Structure

Physi-Chem Properties

Molecular Weight:  862.31
Volume:  792.031
LogP:  -1.727
LogD:  -0.931
LogS:  -2.092
# Rotatable Bonds:  16
TPSA:  346.06
# H-Bond Aceptor:  22
# H-Bond Donor:  13
# Rings:  6
# Heavy Atoms:  22

MedChem Properties

QED Drug-Likeness Score:  0.075
Synthetic Accessibility Score:  5.854
Fsp3:  0.684
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  1
Golden Triangle Rule:  Rejected
Chelating Alert:  1
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -6.843
MDCK Permeability:  8.576508116675541e-05
Pgp-inhibitor:  0.0
Pgp-substrate:  0.999
Human Intestinal Absorption (HIA):  0.994
20% Bioavailability (F20%):  0.976
30% Bioavailability (F30%):  1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.3
Plasma Protein Binding (PPB):  30.89899444580078%
Volume Distribution (VD):  0.314
Pgp-substrate:  23.52850341796875%

ADMET: Metabolism

CYP1A2-inhibitor:  0.001
CYP1A2-substrate:  0.124
CYP2C19-inhibitor:  0.002
CYP2C19-substrate:  0.118
CYP2C9-inhibitor:  0.0
CYP2C9-substrate:  0.028
CYP2D6-inhibitor:  0.0
CYP2D6-substrate:  0.118
CYP3A4-inhibitor:  0.022
CYP3A4-substrate:  0.015

ADMET: Excretion

Clearance (CL):  0.885
Half-life (T1/2):  0.798

ADMET: Toxicity

hERG Blockers:  0.64
Human Hepatotoxicity (H-HT):  0.195
Drug-inuced Liver Injury (DILI):  0.078
AMES Toxicity:  0.081
Rat Oral Acute Toxicity:  0.001
Maximum Recommended Daily Dose:  0.0
Skin Sensitization:  0.406
Carcinogencity:  0.056
Eye Corrosion:  0.003
Eye Irritation:  0.007
Respiratory Toxicity:  0.004

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

  Natural Product: NPC475224

Natural Product ID:  NPC475224
Common Name*:   4'-O-Beta-D-Glucosyl-9-O-(6' '-Deoxysaccharosyl)Olivil
IUPAC Name:   (2S,3R,4S,5S,6R)-2-[4-[[(3S,4R,5S)-4-[[(2R,3S,4S,5S)-3,4-dihydroxy-5-(hydroxymethyl)-5-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxolan-2-yl]methoxymethyl]-3-hydroxy-5-(4-hydroxy-3-methoxyphenyl)oxolan-3-yl]methyl]-2-methoxyphenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
Synonyms:  
Standard InCHIKey:  NVEGRZMDXHGAHQ-ZBBDYMFJSA-N
Standard InCHI:  InChI=1S/C38H54O22/c1-52-21-8-17(4-5-19(21)42)33-18(12-54-13-25-28(45)34(50)38(14-41,59-25)60-36-32(49)30(47)27(44)24(11-40)58-36)37(51,15-55-33)9-16-3-6-20(22(7-16)53-2)56-35-31(48)29(46)26(43)23(10-39)57-35/h3-8,18,23-36,39-51H,9-15H2,1-2H3/t18-,23-,24-,25-,26-,27-,28-,29+,30+,31-,32-,33-,34+,35-,36-,37-,38+/m1/s1
SMILES:  COC1=C(C=CC(=C1)CC2(COC(C2COCC3C(C(C(O3)(CO)OC4C(C(C(C(O4)CO)O)O)O)O)O)C5=CC(=C(C=C5)O)OC)O)OC6C(C(C(C(O6)CO)O)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL501388
PubChem CID:   21591949
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0001392] Lignans, neolignans and related compounds
      • [CHEMONTID:0001511] Lignan 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
NPO17333 Valeriana officinalis Species Caprifoliaceae Eukaryota roots n.a. n.a. PMID[12398547]
NPO17333 Valeriana officinalis Species Caprifoliaceae Eukaryota n.a. root n.a. PMID[18164718]
NPO17333 Valeriana officinalis Species Caprifoliaceae Eukaryota n.a. n.a. n.a. PMID[20853876]
NPO17333 Valeriana officinalis Species Caprifoliaceae Eukaryota n.a. n.a. n.a. PMID[28485933]
NPO17333 Valeriana officinalis Species Caprifoliaceae Eukaryota n.a. root n.a. PMID[547813]
NPO17333 Valeriana officinalis Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO17333 Valeriana officinalis Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO17333 Valeriana officinalis Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO17333 Valeriana officinalis Species Caprifoliaceae 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
NPT1315 Individual Protein Adenosine A1 receptor Rattus norvegicus EC50 = 3980.0 nM PMID[539018]
NPT1315 Individual Protein Adenosine A1 receptor Rattus norvegicus Activity = 126.0 % PMID[539018]
NPT1315 Individual Protein Adenosine A1 receptor Rattus norvegicus Ki = 5280.0 nM PMID[539018]
NPT216 Individual Protein Adenosine A1 receptor Homo sapiens Ki = 26.0 nM PMID[539018]
NPT216 Individual Protein Adenosine A1 receptor Homo sapiens Ki = 23600.0 nM PMID[539018]
NPT1315 Individual Protein Adenosine A1 receptor Rattus norvegicus Inhibition = 80.0 % PMID[539018]
NPT1316 Individual Protein Adenosine A2a receptor Rattus norvegicus Inhibition = 49.0 % PMID[539018]
NPT216 Individual Protein Adenosine A1 receptor Homo sapiens Ki = 31000.0 nM PMID[539018]

