Structure

Physi-Chem Properties

Molecular Weight:  332.2
Volume:  359.342
LogP:  3.094
LogD:  2.229
LogS:  -3.663
# Rotatable Bonds:  4
TPSA:  60.44
# H-Bond Aceptor:  4
# H-Bond Donor:  0
# Rings:  2
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.342
Synthetic Accessibility Score:  5.144
Fsp3:  0.65
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.663
MDCK Permeability:  2.3023820176604204e-05
Pgp-inhibitor:  0.588
Pgp-substrate:  0.002
Human Intestinal Absorption (HIA):  0.006
20% Bioavailability (F20%):  0.016
30% Bioavailability (F30%):  0.203

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.871
Plasma Protein Binding (PPB):  81.49723815917969%
Volume Distribution (VD):  0.861
Pgp-substrate:  20.668264389038086%

ADMET: Metabolism

CYP1A2-inhibitor:  0.151
CYP1A2-substrate:  0.58
CYP2C19-inhibitor:  0.776
CYP2C19-substrate:  0.824
CYP2C9-inhibitor:  0.481
CYP2C9-substrate:  0.09
CYP2D6-inhibitor:  0.074
CYP2D6-substrate:  0.221
CYP3A4-inhibitor:  0.818
CYP3A4-substrate:  0.327

ADMET: Excretion

Clearance (CL):  13.233
Half-life (T1/2):  0.205

ADMET: Toxicity

hERG Blockers:  0.036
Human Hepatotoxicity (H-HT):  0.491
Drug-inuced Liver Injury (DILI):  0.338
AMES Toxicity:  0.057
Rat Oral Acute Toxicity:  0.107
Maximum Recommended Daily Dose:  0.701
Skin Sensitization:  0.506
Carcinogencity:  0.269
Eye Corrosion:  0.347
Eye Irritation:  0.396
Respiratory Toxicity:  0.945

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

  Natural Product: NPC222011

Natural Product ID:  NPC222011
Common Name*:   (3R,4S,5R,7S,9R)-3-Hydroxy-9-Tigloyloxysolavetivone
IUPAC Name:   [(2S,4R,5R,6S,7R)-7-hydroxy-6,10-dimethyl-8-oxo-2-prop-1-en-2-ylspiro[4.5]dec-9-en-4-yl] (E)-2-methylbut-2-enoate
Synonyms:  
Standard InCHIKey:  PRZHJEFHHOMZQJ-UFXSKVETSA-N
Standard InCHI:  InChI=1S/C20H28O4/c1-7-12(4)19(23)24-17-9-15(11(2)3)10-20(17)13(5)8-16(21)18(22)14(20)6/h7-8,14-15,17-18,22H,2,9-10H2,1,3-6H3/b12-7+/t14-,15-,17-,18-,20+/m1/s1
SMILES:  C/C=C(C)/C(=O)O[C@@H]1C[C@H](C[C@]21C(=CC(=O)[C@@H]([C@H]2C)O)C)C(=C)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL518719
PubChem CID:   10471966
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001550] Sesquiterpenoids

*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
NPO14489 Hyoscyamus albus Species Solanaceae Eukaryota Hairy roots n.a. n.a. PMID[9868154]
NPO16093 Achillea atrata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25348 Metapochonia suchlasporia Species Clavicipitaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14489 Hyoscyamus albus Species Solanaceae 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 MIC = 100.0 ug.mL-1 PMID[480076]
NPT79 Organism Bacillus subtilis Bacillus subtilis MIC = 250.0 ug.mL-1 PMID[480076]

