Structure

Physi-Chem Properties

Molecular Weight:  430.34
Volume:  479.716
LogP:  5.936
LogD:  5.248
LogS:  -5.276
# Rotatable Bonds:  4
TPSA:  60.69
# H-Bond Aceptor:  3
# H-Bond Donor:  3
# Rings:  4
# Heavy Atoms:  3

MedChem Properties

QED Drug-Likeness Score:  0.516
Synthetic Accessibility Score:  5.013
Fsp3:  0.857
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
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:  -4.672
MDCK Permeability:  2.016383223235607e-05
Pgp-inhibitor:  0.017
Pgp-substrate:  0.635
Human Intestinal Absorption (HIA):  0.015
20% Bioavailability (F20%):  0.79
30% Bioavailability (F30%):  0.561

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.323
Plasma Protein Binding (PPB):  87.53759002685547%
Volume Distribution (VD):  1.037
Pgp-substrate:  1.8250802755355835%

ADMET: Metabolism

CYP1A2-inhibitor:  0.044
CYP1A2-substrate:  0.475
CYP2C19-inhibitor:  0.027
CYP2C19-substrate:  0.872
CYP2C9-inhibitor:  0.139
CYP2C9-substrate:  0.056
CYP2D6-inhibitor:  0.007
CYP2D6-substrate:  0.049
CYP3A4-inhibitor:  0.86
CYP3A4-substrate:  0.882

ADMET: Excretion

Clearance (CL):  2.82
Half-life (T1/2):  0.054

ADMET: Toxicity

hERG Blockers:  0.031
Human Hepatotoxicity (H-HT):  0.202
Drug-inuced Liver Injury (DILI):  0.024
AMES Toxicity:  0.003
Rat Oral Acute Toxicity:  0.96
Maximum Recommended Daily Dose:  0.98
Skin Sensitization:  0.126
Carcinogencity:  0.081
Eye Corrosion:  0.004
Eye Irritation:  0.041
Respiratory Toxicity:  0.983

Download Data

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

  Natural Product: NPC133588

Natural Product ID:  NPC133588
Common Name*:   2Beta,3Alpha,9Alpha-Trihydroxy-5Alpha-Ergosta-7,22-Diene
IUPAC Name:   (2S,3S,5S,9S,10S,13R,14R,17R)-17-[(E,2R,5R)-5,6-dimethylhept-3-en-2-yl]-10,13-dimethyl-1,2,3,4,5,6,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthrene-2,3,9-triol
Synonyms:  
Standard InCHIKey:  RVWGLBNUTMYAOL-DABZZXQESA-N
Standard InCHI:  InChI=1S/C28H46O3/c1-17(2)18(3)7-8-19(4)21-11-12-22-23-10-9-20-15-24(29)25(30)16-27(20,6)28(23,31)14-13-26(21,22)5/h7-8,10,17-22,24-25,29-31H,9,11-16H2,1-6H3/b8-7+/t18-,19+,20-,21+,22-,24-,25-,26+,27-,28+/m0/s1
SMILES:  CC([C@H](/C=C/[C@H]([C@H]1CC[C@@H]2[C@]1(C)CC[C@]1(C2=CC[C@@H]2[C@]1(C)C[C@H](O)[C@H](C2)O)O)C)C)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL491165
PubChem CID:   44566406
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000258] Steroids and steroid derivatives
        • [CHEMONTID:0003567] Ergostane steroids
          • [CHEMONTID:0001403] Ergosterols and derivatives

