Structure

Physi-Chem Properties

Molecular Weight:  694.48
Volume:  772.974
LogP:  11.912
LogD:  5.861
LogS:  -2.845
# Rotatable Bonds:  26
TPSA:  114.04
# H-Bond Aceptor:  7
# H-Bond Donor:  2
# Rings:  2
# Heavy Atoms:  7

MedChem Properties

QED Drug-Likeness Score:  0.027
Synthetic Accessibility Score:  4.21
Fsp3:  0.651
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  1
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.887
MDCK Permeability:  1.1765568160626572e-05
Pgp-inhibitor:  0.555
Pgp-substrate:  0.526
Human Intestinal Absorption (HIA):  0.011
20% Bioavailability (F20%):  0.997
30% Bioavailability (F30%):  0.982

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.308
Plasma Protein Binding (PPB):  97.0148696899414%
Volume Distribution (VD):  3.964
Pgp-substrate:  1.8328707218170166%

ADMET: Metabolism

CYP1A2-inhibitor:  0.052
CYP1A2-substrate:  0.159
CYP2C19-inhibitor:  0.386
CYP2C19-substrate:  0.058
CYP2C9-inhibitor:  0.163
CYP2C9-substrate:  0.992
CYP2D6-inhibitor:  0.004
CYP2D6-substrate:  0.031
CYP3A4-inhibitor:  0.161
CYP3A4-substrate:  0.037

ADMET: Excretion

Clearance (CL):  4.714
Half-life (T1/2):  0.019

ADMET: Toxicity

hERG Blockers:  0.013
Human Hepatotoxicity (H-HT):  0.192
Drug-inuced Liver Injury (DILI):  0.669
AMES Toxicity:  0.02
Rat Oral Acute Toxicity:  0.219
Maximum Recommended Daily Dose:  0.182
Skin Sensitization:  0.88
Carcinogencity:  0.05
Eye Corrosion:  0.003
Eye Irritation:  0.01
Respiratory Toxicity:  0.603

Download Data

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

  Natural Product: NPC470910

Natural Product ID:  NPC470910
Common Name*:   (E)-6-(3,7-Dimethylocta-2,6-Dienyl)-5-Hydroxy-4-(1-Hydroxypropyl)-8-(2-Methylbutanoyl)-2-Oxo-2H-Chromen-7-Yl Palmitate
IUPAC Name:   [6-[(2E)-3,7-dimethylocta-2,6-dienyl]-5-hydroxy-4-(1-hydroxypropyl)-8-(2-methylbutanoyl)-2-oxochromen-7-yl] hexadecanoate
Synonyms:  
Standard InCHIKey:  RQNQRJYBGOLVRS-TVKQRKNISA-N
Standard InCHI:  InChI=1S/C43H66O7/c1-8-11-12-13-14-15-16-17-18-19-20-21-22-26-36(45)49-42-33(28-27-31(6)25-23-24-30(4)5)41(48)38-34(35(44)10-3)29-37(46)50-43(38)39(42)40(47)32(7)9-2/h24,27,29,32,35,44,48H,8-23,25-26,28H2,1-7H3/b31-27+
SMILES:  CCCCCCCCCCCCCCCC(=O)OC1=C(C2=C(C(=CC(=O)O2)C(CC)O)C(=C1CC=C(C)CCC=C(C)C)O)C(=O)C(C)CC
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL2312455
PubChem CID:   71716724
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001283] Terpene lactones

*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
NPO32974 mammea siamensis Species Calophyllaceae Eukaryota n.a. n.a. n.a. PMID[22831798]
NPO32974 mammea siamensis Species Calophyllaceae Eukaryota flower n.a. n.a. PMID[23206866]

