Structure

Physi-Chem Properties

Molecular Weight:  562.17
Volume:  520.027
LogP:  0.545
LogD:  0.482
LogS:  -2.494
# Rotatable Bonds:  6
TPSA:  182.83
# H-Bond Aceptor:  13
# H-Bond Donor:  5
# Rings:  6
# Heavy Atoms:  13

MedChem Properties

QED Drug-Likeness Score:  0.295
Synthetic Accessibility Score:  4.602
Fsp3:  0.519
Lipinski Rule-of-5:  Rejected
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:  -6.264
MDCK Permeability:  3.988061871496029e-05
Pgp-inhibitor:  0.007
Pgp-substrate:  0.979
Human Intestinal Absorption (HIA):  0.009
20% Bioavailability (F20%):  0.009
30% Bioavailability (F30%):  0.016

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.043
Plasma Protein Binding (PPB):  92.73946380615234%
Volume Distribution (VD):  0.74
Pgp-substrate:  5.622928619384766%

ADMET: Metabolism

CYP1A2-inhibitor:  0.019
CYP1A2-substrate:  0.926
CYP2C19-inhibitor:  0.02
CYP2C19-substrate:  0.832
CYP2C9-inhibitor:  0.02
CYP2C9-substrate:  0.215
CYP2D6-inhibitor:  0.019
CYP2D6-substrate:  0.159
CYP3A4-inhibitor:  0.669
CYP3A4-substrate:  0.753

ADMET: Excretion

Clearance (CL):  3.907
Half-life (T1/2):  0.465

ADMET: Toxicity

hERG Blockers:  0.208
Human Hepatotoxicity (H-HT):  0.349
Drug-inuced Liver Injury (DILI):  0.3
AMES Toxicity:  0.32
Rat Oral Acute Toxicity:  0.045
Maximum Recommended Daily Dose:  0.839
Skin Sensitization:  0.055
Carcinogencity:  0.114
Eye Corrosion:  0.003
Eye Irritation:  0.014
Respiratory Toxicity:  0.18

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

  Natural Product: NPC14294

Natural Product ID:  NPC14294
Common Name*:   4-Demethyl-Podophyllotoxin-7'-O-Beta-D-Glucopyranoside
IUPAC Name:   (5R,5aR,8aR,9R)-9-(4-hydroxy-3,5-dimethoxyphenyl)-5-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[6,5-f][1,3]benzodioxol-8-one
Synonyms:  
Standard InCHIKey:  FOVRGQUEGRCWPD-CZIVDZDDSA-N
Standard InCHI:  InChI=1S/C27H30O13/c1-34-16-3-10(4-17(35-2)21(16)29)19-11-5-14-15(38-9-37-14)6-12(11)25(13-8-36-26(33)20(13)19)40-27-24(32)23(31)22(30)18(7-28)39-27/h3-6,13,18-20,22-25,27-32H,7-9H2,1-2H3/t13-,18+,19+,20-,22+,23-,24+,25-,27-/m0/s1
SMILES:  OC[C@H]1O[C@@H](O[C@@H]2[C@H]3COC(=O)[C@@H]3[C@@H](c3c2cc2OCOc2c3)c2cc(OC)c(c(c2)OC)O)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1778162
PubChem CID:   170385
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0001392] Lignans, neolignans and related compounds
      • [CHEMONTID:0001510] Lignan lactones
        • [CHEMONTID:0000047] Podophyllotoxins

