Structure

Physi-Chem Properties

Molecular Weight:  964.52
Volume:  934.741
LogP:  1.23
LogD:  2.167
LogS:  -2.664
# Rotatable Bonds:  15
TPSA:  324.44
# H-Bond Aceptor:  20
# H-Bond Donor:  12
# Rings:  7
# Heavy Atoms:  20

MedChem Properties

QED Drug-Likeness Score:  0.069
Synthetic Accessibility Score:  6.529
Fsp3:  0.979
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:  -6.391
MDCK Permeability:  0.0005311262793838978
Pgp-inhibitor:  0.052
Pgp-substrate:  0.999
Human Intestinal Absorption (HIA):  0.995
20% Bioavailability (F20%):  0.013
30% Bioavailability (F30%):  1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.033
Plasma Protein Binding (PPB):  45.815818786621094%
Volume Distribution (VD):  0.012
Pgp-substrate:  15.437070846557617%

ADMET: Metabolism

CYP1A2-inhibitor:  0.001
CYP1A2-substrate:  0.038
CYP2C19-inhibitor:  0.001
CYP2C19-substrate:  0.08
CYP2C9-inhibitor:  0.0
CYP2C9-substrate:  0.005
CYP2D6-inhibitor:  0.003
CYP2D6-substrate:  0.032
CYP3A4-inhibitor:  0.012
CYP3A4-substrate:  0.019

ADMET: Excretion

Clearance (CL):  0.592
Half-life (T1/2):  0.766

ADMET: Toxicity

hERG Blockers:  0.852
Human Hepatotoxicity (H-HT):  0.271
Drug-inuced Liver Injury (DILI):  0.129
AMES Toxicity:  0.08
Rat Oral Acute Toxicity:  0.036
Maximum Recommended Daily Dose:  0.007
Skin Sensitization:  0.891
Carcinogencity:  0.051
Eye Corrosion:  0.003
Eye Irritation:  0.007
Respiratory Toxicity:  0.952

Download Data

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

  Natural Product: NPC470591

Natural Product ID:  NPC470591
Common Name*:   Chamaeliroside C
IUPAC Name:   [(2R,3R,4R,5R,6S)-6-[(3S,4R,6R)-6-[(3S,5S,6R,8R,9S,10R,13S,14S,16S,17R)-6,16-dihydroxy-10,13-dimethyl-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxy-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]-4-hydroxy-2-methylheptan-3-yl]oxy-4,5-dihydroxy-2-methyloxan-3-yl] acetate
Synonyms:   chamaeliroside C
Standard InCHIKey:  ISKGGEOAHJUSOP-OQRWGDMKSA-N
Standard InCHI:  InChI=1S/C47H80O20/c1-18(2)41(67-44-40(60)37(57)42(20(4)62-44)63-21(5)49)29(52)12-19(3)32-28(51)15-25-23-14-27(50)26-13-22(8-10-46(26,6)24(23)9-11-47(25,32)7)64-45-39(59)36(56)34(54)31(66-45)17-61-43-38(58)35(55)33(53)30(16-48)65-43/h18-20,22-45,48,50-60H,8-17H2,1-7H3/t19-,20-,22+,23-,24+,25+,26-,27-,28+,29-,30-,31-,32+,33-,34-,35+,36+,37-,38-,39-,40-,41+,42+,43-,44+,45-,46-,47+/m1/s1
SMILES:  CC1C(C(C(C(O1)OC(C(C)C)C(CC(C)C2C(CC3C2(CCC4C3CC(C5C4(CCC(C5)OC6C(C(C(C(O6)COC7C(C(C(C(O7)CO)O)O)O)O)O)O)C)O)C)O)O)O)O)OC(=O)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL2086411
PubChem CID:   66553741
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000258] Steroids and steroid derivatives
        • [CHEMONTID:0001013] Steroidal glycosides

*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
NPO33234 chamaellirium luteum Species n.a. n.a. roots sourced from Botanical Liaisons Ltd. (USA) and Blessed Herbs Ltd. (USA) n.a. PMID[22880631]

☑ 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
NPT1523 Cell Line NFF Homo sapiens IC50 > 50.0 ug.mL-1 PMID[486706]
NPT165 Cell Line HeLa Homo sapiens IC50 > 50.0 ug.mL-1 PMID[486706]
NPT139 Cell Line HT-29 Homo sapiens IC50 > 50.0 ug.mL-1 PMID[486706]
NPT83 Cell Line MCF7 Homo sapiens IC50 > 50.0 ug.mL-1 PMID[486706]
NPT1524 Cell Line MM96L Homo sapiens IC50 > 50.0 ug.mL-1 PMID[486706]
NPT111 Cell Line K562 Homo sapiens IC50 > 50.0 ug.mL-1 PMID[486706]

