Structure

Physi-Chem Properties

Molecular Weight:  430.34
Volume:  479.716
LogP:  4.955
LogD:  4.457
LogS:  -5.039
# 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:  5.254
Fsp3:  0.857
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.806
MDCK Permeability:  1.955783591256477e-05
Pgp-inhibitor:  0.001
Pgp-substrate:  0.973
Human Intestinal Absorption (HIA):  0.012
20% Bioavailability (F20%):  0.825
30% Bioavailability (F30%):  0.275

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.254
Plasma Protein Binding (PPB):  88.8626937866211%
Volume Distribution (VD):  0.991
Pgp-substrate:  1.4561619758605957%

ADMET: Metabolism

CYP1A2-inhibitor:  0.023
CYP1A2-substrate:  0.855
CYP2C19-inhibitor:  0.05
CYP2C19-substrate:  0.857
CYP2C9-inhibitor:  0.18
CYP2C9-substrate:  0.046
CYP2D6-inhibitor:  0.008
CYP2D6-substrate:  0.062
CYP3A4-inhibitor:  0.85
CYP3A4-substrate:  0.899

ADMET: Excretion

Clearance (CL):  2.068
Half-life (T1/2):  0.131

ADMET: Toxicity

hERG Blockers:  0.279
Human Hepatotoxicity (H-HT):  0.229
Drug-inuced Liver Injury (DILI):  0.007
AMES Toxicity:  0.001
Rat Oral Acute Toxicity:  0.399
Maximum Recommended Daily Dose:  0.984
Skin Sensitization:  0.154
Carcinogencity:  0.003
Eye Corrosion:  0.004
Eye Irritation:  0.048
Respiratory Toxicity:  0.969

Download Data

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

  Natural Product: NPC299068

Natural Product ID:  NPC299068
Common Name*:   Ergosta-6,22-Diene-3,5R,8R-Triol
IUPAC Name:   (3S,5S,8S,9R,10R,13R,14R,17R)-17-[(E,2R,5R)-5,6-dimethylhept-3-en-2-yl]-10,13-dimethyl-2,3,4,9,11,12,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthrene-3,5,8-triol
Synonyms:  
Standard InCHIKey:  UPJVQRZPXLZUET-KGHQQZOUSA-N
Standard InCHI:  InChI=1S/C28H46O3/c1-18(2)19(3)7-8-20(4)22-9-10-23-25(22,5)13-12-24-26(6)14-11-21(29)17-27(26,30)15-16-28(23,24)31/h7-8,15-16,18-24,29-31H,9-14,17H2,1-6H3/b8-7+/t19-,20+,21-,22+,23+,24+,25+,26+,27+,28-/m0/s1
SMILES:  O[C@H]1CC[C@]2([C@@](C1)(O)C=C[C@]1([C@@H]2CC[C@]2([C@H]1CC[C@@H]2[C@@H](/C=C/[C@@H](C(C)C)C)C)C)O)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL464314
PubChem CID:   15251535
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
NPO28014 Garcinia gaudichaudii Species Clusiaceae Eukaryota n.a. bark n.a. PMID[11101460]
NPO27888 Sarcococca saligna Species Buxaceae Eukaryota n.a. n.a. n.a. PMID[14584959]
NPO27888 Sarcococca saligna Species Buxaceae Eukaryota n.a. n.a. n.a. PMID[14643329]
NPO27718 Peperomia dindygulensis Species Piperaceae Eukaryota whole plant Yunnan Province, China 2002-FEB PMID[16309318]
NPO27718 Peperomia dindygulensis Species Piperaceae Eukaryota whole plant Yunnan Province, China 2002-FEB PMID[16724842]
NPO27888 Sarcococca saligna Species Buxaceae Eukaryota n.a. n.a. n.a. PMID[9548847]
NPO27842 Gentiana makinoi Species Gentianaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO27888 Sarcococca saligna Species Buxaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO16710 Pandanus tectorius Species Pandanaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO27888 Sarcococca saligna Species Buxaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO27842 Gentiana makinoi Species Gentianaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO16710 Pandanus tectorius Species Pandanaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO28014 Garcinia gaudichaudii Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO16710 Pandanus tectorius Species Pandanaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO27184 Bonellia macrocarpa Species Primulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27718 Peperomia dindygulensis Species Piperaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27953 Eugenia formosa Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27401 Aniba riparia Species Lauraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17271 Aegialitis annulata Species Plumbaginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27135 Tubularia larynx Species Tubulariidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27362 Hypericum elodes Species Hypericaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28066 Aloe speciosa Species Xanthorrhoeaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28014 Garcinia gaudichaudii Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28133 Geigeria filifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27439 Letharia vulpina Species Parmeliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27842 Gentiana makinoi Species Gentianaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27888 Sarcococca saligna Species Buxaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13728 Metanarthecium luteoviride Species Nartheciaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22405 Litsea monopetala Species Lauraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19590 Daedaleopsis tricolor Species Coriolaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16710 Pandanus tectorius Species Pandanaceae 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
NPT1475 Cell Line WI-38 VA13 Homo sapiens IC50 = 48.1 ug.mL-1 PMID[513083]
NPT65 Cell Line HepG2 Homo sapiens IC50 = 47.9 ug.mL-1 PMID[513083]
NPT668 Individual Protein P-glycoprotein 1 Homo sapiens Inhibition = 97.0 % PMID[513083]
NPT668 Individual Protein P-glycoprotein 1 Homo sapiens Inhibition = 106.0 % PMID[513083]
NPT668 Individual Protein P-glycoprotein 1 Homo sapiens Inhibition = 95.0 % PMID[513083]
NPT668 Individual Protein P-glycoprotein 1 Homo sapiens Inhibition = 109.0 % PMID[513083]
NPT668 Individual Protein P-glycoprotein 1 Homo sapiens Inhibition = 111.0 % PMID[513083]
NPT668 Individual Protein P-glycoprotein 1 Homo sapiens Inhibition = 73.0 % PMID[513083]

