Structure

Physi-Chem Properties

Molecular Weight:  344.2
Volume:  362.161
LogP:  1.655
LogD:  0.815
LogS:  -3.311
# Rotatable Bonds:  1
TPSA:  77.76
# H-Bond Aceptor:  4
# H-Bond Donor:  3
# Rings:  4
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.638
Synthetic Accessibility Score:  5.061
Fsp3:  0.667
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.93
MDCK Permeability:  9.673874956206419e-06
Pgp-inhibitor:  0.573
Pgp-substrate:  0.985
Human Intestinal Absorption (HIA):  0.589
20% Bioavailability (F20%):  0.796
30% Bioavailability (F30%):  0.821

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.65
Plasma Protein Binding (PPB):  62.594261169433594%
Volume Distribution (VD):  1.552
Pgp-substrate:  28.950748443603516%

ADMET: Metabolism

CYP1A2-inhibitor:  0.028
CYP1A2-substrate:  0.178
CYP2C19-inhibitor:  0.023
CYP2C19-substrate:  0.688
CYP2C9-inhibitor:  0.009
CYP2C9-substrate:  0.432
CYP2D6-inhibitor:  0.004
CYP2D6-substrate:  0.111
CYP3A4-inhibitor:  0.16
CYP3A4-substrate:  0.212

ADMET: Excretion

Clearance (CL):  3.21
Half-life (T1/2):  0.466

ADMET: Toxicity

hERG Blockers:  0.014
Human Hepatotoxicity (H-HT):  0.226
Drug-inuced Liver Injury (DILI):  0.038
AMES Toxicity:  0.02
Rat Oral Acute Toxicity:  0.959
Maximum Recommended Daily Dose:  0.947
Skin Sensitization:  0.198
Carcinogencity:  0.942
Eye Corrosion:  0.005
Eye Irritation:  0.052
Respiratory Toxicity:  0.988

Download Data

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

  Natural Product: NPC117133

Natural Product ID:  NPC117133
Common Name*:   Stizophyllin
IUPAC Name:   1-[(2R,3R,9S,10R,12R,13S,14S)-2,3,12-trihydroxy-10,13-dimethyl-2,3,6,9,11,12,14,15-octahydro-1H-cyclopenta[a]phenanthren-17-yl]ethanone
Synonyms:   stizophyllin
Standard InCHIKey:  IWQKGRNFKYKJHS-KQFCJCSDSA-N
Standard InCHI:  InChI=1S/C21H28O4/c1-11(22)14-6-7-15-13-5-4-12-8-17(23)18(24)10-20(12,2)16(13)9-19(25)21(14,15)3/h5-6,8,15-19,23-25H,4,7,9-10H2,1-3H3/t15-,16-,17+,18+,19+,20-,21+/m0/s1
SMILES:  O[C@@H]1C=C2CC=C3[C@@H]([C@]2(C[C@H]1O)C)C[C@H]([C@]1([C@H]3CC=C1C(=O)C)C)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL477890
PubChem CID:   13890847
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000258] Steroids and steroid derivatives
        • [CHEMONTID:0001194] Oxosteroids
          • [CHEMONTID:0003058] 20-oxosteroids

*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
NPO17543 Stizophyllum riparium Species Bignoniaceae Eukaryota n.a. n.a. n.a. PMID[3598599]
NPO17543 Stizophyllum riparium Species Bignoniaceae 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
NPT168 Cell Line P388 Mus musculus ED50 = 0.07 ug ml-1 PMID[501558]

