Structure

Physi-Chem Properties

Molecular Weight:  600.35
Volume:  655.318
LogP:  8.237
LogD:  5.266
LogS:  -4.624
# Rotatable Bonds:  8
TPSA:  100.9
# H-Bond Aceptor:  6
# H-Bond Donor:  2
# Rings:  4
# Heavy Atoms:  6

MedChem Properties

QED Drug-Likeness Score:  0.102
Synthetic Accessibility Score:  6.302
Fsp3:  0.5
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  2
PAINS Alert:  1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.901
MDCK Permeability:  1.4613457096857019e-05
Pgp-inhibitor:  0.916
Pgp-substrate:  0.99
Human Intestinal Absorption (HIA):  0.102
20% Bioavailability (F20%):  0.973
30% Bioavailability (F30%):  0.851

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.019
Plasma Protein Binding (PPB):  90.04169464111328%
Volume Distribution (VD):  1.325
Pgp-substrate:  9.045564651489258%

ADMET: Metabolism

CYP1A2-inhibitor:  0.114
CYP1A2-substrate:  0.244
CYP2C19-inhibitor:  0.903
CYP2C19-substrate:  0.175
CYP2C9-inhibitor:  0.929
CYP2C9-substrate:  0.816
CYP2D6-inhibitor:  0.931
CYP2D6-substrate:  0.031
CYP3A4-inhibitor:  0.918
CYP3A4-substrate:  0.598

ADMET: Excretion

Clearance (CL):  15.555
Half-life (T1/2):  0.038

ADMET: Toxicity

hERG Blockers:  0.011
Human Hepatotoxicity (H-HT):  0.973
Drug-inuced Liver Injury (DILI):  0.89
AMES Toxicity:  0.05
Rat Oral Acute Toxicity:  0.719
Maximum Recommended Daily Dose:  0.727
Skin Sensitization:  0.037
Carcinogencity:  0.298
Eye Corrosion:  0.003
Eye Irritation:  0.056
Respiratory Toxicity:  0.933

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

  Natural Product: NPC46549

Natural Product ID:  NPC46549
Common Name*:   Garcinialiptone B
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  AFHKVDYTQYGRHC-JVFVNDAQSA-N
Standard InCHI:  InChI=1S/C38H48O6/c1-21(2)11-13-26-19-37-20-27(24(7)8)30(17-23(5)6)44-34(37)31(32(41)25-12-14-28(39)29(40)18-25)33(42)38(35(37)43,36(26,9)10)16-15-22(3)4/h11-12,14-15,17-18,26-27,30,39-40H,7,13,16,19-20H2,1-6,8-10H3/t26-,27-,30-,37+,38+/m0/s1
SMILES:  CC(=CC[C@@]12C(=O)C(=C3[C@](C1=O)(C[C@H]([C@@H](O3)C=C(C)C)C(=C)C)C[C@@H](C2(C)C)CC=C(C)C)C(=O)c1ccc(c(c1)O)O)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1077025
PubChem CID:   46184557
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001549] Monoterpenoids
          • [CHEMONTID:0000051] Aromatic monoterpenoids

