Structure

Physi-Chem Properties

Molecular Weight:  316.24
Volume:  349.854
LogP:  3.957
LogD:  3.808
LogS:  -3.832
# Rotatable Bonds:  1
TPSA:  37.3
# H-Bond Aceptor:  2
# H-Bond Donor:  1
# Rings:  4
# Heavy Atoms:  2

MedChem Properties

QED Drug-Likeness Score:  0.722
Synthetic Accessibility Score:  4.228
Fsp3:  0.857
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
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:  -4.616
MDCK Permeability:  1.2901339687232394e-05
Pgp-inhibitor:  0.981
Pgp-substrate:  0.405
Human Intestinal Absorption (HIA):  0.005
20% Bioavailability (F20%):  0.954
30% Bioavailability (F30%):  0.042

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.857
Plasma Protein Binding (PPB):  86.01161193847656%
Volume Distribution (VD):  0.944
Pgp-substrate:  3.9947822093963623%

ADMET: Metabolism

CYP1A2-inhibitor:  0.248
CYP1A2-substrate:  0.29
CYP2C19-inhibitor:  0.161
CYP2C19-substrate:  0.784
CYP2C9-inhibitor:  0.183
CYP2C9-substrate:  0.257
CYP2D6-inhibitor:  0.03
CYP2D6-substrate:  0.458
CYP3A4-inhibitor:  0.645
CYP3A4-substrate:  0.386

ADMET: Excretion

Clearance (CL):  12.049
Half-life (T1/2):  0.684

ADMET: Toxicity

hERG Blockers:  0.52
Human Hepatotoxicity (H-HT):  0.134
Drug-inuced Liver Injury (DILI):  0.668
AMES Toxicity:  0.041
Rat Oral Acute Toxicity:  0.795
Maximum Recommended Daily Dose:  0.402
Skin Sensitization:  0.948
Carcinogencity:  0.698
Eye Corrosion:  0.737
Eye Irritation:  0.643
Respiratory Toxicity:  0.977

Download Data

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

  Natural Product: NPC214043

Natural Product ID:  NPC214043
Common Name*:   20Alpha-Hydroxy-4-Pregnen-3-One
IUPAC Name:   (8S,9S,10R,13S,14S,17S)-17-[(1R)-1-hydroxyethyl]-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one
Synonyms:  
Standard InCHIKey:  RWBRUCCWZPSBFC-SJOKZOANSA-N
Standard InCHI:  InChI=1S/C21H32O2/c1-13(22)17-6-7-18-16-5-4-14-12-15(23)8-10-20(14,2)19(16)9-11-21(17,18)3/h12-13,16-19,22H,4-11H2,1-3H3/t13-,16+,17-,18+,19+,20+,21-/m1/s1
SMILES:  C[C@H]([C@H]1CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@]4(C)[C@H]3CC[C@]12C)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL2112756
PubChem CID:   92747
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000258] Steroids and steroid derivatives
        • [CHEMONTID:0003569] Pregnane steroids
          • [CHEMONTID:0001468] Gluco/mineralocorticoids, progestogins 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

☑ 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
NPT3159 Individual Protein Cytochrome P450 17A1 Homo sapiens IC50 = 2840.0 nM PMID[551382]
NPT3159 Individual Protein Cytochrome P450 17A1 Homo sapiens IC50 = 1430.0 nM PMID[551382]
NPT542 Individual Protein Progesterone receptor Homo sapiens log(RBA) = 0.3 n.a. PMID[551383]
NPT1462 Individual Protein Progesterone receptor Oryctolagus cuniculus log(RBA) = 1.01 n.a. PMID[551383]
NPT24383 SINGLE PROTEIN Progesterone receptor Ovis aries log(RBA) = 0.0 n.a. PMID[551383]
NPT2 Others Unspecified log(RBA) = 0.0 n.a. PMID[551383]

