Structure

Physi-Chem Properties

Molecular Weight:  694.26
Volume:  682.441
LogP:  2.631
LogD:  2.327
LogS:  -3.929
# Rotatable Bonds:  11
TPSA:  198.51
# H-Bond Aceptor:  13
# H-Bond Donor:  5
# Rings:  6
# Heavy Atoms:  13

MedChem Properties

QED Drug-Likeness Score:  0.111
Synthetic Accessibility Score:  5.209
Fsp3:  0.486
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  2
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -6.142
MDCK Permeability:  2.3138416509027593e-05
Pgp-inhibitor:  0.002
Pgp-substrate:  0.035
Human Intestinal Absorption (HIA):  0.935
20% Bioavailability (F20%):  0.43
30% Bioavailability (F30%):  0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.047
Plasma Protein Binding (PPB):  83.3255844116211%
Volume Distribution (VD):  0.429
Pgp-substrate:  8.997042655944824%

ADMET: Metabolism

CYP1A2-inhibitor:  0.025
CYP1A2-substrate:  0.026
CYP2C19-inhibitor:  0.308
CYP2C19-substrate:  0.065
CYP2C9-inhibitor:  0.714
CYP2C9-substrate:  0.199
CYP2D6-inhibitor:  0.155
CYP2D6-substrate:  0.073
CYP3A4-inhibitor:  0.822
CYP3A4-substrate:  0.319

ADMET: Excretion

Clearance (CL):  7.187
Half-life (T1/2):  0.897

ADMET: Toxicity

hERG Blockers:  0.215
Human Hepatotoxicity (H-HT):  0.844
Drug-inuced Liver Injury (DILI):  0.959
AMES Toxicity:  0.099
Rat Oral Acute Toxicity:  0.71
Maximum Recommended Daily Dose:  0.185
Skin Sensitization:  0.323
Carcinogencity:  0.178
Eye Corrosion:  0.004
Eye Irritation:  0.028
Respiratory Toxicity:  0.384

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

  Natural Product: NPC35097

Natural Product ID:  NPC35097
Common Name*:   Chinensiolide E
IUPAC Name:   [(2R,3S,4S,5R,6R)-6-[[(3aS,6R,6aR,8S,9aR,9bS)-6-hydroxy-6-methyl-3,9-dimethylidene-2-oxo-3a,4,5,6a,7,8,9a,9b-octahydroazuleno[4,5-b]furan-8-yl]oxy]-3,4-dihydroxy-5-[2-(4-hydroxyphenyl)acetyl]oxyoxan-2-yl]methyl 2-(4-hydroxyphenyl)acetate
Synonyms:   chinensiolide E
Standard InCHIKey:  GDSPNUSHQQYFSK-MCOQXLJUSA-N
Standard InCHI:  InChI=1S/C37H42O13/c1-18-24-12-13-37(3,45)25-16-26(19(2)30(25)33(24)50-35(18)44)47-36-34(49-29(41)15-21-6-10-23(39)11-7-21)32(43)31(42)27(48-36)17-46-28(40)14-20-4-8-22(38)9-5-20/h4-11,24-27,30-34,36,38-39,42-43,45H,1-2,12-17H2,3H3/t24-,25+,26-,27+,30-,31+,32-,33-,34+,36+,37+/m0/s1
SMILES:  O=C(Cc1ccc(cc1)O)OC[C@H]1O[C@@H](O[C@H]2C[C@@H]3[C@H](C2=C)[C@H]2OC(=O)C(=C)[C@@H]2CC[C@@]3(C)O)[C@@H]([C@H]([C@@H]1O)O)OC(=O)Cc1ccc(cc1)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL507663
PubChem CID:   16091565
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001283] Terpene lactones
          • [CHEMONTID:0001543] Sesquiterpene lactones
            • [CHEMONTID:0001770] Guaianolides 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
NPO10533 Ixeris chinensis Species Asteraceae Eukaryota n.a. whole plant n.a. PMID[15635221]
NPO10533 Ixeris chinensis Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[17067155]
NPO10533 Ixeris chinensis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO10533 Ixeris chinensis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO10533 Ixeris chinensis Species Asteraceae 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
NPT81 Cell Line A549 Homo sapiens IC50 > 100000.0 nM PMID[509336]
NPT1374 Cell Line WI-38 Homo sapiens IC50 = 23000.0 nM PMID[509336]
NPT1475 Cell Line WI-38 VA13 Homo sapiens IC50 = 720.0 nM PMID[509336]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 140000.0 nM PMID[509336]