☑ 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
NPT116 Cell Line HL-60 Homo sapiens IC50 > 50000.0 nM PMID[488720]
NPT65 Cell Line HepG2 Homo sapiens IC50 > 50000.0 nM PMID[488720]
NPT148 Cell Line HCT-15 Homo sapiens IC50 > 50000.0 nM PMID[488720]
NPT15 Cell Line Jurkat Homo sapiens IC50 > 50000.0 nM PMID[488720]
NPT1970 Cell Line THP-1 Homo sapiens IC50 > 50000.0 nM PMID[488720]
NPT466 Cell Line U-937 Homo sapiens IC50 > 50000.0 nM PMID[488720]
NPT27 Others Unspecified IC50 > 50000.0 nM PMID[488720]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 > 50000.0 nM PMID[488720]

☑ 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 NPC470910 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
0.9928 High Similarity NPC133060
0.9928 High Similarity NPC288910
0.9928 High Similarity NPC118059
0.9928 High Similarity NPC470554
0.9856 High Similarity NPC470553
0.9856 High Similarity NPC474939
0.9856 High Similarity NPC96216
0.9856 High Similarity NPC184738
0.9856 High Similarity NPC470909
0.9856 High Similarity NPC307895
0.9856 High Similarity NPC33653
0.9784 High Similarity NPC294432
0.9784 High Similarity NPC470556
0.9784 High Similarity NPC112829
0.9568 High Similarity NPC19476
0.9568 High Similarity NPC241975
0.951 High Similarity NPC285748
0.9504 High Similarity NPC472344
0.9496 High Similarity NPC219584
0.9496 High Similarity NPC470083
0.9496 High Similarity NPC199458
0.9496 High Similarity NPC183639
0.9448 High Similarity NPC474735
0.9448 High Similarity NPC470908
0.9424 High Similarity NPC474624
0.9424 High Similarity NPC131782
0.9424 High Similarity NPC138047
0.9375 High Similarity NPC474108
0.9375 High Similarity NPC177995
0.9315 High Similarity NPC327059
0.9315 High Similarity NPC321387
0.9252 High Similarity NPC290671
0.9178 High Similarity NPC472345
0.9172 High Similarity NPC181388
0.9172 High Similarity NPC470322
0.9167 High Similarity NPC18886
0.9161 High Similarity NPC470555
0.9161 High Similarity NPC476508
0.9155 High Similarity NPC139554
0.9116 High Similarity NPC19238
0.9103 High Similarity NPC1886
0.9103 High Similarity NPC469935
0.9103 High Similarity NPC224714
0.9103 High Similarity NPC196137
0.9103 High Similarity NPC178627
0.9097 High Similarity NPC276565
0.9091 High Similarity NPC221173
0.906 High Similarity NPC256141
0.9054 High Similarity NPC180351
0.9041 High Similarity NPC154217
0.9034 High Similarity NPC94794
0.9034 High Similarity NPC112791
0.9034 High Similarity NPC470296
0.9034 High Similarity NPC87609
0.9034 High Similarity NPC188632
0.9034 High Similarity NPC196459
0.9021 High Similarity NPC472343
0.9007 High Similarity NPC101752
0.9007 High Similarity NPC474609
0.9007 High Similarity NPC129053
0.9007 High Similarity NPC475797
0.9007 High Similarity NPC474738
0.9007 High Similarity NPC78554
0.9007 High Similarity NPC109967
0.9007 High Similarity NPC469936
0.9007 High Similarity NPC321372
0.9 High Similarity NPC470984
0.8993 High Similarity NPC312549
0.8993 High Similarity NPC209142
0.8993 High Similarity NPC185624
0.8986 High Similarity NPC104236
0.8986 High Similarity NPC469932
0.8986 High Similarity NPC164205
0.8986 High Similarity NPC139966
0.8986 High Similarity NPC307052
0.898 High Similarity NPC47388
0.898 High Similarity NPC473133
0.898 High Similarity NPC470670
0.898 High Similarity NPC91902
0.8973 High Similarity NPC470890
0.8966 High Similarity NPC36181
0.8958 High Similarity NPC16455
0.8958 High Similarity NPC471587
0.8958 High Similarity NPC307990
0.8951 High Similarity NPC131130
0.8944 High Similarity NPC470397
0.8944 High Similarity NPC470983
0.8944 High Similarity NPC174999
0.8944 High Similarity NPC470982