☑ 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 NPC214043 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 NPC85774
0.975 High Similarity NPC474733
0.975 High Similarity NPC474732
0.975 High Similarity NPC474778
0.975 High Similarity NPC31564
0.975 High Similarity NPC145879
0.9747 High Similarity NPC473246
0.963 High Similarity NPC475740
0.963 High Similarity NPC58063
0.9625 High Similarity NPC469948
0.95 High Similarity NPC329043
0.95 High Similarity NPC321187
0.95 High Similarity NPC59453
0.95 High Similarity NPC227064
0.95 High Similarity NPC58841
0.95 High Similarity NPC161423
0.95 High Similarity NPC221758
0.95 High Similarity NPC237712
0.95 High Similarity NPC82902
0.9398 High Similarity NPC186688
0.9398 High Similarity NPC1015
0.9398 High Similarity NPC31985
0.9398 High Similarity NPC26959
0.9398 High Similarity NPC309603
0.9398 High Similarity NPC268406
0.9398 High Similarity NPC473999
0.9398 High Similarity NPC477943
0.939 High Similarity NPC93778
0.9383 High Similarity NPC471224
0.9383 High Similarity NPC470574
0.9383 High Similarity NPC474218
0.9286 High Similarity NPC48010
0.9277 High Similarity NPC328539
0.9277 High Similarity NPC471722
0.9268 High Similarity NPC51014
0.9268 High Similarity NPC118648
0.9268 High Similarity NPC475022
0.9268 High Similarity NPC327115
0.9268 High Similarity NPC72133
0.9268 High Similarity NPC222613
0.9268 High Similarity NPC469994
0.9259 High Similarity NPC472265
0.925 High Similarity NPC151519
0.9241 High Similarity NPC472478
0.9241 High Similarity NPC2482
0.9176 High Similarity NPC272746
0.9176 High Similarity NPC473998
0.9176 High Similarity NPC475806
0.9167 High Similarity NPC86319
0.9167 High Similarity NPC275740
0.9157 High Similarity NPC136548
0.9157 High Similarity NPC90652
0.9157 High Similarity NPC317590
0.9146 High Similarity NPC474083
0.907 High Similarity NPC474736
0.907 High Similarity NPC475255
0.9059 High Similarity NPC126993
0.9059 High Similarity NPC191684
0.9059 High Similarity NPC85173
0.9048 High Similarity NPC131470
0.9048 High Similarity NPC470417
0.9048 High Similarity NPC143767
0.9048 High Similarity NPC328313
0.9036 High Similarity NPC473168
0.9036 High Similarity NPC155011
0.9024 High Similarity NPC33913
0.9012 High Similarity NPC193347
0.9012 High Similarity NPC320514
0.8987 High Similarity NPC82635
0.8966 High Similarity NPC245972
0.8966 High Similarity NPC8993
0.8966 High Similarity NPC111015
0.8966 High Similarity NPC196485
0.8953 High Similarity NPC168027
0.8953 High Similarity NPC185936
0.8941 High Similarity NPC76879
0.8941 High Similarity NPC474245
0.8941 High Similarity NPC32830
0.8941 High Similarity NPC326627
0.8941 High Similarity NPC310010
0.8941 High Similarity NPC119416
0.8941 High Similarity NPC2983
0.8929 High Similarity NPC96496
0.8929 High Similarity NPC141292
0.8929 High Similarity NPC474684
0.8929 High Similarity NPC142361
0.8916 High Similarity NPC29447
0.8902 High Similarity NPC278648
0.8902 High Similarity NPC476082
0.8889 High Similarity NPC477372
0.8889 High Similarity NPC147066
0.8889 High Similarity NPC121984
0.8875 High Similarity NPC215843
0.8875 High Similarity NPC472490
0.8864 High Similarity NPC271195
0.8851 High Similarity NPC69454
0.8851 High Similarity NPC12722
0.8851 High Similarity NPC472930
0.8851 High Similarity NPC250575
0.8851 High Similarity NPC474807
