Structure

Physi-Chem Properties

Molecular Weight:  340.13
Volume:  339.826
LogP:  3.887
LogD:  2.964
LogS:  -4.01
# Rotatable Bonds:  1
TPSA:  68.15
# H-Bond Aceptor:  5
# H-Bond Donor:  2
# Rings:  5
# Heavy Atoms:  5

MedChem Properties

QED Drug-Likeness Score:  0.835
Synthetic Accessibility Score:  3.982
Fsp3:  0.4
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.836
MDCK Permeability:  1.2216262803121936e-05
Pgp-inhibitor:  0.008
Pgp-substrate:  0.002
Human Intestinal Absorption (HIA):  0.005
20% Bioavailability (F20%):  0.001
30% Bioavailability (F30%):  0.002

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.167
Plasma Protein Binding (PPB):  98.13362121582031%
Volume Distribution (VD):  0.726
Pgp-substrate:  2.2275400161743164%

ADMET: Metabolism

CYP1A2-inhibitor:  0.179
CYP1A2-substrate:  0.532
CYP2C19-inhibitor:  0.52
CYP2C19-substrate:  0.718
CYP2C9-inhibitor:  0.686
CYP2C9-substrate:  0.919
CYP2D6-inhibitor:  0.721
CYP2D6-substrate:  0.823
CYP3A4-inhibitor:  0.535
CYP3A4-substrate:  0.751

ADMET: Excretion

Clearance (CL):  6.036
Half-life (T1/2):  0.245

ADMET: Toxicity

hERG Blockers:  0.063
Human Hepatotoxicity (H-HT):  0.827
Drug-inuced Liver Injury (DILI):  0.621
AMES Toxicity:  0.724
Rat Oral Acute Toxicity:  0.211
Maximum Recommended Daily Dose:  0.918
Skin Sensitization:  0.331
Carcinogencity:  0.435
Eye Corrosion:  0.003
Eye Irritation:  0.209
Respiratory Toxicity:  0.099

Download Data

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

  Natural Product: NPC474687

Natural Product ID:  NPC474687
Common Name*:   Rautandiol B
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  WZYPWKAIYULRHF-CJESRSHOSA-N
Standard InCHI:  InChI=1S/C20H20O5/c1-20(2,22)18-6-10-5-13-16(8-15(10)24-18)23-9-14-12-4-3-11(21)7-17(12)25-19(13)14/h3-5,7-8,14,18-19,21-22H,6,9H2,1-2H3/t14-,18?,19-/m0/s1
SMILES:  CC(C)(C1CC2=CC3=C(C=C2O1)OCC4C3OC5=C4C=CC(=C5)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL479479
PubChem CID:   11551842
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0002506] Isoflavonoids
        • [CHEMONTID:0002617] Furanoisoflavonoids
          • [CHEMONTID:0001608] Pterocarpans

*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
NPO24293 Neorautanenia mitis Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[16562843]
NPO24293 Neorautanenia mitis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO24293 Neorautanenia mitis Species Fabaceae 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
NPT83 Cell Line MCF7 Homo sapiens IC50 > 5.0 ug.mL-1 PMID[496448]
NPT81 Cell Line A549 Homo sapiens IC50 > 5.0 ug.mL-1 PMID[496448]

