Structure

Physi-Chem Properties

Molecular Weight:  400.12
Volume:  380.856
LogP:  1.284
LogD:  1.45
LogS:  -3.798
# Rotatable Bonds:  3
TPSA:  103.68
# H-Bond Aceptor:  8
# H-Bond Donor:  2
# Rings:  5
# Heavy Atoms:  8

MedChem Properties

QED Drug-Likeness Score:  0.755
Synthetic Accessibility Score:  3.814
Fsp3:  0.381
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  1
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.867
MDCK Permeability:  1.89152287930483e-05
Pgp-inhibitor:  0.103
Pgp-substrate:  0.005
Human Intestinal Absorption (HIA):  0.003
20% Bioavailability (F20%):  0.006
30% Bioavailability (F30%):  0.011

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.05
Plasma Protein Binding (PPB):  96.1812515258789%
Volume Distribution (VD):  1.088
Pgp-substrate:  3.7211530208587646%

ADMET: Metabolism

CYP1A2-inhibitor:  0.079
CYP1A2-substrate:  0.962
CYP2C19-inhibitor:  0.473
CYP2C19-substrate:  0.873
CYP2C9-inhibitor:  0.468
CYP2C9-substrate:  0.857
CYP2D6-inhibitor:  0.284
CYP2D6-substrate:  0.297
CYP3A4-inhibitor:  0.907
CYP3A4-substrate:  0.902

ADMET: Excretion

Clearance (CL):  7.512
Half-life (T1/2):  0.41

ADMET: Toxicity

hERG Blockers:  0.058
Human Hepatotoxicity (H-HT):  0.213
Drug-inuced Liver Injury (DILI):  0.584
AMES Toxicity:  0.024
Rat Oral Acute Toxicity:  0.125
Maximum Recommended Daily Dose:  0.935
Skin Sensitization:  0.147
Carcinogencity:  0.132
Eye Corrosion:  0.003
Eye Irritation:  0.061
Respiratory Toxicity:  0.786

Download Data

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

  Natural Product: NPC150943

Natural Product ID:  NPC150943
Common Name*:   4'-Demethylpodophyllotoxin
IUPAC Name:   (5R,5aR,8aR,9R)-5-hydroxy-9-(4-hydroxy-3,5-dimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[5,6-f][1,3]benzodioxol-8-one
Synonyms:   4'-Demethyl-Podophyllotoxin; 4'-Demethylpodophyllotoxin; 4-Demethyl-Podophyllotoxin
Standard InCHIKey:  YVCVYCSAAZQOJI-BTINSWFASA-N
Standard InCHI:  InChI=1S/C21H20O8/c1-25-15-3-9(4-16(26-2)20(15)23)17-10-5-13-14(29-8-28-13)6-11(10)19(22)12-7-27-21(24)18(12)17/h3-6,12,17-19,22-23H,7-8H2,1-2H3/t12-,17+,18-,19-/m0/s1
SMILES:  COc1cc(cc(c1O)OC)[C@@H]1c2cc3c(cc2[C@@H]([C@H]2COC(=O)[C@H]12)O)OCO3
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL28941
PubChem CID:   122667
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
NPO17807 Dysosma versipellis Species Berberidaceae Eukaryota n.a. root n.a. PMID[17256902]
NPO17807 Dysosma versipellis Species Berberidaceae Eukaryota Roots Panan, Zhejiang Province, China 2004-MAY PMID[17256902]
NPO14752 Sinopodophyllum emodi Species Berberidaceae Eukaryota roots and rhizomes n.a. n.a. PMID[21570846]
NPO17807 Dysosma versipellis Species Berberidaceae Eukaryota n.a. n.a. n.a. PMID[25712646]
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]
NPO3158 Linum album Species Linaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO17807 Dysosma versipellis Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO26868 Diphylleia sinensis Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO3158 Linum album Species Linaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO26868 Diphylleia sinensis Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO17807 Dysosma versipellis Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO30053 Podophyllum emodll Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO26868 Diphylleia sinensis Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO3158 Linum album Species Linaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO17807 Dysosma versipellis 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]
NPO17807 Dysosma versipellis Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
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]
NPO4464 Senecio mexicanus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1362 Swertia paniculata Species Gentianaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26868 Diphylleia sinensis Species Berberidaceae 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]
NPO3158 Linum album Species Linaceae 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
NPT3950 Cell Line GLC4 cell line IC50 = 30.0 nM PMID[515499]
NPT3950 Cell Line GLC4 cell line IC50 = 3100.0 nM PMID[515499]
NPT12 Individual Protein Human immunodeficiency virus type 1 integrase Human immunodeficiency virus 1 Inhibition < 5.0 % PMID[515500]
NPT306 Cell Line PC-3 Homo sapiens IC50 = 82.0 nM PMID[515501]
NPT858 Cell Line LNCaP Homo sapiens IC50 = 56.0 nM PMID[515501]
NPT1044 Individual Protein DNA topoisomerase II alpha Homo sapiens ID50 > 100.0 uM PMID[515502]
NPT1044 Individual Protein DNA topoisomerase II alpha Homo sapiens Activity = 1.1 % PMID[515502]
NPT1044 Individual Protein DNA topoisomerase II alpha Homo sapiens Inhibition = 25.0 % PMID[515504]
NPT91 Cell Line KB Homo sapiens ED50 = 0.045 ug ml-1 PMID[515504]
NPT1044 Individual Protein DNA topoisomerase II alpha Homo sapiens Inhibition = 3.3 % PMID[515504]
NPT168 Cell Line P388 Mus musculus T/C = 144.0 % PMID[515505]
NPT165 Cell Line HeLa Homo sapiens IC50 = 80.0 nM PMID[515506]
NPT91 Cell Line KB Homo sapiens IC50 = 64.0 nM PMID[515506]
NPT320 Protein Family DNA topoisomerase II Homo sapiens Protein-DNA complex formation = 3.3 % PMID[515498]
NPT190 Organism Human herpesvirus 1 Human herpesvirus 1 Activity = 500.0 nM PMID[515503]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Activity > 125.0 uM PMID[515503]
NPT27 Others Unspecified TI = 250.0 n.a. PMID[515503]
NPT190 Organism Human herpesvirus 1 Human herpesvirus 1 IC50 = 100.0 nM PMID[515503]
NPT195 Organism Vesicular stomatitis virus Vesicular stomatitis virus IC50 = 250.0 nM PMID[515503]