☑ 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 NPC475224 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
0.9718 High Similarity NPC112861
0.9718 High Similarity NPC276753
0.9718 High Similarity NPC205796
0.9648 High Similarity NPC22150
0.9648 High Similarity NPC18979
0.9648 High Similarity NPC38041
0.9648 High Similarity NPC279298
0.9577 High Similarity NPC470235
0.9577 High Similarity NPC129417
0.9577 High Similarity NPC471063
0.9577 High Similarity NPC283995
0.9577 High Similarity NPC84181
0.9507 High Similarity NPC113680
0.9507 High Similarity NPC278961
0.9507 High Similarity NPC477898
0.9507 High Similarity NPC185307
0.9507 High Similarity NPC470950
0.9507 High Similarity NPC46092
0.9452 High Similarity NPC98624
0.9437 High Similarity NPC476356
0.9437 High Similarity NPC246947
0.9384 High Similarity NPC35877
0.9384 High Similarity NPC55158
0.9384 High Similarity NPC95392
0.9384 High Similarity NPC51328
0.9384 High Similarity NPC55715
0.9384 High Similarity NPC286235
0.9375 High Similarity NPC469586
0.9366 High Similarity NPC472711
0.9315 High Similarity NPC130449
0.9315 High Similarity NPC304048
0.9315 High Similarity NPC248132
0.9315 High Similarity NPC226153
0.9296 High Similarity NPC106944
0.9247 High Similarity NPC15956
0.9247 High Similarity NPC31325
0.9247 High Similarity NPC39657
0.9247 High Similarity NPC114505
0.9247 High Similarity NPC213074
0.9247 High Similarity NPC275284
0.9247 High Similarity NPC224674
0.9247 High Similarity NPC193473
0.9225 High Similarity NPC156376
0.9205 High Similarity NPC11411
0.9178 High Similarity NPC241846
0.9178 High Similarity NPC93610
0.9167 High Similarity NPC302506
0.9155 High Similarity NPC138738
0.9155 High Similarity NPC470413
0.9155 High Similarity NPC304152
0.9122 High Similarity NPC44452
0.911 High Similarity NPC476301
0.911 High Similarity NPC43508
0.9097 High Similarity NPC471908
0.9091 High Similarity NPC7191
0.9091 High Similarity NPC149873
0.9085 High Similarity NPC52277
0.9085 High Similarity NPC177035
0.9085 High Similarity NPC199459
0.906 High Similarity NPC470934
0.906 High Similarity NPC188393
0.9041 High Similarity NPC187774
0.9041 High Similarity NPC217635
0.9041 High Similarity NPC472713
0.9041 High Similarity NPC79429
0.9041 High Similarity NPC473046
0.9041 High Similarity NPC472712
0.9041 High Similarity NPC118385
0.9041 High Similarity NPC179521
0.9041 High Similarity NPC471667
0.9028 High Similarity NPC55793
0.9014 High Similarity NPC142547
0.9014 High Similarity NPC101624
0.9014 High Similarity NPC184938
0.9014 High Similarity NPC135777
0.8986 High Similarity NPC99183
0.898 High Similarity NPC272619
0.898 High Similarity NPC286245
0.8958 High Similarity NPC193666
0.8958 High Similarity NPC123526
0.8958 High Similarity NPC88640
0.8944 High Similarity NPC470881
0.8944 High Similarity NPC187194
0.8944 High Similarity NPC35731
0.8944 High Similarity NPC476411
0.894 High Similarity NPC478268
0.8933 High Similarity NPC472710
0.8933 High Similarity NPC238140
0.8933 High Similarity NPC472709
0.8919 High Similarity NPC125755
0.8912 High Similarity NPC473045
0.8912 High Similarity NPC25292
0.8912 High Similarity NPC253015
0.8912 High Similarity NPC471065
0.8904 High Similarity NPC253878
0.8904 High Similarity NPC189115
0.8904 High Similarity NPC469559
0.8904 High Similarity NPC5262