*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
NPO25472 Garcinia cowa Species Clusiaceae Eukaryota n.a. n.a. n.a. DOI[10.1071/CH03175]
NPO7006 Garcinia subelliptica Species Clusiaceae Eukaryota n.a. n.a. n.a. PMID[15568764]
NPO7006 Garcinia subelliptica Species Clusiaceae Eukaryota pericarp n.a. n.a. PMID[16038565]
NPO7006 Garcinia subelliptica Species Clusiaceae Eukaryota n.a. n.a. n.a. PMID[18166016]
NPO25472 Garcinia cowa Species Clusiaceae Eukaryota n.a. n.a. n.a. PMID[19299148]
NPO25472 Garcinia cowa Species Clusiaceae Eukaryota twigs n.a. n.a. PMID[20058933]
NPO7006 Garcinia subelliptica Species Clusiaceae Eukaryota n.a. n.a. n.a. PMID[20232858]
NPO15264 Garcinia paucinervis Species Clusiaceae Eukaryota n.a. n.a. n.a. PMID[20594858]
NPO32711 garcinia esculenta Species Clusiaceae Eukaryota twigs n.a. n.a. PMID[24960143]
NPO25472 Garcinia cowa Species Clusiaceae Eukaryota flowers Pakook, Muang District, Chiang Rai Province, Thailand 2013-Feb PMID[25651042]
NPO25472 Garcinia cowa Species Clusiaceae Eukaryota young fruits Khokkhon, Tha Bo District, Nong Khai Province, Thailand 2011-Aug PMID[25651042]
NPO25472 Garcinia cowa Species Clusiaceae Eukaryota Leaves n.a. n.a. PMID[31860303]
NPO7006 Garcinia subelliptica Species Clusiaceae Eukaryota n.a. xylem n.a. Database[Article]
NPO25472 Garcinia cowa Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO7006 Garcinia subelliptica Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25472 Garcinia cowa Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7006 Garcinia subelliptica Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15264 Garcinia paucinervis Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25472 Garcinia cowa Species Clusiaceae 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
NPT139 Cell Line HT-29 Homo sapiens Activity = 73.8 % PMID[540130]
NPT81 Cell Line A549 Homo sapiens IC50 = 6.7 ug.mL-1 PMID[540131]
NPT90 Cell Line DU-145 Homo sapiens IC50 = 7.3 ug.mL-1 PMID[540131]
NPT91 Cell Line KB Homo sapiens IC50 = 5.7 ug.mL-1 PMID[540131]
NPT91 Cell Line KB Homo sapiens IC50 = 6.6 ug.mL-1 PMID[540131]
NPT65 Cell Line HepG2 Homo sapiens IC50 > 10000.0 nM PMID[540134]
NPT83 Cell Line MCF7 Homo sapiens IC50 > 10000.0 nM PMID[540134]
NPT82 Cell Line MDA-MB-231 Homo sapiens IC50 > 10000.0 nM PMID[540134]
NPT113 Cell Line RAW264.7 Mus musculus IC50 = 21300.0 nM PMID[540134]
NPT27 Others Unspecified IC50 > 10000.0 nM PMID[540134]