0.8837 High Similarity NPC320026
0.8837 High Similarity NPC171441
0.8837 High Similarity NPC183283
0.8824 High Similarity NPC310752
0.8824 High Similarity NPC471724
0.8824 High Similarity NPC292491
0.8824 High Similarity NPC193360
0.8824 High Similarity NPC53911
0.881 High Similarity NPC89077
0.881 High Similarity NPC20688
0.881 High Similarity NPC94755
0.8795 High Similarity NPC165064
0.8795 High Similarity NPC144258
0.8736 High Similarity NPC131872
0.8736 High Similarity NPC63748
0.8736 High Similarity NPC19114
0.8736 High Similarity NPC262870
0.8736 High Similarity NPC154101
0.8736 High Similarity NPC233116
0.8721 High Similarity NPC475921
0.8721 High Similarity NPC474704
0.8706 High Similarity NPC99909
0.8706 High Similarity NPC159046
0.8706 High Similarity NPC233836
0.8706 High Similarity NPC136948
0.8706 High Similarity NPC187376
0.869 High Similarity NPC197823
0.869 High Similarity NPC202868
0.8675 High Similarity NPC470047
0.8675 High Similarity NPC470046
0.8667 High Similarity NPC108078
0.8659 High Similarity NPC136150
0.8659 High Similarity NPC3915
0.8659 High Similarity NPC201912
0.8659 High Similarity NPC6434
0.8659 High Similarity NPC38350
0.8652 High Similarity NPC259286
0.8652 High Similarity NPC472932
0.8652 High Similarity NPC476174
0.8642 High Similarity NPC477371
0.8642 High Similarity NPC201459
0.8636 High Similarity NPC233118
0.8636 High Similarity NPC109305
0.8625 High Similarity NPC106078
0.8625 High Similarity NPC197659
0.8621 High Similarity NPC69622
0.8621 High Similarity NPC129913
0.8605 High Similarity NPC472802
0.8605 High Similarity NPC44181
0.8605 High Similarity NPC474677
0.8588 High Similarity NPC28252
0.8588 High Similarity NPC158393
0.8588 High Similarity NPC94666
0.8588 High Similarity NPC55309
0.8588 High Similarity NPC195640
0.8571 High Similarity NPC476412
0.8571 High Similarity NPC180834
0.8571 High Similarity NPC103051
0.8556 High Similarity NPC249954
0.8556 High Similarity NPC192428
0.8556 High Similarity NPC472941
0.8556 High Similarity NPC456
0.8554 High Similarity NPC145143
0.8554 High Similarity NPC477858
0.8554 High Similarity NPC310989
0.8554 High Similarity NPC48362
0.8554 High Similarity NPC260956
0.8554 High Similarity NPC212083
0.8539 High Similarity NPC166906
0.8539 High Similarity NPC174051
0.8539 High Similarity NPC473172
0.8539 High Similarity NPC67831
0.8537 High Similarity NPC164999
0.8523 High Similarity NPC189520
0.8523 High Similarity NPC86266
0.8523 High Similarity NPC212301
0.8523 High Similarity NPC110657
0.8523 High Similarity NPC155304
0.8519 High Similarity NPC469996
0.8506 High Similarity NPC77168
0.8506 High Similarity NPC123912
0.8506 High Similarity NPC102414
0.8506 High Similarity NPC214387
0.8506 High Similarity NPC54689
0.8506 High Similarity NPC474570
0.8506 High Similarity NPC84271
0.8506 High Similarity NPC262043
0.85 High Similarity NPC321381
0.85 High Similarity NPC321016
0.85 High Similarity NPC263582
0.85 High Similarity NPC107059
0.8488 Intermediate Similarity NPC472481
0.8488 Intermediate Similarity NPC472482
0.8488 Intermediate Similarity NPC472484
0.8488 Intermediate Similarity NPC287079
0.8478 Intermediate Similarity NPC154072
0.8471 Intermediate Similarity NPC133954
0.8471 Intermediate Similarity NPC76518
0.8471 Intermediate Similarity NPC274724
0.8471 Intermediate Similarity NPC476426

