Structure

Physi-Chem Properties

Molecular Weight:  346.21
Volume:  364.798
LogP:  2.412
LogD:  2.57
LogS:  -4.408
# Rotatable Bonds:  2
TPSA:  74.6
# H-Bond Aceptor:  4
# H-Bond Donor:  2
# Rings:  4
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.806
Synthetic Accessibility Score:  4.128
Fsp3:  0.81
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:  -4.84
MDCK Permeability:  2.356229924771469e-05
Pgp-inhibitor:  0.978
Pgp-substrate:  0.0
Human Intestinal Absorption (HIA):  0.008
20% Bioavailability (F20%):  0.004
30% Bioavailability (F30%):  0.022

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.963
Plasma Protein Binding (PPB):  90.5670166015625%
Volume Distribution (VD):  0.671
Pgp-substrate:  6.064359664916992%

ADMET: Metabolism

CYP1A2-inhibitor:  0.019
CYP1A2-substrate:  0.72
CYP2C19-inhibitor:  0.159
CYP2C19-substrate:  0.9
CYP2C9-inhibitor:  0.128
CYP2C9-substrate:  0.266
CYP2D6-inhibitor:  0.005
CYP2D6-substrate:  0.522
CYP3A4-inhibitor:  0.131
CYP3A4-substrate:  0.925

ADMET: Excretion

Clearance (CL):  5.184
Half-life (T1/2):  0.82

ADMET: Toxicity

hERG Blockers:  0.055
Human Hepatotoxicity (H-HT):  0.577
Drug-inuced Liver Injury (DILI):  0.044
AMES Toxicity:  0.044
Rat Oral Acute Toxicity:  0.053
Maximum Recommended Daily Dose:  0.909
Skin Sensitization:  0.054
Carcinogencity:  0.454
Eye Corrosion:  0.003
Eye Irritation:  0.012
Respiratory Toxicity:  0.636

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

  Natural Product: NPC326627

Natural Product ID:  NPC326627
Common Name*:   17-Hydroxy-17-(2-Hydroxyacetyl)-10,13-Dimethyl-2,6,7,8,9,11,12,14,15,16-Decahydro-1H-Cyclopenta[A]Phenanthren-3-One
IUPAC Name:   17-hydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-3-one
Synonyms:  
Standard InCHIKey:  WHBHBVVOGNECLV-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C21H30O4/c1-19-8-5-14(23)11-13(19)3-4-15-16(19)6-9-20(2)17(15)7-10-21(20,25)18(24)12-22/h11,15-17,22,25H,3-10,12H2,1-2H3
SMILES:  CC12CCC(=O)C=C1CCC3C2CCC4(C3CCC4(C(=O)CO)O)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1705958
PubChem CID:   227112
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000258] Steroids and steroid derivatives
        • [CHEMONTID:0001295] Hydroxysteroids
          • [CHEMONTID:0003095] 21-hydroxysteroids

*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
NPO30940 Bas taurus n.a. n.a. n.a. n.a. n.a. n.a. Database[TCM_Taiwan]

☑ 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
NPT152 Individual Protein Nuclear factor erythroid 2-related factor 2 Homo sapiens Potency n.a. 6513.1 nM PMID[492550]
NPT135 Individual Protein Chromobox protein homolog 1 Homo sapiens Potency n.a. 79432.8 nM PMID[492550]
NPT10 Individual Protein Geminin Homo sapiens Potency n.a. 115.8 nM PMID[492550]
NPT160 Individual Protein TAR DNA-binding protein 43 Homo sapiens Potency n.a. 354.8 nM PMID[492550]
NPT20 Organism Candida albicans Candida albicans Inhibition = 3.12 % PMID[492551]
NPT85 Organism Filobasidiella neoformans Cryptococcus neoformans Inhibition = -0.13 % PMID[492551]
NPT19 Organism Escherichia coli Escherichia coli Inhibition = -7.68 % PMID[492551]
NPT173 Organism Klebsiella pneumoniae Klebsiella pneumoniae Inhibition = 8.14 % PMID[492551]
NPT18 Organism Pseudomonas aeruginosa Pseudomonas aeruginosa Inhibition = 7.63 % PMID[492551]
NPT747 Organism Acinetobacter baumannii Acinetobacter baumannii Inhibition = 14.88 % PMID[492551]
NPT2922 Organism Staphylococcus aureus subsp. aureus Staphylococcus aureus subsp. aureus Inhibition = 8.54 % PMID[492551]

