385
0.8652 High Similarity NPC47471
0.8652 High Similarity NPC134405
0.8652 High Similarity NPC476377
0.8647 High Similarity NPC83218
0.8647 High Similarity NPC126991
0.8643 High Similarity NPC68092
0.8643 High Similarity NPC205195
0.8643 High Similarity NPC89105
0.8643 High Similarity NPC197316
0.8643 High Similarity NPC81515
0.8643 High Similarity NPC472350
0.8643 High Similarity NPC476383
0.8643 High Similarity NPC64141
0.8633 High Similarity NPC471345
0.863 High Similarity NPC240592
0.863 High Similarity NPC117346
0.8626 High Similarity NPC11724
0.8626 High Similarity NPC55608
0.8601 High Similarity NPC77922
0.8601 High Similarity NPC473281
0.8593 High Similarity NPC225307
0.8582 High Similarity NPC252114
0.8582 High Similarity NPC475530
0.8582 High Similarity NPC473799
0.8581 High Similarity NPC246893
0.8571 High Similarity NPC260425
0.8551 High Similarity NPC28637
0.8551 High Similarity NPC114116
0.855 High Similarity NPC476872
0.8531 High Similarity NPC298257
0.8531 High Similarity NPC476384
0.8531 High Similarity NPC119537
0.8531 High Similarity NPC205864
0.8531 High Similarity NPC247032
0.8531 High Similarity NPC478250
0.8531 High Similarity NPC476375
0.8531 High Similarity NPC476381
0.8531 High Similarity NPC269141
0.8531 High Similarity NPC96795
0.8531 High Similarity NPC112
0.8531 High Similarity NPC476397
0.8531 High Similarity NPC175214
0.8531 High Similarity NPC264632
0.8531 High Similarity NPC76406
0.8531 High Similarity NPC476378
0.8531 High Similarity NPC476380
0.8521 High Similarity NPC137501
0.8521 High Similarity NPC159387
0.8521 High Similarity NPC154262
0.8521 High Similarity NPC7518
0.8511 High Similarity NPC49597
0.8503 High Similarity NPC182350
0.8489 Intermediate Similarity NPC471029
0.8483 Intermediate Similarity NPC473147
0.8483 Intermediate Similarity NPC37838
0.8478 Intermediate Similarity NPC473285
0.8472 Intermediate Similarity NPC64195
0.8472 Intermediate Similarity NPC300894
0.8472 Intermediate Similarity NPC141455
0.8472 Intermediate Similarity NPC196063
0.8472 Intermediate Similarity NPC471028
0.8472 Intermediate Similarity NPC296954
0.8462 Intermediate Similarity NPC265648
0.8462 Intermediate Similarity NPC222433
0.8446 Intermediate Similarity NPC158546
0.8446 Intermediate Similarity NPC289021
0.8446 Intermediate Similarity NPC474620
0.844 Intermediate Similarity NPC78363
0.8435 Intermediate Similarity NPC478234
0.8429 Intermediate Similarity NPC476870
0.8425 Intermediate Similarity NPC473149
0.8414 Intermediate Similarity NPC252292
0.8414 Intermediate Similarity NPC476382
0.8414 Intermediate Similarity NPC34587
0.8414 Intermediate Similarity NPC100998
0.8414 Intermediate Similarity NPC34927
0.8403 Intermediate Similarity NPC204644
0.8403 Intermediate Similarity NPC105005
0.8394 Intermediate Similarity NPC295970
0.8392 Intermediate Similarity NPC80098
0.8389 Intermediate Similarity NPC106818
0.837 Intermediate Similarity NPC123704
0.8357 Intermediate Similarity NPC287597
0.8357 Intermediate Similarity NPC34293
0.8357 Intermediate Similarity NPC886
0.8357 Intermediate Similarity NPC471883
0.8356 Intermediate Similarity NPC229505
0.8356 Intermediate Similarity NPC291153
0.8346 Intermediate Similarity NPC469686
0.8345 Intermediate Similarity NPC194938
0.8344 Intermediate Similarity NPC475484
0.8333 Intermediate Similarity NPC148080
0.8333 Intermediate Similarity NPC469705
0.8333 Intermediate Similarity NPC282409
0.8333 Intermediate Similarity NPC319995
0.8333 Intermediate Similarity NPC17968
0.8333 Intermediate Similarity NPC289415
0.8333 Intermediate Similarity NPC469623
0.8333 Intermediate Similarity NPC87403
0.8333 Intermediate Similarity NPC470122
0.8333 Intermediate Similarity NPC469702
0.8322 Intermediate Similarity NPC475379
0.8311 Intermediate Similarity NPC470933
0.8311 Intermediate Similarity NPC476398
0.8311 Intermediate Similarity NPC259347
