Structure

Physi-Chem Properties

Molecular Weight:  742.17
Volume:  698.367
LogP:  2.511
LogD:  1.622
LogS:  -4.983
# Rotatable Bonds:  18
TPSA:  232.77
# H-Bond Aceptor:  18
# H-Bond Donor:  0
# Rings:  4
# Heavy Atoms:  18

MedChem Properties

QED Drug-Likeness Score:  0.156
Synthetic Accessibility Score:  4.499
Fsp3:  0.371
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.041
MDCK Permeability:  9.605144441593438e-05
Pgp-inhibitor:  0.992
Pgp-substrate:  0.084
Human Intestinal Absorption (HIA):  0.921
20% Bioavailability (F20%):  0.031
30% Bioavailability (F30%):  0.99

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.238
Plasma Protein Binding (PPB):  70.38387298583984%
Volume Distribution (VD):  0.628
Pgp-substrate:  18.03657341003418%

ADMET: Metabolism

CYP1A2-inhibitor:  0.066
CYP1A2-substrate:  0.006
CYP2C19-inhibitor:  0.032
CYP2C19-substrate:  0.052
CYP2C9-inhibitor:  0.177
CYP2C9-substrate:  0.091
CYP2D6-inhibitor:  0.931
CYP2D6-substrate:  0.088
CYP3A4-inhibitor:  0.492
CYP3A4-substrate:  0.164

ADMET: Excretion

Clearance (CL):  1.008
Half-life (T1/2):  0.769

ADMET: Toxicity

hERG Blockers:  0.001
Human Hepatotoxicity (H-HT):  0.97
Drug-inuced Liver Injury (DILI):  0.948
AMES Toxicity:  0.234
Rat Oral Acute Toxicity:  0.149
Maximum Recommended Daily Dose:  0.22
Skin Sensitization:  0.932
Carcinogencity:  0.043
Eye Corrosion:  0.003
Eye Irritation:  0.048
Respiratory Toxicity:  0.033

Download Data

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

  Natural Product: NPC414831

Natural Product ID:  NPC414831
Common Name*:   [(2R,3R,4S,5R,6S)-3,4,5-Triacetyloxy-6-[5-Acetyloxy-2-(3,4-Diacetyloxyphenyl)-4-Oxochromen-7-Yl]Oxyoxan-2-Yl]Methyl Acetate
IUPAC Name:   [(2R,3R,4S,5R,6S)-3,4,5-triacetyloxy-6-[5-acetyloxy-2-(3,4-diacetyloxyphenyl)-4-oxochromen-7-yl]oxyoxan-2-yl]methyl acetate
Synonyms:  
Standard InCHIKey:  JDAPIOVVXOAJOM-VSSHJLDSSA-N
Standard InCHI:  InChI=1S/C35H34O18/c1-15(36)44-14-30-32(48-19(5)40)33(49-20(6)41)34(50-21(7)42)35(53-30)51-23-11-28(47-18(4)39)31-24(43)13-26(52-29(31)12-23)22-8-9-25(45-16(2)37)27(10-22)46-17(3)38/h8-13,30,32-35H,14H2,1-7H3/t30-,32-,33+,34-,35-/m1/s1
SMILES:  CC(=O)OC[C@H]1O[C@@H](Oc2cc(OC(=O)C)c3c(c2)oc(cc3=O)c2ccc(c(c2)OC(=O)C)OC(=O)C)[C@@H]([C@H]([C@@H]1OC(=O)C)OC(=O)C)OC(=O)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL450297
PubChem CID:   16396576
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0000334] Flavonoids
        • [CHEMONTID:0001111] Flavonoid glycosides
          • [CHEMONTID:0001583] Flavonoid O-glycosides
            • [CHEMONTID:0003533] Flavonoid-7-O-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
NPO30745 Chrysanthemum morifolium Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[8158164]
NPO30745 Chrysanthemum morifolium Species Asteraceae Eukaryota n.a. inflorescence n.a. PMID[8158164]
NPO30745 Chrysanthemum morifolium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO30745 Chrysanthemum morifolium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]

