Structure

Physi-Chem Properties

Molecular Weight:  350.21
Volume:  364.849
LogP:  2.765
LogD:  2.551
LogS:  -3.357
# Rotatable Bonds:  3
TPSA:  90.9
# H-Bond Aceptor:  5
# H-Bond Donor:  3
# Rings:  3
# Heavy Atoms:  5

MedChem Properties

QED Drug-Likeness Score:  0.779
Synthetic Accessibility Score:  4.921
Fsp3:  0.75
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
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:  -4.774
MDCK Permeability:  1.9535817045834847e-05
Pgp-inhibitor:  0.001
Pgp-substrate:  0.952
Human Intestinal Absorption (HIA):  0.009
20% Bioavailability (F20%):  0.357
30% Bioavailability (F30%):  0.02

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.875
Plasma Protein Binding (PPB):  92.71812438964844%
Volume Distribution (VD):  1.234
Pgp-substrate:  13.012568473815918%

ADMET: Metabolism

CYP1A2-inhibitor:  0.024
CYP1A2-substrate:  0.176
CYP2C19-inhibitor:  0.041
CYP2C19-substrate:  0.519
CYP2C9-inhibitor:  0.216
CYP2C9-substrate:  0.603
CYP2D6-inhibitor:  0.015
CYP2D6-substrate:  0.541
CYP3A4-inhibitor:  0.136
CYP3A4-substrate:  0.219

ADMET: Excretion

Clearance (CL):  12.357
Half-life (T1/2):  0.754

ADMET: Toxicity

hERG Blockers:  0.049
Human Hepatotoxicity (H-HT):  0.259
Drug-inuced Liver Injury (DILI):  0.052
AMES Toxicity:  0.007
Rat Oral Acute Toxicity:  0.956
Maximum Recommended Daily Dose:  0.95
Skin Sensitization:  0.189
Carcinogencity:  0.696
Eye Corrosion:  0.012
Eye Irritation:  0.039
Respiratory Toxicity:  0.971

Download Data

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

  Natural Product: NPC477950

Natural Product ID:  NPC477950
Common Name*:   3-[2-[(2S,3aS,5R,6R,8aS)-2,8a-dihydroxy-1,1,5,6-tetramethyl-4-oxo-2,3,3a,6,7,8-hexahydroazulen-5-yl]ethyl]-2H-furan-5-one
IUPAC Name:   3-[2-[(2S,3aS,5R,6R,8aS)-2,8a-dihydroxy-1,1,5,6-tetramethyl-4-oxo-2,3,3a,6,7,8-hexahydroazulen-5-yl]ethyl]-2H-furan-5-one
Synonyms:  
Standard InCHIKey:  XDKFKXXCPUQUEE-DBSYTYAISA-N
Standard InCHI:  InChI=1S/C20H30O5/c1-12-5-8-20(24)14(10-15(21)18(20,2)3)17(23)19(12,4)7-6-13-9-16(22)25-11-13/h9,12,14-15,21,24H,5-8,10-11H2,1-4H3/t12-,14-,15+,19-,20+/m1/s1
SMILES:  C[C@@H]1CC[C@@]2([C@H](C[C@@H](C2(C)C)O)C(=O)[C@]1(C)CCC3=CC(=O)OC3)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   n.a.
PubChem CID:   90682204
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0001983] Dihydrofurans
        • [CHEMONTID:0001982] Furanones
          • [CHEMONTID:0002223] Butenolides

*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
NPO23559 Solidago shortii Species Asteraceae Eukaryota above-ground portion Shaw Nature Reserve (Missouri Botanical Garden) (N 38 28.579, W 90 49.500) 2008-SEP PMID[24922615]
NPO23559 Solidago shortii Species Asteraceae 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
NPT16 Organism Staphylococcus aureus Staphylococcus aureus GI = 56 % PMID[24922615]