*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
NPO2085 Ganoderma tsugae Species Ganodermataceae Eukaryota n.a. n.a. n.a. PMID[10785428]
NPO2085 Ganoderma tsugae Species Ganodermataceae Eukaryota n.a. fruit body n.a. PMID[10785428]
NPO2085 Ganoderma tsugae Species Ganodermataceae Eukaryota n.a. fruit body n.a. PMID[21939217]
NPO7576 Brassica oleracea Species Brassicaceae Eukaryota n.a. n.a. n.a. PMID[24014097]
NPO7576 Brassica oleracea Species Brassicaceae Eukaryota n.a. n.a. n.a. PMID[24128451]
NPO2085 Ganoderma tsugae Species Ganodermataceae Eukaryota n.a. n.a. n.a. PMID[9584403]
NPO24693 Prunus cerasus Species Rosaceae Eukaryota n.a. n.a. n.a. PMID[9917288]
NPO4626 Pimpinella anisum Species Apiaceae Eukaryota Essential Oil n.a. n.a. Database[FooDB]
NPO24693 Prunus cerasus Species Rosaceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO7576 Brassica oleracea Species Brassicaceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO4626 Pimpinella anisum Species Apiaceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO24693 Prunus cerasus Species Rosaceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO7576 Brassica oleracea Species Brassicaceae Eukaryota Shoot n.a. n.a. Database[FooDB]
NPO7576 Brassica oleracea Species Brassicaceae Eukaryota Sprout Seedling n.a. n.a. Database[FooDB]
NPO7576 Brassica oleracea Species Brassicaceae Eukaryota Stem n.a. n.a. Database[FooDB]
NPO4626 Pimpinella anisum Species Apiaceae Eukaryota Tissue Culture n.a. n.a. Database[FooDB]
NPO4626 Pimpinella anisum Species Apiaceae Eukaryota n.a. n.a. Database[FooDB]
NPO24693 Prunus cerasus Species Rosaceae Eukaryota n.a. n.a. Database[FooDB]
NPO24693 Prunus cerasus Species Rosaceae Eukaryota Fruits n.a. Database[FooDB]
NPO4626 Pimpinella anisum Species Apiaceae Eukaryota n.a. n.a. Database[FooDB]
NPO7576 Brassica oleracea Species Brassicaceae Eukaryota n.a. n.a. Database[FooDB]
NPO7576 Brassica oleracea Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO4626 Pimpinella anisum Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO7276 Mitragyna macrophylla Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO24693 Prunus cerasus Species Rosaceae Eukaryota Fruits n.a. Database[Phenol-Explorer]
NPO7276 Mitragyna macrophylla Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7576 Brassica oleracea Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO4626 Pimpinella anisum Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7576 Brassica oleracea Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO341 Xylaria obovata Species Xylariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4237 Vepris madagascarica Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24693 Prunus cerasus Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7576 Brassica oleracea Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2085 Ganoderma tsugae Species Ganodermataceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1599 Ormosia pachycarpa Species Limoniidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7276 Mitragyna macrophylla Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5585 Cassia greggii Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6970 Wyethia angustifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8579 Pestalotiopsis longiseta Species Sporocadaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4626 Pimpinella anisum Species Apiaceae 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
NPT610 Others Molecular identity unknown Activity = 50.6 % PMID[504555]
NPT610 Others Molecular identity unknown Activity = 36.8 % PMID[504555]
NPT610 Others Molecular identity unknown Activity = 12.6 % PMID[504555]
NPT610 Others Molecular identity unknown Activity = 55.3 % PMID[504555]
NPT610 Others Molecular identity unknown Activity = 35.0 % PMID[504555]
NPT610 Others Molecular identity unknown Activity = 9.8 % PMID[504555]
NPT610 Others Molecular identity unknown Activity = 35.5 % PMID[504555]
NPT610 Others Molecular identity unknown Activity = 9.2 % PMID[504555]
NPT610 Others Molecular identity unknown Activity = 57.8 % PMID[504555]
NPT610 Others Molecular identity unknown Activity = 37.0 % PMID[504555]
NPT610 Others Molecular identity unknown Activity = 5.2 % PMID[504555]
NPT610 Others Molecular identity unknown IC50 = 87.1 ug.mL-1 PMID[504555]