☑ 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 NPC474687 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
0.9923 High Similarity NPC3049
0.9769 High Similarity NPC117048
0.9769 High Similarity NPC124085
0.9692 High Similarity NPC85435
0.9624 High Similarity NPC475836
0.9621 High Similarity NPC262585
0.9621 High Similarity NPC20829
0.9621 High Similarity NPC18189
0.9615 High Similarity NPC13005
0.9538 High Similarity NPC118114
0.9538 High Similarity NPC300875
0.9538 High Similarity NPC12875
0.9538 High Similarity NPC150011
0.9538 High Similarity NPC280653
0.9538 High Similarity NPC236014
0.9538 High Similarity NPC162801
0.9538 High Similarity NPC206224
0.9538 High Similarity NPC17343
0.9538 High Similarity NPC129106
0.9538 High Similarity NPC164574
0.9538 High Similarity NPC228369
0.9538 High Similarity NPC268917
0.9538 High Similarity NPC129784
0.9538 High Similarity NPC196765
0.9538 High Similarity NPC476166
0.9538 High Similarity NPC207892
0.947 High Similarity NPC225696
0.947 High Similarity NPC115335
0.947 High Similarity NPC198154
0.947 High Similarity NPC223008
0.947 High Similarity NPC296915
0.947 High Similarity NPC97834
0.9462 High Similarity NPC27187
0.9462 High Similarity NPC470225
0.9394 High Similarity NPC92805
0.9389 High Similarity NPC181497
0.9389 High Similarity NPC103799
0.9389 High Similarity NPC271945
0.9308 High Similarity NPC39064
0.9308 High Similarity NPC53986
0.9308 High Similarity NPC38664
0.9308 High Similarity NPC47283
0.9308 High Similarity NPC87224
0.9308 High Similarity NPC222572
0.9242 High Similarity NPC211413
0.9242 High Similarity NPC68205
0.9242 High Similarity NPC293203
0.9242 High Similarity NPC164804
0.9242 High Similarity NPC244888
0.9242 High Similarity NPC118683
0.9237 High Similarity NPC93962
0.916 High Similarity NPC274717
0.9154 High Similarity NPC230479
0.9154 High Similarity NPC283049
0.9154 High Similarity NPC471215
0.9154 High Similarity NPC50315
0.9154 High Similarity NPC26879
0.9154 High Similarity NPC262573
0.9137 High Similarity NPC280092
0.9137 High Similarity NPC12641
0.9137 High Similarity NPC93323
0.9137 High Similarity NPC45257
0.9124 High Similarity NPC309124
0.9124 High Similarity NPC184797
0.9104 High Similarity NPC215037
0.9104 High Similarity NPC77196
0.9078 High Similarity NPC16269
0.9078 High Similarity NPC21776
0.9077 High Similarity NPC103420
0.9077 High Similarity NPC17809
0.9077 High Similarity NPC188022
0.9077 High Similarity NPC285040
0.9077 High Similarity NPC102540
0.9071 High Similarity NPC469557
0.9065 High Similarity NPC85264
0.9065 High Similarity NPC102044
0.9065 High Similarity NPC47633
0.9058 High Similarity NPC87725
0.9058 High Similarity NPC263261
0.9058 High Similarity NPC5155
0.9051 High Similarity NPC236306
0.9051 High Similarity NPC232164
0.9051 High Similarity NPC473739
0.9051 High Similarity NPC70682
0.9051 High Similarity NPC260741
0.9044 High Similarity NPC78047
0.9044 High Similarity NPC126101
0.9008 High Similarity NPC276212
0.9 High Similarity NPC294156
0.9 High Similarity NPC256015
0.9 High Similarity NPC63879
0.9 High Similarity NPC106914
0.9 High Similarity NPC134195
0.9 High Similarity NPC475492
0.9 High Similarity NPC197351
0.9 High Similarity NPC86502
0.9 High Similarity NPC246648
0.8993 High Similarity NPC59841
0.8993 High Similarity NPC2613