0.8944 High Similarity NPC156910
0.894 High Similarity NPC279218
0.894 High Similarity NPC108937
0.8929 High Similarity NPC470988
0.8926 High Similarity NPC476509
0.8919 High Similarity NPC161864
0.8919 High Similarity NPC469933
0.8919 High Similarity NPC208303
0.8919 High Similarity NPC470460
0.8919 High Similarity NPC10097
0.8912 High Similarity NPC472629
0.8897 High Similarity NPC74397
0.8897 High Similarity NPC201820
0.8889 High Similarity NPC23257
0.8881 High Similarity NPC255801
0.8881 High Similarity NPC322301
0.8873 High Similarity NPC84699
0.8873 High Similarity NPC60667
0.8859 High Similarity NPC470461
0.8859 High Similarity NPC5173
0.8851 High Similarity NPC85773
0.8851 High Similarity NPC297886
0.8851 High Similarity NPC202494
0.8851 High Similarity NPC249942
0.8851 High Similarity NPC140120
0.8849 High Similarity NPC21378
0.8849 High Similarity NPC470987
0.8844 High Similarity NPC87486
0.8844 High Similarity NPC206212
0.8844 High Similarity NPC473014
0.8844 High Similarity NPC469953
0.8844 High Similarity NPC294365
0.8844 High Similarity NPC297788
0.8844 High Similarity NPC124780
0.8844 High Similarity NPC235217
0.8844 High Similarity NPC71184
0.8828 High Similarity NPC477272
0.8824 High Similarity NPC269495
0.8819 High Similarity NPC470668
0.8819 High Similarity NPC470669
0.8819 High Similarity NPC36414
0.8819 High Similarity NPC474504
0.8819 High Similarity NPC470672
0.8819 High Similarity NPC474487
0.8819 High Similarity NPC470671
0.8816 High Similarity NPC469934
0.8811 High Similarity NPC470398
0.8811 High Similarity NPC470989
0.8811 High Similarity NPC470985
0.8811 High Similarity NPC268081
0.8808 High Similarity NPC273483
0.8803 High Similarity NPC236974
0.8803 High Similarity NPC144027
0.8803 High Similarity NPC125920
0.88 High Similarity NPC37348
0.88 High Similarity NPC38775
0.88 High Similarity NPC61258
0.8794 High Similarity NPC285054
0.8792 High Similarity NPC145467
0.8792 High Similarity NPC471641
0.8792 High Similarity NPC168085
0.8792 High Similarity NPC240253
0.8792 High Similarity NPC240622
0.8792 High Similarity NPC471642
0.8784 High Similarity NPC474302
0.8784 High Similarity NPC127059
0.8784 High Similarity NPC285630
0.8784 High Similarity NPC476088
0.8784 High Similarity NPC24136
0.8784 High Similarity NPC57470
0.8784 High Similarity NPC187282
0.8784 High Similarity NPC470458
0.8784 High Similarity NPC290133
0.8784 High Similarity NPC474161
0.8776 High Similarity NPC223812
0.8776 High Similarity NPC125894
0.8776 High Similarity NPC77794
0.8776 High Similarity NPC117836
0.8776 High Similarity NPC185276
0.8776 High Similarity NPC81697
0.8776 High Similarity NPC51887
0.8776 High Similarity NPC85162
0.8776 High Similarity NPC476178
0.8776 High Similarity NPC475705
0.8776 High Similarity NPC107177
0.8776 High Similarity NPC278249
0.8767 High Similarity NPC248372
0.8767 High Similarity NPC258630
0.8767 High Similarity NPC470087
0.8767 High Similarity NPC279650
0.8767 High Similarity NPC166689
0.8767 High Similarity NPC110038
0.8767 High Similarity NPC96408
0.8767 High Similarity NPC321980
0.8767 High Similarity NPC282300
0.8767 High Similarity NPC156190
0.8767 High Similarity NPC17170
0.8759 High Similarity NPC471697
0.8759 High Similarity NPC240305
0.8759 High Similarity NPC217186
0.8759 High Similarity NPC472515
0.8759 High Similarity NPC53181
0.8759 High Similarity NPC473209
0.8759 High Similarity NPC37206
0.8758 High Similarity NPC474386
0.875 High Similarity NPC332594
0.875 High Similarity NPC253616
0.875 High Similarity NPC193200
0.875 High Similarity NPC38153
0.8742 High Similarity NPC309512
0.8742 High Similarity NPC317715

