Structure

Physi-Chem Properties

Molecular Weight:  476.18
Volume:  485.229
LogP:  7.954
LogD:  5.656
LogS:  -1.629
# Rotatable Bonds:  2
TPSA:  94.45
# H-Bond Aceptor:  7
# H-Bond Donor:  2
# Rings:  5
# Heavy Atoms:  7

MedChem Properties

QED Drug-Likeness Score:  0.298
Synthetic Accessibility Score:  3.769
Fsp3:  0.321
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  1
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.065
MDCK Permeability:  1.7621261577005498e-05
Pgp-inhibitor:  0.998
Pgp-substrate:  0.0
Human Intestinal Absorption (HIA):  0.88
20% Bioavailability (F20%):  0.966
30% Bioavailability (F30%):  0.06

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.003
Plasma Protein Binding (PPB):  101.30928802490234%
Volume Distribution (VD):  0.867
Pgp-substrate:  3.831611156463623%

ADMET: Metabolism

CYP1A2-inhibitor:  0.311
CYP1A2-substrate:  0.165
CYP2C19-inhibitor:  0.776
CYP2C19-substrate:  0.133
CYP2C9-inhibitor:  0.779
CYP2C9-substrate:  0.915
CYP2D6-inhibitor:  0.051
CYP2D6-substrate:  0.145
CYP3A4-inhibitor:  0.432
CYP3A4-substrate:  0.208

ADMET: Excretion

Clearance (CL):  2.14
Half-life (T1/2):  0.097

ADMET: Toxicity

hERG Blockers:  0.023
Human Hepatotoxicity (H-HT):  0.736
Drug-inuced Liver Injury (DILI):  0.238
AMES Toxicity:  0.014
Rat Oral Acute Toxicity:  1.0
Maximum Recommended Daily Dose:  0.767
Skin Sensitization:  0.791
Carcinogencity:  0.868
Eye Corrosion:  0.003
Eye Irritation:  0.29
Respiratory Toxicity:  0.821

Download Data

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

  Natural Product: NPC85057

Natural Product ID:  NPC85057
Common Name*:   Garcinisidone C
IUPAC Name:   n.a.
Synonyms:   Garcinisidone C
Standard InCHIKey:  REAWMYXWSLIYTD-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C28H28O7/c1-14(2)7-8-16-22-15(9-11-27(3,4)34-22)21(30)20-25(16)32-19-13-18(29)23-17(24(19)33-26(20)31)10-12-28(5,6)35-23/h7,9-13,29-30H,8H2,1-6H3
SMILES:  CC(=CCc1c2Oc3cc(O)c4c(c3OC(=O)c2c(c2c1OC(C)(C)C=C2)O)C=CC(O4)(C)C)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL460040
PubChem CID:   10390233
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0000123] Benzopyrans
        • [CHEMONTID:0003410] 1-benzopyrans
          • [CHEMONTID:0003522] 2,2-dimethyl-1-benzopyrans

*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
NPO32536 Garcinia Genus Clusiaceae Eukaryota n.a. n.a. n.a. PMID[11429990]

☑ 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
NPT80 Cell Line Raji Homo sapiens Activity = 70.0 % PMID[493322]
NPT80 Cell Line Raji Homo sapiens Activity > 80.0 % PMID[493322]
NPT2 Others Unspecified Activity = 0.0 % PMID[493322]
NPT2 Others Unspecified Activity = 41.8 % PMID[493322]
NPT2 Others Unspecified Activity = 72.2 % PMID[493322]
NPT2 Others Unspecified Activity = 93.5 % PMID[493322]
NPT2 Others Unspecified IC50 = 370.0 molar ratio PMID[493322]

