Structure

Physi-Chem Properties

Molecular Weight:  528.27
Volume:  533.237
LogP:  3.789
LogD:  3.219
LogS:  -3.916
# Rotatable Bonds:  8
TPSA:  117.98
# H-Bond Aceptor:  8
# H-Bond Donor:  3
# Rings:  6
# Heavy Atoms:  8

MedChem Properties

QED Drug-Likeness Score:  0.191
Synthetic Accessibility Score:  6.734
Fsp3:  0.7
Lipinski Rule-of-5:  Accepted
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:  -4.825
MDCK Permeability:  2.222114744654391e-05
Pgp-inhibitor:  0.023
Pgp-substrate:  0.044
Human Intestinal Absorption (HIA):  0.011
20% Bioavailability (F20%):  0.578
30% Bioavailability (F30%):  0.332

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.767
Plasma Protein Binding (PPB):  85.8841323852539%
Volume Distribution (VD):  1.946
Pgp-substrate:  10.883159637451172%

ADMET: Metabolism

CYP1A2-inhibitor:  0.023
CYP1A2-substrate:  0.981
CYP2C19-inhibitor:  0.076
CYP2C19-substrate:  0.796
CYP2C9-inhibitor:  0.299
CYP2C9-substrate:  0.02
CYP2D6-inhibitor:  0.004
CYP2D6-substrate:  0.247
CYP3A4-inhibitor:  0.799
CYP3A4-substrate:  0.567

ADMET: Excretion

Clearance (CL):  6.08
Half-life (T1/2):  0.535

ADMET: Toxicity

hERG Blockers:  0.655
Human Hepatotoxicity (H-HT):  0.977
Drug-inuced Liver Injury (DILI):  0.738
AMES Toxicity:  0.8
Rat Oral Acute Toxicity:  0.928
Maximum Recommended Daily Dose:  0.988
Skin Sensitization:  0.9
Carcinogencity:  0.851
Eye Corrosion:  0.004
Eye Irritation:  0.02
Respiratory Toxicity:  0.987

Download Data

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

  Natural Product: NPC251564

Natural Product ID:  NPC251564
Common Name*:   CZCPFHFUOUQBDL-OCLYYHQSSA-N
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  CZCPFHFUOUQBDL-OCLYYHQSSA-N
Standard InCHI:  InChI=1S/C30H40O8/c1-6-7-8-9-10-11-12-13-28-36-23-21-24-27(16-31,35-24)25(33)29(34)20(14-18(4)22(29)32)30(21,38-28)19(5)15-26(23,37-28)17(2)3/h10-14,19-21,23-25,31,33-34H,2,6-9,15-16H2,1,3-5H3/b11-10+,13-12-/t19-,20-,21-,23-,24+,25-,26-,27+,28-,29-,30+/m1/s1
SMILES:  CCCCC/C=C/C=C[C@@]12O[C@@H]3[C@@H]4[C@H]5[C@@](CO)([C@H]([C@]6([C@@H](C=C(C)C6=O)[C@]4([C@H](C)C[C@]3(C(=C)C)O1)O2)O)O)O5
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL453030
PubChem CID:   44559841
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001551] Diterpenoids
          • [CHEMONTID:0003494] Rhamnofolane and daphnane diterpenoids

*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
NPO32646 synaptolepis kirkii Species Thymelaeaceae Eukaryota n.a. n.a. n.a. PMID[11000015]
NPO33116 synaptolepis retusa Species Thymelaeaceae Eukaryota roots n.a. n.a. PMID[3210015]
NPO32646 synaptolepis kirkii Species Thymelaeaceae Eukaryota roots n.a. n.a. PMID[3210015]

☑ 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
NPT32 Organism Mus musculus Mus musculus Activity = 0.15 nmol PMID[448487]
NPT32 Organism Mus musculus Mus musculus Activity = 6.7 /nmol PMID[448487]