☑ 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 NPC299068 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
0.9875 High Similarity NPC470360
0.9524 High Similarity NPC80561
0.9524 High Similarity NPC329596
0.9524 High Similarity NPC204188
0.9524 High Similarity NPC3345
0.9524 High Similarity NPC291484
0.9524 High Similarity NPC11216
0.9412 High Similarity NPC41554
0.9412 High Similarity NPC97404
0.9405 High Similarity NPC470361
0.9286 High Similarity NPC133588
0.9286 High Similarity NPC212596
0.9286 High Similarity NPC4574
0.9277 High Similarity NPC6391
0.9277 High Similarity NPC261266
0.9176 High Similarity NPC138974
0.9176 High Similarity NPC101886
0.9167 High Similarity NPC304083
0.9136 High Similarity NPC249423
0.908 High Similarity NPC310013
0.908 High Similarity NPC27531
0.907 High Similarity NPC192437
0.907 High Similarity NPC470390
0.907 High Similarity NPC14380
0.907 High Similarity NPC270511
0.907 High Similarity NPC245410
0.9059 High Similarity NPC475605
0.9048 High Similarity NPC6605
0.9048 High Similarity NPC139724
0.9036 High Similarity NPC205845
0.9024 High Similarity NPC218616
0.9024 High Similarity NPC49964
0.9024 High Similarity NPC296701
0.9024 High Similarity NPC87489
0.9024 High Similarity NPC50964
0.8989 High Similarity NPC288970
0.8977 High Similarity NPC144202
0.8977 High Similarity NPC127718
0.8977 High Similarity NPC65402
0.8966 High Similarity NPC275671
0.8916 High Similarity NPC82623
0.8902 High Similarity NPC264245
0.8902 High Similarity NPC476646
0.8902 High Similarity NPC23852
0.8902 High Similarity NPC209620
0.8902 High Similarity NPC470383
0.8889 High Similarity NPC209430
0.8889 High Similarity NPC30986
0.8876 High Similarity NPC8774
0.8851 High Similarity NPC295668
0.8837 High Similarity NPC474668
0.8824 High Similarity NPC152808
0.8824 High Similarity NPC201273
0.8824 High Similarity NPC293287
0.881 High Similarity NPC231310
0.881 High Similarity NPC470077
0.8795 High Similarity NPC101462
0.878 High Similarity NPC96362
0.878 High Similarity NPC209944
0.878 High Similarity NPC241290
0.878 High Similarity NPC164840
0.878 High Similarity NPC234193
0.8778 High Similarity NPC12103
0.8778 High Similarity NPC98457
0.8778 High Similarity NPC227583
0.8736 High Similarity NPC109744
0.8721 High Similarity NPC149224
0.8706 High Similarity NPC318390
0.8706 High Similarity NPC274448
0.869 High Similarity NPC470558
0.869 High Similarity NPC193870
0.869 High Similarity NPC477818
0.869 High Similarity NPC134481
0.869 High Similarity NPC113978
0.869 High Similarity NPC141941
0.8681 High Similarity NPC261807
0.8681 High Similarity NPC477226
0.8675 High Similarity NPC47761
0.8659 High Similarity NPC28862
0.8659 High Similarity NPC47982
0.8659 High Similarity NPC84694
0.8659 High Similarity NPC143182
0.8659 High Similarity NPC81306
0.8659 High Similarity NPC80530
0.8659 High Similarity NPC109546
0.8659 High Similarity NPC273410
0.8636 High Similarity NPC475751
0.8636 High Similarity NPC473956
0.8588 High Similarity NPC475798
0.8588 High Similarity NPC127606
0.8588 High Similarity NPC238485
0.8588 High Similarity NPC185568
0.8588 High Similarity NPC474047
0.8588 High Similarity NPC124172
0.8571 High Similarity NPC202389
0.8571 High Similarity NPC210717
0.8571 High Similarity NPC30166
0.8571 High Similarity NPC103165
0.8571 High Similarity NPC470049
0.8554 High Similarity NPC102253
0.8554 High Similarity NPC236237
0.8554 High Similarity NPC322313
0.8537 High Similarity NPC11908
0.8537 High Similarity NPC6978
0.8537 High Similarity NPC244385
0.8537 High Similarity NPC31828
0.8537 High Similarity NPC474216
0.8537 High Similarity NPC285761