☑ 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 NPC35097 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
0.9859 High Similarity NPC120728
0.9577 High Similarity NPC194938
0.931 High Similarity NPC473147
0.8933 High Similarity NPC240592
0.8933 High Similarity NPC117346
0.8912 High Similarity NPC202391
0.8912 High Similarity NPC296659
0.8867 High Similarity NPC96599
0.8784 High Similarity NPC184464
0.8784 High Similarity NPC251062
0.8758 High Similarity NPC257847
0.875 High Similarity NPC289021
0.875 High Similarity NPC158546
0.8716 High Similarity NPC186296
0.8716 High Similarity NPC478250
0.8693 High Similarity NPC478235
0.8662 High Similarity NPC130489
0.8662 High Similarity NPC208676
0.8616 High Similarity NPC109990
0.8601 High Similarity NPC478255
0.859 High Similarity NPC475378
0.8581 High Similarity NPC137501
0.8581 High Similarity NPC7518
0.8581 High Similarity NPC159387
0.8581 High Similarity NPC154262
0.8562 High Similarity NPC471345
0.8553 High Similarity NPC145847
0.8543 High Similarity NPC119773
0.8543 High Similarity NPC143246
0.8543 High Similarity NPC475539
0.8543 High Similarity NPC474268
0.8535 High Similarity NPC187205
0.8526 High Similarity NPC475484
0.8516 High Similarity NPC229354
0.8506 High Similarity NPC475379
0.8503 High Similarity NPC469696
0.8497 Intermediate Similarity NPC478236
0.8497 Intermediate Similarity NPC161955
0.8497 Intermediate Similarity NPC478234
0.8483 Intermediate Similarity NPC164172
0.8477 Intermediate Similarity NPC475528
0.8446 Intermediate Similarity NPC220936
0.8446 Intermediate Similarity NPC31745
0.8425 Intermediate Similarity NPC169398
0.8421 Intermediate Similarity NPC320734
0.8414 Intermediate Similarity NPC471066
0.8414 Intermediate Similarity NPC471095
0.8411 Intermediate Similarity NPC63304
0.8408 Intermediate Similarity NPC38699
0.8405 Intermediate Similarity NPC21956
0.84 Intermediate Similarity NPC148080
0.84 Intermediate Similarity NPC469623
0.8397 Intermediate Similarity NPC299706
0.8397 Intermediate Similarity NPC115466
0.8397 Intermediate Similarity NPC61604
0.8397 Intermediate Similarity NPC245615
0.8392 Intermediate Similarity NPC225307
0.8387 Intermediate Similarity NPC474620
0.8355 Intermediate Similarity NPC210330
0.8354 Intermediate Similarity NPC163635
0.8345 Intermediate Similarity NPC281798
0.8345 Intermediate Similarity NPC235294
0.8345 Intermediate Similarity NPC46137
0.8344 Intermediate Similarity NPC40305
0.8344 Intermediate Similarity NPC293154
0.8333 Intermediate Similarity NPC194705
0.8323 Intermediate Similarity NPC158635
0.8323 Intermediate Similarity NPC229882
0.8322 Intermediate Similarity NPC328273
0.8322 Intermediate Similarity NPC321638
0.8322 Intermediate Similarity NPC288416
0.8322 Intermediate Similarity NPC171134
0.8322 Intermediate Similarity NPC49597
0.8322 Intermediate Similarity NPC321184
0.8302 Intermediate Similarity NPC226759
0.8301 Intermediate Similarity NPC212808
0.8289 Intermediate Similarity NPC473281
0.8289 Intermediate Similarity NPC196063
0.8289 Intermediate Similarity NPC300894
0.8289 Intermediate Similarity NPC77922
0.8289 Intermediate Similarity NPC141455
0.8289 Intermediate Similarity NPC296954
0.8282 Intermediate Similarity NPC469459
0.8282 Intermediate Similarity NPC149002
0.8282 Intermediate Similarity NPC469419
0.8282 Intermediate Similarity NPC469458
0.8282 Intermediate Similarity NPC469396
0.8282 Intermediate Similarity NPC88176
0.828 Intermediate Similarity NPC87403
0.8276 Intermediate Similarity NPC470122
0.8276 Intermediate Similarity NPC17968
0.8276 Intermediate Similarity NPC469705
0.8272 Intermediate Similarity NPC471861
0.8261 Intermediate Similarity NPC477627
0.8255 Intermediate Similarity NPC101686
0.8255 Intermediate Similarity NPC469364
0.8255 Intermediate Similarity NPC65262
0.825 Intermediate Similarity NPC179914
0.8243 Intermediate Similarity NPC263829
0.8243 Intermediate Similarity NPC123988
0.8239 Intermediate Similarity NPC478055
0.8231 Intermediate Similarity NPC28637