0.8904 High Similarity NPC472714
0.8882 High Similarity NPC61604
0.8882 High Similarity NPC299706
0.8882 High Similarity NPC245615
0.8882 High Similarity NPC115466
0.8874 High Similarity NPC473621
0.8873 High Similarity NPC169973
0.8873 High Similarity NPC6836
0.8873 High Similarity NPC25821
0.8867 High Similarity NPC470098
0.8867 High Similarity NPC470826
0.8867 High Similarity NPC473266
0.8861 High Similarity NPC59516
0.8851 High Similarity NPC161700
0.8851 High Similarity NPC277867
0.8851 High Similarity NPC475096
0.8844 High Similarity NPC473044
0.8839 High Similarity NPC478269
0.8836 High Similarity NPC470372
0.8836 High Similarity NPC469661
0.8836 High Similarity NPC471414
0.8831 High Similarity NPC478055
0.8831 High Similarity NPC163635
0.8824 High Similarity NPC159922
0.8819 High Similarity NPC77861
0.8803 High Similarity NPC471505
0.8803 High Similarity NPC259742
0.8803 High Similarity NPC181049
0.8803 High Similarity NPC104077
0.8803 High Similarity NPC219671
0.8803 High Similarity NPC147616
0.8803 High Similarity NPC254275
0.8803 High Similarity NPC4940
0.8803 High Similarity NPC252833
0.8803 High Similarity NPC207400
0.8803 High Similarity NPC106739
0.88 High Similarity NPC301961
0.88 High Similarity NPC280945
0.88 High Similarity NPC116229
0.88 High Similarity NPC270751
0.88 High Similarity NPC166584
0.8792 High Similarity NPC99515
0.8792 High Similarity NPC190714
0.8792 High Similarity NPC476865
0.8784 High Similarity NPC470097
0.8784 High Similarity NPC469313
0.8784 High Similarity NPC76176
0.8784 High Similarity NPC114119
0.8784 High Similarity NPC138227
0.8784 High Similarity NPC168579
0.8784 High Similarity NPC471415
0.8776 High Similarity NPC60249
0.8776 High Similarity NPC48309
0.8767 High Similarity NPC226547
0.8767 High Similarity NPC177868
0.875 High Similarity NPC18576
0.875 High Similarity NPC324517
0.875 High Similarity NPC174191
0.875 High Similarity NPC329343
0.875 High Similarity NPC321972
0.875 High Similarity NPC93783
0.8742 High Similarity NPC259347
0.8742 High Similarity NPC476386
0.8742 High Similarity NPC470933
0.8742 High Similarity NPC471062
0.8742 High Similarity NPC476398
0.8742 High Similarity NPC94871
0.8742 High Similarity NPC473427
0.8742 High Similarity NPC306890
0.8733 High Similarity NPC15538
0.8733 High Similarity NPC473480
0.8733 High Similarity NPC327412
0.8733 High Similarity NPC320970
0.8733 High Similarity NPC328567
0.8733 High Similarity NPC320671
0.8733 High Similarity NPC227902
0.8732 High Similarity NPC9912
0.8732 High Similarity NPC27843
0.8732 High Similarity NPC115207
0.8732 High Similarity NPC228346
0.8732 High Similarity NPC161557
0.8732 High Similarity NPC158079
0.8732 High Similarity NPC248307
0.8732 High Similarity NPC40432
0.8732 High Similarity NPC277804
0.8732 High Similarity NPC476345
0.8732 High Similarity NPC65942
0.8732 High Similarity NPC7171
0.8726 High Similarity NPC478267
0.8725 High Similarity NPC476382
0.8725 High Similarity NPC34927
0.8725 High Similarity NPC287615
0.8725 High Similarity NPC216819
0.8725 High Similarity NPC100998
0.8725 High Similarity NPC252292
0.8725 High Similarity NPC262182
0.8725 High Similarity NPC83743
0.8725 High Similarity NPC476866
0.8725 High Similarity NPC34587
0.8725 High Similarity NPC476869
0.8725 High Similarity NPC476868
0.8725 High Similarity NPC476864

