Structure

Physi-Chem Properties

Molecular Weight:  618.19
Volume:  578.069
LogP:  1.247
LogD:  1.476
LogS:  -3.371
# Rotatable Bonds:  9
TPSA:  177.9
# H-Bond Aceptor:  14
# H-Bond Donor:  3
# Rings:  6
# Heavy Atoms:  14

MedChem Properties

QED Drug-Likeness Score:  0.354
Synthetic Accessibility Score:  4.648
Fsp3:  0.533
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:  -5.455
MDCK Permeability:  6.642563675995916e-05
Pgp-inhibitor:  0.169
Pgp-substrate:  0.902
Human Intestinal Absorption (HIA):  0.004
20% Bioavailability (F20%):  0.003
30% Bioavailability (F30%):  0.021

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.051
Plasma Protein Binding (PPB):  85.74859619140625%
Volume Distribution (VD):  0.696
Pgp-substrate:  11.365888595581055%

ADMET: Metabolism

CYP1A2-inhibitor:  0.013
CYP1A2-substrate:  0.947
CYP2C19-inhibitor:  0.042
CYP2C19-substrate:  0.869
CYP2C9-inhibitor:  0.044
CYP2C9-substrate:  0.089
CYP2D6-inhibitor:  0.025
CYP2D6-substrate:  0.145
CYP3A4-inhibitor:  0.802
CYP3A4-substrate:  0.903

ADMET: Excretion

Clearance (CL):  3.228
Half-life (T1/2):  0.305

ADMET: Toxicity

hERG Blockers:  0.191
Human Hepatotoxicity (H-HT):  0.361
Drug-inuced Liver Injury (DILI):  0.593
AMES Toxicity:  0.251
Rat Oral Acute Toxicity:  0.057
Maximum Recommended Daily Dose:  0.885
Skin Sensitization:  0.036
Carcinogencity:  0.089
Eye Corrosion:  0.003
Eye Irritation:  0.017
Respiratory Toxicity:  0.126

Download Data

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

  Natural Product: NPC100465

Natural Product ID:  NPC100465
Common Name*:   Sinolignan A
IUPAC Name:   [(2R,3S,4S,5R,6R)-6-[[(5R,5aR,8aR,9R)-8-oxo-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[6,5-f][1,3]benzodioxol-5-yl]oxy]-3,4,5-trihydroxyoxan-2-yl]methyl acetate
Synonyms:   sinolignan A
Standard InCHIKey:  DPKLCDRVJXJAEF-TZGCRGLASA-N
Standard InCHI:  InChI=1S/C30H34O14/c1-12(31)39-10-21-24(32)25(33)26(34)30(43-21)44-27-15-8-18-17(41-11-42-18)7-14(15)22(23-16(27)9-40-29(23)35)13-5-19(36-2)28(38-4)20(6-13)37-3/h5-8,16,21-27,30,32-34H,9-11H2,1-4H3/t16-,21+,22+,23-,24+,25-,26+,27-,30-/m0/s1
SMILES:  CC(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)O[C@H]1c2cc3c(cc2[C@@H](c2cc(c(c(c2)OC)OC)OC)[C@@H]2[C@@H]1COC2=O)OCO3)O)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1778158
PubChem CID:   54581698
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]
NPO10903 Sinopodophyllum hexandrum Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
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]
NPO10903 Sinopodophyllum hexandrum Species Berberidaceae 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 = 3770.0 nM PMID[496320]
NPT91 Cell Line KB Homo sapiens IC50 = 8760.0 nM PMID[496320]