0.8224 Intermediate Similarity NPC105005
0.8224 Intermediate Similarity NPC475213
0.8224 Intermediate Similarity NPC152796
0.8219 Intermediate Similarity NPC225384
0.8219 Intermediate Similarity NPC246869
0.8219 Intermediate Similarity NPC138777
0.8217 Intermediate Similarity NPC106818
0.8212 Intermediate Similarity NPC46644
0.821 Intermediate Similarity NPC471850
0.8205 Intermediate Similarity NPC162569
0.8205 Intermediate Similarity NPC179128
0.8205 Intermediate Similarity NPC87630
0.8205 Intermediate Similarity NPC267469
0.8205 Intermediate Similarity NPC116292
0.8205 Intermediate Similarity NPC35160
0.82 Intermediate Similarity NPC324262
0.82 Intermediate Similarity NPC62800
0.8199 Intermediate Similarity NPC269668
0.8194 Intermediate Similarity NPC173150
0.8194 Intermediate Similarity NPC45224
0.8194 Intermediate Similarity NPC469687
0.8194 Intermediate Similarity NPC106677
0.8194 Intermediate Similarity NPC471882
0.8194 Intermediate Similarity NPC103533
0.8194 Intermediate Similarity NPC471881
0.8194 Intermediate Similarity NPC473138
0.8194 Intermediate Similarity NPC35288
0.8194 Intermediate Similarity NPC28776
0.8194 Intermediate Similarity NPC156692
0.8193 Intermediate Similarity NPC254071
0.8193 Intermediate Similarity NPC271755
0.8193 Intermediate Similarity NPC149502
0.8193 Intermediate Similarity NPC222665
0.8193 Intermediate Similarity NPC477617
0.8187 Intermediate Similarity NPC4747
0.8187 Intermediate Similarity NPC104275
0.8182 Intermediate Similarity NPC473867
0.8182 Intermediate Similarity NPC208293
0.8182 Intermediate Similarity NPC229505
0.8169 Intermediate Similarity NPC232454
0.8169 Intermediate Similarity NPC178449
0.8169 Intermediate Similarity NPC470907
0.8158 Intermediate Similarity NPC296643
0.8153 Intermediate Similarity NPC471135
0.8148 Intermediate Similarity NPC117943
0.8148 Intermediate Similarity NPC471858
0.8148 Intermediate Similarity NPC293568
0.8141 Intermediate Similarity NPC478242
0.8138 Intermediate Similarity NPC158673
0.8133 Intermediate Similarity NPC100558
0.8133 Intermediate Similarity NPC84789
0.8133 Intermediate Similarity NPC310252
0.8133 Intermediate Similarity NPC302583
0.8129 Intermediate Similarity NPC473149
0.8129 Intermediate Similarity NPC470330
0.8125 Intermediate Similarity NPC471157
0.8125 Intermediate Similarity NPC228357
0.8125 Intermediate Similarity NPC61181
0.8121 Intermediate Similarity NPC471860
0.8113 Intermediate Similarity NPC322048
0.8113 Intermediate Similarity NPC478232
0.8113 Intermediate Similarity NPC318447
0.8108 Intermediate Similarity NPC114116
0.8105 Intermediate Similarity NPC237872
0.8105 Intermediate Similarity NPC302286
0.8105 Intermediate Similarity NPC116104
0.8105 Intermediate Similarity NPC88754
0.8105 Intermediate Similarity NPC263397
0.8105 Intermediate Similarity NPC89317
0.8105 Intermediate Similarity NPC204644
0.8101 Intermediate Similarity NPC478268
0.8099 Intermediate Similarity NPC471067
0.8098 Intermediate Similarity NPC476011
0.8095 Intermediate Similarity NPC476407
0.8095 Intermediate Similarity NPC254819
0.8092 Intermediate Similarity NPC476377
0.8092 Intermediate Similarity NPC47471
0.8089 Intermediate Similarity NPC69367
0.8086 Intermediate Similarity NPC474936
0.8086 Intermediate Similarity NPC138993
0.8084 Intermediate Similarity NPC148185
0.8082 Intermediate Similarity NPC469549
0.8079 Intermediate Similarity NPC64141
0.8079 Intermediate Similarity NPC472350
0.8079 Intermediate Similarity NPC476383
0.8079 Intermediate Similarity NPC81515
0.8079 Intermediate Similarity NPC89105
0.8079 Intermediate Similarity NPC68092
0.8079 Intermediate Similarity NPC197316
0.8079 Intermediate Similarity NPC220942
0.8077 Intermediate Similarity NPC189631
0.8075 Intermediate Similarity NPC329997
0.8075 Intermediate Similarity NPC49173
0.8067 Intermediate Similarity NPC472132
0.8065 Intermediate Similarity NPC291153
0.8063 Intermediate Similarity NPC186316
0.8063 Intermediate Similarity NPC172920
0.8063 Intermediate Similarity NPC156624