☑ 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 NPC477950 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
0.9263 High Similarity NPC477949
0.8788 High Similarity NPC171759
0.866 High Similarity NPC37408
0.8586 High Similarity NPC141191
0.8571 High Similarity NPC126156
0.8571 High Similarity NPC185553
0.8529 High Similarity NPC309190
0.8485 Intermediate Similarity NPC169205
0.8485 Intermediate Similarity NPC213947
0.8485 Intermediate Similarity NPC108475
0.8485 Intermediate Similarity NPC170143
0.8469 Intermediate Similarity NPC48803
0.8469 Intermediate Similarity NPC193645
0.8469 Intermediate Similarity NPC275960
0.8469 Intermediate Similarity NPC469873
0.8469 Intermediate Similarity NPC90121
0.8416 Intermediate Similarity NPC475099
0.8384 Intermediate Similarity NPC142529
0.8384 Intermediate Similarity NPC18019
0.8384 Intermediate Similarity NPC91771
0.8384 Intermediate Similarity NPC24956
0.8351 Intermediate Similarity NPC284185
0.8333 Intermediate Similarity NPC118405
0.8333 Intermediate Similarity NPC212664
0.8333 Intermediate Similarity NPC168679
0.8333 Intermediate Similarity NPC12872
0.8317 Intermediate Similarity NPC280963
0.83 Intermediate Similarity NPC161493
0.8283 Intermediate Similarity NPC476487
0.8283 Intermediate Similarity NPC476488
0.8252 Intermediate Similarity NPC110989
0.8247 Intermediate Similarity NPC253144
0.82 Intermediate Similarity NPC213078
0.8182 Intermediate Similarity NPC167219
0.8173 Intermediate Similarity NPC203659
0.8163 Intermediate Similarity NPC150978
0.8163 Intermediate Similarity NPC74103
0.8163 Intermediate Similarity NPC70595
0.8163 Intermediate Similarity NPC123177
0.8155 Intermediate Similarity NPC225353
0.8144 Intermediate Similarity NPC117405
0.8144 Intermediate Similarity NPC52198
0.8137 Intermediate Similarity NPC469872
0.8137 Intermediate Similarity NPC469864
0.8125 Intermediate Similarity NPC201658
0.8125 Intermediate Similarity NPC45957
0.8125 Intermediate Similarity NPC471657
0.8119 Intermediate Similarity NPC69385
0.8119 Intermediate Similarity NPC87090
0.8105 Intermediate Similarity NPC245434
0.81 Intermediate Similarity NPC52044
0.81 Intermediate Similarity NPC213698
0.81 Intermediate Similarity NPC67584
0.8095 Intermediate Similarity NPC54737
0.8081 Intermediate Similarity NPC153590
0.8081 Intermediate Similarity NPC60386
0.8081 Intermediate Similarity NPC473263
0.8081 Intermediate Similarity NPC473234
0.8081 Intermediate Similarity NPC473273
0.8081 Intermediate Similarity NPC308656
0.8081 Intermediate Similarity NPC200237
0.8058 Intermediate Similarity NPC206079
0.8058 Intermediate Similarity NPC477356
0.8058 Intermediate Similarity NPC195192
0.8058 Intermediate Similarity NPC304738
0.8039 Intermediate Similarity NPC222011
0.8039 Intermediate Similarity NPC477355
0.8039 Intermediate Similarity NPC64742
0.8039 Intermediate Similarity NPC470188
0.8021 Intermediate Similarity NPC309757
0.8021 Intermediate Similarity NPC236692
0.8021 Intermediate Similarity NPC238593
0.802 Intermediate Similarity NPC9812
0.8018 Intermediate Similarity NPC475305
0.8 Intermediate Similarity NPC100487
0.8 Intermediate Similarity NPC127019
0.8 Intermediate Similarity NPC96541
0.8 Intermediate Similarity NPC477131
0.8 Intermediate Similarity NPC144625
0.8 Intermediate Similarity NPC469632
0.798 Intermediate Similarity NPC221282
0.798 Intermediate Similarity NPC171360
0.798 Intermediate Similarity NPC133888
0.798 Intermediate Similarity NPC35959
0.798 Intermediate Similarity NPC286341
0.798 Intermediate Similarity NPC57304
0.798 Intermediate Similarity NPC261607
0.798 Intermediate Similarity NPC29821
0.798 Intermediate Similarity NPC293001
0.798 Intermediate Similarity NPC475925
0.798 Intermediate Similarity NPC191339
0.798 Intermediate Similarity NPC111114
0.798 Intermediate Similarity NPC63193
0.798 Intermediate Similarity NPC300312
0.7963 Intermediate Similarity NPC257240
0.7963 Intermediate Similarity NPC477103
0.7959 Intermediate Similarity NPC170775
0.7946 Intermediate Similarity NPC475401
0.7941 Intermediate Similarity NPC311904