☑ 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 NPC251564 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 NPC475314
1.0 High Similarity NPC475606
1.0 High Similarity NPC477189
0.9917 High Similarity NPC474508
0.9917 High Similarity NPC473485
0.9754 High Similarity NPC475500
0.9754 High Similarity NPC475154
0.9754 High Similarity NPC223356
0.9754 High Similarity NPC471136
0.9754 High Similarity NPC473548
0.9754 High Similarity NPC182266
0.9754 High Similarity NPC100017
0.9754 High Similarity NPC471137
0.975 High Similarity NPC162495
0.9664 High Similarity NPC217901
0.9597 High Similarity NPC68282
0.959 High Similarity NPC180902
0.959 High Similarity NPC475139
0.9583 High Similarity NPC475273
0.9583 High Similarity NPC168849
0.9187 High Similarity NPC476078
0.9187 High Similarity NPC476091
0.918 High Similarity NPC471939
0.9106 High Similarity NPC471940
0.904 High Similarity NPC475389
0.904 High Similarity NPC473838
0.9016 High Similarity NPC473802
0.8943 High Similarity NPC473709
0.8943 High Similarity NPC473919
0.877 High Similarity NPC142882
0.873 High Similarity NPC236999
0.8583 High Similarity NPC270109
0.8425 Intermediate Similarity NPC222307
0.8413 Intermediate Similarity NPC472399
0.8346 Intermediate Similarity NPC145238
0.8333 Intermediate Similarity NPC257017
0.8333 Intermediate Similarity NPC162009
0.832 Intermediate Similarity NPC317635
0.832 Intermediate Similarity NPC329008
0.8281 Intermediate Similarity NPC225049
0.8254 Intermediate Similarity NPC472401
0.8194 Intermediate Similarity NPC146310
0.8189 Intermediate Similarity NPC19464
0.8175 Intermediate Similarity NPC471128
0.8175 Intermediate Similarity NPC475885
0.8175 Intermediate Similarity NPC157252
0.8175 Intermediate Similarity NPC145182
0.8175 Intermediate Similarity NPC471126
0.8151 Intermediate Similarity NPC181924
0.812 Intermediate Similarity NPC471234
0.811 Intermediate Similarity NPC477046
0.811 Intermediate Similarity NPC102822
0.811 Intermediate Similarity NPC52839
0.8095 Intermediate Similarity NPC49297
0.8095 Intermediate Similarity NPC470186
0.8095 Intermediate Similarity NPC236918
0.8095 Intermediate Similarity NPC156745
0.8077 Intermediate Similarity NPC298841
0.8062 Intermediate Similarity NPC470922
0.8031 Intermediate Similarity NPC185876
0.8031 Intermediate Similarity NPC19336
0.8031 Intermediate Similarity NPC329080
0.8031 Intermediate Similarity NPC472004
0.8031 Intermediate Similarity NPC472759
0.8031 Intermediate Similarity NPC143755
0.803 Intermediate Similarity NPC476852
0.8016 Intermediate Similarity NPC171905
0.8016 Intermediate Similarity NPC472397
0.8016 Intermediate Similarity NPC471125
0.8016 Intermediate Similarity NPC472758
0.8016 Intermediate Similarity NPC146280
0.8016 Intermediate Similarity NPC284707
0.8016 Intermediate Similarity NPC124676
0.8015 Intermediate Similarity NPC473620
0.8 Intermediate Similarity NPC181999
0.8 Intermediate Similarity NPC243014
0.8 Intermediate Similarity NPC477509
0.7984 Intermediate Similarity NPC477126
0.7984 Intermediate Similarity NPC469352
0.797 Intermediate Similarity NPC471855
0.7955 Intermediate Similarity NPC470851
0.7955 Intermediate Similarity NPC476851
0.7955 Intermediate Similarity NPC231529
0.7955 Intermediate Similarity NPC475371
0.7953 Intermediate Similarity NPC472667
0.7953 Intermediate Similarity NPC475775
0.7953 Intermediate Similarity NPC22628
0.7953 Intermediate Similarity NPC471108
0.7953 Intermediate Similarity NPC476529
0.7953 Intermediate Similarity NPC180640
0.7953 Intermediate Similarity NPC275696
0.7953 Intermediate Similarity NPC476107
0.7953 Intermediate Similarity NPC469488
0.7953 Intermediate Similarity NPC5991
0.7953 Intermediate Similarity NPC5989
0.7953 Intermediate Similarity NPC255081
0.7939 Intermediate Similarity NPC287423
0.7939 Intermediate Similarity NPC42399
0.7939 Intermediate Similarity NPC470780
0.7937 Intermediate Similarity NPC156252
0.7937 Intermediate Similarity NPC53396
0.7937 Intermediate Similarity NPC474518