☑ 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 NPC117133 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
0.9111 High Similarity NPC119416
0.9062 High Similarity NPC473424
0.9022 High Similarity NPC134826
0.9022 High Similarity NPC109305
0.8817 High Similarity NPC69454
0.8817 High Similarity NPC474736
0.8804 High Similarity NPC48010
0.8791 High Similarity NPC474677
0.8791 High Similarity NPC471722
0.8778 High Similarity NPC472974
0.8737 High Similarity NPC249954
0.8723 High Similarity NPC472976
0.8723 High Similarity NPC472977
0.871 High Similarity NPC63748
0.871 High Similarity NPC473998
0.871 High Similarity NPC233116
0.871 High Similarity NPC116726
0.8696 High Similarity NPC469319
0.8696 High Similarity NPC309603
0.8696 High Similarity NPC229871
0.8696 High Similarity NPC473999
0.8673 High Similarity NPC293753
0.8673 High Similarity NPC477915
0.8646 High Similarity NPC320306
0.8632 High Similarity NPC259286
0.8632 High Similarity NPC473170
0.8632 High Similarity NPC271195
0.8617 High Similarity NPC472930
0.8614 High Similarity NPC65941
0.8602 High Similarity NPC85173
0.8602 High Similarity NPC191684
0.86 High Similarity NPC149047
0.8571 High Similarity NPC72133
0.8557 High Similarity NPC478056
0.8557 High Similarity NPC471717
0.8557 High Similarity NPC103051
0.8542 High Similarity NPC456
0.8542 High Similarity NPC471463
0.8542 High Similarity NPC472941
0.8529 High Similarity NPC214644
0.8526 High Similarity NPC196227
0.8526 High Similarity NPC8993
0.8515 High Similarity NPC220229
0.8515 High Similarity NPC475060
0.8511 High Similarity NPC131872
0.8511 High Similarity NPC475806
0.8511 High Similarity NPC19114
0.85 High Similarity NPC209502
0.85 High Similarity NPC204833
0.8495 Intermediate Similarity NPC31985
0.8495 Intermediate Similarity NPC32830
0.8495 Intermediate Similarity NPC86319
0.8495 Intermediate Similarity NPC1015
0.8495 Intermediate Similarity NPC275740
0.8495 Intermediate Similarity NPC472983
0.8485 Intermediate Similarity NPC234892
0.8478 Intermediate Similarity NPC475740
0.8469 Intermediate Similarity NPC327431
0.8469 Intermediate Similarity NPC287833
0.8469 Intermediate Similarity NPC316964
0.8469 Intermediate Similarity NPC154072
0.8462 Intermediate Similarity NPC474083
0.8454 Intermediate Similarity NPC474785
0.8454 Intermediate Similarity NPC474938
0.8438 Intermediate Similarity NPC174948
0.8438 Intermediate Similarity NPC318282
0.8438 Intermediate Similarity NPC297199
0.8438 Intermediate Similarity NPC173875
0.8438 Intermediate Similarity NPC469995
0.8438 Intermediate Similarity NPC472932
0.8431 Intermediate Similarity NPC295244
0.8431 Intermediate Similarity NPC217201
0.8416 Intermediate Similarity NPC296945
0.8416 Intermediate Similarity NPC302607
0.8416 Intermediate Similarity NPC50692
0.8416 Intermediate Similarity NPC85829
0.8416 Intermediate Similarity NPC260268
0.8416 Intermediate Similarity NPC476027
0.8416 Intermediate Similarity NPC97202
0.8416 Intermediate Similarity NPC319077
0.8416 Intermediate Similarity NPC150531
0.8416 Intermediate Similarity NPC214264
0.8416 Intermediate Similarity NPC48733
0.8416 Intermediate Similarity NPC202167
0.8416 Intermediate Similarity NPC323834
0.8416 Intermediate Similarity NPC171137
0.8416 Intermediate Similarity NPC152695
0.8416 Intermediate Similarity NPC49958
0.8404 Intermediate Similarity NPC473099
0.8404 Intermediate Similarity NPC126993
0.84 Intermediate Similarity NPC247957
0.84 Intermediate Similarity NPC249187
0.8387 Intermediate Similarity NPC328539
0.8387 Intermediate Similarity NPC131470
0.8387 Intermediate Similarity NPC143767
0.8387 Intermediate Similarity NPC471724
0.8384 Intermediate Similarity NPC81530
0.837 Intermediate Similarity NPC145879
0.837 Intermediate Similarity NPC194417
0.837 Intermediate Similarity NPC474732
0.837 Intermediate Similarity NPC472985
0.837 Intermediate Similarity NPC475022
0.837 Intermediate Similarity NPC118648