☑ 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 NPC100465 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 NPC152424
0.9806 High Similarity NPC222531
0.9744 High Similarity NPC306475
0.9742 High Similarity NPC116759
0.9742 High Similarity NPC14294
0.974 High Similarity NPC115624
0.9682 High Similarity NPC185498
0.9608 High Similarity NPC32373
0.9608 High Similarity NPC237946
0.956 High Similarity NPC179240
0.9548 High Similarity NPC91634
0.9548 High Similarity NPC268718
0.9548 High Similarity NPC150943
0.9545 High Similarity NPC207584
0.9545 High Similarity NPC19947
0.9423 High Similarity NPC96593
0.9423 High Similarity NPC119910
0.9412 High Similarity NPC245948
0.9408 High Similarity NPC210642
0.9408 High Similarity NPC13985
0.9363 High Similarity NPC288149
0.9295 High Similarity NPC163527
0.9295 High Similarity NPC115281
0.9295 High Similarity NPC181168
0.9226 High Similarity NPC103197
0.9226 High Similarity NPC30009
0.9226 High Similarity NPC273578
0.9216 High Similarity NPC149505
0.9161 High Similarity NPC178574
0.9161 High Similarity NPC65591
0.9145 High Similarity NPC80230
0.9145 High Similarity NPC304687
0.9145 High Similarity NPC101755
0.9145 High Similarity NPC104024
0.9145 High Similarity NPC65574
0.9026 High Similarity NPC262455
0.9026 High Similarity NPC177476
0.9026 High Similarity NPC477698
0.8981 High Similarity NPC136757
0.8974 High Similarity NPC56184
0.8968 High Similarity NPC158635
0.8968 High Similarity NPC229882
0.891 High Similarity NPC164082
0.891 High Similarity NPC303519
0.8909 High Similarity NPC129930
0.8909 High Similarity NPC471922
0.8909 High Similarity NPC292712
0.8909 High Similarity NPC312006
0.8909 High Similarity NPC474075
0.8909 High Similarity NPC471920
0.8909 High Similarity NPC20114
0.8909 High Similarity NPC471921
0.8909 High Similarity NPC114550
0.8903 High Similarity NPC474965
0.8903 High Similarity NPC293757
0.8903 High Similarity NPC174512
0.8903 High Similarity NPC668
0.8903 High Similarity NPC477695
0.8875 High Similarity NPC241600
0.8875 High Similarity NPC173726
0.8854 High Similarity NPC302610
0.8854 High Similarity NPC477699
0.8846 High Similarity NPC469706
0.8846 High Similarity NPC218041
0.8846 High Similarity NPC214326
0.8846 High Similarity NPC260781
0.8846 High Similarity NPC24425
0.8846 High Similarity NPC9933
0.8846 High Similarity NPC182368
0.8846 High Similarity NPC145979
0.8846 High Similarity NPC469707
0.8846 High Similarity NPC185955
0.8846 High Similarity NPC225815
0.8816 High Similarity NPC151423
0.8816 High Similarity NPC40237
0.8816 High Similarity NPC287124
0.881 High Similarity NPC35266
0.8805 High Similarity NPC186316
0.8805 High Similarity NPC238834
0.8797 High Similarity NPC245615
0.8797 High Similarity NPC299706
0.8797 High Similarity NPC115466
0.8797 High Similarity NPC61604
0.879 High Similarity NPC477700
0.8788 High Similarity NPC117911
0.8782 High Similarity NPC145569
0.8782 High Similarity NPC216223
0.878 High Similarity NPC474042
0.878 High Similarity NPC174734
0.8757 High Similarity NPC275690
0.8757 High Similarity NPC161609
0.875 High Similarity NPC478055
0.8742 High Similarity NPC348849
0.8742 High Similarity NPC178195
0.8727 High Similarity NPC79322
0.8726 High Similarity NPC473989
0.8718 High Similarity NPC262804
0.8718 High Similarity NPC304821
0.8718 High Similarity NPC40654