☑ 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 NPC133588 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
0.9529 High Similarity NPC329596
0.9529 High Similarity NPC204188
0.9529 High Similarity NPC3345
0.9529 High Similarity NPC291484
0.9529 High Similarity NPC11216
0.9529 High Similarity NPC80561
0.9524 High Similarity NPC474668
0.9419 High Similarity NPC97404
0.9419 High Similarity NPC41554
0.9412 High Similarity NPC470361
0.9286 High Similarity NPC299068
0.9286 High Similarity NPC261266
0.9167 High Similarity NPC470360
0.9157 High Similarity NPC317458
0.9091 High Similarity NPC310013
0.907 High Similarity NPC280556
0.9059 High Similarity NPC6391
0.9059 High Similarity NPC94462
0.9036 High Similarity NPC87489
0.9036 High Similarity NPC50964
0.9036 High Similarity NPC218616
0.9036 High Similarity NPC49964
0.9036 High Similarity NPC296701
0.9024 High Similarity NPC236112
0.9 High Similarity NPC288970
0.8989 High Similarity NPC127718
0.8989 High Similarity NPC65402
0.8977 High Similarity NPC275671
0.8953 High Similarity NPC470620
0.8929 High Similarity NPC207013
0.8929 High Similarity NPC474634
0.8916 High Similarity NPC264245
0.8916 High Similarity NPC474531
0.8916 High Similarity NPC476646
0.8916 High Similarity NPC23852
0.8916 High Similarity NPC209620
0.8902 High Similarity NPC30986
0.8902 High Similarity NPC209430
0.8889 High Similarity NPC8774
0.8864 High Similarity NPC295668
0.8837 High Similarity NPC139724
0.8824 High Similarity NPC205845
0.8824 High Similarity NPC185568
0.8824 High Similarity NPC470077
0.8824 High Similarity NPC231310
0.881 High Similarity NPC30166
0.8795 High Similarity NPC209944
0.8795 High Similarity NPC164840
0.8795 High Similarity NPC96362
0.8795 High Similarity NPC234193
0.8795 High Similarity NPC13554
0.8795 High Similarity NPC287749
0.8795 High Similarity NPC241290
0.8791 High Similarity NPC12103
0.8791 High Similarity NPC72204
0.8791 High Similarity NPC103165
0.8791 High Similarity NPC210717
0.8791 High Similarity NPC227583
0.8791 High Similarity NPC98457
0.875 High Similarity NPC109744
0.875 High Similarity NPC105495
0.875 High Similarity NPC101886
0.8736 High Similarity NPC474657
0.8736 High Similarity NPC186145
0.8721 High Similarity NPC318390
0.8721 High Similarity NPC274448
0.8706 High Similarity NPC82623
0.8706 High Similarity NPC477818
0.8696 High Similarity NPC477226
0.8696 High Similarity NPC261807
0.869 High Similarity NPC47761
0.869 High Similarity NPC249423
0.8675 High Similarity NPC328714
0.8675 High Similarity NPC273410
0.8675 High Similarity NPC28862
0.8675 High Similarity NPC47982
0.8675 High Similarity NPC143182
0.8675 High Similarity NPC84694
0.8675 High Similarity NPC81306
0.8675 High Similarity NPC80530
0.8675 High Similarity NPC109546
0.8659 High Similarity NPC130136
0.8652 High Similarity NPC270511
0.8652 High Similarity NPC14380
0.8652 High Similarity NPC470390
0.8652 High Similarity NPC473956
0.8652 High Similarity NPC475751
0.8652 High Similarity NPC192437
0.8652 High Similarity NPC245410
0.8636 High Similarity NPC475664
0.8636 High Similarity NPC4574
0.8636 High Similarity NPC212596
0.8636 High Similarity NPC67872
0.8621 High Similarity NPC269058
0.8621 High Similarity NPC293287
0.8621 High Similarity NPC152808
0.8621 High Similarity NPC71520
0.8605 High Similarity NPC124172
0.8605 High Similarity NPC15534
0.8605 High Similarity NPC238485
0.8605 High Similarity NPC474047
0.8588 High Similarity NPC7988
0.8588 High Similarity NPC470049
0.8588 High Similarity NPC202389
0.8588 High Similarity NPC101462
0.8571 High Similarity NPC477605
0.8571 High Similarity NPC102253