☑ 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 NPC222011 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
0.989 High Similarity NPC69385
0.9451 High Similarity NPC109414
0.8681 High Similarity NPC36350
0.8673 High Similarity NPC472644
0.8646 High Similarity NPC470974
0.8646 High Similarity NPC470978
0.8641 High Similarity NPC206595
0.8586 High Similarity NPC472643
0.8542 High Similarity NPC53685
0.8529 High Similarity NPC475294
0.8515 High Similarity NPC235889
0.8485 Intermediate Similarity NPC476274
0.8476 Intermediate Similarity NPC221144
0.8476 Intermediate Similarity NPC475524
0.8476 Intermediate Similarity NPC100267
0.8469 Intermediate Similarity NPC474343
0.8431 Intermediate Similarity NPC181265
0.84 Intermediate Similarity NPC476240
0.84 Intermediate Similarity NPC224720
0.84 Intermediate Similarity NPC81530
0.84 Intermediate Similarity NPC476223
0.8384 Intermediate Similarity NPC197386
0.835 Intermediate Similarity NPC44063
0.8333 Intermediate Similarity NPC219874
0.8333 Intermediate Similarity NPC221282
0.8317 Intermediate Similarity NPC118405
0.8317 Intermediate Similarity NPC136289
0.8316 Intermediate Similarity NPC5509
0.8298 Intermediate Similarity NPC312561
0.8257 Intermediate Similarity NPC257457
0.8257 Intermediate Similarity NPC311554
0.8241 Intermediate Similarity NPC148458
0.8235 Intermediate Similarity NPC236390
0.8229 Intermediate Similarity NPC232426
0.8229 Intermediate Similarity NPC281942
0.8218 Intermediate Similarity NPC475099
0.8218 Intermediate Similarity NPC474327
0.82 Intermediate Similarity NPC176845
0.819 Intermediate Similarity NPC258543
0.819 Intermediate Similarity NPC2766
0.819 Intermediate Similarity NPC241927
0.8182 Intermediate Similarity NPC184065
0.8165 Intermediate Similarity NPC239273
0.8163 Intermediate Similarity NPC476596
0.8155 Intermediate Similarity NPC118911
0.8144 Intermediate Similarity NPC141831
0.8137 Intermediate Similarity NPC204450
0.8137 Intermediate Similarity NPC475320
0.8137 Intermediate Similarity NPC195290
0.8137 Intermediate Similarity NPC308726
0.8137 Intermediate Similarity NPC119601
0.8131 Intermediate Similarity NPC71348
0.81 Intermediate Similarity NPC285513
0.81 Intermediate Similarity NPC253826
0.81 Intermediate Similarity NPC208094
0.81 Intermediate Similarity NPC254496
0.81 Intermediate Similarity NPC18319
0.81 Intermediate Similarity NPC87090
0.8095 Intermediate Similarity NPC177064
0.8095 Intermediate Similarity NPC476479
0.8081 Intermediate Similarity NPC469599
0.8081 Intermediate Similarity NPC183012
0.8081 Intermediate Similarity NPC295347
0.8077 Intermediate Similarity NPC60681
0.8077 Intermediate Similarity NPC472645
0.8065 Intermediate Similarity NPC193198
0.8061 Intermediate Similarity NPC139692
0.8061 Intermediate Similarity NPC476597
0.8061 Intermediate Similarity NPC476598
0.8041 Intermediate Similarity NPC51486
0.8039 Intermediate Similarity NPC163372
0.8039 Intermediate Similarity NPC99411
0.8039 Intermediate Similarity NPC477356
0.8039 Intermediate Similarity NPC477950
0.8039 Intermediate Similarity NPC302537
0.8037 Intermediate Similarity NPC214797
0.8037 Intermediate Similarity NPC118860
0.8037 Intermediate Similarity NPC231589
0.802 Intermediate Similarity NPC23364
0.802 Intermediate Similarity NPC235464
0.802 Intermediate Similarity NPC166745
0.802 Intermediate Similarity NPC477355
0.8 Intermediate Similarity NPC96859
0.8 Intermediate Similarity NPC328371
0.8 Intermediate Similarity NPC220478
0.8 Intermediate Similarity NPC472925
0.8 Intermediate Similarity NPC471854
0.8 Intermediate Similarity NPC305483
0.8 Intermediate Similarity NPC328162
0.8 Intermediate Similarity NPC202394
0.8 Intermediate Similarity NPC261721
0.7982 Intermediate Similarity NPC178289
0.7981 Intermediate Similarity NPC309190
0.798 Intermediate Similarity NPC476415
0.798 Intermediate Similarity NPC148463
0.7979 Intermediate Similarity NPC474359
0.7963 Intermediate Similarity NPC264634
0.7963 Intermediate Similarity NPC170487
0.7961 Intermediate Similarity NPC87351
0.7961 Intermediate Similarity NPC308351