☑ 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
NPT759 Cell Line H9 Homo sapiens IC50 = 6000.0 nM PMID[559327]
NPT27 Others Unspecified TI = 1.0 n.a. PMID[559327]
NPT24 Organism Human immunodeficiency virus 1 Human immunodeficiency virus 1 EC50 = 6000.0 nM PMID[559327]

☑ 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 NPC414831 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
0.9808 High Similarity NPC475214
0.9684 High Similarity NPC476180
0.9684 High Similarity NPC477165
0.9623 High Similarity NPC475434
0.9487 High Similarity NPC477164
0.9359 High Similarity NPC117478
0.9304 High Similarity NPC182045
0.925 High Similarity NPC15358
0.925 High Similarity NPC475497
0.925 High Similarity NPC475366
0.925 High Similarity NPC284277
0.9241 High Similarity NPC110349
0.9241 High Similarity NPC321478
0.9212 High Similarity NPC120952
0.9187 High Similarity NPC243930
0.9187 High Similarity NPC88023
0.9187 High Similarity NPC309025
0.9182 High Similarity NPC473516
0.9152 High Similarity NPC473862
0.913 High Similarity NPC22832
0.913 High Similarity NPC311830
0.9108 High Similarity NPC471746
0.9096 High Similarity NPC173837
0.9091 High Similarity NPC198199
0.9085 High Similarity NPC211594
0.9085 High Similarity NPC180918
0.9085 High Similarity NPC153755
0.9085 High Similarity NPC254540
0.9085 High Similarity NPC172807
0.908 High Similarity NPC195257
0.908 High Similarity NPC209296
0.908 High Similarity NPC86008
0.9068 High Similarity NPC284960
0.9068 High Similarity NPC191306
0.9068 High Similarity NPC19709
0.9068 High Similarity NPC270335
0.9068 High Similarity NPC222936
0.9062 High Similarity NPC34376
0.9051 High Similarity NPC155063
0.9048 High Similarity NPC35924
0.9048 High Similarity NPC199172
0.9042 High Similarity NPC471030
0.9038 High Similarity NPC472535
0.9038 High Similarity NPC474388
0.9038 High Similarity NPC474170
0.9036 High Similarity NPC48984
0.9036 High Similarity NPC89127
0.9036 High Similarity NPC471669
0.903 High Similarity NPC472993
0.903 High Similarity NPC88560
0.903 High Similarity NPC175230
0.903 High Similarity NPC172033
0.903 High Similarity NPC4390
0.9024 High Similarity NPC244776
0.9024 High Similarity NPC116864
0.9018 High Similarity NPC135345
0.9018 High Similarity NPC116745
0.9018 High Similarity NPC229729
0.9012 High Similarity NPC475369
0.9006 High Similarity NPC77660
0.9006 High Similarity NPC189142
0.9006 High Similarity NPC473043
0.8994 High Similarity NPC470713
0.8994 High Similarity NPC470720
0.8994 High Similarity NPC470455
0.8994 High Similarity NPC21359
0.8994 High Similarity NPC460984
0.8994 High Similarity NPC470451
0.8994 High Similarity NPC470717
0.8994 High Similarity NPC25946
0.8987 High Similarity NPC222185
0.8982 High Similarity NPC89052
0.8982 High Similarity NPC477895
0.8982 High Similarity NPC251417
0.8982 High Similarity NPC475261
0.8981 High Similarity NPC68882
0.8976 High Similarity NPC473327
0.8976 High Similarity NPC19108
0.8976 High Similarity NPC264735
0.8976 High Similarity NPC16194
0.8976 High Similarity NPC220173
0.8976 High Similarity NPC476472
0.8976 High Similarity NPC294815
0.8976 High Similarity NPC477848
0.8974 High Similarity NPC177839
0.897 High Similarity NPC472386
0.897 High Similarity NPC190003
0.897 High Similarity NPC475155
0.897 High Similarity NPC175107
0.8963 High Similarity NPC219904
0.8963 High Similarity NPC58053
0.8963 High Similarity NPC226294
0.8963 High Similarity NPC293629
0.8963 High Similarity NPC203050
