Structure

Physi-Chem Properties

Molecular Weight:  414.39
Volume:  482.068
LogP:  7.944
LogD:  6.849
LogS:  -6.906
# Rotatable Bonds:  6
TPSA:  20.23
# H-Bond Aceptor:  1
# H-Bond Donor:  1
# Rings:  4
# Heavy Atoms:  1

MedChem Properties

QED Drug-Likeness Score:  0.436
Synthetic Accessibility Score:  4.551
Fsp3:  0.931
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:  -4.622
MDCK Permeability:  3.638622001744807e-05
Pgp-inhibitor:  0.332
Pgp-substrate:  0.229
Human Intestinal Absorption (HIA):  0.004
20% Bioavailability (F20%):  0.992
30% Bioavailability (F30%):  0.8

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.019
Plasma Protein Binding (PPB):  94.54940032958984%
Volume Distribution (VD):  1.295
Pgp-substrate:  1.0943799018859863%

ADMET: Metabolism

CYP1A2-inhibitor:  0.106
CYP1A2-substrate:  0.227
CYP2C19-inhibitor:  0.123
CYP2C19-substrate:  0.918
CYP2C9-inhibitor:  0.274
CYP2C9-substrate:  0.091
CYP2D6-inhibitor:  0.055
CYP2D6-substrate:  0.585
CYP3A4-inhibitor:  0.771
CYP3A4-substrate:  0.595

ADMET: Excretion

Clearance (CL):  8.573
Half-life (T1/2):  0.045

ADMET: Toxicity

hERG Blockers:  0.31
Human Hepatotoxicity (H-HT):  0.132
Drug-inuced Liver Injury (DILI):  0.052
AMES Toxicity:  0.001
Rat Oral Acute Toxicity:  0.022
Maximum Recommended Daily Dose:  0.402
Skin Sensitization:  0.93
Carcinogencity:  0.02
Eye Corrosion:  0.989
Eye Irritation:  0.797
Respiratory Toxicity:  0.431