0.7961 Intermediate Similarity NPC271266
0.7961 Intermediate Similarity NPC56498
0.7961 Intermediate Similarity NPC185530
0.7959 Intermediate Similarity NPC186363
0.7959 Intermediate Similarity NPC233345
0.7944 Intermediate Similarity NPC37116
0.7944 Intermediate Similarity NPC197428
0.7944 Intermediate Similarity NPC5103
0.7941 Intermediate Similarity NPC205899
0.7941 Intermediate Similarity NPC174314
0.7941 Intermediate Similarity NPC474012
0.7941 Intermediate Similarity NPC476299
0.7941 Intermediate Similarity NPC144956
0.7941 Intermediate Similarity NPC117685
0.7941 Intermediate Similarity NPC241221
0.7938 Intermediate Similarity NPC123912
0.7938 Intermediate Similarity NPC168131
0.7925 Intermediate Similarity NPC472825
0.7925 Intermediate Similarity NPC275539
0.7925 Intermediate Similarity NPC295244
0.7925 Intermediate Similarity NPC189075
0.7925 Intermediate Similarity NPC94529
0.7921 Intermediate Similarity NPC84335
0.7921 Intermediate Similarity NPC477949
0.7921 Intermediate Similarity NPC18509
0.7921 Intermediate Similarity NPC202705
0.7921 Intermediate Similarity NPC43747
0.7921 Intermediate Similarity NPC38530
0.7909 Intermediate Similarity NPC190286
0.7909 Intermediate Similarity NPC270958
0.7905 Intermediate Similarity NPC1679
0.7905 Intermediate Similarity NPC469607
0.79 Intermediate Similarity NPC317586
0.79 Intermediate Similarity NPC470016
0.79 Intermediate Similarity NPC209355
0.79 Intermediate Similarity NPC472932
0.79 Intermediate Similarity NPC174948
0.79 Intermediate Similarity NPC173875
0.79 Intermediate Similarity NPC318282
0.79 Intermediate Similarity NPC134067
0.79 Intermediate Similarity NPC469995
0.7895 Intermediate Similarity NPC86316
0.7895 Intermediate Similarity NPC106416
0.7895 Intermediate Similarity NPC189311
0.7895 Intermediate Similarity NPC110405
0.7895 Intermediate Similarity NPC65661
0.789 Intermediate Similarity NPC472926
0.789 Intermediate Similarity NPC194100
0.789 Intermediate Similarity NPC71889
0.789 Intermediate Similarity NPC472929
0.789 Intermediate Similarity NPC202889
0.7885 Intermediate Similarity NPC311612
0.7885 Intermediate Similarity NPC111323
0.7885 Intermediate Similarity NPC159442
0.7885 Intermediate Similarity NPC474775
0.7885 Intermediate Similarity NPC26478
0.7879 Intermediate Similarity NPC477435
0.7879 Intermediate Similarity NPC125180
0.7879 Intermediate Similarity NPC115021
0.7879 Intermediate Similarity NPC477436
0.7876 Intermediate Similarity NPC472001
0.7876 Intermediate Similarity NPC471999
0.7876 Intermediate Similarity NPC472000
0.7872 Intermediate Similarity NPC222358
0.787 Intermediate Similarity NPC96739
0.787 Intermediate Similarity NPC43775
0.787 Intermediate Similarity NPC474871
0.787 Intermediate Similarity NPC260786
0.787 Intermediate Similarity NPC174471
0.7864 Intermediate Similarity NPC473384
0.7864 Intermediate Similarity NPC310981
0.7864 Intermediate Similarity NPC471412
0.7864 Intermediate Similarity NPC472637
0.7864 Intermediate Similarity NPC171759
0.7857 Intermediate Similarity NPC152467
0.7857 Intermediate Similarity NPC477149
0.7857 Intermediate Similarity NPC475041
0.7857 Intermediate Similarity NPC477147
0.7857 Intermediate Similarity NPC471818
0.785 Intermediate Similarity NPC304495
0.785 Intermediate Similarity NPC475941
0.785 Intermediate Similarity NPC474901
0.7843 Intermediate Similarity NPC57079
0.7843 Intermediate Similarity NPC98868
0.7843 Intermediate Similarity NPC316598
0.7843 Intermediate Similarity NPC141191
0.7843 Intermediate Similarity NPC108368
0.7843 Intermediate Similarity NPC114274
0.7843 Intermediate Similarity NPC10364
0.7835 Intermediate Similarity NPC477302
0.7835 Intermediate Similarity NPC294480
0.783 Intermediate Similarity NPC144459
0.783 Intermediate Similarity NPC185
0.783 Intermediate Similarity NPC110496
0.783 Intermediate Similarity NPC91034
0.7822 Intermediate Similarity NPC234993
0.7822 Intermediate Similarity NPC242848
0.7822 Intermediate Similarity NPC202833
0.7822 Intermediate Similarity NPC118159
0.7822 Intermediate Similarity NPC134072