0.837 Intermediate Similarity NPC472986
0.837 Intermediate Similarity NPC474778
0.837 Intermediate Similarity NPC474733
0.837 Intermediate Similarity NPC31564
0.837 Intermediate Similarity NPC222613
0.8367 Intermediate Similarity NPC197386
0.8367 Intermediate Similarity NPC166745
0.8367 Intermediate Similarity NPC235464
0.8352 Intermediate Similarity NPC473246
0.8351 Intermediate Similarity NPC328371
0.835 Intermediate Similarity NPC11710
0.8333 Intermediate Similarity NPC166906
0.8333 Intermediate Similarity NPC196485
0.8333 Intermediate Similarity NPC83744
0.8333 Intermediate Similarity NPC245972
0.8333 Intermediate Similarity NPC474690
0.8333 Intermediate Similarity NPC477916
0.8333 Intermediate Similarity NPC473162
0.8333 Intermediate Similarity NPC469406
0.8333 Intermediate Similarity NPC472925
0.8333 Intermediate Similarity NPC292793
0.8333 Intermediate Similarity NPC299100
0.8317 Intermediate Similarity NPC72255
0.8316 Intermediate Similarity NPC155304
0.8316 Intermediate Similarity NPC185936
0.8316 Intermediate Similarity NPC272746
0.8316 Intermediate Similarity NPC86266
0.8316 Intermediate Similarity NPC212301
0.8316 Intermediate Similarity NPC110657
0.8316 Intermediate Similarity NPC472978
0.8316 Intermediate Similarity NPC168027
0.8315 Intermediate Similarity NPC172013
0.83 Intermediate Similarity NPC195290
0.83 Intermediate Similarity NPC204450
0.83 Intermediate Similarity NPC136289
0.8298 Intermediate Similarity NPC472489
0.8298 Intermediate Similarity NPC473100
0.8298 Intermediate Similarity NPC214387
0.8298 Intermediate Similarity NPC123912
0.8298 Intermediate Similarity NPC472973
0.8283 Intermediate Similarity NPC51370
0.8283 Intermediate Similarity NPC476274
0.828 Intermediate Similarity NPC58063
0.828 Intermediate Similarity NPC136548
0.828 Intermediate Similarity NPC138756
0.8265 Intermediate Similarity NPC161147
0.8265 Intermediate Similarity NPC253826
0.8265 Intermediate Similarity NPC470522
0.8265 Intermediate Similarity NPC108078
0.8265 Intermediate Similarity NPC135685
0.8265 Intermediate Similarity NPC122294
0.8261 Intermediate Similarity NPC471224
0.8261 Intermediate Similarity NPC470574
0.8261 Intermediate Similarity NPC179006
0.8261 Intermediate Similarity NPC474853
0.8252 Intermediate Similarity NPC329417
0.8247 Intermediate Similarity NPC180950
0.8247 Intermediate Similarity NPC470016
0.8247 Intermediate Similarity NPC200702
0.8247 Intermediate Similarity NPC53565
0.8247 Intermediate Similarity NPC317586
0.8242 Intermediate Similarity NPC169941
0.8242 Intermediate Similarity NPC251475
0.8235 Intermediate Similarity NPC166607
0.8235 Intermediate Similarity NPC257353
0.8229 Intermediate Similarity NPC141497
0.8229 Intermediate Similarity NPC472942
0.8229 Intermediate Similarity NPC107674
0.8229 Intermediate Similarity NPC214697
0.8229 Intermediate Similarity NPC475255
0.8229 Intermediate Similarity NPC170220
0.8224 Intermediate Similarity NPC64318
0.8218 Intermediate Similarity NPC311612
0.8218 Intermediate Similarity NPC264048
0.8218 Intermediate Similarity NPC236390
0.8218 Intermediate Similarity NPC111323
0.8211 Intermediate Similarity NPC477147
0.8211 Intermediate Similarity NPC477149
0.8211 Intermediate Similarity NPC134321
0.8211 Intermediate Similarity NPC469400
0.8211 Intermediate Similarity NPC69622
0.8211 Intermediate Similarity NPC183283
0.8202 Intermediate Similarity NPC308038
0.8202 Intermediate Similarity NPC281138
0.82 Intermediate Similarity NPC302537
0.82 Intermediate Similarity NPC476240
0.82 Intermediate Similarity NPC224720
0.82 Intermediate Similarity NPC472637
0.82 Intermediate Similarity NPC472924
0.82 Intermediate Similarity NPC476897
0.82 Intermediate Similarity NPC163372
0.82 Intermediate Similarity NPC476223
0.8191 Intermediate Similarity NPC473229
0.8191 Intermediate Similarity NPC158778
0.8191 Intermediate Similarity NPC242864
0.8191 Intermediate Similarity NPC48107
0.819 Intermediate Similarity NPC472928