☑ 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 NPC85057 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 NPC130920
0.9871 High Similarity NPC8300
0.9808 High Similarity NPC234004
0.9551 High Similarity NPC168616
0.9551 High Similarity NPC83763
0.943 High Similarity NPC259456
0.9423 High Similarity NPC472456
0.9423 High Similarity NPC471985
0.9423 High Similarity NPC276444
0.9367 High Similarity NPC204290
0.9363 High Similarity NPC218871
0.9363 High Similarity NPC476630
0.9308 High Similarity NPC29876
0.9308 High Similarity NPC167678
0.9295 High Similarity NPC170492
0.925 High Similarity NPC261470
0.925 High Similarity NPC83922
0.925 High Similarity NPC472448
0.9245 High Similarity NPC476980
0.9207 High Similarity NPC475669
0.9193 High Similarity NPC189473
0.9193 High Similarity NPC23298
0.9187 High Similarity NPC198829
0.9182 High Similarity NPC238381
0.9182 High Similarity NPC74178
0.9182 High Similarity NPC184755
0.9177 High Similarity NPC191146
0.9177 High Similarity NPC68093
0.9136 High Similarity NPC472450
0.9136 High Similarity NPC50960
0.9136 High Similarity NPC239752
0.9136 High Similarity NPC275780
0.913 High Similarity NPC78332
0.913 High Similarity NPC194427
0.9125 High Similarity NPC192686
0.9125 High Similarity NPC119209
0.9125 High Similarity NPC118256
0.9119 High Similarity NPC476981
0.9119 High Similarity NPC218313
0.9119 High Similarity NPC78225
0.9119 High Similarity NPC474681
0.9119 High Similarity NPC237418
0.9114 High Similarity NPC471800
0.9114 High Similarity NPC234255
0.9114 High Similarity NPC472280
0.9108 High Similarity NPC249570
0.9108 High Similarity NPC471982
0.9108 High Similarity NPC289968
0.9108 High Similarity NPC237994
0.9108 High Similarity NPC199773
0.9103 High Similarity NPC88804
0.9103 High Similarity NPC3825
0.9085 High Similarity NPC471287
0.9085 High Similarity NPC476637
0.908 High Similarity NPC37870
0.908 High Similarity NPC39091
0.908 High Similarity NPC472449
0.9074 High Similarity NPC156082
0.9074 High Similarity NPC303460
0.9074 High Similarity NPC306321
0.9068 High Similarity NPC40037
0.9068 High Similarity NPC258331
0.9068 High Similarity NPC349525
0.9068 High Similarity NPC474038
0.9062 High Similarity NPC469658
0.9062 High Similarity NPC204879
0.9057 High Similarity NPC5322
0.9057 High Similarity NPC6633
0.9057 High Similarity NPC138243
0.9057 High Similarity NPC472455
0.9057 High Similarity NPC282307
0.9057 High Similarity NPC133970
0.9057 High Similarity NPC170026
0.9051 High Similarity NPC47781
0.9051 High Similarity NPC476631
0.9051 High Similarity NPC176775
0.9051 High Similarity NPC231018
0.9051 High Similarity NPC183878
0.9051 High Similarity NPC145379
0.9051 High Similarity NPC475895
0.9051 High Similarity NPC22519
0.9051 High Similarity NPC274327
0.9051 High Similarity NPC160951
0.9051 High Similarity NPC255350
0.9051 High Similarity NPC69394
0.9045 High Similarity NPC154345
0.903 High Similarity NPC109827
0.903 High Similarity NPC101107
0.903 High Similarity NPC124470
0.9024 High Similarity NPC471288
0.9018 High Similarity NPC156432
0.9018 High Similarity NPC8070
0.9018 High Similarity NPC112981
0.9012 High Similarity NPC25152
0.9012 High Similarity NPC329760
0.9012 High Similarity NPC229632
0.9012 High Similarity NPC474150
0.9012 High Similarity NPC474162