Download Data

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

  Natural Product: NPC257347

Natural Product ID:  NPC257347
Common Name*:   24-Ethyl-Cholest-5Alpha-7-En-3-Beta-Ol
IUPAC Name:   (3S,5S,9R,10S,13R,14R,17R)-17-[(2R,5S)-5-ethyl-6-methylheptan-2-yl]-10,13-dimethyl-2,3,4,5,6,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol
Synonyms:  
Standard InCHIKey:  YSKVBPGQYRAUQO-XCFYOIDPSA-N
Standard InCHI:  InChI=1S/C29H50O/c1-7-21(19(2)3)9-8-20(4)25-12-13-26-24-11-10-22-18-23(30)14-16-28(22,5)27(24)15-17-29(25,26)6/h11,19-23,25-27,30H,7-10,12-18H2,1-6H3/t20-,21+,22+,23+,25-,26+,27+,28+,29-/m1/s1
SMILES:  CC[C@@H](CC[C@@H](C)[C@H]1CC[C@H]2C3=CC[C@H]4C[C@H](CC[C@]4(C)[C@H]3CC[C@]12C)O)C(C)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL238597
PubChem CID:   5283639
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000258] Steroids and steroid derivatives
        • [CHEMONTID:0002031] Stigmastanes 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
NPO27323 Cestrum nocturnum Species Solanaceae Eukaryota leaves n.a. n.a. PMID[11170659]
NPO27012 Laurencia pannosa Species Rhodomelaceae Eukaryota n.a. Malaysian n.a. PMID[11374951]
NPO27323 Cestrum nocturnum Species Solanaceae Eukaryota leaves n.a. n.a. PMID[12502329]
NPO27072 Monochaetum vulcanicum Species Melastomataceae Eukaryota n.a. n.a. n.a. PMID[15165161]
NPO18932 Melia azedarach Species Meliaceae Eukaryota n.a. Brazilian n.a. PMID[15387656]
NPO18932 Melia azedarach Species Meliaceae Eukaryota n.a. ripe fruit n.a. PMID[16205005]
NPO40426 Agelas oroides enoyl Strain Agelasidae Eukaryota Tubers n.a. n.a. PMID[17765547]
NPO17223 Agelas oroides Species Agelasidae Eukaryota n.a. n.a. n.a. PMID[32072810]
NPO18932 Melia azedarach Species Meliaceae Eukaryota Fruits n.a. n.a. PMID[33253570]
NPO18932 Melia azedarach Species Meliaceae Eukaryota Seeds n.a. n.a. PMID[3701342]
NPO17794 Streptomyces violaceusniger Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[8557611]
NPO18560 Tripterospermum japonicum Species Gentianaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO27725 Artemisia vestita Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO27323 Cestrum nocturnum Species Solanaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO18932 Melia azedarach Species Meliaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO22242 Phellodendron chinense Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO4002 Lappula intermedia Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO27323 Cestrum nocturnum Species Solanaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO18932.1 Melia azedarach var. toosendan Varieties Meliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO18932 Melia azedarach Species Meliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO27725 Artemisia vestita Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO27773 Rhododendron ovatum Species Ericaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO18560 Tripterospermum japonicum Species Gentianaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO4002 Lappula intermedia Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22242 Phellodendron chinense Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22242 Phellodendron chinense Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO27725 Artemisia vestita Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO27323 Cestrum nocturnum Species Solanaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO18932 Melia azedarach Species Meliaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO18932 Melia azedarach Species Meliaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO22242 Phellodendron chinense Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO18932.1 Melia azedarach var. toosendan Varieties Meliaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO9811 Macrotyloma uniflorum Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26895 Baccharis bigelovii Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11140 Coprinopsis cinerea Species Psathyrellaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27707 Soja hispida Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17223 Agelas oroides Species Agelasidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18932.1 Melia azedarach var. toosendan Varieties Meliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18560 Tripterospermum japonicum Species Gentianaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18932 Melia azedarach Species Meliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27072 Monochaetum vulcanicum Species Melastomataceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27012 Laurencia pannosa Species Rhodomelaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27323 Cestrum nocturnum Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14323 Bossiella orbigniana Species Corallinaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19587 Cordia rothii Species Cordiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27740 Alcantara ekmaniana n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO12920 Erimacrus isenbeckii Species Atelecyclidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27648 Cereus aethiops Species Cactaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27773 Rhododendron ovatum Species Ericaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22488 Leptosphaeria oraemaris Species Leptosphaeriaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27688 Aeonium goochiae Species Crassulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27262 Dryopteris inaequalis Species Dryopteridaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19809 Streptomyces roseoviolaceus Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO20208 Rhinogobius brunneus Species Gobiidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17794 Streptomyces violaceusniger Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO27569 Archangelica officinalis Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16500 Byssochlamys spectabilis Species Thermoascaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22242 Phellodendron chinense Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27191 Schistochila appendiculata Species Schistochilaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27725 Artemisia vestita Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4002 Lappula intermedia Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19260 Zanthoxylum petiolare Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7497 Guatteria blepharophylla Species Annonaceae 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
NPT1333 Individual Protein Enoyl-acyl-carrier protein reductase Plasmodium falciparum IC50 = 18.0 ug.mL-1 PMID[461182]
NPT839 Cell Line L6 Rattus norvegicus IC50 > 90.0 ug.mL-1 PMID[461182]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum IC50 = 16.1 ug.mL-1 PMID[461182]
NPT844 Organism Trypanosoma brucei rhodesiense Trypanosoma brucei rhodesiense IC50 = 14.2 ug.mL-1 PMID[461182]
NPT580 Organism Trypanosoma cruzi Trypanosoma cruzi IC50 > 30.0 ug.mL-1 PMID[461182]
NPT633 Organism Leishmania donovani Leishmania donovani IC50 = 29.5 ug.mL-1 PMID[461182]

☑ 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 NPC257347 and all remaining natural products in the NPASS database.
●  The right table: Most similar natural products (Tc>=0.56 or Top200).

