Structure

Physi-Chem Properties

Molecular Weight:  724.22
Volume:  659.198
LogP:  -0.36
LogD:  -0.294
LogS:  -1.822
# Rotatable Bonds:  9
TPSA:  261.98
# H-Bond Aceptor:  18
# H-Bond Donor:  8
# Rings:  7
# Heavy Atoms:  18

MedChem Properties

QED Drug-Likeness Score:  0.127
Synthetic Accessibility Score:  5.255
Fsp3:  0.606
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  1
Golden Triangle Rule:  Rejected
Chelating Alert:  1
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -6.549
MDCK Permeability:  8.06266107247211e-05
Pgp-inhibitor:  0.002
Pgp-substrate:  0.997
Human Intestinal Absorption (HIA):  0.248
20% Bioavailability (F20%):  0.022
30% Bioavailability (F30%):  0.81

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.076
Plasma Protein Binding (PPB):  85.7008285522461%
Volume Distribution (VD):  0.387
Pgp-substrate:  8.358818054199219%

ADMET: Metabolism

CYP1A2-inhibitor:  0.004
CYP1A2-substrate:  0.597
CYP2C19-inhibitor:  0.013
CYP2C19-substrate:  0.669
CYP2C9-inhibitor:  0.002
CYP2C9-substrate:  0.061
CYP2D6-inhibitor:  0.007
CYP2D6-substrate:  0.119
CYP3A4-inhibitor:  0.172
CYP3A4-substrate:  0.439

ADMET: Excretion

Clearance (CL):  1.286
Half-life (T1/2):  0.559

ADMET: Toxicity

hERG Blockers:  0.411
Human Hepatotoxicity (H-HT):  0.271
Drug-inuced Liver Injury (DILI):  0.253
AMES Toxicity:  0.208
Rat Oral Acute Toxicity:  0.029
Maximum Recommended Daily Dose:  0.063
Skin Sensitization:  0.075
Carcinogencity:  0.153
Eye Corrosion:  0.003
Eye Irritation:  0.011
Respiratory Toxicity:  0.029

Download Data

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

  Natural Product: NPC179240

Natural Product ID:  NPC179240
Common Name*:   Sinolignan B
IUPAC Name:   (5R,5aR,8aS,9R)-9-(4-hydroxy-3,5-dimethoxyphenyl)-5-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxy-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[6,5-f][1,3]benzodioxol-8-one
Synonyms:   sinolignan B
Standard InCHIKey:  PDLSJRZSXQFCFE-APVDPNJASA-N
Standard InCHI:  InChI=1S/C33H40O18/c1-43-17-3-11(4-18(44-2)23(17)35)21-12-5-15-16(48-10-47-15)6-13(12)30(14-8-45-31(42)22(14)21)51-33-29(41)27(39)25(37)20(50-33)9-46-32-28(40)26(38)24(36)19(7-34)49-32/h3-6,14,19-22,24-30,32-41H,7-10H2,1-2H3/t14-,19+,20+,21+,22+,24+,25+,26-,27-,28+,29+,30-,32+,33-/m0/s1
SMILES:  OC[C@H]1O[C@@H](OC[C@H]2O[C@@H](O[C@@H]3[C@H]4COC(=O)[C@H]4[C@@H](c4c3cc3OCOc3c4)c3cc(OC)c(c(c3)OC)O)[C@@H]([C@H]([C@@H]2O)O)O)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1778159
PubChem CID:   54581699
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]
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]
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]

☑ 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 > 100000.0 nM PMID[565909]
NPT91 Cell Line KB Homo sapiens IC50 > 100000.0 nM PMID[565909]