0.9006 High Similarity NPC475784
0.9006 High Similarity NPC292415
0.9006 High Similarity NPC471973
0.9006 High Similarity NPC246478
0.9006 High Similarity NPC139036
0.9 High Similarity NPC36852
0.9 High Similarity NPC223787
0.9 High Similarity NPC284820
0.9 High Similarity NPC27337
0.9 High Similarity NPC262286
0.9 High Similarity NPC52889
0.9 High Similarity NPC473272
0.8994 High Similarity NPC183597
0.8994 High Similarity NPC163780
0.8994 High Similarity NPC286052
0.8994 High Similarity NPC201136
0.8994 High Similarity NPC196439
0.8994 High Similarity NPC256612
0.8994 High Similarity NPC213622
0.8994 High Similarity NPC227325
0.8994 High Similarity NPC92659
0.8994 High Similarity NPC167815
0.8994 High Similarity NPC2476
0.8994 High Similarity NPC20830
0.8994 High Similarity NPC200246
0.8994 High Similarity NPC4455
0.8994 High Similarity NPC146165
0.8994 High Similarity NPC138360
0.8994 High Similarity NPC280339
0.8994 High Similarity NPC50715
0.8994 High Similarity NPC128863
0.8987 High Similarity NPC239128
0.8987 High Similarity NPC71334
0.8987 High Similarity NPC156222
0.8987 High Similarity NPC275836
0.8987 High Similarity NPC37684
0.8987 High Similarity NPC188203
0.8987 High Similarity NPC162313
0.8987 High Similarity NPC157784
0.8987 High Similarity NPC83508
0.8987 High Similarity NPC57030
0.8987 High Similarity NPC301323
0.8987 High Similarity NPC63187
0.8987 High Similarity NPC275722
0.8987 High Similarity NPC187498
0.8987 High Similarity NPC293183
0.8987 High Similarity NPC198826
0.8987 High Similarity NPC241498
0.8987 High Similarity NPC100887
0.8987 High Similarity NPC120163
0.8987 High Similarity NPC212678
0.8987 High Similarity NPC256283
0.8987 High Similarity NPC222830
0.8987 High Similarity NPC131624
0.8987 High Similarity NPC25270
0.897 High Similarity NPC475805
0.897 High Similarity NPC280493
0.8963 High Similarity NPC20216
0.8957 High Similarity NPC472625
0.8957 High Similarity NPC186686
0.8957 High Similarity NPC236521
0.8957 High Similarity NPC152659
0.8957 High Similarity NPC474350
0.8957 High Similarity NPC207690
0.8957 High Similarity NPC248638
0.8951 High Similarity NPC472632
0.8951 High Similarity NPC103201
0.8951 High Similarity NPC266314
0.8951 High Similarity NPC471210
0.8951 High Similarity NPC234644
0.8951 High Similarity NPC303565
0.8951 High Similarity NPC26326
0.8951 High Similarity NPC473106
0.8951 High Similarity NPC61010
0.8944 High Similarity NPC474290
0.8944 High Similarity NPC280680
0.8944 High Similarity NPC250214
0.8944 High Similarity NPC95936
0.8944 High Similarity NPC100123
0.8938 High Similarity NPC278778
0.8938 High Similarity NPC195796
0.8938 High Similarity NPC291878
0.8938 High Similarity NPC49824
0.8938 High Similarity NPC470600
0.8938 High Similarity NPC35038
0.8935 High Similarity NPC113446
0.8931 High Similarity NPC276409
0.8931 High Similarity NPC298802
0.8931 High Similarity NPC75279
0.8931 High Similarity NPC49402
0.8931 High Similarity NPC472408
0.8931 High Similarity NPC273462
0.8931 High Similarity NPC250822
0.8931 High Similarity NPC70433
0.8931 High Similarity NPC33051
0.8931 High Similarity NPC227337
0.8924 High Similarity NPC304295
0.8924 High Similarity NPC59162
0.8924 High Similarity NPC308451
0.8924 High Similarity NPC205046
0.8924 High Similarity NPC226973
0.8924 High Similarity NPC208043