Similarity Score Similarity Level Natural Product ID
1.0 High Similarity NPC141071
1.0 High Similarity NPC471723
0.9857 High Similarity NPC189883
0.9857 High Similarity NPC129165
0.9857 High Similarity NPC134330
0.9714 High Similarity NPC134847
0.9714 High Similarity NPC136188
0.9714 High Similarity NPC285893
0.9714 High Similarity NPC28657
0.9714 High Similarity NPC230301
0.9714 High Similarity NPC304309
0.9714 High Similarity NPC22105
0.9714 High Similarity NPC162742
0.9714 High Similarity NPC288035
0.9577 High Similarity NPC46160
0.9577 High Similarity NPC113733
0.9577 High Similarity NPC202642
0.9577 High Similarity NPC470362
0.9577 High Similarity NPC237460
0.9577 High Similarity NPC321381
0.9577 High Similarity NPC321016
0.9577 High Similarity NPC300324
0.9577 High Similarity NPC107059
0.9577 High Similarity NPC240604
0.9452 High Similarity NPC209430
0.9452 High Similarity NPC1319
0.9452 High Similarity NPC30986
0.9444 High Similarity NPC34019
0.9444 High Similarity NPC155986
0.9444 High Similarity NPC318495
0.9444 High Similarity NPC214570
0.9444 High Similarity NPC198968
0.9437 High Similarity NPC118508
0.9437 High Similarity NPC322353
0.9437 High Similarity NPC121744
0.9324 High Similarity NPC236112
0.9315 High Similarity NPC65897
0.9315 High Similarity NPC138621
0.9315 High Similarity NPC85346
0.9315 High Similarity NPC186191
0.9315 High Similarity NPC205455
0.9315 High Similarity NPC474216
0.9315 High Similarity NPC76931
0.9315 High Similarity NPC307965
0.9315 High Similarity NPC6978
0.9315 High Similarity NPC275910
0.9315 High Similarity NPC477522
0.9315 High Similarity NPC302041
0.9315 High Similarity NPC473943
0.9315 High Similarity NPC167037
0.9315 High Similarity NPC244385
0.9315 High Similarity NPC87604
0.9315 High Similarity NPC285761
0.9315 High Similarity NPC18603
0.9306 High Similarity NPC244488
0.9306 High Similarity NPC247325
0.9306 High Similarity NPC73875
0.9296 High Similarity NPC469593
0.9296 High Similarity NPC469534
0.9296 High Similarity NPC469533
0.92 High Similarity NPC474531
0.9189 High Similarity NPC47982
0.9189 High Similarity NPC81306
0.9189 High Similarity NPC109546
0.9189 High Similarity NPC273410
0.9189 High Similarity NPC328714
0.9189 High Similarity NPC84694
0.9189 High Similarity NPC143182
0.9189 High Similarity NPC80530
0.9189 High Similarity NPC28862
0.9155 High Similarity NPC201373
0.9155 High Similarity NPC474140
0.9155 High Similarity NPC182717
0.913 High Similarity NPC160209
0.9079 High Similarity NPC30166
0.9079 High Similarity NPC470049
0.9067 High Similarity NPC236237
0.9067 High Similarity NPC209944
0.9067 High Similarity NPC102253
0.9067 High Similarity NPC26117
0.9067 High Similarity NPC322313
0.9067 High Similarity NPC13554
0.9067 High Similarity NPC241290
0.9067 High Similarity NPC164840
0.9067 High Similarity NPC234193
0.9054 High Similarity NPC318136
0.9054 High Similarity NPC477514
0.9054 High Similarity NPC312328
0.9041 High Similarity NPC96319
0.9028 High Similarity NPC100334
0.9014 High Similarity NPC111234
0.8961 High Similarity NPC317458
0.8947 High Similarity NPC264245
0.8947 High Similarity NPC47761
0.8947 High Similarity NPC209620
0.8947 High Similarity NPC474731
0.8947 High Similarity NPC23852
0.8947 High Similarity NPC474752
0.8947 High Similarity NPC470383