☑ 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 NPC470591 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
0.978 High Similarity NPC210157
0.967 High Similarity NPC296936
0.9556 High Similarity NPC137004
0.9556 High Similarity NPC172838
0.9468 High Similarity NPC476838
0.9468 High Similarity NPC476839
0.9468 High Similarity NPC475574
0.9348 High Similarity NPC94582
0.9348 High Similarity NPC57964
0.9333 High Similarity NPC65550
0.9263 High Similarity NPC472081
0.9263 High Similarity NPC108227
0.9263 High Similarity NPC476512
0.9247 High Similarity NPC238796
0.9247 High Similarity NPC304011
0.9247 High Similarity NPC203434
0.9247 High Similarity NPC139271
0.9247 High Similarity NPC237071
0.9247 High Similarity NPC121453
0.9239 High Similarity NPC179859
0.9239 High Similarity NPC312678
0.9239 High Similarity NPC475436
0.9239 High Similarity NPC253268
0.9239 High Similarity NPC473851
0.9239 High Similarity NPC174024
0.9239 High Similarity NPC291203
0.9239 High Similarity NPC131693
0.9239 High Similarity NPC291547
0.9239 High Similarity NPC217205
0.9231 High Similarity NPC473830
0.9231 High Similarity NPC204881
0.9167 High Similarity NPC310138
0.9167 High Similarity NPC470029
0.9167 High Similarity NPC134967
0.9167 High Similarity NPC114700
0.9149 High Similarity NPC307534
0.9149 High Similarity NPC476112
0.914 High Similarity NPC473610
0.914 High Similarity NPC107962
0.914 High Similarity NPC206003
0.914 High Similarity NPC6295
0.914 High Similarity NPC473727
0.914 High Similarity NPC211354
0.914 High Similarity NPC19400
0.914 High Similarity NPC475351
0.914 High Similarity NPC107188
0.913 High Similarity NPC88962
0.913 High Similarity NPC250393
0.913 High Similarity NPC473726
0.913 High Similarity NPC144790
0.913 High Similarity NPC477547
0.913 High Similarity NPC48339
0.913 High Similarity NPC234352
0.913 High Similarity NPC177834
0.913 High Similarity NPC297348
0.913 High Similarity NPC249204
0.913 High Similarity NPC325828
0.913 High Similarity NPC477451
0.913 High Similarity NPC149400
0.913 High Similarity NPC141769
0.9111 High Similarity NPC281004
0.9072 High Similarity NPC476837
0.9072 High Similarity NPC97260
0.9072 High Similarity NPC139181
0.9053 High Similarity NPC473518
0.9043 High Similarity NPC470866
0.9043 High Similarity NPC84111
0.9043 High Similarity NPC232037
0.9043 High Similarity NPC195297
0.9043 High Similarity NPC184617
0.9043 High Similarity NPC284104
0.9043 High Similarity NPC97700
0.9043 High Similarity NPC160426
0.9043 High Similarity NPC103616
0.9043 High Similarity NPC116756
0.9043 High Similarity NPC98018
0.9043 High Similarity NPC470865
0.9043 High Similarity NPC473601
0.9043 High Similarity NPC30856
0.9043 High Similarity NPC475625
0.9043 High Similarity NPC132080
0.9043 High Similarity NPC470863
0.9043 High Similarity NPC287483
0.9043 High Similarity NPC470864
0.9043 High Similarity NPC128572
0.9043 High Similarity NPC475643
0.9032 High Similarity NPC151214
0.9032 High Similarity NPC191915
0.9032 High Similarity NPC473774
0.9032 High Similarity NPC252253
0.9032 High Similarity NPC309866
0.9032 High Similarity NPC264101
0.9032 High Similarity NPC294686
0.9032 High Similarity NPC24960
0.9032 High Similarity NPC471464
0.9032 High Similarity NPC45959
0.9032 High Similarity NPC222731
0.9032 High Similarity NPC305418
0.9011 High Similarity NPC473472
0.9011 High Similarity NPC102725