  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 NPC214043 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
0.95 High Similarity NPD4786 Approved
0.95 High Similarity NPD3133 Approved
0.95 High Similarity NPD3665 Phase 1
0.95 High Similarity NPD3666 Approved
0.9398 High Similarity NPD5328 Approved
0.9268 High Similarity NPD3618 Phase 1
0.925 High Similarity NPD3667 Approved
0.9176 High Similarity NPD6079 Approved
0.9036 High Similarity NPD5279 Phase 3
0.9012 High Similarity NPD4221 Approved
0.9012 High Similarity NPD4223 Phase 3
0.8941 High Similarity NPD4753 Phase 2
0.8916 High Similarity NPD5329 Approved
0.8851 High Similarity NPD4202 Approved
0.8795 High Similarity NPD4197 Approved
0.8588 High Similarity NPD4138 Approved
0.8588 High Similarity NPD7334 Approved
0.8588 High Similarity NPD5205 Approved
0.8588 High Similarity NPD7146 Approved
0.8588 High Similarity NPD4693 Phase 3
0.8588 High Similarity NPD6684 Approved
0.8588 High Similarity NPD4690 Approved
0.8588 High Similarity NPD4688 Approved
0.8588 High Similarity NPD6409 Approved
0.8588 High Similarity NPD4689 Approved
0.8588 High Similarity NPD5330 Approved
0.8588 High Similarity NPD7521 Approved
0.8556 High Similarity NPD5222 Approved
0.8556 High Similarity NPD5220 Clinical (unspecified phase)
0.8556 High Similarity NPD4697 Phase 3
0.8556 High Similarity NPD5221 Approved
0.8519 High Similarity NPD3617 Approved
0.8462 Intermediate Similarity NPD5173 Approved
0.8462 Intermediate Similarity NPD6083 Phase 2
0.8462 Intermediate Similarity NPD4755 Approved
0.8462 Intermediate Similarity NPD6084 Phase 2
0.8452 Intermediate Similarity NPD4788 Approved
0.8444 Intermediate Similarity NPD5210 Approved
0.8444 Intermediate Similarity NPD4629 Approved
0.8427 Intermediate Similarity NPD6399 Phase 3
0.8391 Intermediate Similarity NPD7513 Clinical (unspecified phase)
0.8391 Intermediate Similarity NPD5737 Approved
0.8391 Intermediate Similarity NPD6903 Approved
0.8391 Intermediate Similarity NPD6672 Approved
0.8375 Intermediate Similarity NPD7339 Approved
0.8375 Intermediate Similarity NPD6942 Approved
0.8372 Intermediate Similarity NPD5280 Approved
0.8372 Intermediate Similarity NPD4694 Approved
0.8372 Intermediate Similarity NPD5690 Phase 2
0.8353 Intermediate Similarity NPD3668 Phase 3
0.8333 Intermediate Similarity NPD4747 Approved
0.8315 Intermediate Similarity NPD7515 Phase 2
0.828 Intermediate Similarity NPD5285 Approved
0.828 Intermediate Similarity NPD4700 Approved
0.828 Intermediate Similarity NPD5286 Approved
0.828 Intermediate Similarity NPD4696 Approved
0.8205 Intermediate Similarity NPD4137 Phase 3
0.8193 Intermediate Similarity NPD4195 Approved
0.8191 Intermediate Similarity NPD5223 Approved
0.8161 Intermediate Similarity NPD3574 Clinical (unspecified phase)
0.8105 Intermediate Similarity NPD5224 Approved
0.8105 Intermediate Similarity NPD5226 Approved
0.8105 Intermediate Similarity NPD5225 Approved
0.8105 Intermediate Similarity NPD4633 Approved
0.8105 Intermediate Similarity NPD5211 Phase 2
0.8101 Intermediate Similarity NPD4691 Approved
0.8095 Intermediate Similarity NPD4695 Discontinued
0.8049 Intermediate Similarity NPD3701 Clinical (unspecified phase)
0.8046 Intermediate Similarity NPD7520 Clinical (unspecified phase)
0.8043 Intermediate Similarity NPD5695 Phase 3