0.8571 High Similarity NPC236237
0.8571 High Similarity NPC144202
0.8571 High Similarity NPC322313
0.8556 High Similarity NPC210268
0.8554 High Similarity NPC167891
0.8554 High Similarity NPC167037
0.8554 High Similarity NPC244385
0.8554 High Similarity NPC6978
0.8554 High Similarity NPC83351
0.8554 High Similarity NPC285761
0.8554 High Similarity NPC474216
0.8554 High Similarity NPC138621
0.8554 High Similarity NPC87604
0.8539 High Similarity NPC138974
0.8539 High Similarity NPC477606
0.8539 High Similarity NPC187785
0.8539 High Similarity NPC259875
0.8537 High Similarity NPC247325
0.8537 High Similarity NPC134330
0.8537 High Similarity NPC244488
0.8537 High Similarity NPC129165
0.8537 High Similarity NPC253190
0.8537 High Similarity NPC189883
0.8523 High Similarity NPC304083
0.8523 High Similarity NPC149224
0.8523 High Similarity NPC476948
0.8506 High Similarity NPC157257
0.8495 Intermediate Similarity NPC476893
0.8488 Intermediate Similarity NPC193870
0.8488 Intermediate Similarity NPC134481
0.8488 Intermediate Similarity NPC211135
0.8488 Intermediate Similarity NPC216420
0.8488 Intermediate Similarity NPC475789
0.8488 Intermediate Similarity NPC141941
0.8488 Intermediate Similarity NPC85095
0.8488 Intermediate Similarity NPC110778
0.8488 Intermediate Similarity NPC470558
0.8478 Intermediate Similarity NPC476894
0.8471 Intermediate Similarity NPC470383
0.8471 Intermediate Similarity NPC6707
0.8462 Intermediate Similarity NPC27531
0.8454 Intermediate Similarity NPC166607
0.8452 Intermediate Similarity NPC1319
0.8434 Intermediate Similarity NPC91594
0.8434 Intermediate Similarity NPC471798
0.8434 Intermediate Similarity NPC155986
0.8434 Intermediate Similarity NPC470711
0.8434 Intermediate Similarity NPC198968
0.8434 Intermediate Similarity NPC214570
0.8434 Intermediate Similarity NPC318495
0.8434 Intermediate Similarity NPC470758
0.8427 Intermediate Similarity NPC475605
0.8415 Intermediate Similarity NPC141071
0.8415 Intermediate Similarity NPC32832
0.8415 Intermediate Similarity NPC471723
0.8415 Intermediate Similarity NPC257347
0.8409 Intermediate Similarity NPC6605
0.8409 Intermediate Similarity NPC125399
0.8409 Intermediate Similarity NPC24277
0.8409 Intermediate Similarity NPC201273
0.8404 Intermediate Similarity NPC476895
0.8391 Intermediate Similarity NPC475798
0.8391 Intermediate Similarity NPC474493
0.8391 Intermediate Similarity NPC127606
0.8391 Intermediate Similarity NPC209802
0.8372 Intermediate Similarity NPC189972
0.8372 Intermediate Similarity NPC470614
0.8372 Intermediate Similarity NPC1272
0.8372 Intermediate Similarity NPC248886
0.8353 Intermediate Similarity NPC26117
0.8353 Intermediate Similarity NPC22403
0.8352 Intermediate Similarity NPC114389
0.8351 Intermediate Similarity NPC160843
0.8333 Intermediate Similarity NPC301707
0.8333 Intermediate Similarity NPC11908
0.8333 Intermediate Similarity NPC275910
0.8333 Intermediate Similarity NPC473943
0.8313 Intermediate Similarity NPC237460
0.8313 Intermediate Similarity NPC91573
0.8313 Intermediate Similarity NPC240604
0.8313 Intermediate Similarity NPC321016
0.8313 Intermediate Similarity NPC107059
0.8313 Intermediate Similarity NPC202642
0.8313 Intermediate Similarity NPC300324
0.8313 Intermediate Similarity NPC470749
0.8313 Intermediate Similarity NPC470362
0.8313 Intermediate Similarity NPC321381
0.8313 Intermediate Similarity NPC46160
0.8313 Intermediate Similarity NPC113733
0.8313 Intermediate Similarity NPC265588
0.8313 Intermediate Similarity NPC73875
0.8298 Intermediate Similarity NPC210337
0.8295 Intermediate Similarity NPC266511