  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 NPC85057 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
0.9051 High Similarity NPD2801 Approved
0.8812 High Similarity NPD2393 Clinical (unspecified phase)
0.875 High Similarity NPD1934 Approved
0.8718 High Similarity NPD1511 Approved
0.8642 High Similarity NPD3817 Phase 2
0.8608 High Similarity NPD1512 Approved
0.8538 High Similarity NPD4338 Clinical (unspecified phase)
0.8521 High Similarity NPD5844 Phase 1
0.8476 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.8452 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.8452 Intermediate Similarity NPD6166 Phase 2
0.8452 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.8443 Intermediate Similarity NPD6232 Discontinued
0.8428 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.8412 Intermediate Similarity NPD7054 Approved
0.8364 Intermediate Similarity NPD3882 Suspended
0.8363 Intermediate Similarity NPD7074 Phase 3
0.8363 Intermediate Similarity NPD7472 Approved
0.8354 Intermediate Similarity NPD1465 Phase 2
0.8353 Intermediate Similarity NPD3818 Discontinued
0.8323 Intermediate Similarity NPD5494 Approved
0.8313 Intermediate Similarity NPD7075 Discontinued
0.8313 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.8294 Intermediate Similarity NPD7473 Discontinued
0.8282 Intermediate Similarity NPD4380 Phase 2
0.8242 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.8208 Intermediate Similarity NPD6797 Phase 2
0.8193 Intermediate Similarity NPD5402 Approved
0.8182 Intermediate Similarity NPD6801 Discontinued
0.8161 Intermediate Similarity NPD7251 Discontinued
0.8153 Intermediate Similarity NPD2935 Discontinued
0.8133 Intermediate Similarity NPD7819 Suspended
0.8121 Intermediate Similarity NPD7411 Suspended
0.8114 Intermediate Similarity NPD7808 Phase 3
0.8095 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.8047 Intermediate Similarity NPD919 Approved
0.8025 Intermediate Similarity NPD6799 Approved
0.8 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7989 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.795 Intermediate Similarity NPD3750 Approved
0.7937 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7929 Intermediate Similarity NPD7768 Phase 2
0.7898 Intermediate Similarity NPD447 Suspended
0.7882 Intermediate Similarity NPD3749 Approved
0.7879 Intermediate Similarity NPD5403 Approved
0.7875 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.7875 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.787 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.7862 Intermediate Similarity NPD1510 Phase 2
0.7849 Intermediate Similarity NPD1247 Approved
0.7845 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7844 Intermediate Similarity NPD6599 Discontinued
0.7826 Intermediate Similarity NPD1549 Phase 2
0.7816 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.7812 Intermediate Similarity NPD2796 Approved
0.7778 Intermediate Similarity NPD1243 Approved
0.7758 Intermediate Similarity NPD2532 Approved
0.7758 Intermediate Similarity NPD2534 Approved
0.7758 Intermediate Similarity NPD2533 Approved
0.7758 Intermediate Similarity NPD5401 Approved
0.7753 Intermediate Similarity NPD6559 Discontinued
0.775 Intermediate Similarity NPD2799 Discontinued
0.7746 Intermediate Similarity NPD6959 Discontinued
0.7725 Intermediate Similarity NPD1653 Approved
0.7722 Intermediate Similarity NPD1240 Approved
0.7722 Intermediate Similarity NPD943 Approved
0.7692 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7679 Intermediate Similarity NPD3226 Approved
0.7673 Intermediate Similarity NPD230 Phase 1
0.7669 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7665 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7665 Intermediate Similarity NPD920 Approved
0.764 Intermediate Similarity NPD3748 Approved
0.7628 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7625 Intermediate Similarity NPD1607 Approved
0.7595 Intermediate Similarity NPD2313 Discontinued
0.7595 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7593 Intermediate Similarity NPD1551 Phase 2
0.759 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7582 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7568 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7561 Intermediate Similarity NPD2800 Approved
0.7545 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7543 Intermediate Similarity NPD7199 Phase 2
0.753 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.7529 Intermediate Similarity NPD6234 Discontinued
0.7515 Intermediate Similarity NPD4628 Phase 3
0.7515 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD1203 Approved
0.75 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD1613 Approved
0.747 Intermediate Similarity NPD6190 Approved
0.7458 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7458 Intermediate Similarity NPD3926 Phase 2
0.7453 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.7453 Intermediate Similarity NPD5124 Phase 1
0.7453 Intermediate Similarity NPD1933 Approved
0.7439 Intermediate Similarity NPD2346 Discontinued
0.7436 Intermediate Similarity NPD3225 Approved