☑ 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 NPC326627 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 NPC310010
0.9651 High Similarity NPC233118
0.9398 High Similarity NPC237712
0.9398 High Similarity NPC144258
0.9222 High Similarity NPC18509
0.9176 High Similarity NPC327115
0.9167 High Similarity NPC329043
0.9167 High Similarity NPC161423
0.9167 High Similarity NPC58841
0.9167 High Similarity NPC227064
0.9167 High Similarity NPC321187
0.9157 High Similarity NPC193347
0.908 High Similarity NPC477943
0.908 High Similarity NPC76879
0.9022 High Similarity NPC144956
0.8977 High Similarity NPC171441
0.8941 High Similarity NPC214043
0.8941 High Similarity NPC82902
0.8941 High Similarity NPC85774
0.8901 High Similarity NPC49371
0.8876 High Similarity NPC185936
0.8876 High Similarity NPC168027
0.8864 High Similarity NPC474245
0.8864 High Similarity NPC1015
0.8864 High Similarity NPC31985
0.8851 High Similarity NPC90652
0.8851 High Similarity NPC317590
0.8837 High Similarity NPC474218
0.8837 High Similarity NPC469948
0.883 High Similarity NPC87351
0.8817 High Similarity NPC474720
0.8764 High Similarity NPC129913
0.8764 High Similarity NPC320026
0.875 High Similarity NPC470417
0.8737 High Similarity NPC311612
0.8736 High Similarity NPC474732
0.8736 High Similarity NPC474778
0.8736 High Similarity NPC474733
0.8736 High Similarity NPC31564
0.8736 High Similarity NPC51014
0.8736 High Similarity NPC145879
0.8736 High Similarity NPC469994
0.8736 High Similarity NPC20688
0.8721 High Similarity NPC473246
0.869 High Similarity NPC472478
0.8681 High Similarity NPC111015
0.8681 High Similarity NPC196485
0.8681 High Similarity NPC245972
0.8652 High Similarity NPC2983
0.8636 High Similarity NPC472484
0.8636 High Similarity NPC475740
0.8636 High Similarity NPC472482
0.8636 High Similarity NPC58063
0.8636 High Similarity NPC472481
0.8636 High Similarity NPC93778
0.8587 High Similarity NPC472824
0.8587 High Similarity NPC472932
0.8571 High Similarity NPC474807
0.8557 High Similarity NPC257353
0.8542 High Similarity NPC111323
0.8539 High Similarity NPC328539
0.8539 High Similarity NPC328313
0.8523 High Similarity NPC94666
0.8511 High Similarity NPC147954
0.8506 High Similarity NPC59453
0.8506 High Similarity NPC221758
0.8495 Intermediate Similarity NPC192428
0.8488 Intermediate Similarity NPC151519
0.8488 Intermediate Similarity NPC103486
0.8478 Intermediate Similarity NPC8993
0.8471 Intermediate Similarity NPC2482
0.8469 Intermediate Similarity NPC185
0.8469 Intermediate Similarity NPC44063
0.8462 Intermediate Similarity NPC475806
0.8462 Intermediate Similarity NPC473998
0.8462 Intermediate Similarity NPC154101
0.8454 Intermediate Similarity NPC137657
0.8444 Intermediate Similarity NPC476733
0.8444 Intermediate Similarity NPC305039
0.8444 Intermediate Similarity NPC268406
0.8444 Intermediate Similarity NPC26959
0.8444 Intermediate Similarity NPC309603
0.8444 Intermediate Similarity NPC32830
0.8444 Intermediate Similarity NPC473999
0.8444 Intermediate Similarity NPC186688
0.8444 Intermediate Similarity NPC215029
0.8427 Intermediate Similarity NPC96496
0.8427 Intermediate Similarity NPC136948
0.8427 Intermediate Similarity NPC136548
0.8421 Intermediate Similarity NPC154072
0.8409 Intermediate Similarity NPC470574
0.8409 Intermediate Similarity NPC471224
0.8372 Intermediate Similarity NPC121984
0.8372 Intermediate Similarity NPC6434
0.837 Intermediate Similarity NPC475255
0.837 Intermediate Similarity NPC472930
0.837 Intermediate Similarity NPC250575
0.837 Intermediate Similarity NPC472942
0.837 Intermediate Similarity NPC12722
0.8353 Intermediate Similarity NPC472490
0.8353 Intermediate Similarity NPC215843
0.8352 Intermediate Similarity NPC48010
0.8351 Intermediate Similarity NPC191892
0.8351 Intermediate Similarity NPC247957
0.8351 Intermediate Similarity NPC249187