  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 NPC222011 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
0.835 Intermediate Similarity NPD5697 Approved
0.8269 Intermediate Similarity NPD6899 Approved
0.8269 Intermediate Similarity NPD6881 Approved
0.8269 Intermediate Similarity NPD6011 Approved
0.8252 Intermediate Similarity NPD6675 Approved
0.8252 Intermediate Similarity NPD7128 Approved
0.8252 Intermediate Similarity NPD5739 Approved
0.8252 Intermediate Similarity NPD6402 Approved
0.819 Intermediate Similarity NPD6012 Approved
0.819 Intermediate Similarity NPD6014 Approved
0.819 Intermediate Similarity NPD6013 Approved
0.8173 Intermediate Similarity NPD5701 Approved
0.8113 Intermediate Similarity NPD7102 Approved
0.8113 Intermediate Similarity NPD6883 Approved
0.8113 Intermediate Similarity NPD7290 Approved
0.8095 Intermediate Similarity NPD7320 Approved
0.8037 Intermediate Similarity NPD6869 Approved
0.8037 Intermediate Similarity NPD6649 Approved
0.8037 Intermediate Similarity NPD8130 Phase 1
0.8037 Intermediate Similarity NPD6847 Approved
0.8037 Intermediate Similarity NPD6617 Approved
0.8037 Intermediate Similarity NPD6650 Approved
0.8019 Intermediate Similarity NPD6373 Approved
0.8019 Intermediate Similarity NPD6372 Approved
0.7963 Intermediate Similarity NPD6882 Approved
0.7963 Intermediate Similarity NPD8297 Approved
0.7961 Intermediate Similarity NPD5211 Phase 2
0.7941 Intermediate Similarity NPD4696 Approved
0.7941 Intermediate Similarity NPD5285 Approved
0.7941 Intermediate Similarity NPD5286 Approved
0.7921 Intermediate Similarity NPD6084 Phase 2
0.7921 Intermediate Similarity NPD6083 Phase 2
0.7921 Intermediate Similarity NPD4755 Approved
0.79 Intermediate Similarity NPD5695 Phase 3
0.787 Intermediate Similarity NPD6401 Clinical (unspecified phase)
0.7864 Intermediate Similarity NPD5223 Approved
0.7857 Intermediate Similarity NPD5785 Approved
0.781 Intermediate Similarity NPD5141 Approved
0.7788 Intermediate Similarity NPD5224 Approved
0.7788 Intermediate Similarity NPD5226 Approved
0.7788 Intermediate Similarity NPD5225 Approved
0.7788 Intermediate Similarity NPD4633 Approved
0.7778 Intermediate Similarity NPD5693 Phase 1
0.7767 Intermediate Similarity NPD4700 Approved
0.7748 Intermediate Similarity NPD6274 Approved
0.7727 Intermediate Similarity NPD4632 Approved
0.7723 Intermediate Similarity NPD1698 Clinical (unspecified phase)
0.7714 Intermediate Similarity NPD5175 Approved
0.7714 Intermediate Similarity NPD5174 Approved
0.77 Intermediate Similarity NPD6399 Phase 3
0.7679 Intermediate Similarity NPD6317 Approved
0.767 Intermediate Similarity NPD5696 Approved
0.7647 Intermediate Similarity NPD5220 Clinical (unspecified phase)
0.7647 Intermediate Similarity NPD5222 Approved
0.7647 Intermediate Similarity NPD5221 Approved
0.7636 Intermediate Similarity NPD6053 Discontinued
0.7611 Intermediate Similarity NPD6314 Approved
0.7611 Intermediate Similarity NPD6335 Approved
0.7611 Intermediate Similarity NPD6313 Approved
0.7579 Intermediate Similarity NPD4752 Clinical (unspecified phase)
0.7576 Intermediate Similarity NPD4753 Phase 2
0.7573 Intermediate Similarity NPD5173 Approved
0.7547 Intermediate Similarity NPD4754 Approved
0.7544 Intermediate Similarity NPD7100 Approved