☑ 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 NPC150943 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 NPC268718
1.0 High Similarity NPC91634
0.9805 High Similarity NPC14294
0.9805 High Similarity NPC116759
0.9801 High Similarity NPC32373
0.9801 High Similarity NPC237946
0.9737 High Similarity NPC163527
0.9737 High Similarity NPC181168
0.9737 High Similarity NPC115281
0.9737 High Similarity NPC19947
0.9737 High Similarity NPC207584
0.9669 High Similarity NPC30009
0.9669 High Similarity NPC103197
0.9618 High Similarity NPC185498
0.961 High Similarity NPC119910
0.9603 High Similarity NPC245948
0.9603 High Similarity NPC178574
0.9603 High Similarity NPC65591
0.9548 High Similarity NPC288149
0.9548 High Similarity NPC152424
0.9548 High Similarity NPC100465
0.9497 High Similarity NPC179240
0.9484 High Similarity NPC96593
0.947 High Similarity NPC210642
0.947 High Similarity NPC13985
0.9423 High Similarity NPC115624
0.9412 High Similarity NPC136757
0.9367 High Similarity NPC222531
0.9338 High Similarity NPC474965
0.9338 High Similarity NPC174512
0.9338 High Similarity NPC293757
0.9338 High Similarity NPC668
0.9338 High Similarity NPC477695
0.9308 High Similarity NPC306475
0.9286 High Similarity NPC273578
0.9281 High Similarity NPC477699
0.9276 High Similarity NPC149505
0.9276 High Similarity NPC24425
0.9216 High Similarity NPC477700
0.9211 High Similarity NPC216223
0.9211 High Similarity NPC145569
0.9205 High Similarity NPC104024
0.9205 High Similarity NPC65574
0.9205 High Similarity NPC80230
0.9205 High Similarity NPC101755
0.9205 High Similarity NPC304687
0.9193 High Similarity NPC117911
0.9156 High Similarity NPC56184
0.9139 High Similarity NPC212890
0.9103 High Similarity NPC238834
0.9091 High Similarity NPC32079
0.9085 High Similarity NPC177476
0.9085 High Similarity NPC262455
0.9085 High Similarity NPC125570
0.9085 High Similarity NPC477698
0.9073 High Similarity NPC477702
0.9068 High Similarity NPC474042
0.9068 High Similarity NPC174734
0.8974 High Similarity NPC474606
0.8974 High Similarity NPC473236
0.8968 High Similarity NPC475756
0.8968 High Similarity NPC164082
0.8968 High Similarity NPC303519
0.894 High Similarity NPC477697
0.894 High Similarity NPC477696
0.894 High Similarity NPC470811
0.8924 High Similarity NPC478055
0.8916 High Similarity NPC196771
0.891 High Similarity NPC476434
0.891 High Similarity NPC471154
0.8903 High Similarity NPC473989
0.8896 High Similarity NPC311912
0.8896 High Similarity NPC304821
0.8874 High Similarity NPC151423
0.8874 High Similarity NPC40237
0.8874 High Similarity NPC287124
0.8854 High Similarity NPC61604
0.8854 High Similarity NPC299706
0.8854 High Similarity NPC245615
0.8854 High Similarity NPC115466
0.8841 High Similarity NPC88557
0.8816 High Similarity NPC106920
0.8816 High Similarity NPC273657
0.8797 High Similarity NPC312763
0.8797 High Similarity NPC178195
0.8797 High Similarity NPC348849
0.8782 High Similarity NPC185955
0.8782 High Similarity NPC214326
0.8782 High Similarity NPC9933
0.8782 High Similarity NPC218041
0.8782 High Similarity NPC182368
0.8782 High Similarity NPC260781
0.8782 High Similarity NPC469706
0.8782 High Similarity NPC145979
0.8782 High Similarity NPC469707
0.8782 High Similarity NPC225815
0.878 High Similarity NPC79322
0.8774 High Similarity NPC316676
0.8774 High Similarity NPC262804