  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 NPC117133 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 NPD3618 Phase 1
0.8316 Intermediate Similarity NPD6079 Approved
0.8298 Intermediate Similarity NPD5328 Approved
0.8163 Intermediate Similarity NPD5220 Clinical (unspecified phase)
0.8163 Intermediate Similarity NPD4697 Phase 3
0.8163 Intermediate Similarity NPD5221 Approved
0.8163 Intermediate Similarity NPD5222 Approved
0.8152 Intermediate Similarity NPD4786 Approved
0.8132 Intermediate Similarity NPD3667 Approved
0.8119 Intermediate Similarity NPD5211 Phase 2
0.8081 Intermediate Similarity NPD5173 Approved
0.8041 Intermediate Similarity NPD4202 Approved
0.7982 Intermediate Similarity NPD7115 Discovery
0.7979 Intermediate Similarity NPD5279 Phase 3
0.7961 Intermediate Similarity NPD5141 Approved
0.7957 Intermediate Similarity NPD3666 Approved
0.7957 Intermediate Similarity NPD3665 Phase 1
0.7957 Intermediate Similarity NPD3133 Approved
0.7921 Intermediate Similarity NPD5285 Approved
0.7921 Intermediate Similarity NPD5286 Approved
0.7921 Intermediate Similarity NPD4696 Approved
0.79 Intermediate Similarity NPD4755 Approved
0.7843 Intermediate Similarity NPD5223 Approved
0.7789 Intermediate Similarity NPD3574 Clinical (unspecified phase)
0.7767 Intermediate Similarity NPD5224 Approved
0.7767 Intermediate Similarity NPD4633 Approved
0.7767 Intermediate Similarity NPD5226 Approved
0.7767 Intermediate Similarity NPD5225 Approved
0.7755 Intermediate Similarity NPD7515 Phase 2
0.7745 Intermediate Similarity NPD4700 Approved
0.7732 Intermediate Similarity NPD4753 Phase 2
0.77 Intermediate Similarity NPD4629 Approved
0.77 Intermediate Similarity NPD5210 Approved
0.7692 Intermediate Similarity NPD5174 Approved
0.7692 Intermediate Similarity NPD5175 Approved
0.7677 Intermediate Similarity NPD6399 Phase 3
0.7647 Intermediate Similarity NPD4225 Approved
0.7604 Intermediate Similarity NPD5690 Phase 2
0.7604 Intermediate Similarity NPD4519 Discontinued
0.7604 Intermediate Similarity NPD4623 Approved
0.7593 Intermediate Similarity NPD4634 Approved
0.7579 Intermediate Similarity NPD3668 Phase 3
0.7553 Intermediate Similarity NPD4223 Phase 3
0.7553 Intermediate Similarity NPD4221 Approved
0.7527 Intermediate Similarity NPD4695 Discontinued
0.7524 Intermediate Similarity NPD4754 Approved
0.7477 Intermediate Similarity NPD5697 Approved
0.7426 Intermediate Similarity NPD7748 Approved
0.7423 Intermediate Similarity NPD5280 Approved
0.7423 Intermediate Similarity NPD4694 Approved
0.7407 Intermediate Similarity NPD4730 Approved
0.7407 Intermediate Similarity NPD5168 Approved
0.7407 Intermediate Similarity NPD6011 Approved
0.7407 Intermediate Similarity NPD4729 Approved
0.7407 Intermediate Similarity NPD6899 Approved
0.7407 Intermediate Similarity NPD5128 Approved
0.7407 Intermediate Similarity NPD6881 Approved
0.7404 Intermediate Similarity NPD7640 Approved
0.7404 Intermediate Similarity NPD7639 Approved
0.74 Intermediate Similarity NPD5281 Approved
0.74 Intermediate Similarity NPD5284 Approved
0.7396 Intermediate Similarity NPD4197 Approved
0.7387 Intermediate Similarity NPD4632 Approved
0.7383 Intermediate Similarity NPD7128 Approved
0.7383 Intermediate Similarity NPD4767 Approved