0.7544 Intermediate Similarity NPD7101 Approved
0.7522 Intermediate Similarity NPD6009 Approved
0.75 Intermediate Similarity NPD7638 Approved
0.7478 Intermediate Similarity NPD6319 Approved
0.7476 Intermediate Similarity NPD4697 Phase 3
0.7475 Intermediate Similarity NPD5737 Approved
0.7475 Intermediate Similarity NPD6672 Approved
0.7449 Intermediate Similarity NPD6684 Approved
0.7449 Intermediate Similarity NPD5279 Phase 3
0.7449 Intermediate Similarity NPD7334 Approved
0.7449 Intermediate Similarity NPD7521 Approved
0.7449 Intermediate Similarity NPD7146 Approved
0.7449 Intermediate Similarity NPD6409 Approved
0.7449 Intermediate Similarity NPD5330 Approved
0.7431 Intermediate Similarity NPD4729 Approved
0.7431 Intermediate Similarity NPD5128 Approved
0.7431 Intermediate Similarity NPD4730 Approved
0.7429 Intermediate Similarity NPD7639 Approved
0.7429 Intermediate Similarity NPD7640 Approved
0.7426 Intermediate Similarity NPD6079 Approved
0.7423 Intermediate Similarity NPD3666 Approved
0.7423 Intermediate Similarity NPD3133 Approved
0.7423 Intermediate Similarity NPD3665 Phase 1
0.7414 Intermediate Similarity NPD5983 Phase 2
0.7414 Intermediate Similarity NPD6291 Clinical (unspecified phase)
0.7407 Intermediate Similarity NPD6008 Approved
0.7407 Intermediate Similarity NPD4767 Approved
0.7407 Intermediate Similarity NPD4768 Approved
0.74 Intermediate Similarity NPD6904 Approved
0.74 Intermediate Similarity NPD6080 Approved
0.74 Intermediate Similarity NPD6673 Approved
0.74 Intermediate Similarity NPD5328 Approved
0.7396 Intermediate Similarity NPD6435 Approved
0.7379 Intermediate Similarity NPD5210 Approved
0.7379 Intermediate Similarity NPD4629 Approved
0.7368 Intermediate Similarity NPD7115 Discovery
0.7353 Intermediate Similarity NPD4202 Approved
0.7347 Intermediate Similarity NPD5363 Approved
0.7333 Intermediate Similarity NPD4225 Approved
0.7327 Intermediate Similarity NPD5692 Phase 3
0.732 Intermediate Similarity NPD5362 Discontinued
0.73 Intermediate Similarity NPD7513 Clinical (unspecified phase)
0.73 Intermediate Similarity NPD6903 Approved
0.7297 Intermediate Similarity NPD5247 Approved
0.7297 Intermediate Similarity NPD5250 Approved
0.7297 Intermediate Similarity NPD5134 Clinical (unspecified phase)
0.7297 Intermediate Similarity NPD5169 Approved
0.7297 Intermediate Similarity NPD6371 Approved
0.7297 Intermediate Similarity NPD5135 Approved
0.7297 Intermediate Similarity NPD5251 Approved
0.7297 Intermediate Similarity NPD5248 Approved
0.7297 Intermediate Similarity NPD5249 Phase 3
0.7297 Intermediate Similarity NPD4634 Approved
0.7288 Intermediate Similarity NPD7604 Phase 2
0.7281 Intermediate Similarity NPD6868 Approved
0.7273 Intermediate Similarity NPD5690 Phase 2
0.7273 Intermediate Similarity NPD5786 Approved
0.7265 Intermediate Similarity NPD6908 Approved
0.7265 Intermediate Similarity NPD6909 Approved
0.7255 Intermediate Similarity NPD6050 Approved
0.7255 Intermediate Similarity NPD5281 Approved
0.7255 Intermediate Similarity NPD5694 Approved
0.7255 Intermediate Similarity NPD5284 Approved
0.7245 Intermediate Similarity NPD4786 Approved
0.7245 Intermediate Similarity NPD4197 Approved
0.7232 Intermediate Similarity NPD5216 Approved
0.7232 Intermediate Similarity NPD5217 Approved
0.7232 Intermediate Similarity NPD5215 Approved