0.7925 Intermediate Similarity NPC243998
0.7925 Intermediate Similarity NPC179891
0.7921 Intermediate Similarity NPC170120
0.7921 Intermediate Similarity NPC163228
0.7905 Intermediate Similarity NPC475945
0.7905 Intermediate Similarity NPC475871
0.79 Intermediate Similarity NPC135776
0.79 Intermediate Similarity NPC37816
0.79 Intermediate Similarity NPC125180
0.789 Intermediate Similarity NPC474750
0.789 Intermediate Similarity NPC287311
0.7885 Intermediate Similarity NPC150923
0.7885 Intermediate Similarity NPC116139
0.7879 Intermediate Similarity NPC129419
0.7879 Intermediate Similarity NPC297474
0.7879 Intermediate Similarity NPC77337
0.7879 Intermediate Similarity NPC35809
0.7879 Intermediate Similarity NPC216284
0.7879 Intermediate Similarity NPC54065
0.7876 Intermediate Similarity NPC477092
0.787 Intermediate Similarity NPC477102
0.787 Intermediate Similarity NPC139838
0.787 Intermediate Similarity NPC59489
0.787 Intermediate Similarity NPC475941
0.787 Intermediate Similarity NPC474901
0.787 Intermediate Similarity NPC47951
0.7864 Intermediate Similarity NPC244411
0.7864 Intermediate Similarity NPC54843
0.7864 Intermediate Similarity NPC221615
0.785 Intermediate Similarity NPC204884
0.785 Intermediate Similarity NPC473911
0.7835 Intermediate Similarity NPC70555
0.7835 Intermediate Similarity NPC104961
0.7835 Intermediate Similarity NPC70422
0.7822 Intermediate Similarity NPC53685
0.7822 Intermediate Similarity NPC470010
0.7822 Intermediate Similarity NPC323008
0.7822 Intermediate Similarity NPC198853
0.7822 Intermediate Similarity NPC90453
0.7822 Intermediate Similarity NPC262133
0.7822 Intermediate Similarity NPC473331
0.7822 Intermediate Similarity NPC470013
0.7822 Intermediate Similarity NPC289004
0.7818 Intermediate Similarity NPC123855
0.7818 Intermediate Similarity NPC138757
0.7818 Intermediate Similarity NPC76550
0.7812 Intermediate Similarity NPC53011
0.7812 Intermediate Similarity NPC37005
0.7812 Intermediate Similarity NPC154893
0.7812 Intermediate Similarity NPC16887
0.781 Intermediate Similarity NPC105725
0.781 Intermediate Similarity NPC474747
0.781 Intermediate Similarity NPC66110
0.781 Intermediate Similarity NPC49393
0.78 Intermediate Similarity NPC131209
0.78 Intermediate Similarity NPC184063
0.78 Intermediate Similarity NPC290651
0.78 Intermediate Similarity NPC472705
0.78 Intermediate Similarity NPC133698
0.7798 Intermediate Similarity NPC41551
0.7798 Intermediate Similarity NPC206595
0.7798 Intermediate Similarity NPC50223
0.7788 Intermediate Similarity NPC161060
0.7778 Intermediate Similarity NPC155935
0.7778 Intermediate Similarity NPC215556
0.7778 Intermediate Similarity NPC32922
0.7778 Intermediate Similarity NPC308191
0.7778 Intermediate Similarity NPC268298
0.7768 Intermediate Similarity NPC72772
0.7768 Intermediate Similarity NPC469794
0.7767 Intermediate Similarity NPC471150
0.7759 Intermediate Similarity NPC1538
0.7757 Intermediate Similarity NPC190867
0.7757 Intermediate Similarity NPC473488
0.7757 Intermediate Similarity NPC475661
0.7757 Intermediate Similarity NPC291643
0.7757 Intermediate Similarity NPC223450
0.7755 Intermediate Similarity NPC237540
0.7748 Intermediate Similarity NPC209058
0.7748 Intermediate Similarity NPC46269
0.7748 Intermediate Similarity NPC106395
0.7748 Intermediate Similarity NPC9848
0.7748 Intermediate Similarity NPC312017
0.7745 Intermediate Similarity NPC304886
0.7745 Intermediate Similarity NPC476053
0.7745 Intermediate Similarity NPC474490
0.7745 Intermediate Similarity NPC472873
0.7739 Intermediate Similarity NPC471999
0.7739 Intermediate Similarity NPC472000
0.7736 Intermediate Similarity NPC474775
0.7732 Intermediate Similarity NPC78089
0.7731 Intermediate Similarity NPC13071
0.7727 Intermediate Similarity NPC475495
0.7723 Intermediate Similarity NPC109414
0.7723 Intermediate Similarity NPC477361
0.7723 Intermediate Similarity NPC202824
0.7714 Intermediate Similarity NPC133907
0.7714 Intermediate Similarity NPC110443
0.7714 Intermediate Similarity NPC46998
0.7714 Intermediate Similarity NPC472753
0.7714 Intermediate Similarity NPC62670