0.8041 Intermediate Similarity NPD7128 Approved
0.8041 Intermediate Similarity NPD6675 Approved
0.8041 Intermediate Similarity NPD6402 Approved
0.8041 Intermediate Similarity NPD5739 Approved
0.8025 Intermediate Similarity NPD5733 Approved
0.8021 Intermediate Similarity NPD4754 Approved
0.8021 Intermediate Similarity NPD5175 Approved
0.8021 Intermediate Similarity NPD5174 Approved
0.7979 Intermediate Similarity NPD5696 Approved
0.7955 Intermediate Similarity NPD4623 Approved
0.7955 Intermediate Similarity NPD4519 Discontinued
0.7938 Intermediate Similarity NPD5141 Approved
0.7935 Intermediate Similarity NPD7748 Approved
0.7912 Intermediate Similarity NPD5284 Approved
0.7912 Intermediate Similarity NPD5281 Approved
0.7889 Intermediate Similarity NPD6080 Approved
0.7889 Intermediate Similarity NPD6904 Approved
0.7889 Intermediate Similarity NPD6673 Approved
0.7882 Intermediate Similarity NPD7525 Registered
0.7879 Intermediate Similarity NPD6881 Approved
0.7879 Intermediate Similarity NPD6899 Approved
0.7879 Intermediate Similarity NPD7320 Approved
0.7857 Intermediate Similarity NPD4767 Approved
0.7857 Intermediate Similarity NPD4768 Approved
0.7805 Intermediate Similarity NPD6926 Approved
0.7805 Intermediate Similarity NPD6924 Approved
0.7805 Intermediate Similarity NPD4058 Approved
0.7805 Intermediate Similarity NPD4687 Approved
0.7802 Intermediate Similarity NPD4096 Approved
0.78 Intermediate Similarity NPD6373 Approved
0.78 Intermediate Similarity NPD6372 Approved
0.7791 Intermediate Similarity NPD4692 Approved
0.7791 Intermediate Similarity NPD4139 Approved
0.7778 Intermediate Similarity NPD5208 Approved
0.7778 Intermediate Similarity NPD5697 Approved
0.7778 Intermediate Similarity NPD4809 Clinical (unspecified phase)
0.7778 Intermediate Similarity NPD4808 Clinical (unspecified phase)
0.7778 Intermediate Similarity NPD6412 Phase 2
0.7778 Intermediate Similarity NPD5276 Approved
0.7778 Intermediate Similarity NPD4243 Approved
0.7778 Intermediate Similarity NPD5701 Approved
0.7753 Intermediate Similarity NPD6098 Approved
0.7723 Intermediate Similarity NPD7290 Approved
0.7723 Intermediate Similarity NPD6883 Approved
0.7723 Intermediate Similarity NPD7102 Approved
0.77 Intermediate Similarity NPD4730 Approved
0.77 Intermediate Similarity NPD5168 Approved
0.77 Intermediate Similarity NPD5128 Approved
0.77 Intermediate Similarity NPD6011 Approved
0.77 Intermediate Similarity NPD4729 Approved
0.7692 Intermediate Similarity NPD3171 Clinical (unspecified phase)
0.7684 Intermediate Similarity NPD7902 Approved
0.766 Intermediate Similarity NPD6356 Clinical (unspecified phase)
0.7654 Intermediate Similarity NPD4789 Approved
0.7654 Intermediate Similarity NPD4245 Approved
0.7654 Intermediate Similarity NPD4244 Approved
0.7647 Intermediate Similarity NPD6401 Clinical (unspecified phase)
0.7647 Intermediate Similarity NPD8130 Phase 1
0.7647 Intermediate Similarity NPD6650 Approved
0.7647 Intermediate Similarity NPD6617 Approved
0.7647 Intermediate Similarity NPD6869 Approved
0.7647 Intermediate Similarity NPD6847 Approved
0.7647 Intermediate Similarity NPD6649 Approved
0.7634 Intermediate Similarity NPD5133 Approved
0.7625 Intermediate Similarity NPD3621 Clinical (unspecified phase)
0.7624 Intermediate Similarity NPD6014 Approved
