Structure

Physi-Chem Properties

Molecular Weight:  346.21
Volume:  364.798
LogP:  2.165
LogD:  1.735
LogS:  -2.868
# 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:  0.754
Synthetic Accessibility Score:  4.493
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:  -4.758
MDCK Permeability:  1.2272579624550417e-05
Pgp-inhibitor:  0.385
Pgp-substrate:  0.778
Human Intestinal Absorption (HIA):  0.007
20% Bioavailability (F20%):  0.914
30% Bioavailability (F30%):  0.016

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.538
Plasma Protein Binding (PPB):  45.63043975830078%
Volume Distribution (VD):  0.607
Pgp-substrate:  39.97221755981445%

ADMET: Metabolism

CYP1A2-inhibitor:  0.013
CYP1A2-substrate:  0.36
CYP2C19-inhibitor:  0.016
CYP2C19-substrate:  0.33
CYP2C9-inhibitor:  0.024
CYP2C9-substrate:  0.093
CYP2D6-inhibitor:  0.003
CYP2D6-substrate:  0.161
CYP3A4-inhibitor:  0.53
CYP3A4-substrate:  0.265

ADMET: Excretion

Clearance (CL):  7.432
Half-life (T1/2):  0.949

ADMET: Toxicity

hERG Blockers:  0.037
Human Hepatotoxicity (H-HT):  0.078
Drug-inuced Liver Injury (DILI):  0.157
AMES Toxicity:  0.053
Rat Oral Acute Toxicity:  0.803
Maximum Recommended Daily Dose:  0.854
Skin Sensitization:  0.145
Carcinogencity:  0.681
Eye Corrosion:  0.221
Eye Irritation:  0.175
Respiratory Toxicity:  0.952

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

  Natural Product: NPC185936

Natural Product ID:  NPC185936
Common Name*:   (8S,10R,11S,13S,14S,17S)-11-Hydroxy-17-(2-Hydroxyacetyl)-10,13-Dimethyl-1,2,6,7,8,9,11,12,14,15,16,17-Dodecahydrocyclopenta[A]Phenanthren-3-One
IUPAC Name:   (8S,10R,11S,13S,14S,17S)-11-hydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one
Synonyms:  
Standard InCHIKey:  OMFXVFTZEKFJBZ-KRGAXNBZSA-N
Standard InCHI:  InChI=1S/C21H30O4/c1-20-8-7-13(23)9-12(20)3-4-14-15-5-6-16(18(25)11-22)21(15,2)10-17(24)19(14)20/h9,14-17,19,22,24H,3-8,10-11H2,1-2H3/t14-,15-,16+,17-,19?,20-,21-/m0/s1
SMILES:  OCC(=O)[C@H]1CC[C@@H]2[C@]1(C)C[C@H](O)C1[C@H]2CCC2=CC(=O)CC[C@]12C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1513569
PubChem CID:   16758819
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
NPO9165 Asclepias curassavica Species Apocynaceae Eukaryota n.a. n.a. n.a. PMID[16252914]
NPO9165 Asclepias curassavica Species Apocynaceae Eukaryota n.a. n.a. n.a. PMID[19251412]
NPO12323 Bos taurus Species Bovidae Eukaryota n.a. n.a. n.a. PMID[24211545]
NPO12323 Bos taurus Species Bovidae Eukaryota Urine n.a. n.a. PMID[6330305]
NPO12323 Bos taurus Species Bovidae Eukaryota n.a. n.a. n.a. PMID[932730]
NPO12323 Bos taurus Species Bovidae Eukaryota n.a. n.a. Database[FooDB]
NPO12323 Bos taurus Species Bovidae Eukaryota n.a. n.a. Database[FooDB]
NPO17393 Bubalus bubalis Species Bovidae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO9165 Asclepias curassavica Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO12323 Bos taurus Species Bovidae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO17393 Bubalus bubalis Species Bovidae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO12323 Bos taurus Species Bovidae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO9165 Asclepias curassavica Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO17393 Bubalus bubalis Species Bovidae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO12323 Bos taurus Species Bovidae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO9165 Asclepias curassavica Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12323 Bos taurus Species Bovidae 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
NPT51 Individual Protein Microtubule-associated protein tau Homo sapiens Potency = 125.9 nM PMID[493244]
NPT483 Individual Protein Prelamin-A/C Homo sapiens Potency = 25118.9 nM PMID[493244]
NPT58 Individual Protein Bloom syndrome protein Homo sapiens Potency = 89125.1 nM PMID[493244]
NPT5 Individual Protein Histone-lysine N-methyltransferase, H3 lysine-9 specific 3 Homo sapiens Potency n.a. 22.4 nM PMID[493244]
NPT49 Individual Protein DNA-(apurinic or apyrimidinic site) lyase Homo sapiens Potency n.a. 8912.5 nM PMID[493244]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Potency = 12589.3 nM PMID[493244]
NPT93 Individual Protein Survival motor neuron protein Homo sapiens Potency = 7943.3 nM PMID[493244]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Potency = 11220.2 nM PMID[493244]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Potency = 8912.5 nM PMID[493244]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Potency = 10000.0 nM PMID[493244]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum Potency n.a. 18526.0 nM PMID[493244]