0.8774 High Similarity NPC325720
0.8774 High Similarity NPC40654
0.8766 High Similarity NPC3982
0.8765 High Similarity NPC22130
0.8765 High Similarity NPC116838
0.8758 High Similarity NPC474770
0.8758 High Similarity NPC27159
0.8758 High Similarity NPC218841
0.8758 High Similarity NPC475000
0.8758 High Similarity NPC166884
0.8758 High Similarity NPC141569
0.8758 High Similarity NPC92693
0.8758 High Similarity NPC477701
0.875 High Similarity NPC52664
0.875 High Similarity NPC191231
0.875 High Similarity NPC210354
0.875 High Similarity NPC176586
0.8742 High Similarity NPC177868
0.8742 High Similarity NPC38699
0.8742 High Similarity NPC476065
0.8735 High Similarity NPC471181
0.8701 High Similarity NPC223185
0.8696 High Similarity NPC474043
0.8696 High Similarity NPC215400
0.8696 High Similarity NPC230531
0.8693 High Similarity NPC12728
0.8693 High Similarity NPC185071
0.8693 High Similarity NPC474288
0.8688 High Similarity NPC163635
0.8684 High Similarity NPC282291
0.8684 High Similarity NPC100675
0.8684 High Similarity NPC29599
0.8684 High Similarity NPC166137
0.8679 High Similarity NPC473425
0.8679 High Similarity NPC198461
0.8667 High Similarity NPC167231
0.8667 High Similarity NPC215802
0.8662 High Similarity NPC158635
0.8662 High Similarity NPC229882
0.8654 High Similarity NPC130449
0.8654 High Similarity NPC248132
0.865 High Similarity NPC76687
0.8645 High Similarity NPC193779
0.8645 High Similarity NPC252286
0.8645 High Similarity NPC33832
0.8645 High Similarity NPC154971
0.8642 High Similarity NPC470637
0.8636 High Similarity NPC187774
0.8636 High Similarity NPC472713
0.8636 High Similarity NPC118385
0.8636 High Similarity NPC177644
0.8636 High Similarity NPC473046
0.8636 High Similarity NPC472712
0.8636 High Similarity NPC191158
0.8634 High Similarity NPC475592
0.8631 High Similarity NPC469438
0.8631 High Similarity NPC193377
0.8625 High Similarity NPC234730
0.8625 High Similarity NPC186316
0.8623 High Similarity NPC129930
0.8623 High Similarity NPC20114
0.8623 High Similarity NPC312006
0.8623 High Similarity NPC474075
0.8623 High Similarity NPC178737
0.8623 High Similarity NPC114550
0.8623 High Similarity NPC471922
0.8623 High Similarity NPC471920
0.8623 High Similarity NPC471921
0.8623 High Similarity NPC292712
0.8616 High Similarity NPC24562
0.8609 High Similarity NPC474039
0.8606 High Similarity NPC320471
0.8606 High Similarity NPC83049
0.8606 High Similarity NPC118162
0.8599 High Similarity NPC55158
0.8599 High Similarity NPC51328
0.8599 High Similarity NPC286235
0.8598 High Similarity NPC475865
0.8598 High Similarity NPC469518
0.8598 High Similarity NPC469475
0.859 High Similarity NPC116019
0.8589 High Similarity NPC191352
0.8589 High Similarity NPC239890
0.8589 High Similarity NPC258322
0.8589 High Similarity NPC209411
0.8581 High Similarity NPC189239
0.8581 High Similarity NPC475868
0.8581 High Similarity NPC197352
0.8581 High Similarity NPC166506
0.8581 High Similarity NPC110763
0.858 High Similarity NPC473713
0.858 High Similarity NPC173726
0.858 High Similarity NPC23593
0.858 High Similarity NPC469397
0.858 High Similarity NPC241600
0.8571 High Similarity NPC29727
0.8571 High Similarity NPC255566
0.8571 High Similarity NPC228357
0.8571 High Similarity NPC165483
0.8571 High Similarity NPC298317
0.8571 High Similarity NPC184624