0.8311 Intermediate Similarity NPC476386
0.8311 Intermediate Similarity NPC94871
0.8311 Intermediate Similarity NPC473427
0.8311 Intermediate Similarity NPC306890
0.8311 Intermediate Similarity NPC471062
0.8311 Intermediate Similarity NPC478242
0.8311 Intermediate Similarity NPC478236
0.8308 Intermediate Similarity NPC148055
0.8299 Intermediate Similarity NPC97240
0.8299 Intermediate Similarity NPC232992
0.8299 Intermediate Similarity NPC175275
0.8284 Intermediate Similarity NPC476142
0.8276 Intermediate Similarity NPC263397
0.8276 Intermediate Similarity NPC302286
0.8276 Intermediate Similarity NPC88754
0.8276 Intermediate Similarity NPC116104
0.8276 Intermediate Similarity NPC237872
0.8271 Intermediate Similarity NPC476445
0.8271 Intermediate Similarity NPC469548
0.8271 Intermediate Similarity NPC201402
0.8271 Intermediate Similarity NPC469704
0.8271 Intermediate Similarity NPC469703
0.8271 Intermediate Similarity NPC476448
0.8271 Intermediate Similarity NPC160854
0.8267 Intermediate Similarity NPC203664
0.8264 Intermediate Similarity NPC46644
0.8264 Intermediate Similarity NPC79908
0.8261 Intermediate Similarity NPC477293
0.8261 Intermediate Similarity NPC477294
0.8261 Intermediate Similarity NPC229784
0.8255 Intermediate Similarity NPC470927
0.8255 Intermediate Similarity NPC188393
0.8255 Intermediate Similarity NPC35097
0.8255 Intermediate Similarity NPC257970
0.8255 Intermediate Similarity NPC470934
0.8255 Intermediate Similarity NPC107197
0.8252 Intermediate Similarity NPC220942
0.8252 Intermediate Similarity NPC324262
0.8252 Intermediate Similarity NPC171134
0.8252 Intermediate Similarity NPC321638
0.8252 Intermediate Similarity NPC321184
0.8252 Intermediate Similarity NPC328273
0.8252 Intermediate Similarity NPC62800
0.8243 Intermediate Similarity NPC220282

  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 NPC101686 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
0.8643 High Similarity NPD7266 Discontinued
0.7806 Intermediate Similarity NPD8455 Phase 2
0.7771 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.7636 Intermediate Similarity NPD7685 Pre-registration
0.7622 Intermediate Similarity NPD7472 Approved
0.7597 Intermediate Similarity NPD1653 Approved
0.7561 Intermediate Similarity NPD7054 Approved
0.7561 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.7554 Intermediate Similarity NPD1091 Approved
0.7551 Intermediate Similarity NPD7097 Phase 1
0.755 Intermediate Similarity NPD6190 Approved
0.753 Intermediate Similarity NPD7251 Discontinued
0.75 Intermediate Similarity NPD7228 Approved
0.7485 Intermediate Similarity NPD7808 Phase 3
0.747 Intermediate Similarity NPD6797 Phase 2
0.7432 Intermediate Similarity NPD4978 Clinical (unspecified phase)
0.741 Intermediate Similarity NPD7074 Phase 3
0.7391 Intermediate Similarity NPD9545 Approved
0.7389 Intermediate Similarity NPD4380 Phase 2
0.7368 Intermediate Similarity NPD4628 Phase 3
0.7337 Intermediate Similarity NPD8313 Approved
0.7337 Intermediate Similarity NPD8312 Approved
0.7279 Intermediate Similarity NPD6233 Phase 2
0.7278 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.723 Intermediate Similarity NPD7966 Clinical (unspecified phase)
0.7226 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7222 Intermediate Similarity NPD7075 Discontinued
0.7219 Intermediate Similarity NPD7240 Approved
0.7211 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.719 Intermediate Similarity NPD1652 Phase 2
0.7188 Intermediate Similarity NPD37 Approved
0.7186 Intermediate Similarity NPD3818 Discontinued
0.7181 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.7181 Intermediate Similarity NPD5124 Phase 1
0.7179 Intermediate Similarity NPD8389 Clinical (unspecified phase)
0.7178 Intermediate Similarity NPD6234 Discontinued
0.716 Intermediate Similarity NPD4965 Approved
0.716 Intermediate Similarity NPD4967 Phase 2