0.8351 Intermediate Similarity NPC117185
0.8333 Intermediate Similarity NPC471722
0.8333 Intermediate Similarity NPC472483
0.8333 Intermediate Similarity NPC471941
0.8333 Intermediate Similarity NPC44181
0.8315 Intermediate Similarity NPC475022
0.8315 Intermediate Similarity NPC72133
0.8315 Intermediate Similarity NPC473168
0.8315 Intermediate Similarity NPC222613
0.8315 Intermediate Similarity NPC118648
0.83 Intermediate Similarity NPC2766
0.83 Intermediate Similarity NPC214644
0.8295 Intermediate Similarity NPC472480
0.8295 Intermediate Similarity NPC472265
0.8283 Intermediate Similarity NPC58370
0.8283 Intermediate Similarity NPC43285
0.828 Intermediate Similarity NPC174051
0.828 Intermediate Similarity NPC473172
0.828 Intermediate Similarity NPC67831
0.8276 Intermediate Similarity NPC320514
0.8265 Intermediate Similarity NPC235889
0.8265 Intermediate Similarity NPC72255
0.8261 Intermediate Similarity NPC272746
0.8261 Intermediate Similarity NPC131872
0.8261 Intermediate Similarity NPC19114
0.8261 Intermediate Similarity NPC262870
0.8247 Intermediate Similarity NPC22388
0.8247 Intermediate Similarity NPC477915
0.8242 Intermediate Similarity NPC474704
0.8242 Intermediate Similarity NPC119416
0.8242 Intermediate Similarity NPC86319
0.8242 Intermediate Similarity NPC472475
0.8242 Intermediate Similarity NPC275740
0.8242 Intermediate Similarity NPC472477
0.8242 Intermediate Similarity NPC54689
0.8242 Intermediate Similarity NPC475921
0.8242 Intermediate Similarity NPC262043
0.8235 Intermediate Similarity NPC82635
0.8229 Intermediate Similarity NPC83709
0.8229 Intermediate Similarity NPC15390
0.8222 Intermediate Similarity NPC99909
0.8218 Intermediate Similarity NPC235077
0.8211 Intermediate Similarity NPC107243
0.8211 Intermediate Similarity NPC57416
0.8211 Intermediate Similarity NPC473161
0.8202 Intermediate Similarity NPC6185
0.8202 Intermediate Similarity NPC36350
0.8202 Intermediate Similarity NPC474083
0.8202 Intermediate Similarity NPC241512
0.8202 Intermediate Similarity NPC29447
0.8202 Intermediate Similarity NPC323765
0.8191 Intermediate Similarity NPC472485
0.8191 Intermediate Similarity NPC271195
0.8191 Intermediate Similarity NPC469599
0.8191 Intermediate Similarity NPC280725
0.8191 Intermediate Similarity NPC473170
0.8182 Intermediate Similarity NPC477852
0.8182 Intermediate Similarity NPC181265
0.8182 Intermediate Similarity NPC196528
0.8182 Intermediate Similarity NPC60681
0.8172 Intermediate Similarity NPC66429
0.8172 Intermediate Similarity NPC152897
0.8172 Intermediate Similarity NPC470376
0.8172 Intermediate Similarity NPC243866
0.8172 Intermediate Similarity NPC474736
0.8172 Intermediate Similarity NPC470375
0.8161 Intermediate Similarity NPC116797
0.8161 Intermediate Similarity NPC55869
0.8161 Intermediate Similarity NPC477372
0.8161 Intermediate Similarity NPC147066
0.8152 Intermediate Similarity NPC191684
0.8152 Intermediate Similarity NPC126993
0.8152 Intermediate Similarity NPC69622
0.8152 Intermediate Similarity NPC85173
0.8137 Intermediate Similarity NPC43775
0.8132 Intermediate Similarity NPC193360
0.8132 Intermediate Similarity NPC310752
0.8132 Intermediate Similarity NPC292491
0.8132 Intermediate Similarity NPC131470
0.8132 Intermediate Similarity NPC143767
0.8125 Intermediate Similarity NPC191565
0.8125 Intermediate Similarity NPC235464
0.8125 Intermediate Similarity NPC197386
0.8125 Intermediate Similarity NPC166745
0.8119 Intermediate Similarity NPC470257
0.8119 Intermediate Similarity NPC304495
0.8118 Intermediate Similarity NPC106078
0.8111 Intermediate Similarity NPC472491
0.8111 Intermediate Similarity NPC155011
0.8111 Intermediate Similarity NPC195640
0.8111 Intermediate Similarity NPC89077
0.8111 Intermediate Similarity NPC472494
0.8105 Intermediate Similarity NPC328162
0.8105 Intermediate Similarity NPC249954
0.8105 Intermediate Similarity NPC305483