☑ 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 NPC185936 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 NPC168027
0.9647 High Similarity NPC328539
0.9551 High Similarity NPC192428
0.9444 High Similarity NPC18509
0.9326 High Similarity NPC245972
0.9326 High Similarity NPC196485
0.931 High Similarity NPC275740
0.931 High Similarity NPC86319
0.9239 High Similarity NPC144956
0.9195 High Similarity NPC143767
0.9195 High Similarity NPC131470
0.9186 High Similarity NPC327115
0.9176 High Similarity NPC237712
0.9121 High Similarity NPC305483
0.9121 High Similarity NPC96859
0.9121 High Similarity NPC328162
0.9091 High Similarity NPC474245
0.9091 High Similarity NPC1015
0.9091 High Similarity NPC31985
0.908 High Similarity NPC475740
0.907 High Similarity NPC470574
0.9 High Similarity NPC12722
0.9 High Similarity NPC475255
0.9 High Similarity NPC69454
0.8989 High Similarity NPC183283
0.8977 High Similarity NPC471722
0.8966 High Similarity NPC51014
0.8966 High Similarity NPC474733
0.8966 High Similarity NPC474732
0.8966 High Similarity NPC31564
0.8966 High Similarity NPC145879
0.8966 High Similarity NPC72133
0.8966 High Similarity NPC20688
0.8966 High Similarity NPC474778
0.8953 High Similarity NPC85774
0.8953 High Similarity NPC214043
0.8925 High Similarity NPC114274
0.8913 High Similarity NPC249954
0.8901 High Similarity NPC166906
0.8901 High Similarity NPC111015
0.8889 High Similarity NPC63748
0.8889 High Similarity NPC272746
0.8889 High Similarity NPC473998
0.8876 High Similarity NPC326627
0.8876 High Similarity NPC119416
0.8876 High Similarity NPC477943
0.8876 High Similarity NPC309603
0.8876 High Similarity NPC186688
0.8876 High Similarity NPC310010
0.8876 High Similarity NPC473999
0.8864 High Similarity NPC58063
0.8851 High Similarity NPC469948
0.883 High Similarity NPC15390
0.8817 High Similarity NPC43747
0.8804 High Similarity NPC473170
0.8804 High Similarity NPC280725
0.8804 High Similarity NPC259286
0.8804 High Similarity NPC470016
0.8804 High Similarity NPC317586
0.8791 High Similarity NPC472930
0.8778 High Similarity NPC126993
0.8778 High Similarity NPC48010
0.8778 High Similarity NPC191684
0.8778 High Similarity NPC129913
0.8778 High Similarity NPC85173
0.8764 High Similarity NPC53911
0.8736 High Similarity NPC473246
0.8736 High Similarity NPC221758
0.8736 High Similarity NPC161423
0.8736 High Similarity NPC59453
0.8736 High Similarity NPC227064
0.8736 High Similarity NPC58841
0.8736 High Similarity NPC329043
0.8736 High Similarity NPC321187
0.8721 High Similarity NPC48362
0.8721 High Similarity NPC151519
0.871 High Similarity NPC49371
0.8696 High Similarity NPC8993
0.8681 High Similarity NPC99380
0.8681 High Similarity NPC475806
0.8673 High Similarity NPC44063
0.8667 High Similarity NPC475921
0.8667 High Similarity NPC474704
0.8667 High Similarity NPC26959
0.8667 High Similarity NPC268406
0.8667 High Similarity NPC32830
0.8667 High Similarity NPC76879
0.8652 High Similarity NPC141292
0.8652 High Similarity NPC474684
0.8652 High Similarity NPC142361
0.8646 High Similarity NPC477915
0.8636 High Similarity NPC197823
0.8621 High Similarity NPC64600
0.8621 High Similarity NPC476082
0.8621 High Similarity NPC278648
0.8617 High Similarity NPC190554
0.8617 High Similarity NPC108078
0.8602 High Similarity NPC271195
0.8587 High Similarity NPC233118
0.8587 High Similarity NPC477855
0.8557 High Similarity NPC311612
0.8557 High Similarity NPC247957
0.8557 High Similarity NPC249187
0.8557 High Similarity NPC191892
0.8556 High Similarity NPC292491
0.8556 High Similarity NPC158778
0.8556 High Similarity NPC310752
0.8556 High Similarity NPC193360