0.716 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.716 Intermediate Similarity NPD4966 Approved
0.7153 Intermediate Similarity NPD3225 Approved
0.7152 Intermediate Similarity NPD7033 Discontinued
0.7151 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7133 Intermediate Similarity NPD6653 Approved
0.7118 Intermediate Similarity NPD6559 Discontinued
0.7107 Intermediate Similarity NPD7458 Discontinued
0.7095 Intermediate Similarity NPD6798 Discontinued
0.7089 Intermediate Similarity NPD5403 Approved
0.7081 Intermediate Similarity NPD6801 Discontinued
0.7078 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7067 Intermediate Similarity NPD230 Phase 1
0.7067 Intermediate Similarity NPD6355 Discontinued
0.7045 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7037 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.7032 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7032 Intermediate Similarity NPD8166 Discontinued
0.7019 Intermediate Similarity NPD7411 Suspended
0.6988 Remote Similarity NPD7199 Phase 2
0.698 Remote Similarity NPD3268 Approved
0.6968 Remote Similarity NPD6674 Discontinued
0.6963 Remote Similarity NPD1358 Approved
0.6962 Remote Similarity NPD5401 Approved
0.6959 Remote Similarity NPD7993 Clinical (unspecified phase)
0.6957 Remote Similarity NPD7843 Approved
0.6954 Remote Similarity NPD4340 Discontinued
0.6944 Remote Similarity NPD422 Phase 1
0.6933 Remote Similarity NPD4062 Phase 3
0.6913 Remote Similarity NPD3027 Phase 3
0.6899 Remote Similarity NPD6799 Approved
0.6892 Remote Similarity NPD5736 Approved
0.689 Remote Similarity NPD5402 Approved
0.689 Remote Similarity NPD8443 Clinical (unspecified phase)
0.6889 Remote Similarity NPD3134 Approved
0.6884 Remote Similarity NPD969 Suspended
0.6875 Remote Similarity NPD6980 Clinical (unspecified phase)
0.6871 Remote Similarity NPD2797 Approved
0.6871 Remote Similarity NPD6362 Approved
0.6867 Remote Similarity NPD3764 Approved
0.6864 Remote Similarity NPD6167 Clinical (unspecified phase)
0.6864 Remote Similarity NPD6166 Phase 2
0.6864 Remote Similarity NPD6168 Clinical (unspecified phase)
0.6855 Remote Similarity NPD7004 Clinical (unspecified phase)
0.6846 Remote Similarity NPD4908 Phase 1
0.6835 Remote Similarity NPD5058 Phase 3
0.6824 Remote Similarity NPD5647 Approved
0.6815 Remote Similarity NPD6398 Clinical (unspecified phase)
0.6815 Remote Similarity NPD3750 Approved
0.681 Remote Similarity NPD7615 Clinical (unspecified phase)
0.6809 Remote Similarity NPD7157 Approved
0.6806 Remote Similarity NPD5125 Phase 3
0.6806 Remote Similarity NPD5126 Approved
0.6805 Remote Similarity NPD7184 Clinical (unspecified phase)
0.68 Remote Similarity NPD7095 Approved
0.6795 Remote Similarity NPD1549 Phase 2
0.6795 Remote Similarity NPD970 Clinical (unspecified phase)
0.6788 Remote Similarity NPD2684 Approved
0.6788 Remote Similarity NPD3817 Phase 2
0.6786 Remote Similarity NPD8127 Discontinued
0.6776 Remote Similarity NPD1613 Approved
0.6776 Remote Similarity NPD4060 Phase 1
0.6776 Remote Similarity NPD1612 Clinical (unspecified phase)
0.6768 Remote Similarity NPD1934 Approved
0.6759 Remote Similarity NPD3847 Discontinued
0.6755 Remote Similarity NPD4907 Clinical (unspecified phase)
0.6744 Remote Similarity NPD5844 Phase 1
0.6742 Remote Similarity NPD8397 Clinical (unspecified phase)
0.6735 Remote Similarity NPD4379 Clinical (unspecified phase)
0.6731 Remote Similarity NPD6005 Phase 3
0.6731 Remote Similarity NPD6003 Clinical (unspecified phase)
0.6731 Remote Similarity NPD6004 Phase 3
0.6731 Remote Similarity NPD1550 Clinical (unspecified phase)
0.6731 Remote Similarity NPD6006 Clinical (unspecified phase)
0.6731 Remote Similarity NPD1552 Clinical (unspecified phase)
0.6731 Remote Similarity NPD6002 Phase 3
0.6727 Remote Similarity NPD2393 Clinical (unspecified phase)
0.6727 Remote Similarity NPD7819 Suspended