  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 NPC150943 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
0.9934 High Similarity NPD6234 Discontinued
0.9801 High Similarity NPD4966 Approved
0.9801 High Similarity NPD4965 Approved
0.9801 High Similarity NPD4967 Phase 2
0.9618 High Similarity NPD7228 Approved
0.9603 High Similarity NPD37 Approved
0.9024 High Similarity NPD7240 Approved
0.882 High Similarity NPD7199 Phase 2
0.8639 High Similarity NPD7090 Clinical (unspecified phase)
0.8598 High Similarity NPD7184 Clinical (unspecified phase)
0.858 High Similarity NPD7237 Clinical (unspecified phase)
0.8389 Intermediate Similarity NPD7680 Approved
0.8372 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.8225 Intermediate Similarity NPD3818 Discontinued
0.8121 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.8113 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.8095 Intermediate Similarity NPD6232 Discontinued
0.8059 Intermediate Similarity NPD7473 Discontinued
0.7965 Intermediate Similarity NPD5844 Phase 1
0.7963 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7961 Intermediate Similarity NPD3027 Phase 3
0.7919 Intermediate Similarity NPD7074 Phase 3
0.7886 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.7861 Intermediate Similarity NPD7054 Approved
0.7829 Intermediate Similarity NPD6559 Discontinued
0.7816 Intermediate Similarity NPD7472 Approved
0.7805 Intermediate Similarity NPD1653 Approved
0.7784 Intermediate Similarity NPD1465 Phase 2
0.775 Intermediate Similarity NPD6674 Discontinued
0.7727 Intermediate Similarity NPD7685 Pre-registration
0.7725 Intermediate Similarity NPD1934 Approved
0.7722 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7692 Intermediate Similarity NPD1613 Approved
0.7692 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7688 Intermediate Similarity NPD6166 Phase 2
0.7688 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.7688 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.7679 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.767 Intermediate Similarity NPD6797 Phase 2
0.767 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7656 Intermediate Similarity NPD7827 Phase 1
0.7654 Intermediate Similarity NPD6190 Approved
0.7627 Intermediate Similarity NPD7251 Discontinued
0.7625 Intermediate Similarity NPD7266 Discontinued
0.7622 Intermediate Similarity NPD2533 Approved
0.7622 Intermediate Similarity NPD2532 Approved
0.7622 Intermediate Similarity NPD2534 Approved
0.7616 Intermediate Similarity NPD8127 Discontinued
0.7588 Intermediate Similarity NPD3882 Suspended
0.7584 Intermediate Similarity NPD7808 Phase 3
0.758 Intermediate Similarity NPD3619 Clinical (unspecified phase)
0.758 Intermediate Similarity NPD3620 Phase 2
0.7574 Intermediate Similarity NPD2801 Approved
0.7574 Intermediate Similarity NPD8455 Phase 2
0.7572 Intermediate Similarity NPD7229 Phase 3
0.755 Intermediate Similarity NPD3705 Approved
0.7544 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.7542 Intermediate Similarity NPD8313 Approved
0.7542 Intermediate Similarity NPD8312 Approved
0.7541 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7529 Intermediate Similarity NPD3817 Phase 2
0.7484 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7471 Intermediate Similarity NPD3787 Discontinued
0.7457 Intermediate Similarity NPD5494 Approved