  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 NPC326627 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
1.0 High Similarity NPD4753 Phase 2
0.9432 High Similarity NPD4629 Approved
0.9432 High Similarity NPD5210 Approved
0.9398 High Similarity NPD4197 Approved
0.9286 High Similarity NPD5329 Approved
0.9222 High Similarity NPD6084 Phase 2
0.9222 High Similarity NPD4755 Approved
0.9222 High Similarity NPD6083 Phase 2
0.9167 High Similarity NPD3666 Approved
0.9167 High Similarity NPD3665 Phase 1
0.9167 High Similarity NPD3133 Approved
0.9157 High Similarity NPD4221 Approved
0.9157 High Similarity NPD4223 Phase 3
0.9022 High Similarity NPD5285 Approved
0.9022 High Similarity NPD4700 Approved
0.9022 High Similarity NPD4696 Approved
0.9022 High Similarity NPD5286 Approved
0.9 High Similarity NPD5695 Phase 3
0.8953 High Similarity NPD5280 Approved
0.8953 High Similarity NPD4694 Approved
0.8953 High Similarity NPD5690 Phase 2
0.8913 High Similarity NPD5696 Approved
0.883 High Similarity NPD4633 Approved
0.883 High Similarity NPD5225 Approved
0.883 High Similarity NPD5224 Approved
0.883 High Similarity NPD5226 Approved
0.883 High Similarity NPD5211 Phase 2
0.8778 High Similarity NPD4202 Approved
0.8737 High Similarity NPD5175 Approved
0.8737 High Similarity NPD5174 Approved
0.8736 High Similarity NPD4693 Phase 3
0.8736 High Similarity NPD5205 Approved
0.8736 High Similarity NPD4689 Approved
0.8736 High Similarity NPD4138 Approved
0.8736 High Similarity NPD4690 Approved
0.8736 High Similarity NPD4688 Approved
0.8736 High Similarity NPD5279 Phase 3
0.8723 High Similarity NPD5223 Approved
0.8646 High Similarity NPD5141 Approved
0.8557 High Similarity NPD7128 Approved
0.8557 High Similarity NPD4767 Approved
0.8557 High Similarity NPD4768 Approved
0.8557 High Similarity NPD6675 Approved
0.8557 High Similarity NPD5739 Approved
0.8557 High Similarity NPD6402 Approved
0.8542 High Similarity NPD4754 Approved
0.8523 High Similarity NPD3618 Phase 1
0.8506 High Similarity NPD4786 Approved
0.8495 Intermediate Similarity NPD5220 Clinical (unspecified phase)
0.8495 Intermediate Similarity NPD5221 Approved
0.8495 Intermediate Similarity NPD5222 Approved
0.8495 Intermediate Similarity NPD4697 Phase 3
0.8488 Intermediate Similarity NPD3667 Approved
0.8469 Intermediate Similarity NPD5701 Approved
0.8469 Intermediate Similarity NPD5697 Approved
0.8452 Intermediate Similarity NPD3617 Approved
0.8444 Intermediate Similarity NPD6904 Approved
0.8444 Intermediate Similarity NPD5328 Approved
0.8444 Intermediate Similarity NPD6673 Approved
0.8444 Intermediate Similarity NPD6080 Approved
0.8404 Intermediate Similarity NPD5173 Approved
0.8391 Intermediate Similarity NPD4788 Approved
0.8384 Intermediate Similarity NPD7320 Approved
0.8384 Intermediate Similarity NPD5128 Approved
0.8384 Intermediate Similarity NPD6899 Approved
0.8384 Intermediate Similarity NPD6881 Approved
0.8384 Intermediate Similarity NPD4730 Approved
0.8384 Intermediate Similarity NPD4729 Approved
0.8353 Intermediate Similarity NPD4195 Approved
0.8333 Intermediate Similarity NPD5737 Approved
0.8333 Intermediate Similarity NPD6672 Approved
0.8315 Intermediate Similarity NPD3574 Clinical (unspecified phase)