0.8947 High Similarity NPC474759
0.8947 High Similarity NPC474683
0.8947 High Similarity NPC82986
0.8947 High Similarity NPC7505
0.8889 High Similarity NPC195489
0.8889 High Similarity NPC471799
0.8873 High Similarity NPC145498
0.8873 High Similarity NPC475728
0.8873 High Similarity NPC45296
0.8857 High Similarity NPC208999
0.8846 High Similarity NPC478102
0.8846 High Similarity NPC209802
0.8846 High Similarity NPC124172
0.8846 High Similarity NPC474047
0.8846 High Similarity NPC470077
0.8831 High Similarity NPC248886
0.8831 High Similarity NPC201852
0.8831 High Similarity NPC296701
0.8831 High Similarity NPC470614
0.8831 High Similarity NPC49964
0.8831 High Similarity NPC218616
0.8831 High Similarity NPC50964
0.8831 High Similarity NPC101462
0.8831 High Similarity NPC202389
0.8831 High Similarity NPC20853
0.8831 High Similarity NPC1272
0.8831 High Similarity NPC189972
0.8831 High Similarity NPC5985
0.8831 High Similarity NPC87489
0.8784 High Similarity NPC30590
0.8784 High Similarity NPC265328
0.8784 High Similarity NPC120098
0.8784 High Similarity NPC290598
0.8784 High Similarity NPC27765
0.8784 High Similarity NPC122418
0.8767 High Similarity NPC471797
0.8767 High Similarity NPC243342
0.8767 High Similarity NPC196358
0.8767 High Similarity NPC5046
0.8767 High Similarity NPC145552
0.8767 High Similarity NPC254509
0.8767 High Similarity NPC477138
0.8767 High Similarity NPC25511
0.8767 High Similarity NPC192638
0.8767 High Similarity NPC62657
0.8767 High Similarity NPC49168
0.8767 High Similarity NPC91858
0.875 High Similarity NPC110799
0.875 High Similarity NPC242001
0.875 High Similarity NPC167706
0.8734 High Similarity NPC318390
0.8718 High Similarity NPC110778
0.8718 High Similarity NPC477818
0.8718 High Similarity NPC475789
0.8718 High Similarity NPC474634
0.8718 High Similarity NPC113978
0.8718 High Similarity NPC207013
0.8714 High Similarity NPC197805
0.8701 High Similarity NPC6707
0.8684 High Similarity NPC472463
0.8667 High Similarity NPC90979
0.8667 High Similarity NPC40394
0.8667 High Similarity NPC101475
0.8667 High Similarity NPC34177
0.8667 High Similarity NPC471798
0.8667 High Similarity NPC472805
0.8667 High Similarity NPC157996
0.8649 High Similarity NPC138374
0.8649 High Similarity NPC66566
0.8649 High Similarity NPC477923
0.8649 High Similarity NPC240235
0.8649 High Similarity NPC34700
0.8649 High Similarity NPC200243
0.8649 High Similarity NPC104387
0.8649 High Similarity NPC178383
0.8649 High Similarity NPC185536
0.8649 High Similarity NPC231256
0.8649 High Similarity NPC291503
0.8649 High Similarity NPC230704
0.8649 High Similarity NPC3403
0.8649 High Similarity NPC70982
0.8649 High Similarity NPC471468
0.8649 High Similarity NPC103822
0.8649 High Similarity NPC212879
0.8625 High Similarity NPC125399
0.8625 High Similarity NPC6391
0.8625 High Similarity NPC261266
0.8625 High Similarity NPC477604
0.8625 High Similarity NPC24277
0.8625 High Similarity NPC474970
0.8625 High Similarity NPC94462
0.8608 High Similarity NPC59453
0.8608 High Similarity NPC33913
0.8608 High Similarity NPC472265
0.8608 High Similarity NPC231310
0.8608 High Similarity NPC185568
0.8608 High Similarity NPC205845
0.8608 High Similarity NPC238485
0.8608 High Similarity NPC221758
0.8571 High Similarity NPC222366
0.8571 High Similarity NPC286669