☑ 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 NPC179240 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
0.9874 High Similarity NPC185498
0.9811 High Similarity NPC306475
0.9686 High Similarity NPC116759
0.9686 High Similarity NPC14294
0.956 High Similarity NPC100465
0.956 High Similarity NPC152424
0.9497 High Similarity NPC150943
0.9497 High Similarity NPC268718
0.9497 High Similarity NPC91634
0.9383 High Similarity NPC222531
0.9317 High Similarity NPC115624
0.9308 High Similarity NPC237946
0.9308 High Similarity NPC32373
0.925 High Similarity NPC19947
0.925 High Similarity NPC115281
0.925 High Similarity NPC207584
0.925 High Similarity NPC181168
0.925 High Similarity NPC163527
0.9182 High Similarity NPC103197
0.9182 High Similarity NPC30009
0.9136 High Similarity NPC119910
0.9119 High Similarity NPC178574
0.9119 High Similarity NPC65591
0.9119 High Similarity NPC245948
0.908 High Similarity NPC288149
0.9018 High Similarity NPC96593
0.8994 High Similarity NPC210642
0.8994 High Similarity NPC13985
0.8944 High Similarity NPC136757
0.887 High Similarity NPC476358
0.8868 High Similarity NPC668
0.8868 High Similarity NPC174512
0.8868 High Similarity NPC477695
0.8868 High Similarity NPC474965
0.8868 High Similarity NPC293757
0.8855 High Similarity NPC25889
0.8837 High Similarity NPC275690
0.8837 High Similarity NPC161609
0.8827 High Similarity NPC273578
0.882 High Similarity NPC477699
0.8812 High Similarity NPC149505
0.8812 High Similarity NPC185955
0.8812 High Similarity NPC225815
0.8812 High Similarity NPC214326
0.8812 High Similarity NPC469706
0.8812 High Similarity NPC260781
0.8812 High Similarity NPC218041
0.8812 High Similarity NPC182368
0.8812 High Similarity NPC24425
0.8812 High Similarity NPC9933
0.8812 High Similarity NPC145979
0.8812 High Similarity NPC469707
0.8773 High Similarity NPC238834
0.8765 High Similarity NPC115466
0.8765 High Similarity NPC61604
0.8765 High Similarity NPC245615
0.8765 High Similarity NPC299706
0.8758 High Similarity NPC477700
0.8757 High Similarity NPC117911
0.875 High Similarity NPC145569
0.875 High Similarity NPC59516
0.875 High Similarity NPC216223
0.8742 High Similarity NPC101755
0.8742 High Similarity NPC65574
0.8742 High Similarity NPC104024
0.8742 High Similarity NPC304687
0.8742 High Similarity NPC80230
0.8729 High Similarity NPC473803
0.8721 High Similarity NPC472723
0.8721 High Similarity NPC469397
0.872 High Similarity NPC478055
0.8704 High Similarity NPC56184
0.8686 High Similarity NPC114120
0.8686 High Similarity NPC167045
0.8679 High Similarity NPC212890
0.8678 High Similarity NPC188217
0.8663 High Similarity NPC469354
0.8659 High Similarity NPC38699
0.8655 High Similarity NPC135334
0.8655 High Similarity NPC295941
0.8655 High Similarity NPC469776
0.8655 High Similarity NPC469774
0.8655 High Similarity NPC469777
0.8655 High Similarity NPC469772
0.8655 High Similarity NPC469773
0.8655 High Similarity NPC32723
0.8655 High Similarity NPC469775
0.8655 High Similarity NPC100925
0.8655 High Similarity NPC469778
0.865 High Similarity NPC474606
0.8642 High Similarity NPC32079
0.8639 High Similarity NPC474042
0.8639 High Similarity NPC174734
0.8634 High Similarity NPC477698
0.8634 High Similarity NPC177476
0.8634 High Similarity NPC262455
0.8634 High Similarity NPC35877
0.8634 High Similarity NPC95392
0.8634 High Similarity NPC125570
0.8634 High Similarity NPC55715
0.8629 High Similarity NPC473205
0.8629 High Similarity NPC473776
0.8621 High Similarity NPC195114
0.8616 High Similarity NPC477702