0.8537 High Similarity NPC167037
0.8537 High Similarity NPC87604
0.8537 High Similarity NPC138621
0.8519 High Similarity NPC247325
0.8519 High Similarity NPC134330
0.8519 High Similarity NPC129165
0.8519 High Similarity NPC244488
0.8519 High Similarity NPC253190
0.8519 High Similarity NPC189883
0.8511 High Similarity NPC300399
0.8511 High Similarity NPC471482
0.8506 High Similarity NPC186145
0.8506 High Similarity NPC474657
0.8506 High Similarity NPC470620
0.8488 Intermediate Similarity NPC157257
0.8488 Intermediate Similarity NPC266511
0.8471 Intermediate Similarity NPC470384
0.8471 Intermediate Similarity NPC317458
0.8471 Intermediate Similarity NPC474634
0.8471 Intermediate Similarity NPC475789
0.8471 Intermediate Similarity NPC110778
0.8434 Intermediate Similarity NPC1319
0.8415 Intermediate Similarity NPC91594
0.8415 Intermediate Similarity NPC155986
0.8415 Intermediate Similarity NPC471798
0.8415 Intermediate Similarity NPC470711
0.8415 Intermediate Similarity NPC198968
0.8415 Intermediate Similarity NPC318495
0.8415 Intermediate Similarity NPC214570
0.8415 Intermediate Similarity NPC470758
0.8409 Intermediate Similarity NPC475664
0.8409 Intermediate Similarity NPC67872
0.8409 Intermediate Similarity NPC280556
0.8395 Intermediate Similarity NPC103822
0.8395 Intermediate Similarity NPC32832
0.8395 Intermediate Similarity NPC471723
0.8395 Intermediate Similarity NPC141071
0.8395 Intermediate Similarity NPC257347
0.8391 Intermediate Similarity NPC269058
0.8391 Intermediate Similarity NPC94462
0.8391 Intermediate Similarity NPC24277
0.8391 Intermediate Similarity NPC71520
0.8372 Intermediate Similarity NPC474493
0.8372 Intermediate Similarity NPC15534
0.8372 Intermediate Similarity NPC209802
0.8353 Intermediate Similarity NPC189972
0.8353 Intermediate Similarity NPC470614
0.8353 Intermediate Similarity NPC1272
0.8353 Intermediate Similarity NPC248886
0.8352 Intermediate Similarity NPC477605
0.8333 Intermediate Similarity NPC475679
0.8333 Intermediate Similarity NPC13554
0.8333 Intermediate Similarity NPC236112
0.8333 Intermediate Similarity NPC210268
0.8333 Intermediate Similarity NPC324772
0.8333 Intermediate Similarity NPC26117
0.8316 Intermediate Similarity NPC37207
0.8316 Intermediate Similarity NPC471889
0.8315 Intermediate Similarity NPC259875
0.8315 Intermediate Similarity NPC187785
0.8313 Intermediate Similarity NPC301707
0.8313 Intermediate Similarity NPC148977
0.8313 Intermediate Similarity NPC275910
0.8313 Intermediate Similarity NPC473943
0.8295 Intermediate Similarity NPC475313
0.8293 Intermediate Similarity NPC240604
0.8293 Intermediate Similarity NPC321016
0.8293 Intermediate Similarity NPC237460
0.8293 Intermediate Similarity NPC63958
0.8293 Intermediate Similarity NPC470749
0.8293 Intermediate Similarity NPC202642
0.8293 Intermediate Similarity NPC470362
0.8293 Intermediate Similarity NPC46160
0.8293 Intermediate Similarity NPC107059
0.8293 Intermediate Similarity NPC300324
0.8293 Intermediate Similarity NPC321381
0.8293 Intermediate Similarity NPC73875
0.8293 Intermediate Similarity NPC113733
0.8293 Intermediate Similarity NPC265588
0.828 Intermediate Similarity NPC476893
0.8272 Intermediate Similarity NPC469533
0.8272 Intermediate Similarity NPC469534
0.8272 Intermediate Similarity NPC306727
0.8272 Intermediate Similarity NPC201048
0.8272 Intermediate Similarity NPC91858
0.8272 Intermediate Similarity NPC476366
0.8272 Intermediate Similarity NPC469593
0.8261 Intermediate Similarity NPC271195
0.8256 Intermediate Similarity NPC232023
0.8256 Intermediate Similarity NPC216420
0.8256 Intermediate Similarity NPC470929
0.8256 Intermediate Similarity NPC211135