0.9011 High Similarity NPC131466
0.898 High Similarity NPC469827
0.8969 High Similarity NPC80191
0.8969 High Similarity NPC310031
0.8947 High Similarity NPC477223
0.8947 High Similarity NPC274200
0.8947 High Similarity NPC477222
0.8947 High Similarity NPC232611
0.8947 High Similarity NPC303069
0.8947 High Similarity NPC115165
0.8947 High Similarity NPC51520
0.8947 High Similarity NPC470861
0.8947 High Similarity NPC470862
0.8947 High Similarity NPC83137
0.8936 High Similarity NPC92196
0.8936 High Similarity NPC474399
0.8913 High Similarity NPC473542
0.8913 High Similarity NPC279329
0.8913 High Similarity NPC223143
0.8854 High Similarity NPC209798
0.8854 High Similarity NPC291548
0.8854 High Similarity NPC471374
0.8854 High Similarity NPC471375
0.8842 High Similarity NPC476510
0.8842 High Similarity NPC142264
0.8842 High Similarity NPC252056
0.8824 High Similarity NPC469824
0.8817 High Similarity NPC473637
0.8817 High Similarity NPC229801
0.8817 High Similarity NPC36372
0.8817 High Similarity NPC307167
0.8817 High Similarity NPC293609
0.8817 High Similarity NPC149966
0.8817 High Similarity NPC5632
0.8817 High Similarity NPC476668
0.8817 High Similarity NPC210759
0.8791 High Similarity NPC43912
0.8791 High Similarity NPC140446
0.8763 High Similarity NPC471428
0.8763 High Similarity NPC51579
0.8763 High Similarity NPC470030
0.8763 High Similarity NPC471426
0.8763 High Similarity NPC471427
0.8763 High Similarity NPC20028
0.875 High Similarity NPC233649
0.875 High Similarity NPC475207
0.875 High Similarity NPC470028
0.8737 High Similarity NPC477494
0.8723 High Similarity NPC277774
0.8723 High Similarity NPC476669
0.8723 High Similarity NPC311246
0.8723 High Similarity NPC167644
0.8713 High Similarity NPC472079
0.8713 High Similarity NPC469826
0.8673 High Similarity NPC477172
0.866 High Similarity NPC473616
0.8646 High Similarity NPC156377
0.8632 High Similarity NPC3538
0.8632 High Similarity NPC473503
0.8632 High Similarity NPC113500
0.8632 High Similarity NPC475325
0.8632 High Similarity NPC477224
0.8632 High Similarity NPC175
0.8627 High Similarity NPC228190
0.8627 High Similarity NPC236753
0.8627 High Similarity NPC469825
0.8602 High Similarity NPC82955
0.8602 High Similarity NPC20822
0.8571 High Similarity NPC41843
0.8571 High Similarity NPC290612
0.8557 High Similarity NPC472273
0.8542 High Similarity NPC215570
0.8542 High Similarity NPC473067
0.8542 High Similarity NPC473064
0.8542 High Similarity NPC473065
0.8542 High Similarity NPC469710
0.8529 High Similarity NPC475319
0.8529 High Similarity NPC92890
0.8529 High Similarity NPC202898
0.8526 High Similarity NPC224003
0.8526 High Similarity NPC470623
0.8526 High Similarity NPC323231
0.8526 High Similarity NPC171741
0.8526 High Similarity NPC18724
0.8515 High Similarity NPC215408
0.8485 Intermediate Similarity NPC478106
0.8469 Intermediate Similarity NPC292775
0.8469 Intermediate Similarity NPC473638
0.8462 Intermediate Similarity NPC114188
0.8462 Intermediate Similarity NPC204392
0.8462 Intermediate Similarity NPC65167
0.8462 Intermediate Similarity NPC1876
0.8462 Intermediate Similarity NPC240734
0.8462 Intermediate Similarity NPC275668
0.8462 Intermediate Similarity NPC91838
0.8454 Intermediate Similarity NPC473287
0.8447 Intermediate Similarity NPC92297
0.8447 Intermediate Similarity NPC220836
0.8447 Intermediate Similarity NPC233433
0.8447 Intermediate Similarity NPC473817