0.871 High Similarity NPC212890
0.8701 High Similarity NPC477701
0.8701 High Similarity NPC475000
0.8701 High Similarity NPC141569
0.8701 High Similarity NPC92693
0.8701 High Similarity NPC218841
0.8701 High Similarity NPC166884
0.8693 High Similarity NPC176586
0.8693 High Similarity NPC210354
0.8688 High Similarity NPC38699
0.8679 High Similarity NPC474606
0.8671 High Similarity NPC32079
0.8667 High Similarity NPC320471
0.8667 High Similarity NPC83049
0.8667 High Similarity NPC118162
0.8662 High Similarity NPC35877
0.8662 High Similarity NPC95392
0.8662 High Similarity NPC55715
0.8662 High Similarity NPC125570
0.8645 High Similarity NPC477702
0.8642 High Similarity NPC474043
0.8639 High Similarity NPC469397
0.8636 High Similarity NPC474288
0.8634 High Similarity NPC163635
0.8634 High Similarity NPC29727
0.8631 High Similarity NPC184624
0.8625 High Similarity NPC473425
0.8625 High Similarity NPC198461
0.8625 High Similarity NPC312763
0.8616 High Similarity NPC471154
0.8614 High Similarity NPC473531
0.8614 High Similarity NPC475453
0.8605 High Similarity NPC167045
0.8605 High Similarity NPC114120
0.8599 High Similarity NPC248132
0.8599 High Similarity NPC325720
0.8599 High Similarity NPC270751
0.8599 High Similarity NPC316676
0.8599 High Similarity NPC130449
0.8596 High Similarity NPC188217
0.859 High Similarity NPC3982
0.859 High Similarity NPC193779
0.859 High Similarity NPC321958
0.859 High Similarity NPC321696
0.8589 High Similarity NPC470637
0.8589 High Similarity NPC474770
0.8588 High Similarity NPC260300
0.8581 High Similarity NPC187774
0.8581 High Similarity NPC472713
0.8581 High Similarity NPC191158
0.8581 High Similarity NPC473046
0.8581 High Similarity NPC472712
0.8581 High Similarity NPC118385
0.8581 High Similarity NPC177644
0.858 High Similarity NPC193377
0.858 High Similarity NPC475244
0.858 High Similarity NPC476358
0.8571 High Similarity NPC234730
0.8571 High Similarity NPC38438
0.8562 High Similarity NPC24562
0.8562 High Similarity NPC217708
0.8562 High Similarity NPC308739
0.8562 High Similarity NPC16791
0.8562 High Similarity NPC53669
0.8562 High Similarity NPC473236
0.8562 High Similarity NPC77237
0.8562 High Similarity NPC126405
0.8562 High Similarity NPC297271
0.8554 High Similarity NPC471923
0.8553 High Similarity NPC475756
0.8553 High Similarity NPC224472
0.8553 High Similarity NPC283949
0.8547 High Similarity NPC473205
0.8547 High Similarity NPC473776
0.8545 High Similarity NPC25889
0.8544 High Similarity NPC55158
0.8544 High Similarity NPC51328
0.8544 High Similarity NPC286235
0.8537 High Similarity NPC209411
0.8537 High Similarity NPC258322
0.8537 High Similarity NPC239890
0.8537 High Similarity NPC191352
0.8529 High Similarity NPC196771
0.8526 High Similarity NPC272619
0.8526 High Similarity NPC327651
0.8526 High Similarity NPC286245
0.8526 High Similarity NPC318286
0.8519 High Similarity NPC228357
0.8516 High Similarity NPC477696
0.8516 High Similarity NPC470811
0.8516 High Similarity NPC477697
0.8506 High Similarity NPC313063
0.8506 High Similarity NPC286301
0.8503 High Similarity NPC311912
0.85 High Similarity NPC21902
0.85 High Similarity NPC476434
0.8497 Intermediate Similarity NPC156376
0.8494 Intermediate Similarity NPC475738
0.8491 Intermediate Similarity NPC472709
0.8491 Intermediate Similarity NPC472710
0.8491 Intermediate Similarity NPC238140