  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 NPC477950 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
0.8469 Intermediate Similarity NPD1698 Clinical (unspecified phase)
0.8061 Intermediate Similarity NPD5785 Approved
0.7963 Intermediate Similarity NPD6371 Approved
0.7789 Intermediate Similarity NPD6435 Approved
0.7685 Intermediate Similarity NPD7899 Clinical (unspecified phase)
0.7658 Intermediate Similarity NPD6053 Discontinued
0.7653 Intermediate Similarity NPD5786 Approved
0.7579 Intermediate Similarity NPD5368 Approved
0.7551 Intermediate Similarity NPD6082 Clinical (unspecified phase)
0.7551 Intermediate Similarity NPD5363 Approved
0.75 Intermediate Similarity NPD5369 Approved
0.7455 Intermediate Similarity NPD7320 Approved
0.7431 Intermediate Similarity NPD6402 Approved
0.7431 Intermediate Similarity NPD5739 Approved
0.7431 Intermediate Similarity NPD6675 Approved
0.7431 Intermediate Similarity NPD7128 Approved
0.7423 Intermediate Similarity NPD4270 Approved
0.7423 Intermediate Similarity NPD4269 Approved
0.7387 Intermediate Similarity NPD6373 Approved
0.7387 Intermediate Similarity NPD6372 Approved
0.7364 Intermediate Similarity NPD5697 Approved
0.7364 Intermediate Similarity NPD5701 Approved
0.7347 Intermediate Similarity NPD5362 Discontinued
0.7297 Intermediate Similarity NPD6899 Approved
0.7297 Intermediate Similarity NPD6881 Approved
0.7264 Intermediate Similarity NPD6084 Phase 2
0.7264 Intermediate Similarity NPD6083 Phase 2
0.7257 Intermediate Similarity NPD6650 Approved
0.7257 Intermediate Similarity NPD6649 Approved
0.7255 Intermediate Similarity NPD1695 Approved
0.7238 Intermediate Similarity NPD5695 Phase 3
0.7232 Intermediate Similarity NPD6014 Approved
0.7232 Intermediate Similarity NPD6013 Approved
0.7232 Intermediate Similarity NPD6012 Approved
0.7216 Intermediate Similarity NPD4820 Approved
0.7216 Intermediate Similarity NPD4819 Approved
0.7216 Intermediate Similarity NPD4822 Approved
0.7216 Intermediate Similarity NPD5790 Clinical (unspecified phase)
0.7216 Intermediate Similarity NPD4252 Approved
0.7216 Intermediate Similarity NPD4821 Approved
0.7196 Intermediate Similarity NPD5696 Approved
0.7188 Intermediate Similarity NPD5784 Clinical (unspecified phase)
0.7168 Intermediate Similarity NPD7290 Approved
0.7168 Intermediate Similarity NPD7102 Approved
0.7168 Intermediate Similarity NPD6883 Approved
0.7154 Intermediate Similarity NPD7319 Approved
0.7143 Intermediate Similarity NPD6011 Approved
0.7105 Intermediate Similarity NPD6869 Approved
0.7105 Intermediate Similarity NPD6847 Approved
0.7105 Intermediate Similarity NPD6617 Approved
0.7105 Intermediate Similarity NPD8130 Phase 1
0.7103 Intermediate Similarity NPD4755 Approved
0.7094 Intermediate Similarity NPD7115 Discovery
0.7049 Intermediate Similarity NPD7507 Approved
0.7043 Intermediate Similarity NPD6882 Approved
0.7043 Intermediate Similarity NPD8297 Approved
0.701 Intermediate Similarity NPD4268 Approved
0.701 Intermediate Similarity NPD4271 Approved
0.7 Intermediate Similarity NPD5211 Phase 2
0.7 Intermediate Similarity NPD7154 Phase 3