0.8556 High Similarity NPC474677
0.8556 High Similarity NPC471724
0.8542 High Similarity NPC163372
0.8542 High Similarity NPC302537
0.8539 High Similarity NPC222613
0.8539 High Similarity NPC118648
0.8539 High Similarity NPC475022
0.8539 High Similarity NPC94666
0.8539 High Similarity NPC94755
0.8526 High Similarity NPC147954
0.8523 High Similarity NPC82902
0.8523 High Similarity NPC146683
0.8523 High Similarity NPC472265
0.8523 High Similarity NPC144258
0.85 High Similarity NPC2766
0.85 High Similarity NPC214644
0.8495 Intermediate Similarity NPC471207
0.8495 Intermediate Similarity NPC23170
0.8488 Intermediate Similarity NPC472478
0.8488 Intermediate Similarity NPC164999
0.8485 Intermediate Similarity NPC472925
0.8485 Intermediate Similarity NPC185
0.8478 Intermediate Similarity NPC131872
0.8478 Intermediate Similarity NPC19114
0.8478 Intermediate Similarity NPC189520
0.8478 Intermediate Similarity NPC472978
0.8478 Intermediate Similarity NPC233116
0.8478 Intermediate Similarity NPC212301
0.8478 Intermediate Similarity NPC86266
0.8478 Intermediate Similarity NPC155304
0.8478 Intermediate Similarity NPC110657
0.8469 Intermediate Similarity NPC72255
0.8469 Intermediate Similarity NPC209502
0.8469 Intermediate Similarity NPC204833
0.8469 Intermediate Similarity NPC137657
0.8462 Intermediate Similarity NPC472973
0.8454 Intermediate Similarity NPC308726
0.8454 Intermediate Similarity NPC473424
0.8454 Intermediate Similarity NPC119601
0.8454 Intermediate Similarity NPC87351
0.8444 Intermediate Similarity NPC90652
0.8444 Intermediate Similarity NPC187376
0.8444 Intermediate Similarity NPC136548
0.8444 Intermediate Similarity NPC174619
0.8444 Intermediate Similarity NPC93778
0.8444 Intermediate Similarity NPC317590
0.8444 Intermediate Similarity NPC159046
0.8444 Intermediate Similarity NPC153604
0.8444 Intermediate Similarity NPC233836
0.8438 Intermediate Similarity NPC154072
0.8438 Intermediate Similarity NPC88198
0.8438 Intermediate Similarity NPC327431
0.8438 Intermediate Similarity NPC316964
0.8438 Intermediate Similarity NPC474720
0.8438 Intermediate Similarity NPC110149
0.8438 Intermediate Similarity NPC157787
0.8427 Intermediate Similarity NPC36350
0.8427 Intermediate Similarity NPC474218
0.8427 Intermediate Similarity NPC471224
0.8427 Intermediate Similarity NPC202868
0.8416 Intermediate Similarity NPC235077
0.8409 Intermediate Similarity NPC118800
0.8404 Intermediate Similarity NPC139570
0.8404 Intermediate Similarity NPC174948
0.8404 Intermediate Similarity NPC255809
0.8404 Intermediate Similarity NPC472932
0.8404 Intermediate Similarity NPC200702
0.8404 Intermediate Similarity NPC318282
0.8404 Intermediate Similarity NPC173875
0.8404 Intermediate Similarity NPC469995
0.84 Intermediate Similarity NPC295244
0.8387 Intermediate Similarity NPC470376
0.8387 Intermediate Similarity NPC170220
0.8387 Intermediate Similarity NPC474807
0.8387 Intermediate Similarity NPC141497
0.8387 Intermediate Similarity NPC470375
0.8387 Intermediate Similarity NPC134826
0.8387 Intermediate Similarity NPC109305
0.8387 Intermediate Similarity NPC107674
0.8384 Intermediate Similarity NPC319077
0.8384 Intermediate Similarity NPC257353
0.8384 Intermediate Similarity NPC97202
0.8384 Intermediate Similarity NPC260268
0.8384 Intermediate Similarity NPC152695
0.8384 Intermediate Similarity NPC476027
0.8384 Intermediate Similarity NPC49958
0.8384 Intermediate Similarity NPC85829
0.8384 Intermediate Similarity NPC171137
0.8384 Intermediate Similarity NPC202167
0.8384 Intermediate Similarity NPC149047
0.8384 Intermediate Similarity NPC48733
0.8384 Intermediate Similarity NPC214264