*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
NPO14752 Sinopodophyllum emodi Species Berberidaceae Eukaryota roots and rhizomes n.a. n.a. PMID[21570846]
NPO11163 Methylobacterium organophilum Species Methylobacteriaceae Bacteria n.a. n.a. n.a. PMID[26032177]
NPO10903 Sinopodophyllum hexandrum Species Berberidaceae Eukaryota n.a. n.a. n.a. PMID[26359402]
NPO11163 Methylobacterium organophilum Species Methylobacteriaceae Bacteria n.a. n.a. n.a. PMID[3928379]
NPO1362 Swertia paniculata Species Gentianaceae Eukaryota n.a. n.a. n.a. Database[Article]
NPO30053 Podophyllum emodll Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO10903 Sinopodophyllum hexandrum Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO10903 Sinopodophyllum hexandrum Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6738 Cladonia incrassata Species Cladoniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1362 Swertia paniculata Species Gentianaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4464 Senecio mexicanus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6893 Dimorphotheca sinuata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14752 Sinopodophyllum emodi Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3025 Schefflera capitata Species Araliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11163 Methylobacterium organophilum Species Methylobacteriaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO11417 Gesneria cardinalis Species Crambidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4534 Croton nitens Species Euphorbiaceae 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
NPT165 Cell Line HeLa Homo sapiens IC50 = 5330.0 nM PMID[448998]
NPT91 Cell Line KB Homo sapiens IC50 = 9510.0 nM PMID[448998]