0.7937 Intermediate Similarity NPC98249
0.7937 Intermediate Similarity NPC27999
0.7937 Intermediate Similarity NPC477116
0.7933 Intermediate Similarity NPC275477
0.7933 Intermediate Similarity NPC477188
0.7933 Intermediate Similarity NPC43304
0.7933 Intermediate Similarity NPC477190
0.7923 Intermediate Similarity NPC24651
0.791 Intermediate Similarity NPC168879
0.7895 Intermediate Similarity NPC476863
0.7895 Intermediate Similarity NPC476855
0.7895 Intermediate Similarity NPC476862
0.7891 Intermediate Similarity NPC112038
0.7891 Intermediate Similarity NPC107338
0.7891 Intermediate Similarity NPC475003
0.7891 Intermediate Similarity NPC109607
0.7881 Intermediate Similarity NPC322420
0.7879 Intermediate Similarity NPC476859
0.7879 Intermediate Similarity NPC470850
0.7874 Intermediate Similarity NPC472760
0.7874 Intermediate Similarity NPC204552
0.7874 Intermediate Similarity NPC188667
0.7869 Intermediate Similarity NPC29827
0.7863 Intermediate Similarity NPC473635
0.7863 Intermediate Similarity NPC293112
0.7857 Intermediate Similarity NPC154363
0.7857 Intermediate Similarity NPC234858
0.7857 Intermediate Similarity NPC471172
0.7857 Intermediate Similarity NPC471127
0.7852 Intermediate Similarity NPC242486
0.7852 Intermediate Similarity NPC15215
0.7846 Intermediate Similarity NPC471392
0.7846 Intermediate Similarity NPC91693
0.7846 Intermediate Similarity NPC11895
0.7846 Intermediate Similarity NPC18945
0.7846 Intermediate Similarity NPC105926
0.7846 Intermediate Similarity NPC265557
0.7846 Intermediate Similarity NPC67251
0.784 Intermediate Similarity NPC469463
0.784 Intermediate Similarity NPC469454
0.784 Intermediate Similarity NPC469496
0.7836 Intermediate Similarity NPC33378
0.7836 Intermediate Similarity NPC102316
0.7836 Intermediate Similarity NPC254614
0.7836 Intermediate Similarity NPC100390
0.7836 Intermediate Similarity NPC254146
0.7836 Intermediate Similarity NPC6274
0.7836 Intermediate Similarity NPC470185
0.7829 Intermediate Similarity NPC310511
0.7829 Intermediate Similarity NPC470779
0.782 Intermediate Similarity NPC471407
0.782 Intermediate Similarity NPC175186
0.782 Intermediate Similarity NPC473593
0.782 Intermediate Similarity NPC470880
0.782 Intermediate Similarity NPC104382
0.782 Intermediate Similarity NPC476854
0.7812 Intermediate Similarity NPC9674
0.7812 Intermediate Similarity NPC19028
0.781 Intermediate Similarity NPC596
0.7803 Intermediate Similarity NPC476008
0.7803 Intermediate Similarity NPC470882
0.7803 Intermediate Similarity NPC473253
0.7803 Intermediate Similarity NPC305496
0.7801 Intermediate Similarity NPC48813
0.7801 Intermediate Similarity NPC194854
0.7795 Intermediate Similarity NPC97908
0.7795 Intermediate Similarity NPC474654
0.7795 Intermediate Similarity NPC122033
0.7795 Intermediate Similarity NPC470854
0.7795 Intermediate Similarity NPC23046
0.7795 Intermediate Similarity NPC10721
0.7795 Intermediate Similarity NPC469684
0.7795 Intermediate Similarity NPC287343
0.7795 Intermediate Similarity NPC153651
0.7787 Intermediate Similarity NPC474716
0.7786 Intermediate Similarity NPC8369
0.7786 Intermediate Similarity NPC476729
0.7786 Intermediate Similarity NPC81736
0.7786 Intermediate Similarity NPC172154
0.7778 Intermediate Similarity NPC238667
0.7778 Intermediate Similarity NPC73314
0.7778 Intermediate Similarity NPC88668
0.7778 Intermediate Similarity NPC61891
0.7778 Intermediate Similarity NPC472400
0.7778 Intermediate Similarity NPC474872
0.7769 Intermediate Similarity NPC170538
0.7769 Intermediate Similarity NPC474741
0.7769 Intermediate Similarity NPC222688
0.7769 Intermediate Similarity NPC312833
0.7761 Intermediate Similarity NPC471170
0.776 Intermediate Similarity NPC475391
0.7752 Intermediate Similarity NPC4548
0.7752 Intermediate Similarity NPC48692
0.7746 Intermediate Similarity NPC475462
0.7746 Intermediate Similarity NPC16729
0.7744 Intermediate Similarity NPC311534
0.7744 Intermediate Similarity NPC473888
0.7742 Intermediate Similarity NPC46407