  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 NPC185936 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
0.9551 High Similarity NPD5221 Approved
0.9551 High Similarity NPD5220 Clinical (unspecified phase)
0.9551 High Similarity NPD5222 Approved
0.9551 High Similarity NPD4697 Phase 3
0.9535 High Similarity NPD5328 Approved
0.9444 High Similarity NPD4755 Approved
0.9444 High Similarity NPD5173 Approved
0.9318 High Similarity NPD6079 Approved
0.9239 High Similarity NPD5286 Approved
0.9239 High Similarity NPD5285 Approved
0.9239 High Similarity NPD4700 Approved
0.9239 High Similarity NPD4696 Approved
0.9186 High Similarity NPD3618 Phase 1
0.914 High Similarity NPD5223 Approved
0.9043 High Similarity NPD5226 Approved
0.9043 High Similarity NPD5224 Approved
0.9043 High Similarity NPD5225 Approved
0.9043 High Similarity NPD4633 Approved
0.9043 High Similarity NPD5211 Phase 2
0.8947 High Similarity NPD5175 Approved
0.8947 High Similarity NPD4754 Approved
0.8947 High Similarity NPD5174 Approved
0.8876 High Similarity NPD4753 Phase 2
0.8854 High Similarity NPD5141 Approved
0.8791 High Similarity NPD4202 Approved
0.8763 High Similarity NPD4767 Approved
0.8763 High Similarity NPD5739 Approved
0.8763 High Similarity NPD4768 Approved
0.8763 High Similarity NPD7128 Approved
0.8763 High Similarity NPD6675 Approved
0.8763 High Similarity NPD6402 Approved
0.875 High Similarity NPD5279 Phase 3
0.8736 High Similarity NPD4786 Approved
0.8736 High Similarity NPD3666 Approved
0.8736 High Similarity NPD3665 Phase 1
0.8736 High Similarity NPD3133 Approved
0.8721 High Similarity NPD3667 Approved
0.8673 High Similarity NPD5697 Approved
0.8673 High Similarity NPD5701 Approved
0.8586 High Similarity NPD7320 Approved
0.8586 High Similarity NPD6881 Approved
0.8586 High Similarity NPD6899 Approved
0.8586 High Similarity NPD6011 Approved
0.8586 High Similarity NPD5128 Approved
0.8586 High Similarity NPD5168 Approved
0.8586 High Similarity NPD4729 Approved
0.8586 High Similarity NPD4730 Approved
0.8523 High Similarity NPD4197 Approved
0.85 High Similarity NPD6013 Approved
0.85 High Similarity NPD6014 Approved
0.85 High Similarity NPD6012 Approved
0.85 High Similarity NPD6373 Approved
0.85 High Similarity NPD6372 Approved
0.8427 Intermediate Similarity NPD5329 Approved
0.8416 Intermediate Similarity NPD5134 Clinical (unspecified phase)
0.8416 Intermediate Similarity NPD5169 Approved
0.8416 Intermediate Similarity NPD5250 Approved
0.8416 Intermediate Similarity NPD5251 Approved
0.8416 Intermediate Similarity NPD5247 Approved
0.8416 Intermediate Similarity NPD6883 Approved
0.8416 Intermediate Similarity NPD7290 Approved
0.8416 Intermediate Similarity NPD4634 Approved
0.8416 Intermediate Similarity NPD5135 Approved
0.8416 Intermediate Similarity NPD5248 Approved
0.8416 Intermediate Similarity NPD7102 Approved
0.8416 Intermediate Similarity NPD5249 Phase 3
0.8404 Intermediate Similarity NPD4629 Approved
0.8404 Intermediate Similarity NPD5210 Approved
0.8333 Intermediate Similarity NPD6617 Approved
0.8333 Intermediate Similarity NPD5127 Approved
0.8333 Intermediate Similarity NPD6847 Approved
0.8333 Intermediate Similarity NPD6401 Clinical (unspecified phase)