  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 NPC475224 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
0.8344 Intermediate Similarity NPD7228 Approved
0.8322 Intermediate Similarity NPD7266 Discontinued
0.8212 Intermediate Similarity NPD6674 Discontinued
0.8082 Intermediate Similarity NPD3027 Phase 3
0.8041 Intermediate Similarity NPD1613 Approved
0.8041 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.8025 Intermediate Similarity NPD6234 Discontinued
0.7929 Intermediate Similarity NPD7240 Approved
0.7917 Intermediate Similarity NPD7472 Approved
0.7917 Intermediate Similarity NPD7074 Phase 3
0.7901 Intermediate Similarity NPD4965 Approved
0.7901 Intermediate Similarity NPD4967 Phase 2
0.7901 Intermediate Similarity NPD4966 Approved
0.7857 Intermediate Similarity NPD7054 Approved
0.7824 Intermediate Similarity NPD7685 Pre-registration
0.7799 Intermediate Similarity NPD1653 Approved
0.7778 Intermediate Similarity NPD8455 Phase 2
0.7778 Intermediate Similarity NPD7808 Phase 3
0.7778 Intermediate Similarity NPD3705 Approved
0.777 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7746 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7719 Intermediate Similarity NPD7251 Discontinued
0.7716 Intermediate Similarity NPD37 Approved
0.7711 Intermediate Similarity NPD7199 Phase 2
0.7707 Intermediate Similarity NPD5058 Phase 3
0.7703 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7703 Intermediate Similarity NPD2861 Phase 2
0.7692 Intermediate Similarity NPD3818 Discontinued
0.7661 Intermediate Similarity NPD6797 Phase 2
0.7655 Intermediate Similarity NPD1091 Approved
0.7569 Intermediate Similarity NPD1357 Approved
0.7547 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7533 Intermediate Similarity NPD4908 Phase 1
0.7515 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD7680 Approved
0.7473 Intermediate Similarity NPD7237 Clinical (unspecified phase)
0.7451 Intermediate Similarity NPD3620 Phase 2
0.7451 Intermediate Similarity NPD3619 Clinical (unspecified phase)
0.7434 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7394 Intermediate Similarity NPD5283 Phase 1
0.7371 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.7368 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.7368 Intermediate Similarity NPD6166 Phase 2
0.7368 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.7349 Intermediate Similarity NPD2977 Approved
0.7349 Intermediate Similarity NPD2978 Approved
0.7341 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.733 Intermediate Similarity NPD8312 Approved
0.733 Intermediate Similarity NPD8313 Approved
0.7324 Intermediate Similarity NPD7843 Approved
0.7321 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.7308 Intermediate Similarity NPD7097 Phase 1
0.7297 Intermediate Similarity NPD1610 Phase 2
0.7296 Intermediate Similarity NPD5698 Clinical (unspecified phase)
0.7292 Intermediate Similarity NPD7157 Approved
0.729 Intermediate Similarity NPD5735 Approved
0.7289 Intermediate Similarity NPD1934 Approved
0.7278 Intermediate Similarity NPD1375 Discontinued
0.7262 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7261 Intermediate Similarity NPD5588 Approved
0.7254 Intermediate Similarity NPD228 Approved
0.7226 Intermediate Similarity NPD4060 Phase 1
0.7219 Intermediate Similarity NPD7975 Clinical (unspecified phase)