  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 NPC35097 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
0.8144 Intermediate Similarity NPD7685 Pre-registration
0.8079 Intermediate Similarity NPD7266 Discontinued
0.7953 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7798 Intermediate Similarity NPD7228 Approved
0.7778 Intermediate Similarity NPD8455 Phase 2
0.7697 Intermediate Similarity NPD6234 Discontinued
0.7683 Intermediate Similarity NPD4965 Approved
0.7683 Intermediate Similarity NPD4966 Approved
0.7683 Intermediate Similarity NPD4967 Phase 2
0.7667 Intermediate Similarity NPD3764 Approved
0.7643 Intermediate Similarity NPD6190 Approved
0.7607 Intermediate Similarity NPD37 Approved
0.7566 Intermediate Similarity NPD7966 Clinical (unspecified phase)
0.7547 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.753 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD7199 Phase 2
0.7468 Intermediate Similarity NPD4628 Phase 3
0.7429 Intermediate Similarity NPD8312 Approved
0.7429 Intermediate Similarity NPD8313 Approved
0.7414 Intermediate Similarity NPD6559 Discontinued
0.7414 Intermediate Similarity NPD7240 Approved
0.7403 Intermediate Similarity NPD6355 Discontinued
0.74 Intermediate Similarity NPD6007 Clinical (unspecified phase)
0.7386 Intermediate Similarity NPD6663 Approved
0.7384 Intermediate Similarity NPD3818 Discontinued
0.7341 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.7333 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.731 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7283 Intermediate Similarity NPD7799 Discontinued
0.7278 Intermediate Similarity NPD6006 Clinical (unspecified phase)
0.7278 Intermediate Similarity NPD6005 Phase 3
0.7278 Intermediate Similarity NPD6002 Phase 3
0.7278 Intermediate Similarity NPD6004 Phase 3
0.7278 Intermediate Similarity NPD6003 Clinical (unspecified phase)
0.7237 Intermediate Similarity NPD5736 Approved
0.7219 Intermediate Similarity NPD7075 Discontinued
0.72 Intermediate Similarity NPD7074 Phase 3
0.7197 Intermediate Similarity NPD7097 Phase 1
0.7197 Intermediate Similarity NPD4978 Clinical (unspecified phase)
0.7169 Intermediate Similarity NPD4380 Phase 2
0.716 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD7054 Approved
0.7143 Intermediate Similarity NPD8166 Discontinued
0.7134 Intermediate Similarity NPD6653 Approved
0.7108 Intermediate Similarity NPD7458 Discontinued
0.7102 Intermediate Similarity NPD7472 Approved
0.7093 Intermediate Similarity NPD8127 Discontinued
0.7091 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7079 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.7079 Intermediate Similarity NPD7808 Phase 3
0.7073 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7073 Intermediate Similarity NPD8389 Clinical (unspecified phase)
0.7059 Intermediate Similarity NPD5647 Approved
0.7051 Intermediate Similarity NPD6233 Phase 2
0.7047 Intermediate Similarity NPD5125 Phase 3
0.7047 Intermediate Similarity NPD5126 Approved
0.7044 Intermediate Similarity NPD7033 Discontinued
0.7041 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.7037 Intermediate Similarity NPD7680 Approved
0.7032 Intermediate Similarity NPD5952 Clinical (unspecified phase)