  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 NPC257347 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
0.9714 High Similarity NPD6942 Approved
0.9714 High Similarity NPD7339 Approved
0.9067 High Similarity NPD7525 Registered
0.9041 High Similarity NPD3701 Clinical (unspecified phase)
0.875 High Similarity NPD4243 Approved
0.8608 High Similarity NPD4786 Approved
0.8514 High Similarity NPD6924 Approved
0.8514 High Similarity NPD4784 Approved
0.8514 High Similarity NPD4785 Approved
0.8514 High Similarity NPD6926 Approved
0.8493 Intermediate Similarity NPD7152 Approved
0.8493 Intermediate Similarity NPD7150 Approved
0.8493 Intermediate Similarity NPD7151 Approved
0.8472 Intermediate Similarity NPD6923 Approved
0.8472 Intermediate Similarity NPD6922 Approved
0.8442 Intermediate Similarity NPD7645 Phase 2
0.8356 Intermediate Similarity NPD7144 Approved
0.8356 Intermediate Similarity NPD7143 Approved
0.8354 Intermediate Similarity NPD3667 Approved
0.8313 Intermediate Similarity NPD5328 Approved
0.8289 Intermediate Similarity NPD6933 Approved
0.8171 Intermediate Similarity NPD3618 Phase 1
0.8158 Intermediate Similarity NPD5275 Approved
0.8158 Intermediate Similarity NPD4190 Phase 3
0.8118 Intermediate Similarity NPD6079 Approved
0.8101 Intermediate Similarity NPD4748 Discontinued
0.8072 Intermediate Similarity NPD4751 Clinical (unspecified phase)
0.7975 Intermediate Similarity NPD6929 Approved
0.7927 Intermediate Similarity NPD3665 Phase 1
0.7927 Intermediate Similarity NPD3666 Approved
0.7927 Intermediate Similarity NPD3133 Approved
0.7875 Intermediate Similarity NPD6930 Phase 2
0.7875 Intermediate Similarity NPD7509 Discontinued
0.7875 Intermediate Similarity NPD6931 Approved
0.7816 Intermediate Similarity NPD4202 Approved
0.775 Intermediate Similarity NPD4195 Approved
0.7722 Intermediate Similarity NPD5776 Phase 2
0.7722 Intermediate Similarity NPD6925 Approved
0.7722 Intermediate Similarity NPD6932 Approved
0.7625 Intermediate Similarity NPD7145 Approved
0.7619 Intermediate Similarity NPD7520 Clinical (unspecified phase)
0.7614 Intermediate Similarity NPD6399 Phase 3
0.759 Intermediate Similarity NPD6695 Phase 3
0.7556 Intermediate Similarity NPD5220 Clinical (unspecified phase)
0.7556 Intermediate Similarity NPD5222 Approved
0.7556 Intermediate Similarity NPD4697 Phase 3
0.7556 Intermediate Similarity NPD5221 Approved
0.7531 Intermediate Similarity NPD6683 Phase 2
0.7529 Intermediate Similarity NPD5279 Phase 3
0.75 Intermediate Similarity NPD3668 Phase 3
0.75 Intermediate Similarity NPD7338 Clinical (unspecified phase)
0.7473 Intermediate Similarity NPD4755 Approved
0.7473 Intermediate Similarity NPD5173 Approved
0.7471 Intermediate Similarity NPD4753 Phase 2
0.747 Intermediate Similarity NPD4221 Approved
0.747 Intermediate Similarity NPD4223 Phase 3
0.7468 Intermediate Similarity NPD8264 Approved
0.7439 Intermediate Similarity NPD7514 Phase 3
0.7412 Intermediate Similarity NPD5329 Approved
0.7412 Intermediate Similarity NPD6893 Approved
0.7407 Intermediate Similarity NPD7322 Clinical (unspecified phase)
0.7349 Intermediate Similarity NPD6902 Approved
0.7312 Intermediate Similarity NPD5286 Approved