  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 NPC133588 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
0.8571 High Similarity NPD7525 Registered
0.8315 Intermediate Similarity NPD4751 Clinical (unspecified phase)
0.8193 Intermediate Similarity NPD6942 Approved
0.8193 Intermediate Similarity NPD7339 Approved
0.7931 Intermediate Similarity NPD6931 Approved
0.7931 Intermediate Similarity NPD6930 Phase 2
0.7931 Intermediate Similarity NPD7514 Phase 3
0.7912 Intermediate Similarity NPD7524 Approved
0.7882 Intermediate Similarity NPD3701 Clinical (unspecified phase)
0.7882 Intermediate Similarity NPD6933 Approved
0.7816 Intermediate Similarity NPD6929 Approved
0.7778 Intermediate Similarity NPD7338 Clinical (unspecified phase)
0.7727 Intermediate Similarity NPD7332 Phase 2
0.7701 Intermediate Similarity NPD7145 Approved
0.7667 Intermediate Similarity NPD6695 Phase 3
0.7647 Intermediate Similarity NPD4785 Approved
0.7647 Intermediate Similarity NPD4784 Approved
0.7647 Intermediate Similarity NPD6926 Approved
0.7647 Intermediate Similarity NPD6924 Approved
0.764 Intermediate Similarity NPD6902 Approved
0.7619 Intermediate Similarity NPD4243 Approved
0.7614 Intermediate Similarity NPD7645 Phase 2
0.7586 Intermediate Similarity NPD6925 Approved
0.7586 Intermediate Similarity NPD6932 Approved
0.7586 Intermediate Similarity NPD5776 Phase 2
0.7582 Intermediate Similarity NPD4786 Approved
0.7579 Intermediate Similarity NPD6079 Approved
0.7553 Intermediate Similarity NPD5328 Approved
0.75 Intermediate Similarity NPD7322 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD6893 Approved
0.75 Intermediate Similarity NPD4202 Approved
0.7426 Intermediate Similarity NPD5211 Phase 2
0.7419 Intermediate Similarity NPD3618 Phase 1
0.7412 Intermediate Similarity NPD7150 Approved
0.7412 Intermediate Similarity NPD7152 Approved
0.7412 Intermediate Similarity NPD7151 Approved
0.74 Intermediate Similarity NPD7640 Approved
0.74 Intermediate Similarity NPD7639 Approved
0.7363 Intermediate Similarity NPD3667 Approved
0.7356 Intermediate Similarity NPD8264 Approved
0.734 Intermediate Similarity NPD7750 Discontinued
0.7333 Intermediate Similarity NPD7509 Discontinued
0.7333 Intermediate Similarity NPD4748 Discontinued
0.73 Intermediate Similarity NPD7638 Approved
0.7294 Intermediate Similarity NPD7143 Approved
0.7294 Intermediate Similarity NPD7144 Approved
0.7282 Intermediate Similarity NPD5141 Approved
0.7264 Intermediate Similarity NPD4634 Approved
0.7253 Intermediate Similarity NPD6898 Phase 1
0.7228 Intermediate Similarity NPD5286 Approved
0.7228 Intermediate Similarity NPD4696 Approved
0.7228 Intermediate Similarity NPD5285 Approved
0.7222 Intermediate Similarity NPD4195 Approved
0.7222 Intermediate Similarity NPD6683 Phase 2
0.72 Intermediate Similarity NPD4755 Approved
0.7176 Intermediate Similarity NPD4267 Clinical (unspecified phase)
0.7176 Intermediate Similarity NPD6922 Approved
0.7176 Intermediate Similarity NPD6923 Approved
0.7159 Intermediate Similarity NPD4190 Phase 3
0.7159 Intermediate Similarity NPD5275 Approved