0.8993 High Similarity NPC204347
0.8993 High Similarity NPC475891
0.8993 High Similarity NPC107161
0.8986 High Similarity NPC27495
0.8978 High Similarity NPC477938
0.8971 High Similarity NPC473413
0.8971 High Similarity NPC151224
0.8947 High Similarity NPC134360
0.8944 High Similarity NPC101376
0.8939 High Similarity NPC149796
0.8936 High Similarity NPC180953
0.8931 High Similarity NPC278552
0.8931 High Similarity NPC167571
0.8931 High Similarity NPC81641
0.8931 High Similarity NPC207179
0.8929 High Similarity NPC184607
0.8923 High Similarity NPC76465
0.8923 High Similarity NPC38761
0.8921 High Similarity NPC100482
0.8921 High Similarity NPC35216
0.8921 High Similarity NPC247291
0.8921 High Similarity NPC277331
0.8913 High Similarity NPC32630
0.8905 High Similarity NPC230734
0.8905 High Similarity NPC474639
0.8905 High Similarity NPC265433
0.8905 High Similarity NPC270456
0.8905 High Similarity NPC248727
0.8905 High Similarity NPC162659
0.8905 High Similarity NPC227503
0.8905 High Similarity NPC327735
0.8905 High Similarity NPC470802
0.8904 High Similarity NPC159922
0.8897 High Similarity NPC473107
0.8881 High Similarity NPC71726
0.8873 High Similarity NPC324492
0.8873 High Similarity NPC260397
0.8873 High Similarity NPC317053
0.8865 High Similarity NPC473108
0.8857 High Similarity NPC472353
0.8857 High Similarity NPC470937
0.8849 High Similarity NPC160283
0.8849 High Similarity NPC259519
0.8849 High Similarity NPC254759
0.8846 High Similarity NPC150026
0.8846 High Similarity NPC100099
0.8846 High Similarity NPC36016
0.8832 High Similarity NPC121812
0.8832 High Similarity NPC470356
0.8832 High Similarity NPC61946
0.8832 High Similarity NPC99572
0.8832 High Similarity NPC94750
0.8832 High Similarity NPC125579
0.8832 High Similarity NPC164787
0.8832 High Similarity NPC112246
0.8832 High Similarity NPC126409
0.8832 High Similarity NPC112939
0.8832 High Similarity NPC474206
0.8824 High Similarity NPC11060
0.8811 High Similarity NPC320671
0.8811 High Similarity NPC327412
0.8811 High Similarity NPC320970
0.8811 High Similarity NPC328567
0.8803 High Similarity NPC181615
0.8794 High Similarity NPC81638
0.8786 High Similarity NPC471389
0.8786 High Similarity NPC108674
0.8786 High Similarity NPC265075
0.8779 High Similarity NPC474160
0.8777 High Similarity NPC471388
0.8777 High Similarity NPC245207
0.8777 High Similarity NPC127218
0.8777 High Similarity NPC319647
0.8777 High Similarity NPC25966
0.8777 High Similarity NPC292882
0.8769 High Similarity NPC193364
0.8769 High Similarity NPC54972
0.8769 High Similarity NPC97432
0.8769 High Similarity NPC190454
0.8768 High Similarity NPC156502
0.8768 High Similarity NPC477939
0.8768 High Similarity NPC209985
0.8768 High Similarity NPC234952
0.8768 High Similarity NPC306441
0.8768 High Similarity NPC10737
0.8768 High Similarity NPC302701
0.8768 High Similarity NPC472800
0.8768 High Similarity NPC263367
0.8768 High Similarity NPC173660
0.8768 High Similarity NPC269091
0.8768 High Similarity NPC54743
0.8768 High Similarity NPC471522
0.8768 High Similarity NPC16435
0.8768 High Similarity NPC177160
0.8768 High Similarity NPC29799
0.8767 High Similarity NPC160196
0.8759 High Similarity NPC317380
0.8759 High Similarity NPC187616
0.8759 High Similarity NPC193026
0.8759 High Similarity NPC49603
0.875 High Similarity NPC20757