0.8963 High Similarity NPC61791
0.8963 High Similarity NPC223747
0.8963 High Similarity NPC186807
0.8963 High Similarity NPC105025
0.8963 High Similarity NPC201292
0.8963 High Similarity NPC93337
0.8963 High Similarity NPC475942
0.8963 High Similarity NPC469931
0.8963 High Similarity NPC120099
0.8963 High Similarity NPC225434
0.8963 High Similarity NPC45638
0.8957 High Similarity NPC115674
0.8957 High Similarity NPC197285
0.8957 High Similarity NPC5778
0.8957 High Similarity NPC8856
0.8957 High Similarity NPC236934
0.8957 High Similarity NPC210073
0.8957 High Similarity NPC21100
0.8951 High Similarity NPC168822
0.8941 High Similarity NPC474093
0.8941 High Similarity NPC295625
0.8941 High Similarity NPC104910
0.8941 High Similarity NPC470719
0.8941 High Similarity NPC473554
0.8938 High Similarity NPC43761
0.8935 High Similarity NPC470447
0.8935 High Similarity NPC156785
0.8935 High Similarity NPC470718
0.8935 High Similarity NPC470446
0.8935 High Similarity NPC162394
0.8935 High Similarity NPC470449
0.8935 High Similarity NPC241781
0.8935 High Similarity NPC470445
0.8931 High Similarity NPC257277
0.8929 High Similarity NPC192539
0.8929 High Similarity NPC473895
0.8924 High Similarity NPC186507
0.8922 High Similarity NPC233994
0.8922 High Similarity NPC255799
0.8922 High Similarity NPC472385
0.8922 High Similarity NPC211532
0.8922 High Similarity NPC14187
0.8922 High Similarity NPC202908
0.8922 High Similarity NPC219043
0.8922 High Similarity NPC198324
0.8922 High Similarity NPC122467
0.8922 High Similarity NPC292019
0.8916 High Similarity NPC204693
0.8916 High Similarity NPC25724
0.8916 High Similarity NPC208668
0.891 High Similarity NPC474648
0.8909 High Similarity NPC206123
0.8909 High Similarity NPC177731
0.8909 High Similarity NPC149011
0.8909 High Similarity NPC293004
0.8909 High Similarity NPC105095
0.8909 High Similarity NPC204937
0.8909 High Similarity NPC51326
0.8909 High Similarity NPC20505
0.8909 High Similarity NPC231194
0.8909 High Similarity NPC194483
0.8909 High Similarity NPC52353
0.8909 High Similarity NPC79056
0.8909 High Similarity NPC155763
0.8909 High Similarity NPC67105
0.8909 High Similarity NPC105511
0.8909 High Similarity NPC44328
0.8909 High Similarity NPC235260
0.8909 High Similarity NPC285197
0.8902 High Similarity NPC52550
0.8902 High Similarity NPC45618
0.8902 High Similarity NPC146792
0.8902 High Similarity NPC226304
0.8902 High Similarity NPC317489
0.8902 High Similarity NPC325555
0.8902 High Similarity NPC223424
0.8902 High Similarity NPC265530
0.8902 High Similarity NPC173637
0.8902 High Similarity NPC58716
0.8902 High Similarity NPC84362
0.8902 High Similarity NPC127546
0.8896 High Similarity NPC277205
0.8889 High Similarity NPC475179
0.8889 High Similarity NPC70853
0.8889 High Similarity NPC300537
0.8889 High Similarity NPC127782
0.8889 High Similarity NPC298171
0.8889 High Similarity NPC9966
0.8882 High Similarity NPC275977
0.8882 High Similarity NPC223860
0.8882 High Similarity NPC249560
0.8875 High Similarity NPC108456
0.8875 High Similarity NPC258644
0.8869 High Similarity NPC241196
0.8869 High Similarity NPC139571
0.8869 High Similarity NPC217520
0.8868 High Similarity NPC284353
0.8868 High Similarity NPC122623
0.8868 High Similarity NPC241774
0.8868 High Similarity NPC34725
0.8868 High Similarity NPC276059
0.8862 High Similarity NPC101191
0.8862 High Similarity NPC49344
0.8862 High Similarity NPC210094
0.8862 High Similarity NPC253685
0.8862 High Similarity NPC237435