  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 NPC470910 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
0.8716 High Similarity NPD4378 Clinical (unspecified phase)
0.8591 High Similarity NPD2534 Approved
0.8591 High Similarity NPD2533 Approved
0.8591 High Similarity NPD2532 Approved
0.8581 High Similarity NPD7075 Discontinued
0.8571 High Similarity NPD8443 Clinical (unspecified phase)
0.8506 High Similarity NPD7096 Clinical (unspecified phase)
0.8506 High Similarity NPD7819 Suspended
0.8503 High Similarity NPD2800 Approved
0.8472 Intermediate Similarity NPD6651 Approved
0.8442 Intermediate Similarity NPD6801 Discontinued
0.8435 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.8431 Intermediate Similarity NPD4380 Phase 2
0.8387 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.8377 Intermediate Similarity NPD7411 Suspended
0.8367 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.8367 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.8344 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.8333 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.8311 Intermediate Similarity NPD1549 Phase 2
0.8299 Intermediate Similarity NPD2796 Approved
0.828 Intermediate Similarity NPD7768 Phase 2
0.8276 Intermediate Similarity NPD5124 Phase 1
0.8276 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.8255 Intermediate Similarity NPD1243 Approved
0.8235 Intermediate Similarity NPD920 Approved
0.8231 Intermediate Similarity NPD1510 Phase 2
0.8228 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.8158 Intermediate Similarity NPD6799 Approved
0.8148 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.8105 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.8092 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.8089 Intermediate Similarity NPD1934 Approved
0.8082 Intermediate Similarity NPD1240 Approved
0.8079 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.8069 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.8013 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7987 Intermediate Similarity NPD3817 Phase 2
0.7973 Intermediate Similarity NPD1607 Approved
0.7963 Intermediate Similarity NPD6959 Discontinued
0.7962 Intermediate Similarity NPD6599 Discontinued
0.7961 Intermediate Similarity NPD3750 Approved
0.7933 Intermediate Similarity NPD2935 Discontinued
0.7933 Intermediate Similarity NPD1551 Phase 2
0.7925 Intermediate Similarity NPD2801 Approved
0.7922 Intermediate Similarity NPD1511 Approved
0.7914 Intermediate Similarity NPD5711 Approved
0.7914 Intermediate Similarity NPD5710 Approved
0.7892 Intermediate Similarity NPD7054 Approved
0.7892 Intermediate Similarity NPD7286 Phase 2
0.7885 Intermediate Similarity NPD5403 Approved
0.7879 Intermediate Similarity NPD7473 Discontinued
0.7867 Intermediate Similarity NPD2799 Discontinued
0.7844 Intermediate Similarity NPD7074 Phase 3
0.7844 Intermediate Similarity NPD7472 Approved
0.7831 Intermediate Similarity NPD3818 Discontinued
0.7826 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7823 Intermediate Similarity NPD2313 Discontinued
0.7821 Intermediate Similarity NPD1512 Approved
0.7818 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.7818 Intermediate Similarity NPD6166 Phase 2
0.7818 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.7811 Intermediate Similarity NPD7808 Phase 3
0.7798 Intermediate Similarity NPD5953 Discontinued