  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 NPC474687 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
0.9023 High Similarity NPD4907 Clinical (unspecified phase)
0.8872 High Similarity NPD4908 Phase 1
0.8769 High Similarity NPD1610 Phase 2
0.8613 High Similarity NPD1612 Clinical (unspecified phase)
0.8613 High Similarity NPD1613 Approved
0.8456 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.8394 Intermediate Similarity NPD4625 Phase 3
0.8382 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.8382 Intermediate Similarity NPD2861 Phase 2
0.8321 Intermediate Similarity NPD1548 Phase 1
0.8261 Intermediate Similarity NPD3027 Phase 3
0.8222 Intermediate Similarity NPD4749 Approved
0.8201 Intermediate Similarity NPD6410 Clinical (unspecified phase)
0.8028 Intermediate Similarity NPD5124 Phase 1
0.8028 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.8014 Intermediate Similarity NPD5698 Clinical (unspecified phase)
0.7986 Intermediate Similarity NPD5588 Approved
0.7973 Intermediate Similarity NPD5058 Phase 3
0.7958 Intermediate Similarity NPD4060 Phase 1
0.7922 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7917 Intermediate Similarity NPD4537 Clinical (unspecified phase)
0.7917 Intermediate Similarity NPD4536 Approved
0.7917 Intermediate Similarity NPD4538 Approved
0.7899 Intermediate Similarity NPD8651 Approved
0.7843 Intermediate Similarity NPD4380 Phase 2
0.7834 Intermediate Similarity NPD6234 Discontinued
0.781 Intermediate Similarity NPD1091 Approved
0.7771 Intermediate Similarity NPD7075 Discontinued
0.7756 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.7748 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.7742 Intermediate Similarity NPD1934 Approved
0.774 Intermediate Similarity NPD5960 Phase 3
0.7718 Intermediate Similarity NPD7466 Approved
0.7707 Intermediate Similarity NPD4966 Approved
0.7707 Intermediate Similarity NPD4967 Phase 2
0.7707 Intermediate Similarity NPD4965 Approved
0.7703 Intermediate Similarity NPD2424 Discontinued
0.7692 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.7692 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7682 Intermediate Similarity NPD7213 Phase 3
0.7682 Intermediate Similarity NPD7212 Phase 2
0.7677 Intermediate Similarity NPD7615 Clinical (unspecified phase)
0.7655 Intermediate Similarity NPD6355 Discontinued
0.7651 Intermediate Similarity NPD1652 Phase 2
0.7635 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.7635 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.7632 Intermediate Similarity NPD7447 Phase 1
0.7607 Intermediate Similarity NPD7228 Approved
0.7584 Intermediate Similarity NPD1549 Phase 2
0.7571 Intermediate Similarity NPD3600 Clinical (unspecified phase)
0.7568 Intermediate Similarity NPD6099 Approved
0.7568 Intermediate Similarity NPD6100 Approved
0.7562 Intermediate Similarity NPD5494 Approved
0.7557 Intermediate Similarity NPD2684 Approved
0.7556 Intermediate Similarity NPD6671 Approved
0.7556 Intermediate Similarity NPD7157 Approved
0.7554 Intermediate Similarity NPD422 Phase 1
0.7547 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.7535 Intermediate Similarity NPD6917 Clinical (unspecified phase)
0.7534 Intermediate Similarity NPD5735 Approved
0.7533 Intermediate Similarity NPD6674 Discontinued
0.753 Intermediate Similarity NPD6559 Discontinued
0.7518 Intermediate Similarity NPD6696 Suspended
0.7517 Intermediate Similarity NPD6006 Clinical (unspecified phase)
0.7517 Intermediate Similarity NPD6004 Phase 3
0.7517 Intermediate Similarity NPD6003 Clinical (unspecified phase)
0.7517 Intermediate Similarity NPD6005 Phase 3
0.7517 Intermediate Similarity NPD6002 Phase 3
0.7516 Intermediate Similarity NPD37 Approved
0.7516 Intermediate Similarity NPD7199 Phase 2
0.7484 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7483 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7481 Intermediate Similarity NPD290 Approved
0.7463 Intermediate Similarity NPD7843 Approved
0.7455 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.7452 Intermediate Similarity NPD6072 Discontinued
0.7448 Intermediate Similarity NPD6798 Discontinued
0.7432 Intermediate Similarity NPD7097 Phase 1
0.7423 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.741 Intermediate Similarity NPD5125 Phase 3
0.741 Intermediate Similarity NPD5126 Approved
0.7405 Intermediate Similarity NPD6801 Discontinued
0.7403 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.74 Intermediate Similarity NPD5762 Approved
0.74 Intermediate Similarity NPD5763 Approved
0.7383 Intermediate Similarity NPD7033 Discontinued
0.7378 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.7378 Intermediate Similarity NPD6166 Phase 2
0.7378 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.7375 Intermediate Similarity NPD3882 Suspended
0.7375 Intermediate Similarity NPD7768 Phase 2
0.7372 Intermediate Similarity NPD1653 Approved
0.7368 Intermediate Similarity NPD3892 Phase 2
0.7368 Intermediate Similarity NPD3750 Approved
0.7368 Intermediate Similarity NPD4535 Phase 3
0.7362 Intermediate Similarity NPD7229 Phase 3
0.7361 Intermediate Similarity NPD3018 Phase 2
0.7358 Intermediate Similarity NPD2801 Approved