0.7312 Intermediate Similarity NPD4700 Approved
0.7312 Intermediate Similarity NPD4696 Approved
0.7312 Intermediate Similarity NPD5285 Approved
0.7303 Intermediate Similarity NPD7515 Phase 2
0.7294 Intermediate Similarity NPD4197 Approved
0.7273 Intermediate Similarity NPD4267 Clinical (unspecified phase)
0.7241 Intermediate Similarity NPD7750 Discontinued
0.7241 Intermediate Similarity NPD7524 Approved
0.7234 Intermediate Similarity NPD5223 Approved
0.7229 Intermediate Similarity NPD7332 Phase 2
0.7204 Intermediate Similarity NPD5290 Discontinued
0.7204 Intermediate Similarity NPD7638 Approved
0.7179 Intermediate Similarity NPD4787 Phase 1
0.7176 Intermediate Similarity NPD4788 Approved
0.7158 Intermediate Similarity NPD5225 Approved
0.7158 Intermediate Similarity NPD5224 Approved
0.7158 Intermediate Similarity NPD5211 Phase 2
0.7158 Intermediate Similarity NPD4633 Approved
0.7158 Intermediate Similarity NPD5226 Approved
0.7143 Intermediate Similarity NPD6898 Phase 1
0.7128 Intermediate Similarity NPD7640 Approved
0.7128 Intermediate Similarity NPD7639 Approved
0.7126 Intermediate Similarity NPD4138 Approved
0.7126 Intermediate Similarity NPD4693 Phase 3
0.7126 Intermediate Similarity NPD4689 Approved
0.7126 Intermediate Similarity NPD4690 Approved
0.7126 Intermediate Similarity NPD4688 Approved
0.7126 Intermediate Similarity NPD7521 Approved
0.7126 Intermediate Similarity NPD7334 Approved
0.7126 Intermediate Similarity NPD5205 Approved
0.7126 Intermediate Similarity NPD6684 Approved
0.7126 Intermediate Similarity NPD7146 Approved
0.7126 Intermediate Similarity NPD6409 Approved
0.7126 Intermediate Similarity NPD5330 Approved
0.7113 Intermediate Similarity NPD7128 Approved
0.7113 Intermediate Similarity NPD5739 Approved
0.7113 Intermediate Similarity NPD6675 Approved
0.7113 Intermediate Similarity NPD6402 Approved
0.7097 Intermediate Similarity NPD6084 Phase 2
0.7097 Intermediate Similarity NPD6083 Phase 2
0.7089 Intermediate Similarity NPD4808 Clinical (unspecified phase)
0.7089 Intermediate Similarity NPD4809 Clinical (unspecified phase)
0.7083 Intermediate Similarity NPD4754 Approved
0.7083 Intermediate Similarity NPD5175 Approved
0.7083 Intermediate Similarity NPD5174 Approved
0.7079 Intermediate Similarity NPD6051 Approved
0.7065 Intermediate Similarity NPD5210 Approved
0.7065 Intermediate Similarity NPD4629 Approved
0.701 Intermediate Similarity NPD5141 Approved
0.6988 Remote Similarity NPD3617 Approved
0.697 Remote Similarity NPD7320 Approved
0.697 Remote Similarity NPD6881 Approved
0.697 Remote Similarity NPD6899 Approved
0.6966 Remote Similarity NPD4723 Approved
0.6966 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6966 Remote Similarity NPD6672 Approved
0.6966 Remote Similarity NPD4722 Approved
0.6966 Remote Similarity NPD5737 Approved
0.6966 Remote Similarity NPD6903 Approved
0.6957 Remote Similarity NPD7748 Approved
0.6939 Remote Similarity NPD4768 Approved
0.6939 Remote Similarity NPD4767 Approved
0.6932 Remote Similarity NPD3574 Clinical (unspecified phase)
0.6932 Remote Similarity NPD4694 Approved
0.6932 Remote Similarity NPD5280 Approved
0.6932 Remote Similarity NPD5690 Phase 2