  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 NPC414831 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
0.9141 High Similarity NPD7472 Approved
0.9091 High Similarity NPD7808 Phase 3
0.908 High Similarity NPD7054 Approved
0.8916 High Similarity NPD7251 Discontinued
0.8909 High Similarity NPD7074 Phase 3
0.8868 High Similarity NPD3817 Phase 2
0.8862 High Similarity NPD4338 Clinical (unspecified phase)
0.8855 High Similarity NPD6797 Phase 2
0.8675 High Similarity NPD3818 Discontinued
0.8642 High Similarity NPD4381 Clinical (unspecified phase)
0.8512 High Similarity NPD7804 Clinical (unspecified phase)
0.8509 High Similarity NPD1934 Approved
0.8428 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.8424 Intermediate Similarity NPD5494 Approved
0.8344 Intermediate Similarity NPD7819 Suspended
0.8344 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.8344 Intermediate Similarity NPD2801 Approved
0.8333 Intermediate Similarity NPD6166 Phase 2
0.8333 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.8333 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.8258 Intermediate Similarity NPD2796 Approved
0.8242 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.8232 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.8193 Intermediate Similarity NPD7075 Discontinued
0.8144 Intermediate Similarity NPD919 Approved
0.8125 Intermediate Similarity NPD6799 Approved
0.8125 Intermediate Similarity NPD1511 Approved
0.8117 Intermediate Similarity NPD1933 Approved
0.8081 Intermediate Similarity NPD5844 Phase 1
0.8072 Intermediate Similarity NPD5402 Approved
0.8061 Intermediate Similarity NPD6801 Discontinued
0.8049 Intermediate Similarity NPD4380 Phase 2
0.8046 Intermediate Similarity NPD6559 Discontinued
0.8025 Intermediate Similarity NPD1512 Approved
0.8024 Intermediate Similarity NPD3882 Suspended
0.8 Intermediate Similarity NPD7411 Suspended
0.7989 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7975 Intermediate Similarity NPD5403 Approved
0.7965 Intermediate Similarity NPD7473 Discontinued
0.7964 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.7963 Intermediate Similarity NPD5401 Approved
0.7927 Intermediate Similarity NPD1653 Approved
0.7895 Intermediate Similarity NPD6232 Discontinued
0.7862 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.7862 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.7853 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.7841 Intermediate Similarity NPD7685 Pre-registration
0.7836 Intermediate Similarity NPD7199 Phase 2
0.7831 Intermediate Similarity NPD6599 Discontinued
0.7812 Intermediate Similarity NPD1549 Phase 2
0.7798 Intermediate Similarity NPD1465 Phase 2
0.7792 Intermediate Similarity NPD6832 Phase 2
0.7758 Intermediate Similarity NPD920 Approved
0.7753 Intermediate Similarity NPD8312 Approved
0.7753 Intermediate Similarity NPD8313 Approved
0.7747 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7746 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7746 Intermediate Similarity NPD3926 Phase 2
0.7736 Intermediate Similarity NPD3748 Approved
0.7735 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7733 Intermediate Similarity NPD1247 Approved
0.7701 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.7692 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7692 Intermediate Similarity NPD8455 Phase 2