0.6981 Remote Similarity NPD5282 Discontinued
0.6972 Remote Similarity NPD5286 Approved
0.6972 Remote Similarity NPD4700 Approved
0.6972 Remote Similarity NPD5285 Approved
0.6972 Remote Similarity NPD4696 Approved
0.6964 Remote Similarity NPD6008 Approved
0.6961 Remote Similarity NPD4249 Approved
0.6957 Remote Similarity NPD6401 Clinical (unspecified phase)
0.6952 Remote Similarity NPD5284 Approved
0.6952 Remote Similarity NPD5281 Approved
0.6952 Remote Similarity NPD5693 Phase 1
0.6923 Remote Similarity NPD4753 Phase 2
0.6917 Remote Similarity NPD6319 Approved
0.69 Remote Similarity NPD4752 Clinical (unspecified phase)
0.69 Remote Similarity NPD5209 Approved
0.6893 Remote Similarity NPD4251 Approved
0.6893 Remote Similarity NPD4250 Approved
0.6887 Remote Similarity NPD6399 Phase 3
0.6881 Remote Similarity NPD4225 Approved
0.6881 Remote Similarity NPD7638 Approved
0.6875 Remote Similarity NPD5141 Approved
0.6864 Remote Similarity NPD6274 Approved
0.6847 Remote Similarity NPD4633 Approved
0.6847 Remote Similarity NPD5226 Approved
0.6847 Remote Similarity NPD5224 Approved
0.6847 Remote Similarity NPD5225 Approved
0.6832 Remote Similarity NPD5332 Approved
0.6832 Remote Similarity NPD5331 Approved
0.6829 Remote Similarity NPD7492 Approved
0.6827 Remote Similarity NPD6903 Approved
0.6818 Remote Similarity NPD7640 Approved
0.6818 Remote Similarity NPD7639 Approved
0.68 Remote Similarity NPD4790 Discontinued
0.6796 Remote Similarity NPD7521 Approved
0.6796 Remote Similarity NPD7334 Approved
0.6796 Remote Similarity NPD7146 Approved
0.6796 Remote Similarity NPD6684 Approved
0.6796 Remote Similarity NPD6409 Approved
0.6796 Remote Similarity NPD5330 Approved
0.6792 Remote Similarity NPD6411 Approved
0.6786 Remote Similarity NPD5175 Approved
0.6786 Remote Similarity NPD5174 Approved
0.6777 Remote Similarity NPD6059 Approved
0.6777 Remote Similarity NPD6054 Approved
0.6774 Remote Similarity NPD6616 Approved
0.6765 Remote Similarity NPD3666 Approved
0.6765 Remote Similarity NPD3665 Phase 1
0.6765 Remote Similarity NPD3133 Approved
0.6759 Remote Similarity NPD6356 Clinical (unspecified phase)
0.6759 Remote Similarity NPD5210 Approved
0.6759 Remote Similarity NPD4629 Approved
0.6757 Remote Similarity NPD5223 Approved
0.6729 Remote Similarity NPD5778 Approved
0.6729 Remote Similarity NPD4202 Approved
0.6729 Remote Similarity NPD5779 Approved
0.6724 Remote Similarity NPD4634 Approved
0.6721 Remote Similarity NPD6016 Approved
0.6721 Remote Similarity NPD6015 Approved
0.6721 Remote Similarity NPD6291 Clinical (unspecified phase)
0.672 Remote Similarity NPD8293 Discontinued
0.672 Remote Similarity NPD7078 Approved
0.6699 Remote Similarity NPD1694 Approved
0.6698 Remote Similarity NPD46 Approved
0.6698 Remote Similarity NPD5207 Approved
0.6698 Remote Similarity NPD6698 Approved
0.6696 Remote Similarity NPD6686 Approved
0.6695 Remote Similarity NPD4632 Approved
0.6694 Remote Similarity NPD7101 Approved
0.6694 Remote Similarity NPD7100 Approved
0.6667 Remote Similarity NPD6317 Approved