☑ 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 NPC46549 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 NPC264229
0.9577 High Similarity NPC144247
0.9577 High Similarity NPC145301
0.9577 High Similarity NPC294679
0.9577 High Similarity NPC469375
0.9577 High Similarity NPC8493
0.9448 High Similarity NPC132810
0.9437 High Similarity NPC30846
0.9437 High Similarity NPC471972
0.9437 High Similarity NPC469855
0.9437 High Similarity NPC471971
0.9392 High Similarity NPC305710
0.931 High Similarity NPC273798
0.931 High Similarity NPC471970
0.9306 High Similarity NPC469854
0.9306 High Similarity NPC469856
0.9291 High Similarity NPC297797
0.9291 High Similarity NPC289358
0.9291 High Similarity NPC46242
0.9291 High Similarity NPC50615
0.9291 High Similarity NPC473479
0.9291 High Similarity NPC51531
0.9291 High Similarity NPC5014
0.9291 High Similarity NPC165191
0.9291 High Similarity NPC149773
0.9291 High Similarity NPC245760
0.9291 High Similarity NPC42384
0.9291 High Similarity NPC91887
0.9291 High Similarity NPC28592
0.9291 High Similarity NPC473779
0.9291 High Similarity NPC469857
0.9291 High Similarity NPC23667
0.9291 High Similarity NPC114333
0.9291 High Similarity NPC157284
0.9291 High Similarity NPC477849
0.9252 High Similarity NPC237441
0.9225 High Similarity NPC294330
0.9161 High Similarity NPC473527
0.9149 High Similarity NPC7464
0.9021 High Similarity NPC469681
0.9021 High Similarity NPC469680
0.9021 High Similarity NPC471974
0.8951 High Similarity NPC118366
0.8889 High Similarity NPC471968
0.869 High Similarity NPC471152
0.8652 High Similarity NPC25736
0.8528 High Similarity NPC471969
0.8523 High Similarity NPC477873
0.8523 High Similarity NPC469447
0.8442 Intermediate Similarity NPC48949
0.8411 Intermediate Similarity NPC53520
0.84 Intermediate Similarity NPC229218
0.84 Intermediate Similarity NPC141817
0.84 Intermediate Similarity NPC169214
0.84 Intermediate Similarity NPC192597
0.84 Intermediate Similarity NPC176030
0.8395 Intermediate Similarity NPC478059
0.8395 Intermediate Similarity NPC471975
0.8395 Intermediate Similarity NPC478060
0.8395 Intermediate Similarity NPC470374
0.8395 Intermediate Similarity NPC470377
0.8389 Intermediate Similarity NPC470035
0.8366 Intermediate Similarity NPC52692
0.8355 Intermediate Similarity NPC258856
0.8355 Intermediate Similarity NPC470038
0.8344 Intermediate Similarity NPC199936
0.8311 Intermediate Similarity NPC277559
0.8288 Intermediate Similarity NPC474715
0.8288 Intermediate Similarity NPC4170
0.8288 Intermediate Similarity NPC138472
0.8278 Intermediate Similarity NPC184935
0.8269 Intermediate Similarity NPC144283
0.8235 Intermediate Similarity NPC8102
0.8235 Intermediate Similarity NPC66894
0.8235 Intermediate Similarity NPC75295
0.8224 Intermediate Similarity NPC224884
0.8224 Intermediate Similarity NPC46161
0.8224 Intermediate Similarity NPC209085
0.8224 Intermediate Similarity NPC239608
0.8221 Intermediate Similarity NPC263212
0.8212 Intermediate Similarity NPC472410
0.821 Intermediate Similarity NPC100420
0.8205 Intermediate Similarity NPC470037
0.8205 Intermediate Similarity NPC473680
0.8205 Intermediate Similarity NPC473579
0.8205 Intermediate Similarity NPC475454
0.8205 Intermediate Similarity NPC118033
0.8205 Intermediate Similarity NPC475311
0.8199 Intermediate Similarity NPC266365
0.8188 Intermediate Similarity NPC49911
0.8188 Intermediate Similarity NPC119542
0.8182 Intermediate Similarity NPC472803
0.8176 Intermediate Similarity NPC43353
0.817 Intermediate Similarity NPC309169
0.817 Intermediate Similarity NPC196941
0.8163 Intermediate Similarity NPC111845
0.8158 Intermediate Similarity NPC248068
0.8153 Intermediate Similarity NPC473773
0.8153 Intermediate Similarity NPC475579
0.8146 Intermediate Similarity NPC27518
0.8146 Intermediate Similarity NPC471853
0.8146 Intermediate Similarity NPC476534
0.8146 Intermediate Similarity NPC304110
0.8141 Intermediate Similarity NPC327962