0.7216 Intermediate Similarity NPD6559 Discontinued
0.7208 Intermediate Similarity NPD6410 Clinical (unspecified phase)
0.7197 Intermediate Similarity NPD4538 Approved
0.7197 Intermediate Similarity NPD4536 Approved
0.7197 Intermediate Similarity NPD4537 Clinical (unspecified phase)
0.7193 Intermediate Similarity NPD8127 Discontinued
0.7191 Intermediate Similarity NPD7090 Clinical (unspecified phase)
0.7167 Intermediate Similarity NPD7906 Approved
0.7162 Intermediate Similarity NPD5125 Phase 3
0.7162 Intermediate Similarity NPD5126 Approved
0.7159 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7152 Intermediate Similarity NPD8651 Approved
0.7143 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD7095 Approved
0.7135 Intermediate Similarity NPD7310 Approved
0.7135 Intermediate Similarity NPD7311 Approved
0.7135 Intermediate Similarity NPD7313 Approved
0.7135 Intermediate Similarity NPD7312 Approved
0.7115 Intermediate Similarity NPD1558 Phase 1
0.7113 Intermediate Similarity NPD3021 Approved
0.7113 Intermediate Similarity NPD3022 Approved
0.7095 Intermediate Similarity NPD7309 Approved
0.7086 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.7086 Intermediate Similarity NPD4749 Approved
0.707 Intermediate Similarity NPD6355 Discontinued
0.7069 Intermediate Similarity NPD27 Approved
0.7069 Intermediate Similarity NPD2489 Approved
0.7066 Intermediate Similarity NPD7028 Phase 2
0.7063 Intermediate Similarity NPD5763 Approved
0.7063 Intermediate Similarity NPD5762 Approved
0.7055 Intermediate Similarity NPD6671 Approved
0.7044 Intermediate Similarity NPD6029 Clinical (unspecified phase)
0.7044 Intermediate Similarity NPD6028 Clinical (unspecified phase)
0.7044 Intermediate Similarity NPD4108 Discontinued
0.7044 Intermediate Similarity NPD5960 Phase 3
0.7042 Intermediate Similarity NPD2684 Approved
0.7037 Intermediate Similarity NPD4109 Clinical (unspecified phase)
0.7037 Intermediate Similarity NPD4110 Phase 3
0.7037 Intermediate Similarity NPD6331 Phase 2
0.7035 Intermediate Similarity NPD5494 Approved
0.7032 Intermediate Similarity NPD4625 Phase 3
0.7025 Intermediate Similarity NPD6653 Approved
0.7017 Intermediate Similarity NPD4663 Approved
0.7011 Intermediate Similarity NPD2970 Approved
0.7011 Intermediate Similarity NPD2969 Approved
0.7 Intermediate Similarity NPD6374 Clinical (unspecified phase)
0.6994 Remote Similarity NPD6190 Approved
0.6988 Remote Similarity NPD6980 Clinical (unspecified phase)
0.6982 Remote Similarity NPD7945 Clinical (unspecified phase)
0.6978 Remote Similarity NPD7243 Clinical (unspecified phase)
0.6975 Remote Similarity NPD4237 Approved
0.6975 Remote Similarity NPD4236 Phase 3
0.6974 Remote Similarity NPD2983 Phase 2
0.6974 Remote Similarity NPD2982 Phase 2
0.697 Remote Similarity NPD7004 Clinical (unspecified phase)
0.6959 Remote Similarity NPD3882 Suspended
0.6957 Remote Similarity NPD2029 Clinical (unspecified phase)
0.6954 Remote Similarity NPD3787 Discontinued
0.6954 Remote Similarity NPD3051 Approved
0.6951 Remote Similarity NPD6783 Clinical (unspecified phase)
0.6949 Remote Similarity NPD5844 Phase 1
0.6944 Remote Similarity NPD4577 Approved
0.6944 Remote Similarity NPD4578 Approved
0.6941 Remote Similarity NPD5772 Approved
0.6941 Remote Similarity NPD2801 Approved
0.6941 Remote Similarity NPD1465 Phase 2
0.6941 Remote Similarity NPD5773 Approved