0.7683 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7654 Intermediate Similarity NPD1243 Approved
0.7636 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.7636 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7633 Intermediate Similarity NPD37 Approved
0.763 Intermediate Similarity NPD6959 Discontinued
0.7625 Intermediate Similarity NPD1510 Phase 2
0.7622 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.7614 Intermediate Similarity NPD7228 Approved
0.7602 Intermediate Similarity NPD4967 Phase 2
0.7602 Intermediate Similarity NPD4965 Approved
0.7602 Intermediate Similarity NPD7768 Phase 2
0.7602 Intermediate Similarity NPD4966 Approved
0.76 Intermediate Similarity NPD7784 Clinical (unspecified phase)
0.7593 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7569 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7547 Intermediate Similarity NPD1899 Clinical (unspecified phase)
0.7547 Intermediate Similarity NPD447 Suspended
0.7544 Intermediate Similarity NPD5353 Approved
0.7542 Intermediate Similarity NPD7240 Approved
0.7514 Intermediate Similarity NPD6234 Discontinued
0.7513 Intermediate Similarity NPD8151 Discontinued
0.75 Intermediate Similarity NPD3750 Approved
0.75 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7486 Intermediate Similarity NPD3787 Discontinued
0.7457 Intermediate Similarity NPD3749 Approved
0.7423 Intermediate Similarity NPD7266 Discontinued
0.7416 Intermediate Similarity NPD3751 Discontinued
0.7375 Intermediate Similarity NPD1240 Approved
0.7368 Intermediate Similarity NPD6385 Approved
0.7368 Intermediate Similarity NPD6386 Approved
0.7362 Intermediate Similarity NPD1551 Phase 2
0.7347 Intermediate Similarity NPD7783 Phase 2
0.7347 Intermediate Similarity NPD7782 Clinical (unspecified phase)
0.7345 Intermediate Similarity NPD5242 Approved
0.7333 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.732 Intermediate Similarity NPD7584 Approved
0.7292 Intermediate Similarity NPD5006 Approved
0.7292 Intermediate Similarity NPD5005 Approved
0.7289 Intermediate Similarity NPD4628 Phase 3
0.7284 Intermediate Similarity NPD1607 Approved
0.7256 Intermediate Similarity NPD2935 Discontinued
0.7254 Intermediate Similarity NPD7435 Discontinued
0.7251 Intermediate Similarity NPD7458 Discontinued
0.7251 Intermediate Similarity NPD3226 Approved
0.7232 Intermediate Similarity NPD8127 Discontinued
0.7231 Intermediate Similarity NPD7583 Approved
0.7226 Intermediate Similarity NPD1547 Clinical (unspecified phase)
0.7222 Intermediate Similarity NPD230 Phase 1
0.7219 Intermediate Similarity NPD2533 Approved
0.7219 Intermediate Similarity NPD2532 Approved
0.7219 Intermediate Similarity NPD2534 Approved
0.7211 Intermediate Similarity NPD8090 Clinical (unspecified phase)
0.7194 Intermediate Similarity NPD7585 Approved
0.7173 Intermediate Similarity NPD4420 Approved
0.7165 Intermediate Similarity NPD7698 Approved
0.7165 Intermediate Similarity NPD7696 Phase 3
0.7165 Intermediate Similarity NPD7697 Approved
0.716 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.716 Intermediate Similarity NPD1613 Approved
0.7152 Intermediate Similarity NPD3266 Approved
0.7152 Intermediate Similarity NPD3267 Approved
0.7151 Intermediate Similarity NPD8434 Phase 2
0.7143 Intermediate Similarity NPD2313 Discontinued
0.7135 Intermediate Similarity NPD8285 Discontinued
0.7128 Intermediate Similarity NPD7871 Phase 2
0.7128 Intermediate Similarity NPD7870 Phase 2