0.7784 Intermediate Similarity NPD5844 Phase 1
0.7778 Intermediate Similarity NPD3749 Approved
0.7764 Intermediate Similarity NPD5402 Approved
0.7756 Intermediate Similarity NPD5401 Approved
0.7751 Intermediate Similarity NPD6559 Discontinued
0.7751 Intermediate Similarity NPD7251 Discontinued
0.773 Intermediate Similarity NPD919 Approved
0.7727 Intermediate Similarity NPD4628 Phase 3
0.7727 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7716 Intermediate Similarity NPD3882 Suspended
0.7706 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.7706 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.7697 Intermediate Similarity NPD6232 Discontinued
0.7692 Intermediate Similarity NPD6797 Phase 2
0.7692 Intermediate Similarity NPD422 Phase 1
0.7687 Intermediate Similarity NPD6832 Phase 2
0.7683 Intermediate Similarity NPD5494 Approved
0.7639 Intermediate Similarity NPD9717 Approved
0.7632 Intermediate Similarity NPD3748 Approved
0.7632 Intermediate Similarity NPD7033 Discontinued
0.7603 Intermediate Similarity NPD1203 Approved
0.7588 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7584 Intermediate Similarity NPD8090 Clinical (unspecified phase)
0.7584 Intermediate Similarity NPD3268 Approved
0.7578 Intermediate Similarity NPD7615 Clinical (unspecified phase)
0.7562 Intermediate Similarity NPD3226 Approved
0.7532 Intermediate Similarity NPD6002 Phase 3
0.7532 Intermediate Similarity NPD6003 Clinical (unspecified phase)
0.7532 Intermediate Similarity NPD6006 Clinical (unspecified phase)
0.7532 Intermediate Similarity NPD6005 Phase 3
0.7532 Intermediate Similarity NPD6004 Phase 3
0.7483 Intermediate Similarity NPD2797 Approved
0.7472 Intermediate Similarity NPD4363 Phase 3
0.7472 Intermediate Similarity NPD4360 Phase 2
0.7468 Intermediate Similarity NPD6099 Approved
0.7468 Intermediate Similarity NPD6100 Approved
0.7467 Intermediate Similarity NPD1699 Clinical (unspecified phase)
0.7434 Intermediate Similarity NPD230 Phase 1
0.7419 Intermediate Similarity NPD2346 Discontinued
0.736 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7356 Intermediate Similarity NPD8312 Approved
0.7356 Intermediate Similarity NPD8313 Approved
0.7351 Intermediate Similarity NPD1296 Phase 2
0.7351 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7325 Intermediate Similarity NPD1652 Phase 2
0.7321 Intermediate Similarity NPD1247 Approved
0.732 Intermediate Similarity NPD1899 Clinical (unspecified phase)
0.732 Intermediate Similarity NPD447 Suspended
0.7315 Intermediate Similarity NPD1019 Discontinued
0.7312 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7308 Intermediate Similarity NPD2344 Approved
0.7308 Intermediate Similarity NPD2343 Clinical (unspecified phase)
0.7292 Intermediate Similarity NPD9545 Approved
0.729 Intermediate Similarity NPD4308 Phase 3
0.7278 Intermediate Similarity NPD7229 Phase 3
0.7273 Intermediate Similarity NPD1465 Phase 2
0.7248 Intermediate Similarity NPD3267 Approved
0.7248 Intermediate Similarity NPD3266 Approved
0.7239 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7239 Intermediate Similarity NPD7458 Discontinued
0.7238 Intermediate Similarity NPD4361 Phase 2
0.7238 Intermediate Similarity NPD4362 Clinical (unspecified phase)
0.7237 Intermediate Similarity NPD411 Approved
0.7232 Intermediate Similarity NPD8434 Phase 2
0.7219 Intermediate Similarity NPD4908 Phase 1
0.7215 Intermediate Similarity NPD2654 Approved