  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 NPC470591 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
0.913 High Similarity NPD8171 Discontinued
0.86 High Similarity NPD8170 Clinical (unspecified phase)
0.8131 Intermediate Similarity NPD8133 Approved
0.8018 Intermediate Similarity NPD8377 Approved
0.8018 Intermediate Similarity NPD8294 Approved
0.7946 Intermediate Similarity NPD8296 Approved
0.7946 Intermediate Similarity NPD8335 Approved
0.7946 Intermediate Similarity NPD8378 Approved
0.7946 Intermediate Similarity NPD8380 Approved
0.7946 Intermediate Similarity NPD8379 Approved
0.7826 Intermediate Similarity NPD6928 Phase 2
0.7788 Intermediate Similarity NPD8033 Approved
0.7522 Intermediate Similarity NPD7328 Approved
0.7522 Intermediate Similarity NPD7327 Approved
0.7456 Intermediate Similarity NPD7516 Approved
0.7273 Intermediate Similarity NPD8132 Clinical (unspecified phase)
0.7179 Intermediate Similarity NPD7503 Approved
0.713 Intermediate Similarity NPD8295 Clinical (unspecified phase)
0.7083 Intermediate Similarity NPD7507 Approved
0.7053 Intermediate Similarity NPD6114 Approved
0.7053 Intermediate Similarity NPD6697 Approved
0.7053 Intermediate Similarity NPD6115 Approved
0.7053 Intermediate Similarity NPD6118 Approved
0.7043 Intermediate Similarity NPD6940 Discontinued
0.7041 Intermediate Similarity NPD3670 Clinical (unspecified phase)
0.7041 Intermediate Similarity NPD3669 Approved
0.6952 Remote Similarity NPD7991 Discontinued
0.6947 Remote Similarity NPD6116 Phase 1
0.6937 Remote Similarity NPD6412 Phase 2
0.6923 Remote Similarity NPD4267 Clinical (unspecified phase)
0.6917 Remote Similarity NPD8328 Phase 3
0.6911 Remote Similarity NPD7319 Approved
0.6842 Remote Similarity NPD6117 Approved
0.6809 Remote Similarity NPD1810 Approved
0.6809 Remote Similarity NPD1811 Approved
0.6694 Remote Similarity NPD7736 Approved
0.6667 Remote Similarity NPD7532 Clinical (unspecified phase)
0.6632 Remote Similarity NPD6113 Clinical (unspecified phase)
0.6509 Remote Similarity NPD8035 Phase 2
0.6509 Remote Similarity NPD8034 Phase 2
0.6489 Remote Similarity NPD2687 Approved
0.6489 Remote Similarity NPD2686 Approved
0.6489 Remote Similarity NPD2254 Approved
0.648 Remote Similarity NPD8293 Discontinued
0.6435 Remote Similarity NPD8174 Phase 2
0.6435 Remote Similarity NPD6686 Approved
0.6434 Remote Similarity NPD8450 Suspended
0.6392 Remote Similarity NPD3702 Approved
0.6357 Remote Similarity NPD8449 Approved
0.6337 Remote Similarity NPD1780 Approved
0.6337 Remote Similarity NPD1779 Approved
0.6316 Remote Similarity NPD4787 Phase 1
0.6306 Remote Similarity NPD7638 Approved
0.629 Remote Similarity NPD6370 Approved
0.625 Remote Similarity NPD7520 Clinical (unspecified phase)
0.625 Remote Similarity NPD4808 Clinical (unspecified phase)
0.625 Remote Similarity NPD7640 Approved
0.625 Remote Similarity NPD7639 Approved
0.625 Remote Similarity NPD5777 Approved
0.625 Remote Similarity NPD4809 Clinical (unspecified phase)
0.6232 Remote Similarity NPD7625 Phase 1
0.6224 Remote Similarity NPD3703 Phase 2
0.6218 Remote Similarity NPD6882 Approved
0.6218 Remote Similarity NPD8297 Approved
0.619 Remote Similarity NPD7492 Approved
0.6148 Remote Similarity NPD6009 Approved
0.6146 Remote Similarity NPD4245 Approved
0.6146 Remote Similarity NPD4244 Approved
0.6142 Remote Similarity NPD6616 Approved
0.614 Remote Similarity NPD7632 Discontinued
0.6129 Remote Similarity NPD6054 Approved
0.6129 Remote Similarity NPD6319 Approved
0.6129 Remote Similarity NPD6059 Approved
0.6094 Remote Similarity NPD7078 Approved
0.608 Remote Similarity NPD8516 Approved
0.608 Remote Similarity NPD8515 Approved
0.608 Remote Similarity NPD8513 Phase 3
0.608 Remote Similarity NPD8517 Approved
0.6068 Remote Similarity NPD7646 Clinical (unspecified phase)
0.6053 Remote Similarity NPD1700 Approved