0.8138 Intermediate Similarity NPC470747
0.8133 Intermediate Similarity NPC230811
0.8133 Intermediate Similarity NPC182249
0.8129 Intermediate Similarity NPC476821
0.8117 Intermediate Similarity NPC160777
0.8117 Intermediate Similarity NPC73416
0.8113 Intermediate Similarity NPC472807
0.811 Intermediate Similarity NPC200726
0.8108 Intermediate Similarity NPC194970
0.8105 Intermediate Similarity NPC25491
0.8101 Intermediate Similarity NPC164912
0.8092 Intermediate Similarity NPC84273
0.8082 Intermediate Similarity NPC117609
0.8079 Intermediate Similarity NPC473591
0.8079 Intermediate Similarity NPC271494
0.8079 Intermediate Similarity NPC155192
0.8069 Intermediate Similarity NPC234175
0.8067 Intermediate Similarity NPC264022
0.8067 Intermediate Similarity NPC475957
0.8065 Intermediate Similarity NPC143685
0.8061 Intermediate Similarity NPC177362
0.8054 Intermediate Similarity NPC477874
0.8054 Intermediate Similarity NPC153088
0.8054 Intermediate Similarity NPC173569
0.805 Intermediate Similarity NPC62051
0.8041 Intermediate Similarity NPC59459
0.8041 Intermediate Similarity NPC327410
0.8041 Intermediate Similarity NPC294226
0.8039 Intermediate Similarity NPC11314
0.8038 Intermediate Similarity NPC221249
0.8038 Intermediate Similarity NPC124842
0.8038 Intermediate Similarity NPC118427
0.8026 Intermediate Similarity NPC82336
0.8026 Intermediate Similarity NPC472801
0.8026 Intermediate Similarity NPC172311
0.8026 Intermediate Similarity NPC78987
0.8025 Intermediate Similarity NPC185617
0.8025 Intermediate Similarity NPC474310
0.8013 Intermediate Similarity NPC325032
0.8013 Intermediate Similarity NPC10842
0.8013 Intermediate Similarity NPC477483
0.8012 Intermediate Similarity NPC476017
0.8012 Intermediate Similarity NPC266545
0.8012 Intermediate Similarity NPC202428
0.8 Intermediate Similarity NPC470733
0.8 Intermediate Similarity NPC84786
0.8 Intermediate Similarity NPC249817
0.8 Intermediate Similarity NPC316553
0.8 Intermediate Similarity NPC225351
0.8 Intermediate Similarity NPC324929
0.7988 Intermediate Similarity NPC476295
0.7988 Intermediate Similarity NPC475054
0.7987 Intermediate Similarity NPC205392
0.7987 Intermediate Similarity NPC469615
0.7987 Intermediate Similarity NPC105942
0.7975 Intermediate Similarity NPC475718
0.7975 Intermediate Similarity NPC295977
0.7975 Intermediate Similarity NPC58310
0.7975 Intermediate Similarity NPC472275
0.7975 Intermediate Similarity NPC472906
0.7973 Intermediate Similarity NPC50763
0.7973 Intermediate Similarity NPC477407
0.7964 Intermediate Similarity NPC475058
0.7963 Intermediate Similarity NPC210459
0.7963 Intermediate Similarity NPC197856
0.7962 Intermediate Similarity NPC473719
0.7962 Intermediate Similarity NPC474903
0.7961 Intermediate Similarity NPC474784
0.795 Intermediate Similarity NPC478223
0.7949 Intermediate Similarity NPC474991
0.7947 Intermediate Similarity NPC198621
0.7947 Intermediate Similarity NPC216940
0.7947 Intermediate Similarity NPC475482
0.7947 Intermediate Similarity NPC22676
0.7941 Intermediate Similarity NPC469418
0.7939 Intermediate Similarity NPC472277
0.7937 Intermediate Similarity NPC475770
0.7937 Intermediate Similarity NPC25127
0.7935 Intermediate Similarity NPC469683
0.7935 Intermediate Similarity NPC307205
0.7935 Intermediate Similarity NPC280717
0.7935 Intermediate Similarity NPC79627
0.7935 Intermediate Similarity NPC271607
0.7933 Intermediate Similarity NPC89504
0.7933 Intermediate Similarity NPC258502
0.7933 Intermediate Similarity NPC95485
0.7933 Intermediate Similarity NPC88065
0.7927 Intermediate Similarity NPC201800
0.7925 Intermediate Similarity NPC227485
0.7925 Intermediate Similarity NPC473201
0.7925 Intermediate Similarity NPC306011
0.7925 Intermediate Similarity NPC302783
0.7925 Intermediate Similarity NPC472838
0.7922 Intermediate Similarity NPC235557
0.7922 Intermediate Similarity NPC285550
0.7919 Intermediate Similarity NPC477139