  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 NPC100465 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
0.9682 High Similarity NPD7228 Approved
0.9608 High Similarity NPD4966 Approved
0.9608 High Similarity NPD4967 Phase 2
0.9608 High Similarity NPD4965 Approved
0.9484 High Similarity NPD6234 Discontinued
0.9441 High Similarity NPD7240 Approved
0.9412 High Similarity NPD37 Approved
0.8765 High Similarity NPD7199 Phase 2
0.8636 High Similarity NPD7237 Clinical (unspecified phase)
0.8545 High Similarity NPD7184 Clinical (unspecified phase)
0.8444 Intermediate Similarity NPD7680 Approved
0.8372 Intermediate Similarity NPD7090 Clinical (unspecified phase)
0.8324 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.8153 Intermediate Similarity NPD6674 Discontinued
0.8023 Intermediate Similarity NPD5844 Phase 1
0.7977 Intermediate Similarity NPD7074 Phase 3
0.7965 Intermediate Similarity NPD3818 Discontinued
0.7964 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7952 Intermediate Similarity NPD8455 Phase 2
0.795 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7919 Intermediate Similarity NPD7054 Approved
0.7914 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7907 Intermediate Similarity NPD7473 Discontinued
0.7874 Intermediate Similarity NPD7472 Approved
0.7841 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.7836 Intermediate Similarity NPD6232 Discontinued
0.7784 Intermediate Similarity NPD6559 Discontinued
0.7784 Intermediate Similarity NPD7685 Pre-registration
0.7778 Intermediate Similarity NPD8127 Discontinued
0.774 Intermediate Similarity NPD7808 Phase 3
0.7697 Intermediate Similarity NPD8312 Approved
0.7697 Intermediate Similarity NPD8313 Approved
0.7692 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7688 Intermediate Similarity NPD7266 Discontinued
0.7684 Intermediate Similarity NPD7251 Discontinued
0.7651 Intermediate Similarity NPD1653 Approved
0.7633 Intermediate Similarity NPD1465 Phase 2
0.763 Intermediate Similarity NPD3787 Discontinued
0.763 Intermediate Similarity NPD7229 Phase 3
0.7627 Intermediate Similarity NPD6797 Phase 2
0.7616 Intermediate Similarity NPD5494 Approved
0.7602 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.7582 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7564 Intermediate Similarity NPD3027 Phase 3
0.7543 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.7543 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.7543 Intermediate Similarity NPD6166 Phase 2
0.7529 Intermediate Similarity NPD7819 Suspended
0.7528 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7514 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD3705 Approved
0.75 Intermediate Similarity NPD7097 Phase 1
0.7485 Intermediate Similarity NPD3817 Phase 2
0.7471 Intermediate Similarity NPD1934 Approved
0.747 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7461 Intermediate Similarity NPD8151 Discontinued
0.7456 Intermediate Similarity NPD7028 Phase 2
0.7436 Intermediate Similarity NPD7827 Phase 1
0.7427 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7421 Intermediate Similarity NPD1613 Approved
0.7421 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7405 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7375 Intermediate Similarity NPD6355 Discontinued
0.7365 Intermediate Similarity NPD2533 Approved
0.7365 Intermediate Similarity NPD2534 Approved
0.7365 Intermediate Similarity NPD2532 Approved
0.736 Intermediate Similarity NPD3751 Discontinued
0.7353 Intermediate Similarity NPD4380 Phase 2
0.7333 Intermediate Similarity NPD4109 Clinical (unspecified phase)
0.7333 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7333 Intermediate Similarity NPD4110 Phase 3
0.7326 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.7312 Intermediate Similarity NPD7296 Approved
0.731 Intermediate Similarity NPD7615 Clinical (unspecified phase)
0.7301 Intermediate Similarity NPD2438 Suspended
0.7299 Intermediate Similarity NPD7075 Discontinued
0.7292 Intermediate Similarity NPD7435 Discontinued
0.7289 Intermediate Similarity NPD6190 Approved
0.7273 Intermediate Similarity NPD6959 Discontinued
0.7256 Intermediate Similarity NPD5762 Approved
0.7256 Intermediate Similarity NPD5763 Approved
0.7241 Intermediate Similarity NPD3882 Suspended
0.724 Intermediate Similarity NPD5005 Approved
0.724 Intermediate Similarity NPD5006 Approved
0.7225 Intermediate Similarity NPD2801 Approved
0.7219 Intermediate Similarity NPD6273 Approved
0.7215 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7205 Intermediate Similarity NPD3619 Clinical (unspecified phase)
0.7205 Intermediate Similarity NPD3620 Phase 2
0.7195 Intermediate Similarity NPD6100 Approved
0.7195 Intermediate Similarity NPD6099 Approved
0.7193 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7193 Intermediate Similarity NPD7458 Discontinued
0.7188 Intermediate Similarity NPD6798 Discontinued
0.7188 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7184 Intermediate Similarity NPD5402 Approved