0.7358 Intermediate Similarity NPD8455 Phase 2
0.7358 Intermediate Similarity NPD7819 Suspended
0.7349 Intermediate Similarity NPD5844 Phase 1
0.7342 Intermediate Similarity NPD7411 Suspended
0.7333 Intermediate Similarity NPD2796 Approved
0.7301 Intermediate Similarity NPD6959 Discontinued
0.729 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7289 Intermediate Similarity NPD3818 Discontinued
0.7286 Intermediate Similarity NPD5846 Approved
0.7286 Intermediate Similarity NPD6516 Phase 2
0.7279 Intermediate Similarity NPD6233 Phase 2
0.7279 Intermediate Similarity NPD5283 Phase 1
0.7273 Intermediate Similarity NPD968 Approved
0.7267 Intermediate Similarity NPD1510 Phase 2
0.726 Intermediate Similarity NPD7095 Approved
0.7255 Intermediate Similarity NPD4628 Phase 3
0.725 Intermediate Similarity NPD5929 Approved
0.7248 Intermediate Similarity NPD6353 Approved
0.7231 Intermediate Similarity NPD940 Approved
0.7231 Intermediate Similarity NPD846 Approved
0.723 Intermediate Similarity NPD2238 Phase 2
0.723 Intermediate Similarity NPD3619 Clinical (unspecified phase)
0.723 Intermediate Similarity NPD5837 Clinical (unspecified phase)
0.723 Intermediate Similarity NPD3620 Phase 2
0.7226 Intermediate Similarity NPD1511 Approved
0.7226 Intermediate Similarity NPD6799 Approved
0.7222 Intermediate Similarity NPD2797 Approved
0.7219 Intermediate Similarity NPD7240 Approved
0.7203 Intermediate Similarity NPD6583 Phase 3
0.7203 Intermediate Similarity NPD6582 Phase 2
0.7203 Intermediate Similarity NPD5327 Phase 3
0.7203 Intermediate Similarity NPD2982 Phase 2
0.7203 Intermediate Similarity NPD2983 Phase 2
0.7202 Intermediate Similarity NPD7074 Phase 3
0.719 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.719 Intermediate Similarity NPD2800 Approved
0.7172 Intermediate Similarity NPD6584 Phase 3
0.717 Intermediate Similarity NPD6599 Discontinued
0.7169 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.7161 Intermediate Similarity NPD3122 Phase 3
0.7161 Intermediate Similarity NPD6667 Approved
0.7161 Intermediate Similarity NPD6666 Approved
0.7143 Intermediate Similarity NPD7054 Approved
0.7143 Intermediate Similarity NPD6331 Phase 2
0.7143 Intermediate Similarity NPD7741 Discontinued
0.7134 Intermediate Similarity NPD1512 Approved
0.7133 Intermediate Similarity NPD4097 Suspended
0.7133 Intermediate Similarity NPD2981 Phase 2
0.7133 Intermediate Similarity NPD2157 Approved
0.7122 Intermediate Similarity NPD7340 Approved
0.7117 Intermediate Similarity NPD3749 Approved
0.7115 Intermediate Similarity NPD7040 Clinical (unspecified phase)
0.7115 Intermediate Similarity NPD7041 Phase 2
0.7114 Intermediate Similarity NPD1240 Approved
0.7114 Intermediate Similarity NPD4140 Approved
0.7111 Intermediate Similarity NPD4750 Phase 3
0.7103 Intermediate Similarity NPD3094 Phase 2
0.7101 Intermediate Similarity NPD7472 Approved
0.7099 Intermediate Similarity NPD3817 Phase 2
0.7097 Intermediate Similarity NPD2677 Approved
0.7095 Intermediate Similarity NPD3268 Approved
0.7089 Intermediate Similarity NPD5403 Approved
0.7086 Intermediate Similarity NPD2200 Suspended
0.7081 Intermediate Similarity NPD4433 Discontinued
0.708 Intermediate Similarity NPD5535 Approved
0.7077 Intermediate Similarity NPD3020 Approved
0.7076 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.7076 Intermediate Similarity NPD7549 Discontinued
0.707 Intermediate Similarity NPD2532 Approved
0.707 Intermediate Similarity NPD7019 Approved
0.707 Intermediate Similarity NPD2534 Approved
0.707 Intermediate Similarity NPD7020 Approved
0.707 Intermediate Similarity NPD2533 Approved
0.7067 Intermediate Similarity NPD4340 Discontinued
0.7063 Intermediate Similarity NPD3705 Approved
0.7059 Intermediate Similarity NPD6797 Phase 2
0.7059 Intermediate Similarity NPD2029 Clinical (unspecified phase)
0.7055 Intermediate Similarity NPD3691 Phase 2
0.7055 Intermediate Similarity NPD3690 Phase 2
0.7052 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7048 Intermediate Similarity NPD3787 Discontinued
0.7048 Intermediate Similarity NPD6232 Discontinued
0.7039 Intermediate Similarity NPD3748 Approved
0.7039 Intermediate Similarity NPD3846 Clinical (unspecified phase)
0.7035 Intermediate Similarity NPD4578 Approved
0.7035 Intermediate Similarity NPD7312 Approved
0.7035 Intermediate Similarity NPD7311 Approved
0.7035 Intermediate Similarity NPD4577 Approved
0.7035 Intermediate Similarity NPD7313 Approved
0.7035 Intermediate Similarity NPD7310 Approved
0.7029 Intermediate Similarity NPD1398 Phase 1
0.7025 Intermediate Similarity NPD7314 Clinical (unspecified phase)
0.7024 Intermediate Similarity NPD7473 Discontinued
0.702 Intermediate Similarity NPD6653 Approved
0.702 Intermediate Similarity NPD1607 Approved
0.7018 Intermediate Similarity NPD7251 Discontinued
0.7013 Intermediate Similarity NPD7037 Approved
0.7012 Intermediate Similarity NPD7975 Clinical (unspecified phase)
0.7011 Intermediate Similarity NPD4663 Approved
0.7007 Intermediate Similarity NPD228 Approved
0.7006 Intermediate Similarity NPD2970 Approved
0.7006 Intermediate Similarity NPD2969 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