☑ 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 NPC14294 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 NPC116759
0.9809 High Similarity NPC185498
0.9805 High Similarity NPC91634
0.9805 High Similarity NPC268718
0.9805 High Similarity NPC150943
0.9742 High Similarity NPC100465
0.9742 High Similarity NPC152424
0.9686 High Similarity NPC179240
0.9615 High Similarity NPC115624
0.961 High Similarity NPC237946
0.961 High Similarity NPC32373
0.9557 High Similarity NPC222531
0.9548 High Similarity NPC115281
0.9548 High Similarity NPC163527
0.9548 High Similarity NPC181168
0.9548 High Similarity NPC19947
0.9548 High Similarity NPC207584
0.9497 High Similarity NPC306475
0.9481 High Similarity NPC30009
0.9481 High Similarity NPC103197
0.9427 High Similarity NPC119910
0.9416 High Similarity NPC65591
0.9416 High Similarity NPC178574
0.9416 High Similarity NPC245948
0.9367 High Similarity NPC288149
0.9304 High Similarity NPC96593
0.9286 High Similarity NPC13985
0.9286 High Similarity NPC210642
0.9231 High Similarity NPC136757
0.9156 High Similarity NPC293757
0.9156 High Similarity NPC668
0.9156 High Similarity NPC174512
0.9156 High Similarity NPC477695
0.9156 High Similarity NPC474965
0.9108 High Similarity NPC273578
0.9103 High Similarity NPC477699
0.9097 High Similarity NPC24425
0.9097 High Similarity NPC149505
0.9038 High Similarity NPC477700
0.9032 High Similarity NPC145569
0.9032 High Similarity NPC216223
0.9026 High Similarity NPC80230
0.9026 High Similarity NPC101755
0.9026 High Similarity NPC304687
0.9026 High Similarity NPC104024
0.9026 High Similarity NPC65574
0.9024 High Similarity NPC117911
0.8994 High Similarity NPC478055
0.8981 High Similarity NPC56184
0.8974 High Similarity NPC145979
0.8974 High Similarity NPC469707
0.8974 High Similarity NPC185955
0.8974 High Similarity NPC260781
0.8974 High Similarity NPC469706
0.8974 High Similarity NPC214326
0.8974 High Similarity NPC225815
0.8974 High Similarity NPC218041
0.8974 High Similarity NPC9933
0.8974 High Similarity NPC182368
0.8961 High Similarity NPC212890
0.8931 High Similarity NPC238834
0.8924 High Similarity NPC115466
0.8924 High Similarity NPC245615
0.8924 High Similarity NPC61604
0.8924 High Similarity NPC299706
0.8917 High Similarity NPC32079
0.891 High Similarity NPC125570
0.891 High Similarity NPC262455
0.891 High Similarity NPC477698
0.891 High Similarity NPC177476
0.8902 High Similarity NPC474042
0.8902 High Similarity NPC174734
0.8896 High Similarity NPC477702
0.8812 High Similarity NPC38699
0.881 High Similarity NPC193377
0.8805 High Similarity NPC473236
0.8805 High Similarity NPC474606
0.8802 High Similarity NPC292712
0.8802 High Similarity NPC471921
0.8802 High Similarity NPC114550
0.8802 High Similarity NPC129930
0.8802 High Similarity NPC474075
0.8802 High Similarity NPC471920
0.8802 High Similarity NPC471922
0.8802 High Similarity NPC312006
0.8802 High Similarity NPC20114
0.8797 High Similarity NPC303519
0.8797 High Similarity NPC164082
0.8797 High Similarity NPC475756
0.8766 High Similarity NPC470811
0.8766 High Similarity NPC477697
0.8766 High Similarity NPC477696
0.8758 High Similarity NPC163635
0.8757 High Similarity NPC469397
0.8757 High Similarity NPC196771
0.8742 High Similarity NPC21902
0.8742 High Similarity NPC476434
0.8742 High Similarity NPC471154