0.7232 Intermediate Similarity NPD5127 Approved
0.7227 Intermediate Similarity NPD7492 Approved
0.7216 Intermediate Similarity NPD3667 Approved
0.7188 Intermediate Similarity NPD4695 Discontinued
0.7188 Intermediate Similarity NPD5368 Approved
0.7179 Intermediate Similarity NPD6054 Approved
0.7172 Intermediate Similarity NPD5329 Approved
0.7172 Intermediate Similarity NPD1694 Approved
0.7172 Intermediate Similarity NPD6082 Clinical (unspecified phase)
0.7167 Intermediate Similarity NPD6336 Discontinued
0.7167 Intermediate Similarity NPD6616 Approved
0.7158 Intermediate Similarity NPD5784 Clinical (unspecified phase)
0.7119 Intermediate Similarity NPD6015 Approved
0.7119 Intermediate Similarity NPD6016 Approved
0.7117 Intermediate Similarity NPD6686 Approved
0.7115 Intermediate Similarity NPD7748 Approved
0.7107 Intermediate Similarity NPD7078 Approved
0.71 Intermediate Similarity NPD6098 Approved
0.71 Intermediate Similarity NPD5280 Approved
0.71 Intermediate Similarity NPD4694 Approved
0.71 Intermediate Similarity NPD3618 Phase 1
0.7087 Intermediate Similarity NPD7515 Phase 2
0.7087 Intermediate Similarity NPD6411 Approved
0.7075 Intermediate Similarity NPD7902 Approved
0.7059 Intermediate Similarity NPD6370 Approved
0.7059 Intermediate Similarity NPD5988 Approved
0.7049 Intermediate Similarity NPD7736 Approved
0.7043 Intermediate Similarity NPD5167 Approved
0.7041 Intermediate Similarity NPD4223 Phase 3
0.7041 Intermediate Similarity NPD4269 Approved
0.7041 Intermediate Similarity NPD4221 Approved
0.7041 Intermediate Similarity NPD4270 Approved
0.7034 Intermediate Similarity NPD6059 Approved
0.7027 Intermediate Similarity NPD7899 Clinical (unspecified phase)
0.7025 Intermediate Similarity NPD7507 Approved
0.7019 Intermediate Similarity NPD5778 Approved
0.7019 Intermediate Similarity NPD5779 Approved
0.701 Intermediate Similarity NPD5790 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD1696 Phase 3
0.699 Remote Similarity NPD46 Approved
0.699 Remote Similarity NPD6698 Approved
0.6967 Remote Similarity NPD8293 Discontinued
0.6964 Remote Similarity NPD5168 Approved
0.6961 Remote Similarity NPD5208 Approved
0.6939 Remote Similarity NPD5369 Approved
0.6893 Remote Similarity NPD6051 Approved
0.6893 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6893 Remote Similarity NPD6101 Approved
0.6887 Remote Similarity NPD5654 Approved
0.6887 Remote Similarity NPD6356 Clinical (unspecified phase)
0.688 Remote Similarity NPD7260 Phase 2
0.6875 Remote Similarity NPD6412 Phase 2
0.6869 Remote Similarity NPD5209 Approved
0.6863 Remote Similarity NPD3573 Approved
0.6855 Remote Similarity NPD7319 Approved
0.6837 Remote Similarity NPD4252 Approved
0.6837 Remote Similarity NPD4819 Approved
0.6837 Remote Similarity NPD4821 Approved
0.6837 Remote Similarity NPD4822 Approved
0.6837 Remote Similarity NPD4820 Approved
0.6827 Remote Similarity NPD5207 Approved
0.6818 Remote Similarity NPD7632 Discontinued
0.6804 Remote Similarity NPD4271 Approved
0.6804 Remote Similarity NPD4268 Approved
0.68 Remote Similarity NPD5332 Approved
0.68 Remote Similarity NPD5331 Approved
0.68 Remote Similarity NPD7154 Phase 3
0.6792 Remote Similarity NPD5282 Discontinued

  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