  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 NPC299068 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
0.8554 High Similarity NPD7525 Registered
0.8333 Intermediate Similarity NPD6931 Approved
0.8333 Intermediate Similarity NPD6930 Phase 2
0.8333 Intermediate Similarity NPD7514 Phase 3
0.8295 Intermediate Similarity NPD4751 Clinical (unspecified phase)
0.8214 Intermediate Similarity NPD6929 Approved
0.8171 Intermediate Similarity NPD6942 Approved
0.8171 Intermediate Similarity NPD7339 Approved
0.8161 Intermediate Similarity NPD7338 Clinical (unspecified phase)
0.8118 Intermediate Similarity NPD7332 Phase 2
0.8095 Intermediate Similarity NPD7145 Approved
0.8046 Intermediate Similarity NPD6695 Phase 3
0.8023 Intermediate Similarity NPD6902 Approved
0.7976 Intermediate Similarity NPD6925 Approved
0.7976 Intermediate Similarity NPD5776 Phase 2
0.7976 Intermediate Similarity NPD6932 Approved
0.7865 Intermediate Similarity NPD6893 Approved
0.7857 Intermediate Similarity NPD3701 Clinical (unspecified phase)
0.7791 Intermediate Similarity NPD7645 Phase 2
0.7692 Intermediate Similarity NPD7750 Discontinued
0.7692 Intermediate Similarity NPD7524 Approved
0.7619 Intermediate Similarity NPD4784 Approved
0.7619 Intermediate Similarity NPD6924 Approved
0.7619 Intermediate Similarity NPD6926 Approved
0.7619 Intermediate Similarity NPD4785 Approved
0.7614 Intermediate Similarity NPD6898 Phase 1
0.759 Intermediate Similarity NPD4243 Approved
0.7586 Intermediate Similarity NPD6683 Phase 2
0.7576 Intermediate Similarity NPD5211 Phase 2
0.7556 Intermediate Similarity NPD4786 Approved
0.7553 Intermediate Similarity NPD6079 Approved
0.7527 Intermediate Similarity NPD5328 Approved
0.7474 Intermediate Similarity NPD4202 Approved
0.7471 Intermediate Similarity NPD7322 Clinical (unspecified phase)
0.7442 Intermediate Similarity NPD6933 Approved
0.7426 Intermediate Similarity NPD5141 Approved
0.7391 Intermediate Similarity NPD3618 Phase 1
0.7381 Intermediate Similarity NPD7151 Approved
0.7381 Intermediate Similarity NPD7150 Approved
0.7381 Intermediate Similarity NPD7152 Approved
0.7374 Intermediate Similarity NPD5285 Approved
0.7374 Intermediate Similarity NPD7639 Approved
0.7374 Intermediate Similarity NPD5286 Approved
0.7374 Intermediate Similarity NPD4696 Approved
0.7374 Intermediate Similarity NPD7640 Approved
0.7368 Intermediate Similarity NPD7087 Discontinued
0.7347 Intermediate Similarity NPD4755 Approved
0.7333 Intermediate Similarity NPD3667 Approved
0.7326 Intermediate Similarity NPD8264 Approved
0.7303 Intermediate Similarity NPD7509 Discontinued
0.7303 Intermediate Similarity NPD4748 Discontinued
0.7273 Intermediate Similarity NPD7638 Approved
0.7262 Intermediate Similarity NPD7144 Approved
0.7262 Intermediate Similarity NPD7143 Approved
0.7228 Intermediate Similarity NPD5226 Approved
0.7228 Intermediate Similarity NPD5224 Approved
0.7228 Intermediate Similarity NPD4633 Approved
0.7228 Intermediate Similarity NPD5225 Approved
0.72 Intermediate Similarity NPD4700 Approved
0.7191 Intermediate Similarity NPD4195 Approved
0.7188 Intermediate Similarity NPD7637 Suspended