0.703 Intermediate Similarity NPD6273 Approved
0.7027 Intermediate Similarity NPD9545 Approved
0.7026 Intermediate Similarity NPD7930 Approved
0.7022 Intermediate Similarity NPD7251 Discontinued
0.7017 Intermediate Similarity NPD8150 Discontinued
0.7017 Intermediate Similarity NPD8434 Phase 2
0.7005 Intermediate Similarity NPD7237 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD8319 Approved
0.7 Intermediate Similarity NPD8320 Phase 1
0.6987 Remote Similarity NPD6798 Discontinued
0.6966 Remote Similarity NPD6797 Phase 2
0.6966 Remote Similarity NPD7993 Clinical (unspecified phase)
0.6964 Remote Similarity NPD7028 Phase 2
0.6963 Remote Similarity NPD7999 Approved
0.6962 Remote Similarity NPD230 Phase 1
0.6951 Remote Similarity NPD5058 Phase 3
0.6946 Remote Similarity NPD1653 Approved
0.6941 Remote Similarity NPD7819 Suspended
0.694 Remote Similarity NPD8397 Clinical (unspecified phase)
0.6933 Remote Similarity NPD1878 Clinical (unspecified phase)
0.6906 Remote Similarity NPD7090 Clinical (unspecified phase)
0.6903 Remote Similarity NPD2861 Phase 2
0.6901 Remote Similarity NPD8443 Clinical (unspecified phase)
0.6883 Remote Similarity NPD3094 Phase 2
0.6882 Remote Similarity NPD6801 Discontinued
0.6879 Remote Similarity NPD6859 Clinical (unspecified phase)
0.6871 Remote Similarity NPD7421 Clinical (unspecified phase)
0.6862 Remote Similarity NPD7699 Phase 2
0.6862 Remote Similarity NPD7700 Phase 2
0.686 Remote Similarity NPD7768 Phase 2
0.6859 Remote Similarity NPD7435 Discontinued
0.6854 Remote Similarity NPD8470 Clinical (unspecified phase)
0.6852 Remote Similarity NPD5762 Approved
0.6852 Remote Similarity NPD5763 Approved
0.6842 Remote Similarity NPD1091 Approved
0.6832 Remote Similarity NPD2799 Discontinued
0.6829 Remote Similarity NPD6398 Clinical (unspecified phase)
0.6829 Remote Similarity NPD3750 Approved
0.6824 Remote Similarity NPD7615 Clinical (unspecified phase)
0.6815 Remote Similarity NPD7095 Approved
0.681 Remote Similarity NPD5958 Discontinued
0.6802 Remote Similarity NPD5402 Approved
0.6797 Remote Similarity NPD1608 Approved
0.6791 Remote Similarity NPD6534 Approved
0.6791 Remote Similarity NPD6535 Approved
0.679 Remote Similarity NPD2438 Suspended
0.679 Remote Similarity NPD2935 Discontinued
0.6786 Remote Similarity NPD5403 Approved
0.6784 Remote Similarity NPD1934 Approved
0.6774 Remote Similarity NPD2797 Approved
0.6774 Remote Similarity NPD6362 Approved
0.676 Remote Similarity NPD5844 Phase 1
0.6757 Remote Similarity NPD2629 Approved
0.6747 Remote Similarity NPD7236 Approved
0.6744 Remote Similarity NPD2393 Clinical (unspecified phase)
0.6744 Remote Similarity NPD5761 Phase 2
0.6744 Remote Similarity NPD5760 Phase 2
0.6742 Remote Similarity NPD7473 Discontinued
0.6735 Remote Similarity NPD7874 Approved
0.6735 Remote Similarity NPD7875 Clinical (unspecified phase)
0.6732 Remote Similarity NPD3092 Approved
0.673 Remote Similarity NPD4062 Phase 3
0.6727 Remote Similarity NPD4109 Clinical (unspecified phase)
0.6727 Remote Similarity NPD4110 Phase 3
0.6725 Remote Similarity NPD7411 Suspended
0.6724 Remote Similarity NPD3749 Approved
0.6719 Remote Similarity NPD6823 Phase 2
0.6711 Remote Similarity NPD3019 Approved
0.6711 Remote Similarity NPD2932 Approved