0.7209 Intermediate Similarity NPD7893 Clinical (unspecified phase)
0.7208 Intermediate Similarity NPD6355 Discontinued
0.72 Intermediate Similarity NPD2798 Approved
0.7181 Intermediate Similarity NPD3225 Approved
0.7179 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.7169 Intermediate Similarity NPD8455 Phase 2
0.7162 Intermediate Similarity NPD1608 Approved
0.7153 Intermediate Similarity NPD9493 Approved
0.7151 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD7390 Discontinued
0.7128 Intermediate Similarity NPD7584 Approved
0.7125 Intermediate Similarity NPD2309 Approved
0.7124 Intermediate Similarity NPD6410 Clinical (unspecified phase)
0.7108 Intermediate Similarity NPD37 Approved
0.7095 Intermediate Similarity NPD1610 Phase 2
0.7095 Intermediate Similarity NPD1547 Clinical (unspecified phase)
0.7093 Intermediate Similarity NPD7784 Clinical (unspecified phase)
0.7083 Intermediate Similarity NPD4967 Phase 2
0.7083 Intermediate Similarity NPD4965 Approved
0.7083 Intermediate Similarity NPD4966 Approved
0.7073 Intermediate Similarity NPD1653 Approved
0.7055 Intermediate Similarity NPD6273 Approved
0.7055 Intermediate Similarity NPD1548 Phase 1
0.7053 Intermediate Similarity NPD8151 Discontinued
0.7048 Intermediate Similarity NPD5890 Approved
0.7048 Intermediate Similarity NPD5889 Approved
0.7044 Intermediate Similarity NPD2424 Discontinued
0.7039 Intermediate Similarity NPD8150 Discontinued
0.7032 Intermediate Similarity NPD943 Approved
0.7032 Intermediate Similarity NPD4307 Phase 2
0.7029 Intermediate Similarity NPD1729 Discontinued
0.7024 Intermediate Similarity NPD4288 Approved
0.7024 Intermediate Similarity NPD5353 Approved
0.7018 Intermediate Similarity NPD7199 Phase 2
0.7013 Intermediate Similarity NPD6798 Discontinued
0.7012 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD6234 Discontinued
0.7 Intermediate Similarity NPD7585 Approved
0.6994 Remote Similarity NPD2403 Approved
0.6993 Remote Similarity NPD1008 Clinical (unspecified phase)
0.6979 Remote Similarity NPD7782 Clinical (unspecified phase)
0.6979 Remote Similarity NPD7783 Phase 2
0.6975 Remote Similarity NPD6667 Approved
0.6975 Remote Similarity NPD6666 Approved
0.6964 Remote Similarity NPD5761 Phase 2
0.6964 Remote Similarity NPD5760 Phase 2
0.6961 Remote Similarity NPD4287 Approved
0.6959 Remote Similarity NPD17 Approved
0.6957 Remote Similarity NPD7003 Approved
0.6949 Remote Similarity NPD6104 Discontinued
0.6947 Remote Similarity NPD7583 Approved
0.6936 Remote Similarity NPD3926 Phase 2
0.6923 Remote Similarity NPD1613 Approved
0.6923 Remote Similarity NPD4060 Phase 1
0.6923 Remote Similarity NPD1612 Clinical (unspecified phase)
0.6919 Remote Similarity NPD8127 Discontinued
0.6919 Remote Similarity NPD8366 Approved
0.6918 Remote Similarity NPD5406 Approved
0.6918 Remote Similarity NPD4477 Approved
0.6918 Remote Similarity NPD4476 Approved
0.6918 Remote Similarity NPD5408 Approved
0.6918 Remote Similarity NPD5405 Approved
0.6918 Remote Similarity NPD5404 Approved
0.6914 Remote Similarity NPD7228 Approved
0.6908 Remote Similarity NPD1164 Approved
0.6905 Remote Similarity NPD6844 Discontinued
0.6903 Remote Similarity NPD7985 Registered
0.6901 Remote Similarity NPD5537 Clinical (unspecified phase)
0.6889 Remote Similarity NPD8055 Clinical (unspecified phase)
0.6887 Remote Similarity NPD4749 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