0.7126 Intermediate Similarity NPD1652 Phase 2
0.7121 Intermediate Similarity NPD7874 Approved
0.7121 Intermediate Similarity NPD7875 Clinical (unspecified phase)
0.7118 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7108 Intermediate Similarity NPD2346 Discontinued
0.7107 Intermediate Similarity NPD1019 Discontinued
0.7107 Intermediate Similarity NPD2798 Approved
0.7104 Intermediate Similarity NPD5953 Discontinued
0.7098 Intermediate Similarity NPD7501 Clinical (unspecified phase)
0.7098 Intermediate Similarity NPD6779 Approved
0.7098 Intermediate Similarity NPD6776 Approved
0.7098 Intermediate Similarity NPD6782 Approved
0.7098 Intermediate Similarity NPD6781 Approved
0.7098 Intermediate Similarity NPD6780 Approved
0.7098 Intermediate Similarity NPD6777 Approved
0.7098 Intermediate Similarity NPD6778 Approved
0.7091 Intermediate Similarity NPD2799 Discontinued
0.7091 Intermediate Similarity NPD7033 Discontinued
0.7088 Intermediate Similarity NPD7286 Phase 2
0.7055 Intermediate Similarity NPD943 Approved
0.7055 Intermediate Similarity NPD4307 Phase 2
0.7044 Intermediate Similarity NPD1203 Approved
0.7041 Intermediate Similarity NPD6190 Approved
0.7037 Intermediate Similarity NPD3268 Approved
0.7037 Intermediate Similarity NPD1296 Phase 2
0.7029 Intermediate Similarity NPD6844 Discontinued
0.7024 Intermediate Similarity NPD6674 Discontinued
0.702 Intermediate Similarity NPD7701 Phase 2
0.7019 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7012 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.7012 Intermediate Similarity NPD5124 Phase 1
0.6987 Remote Similarity NPD17 Approved
0.6982 Remote Similarity NPD6398 Clinical (unspecified phase)
0.6981 Remote Similarity NPD3225 Approved
0.6977 Remote Similarity NPD1940 Clinical (unspecified phase)
0.6975 Remote Similarity NPD3027 Phase 3
0.6971 Remote Similarity NPD5890 Approved
0.6971 Remote Similarity NPD7615 Clinical (unspecified phase)
0.6971 Remote Similarity NPD5889 Approved
0.6968 Remote Similarity NPD8150 Discontinued
0.6962 Remote Similarity NPD9717 Approved
0.6957 Remote Similarity NPD3018 Phase 2
0.6957 Remote Similarity NPD1530 Clinical (unspecified phase)
0.6954 Remote Similarity NPD8320 Phase 1
0.6954 Remote Similarity NPD8319 Approved
0.6954 Remote Similarity NPD8158 Clinical (unspecified phase)
0.6946 Remote Similarity NPD6099 Approved
0.6946 Remote Similarity NPD6100 Approved
0.6941 Remote Similarity NPD3887 Approved
0.694 Remote Similarity NPD7893 Clinical (unspecified phase)
0.6939 Remote Similarity NPD6823 Phase 2
0.6937 Remote Similarity NPD2797 Approved
0.6935 Remote Similarity NPD7549 Discontinued
0.6933 Remote Similarity NPD6798 Discontinued
0.6928 Remote Similarity NPD7097 Phase 1
0.6923 Remote Similarity NPD2800 Approved
0.6923 Remote Similarity NPD2654 Approved
0.6919 Remote Similarity NPD3146 Approved
0.6919 Remote Similarity NPD3688 Clinical (unspecified phase)
0.6915 Remote Similarity NPD7801 Approved
0.6909 Remote Similarity NPD6355 Discontinued
0.6907 Remote Similarity NPD7699 Phase 2
0.6907 Remote Similarity NPD7700 Phase 2
0.6906 Remote Similarity NPD7229 Phase 3
0.6904 Remote Similarity NPD7680 Approved
0.6903 Remote Similarity NPD5536 Phase 2
0.6899 Remote Similarity NPD3705 Approved
0.6899 Remote Similarity NPD422 Phase 1
0.689 Remote Similarity NPD6233 Phase 2

  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