0.8735 High Similarity NPC311912
0.8734 High Similarity NPC473989
0.8734 High Similarity NPC229882
0.8734 High Similarity NPC158635
0.8726 High Similarity NPC130449
0.8726 High Similarity NPC304821
0.8726 High Similarity NPC248132
0.8713 High Similarity NPC188217
0.871 High Similarity NPC472712
0.871 High Similarity NPC118385
0.871 High Similarity NPC472713
0.871 High Similarity NPC187774
0.871 High Similarity NPC473046
0.8706 High Similarity NPC260300
0.8701 High Similarity NPC151423
0.8701 High Similarity NPC287124
0.8701 High Similarity NPC40237
0.8698 High Similarity NPC469438
0.8696 High Similarity NPC186316
0.8693 High Similarity NPC476358
0.8683 High Similarity NPC88557
0.8671 High Similarity NPC286235
0.8671 High Similarity NPC55158
0.8671 High Similarity NPC51328
0.8667 High Similarity NPC25889
0.8654 High Similarity NPC286245
0.8654 High Similarity NPC272619
0.865 High Similarity NPC241600
0.865 High Similarity NPC173726
0.8647 High Similarity NPC472723
0.8647 High Similarity NPC473713
0.8645 High Similarity NPC273657
0.8645 High Similarity NPC106920
0.8642 High Similarity NPC228357
0.8642 High Similarity NPC165483
0.8634 High Similarity NPC312763
0.8634 High Similarity NPC178195
0.8634 High Similarity NPC348849
0.8625 High Similarity NPC302610
0.8623 High Similarity NPC167231
0.8623 High Similarity NPC79322
0.8623 High Similarity NPC215802
0.8616 High Similarity NPC472709
0.8616 High Similarity NPC472710
0.8614 High Similarity NPC475738
0.8608 High Similarity NPC262804
0.8608 High Similarity NPC325720
0.8608 High Similarity NPC316676
0.8608 High Similarity NPC40654
0.8606 High Similarity NPC116838
0.8606 High Similarity NPC22130
0.8605 High Similarity NPC53680
0.8605 High Similarity NPC208797
0.8605 High Similarity NPC170203
0.8599 High Similarity NPC3982
0.8598 High Similarity NPC474770
0.8598 High Similarity NPC24627
0.8596 High Similarity NPC80360
0.8596 High Similarity NPC35266
0.859 High Similarity NPC141569
0.859 High Similarity NPC253015
0.859 High Similarity NPC471065
0.859 High Similarity NPC166884
0.859 High Similarity NPC475000
0.859 High Similarity NPC218841
0.859 High Similarity NPC92693
0.859 High Similarity NPC477701
0.859 High Similarity NPC27159
0.8589 High Similarity NPC472860
0.8588 High Similarity NPC469354
0.8581 High Similarity NPC5262
0.8581 High Similarity NPC210354
0.8581 High Similarity NPC191231
0.8581 High Similarity NPC52664
0.8581 High Similarity NPC472714
0.8581 High Similarity NPC176586
0.858 High Similarity NPC471181
0.858 High Similarity NPC476065
0.8571 High Similarity NPC177868
0.8563 High Similarity NPC59516
0.8556 High Similarity NPC473803
0.8553 High Similarity NPC44452
0.8547 High Similarity NPC212290
0.8547 High Similarity NPC195114
0.8547 High Similarity NPC161609
0.8547 High Similarity NPC275690
0.8545 High Similarity NPC109061
0.8545 High Similarity NPC177100
0.8545 High Similarity NPC139540
0.8544 High Similarity NPC39657
0.8538 High Similarity NPC79736
0.8538 High Similarity NPC67629
0.8538 High Similarity NPC297574
0.8537 High Similarity NPC474043
0.8537 High Similarity NPC230531
0.8537 High Similarity NPC215400
0.8535 High Similarity NPC223185
0.8529 High Similarity NPC166674
0.8529 High Similarity NPC184624
0.8529 High Similarity NPC46640
0.8529 High Similarity NPC219600
0.8529 High Similarity NPC263119