  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 NPC251564 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
0.7752 Intermediate Similarity NPD6054 Approved
0.7634 Intermediate Similarity NPD6370 Approved
0.7557 Intermediate Similarity NPD6016 Approved
0.7557 Intermediate Similarity NPD6015 Approved
0.7556 Intermediate Similarity NPD7319 Approved
0.7519 Intermediate Similarity NPD7492 Approved
0.75 Intermediate Similarity NPD5988 Approved
0.75 Intermediate Similarity NPD7899 Clinical (unspecified phase)
0.7481 Intermediate Similarity NPD6059 Approved
0.7463 Intermediate Similarity NPD6616 Approved
0.744 Intermediate Similarity NPD5345 Clinical (unspecified phase)
0.7424 Intermediate Similarity NPD8516 Approved
0.7424 Intermediate Similarity NPD8515 Approved
0.7424 Intermediate Similarity NPD8517 Approved
0.7424 Intermediate Similarity NPD8513 Phase 3
0.7407 Intermediate Similarity NPD7078 Approved
0.7353 Intermediate Similarity NPD7736 Approved
0.7333 Intermediate Similarity NPD7507 Approved
0.7252 Intermediate Similarity NPD7115 Discovery
0.7218 Intermediate Similarity NPD6319 Approved
0.7188 Intermediate Similarity NPD6371 Approved
0.7153 Intermediate Similarity NPD8074 Phase 3
0.7153 Intermediate Similarity NPD8293 Discontinued
0.7143 Intermediate Similarity NPD7516 Approved
0.7097 Intermediate Similarity NPD5344 Discontinued
0.7077 Intermediate Similarity NPD6882 Approved
0.7068 Intermediate Similarity NPD7327 Approved
0.7068 Intermediate Similarity NPD7328 Approved
0.7059 Intermediate Similarity NPD8328 Phase 3
0.7031 Intermediate Similarity NPD6686 Approved
0.7016 Intermediate Similarity NPD6648 Approved
0.6992 Remote Similarity NPD6009 Approved
0.6978 Remote Similarity NPD6033 Approved
0.6977 Remote Similarity NPD4061 Clinical (unspecified phase)
0.6947 Remote Similarity NPD8297 Approved
0.6944 Remote Similarity NPD7966 Clinical (unspecified phase)
0.6923 Remote Similarity NPD4634 Approved
0.6923 Remote Similarity NPD5955 Clinical (unspecified phase)
0.6912 Remote Similarity NPD7503 Approved
0.6912 Remote Similarity NPD6921 Approved
0.6894 Remote Similarity NPD4632 Approved
0.687 Remote Similarity NPD6650 Approved
0.687 Remote Similarity NPD6649 Approved
0.687 Remote Similarity NPD8413 Clinical (unspecified phase)
0.6829 Remote Similarity NPD1698 Clinical (unspecified phase)
0.68 Remote Similarity NPD8029 Clinical (unspecified phase)
0.68 Remote Similarity NPD4225 Approved
0.6788 Remote Similarity NPD8380 Approved
0.6788 Remote Similarity NPD8335 Approved
0.6788 Remote Similarity NPD8296 Approved
0.6788 Remote Similarity NPD8378 Approved
0.6788 Remote Similarity NPD8379 Approved
0.6788 Remote Similarity NPD8033 Approved
0.6777 Remote Similarity NPD46 Approved
0.6777 Remote Similarity NPD6698 Approved
0.6769 Remote Similarity NPD6899 Approved
0.6769 Remote Similarity NPD6881 Approved
0.6748 Remote Similarity NPD5282 Discontinued
0.6744 Remote Similarity NPD6008 Approved
0.6741 Remote Similarity NPD8295 Clinical (unspecified phase)
0.6718 Remote Similarity NPD6373 Approved