0.7157 Intermediate Similarity NPD5223 Approved
0.71 Intermediate Similarity NPD5222 Approved
0.71 Intermediate Similarity NPD5220 Clinical (unspecified phase)
0.71 Intermediate Similarity NPD5221 Approved
0.7087 Intermediate Similarity NPD5226 Approved
0.7087 Intermediate Similarity NPD5224 Approved
0.7087 Intermediate Similarity NPD4633 Approved
0.7087 Intermediate Similarity NPD5225 Approved
0.7064 Intermediate Similarity NPD4632 Approved
0.7059 Intermediate Similarity NPD4700 Approved
0.7054 Intermediate Similarity NPD7516 Approved
0.7041 Intermediate Similarity NPD7087 Discontinued
0.703 Intermediate Similarity NPD5173 Approved
0.7027 Intermediate Similarity NPD7115 Discovery
0.7021 Intermediate Similarity NPD3133 Approved
0.7021 Intermediate Similarity NPD3666 Approved
0.7021 Intermediate Similarity NPD3665 Phase 1
0.7019 Intermediate Similarity NPD5175 Approved
0.7019 Intermediate Similarity NPD5174 Approved
0.699 Remote Similarity NPD4159 Approved
0.697 Remote Similarity NPD6399 Phase 3
0.6964 Remote Similarity NPD7327 Approved
0.6964 Remote Similarity NPD7328 Approved
0.6951 Remote Similarity NPD368 Approved
0.6947 Remote Similarity NPD7520 Clinical (unspecified phase)
0.6931 Remote Similarity NPD4697 Phase 3
0.693 Remote Similarity NPD7503 Approved
0.6916 Remote Similarity NPD6899 Approved
0.6916 Remote Similarity NPD6881 Approved
0.6887 Remote Similarity NPD6402 Approved
0.6887 Remote Similarity NPD5739 Approved
0.6887 Remote Similarity NPD7128 Approved
0.6887 Remote Similarity NPD6675 Approved
0.6869 Remote Similarity NPD7637 Suspended
0.6857 Remote Similarity NPD4754 Approved
0.6842 Remote Similarity NPD8294 Approved
0.6842 Remote Similarity NPD8377 Approved
0.6837 Remote Similarity NPD6051 Approved
0.6837 Remote Similarity NPD4753 Phase 2
0.6822 Remote Similarity NPD5697 Approved
0.6818 Remote Similarity NPD8297 Approved
0.6809 Remote Similarity NPD4223 Phase 3
0.6809 Remote Similarity NPD4221 Approved
0.6796 Remote Similarity NPD5290 Discontinued
0.6789 Remote Similarity NPD7102 Approved
0.6789 Remote Similarity NPD7290 Approved
0.6789 Remote Similarity NPD6883 Approved
0.6783 Remote Similarity NPD8380 Approved
0.6783 Remote Similarity NPD8379 Approved
0.6783 Remote Similarity NPD8296 Approved
0.6783 Remote Similarity NPD8378 Approved
0.6783 Remote Similarity NPD8335 Approved
0.6783 Remote Similarity NPD8033 Approved
0.6771 Remote Similarity NPD5329 Approved
0.6762 Remote Similarity NPD7632 Discontinued
0.6759 Remote Similarity NPD4730 Approved
0.6759 Remote Similarity NPD4729 Approved
0.6759 Remote Similarity NPD7320 Approved
0.6759 Remote Similarity NPD6011 Approved
0.6729 Remote Similarity NPD4767 Approved
0.6729 Remote Similarity NPD4768 Approved
0.6727 Remote Similarity NPD8130 Phase 1
0.6727 Remote Similarity NPD6869 Approved
0.6727 Remote Similarity NPD6649 Approved
0.6727 Remote Similarity NPD6847 Approved
0.6727 Remote Similarity NPD6617 Approved
0.6727 Remote Similarity NPD6650 Approved
0.6726 Remote Similarity NPD6009 Approved
0.6701 Remote Similarity NPD4623 Approved
0.6701 Remote Similarity NPD5279 Phase 3