  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 NPC14294 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
0.9809 High Similarity NPD7228 Approved
0.974 High Similarity NPD6234 Discontinued
0.961 High Similarity NPD4966 Approved
0.961 High Similarity NPD4965 Approved
0.961 High Similarity NPD4967 Phase 2
0.9416 High Similarity NPD37 Approved
0.9207 High Similarity NPD7240 Approved
0.875 High Similarity NPD7237 Clinical (unspecified phase)
0.8659 High Similarity NPD7199 Phase 2
0.8556 High Similarity NPD7680 Approved
0.8488 Intermediate Similarity NPD7090 Clinical (unspecified phase)
0.8443 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.8439 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.8193 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.8187 Intermediate Similarity NPD3818 Discontinued
0.8092 Intermediate Similarity NPD7074 Phase 3
0.8057 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.8035 Intermediate Similarity NPD7054 Approved
0.8035 Intermediate Similarity NPD5844 Phase 1
0.7989 Intermediate Similarity NPD7472 Approved
0.7963 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7953 Intermediate Similarity NPD6232 Discontinued
0.7937 Intermediate Similarity NPD6674 Discontinued
0.7919 Intermediate Similarity NPD7473 Discontinued
0.7898 Intermediate Similarity NPD7685 Pre-registration
0.7898 Intermediate Similarity NPD6559 Discontinued
0.7879 Intermediate Similarity NPD1653 Approved
0.7857 Intermediate Similarity NPD1465 Phase 2
0.7841 Intermediate Similarity NPD6797 Phase 2
0.7818 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7812 Intermediate Similarity NPD7266 Discontinued
0.7806 Intermediate Similarity NPD3027 Phase 3
0.7797 Intermediate Similarity NPD7251 Discontinued
0.7759 Intermediate Similarity NPD6166 Phase 2
0.7759 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.7759 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.7753 Intermediate Similarity NPD7808 Phase 3
0.7751 Intermediate Similarity NPD8455 Phase 2
0.774 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7719 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.7709 Intermediate Similarity NPD8313 Approved
0.7709 Intermediate Similarity NPD8312 Approved
0.7705 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7692 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7692 Intermediate Similarity NPD1934 Approved
0.7658 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7658 Intermediate Similarity NPD1613 Approved
0.7647 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7586 Intermediate Similarity NPD8127 Discontinued
0.7543 Intermediate Similarity NPD3787 Discontinued
0.7538 Intermediate Similarity NPD7827 Phase 1
0.7529 Intermediate Similarity NPD5494 Approved
0.7528 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.7515 Intermediate Similarity NPD6190 Approved
0.7485 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7485 Intermediate Similarity NPD2532 Approved
0.7485 Intermediate Similarity NPD2533 Approved
0.7485 Intermediate Similarity NPD2534 Approved
0.7474 Intermediate Similarity NPD8151 Discontinued
0.7471 Intermediate Similarity NPD4380 Phase 2
0.7457 Intermediate Similarity NPD3882 Suspended
0.7452 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7443 Intermediate Similarity NPD7229 Phase 3
0.7442 Intermediate Similarity NPD2801 Approved
0.7438 Intermediate Similarity NPD3620 Phase 2
0.7438 Intermediate Similarity NPD3619 Clinical (unspecified phase)
0.7405 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7403 Intermediate Similarity NPD3705 Approved
0.7399 Intermediate Similarity NPD3817 Phase 2
0.7386 Intermediate Similarity NPD6959 Discontinued
0.7374 Intermediate Similarity NPD3751 Discontinued
0.7368 Intermediate Similarity NPD7028 Phase 2
0.7349 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7341 Intermediate Similarity NPD7819 Suspended
0.7314 Intermediate Similarity NPD7075 Discontinued
0.7312 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7306 Intermediate Similarity NPD7435 Discontinued
0.7301 Intermediate Similarity NPD7097 Phase 1
0.7296 Intermediate Similarity NPD4908 Phase 1
0.7284 Intermediate Similarity NPD230 Phase 1
0.7246 Intermediate Similarity NPD4110 Phase 3
0.7246 Intermediate Similarity NPD8166 Discontinued
0.7246 Intermediate Similarity NPD4109 Clinical (unspecified phase)
0.7246 Intermediate Similarity NPD3750 Approved
0.724 Intermediate Similarity NPD6782 Approved
0.724 Intermediate Similarity NPD6781 Approved
0.724 Intermediate Similarity NPD6777 Approved
0.724 Intermediate Similarity NPD6778 Approved
0.724 Intermediate Similarity NPD6779 Approved
0.724 Intermediate Similarity NPD6780 Approved
0.724 Intermediate Similarity NPD6776 Approved
0.7229 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7225 Intermediate Similarity NPD7615 Clinical (unspecified phase)
0.7222 Intermediate Similarity NPD4060 Phase 1
0.7212 Intermediate Similarity NPD2438 Suspended
0.7212 Intermediate Similarity NPD6099 Approved
0.7212 Intermediate Similarity NPD6100 Approved