0.7157 Intermediate Similarity NPD5174 Approved
0.7157 Intermediate Similarity NPD5175 Approved
0.7143 Intermediate Similarity NPD4267 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD6923 Approved
0.7143 Intermediate Similarity NPD6922 Approved
0.7129 Intermediate Similarity NPD5223 Approved
0.7126 Intermediate Similarity NPD5275 Approved
0.7126 Intermediate Similarity NPD4190 Phase 3
0.7075 Intermediate Similarity NPD4634 Approved
0.7071 Intermediate Similarity NPD5221 Approved
0.7071 Intermediate Similarity NPD5220 Clinical (unspecified phase)
0.7071 Intermediate Similarity NPD5222 Approved
0.7048 Intermediate Similarity NPD6881 Approved
0.7048 Intermediate Similarity NPD6899 Approved
0.7019 Intermediate Similarity NPD7128 Approved
0.7019 Intermediate Similarity NPD6675 Approved
0.7019 Intermediate Similarity NPD6402 Approved
0.7019 Intermediate Similarity NPD5739 Approved
0.7 Intermediate Similarity NPD5173 Approved
0.6989 Remote Similarity NPD3133 Approved
0.6989 Remote Similarity NPD3665 Phase 1
0.6989 Remote Similarity NPD3666 Approved
0.6979 Remote Similarity NPD4753 Phase 2
0.6952 Remote Similarity NPD5697 Approved
0.6939 Remote Similarity NPD6399 Phase 3
0.6937 Remote Similarity NPD7327 Approved
0.6937 Remote Similarity NPD7328 Approved
0.6916 Remote Similarity NPD6883 Approved
0.6916 Remote Similarity NPD7290 Approved
0.6916 Remote Similarity NPD7102 Approved
0.6915 Remote Similarity NPD7520 Clinical (unspecified phase)
0.6914 Remote Similarity NPD368 Approved
0.6907 Remote Similarity NPD7136 Phase 2
0.69 Remote Similarity NPD4697 Phase 3
0.6887 Remote Similarity NPD4729 Approved
0.6887 Remote Similarity NPD7320 Approved
0.6887 Remote Similarity NPD4730 Approved
0.6875 Remote Similarity NPD7516 Approved
0.6857 Remote Similarity NPD4768 Approved
0.6857 Remote Similarity NPD4767 Approved
0.6852 Remote Similarity NPD8130 Phase 1
0.6852 Remote Similarity NPD6650 Approved
0.6852 Remote Similarity NPD6617 Approved
0.6852 Remote Similarity NPD6869 Approved
0.6852 Remote Similarity NPD6649 Approved
0.6852 Remote Similarity NPD6847 Approved
0.6847 Remote Similarity NPD7115 Discovery
0.6827 Remote Similarity NPD4754 Approved
0.6822 Remote Similarity NPD6373 Approved
0.6822 Remote Similarity NPD6013 Approved
0.6822 Remote Similarity NPD6014 Approved
0.6822 Remote Similarity NPD6012 Approved
0.6822 Remote Similarity NPD6372 Approved
0.6804 Remote Similarity NPD6051 Approved
0.68 Remote Similarity NPD5210 Approved
0.68 Remote Similarity NPD4629 Approved
0.6796 Remote Similarity NPD4159 Approved
0.6792 Remote Similarity NPD5701 Approved
0.6789 Remote Similarity NPD6882 Approved
0.6789 Remote Similarity NPD8297 Approved
0.6774 Remote Similarity NPD4223 Phase 3
0.6774 Remote Similarity NPD4221 Approved
0.6765 Remote Similarity NPD5290 Discontinued
0.6759 Remote Similarity NPD5247 Approved
0.6759 Remote Similarity NPD5249 Phase 3
0.6759 Remote Similarity NPD5250 Approved
0.6759 Remote Similarity NPD5251 Approved
0.6759 Remote Similarity NPD5248 Approved
0.6754 Remote Similarity NPD8379 Approved
0.6754 Remote Similarity NPD8378 Approved