0.8333 Intermediate Similarity NPD5215 Approved
0.8333 Intermediate Similarity NPD6650 Approved
0.8333 Intermediate Similarity NPD8130 Phase 1
0.8333 Intermediate Similarity NPD5216 Approved
0.8333 Intermediate Similarity NPD5217 Approved
0.8333 Intermediate Similarity NPD6649 Approved
0.8333 Intermediate Similarity NPD6869 Approved
0.8295 Intermediate Similarity NPD4223 Phase 3
0.8295 Intermediate Similarity NPD4221 Approved
0.828 Intermediate Similarity NPD7515 Phase 2
0.8256 Intermediate Similarity NPD3617 Approved
0.8252 Intermediate Similarity NPD6882 Approved
0.8252 Intermediate Similarity NPD8297 Approved
0.8229 Intermediate Similarity NPD6083 Phase 2
0.8229 Intermediate Similarity NPD6084 Phase 2
0.8173 Intermediate Similarity NPD4632 Approved
0.8152 Intermediate Similarity NPD5737 Approved
0.8152 Intermediate Similarity NPD6672 Approved
0.8132 Intermediate Similarity NPD3574 Clinical (unspecified phase)
0.8132 Intermediate Similarity NPD5280 Approved
0.8132 Intermediate Similarity NPD4694 Approved
0.8132 Intermediate Similarity NPD5690 Phase 2
0.8111 Intermediate Similarity NPD3668 Phase 3
0.8095 Intermediate Similarity NPD5167 Approved
0.8068 Intermediate Similarity NPD4695 Discontinued
0.8021 Intermediate Similarity NPD5695 Phase 3
0.8019 Intermediate Similarity NPD6274 Approved
0.8019 Intermediate Similarity NPD6868 Approved
0.8 Intermediate Similarity NPD6399 Phase 3
0.7959 Intermediate Similarity NPD5696 Approved
0.7944 Intermediate Similarity NPD6317 Approved
0.7944 Intermediate Similarity NPD6009 Approved
0.7935 Intermediate Similarity NPD4138 Approved
0.7935 Intermediate Similarity NPD4689 Approved
0.7935 Intermediate Similarity NPD4693 Phase 3
0.7935 Intermediate Similarity NPD5205 Approved
0.7935 Intermediate Similarity NPD4690 Approved
0.7935 Intermediate Similarity NPD4688 Approved
0.7917 Intermediate Similarity NPD7748 Approved
0.787 Intermediate Similarity NPD6314 Approved
0.787 Intermediate Similarity NPD6335 Approved
0.787 Intermediate Similarity NPD6313 Approved
0.7865 Intermediate Similarity NPD7525 Registered
0.7826 Intermediate Similarity NPD7520 Clinical (unspecified phase)
0.7798 Intermediate Similarity NPD7100 Approved
0.7798 Intermediate Similarity NPD7101 Approved
0.7742 Intermediate Similarity NPD6684 Approved
0.7742 Intermediate Similarity NPD7334 Approved
0.7742 Intermediate Similarity NPD7521 Approved
0.7742 Intermediate Similarity NPD6409 Approved
0.7742 Intermediate Similarity NPD7146 Approved
0.7742 Intermediate Similarity NPD5330 Approved
0.7727 Intermediate Similarity NPD6319 Approved
0.7727 Intermediate Similarity NPD6054 Approved
0.7727 Intermediate Similarity NPD6059 Approved
0.7701 Intermediate Similarity NPD6942 Approved
0.7701 Intermediate Similarity NPD7339 Approved
0.7684 Intermediate Similarity NPD6080 Approved
0.7684 Intermediate Similarity NPD6673 Approved
0.7684 Intermediate Similarity NPD6904 Approved
0.7677 Intermediate Similarity NPD7902 Approved
0.767 Intermediate Similarity NPD6008 Approved
0.7658 Intermediate Similarity NPD6908 Approved
0.7658 Intermediate Similarity NPD5983 Phase 2
0.7658 Intermediate Similarity NPD6291 Clinical (unspecified phase)
0.7658 Intermediate Similarity NPD6015 Approved