  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 NPC46549 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
0.8581 High Similarity NPD8166 Discontinued
0.7826 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7669 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.7654 Intermediate Similarity NPD1934 Approved
0.7557 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7547 Intermediate Similarity NPD7422 Clinical (unspecified phase)
0.7517 Intermediate Similarity NPD9494 Approved
0.7516 Intermediate Similarity NPD4628 Phase 3
0.75 Intermediate Similarity NPD943 Approved
0.7486 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7469 Intermediate Similarity NPD7458 Discontinued
0.7448 Intermediate Similarity NPD2932 Approved
0.7423 Intermediate Similarity NPD4380 Phase 2
0.7415 Intermediate Similarity NPD3972 Approved
0.7412 Intermediate Similarity NPD6166 Phase 2
0.7412 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.7412 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.741 Intermediate Similarity NPD3882 Suspended
0.741 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7394 Intermediate Similarity NPD2801 Approved
0.7394 Intermediate Similarity NPD7819 Suspended
0.7391 Intermediate Similarity NPD6273 Approved
0.7381 Intermediate Similarity NPD5494 Approved
0.7368 Intermediate Similarity NPD7473 Discontinued
0.7365 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.7345 Intermediate Similarity NPD8434 Phase 2
0.7345 Intermediate Similarity NPD8150 Discontinued
0.7341 Intermediate Similarity NPD7074 Phase 3
0.7338 Intermediate Similarity NPD230 Phase 1
0.7329 Intermediate Similarity NPD3019 Approved
0.732 Intermediate Similarity NPD6663 Approved
0.7285 Intermediate Similarity NPD5736 Approved
0.7283 Intermediate Similarity NPD7054 Approved
0.7267 Intermediate Similarity NPD1511 Approved
0.7267 Intermediate Similarity NPD1470 Approved
0.7262 Intermediate Similarity NPD7075 Discontinued
0.7257 Intermediate Similarity NPD7685 Pre-registration
0.725 Intermediate Similarity NPD6190 Approved
0.7241 Intermediate Similarity NPD7472 Approved
0.7235 Intermediate Similarity NPD8127 Discontinued
0.7233 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7225 Intermediate Similarity NPD3818 Discontinued
0.7215 Intermediate Similarity NPD2346 Discontinued
0.7215 Intermediate Similarity NPD2344 Approved
0.7212 Intermediate Similarity NPD7028 Phase 2
0.7211 Intermediate Similarity NPD3412 Clinical (unspecified phase)
0.7205 Intermediate Similarity NPD3300 Phase 2
0.7197 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.7197 Intermediate Similarity NPD2799 Discontinued
0.7197 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.7193 Intermediate Similarity NPD6232 Discontinued
0.7188 Intermediate Similarity NPD7003 Approved
0.7186 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.7184 Intermediate Similarity NPD5844 Phase 1
0.7178 Intermediate Similarity NPD1512 Approved
0.7175 Intermediate Similarity NPD3534 Clinical (unspecified phase)
0.717 Intermediate Similarity NPD1549 Phase 2
0.7169 Intermediate Similarity NPD7411 Suspended
0.7161 Intermediate Similarity NPD3619 Clinical (unspecified phase)
0.7161 Intermediate Similarity NPD3620 Phase 2
0.7159 Intermediate Similarity NPD7251 Discontinued