0.6718 Remote Similarity NPD6372 Approved
0.6715 Remote Similarity NPD8294 Approved
0.6715 Remote Similarity NPD8377 Approved
0.6692 Remote Similarity NPD6412 Phase 2
0.6692 Remote Similarity NPD5697 Approved
0.6692 Remote Similarity NPD5954 Clinical (unspecified phase)
0.6692 Remote Similarity NPD6053 Discontinued
0.6691 Remote Similarity NPD7604 Phase 2
0.6691 Remote Similarity NPD7830 Approved
0.6691 Remote Similarity NPD7829 Approved
0.6667 Remote Similarity NPD7290 Approved
0.6667 Remote Similarity NPD7102 Approved
0.6667 Remote Similarity NPD6883 Approved
0.6641 Remote Similarity NPD5211 Phase 2
0.6641 Remote Similarity NPD7320 Approved
0.6639 Remote Similarity NPD7838 Discovery
0.6617 Remote Similarity NPD6847 Approved
0.6617 Remote Similarity NPD6617 Approved
0.6617 Remote Similarity NPD8130 Phase 1
0.6617 Remote Similarity NPD6869 Approved
0.6615 Remote Similarity NPD6675 Approved
0.6615 Remote Similarity NPD7128 Approved
0.6615 Remote Similarity NPD6402 Approved
0.6615 Remote Similarity NPD5739 Approved
0.6614 Remote Similarity NPD5285 Approved
0.6614 Remote Similarity NPD5286 Approved
0.6614 Remote Similarity NPD4696 Approved
0.6608 Remote Similarity NPD8055 Clinical (unspecified phase)
0.6597 Remote Similarity NPD7260 Phase 2
0.6591 Remote Similarity NPD6014 Approved
0.6591 Remote Similarity NPD6013 Approved
0.6591 Remote Similarity NPD6012 Approved
0.6585 Remote Similarity NPD7983 Approved
0.6571 Remote Similarity NPD7642 Approved
0.6557 Remote Similarity NPD1695 Approved
0.6547 Remote Similarity NPD5983 Phase 2
0.6538 Remote Similarity NPD5141 Approved
0.6532 Remote Similarity NPD5778 Approved
0.6532 Remote Similarity NPD5779 Approved
0.6528 Remote Similarity NPD5956 Approved
0.6519 Remote Similarity NPD8133 Approved
0.6515 Remote Similarity NPD6011 Approved
0.6512 Remote Similarity NPD5225 Approved
0.6512 Remote Similarity NPD5226 Approved
0.6512 Remote Similarity NPD4633 Approved
0.6512 Remote Similarity NPD5224 Approved
0.6479 Remote Similarity NPD6336 Discontinued
0.6466 Remote Similarity NPD8132 Clinical (unspecified phase)
0.6462 Remote Similarity NPD5175 Approved
0.6462 Remote Similarity NPD5174 Approved
0.6457 Remote Similarity NPD4755 Approved
0.6439 Remote Similarity NPD5701 Approved
0.6438 Remote Similarity NPD8338 Approved
0.6438 Remote Similarity NPD6845 Suspended
0.6434 Remote Similarity NPD5223 Approved
0.6429 Remote Similarity NPD7799 Discontinued
0.6406 Remote Similarity NPD7638 Approved
0.6391 Remote Similarity NPD4729 Approved
0.6391 Remote Similarity NPD4730 Approved
0.6364 Remote Similarity NPD8451 Approved
0.6358 Remote Similarity NPD8407 Phase 2
0.6357 Remote Similarity NPD7639 Approved
0.6357 Remote Similarity NPD4700 Approved
0.6357 Remote Similarity NPD7640 Approved
0.6319 Remote Similarity NPD8448 Approved
0.6312 Remote Similarity NPD6291 Clinical (unspecified phase)
0.6308 Remote Similarity NPD1700 Approved
0.6296 Remote Similarity NPD5248 Approved
0.6296 Remote Similarity NPD5249 Phase 3
0.6296 Remote Similarity NPD5250 Approved
0.6296 Remote Similarity NPD5251 Approved