0.6044 Remote Similarity NPD6123 Approved
0.6042 Remote Similarity NPD3699 Clinical (unspecified phase)
0.6042 Remote Similarity NPD3700 Clinical (unspecified phase)
0.6042 Remote Similarity NPD3698 Phase 2
0.6034 Remote Similarity NPD4056 Clinical (unspecified phase)
0.6034 Remote Similarity NPD4057 Clinical (unspecified phase)
0.6033 Remote Similarity NPD4632 Approved
0.6022 Remote Similarity NPD371 Approved
0.6017 Remote Similarity NPD5345 Clinical (unspecified phase)
0.5984 Remote Similarity NPD6067 Discontinued
0.5983 Remote Similarity NPD6675 Approved
0.5983 Remote Similarity NPD7128 Approved
0.5983 Remote Similarity NPD5739 Approved
0.5983 Remote Similarity NPD6402 Approved
0.5966 Remote Similarity NPD6373 Approved
0.5966 Remote Similarity NPD6372 Approved
0.5965 Remote Similarity NPD8418 Phase 2
0.5952 Remote Similarity NPD6016 Approved
0.5952 Remote Similarity NPD6015 Approved
0.5922 Remote Similarity NPD7525 Registered
0.5918 Remote Similarity NPD6081 Approved
0.5906 Remote Similarity NPD5988 Approved
0.5882 Remote Similarity NPD6881 Approved
0.5882 Remote Similarity NPD6899 Approved
0.5882 Remote Similarity NPD7320 Approved
0.5868 Remote Similarity NPD6650 Approved
0.5868 Remote Similarity NPD8130 Phase 1
0.5868 Remote Similarity NPD6649 Approved
0.5833 Remote Similarity NPD4061 Clinical (unspecified phase)
0.5825 Remote Similarity NPD7329 Approved
0.5816 Remote Similarity NPD4789 Approved
0.5812 Remote Similarity NPD7912 Approved
0.5812 Remote Similarity NPD7987 Approved
0.5812 Remote Similarity NPD7911 Approved
0.5812 Remote Similarity NPD7986 Approved
0.5804 Remote Similarity NPD7748 Approved
0.5798 Remote Similarity NPD5701 Approved
0.5798 Remote Similarity NPD5697 Approved
0.5789 Remote Similarity NPD7902 Approved
0.5785 Remote Similarity NPD6883 Approved
0.5785 Remote Similarity NPD7290 Approved
0.5785 Remote Similarity NPD7102 Approved
0.5773 Remote Similarity NPD5360 Phase 3
0.5773 Remote Similarity NPD5361 Clinical (unspecified phase)
0.5738 Remote Similarity NPD6847 Approved
0.5738 Remote Similarity NPD6617 Approved
0.5738 Remote Similarity NPD8413 Clinical (unspecified phase)
0.5738 Remote Similarity NPD6869 Approved
0.5736 Remote Similarity NPD7604 Phase 2
0.5729 Remote Similarity NPD4224 Phase 2
0.5728 Remote Similarity NPD4238 Approved
0.5728 Remote Similarity NPD4802 Phase 2
0.5726 Remote Similarity NPD8085 Approved
0.5726 Remote Similarity NPD8083 Approved
0.5726 Remote Similarity NPD8138 Approved
0.5726 Remote Similarity NPD8086 Approved
0.5726 Remote Similarity NPD8139 Approved
0.5726 Remote Similarity NPD8084 Approved
0.5726 Remote Similarity NPD8082 Approved
0.5714 Remote Similarity NPD8040 Discontinued
0.5714 Remote Similarity NPD6399 Phase 3
0.5714 Remote Similarity NPD8393 Approved
0.5703 Remote Similarity NPD5983 Phase 2
0.5702 Remote Similarity NPD6013 Approved
0.5702 Remote Similarity NPD6012 Approved
0.5702 Remote Similarity NPD6014 Approved
0.5682 Remote Similarity NPD6033 Approved
0.5678 Remote Similarity NPD8275 Approved
0.5678 Remote Similarity NPD8276 Approved
0.5673 Remote Similarity NPD7645 Phase 2
0.5667 Remote Similarity NPD7990 Approved
0.5667 Remote Similarity NPD7989 Approved
0.5656 Remote Similarity NPD5955 Clinical (unspecified phase)
0.5652 Remote Similarity NPD6083 Phase 2
0.5652 Remote Similarity NPD6084 Phase 2
0.5649 Remote Similarity NPD6336 Discontinued
0.5635 Remote Similarity NPD7115 Discovery
0.563 Remote Similarity NPD8081 Approved
0.5625 Remote Similarity NPD7515 Phase 2
0.5625 Remote Similarity NPD3171 Clinical (unspecified phase)
0.562 Remote Similarity NPD6011 Approved
0.561 Remote Similarity NPD6401 Clinical (unspecified phase)

  Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity
B: biological targets similarity
C: networks similarity
D: cell-based bioactivity similarity
E: similarity based on clinical data