0.7209 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7205 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.72 Intermediate Similarity NPD5402 Approved
0.72 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.7178 Intermediate Similarity NPD6355 Discontinued
0.7165 Intermediate Similarity NPD6823 Phase 2
0.7165 Intermediate Similarity NPD5006 Approved
0.7165 Intermediate Similarity NPD5005 Approved
0.7143 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD7296 Approved
0.7143 Intermediate Similarity NPD4628 Phase 3
0.7136 Intermediate Similarity NPD7782 Clinical (unspecified phase)
0.7136 Intermediate Similarity NPD7783 Phase 2
0.7135 Intermediate Similarity NPD6273 Approved
0.7126 Intermediate Similarity NPD7411 Suspended
0.7119 Intermediate Similarity NPD3749 Approved
0.7118 Intermediate Similarity NPD1511 Approved
0.711 Intermediate Similarity NPD7458 Discontinued
0.7099 Intermediate Similarity NPD6798 Discontinued
0.7086 Intermediate Similarity NPD6801 Discontinued
0.7085 Intermediate Similarity NPD7874 Approved
0.7085 Intermediate Similarity NPD7875 Clinical (unspecified phase)
0.7076 Intermediate Similarity NPD7422 Clinical (unspecified phase)
0.7066 Intermediate Similarity NPD5763 Approved
0.7066 Intermediate Similarity NPD5762 Approved
0.7066 Intermediate Similarity NPD6004 Phase 3
0.7066 Intermediate Similarity NPD6002 Phase 3
0.7066 Intermediate Similarity NPD6005 Phase 3
0.7066 Intermediate Similarity NPD6006 Clinical (unspecified phase)
0.7066 Intermediate Similarity NPD6003 Clinical (unspecified phase)
0.7062 Intermediate Similarity NPD7768 Phase 2
0.7056 Intermediate Similarity NPD5710 Approved
0.7056 Intermediate Similarity NPD5711 Approved
0.7055 Intermediate Similarity NPD6663 Approved
0.7055 Intermediate Similarity NPD6233 Phase 2
0.7047 Intermediate Similarity NPD4420 Approved
0.7044 Intermediate Similarity NPD1283 Approved
0.7041 Intermediate Similarity NPD7696 Phase 3
0.7041 Intermediate Similarity NPD7698 Approved
0.7041 Intermediate Similarity NPD7697 Approved
0.7037 Intermediate Similarity NPD4625 Phase 3
0.7035 Intermediate Similarity NPD1512 Approved
0.7026 Intermediate Similarity NPD2494 Approved
0.7026 Intermediate Similarity NPD2493 Approved
0.7021 Intermediate Similarity NPD8150 Discontinued
0.7021 Intermediate Similarity NPD8434 Phase 2
0.7012 Intermediate Similarity NPD2979 Phase 3
0.7012 Intermediate Similarity NPD4140 Approved
0.7005 Intermediate Similarity NPD8319 Approved
0.7005 Intermediate Similarity NPD7871 Phase 2
0.7005 Intermediate Similarity NPD4583 Approved
0.7005 Intermediate Similarity NPD8320 Phase 1
0.7005 Intermediate Similarity NPD7870 Phase 2
0.7005 Intermediate Similarity NPD4582 Approved
0.6994 Remote Similarity NPD5403 Approved
0.6994 Remote Similarity NPD3764 Approved
0.6994 Remote Similarity NPD6410 Clinical (unspecified phase)
0.6985 Remote Similarity NPD7701 Phase 2
0.6982 Remote Similarity NPD5698 Clinical (unspecified phase)
0.6981 Remote Similarity NPD6723 Discontinued
0.6979 Remote Similarity NPD6535 Approved
0.6979 Remote Similarity NPD6534 Approved
0.6978 Remote Similarity NPD7852 Clinical (unspecified phase)
0.697 Remote Similarity NPD5123 Clinical (unspecified phase)
0.697 Remote Similarity NPD5124 Phase 1
0.6965 Remote Similarity NPD7801 Approved
0.6962 Remote Similarity NPD1091 Approved
0.6962 Remote Similarity NPD1610 Phase 2
0.6954 Remote Similarity NPD4004 Approved
0.6954 Remote Similarity NPD4002 Approved
0.6946 Remote Similarity NPD3748 Approved
0.6946 Remote Similarity NPD7930 Approved
0.6943 Remote Similarity NPD5126 Approved
0.6943 Remote Similarity NPD5125 Phase 3
0.6941 Remote Similarity NPD1878 Clinical (unspecified phase)
0.6939 Remote Similarity NPD3450 Approved
0.6939 Remote Similarity NPD3452 Approved
0.6914 Remote Similarity NPD2861 Phase 2
0.6914 Remote Similarity NPD3226 Approved
0.6914 Remote Similarity NPD5736 Approved
0.6911 Remote Similarity NPD2488 Approved
0.6911 Remote Similarity NPD2490 Approved
0.691 Remote Similarity NPD5353 Approved
0.6905 Remote Similarity NPD2935 Discontinued
0.6898 Remote Similarity NPD7549 Discontinued
0.6895 Remote Similarity NPD6841 Approved
0.6895 Remote Similarity NPD6843 Phase 3
0.6895 Remote Similarity NPD6842 Approved
0.689 Remote Similarity NPD1699 Clinical (unspecified phase)
0.6886 Remote Similarity NPD4978 Clinical (unspecified phase)
0.6884 Remote Similarity NPD7999 Approved
0.6879 Remote Similarity NPD5401 Approved
0.6879 Remote Similarity NPD4378 Clinical (unspecified phase)
0.6879 Remote Similarity NPD1357 Approved
0.6875 Remote Similarity NPD4749 Approved
0.6875 Remote Similarity NPD4379 Clinical (unspecified phase)
0.6875 Remote Similarity NPD6599 Discontinued
0.6872 Remote Similarity NPD7700 Phase 2
0.6872 Remote Similarity NPD7699 Phase 2
0.6867 Remote Similarity NPD5735 Approved
0.6864 Remote Similarity NPD1552 Clinical (unspecified phase)
0.6864 Remote Similarity NPD1550 Clinical (unspecified phase)
0.686 Remote Similarity NPD5058 Phase 3

  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