0.7152 Intermediate Similarity NPD3226 Approved
0.7152 Intermediate Similarity NPD2935 Discontinued
0.7135 Intermediate Similarity NPD6959 Discontinued
0.7119 Intermediate Similarity NPD7808 Phase 3
0.7114 Intermediate Similarity NPD1201 Approved
0.711 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.7107 Intermediate Similarity NPD1471 Phase 3
0.7107 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.7107 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.7107 Intermediate Similarity NPD7266 Discontinued
0.7102 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7102 Intermediate Similarity NPD6797 Phase 2
0.7099 Intermediate Similarity NPD7236 Approved
0.7089 Intermediate Similarity NPD3299 Clinical (unspecified phase)
0.7089 Intermediate Similarity NPD1510 Phase 2
0.7088 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7081 Intermediate Similarity NPD4109 Clinical (unspecified phase)
0.7081 Intermediate Similarity NPD4110 Phase 3
0.7079 Intermediate Similarity NPD8312 Approved
0.7079 Intermediate Similarity NPD8313 Approved
0.7059 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.7055 Intermediate Similarity NPD405 Clinical (unspecified phase)
0.7048 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7048 Intermediate Similarity NPD3455 Phase 2
0.7044 Intermediate Similarity NPD6099 Approved
0.7044 Intermediate Similarity NPD6100 Approved
0.7042 Intermediate Similarity NPD3021 Approved
0.7042 Intermediate Similarity NPD3022 Approved
0.7037 Intermediate Similarity NPD2309 Approved
0.7032 Intermediate Similarity NPD3764 Approved
0.7027 Intermediate Similarity NPD4196 Clinical (unspecified phase)
0.7022 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.7012 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.7006 Intermediate Similarity NPD6599 Discontinued
0.6993 Remote Similarity NPD2798 Approved
0.6989 Remote Similarity NPD7804 Clinical (unspecified phase)
0.6987 Remote Similarity NPD8032 Phase 2
0.6982 Remote Similarity NPD1465 Phase 2
0.6975 Remote Similarity NPD6398 Clinical (unspecified phase)
0.6974 Remote Similarity NPD1876 Approved
0.6962 Remote Similarity NPD1607 Approved
0.6962 Remote Similarity NPD6651 Approved
0.6959 Remote Similarity NPD9545 Approved
0.6957 Remote Similarity NPD970 Clinical (unspecified phase)
0.6951 Remote Similarity NPD6143 Clinical (unspecified phase)
0.6951 Remote Similarity NPD7390 Discontinued
0.6943 Remote Similarity NPD1240 Approved
0.6941 Remote Similarity NPD3817 Phase 2
0.6937 Remote Similarity NPD5408 Approved
0.6937 Remote Similarity NPD5405 Approved
0.6937 Remote Similarity NPD2796 Approved
0.6937 Remote Similarity NPD5404 Approved
0.6937 Remote Similarity NPD5406 Approved
0.6933 Remote Similarity NPD3026 Approved
0.6933 Remote Similarity NPD3023 Approved
0.6932 Remote Similarity NPD7228 Approved
0.6919 Remote Similarity NPD6234 Discontinued
0.6915 Remote Similarity NPD7501 Clinical (unspecified phase)
0.6914 Remote Similarity NPD2800 Approved
0.6913 Remote Similarity NPD3025 Approved
0.6913 Remote Similarity NPD3024 Approved
0.6909 Remote Similarity NPD2532 Approved
0.6909 Remote Similarity NPD2534 Approved
0.6909 Remote Similarity NPD7004 Clinical (unspecified phase)
0.6909 Remote Similarity NPD7410 Clinical (unspecified phase)
0.6909 Remote Similarity NPD2533 Approved