0.694 Remote Similarity NPD8397 Clinical (unspecified phase)
0.6933 Remote Similarity NPD4628 Phase 3
0.6918 Remote Similarity NPD6353 Approved
0.6913 Remote Similarity NPD1548 Phase 1
0.6908 Remote Similarity NPD2981 Phase 2
0.6905 Remote Similarity NPD6055 Clinical (unspecified phase)
0.6903 Remote Similarity NPD3018 Phase 2
0.6899 Remote Similarity NPD4140 Approved
0.6894 Remote Similarity NPD2161 Phase 2
0.689 Remote Similarity NPD5084 Clinical (unspecified phase)
0.6871 Remote Similarity NPD3060 Approved
0.6871 Remote Similarity NPD5177 Phase 3
0.6865 Remote Similarity NPD7879 Clinical (unspecified phase)
0.6863 Remote Similarity NPD5327 Phase 3
0.6857 Remote Similarity NPD6071 Discontinued
0.6855 Remote Similarity NPD5123 Clinical (unspecified phase)
0.6855 Remote Similarity NPD5124 Phase 1
0.6845 Remote Similarity NPD4210 Discontinued
0.6842 Remote Similarity NPD6818 Clinical (unspecified phase)
0.6839 Remote Similarity NPD6584 Phase 3
0.6835 Remote Similarity NPD6233 Phase 2
0.6832 Remote Similarity NPD7033 Discontinued
0.6826 Remote Similarity NPD7527 Clinical (unspecified phase)
0.6826 Remote Similarity NPD7526 Approved
0.6826 Remote Similarity NPD52 Approved
0.6821 Remote Similarity NPD7833 Phase 2
0.6821 Remote Similarity NPD7831 Phase 2
0.6821 Remote Similarity NPD5846 Approved
0.6821 Remote Similarity NPD7832 Clinical (unspecified phase)
0.6821 Remote Similarity NPD6516 Phase 2
0.6818 Remote Similarity NPD6696 Suspended
0.6813 Remote Similarity NPD8054 Approved
0.6813 Remote Similarity NPD8053 Approved
0.6802 Remote Similarity NPD8443 Clinical (unspecified phase)
0.6802 Remote Similarity NPD2563 Approved
0.6802 Remote Similarity NPD2560 Approved
0.6802 Remote Similarity NPD3817 Phase 2
0.6798 Remote Similarity NPD3751 Discontinued
0.6796 Remote Similarity NPD7549 Discontinued
0.6793 Remote Similarity NPD6842 Approved
0.6793 Remote Similarity NPD6843 Phase 3
0.6793 Remote Similarity NPD6841 Approved
0.6792 Remote Similarity NPD2238 Phase 2
0.6788 Remote Similarity NPD2677 Approved
0.6786 Remote Similarity NPD2122 Discontinued
0.6784 Remote Similarity NPD3383 Approved
0.6784 Remote Similarity NPD3382 Approved
0.6784 Remote Similarity NPD3384 Approved
0.6774 Remote Similarity NPD3094 Phase 2
0.6772 Remote Similarity NPD6798 Discontinued
0.6768 Remote Similarity NPD4162 Approved
0.6766 Remote Similarity NPD1754 Clinical (unspecified phase)
0.6766 Remote Similarity NPD4123 Phase 3
0.6766 Remote Similarity NPD4160 Clinical (unspecified phase)
0.6765 Remote Similarity NPD4380 Phase 2
0.6753 Remote Similarity NPD3600 Clinical (unspecified phase)
0.6753 Remote Similarity NPD3685 Discontinued
0.6752 Remote Similarity NPD5752 Clinical (unspecified phase)
0.6748 Remote Similarity NPD6002 Phase 3
0.6748 Remote Similarity NPD6006 Clinical (unspecified phase)
0.6748 Remote Similarity NPD6003 Clinical (unspecified phase)
0.6748 Remote Similarity NPD6004 Phase 3
0.6748 Remote Similarity NPD6005 Phase 3
0.6746 Remote Similarity NPD3687 Approved
0.6746 Remote Similarity NPD3686 Approved
0.6744 Remote Similarity NPD5563 Clinical (unspecified phase)
0.6739 Remote Similarity NPD8434 Phase 2
0.6736 Remote Similarity NPD290 Approved
0.673 Remote Similarity NPD1726 Clinical (unspecified phase)
0.6727 Remote Similarity NPD6658 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