0.6701 Remote Similarity NPD4519 Discontinued
0.67 Remote Similarity NPD7515 Phase 2
0.6697 Remote Similarity NPD6013 Approved
0.6697 Remote Similarity NPD4061 Clinical (unspecified phase)
0.6697 Remote Similarity NPD6014 Approved
0.6697 Remote Similarity NPD6373 Approved
0.6697 Remote Similarity NPD6372 Approved
0.6697 Remote Similarity NPD6012 Approved
0.6696 Remote Similarity NPD6319 Approved
0.6696 Remote Similarity NPD6054 Approved
0.6667 Remote Similarity NPD4629 Approved
0.6667 Remote Similarity NPD5344 Discontinued
0.6667 Remote Similarity NPD4197 Approved
0.6667 Remote Similarity NPD6882 Approved
0.6667 Remote Similarity NPD6412 Phase 2
0.6667 Remote Similarity NPD3668 Phase 3
0.6667 Remote Similarity NPD5701 Approved
0.6667 Remote Similarity NPD5210 Approved
0.6636 Remote Similarity NPD5135 Approved
0.6636 Remote Similarity NPD5250 Approved
0.6636 Remote Similarity NPD5247 Approved
0.6636 Remote Similarity NPD5248 Approved
0.6636 Remote Similarity NPD5169 Approved
0.6636 Remote Similarity NPD5249 Phase 3
0.6636 Remote Similarity NPD5251 Approved
0.6636 Remote Similarity NPD5134 Clinical (unspecified phase)
0.6635 Remote Similarity NPD4225 Approved
0.6606 Remote Similarity NPD5128 Approved
0.66 Remote Similarity NPD7136 Phase 2
0.6581 Remote Similarity NPD6370 Approved
0.6577 Remote Similarity NPD6401 Clinical (unspecified phase)
0.6577 Remote Similarity NPD5215 Approved
0.6577 Remote Similarity NPD5217 Approved
0.6577 Remote Similarity NPD5216 Approved
0.6577 Remote Similarity NPD5127 Approved
0.6562 Remote Similarity NPD4788 Approved
0.6555 Remote Similarity NPD7507 Approved
0.6552 Remote Similarity NPD6059 Approved
0.6538 Remote Similarity NPD6084 Phase 2
0.6538 Remote Similarity NPD6083 Phase 2
0.6535 Remote Similarity NPD8034 Phase 2
0.6535 Remote Similarity NPD8035 Phase 2
0.6531 Remote Similarity NPD3574 Clinical (unspecified phase)
0.6531 Remote Similarity NPD5205 Approved
0.6531 Remote Similarity NPD5690 Phase 2
0.6531 Remote Similarity NPD4690 Approved
0.6531 Remote Similarity NPD4138 Approved
0.6531 Remote Similarity NPD4689 Approved
0.6531 Remote Similarity NPD4693 Phase 3
0.6531 Remote Similarity NPD4688 Approved
0.6525 Remote Similarity NPD7604 Phase 2
0.6517 Remote Similarity NPD4787 Phase 1
0.6496 Remote Similarity NPD5983 Phase 2
0.6496 Remote Similarity NPD6016 Approved
0.6496 Remote Similarity NPD6015 Approved
0.6471 Remote Similarity NPD7492 Approved
0.6455 Remote Similarity NPD5168 Approved
0.6441 Remote Similarity NPD5988 Approved
0.6422 Remote Similarity NPD6008 Approved
0.6417 Remote Similarity NPD6336 Discontinued
0.6417 Remote Similarity NPD6616 Approved
0.6408 Remote Similarity NPD7748 Approved
0.6404 Remote Similarity NPD5167 Approved
0.64 Remote Similarity NPD4723 Approved
0.64 Remote Similarity NPD4722 Approved
0.6393 Remote Similarity NPD7319 Approved
0.6383 Remote Similarity NPD6115 Approved
0.6383 Remote Similarity NPD6118 Approved
0.6383 Remote Similarity NPD6697 Approved
0.6383 Remote Similarity NPD6114 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