0.8614 High Similarity NPC173726
0.8614 High Similarity NPC241600
0.8613 High Similarity NPC297574
0.8606 High Similarity NPC163635
0.8589 High Similarity NPC471154
0.8588 High Similarity NPC286301
0.8588 High Similarity NPC313063
0.858 High Similarity NPC229882
0.858 High Similarity NPC158635
0.8571 High Similarity NPC130449
0.8571 High Similarity NPC53680
0.8571 High Similarity NPC208797
0.8571 High Similarity NPC248132
0.8563 High Similarity NPC80360
0.8563 High Similarity NPC260300
0.8555 High Similarity NPC473630
0.8555 High Similarity NPC193377
0.8553 High Similarity NPC472712
0.8553 High Similarity NPC118385
0.8553 High Similarity NPC472713
0.8553 High Similarity NPC187774
0.8553 High Similarity NPC473046
0.8547 High Similarity NPC292712
0.8547 High Similarity NPC312006
0.8547 High Similarity NPC474075
0.8547 High Similarity NPC471921
0.8547 High Similarity NPC473697
0.8547 High Similarity NPC114550
0.8547 High Similarity NPC20114
0.8547 High Similarity NPC471920
0.8547 High Similarity NPC471922
0.8547 High Similarity NPC129930
0.8539 High Similarity NPC7839
0.8539 High Similarity NPC142291
0.8538 High Similarity NPC197708
0.8538 High Similarity NPC658
0.8537 High Similarity NPC473236
0.8528 High Similarity NPC303519
0.8528 High Similarity NPC475756
0.8528 High Similarity NPC164082
0.8519 High Similarity NPC286235
0.8519 High Similarity NPC51328
0.8519 High Similarity NPC55158
0.8514 High Similarity NPC80956
0.8512 High Similarity NPC149873
0.8512 High Similarity NPC7191
0.8512 High Similarity NPC109061
0.8506 High Similarity NPC473713
0.8506 High Similarity NPC79736
0.8506 High Similarity NPC67629
0.8506 High Similarity NPC196771
0.85 High Similarity NPC272619
0.85 High Similarity NPC286245
0.8497 Intermediate Similarity NPC46640
0.8497 Intermediate Similarity NPC219600
0.8497 Intermediate Similarity NPC316539
0.8497 Intermediate Similarity NPC34436
0.8497 Intermediate Similarity NPC263119
0.8497 Intermediate Similarity NPC166674
0.8497 Intermediate Similarity NPC473550
0.8494 Intermediate Similarity NPC228357
0.8494 Intermediate Similarity NPC11411
0.8491 Intermediate Similarity NPC477697
0.8491 Intermediate Similarity NPC470811
0.8491 Intermediate Similarity NPC477696
0.848 Intermediate Similarity NPC311912
0.8476 Intermediate Similarity NPC21902
0.8476 Intermediate Similarity NPC476434
0.8476 Intermediate Similarity NPC289967
0.8476 Intermediate Similarity NPC472611
0.8476 Intermediate Similarity NPC472612
0.8476 Intermediate Similarity NPC478268
0.8476 Intermediate Similarity NPC302610
0.8471 Intermediate Similarity NPC475738
0.8466 Intermediate Similarity NPC170203
0.8466 Intermediate Similarity NPC473989
0.8466 Intermediate Similarity NPC475224
0.8466 Intermediate Similarity NPC472710
0.8466 Intermediate Similarity NPC472709
0.8462 Intermediate Similarity NPC246024
0.8457 Intermediate Similarity NPC304821
0.8457 Intermediate Similarity NPC241196
0.8457 Intermediate Similarity NPC35266
0.8457 Intermediate Similarity NPC267549
0.8452 Intermediate Similarity NPC24627
0.8452 Intermediate Similarity NPC100936
0.8452 Intermediate Similarity NPC1253
0.8448 Intermediate Similarity NPC475244
0.8448 Intermediate Similarity NPC469438
0.8444 Intermediate Similarity NPC264302
0.8443 Intermediate Similarity NPC471878
0.8443 Intermediate Similarity NPC475592
0.8439 Intermediate Similarity NPC38438
0.8439 Intermediate Similarity NPC102851
0.8439 Intermediate Similarity NPC5786
0.8438 Intermediate Similarity NPC253015