0.83 Intermediate Similarity NPD6013 Approved
0.83 Intermediate Similarity NPD6014 Approved
0.83 Intermediate Similarity NPD6012 Approved
0.83 Intermediate Similarity NPD6373 Approved
0.83 Intermediate Similarity NPD6372 Approved
0.8261 Intermediate Similarity NPD5693 Phase 1
0.8261 Intermediate Similarity NPD5281 Approved
0.8261 Intermediate Similarity NPD6079 Approved
0.8261 Intermediate Similarity NPD5284 Approved
0.8256 Intermediate Similarity NPD4695 Discontinued
0.8218 Intermediate Similarity NPD5250 Approved
0.8218 Intermediate Similarity NPD5247 Approved
0.8218 Intermediate Similarity NPD5248 Approved
0.8218 Intermediate Similarity NPD6883 Approved
0.8218 Intermediate Similarity NPD5249 Phase 3
0.8218 Intermediate Similarity NPD7102 Approved
0.8218 Intermediate Similarity NPD7290 Approved
0.8218 Intermediate Similarity NPD5251 Approved
0.8218 Intermediate Similarity NPD4634 Approved
0.82 Intermediate Similarity NPD6011 Approved
0.8172 Intermediate Similarity NPD5133 Approved
0.8152 Intermediate Similarity NPD5692 Phase 3
0.8137 Intermediate Similarity NPD6869 Approved
0.8137 Intermediate Similarity NPD8130 Phase 1
0.8137 Intermediate Similarity NPD5217 Approved
0.8137 Intermediate Similarity NPD5216 Approved
0.8137 Intermediate Similarity NPD6649 Approved
0.8137 Intermediate Similarity NPD6847 Approved
0.8137 Intermediate Similarity NPD6617 Approved
0.8137 Intermediate Similarity NPD5215 Approved
0.8137 Intermediate Similarity NPD6650 Approved
0.8111 Intermediate Similarity NPD7334 Approved
0.8111 Intermediate Similarity NPD6684 Approved
0.8111 Intermediate Similarity NPD6098 Approved
0.8111 Intermediate Similarity NPD7521 Approved
0.8111 Intermediate Similarity NPD6409 Approved
0.8111 Intermediate Similarity NPD7146 Approved
0.8111 Intermediate Similarity NPD5330 Approved
0.8065 Intermediate Similarity NPD5694 Approved
0.8065 Intermediate Similarity NPD6050 Approved
0.8061 Intermediate Similarity NPD5091 Approved
0.8058 Intermediate Similarity NPD8297 Approved
0.8058 Intermediate Similarity NPD6882 Approved
0.8039 Intermediate Similarity NPD5135 Approved
0.8039 Intermediate Similarity NPD5134 Clinical (unspecified phase)
0.8039 Intermediate Similarity NPD5169 Approved
0.7961 Intermediate Similarity NPD5127 Approved
0.7961 Intermediate Similarity NPD6401 Clinical (unspecified phase)
0.7957 Intermediate Similarity NPD4096 Approved
0.7955 Intermediate Similarity NPD4139 Approved
0.7955 Intermediate Similarity NPD4692 Approved
0.7935 Intermediate Similarity NPD6903 Approved
0.7935 Intermediate Similarity NPD5208 Approved
0.7935 Intermediate Similarity NPD7513 Clinical (unspecified phase)
0.7889 Intermediate Similarity NPD3668 Phase 3
0.7831 Intermediate Similarity NPD4747 Approved
0.783 Intermediate Similarity NPD6274 Approved
0.7812 Intermediate Similarity NPD6356 Clinical (unspecified phase)
0.781 Intermediate Similarity NPD4632 Approved
0.7791 Intermediate Similarity NPD3701 Clinical (unspecified phase)
0.7789 Intermediate Similarity NPD6399 Phase 3
0.7745 Intermediate Similarity NPD6412 Phase 2
0.7742 Intermediate Similarity NPD4518 Approved
0.7738 Intermediate Similarity NPD4243 Approved
0.7736 Intermediate Similarity NPD5167 Approved