0.6923 Remote Similarity NPD7087 Discontinued
0.6923 Remote Similarity NPD8035 Phase 2
0.6923 Remote Similarity NPD8034 Phase 2
0.6914 Remote Similarity NPD6113 Clinical (unspecified phase)
0.69 Remote Similarity NPD6373 Approved
0.69 Remote Similarity NPD6372 Approved
0.6869 Remote Similarity NPD5701 Approved
0.6869 Remote Similarity NPD5697 Approved
0.6835 Remote Similarity NPD3700 Clinical (unspecified phase)
0.6835 Remote Similarity NPD3699 Clinical (unspecified phase)
0.6832 Remote Similarity NPD7290 Approved
0.6832 Remote Similarity NPD7102 Approved
0.6832 Remote Similarity NPD6883 Approved
0.68 Remote Similarity NPD4729 Approved
0.68 Remote Similarity NPD6011 Approved
0.68 Remote Similarity NPD4730 Approved
0.68 Remote Similarity NPD5168 Approved
0.68 Remote Similarity NPD5128 Approved
0.6765 Remote Similarity NPD6869 Approved
0.6765 Remote Similarity NPD6649 Approved
0.6765 Remote Similarity NPD6847 Approved
0.6765 Remote Similarity NPD8130 Phase 1
0.6765 Remote Similarity NPD6650 Approved
0.6765 Remote Similarity NPD6617 Approved
0.6765 Remote Similarity NPD6401 Clinical (unspecified phase)
0.675 Remote Similarity NPD4747 Approved
0.6747 Remote Similarity NPD6117 Approved
0.6744 Remote Similarity NPD4139 Approved
0.6744 Remote Similarity NPD4692 Approved
0.6742 Remote Similarity NPD6098 Approved
0.6737 Remote Similarity NPD7902 Approved
0.6733 Remote Similarity NPD6012 Approved
0.6733 Remote Similarity NPD6014 Approved
0.6733 Remote Similarity NPD6013 Approved
0.6709 Remote Similarity NPD3621 Clinical (unspecified phase)
0.6702 Remote Similarity NPD5695 Phase 3
0.6699 Remote Similarity NPD6882 Approved
0.6699 Remote Similarity NPD8297 Approved
0.6667 Remote Similarity NPD5169 Approved
0.6667 Remote Similarity NPD342 Phase 1
0.6667 Remote Similarity NPD5248 Approved
0.6667 Remote Similarity NPD5247 Approved
0.6667 Remote Similarity NPD5135 Approved
0.6667 Remote Similarity NPD4634 Approved
0.6667 Remote Similarity NPD6116 Phase 1
0.6667 Remote Similarity NPD5696 Approved
0.6667 Remote Similarity NPD5251 Approved
0.6667 Remote Similarity NPD5134 Clinical (unspecified phase)
0.6667 Remote Similarity NPD5250 Approved
0.6667 Remote Similarity NPD5249 Phase 3
0.6628 Remote Similarity NPD4695 Discontinued
0.6625 Remote Similarity NPD4137 Phase 3
0.6602 Remote Similarity NPD5215 Approved
0.6602 Remote Similarity NPD5127 Approved
0.6602 Remote Similarity NPD5217 Approved
0.6602 Remote Similarity NPD5216 Approved
0.6588 Remote Similarity NPD6697 Approved
0.6588 Remote Similarity NPD6118 Approved
0.6588 Remote Similarity NPD6114 Approved
0.6588 Remote Similarity NPD6115 Approved
0.6579 Remote Similarity NPD368 Approved
0.6559 Remote Similarity NPD7637 Suspended
0.6559 Remote Similarity NPD5281 Approved
0.6559 Remote Similarity NPD5284 Approved
0.6556 Remote Similarity NPD4519 Discontinued
0.6556 Remote Similarity NPD4623 Approved
0.6543 Remote Similarity NPD6938 Clinical (unspecified phase)
0.6543 Remote Similarity NPD4245 Approved
0.6543 Remote Similarity NPD4244 Approved
0.6543 Remote Similarity NPD6939 Phase 2
0.6543 Remote Similarity NPD4789 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