0.7436 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7421 Intermediate Similarity NPD230 Phase 1
0.741 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7396 Intermediate Similarity NPD7028 Phase 2
0.7396 Intermediate Similarity NPD4380 Phase 2
0.7378 Intermediate Similarity NPD4110 Phase 3
0.7378 Intermediate Similarity NPD4109 Clinical (unspecified phase)
0.7378 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7368 Intermediate Similarity NPD7819 Suspended
0.7362 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.736 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.7358 Intermediate Similarity NPD4060 Phase 1
0.7346 Intermediate Similarity NPD2438 Suspended
0.7342 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7341 Intermediate Similarity NPD7075 Discontinued
0.732 Intermediate Similarity NPD8151 Discontinued
0.7314 Intermediate Similarity NPD6959 Discontinued
0.7312 Intermediate Similarity NPD6355 Discontinued
0.7303 Intermediate Similarity NPD3751 Discontinued
0.7273 Intermediate Similarity NPD4628 Phase 3
0.7273 Intermediate Similarity NPD3750 Approved
0.7273 Intermediate Similarity NPD8166 Discontinued
0.7258 Intermediate Similarity NPD7296 Approved
0.7251 Intermediate Similarity NPD7615 Clinical (unspecified phase)
0.7246 Intermediate Similarity NPD1511 Approved
0.7239 Intermediate Similarity NPD6100 Approved
0.7239 Intermediate Similarity NPD6099 Approved
0.7233 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7233 Intermediate Similarity NPD6798 Discontinued
0.7225 Intermediate Similarity NPD5402 Approved
0.7222 Intermediate Similarity NPD7097 Phase 1
0.7215 Intermediate Similarity NPD4908 Phase 1
0.7209 Intermediate Similarity NPD6801 Discontinued
0.7195 Intermediate Similarity NPD6004 Phase 3
0.7195 Intermediate Similarity NPD5762 Approved
0.7195 Intermediate Similarity NPD6002 Phase 3
0.7195 Intermediate Similarity NPD6003 Clinical (unspecified phase)
0.7195 Intermediate Similarity NPD6005 Phase 3
0.7195 Intermediate Similarity NPD6006 Clinical (unspecified phase)
0.7195 Intermediate Similarity NPD5763 Approved
0.7188 Intermediate Similarity NPD5005 Approved
0.7188 Intermediate Similarity NPD6233 Phase 2
0.7188 Intermediate Similarity NPD5006 Approved
0.7188 Intermediate Similarity NPD6663 Approved
0.7179 Intermediate Similarity NPD1283 Approved
0.7168 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.716 Intermediate Similarity NPD6273 Approved
0.716 Intermediate Similarity NPD1512 Approved
0.715 Intermediate Similarity NPD7435 Discontinued
0.7143 Intermediate Similarity NPD4140 Approved
0.7143 Intermediate Similarity NPD2979 Phase 3
0.7135 Intermediate Similarity NPD7458 Discontinued
0.7135 Intermediate Similarity NPD8434 Phase 2
0.7135 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7126 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.7125 Intermediate Similarity NPD3764 Approved
0.7101 Intermediate Similarity NPD7422 Clinical (unspecified phase)
0.7086 Intermediate Similarity NPD7768 Phase 2
0.7083 Intermediate Similarity NPD6780 Approved
0.7083 Intermediate Similarity NPD6781 Approved
0.7083 Intermediate Similarity NPD6776 Approved
0.7083 Intermediate Similarity NPD6778 Approved
0.7083 Intermediate Similarity NPD6777 Approved
0.7083 Intermediate Similarity NPD6779 Approved
0.7083 Intermediate Similarity NPD6782 Approved
0.7079 Intermediate Similarity NPD5711 Approved