  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 NPC179240 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
0.9874 High Similarity NPD7228 Approved
0.9434 High Similarity NPD6234 Discontinued
0.9394 High Similarity NPD7240 Approved
0.9308 High Similarity NPD4965 Approved
0.9308 High Similarity NPD4966 Approved
0.9308 High Similarity NPD4967 Phase 2
0.9119 High Similarity NPD37 Approved
0.882 High Similarity NPD7237 Clinical (unspecified phase)
0.8729 High Similarity NPD7680 Approved
0.8409 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.8402 Intermediate Similarity NPD7199 Phase 2
0.8352 Intermediate Similarity NPD7090 Clinical (unspecified phase)
0.8198 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.8171 Intermediate Similarity NPD7074 Phase 3
0.8171 Intermediate Similarity NPD7472 Approved
0.8114 Intermediate Similarity NPD7054 Approved
0.8047 Intermediate Similarity NPD8455 Phase 2
0.8034 Intermediate Similarity NPD7808 Phase 3
0.7989 Intermediate Similarity NPD8313 Approved
0.7989 Intermediate Similarity NPD8312 Approved
0.7978 Intermediate Similarity NPD7251 Discontinued
0.7955 Intermediate Similarity NPD3818 Discontinued
0.7953 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7921 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7921 Intermediate Similarity NPD6797 Phase 2
0.7877 Intermediate Similarity NPD7685 Pre-registration
0.7833 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.7809 Intermediate Similarity NPD5844 Phase 1
0.7805 Intermediate Similarity NPD6674 Discontinued
0.7797 Intermediate Similarity NPD7473 Discontinued
0.7791 Intermediate Similarity NPD7266 Discontinued
0.7784 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7772 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.774 Intermediate Similarity NPD6166 Phase 2
0.774 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.774 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.7733 Intermediate Similarity NPD1465 Phase 2
0.7732 Intermediate Similarity NPD8151 Discontinued
0.7727 Intermediate Similarity NPD6232 Discontinued
0.7725 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7709 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.768 Intermediate Similarity NPD6559 Discontinued
0.7647 Intermediate Similarity NPD1653 Approved
0.7588 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7571 Intermediate Similarity NPD8127 Discontinued
0.7562 Intermediate Similarity NPD3027 Phase 3
0.7525 Intermediate Similarity NPD7827 Phase 1
0.75 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.7471 Intermediate Similarity NPD1934 Approved
0.743 Intermediate Similarity NPD3787 Discontinued
0.7429 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7423 Intermediate Similarity NPD1613 Approved
0.7423 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7416 Intermediate Similarity NPD5494 Approved
0.7374 Intermediate Similarity NPD6959 Discontinued
0.7337 Intermediate Similarity NPD8166 Discontinued
0.7333 Intermediate Similarity NPD7229 Phase 3
0.733 Intermediate Similarity NPD7819 Suspended
0.73 Intermediate Similarity NPD7782 Clinical (unspecified phase)
0.73 Intermediate Similarity NPD7783 Phase 2
0.7296 Intermediate Similarity NPD7435 Discontinued
0.7294 Intermediate Similarity NPD6190 Approved
0.7289 Intermediate Similarity NPD7097 Phase 1
0.7268 Intermediate Similarity NPD3751 Discontinued
0.7267 Intermediate Similarity NPD2534 Approved
0.7267 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7267 Intermediate Similarity NPD2532 Approved
0.7267 Intermediate Similarity NPD2533 Approved
0.7257 Intermediate Similarity NPD4380 Phase 2
0.7247 Intermediate Similarity NPD3882 Suspended
0.7235 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7232 Intermediate Similarity NPD2801 Approved
0.7222 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7212 Intermediate Similarity NPD3620 Phase 2
0.7212 Intermediate Similarity NPD3619 Clinical (unspecified phase)
0.7208 Intermediate Similarity NPD7697 Approved
0.7208 Intermediate Similarity NPD7698 Approved
0.7208 Intermediate Similarity NPD7696 Phase 3
0.7207 Intermediate Similarity NPD7075 Discontinued
0.7191 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.7191 Intermediate Similarity NPD3817 Phase 2
0.7178 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7172 Intermediate Similarity NPD8319 Approved
0.7172 Intermediate Similarity NPD8320 Phase 1
0.717 Intermediate Similarity NPD3705 Approved
0.7164 Intermediate Similarity NPD7874 Approved
0.7164 Intermediate Similarity NPD7875 Clinical (unspecified phase)
0.7159 Intermediate Similarity NPD7028 Phase 2
0.7157 Intermediate Similarity NPD6823 Phase 2
0.715 Intermediate Similarity NPD7701 Phase 2
0.7143 Intermediate Similarity NPD6782 Approved
0.7143 Intermediate Similarity NPD6780 Approved
0.7143 Intermediate Similarity NPD6779 Approved
0.7143 Intermediate Similarity NPD6778 Approved
0.7143 Intermediate Similarity NPD6781 Approved