0.6667 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6667 Remote Similarity NPD5988 Approved
0.6667 Remote Similarity NPD4767 Approved
0.6667 Remote Similarity NPD4768 Approved
0.6667 Remote Similarity NPD6370 Approved
0.6667 Remote Similarity NPD7736 Approved
0.6637 Remote Similarity NPD4754 Approved
0.6636 Remote Similarity NPD7983 Approved
0.6636 Remote Similarity NPD7637 Suspended
0.6612 Remote Similarity NPD6314 Approved
0.6612 Remote Similarity NPD6335 Approved
0.6612 Remote Similarity NPD6313 Approved
0.6604 Remote Similarity NPD6904 Approved
0.6604 Remote Similarity NPD6673 Approved
0.6604 Remote Similarity NPD6101 Approved
0.6604 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6604 Remote Similarity NPD6080 Approved
0.6604 Remote Similarity NPD5328 Approved
0.6585 Remote Similarity NPD6908 Approved
0.6585 Remote Similarity NPD6909 Approved
0.6569 Remote Similarity NPD4221 Approved
0.6569 Remote Similarity NPD4223 Phase 3
0.6552 Remote Similarity NPD4729 Approved
0.6552 Remote Similarity NPD5128 Approved
0.6552 Remote Similarity NPD4730 Approved
0.6545 Remote Similarity NPD4697 Phase 3
0.6542 Remote Similarity NPD5692 Phase 3
0.6529 Remote Similarity NPD6009 Approved
0.6514 Remote Similarity NPD6001 Approved
0.6509 Remote Similarity NPD5208 Approved
0.6509 Remote Similarity NPD6672 Approved
0.6509 Remote Similarity NPD5737 Approved
0.6481 Remote Similarity NPD6050 Approved
0.6481 Remote Similarity NPD6079 Approved
0.6481 Remote Similarity NPD5694 Approved
0.6476 Remote Similarity NPD5279 Phase 3
0.6476 Remote Similarity NPD3574 Clinical (unspecified phase)
0.6476 Remote Similarity NPD3618 Phase 1
0.6475 Remote Similarity NPD7328 Approved
0.6475 Remote Similarity NPD7327 Approved
0.6466 Remote Similarity NPD6412 Phase 2
0.6452 Remote Similarity NPD5983 Phase 2
0.6452 Remote Similarity NPD8033 Approved
0.6449 Remote Similarity NPD6051 Approved
0.6442 Remote Similarity NPD4197 Approved
0.6441 Remote Similarity NPD5251 Approved
0.6441 Remote Similarity NPD5249 Phase 3
0.6441 Remote Similarity NPD5250 Approved
0.6441 Remote Similarity NPD5247 Approved
0.6441 Remote Similarity NPD5248 Approved
0.6423 Remote Similarity NPD7516 Approved
0.6408 Remote Similarity NPD4800 Clinical (unspecified phase)
0.6396 Remote Similarity NPD5222 Approved
0.6396 Remote Similarity NPD5221 Approved
0.6396 Remote Similarity NPD5220 Clinical (unspecified phase)
0.6387 Remote Similarity NPD5215 Approved
0.6387 Remote Similarity NPD5216 Approved
0.6387 Remote Similarity NPD5217 Approved
0.6381 Remote Similarity NPD1733 Clinical (unspecified phase)
0.6381 Remote Similarity NPD5329 Approved
0.6371 Remote Similarity NPD8294 Approved
0.6371 Remote Similarity NPD8377 Approved
0.6356 Remote Similarity NPD4061 Clinical (unspecified phase)
0.6349 Remote Similarity NPD7604 Phase 2
0.6339 Remote Similarity NPD5173 Approved
0.6339 Remote Similarity NPD7902 Approved
0.6321 Remote Similarity NPD4690 Approved
0.6321 Remote Similarity NPD5690 Phase 2
0.6321 Remote Similarity NPD4694 Approved
0.6321 Remote Similarity NPD5205 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