0.7184 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.717 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.717 Intermediate Similarity NPD4908 Phase 1
0.715 Intermediate Similarity NPD6823 Phase 2
0.7143 Intermediate Similarity NPD6233 Phase 2
0.7135 Intermediate Similarity NPD6781 Approved
0.7135 Intermediate Similarity NPD6779 Approved
0.7135 Intermediate Similarity NPD6777 Approved
0.7135 Intermediate Similarity NPD6776 Approved
0.7135 Intermediate Similarity NPD6778 Approved
0.7135 Intermediate Similarity NPD6780 Approved
0.7135 Intermediate Similarity NPD6782 Approved
0.7134 Intermediate Similarity NPD1283 Approved
0.7126 Intermediate Similarity NPD3750 Approved
0.7126 Intermediate Similarity NPD8166 Discontinued
0.7126 Intermediate Similarity NPD4628 Phase 3
0.7121 Intermediate Similarity NPD7782 Clinical (unspecified phase)
0.7121 Intermediate Similarity NPD7783 Phase 2
0.712 Intermediate Similarity NPD4420 Approved
0.711 Intermediate Similarity NPD7411 Suspended
0.7108 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7099 Intermediate Similarity NPD4060 Phase 1
0.7099 Intermediate Similarity NPD4140 Approved
0.7099 Intermediate Similarity NPD2979 Phase 3
0.7097 Intermediate Similarity NPD8434 Phase 2
0.7086 Intermediate Similarity NPD5353 Approved
0.7071 Intermediate Similarity NPD7874 Approved
0.7071 Intermediate Similarity NPD7875 Clinical (unspecified phase)
0.7069 Intermediate Similarity NPD6801 Discontinued
0.7066 Intermediate Similarity NPD5698 Clinical (unspecified phase)
0.7059 Intermediate Similarity NPD6843 Phase 3
0.7059 Intermediate Similarity NPD6841 Approved
0.7059 Intermediate Similarity NPD6842 Approved
0.7055 Intermediate Similarity NPD230 Phase 1
0.7055 Intermediate Similarity NPD5735 Approved
0.7048 Intermediate Similarity NPD6003 Clinical (unspecified phase)
0.7048 Intermediate Similarity NPD6004 Phase 3
0.7048 Intermediate Similarity NPD6002 Phase 3
0.7048 Intermediate Similarity NPD6006 Clinical (unspecified phase)
0.7048 Intermediate Similarity NPD6005 Phase 3
0.7045 Intermediate Similarity NPD7768 Phase 2
0.7041 Intermediate Similarity NPD7999 Approved
0.7037 Intermediate Similarity NPD6663 Approved
0.7037 Intermediate Similarity NPD8032 Phase 2
0.7032 Intermediate Similarity NPD5125 Phase 3
0.7032 Intermediate Similarity NPD5126 Approved
0.703 Intermediate Similarity NPD3748 Approved
0.7026 Intermediate Similarity NPD7698 Approved
0.7026 Intermediate Similarity NPD7697 Approved
0.7026 Intermediate Similarity NPD7696 Phase 3
0.7019 Intermediate Similarity NPD7095 Approved
0.7006 Intermediate Similarity NPD3749 Approved
0.7006 Intermediate Similarity NPD7975 Clinical (unspecified phase)
0.7005 Intermediate Similarity NPD8150 Discontinued
0.699 Remote Similarity NPD8320 Phase 1
0.699 Remote Similarity NPD7870 Phase 2
0.699 Remote Similarity NPD8319 Approved
0.699 Remote Similarity NPD7871 Phase 2
0.6977 Remote Similarity NPD5403 Approved
0.6975 Remote Similarity NPD6410 Clinical (unspecified phase)
0.6975 Remote Similarity NPD1699 Clinical (unspecified phase)
0.697 Remote Similarity NPD7701 Phase 2
0.6959 Remote Similarity NPD5401 Approved
0.6954 Remote Similarity NPD6599 Discontinued
0.6951 Remote Similarity NPD5123 Clinical (unspecified phase)
0.6951 Remote Similarity NPD5124 Phase 1
0.695 Remote Similarity NPD7801 Approved
0.6944 Remote Similarity NPD5710 Approved
0.6944 Remote Similarity NPD5711 Approved
0.6943 Remote Similarity NPD1281 Approved
0.6943 Remote Similarity NPD1091 Approved
0.6941 Remote Similarity NPD5058 Phase 3
0.6937 Remote Similarity NPD6917 Clinical (unspecified phase)
0.6931 Remote Similarity NPD7930 Approved
0.6914 Remote Similarity NPD4625 Phase 3
0.6909 Remote Similarity NPD6653 Approved
0.6906 Remote Similarity NPD5242 Approved
0.6901 Remote Similarity NPD6799 Approved
0.6901 Remote Similarity NPD1511 Approved
0.6899 Remote Similarity NPD1608 Approved
0.6897 Remote Similarity NPD3226 Approved
0.6894 Remote Similarity NPD5736 Approved
0.6894 Remote Similarity NPD3018 Phase 2
0.6891 Remote Similarity NPD2973 Approved
0.6891 Remote Similarity NPD2975 Approved
0.6891 Remote Similarity NPD2974 Approved
0.6882 Remote Similarity NPD7549 Discontinued
0.6882 Remote Similarity NPD5084 Clinical (unspecified phase)
0.6875 Remote Similarity NPD6535 Approved
0.6875 Remote Similarity NPD6534 Approved
0.6872 Remote Similarity NPD919 Approved
0.6872 Remote Similarity NPD4580 Approved
0.6871 Remote Similarity NPD7985 Registered
0.6871 Remote Similarity NPD3764 Approved
0.6868 Remote Similarity NPD7852 Clinical (unspecified phase)
0.6864 Remote Similarity NPD1652 Phase 2
0.686 Remote Similarity NPD7422 Clinical (unspecified phase)
0.686 Remote Similarity NPD7446 Clinical (unspecified phase)
0.6859 Remote Similarity NPD1357 Approved
0.6856 Remote Similarity NPD7700 Phase 2
0.6856 Remote Similarity NPD7699 Phase 2
0.6855 Remote Similarity NPD2983 Phase 2
0.6855 Remote Similarity NPD2982 Phase 2
0.6851 Remote Similarity NPD3051 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