0.7143 Intermediate Similarity NPD6777 Approved
0.7143 Intermediate Similarity NPD6776 Approved
0.7119 Intermediate Similarity NPD7615 Clinical (unspecified phase)
0.7105 Intermediate Similarity NPD8434 Phase 2
0.7105 Intermediate Similarity NPD8150 Discontinued
0.7102 Intermediate Similarity NPD7458 Discontinued
0.7101 Intermediate Similarity NPD6099 Approved
0.7101 Intermediate Similarity NPD6100 Approved
0.7091 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7091 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7085 Intermediate Similarity NPD7871 Phase 2
0.7085 Intermediate Similarity NPD7870 Phase 2
0.7073 Intermediate Similarity NPD4908 Phase 1
0.7066 Intermediate Similarity NPD230 Phase 1
0.7066 Intermediate Similarity NPD6355 Discontinued
0.7056 Intermediate Similarity NPD7768 Phase 2
0.7047 Intermediate Similarity NPD7296 Approved
0.7044 Intermediate Similarity NPD7801 Approved
0.7041 Intermediate Similarity NPD7700 Phase 2
0.7041 Intermediate Similarity NPD7699 Phase 2
0.7039 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.7035 Intermediate Similarity NPD4109 Clinical (unspecified phase)
0.7035 Intermediate Similarity NPD4110 Phase 3
0.7035 Intermediate Similarity NPD3750 Approved
0.7018 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7006 Intermediate Similarity NPD4060 Phase 1
0.7006 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD5402 Approved
0.7 Intermediate Similarity NPD2438 Suspended
0.6985 Remote Similarity NPD5005 Approved
0.6985 Remote Similarity NPD5006 Approved
0.6973 Remote Similarity NPD7852 Clinical (unspecified phase)
0.6959 Remote Similarity NPD5762 Approved
0.6959 Remote Similarity NPD5763 Approved
0.6946 Remote Similarity NPD6663 Approved
0.6942 Remote Similarity NPD7930 Approved
0.6936 Remote Similarity NPD4628 Phase 3
0.6932 Remote Similarity NPD6273 Approved
0.6927 Remote Similarity NPD7411 Suspended
0.6923 Remote Similarity NPD3749 Approved
0.6914 Remote Similarity NPD1511 Approved
0.6889 Remote Similarity NPD6801 Discontinued
0.6888 Remote Similarity NPD6535 Approved
0.6888 Remote Similarity NPD6534 Approved
0.6886 Remote Similarity NPD6798 Discontinued
0.6886 Remote Similarity NPD6410 Clinical (unspecified phase)
0.6881 Remote Similarity NPD7999 Approved
0.6875 Remote Similarity NPD7422 Clinical (unspecified phase)
0.6869 Remote Similarity NPD4420 Approved
0.6865 Remote Similarity NPD5710 Approved
0.6865 Remote Similarity NPD5711 Approved
0.686 Remote Similarity NPD6004 Phase 3
0.686 Remote Similarity NPD6002 Phase 3
0.686 Remote Similarity NPD6005 Phase 3
0.686 Remote Similarity NPD6003 Clinical (unspecified phase)
0.686 Remote Similarity NPD6006 Clinical (unspecified phase)
0.685 Remote Similarity NPD2494 Approved
0.685 Remote Similarity NPD2493 Approved
0.6845 Remote Similarity NPD6233 Phase 2
0.6845 Remote Similarity NPD8032 Phase 2
0.684 Remote Similarity NPD5619 Clinical (unspecified phase)
0.6836 Remote Similarity NPD1512 Approved
0.6832 Remote Similarity NPD4583 Approved
0.6832 Remote Similarity NPD4582 Approved
0.6831 Remote Similarity NPD7975 Clinical (unspecified phase)
0.6829 Remote Similarity NPD1283 Approved
0.6826 Remote Similarity NPD4625 Phase 3
0.6825 Remote Similarity NPD8155 Clinical (unspecified phase)
0.682 Remote Similarity NPD6723 Discontinued
0.6813 Remote Similarity NPD5353 Approved
0.6807 Remote Similarity NPD5736 Approved
0.6806 Remote Similarity NPD7549 Discontinued
0.6805 Remote Similarity NPD4140 Approved
0.6805 Remote Similarity NPD2979 Phase 3
0.6804 Remote Similarity NPD6841 Approved
0.6804 Remote Similarity NPD6843 Phase 3
0.6804 Remote Similarity NPD7906 Approved
0.6804 Remote Similarity NPD6842 Approved
0.6798 Remote Similarity NPD5403 Approved
0.6786 Remote Similarity NPD3764 Approved
0.6782 Remote Similarity NPD4004 Approved
0.6782 Remote Similarity NPD4002 Approved
0.6782 Remote Similarity NPD5698 Clinical (unspecified phase)
0.6766 Remote Similarity NPD3452 Approved
0.6766 Remote Similarity NPD3450 Approved
0.6765 Remote Similarity NPD5123 Clinical (unspecified phase)
0.6765 Remote Similarity NPD5124 Phase 1
0.6765 Remote Similarity NPD5735 Approved
0.6748 Remote Similarity NPD1610 Phase 2
0.6748 Remote Similarity NPD1091 Approved
0.6747 Remote Similarity NPD6917 Clinical (unspecified phase)
0.6744 Remote Similarity NPD3748 Approved
0.6743 Remote Similarity NPD1878 Clinical (unspecified phase)
0.6743 Remote Similarity NPD7003 Approved
0.6736 Remote Similarity NPD8054 Approved
0.6736 Remote Similarity NPD8053 Approved
0.6735 Remote Similarity NPD2488 Approved
0.6735 Remote Similarity NPD2490 Approved
0.6728 Remote Similarity NPD5126 Approved
0.6728 Remote Similarity NPD5125 Phase 3
0.6726 Remote Similarity NPD8152 Approved
0.6726 Remote Similarity NPD8153 Approved
0.6726 Remote Similarity NPD7095 Approved
0.6725 Remote Similarity NPD6653 Approved
0.6722 Remote Similarity NPD3226 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