0.6709 Remote Similarity NPD3027 Phase 3
0.6707 Remote Similarity NPD6799 Approved
0.6707 Remote Similarity NPD1549 Phase 2
0.6704 Remote Similarity NPD3751 Discontinued
0.6702 Remote Similarity NPD6777 Approved
0.6702 Remote Similarity NPD6781 Approved
0.6702 Remote Similarity NPD6779 Approved
0.6702 Remote Similarity NPD6780 Approved
0.6702 Remote Similarity NPD6778 Approved
0.6702 Remote Similarity NPD6776 Approved
0.6702 Remote Similarity NPD6782 Approved
0.6701 Remote Similarity NPD7783 Phase 2
0.6701 Remote Similarity NPD7782 Clinical (unspecified phase)
0.6689 Remote Similarity NPD7741 Discontinued
0.6687 Remote Similarity NPD4060 Phase 1
0.6687 Remote Similarity NPD4140 Approved
0.6685 Remote Similarity NPD6168 Clinical (unspecified phase)
0.6685 Remote Similarity NPD6166 Phase 2
0.6685 Remote Similarity NPD7852 Clinical (unspecified phase)
0.6685 Remote Similarity NPD6167 Clinical (unspecified phase)
0.6684 Remote Similarity NPD8151 Discontinued
0.6684 Remote Similarity NPD7696 Phase 3
0.6684 Remote Similarity NPD7697 Approved
0.6684 Remote Similarity NPD7698 Approved
0.6667 Remote Similarity NPD6674 Discontinued
0.6667 Remote Similarity NPD3882 Suspended
0.6667 Remote Similarity NPD6232 Discontinued
0.6667 Remote Similarity NPD3787 Discontinued
0.6667 Remote Similarity NPD6599 Discontinued
0.6667 Remote Similarity NPD3268 Approved
0.6667 Remote Similarity NPD5401 Approved
0.6667 Remote Similarity NPD6685 Approved
0.6667 Remote Similarity NPD969 Suspended
0.6649 Remote Similarity NPD7871 Phase 2
0.6649 Remote Similarity NPD7870 Phase 2
0.6648 Remote Similarity NPD5494 Approved
0.6647 Remote Similarity NPD7239 Suspended
0.6647 Remote Similarity NPD1465 Phase 2
0.6646 Remote Similarity NPD5735 Approved
0.6646 Remote Similarity NPD1550 Clinical (unspecified phase)
0.6646 Remote Similarity NPD4908 Phase 1
0.6646 Remote Similarity NPD1552 Clinical (unspecified phase)
0.6646 Remote Similarity NPD2343 Clinical (unspecified phase)
0.6633 Remote Similarity NPD7701 Phase 2
0.6633 Remote Similarity NPD7585 Approved
0.663 Remote Similarity NPD8407 Phase 2
0.6627 Remote Similarity NPD3400 Discontinued
0.6626 Remote Similarity NPD1510 Phase 2
0.6625 Remote Similarity NPD8032 Phase 2
0.6624 Remote Similarity NPD2798 Approved
0.6616 Remote Similarity NPD7801 Approved
0.6609 Remote Similarity NPD3817 Phase 2
0.6608 Remote Similarity NPD3455 Phase 2
0.6608 Remote Similarity NPD5808 Clinical (unspecified phase)
0.6606 Remote Similarity NPD2424 Discontinued
0.6606 Remote Similarity NPD4534 Discontinued
0.6603 Remote Similarity NPD1876 Approved
0.6603 Remote Similarity NPD1283 Approved
0.6601 Remote Similarity NPD17 Approved
0.6596 Remote Similarity NPD7296 Approved
0.6585 Remote Similarity NPD7137 Phase 2
0.6584 Remote Similarity NPD1613 Approved
0.6584 Remote Similarity NPD2979 Phase 3
0.6584 Remote Similarity NPD1612 Clinical (unspecified phase)
0.6582 Remote Similarity NPD7583 Approved
0.6581 Remote Similarity NPD1481 Phase 2
0.6579 Remote Similarity NPD3091 Approved
0.6573 Remote Similarity NPD7229 Phase 3
0.6568 Remote Similarity NPD4378 Clinical (unspecified phase)
0.6568 Remote Similarity NPD2532 Approved
0.6568 Remote Similarity NPD2534 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