0.7383 Intermediate Similarity NPD6675 Approved
0.7383 Intermediate Similarity NPD4768 Approved
0.7383 Intermediate Similarity NPD6402 Approved
0.7383 Intermediate Similarity NPD5739 Approved
0.7379 Intermediate Similarity NPD7902 Approved
0.7364 Intermediate Similarity NPD6649 Approved
0.7364 Intermediate Similarity NPD6650 Approved
0.7353 Intermediate Similarity NPD5695 Phase 3
0.7339 Intermediate Similarity NPD6373 Approved
0.7339 Intermediate Similarity NPD6014 Approved
0.7339 Intermediate Similarity NPD6013 Approved
0.7339 Intermediate Similarity NPD6012 Approved
0.7339 Intermediate Similarity NPD6372 Approved
0.732 Intermediate Similarity NPD5329 Approved
0.732 Intermediate Similarity NPD1696 Phase 3
0.7315 Intermediate Similarity NPD5701 Approved
0.7308 Intermediate Similarity NPD7638 Approved
0.7297 Intermediate Similarity NPD8297 Approved
0.7273 Intermediate Similarity NPD5247 Approved
0.7273 Intermediate Similarity NPD5249 Phase 3
0.7273 Intermediate Similarity NPD5248 Approved
0.7273 Intermediate Similarity NPD5135 Approved
0.7273 Intermediate Similarity NPD5169 Approved
0.7273 Intermediate Similarity NPD5251 Approved
0.7273 Intermediate Similarity NPD5250 Approved
0.7273 Intermediate Similarity NPD5134 Clinical (unspecified phase)
0.7273 Intermediate Similarity NPD7290 Approved
0.7273 Intermediate Similarity NPD7102 Approved
0.7273 Intermediate Similarity NPD6883 Approved
0.7248 Intermediate Similarity NPD7320 Approved
0.7245 Intermediate Similarity NPD4138 Approved
0.7245 Intermediate Similarity NPD4690 Approved
0.7245 Intermediate Similarity NPD4693 Phase 3
0.7245 Intermediate Similarity NPD5205 Approved
0.7245 Intermediate Similarity NPD4689 Approved
0.7245 Intermediate Similarity NPD4688 Approved
0.7212 Intermediate Similarity NPD6083 Phase 2
0.7212 Intermediate Similarity NPD6084 Phase 2
0.7207 Intermediate Similarity NPD8130 Phase 1
0.7207 Intermediate Similarity NPD5217 Approved
0.7207 Intermediate Similarity NPD6847 Approved
0.7207 Intermediate Similarity NPD6617 Approved
0.7207 Intermediate Similarity NPD5216 Approved
0.7207 Intermediate Similarity NPD5215 Approved
0.7207 Intermediate Similarity NPD5127 Approved
0.7207 Intermediate Similarity NPD6869 Approved
0.7174 Intermediate Similarity NPD6942 Approved
0.7174 Intermediate Similarity NPD7339 Approved
0.7158 Intermediate Similarity NPD7525 Registered
0.7143 Intermediate Similarity NPD5696 Approved
0.7143 Intermediate Similarity NPD1694 Approved
0.7143 Intermediate Similarity NPD7520 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD6882 Approved
0.7128 Intermediate Similarity NPD3617 Approved
0.7113 Intermediate Similarity NPD4788 Approved
0.71 Intermediate Similarity NPD6672 Approved
0.71 Intermediate Similarity NPD5737 Approved
0.7097 Intermediate Similarity NPD3701 Clinical (unspecified phase)
0.7087 Intermediate Similarity NPD7900 Approved
0.7087 Intermediate Similarity NPD7901 Clinical (unspecified phase)
0.7071 Intermediate Similarity NPD7146 Approved
0.7071 Intermediate Similarity NPD6409 Approved
0.7071 Intermediate Similarity NPD6684 Approved
0.7071 Intermediate Similarity NPD5330 Approved
0.7071 Intermediate Similarity NPD7521 Approved