0.7717 Intermediate Similarity NPD4519 Discontinued
0.7717 Intermediate Similarity NPD4623 Approved
0.7711 Intermediate Similarity NPD4137 Phase 3
0.7684 Intermediate Similarity NPD7515 Phase 2
0.767 Intermediate Similarity NPD5168 Approved
0.7629 Intermediate Similarity NPD5654 Approved
0.7619 Intermediate Similarity NPD4691 Approved
0.7615 Intermediate Similarity NPD7100 Approved
0.7615 Intermediate Similarity NPD4522 Approved
0.7615 Intermediate Similarity NPD7101 Approved
0.7593 Intermediate Similarity NPD6317 Approved
0.7593 Intermediate Similarity NPD6009 Approved
0.7579 Intermediate Similarity NPD5207 Approved
0.7558 Intermediate Similarity NPD4785 Approved
0.7558 Intermediate Similarity NPD4784 Approved
0.7545 Intermediate Similarity NPD6054 Approved
0.7545 Intermediate Similarity NPD6319 Approved
0.7545 Intermediate Similarity NPD6059 Approved
0.7526 Intermediate Similarity NPD6001 Approved
0.7523 Intermediate Similarity NPD6313 Approved
0.7523 Intermediate Similarity NPD6335 Approved
0.7523 Intermediate Similarity NPD6314 Approved
0.7477 Intermediate Similarity NPD6908 Approved
0.7477 Intermediate Similarity NPD6016 Approved
0.7477 Intermediate Similarity NPD6015 Approved
0.7477 Intermediate Similarity NPD6909 Approved
0.7475 Intermediate Similarity NPD5959 Approved
0.7474 Intermediate Similarity NPD7285 Clinical (unspecified phase)
0.7471 Intermediate Similarity NPD6942 Approved
0.7471 Intermediate Similarity NPD4190 Phase 3
0.7471 Intermediate Similarity NPD5275 Approved
0.7471 Intermediate Similarity NPD7339 Approved
0.7444 Intermediate Similarity NPD7525 Registered
0.7412 Intermediate Similarity NPD4789 Approved
0.7411 Intermediate Similarity NPD5988 Approved
0.7411 Intermediate Similarity NPD6370 Approved
0.7356 Intermediate Similarity NPD4687 Approved
0.7356 Intermediate Similarity NPD4058 Approved
0.7356 Intermediate Similarity NPD5733 Approved
0.7347 Intermediate Similarity NPD7748 Approved
0.7326 Intermediate Similarity NPD5276 Approved
0.7321 Intermediate Similarity NPD6291 Clinical (unspecified phase)
0.7321 Intermediate Similarity NPD5983 Phase 2
0.7308 Intermediate Similarity NPD6008 Approved
0.7294 Intermediate Similarity NPD3698 Phase 2
0.7281 Intermediate Similarity NPD7492 Approved
0.7263 Intermediate Similarity NPD4751 Clinical (unspecified phase)
0.7238 Intermediate Similarity NPD6614 Approved
0.7234 Intermediate Similarity NPD7520 Clinical (unspecified phase)
0.7229 Intermediate Similarity NPD3171 Clinical (unspecified phase)
0.7228 Intermediate Similarity NPD7638 Approved
0.7217 Intermediate Similarity NPD6616 Approved
0.7209 Intermediate Similarity NPD4245 Approved
0.7209 Intermediate Similarity NPD4244 Approved
0.7193 Intermediate Similarity NPD7604 Phase 2
0.7182 Intermediate Similarity NPD6868 Approved
0.7176 Intermediate Similarity NPD3621 Clinical (unspecified phase)
0.7159 Intermediate Similarity NPD6926 Approved
0.7159 Intermediate Similarity NPD6924 Approved
0.7157 Intermediate Similarity NPD7640 Approved
0.7157 Intermediate Similarity NPD7639 Approved
0.7155 Intermediate Similarity NPD7078 Approved
0.7155 Intermediate Similarity NPD8293 Discontinued

  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