0.6901 Remote Similarity NPD7768 Phase 2
0.6892 Remote Similarity NPD5536 Phase 2
0.6887 Remote Similarity NPD3092 Approved
0.6887 Remote Similarity NPD1547 Clinical (unspecified phase)
0.6886 Remote Similarity NPD7239 Suspended
0.6882 Remote Similarity NPD5761 Phase 2
0.6882 Remote Similarity NPD5760 Phase 2
0.6871 Remote Similarity NPD3750 Approved
0.6863 Remote Similarity NPD1283 Approved
0.6859 Remote Similarity NPD5952 Clinical (unspecified phase)
0.6846 Remote Similarity NPD3091 Approved
0.6842 Remote Similarity NPD5978 Approved
0.6842 Remote Similarity NPD9269 Phase 2
0.6842 Remote Similarity NPD5977 Approved
0.6828 Remote Similarity NPD1609 Clinical (unspecified phase)
0.6824 Remote Similarity NPD7577 Discontinued
0.6824 Remote Similarity NPD6844 Discontinued
0.6824 Remote Similarity NPD6801 Discontinued
0.6818 Remote Similarity NPD3094 Phase 2
0.6815 Remote Similarity NPD2313 Discontinued
0.6815 Remote Similarity NPD3268 Approved
0.68 Remote Similarity NPD1651 Approved
0.6792 Remote Similarity NPD5735 Approved
0.6792 Remote Similarity NPD6355 Discontinued
0.6792 Remote Similarity NPD447 Suspended
0.6778 Remote Similarity NPD6559 Discontinued
0.6765 Remote Similarity NPD6873 Phase 2
0.6763 Remote Similarity NPD3749 Approved
0.6757 Remote Similarity NPD2490 Approved
0.6757 Remote Similarity NPD2488 Approved
0.6754 Remote Similarity NPD2491 Approved
0.6752 Remote Similarity NPD7095 Approved
0.6752 Remote Similarity NPD7008 Discontinued
0.6747 Remote Similarity NPD6799 Approved
0.6742 Remote Similarity NPD7893 Clinical (unspecified phase)
0.6742 Remote Similarity NPD3751 Discontinued
0.6735 Remote Similarity NPD1241 Discontinued
0.673 Remote Similarity NPD4060 Phase 1
0.673 Remote Similarity NPD2979 Phase 3
0.673 Remote Similarity NPD4140 Approved
0.6728 Remote Similarity NPD2438 Suspended
0.6727 Remote Similarity NPD7910 Clinical (unspecified phase)
0.6726 Remote Similarity NPD6980 Clinical (unspecified phase)
0.6725 Remote Similarity NPD37 Approved
0.6724 Remote Similarity NPD5537 Clinical (unspecified phase)
0.672 Remote Similarity NPD7700 Phase 2
0.672 Remote Similarity NPD7699 Phase 2
0.6711 Remote Similarity NPD7457 Clinical (unspecified phase)
0.6707 Remote Similarity NPD4160 Clinical (unspecified phase)
0.6705 Remote Similarity NPD4965 Approved
0.6705 Remote Similarity NPD4967 Phase 2
0.6705 Remote Similarity NPD4966 Approved
0.6689 Remote Similarity NPD2629 Approved
0.6688 Remote Similarity NPD5327 Phase 3
0.6685 Remote Similarity NPD8368 Discontinued
0.6684 Remote Similarity NPD8320 Phase 1
0.6684 Remote Similarity NPD8319 Approved
0.6683 Remote Similarity NPD7907 Approved
0.6667 Remote Similarity NPD3926 Phase 2
0.6667 Remote Similarity NPD6385 Approved
0.6667 Remote Similarity NPD3448 Approved
0.6667 Remote Similarity NPD3057 Approved
0.6667 Remote Similarity NPD1281 Approved
0.6667 Remote Similarity NPD6386 Approved
0.6649 Remote Similarity NPD6534 Approved
0.6649 Remote Similarity NPD6782 Approved
0.6649 Remote Similarity NPD6778 Approved
0.6649 Remote Similarity NPD6781 Approved
0.6649 Remote Similarity NPD6780 Approved
0.6649 Remote Similarity NPD6776 Approved
0.6649 Remote Similarity NPD6777 Approved
0.6649 Remote Similarity NPD6535 Approved
0.6649 Remote Similarity NPD6779 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