0.7071 Intermediate Similarity NPD7334 Approved
0.7064 Intermediate Similarity NPD6008 Approved
0.7054 Intermediate Similarity NPD6401 Clinical (unspecified phase)
0.7053 Intermediate Similarity NPD4195 Approved
0.7043 Intermediate Similarity NPD6009 Approved
0.7019 Intermediate Similarity NPD6356 Clinical (unspecified phase)
0.7018 Intermediate Similarity NPD5167 Approved
0.7009 Intermediate Similarity NPD6319 Approved
0.7 Intermediate Similarity NPD6412 Phase 2
0.7 Intermediate Similarity NPD4751 Clinical (unspecified phase)
0.6979 Remote Similarity NPD8259 Clinical (unspecified phase)
0.697 Remote Similarity NPD5363 Approved
0.6961 Remote Similarity NPD5785 Approved
0.6961 Remote Similarity NPD4096 Approved
0.6957 Remote Similarity NPD6274 Approved
0.6957 Remote Similarity NPD6868 Approved
0.6947 Remote Similarity NPD5784 Clinical (unspecified phase)
0.6931 Remote Similarity NPD4518 Approved
0.6931 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6931 Remote Similarity NPD6903 Approved
0.6923 Remote Similarity NPD4691 Approved
0.6923 Remote Similarity NPD4747 Approved
0.6916 Remote Similarity NPD6404 Discontinued
0.6907 Remote Similarity NPD4692 Approved
0.6907 Remote Similarity NPD4139 Approved
0.6897 Remote Similarity NPD6317 Approved
0.6893 Remote Similarity NPD8034 Phase 2
0.6893 Remote Similarity NPD8035 Phase 2
0.6882 Remote Similarity NPD4687 Approved
0.6882 Remote Similarity NPD5733 Approved
0.6875 Remote Similarity NPD4061 Clinical (unspecified phase)
0.6864 Remote Similarity NPD6054 Approved
0.6863 Remote Similarity NPD7285 Clinical (unspecified phase)
0.6848 Remote Similarity NPD5276 Approved
0.6838 Remote Similarity NPD6313 Approved
0.6838 Remote Similarity NPD6314 Approved
0.6838 Remote Similarity NPD6335 Approved
0.6837 Remote Similarity NPD4752 Clinical (unspecified phase)
0.6832 Remote Similarity NPD3573 Approved
0.6827 Remote Similarity NPD5133 Approved
0.6822 Remote Similarity NPD5290 Discontinued
0.6813 Remote Similarity NPD4137 Phase 3
0.6809 Remote Similarity NPD8264 Approved
0.6807 Remote Similarity NPD6016 Approved
0.6807 Remote Similarity NPD5983 Phase 2
0.6807 Remote Similarity NPD6291 Clinical (unspecified phase)
0.6807 Remote Similarity NPD6015 Approved
0.6804 Remote Similarity NPD4748 Discontinued
0.6796 Remote Similarity NPD5692 Phase 3
0.6796 Remote Similarity NPD5207 Approved
0.6789 Remote Similarity NPD7632 Discontinued
0.6789 Remote Similarity NPD5091 Approved
0.6786 Remote Similarity NPD6686 Approved
0.678 Remote Similarity NPD7101 Approved
0.678 Remote Similarity NPD7100 Approved
0.6768 Remote Similarity NPD5362 Discontinued
0.6762 Remote Similarity NPD6001 Approved
0.675 Remote Similarity NPD5988 Approved
0.675 Remote Similarity NPD6370 Approved
0.6737 Remote Similarity NPD6933 Approved
0.6731 Remote Similarity NPD5694 Approved
0.6731 Remote Similarity NPD6050 Approved
0.6731 Remote Similarity NPD6411 Approved
0.6731 Remote Similarity NPD5693 Phase 1
0.6723 Remote Similarity NPD6059 Approved
0.6702 Remote Similarity NPD4058 Approved
0.6701 Remote Similarity NPD7645 Phase 2
0.6699 Remote Similarity NPD6080 Approved
0.6699 Remote Similarity NPD6673 Approved
0.6699 Remote Similarity NPD6904 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