0.7423 Intermediate Similarity NPD4308 Phase 3
0.7421 Intermediate Similarity NPD3027 Phase 3
0.741 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7403 Intermediate Similarity NPD5953 Discontinued
0.7389 Intermediate Similarity NPD7286 Phase 2
0.7389 Intermediate Similarity NPD2797 Approved
0.7375 Intermediate Similarity NPD3268 Approved
0.7363 Intermediate Similarity NPD7685 Pre-registration
0.7355 Intermediate Similarity NPD422 Phase 1
0.7341 Intermediate Similarity NPD37 Approved
0.7333 Intermediate Similarity NPD7228 Approved
0.7322 Intermediate Similarity NPD7549 Discontinued
0.7317 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.7317 Intermediate Similarity NPD7033 Discontinued
0.7316 Intermediate Similarity NPD8090 Clinical (unspecified phase)
0.7314 Intermediate Similarity NPD4966 Approved
0.7314 Intermediate Similarity NPD4967 Phase 2
0.7314 Intermediate Similarity NPD4965 Approved
0.7308 Intermediate Similarity NPD9717 Approved
0.7278 Intermediate Similarity NPD7390 Discontinued
0.7273 Intermediate Similarity NPD6100 Approved
0.7273 Intermediate Similarity NPD7782 Clinical (unspecified phase)
0.7273 Intermediate Similarity NPD7783 Phase 2
0.7273 Intermediate Similarity NPD6099 Approved
0.725 Intermediate Similarity NPD6832 Phase 2
0.7239 Intermediate Similarity NPD1899 Clinical (unspecified phase)
0.7238 Intermediate Similarity NPD3751 Discontinued
0.7228 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.7212 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.7207 Intermediate Similarity NPD5710 Approved
0.7207 Intermediate Similarity NPD5711 Approved
0.7207 Intermediate Similarity NPD3787 Discontinued
0.7202 Intermediate Similarity NPD7501 Clinical (unspecified phase)
0.7197 Intermediate Similarity NPD9269 Phase 2
0.7197 Intermediate Similarity NPD1608 Approved
0.7195 Intermediate Similarity NPD6651 Approved
0.7189 Intermediate Similarity NPD8313 Approved
0.7189 Intermediate Similarity NPD8312 Approved
0.7179 Intermediate Similarity NPD7435 Discontinued
0.7178 Intermediate Similarity NPD4307 Phase 2
0.7169 Intermediate Similarity NPD5405 Approved
0.7169 Intermediate Similarity NPD5406 Approved
0.7169 Intermediate Similarity NPD5404 Approved
0.7169 Intermediate Similarity NPD5408 Approved
0.7167 Intermediate Similarity NPD5242 Approved
0.7166 Intermediate Similarity NPD8150 Discontinued
0.7166 Intermediate Similarity NPD8434 Phase 2
0.716 Intermediate Similarity NPD411 Approved
0.716 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.716 Intermediate Similarity NPD1296 Phase 2
0.7159 Intermediate Similarity NPD4288 Approved
0.7135 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7126 Intermediate Similarity NPD2344 Approved
0.7117 Intermediate Similarity NPD6233 Phase 2
0.7113 Intermediate Similarity NPD6782 Approved
0.7113 Intermediate Similarity NPD6781 Approved
0.7113 Intermediate Similarity NPD6778 Approved
0.7113 Intermediate Similarity NPD6780 Approved
0.7113 Intermediate Similarity NPD6776 Approved
0.7113 Intermediate Similarity NPD6779 Approved
0.7113 Intermediate Similarity NPD6777 Approved
0.7111 Intermediate Similarity NPD7229 Phase 3
0.7099 Intermediate Similarity NPD4625 Phase 3
0.7086 Intermediate Similarity NPD7615 Clinical (unspecified phase)
0.7081 Intermediate Similarity NPD9494 Approved
0.7073 Intermediate Similarity NPD4060 Phase 1
0.7071 Intermediate Similarity NPD7584 Approved
0.7069 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7069 Intermediate Similarity NPD7458 Discontinued
0.7063 Intermediate Similarity NPD3267 Approved
0.7063 Intermediate Similarity NPD3266 Approved
0.7056 Intermediate Similarity NPD8127 Discontinued
0.7055 Intermediate Similarity NPD6798 Discontinued
0.7044 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.7041 Intermediate Similarity NPD1652 Phase 2
0.7037 Intermediate Similarity NPD4908 Phase 1
0.7035 Intermediate Similarity NPD7422 Clinical (unspecified phase)
0.7035 Intermediate Similarity NPD7585 Approved
0.7031 Intermediate Similarity NPD4360 Phase 2
0.7031 Intermediate Similarity NPD4363 Phase 3
0.7019 Intermediate Similarity NPD2798 Approved
0.7006 Intermediate Similarity NPD17 Approved
0.7006 Intermediate Similarity NPD8455 Phase 2
0.7 Intermediate Similarity NPD8151 Discontinued
0.7 Intermediate Similarity NPD4287 Approved
0.6994 Remote Similarity NPD1940 Clinical (unspecified phase)
0.6994 Remote Similarity NPD5049 Phase 3
0.6994 Remote Similarity NPD7095 Approved
0.6989 Remote Similarity NPD6385 Approved
0.6989 Remote Similarity NPD6386 Approved
0.6985 Remote Similarity NPD7583 Approved
0.6981 Remote Similarity NPD1481 Phase 2
0.6966 Remote Similarity NPD5353 Approved
0.6965 Remote Similarity NPD7875 Clinical (unspecified phase)
0.6965 Remote Similarity NPD7874 Approved
0.6959 Remote Similarity NPD2309 Approved
0.6959 Remote Similarity NPD2354 Approved
0.6951 Remote Similarity NPD3764 Approved
0.6943 Remote Similarity NPD9268 Approved
0.694 Remote Similarity NPD7784 Clinical (unspecified phase)
0.6932 Remote Similarity NPD6585 Discontinued

  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