0.6296 Remote Similarity NPD5247 Approved
0.629 Remote Similarity NPD6101 Approved
0.629 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6286 Remote Similarity NPD7101 Approved
0.6286 Remote Similarity NPD7100 Approved
0.6279 Remote Similarity NPD8368 Discontinued
0.625 Remote Similarity NPD5222 Approved
0.625 Remote Similarity NPD5221 Approved
0.625 Remote Similarity NPD5220 Clinical (unspecified phase)
0.625 Remote Similarity NPD6401 Clinical (unspecified phase)
0.625 Remote Similarity NPD7839 Suspended
0.6241 Remote Similarity NPD4768 Approved
0.6241 Remote Similarity NPD4767 Approved
0.6224 Remote Similarity NPD6067 Discontinued
0.6214 Remote Similarity NPD6335 Approved
0.6214 Remote Similarity NPD7641 Discontinued
0.6202 Remote Similarity NPD5173 Approved
0.6197 Remote Similarity NPD8444 Approved
0.619 Remote Similarity NPD8390 Approved
0.619 Remote Similarity NPD6411 Approved
0.619 Remote Similarity NPD8392 Approved
0.619 Remote Similarity NPD8391 Approved
0.619 Remote Similarity NPD6079 Approved
0.6187 Remote Similarity NPD6274 Approved
0.6181 Remote Similarity NPD8299 Approved
0.6181 Remote Similarity NPD8342 Approved
0.6181 Remote Similarity NPD8340 Approved
0.6181 Remote Similarity NPD8341 Approved
0.6148 Remote Similarity NPD5128 Approved
0.6143 Remote Similarity NPD6317 Approved
0.6138 Remote Similarity NPD8273 Phase 1
0.6133 Remote Similarity NPD8415 Approved
0.6131 Remote Similarity NPD5215 Approved
0.6131 Remote Similarity NPD5216 Approved
0.6131 Remote Similarity NPD5217 Approved
0.6124 Remote Similarity NPD4697 Phase 3
0.6099 Remote Similarity NPD6313 Approved
0.6099 Remote Similarity NPD6314 Approved
0.6098 Remote Similarity NPD1733 Clinical (unspecified phase)
0.6093 Remote Similarity NPD8387 Clinical (unspecified phase)
0.609 Remote Similarity NPD4754 Approved
0.6084 Remote Similarity NPD8266 Approved
0.6084 Remote Similarity NPD8268 Approved
0.6084 Remote Similarity NPD8267 Approved
0.6084 Remote Similarity NPD8269 Approved
0.6077 Remote Similarity NPD6084 Phase 2
0.6077 Remote Similarity NPD6083 Phase 2
0.6063 Remote Similarity NPD7637 Suspended
0.6058 Remote Similarity NPD5134 Clinical (unspecified phase)
0.6058 Remote Similarity NPD5169 Approved
0.6058 Remote Similarity NPD5135 Approved
0.6054 Remote Similarity NPD8336 Approved
0.6054 Remote Similarity NPD8337 Approved
0.6047 Remote Similarity NPD5210 Approved
0.6047 Remote Similarity NPD4629 Approved
0.6045 Remote Similarity NPD8170 Clinical (unspecified phase)
0.6042 Remote Similarity NPD8080 Discontinued
0.6032 Remote Similarity NPD5328 Approved
0.6014 Remote Similarity NPD5127 Approved
0.6011 Remote Similarity NPD8434 Phase 2
0.6 Remote Similarity NPD7524 Approved
0.5984 Remote Similarity NPD3168 Discontinued
0.5984 Remote Similarity NPD5785 Approved
0.5972 Remote Similarity NPD6908 Approved
0.5972 Remote Similarity NPD6909 Approved
0.5968 Remote Similarity NPD1696 Phase 3
0.5968 Remote Similarity NPD1694 Approved
0.5957 Remote Similarity NPD6868 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