0.7658 Intermediate Similarity NPD6909 Approved
0.7658 Intermediate Similarity NPD6016 Approved
0.7647 Intermediate Similarity NPD4747 Approved
0.7614 Intermediate Similarity NPD3701 Clinical (unspecified phase)
0.7609 Intermediate Similarity NPD4788 Approved
0.76 Intermediate Similarity NPD7638 Approved
0.7589 Intermediate Similarity NPD5988 Approved
0.7589 Intermediate Similarity NPD6370 Approved
0.7579 Intermediate Similarity NPD7513 Clinical (unspecified phase)
0.7579 Intermediate Similarity NPD6903 Approved
0.7556 Intermediate Similarity NPD4195 Approved
0.7529 Intermediate Similarity NPD4137 Phase 3
0.7526 Intermediate Similarity NPD5693 Phase 1
0.7526 Intermediate Similarity NPD5281 Approved
0.7526 Intermediate Similarity NPD5284 Approved
0.7525 Intermediate Similarity NPD7640 Approved
0.7525 Intermediate Similarity NPD7639 Approved
0.7522 Intermediate Similarity NPD7604 Phase 2
0.75 Intermediate Similarity NPD3703 Phase 2
0.7475 Intermediate Similarity NPD6356 Clinical (unspecified phase)
0.7474 Intermediate Similarity NPD3573 Approved
0.7456 Intermediate Similarity NPD7492 Approved
0.7449 Intermediate Similarity NPD5133 Approved
0.7442 Intermediate Similarity NPD4691 Approved
0.7423 Intermediate Similarity NPD5692 Phase 3
0.7391 Intermediate Similarity NPD6616 Approved
0.7391 Intermediate Similarity NPD6336 Discontinued
0.7379 Intermediate Similarity NPD5091 Approved
0.7374 Intermediate Similarity NPD7900 Approved
0.7374 Intermediate Similarity NPD7901 Clinical (unspecified phase)
0.7368 Intermediate Similarity NPD4623 Approved
0.7368 Intermediate Similarity NPD4519 Discontinued
0.7368 Intermediate Similarity NPD6098 Approved
0.7356 Intermediate Similarity NPD4809 Clinical (unspecified phase)
0.7356 Intermediate Similarity NPD4808 Clinical (unspecified phase)
0.7347 Intermediate Similarity NPD8035 Phase 2
0.7347 Intermediate Similarity NPD5694 Approved
0.7347 Intermediate Similarity NPD6050 Approved
0.7347 Intermediate Similarity NPD8034 Phase 2
0.7328 Intermediate Similarity NPD8293 Discontinued
0.7328 Intermediate Similarity NPD7078 Approved
0.7326 Intermediate Similarity NPD3699 Clinical (unspecified phase)
0.7326 Intermediate Similarity NPD3700 Clinical (unspecified phase)
0.732 Intermediate Similarity NPD7285 Clinical (unspecified phase)
0.7297 Intermediate Similarity NPD7115 Discovery
0.7283 Intermediate Similarity NPD8259 Clinical (unspecified phase)
0.7265 Intermediate Similarity NPD6033 Approved
0.7265 Intermediate Similarity NPD7736 Approved
0.7264 Intermediate Similarity NPD6412 Phase 2
0.7255 Intermediate Similarity NPD5290 Discontinued
0.7245 Intermediate Similarity NPD4096 Approved
0.7241 Intermediate Similarity NPD4789 Approved
0.7222 Intermediate Similarity NPD6117 Approved
0.7216 Intermediate Similarity NPD5208 Approved
0.7204 Intermediate Similarity NPD4139 Approved
0.7204 Intermediate Similarity NPD4692 Approved
0.72 Intermediate Similarity NPD6001 Approved
0.7191 Intermediate Similarity NPD4058 Approved
0.7191 Intermediate Similarity NPD5733 Approved
0.7191 Intermediate Similarity NPD4687 Approved
0.7174 Intermediate Similarity NPD7645 Phase 2
0.7159 Intermediate Similarity NPD5276 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