0.6721 Remote Similarity NPD7237 Clinical (unspecified phase)
0.672 Remote Similarity NPD8319 Approved
0.672 Remote Similarity NPD8320 Phase 1
0.6715 Remote Similarity NPD9265 Clinical (unspecified phase)
0.6712 Remote Similarity NPD3705 Approved
0.6712 Remote Similarity NPD1535 Discovery
0.6711 Remote Similarity NPD6007 Clinical (unspecified phase)
0.6711 Remote Similarity NPD6663 Approved
0.671 Remote Similarity NPD1510 Phase 2
0.6702 Remote Similarity NPD7585 Approved
0.669 Remote Similarity NPD1778 Approved
0.6688 Remote Similarity NPD2424 Discontinued
0.6686 Remote Similarity NPD3751 Discontinued
0.6667 Remote Similarity NPD1608 Approved
0.6667 Remote Similarity NPD6647 Phase 2
0.6667 Remote Similarity NPD1894 Discontinued
0.6667 Remote Similarity NPD2935 Discontinued
0.6667 Remote Similarity NPD7680 Approved
0.6667 Remote Similarity NPD7852 Clinical (unspecified phase)
0.6667 Remote Similarity NPD1548 Phase 1
0.6667 Remote Similarity NPD2861 Phase 2
0.6667 Remote Similarity NPD7435 Discontinued
0.6667 Remote Similarity NPD8151 Discontinued
0.6667 Remote Similarity NPD1481 Phase 2
0.6649 Remote Similarity NPD7583 Approved
0.6647 Remote Similarity NPD7768 Phase 2
0.6647 Remote Similarity NPD3787 Discontinued
0.6646 Remote Similarity NPD7410 Clinical (unspecified phase)
0.6646 Remote Similarity NPD6599 Discontinued
0.6646 Remote Similarity NPD4378 Clinical (unspecified phase)
0.6645 Remote Similarity NPD4538 Approved
0.6645 Remote Similarity NPD4537 Clinical (unspecified phase)
0.6645 Remote Similarity NPD4536 Approved
0.6644 Remote Similarity NPD3267 Approved
0.6644 Remote Similarity NPD3266 Approved
0.6643 Remote Similarity NPD9493 Approved
0.6629 Remote Similarity NPD8434 Phase 2
0.6629 Remote Similarity NPD8150 Discontinued
0.6627 Remote Similarity NPD2801 Approved
0.6627 Remote Similarity NPD1465 Phase 2
0.6625 Remote Similarity NPD6652 Clinical (unspecified phase)
0.6624 Remote Similarity NPD5763 Approved
0.6624 Remote Similarity NPD5762 Approved
0.6623 Remote Similarity NPD1933 Approved
0.6623 Remote Similarity NPD6832 Phase 2
0.6621 Remote Similarity NPD1357 Approved
0.662 Remote Similarity NPD2629 Approved
0.6599 Remote Similarity NPD1610 Phase 2
0.6596 Remote Similarity NPD5535 Approved
0.6594 Remote Similarity NPD290 Approved
0.6577 Remote Similarity NPD8651 Approved
0.6576 Remote Similarity NPD7699 Phase 2
0.6576 Remote Similarity NPD7700 Phase 2
0.6569 Remote Similarity NPD5048 Discontinued
0.6561 Remote Similarity NPD2239 Approved
0.6561 Remote Similarity NPD2438 Suspended
0.6561 Remote Similarity NPD2796 Approved
0.6561 Remote Similarity NPD2240 Approved
0.6561 Remote Similarity NPD7584 Approved
0.6558 Remote Similarity NPD1240 Approved
0.6552 Remote Similarity NPD8470 Clinical (unspecified phase)
0.6549 Remote Similarity NPD1241 Discontinued
0.6543 Remote Similarity NPD3536 Discontinued
0.6533 Remote Similarity NPD3094 Phase 2
0.6532 Remote Similarity NPD7473 Discontinued
0.6531 Remote Similarity NPD3496 Discontinued
0.6528 Remote Similarity NPD694 Clinical (unspecified phase)
0.6522 Remote Similarity NPD7440 Discontinued
0.6515 Remote Similarity NPD2934 Approved
0.6515 Remote Similarity NPD2933 Approved
0.6513 Remote Similarity NPD1529 Clinical (unspecified phase)
0.651 Remote Similarity NPD7783 Phase 2
0.651 Remote Similarity NPD3685 Discontinued
0.651 Remote Similarity NPD7782 Clinical (unspecified phase)
0.6507 Remote Similarity NPD5585 Approved
0.6506 Remote Similarity NPD6677 Suspended
0.6505 Remote Similarity NPD6778 Approved
0.6505 Remote Similarity NPD6779 Approved
0.6505 Remote Similarity NPD6780 Approved
0.6505 Remote Similarity NPD6782 Approved
0.6505 Remote Similarity NPD6777 Approved
0.6505 Remote Similarity NPD6781 Approved
0.6505 Remote Similarity NPD6776 Approved
0.6503 Remote Similarity NPD6273 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