0.6754 Remote Similarity NPD8296 Approved
0.6754 Remote Similarity NPD8380 Approved
0.6754 Remote Similarity NPD8335 Approved
0.6754 Remote Similarity NPD7503 Approved
0.6737 Remote Similarity NPD5329 Approved
0.6731 Remote Similarity NPD7632 Discontinued
0.6729 Remote Similarity NPD6011 Approved
0.6729 Remote Similarity NPD5128 Approved
0.6727 Remote Similarity NPD4632 Approved
0.6697 Remote Similarity NPD5217 Approved
0.6697 Remote Similarity NPD5215 Approved
0.6697 Remote Similarity NPD5216 Approved
0.6667 Remote Similarity NPD6083 Phase 2
0.6667 Remote Similarity NPD4787 Phase 1
0.6667 Remote Similarity NPD6054 Approved
0.6667 Remote Similarity NPD6084 Phase 2
0.6667 Remote Similarity NPD7515 Phase 2
0.6667 Remote Similarity NPD4623 Approved
0.6667 Remote Similarity NPD5279 Phase 3
0.6667 Remote Similarity NPD8377 Approved
0.6667 Remote Similarity NPD4519 Discontinued
0.6667 Remote Similarity NPD8294 Approved
0.6632 Remote Similarity NPD3668 Phase 3
0.6632 Remote Similarity NPD4197 Approved
0.6609 Remote Similarity NPD8033 Approved
0.6606 Remote Similarity NPD5134 Clinical (unspecified phase)
0.6606 Remote Similarity NPD5169 Approved
0.6606 Remote Similarity NPD5135 Approved
0.6559 Remote Similarity NPD4821 Approved
0.6559 Remote Similarity NPD4822 Approved
0.6559 Remote Similarity NPD4819 Approved
0.6559 Remote Similarity NPD4820 Approved
0.6552 Remote Similarity NPD6370 Approved
0.6549 Remote Similarity NPD6009 Approved
0.6545 Remote Similarity NPD5127 Approved
0.6545 Remote Similarity NPD6401 Clinical (unspecified phase)
0.6526 Remote Similarity NPD4788 Approved
0.6522 Remote Similarity NPD6118 Approved
0.6522 Remote Similarity NPD6114 Approved
0.6522 Remote Similarity NPD6319 Approved
0.6522 Remote Similarity NPD6059 Approved
0.6522 Remote Similarity NPD6115 Approved
0.6522 Remote Similarity NPD5784 Clinical (unspecified phase)
0.6522 Remote Similarity NPD6697 Approved
0.6517 Remote Similarity NPD4732 Discontinued
0.6514 Remote Similarity NPD4061 Clinical (unspecified phase)
0.65 Remote Similarity NPD8034 Phase 2
0.65 Remote Similarity NPD8035 Phase 2
0.6495 Remote Similarity NPD4689 Approved
0.6495 Remote Similarity NPD3574 Clinical (unspecified phase)
0.6495 Remote Similarity NPD5205 Approved
0.6495 Remote Similarity NPD4693 Phase 3
0.6495 Remote Similarity NPD4688 Approved
0.6495 Remote Similarity NPD4138 Approved
0.6495 Remote Similarity NPD4690 Approved
0.6495 Remote Similarity NPD5690 Phase 2
0.6481 Remote Similarity NPD6412 Phase 2
0.6476 Remote Similarity NPD5344 Discontinued
0.6466 Remote Similarity NPD6015 Approved
0.6466 Remote Similarity NPD6016 Approved
0.6442 Remote Similarity NPD4225 Approved
0.6441 Remote Similarity NPD7492 Approved
0.6435 Remote Similarity NPD7101 Approved
0.6435 Remote Similarity NPD7100 Approved
0.6422 Remote Similarity NPD5168 Approved
0.6413 Remote Similarity NPD6116 Phase 1
0.641 Remote Similarity NPD5988 Approved
0.6404 Remote Similarity NPD4809 Clinical (unspecified phase)
0.6404 Remote Similarity NPD4808 Clinical (unspecified phase)

  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