0.7624 Intermediate Similarity NPD6013 Approved
0.7624 Intermediate Similarity NPD6012 Approved
0.7619 Intermediate Similarity NPD6933 Approved
0.7604 Intermediate Similarity NPD7638 Approved
0.759 Intermediate Similarity NPD4784 Approved
0.759 Intermediate Similarity NPD4785 Approved
0.7582 Intermediate Similarity NPD4518 Approved
0.7573 Intermediate Similarity NPD6882 Approved
0.7573 Intermediate Similarity NPD8297 Approved
0.7549 Intermediate Similarity NPD5169 Approved
0.7549 Intermediate Similarity NPD5250 Approved
0.7549 Intermediate Similarity NPD5248 Approved
0.7549 Intermediate Similarity NPD5249 Phase 3
0.7549 Intermediate Similarity NPD5251 Approved
0.7549 Intermediate Similarity NPD5134 Clinical (unspecified phase)
0.7549 Intermediate Similarity NPD5247 Approved
0.7549 Intermediate Similarity NPD4634 Approved
0.7549 Intermediate Similarity NPD5135 Approved
0.7531 Intermediate Similarity NPD6922 Approved
0.7531 Intermediate Similarity NPD3698 Phase 2
0.7531 Intermediate Similarity NPD6923 Approved
0.7531 Intermediate Similarity NPD3699 Clinical (unspecified phase)
0.7531 Intermediate Similarity NPD3700 Clinical (unspecified phase)
0.7527 Intermediate Similarity NPD6050 Approved
0.7527 Intermediate Similarity NPD5693 Phase 1
0.7526 Intermediate Similarity NPD7640 Approved
0.7526 Intermediate Similarity NPD7639 Approved
0.75 Intermediate Similarity NPD7285 Clinical (unspecified phase)
0.7476 Intermediate Similarity NPD5217 Approved
0.7476 Intermediate Similarity NPD5216 Approved
0.7476 Intermediate Similarity NPD5215 Approved
0.7476 Intermediate Similarity NPD5127 Approved
0.7442 Intermediate Similarity NPD5784 Clinical (unspecified phase)
0.7439 Intermediate Similarity NPD7143 Approved
0.7439 Intermediate Similarity NPD7144 Approved
0.7419 Intermediate Similarity NPD5692 Phase 3
0.7419 Intermediate Similarity NPD5207 Approved
0.7381 Intermediate Similarity NPD6113 Clinical (unspecified phase)
0.7374 Intermediate Similarity NPD5091 Approved
0.7368 Intermediate Similarity NPD7900 Approved
0.7368 Intermediate Similarity NPD7901 Clinical (unspecified phase)
0.7368 Intermediate Similarity NPD6001 Approved
0.7358 Intermediate Similarity NPD6868 Approved
0.7356 Intermediate Similarity NPD7645 Phase 2
0.7356 Intermediate Similarity NPD6929 Approved
0.7349 Intermediate Similarity NPD7152 Approved
0.7349 Intermediate Similarity NPD7150 Approved
0.7349 Intermediate Similarity NPD7151 Approved
0.734 Intermediate Similarity NPD8035 Phase 2
0.734 Intermediate Similarity NPD8034 Phase 2
0.734 Intermediate Similarity NPD5694 Approved
0.7333 Intermediate Similarity NPD4632 Approved
0.7294 Intermediate Similarity NPD4190 Phase 3
0.7294 Intermediate Similarity NPD5275 Approved
0.729 Intermediate Similarity NPD7115 Discovery
0.7283 Intermediate Similarity NPD4751 Clinical (unspecified phase)
0.7273 Intermediate Similarity NPD6931 Approved
0.7273 Intermediate Similarity NPD6930 Phase 2
0.7264 Intermediate Similarity NPD5167 Approved
0.7245 Intermediate Similarity NPD5290 Discontinued
0.7222 Intermediate Similarity NPD6335 Approved
0.7209 Intermediate Similarity NPD6117 Approved
0.7196 Intermediate Similarity NPD6274 Approved
0.7195 Intermediate Similarity NPD5360 Phase 3

  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