0.7079 Intermediate Similarity NPD5710 Approved
0.7068 Intermediate Similarity NPD4420 Approved
0.7066 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7063 Intermediate Similarity NPD4625 Phase 3
0.7052 Intermediate Similarity NPD7411 Suspended
0.7045 Intermediate Similarity NPD3749 Approved
0.7044 Intermediate Similarity NPD5736 Approved
0.7035 Intermediate Similarity NPD3226 Approved
0.703 Intermediate Similarity NPD2935 Discontinued
0.7019 Intermediate Similarity NPD6410 Clinical (unspecified phase)
0.7019 Intermediate Similarity NPD1699 Clinical (unspecified phase)
0.7018 Intermediate Similarity NPD5403 Approved
0.7013 Intermediate Similarity NPD1357 Approved
0.701 Intermediate Similarity NPD6823 Phase 2
0.7006 Intermediate Similarity NPD5698 Clinical (unspecified phase)
0.7006 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD6723 Discontinued
0.7 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.6994 Remote Similarity NPD6599 Discontinued
0.6994 Remote Similarity NPD5735 Approved
0.6987 Remote Similarity NPD1281 Approved
0.6987 Remote Similarity NPD1610 Phase 2
0.6985 Remote Similarity NPD7783 Phase 2
0.6985 Remote Similarity NPD7782 Clinical (unspecified phase)
0.6981 Remote Similarity NPD6917 Clinical (unspecified phase)
0.6975 Remote Similarity NPD8032 Phase 2
0.697 Remote Similarity NPD7033 Discontinued
0.697 Remote Similarity NPD3748 Approved
0.6968 Remote Similarity NPD5125 Phase 3
0.6968 Remote Similarity NPD5126 Approved
0.6966 Remote Similarity NPD6746 Phase 2
0.6959 Remote Similarity NPD2493 Approved
0.6959 Remote Similarity NPD2494 Approved
0.6957 Remote Similarity NPD7095 Approved
0.6952 Remote Similarity NPD8150 Discontinued
0.6951 Remote Similarity NPD6653 Approved
0.6949 Remote Similarity NPD7975 Clinical (unspecified phase)
0.6944 Remote Similarity NPD5242 Approved
0.6943 Remote Similarity NPD1608 Approved
0.6941 Remote Similarity NPD6799 Approved
0.6939 Remote Similarity NPD4583 Approved
0.6939 Remote Similarity NPD4582 Approved
0.6937 Remote Similarity NPD3018 Phase 2
0.6937 Remote Similarity NPD2861 Phase 2
0.6935 Remote Similarity NPD7874 Approved
0.6935 Remote Similarity NPD7875 Clinical (unspecified phase)
0.6932 Remote Similarity NPD5353 Approved
0.6923 Remote Similarity NPD5084 Clinical (unspecified phase)
0.6918 Remote Similarity NPD2797 Approved
0.691 Remote Similarity NPD919 Approved
0.6906 Remote Similarity NPD7852 Clinical (unspecified phase)
0.6905 Remote Similarity NPD7421 Clinical (unspecified phase)
0.6901 Remote Similarity NPD5401 Approved
0.6899 Remote Similarity NPD4749 Approved
0.6899 Remote Similarity NPD2983 Phase 2
0.6899 Remote Similarity NPD2982 Phase 2
0.689 Remote Similarity NPD5124 Phase 1
0.689 Remote Similarity NPD5123 Clinical (unspecified phase)
0.6888 Remote Similarity NPD4002 Approved
0.6888 Remote Similarity NPD4004 Approved
0.6888 Remote Similarity NPD7697 Approved
0.6888 Remote Similarity NPD7696 Phase 3
0.6888 Remote Similarity NPD7698 Approved
0.6886 Remote Similarity NPD1552 Clinical (unspecified phase)
0.6886 Remote Similarity NPD1550 Clinical (unspecified phase)
0.6882 Remote Similarity NPD5058 Phase 3
0.6881 Remote Similarity NPD7930 Approved
0.6879 Remote Similarity NPD1091 Approved
0.6875 Remote Similarity NPD2977 Approved
0.6875 Remote Similarity NPD2978 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